New derivatives of the amino-2 phénéthylamines and their preparation.
The present invention relates to novel derivatives1aninc-to-2 phenethylamines and their preparation method. These products are characterized by the following general formula (formula I): wherein R ^=phenyl unsubstituted or substituted by one or more substituents such as halogeno, THE R ^ branched or unbranched of c1 to 06, the R ^ can be equal to hr where RG is a branched alkyl. Further regenerating complementary and R? the R had form with the nitrogen atom to which they are bound " o-o - o - 0 - - (CK202 )the n with n=1 - 0 - 2 - or - or c-ch-ch-- ^ - 05 -. The rr.hén ethylamines emrloyées of formula I may be in the form of free base or salts thereof therapeutically compatible such as hydrochlorides, citrate, berzilates. The orthoarylydèneajninophénéthylsmines which is contemplated by the present invention are novel chemical products. The scientific literature mentions little dfort - énéthyla - lead e in include for example Dir. yl 2 aniline compounds synthesized by a Kr J of £PCHO & al, the MED J. Mal. 1966, 00 09 - 12, As a synthetic intermediate cinnamanilides to prorriétéshyrotensives and antisérotonines, the aminoéthyl-to-2 dinydroxy-to-4.5 e ^ iline described in French Patent no. 2644 drug properties or the tower anthypertensivesdihalogénoaminophénéthylsmines reported in the French Patent no. 6923 drug. We have now discovered ore imines derived from ortho-amino-phenethylamines, although their structures are different structures products commonly used in this field, exert psychotropic actions be recovering from their emrlovées as medicines with anxiolytic activities antidénre and located. The products forming the subject of the present invention are obtained generally by a reaction involving an amine of formula II and an aldehyde of formula III according to the scheme: The substituents R to R ^ ^ having the meanings inai-to-uéesrlus high. The amines of formula II are ootenues ARs therein various methods according to the substituents R ^ ^ to Β. The invention will be described so there read is detailed in the following examples illustrate without however the YES 1 ^ exrcsés thus reduce single points. Æ3ÔE 3 Synthesis of n - dimethylaminoethyl-6 (ryri convert it 1 I to do 3 ^ - ^ - phenylalkyl, 3 yl 5 amino (formula I - 0 -) and its Quinuclidinyl (ORC 01,170). 1 -<dd Synthesis (hr, n DlM greatly accelerated the Thyl Amin to o - 2 ethyl)~6 benzodio --xol-a 1" 3 yl 5 amino 400 cm. ^ of thionyl chloride are added ε " 20 g acid benzcdioxole-to-1.3-acetic 5. The mixture is kept stirring overnight at room temperature. The excess of thionyl chloride is evaporated. Acid chloride phenylalkyl T, 3-acetic 5 is distilled (RBs 100°=0.2 mm Hg at the c). Yield 92 jfc * ^ a volume of 100 cm. of dimethylamine is carried to 0° C.. 100 g of the acid chloride of the phenylalkyl-a 1, 3-acetic 5 are added very slowly with stirring. The mixture is kept under stirring for one hour and then filtered. After evaporation and distillation of the filtrate, obtained acid dimethylamide phenylalkyl-to-1.3-acetic 5 *=0.3 mm Hg at RBs 145° c. yielding 90 9 g of LiAlH ^ are poured into a Grignard litree 2. 400 cm. ^ very dry ethyl ether are added and the mixture is refluxed. A solution of 24 g of dimethylamide in 300 After decanting the ether layer is evaporated and the dimethylamino derivative distilled. 0.1 Mm hg=95 °c to RB. Yield 89 40 g of the nitrated product are suspended in 1.8 liter of methanol and then reduced under a hydrogen atmosphere in the presence of Raney nickel at room temperature. After filtration and evaporation of the solvent n, n diméthylaffiinoéthyl-to-6 phenylalkyl-to-1.3 y1-to-5 amine is distilled. 0.06 Mm Hg at the c=125° RBs. Yield 70 2 - Formation of the imine A mixture comprising 0,025 mole of the amine previously prepared (5.25 grams), 0.05 mole of pyridinecarboxaldehyde 3 (5.35 gm) and 100 centimeters ^ of benzene is heated to 120° c in stirring. Water formed popcorn Peppers of reaction is removed using a Dean and Stark trap. When 0,025 mole of water has been collected (0.45 centimeters-to-'J benzene is evaporated, the excess aldehyde distilled then 1' imine compound. RB is 0.02 mm Hg at ≈ 165®C f=66" 0, * round? feels ≈ 6? cents. 3 Salinization This gives the Quinuclidinyl the dimethylamino ethyl-6 n-(pyridylidene and 3) phenylalkyl-to-1.3 yl 5 amine or COH from 01,170. P=13g °C. prepared similarly citrate 01,201 cOH group or the amine (hygroscopic). More imine derived from the (n-, N-dimethylamino-2 ethyl) phenylalkyl-to-1.3 -6 yl 5 amine are prepared following the method described in the example I these are the products of formula I such that Rgrams The R=^ ^ ^===R-R-H-, GB " the R ^==the rg CNY ' 10=- 0 - - 0 - and Ch quinuclidinyl, free base, R .