FR2499992A2 - 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80) - Google Patents

Abstract

Nortropane derivs. of formula (I) and their acid-addn. salts are new. In (I) (a) R is benzyl and A is 2-amino-4-ethoxy-5-pyrimidinyl, 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-nitrophenyl, 2-methoxy-5-hydroxyphenyl, 2-methoxy-4-amino-5-bromophenyl, 2-methoxy-4-acetamido-5-bromophenyl, 2-methoxy-4-acetamido-5-chlorophenyl, 2-methoxy-4-trifluoroacetamido-5-chlorophenyl, 2-ethoxy-4-amino-5-bromophenyl, 2-methoxy-4-aminophenyl, 2,4,5-trimethoxyphenyl, 2,4-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl or 2-methoxy-3,5-dibromo-4-aminophenyl; (b) R is m-methy-, m-CF3- or m-halobenzyl and A is 2-methoxy-4-amino-5-bromophenyl; (c) R is p-methyl-, p-methoxy-, p-bromo- or p-chlorobenzyl and A is 2-amino-4-methoxy-5-pyrimidinyl; (d) R is benzyl p-substd. by l lower alkyl, CF3, Cl, Br, or F and A is 2-methoxy-4-amino-5-bromophenyl; (e) R is 3,4-dichlorobenzyl, 2-thenyl or 3-thenyl and A is 2-methoxy-4-amino-5-bromophenyl; (f) R is 2-thenyl, 3-thenyl or 2-furfuryl and A is 2-methoxy-4-amino-5-chlorophenyl; or (g) R is cyclohexylmethyl and A is 2-methoxy-4-amino-5-bromophenyl). Intermediates 2-amino-4-methoxy-5-pyrimidine-carboxylic acid, 2-amino-4-ethoxy-5-pyrimidine-carboxylic acid, methyl 2-amino-4-methoxy-5-pyrimidine-carboxylate and ethyl 2-amino-4-ethoxy-5-pyrimidine-carboxylate are also new. (I) are neuroleptic agents with higher activity and generally lower toxicity than sulpiride.

Description

ainsi que leur procédé de préparation, ces nouveaux dérivés étant utiles comme intermédiaires de synthèse pour la préparation de médicaments.The main patent application No. 81.02714 resulting from the division of the patent application No. 79.00971 relates to new derivatives of the nor

as well as their process of preparation, these new derivatives being useful as synthesis intermediates for the preparation of medicaments.

This application for a certificate of addition relates to compounds having the same basic structure as the derivatives of formula (I) and find
o also their application as synthesis intermediates for the preparation of drugs.

dans laquelle R représente
- soit un atome d'hydrogène ou un groupe benzyle, méthyl-3 benzyle, chloro-3
benzyle, fluoro-3 benzyle, méthyl-4 benzyle, fluoro-4 benzyle, chloro-h
benzyle ou cyclohexylméthyle, Y représentant alors un groupement éthoxy carbonyle
- soit un groupe chloro-2 benzyle, méthoxy-2 benzyle, méthoxy-3 benzyle,
trifluorométhyl-3 benzyle, bromo-3 benzyle, cyano-4 benzyle, bromo-4
benzyle, alkyl inférieur-4 benzyle dont le groupe alkyle comporte au
moins deux atomes de carbone, trifluorométhyl-4 benzyle, dichloro-3,4

More specifically, the present application relates to new derivatives of ss-amino-3 nor-tropane which correspond to the formula

in which R represents
- a hydrogen atom or a benzyl group, 3-methylbenzyl, 3-chloro
benzyl, 3-fluoro-benzyl, 4-methyl-benzyl, 4-fluoro-benzyl, chloro-h
benzyl or cyclohexylmethyl, Y then representing an ethoxycarbonyl group
- a 2-chlorobenzyl group, 2-methoxy benzyl, 3-methoxy benzyl,
3-trifluoromethyl benzyl, 3-bromo benzyl, 4-cyano benzyl, 4-bromo
benzyl, 4-lower alkylbenzyl, the alkyl group of which has
minus two carbon atoms, 4-trifluoromethylbenzyl, 3,4-dichloro

 of hydrogen or an acetyl or ethoxycarbonyl group.

dans laquelle R' représente :
- soit un noyau benzyle, auquel cas A-C0- désigne
un noyau aroyle de formule

dans laquelle le couple (R1, R2) prend l'une quelconque des valeurs suivantes : (C2H5,H), (CH3,H), (CH3,Br), (CH3,Cl), (CH3,F), (CH3,I), (CH3,NO2), (CH3,NH2), (CH3,OH), (CH3,C6H5CH2O), (CH3,CH3O), (CH3,CN), (CH3,CH3SO2), (CH3,C2H5SO2), (CH3,CHO), (CH3,C3H7(n)CO),

un noyau aroyle de formule

As for the drugs that can be obtained from the derivatives of formula (I), they correspond to the formula

in which R 'represents:
or a benzyl ring, in which case A-C0-
an aroyl nucleus of formula

in which the pair (R1, R2) has any of the following values: (C2H5, H), (CH3, H), (CH3, Br), (CH3, Cl), (CH3, F), (CH3) , (CH3, NO2), (CH3, NH2), (CH3, OH), (CH3, C6H5CH2O), (CH3, CH3O), (CH3, CN), (CH3, CH3SO2), (CH3, C2H5SO2) ), (CH3, CHO), (CH3, C3H7 (n) CO),

an aroyl nucleus of formula

wherein the set (R1, R3, Rq) takes any one of
following values: (CH3, CH3CONH, Br), (CH3, CF3CONH, Br),
(CH3, CH3CONH, C1), (CH3, CF3CONH, Cl), (C2H5, NH2, Br),
(CH3, CH3CONH, H), (CH3, NH2, H), (CH3, CH3O, CH3O), (CH3, CH3O.H) an aroyl ring of formula

- soit un noyau benzyle monosubstitu en position ortho de formule

dans laquelle R6 représente un atome de chlore ou un groupe méthoxy, auquel cas A-CO- désigne le noyau amino-2 méthoxy-4 pyrimidinyl-5 carbonyle de formule

- soit un noyau benzyle mono substitue en position méta de formule

dans laquelle R7 représente
un groupe méthoxy, auquel cas A-CO- désigne le groupe amino-2
méthoxy-4 pyrimidinyl-5 carbonyle, ou
un groupe méthyle ou trifluorométhyle OU un atome d'halogène,
auquel cas A-CO- désigne le noyau méthoxy-2 amino-4 bromo-5
benzoyle, - soit un noyau benzyle monosubstitué en position para de formule ::

dans laquelle R8 représente
, un groupe cyano ou un atome de brome, auquel cas A-CO- représente
le noyau amino-2 methoxy-4 pyrimidinyl-5 carbonyle
un groupe alkyle inférieur, trifluorométhyle ou cyano ou un atome
d'halogène, auquel cas A-CO- représente un noyau méthoxy-2 amino-4
bromo-5 benzoyle, ou
un atome de fluor, auquel cas A-CO- représente un noyau méthyl-2
éthoxy-4 pyrimidinyl-5 carbonyle de formule

wherein R5 represents a member selected from the group
comprising: methoxy-3, methoxy-4, fluoro-4, chloro-4, methyl-4,
chloro-3, nitro-3, a group chosen from the following: 2,3,4-trimethoxybenzoyl;
2,3-dimethoxybenzoyl; 2,6-dimethoxybenzoyl; methoxy-2 nitro
3-bromo-5-benzoyl; 2-methoxy-3,5-dibromo-4-amino benzoyl;
3,5-dimethoxybenzoyl; 3,4-methylenedioxybenzyl; dinitro-3,5
benzoyl; 3,4,5-trimethoxybenzoyl; or a nicotinoyl nucleus of formula

or a benzyl monosubstitu ring in the ortho position of formula

in which R 6 represents a chlorine atom or a methoxy group, in which case A-CO- denotes the 2-amino-4-methoxy-5-pyrimidinylcarbonyl nucleus of formula

or a mono benzyl ring substituted in the meta position of formula

in which R7 represents
a methoxy group, in which case A-CO- denotes the 2-amino group
4-methoxy-5-pyrimidinylcarbonyl, or
a methyl or trifluoromethyl group OR a halogen atom,
in which case A-CO- denotes the 2-methoxy-4-amino-bromo-5-ring
benzoyl, or a monosubstituted benzyl ring in the para position of formula:

in which R8 represents
, a cyano group or a bromine atom, in which case A-CO- represents
the 2-amino-4-methoxy-5-pyrimidinylcarbonyl nucleus
a lower alkyl, trifluoromethyl or cyano group or an atom
halogen, in which case A-CO- represents a 2-methoxy-4-amino-nucleus
5-bromo-benzoyl, or
a fluorine atom, in which case A-CO- represents a methyl-2 ring
4-ethoxy-5-pyrimidinylcarbonyl of formula

in which case A-CO- represents a 2-methoxy-4-amino-5-bromo-benzoyl nucleus
or 2-methoxy-4-amino-5-chlorobenzoyl,
or a cyclohexylmethyl group, in which case A-CC-- represents a
2-methoxy-4-amino-5-bromo-5-benzoyl nucleus.

