PROCEDURE FOR MANUFACTURING NEW CARBOSTYRILDERIVATEN AND THEIR ACID ADDITION SALTS

26-11-1984 дата публикации
Номер:
AT0000376432B
Автор:
Принадлежит: Otsuka Pharma Co Ltd
Контакты:
Номер заявки: 235179
Дата заявки: 29-03-1979

[1]

The invention concerns a procedure for manufacturing new Carbostyrilderivate of the general formula (i) where RL hydrogen, an alkyl group with 1 to 6 carbon atoms, a group of alkenyls with 2 to 4 carbon atoms, a Alkinylgruppe with 2 to 4 carbon atoms or a Phenylalkylgruppe with a group of alkyls with i to 4 carbon atoms, R2 hydrogen, an alkyl group with I to 4 carbon atoms or a Phenylgruppe, R hydrogen, a hydroxy group or an alkyl group with I to 4 carbon atoms, I0 a Alkanoyloxygruppe with i to 4 carbon atoms or a 3,4,5-Trimethoxybenzoyloxygruppe, R " hydrogen or an alkyl group with I to 4 Koblenstoffatomen, R-S a Cycloalkylgruppe with 3 to 8 carbon atoms, a Phenylgruppe, the I to 3 substituent from the group halogen atom, alkyl group with I as far as 4 carbon atoms and alkoxy group with 1 to 4 carbon atoms to carry, a substituted alkyl group with 1 to 4 carbon atoms with a Phenylgruppe or Alkanoyloxygruppe with 1 to 4 carbon atoms can mean as substituent, a Alkanoylgruppe with 1 to 4 carbon atoms or a group of benzyles and an X a halogen atom meant equal n is 0, 1 or 2, equal q is 2 or 3 and 1 and m in each case 0 or whole numbers from 1 to 6 and hiebei the sum of 1 and m 6 does not exceed, whereby the carbon carbon connection between the 3und of the 4-Stellung in the Carbostyrilgerüst a Einfachoder double bond is and the Seitenkette a'/(CH2) - Oh (CHz) 1 - CH (CH z) N N-R-S under the condition in the 4, 5, 6, 7oder 8-Stellung it is that, if this Seitenkette stands in 4-Stellung R2 is void, and R-S then no alkyl group with 1 to 4 carbon atoms, exhibiting a Phenylgruppe as substituents, to be can, if R is a Phenylgruppe, as well as of their acid addition salts. Producible the according to invention connections possess antihistamine effect and tax effect on the central nervous system, why they as Antihistaminika and 6teuerungsmittel for the central nervous system are useful. 3S like it in different articles of the medical and pharmaceutical literature, for example in Goodman, Gilman: “Pharmacology” (volume 1); “YAKUBUTSU CHIRYO NO KISO TON of RINSHO” bases and clinical the Pharmacotherapie), P. 781 to 835 (given change by Hirokawa Shoten CO.,; “SBIN OYO YAKURIGAKU” (new applied pharmacology) of H [eashi UN, P. 307 to 319 (given change by nail Shoten CO.,); “SHIN YAKU TON of RINSHO” (magazine for new cures & hospital), volume 20, Nr.ll, P. 129 to 133; and “KISO TON of RINSHO” (laboratory and hospital) volume 10, Nr.10, P. 17 to 27, descriptive is inhibiert, in the s a general antihistamine means not the isolation of a combined histamine type, which is formed by the antigen antibody reaction of a11ergie, but inhibiert the combination (a kompetitiver antagonism) of an active Histamlntypus with a histamine acceptor, whereby the antihistamine effect results. Therefore producible the according to invention Antihistaminika effective as treatment means and preventive means for different allergische I0 illnesses and symptoms are, like chronic sneezing and/or cold, burning the eyes, nose and throat, a11ergische of symptoms of the breathing ways, hay cold, Polynosis, acute Uritiearie (, edemas, swelling itch u.dgl.), vascular edemas, Pruritus, atopische Dermatitis, insect bites, Dermatitis of the contact type, like “Urushi Kabure”, Ulticarie with serum illness, desert-mix disturbances, allergische Rhinitis, allergische Conjuctivitis or orneitis devoted from the combination of histamine and histamine acceptor. Beyond that the antihistamine means can serve also as an additive for the healing of the general Anaphylaxe, whereby from histamine different Autacoide can play an important role. Beyond that an antihistamine means can serve the gastric acid concentration also as a diagnostic reagent for the measurement. In the pharmaceutical literature it was reported that 5 (3-tert. Butylamino-2-hydroxy) - - propoxy-3,4-dihydro¢arboetyril. Hydrochloride of the following formula l H in a certain extent an antihistamine effect (pA2 = 5.02), {OYO YAKURI (applied Pharmacologie), volume ii, Nr.4, S.437 to 462} shows. Beyond that are in the DE-OS 2302027 2s (those the US-PS Nr.3910924 corresponds) (2-Hydroxy-3-amino) - propoxy (3,4-dihydro) - carbostyril - derivatives described, which exhibit an B-adrenergic blocking effect. Producible the according to invention new connections with antihistamine effect and control effect on the central nervous system are not however so far become known. The control controlling producible of the according to invention connections on the central nervous system is characterized by that they affect the combat movement of a mouse, which was alone isolated from others during a long period. Compared with diazepam, which admits as connection with strong such activities is, producible the according to invention connections exhibited unusual tax effects on the combat movement of the mouse, why producible the according to invention connections are applicable in particular as Sedativa, drugs against fear and antimanisch depressive Psychosedrogen. Beyond that producible the according to invention connections possess a strong effect on the increasing anaesthesia and the sleep, if they are used in combination with anaesthetics and Hypnoseagentien. Producible the according to invention connections are also for the Preanästhesie and useful as sleep-inducing Agentien additionally to that managing mentioned strong Steuerungemechaniemen during the combat movement of the mouse. Beyond that producible the according to invention connections have different pharmakologische effects, like a muscle relaxation effect, regarding their control effect on the central nervous system a Apomorphin vomit Inhibitorwirkung, Ptosiewirkung, hypothermia effect, a control effect on the spontaneous movement, a control effect on the over movement of rats, a Antimethanphetaminwirkung, an effect on the sinking of the toxicity of the Methanphetamingruppe, analgetische effect and anti- Noradrenalinwirkung, whereby however only weak effects with the Anticholinwirkung, Cardioinhibitorwir $ kung and the catalepsis-inducing effect to be present. Therefore producible the according to invention connections are as Steuerungsagentien of the central nervous system as as central Muskelrelaxierungsagentien, sleep-inducing means, before-operational drugs, Antlschizophreniemittel, Sedativa, anti-fear drugs, antimanisch depressive Psychosemittel” Antipyretika, analgetische means and Depressoren useful, without they show side effects such as thirst feeling, Konstipation, Tachycardie, Parkinsonismus and/or retarded Dyscinesie, which are shown by conventional Steuerungsagentien for the central nervous system. The designation “an alkyl group with 1 to 6 carbon atoms” means an alkyl group, which geradkettig or can be branched out and 1 to 6 carbon atoms exhibits, whereby the examples groups of methyls, groups of ethyls, Propylgruppen, Isobutylgruppen, Butylgruppen, tert Isobutylgruppen. Butylgruppen, sec. Butylgruppen, Pentylgruppen, Hexylgruppen u.dgl, cover. The designation “a group of alkenyls with 2 to 4 carbon atoms” means a group of alkenyls, which can exhibit a straight or branched nice, with 2 to 4 Kohlenstoffatoraen, whereby the examples a Vinylgruppe, allyl group, 2-Butenylgruppe, 1-Methylallylgruppe u.dgl. cover. Examples of the designation “a Alkinylgruppe with 2 to 4 carbon atoms” cover Äthinylgruppen, 2-Propinylgruppen, 2-Butinylgruppen, 1-Methyl-2-propinylgruppen u.dgl. The designation “a Phenylalkylgruppe, their group of alkyls of 1 to 4 carbon atoms exhibits” means a Phenylalkylgruppe, which is compound from a Phenylgruppe with a group of alkyls, which geradkettig or can be branched out and 1 to 4 carbon atoms exhibits, whereby the examples the benzyle, 2-Phenäthylgruppe, 1-Phenäthylgruppe, 3-Phenylpropylgruppe, 4-Phenylbutylgruppe, 1,1-Dimethyl-2-phenäthylgruppe u.dgl, to cover. The designation “an alkyl group with 1 to 4 carbon atoms” means an alkyl group with straight lines or branched chain with 1 to 4 carbon atoms, whereby the examples hiefür groups of methyls, groups of ethyls, Propylgruppen, Isopropylgruppen, Butylgruppen, tert Isobutylgruppen. Butylgruppen u.dgl, cover. The examples of the designation “a halogen atom” cover the fluorine, chlorine, bromine and iodine. The designation “a Alkanoyloxygruppe with 1 to 4 carbon atoms means a Alkanoyloxygruppe with straight lines or branched chain with 1 to 4 carbon atoms, whereby the examples hiefür the Formyloxygruppe, which cover Acetyloxygruppe, Propionyloxygruppe, Butyryloxygruppe u.dgl. The designation “C3,8 - Cycloalkylgruppe, means a Cyc! oalkylgruppe with 3 to 8 carbon atoms, whereby the examples cover hiefür the Cyclopropylgruppe, Cyclopentylgruppe, Cyolohexylgruppe, Cycloheptylgruppe, Cyclooctylgruppe u.dgl. The designation “C - alkoxy group” means a geradkettige or branched Alkoxygrup1-4 PE with I to 4 carbon atoms, whereby the examples the Methoxygruppe, Äthoxygruppe, Propoxygruppe, Isopropoxygruppe, Butoxygruppe, tert lsobutoxygruppe. Butoxygruppe u.dgl, cover. Concerning the concrete examples of a Phenylgruppe, which can exhibit up to three groups of substituents, those under groups of halogens, c1 _4 - alkyl groups and C1_4-Alkoxygruppen are selected, can the Phenylgruppe, 2-Methoxyphenylgruppe, 4-Methoxyphenylgruppe, 3-Methoxyphenylgruppe, 2 - Äthoxyphenylgruppe, 4 - Butoxyphenylgruppe, 3.4 - Dimethoxyphenylgruppe, 3.4, 5-Trimethoxyphenylgruppe, 3-Isopropoxyphenylgruppe, 2-Methylphenylgruppe, 3-Methylphenylgruppe, 4-Methylphenylgruppe, 2-Äthylphenylgruppe, 4-Butylphenylgruppe, 3,4-Diäthylphenylgruppe, 3,4,5-Trimethylphenylgruppe, 2-Chlorphenylgruppe, 3-Bromphenylgruppe, 4-Fluorphenylgruppe, 3-Chlorphenylgruppe, 4-Chlorphenylgruppe, 2-Fluorphenylgruppe, 3,4-Dichlorphenylgruppe, 3,4,5-Trichlorphenylgruppe, 4-Chlor-3-methylphenylgruppe, 2-Methoxy-3-chlorphenylgruppe, 4-Bromphenylgruppe, 2-Bromphenylgruppe, 4--Jodphenylgruppe u.dgl, to be mentioned, the designation “C - Alkanoylgruppe” means a geradkettige or branched Alkanoyl1-4 group with 1 to 4 carbon atoms, whereby the examples cover hiefür the Formylgruppe, acetyl group, Proptonylgruppe, Butyrylgruppe, Isobutyrylgruppe u, dgl, the concrete examples of the c1. “- Alkyl group, which the Hydroxymethylgruppe, 2-Hydroxyäthylgruppe, 3-Hydroxypropylgruppe, 4-Hdroxybutylgruppe, 2-Hydroxypropylgruppe, Acetyloxymethylgruppe, 2-Acetyloxyäthylgruppe, 2-Propionyloxyäthylgruppe, 3-Acetyloxypropylgruppe, 4-Butyryloxybutylgruppe, 2-Acetyloxypropylgruppe, group of benzyles, 2-Phenäthylgruppe, 1-Phenäthylgruppe, 3-Phenylpropylgruppe, 4-Phenylbutylgruppe, 1,1-Dimethyl-2-phenS group of ethyls cover a group of substituents, as the hydroxy group, Phenylgruppe or C1-4-Alkanoylgruppe can exhibit, u.dgl. Below representative examples producible of the according to invention connections are indicated. The designation “3,4-Dehydroverbindung”, which is specified in the respective connections, means that the carbon carbon connection represents zwische.n the 3und 4-Stellungen in the Carbostyrilgerüst a double bond. For example “5 [2-Hydroxy-3 (4 - - phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and 5 become - [2-Hydroxy-3 (4-phenylpiperazinyl) - - propoxy] - carbostyril” here as, 5 [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and its 3,4-Dehydroverbindung” described. 6- [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 [3-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 [4-Hydroxy-5 (4-phenylpiperazinyl) - pentyloxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-5 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Äthyl-6 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 2S 1-Methyl-7 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-8 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1 (3-Methylbutyl) - 5 - [2-hydroxy-3 (4-phenylpiperazinyl) -propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Hexyl-6 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Allyl-5 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 1 (2-Butenyl) - 6 - [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Allyl-7 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-5 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1 (3-Phenylpropyl) - 5 {2-hydroxy-3 [4 (4-methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1 (4-Phenylbutyl) - 6 - [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] - 3,4dihydrocarbostyril and their 3,4-Dehydroverbindung 4S 1-Benzyl-7 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-8 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-5-brom-6 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6-Fluor-7 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-5-chlor-8 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6,8-Dichler-5 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6-Chlor-8-brom-7 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-5,6-dibrom-8 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1-Methyl-5 {2-hydroxy-3 [4 (2-chlorphenyl) - piperazinyl.] - propoxy) -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 6f 2-Hydroxy-3 [4 (3-bromphenyl) - piperazinyl] - propoxy} -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 7 - {2-Hydroxy-3 [4 (4-fluorphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - {2-Hydroxy-3 [4 (2-methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l-Benzyl-6 {2-hydroxy-3 [4 (3-methylphenyl) - piperazinyl] - propoxy} -3,4-dihydroearbostyril and their 3,4-Dehydroverblndung l-Methyl-5 {2-hydroxy-3 [4 (4-äthylphenyl) - plperazinyl] - propoxy) - 3,4-dihydroearboatyril and their 3,4-Dehydroverblndung 6 - (2-Hydroxy-3 [4 (2-propylphenyl) - piperazinyl] - propoxy} -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 5- {2-Hydroxy-3 [4 (2-methoxyphenyl) - piperazinyl] - propoxy) -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-6 {2-hydroxy-3 [4 - (3-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {2-Hydroxy-3 [4 (4-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3, 4-Dehydroverbindung 6 - {2-Hydroxy-3 [4 (2-äthoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydroearbostyrii and their 3,4-Dehydroverbindung SO 8-Chlor-5 {2-hydroxy-3 [4 (4-chlorphenyl) - piperaz nyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-6-chlor-7 {2-hydroxy-3 [4 (4-chlorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Allyl-6-chlor-7 {2-hydroxy-3 [4(4-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,6-Dehydroverbindung 6-Chlor-5 {2-hydroxy-3 [4 (4-methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverb ndung 6,8-Dibrom-5 {2-hydroxy-3 [4 (4-methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 (4-Phenylpiperazinyl) - methoxy-3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 [2 (4-Phenylpiperazinyl) - äthoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 [2 (4-Phenylpiperazinyl) - äthoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 8 [2 (4-Phenylpiperazinyl) - äthoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 [3 (4-Phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4S 7 [3 (4-Phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 [7 (4-Phenylpiperazinyl) - heptyloxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 [4 (4-PhenylpLperazinyl) - butoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 [4 (4-Phenylpiperazinyl) - butoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 [S (4-Phenylpiperazinyl) - pentyloxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung so 8 [5 (4-Phenylplperazinyl) - pentyloxy] - 3,4-dlhydrocarbostyril and their 3,4-Dehydroverbindung 7 - [6 (4-Phenylplperazinyl) - hexyloxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1-Methyl-5 [2 - (4-phenylpiperazinyl) - äthoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l-Methyl-6 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyrll and their 3,4-Dehydroverbindung l-Methyl-7 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung S 1-Hexyl-6 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l-Allyl-5 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Allyl-6 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l (l-Metbylallyl-7 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1 (2-Propinyl) - 7 - [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l-Benzyl-5 [2 (4-phenylpiperazinyl) - thoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1 (2-Phenyläthyl) - 6 - [3 (4-phenylptperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1 (4-Phenylbutyl) - 5 - [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l-Benzyl-7 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - {3 [4 (2-Methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyrLl and their 3,4-Dehydroverbindung 5 - {3 - [4 (3-Methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 - {3 - [4 (4-Methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyrll and their 3,4-Dehydroverbindung 7 - {2 - [4 (4-Propylphenyl) - piperazinyl] - Rthoxy} -3,4-dihydrocarboetyril and their 3,4-Dehydroverbindung 5 {3 [4 (4-Chlorphenyl} - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 {3 [4 (4-Bromphenyl) - piperazinyl] - propoxy} - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 7 - {2 - [4 (2-ChlorphenyI) - piperazinyl] - äthoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-5 [3 - [4 (4-chlorphenyl) - piperazinyL] - propoxy} -3,4-dihydrocarbostyril 3,4-Dehydroverbindung 1-Benzyl-6 {2 - [¢ (2-bromphenyl) - piperazinyl] - äthoxy} -3,4-dihydrocarbostyril 3,4-Dehydroverbindung and of them and their 1-Allyl-7 {4 [- (4-bromphenyl} - piperazinyl] - butoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-6 {3 - [4 (4-methylphenyl)- piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-53 [4 (2-methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 {3 - [4 (4-methoxyphenyl} - piperazinyl] - propoxy) -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1-Benzy! - 5 - {3 - [4 (4-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 8-Brom-5 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-5-brom-6 [2 (4-phenylpiperazinyl) - .thoxy] -3,4-dihydrocarbostyril and their 3 4-Dehydroverbindung 6-Fluor-7 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6-Chlor-5 [2 (4-phenylpiperazinyl) - äthexy] -3,4-dihydrocarbestyri! and their 3,4-Dehydroverbindung 6-Chlor-5 {4 - [4 (4-methylphenyl) - piperaziny! ] - butoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Allyl-6-chlor-7 {2 - [4 (4-methoxyphenyl) - piperazinyl] - .äthoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6,8-Dichlor-5 [2 (4-phenylpiperazinyl) - äthoxy] -3,4-dihydrccarbostyril and their 3,4-Dehydroverbindung 6-Chlor-8-br m-7 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrccarbostyril and their 3,4-Dehydroverbindung 1-Methyl-5,6-dibrom-8 [2 - (4-phenylpiperazinyl) - äthoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 8-Chlor-5 {3 - [4 (4-chlorphenyl) - piperazinyl] - propoxy} -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1-Methyl-6-chl r-7 (2 - [4 (4-chlorphenyl) - piperazinyl] - äthoxy) -3,4-dihydrecarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-6,8-dicblor-5 {2 - [4 (2-bromphenyl) - piperazinyl] - ithoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 (3 [4 (2-Methoxyphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 (3 [4 (3-Methoxyphenyl) - piperazinyl] - propoxy} - 3 4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 - [4 (4-Methoxyphenyl) - piperazinyl] - propoxy) -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {3 [4 (2-Äthoxyphenyl) - piperazinyl] - propoxy) - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 {3 - [4 (2-methoxyphenyl) - piperazinyl] - propoxy -3,4-dihydroearbostyril and their 3 4-Dehydroverbindung 1-Allyl-7 {3 - [4 (2-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l-Benzyl-7 {3 - [4 (2-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l (2-Propinyl) - 7 (3 - [4 (2-methoxyphenyl) - piperazinyl] - propoxy) - 3 4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {3 [4 (3,4-Dimethoxyphenyl) - piperazinyl] - propoxy) - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 - [4 (3,4,5-Trimethoxyphenyl) - piperazinyl] - propoxy) -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 {3 [4 (3,4-Dimethoxyphenyl) - piperazinyl] - propoxy} - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 {3 - [4 (3 4-dimethoxyphenyl) - piperazinyl] -propoxy} -3,4-dihydrocarbostyril and “s their 3,4-Dehydroverbindung 1-Benzyl-7 {3 - [4-E-3,4-diehlorphenyl) - piperazinyl] - propoxy} -3 4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {3 [4 (3,4, Dimethylphenyl) - piperazinyl] - propoxy} - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung SO 5 - [2-Methyl-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [2-Methyl-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 4-Methyl-6 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [4-Methyl-5 (4-phenylpiperaztnyl) - pentyloxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [2-Äthyl-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 [ 2-methyl-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-7 [2-methyl-3 (4-phenylpiperazinyl} - propoxy] -3,4-dihydrecarbostyril and their 3,4-Dehydroverbindung 1-Allyl-7 [2-methyl-3 (4-phenylpiperazinyl) - prepoxy] -3,4-dihydrecarbostyril and their 3,4-Dehydroverbindung 1 (2-Propinyl) - 7 - [2-methyl-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydreverbindung 6-Chlor-5 [2-methyl-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6-Chlor-8-brom-7 [2-methyl-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {2-Methyl-3 [4 (2-methoxyphenyl) - piperazinyl] - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-5 (2-methyl-4 [4 (4-methylphenyl) - piperazinyl] - butoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {2-Methyl-3 [4 (3,4-dimethoxyphenyl) - p perazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [2-Methyl-3 (3-methyl-4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - [2-Acetyloxy-3 (4-phenylptperazinyl) - propoxy] -3,4-dihydrocarbostyrll and their 3,4-Dehydroverbindung 1-Methyl-6 [2-propionyloxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - (2-Aeetyloxy-3 [4 (2-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3-Acetyloxy-5 [4 (4-methylphenyl) - piperazinyl] - pentyloxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl {2-acetyloxy -3 - [4 (4-chlorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Allyl-8 [2-acetyloxy-3(4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6-Chlor-5 [2-acetyloxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Äthyl-7 [2-acetyloxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1 (2-Propinyl) - 7 - [2-acetyloxy-3 (4-phenylpiperazinyl) - propoxy] -3 4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4s 7 - {2-Isobutyryloxy-3 [4 (2-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 4 [2-Acetyloxy-3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Methyl-7 [2-acetyloxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3 4-Dehydroverbindung 4-Phenyl-7 [2-acetylexy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - [ 2 (3,4,5-Trimethoxybenzoyloxy) - 3 (4-phenylpiperazinyl) - propoxy] -3 4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-6 [2 (3,4,5-trimethoxybenzoyloxy) - 3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [2 (3,4,5-Trimethoxybenzoyloxy) - 3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 [2 (3,4,5-trimethoxybenzoyloxy) - 3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7f2 (,3, 4,5-Trimethoxybenzoyloxy) - 3 [4 (2-methoxyphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-7 [2 (3,4,5-trimethoxybenzoyloxy) - 3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Methyl-7 [2 (3,4,5-trimethoxybenzoyloxy) - 3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Phenyl-8 [2 (3,4,5-trimethoxybenzoyloxy) - 3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Allyl-6-chlor-72 (3,4,5-trimethoxybenzoyloxy) - 3 - [4 (3,4-dimethoxyphenyl) - piperazinyl] - ~propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [2-11ydroxy-3 (3-methyl-4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 [3 (3-Methyl-4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 73 - [3-Methyl-4 (4-chlorphenyl) - piperazinyl] - propoxy) -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 [3 (3-Methyl-4-phenylpiperaziny1) - pr0p0xy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 - [3-Methyl-4 (2-methoxyphenyl) - piperazinyl] - propoxy) - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 8 [3 (3-Äthyl-4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4 - [3 (3-Methyl-4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung l-methyl [3 (3-methyl-4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbi ndung l-benzyle [3 (2-methyl-4-phenylpiperazinyl) - propoxy] - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 4-Methyl-7 [3= (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Phenyl-7 {3 - [4 (2-methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4 [3 (4-Phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Äthyl-7 {3- [4 (2-methoxyphenyl) - piperazinyl) - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1,4-Dimethyl-7 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-4-phenyl-7 {3 - [4 (2-chlorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril t5 and their 3,4-Dehydroverbindung 5 [2-Hydroxy-3 (4-cyclohexylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyrll and their 3,4-Dehydroverbindung 6 [2-Acetyloxy-3 (4-cycloheptylpiperazinyl) - propoxy] - 3,4-dlhydrocarbostyril and their 3,4-Dehydroverbindung SO 7 - [3 (4-Cyclohexylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4 - [3 (4-Cyelohexylpiperazinyl} - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 [3 (4-cyclohexylpiperazinyi) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-7 [2-methyl-3 {4-cyclohexylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3 4-Dehydroverbindung 5 [3 (4-Cyclohexylpiperazinyl) - propoxy] -3,4-dibydrecarbostyril and their 3,4-Dehydroverbindung 4-Methyl-7 [3 (4-cyc [ohexylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Phenyl-6 [2-methyl-3 {4-eyclohexylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Debydroverbindung 1 {2-PropinyD-7 [4 (4-cyclobexylpiperazinyl) - butoxy] -3,4-dihydrocarbostyril and their 3 4-Dehydroverbindung 6,8-Dichlor-5 [3 (4-cyclohexylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - [2-Acetyloxy-3 (4-benzy [piperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 [2-Hydroxy-3 (4-benzylpiperazinyi) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 [3 (4-Benzylpiperazinyl) -propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4 [3 (4-Benzylpiperaziny!)- propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 [3 (4-Benzylpiperaztnyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 [2-methyl-3 (4-benz.ylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-7 [3 (4-benzylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Methyl-7 [3 (4-benzylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Phenyl-7 [3 (4-benzylpiperazinyl) - propoxy] -3,4-dihydrocarbostyrtl and their 3,4-Dehydroverbindung 1-Allyl-6 [4 (4-benzylpiperazinyl) - butoxy] -3,4-dibydrocarbostyril and their 3,4-Dehydroverbindung 1 (2-Propinyl) - 8 [2 (4-benzylpiperazinyl) - äthoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 6,8-Dichlor-5 [3 (4-benzylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7- [2-Acetyloxy-3 (4-benzylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 - [4 (1-Pbenyläthyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {3 [4 (4-Phenylbutyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - {2-Hydroxy-3 [4 (2-acetyloxyäthyl) - piperazinyl] - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {3 [4 (2-Acetyloxyäthyl) - piperazinyl] - propoxy} - 3 4-dihydrocarbostyril and their 3,4-Dehydroverbindung 8 {2-Methyl-3 [4 (2-acetyloxyäthyl) - piperazinyl] - propoxy} - 3 4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4 {3 [4 (2-Acetyloxyät'hyl)- piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 - [4 (4-Butyryloxybutyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-7-E 3 - [4 (2-acetyloxyäthyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3 - Debydroverbindung 4-Phenyl-7 {3 - [4 - (2-acetyloxyäthyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {2-Hydroxy-3 [4 (2-acetyloxyäthyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - {2-Acetyloxy-3 [4 (2-hydroxyäthyl) - piperazinyl] - propoxy} -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 7 {3 [4 (2-Hydroxyäthyl) -piperazinyl] - propoxy} - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 7 - {3 [4 (4-Hydroxybutyl) - piperazinyl] - propoxy} - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 7 {3 - [4 (1-HydroxyRthyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4 - {2 - [4 (2-Hydroxyäthyl) - plperazlnyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Methyl-7 {3 - [4 (2-hydroxyäthyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {2-Hydroxy-3 [4 (2-hydroxyäthyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - [3 (4-Benzoylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and of them 3,4-Dehydroverbindung 7 - [2-Acetyloxy-3 (4-benzoylpiperazinyl) - propoxy] -3,4-dlhydrocarbostyril and their 3,4-Dehydroverbindung 7 - [3 (4-Benzoylpiperazinyl) - propoxy] -3,4-dihydroc rbostyril and their 3,4-Dehydroverbindung 2S 8 [3 (4-Benzoylpiper zinyl) - propoxy] - 3,4-dihydroc rbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 [3 (4-benzoylpiperazinyl) - propoxy] - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 4-Phenyl-7 [3 (4-benzoylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung a0 1 (2-Propiny!)- 5 [2 (4-benzoylpiperazinyl) - äthoxy] - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 6-Chlor-a [4 (4-benzoylpiperazinyl) - butoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 [3 (4-Aeetylpiperazinyl) - propoxy] - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung - 5 7 [3 (4-Acetylpiperazinyl) - propoxy] - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 8 [2-Aeetyloxy-3 (4-acetylpiperazinyl) - propoxy] - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 1-Benzyl-7 [3 (4-aeetylpiperazinyl) - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 4-Methyl-7 [3 (4-acetylpiperazinyl) - propoxy] -3,4-dihydroearbostyril and their 3 4-Dehydroverbindung 4 [3 (4-Acetylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [3 (4-Butyrylpiperazinyl)- propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 4S 1-Methyl [4 (4-propionylpiperazinyl) - butoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 8-Brom-5 [3 (4-acetylpiperazinyl) - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 7 - [3 (4-Phenylhexahydre! , 4-diazepin-l-yl) - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 6 - [3 (4-Phenylhexahydro-l, 4-diazepin-l-yl) - propoxy] -3,4-dihydro¢arbostyril 3,4-Dehydroverbindung 5 - [3 (4-Phenylhexahydro-l, 4-dlazepin-l-yl) - propoxy] -3,4-dihydrocarbostyril and of them and their 3,4-Dehydroverbindung 4 [4 (4-Phenylhexahydro-l, 4-diazepin-l-yl) - butoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 [4 (2-Methoxyphenyl) - hexahydro l, 4-diazepin-l-yl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6 - {2 - [4 (4-Chlorphenyl) - hexahydro l, 4-diazepin-l-yl] - äthoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - [3 (4-Benzylhexahydro-l, 4-diazepin-l-yl) - propoxy] -3,4-dihyc rocarbostyril and their 3,4-Dehydroverbindung I0 7 - [2-Hydroxy-3 (4-phenylhexahydro-l, 4-diazepin-l-yl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung B [2-Methyl-3 (4-phenylhexahydro-l, 4-deazepin-l-yl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-7 [3 (4-phenylhexahydro-l, 4-diazepin-l-yl) - propoxy] - 3,4-dihydrocarbostyril and LS their 3,4-Dehydroverbindung 1-Benzyl-7 [3 (4-phenylhexahydro-l, 4-diazepin-l-yl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 4-Phenyl-7 [3 (4-phenylhexahydro-l, 4-diazepin-l-yl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Deh. ydroverbindung 8-Chlor-5 [3 (4-phenylhexahydro-l, 4-diazepin-l-yl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {2-Hydroxy-3 [4 (4-chlorphen, yl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6-Chlor-7 {2-hydroxy-3 [4 (2-methoxyphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril 2S and their 3,4-Dehydroverbindung 4-Methyl-7 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverhindung 6 - {3 - [4 (2-Methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Methyl-5 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - {2 [4 (4-Methylphenyl) - piperazinyl] - äthoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 8 {3 [4 (2-Methoxyphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 - [4 (4-Methylphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 {3 [4 (2-Äthoxyphenyl) - piperazinyl] - propoxy} - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 6-Chlor-7 [3 (4-phenylptperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 6-Brom-7 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 7 - {3 [4 (2-Chlorphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {3 [4 (3-Chlorphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 [4 (4-Chlorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung SO l-Allyl-7 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Hexyl-q [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 1-Benzyl-5 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 - {3 [4 (3-Fluorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 5 - {3 [4 - (2-Fluorphenyl) - piperazinyl] - propoxy) -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung 7 {3 - [4 (2-Fluorphenyl) - piperazinyl] -propoxy} - 3,4-dihydroearbostyril and their 3,4-Dehydroverbindung 5 - {3 [4 - (3-Fluorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydrol0 connection 5 {3 - [4 (3,4,5-Trimethoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril and their 3,4-Dehydroverbindung. The connections of the general formula (I) in accordance with the invention thereby it is manufactured that a connection of the general formula O (A) i (II) R3a, /o \ where A a group of the general formula - (CH2) I (CH2) X or - CH - CH-CH represents and hiebei R, R2, X, I, m, n and the carbon carbon connection between the 3und of the 4-Stellung in the Carbostyrilgerüst the meaning indicated above to have, to R3a hydrogen, a hydroxy group or an alkyl group with 1 to 4 carbon atoms is and X1 a halogen atom or a similar substitution reaction as a halogen atom making possible group, e.g. a Mesityloxyoder Tosyloxygruppe, represents, with a connection the general formula J (CH2) q R (REAR ONE) where R, R-S and q have the meaning indicated above, it is converted, on which, if in the received connection of of the allgemeßnen formula (I) R3 a hydroxy group, the received represents connection gewünschtenfalls with a connection of of the general formula R3b X2 or (R3b) z O (iv) (v) where R3b a Alkanoylgruppe with 1 to 4 carbon atoms or a 3” 4,5-Trimethoxybenzoylgruppe is and X2 means a halogen atom, gewünsehtenfalls a received connection of the general formula (I) with the meaning of hydrogen for R into a connection with one of the remaining meanings of R 8bergeführt is converted becomes, gewtlnschtenfalls a received Carbostyri derivative to a 3,4-Dihydrocarbostyrilderivat is hydrogenated and gewünsohtenfalls a received connection of the general formula (I) into an acid addition salt one transfers. The procedure according to invention punt by the following reaction patterns 1, 2 and to be described. Reaction pattern 1 (x) i n (IL) (III) R3a/(CH2) q O (CH2) 1CH (CH2) N. N-as where g 1 2 R 3a 4 R5 1, R, R, X, X, l, m, n, q the carbon carbon connection in 8und 4-Stellung in the Carbostyrilgerüst as well as the position of the Seitenkette 3a I/(CH2) “N R5) N -0 (cH2) i CH have (CH2 m // the meaning indicated above. The conversion between a connection of the general formula (II) and a connection of the general formula (IIIi can be preferably terminated in absence or in presence of an inert solvent with Raumteraperatur up to 200°C, at a temperature within the range of 60 to 120°C, in the course of several hours up to 24 h. As inert solvent one can use an ether, like Dioxan, tetrahydrofurane, ethylen glycol, Dimethyläther u.dgl., an aromatic hydrocarbon such as benzene, toluol, xylene u.dgl., a low alcohol such as methanol, ethanol, isopropanol u.dgl., or a aprotisches polar solvent such as dimethylformamide, Dimethylsulfoxyd u.dgl. 1 the conversion is preferably accomplished using a basic connection as Dehydrohalogenierungsmittel. The basic connection used during the conversion can be selected from a large multiplicity of well-known basic connections such as potassium carbonate, Natriumcarbonat, sodium hydroxide, Natriumhydrogencarbonat, sodium amide, sodium hydride, a tertiary amine such as tri ethyl amine, Tripropylamin, P yridin or Chinolin. The conversion can be accomplished also using an alkali] odids like potassium iodide or sodium iodide as Reaktlonsbeschleuniger. 'The relationship of the quantity of the connection of the general formula (II) to the connection of the general formula (III) during the above conversion is subject to no special restriction and can be selected within a wide range, however it is generally desirable, the latter äquimolar or in the surplus, preferably äquimolar 2 up to that kindles molecular quantity of the first connection, in particular äquimolar up to the 1,2lachen of the molecular quantity of the first connection to use. A connection of the general formula (I), where R3 is a Alkanoyloxygruppe with I to 4 carbon atoms or a 3,4,5-Trimethoxybenzoyloxygruppe, one can manufacture according to the following reaction pattern 2. Reaktionschema 2 OH CH [/ₜ 21 “O (CH2)! CH (CH2) m N 2N-R \ R2 \/. R4 (Ia, R3aa - OH) B ß " N + R3b X2 or (R3b) 2 0 (X 11 0 (IV) (V) OR3b (CH2) q 0 CH C H CH Nj I N R5 z) 1 (2)= I /- ./v % R, - Alkano, lox, or (X) n 1,3.4, 5-Trimethoxybenzoyl), where RI, R2, R3a, R3b, RA, R5, X, X2, I, m, n, q the carbon carbon connection/&lt in the 3und 4-Stellung of the Carbostyrilgerüstes and the position of the Seitenkette oR3b1; CH) N R - O (CH2) I CH (CH2) N the before indicated meaning have. One can make thus a connection of the general formula (Ib) in accordance with the invention, by one a Hydroxyalkoxycarbostyrilderivat of the general formula (Ia) with a Säurehalogenid or a Säureanhydrid of the general formulas (IV) or (V) converts. The conversion of a connection of the general formula (Ia) with a connection of the general formulas (IV) or (V) can take place in present or in absence of a suitable solvent and in present or in absence of a suitable basic connection. Preferably the conversion to presence of a basic connection is accomplished. As solvents an aromatic hydrocarbon can be used such as benzene, toluol or xylene, a Halogenkohlenwasserstoff such as chloroform or dichloromethane, acetone, Pyridin, Dimethylsulfoxyd, dimethylformamide u.dgl, with the above reaction. As basic connection a tertiary amine can be used such as tri ethyl amine or Pyridin, sodium hydroxide, potassium hydroxide or sodium hydride u.dgl, during the conversion mentioned above. The Verhältni of the quantity of a connection of of the general formulas (IV) or (V) to a connection of of the general formula (Ia) can be like that the first in a at least äquimolaren quantity of the latters is preferably used, in a äquimolaren quantity of the latters molecular up to the 5fachen. The above reaction is preferably accomplished at a temperature between ambient temperature to 150°C, in the range between ambient temperature and 100°C several hours up to 15 h. The basic material of the general formula (II) used with the invention is either from the US-PS Nr.4, 072.683 well-known or again and can according to the following reaction patterns (3) and (4) in simple way to be manufactured. 2 R2 OH R OR6 (Vl) J1 Halogenierungsmittel (VIII) Halogenierungsmittel (X) n, Rl (X) n, R (VII) (IX) S where R, R2, X and the carbon carbon connection between the 3und of the 4-Stellung in the Carbostyrilgerüst the before indicated meaning possess and the hydroxy group to the 4, 5, 6, 7oder 8-Stellung in the Carbostyrilgerüst stand can, n' is alike means 1 or 2 and R-S an alkyl group with 1 to 4 carbon atoms or a Alkanoylgruppe with I to 4 carbon atoms. In the reaction pattern 3 one receives a connection of the general formula (VII) by shifting of a Hydrocarbostyrils of the general formula (VI) with a Halogenierungsmittel or by hydrolysis of a connection of the general formula (IX), which is manufactured by shifting of a Alkoxyoder Alkanoyloxycarbostyrils of the general formula (VIII) with a Halogenierungsmittel. The above-mentioned Halogenierungsreaktion can take place using well-known HalogelS nierungsmitiel. Examples of such Halogenierungsmittel are fluorine, chlorine, bromine, iodine, Xenondifluorid, Sulfurylchlorid, sodium hypochlorite, hypochlorous acid, unterbromige acid, bleaching powder, iodine chloride u.dgl. the quantity of the Halogenierungsmittels within a broad range are in such a way selected, as it requires the number in the connection (VI) or (VIII) halogen atoms which can be introduced. If only one halogen atom is to be introduced, the Halogenierungsmittel is used generally äquimolar or in the surplus, preferably in the 1bis 1, Sfachen molecular quantity of the parent compound. If 2 halogen atoms are introduced, then the Halogenierungsmittel is used into the 2fachen molecular quantity up to a large surplus, preferably into the 2bis 3fachen molecular quantity of the respective parent compound. The Halogenierungsreakti'on is accomplished generally in a solvent such as water, methanol, ethanol, 2s chloroform, carbon tetrachloride, acetic acid or a mixture of it. The reaction temperature is subject to no special restriction and can be selected within a wide range, however it is appropriate for 0°C to ambient temperature generally with approximately -20 to 100°C, preferably. The reaction runs within a time of 30 min to 20 h completely off. The hydrolysis reaction of a connection of the general formula (IX) varies depending upon the 0 kind of R6 in the formula (IX). If R6 is e.g. a Alkanoylgruppe with 1 to 4 carbon atoms, then the hydrolysis under conditions of a usual hydrolysis reaction of an ester is accomplished. More exactly said, the hydrolysis can be accomplished in presence of a basic connection such as sodium hydroxide, potassium hydroxide, barium hydroxide, Natriumcarbonat, potassium hydrogencarbonate, a mineral acid such as sulfuric acid or hydrochloric acid, an organic acid such as acetic acid, an aromatic sulfone acid in a solvent such as water, methanol, ethanol, acetone, Dioxan, tetrahydrofurane or benzene. The reaction temperature is in the alIgemeinen between ambient temperature and 150°C, preferably about 50 to 100°C. After i to 19 h the reaction ran completely. If on the other hand RH is an alkyl group with 1 to 4 carbon atoms, SE can be accomplished the hydrolysis reaction on the usual hydrolysis conditions for an ether. More exactly said, the conversion can be accomplished using aluminum chloride, boron tri fluoride, boron tri bromide, hydrobromic acid or Trimethylstlylchlorid than catalyst and in a solvent such as water, methanol, ethanol, benzene, dichloromethane or chloroform at a temperature within the range of 0 to 200 C, preferably between ambient temperature and 120°C, during several up to 19 h. With both hydrolysis reactions the quantity of the used catalyst is not subject to special restrictions, whereby the catalyst is used generally in the surplus in relation to the too hydrolysterenden connection (IX). IS reaction pattern 4 R A X3 (CH2) I (CH2) mXl (Xl) R3a (CH2) 1 H (CH2) mX1 RZ] R* (x) ù R11 (x) (n) where g 1, R2, R3a, X, X1, 1, m, n, the carbon carbon connection in the 3und of the 4-StelR3a I xl lung in the Carbostyrilgerüst and is bound the position of the Seitenkette - O (CH2) CH (CH2) m the before indicated meaning have, X' a halogen atom is and the hydroxy group at the 4, 5, 6, 7 - or 8-Stellung of the Carbostyrilgerüstes. In the reaction pattern 4 the conversion of a connection of of the general formula (X) with a connection of of the general formula (XI) becomes preferably using a basic connection as Dehydrohalogenierungsmittel accomplished in a suitable solvent at ambient temperature to 200°C, preferably 50 to 150°C, during several to 15 h. Examples of suitable solvents are low alcohols such as methanol, ethanol or isopropanol, a Keton such as acetone or methylethylketone, an ether such as Dioxan, Diäthylenglykoldimethyläther, an aromatic hydrocarbon such as toluol or xylene, dimethylformamide, Dimethylsulfoxyd or Hexamethylphosphoryltriamid. Examples of basic connections usable as Dehydrohalogenierungsmittel are sodium hydroxide, potassium hydroxide, Natriumcarbonat, potassium carbonate, Natriummethoxyd, Natriumäthoxyd, Kaliumäthoxyd, sodium hydride, metallic potassium, metallic sodium, a tertiary amine such as Pyridin, Chinolin, tri ethyl amine or Tripropylamin. With the above reaction an alkali iodide can be erwendet such as potassium iodide or sodium iodide as reaction accelerators. The relationship of the connection of of the general formula (X) to the connection of of the general formula (Xl) during the conversion mentioned above is not limited particularly, however it is echenswert wün3S, the latter in äquimolarer quantity or larger quantity, generally in a 1bis 1 preferably kindles and 1bis 1,2fachen molecular quantity to use related to the first. One receives a connection of the general formula (II), which is used with the invention as raw material to EO. In the Reaktiensschemata 3 and 4 closes the connections of the general formulas (VI), used as basic materials, (VIII) and (X) new connections in, where R is an alkyl group with I to 6 carbon atoms, elne group of alkenyls with 2 to 4 carbon atoms, a Alkinylgruppe with 2 bie 4 carbon atoms or a Phenylalkylgruppe with an alkyl group with 1 to 4 carbon atoms. These connections know 0°C to ambient temperature, in simpler by shifting of a well-known l Hydroxycarbostyrils, with which R is a hydrogen atom, with an alkyl halide, a AlkenylS halide, a Alkinylhalogen£d or a Phenylalkylhalogenid in presence of a basic connection like an alkali metal, a e.g. metallic sodium or a metallic potassium, an alkali amide such as sodium amide or potassium amide or sodium hydride in a suitable solvent such as benzene, tetrahydrofurane, Dioxan, Dimethylsulfoxyd, Dimethylforma ID, Hexamethylphosphoryltriamid, pray a temperature from 0 to 70°C, preferably eat way to be manufactured, whereby the conversion to 30 min to 12 h runs. In such a way received connection is then hydrolyzed under similar conditions, as with the hydrolysis of a connection of the general formula (IX), with which the alkyl group has R6 1 to 4 carbon atoms and like this in the reaction pattern 3 was shown. With the above reaction the relationship of the quantity of the basic connection, the alkyl halide, alkenyl halide, Alkinylhalogenids or Phenylalkylhalogenids to the raw material can be selected within a wide range, however the quantity is to 2bis 4fachen molecular quantity, the parent compound generally with the 2bis 10fachen molecular quantity, preferably. Of the connections that. general formula (I) can do one those the general formula (IC), where 1 and m 1 in each case mean and R-S a hydroxy group is, according to the following reaction pattern 5 to manufacture. 