^ ^=■" HM=HM -, triethyl citrate, I, = R=brr - kg. JQL B 1= B 1 eOPA - @ - , citrates, , citrates, , citrates, , citrates, , citrates, , citrates, , citrates, THE COR 01,151, P=139 °C The COR 01,169 "w=151° C. CORs 01,171, w=117° C. CORs 01,176, w=144° C. CORs 01,179, w=171° C. CORs 01,181, w=c-ORC 171° 01,203" hygroscopic CORs 01,206, p=176®Q-ORC 01,207, hygroscopic CORs 01,208, hygroscopic CORs 01,209, P-≈ 178o C. R 1 , citrates, The COR 01,210, hygroscoricue ■aTCaTT 3 in. Synthesis (the n-piperidino-2 ethyl) -6 n thienylidene and 2) yl 5 berber.zodioxol-to-1.3 amine derivatives (formula I, the R ^ " .h, =has, ≈ B4 =B.5 =H a, b.6 - B.7 =(OH-O )5 , b.8 D=,,=O, R.9 - b.10 - -=0) and its oenzilgte•(ORC 01,175) 0.25 moles (49.5 grams) acid chloride phenylalkyl~1, 3-acetic 5 are poured dropwise at room temperature in a mixture of 0.5 mole of piperidine derivatives, 0.5 mole of triéthylaraine, 40g ^ cm in benzene, the mixture is kept under stirring for one hour at room temperature. After filtration, the filtrate is washed with water, evaporated and distilled (BSI 175°=0.15 mm Hg at the c). A mixture of 0.26 moles of Li a1h. (10 grams) in susprension 40c in the solvent is evaporated; the amine is distilled (JSB 98.0 0.02 mm hg * 110 °c). 0.12 ' mole of pipéridinoéthyl-to-5 phenylalkyl-to-1.3 thus prepared is poured dropwise with stirring in 24c cms ^ nitric acid " 1.2 by maintaining the temperature between 25 and 30 °c. the mixture is kept under stirring for one hour. After cooling the nitro compound precipitates. It is filtered, washed with a little water and dried p=207 °c. Yield 76 25 g of the nitro compound are suspended in 2 liters of methanol and then reduced under a hydrogen atmosphere in the presence of Raney nickel. After filtration and solvent evaroration the amine is distilled. JSB 98.0 0.05 mm hg=160 °c, yield 64, 4 * the mixture of 6.2 g of the amine (0,025 months), 5.6 g of thiophene compounds carboxaldehyde and 2 (0.05 moles) and 50 cm.* ^ of benzene is refluxed, the water formed during the reaction is removed using a Dean-Stark trap. the excess aldehyde is distilled and the imine is racristallized in petroleum ether. To a solution containing 0.1 mole of imine in dry ether éthylioue, cooled to 0° c is added dropwise to 0.1 mole of benzilic acid dissolved in dry ethyl ether. The benzilgte is separated by filtration and dried. P=162 °C. The method described in the example 3 allows the synthesis of derivatives of formula I with the rg=R-R-R-^ ^ ^===hr, the rg - ≈ 0-to-Ch a-c, I-the rg=' hr -H *' B., the rg-to-LF==" CHgCHgOCHgCHg -, citrates alamin 01,204 P=2100 C. 5 iSCs-to-aMPLii Synthesis of R-cinnamylidene (D, N-dimethylamino-2 ethyl) -2 aniline compounds (formula I, wherein R=- ch-ch-=^, ^ ^=≈ Β Β Β ^ ^==b-O, The rg Β γ====RG are Y-ch-b-s * h ^ Q-GB) and its citrate salt (ORC 01,185). 50 grams of o-to-nitrophénéthylslcool are added dropwise to 425 cms ^ hydrobromic acid 48 to the mixture is heated under stirring for 3 hours at 100° C. cooling, it is extracted by ether. The ether layer is washed with water and dried on na2s0 ^ and then the solvent is 3 removed by evaporation. After cooling to 30 °c - (bromo-' 2 ethyl) the nitro 1~2 benzene crystallizes, it is purified by washing eth&nol, w govgov.tte to drop to 100 cm dimethylamine cooled 0° c the mixture is kept under stirring for one hour at room temperature and then heated to C. for 4 hours 70°. The alcohol is evaporated, the residue is tough cooling dissolved in an aqueous solution of hydrochloric. The unreacted product is extracted with ether. The acid solution is alkalized and extracted with ether. The ether layer is washed to neutrality, dried, evaporated. N, n-dimethyl ethyl amine rr.hén nitro 2 is separated by distillation JSB 98.0 * 0.2 mm hg=95 °c yield=81 hygroscopic product♦ hygroscopic product 7 BZBMPLB The Syrthèse (D, N-dimethylamino-2 ethyl-methyl-methyl 1) -2:; the aniline - pyridylidene and 3; (formula 1 with R ^= ~S 5= R 3=HM3 , R 8- R. 9THE R= 10 -=H L 11 its citrate salt (ORC 01,123)" the mixture consisting of 50 g of o-nitrophenylacetic, 500 cm in methanol ^, ^ 4 cm in concentrated sulfuric acid is heated to reflux methanol overnight. After cooling and neutralization by sodium hydroxide dissolved in methanol, alcohol is evaporated and then the residue is dissolved in ethyl ether. the ether layer is washed with a dilute solution of sodium hydroxide and then with water and then finally dried and evaporated dry. With a suspension of 0.65 moles of NaH (16 grams) in 250 ml triamide this acid phosphoric hexsméthyl (HMTT) is added dropwise with stirring orthonitrophénylscétate 0.53 mole of methyl (103 grams) dissolved in 20 ml of hexamethylphosphoric triamide, then 0.53 mole of methyl iodide (76 grams). The mixture is kept under stirring at ambient temperature overnight then poured into ice water. Added ^ of ECU 250 cm. after extraction with dilute to benzene, the phases benzèniquas are washed to a neutral reaction, further dried and evaporated, and the distilled twice. The BB 0.03 mm ^ ® 92°<3 . 24 kilograms of 1' the ortho, nitro-phenyl-2 pronionate methyl are dissolved in 300 - 400 cmJ anhydrous ethanol. 