 It should be noted that in the formula (I '), the sequence A-CO-NH is in the equatorial position and the nor-tropanes bearing such a substituent in the equatorial position will be referred to as ss in what follows.

 The processes for the preparation of the derivatives of formula (I) and of the medicaments of formula (I ') are described below.

dans laquelle R' a la meme signification que dans la formule (I') et dont une partie constitue certains des dérivés de formule (I).Compounds of formula (I '), with the exception of those where A-CO- represents [(1-hydroxy-butyl) -5-methoxy-2-benzoyl] and [(1-hydroxy-2-methyl-propyl) groups). 5-methoxy-2-benzoyl are obtained by condensing, by the mixed anhydride method, the acids of formula
A '- COCH (II) in which A'-CO- has the same meanings as A-CO- in the formula (r), with the exception of the following meanings: [(1-hydroxy-butyl) -5 methoxy-2 ] benzoyl, [(1-hydroxy-2-methyl-propyl) -5-methoxy] benzoyl, with the corresponding -amino-3-nor-tropanes of the formula

in which R 'has the same meaning as in formula (I') and a part of which constitutes some of the derivatives of formula (I).

avec le composé de formule (III) où R'.représente le groupe benzyle.The compounds of formula (I) in which A-CO- represents [1- [1-hydroxy-butyl] -2-methoxy] benzoyl and [(1-hydroxy-2-methylpropyl) -5-methoxy] benzoyl are, as for them, obtained by reduction, preferably by sodium borohydride in methanolic medium, respectively of the compound of formula (I) for which A-CO- represents the group [(oxo-1-butyl) -5 methoxy-2] benzoyl and ss - {[(1-oxo-2-methylpropyl) -2-methoxy] benzoyl} 3-amino-N-benzyl nor-tropane. The latter is obtained by condensing, by the mixed anhydride method, the acid of formula

with the compound of formula (III) where R 'is the benzyl group.

The compound of formula (III) in which R 'represents the benzyl group is new and results from the reduction by sodium in amyl alcohol, of the oxime of N-benzyl nor-tropinone-3 of formula

dans lesquelles R6, R7 et R8 ont les mêmes significations que dans la formule (I') sur les composts de formule :

dans laquelle R9 représente les groupes méthyle ou éthoxy, cette condensation étant de préférence réalisée au reflux dans un solvant organique tel que l'acétone, l'acétonitrile ou le DMF en présence de carbonate de potassium ou de triéthylamine, puis à hydrolyser le groupe acétyle ou carbéthoxy des composés obtenus constituant certains des dérivés de formule (I). The compounds of formula (III) in which R'a have the same meanings as in formula (I '), with the exception of the benzyl group, are also new and are obtained by a two-step synthesis which consists in condensing the chloride cyclohexylmethyl, 3,4-dichlorobenzyl chloride, 2-chloromethyl thiophene, 3-chloromethyl thiophene, 2-chloromethyl furan or chlorides of formulas

in which R6, R7 and R8 have the same meanings as in formula (I ') on the composts of formula:

in which R 9 represents methyl or ethoxy groups, this condensation preferably being carried out under reflux in an organic solvent such as acetone, acetonitrile or DMF in the presence of potassium carbonate or triethylamine, and then hydrolyzing the acetyl group or carbethoxy compounds obtained constituting some of the derivatives of formula (I).

The novel compounds of formula (VI) are obtained by a two-step synthesis of treating the compound of formula (III) in which
R 'represents the benzyl group by acetyl chloride or ethyl chloroformate, in addition to tetrahydrofuran and in the presence of such an organic base. pyridine or triethylamine, and then hydrogenolyzing the product obtained which is one of the derivatives of formula (I), for example in the presence of 10% palladium on charcoal in an ethanolic medium, at a temperature of 60 ° C. and under a temperature of 60 ° C. pressure of 15 bar.

et où R'est différent du groupe benzyle, peuvent égarement être obtenus par condensation des composés de formules (V), (Va) où R7 = OCH3 et (Vb) où
R8 = CN, Br, avec le composé de formule :

The compounds of formula (r) in which the unit A-CO represents the group of formula

and where R is different from the benzyl group, can be misleadingly obtained by condensation of compounds of formulas (V), (Va) where R7 = OCH3 and (Vb) where
R8 = CN, Br, with the compound of formula:

 This condensation is preferably carried out according to a method identical to that used for the synthesis of the compounds of formula (III) where R is different from the benzyl group.

Finally, the compound of formula (VII) also new, is obtained by hydrogenolysis - preferably in an acidic medium, in the presence of 10% palladium on carbon, at room temperature, under a pressure of 90 mbar and in an alcoholic medium. compound of formula

avec le composé de formule (III) où R' est un groupe benzyle.The latter compound is prepared according to the process described above for the preparation of the compounds of formula (I ') [mixed anhydride method by condensing the acid of formula

with the compound of formula (III) where R 'is a benzyl group.

 The acid addition salts of the compounds of formula (I) can be obtained according to the usual methods. For example, the acid, such as hydrochloric, oxalic, maleic or fumaric acid, is added to the compounds of formula (r) in base form, in the presence of a suitable solvent such as ethanol for example.

 The following preparations are given by way of example to illustrate the invention.

Example 1: ss - [(4-amino-5-bromo-2-methoxy) benzoyl] 3-amino-N-parafluorobenzyl
nor-tropane hydrochloride (I ')
Code number 19
To a solution of 8.35 g of 4-amino-5-bromo-2-methoxybenzoic acid (II) in 200 ml of tetrahydrofuran cooled to 00 ° C., 5.18 ml of triethylamine and then 3.5 ml of chloroformate are added. ethyl. After 45 minutes at 00 ° C., 8.6 g of 3-amino-3-N-parafluorobenzyl nor-tropane [(III), prepared according to example 3, code number 1033 and stirring for 3 hours are added. The solvent is evaporated, the residue is taken up in methylene chloride, washed with carbonated water, then with water, dried over sodium sulfate, filtered and the solvent evaporated. The residue is crystallized in isopropyl ether. The precipitate obtained (12.9 g) is dissolved in 150 ml of ethanol, 6.5N hydrochloric ethanol is added, the precipitate obtained is filtered off, the residue is rinsed. the ether on the filter and recrystallizes it in absolute alcohol. 5 g of the expected product are thus obtained.

e Yield * 36%
; Melting point:> 265 C
. Molecular weight: 498.82
. Gross formula: C22H26BrClFN3O2
. Elemental analysis:

<tb><SEP> C <SEP> H <SEP> N
<tb> Calculated <SEP> (%) <SEP> 52.97 <SEP> 5.25 <SEP> 8.42
<tb> Found <SEP> (%) <SEP> 52.92 <SEP> 4.93 <SEP> 8.26
<Tb>
By the same method, but from the corresponding reagents, the compounds of formula (I ') appearing in Table I below, with the exception of compounds of code numbers 46 and 52, are obtained. TABLE I

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal. <SEP> 63.45 <SEP> 6.85 <SEP> 17.62
<tb> 17 <SEP> H2N # -CO- <SEP> -CH2- # <SEP> Base <SEP> C21H27N5O3 <SEP> 397.47 <SEP> 147 <SEP> 80 <SEP> Tr.
<Tb>