4, 8, 6, 7oder 8-Stellung in R Carbostyrilgerüst finds. With the reaction pattern the conversion of a Hydrocarbostyrilderivates of of the general formula (X) with a Ep can [halogenhydrin the general formula (XII) accomplished in presence 0 of a suitable basic connection as for example an inorganic basic compound such as sodium hydroxide, potassium hydroxide, Natriumcarbonat, potassium carbonate, Natriummethoxyd, Natriumäthoxyd, Natriunlhydrid, metallic sodium, metallic potassium, sodium amide, or an organic basic compound such as Piperidin, Pyridin, tri ethyl amine in absence or in presence of a Lösungsnlittels, e.g. a low alcohol such as methanol, ethanol or isopropanol, S a Keton such as acetone or methylethylketone, an ether such as ether, Dioxan, Diäthylenglykolmethyläther, an aromatic hydrocarbon, like benzene, toluol, xylene or by water become. During this conversion the quantity of the connection within a wide range, indicated by the general formula (XII), selected, ever nevertheless lies above it generally with a äquimolaren quantity or, preferably with the 5bis 10lachen molecular quantity of the connection described by the general formula {X). The conversion runs at a temperature between 0 and 150°C, preferably between 50 and 100°C. During the above conversion an epihalogenohydrin of the general formula (XII) with the hydroxy group of the connection of the general formula (X) and one receives connections, which one (2,3-Epoxy) reacts - propoxygruppe or 3-Halogen-2-hydroxypropoxygruppe have. Generally the reaction products are received as LS mixture of these connections. In such a way received reaction product can directly, thus without previous separation or cleaning, according to invention with an amine of the formula (III) to be converted. Further the reaction product with an amine of the formula (III) can to be converted after it was cleaned by usual separation, recrystallizing or Säulenchromatographie, whereby one receives a cleaned product with a 2,3-Epoxypropoxygruppe or a 3-Halogen-2-hydroxypropoxygruppe. In this case the conversion of a connection of the general formula (II) with a connection of the general formula (III) in absence or in presence of an inert can, usually Lösungsnlittels used 60 to 120°C, to be accomplished, with Raunltemperatur to 200°C, preferably whereby the conversion runs within a time of several hours to 24 h completely. With the above Unlsetzung are examples of lnerte solvent ether such as Dioxan, tetrahydrofurane, ethylen glycol and Dimethyläther, aromatic hydrocarbons such as benzene, toluol and xylene, low alcohols such as methanol, ethanol, isopropanol or polar solvents such as Dimethylformanlid or Dinlethylsulfoxyd. Further one can add a basic connection during the above conversion. Examples of basic connections are inorganic basic compounds such as potassium carbonate, Natriumcarbonat, sodium hydroxide, Natriumhydrogencarbonat and Natriunlanlid and tertiary amines such as tri ethyl amine, Tripropylamin, Pyridin and Chinolin. The relationship of the quantities of the connections unlgesetzten in each case can lie within a wide range, however it is in allgeSS means desirable that the connection of the general formula (III) in a äquimolaren quantity or in a surplus quantity, preferably in a äquinlolaren quantity up to the 5fachen molecular quantity and in particular the 1bis 2fachen nlolaren quantity of the connection of the general formula (II) is present. Connection general formula (I), in which R an alkyl group with 1 to 6 carbon atoms, meant, a group of alkenyls with 2 to 4 carbon atoms, knows a Phenylalkylgruppe, in which the group of alkyls has 1 to 4 carbon atoms, by shifting of a connection of of the general formula (I), in which R a Wasserstoffat0 n1 means, with a halogen connection of of the general formula (XIII), as in the following reaction pattern 6 one shows, to be manufactured. Reaction pattern 6 (X) ù I H (ID) Rle X5 (XIII) R3 (CH2) q R2 R “f (X) n Rle (IE) where R R-S R, R-S, X, 1, m, n, q, the carbon carbon connection between the 3und of the 4-Stellung of the Carbostyrilgerüstes and the position of the Seitenkette I: {3/(CI'I2) q I - (C [[2) 1 CH (CH2 the before indicated meaning have, Rle an alkyl group with 1 to 6 carbon atoms, a group of alkenyls with 2 to 4 carbon atoms, a Alkinylgruppe with 2 to 4 carbon atoms, a Phenylalkylgruppe, in which the group of alkyls has 1 to 4 carbon atoms, and X5 a halogen atom is. During the conversion of a connection of the general formula {ID) with a connection of the general formula (XIII) the latter in a äquimolaren quantity up to the 3lachen molecular quantity is used opposite the first, preferably in äquimolarer quantity opposite the first. Hiebei can be used the same reaction conditions, as they were indicated in connection with the reaction patterns 3 and 4. Connections of the general formula (I) can be transferred easily into the acid addition salts by conversion with pharmaceutical acceptable acids. Examples of such acids are inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, hydrobromic acid u.dgl, and organiscl e acids such as oxalic acid, maleic acid, fumaric acid, malic acid, tartaric acid, Citronensäure, benzoic acid u.dgl. the connections manufactured according to the different reaction patterns can be isolated and cleaned by usual procedures such as solvent extraction, solvent dilution, recrystallizing, Säulenchromatographie, präparative Dünnschichtchromatographie. Producible the according to invention connections include also optical isomers. As antihistamine means and means as a check of the central nervous system the connections of the formula (I) can in the form of pharmaceutical preparations as well as pharmaceutical acceptable carriers to be used. The used carriers depend ExzipientLa on the kind of the pharmaceutical preparation and include ¥erdünnungsmittel and such as fillers, Verdüns nungsmittel, bonding agents, humidification means, decay means, surface-active materials and lubricants. Regarding the administration units no special restrictions and the connections exist can in each desired unit form al.s antihistamine means and means as a check of the Zentralnerveneysteme be used and typical single dosage forms are le tablets, pills, powder, liquid Zuberettungen, Suspen ions, emulsions, granulates, caps, Suppositorien, injection preparations (solutions and suspensions) and ointments. For the shaping to tablets common carriers, e.g. Exzipientia, know like lactose, Rohrzucker, sodium chloride, solutions oil hydrogenated by glucose, urea, strength, Calciumcarbonat0 kaolin, crystalline cellulose or silicic acid, bonding agent such as water, ethanol, Propanol, simple syrups, glucose, starch solutions, gel solutions, Carboxymethylcellulose, shellac, methyl cellulose, calcium phosphate and Polyvinylpyrrolidon, decay means like dry strength, Natriumalginat, agar - agar powder, Laminalien powder, Natriumhydrogencarbonat, calcium carbonate, Polyoxyäthylensorbitanfettsäureester, Natriumlaurylsulfat, Monoglycerid of stearic acid, strength, lactose, decay inhibitors, like Rohrzucker, Stearin, coconut butter, in this area; Absorption accelerator, like quaternäre ammonium bases, Natriumlaurylsulfat; Befeuchtungamittel, like Glycerin or strength; Absorbent, like strength, lactose, kaolin, Bentonit, colloidale silicic acid; Lubricant, like cleaned talc, stearic acid salt, boric acid powder, PL glycol and firm PL glycol. For deformation to pills hiefür admitted carriers, Exzipientia such as glucose, know lactose, strength, coconut butter, hydrogenated vegetable oils, kaolin and talc, bonding agent like powdered rubber arabicum, powdered Traganth, gel and ethanol, decay means such as Laminarien and agar agar being e.g. used. Tablets can be manufactured with usual Überzugsmaterialien such as sugar, gel coats or with enterischen coatings, whereby also simple, double or multilayered coats to be planned to be able. Suppositorien manufactured using in this area admitted to carriers, e.g. PL glycol, coconut butter, higher alcohols, esters of higher alcohols, gel and halfsynthetic Glyceriden. Inject-cash preparations, solutions and suspensions are sterilized and are preferably isotone to blood. During the production of injectable preparations all know carriers to be used, e.g. water, ethyl alcohol, propylene glycol, äthoxylierter Isostearylalkohol, polyoxylierter Isostearylalkohol, Polyoxyäthylensorbit or Sorbitanester for such preparations admitted. In this case the preparations with appropriate quantities of sodium chloride, glucose or Glycerin isotone can be made. In addition know the usual solution center! , Buffers, Analgesierungsmittel, preservatives and just as means, odoriferous substances, taste materials, Süßstoffe also colorgiving and other drugs, the desired preparations if required added who “0 that. For the production of pastes or creams for this area admitted diluents like white vaseline, paraffin, Glycerin, cellulose derivatives, PL glycol, silicones and Bentonit used. The quantity of the connection of the general formula (I) or an acid addition salt hievon in the antihistamine means or in the means for control of the central nervous system is contained, is not limited particularly and preferably amounts to 1 to 70 Gew. - %, related to the entire preparation. The mentioned Antihietaminmittel and means as a check of the central nervous system can be used without restriction for the respective purpose in the different forms. For example one can give tablets, pills, solutions, Suapenelonen, Emulaionen, granulates and caps orally and injectable preparations intravenously separately or with Injektionstransfusionen such as Gluceeelöaungen and Aminosäurelöaungen or erforderliehenfalls intramuekulär, intrakutan, eubkutan or intraperitoneal, the dose of the antihistamine means and means for steering the central nervous system, depending upon the use to the purpose and the conditions and symptoms is selected, whereby generally the pharmaceutical preparation 3bis 4mal is given to body weight daily with a daily active substance quantity from 40 g to 2 mg/kg. Example of the production of tablets (1) 7 - [3 (4-Phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Dihydrochlorid 6 mg Maisst rke 132 mg magnesium stearate 18 mg lactose 45 m entirely 200 mg example of the production of tablets (2) 7 [3 (4-Phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Dihydrochlorid l0 mg corn strength 130 ME magnesium stearate 18 mg lactose 42 m entirely 200 mg the tablets are made of the above components in usual procedures. In the following the results are brought of connections manufactured according to invention by pharmakologischen examinations. (I) examination on antihistamine effect for the determination of the antihistamine effect of a connection in vitro a procedure is used, with which a cut out Ileum of a guinea pig is used. A male sea pig with 300 to 500 g body weight is killed by Ausbluten. A piece of Ileum of a length of 15 cm is cut out from the ileozäkalen region and dipped into Tyrode's solution (made of 0,8 g NaC1, 0.2 g KC1, 0.2 g CaC12, 1.0 g glucose, 1.0 g NaHCOs 0,065 g NaHPO .2H2 0 and 0 2135 g MgC12 .6H2 0 and water up to a total quantity of 1000 valley). Then the Ileumgewebe is cut to lengths from 2,5 to 30 cm and suspended in an organ bath, which is filled with 30 ml Tyrode's solution. The organ bath is held at a temperature of 36°C and blown by the bath a Dowson gas from 5% CO2 and 95% 02. one admits 10-6 M histamine to 10 min after injecting to the bath, in order to measure the sensitivity of the fabric, and one receives a reaction curve (control) regarding the dosage from histamine. As soon as the dosage of the histamine reaction curve (Konstrolle) becomes constant, one gives 10-6 g/tal to the connection to the bath, which can be examined, and further one admits 5 min late histamine, in order to receive a dosage reaction curve. The Retraktion of the Ileum is aufgezeiehnet by means of a writer at a isotonischen transfer equipment (TD-112S, manufactured of Nihon Koden). The antihistamine effect of the examined connection becomes as pA2 - after value “Van Rossam” - method (J.M. Van Lossam: Arch. Inst. Pharmacodyn., 143, expressed 299 [19633), u.zw like that the msximale Retraktion of the Ileums is caused like her by histamine, in the control curve 100% is. The results are shown in table I. Examined connections (connections manufactured according to invention (No. 1-39)) connection 1 i0 11 12 13 14 16 17 18 19 name of the connections 5 [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Mono hydrochloride 7 [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydroearbostyril. Monobydroehlorid 8-Chlor-5 (2-hydroxy-3 [4 (4-chlorphenyl) - - piperazinyl] - propoxy} -3,4-dihydroearbostyril. Mono hydrochloride 6, 8-Dichlor-5 [2-hydroxy-3 (4-phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril. Mono hydrochloride 5 [3 (4-Phenylpiperazinyl) - propoxy] -3,4-dihydroearbostyril. Dibydrochlorid 7 - [3 - (4-Phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril. Dihydrochlorid 1-Methyl-5 [2-hydroxy-3 (4-phenylpiperazinyl) - - propoxy] - 3,4-dihydrocarbostyril. Mono hydrochloride 1-Benzyl-5 [2-hydroxy-3 (4-phenylpiperazinyl) - - propoxy] -3,4-dibydrocarbostyril. Monobydrochlor£d 1-Methyl-5 [3 - {4-pheny lpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Monohydroch orid 5 - {4 - [4 - (4-Methylphenyl) - piper azinyl] - butoxy} - -3,4-dihydrocarbostyril 1-Allyl-5 {2-hydroxy-3 [4 (4-methylphenyl) - - piperazinyI] - propoxy} - 3,4-dihydrocarbostyril 1-Benzyl-7 [3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril 4-Methy1-7 [3 - (4-pheny piperazinyl) - propoxy] - - earbostyril 7 [3 (4-Benzylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril 713 [4 (4-Methylphenyl) - piperazinyl] - propoxy] - -3,4-dihydrocarbostyril 7 - {3 - [4 (4-Chlorphenyl) - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 7 {3 [4 - (2-Methoxyphenyl) - piperazinyl] - -propoxy} - 3,4-dihydrocarbostyril 7 - {3 - [3-Methyl-4 (4-chlorphenyl) - piper azinyl] - - propoxy} - 3,4-dihydrocarbostyril. Dihydrochlorid 8 - [3 - (4-Phenylpiper aziny 1) - propoxy] -3,4-di - hydrocarbostyril Nr.376432 table (continuation). Connection 21 22 23 24 26 27 28 29 31 32 33 34 36 37 38 39 name of the connections 5 [2-Acetyloxy-3 (4-phenylpiperazinyl) - - propoxy] - 3,4-dihydrocarbostyril 5 [2 - (3.4, 5-Trimethoxybenzoyloxy) -3 - (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril 7 - {3 - [4 - (2-Methoxyphenyl) - piperazinyl] - - propoxy} - carbostyril. Dihydrochlorid 1 (2-Propinyl) - 7 [3 (4-phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbost yril. Dihydrochlorid 7 - {3 [4 (3-Fluorphenyl) - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 7 [2-Methyl-3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril 4 [3 (4-Phenylpiperazinyl) - propoxy] - carbostyril 4-Phenyl-7 [3 - (4-phenylpiperazinyl) - propoxy] - - carbostyril 6 - chlorine -8 - bromine -7 - [3 - (4-phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril. Dihydrochlorid 7 - {3 - [4 - (3,4,5-Trimethoxy phenyl) - piperazinyl] - - propoxy} -3,4-dihydrocarbost yril. Dihydrochlori D 5 [3 - (4-Cyclohexylpiperazinyl) - propoxy] -3,4-dihydrocarbostyri! 5 [3 - (4-Phenylhomopiperazinyl) - propoxy] - -3,4-dihyrocarbostyril 5 - {3 - [4 - (2-Acetyloxyäthyl) - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 5 - {3 [4 (2-Hydroxyäthyl) - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 5 [3 - (4-Acetylpiperazinyl) - propoxy] -3,4-di - hydrocarbostyril 5 [3 (4-Benzoylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril 6 [3 (4-Phenylpiperazinyl) - propoxy] - carbostyril 7 [3 - (4-Phenylpiperazinyl) - propoxy] - carbostyril 1-Hexyl-7 [3 - (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Dihydrochlorid 7 - {3 [4 (3-Chlorphenyl) - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril table I Nr.376432 examined connection No. 1 2 3 4 6 7 8 9 pA= 8.08 7.76 8.31 8.95 8.87 9.34 9.88 10.80 10.58 Geprüße connection No. 21 22 23 24 2S 28 27 28 29 11 12 13 14 16 17 18 19 8.90 9.21 8.21 9.39 9.10 9.48 9.63 9.06 8.66 7.99 8.91 31 32 33 34 36 37 38 39 pA= 9.04 7.93 9.23 9.59 9.21 8.66 9.01 9.64 8.57 7.35 9.58 7.52 7.02 7.24 8.58 7.99 9.53 8.93 9.74 RST (II) anästhesie-und sleep-increasing effect (A) the anaesthesia by Halothanan intensifying effect male mice with a weight were used by 20 g of the ddy trunk. An experimental group consisted of 10 mice. An aqueous Gummiarabikum suspension of the connection which can be examined (80 mg of one connection which can be examined and 1 g Gummiarabikum/100 ml physiologlsche NaC1-Lösung) is orally given to each mouse in a dose by 80 mg of the Prüfverbindung/kg body weight. 1 h after the administration is given each mouse to a Gasrespirationskammer (13 × 13 × 24 cm) and oxygen gas, containing 4% Halothan (2-Brom-2-chlor-l, l, l-trifluoräthan) is blown into the chamber during 3 min in a quantity of 2 I/min. The anästhesierte mouse is taken from the chamber, on which the time between the introduction of the anaesthesia up to waking up is measured. The mice of the control group kept a l%ige aqueous solution oral from Gummiarabicum in a dose from 0,1 tal/10 g K0rpergewieht (reference: M.J. turn bulletin and J.W. Watkins: Br. J. Pharmac., 5__88, 27 to 35). The results are shown in table II. Table II Nr.376432 (dose: 8 mg/kg) examined connection No. 1 2 3 4 6 7 8 9! 1! 2! 3 14 16 17 18 19 time (min) 9.3 ± 4.9 11.7 - + 0.6,7.9 ± 3.4,7.4 - + 2.7 16.9 2 7.9 16.8 ± 6.2,8.9 ± 2,4. 7,5 + - 3.3,9.5 + 3,2. 7,9 ± 3.7,6.8 ± 2.2,7.6 ± 3.5,8.1 ± 2.7,7.6 ± 4.3 12.7 - + 3.5 11.4 + 5.6 13.6 ± 0.2,8.4 ± 2.5,9.3 - + 3.5,9.8 + - 3.7 examined connection No. Time (min) 21 22 23 24 26 27 28 29 3! 32 33 34 36 37 39 8.1 ± 3.9 10.4 ± 4.1,7.6 ± 4.2 ii, 6 ± 6.7,7.8 ± 3.3,8.6 ± 3.7,7.8 ± 3.2 10.2 ± 5.8,9.3 ± 4.4,7.9 ± 3.7,8.2 ± 3.9,7.9 ± 3.1,7.4 ± 2.6,7.8 ± 3.4,8.2 ± 3.7 15.3 ± 3.1 13.1 ± 6.0,5.0 ± 2.9 (B) the anaesthesia by Halothan intensifying effect the same procedure as becomes under (II) - (A) described used with the exception that the quantity of the orally given connection on 4 dosage stages, which can be examined, is divided of 0,5, 1, 2 and 4 mg/kg, and the relationship between the dose and that Degree of the anaesthesia-strengthening effect is measured. The results are shown in table III. Examined connection reference example Haloperidol Pentabarbital according to invention manufactured connection connection 6 7 29 table III anaesthesia-strengthening effect (min) 0 mg/kg 0.5 mg/kg 1 mg/kg [10.3 ± 3.3,7.4 ± 3.1,6.6 ± 3.1,9.6 ± 4.1 12.1 ± 4.2,9.5 ± 3.8,8.3 ± 3.7 10.2 ± 3.7,8.1 ± 3.1 12.7 ± 3.9 16.6 ± 5.1 13.7 ± 4.7 13.6 ± 4.9 t oo ù-3 O (C) by Hexabarbital sehlaferh0hende effect caused 2 mg/kg 4 mg/kg 5.3 ± 2.9,5.3 ± 2.6,5.1 ± 2.5,4.9 ± 3.5,4.9 ± 2.5,5.5 - + 2.1,4.8 ± 3.1,5.1 - + 2.6,5.2 ± 2.1,8.2 ± 2.6,5.3 ± 2.5,5.6 ± 2.8,6.5 ± 3.5 Male mice of the ddy trunk with a Körpergewieht from 20 to 25 g 24 h chamfered left. A group consisted of 10 mice. A suspension of the connection from a wässer±gen solution of Gummiarabieum (0.05 g of the connection which can be examined and 1 g Gummiarabikum/100 ml physiological NaC1 - solution), which can be examined, is given orally in the dose mentioned in table IV. 1 h after the administration are given to 0.7% by hexadecimal bar bit Al well salt intraperitoneal in a dose of 70 mg/kg body weight. The time .zwischen the Schlafe±nie± tung up to awaking is measured, whereby the “putting up reflex” is used as index (reference: A.M. Hjort, De E.J. Beer and D.W. Fassett; J. Parmac. Exptl. Ther., 63, 421). Table IV dose sleep time (min) (mg/kg) (means ± 3D) examined connection according to invention manufactured connection physiological saline solution connection 6 connection 6 connection 6 connection 6 connection 6 physiological saline solution connection 17 connection 17 connection 17 connection 17,0.5,1.0,2.0,4.0,8.0 0.125 0.25 0.5,1.0 36.52 ± 10.15 43.76 ± 61 09 51.24 ± 11.75 B4,11 ± 7.80 65113 ± 11.59 86.83 ± 12.24 32 14 ± 6.25 39.51 ± 8.45 45.57 ± 10.05 51.77 ± 6.60 56.92 ± 6.13 acquaintance comparison connection physiological saline solution Haloperidol Haloperidol Haloperidol 4 8 16 35.07 ± 4.98 43.01 ± 19.22 46.83 ± 13.94 66.81 ± 14.32 (III) effect regarding the combat desire of a mouse, the long time was insulating. Particulars, male mice of the ddy trunk with 15 to 20 g Körpergewlcht were kept 1 month separate in cages. An experimental group consisted in each case of 10 pairs of mice. Each member of a pair of mice was in such a way selected that, if a mouse were given to others to the cage or two these constantly fought over 30 s. OD - values were computed, by giving those connection of each group of the mice which can be examined in each case. The effect for the Inhibierung of the combat desire of the examined connections is called positive, if the mouse continues a fighting only within 5 s during 1 min. The mouse fights longer than 5 s, EO became the mice again to getrennt1 for the number of injured mice to keep low, (reference: C.Y. Ven, R.L. Stanger and N. Millman: Arch. Int. Pharmacodyn., 123, 1979). The results are shown in table V. Table V Nr.376432 Geprüße connection according to invention manufactured connection connection 6 connection 9 connection 37 connection 39 connection 17 comparison connection: Diazepam OD o (mg/kg) 1.28 (0.63 - 2.72) 0.70 (0.51 - 1.12) 1.52 (0.78 - 3.53) 0.78 (0.22 - 1.38) 0.96 (0.52 - 2.31) 0.92 (0.38 - 1.59) 7.29 (4.04 - 18.6) (IV) Analgeti effect male mice were used by the ddy trunk with a body weight from 15 to 23 g. An experimental group consisted of 10 mice. The connections which can be examined became oral after in (II) described procedures given. 80 min after the administration was intraperitoneal injected 0.1 ml a 0,6%igen acetic acid, aqueous Lösung/10 g body weight. With the mice, to which orally the Vergleiehsverbindung (Haloperidol) had been given, the injection 110 is given to min after the administration. The number of curvatures after 10 min 10 min is noted, whereby the EDs0 was set - values of the respective connections in comparison to the number of curvatures with the control group (reference: R. Koster, M. Anderson and E.I.Debber: Fed. Proe., 1_88, 412,). The results are shown in table Vl. Table VI examined connection EDso (mg/kg) according to invention manufactured connection No. 6 connection Nr.37 connection Nr.31 acquaintance comparison connection Haloperidol 2.31 (1.53 - 3.46) 1.52 (0.71 - 3.15) 1.92 (1.28 - 4.31) 2.31 (1.26 - 5.31) (V) of acutes toxicity (LDs0) mice were used by the ddy trunk with 20 to 22 g body weight. An experimental group consisted of 10 mice. Oral Verabreiehung: The connection which can be examined becomes in a 1 Gew. - % Gummiarabikum containing physiological NaC1-Lösung (water) suspends. Intravenous Verabreiehung: The connection which can be examined is solved in 50%iger of aqueous propylene glycol solution. The results are shown in table VII. Table VII Nr.376432 (LD o) examined connection according to invention manufactured connection No. 6 7 39 17 31 acquaintance connection diazepam male mice oral (mg/kg) 920 1600 1206 898,870 intravenous (mg/kg) of 240,424,310,218,256 female mice oral intravenous (mg/kg) (mg/kg) i 890,250 1650 432 ii00 293,860,216,923,248 59 58 LDs0-Werte (oral administration) of the available connections, which were not the connections 6, 7, 17, 31 and 39, were also determined over 800 mg/kg when using male mice of the ddy trunk. In the following some reference examples are brought to the production of basic materials for the procedure according to invention. Reference example 1:20,0 g 8-Chlor-5-hydroxy-3,4-dihydrocarbostyril and 18 g potassium carbonate were suspended in 160 ml isopropyl alcohol, on which 40 ml epichlorohydrin was admitted and the Beaktionsgemisch was held during 6 h with 70 to 80°C. The reaction mixture was concentrated under reduced pressure, on which hiebei the received arrears with 100 ml 2n caustic soda solution under cooling were agitated. Insoluble was filtered off, washed and dried with water. The raw crystals were recrystallized from isopropanol, with which 18.5 g 8-Chlor-5 (2,3-epoxypropoxy) - 3,4-dihydrocarbostyril in form of colorless, needle-like crystals with Fp. = 161 to 165°C were received. Reference example 2: A mixture from 20,0 g 6-Chlor-7-hydroxy-3,4-dihydrocarbostyril, 3.7 g sodium hydroxide and 100 ml methanol was warmed up under agitating 3 h to 40 to 50°C. Then 150 was in addition-given ml epichlorohydrin, on which the reaction mixture 5 h under return flow was heated up. After completion of the reaction the reaction mixture under reduced pressure was evaporated to dry ones. Hiebei the received arrears were mixed with 100 ml 2n caustic soda solution and agitated well. Insoluble was filtered off, washed and dried with water. Hiebei the received raw crystals were recrystallized from methanol ethanol, with which 19.7 g 6-Chlor-7 (2,3-epoxypropoxy) - 3,4-dihydrocarbostyril in form of colorless crystals with Fp. = 190 to 192°C were received. Reference examples 3 to 6: In the procedure of the reference examples 1 and 2 the following connections were received: Reference example connection 6-Chlor-5 (2,3-epoxypropoxy) - 3,4-dihydroearbostyril 6,8-Dichlor-5 (2.3 - - epoxypropoxy) - 3.4 - - dihydrccarbostyril 8-Brom-5 (2,3-epoxypropoxy) - 3,4-dihydroearbostyril 5,6-Dichlor-8 (2.3 - - epoxypropoxy) - 3.4 - - dihydrocarbostyril crystalline form (recrystallization means) colorless crystals (isopropanol) colorless crystals (methanol) colorless, needle-like crystals (methanol) colorless crystals (methanol) fusion point °C 218 - 221,177 - 178,220 - 222,183 - 184 Nr.376432 reference example 7: A mixture from 24,3 g 8-Brom-5-hydroxy-3,4-dihydrocarbostyril, 9 g Kaliumhyroxyd and 150 ml isopropanol was agitated with 70 to 80°C during 30 min and shifted then with 25 g 1,3-Bromchlorpropan, on which the reaction mixture 6 h under return flow was heated up and cast in after terminated conversion to 200 ml aqueous 2n caustic soda solution. Hiebei developed insoluble was filtered off, washed and dried with water. Hiedurch the received raw crystals were recrystallized from ethanol, with which 21.5 g 8-Brom-5 (3-ehlorpropoxy) - 3,4-dihydrocarbostyril in form of colorless, needle-like crystals with Fp. = 184 to 185°C were received. Reference example 8:5 g 6-Chlor-8-brom-7-hydroxy-3,4-dihydroearbostyril and 3 g potassium hydroxide were mixed with 120 ml isopropanol and agitated with 50 to 60°C during 1 h. Then 10 ml 3-Brom-l-chlorpropan were in addition-given and it was agitated during 6 h with 70 to 80°C. The reaction mixture was concentrated under reduced pressure to dry ones and hiedurch the received arrears with chloroform were extracted. The chloroform layer was more ser washed and dried with WaslS. Then the chloroform was removed for 3,4-dihydrecarbostyril in form of colorless, needle-like crystals with Fp by distillation and hiedurch the formed arrears from ethanol under receipt from 6,2 g 6-Chlor-8-brom-7 (3-chlorpropoxy) -. = 87 to 88°C recrystallizes. Reference examples 9 to 12: In the procedure in accordance with reference example 8 the following connections were received: Reference example 11 12 connection 4-Methyl-6 (3-chlorpropoxy} - carbostyril 4-Methyl-7 (3-chlorpropoxy) - carbostyril 5 (2-Methyl-3-chlerpropoxy) - S, 4-dihydrocarbostyril 7 (2-Methyl-3-chlorpropoxy) - 3.4 - - dihydrocarbostyriI crystalline form (recrystallization means colorless, needle-like crystals (ethanol) colorless, needle-like crystals (Äth anol) colorless, needle-like crystals (ethanol) colorless, needle-like crystals (ethanol water) fusion point °C 183,169 - 170,139 - 140 - 78 reference example 13; A mixture from 18,3 g 3,4,5-Trimethoxyanilin, 31.2 g until (B-bromäthyl) - - amine. Mono hydraulic bromide and 170 ml methanol were held under a nitrogen gas flow during 10 h return flow temperature. After cooling of the reaction mixture 5.3 g water-free Natriumcarbonat were then added, on which the received mixture was heated up during further 10 h under return flow. Under reduced pressure about 70 was removed ml methanol by distillation and the mixture was left at ambient temperature cooling. Hiedurch the failed crystals were collected by filtration and washed with a small ethanol quantity. By recrystallization from ethanol 38 g became 4 (3; 4,5-Trimethoxyphenyl) - piperazin. Mono hydraulic bromide I0 in form of colorless, panel-like crystals with a fusion point from 227 to 228°C receive. Then this connection in 20%iger of aqueous sodium hydroxide solution is solved and the solution with chloroform is extracted. The chlorine form layer is three times washed with satisfied sodium chlorid solution, dried then and released by distilling from chloroform. The free form of 4 (3,4,5-Trimethoxyphenyl) - piperazin as only substance in form of a colorless, viskesen, oily material one receives. The chemical structure of this connection is confirmed by the NMRund the IR spectrum. Example 1:4,4 g 5 (2,3-Epoxypropoxy) - 3,4-dihydrocarbestyril and 3.4 g 4-Phenylpiperazin are dispersed in 60 ml Methanel and converted with 50 to 60°C during 3 h. After completion of the reaction the reaction mixture under reduced pressure is concentrated. Hiedurch the received arrears 5 becomes ml konz. Hydrochloric acid and 30 ml ethanol for the even dissolution of the arrears. in addition-given and far 200 ml are in addition-given to acetone. The failed crystals are collected and dried by filtration. By recrystallizing from water 6.5 g become 5 [2-HydroxY-3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril. Mono hydrochloride in form of colorless, needle-like crystals with a fusion point from 239 to 241°C receive. Example 2:4,4 g 6 (2,3-Epoxypropoxy) - 3,4-dihydrocarbostyril and 3.4 g 4-Phenylpiperazin are dissolved in 80 ml isopropanol and converted with 50 to 60°C during 3 h on agitating conditions. Then 5 becomes ml konz. Hydrochloric acid in addition-given and under reduced pressure is concentrated to dry ones. Hiedurch the received arrears becomes from hot water in such a way under receipt of 6,1 g 6 - [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril. Mono hydrochloride 1/2 hydrate in form of colorless, needle-like crystals with a fusion point from 223 to 224°C recrystallizes. Example 3:2,9 g 1 (3-Methylbutyl) - 5 (2,3-epoxypropoxy) - 3,4-dihydrocarbostyril and 1.7 g 4-Phenylpiperazln are mixed with 50 ml methanol and converted with 50 to 60°C during 3 h. The reaction mixture is concentrated under reduced pressure and hiedurch the received arrears in 50 are dissolved ml acetone. To this solution 20 is in addition-given ml to an acetone solution, which contains 1.1 g oxalic acid, then hiedurch the formed precipitation is separated by filtration, washed and dried with acetone. By UmkristaIlisierung from ethanol ether 2.1 g 1 (3-Methylbutyl) become - 5 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril. Mono oxalate in form of colorless crystals receive. This product is confirmed as individual connection by silicagel thin section chromatography (development solution center!: Chloroform: Methanel = 9: I) Elementary analysis: C gH” O N, computes (tons) C 64.30, H 7.26, N 7.76 found (tons) C 64.52, H 7.10, N 7.48 I0 IR (I nfrarotabsorptionsspektrum) 3400 cm-i (OH), 1680-I (_CO_) NMRI: ö = 6.8 - 7.3 ppm (aromatic proton 8H) = 0.92 ppm (methyl proton, 6H) (i: The NMR measurements were neutralized with d6-DMSO accomplished) IS hiedurch the received connection according to usual method and the raw crystals will become made of ethanol under receipt of 1 (3-Methylbutyl) - 5 [hydroxy-3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril inForm colorless, prism-like crystals with a fusion point of 156-157°C recrystallizes. Example 4 " 3.4 g l (3-Phenylpropyl) - 5 (2,3-epoxypropoxy) - 3,4-dihydrocarbostyril and 2.0 g 4 (4-Methylphenyl) - piperazin with 50 ml methanol are mixed and converted by a procedure, which was similar to the understanding example 3. Hiedurch the received raw crystals become from methanol ether under receipt of 4,2 g 1 (3-Phenylpropyl) - 5 - {2-hydroxy-3 - [4 (4-methylphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril. Mono oxalate in form of colorless crystals recrystallizes. Elementary analysis: C s H 07 N computes (tons) C 67.64, H 6.85, N 6.96 found (%) C 67.86, H 6, B2, N 6.81 IR (infrared absorption spectrum) 3480 cm-1 (OH, 1676 cm-1 (C=O) NMRtB: ö = 6.6 - 7.4 ppm (aromatic proton, 12H) = 2.30 ppm (methyl protons, 3H) (ß: The NMR measurements were accomplished with d6 .DMSO.) Examples 5 to 23: After the function in accordance with the examples 1 to 4, the following connections were received: Example connection 8 [2-Hydroxy-3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril 6 - (2 - Hydroxy-3 - [4 - - (4-ehlorphenyl) - - more piper azlnyl] - propoxy) - -3,4-dihydrocarbostyril. Monohydrechlorid. 