15 g of EaBE ^ are added to the solution which is refluxed with stirring for 17 hours and. After cooling the excess NaBH ^ is. destroyed by acetic acid. The alcohol evaporated; water and ethyl ether are added to the evaporation residue. Chase ethereal is washed with water, dried on the Na " s0. and distilled. The BB °C. 27 g of 0.03 mm hg=105 - 110 (orthonitrorhényl) -2 rronanol are added to 220 cm in hydrobromic acid 48 ρ th ^. The mixture is heated to C. for 6 hours 100°, extracted with ether. The ether layer is washed with water, dried on KajSO ^, évarorée and distilled. The BB=0.02 mm Hg at 90 ESA 112° c. yielding 35 g of the solution of bromo-1 (o-nitrophenyl) diluted in 100 ml propan -2 of absolute ethanol is added to 60 cms ^ dimethylamine cooled 0° C. the mixture is heated to 70 °c during 20 hours. The alcohol is evaporated. The residue is dissolved in a dilute hydrochloric acid solution and extracted twice with ethyl ether. The acidic aqueous phase is alkalized, chloroform extracts, dried on NagSO ^, evaporated and distilled the mixture comprising 0.02 mole of (n-, N-dimethylamino-2 methyl-1 ethyl) aniline--2, 0.04 mole of nicotinaldéhyde, 120 cm in anhydrous benzene ^ 120° is heated to C. the water formed during the reaction is removed using a Dean-Stark trap. the benzene is evaporated and then the excess aldehyde nicotinic distilled. The imine is obtained by distillation. 0.03 Mm Hg at RBs 135° C=4" 16 g of the imine (0,015 mol) are dissolved in a liter of anhydrous ethyl ether. After cooling to approximately 32 -5 is added dropwise, 2.88 g acid citricue (0,015 moles) dissolved in the minimum of anhydrous methanol. the citrate is obtained after filtration and drying at vacuum tomre 4c to 0 degrees " hygroscorioue product. _ 8 jgflrFIS Synthesis of (n-, N-dimethylamino-2 methyl-2 ethyl} - 2 n ryriaylidene-to-3 aniline derivatives (formula I with R ^ -, R.grams THE R ^== =hr, Rç=^ j-ch-ch-the rg Η γ==^ I-= ≈= Hr=^ K-) and its citrate salt (ORC 01,214)• A solution of 78 grams (0.6 moles) of ethyl acetoacetate in 50 ml of hexaméthylphosphorotriamide ^ (HKPï) is added dropwise to 21.6 grams (0.9 moles) of NaH in 110 ml of hmrî. F.<^ 50° C. a mixture containing 15 g of ' this alcohol in 12ô cms ^ ^ 48 to hydrobromic acid is heated for 2 hours at 100 °c. After cooling and extraction with ether, the ether layer is washed with water, dried and evaporated. The bromo 2 (o-nitrophenyl) -1 propane is separated by distillation the BB 0.02 mm Hg at ® 120° C.. Yield ≈ 86 a mixture containing 11 g of this product, 40 cm. ^ dimethylamine, 20 cm from ^ of absolute ethanol is heated overnight to 70° c in an autoclave. The solvantB * are evaporated the residue is dissolved in a solution of HS foix extracted two and diluted with ethyl ether. The aqueous phase is alkalized, extracted, chloroform, dried on sodium sulfate, evaporated and distilled. The BB 0.2 mm Hg at 90° C=9.5 gm of n, n-dimethyl-O-nitrophenyl 1 propyl amine and 2 thus prepared are dissolved in 500 cm3 methanol and reduced under a hydrogen atmosphere in the presence of Raney îtickel. After filtration and evaporation of the filtrate (the n, n diméthylemino and 2 methyl-2 ethyl) -2 aniline is separated by distillation. The formed mixture of 5.9 g of the amine (0,033 moles), 0,066 mole of aldehyde nieotinic ^ heart 150 and is heated to anhydrous benzene 120° 0. The water formed during the reaction is removed by means of a trap DeanSiark. The benzene is evaporated. Distillation eliminates the excess aldehyde nieotinic and retrieve the imine. 7.37 g of thereof (0,027 moles) are placed in solution in 1.5 liter of anhydrous ethyl ether. To this cooled solution and a driving -5 -10 °c are added dropwise 5.18 g citric acid (0,027 moles) dissolved in the minimum of anhydrous methanol. The citrate is obtained by filtration and drying under vacuum to 40° C.. hygroseopic product. 9 jgBIPLB Synthesis of n - (where n, n dimé polyethylene resins 2 - amino-ethyl) benzo dioxol-to-1.3 -6 yl 5 formimidoyl-to-2 benzoic, inner salt ii (formula I,V. C00H 7.5 g (0.05 moles) phtalalaehydic acid are suspended in 800 centimeters ^ benzene. the mixture is heated at reflux of the benzene. Added 0,055 mole of (n-, N-dimethylamino-2 ethyl) -6 bensodioxol-to-1.3 yl 5 amino (11.4 grams) diluted in 200 cm in ^ benzene, water formed during the reaction is removed by means of a trap Eean-Stark apparatus, the precipitate is sénsré by hot filtration, washed with benzene and dried under vacuum. Yield 70 the products of the present " invention have been determinations following physicochemical ii 1 - NMR spectra, internal standard msec The COR 01,142, methyl ester prepared by diazotization, solvent CISC3 2.3 ppm 6 proton; the j ^ néch singlet),, 2.2 - 3.2 Ppm 4 proton} massive complex; - Ch-to-CKG's K-3.9 ppm 3 proton; singlet; CHyO 5.9 ppm 2 I-proton singulot; O CH.,-to-0 6.7 ppm 2 proton ii 2 singlets j-aromatic protons (benzodioxolyl) 7.2 - 8.4 ppm 4 proton; massive complex; (benzylidene) proton aromar ticks 9, 1 ppm 1 proton abstraction; singlet; -=Ν: 0 - Ε The COR 01,151 solvent-DMSO d6 2.7 rpm 6 