<SEP> OMe <SEP> 63.51 <SEP> 6.60 <SEP> 17.85
<tb> 18 <SEP>"<SEP> -CH2- # <SEP>"<SEP> C21H27N5O3 <SEP> 397.47 <SEP> 215 <SEP> 70 <SEP> Cal. <SEP> 63.45 <SEP> 6.85 <SEP> 17.62
<tb><SEP> MeO <SEP> Tr. <SEP> 63.20 <SEP> 6.90 <SEP> 17.52
<tb><SEP> OMe <SEP> Cal. <SEP> 52.97 <SEP> 5.25 <SEP> 8.42
<tb> 19 <SEP> H2N - # - CO- <SEP> -CH2 - # - F <SEP> HCl <SEP> C22H26BrClFN3O2 <SEP> 498.82 <SEP>> 260 <SEP> 36
<tb><SEP> Br <SEP> Tr. <SEP> 52.91 <SEP> 4.93 <SEP> 8.26
<tb> 20 <SEP>"<SEP> -CH2 - # - Br <SEP> Base <SEP> C22H25Br2N3O2 <SEP> 523.26 <SEP> 223 <SEP> 67 <SEP> Cal. <SEP> 50.49 <SEP> 4.82 <SEP> 8.03
<tb><SEP> Tr. <SEP> 50.68 <SEP> 4.67 <SEP> 7.86
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal. <SEP> 53.91 <SEP> 4.92 <SEP> 8.20
<tb> 21 <SEP> HWN - # - CO- <SEP> -CH2- # <SEP> Base <SEP> C23H25BrF3N3O2 <SEP> 529.36 <SEQ> 165 <SEP> 72
<tb><SEP> Br <SEP> CF3 <SEP> Tr. <SEP> 53.85 <SEP> 4.68 <SEP> 8.05
<tb><SEP> Cal. <SEP> 55.18 <SEP> 5.26 <SEP> 8.78
<tb> 22 <SEP>"<SEP> -CH2 - # - Cl <SEP>"<SEP> C22H25BrClN3O2 <SEP> 478.81 <SEP> 216 <SEP> 70 <SEP> Tr. <SEP> 55.12 <SEP> 5.24 <SEP> 8.86
<tb><SEP> Cal. <SEP> 60.26 <SEP> 6.16 <SEP> 9.17
<tb> 23 <SEP>"<SEP> -CH2 - # - CH3 <SEP>"<SEP> C23H28BrN3O2 <SEP> 458.39 <SEP> 217 <SEP> 71 <SEP> Tr. <SEP> 60.44 <SEP> 6.13 <SEP> 9.27
### , 16 <SEP> 9.17
<tb><SEP> CH3 <SEP> Tr. <SEP> 60.28 <SEP> 6.41 <SEP> 9.23
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cl <SEP> Cal. <SEP> 55.18 <SEP> 5.26 <SEP> 8.78
<tb> 25 <SEP> H2N - # - CO- <SEP> -CH2- # <SEP> Base <SEP> C22H25BrClN3O2 <SEP> 478.81 <SEQ> 189 <SEP> 58
<tb><SEP> Br <SEP> Tr. <SEP> 55.48 <SEP> 5.11 <SEP> 8.77
<tb><SEP> F <SEP> Cal. <SEP> 57.15 <SEP> 5.45 <SEP> 9.09
<tb> 26 <SEP>"<SEP> -CH2- # <SEP>"<SEP> C22H25BrFN3O2 <SEP> 462.35 <SEP> 167 <SEP> 55 <SEP> Tr. <SEP> 57.43 <SEP > 5.29 <SEP> 9.01
<tb><SEP> Br <SEP> Cal. <SEP> 51.49 <SEP> 4.82 <SEP> 8.03
<tb> 27 <SEP>"<SEP> -CH2- # <SEP>"<SEP> C22H25Br2N3O2 <SEP> 523.26 <SEP> 204 <SEP> 78 <SEP> Tr. <SEP> 50.58 <SEP > 4.79 <SEP> 8.27
<tb><SEP> Cl <SEP> Cal. <SEP> 51.48 <SEP> 4.71 <SEP> 8.19
<tb> 28 <SEP>"<SEP> -CH2 - # - Cl <SEP>"<SEP> C22H24BrCl2N3O2 <SEP> 513.26 <SEP> 193 <SEP> 76 <SEP> Tr. <SEP> 51.67 <SEP> 4.77 <SEP> 8.40
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal. <SEP> 53.33 <SEP> 5.37 <SEP> 9.33
<tb> 29 <SEP> H2N - # - CO- <SEP> -CH2- # <SEP> Base <SEP> C20H24BrN3O2S <SEP> 450.39 <SEP> 213 <SEP> 54
<tb><SEP> Br <SEP> Tr. <SEP> 53.15 <SEP> 5.26 <SEP> 9.40
<tb> 30 <SEP>"<SEP> -CH2 - # - And <SEP>"<SEP> C24H30BrN3O2 <SEP> 472.41 <SEP> 182 <SEP> 81 <SEP> Cal. <SEP> 61.01 <SEP> 6.40 <SEP> 8.90
<tb><SEP> Tr. <SEP> 60.92 <SEP> 6.45 <SEP> 8.98
<tb> 31 <SEP>"<SEP> -CH2- # <SEP>"<SEP> C20H24BrN3O3 <SEP> 434.32 <SEP> 210 <SEP> 76 <SEP> Cal. <SEP> 55.30 <SEP> 5.57 <SEP> 9.68
<tb><SEP> Tr. <SEP> 55.10 <SEP> 5.46 <SEP> 9.70
<tb> 32 <SEP>"<SEP> -CH2 # <SEP>"<SEP> C20H24BrN3O2S <SEP> 450.39 <SEP> 220 <SEP> 67 <SEP> Cal. <SEP> 53.33 <SEP> 5.37 <SEP> 9.33
<tb><SEP> Tr. <SEP> 53.40 <SEP> 5.44 <SEP> 9.31
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal. <SEP> 53.92 <SEP> 4.92 <SEP> 8.20
<tb> 33 <SEP> H2N - # - CO- <SEP> -CH2 - # - CF3 <SEP> Base <SEP> C23H25BrF3N3O2 <SEP> 512.36 <SEP> 201 <SEP> 58
<tb><SEP> Br <SEP> Tr. <SEP> 53.74 <SEP> 4.93 <SEP> 8.33
<tb> 34 <SEP>"<SEP> -CH2 - # - CN <SEP> Oxalste <SEP> C25H27BrN4O6 <SEP> 559.41 <SEP> 232 <SEQ> 45 <SEP> Cal. <SEQ> 53.67 <SEP> 4.87 <SEP> 10.02
<tb><SEP> Tr. <SEP> 53.39 <SEP> 4.98 <SEP> 9.72
<tb><SEP> Maleate <SEP> Cal. <SEP> 53.76 <SEP> 6.52 <SEP> 7.23
<tb> 35 <SEP>"<SEP> -CH2- # <SEP> + <SEP> 4/5 <SEP> H2O <SEP> C26H36BrN3O6 <SEP> 566.48 <SE> 160 <SEP> 48
<tb><SEP> +4/5 <SEP> H2O <SEP> Tr. <SEP> 53.50 <SEP> 5.16 <SEP> 7.23
<tb><SEP> OMe <SEP> Cal. <SEP> 64.27 <SEP> 6.16 <SEP> 21.42
<tb> 36 <SEP> H2N - # - CO- <SEP> -CH2 - # - CN <SEP> Base <SEP> C21H24N6O2 <SEP> 392.45 <SEP> 160 <SEP> 62 <SEP> Tr. <SEP> 64.02 <SEP> 6.11 <SEP> 21.23
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal. <SEP> 49.75 <SEP> 5.22 <SEP> 14.51
<tb> 37 <SEP> H2N - # - CO- <SEP> -CH2 - # - Br <SEP> HCl <SEP> C20H25BrClN5O2 <SEP> 482.81 <SEP> 230 <SEP> 51 <SEP> Tr. <SEP> 49.56 <SEP> 5.15 <SEP> 14.58
<tb> 38 <SEP>"<SEP> -CH2- # <SEP>"<SEP> C20H24ClN5O2 <SEP> 401.89 <SEP> 120 <SEP> 59 <SEP> Cal. <SEP> 59.77 <SEP> 6.02 <SEP> 17.43
<tb><SEP> Cl <SEP> Tr. <SEP> 60.03 <SEP> 6.14 <SEP> 17.63
<tb><SEP> EtO <SEP> 1.35 <SEP> Smoke <SEP> C22H27FN4O2 <SEP> 562.37 <SEP> 124 <SEP> 45 <SEP> Cal. <SEP> 58.52 <SEP> 5.95 <SEP> 9.96
<tb> 39 <SEP> CH3 - # - CO <SEP> -CH2 - # - F <SEP> spleen <SEP> + <SEP> + <SEP> 1.34 <SEP> fumarate
<tb><SEP> 2/5 <SEP> H2O <SEP> + <SEP> 2/5 <SEP> H2O <SEP> Tr. <SEP> 58.29 <SEP> 5.79 <SEQ> 9.59
<tb><SEP> OME <SEP> HCl <SEP> Cal. <SEP> 52.99 <SEP> 5.81 <SEP> 7.73
<tb> 40 <SEP> CH3CONH - # - CO- <SEP> -CH2- # <SEP> + <SEP> C24H29BrClN3O3 <SEP> 543.88 <SEQ> 217 <SEP> 54
<tb><SEP> Br <SEP> 1/6 <SEP> H2O <SEP> + <SEP> 1/6 <SEP> H2O <SEP> Tr. <SEP> 53.25 <SEP> 5.61 <SEP > 7.76
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal <SEP> 53.34 <SEP> 4.66 <SEP> 7.78