1/2 hydrate crystalline form (recrystallization means) colorless crystals (methanol - ethers) colorless, needle-like crystals (ethanol) fusion point °C 263,212 - 214 table (continuation) example 11 12 13 14 connection 7 - {2-Hydroxy-3 [4 - - (4-chlorphenyl) - - piperazinyl] - propoxy} - -3,4-dihydroearbostyril. Mono hydrochloride. Mono hydrate 8-Brom-5 [2-hydroxy -3 (4-phenylpiperazinyl) - propoxy] -3.4 - - dihydrocarbostyril 8-Chlor-5 [2-hydroxy -3 (4-phenylpiperazinyl) - propoxy] -3.4 - - dihydrocarbostyril. Mono hydrochloride. .3/2 hydrate 8-Chlor-5 {2-hydroxy -3 [4 - (4-chlorphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril. Mono hydrochloride 6-Chlor-5 [2-hydroxy -3 (4-phenylpiperazinyl) - propoxy] -3,4dihydroearbostyril. Di' bydrochlorid. Monöhydrat 6,8-Dichlor-5 [2 - - hydroxy-3 (4-phenylpiperazinyl) - - propoxy] - 3,4-dihydrocarbostyril. Mono hydrochloride 8-Chlor-5 {2-hydroxy -3 [4 (2-chlorphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 8-Brom-5 {2-hydroxy -3 [4 - (2-methoxyphenyl) - - piperazinyl] - propoxy} - -3,4-dihydreearbestyril. Dihydrochlorid crystalline form (Umkr [stallisierungsmittel) colorless, needle-like crystals (isopropanol) colorless crystals (methanol) colorless crystals (methanol - ethers) colorless, needle-like crystals (methanol - ether) colorless, needle-like crystals (methanol - ethers) colorless crystals (water) colorless crystals (ethanol) colorless crystals (methanol - ether) fusion point degrees of 66 - 174 - 176,226 - 228,228 - 230,218 - 225,251 - 253,156 - 158,226 - 228 table (continuation) example 16 17 18 19 21 22 23 connection 6-Chlor-7 [2-hydroxy -3 (4-phenylpiperazinyl) - propoxy] -3.4 - - dihydrocarbostyril 6-Chlor-7 {2-hydroxy -3 [4 (2-methoxy - phenyl) - piperazinyl] - - propoxy) - 3,4-dihydrocarbostyril 1-Methyl-5 [2-hydroxy -3 (4-phenylpiperazinyl) - propoxy] -3.4 - - dihydroearbostyril 1-Äthyl-5 [2-hydroxy -3 - (4 - pheny Ipiper - azinyl) - propoxy] -3.4 - - dihydrocarbostyrll. • mono oxalate l-Allyl-5 {2-hydroxy -3 [4 - (4-methylphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 1-Benzyl-5 [2-hydroxy -3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril 6 [2-Hydroxy-3 (4 - - phenylpiperazinyl) - - propoxy] - carbostyril. .1/2 hydrate 8-Brom-5 [2 - - hydroxy-3 (4 - - phenylplperazinyl) - - propoxy] - earbostyril 6,8-Dichlor-5 {2 - - hydroxy-3 [4 (4 - - ehlorophenyl) - piperazinyl] - propoxy) - 3.4 - - dihydrocarbostyril. Monohydroehlorid. • 1/2 hydrate crystalline form (recrystallization means) colorless, nadelartiga crystals (methanol - wet) colorless crystals (ethanol) colorless, needle-like crystals (n-hexane - benzene colorless crystals (ethanol - ethers) colorless, needle-like crystals (Ligroin - benzene) colorless, nadelart£ge crystals (petroleum ether - ethers) colorless crystals (methanol) colorless, panel-like crystals (methanol) colorless, puderförmige crystals (methanol) fusion point degrees of 171 - 173,183 - 184,143 - 145,201 - 203,123 - 124,148 - 150,218 - 219,179 - 182,158 - 161 example 24:2,4 g 4-Methyl-7 (2,3-epoxypropoxy) - carbostyril and 1.8 g 4-Phenylpiperazin become with 30 ml ethanol mixed and during 3 h on return flow conditions heats up. After cooling of the reaction mixture hiedurch the failed crystals are collected by filtration and washed with ether. Hiedurch the received raw crystals become in 50 ml s methanol and 3 ml konz. Hydrochloric acid dissolved and the mixture is then evaporated under reduced pressure to dry ones. Hiedurch the received arrears become from ethanol - ethers under receipt of 2,7 g (yield 63%) 4-Methyl-7 [2-hydroxy-3 (4-phenylpiperazinyl) - - propoxy] - earboetyril. Mono hydrochloride in form of colorless crystals with a fusion point from 190 to 191°C recrystallizes. Example 25: To the procedure of the example 24 4-Methyl-6 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] becomes similar - carbostyril.1/2 hydrate in form of colorless crystals (recrystallized from ethanol) with a fusion point from 212 to 213°C receive, example 26:4,8 g 5 (3-Chlorpropoxy) - 3,4-dihydrocarbostyril and 4 g 4-Phenylpiperazin are mixed with 40 ml toluol and heated up during 24 h on return flow conditions. Then LS is concentrated the reaction mixture under decreased pressure to dry ones. Hiedurch the received arrears are dissolved in 80 ml chloroform and the chloroform layer is washed twice washed with 5,0% of aqueous sodium hydrogencarbonate solution then twice with water, removed with water-free sodium sulfate dried and the chloroform by distillation. To hiedureh the received arrears hexane hlnzugegeben and the insoluble material is collected by filtration, the insoluble material in 30 ml 6% HCI Methanollösung and concentrated under reduced pressure to the Troekne is then dissolved. Hiedurch the received arrears become from methanol ether under Erhalt' of 3,2 g 5 [3 (4-Phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril. Mono hydrochloride in form of colorless crystals with a fusion point of 262°¢ (decomposition) recrystallizes. Example 27:4,5 g 6 (2-Chloräthoxy) - 3,4-dihydrocarbostyril and 3.3 g sodium iodide are mixed with 50 ml acetone and heated up during 5 h on return flow conditions. Then ml dimethylformamide to the reaction mixture and the acetone is removed distillative are in addition-given with 40 to 45°C under decreased pressure. Further 3.8 g 4-Phenylhydrazin are in addition-given to the reaction mixture and the reaction is accomplished with 60 to 70°C during 7 h on agitating conditions. The reaction mixture is concentrated under reduced pressure to dry ones and hiedurch the received arrears are dissolved in 80 ml chloroform. The chloroform layer is washed twice with aqueous 5% sodium hydrogencarbonate solution and then twice with water. After drying the chloroform layer the chloroform is removed by distillation. Hiedurch the received arrears become by silicagel Säulenchromategraphie (silicagel: Wako gel C-200, registered trade mark, manufactured and drove out by Wako Chemical CO., Ltd. ; Elutionslösungsmittel chloroform: Methanol = 20: 1), and the desired connection is transferred into the hydrochloride using ethanol, which is satisfied with Chlorwassersto£f, whereby ethanol is removed by distillation under reduced pressure. Hiedurch the received arrears become from methanol ether under receipt of 3,8 g 6 [2 (4-Phenylpiperazfnyl) - 0 - äthoxy] - 3,4-dihydrocarbostyril. mono hydrochloride mono hydrate in form of colorless crystals with a fusion point from 196 to 198°C recrystallizes. Examples 28 to 72: After the function in accordance with the examples 26 and 27 is received the following connections: Example 28 29 31 82 33 34 36 87 connection 5 - [2 (4-Phenylpiperazinyl) - äthoxy] -3.4 - - dihydrocarbostyril. • Dihydrochlorid 6 - {3 [4 (2-Methoxyphenyl) - piperazinyl] - - propoxy} - carbostyril. • Dihydrochlorid 7 [2 (4-Phenylpiperazinyl) - äthoxy] - -3,4-dihydroearbostyril 7 [3 (4-Phenylpiperazinyl) - propoxy] - -3,4-dihyrocarbostyril-dihydrochlorid.3/4 hydrate 8 [2 (4-Phenylpiperazinyl) - äthoxy] - -3,4-dihydrocarbostyril. • Dihydrochlorid. .1/4 hydrate 1-Methyl-5 [3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril. Dihydrochlorid. 1/2 hydrate 8-Brom-5 {3 - [4 - - (4-methylphenyl) - - piperazinyl] - propoxy} - -3,4-dihyrocarbostyril 5 - {4 [4 (4-Methylphenyl) - piperazinyl] - - butoxy) -3.4 - - dihydroearbostyril 5 - {5 - [4 (2-Methoxyphenyl) - piperazinyl] - pentyloxy} - 3.4 - - dihydrocarbostyril S - {2 - [4 - (4 - methyl - phenyl) - piperazinyl] - - äthoxy} -3.4 - - dihydrocarbostyril crystalline form (recrystallization means) colorless, shed-like crystals (methanol - ethers} colorless crystals (methanol) colorless, needle-like crystals (ethanol) colorless, needle-like crystals (methanol - Ether) colorless crystals (methanol - ethers) colorless crystals (ethanol - ether) weakly yellow, needle-like crystals (Ligroin - benzene) colorless, plüttchenartige crystals (methanol} colorless, needle-like crystals (ethanol) colorless, panel-like crystals (ethanol) No. 376432 fusion point °C 27O (decomposition) 241 - 242 (decomposition) 171 - 175,213 - 215,255 (decomposition) 226 - 228,181 - 182,170 - 172,154 - 156,179 - 182 table (continuation) Krist all form fusion with (Umkristallipunkt play connection sierungsmittel) °C 38 39 41 42 43 44 46 47 6 3 (4-Phenylpiperazinyl) - propoxy] - -carbostyril 8 - {3 - [4 - (2-Methoxyphenyl) - piperazinyl] - - propoxy} - carbostyril. • Dihydrochlorid 7 - [3 (4-Phenylpiperazinyl) - - propoxy] - carbostyril 8-Brom-5 [3 (4-phenylpiperazinyl) - - propoxy] - carbostyril. • Dihydrochlorid. • Monobydrat 7 {3 [4 (4-Methylphenyl) - piper azinyl] - - propoxy} -3.4 - - dihydrocarbostyril - {3 - [4 - (2-Äthoxyphenyl) - piperazinyl] - - propoxy} - 3.4 - - dihydrocarbostyril 7 {3 - [4 (2-Äthoxyphenyl) - piperazinyl] - - propoxy} -3.4 - - dihydrocarbostyril 6-Chlor-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3.4 - - dihydroearbostyril. • Dihydrocblorid. • mono hydrate 6-Brom-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3.4 - - dihydrocarbostyril. • Dihydrochlorid 7 {3 [4 (2-Chlorphenyl) - piperazinyl] - - propoxy} -3.4 - - dihydrocarbostyril colorless, shed-like crystals (methanol) colorless, needle-like crystals (ether) yellowish, needle-like crystals (methanol) colorless, needle-like crystals (methanol yellowish, needle-like crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, needle-like crystals (methanol - ethers) colorless, needle-like crystals (methanol - ethers) weakly yellowish, prismaförmige crystals (ethanol 226 - 227,242 - 245 (decomposition) 237 - 238,206,149 - 150,155 - 156,140 - 142,280 (decomposition) 255 - 258,146 - 147 Nr.376432 table (continuation) crystalline form fusion with (Umkristallipunkt play connection sierungsmittel) QC 48,156 - 158 49 51 52 53 54 56 57 58 7 {3 [4 (3-Chlorphenyl) - piper azinyl] - - propoxy} -3.4 - - dihydroearbostyril 7-13 [4 (4-Chlorpheny 1) - piperazinyl] - - propoxy} -3.4 - - dihydrocarbostyril 7 {3 - [4 (2-Methoxyphenyl) - piperazinyl] - - propoxy} -3.4 - - dihydrocarbostyril 7 {3 [4 - (4-Methoxyphenyl) - piperazinyl] - - propoxy) -3.4 - - dihydrocarbostyril 6 [3 (4-Phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril 8 - [3 (4-Phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril 7 [4 (4-Phenylpiperazinyl) - butoxy] - -3,4-dihydrocarbostyril 5 - {3 - [4 (2-Methoxyphenyl) - piperazinyl] - - propoxy} -3.4 - - dihydrocarbostyril 7 {3 - [4 (2-Methoxyphenyl) - piperazinyl] - - propoxy} - arbostyril 1-Benzyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3, 4-dihydrooarbostyril 1-Ally! - 7 [3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Dihydrochlorid colorless, needle-like crystals (ethanol) weakly yellowish, prismaförmige crystals (ethanol) colorless, powdery crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, plate-like crystals (ethanol) colorless, plate-like crystals (ethanol) colorless, needle-like crystals (isopropanol) colorless, prismaförmige crystals (methanol) colorless, powdery crystals (ethanol) weakly yellowish, needle-like crystals (ethanol) colorless, crystals (ethanol) 200 - 202,134 - 137,146 - 149,184 - 185,112 - 114,123 - 124,194 - 196,229 - 232,125 - 127,189 - 192 table (continuation) example 59 61 62 63 64 66 67 connection l-Propargyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3.4 - - dihydroearbostyril. • Dihydrochlorid l-Hexyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3.4 - - dihydrocarbostyril. • Dihydrochlorid 1 (3-Phenylpr pyl) - -7 - [3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. • Monohydreehlorid 1-Benzyl-5 [3 (4 - - phenylpiperazinyl) - - propoxy] -3.4 - - dihydrocarbostyril 1-Äthyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril Dihydrochlorid 1-Methyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3.4 - - dihydrocarbostyril. • Dihydroehlorid 4-Methyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydroearbostyril. • Dihydrochlorid. • dihydrate 5 [3 (4-Acetylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril 5 [3 (4-Benzoylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Hydroehlorid crystalline form (recrystallization means) weakly bräunliehe, needle-like crystals (methanol) colorless crystals (ethanol - acetone ethers) colorless, shed-like crystals (ethanol) weakly yellowish, needle-like crystals (Ligroin) colorless crystals (ethanol) colorless crystals (ethanol) colorless crystals (methanol - ether} colorless, needle-like crystals (ethanol) colorless, plate-like crystals (methanol ether) fusion point °C 215 - 216,176 - 181,201 - 202,113,222 - 224,204 - 207,260 - 265,143 - 145 24O (decomposition) table (continuation) example 68 69 71 72 73 74 7S 76 77 78 connection 5 {3 - [4 (2-Acetyloxyäthyl) -piperKristallform (recrystallization means) colorless, needle-like Sehmelzpunkt °C 131 - 132 azinyl] - propoxy} -3.4 - - dihydrocarbostyril 5 {3 [4 (2-Hydroxyäthyl) - piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 4-Phenyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] - carbostyril 4-Phenyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril 4-Phenyl-7-13 [4 (2 - - methoxyphenyl) -1-piperazinyl] - propoxy} - carbostyril 7 {3 [4 (2,3-Dimethylphenyl) -1-piperazinyl] - - propoxy] - carbostyril. Mono hydrochloride mono hydrate 7 {3 - [4 (2,5-Dimethylphenyl) -1-piperazinyl] - - propoxy] - carbostyril 7 {3 - [4 - (2,5-Dichlorphenyl) - l-piperazinyl] - - propoxy] - carbostyril 7 {3 - [4 (2-Methyl-5 - chlorphenyl) -1-piperazinyl] - propoxy} - carbostyril 7 {3. [4 (2-Chlor-4 - methylphenyl) -1-piperazinyl] - propoxy} - carbostyril 7 {3 [4 (2-Methyl-3 - ehlorphenyl) -1-piperazinyl] - propoxy} - earbostyril crystals (isopropanol) colorless, sohuppenartige crystals (water) colorless, needle-like crystals (methanol) colorless, needle-like crystals (ether hexane) colorless, needle-like crystals (isopropanol - Water) colorless, needle-like crystals. (Methanol) colorless, flaky crystals (isopropanol) colorless, needle-like crystals (ethanol) colorless, prismatisehe crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, flaky crystals (ethanol) 158 - 159,198 - 199,138 - 140,161 - 162,262 - 263,162 - 163,187 - 189,182 - 183,209 - 210,192 - 193 table (continuation) example 79 81 82 83 84 86 87 connection 7 {3 [4 (2,3-Dichlorphenyl) -1-piperazinyl] - - propoxy} - carbostyril 7 - {3 [4 (3,4-Dichlorphenyl) -1-piperazinyl] - - propoxy} - carbostyril 6-Chlor-7 {3 [4 (2,3-dimethylphenyl) -1-piperazinyl] - propoxy} - 3,4-dihydrocarbostyril. • 1/2 hydrate 1-n-Hexyl-6-chlor-7 - {3 [4 (2,3-dimethylphenyl) -1-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril. Mono oxalate 1-Allyl-6-chlor-7 {3 - [4 - - (2,3-dimethylphenyl) - l - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril. • mono oxalate 1 (3-Phenylpropyl) -6 - - chlor-7 {3 - [4 (2,3-dimethylphenyl) -1-piperazinyl] - propoxy} -3,4-dihydroearbostyril. Mono oxalate 8-Brom-5 [6 [4 (2,5-dichlorphenyl) -1-piperazinyl] - hexyloxy} - carbostyril 5 {3 [4 - (2-Chlor-6 - methylphenyl) -1-piperazinyl] - propoxy} -3,4-dihydrocarbostyril 7 {3 [4 (2-Chlor-6 - methylphenyl) - l-piperazinyl] - propoxy} -3,4-dihydrocarbostyril crystalline form (recrystallization means) colorless, prism tables of crystals. (Ethanol chloroform) brownish, prismatisehe crystals (ethanol chloroform) colorless, needle-like crystals (methanol - ethanol) colorless, needle-like crystals (lsopropanol) colorless, needle-like crystals (I sopropanol) colorless, needle-like crystals (methanol water) colorless, needle-like crystals (ethanol) colorless, flaky crystals (ethanol) colorless, prismatisehe crystals (ethanol) fusion point °C 192 - 195,209 - 210 IS5 - 156,178,171 - 172,218 - 219,125 - 126,206 - 209,162 - 164 table (continuation) example 88 89 9O 91 92 93 94 95 96 97 connection 5 {3 - [4 - (2,3-Dimethylphenyl) -1-piperazinyl] - - propoxy ] - 3,4-dihydrooarbostyri! 7 - {3 [4 (2,3-Dimethylphenyl) - 1-piperazinyl] - - propoxy} -3,4-dihydrooarbostyril 7 - {3 [4 (3,4-Dichlorphenyl) -1-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 7 - {3 [4 (2,3-Dimethylphenyl) - l-pipe azinyl - - propoxy} - earbostyril. • mono hydraulic hlorid. Mono hydrate 5 - {3 [4 - (2,5-Dichlorphenyl) -1-piper azinyl] - - propoxy} -3,4-dihydroearbostyril 7 {3 [4 (2,5-Diohlorphenyl) - l-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 5 {3 [4 (2,3-Diehlorphenyl) - l-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 7 - {3 - [4 (2,3-Diehlorphenyl) - l-piperazinyl] - - propoxy} -3,4-dihydrocarbostyril 5 {3 [4 (3,4-Dichlorphenyl) - l-piperazinyl] - - propoxy} - 3,4-dihydrooarbostyril 7 {3 [4 (3,4-Dichlorphenyl) - l-piperazinyl - - propoxy l-3,4-dihydrocarbostyril crystalline form (recrystallization means) colorless, plate-like “crystals (ethyl acetate) colorless, nade! - well-behaved crystals (ethanol) lightyellow, needle-like crystals colorless, needle-like crystals (Methano!) colorless, prism tables of crystals (ethanol chloroform) colorless, flaky crystals (Äthanel chloroform) colorless, prism tables of crystals (ethanol chloroform) colorless, prism tables of crystals (Äthano! - Chloroform) colorless, needle-like crystals (ethanol ¢hloreform) colorless, prism tables of crystals (ethanol chloroform) fusion point “C 197 - 198,153 - 154,225 - 226,262 - 263,170 - 172,153 - 155,206 - 207,170 - 172,188 - 190,180 - 182 table (continuation) example 98 99 I00 101,102 I03 104 i05 106,107,108 connection 5 {3 [4 (3,5-Dichlorphenyl) - l-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 5 - (3 [4 (3,4-Dimethylphenyl) -1-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 7 - {3 [4 - (3,4-Dimethyl - phenyl) -1-piperazinyl] - - propoxy} -3,4-dihydrocarbostyril 5 - {3 [4 (3-Chlor-4 - methylphenyl) -1-piperazinyl] - propoxy} - 3,4-dihydrocarbostyril 7 - {8 [4 (3-Chlor-4 - methylphenyl) -1-piperazinyl] - propoxy} -3,4-dihydrocarbostyril 5 - {3 [4 (2-Methyl-3 - chlorphenyl) -1-piperazinyl] - propoxy} -3,4-dihydrocarbostyril 5 {3 [4 (2-Methyl-5 - CH [orphenyl) - l-piperazinyl] - propoxy} -3,4-dihydrocarbostyril 7 {3 [4 (2-Methyl-3 - chlorphenyl) - l-piperazinyl] - propoxy} - 3,4-dihydroearbostyril 7 - {3 - [4 - (2-Methyl-5 - chlorphenyl) - l-piperazinyl] - propoxy} -3,4-dihydrocarbostyril 5 {3 [4 (3,5-Dimethylphenyl) - l-piperazinyl ] - - propoxy 1-3,4-dihydrocarbostyril 5 - {3 [4 (2,5-Dimethylphenyl) - l-piperazinyl] - - propoxy) -3,4-dihydrocarbostyril crystalline form (recrystallization means) colorless, prism tables of crystals. (Ethanol chloroform) colorless, needle-like of crystal (methanol) yellowish, prism tables of crystals (ethanol) lightyellow, needle-like crystals (methanol chloroform) lightyellow, needle-like crystals (ethanol) colorless, plate-like crystals (ethanol chloroform) colorless, prism tables of crystals (ethanol chloroform) colorless, prlsmatische crystals (ethanol chloroform) colorless, prlsmatische crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, prism tables of crystals (ethanol) fusion point °C 224 - 225,200 - 201,170 - 171,192 - 193,157 - 158,202 - 203,173 - 176,162 - 163,138 - 139,208 - 209,166 - 167 Nr.376432 table (continuation) crystalline form fusion with (Umkristallipunkt play connection sierungsmittel ) °C 109,167 - 168 II0 iii 112,113,114,115,116 1! 