proton; singlet; ^ ^ (ch-^) 2, 9 - 3, 2 4 pNM are proton; massive complex - Ch-to-SDOH n 6.0 ppm 2 proton; singlet 8.8 ppm 1 j of the proton singlet; - the K=HM - CRC 01,163 solvent DfêSO d-6 2.8 ppm 6 proton; singlet; NCCK ^) ^ 3, 0 - 3, 4 ppm 4 proton; massive complex; - EMC Ch 6.0 ppm 2 - ^ n-proton; singlet; - O Ch O - 6, 8 - 8, 0 ppm proton; massive complex? aromatic protons 8.8 ppm 1 proton abstraction; singlet; d=- CH2 - 11 rpm 1 proton abstraction; singlet; labile proton exchangeable L.ave C. BMD CCHs 01,169 CDC1 solvent, 2.5 ppm 3 proton; singlet; thienyl Ch ^ 2.7 ppm 6. proton; singlet; NtOH ^) ^ 2.8 - 3.2 ppm 4 proton; massive complex; - Ch-to-Ch-to-ii 5.9 ppm 2 proton; singlet; - the O-CH2 - O-- ^ 6.4 - 7.8 ppm 14 proton; massive complex; aromatic protons 8.3 ppm 1 proton abstraction; singlet; d=- CH2 - 8.5 - 10 rpm 2 proton; peak spread; labile proton exchangeable with d ^ the O 0 - 1 170-solvent CCD ^ COI structure 2.6 ppm 6 j-proton singlet; d (HM3 )2 2.9 - 3.2 ppm 4 proton; massive complex; - Ch-to-EMC-n-5.9 ppm 2 proton; singlet; - O Ch O - 6.5 - 9.0 ppm 17 proton; massive complex which singlet to 8.3 ppm aromatic protons + n-CH2 -= 9 - 10, 5 ppm 2 proton; peak spread I-labile proton exchangeable with BMD COH from 01,171 solvent 2.3 rpm 6 proton ii singlet; d (HM3 ) grams . 2, 2 - 3, 2 ppm 4 proton 6, 6 - 7, 5 ppm 5 j-proton massive complex; aromatic protons 8.4 ppm 1 proton from F. singlet; d=- CH2 - CRC 01,173 solvent GDCl ^ 1.6 - 2.1 ppm 4 proton 9.ï massive complex; c Ch-PMF-C. 2.7 - 3.4 ppm 8 proton; massive complex; Ch-to-to CKG n (to CKG)2 ~, 5.9 ppm 2 proton ii singlet; - O Ch O - 6, 5 - 9, 0 ppm 17 proton ii massive complex which singlet to 8.3 ppm aromatic protons + n-CH2 -= 5 - 11 2 ppm by proton; peak very spread; labile proton exchangeable with BMD The COR 01,174 solvent CDC1 -, 3 1, 2 - 2, 0 ppm 6 proton; massive complex; 0 - {HM2 )3 2.4 - 3.3 Ppm 8 - C. proton; massive complex; HM2 - HC2 THE N - - (THIS2 )2 5.9 ppm 2 proton; singlet; - O SDOH O - 6.4 - 9.1 ppm 17 proton; massive complex which singlet to 8.3 ppm aromatic protons + - n-Ch - 6.5 - 10 ppm 2 proton, · peak very spread EOC 01,175 solvent odcï ^ 1.3 - 2.0 ppm 6 proton; massive complex; 2, 5 - 3, 4 Proton of FF®8; massive complex 5.9 PPs®2 proton 6.4 - 7.8 ppm 16 proton? massive complex having a singlet to c - (CH22 )3 - c. 8.4 PPs®; aromatic protons +=n-human gh - 6 - 10 ppm to 2 proton; labile proton peak toroids spread ii EOC 01 exchangeable with dgrams 0 176 solvent dms0 - d6 2.6 ppm 4 proton; singlet; - Ch O-Ch - 2.8 ppm 6 j-proton singlet; d - (human gh3 ) grams 2.9 - 3.3 PPs®4 proton; massive complex; Ch-to-to CKG n 6.0 ppm 2 j-proton singlet; - O SDOH O - 6.9 - 7.9 ppm 9 j-proton massive complex; aromatic protons + - 0 0 - Η Η ≈ 6.4 ppm 1 proton abstraction} dipole; - the n=- HC 10.4 rpm 4 proton; broad peak; labile proton exchangeable with BMD EOC 01,179 solvent ms0 - d6 2.6 ppm 4 proton; singlet; - Ch c-Ch - 2.8 ppm 6 proton; singlet ii the n (HM3 )grams 2.9 - 3.3 PPs®4 proton? massive complex} Ch-to-Ch n 6.0 ppm 2 j-proton singlet; - O Ch O - 6.9 - 7.9 PPs®5 proton; massive complex; aromatic protons 8.8 ppm 1 proton abstraction; singlet; d=human gh - - 10.6 ppm 4 j-proton RIE etching wide; labile proton exchangeable with BMD C1 180 EOC bks0 - d6 solvent 2.4 - 3.2 ppm 12 proton; massive complex HM2 - hC2 - hence he (HM2 )2 2.4 - 4.0 ppm 4 proton? massive complex; 6.0 ppm 2 proton; singlet; - O Ch O - 6, 6 - 7, 9. 5 ppm based proton; massive complex; ; hM2 - c. Ch2 + - this2 - o-OH2 - aromatic protons 8.7 pPs®1 j is the proton singlet; d=- HC 10.5 ppm 4 proton, broad peak; labile proton exchangeable with dgrams 0 PCC. 0 '13' 1 solvent dks0 - d6 THE K (THE CK3 )2CHgCHgN + 2.4 - 3 - " 5 ppm 14 proton; massive comrlexe; Ch O-SDOH + 6.0 discount. 2 proton; singlet; - the O-CH2 - O-- ^ 6.8 -7 , 4 6 rRMs letlet us rrotons; massive comrlexe; aromatic proton-proton 8.7 ppm 1; singlet; d=- Ciï 9.5 - ^ ΐ MPI 4 proton; peak spread; labile proton exchangeable with BMD ORC 0 * 184 solvent dms0 - d6 2 4 6 rpia proton; singlet; - Ch c-Ch- 2.7 ppm 6 letlet us rrotons; singlet; NtCK ^ grams 2.9 - 3.3 Ppm 4 proton; massive complex; Ch Ch ^ - n-T-, 1 - 9, 2 ppm 9 proton; massive complex having a singlet to 8.7 RRMs; aromatic protons +=- HM - N. 11 ppm 4 proton; broad peak; labile proton exchangeable with BMD CRC 01,185 solvent dks0 - d6 2.6 ppm 4 proton; singlet, •HM - ^ c CHj) 2.7the RR the m 6 proton; singlet; NCGH ^) ^ 2.9 - 3.3 ppm 4 proton; massive complex; Ch Ch ^ n-proton - 6.9 - 7.9 PPs®11; massive complex; aromatic protons +=- ch-ch-- 8.3 rpm 1 proton abstraction; dipole;=n-CH2 - 10.2 ppm 4 letlet us rrotons; a dome; ^ 2° exchangeable with labile proton COPS. 0<186 solvent bks0 - d6 1, 7 - 2, 2 ppm 4 proton; massive complex; O OHj-to-OKg O 2.6 ypm 4 proton; singlet - Ch O-EMC - 2.9 - 3.5 ppm 8 proton ii massive comrlexe; HM2 - HC2 THE N - (HC2 >2 6.0 letlet us rrotons' R-m 2; singlet; - O CEîg O - 6.9 - 9.2 rRMs 7 proton; massive complex having a Sign-Land to 8.7the R rm.; ii=HC + aromatic protons. 