<tb> 41 <SEP> CF3CONH- # <SEP> -CH2- # <SEP> Base <SEP> C24H25BrF3N3O3 <SEP> 540.37 <SEP> 191 <SEP> 90
<tb><SEP> Br <SEP> Tr. <SEP> 53.64 <SEP> 4.92 <SEP> 7.92
<tb><SEP> OMe <SEP> Cal. <SEP> 65.22 <SEP> 6.39 <SEP> 9.51
<tb> 42 <SEP> CH2CONH - # - CO- <SEP>"<SEP>"<SEP> C24H28ClN3O3 <SEP> 441.94 <SE> 180 <SEP> 63
<tb><SEP> Cl <SEP> Tr. <SEP> 64.99 <SEQ> 6.69 <SEQ> 9.34
<tb><SEP> OMe <SEP> Cal. <SEP> 58.12 <SEP> 5.08 <SEP> 8.47
<tb> 43 <SEP> CF3CONH - # - CO- <SEP>"<SEP>"<SEP> C24H25ClF3N3O3 <SEP> 495.92 <SEQ> 181 <SEP> 63
<tb><SEP> Cl <SEP> Tr. <SEP> 58.35 <SEP> 5.35 <SEP> 8.60
<tb><SEP> OMe <SEP> Cal. <SEP> 61.54 <SEP> 5.87 <SEP> 6.53
<tb> 44 <SEP># -CO- <SEP>"<SEP>"<SEP> C22H25BrN2O2 <SEP> 429.34 <SEP> 146 <SEP> 87
<tb><SEP> Br <SEP> Tr. <SEP> 61.48 <SEP> 5.97 <SEP> 6.27
<tb> TABLE I (continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal. <SEP> 74.25 <SEP> 7.67 <SEP> 6.66
<tb> 45 <SEP> C3H7 # -CO- <SEP> -CH2 - # - Br <SEP> Base <SEP> C26H32N2O3 <SEP> 420.52 <SEP> 142 <SEP> 74 <SEP> Tr. <SEP > 74.39 <SEP> 7.91 <SEP> 6.56
<tb><SEP> O
<tb><SEP> OMe <SEP> Cal. <SEP> 73.90 <SEP> 8.11 <SEP> 6.63
<tb> 46 <SEP> C3H7 # -CO- <SEP>"<SEP>"<SEP> C26H34N2O3 <SEP> 422.55 <SEP> 150 <SEP> 59
<tb><SEP> OH <SEP> Tr. <SEP> 73.92 <SEP> 8.37 <SEP> 6.53
<tb><SEP> OMe <SEP> Cal. <SEP> 68.65 <SEP> 6.55 <SEP> 7.28
<tb> 47 <SEP># -CO- <SEP>"<SEP>"<SEP> C22H25ClN2O2 <SEP> 384.89 <SE> 132 <SEP> 82
<tb><SEP> Cl <SEP> Tr. <SEP> 68.50 <SEP> 6.46 <SEP> 7.01
<tb><SEP> OMe <SEP> Cal. <SEP> 66.82 <SEP> 6.37 <SEP> 10.63
<tb> 48 <SEP># -CO- <SEP>"<SEP>"<SEP> C22H25N3O4 <SEP> 355.44 <SE> 138 <SEP> 77
<tb><SEP> O2N <SEP> Tr. <SEP> 66.59 <SEP> 6.55 <SEP> 10.79
<tb> TABLE I (continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal <SEP> 71.71 <SEP> 6.84 <SEP> 7.60
<tb> 49 <SEP># -CO- <SEP> -CH2- # <SEP> Base <SEP> C22H25N2FO2 <SEP> 368.44 <SEP> 96 <SEP> 81
<tb><SEP> F <SEP> Tr. <SEP> 71.60 <SEP> 7.10 <SEP> 7.65
<tb><SEP> OMe <SEP> Cal. <SEP> 76.29 <SEP> 7.06 <SEP> 6.14
<tb> 50 <SEP># -CO- <SEP>"<SEP>"<SEP> C29H32N2O3 <SEP> 456.56 <SEP> 130 <SEP> 75
<tb><SEP>#<SEP> Tr. <SEP> 76.15 <SEP> 7.20 <SEP> 6.14
<tb><SEP> OMe <SEP> Cal. <SEP> 72.10 <SEP> 7.15 <SEP> 7.65
<tb> 51 <SEP># -CO- <SEP>"<SEP>"<SEP> C22H26N2O3 <SEP> 366.44 <SE> 195 <SEP> 57
<tb><SEP> HO <SEP> Tr. <SEP> 72.29 <SEP> 7.42 <SEP> 7.62
<tb><SEP> OMe <SEP> Cal. <SEP> 73.90 <SEP> 8.11 <SEP> 6.63
<tb> 52 <SEP># -CO- <SEP>"<SEP>"<SEP> C26H34H2O3 <SEP> 422.55 <SEQ> 180 <SEP> 62
<tb><SEP> OH <SEP> Tr. <SEP> 74.06 <SEP> 8.24 <SEP> 6.61
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> OMe <SEP> Cal. <SEP> 65.13 <SEP> 6.83 <SEP> 6.33
<tb> 53 <SEP># -CO- <SEP> -CH2- # <SEP> Base <SEP> C24H30N2O4S <SEP> 442.56 <SEP> 200 <SEP> 45
<tb><SEP> EtSO2 <SEP> Tr. <SEP> 65.08 <SEP> 6.93 <SEP> 6.31
<tb><SEP> OMe <SEP> Cal. <SEP> 72.99 <SEP> 6.93 <SEP> 7.40
<tb> 54 <SEP># -CO- <SEP>"<SEP>"<SEP> C23H26N2O3 <SEP> 378.45 <SE> 128 <SEP> 48
<tb><SEP> OCH <SEP> Tr. <SEP> 72.87 <SEP> 7.37 <SEP> 7.25
<tb><SEP> OMe <SEP> Cal. <SEP> 55.47 <SEP> 5.29 <SEP> 5.88
<tb> 55 <SEP># -CO- <SEP>"<SEP>"<SEP> C22H25N2IO2 <SEP> 476.34 <SEP> 153 <SEP> 69
<tb><SEP> I <SEP> Tr. <SEP> 55.56 <SEP> 5.28 <SEP> 6.05
<tb><SEP> OMe <SEP> Cal. <SEP> 72.30 <SEP> 7.45 <SEP> 11.50
<tb> 56 <SEP># -CO- <SEP>"<SEP>"<SEP> C22H27N3O2 <SEP> 365.46 <SE> 140 <SEP> 38
<tb><SEP> H2N <SEP> Tr. <SEP> 72.02 <SEP> 7.69 <SEP> 11.47
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> Cal. <SEP> 72.60 <SEP> 7.42 <SEP> 7.36
<tb><SEP> 57 <SEP>#<SEP>#<SEP> Base <SEP> C23H28N3O2 <SEP> 380.47 <SE> 134 <SEP> 82
<tb><SEP> Tr. <SEP> 72.75 <SEP> 7.15 <SEP> 7.51
<tb><SEP> Cal. <SEP> 73.57 <SEP> 6.71 <SEP> 11.19
<tb><SEP> 58 <SEP>#<SEP>"<SEP>"<SEP> C23H25N3O2 <SEP> 375.45 <SE> 127 <SEP> 76
<tb><SEP> Tr. <SEP> 71.41 <SEP> 6.71 <SEP> 10.64
<tb><SEP> Cal. <SEP> 64.46 <SEP> 6.59 <SEP> 6.54
<tb><SEP> 59 <SEP>#<SEP>"<SEP>"<SEP> C23H28N2O4S <SEP> 428.54 <SEP> 186 <SEP> 68
<tb><SEP> Tr. <SEP> 64.27 <SEP> 6.56 <SEP> 6.59
<tb><SEP> Cal. <SEP> 70.22 <SEP> 7.37 <SEP> 6.82
<tb><SEP> 60 <SEP>#<SEP>"<SEP>"<SEP> C23H30N2O4 <SEP> 410.49 <SE> 130 <SEP> 73
<tb><SEP> Tr. <SEP> 70.07 <SEP> 7.18 <SEP> 6.72
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> HCl <SEP> Cal. <SEP> 62.97 <SEP> 7.09 <SEP> 6.12
<tb><SEP> 61 <SEP>#<SEP>#<SEP> + <SEP> C24H31N4O2 <SEP> 457.77 <SEP> 220 <SEP> 57
<tb><SEP> 3/5 <SEP> H2O <SEP> +3 / 5 <SEP> H2O <SEP> Tr. <SEP> 63.26 <SEP> 7.11 <SEP> 6.08
<tb><SEP> HCl <SEP> Cal. <SEP> 68.29 <SEP> 7.03 <SEP> 7.24
<tb><SEP> 62 <SEP>#<SEP>"<SEP> + <SEP> C22H27N2O2 <SEP> 390.51 <SEP>> 260 <SEP> 61
<tb><SEP> 1/5 <SEP> H2O <SEP> + <SEP> 1/5 <SEP> H2O <SEP> Tr. <SEP> 67.78 <SEP> 7.36 <SEP> 7.46
<tb><SEP> Cal. <SEP> 68.90 <SEP> 7.29 <SEP> 6.99
<tb><SEP> 63 <SEP>#<SEP>"<SEP> HCl <SEP> C23H29N2O2 <SEP> 400.93 <SEP>> 260 <SEP> 68
<tb><SEP> Tr. <SEP> 68.61 <SEP> 7.63 <SEP> 6.84
<tb><SEP> Base <SEP> Cal. <SEP> 70.38 <SEP> 7.50 <SEP> 7.14
<tb><SEP> 64 <SEP>#<SEP>"<SEP> + <SEP> C23H28N2O3 <SEP> 392.48 <SE> 78 <SEP> 85
<tb><SEP> 2/3 <SEP> H2O <SEP> + <SEP> 2/3 <SEP> H2O <SEP> Tr. <SEP> 70.23 <SEP> 7.39 <SE> 7.04
<tb> TABLE (Suite0