7,118,119,120 7 {3 [4 (3,5-Dimethylpheny) -1-piperazinyl] - - propoxy} -3,4-dihydroearbostyril 7 {3 [4 - (2,5-Dimethylphenyl) -1-piperazinyl] - - propoxy] -3,4-dihydroearbostyril 7 - {3 [4 (3-Chlorphenyl) - -1-piperaziny!] - propoxy} - - earbostyril. Monohydroeh! orid 5-13 [4 (3-Chlorphenyl) - -1-piperazinyl] - propcxy} - -3,4-dihydroearbostyril 5 (3 [4 (3-Fluorphenyl) - -1-piperazinyl] - propoxy} - -3,4-dihydroearbostyril 7-13 [4 - (4-Fluorphenyl) - -1-piperazinyl] - propoxy} - -3,4-dihydroearbostyril 7 - {3 [4 (2-Äthoxyphenyl) -1-piper azinyl] - - propoxy} - earbostyril 5 {3 [4 (2-Methylphenyl) -1-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 5 {3 [4 (3-Methylphenyi) -1-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 5 - (3 [4 (4-Methylphenyl) -1 - piperazi ny! ] - - propoxy} -3,4-dihydrocarbostyril 7 (3 [4 (2-Methylphenyl) - l-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 7 - (3 [4 (3-Methylphenyl) -1-piperazinyl] - - propoxy} -3,4-dihydro - carbostyril colorless, prismatisehe crystals (methanol) colorless, prism tables of crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, needle-like crystals (ethanol water) colorless, needle-like crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, amorphously (ethanol water) colorless, flaky crystals (ethanol) colorless, needle-like crystals (ethanol) colorless, flaky crystals (ethanol) colorless, prism tables of crystals (ethanol) colorless, prism tables Crystals (ethanol) 148 - 150,236 - 237,265 - 268,187 - 188,168 - 169,128 - 131,177 - 179,171 - 172,195 - 196,151 - 153,169 - 171 table (continuation} example 121,122,123,124,125,126,127,128,129,130,131 connection crystal form (recrystallization means) 5 (3 [4 (2-Chlorphenyl) - - l-piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 5 {3 [4 (3-Bromphenyl) - -1-piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 7 - {3 [4 (3-Bromphenyl) - - l-pipsrazinyl] - propoxy} - -3,4-dihydroearbostyril 5 - {3 - [4 - (4-n - Buty 1phenyl) -1-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 7 - {3 - [4 - (4-n-Butylphenyl) - l'piperazinyl] - - propoxy} -3,4-dihydrocarbostyril 6,8-Dichlor-5 {2-methyl -3 [4 (3-fluormethyl) -1 - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 1 - Benzyl-6-chlor-5 [3 - - (4-benzyl-l-hnmopiperazinyl) - propoxy] -3,4-dl - hydroearbostyril oily substance 27 lp = 1.5738 6-Chlor-5 [3 (4-benzyt -1-homopiperazinyl) - propoxy] -3,4-dihydrocarbostyril 7 - [5 (4-Phenyl-l-piperazi ny l) - pentyloxy] -3,4-dihydrocarbostyril 1-Äthyl-7 {3 - [4-bromphenyl) - l-piperazinyl] - - propoxy) -3.4 - dihy drocarbostyril. Mono hydraulic bromide 7 - {3 [4 (4-Bromphenyl) - - l-piperazinyl] - propoxy} - -3,4-dihydrocarbostyril colorless, flaky crystals () thanol) colorless, plate-like crystals (chloroform - ethanol) colorless, needle-like crystals (ethanol) colorless, plate-like crystals colorless, plate-like crystals (isopropanol) colorless, prism tables of crystals colorless, prism tables of crystals (ÄthanoI) yellow, needle-like crystals (ethanol) colorless, needle-like crystals colorless, needle-like crystals Sehmelzpunkt °C 168 - 169,190 - 192,159 - 160,184 - 185,134 - 135,133 - 135,121 - 124,156 - 158,144 - 145,220 - 222 table (continuation) crystalline form SehmelzBei (Umkristallipunkt play sierungsmittel) °C 132 Nr.376432 133,134,135,136,137,138,139,140,141,142,143,144 connection 8-Chlor-5 {3 [of 4 (3 - “- chlorphenyl) - l-piperfarblose, sehuppige crystals azinyl] - propoxyl-3,4-dihydrocarbostyril 1-Methyl-7 {3 [4 (3 - - chlorphenyl) - l-piperazinyl] - propoxy} - 3,4-dihydrocarbostyril 8-Chlor-5 [3 (4-phenyl -1-piperazinyl) - propoxy] - (ethanol) colorless, needle-like crystals (isopropanol - water) colorless, priematis¢he crystals -3,4-dihydroearbostyril 6 - bromine -5 - [3 - (4-phenyl -1-piperazi nyl) - propoxy] - -3,4-dihydrocarbostyril 4 - Phenyl-6 - [3 - (4-phenyl -1-piperazinyl) - propoxy] - -3,4-dihydroearbostyril 6 ' {3 [4 (2-Methoxyphenyl) -1-piper azinyl] - - propoxy} -3,4-dihydrocarbostyril 6 - {3 [4 - (4-Methylphenyl) -1-piperazinyl] - - propoxy} - 3,4-dihydroearbostyril 1-Äthyl-6 [3 (4-phenyl -1-piperazinyI) - propoxy 1 - -3,4-dihydrocarbostyril 1-Benzyl-6 [3 (4-phenyl -1-piperazinyl) - propoxy] - -3,4-dihydroearbostyril 1-Benzyl-5 [3 (4-benzyl -1-piperazinyl) - propoxy] - -3,4-dihydrocarbostyril 4-Methyl-6 [3 (4-phenyl -1-pipsrazinyl) - propoxy] - - carbostyril. i/4 hydrate 6 [4 (4-Phenyl-l-piperazinyl) - butoxy] -3,4-dihydrocarbostyril 8 - {3 - [4 - (4-Fluorphenyl) - -1-piperazinyl] - propoxy} - -3,4-dihydroearbostyril (tbanol) colorless, needle-like crystals (isopropanol) colorless, needle-like crystals (ethanol) colorless, prismatlsehe crystals (isopropanol - water) lightyellow urismatische crystals (methanol) colorless, prism tables of crystals (Ligroin) colorless, needle-like crystals (Ligroin ether) colorless, needle-like crystals isopropanol) colorless, flaky crystals (methanol) colorless, needle-like crystals (ethanol) colorless, prism tables of crystals (ethanol) 133 - 134 78 - 79,138 - 134,160 - 161,163 - 165,147 - 149,193 - 194 i00 95,108 - 110,157 - 159,142 - 144,201 - 202 table (continuation) - play 145,146,147,148,149,150,151,152,153,154,155 connection 7 {3 [4 (2,5-Diohlorphenyl) - l-piperazinyl] - - propoxy} - earbostyril 7 {3 [4 (2-Methyl-5 - ehlorphenyl) - l-piperazinyl] - propoxy} - earbostyril 7 {3 [4 (3,4-Dichlorphenyl) - l-piperazinyl] - - propoxy} - carbostyril 7 (3 [4 (2,5-Dimethylphenyl) - l-pfpsrazinyl] - - propoxy} - carbostyril 1-Äthyl-5 [3 - (4-phenyl - - l-piperazinyl) - propoxy] - -3,4-dihydroearbostyril. Mono hydrochloride. • 1/2 hydrate 1-Propyl-5 [3 (4-phenyl -1-piperazinyl) - propoxy] - -3,4-dihydrocarbostyril 8 - {3 [4 (4-Methylphenyl) -1-piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 6 - {3 [4 (4-Fluorphenyl) - - l-piperazinyl] - propoxy} - -3,4-dihydroearbostyril 4 {3 [4 (4-Fluorphenyl) - -1-plperazinyl] - propoxy} - - earbostyril 7 - {3 [4 (3-Chlor-4 - methylphenyl) -1-piperazinyl] - propoxy} - earbostyril 7 {3 [4 (2-Methyl-3 - chlorphenyl) -1-piperazinyl] - propoxy} - earbostyril crystalline form (recrystallization means) colorless, needle-like crystals (ethanol) colorless, prismatisehe crystals (ethanol) bräunliehe, prism tables of crystals (ethanol chloroform) colorless, flaky crystals (isopropanol) colorless, powdery crystals (ethanol) - colorless, prismatisohe crystals (Ligroin) colorless, needle-like crystals ethanol) yellow prism tables of crystals (chloroform - ethanol) colorless, prism tables of crystals (ethanol Chloroformt colorless, needle-like crystals (ethanol) colorless, flaky crystals (ethanol) fusion point °C 187 - 189,182 - 183,209 - 210,162 - 163,198 - 199 88 - 89,139 - 141,180 - 181,231 - 232,209 - 210,192 - 193 table (continuation) example 156,157,158,159 connection 7 {3 [4 (2,3-Dichlor phenyl) -1-piperazinyl] - - propoxy} - earbostyril 1-Isopropyl-5 [3 (4 - - phenyl l piperazinyl) - - propoxy] - 3,4-dihydrocarbostyril 8-Chlor-5 [3 (4-phenylKristallform (recrystallization means) colorless, prism tables. Crystals (ethanol chloroform) lightyellow, powdery crystals (Ligroin) lightyellow, needle -1-piperazinyl) - propoxy] - -3,4-dihydrocarbostyril 8-Chlor-5 {3 - [4 (4 - - cblorphenyl) -1-piperazinyl] - per poxy} -3,4-dihydrocarbostyril well-behaved crystals (ethanol) lightyellow, powdery crystals (Ätbanol) fusion point degrees of 192 - 195 90 - 91,135 - 136,168 - 169 example 160:4,8 g 7 (3-Chlorpropoxy) - 3,4-dihydrocarbostyril and 3.5 g sodium iodide are mixed with 50 ml acetone and heated up during 3 h on return flow conditions. Then 40 ml dimethylformamide hinzugegeben-und the acetone is driven out by distillation with 40 to 45°C under reduced pressure. Further 4.0 g are in addition-given to 4 (3-Fluorphenyl) - piperazin and 3.0 g tri ethyl amine, whereby the reaction is accomplished with 70 to 80°C during 7 h under agitating. The reaction mixture is concentrated under reduced pressure to the Troekne. To hiedureh the received arrears 60 is in addition-given ml to an aqueous 5% sodium hydrogencarbonate solution and it is extracted with chloroform. The chloroform layer is extracted and getroeknet twice with water and removed then the chloroform by distillation. To hiedurch the received arrears ether is in addition-given, whereby the insoluble material is collected and dried by filtration. By recrystallization from methanol 6.2 g become 7 - {3 - [4 (3-Fluorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril in form of weakly yellowish, needle-like crystals with a fusion point from 174 to 176°C (decomposition) receive. Example 161:2,4 g 7 (3-Chlorpropoxy) - 3,4-dihydrocarbostyril, 1 g Pyridin and 2.6 g 4 (3,4,5-Trimethoxyphenyl) - piperazin in 20 ml Dimethylsulfoxyd are mixed and agitated then with to 90°C during 5 h. The Reaktionsgemiseh is poured in 80 ml 2%ige aqueous Natriumhydrogenearbonatlösung and the organic layer with chloroform is extracted. The Chloroformsehieht is washed, getroeknet with water and discharger-harvested the chloroform by distillation. Hiedureh the received arrears are dissolved in 30 ml ethanol and it become dry hydrogen chloride gas into the ethanol solution enter-read. Hiedurch the failed crystals are collected by filtration and from methanol ethanol under receipt of 3,2 g (yield 61%) 7 {3 - [4 (3,4,5-Trimethoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydreearbostyril. Dihydroehlorid in form of colorless, needle-like crystals with a Sehmelzpunkt from 225 to 227°C umkristalli siert. Examples 162 to 167: After the function gem£f the following connections were received to example 161: Example 162,163,164,165,166,167 connection 5 {3 [4 (2-Fluorphenyl) - ptperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 7 {3 [4 (2-Fluorphenyl) - piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 5 - {3 - [4 (3-Fluorphenyl) - piperazinyl] - - propoxy} - 3,4-dihydrocarbostyril 5 {3 - [4 (3,4,5-Trimethoxyphenyl) - piperazinyl] - propoxy) -3,4-dlhydrocarbostyril - dihydrochlorid 5 {3 [4 (3,4-Dimethoxyphe nyl) - piperazinyl] - - propoxy} -3,4-dihydrocarbostyril 7 {3 [4 (3,4-Dimethoxyphenyl) - piperazinyl] - - propoxy} -3.4 - dihy drocar - bostyril crystalline form (recrystallization means) colorless, needle-like crystals (methanol) colorless, needle-like crystals (methanol) colorless, needle-like crystals (methanol) colorless crystals (methanol - ethers) weakly gelbli-- che, needle-like crystals (ethanol) weakly brownish, needle-like crystals (ethanol) fusion point °C 175 - 178,154 - 156,178 - 180,205 - 208 (decomposition) 190 - 192,146 - 147 example 168:2,5 g 7 (3-Chlor-2-methylpropoxy) - 3,4-dihydrocarbostyril and 1.8 g sodium iodide are mixed with 30 ml acetone and agitated at ambient temperature over night. Then 20 ml Dimethylform.amid are in addition-given and the acetone is removed by distillation under decreased pressure. Further 1.5 g tri ethyl amine and 1.8 g 4-Phenylpiperazin are in addition-given and the reaction is accomplished with 70 to 80°C during 6 h under agitating. The reaction mixture is poured in 70 ml a 2%igen aqueous sodium hydrogencarbonate solution and the organic layer is then extracted with chloroform. The chloroform layer is washed and getroeknet with water. Then the chloroform is removed destillatlv and hiedureh to the erhalI0 tene arrears with petroleum ether is washed. By recrystallizing from methanol water 2.8 g (yield 74%) become 7 - [2-Methyl-3 (4-phenylpiperazinyl) - propoxy] from 146 to 147°C receive -3,4-dihydrocarbostyril in form of colorless, flöckchenartiger crystals with a fusion point. Example 169: Similarly as in example 168 5 [2-Methyl-3 (4-phenylpiperazinyI) - propoxy] becomes - -3,4-dihydroearbostyril in form of colorless, needle-like crystals (recrystallization means ethanol) with a fusion point from 167 to 169°C receive. Example 170:2,7 g 4-Methyl-7 (3-chlorpropoxy) - carbostyril and 1.8 g sodium iodide are mixed with 50 ml acetone and heated up during 3 h under Rüekflußbedingungen. Then ml dimethylformamide are in addition-given and the Aeeton is removed distillative under reduced pressure. Then 1.5 g tri ethyl amine and 1.8 g 4-Phenylpiperazin are in addition-given and it is agitated during 3 h with 80 to 90°C, whereby dimethylformamide is then removed by distillation under reduced pressure. To hiedureh the received arrears a 5% aqueous sodium hydrogencarbonate solution for effectuation are in addition-given to the crystallization of the product and washed the formed precipitation by filtration collected, with wet washed, with isopropanol, continued to wash and dried with ether. Hiedurch the received raw crystals are dispersed in 80 ml methanol and by addition of 5 ml konz. Hydrochloric acid solved, according to which under reduced pressure to dry one is concentrated. Hiedurch the received arrears become from methanol ether under receipt of 3,6 g (yield 80%) 4-Methyl-7 [3 - - (4-phenylpiperazinyl) - propoxy] - carbostyril dihydrochlorid in form of colorless crystals with a fusion point from 253 to 254°C (decomposition) recrystallizes. Example 171: Similarly as in example 170 4-Methyl-6 becomes. - [3 (4-phenylpiperazinyl) - propoxy] - - carbostyril. Dihydrochlorid.Trihydrat in form of weakly brownish crystals (from ethanol) with a fusion point from 285 to 290°C (decomposition) receive. Example 172:2,4 g 5 (3-Chlorpropoxy) - 3,4-dihydroearbostyril and 1.7 g sodium iodide are mixed with 30 ml acetone and heated up during 3 h on return flow conditions. Then 30 is in addition-given ml dimethylformamide to the Reaktionsgemiseh and the acetone is removed by distillation under reduced pressure. Next 1.5 g are in addition-given to tri ethyl amine, 1.8 g 4-Phenylhomopiperazin and it is heated up on 60 to 70°C during 5 h under agitating. The reaction mixture is poured in 80 ml a 3%igen aqueous sodium hydrogencarbonate solution and the organic layer is extracted with chloroform. The chloroform layer is washed, dried with water and removed the chloroform by distillation. Hiedurch the received arrears become from Ligroin benzene under receipt of 3,2 g (yield 83%) 5 [3 (4-Phenylhomopiperazinyl) - propoxy] - 3,4-dihydrocarbostyril in form of colorless, sehuppenartiger crystals with a Sehmelzpunkt from 122 to 125°C recrystallizes. Examples 173 to 175: Similarly as in example 172 the following Verhindungen is received: Example 173,174,175 connection 7 [3 (4-Phenylhomopiperazinyl) - propoxy] -3.4 - - dihydroearbostyril 5 [3 (4-Cyclohexylpiper azinyl) - propoxy] - -3,4-dihydroearbostyril 7 [3 (4-Cyelohexylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril crystalline form (Umkristallisieru ngsmittel) weakly yellowish shed-like crystals (petroleum ether) kp. = 60 to 80°C) colorless, needle-like crystals (ethanol) colorless, needle-like crystals (Ligroin benzene) fusion point °C 72 - 74,173 -! 76,115 - 125 example 176:24 g 5 (3-Chlorpropoxy) - 3,4-dihydrocarbostyril and 17 g sodium iodide are mixed with 300 ml acetone and heated up during 3 h on return flow conditions. Then 300 is in addition-given ml dimethylformamide, to 12 g tri methyl amine and 18 g 4-Benzylpiperazin and the reaction is accomplished with 60 to 70°C during 7 h on agitating conditions. The reaction mixture will become under reduced pressure under receipt of a viscous liquid concentrated and it then 300 ml a 3%igen aqueous Natriumhydrogenearbonatlösung in addition-given. The organic layer is extracted with chloroform and washed with water. After drying the Chlorof0rmschicht the chloroform is removed by distillation. Hiedurch the received arrears will be washed with ether and received from methanol recrystallized, whereby 32 g (yield 84%) 5 - [3 (4-Benzylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril in form of colorless, needle-like crystals with a Sohmelzpunkt from 157 to 159°C. Examples 177 and 178: Similarly as in example 176 the following connections are received: Example 177,178 connection 6 [3 - (4-Benzylpiperazinyl) - - propoxy] -3,4-dihydroearbostyril 7 [3 - (4-Benzylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril crystalline form (Umkristalli8ierungsmittel) colorless, needle-like crystals (isopropanol) colorless, needle-like crystals (ethyl acetate ether) point of fusion °C 114 - 116,126 - 127 example 179:2,4 g 7 (3-Chlorpropoxy) - 3,4-dihydroearbostyril and 1.8 g sodium iodide are mixed with 30 ml acetone and agitated with g0 to 60°C during 3 h. Then 30 is in addition-given ml dimethylformamide. After distance of the acetone by distillation under reduced pressure 1.5 g become tri ethyl amine and 2.3 g 4 (4-Chlorphenyl) - 3-methylpiperazin thereby mixes and with 70 to 80°C during 7 h agitated. The Reaktionsgemiseh will become under reduced pressure concentrated and it 50 ml an aqueous 3%igen Natriumhydrogenearbonatlösung hiedurch the received viscous arrears admitted and the organic layer with chloroform is extracted. The chloroform layer is washed, dried with water and removed the chloroform destillaLo tiv. Hledurch the received arrears 50 becomes ml methanol and 5 ml konz. Hydrochloric acid in addition-given, whereby the mixture under reduced pressure is evaporated to dry ones. The arrears become from ethanol under receipt of 3,1 g (yield 75%) 7 - {3 [3-Methyl-4 (4-chlorphenyl) - piperazin] - propoxy} -3,4-dihydrocarbostyril. Dihydrochlorid in form of colorless crystals with a fusion point from 235 to 242°C recrystallizes. Examples 180 and 181: Similarly as in example 179 the following connections are received: - Play 180,181 connection 8-Brom-6-chlor-7 [3 - - (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril-dihydrochlorid (3.7 g (yield 67%)) 4 [3 (4-Phenylpiperazinyl) - - propoxy] - carbcstyril crystalline form (Umkristalli - sierungsmittel) colorless, needle-like crystals (ethanol) colorless, shed-like crystals (ethanol) fusion point °C 229 - 232 (decomposition) 206 - 208 example 182:5,1 g 7 (3-Chlor-2-hydroxypropoxy) - 3,4-dihydrocarbostyril and 8 g 4-Phenylpiperazin are mixed with 50 ml dimethylformamide and converted with 50 to 60°C during 5 h on agitating conditions. The reaction mixture is restricted under reduced pressure to dry ones and hiedurch the received arrears are dissolved in 80 ml chloroform. Then the chloroform layer is washed three times mit= to 5% aqueous sodium hydrogencarbonate solution and washed afterwards afterwards three times with water and dried with water-free sodium sulfate. The chloroform is removed by distillation under decreased pressure and hiedurch the received arrears by silicagel column chromatography (silicagel: Wako C-200, extraction solvent: Chloroform: Methanol = 30: 1 (v/v)) cleaned. Then the extracted product into its hydrochloride using ethanol, contains is removed for hydrogen chloride, transferred and ethanol by distillation under reduced pressure. Hiedurch the received arrears become from water under receipt of 5,6 g 7 [2-Hydroxy-B (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril. Mono hydrochloride 1/2 hydrate in form of colorless crystals with a fusion point of 122°C (decomposition) recrystallizes. Examples 183 to 202: Similarly as in example 182 the following connections are received: Example 183,184,185,186,187,188,189,190 connection 5 [2 Hydroxy-3 (4 - - phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. • mono hydrochloride 6 [2-Hydroxy-3 (4 - - phenylpiperazinyl) - - propoxy] - 3.4 - - dihydroearbostyril. • Monohydroehlorid. • 1/2 hydrate 8-Chlor-5 [2-hydroxy -3 - (4-phenylpiperazinyl) - propoxy] -3.4 - - dihydrocarbostyril. • Monohydroehlorid. • 3/2 hydrate 8-Chlor-5 {2-hydroxy -3 - [4 - (4-chlorphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril. • mono hydrochloride 6-Chlor-5 [2-hydroxy -3 - (4-phenylpiperaziny 1) - propoxy] -3.4 - - dihydrocarbostyril. • Dihy drochlorid. • mono hydrate 6,8-Dtchlor-5 [2 - - hydroxy-3 (4-phenylpiper azinyl) - propoxy] - -3,4-dihydrocarbostyril. . Monohyrochlorid 8 [2-Hydroxy-3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihy dro - carbostyril. Monohydro¢hlorid 6 {2-Hydroxy-3 [4 - - (4-chlorphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarboetyril. Mono hydrochloride 1/2 hydrate crystalline form (recrystallization means) colorless, needle-like crystals (water) colorless, needle-like crystals (water) colorless, amorphous crystals (methanol - ethanol) colorless, needle-like crystals (methanol - ether) colorless, needle-like crystals (methanol - ethers) colorless crystals (water) colorless crystals (methanol - ether) colorless, needle-like crystals (ethanol) fusion point °C 239 - 241,223 - 224,226 - 228,228 - 230 218 - 225,251 - 253,263,212 - 214 table (continuation) example 191,192,193,194,195,196,197,198,199 connection 7 {2-Hydroxy-3 [4 - - (4-ehlorphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril. • Monohydroehlorid 8-Brom-5 [2-hydroxy - -3 (4-phenylpiperazinyl) - propoxy] -3.4 - - dihydrocarbostyril 8-Brom-5 {2-hydroxy -3 [4 (2-methoxyphenyl) - piperazinyl] - - propoxy} - 3,4-dihydrocarbostyriI, Dihydrochlorid 6-Chlor-7 [2-hydroxy -3 - (-4-phenylpiperazinyl) - propoxy] -3.4 - - dihydrocarbostyril 6-Chlor-7 {2-hydroxy -3 - [4 - (2-methoxyphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyril 1-Methyl-5 [2-hydroxy -3 (4-phenylpiperazinyl) - propoxy] -3.4 - - dihydrocarbostyril 1-Äthyl-5 [2-hydroxy-3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. Mono oxalate 8-Chlor-5 {2-hydroxy -3 [4 (2-chlorphenyl) - - piperazinyl] - propoxy} - -3,4-dihydrocarbostyri] 1-Allyl-5 {2-hydroxy -3 - [4 - (4-methylphenyl) - - piperazinyl] - propoxy} - -3,4-dthydroearbostyril crystalline form (recrystallization means) colorless, needle-like crystals (isopropanol) colorless crystals (methanol) colorless crystals (methanol - ethers) colorless, needle-like crystals (MethanoI - water) colorless crystals (ethanol) colorless, needle-like crystals (n-hexane benzene) colorless crystals (ethanol ether) colorless crystals (ethanol) colorless, needle-like crystals (Ligroin benzene) fusion point degrees of 66 - 174 - 176,226 - 228,171 - 173,183 - 184,143 - 145,201 - 203 (decomposition) 156 - 158,123 - 124 table (continuation) example 200,201,202 2O3 204 205 connection 1-Benzyl-5 [2-hydroxy -3 (4-phenylpiperazinyl) - propcxy] -3,4-dihydrocarbostyril 6-1 2-Hydroxy-3 (4 - - phenylpiperazinyl) - - prcpcxy] -3,4-dihydrocarbostyril. 1/2 hydrate 8-Brom-5 [2-hydroxy -3 (4-phenylpiperazinyl) - - propoxy] - carbostyril 7 - {2-Hydroxy-3 [4 (3 - - ohlorphenyl) -1-piperaziny I] - propoxy} -3,4-dlhydrocerbostyril l-Äthyl-5 [2-hydroxy -3 (4-phenyl-l-piperaZinyl) - propoxy] -3,4-dihydrocarbostyril 6 [2-Hydroxy-3 (4 - - phenyl l piperazinyl) - - propoxy] - carbostyril crystalline form (recrystallization means) colorless, needle-like crystals (petroleum ether kp. = 60 to 80°C) colorless, amorphously (methanol) colorless, panel-like crystals (methanol) colorless, prism tables of crystals (chloroform - ethanol) colorless, needle-like crystals (Ligroin benzene) colorless, prism tables of crystals (ethanol chloroform) fusion point degrees of 148 - 150,218 - 219,179 - 182,172 - 174,111,221 - 224 example 206:0,55 g sodium hydride (about 50% in oil) with petroleum ether washed and then will become 30 ml dimethylformamide and 36 g 7 [3 (4-Phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril in addition-given, whereby at ambient temperature with 1 h one agitates. To the reaction mixture 1.2 g ethyl bromide are in addition-given and it is agitated at ambient temperature during 3 h. The reaction mixture is poured in 150 ml wet and the organic layer with chloroform is extracted. The Chloroformechidh is twice washed with wet, dried with water-free sodium sulfate and driven out the chloroform distillative. To hiedurch the received " arrears a small quantity ethanol will course-go to the precipitation from crystals. The KrilO stable is collected by filtration and in 70 ml methanol and 3 ml konz. Hydrochloric acid dissolved, according to which under reduced pressure to dry one is restricted. The arrears become from ethanol under receipt of 4,1 g (yield 88%) l-Äthyl-7 [3 (4-phenylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril. Dihydrochlorid in form of colorless crystals with a fusion point from 222 to 224°C recrystallizes. Example 207:0,3 g Natriummetall in 80 ml ethanol dissolved and this solution 3.6 g 5 [3 (4-Phenylpiperazinyl) - propoxy] will become - 3,4-dihydrocarbostyril and then 1.5 g Benzylchlorld given, whereby during 5 h on return flow conditions one heats up. The reaction mixture is concentrated under reduced pressure to dry ones. To hiedurch the received arrears water is in addition-given and the unsolvable subject by filtration is collected, washed and dried these with water. The raw crystals are recrystallized from Ligroin under receipt by 3,9 g (yield 86%) 1-Benzyl-5 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril in form of weakly yellowish, needle-like crystals with a fusion point by 113°C. Betepiele 208 bie 213: Similarly as in example 117 the following connections are received: Crystalline form fusion with (Umkristallipunkt play connection sierungsmittel) °C 208,125 - 127,209,210,211,212,213 1-Benzyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril 1-Methyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3 4-dihydrocarbostyril 1-Allyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril • • Dihydrochlorid 1-Propargyl-7 [3 - (4 - - phenylpiperazinyl) - - propoxy] -3,4-dihydrocarbostyril. • Dihydrochlorid 1-Hexyl-7 [3 (4 - - phenylpiperazinyl) - - propoxy] -3.4 - di - hydrocarbostyril. • Dihydrochlorid 1 - (3-Phenylpropyl) - -7 [3 (4-phenylpiperazinyl) - propoxy] - -3,4-dihydrocarbostyril. • mono hydrochloride weakly yellowish crystals (ethanol) colorless crystals (ethanol) colorless crystals (ethanol) weakly yellowish crystals (methanol) colorless crystals (ethanol acetone - ethers) colorless, shed-like crystals (ethanol (204 - 207,189 - 192,215 - 216,176 - 181,201 - 202 example 214:1,0 g 4-Methyl-7 [3 (4-phenylpfperazinyl) - propoxy] - carbostyril. Dihydrochlorid and 0.3 g palladium-black are dispersed in 200 ml ethanol and a hydrogen printing ven 2 bar at ambient temperature are maintained, whereby the catalytic reduction is accomplished with to 80°C during 8 h. After cooling of the reaction mixture palladium-black by filtration is removed and the mother liquor to dry ones concentrated • the arrears is recrystallized from a mixture methanol ether under receipt by 0,6 g (yield 60%) 4-Methyl-7 [3 - - (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril. Dihydrochlorid.Dihydrat in form of colorless crystals with a fusion point from 260 to 265°C. RST example 215:2 g 5 - [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydroearbostyril will become mixed with 30 ml acetone and it far 12 ml acetyl chloride in addition-given, according to which during 10 h on return flow conditions one heats up. After cooling of the reaction mixture the failed product is collected by filtration and washed with acetone. Hiedruch the received raw crystals are dissolved in 80 ml water, made basic with ammonia liquor and extracted, dried then with chloroform and removed the chloroform by distillation. The arrears become by silicagel column chromatography under receipt of 0,5 g 5 - [2-Acetyloxy-3 (4-phenylpiperazinyl) - prepoxy] -3,4-dihydrocarbostyril cleaned in form of colorless crystals with a fusion point from 159 to 161°C. Example 216: Similarly as in example 215 7 [2-acetyloxy-3 (4-phenylpiperazinyl) - - propoxy] becomes - 3,4-dihydrocarbostyril in form of colorless crystals with a fusion point from 130 to 132°C receive. Example 217:1,9 g 5 - [2-Hydroxy-3 (4-phenylpiperazinyl} - propoxy] -3,4-dihydrocarbostyril and 0.24 g sodium hydride in 40 ml xylene are dispersed and during 1 h on return flow conditions heated up. Subsequently, the temperature of the bath will become lowered on 130°C and it 1.40 g 3,4,5-Trimethoxybenzoylchlorid gradually in addition-given, whereby during 8 h on return flow conditions one heats up. The xylene is removed from the reaction mixture distillative, the arrears in 80 are then poured ml water and extracted with Chlcroform. The chloroform layer is washed, dried with water and removed the chloroform by distillation. The arrears are recrystallized from ethanol under receipt by 1,5 g 5 [2 (3,4,5-Trimethoxybenzoyloxy} - 3 - - (4-phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril in form of colorless crystals with a fusion point from 125 to 127°C.