9, 5 - 10, 5 ppm 4 proton; dome; labile proton exchangeable with BMD The COR 01,195 solvent 33eso - d6 1.3the R r-proton®9; T-singule; C. (HM3 )3 2.6 ppm 4 proton; singlet; Ch c-Ch - 2.9 - 3" 3 ppm 4 proton; massive comrlexe ii - 2 - CHgCHgS and 6.0 ppm based proton; singlet; O Ch O 6.9 - 9" 2 ppm 7 proton; massive complex whose starting motor. singlet 8.7 PPs®ii proton aromatiaues Ν ≈ + (2 - Η 5 - 11 ppm to 5 proton; peak spread; labile proton exchangeable with BMD The COB 01,200 solvent'd?.' a SC-d6 1 7 - 2, 3 ppm 4 proton; massive complex 2.6 ppm 4 proton; singlet; Ch c-HC 2.9 - 3.6 rpm 8 proton; massive complex 6.0 ppm 2 proton; singlet; O Ch O 6.9 - 7.9 PPs m-proton; massive complex; ; C. CH2 - HC2 - i 2 ; HM2 - HC2 THE N (HM2 )2 aromatic proton " + - g K=HM ' 6.4 ppm 1 Croton Tiglium; dipole;=n-CH2 - 9.5 - 11 ppm 4 proton; dome; labile proton exchangeable with d2 0 The COB 01,201 solvent dks0 - d6 2.6 ppm 4 proton 2.7 ppm 6 proton; singlet 2.9 - 3.2 ppm 4 proton; massive comrlexe 6.0 ppm 2 proton; singlet; toilet 1800 to U-shapes 6.9 - 9.2 ppm 7 proton; massive comrlexe which a singlet to 8.7 ppm} proton Ν ≈ 0 - + aromatinues Κ HM2 - C. CH2 CEgCHjJ: - 9, 5 - 10, 5 ppm 4 proton; peak spread; labile proton exchangeable with BMD The COB 01,202 solvent diis0 - d6 1, 3 - 2, 1 ppm 6 letlet us rrotons; massive comrlexe; C. - (HC "), - C. 2.6 ppm 4 proton; singlet; - Ch c-Ch - 2 ,t above 3.5 ppm to 8 j-proton massive comrlexe; ch-ch-^0 W ' (Cïï *)2 6.0 ppm 2 proton; singlet 6, 9 - 9, 2 ppm 7 proton; massive comrlexe which a singlet to 8.7 ppm; aromatic protons + -=- OH-Ν 4 Lo Prom proton; broad peak; labile proton exchangeable with BMD The COR 01,203 solvent bes0 - d6 2.6 ppm 4 proton; singlet; LEC c-HM, . 6 4a 2.7 ppm 6 proton ii singlet, ii * - {HM,)0 _ 2.8 - 3.3 PPs®4 proton; massive comrlexe; ch"c7,jf 6.0 rRMs 2 proton; singlet; - C. Ch ^ - C. 6.8 - 8.8 7 rTMs proton•massive comrlexe which a singlet to 8.6 ppm; aromatic protons + - 0 - Η Ν ≈ 10.1 ppm 4 proton; broad peak; proton Irbiles exchangeable with BMD 01 2C4 bms0 - d6 COH from solvent 2, 5 - 3, 3 12 PFMs proton; massive comrlexe; Ch g-ch-■Ch + ^2 - hC2 hr (HM2 )2 3.4 - 4.0 ppm 4 proton; massive complex; Ch O-Ch 6.0 ppm 2 proton; singlet; - the O-CH2 - O-- ^ 6 "9 - 9" 2 ppm 7 proton ii massive complex having a singlet to 8.7 ppm; aromatic protons + -=- OH-Ν Lo, 2 ppm 4 letlet us nrotons; broad peak; labile proton exchangeable with BMD C1 205 CORs dms0 - d6 solvent 2.3 - 3" 2 ppm 19 proton} massive complex; Ch O-Ch + n-Ch3 EMC-to-Ch n + (CHgCHg) grams 6.9 - 9.2 ppm 9 proton; massive complex having a singlet to 8.6 ppm ii aromatic protons + NeCH - - 10.3 ppm 4 proton; broad peak; labile proton exchangeable with BMD The COR 01,206 solvent dms0 - d6 2.4 rpm 3 proton ii singlet j. CNY-C. 2.6 ppm 4 proton; singlet $Ch c-Ch 2.7 ppm 6 j-proton singlet; nçch ^) ^ 2.9 - 3.2 ppm 4 proton; massive complex; Ch-to-CHgN 6.0 ppm 2 proton 6.9 - 8.0 ppm 6 proton *, ** AA which system the BB + 2 singlets; aromatic protons 8.5 mPI 1 proton abstraction; singlet; Η Ν ≈ 0 - 8.5 - 10 ppm 4 proton; peak spread; labile proton exchangeable with BMD The COR 01,207 solvent dks0 - d6 2.6 ppm 4 proton; singlet; HM - ^ c EMC 2.8 ppm 6 proton; singlet; NCCH ^) ^ 3, 0 - 3, 3 I-PM 4 proton; massive complex; CHgCHgN 6.0 ppm 2 proton; singlet; O Ch O 6.9 - 8.2 Ppm 5 proton; massive complex; aromatic protons 8.6 ppm 1 proton abstraction; singlet; d=- HC 10.5 ppm 4 proton; IEP wide; labile proton exchangeable with BMD The COR 01,208 solvent dks0 - d6 2.6 ppm 4 proton; singlet; Ch O-Ch 2.7 ppm 6 proton singlet therein|HCCH ^ 2.9 - 3" 2 ppm 4 willwill prprons; massive complex; GKgCEgK 6.0 ppm 2 proton; singlet; O to CKG O 6.9 - 8.1 ppm 6 proton ii system AAs + 2 singlets' the BB ' j-aromatic protons 8.6 ppm 1 nroton; singlet; d=human gh - 8 - 10 ppm of proton 4; peak spread; labile proton exchangeable with BMD The COB 01,209 solvent DKSC-to-d6 2.6 ppm 4 proton; singlet; Ch O-SDOH 2.7 ppm 6 proton; singlet; d (HM3 ) grams 2.9 - 3.2 ppm 4 proton; massive complex} OOTW-to-CHgN 6.0 ppm 2 proton ii singlet; O Ch O 6.9 - 8.1 ppm 7 proton; massive complex; aromatic protons 8.6 ppm 1 proton abstraction; singlet; d=- HC 9.8 4 proton; broad peak; labile proton exchangeable with BMD The COB 01,210 solvent dms0 - d6 2.6 ppm 4 proton; singlet; Ch O-EMC 2.7 rpm 6 proton; singlet; d (ch-^) grams 2.9 - 3.3 ppm 4 proton; massive complex; CE cu ir ^ 3.8 ppm 3 proton; singlet; ^ Osh 6.0 ppm 2 proton; singlet; O Ch O 6, 7 - 8, 0 ppm 6 NRs ο tones; massive complex; aromatic proton-proton 8.5 ppm 1; singlet; d=- HC 9.9 ppm 4 proton; broad peak; rrotcns labile exchangeable with BMD. The COB 01,213 solvent dms0 - d6 1.3 Celaton 3 proton; dipole ii HM ^ - C. 2.4 - 4.2 rpm 13 proton; massive complex To CKG and 0 to-Œïg Ν + (HC3 ) CHCHg n + grams 7, 1 - 9, 2 ppm 9 proton; massive complex having a singlet to 8.7 ppm, aromatic protons +=- HM - K. 10.6 ppm 4 proton; broad peak; labile proton exchangeable with