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> Cal. <SEP> 71.76 <SEP> 7.17 <SEP> 11.96
<tb><SEP> 65 <SEP>#<SEP>#<SEP> Base <SEP> C21H25N3O2 <SEP> 351.45 <SEQ> 142 <SEP> 62
<tb><SEP> Tr. <SEP> 71.36 <SEP> 7.30 <SEP> 11.90
<tb><SEP> Cal. <SEP> 72.60 <SEP> 7.42 <SEP> 7.36
<tb><SEP> 66 <SEP>#<SEP>"<SEP>"<SEP> C23H28N2O3 <SEP> 385.47 <SE> 154 <SEP> 87
<tb><SEP> Tr. <SEP> 72.59 <SEP> 7.67 <SEP> 7.14
<tb><SEP> Cal. <SEP> 72.30 <SEP> 7.45 <SEP> 11.50
<tb><SEP> 67 <SEP>#<SEP>"<SEP>"<SEP> C22H27N3O2 <SEP> 365.46 <SE> 145 <SEP> 47
<tb><SEP> Tr. <SEP> 72.40 <SEP> 7.78 <SEP> 11.37
<tb><SEP> Cal. <SEP> 66.25 <SEP> 7.01 <SEP> 6.72
<tb><SEP> 68 <SEP>#<SEP>"<SEP> HCl <SEP> C23H29N2O3 <SEP> 416.93 <SEP> 209 <SEP> 53
<tb><SEP> Tr. <SEP> 66.18 <SEP> 7.11 <SEP> 6.85
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> Cal. <SEP> 55.70 <SEP> 5.10 <SEP> 8.86
<tb><SEP> 69 <SEP>#<SEP>#<SEP> Base <SEP> C22H24BrN3O4 <SEP> 474.34 <SEQ> 142 <SEP> 73
<tb><SEP> Tr. <SEP> 55.46 <SEP> 5.13 <SEP> 8.92
<tb><SEP> Base <SEP> Cal. <SEP> 69.96 <SEP> 7.22 <SEP> 10.20
<tb><SEP> 70 <SEP>#<SEP>"<SEP> + <SEP> C24H29N3O3 <SEP> 412.00 <SE> 206 <SEP> 49
<tb><SEP> 1/4 <SEP> H2O <SEP> + <SEP> 1/4 <SEP> H2O <SEP> Tr. <SEP> 70.29 <SEP> 7.50 <SEP> 10.40
<tb><SEP> Cal. <SEP> 61.61 <SEP> 6.21 <SEP> 10.78
<tb><SEP> 71 <SEP>#<SEP>#<SEP> Base <SEP> C20H24ClN3O2 <SEP> 389.87 <SEP> 220 <SEP> 51
<tb><SEP> Tr. <SEP> 61.92 <SEP> 6.34 <SEP> 11.02
<tb><SEP> Cal. <SEP> 59.17 <SEP> 5.96 <SEP> 10.35
<tb><SEP> 72 <SEP>"<SEP>#<SEP>"<SEP> C20H24ClN3O2S <SEP> 405.94 <SEP> 227 <SEP> 58
<tb><SEP> Tr. <SEP> 59.15 <SEP> 5.91 <SEP> 10.12
<tb> Table I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> Cal. <SEP> 59.17 <SEP> 5.96 <SEP> 10.35
<tb><SEP> 73 <SEP>#<SEP>#<SEP> Base <SEP> C20H24N3O2S <SEP> 405.94 <SEP> 215 <SEP> 47
<tb><SEP> Tr. <SEP> 59.13 <SEP> 5.64 <SEP> 10.37
<tb><SEP> HCl <SEP> Cal. <SEP> 45.45 <SEP> 4.92 <SEP> 7.23
<tb><SEP> 74 <SEP>#<SEP>#<SEP> + <SEP> C22H26Br2ClN3O2 <SEP> 581.35 <SEQ> 208 <SEP> 36
<tb><SEP> 1.2 <SEP> H2O <SEP> + <SEP> 1.2 <SEP> H2O <SEP> Tr. <SEP> 45.69 <SEP> 4.77 <SEP> 7.11
<tb><SEP> Cal. <SEP> 56.45 <SEP> 5.62 <SEP> 7.32
<tb><SEP> 75 <SEP>#<SEP>"<SEP> fumarate <SEP> C27H32BrN3O6 <SEP> 574.46 <SEP> 212 <SEP> 45
<tb><SEP> Tr. <SEP> 56.45 <SEP> 5.74 <SEP> 7.33
<tb><SEP> Cal. <SEP> 66.93 <SEP> 6.48 <SEP> 6.01
<tb><SEP> 76 <SEP>#<SEP>"<SEP> maleate <SEP> C26H30N2O6 <SEP> 466.52 <SEQ> 198 <SEP> 53
<tb><SEP> Tr. <SEP> 66.84 <SEP> 6.58 <SEP> 5.98
<tb> TABLE (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> Cal. <SEP> 68.29 <SEP> 7.03 <SEP> 7.24
<tb><SEP> 77 <SEP>#<SEP>#<SEP> HCl <SEP> C22H27N2O2 <SEP> 386.91 <SE> 222 <SEP> 65
<tb><SEP> Tr. <SEP> 68.01 <SEP> 7.15 <SEP> 7.25
<tb><SEP> Cal. <SEP> 67.28 <SEP> 6.18 <SEP> 7.47
<tb><SEP> 78 <SEP>#<SEP>"<SEP>"<SEP> C21H24ClFN2O <SEP> 374.87 <SE>> 260 <SEP> 58
<tb><SEP> Tr. <SEP> 67.50 <SEP> 6.56 <SEP> 7.47
<tb><SEP> Cal. <SEP> 64.45 <SEP> 6.18 <SEP> 7.16
<tb><SEP> 79 <SEP>#<SEP>"<SEP>"<SEP> C21H24Cl2N2O <SEP> 391.33 <SEP>> 260 <SEP> 65
<tb><SEP> Tr. <SEP> 64.33 <SEP> 6.43 <SEP> 7.07
<tb><SEP> Cal. <SEP> 71,24 <SEP> 7,34 <SEP> 7,55
<tb><SEP> 80 <SEP>#<SEP>"<SEP>"<SEP> C22H27ClN2O <SEP> 370.91 <SEP>> 64 <SEP> 64
<tb><SEP> Tr. <SEP> 71.49 <SEP> 7.59 <SEP> 7.29
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> Cal. <SEP> 64.45 <SEP> 6.18 <SEP> 7.16
<tb><SEP> 81 <SEP>#<SEP>#<SEP> HCl <SEP> C21H24Cl2N2O <SEP> 391.33 <SEQ> 240 <SEP> 55
<tb><SEP> Tr. <SEP> 64.14 <SEP> 6.34 <SEP> 7.16
<tb><SEP> Cal. <SEP> 69.02 <SEP> 6.34 <SEP> 11.50
<tb><SEP> 82 <SEP>#<SEP>"<SEP> Base <SEP> C21H23N3O3 <SEP> 365.42 <SE> 140 <SEP> 81
<tb><SEP> Tr. <SEP> 69.04 <SEP> 6.43 <SEP> 11.60
<tb><SEP> Cal. <SEP> 72.60 <SEP> 7.42 <SEP> 7.36
<tb><SEP> 83 <SEP>#<SEP>#<SEP>"<SEP> C23H28N2O3 <SEP> 380.47 <SE> 182 <SEP> 91
<tb><SEP> Tr. <SEP> 72.52 <SEP> 7.41 <SEP> 7.25
<tb><SEP> HCl <SEP> Cal. <SEP> 63.07 <SEP> 6.50 <SEP> 6.69
<tb><SEP> 84 <SEP>#<SEP>"<SEP> + <SEP> C22H27ClN2O4 <SEP> 418.91 <SE> 168 <SEP> 56
<tb><SEP> 1 <SEP> H2O <SEP> Tr. <SEP> 63.04 <SEP> 6.80 <SEP> 6.63
<tb> TABLE I (Continued)