[2]

Carbostyril derivatives having antihistamic action and central nervous controlling action are useful as antihistamic agents or central nervous controlling agents. The derivatives are represented by the general formula, <IMAGE> (1) wherein R1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, an alkynyl group having 2 to 4 carbon atoms or a phenylalkyl group having an alkylene group containing 1 to 4 carbon atoms; R2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a phenyl group; R3 is a hydrogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkanolyoxy group having 1 to 4 carbon atoms or a 3,4,5-trimethoxybenzoyloxy group; R4 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R5 is a cycloalkyl group having 3 to 8 carbon atoms, a phenyl group (which may have 1 to 3 substituted groups selected from the group consisting of halogen atoms, alkyl groups having 1 to 4 carbon atoms and alkoxy groups having 1 to 4 carbon atoms), an alkyl group having 1 to 4 carbon atoms (having one substituted group such as a hydroxy group, a phenyl group or an alkanoyloxy group having 1 to 4 carbon atoms), an alkanoyl group having 1 to 4 carbon atoms or benzoyl group; X is a halogen atom; n is 0, or an integer of 1 or 2; Q is an integer of 2 or 3, l and m are respectively an integer of 0 or 1-6, but the sum of l and m should not exceed 6; the carbon-carbon bond at the 3- and 4-positions in the carbostyril skeleton is a single or double bond; and the substituted position of the side chain of <IMAGE> is any one of the 4-, 5-, 6-, 7- or 8-positions.