BMD. The COB 01,214 solvent dms0 - d6 1.1 ppm 3 proton; dipole; HM - ^ - C. 2.4 - 3.8 ppm 13 proton; massive complex Ch c-Ch + n-(HM3 )2 + Ch Ch n - 7.0 - 9.2 ppm 9 j-proton massive complex which a singlet to 8.7 ppm; aromatic protons +=- OH-Ν Lo, 5 ppm; 4 proton; broad peak; labile proton exchangeable with BMD 2 - Elemental microanalysis GEA nroduits which is contemplated by the present invention have undergone various pharmacological tests which we give the following results. The percentages of induced by the products of the present invention orally available oral Swiss mouse are shown in table 1. Animals free of specific pathogenic organisms are stalled in 24 to 48 hours climatic room before the start of the experiment. They are sorted into batches of 5 male and 5 female. In animals fasted from 24 hours, the substances are administered intrags e sorting that in a julep of gum arabic 6 The analgesic activity was determined in mouse a male Swiss in using as the nociceptive phénylbenzoquinone (iBQ) (variant of the method of Siegmund & transporter. Process. Share. Med.iîxr.., 1975, 95,729 - 31)•twenty five minutes followed by administrationT- the R - - oral products testing suspended in a julep gummy to 6 is injected into the solution and then observing the L<FBQ - e mouse after 5 min making the 5 minutes thereafter " the results are gathered in table 2. The psychotropic profile of the present invention has been characterized in animals by several tests with a few results are shown below. The products of 1' invention are always administered orally in a julep gummy to 6 £>. The table no. 3 indicates the effect induced in the test of the evasion in mouse and expressed by the percentage of change of the number of outputs of the animal in 5 min. Toxicity in the mouse e # mortality in a dose dependent manner C0H 01,186 50 : following table η0 1 - - - - - Products: $mortality ergeant n° dosage: mgs administréeen&kg. table The Te ST 1' evasion the mention nsec signifies unterstanding the products of the rrésente only have generally not activity cateleptic high potency. Only the ORC 01,176 has caused a slight catalepsy to 400 mgs/kg of 60c and. Few derivatives exhibit antagonism as it relates to the R to apomorphine stereotypies effect in the COR 01,176, 202, 206, 209, 210. The test results are shown in the table no. 4 * Inhibition assay is the toxicity of the amphetamine-induced group was rejecting the hypothesis of activity for these derivatives neurolertic. A number of products have anxiolytic activity highlighted in the test of the LAN^4 - uies Dr Chee the mouse (table no. 5) 5 TÜBLBTÜBLB.AÜ confectioneries * increase in the number of displacements: the animal with respect to the dose expressed as mg/kg. Some tests were to demonstrate antidepressant activities. It e1 acts tests of antagonizing the effects of reserpine, an L * of the oxotrémtfrine @ Bverett after G.K. & al, forensic science, 1956, 124, 79 and Levÿ J & transporter. Therapy 1965, 20, 265) and despair (based Forsolt r.33. Hyg ., 1978, 47, 379 - 91)•autostart results are shown in tables 6, 7, 8. TABLE 7 8 TA3LÜAU None of the tested products does activity in the test at 5 Hepreceptor; derivatives which is contemplated by the present invention have heretofore not inhibitory activity of monoamine oxidase. Some products have anticholinergic activity detected in the inhibition test of the pilocarpine-induced salivation (table's French). In view of their pharmacological properties characterized by an analgesic activity, activity antidérressive not IN O, anxiolytic activity and - for some anticholinergic activity, these activities manifested to IERs dose very lower than the toxic doses, the products forming the subject of the present invention may be employed for example in the treatment of depressive conditions of various etiologies to component of anxiety, in the treatment of anxiety states observed during certain psychiatric or organic, in the treatment of the depressive component and entertainment akinetic Parkinson's disease; in children, they will treat insomnia, tics, the stammerings, enuresis, nocturnal scare; the elderly, they will be useful for the treatment of insomnia, relational difficulties with the surrounding, psychiatric disorders involution; they can also be employed for the preparation to the small procedures and treatment for certain pain. Dosages and treatment regimens will be dependent on the subject, generally fine, instituting a dosage should be gradual and-matter ' from the progressively tert. The products forming the subject of the present invention may be admitted. nistrés EOR orally (e.g. in the form of capsules, comtrimes, drinkable drops) or by injection (solute injectsbls intramuscularly or intravenously; intravenous perfusion). Following the indications the daily dose will vary from 3 to 300 mg in one to three doses. The vaccine following non-limiting examples of formulation. The COR 01,176 0.6 g of base per vial of 30 ml or 0.5 mg per drop Comrrimés ' 01,184 