No. <SEP> Weight <SEP> Item <SEP> ANALYSIS <SEP> ELEMENTARY
<tb> of <SEP> A-CO- <SEP> R '<SEP> Form <SEP> Formula <SEP> Raw <SEP> Molecule <SEP> of <SEP> Rende
Code <SEP> laire <SEP> merge <SEP> ment
<tb><SEP> (C) <SEP> (%) <SEP>% <SEP> C <SEP> H <SEP> N
<tb><SEP> Cal. <SEP> 61.45 <SEP> 5.40 <SEP> 13.65
<tb><SEP> 85 <SEP>#<SEP>#<SEP> Base <SEP> C21H22N4O5 <SEP> 410.42 <SEQ> 169 <SEP> 82
<tb><SEP> Tr. <SEP> 61.38 <SEP> 5.26 <SEP> 13.84
<tb><SEP> Cal. <SEP> 70.22 <SEP> 7.37 <SEP> 6.82
<tb><SEP> 86 <SEP>#<SEP>"<SEP>"<SEP> C24H30N2O4 <SEP> 410.49 <SEP> 188 <SEP> 79
<tb><SEP> Tr. <SEP> 70.30 <SEP> 7.48 <SEP> 6.83
<tb><SEP> Cal.
<Tb>

<SEP> Tr.
<Tb>

<SEP> Cal.
<Tb>

<SEP> Tr.
<Tb>

Example 2: ss - [(2-Amino-4-methoxy-pyrimidinyl) -5-carbonyl] amino-3N-para
bromobenzyl nor-tropane (I ')
Code number: 37
1st stage: ss- [(2-amino-4-methoxy-pyrimidinyl) -5-carbon)
amino-3 nor-tropane (VII)
The autoclave is hydrogenolyzed at room temperature and under a pressure of 90 mbar in the presence of 25 g of 10% palladium on carbon, a solution of 148.5 g of ss - [(2-amino-4-methoxy-pyrimidinyl) maleate) 5-carbonyl] 3-amino-N-benzyl nor-tropane {(I '), obtained according to Example 1,
Melting point: 1850 C, empirical formula: C20H25N5O2 + 1/6 H20,
Elemental analysis: Calculated (%): C, 64.84; H, 6.89; N: 18.91
Found (%): C, 64.62; H, 6.86; N: 19.35 in 1500 ml of 50% alcohol. The mixture is then filtered, the solvent evaporated, the residue crystallized from acetone and recrystallized from 90% alcohol. Thus, 120 g of the desired product are isolated.

. Yield: 96 S
Melting point: 2200 C
. Molecular Weight ": 412.41
. Gross formula: C17H25N5O6 + 7/5 H2O
. Elemental analysis:

<tb><SEP> C <SEP>#<SEP><SEP> H <SEP> N
<tb> Calculated <SEP> (%) <SEP> 48.69 <SEP> 6.01 <SEP> 16.98
<tb> Found <SEP> (%) <SEP> 48.97 <SEP> 6.19 <SEP> 16.84
<Tb>
2nd stage: ss - [(2-amino-4-methoxy-pyrimidinyl) -5 carbonyl]
amino-3 N-para bromobenzyl nor-tropane hydrochloride (I)
Code number: 37
To a solution of 7 g of succinate of the compound (VII) obtained previously in 100 ml of acetone is added 9.8 g of potassium carbonate and then.

5.3 g of para-bromobenzyl chloride. The mixture is then refluxed for 39 hours, the solvent is evaporated off, the residue is diluted with water and extracted with chloroform. It is dried over sodium sulfate, the solvent is evaporated off, the residue is crystallized from isopropyl ether and recrystallized from normal butyl alcohol. The product obtained is dissolved in the alcohol and the hydrochloric ethanol # 6.5 N is added, and the precipitate obtained is filtered off.

. Yield: 51%. Melting point: 2300 ° C. Molecular weight: 482.81. Crude formula: C20H25BrClN5O2. Elemental analysis:

<tb><SEP> C <SEP> H <SEP> H <SEP> N
<tb> Calculated <SEP> (g) <SEP> 49.75 <SEP> 5.22 <SEP> 14.51
<tb> Found <SEP> (%) <SEP> 49.56 <SEP> 5, t5 <SEP> 14.58
<Tb>
By the same method, but from the corresponding reagents, the compounds of formula (I ') appearing in Table I and bearing the code numbers: 17, 18, 36 and 38 are obtained.

Example 3: 3-amino-3-N-parafluorobenzyl-nor-tropane (III)
Code number: 103
1st stage: ss-acetamido-3 nor-tropane (VI)
To a cooled solution at 0 ° C of 96 g of ss-amino-3-N-benzyl nor-tropane (III) in 70 ml of triethylamine and 900 ml of tetrahydrofuran, 28 ml of acetyl chloride are added slowly. After 12 hours at room temperature, 50 ml of water are added, the solvent is evaporated, the remaining aqueous phase is extracted with methylene chloride (200 ml), washed with water, dried over sodium sulphate and the solvent is evaporated. 80 g of crude product which is dissolved in 1000 ml of alcohol 1 l of 5N hydrochloric alcohol ei; The solution is hydrogenolyzed in the presence of 8 g of 10% palladium on carbon, in an autoclave, at a temperature of 60 ° C. and a pressure of 15 bar. Then filtered, evaporated the filtrate and crystallized the residue in ethyl acetate
52 g of the expected product are thus isolated.

Yield: 77%
NMR spectrum: CDCl3:
#ppm = 6.38, d, (J = 7 Hz) - CONH- (exchangeable); focused on
m, 1H tropanic at 3;
3.60, m, tropanic protons in 1 and 5
2.70, s, 1 H - ME -, exchangeable;
% 1.96, s, 3H (CH3CO)
By the same method, using ethyl chloroformate instead of acetyl chloride, there is obtained 3-ethoxycarbonyl-3-aminopropane (VI).

. Melting point: 2520 ° C
. Molecular weight: 234.72
. Crude formula: C10H19ClN2O2 Elemental analysis

<tb> c <SEP> H <SEP> R
<tb><SEP> Calculated <SEP> (%) <SEP> 51.17 <SEP> 8.16 <SEP> 11.94
<tb><SEP> Found <SEP> (%) <SEP> 50.98 <SEP> 8.05 <SEP> 11.98
<Tb>
NMR Spectrum (CDCl3)
# ppm: 5.55, d, -NH-COO 4.08, q, g, and 1.18, t (J = 7 Hz) - COOCH2-CH3
1.96 s, NH
3.51, m, tropanic protons in 1 and 5
3.91, m, 1 tropanic proton in 3
centered on 1.72, m, tropanic protons in 2, 4, 6 and 7
2nd stage:, S-amino3 N-parafluorobenzyl nor-tropane (III)
Code number: 103
A solution of 17 g of ss-acetamido-3-nor-tropane VI (obtained in the preceding stage) is refluxed for 12 hours. 21 ml of p-fluorobenzyl chloride and 18 ml of triethylamine in 250 ml of acetone. Then the mixture is filtered, the filtrate is evaporated, the residue dissolved in methylene chloride (200 ml), washed with water, dried over sodium sulphate and the solvent evaporated. 21 g of crude product are obtained, which is dissolved in 250 ml of 10% sulfuric acid, and the solution is refluxed for 24 hours. It is washed with 100 ml of methylene chloride and the aqueous solution is made alkaline with water. the concentrated potash, extracted with methylene chloride, dried over sodium sulphate and evaporated the solvent. 17 g of crude product (yield: 96%) is obtained which is used directly in the synthesis of the corresponding compound of formula (I) (code number 19) described in Example 1.