1. Procedure for manufacturing new Carbostyrilderivate of the general formula (i) where R* hydrogen, an alkyl group with 1 to 6 carbon atoms, a Alkenylgrupp.e with 2 to 4 carbon atoms, a Alkinylgruppe with 2 to 4 carbon atoms or a Phenylalkylgruppe with a group of alkyls with 1 to 4 carbon atoms, R2 hydrogen, an alkyl group with 1 to 4 carbon atoms or a Phenylgruppe, R3 hydrogen, a hydroxy group or an alkyl group with 1 to 4 carbon atoms, a Alkanoyloxygruppe with 1 to 4 carbon atoms or a 3,4,5-Trimethoxybenzoyloxygruppe, R hydrogen or an alkyl group with I to 4 carbon atoms, R5 a Cycloalkylgruppe with 3 to 8 carbon atoms, a Phenylgruppe, the I to 3 substituents from the group halogen, Alkyl group with 1 to 4 carbon atoms and alkoxy group with 1 to 4 carbon atoms. to carry, a substituted alkyl group with 1 to 4 carbon atoms with a Phenylgruppe or Alkanoyloxygruppe with 1 to 4 carbon atoms can mean as substituents, a Alkanoylgruppe with 1 to 4 carbon atoms or a Benzoylgruppe and an X a halogen atom meant equal n is 0, 1 or 2, equal q is 2 or 3 and 1 and m in each case 0 or whole numbers from 1 to 6 and hiebei the sum of 1 and m 6 does not exceed, whereby the carbon carbon connection between the 3und of the 4-Stellung in the Carbostyrilgerüst a Einfachoder double bond is and the Seitenkette - B9 - R31/(CH2) - o (CH2) I - CH (CH2) mN /N-R Nr.376482 itself under the condition in the 4, 8, 6, 7oder 8-Stellung it finds that, if this Seitenkette stands in 4-Stellung R escapes, and R-S then no a Phenylgruppe as substituent aufwe [send alkyl group with 1 to 4 carbon atoms to be can, if R is a Phenylgruppe, as well as characterized by their acid addition salts, thereby that a connection of the general formula (A) RZ (IL) (x') n R: R3a where A a group of the general formula - (CH2) I CH (CH2) MX! or - CH2-C'H '- CH2 represents and hiebei R*, R, M, l, m, n and the carbon carbon connection between the 3und of the 4-StelI0 lung in the Carbostyrilgerüst the meaning indicated above has, to R3a hydrogen, a hydroxy group or an alkyl group with I to 4 carbon atoms is and M a halogen atom or a similar substitution reaction as a halogen atom making possible group, e.g. a Mesityloxyoder Tosyloxygruppe, represents, with a connection of the general formula (CH2) q HN N - R5 (nl) where R, R5 and q the meaning indicated above to have, are converted, on which, if in the received connection of the general formula (1) R-S a hydroxy group , the received connection represents gewünschtenfalls with a connection of the general formula R3bx2 or (R3b) 2 0 (IV) (V) where R3b a Alkanoylgruppe with 1 to 4 carbon atoms or a 3,4,5-Trimethoxybenzoylgruppe is transferred and X2 means a halogen atom, gewünsehtenfalls a received connection of the general formula (I) with the meaning of hydrogen for R into a connection with one of the remaining meanings of R is converted, gewünschtenfalls a received Carbostyrilderivat is transferred to a 8,4-Dihydroearbostyrilderivat is hydrogenated and gewünschtenfalls a received connection of the general formula (I) into a S ureadditionssalz.