Tablets containing 25 mg CORs base The COR 01,173 tablets containing 100 mg base The COR 01,202 comrrimés dosed to 5 mg base The COR 1,202 injectable ampoules apportioned 25 mg base EOC 1,184 injectable ampoules apportioned 25 mg base Compounds, exhibiting central nervous system activity, of the formula <IMAGE> (I) wherein R1 is phenyl which is unsubstituted or substituted by at least one member selected from the group consisting of halogen, CF3, C1-C4 alkyl, C1-C4 alkoxy and COOH, or R1 is <IMAGE> or R1 is a heterocycle selected from the group consisting of <IMAGE> +TR <IMAGE> R2+L, R3+L, R4 and R5, which may be identical or different, are H or CH3; R6 and R7, which may be identical or different, are C1-C6 alkyl, which may be straight-chained or branched, or R7 can be H when R6 is a branched-chain alkyl, or R6 and R7 can form, with the nitrogen to which they are bonded, a heterocycle selected from the group consisting of <IMAGE> +TR <IMAGE> R8+L, R9+L, R10 and R11, which may be identical or different, are H, halogen, CF3, hydroxy or C1-C4 alkoxy, or two contiguous members of R8+L, R9, R10 and R11 may together form a chain -O-(CH2)n-O-, where n=1 or 2, or a chain -O-CH2-O-CH2-; and pharmaceutically acceptable addition salts thereof are disclosed, along with a method of producing the same, and pharmaceutical compositions comprising the same. 1. - Novel products of general formula THE R, The RR with R a-j=phenyl substitute ' or not by one or more substituents as hslogéno, FS ^ I-lower alkyl of c1 to c4, lower alkoxy of 01 to 04, the COOH, or R ^ ^ 0===CK from HM - or heterocyclic radical such as (LQ fifeJgJL " with with the rg "RG represents" hr10 , R is the same or different ^ ≈ hr, halo, MC ^>hydroScy, ai 01 to 04 coxy lower, two substitiu 2. - Novel products made up acid salts such as hydrochloric acid, benzilic acid, citric acid products according to the paragrrrhe 1; ^ 3. - New products according to paragraphs 1 and 2 of the R====^ Q-O. 4. - New products - according to paragraphs 1 and 2 such as the rg s - h, Rç R ^ Q-forming together a CH sinc - O HM - ^ - erffective powerU. 5. - Method of preparation of the products according to paragraphs 1 to 4 characterized in that comprises reacting an amine of formula with the rg, the R ^=same or different lower alkyl branched or not c1 to c6, R-T-. ^ ouvant be equal to H in the case where Rg rerrésente a branched alkyl; moreover the rg and R ^ may form with the rg, R.oCR10 , The R ^=K to the same or different, halogen, CP-a-j, hydroxyl, lower alkoxy Cl to c4, two substitute; - e contiguous rouvant together constitute a CH groin - 0 - (Ch)the R n=1 - 0 and suitable method or 2 or - O Ch O-Ch -, and an aldehyde of formula R CHO-^=phenyl unsubstituted or substituted with the R? R or olusieurs substituents as-HR logéno, MC ^, lower alkyl c1 to c c1 c4 to lower alkoxy, COOH group, or R1 = = HM=HM - or R=heterocyclic radical such as - Qt CPLI. (§>R.5• HR, R.9 - R. * 1= LQ B., = CL 20B 1 * WHEREIN GX B 1= LQ 0 - Ch a-c, I-the rg= ' hr -H *' 10 " 1 , RG represents R-P- - (cH22 )4 - B 1 - Çr "RG are" " ^® 15 B 1 ■ " R.the R THE R ^ - ŒgOHjOOH B 1 , Βς - Η γ ≈ B 1 , Β γ ≈ hr, B6 =- TBU such 20 B 1 - CH-CH-==^ - , Βς - Η ^= B 1 ■Φ- , The rg-to-of Rj= 5 - Product CARBON HYDROGEN NITROGEN OXYGEN: " theory found theory found theory found theory found 10 01,151 67.90 67.10 5.70 5.88 5.28 4.89 15.08 14.54 * 01,169 68.36 69.17 5.92 6.27 5.14 4.95 14.69 * 14.01 9.ï•9.ï 01,170 70.84 70.94 5.95 5.96 7.99 8.18 15.22 15, 20 01,173 71.85 71.08 6.03 6.49 7.62 7.46 14.50 ** 13.95 01,174 72.19 72.07 6.24 ; 6.16 7.43 7.42 14.14 e 13.75 01,175 69.45 69.26 6.00 6.00 4.91 4.77 14.02 13.68 9.ï•" 01,176 60.69 59.90 5.88 5.84 5.44 5.35 27.99 27.88 e 01,179 55.45 53.15 5.30 5.84 5.66 4.92 29.12 •• 25 01,181 46.08 46.25 4.39 4.65 4.89 4.31 25.11 25.59 i-I 01,185 63,&2 64.08< 6.43 6.70 5.95 5.85 23.80 23.18•* e 30 01,195 58.02 58.88 6.04 6.73 8.12 7.87 27.82 28.17 ii 01,200 62.21 62.93 5.97 6.46 5.18 4.74 26.64 26.59 seconds 35 01,201. 56.44 56.67 5.56 5.95 8.50 8.54 29.42 30.25 ii ** 01,203 54.65 54.90 5.38 5.59 8.31 8.17 31.65 T- 01,204 56.49 56.60 5.50 5.67 7.91 7.36 30.10 •29.85 ii 01,205 59.99 59.59 6.44 6.50 11.19 10.56 ' 22.37 01,206 59.75 59.77 6.02 6.17 5.57 5.33 26.66 29.62! ii G1 207 51.72 51.88 4.70 5.17 5.03 4.67 25.83 ♦25.02! : 01,208 55.12 55.25 5.20 5.54 5.36 4.90 27.54 ** 27.33: 01,209 59.00 58.98 5.78 6.0 8 5.73 5.17 29.48 29.66 ii 1 e n° e expressed as mg/kg body weight administered: ***••••••••••••: I-150, 5 250! 500 750, 8 1000 9.ï: 1500 2000•I-e "§••!" ** 1 EOC 01,142 ! ""••••9.ï ii ii ii 0:! 50! ••••••••••0••" THE COR 01,151• 0 * 10 * 40 * 60 : 01,163 EOC 25 * 70:100: ii ii e ii••••••th : ALAMIN 01,169 ::: ii the COB 9.ï 01,170 ::: i-0 the I100 :: : 01,171 EOC 20! 80 * 90 *: * ii 9.ï: ii::::: : ORC 01,173 ii: 0 sec. 30 sec.:::: ii::::: :: EOC 01,174: : ii 0:: 10 sec. 9.ï 50: "••••••• ii alamin 01,175 : 0 ii 10 ii 10 ii e ii: : ORC 01,176 **•••••0:: O:: ii: ii EOC 01,179 : : ORC ' 01,180 ::: 8 e:: ii ii 0 ii: 70 ii e ii••■••••• : ORC 01,181 :: i '•••••"•"•#•♦*••••9.