. NMR spectrum of the compound of code number 103 (CDCl 3)
# mmp = center on 7,08, m, and 3,52, s, 6H benzyl.

centered on 3.15, m, tropanic protons in 1 and 5
centered on 2.94, m, 1 tropanic proton in 3
between 2.20 and 1.15, m, 8 tropanic protons
1,11, s, NH2 * exchangeable
By the same method, but starting from the ss-ethoxycarbonyl amino-3-nor tropane VI described in the previous stage, there is also obtained 0-amino-3-N para-fluorobenzyl nor-tropane (III) of code number 103.

 By the same method, but from the corresponding reagents, are obtained ss-amino-3 N-nor tropanes (III). Except for the few compounds of structure (III) collected in Table II below, the majority of the compounds (III) were used crude (after control by thin layer chromatography) in the synthesis of the corresponding compounds (r).

Example 4: ss {[(1-hydroxy-butyl) -5-methoxy-2] benzoylamino-3 N-benzyl
nr-tropane (I ')
Code number: 46
To a suspension of 8.5 g of ss {[(1-oxo-1-butyl) -2-methoxy] benzoyl} 3-amino-N-benzyl nor-tropane [(I), code number 45, obtained according to the example 1] in 200 ml of methanol cooled to 5 ° C., 2.7 g of sodium borohydride are added. Then it is allowed to return to ambient temperature for 1 hour, the methanol is evaporated off, the residue is taken up in a mixture of water and ethyl acetate, acidified with 5% HCl, rendered alkaline with dilute NaOH, the phase decanted. The mixture is washed with water and dried over sodium sulfate. The mixture is filtered, the filtrate is evaporated and crystallized and the residue is recrystallized from absolute alcohol (5 g).

. Yield: 59%
. Melting point: 1500 C
. Molecular weight: 422.59
Gross formula: C26H34N203
. Elemental analysis

<tb><SEP> C <SEP> H <SEP> N
<tb> Calculated <SEP> (%) <SEP> 73.90 <SEP> 8.11 <SEP> 6.63
<tb> Found <SEP> (%) <SEP> 73.92 <SEP> 8.37 <SEP> 6.54
<Tb>
By the same method, but starting from ss - {[(1-oxo-2-methylpropyl) -5-methoxy] benzoyl} 3-amino-N-benzyl nor-tropane [prepared according to the protocol described in Example 1, point melting point: 1980 C; crude formula C26H32N2O3 molecular weight: 420.53; elemental analysis. Calculates (%) C: 74.25
H: 7.67, N: 6.66 - Found (%) C, 74.54; H, 7.80; N is obtained the compound of formula (I ') of code number 52 appearing in Table I.

TABLE II

<SEP> Point
<tb> No. <SEP> Weight <SEP> of <SEP> Rendede <SEP> R '<SEP> Form <SEP> Formula <SEP> gross <SEP> molecular- <SEP> merge <SEP> ment <SEP><SEP> elementary analysis <SEP> or <SEP> spectrum <SEP> NMR
<tb> Code <SEP> laire <SEP> (C) <SEP> (%)
<tb><SEP> C <SEP> H <SEP> N
<tb><SEP> 98 <SEP>#<SEP> dimaleate <SEP> C22H28N2O8 <SEP> 462.87 <SEP> 150 <SEP> 59 <SEP> Calculated <SEP> (%) <SEP> 57.08 <SEP> 6.45 <SEP> 6.05
<tb><SEP> + <SEP> 4.5 <SEP> H2O <SEP> Found <SEP> (%) <SEP> 57.14 <SEP> 6.19 <SEP> 5.92
<tb><SEP> NMR <SEP> (CDCl3) <SEP>#<SEP> ppm = 7.32, m, <SEP> and <SEP> 3.48, s <SEP> 6H <SEP> CH2 # - Br
<tb><SEP> = 3.15, m <SEP>: <SEP> H <SEP> in <SEP> 1 <SEP> and <SEP> 5
<tb><SEP> 99 <SEP>#<SEP> base <SEP> C14H19BrN2 <SEP> 295.22 <SEP> (oil) <SEP> 63 <SEP> = <SEP> 2.94, m <SEP> : <SEP> H <SEP> in <SEP> 3
<tb><SEP> between <SEP> 2.20 <SEP> and <SEP> 1.25, <SEP> m, <SEP> H <SEP> in <SEP> 2,4,6 <SEP> and <SEP> 7
<tb><SEP> = <SEP> 1.10. <SEP> s: <SEP> NH2
<tb><SEP> NMR <SEP> (CDCl3) <SEP># ppm = 7.51, m <SEP> and <SEP> 3.59, s <SEP> 6H <SEP> CH2 # CF3
<tb><SEP> = 3.15, m <SEP>: <SEP> H <SEP> in <SEP> 1 <SEP> and <SEP> 5
<tb> 100 <SEP>#<SEP> base <SEP> C15H19F3N2 <SEP> 284.32 <SEP> (oil) <SEP> 71 <SEP> = <SEP> 2.92 <SEP>: <SEP> H <SEP> in <SEP> 3
<tb><SEP> between <SEP> 2.20 <SEP> and <SEP> 1.15, <SEP> m <SEP>: <SEP> H <SEP> in <SEP> 2,4,6, <SEP> and <SEP> 7
<tb><SEP> = <SEP> 1, <SEP> 17, <SEP> s <SEP>: <SEP> NH2
<tb><SEP> NMR <SEP> (CDCl3) <SEP># ppm = 7.47, m <SEP> and <SEP> 3.58, s <SEP> 6H <SEP> CH2 # Br
<tb><SEP> = 3.15, m <SEP>: <SEP> and <SEP> 2.95, m <SEP>: <SEP> H <SEP> into <SEP> 1.3 <SEP> and <SEP> 5
<tb> 101 <SEP>#<SEP> base <SEP> C14H19BrN2 <SEP> 295.22 <SEP> (oil) <SEP> 52 <SEP> between <SEP> 2.20 <SEP> and <SEP> 1 , 50, <SEP> m <SEP>: <SEP> H <SEP> in <SEP> 2,4,6 <SEP> and <SEP> 7
<tb><SEP> = <SEP> 1.42, <SEP> s, <SEP>: <SEP> NH2
<tb> TABLE II (Continued)

<SEP> Point
<tb> No. <SEP> Weight <SEP> of <SEP> Rendede <SEP> R '<SEP> Form <SEP> Formula <SEP> gross <SEP> molecular- <SEP> merge <SEP> ment <SEP><SEP> elementary analysis <SEP> or <SEP> spectrum <SEP> NMR
<tb> Code <SEP> laire <SEP> (C) <SEP> (%)
<tb><SEP> NMR <SEP> (CDCl3) <SEP>#<SEP> ppm = 7.10, m, <SEP> and <SEP> 3.55, s <SEP> 6H <SEP> CH2 #
<tb><SEP> = 3.15, m <SEP>: <SEP> and <SEP> 2.94m <SEP>: <SEP> H <SEP> in <SEP> 1.3 <SEP> and <SEP > 5
<tb> 102 <SEP>#<SEP> base <SEP> C14H19FN2 <SEP> 234.31 <SEP> (oil) <SEP> 66 <SEP> between <SEP> 2.20 <SEP> and <SEP> 1 , 18, <SEP> m, <SEP>: <SEP> H <SEP> in <SEP> 2,4,6 <SEP> and <SEP> 7
<tb><SEP> = <SEP> 1.14, s, <SEP> NH2
<tb><SEP> NMR <SEP> (CDCl3) <SEP># ppm = 7.08, m <SEP> and <SEP> 3.52, s <SEP> 6H <SEP> CH2 # F
<tb><SEP> = 3.15, m <SEP>: <SEP> H <SEP> in <SEP> 1 <SEP> and <SEP> 5
<tb> 103 <SEP>#<SEP> basis <SEP> C14H19FN2 <SEP> 234.31 <SEP> (oil) <SEP> 96 <SEP> = <SEP> 2.94 <SEP>: <SEP> H <SEP> in <SEP> 3
<tb><SEP> between <SEP> 2.20 <SEP> and <SEP> 1.15, <SEP> m <SEP>: <SEP> H <SEP> in <SEP> 2,4,6, <SEP> and <SEP> 7
<tb><SEP> = <SEP> 1, <SEP> 11, <SEP> s, <SEP>: <SEP> NH2
<Tb>
The tormule drifts (I ') have been studied in laboratory animals and have shown neuroleptic properties.