2. Procedure according to requirement i, thereby is manufactured characterized that by choice of appropriate basic materials and process steps 7 - [3 (4-Phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril or an acid addition salt hievon.

8. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 - {3 [2-Methoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydros0 is manufactured carbostyril or an acid ADD tionssalz hievon.

4. Procedure according to requirement i, thereby is manufactured characterized that by choice of appropriate basic materials and process steps 7 - {3 [4 (3-Chlorphenyl) - piperazinyl] - propoxy 1-3,4-dihydrocarbostyril or an acid addition salt hievon. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 - {3 - [4 (2-Fluorphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril or an acid addition salt is manufactured hievon.

6. Procedure according to requirement i, thereby is manufactured characterized that by choice of appropriate basic materials and process steps 7 - [3 (4-Phenylpiperazinyl) - propoxy] - carbostyril or an acid addition salt hievon.

7. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 - {3 - [4 (2-Äthoxyphenyl) - piperazinyl] - propoxy} -3,4-dihydrocarbostyril or an acid addition salt is manufactured hievon.

8. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 1-Methyl-7 [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydroIS is manufactured carbostyril or an acid addition salt hievon.

9. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 [4 (4-Phenylpiperazinyl) - butoxy] -3,4-dihydroearbostyril or an acid addition salt is manufactured hievon. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 5 - [3 (Phenylpiperazinyl) - propoxy] -3,4-dihydrocarbostyril or an acid addition salt is manufactured hievon.

11. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 - {3 - [4 (2-Chlorphenyl) - piperazinyl] - propoxy} - 3,4-dihydrocarbostyril or an acid addition salt is manufactured hievon. 2S 12. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 - [2-Hydroxy-3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydrooarbostyril or an acid addition salt is manufactured hievon.

13. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 8-Brom-5 [3 (4-phenylpiperazinyl) - propoxy] - carbostyril or an acid addition salt is manufactured hievon.

14. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 - {3 - [4 (2-Methoxyphenyl) - piperazinyl] - propoxy) - carbostyril or an acid addition salt is manufactured hievon. Procedure according to requirement 1, by it characterized that by choice of appropriate basic materials and process steps 7 - {3 - [4 (4-Methylphenyl) - piperazinyl] - propoxy} -3,4-d£ is manufactured hydrocarbostyril or an acid addition salt hievon.

16. Procedure according to requirement i, thereby is manufactured characterized that by choice of appropriate basic materials and process steps 7 - [3 (4-Benzylpiperazinyl) - propoxy] - 3,4-dihydrocarbostyril or an acid addition salt hievon.

17. Procedure according to requirement l, thereby characterized that by choice of appropriate basic materials and process steps 1-Benzyl-5 [2-hydroxy-3 (4 - phenylpiperazinyl) - prop. - oxy] - 3,4-dihydrocarbostyril or a Säureadditionssa z hievon is manufactured.

18. Procedure according to requirement 1, by characterized that by choice of appropriate basic materials and process steps 1-Benzy! - 5 - [3 (4-phenylpiperazinyl) - propoxy] -3,4-dihydro4S is manufactured carbostyril or an acid addition salt hievon. Pressure: Ing.E.Voytjech, Vienna