ï alamin 01,184 9.ï: ii: e: 0 9.ï 30 ii : ii 9.ï: O:: I-: ii EOC 01,185 ii ii 150 250 500 750 1000 1500 2000 : COH FROM 01,195 0 20 30 : ORC 01,199 0 50 ! 01,200 COH FROM 0 10 70 : ORC 01,201 10 30 : ORC 01,202 10 ' 30 60 the COR 9.ï 01,203 0 10 40 : ORC 01,204 0 10 : ORC 01,205 0 10 10 : ORC 01,206 0 50 : ORC 01,207 0 20 20 40 : ORC 01,208 0 30 20 20 80 the COR 9.ï 01,209 " 0 40 60 ! THE COR 01,210 O 0 10 20 i-ORC 01,213 0 j-ORC 01,214: I 0 30 70 Product n° 50 100 200 ii THE COR 01,142 22 20 10: THE COR 01,151 41 79 •"•• THE COR 01,163 17.5 *•• THE COR 01,169 7 43. ""• THE COR 01,170 30 39 9.ï THE COR 01,171 51 THE COR 01,174 48 18 THE COR 01,175 13 71 the I THE COR 01,176 23 39 j. THE COR 01,180 18 34: *" THE COR 01,181 25 42 "•" 1 THE COR 01,184 34 44 55 sec. THE COR 01,195 24 31! THE COR 01,199 8 24.5 56.5: THE COR 01,202 2 0 33 j. THE COR 01,203 0 36 47 sec. ; Product η0 $analgetic activity in; a dose dependent expri -: mée in mg/kg body weight: 50:100: 200 ii ; 00 Β 01,204 •"s * 0 ii 45 ii 42 ii•*" : ORC 01,205 : 10 ii 36 : ALAMIN 01,209 The I -•■-••' *: -: 17. :..: - ii ' - - 9.ï■ the COR ΐ 01,210 : o•T-O 27. 33 t. ! THE COR 01,214 - ^ ;;· · · *...: ' 21. t-VBE1 - 30 ii acetylsalicylic îicide : 55 61 ii: ; - - 9.ï■•■•'; -■•••■■*••-••• i-J. ; the O, 5 1! 1 of i 3 j is the j I-I-5 10 !; 25 J. 5° 75 100 {150 r; 200; !; CRC C1 151 ! 1, 1 the j; the j; i-J. t-T- THE HS nsec; NSEC -41; i-j of the j? of i CCHS 01 the I ^ Oj is ; j. t-T- ii ii i-J. t-J. nsec; NSEC - 32j of i - 59 ΐ ; i-J. COH FROM 01 173; i-J. ; i- i-J. *" 33j !; -13 -29; -26 -50; -55 ; - 9oi 5 j is the j THE COB 01 176•-29 i 40 t-F. -39 of i '33 the I !; -32 " 37; -33; I-43 ! t-T- GÛB 01 -•80; i-J. ;! the R ii nsec; NSEC j is the j NSEC - 2l| -37; ; - 75; j is the j ORC 01 184; 1! ; j. the I; -34| -26 " t- -23 " 34; -47; ;|- 46 i-I- ORC 01 195; THE RS !; NSEC 1 + 54 the I; + 53; NSEC ; i- NSEC + 19; + 28; i-I-; nsec; i-J. ORC 01 200; i-J. t-J. i-I- nsec; + 25 ; j. NSEC + 38; NSEC NSEC; ; i-I-J. 10 i-I- ORC 01 202; t-J. THE HS ; i- the T! NSEC; NSEC of i NSEC nsec; NSEC ; j. ! the I; J. ; L. ORC 01 203; ; r. t-J. T-J. NSEC; j is the j NSEC nsec; NSEC; ; j.; the I ; ii ORC 01 204; ; i- the j ii 1! -28; NSEC " j. -31 -24; -20 -15; ; - 24; j is the j CRC 01 205; i-J. T- the T! NSEC; - ii! •NSEC nsec; NSEC ; t- a j-34j ! j_ ORC LC 206; the j ii 1 i- 1! ; i- NSEC t-T- -18 -28; -63; 1! 1! 15 Y ORC 01 209; 1! i-J. J.| -20; J IS 1 -38 -32| -37 ; 1 ^! ; - ^ the V; t-I- CRC 01 210; [t- ; i- 1 t. NSEC; 1, 1 NSEC NSEC; -20; - 26 ! * "! ! CRC 01 213| THE I 1 THE HS i-ii T-J. ; t- NSEC 1 j. the j; NSEC -20; NSEC 1 W! F. t-J. CRC 01 214; t-J. THE HS r. J. 1 J. j is the j NSEC I-J. of i i-nsec; 1! 1 I- ïroduit n° ,Q " pick the j {dosage as such the ictivity s by the pomorphine in administered expressed stereotypic infonction mgs/kg of said SN !25 ; 50 i-I-; 75; 100 ! Y 150; 200 ORC 01 176 ; i- i-J. j-j-j-j is ! ! ;; -64 ORC 01 202 ! ~35 ! "32 ! NSEC ; j. t-T- -20 ORC 01 206 ; nsec j - 53 T-I-j-; -71 I-J. the j; -22 ORC 01 209 i-J. |-54 j is the j; T- -51 j is the j T- -42 ORC 01 210 ; i-I- i-I-I- ;; 1, 1 i - 33! T-I-I- -33 of i the R 1.5 3 ii 5 10 20 25 40 50 60 75 icOR 01,170 + 18 + 57 + 36 + 69 + 72 THE COR•01,173 NSEC + 30 + 47 + 60 + 82 tCOR 01,176 NSEC + 101 117 + + 72 + 72 + 66 NSEC : CRC 01,180 NSEC NSEC + 6, 9 + 88 + 35 : ORC 01,184 + 89 + 73 + 56 + 61 NSEC : C0E 01,200 + 112 + 180 + 292 + 142 + 84 THE COR 01,202• + 48 + 96 ptotic PGRs induced inhibition of the reserpine as a function of the orally administered dose expressed as mg/kg. 2.5 5 10 25 50 75 100 200 THE COR 01,173 -12 -21 -23 The COR 8 01 ΐ θ -18 -34 -26 -20 NSEC THE COR 01,184 -13 -39 -34 THE COR 01,195 NSEC -22 -22 01,200 ORC NSEC -28 NSEC -24 THE COR 01,203 NSEC -33 -27 C1 205 ORC NSEC -31 -25 -31 THE COR 01,209 NSEC -45 THE COR 01,210 NSEC -21 -38 t-ii 25 50 75 the T; 100 1 j. ! .150 ! 200 1, 1 ORC 01 170 j. -40 i-I- -50 the T; the R; -78 1 T. ORC 01 173; -20 -20 -40 1; -60 ; -70; t-9.ï ORC 01 176 the j -40 1| -50 t-T- THE T! -20 t-T- ORC LC 180 j. -22 the j! -44 ; t- T-J. -44 t-T- ORC 01 184 the j -20 0 ; j. -22 1 r. 1; -17 T-T- ORC iC 202; 0 -67 -44 ; I- t-T- the T! T-ii ORC 01 203 j. -70 1 j. -50 ;; ! ! -20 1! ORC 01 1,204!; -30 ! ;! -20 ; t-1 1; 1 -30 t-j-| ORC 01 205; -30 1; -30 1; 1, 1 -40 1; ORC 01 209| -60 -60 1! -55 ; 1 -60; -30 T-T- o-O DCFs 01 210 -50 -40 j is the j -50 1 t. -30; -50 ii ii 1 ; T T- Iroduits n° Testing the despair of antagonism $j is a function of the dose administered orally department NAR MgAg and expressed 50 100 200 01,170 COH FROM " 39 -39 -33 THE COR 01,173 -18 " 41 " 53 THE COR 01,184 " 20 -18 THE COR 01,202 -49 -67 :•productthe n the O $inhibiting soiled -: lower power requirements induced OLIN -: carpine depending on the: dose administered expressed: in mg/kg body weight: 50 75 100 200: : ORC 01,170 NSEC -18 -57; : ORC 01,173 NSEC -39 -48 -76: : ORC 01,184 " 23 sec. : ORC 01,203 - L. -32 NSEC -30: Oral drops
Injectable solutions