 These properties have been demonstrated in mice, in particular by the apomorphine uptake antagonism test, carried out according to the protocol described by G. GOURET et al. in J. Pharmacol. (Paris) 1973, k, 341.

 The effective doses obtained by intraperitoneally administering, according to the above test, the derivatives of formula (I ') and SULPIRIDE chosen as the control compound are shown in Table III below.

 Acute toxicity was studied in the mouse intraperitoneally and the lethal doses estimated according to the method described by Miller and Thinter Proc. Soc. Exper. Biol. Med. 1944, 57, 261, are also listed in Table III.

TABLE III

<tb> Compounds <SEP> tested <SEP> Toxicity <SEP> acute <SEP> (mouse) <SEP> Recovery <SEP> apomorphine
<tb><SEP> LD <SEP> 50 <SEP> mg / kg / ip) <SEP> DE <SEP> 50 <SEP> (mg / kg / ip)
<tb><SEP> SULPIRIDE <SEP> 170 <SEP> 37
<tb><SEP> 17
<tb><SEP> 18
<tb><SEP> 19
<tb><SEP> 20 <SEP>> 400 <SEP> 0.03
<tb><SEP> 21 <SEP> 85 <SEP> 0.07
<tb><SEP> 22 <SEP> 140 <SEP> 0.021
<tb><SEP>.<SEP> 23 <SEP>><SEP> 400 <SEP> 0.07
<tb><SEP> 24 <SEP> 160 <SEP> 0.05
<tb><SEP> 25 <SEP> 100 <SEP> 0.03
<tb><SEP> 26 <SEP> 140 <SEP> 0.011
<tb><SEP> 27
<tb><SEP> 28 <SEP>#<SEP>><SEP> 400 <SEP> 0.12
<tb><SEP> 29 <SEP> 180 <SEP> 0.012
<tb><SEP> 30 <SEP> 230 <SEP> 0.3
<tb><SEP> 31 <SEP> 150 <SEP> 0.17
<tb><SEP> 32 <SEP> 140 <SEP> 0.05
<tb><SEP> 33 <SEP>><SEP> 400 <SEP> 0.19
<tb><SEP> 34 <SEP> 50 <SEP> 0.06
<tb><SEP> 35 <SEP> 80 <SEP> 0.07
<tb><SEP> 36 <SEP> 275 <SEP> 0.9
<tb><SEP> 37 <SEP> 170 <SEP> 0.16
<tb><SEP> 38 <SEP> 150 <SEP>, 17 <SEP>
<tb><SEP> 39 <SEP> 140 <SEP> o, <SEP> i8 <SEP>
<tb><SEP> 40 <SEP> 130 <SEP> 0.05
<tb><SEP> 41 <SEP> 225 <SEP> 0.03
<tb><SEP> 42 <SEP> 61 <SEP> 0.05
<tb><SEP> 43 <SEP> 120 <SEP> 0.03
<tb><SEP> 44 <SEP> 140 <SEP> 0.25
<tb><SEP> 45 <SEP> 55 <SEP> 2.5
<tb><SEP> 46 <SEP> 125 <SEP> 3
<tb><SEP> 47 <SEP> 100 <SEP> 0.16
<Tb>
TABLE III (Continued)

<tb> Compounds <SEP> tested <SEP> Toxicity <SEP> acute <SEP> (mouse <SEP> Recovery <SEP> apomorphine
<tb><SEP> LD <SEP> 50 <SEP> mg / kg / ip) <SEP> DE <SEP> 50 <SEP> (mg / kg / ip) <SEP>
<tb><SEP> 48 <SEP> 310 <SEP> 0.21
<tb><SEP> 49 <SEP> 120 <SEP> 9.08 <SEP>
<tb><SEP> 50 <SEP> 300 <SEP> 0.32
<tb><SEP> 51 <SEP> 140 <SEP> 0.03
<tb><SEP> 52 <SEP> 140 <SEP> 0.95
<tb><SEP> 53 <SEP> 350 <SEP> 12.5
<tb><SEP> 54 <SEP> 330 <SEP> 8.8
<tb><SEP> 55 <SEP> 85 <SEP> 0.48
<tb><SEP> 56 <SEP> 80 <SEP> 0.84
<tb><SEP> 57 <SEP> 105 <SEP> 0.09
<tb><SEP> 58 <SEP> 85 <SEP> 0.96
<tb><SEP> 59 <SEP> 325 <SEP> 1.6
<tb><SEP> 60 <SEP> 75 <SEP> 0.027
<tb><SEP> 61 <SEP> 80 <SEP> 0.02
<tb><SEP> 62 <SEP> 60 <SEP> 0.04
<tb><SEP> 63 <SEP> 65 <SEP> 0.12
<tb><SEP> 64 <SEP> 83 <SEP> 0.008
<tb><SEP> 65 <SEP> 180 <SEP> 3.1
<tb><SEP> 66 <SEP> 160 <SEP>#<SEP> 0.11
<tb><SEP> 67 <SEP> 100 <SEP> 0.038
<tb><SEP> 68 <SEP> 47 <SEP> 0.02
<tb><SEP> 69 <SEP> 85 <SEP> 0.36
<tb><SEP> 70 <SEP> 190 <SEP> 0.3
<tb><SEP> 71 <SEP> 120 <SEP> 0.11
<tb><SEP> 72 <SEP> 110 <SEP> 0.04
<tb><SEP> 73 <SEP> 170 <SEP> 0.02
<tb><SEP> 74 <SEP> 250 <SEP> 0.035
<tb><SEP> 75 <SEP>><SEP> 400 <SEP> 0.021
<tb><SEP> 76 <SEP> 110 <SEP> 1.40
<tb><SEP> 77 <SEP> 85 <SEP> 3
<tb><SEP> 78 <SEP> 24 <SEP> 0.85
<tb><SEP> 79 <SEP> 87 <SEP> 0.34
<tb><SEP> 80 <SEP> 77 <SEP> 2,3
<Tb>
TABLE III (Continued)

<tb> Compounds <SEP> tested <SEP> Toxicity <SEP> acute <SEP> (mouse <SEP> Recovery <SEP> apomorphine
<tb><SEP> LD <SEP> 50 <SEP> mg / kg / ip) <SEP> DE <SEP> 50 <SEP> (mg / kg / ip)
<tb><SEP> 81 <SEP> 60 <SEP> 1.6
<tb><SEP> 82 <SEP> 80 <SEP> 2.7
<tb><SEP> 83 <SEP> 140 <SEP> 0.031
<tb><SEP> 84 <SEP> 432 <SEP> 0.9
<tb><SEP> 85 <SEP> 325 <SEP> 2,2
<tb><SEP> 86 <SEP> 200 <SEP> 3.8
<Tb>
As can be seen from the results expressed in this table, the difference between the effective doses and the lethal doses 50 is sufficient to allow the use of derivatives of formula (I ') as therapeutics.

 These are particularly indicated in the treatment of psyche disorders.

 They will be administered orally in the form of tablets, dragees or capsules containing from 50 to 300 mg of active ingredient (3 to 8 per day), in the form of a solution containing 0.1 to 1% of active principle (10 to 60 drops). , one to three times daily), parenterally in the form of injectable ampoules containing 5 to 100 mg of active ingredient (3 to 8 ampoules per day)

Claims (1)

 CLAIM  Novel 3-amino-3-nor-tropane derivatives, characterized in that they correspond to the formula

 in which R represents  - a hydrogen atom or a benzoyl group, methyl-3 benzoyl,  3-chlorobenzoyl, 3-fluorobenzyl, 4-methylbenzyl, 4-fluoro-benzyl,  4-chlorobenzyl or cyclohexylmethyl, Y being then a group  ethoxycarbonyl  - a 2-chlorobenzyl group, 2-methoxy benzyl, 3-methoxy benzyl,  3-trifluoromethyl benzyl, 3-bromo benzyl, 4-cyano benzyl, 4-bromo  benzyl, 4-lower alkylbenzyl, the alkyl group of which has  minus two carbon atoms, 4-trifluoromethylbenzyl, 3,4-dichloro

 hydrogen or an acetyl or ethoxyearbonyl group.