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Home Vasodialators Derivatives-of-cis-endo-2-azabicyclo-5-3-0-decane-3-carboxylic-acid-and-their-use-for-treating-hypertension

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 Derivatives of cis, endo-2-azabicyclo[5.3.0]decane-3-carboxylic acid, and their use for treating hypertension

Details
Inventors: Urbach, Hansjorg; Henning, Rainer; Teetz, Volker; Becker, Reinhard;
Assignee: Hoechst Aktiengesellschaft (DE)
Primary Examiner: Bond; Robert T.
Assistant Examiner: Springer; D. B.
Attorney, Agent or Firm: Finnegan, Henderson, Farabow, Garrett & Dunner

The invention relates to derivatives of cis,endo-2-azabicyclo[5.3.0]decane-3-carboxylic acid of the formula I ##STR1## in which R denotes hydrogen, alkyl, alkenyl or aralkyl, R.sup.1 denotes hydrogen, allyl, vinyl or a side chain of an optionally protected naturally occurring .alpha.-aminoacid, R.sup.2 denotes hydrogen, alkyl, alkenyl or aralkyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen, or Y and Z together denote oxygen, X denotes alkyl, alkenyl, cycloalkyl, aryl which can be substituted once, twice or three times by alkyl, alkoxy, hydroxyl, halogen, nitro, amino, alkylamino, dialkylamino or methylenedioxy, or denotes indol-3-yl, and their physiologically acceptable salts, a process for their preparation, agents containing them and their use.

DETAILED DESCRIPTION We claim: 1.
A compound of the formula I ##STR11## in which the hydrogen atoms on the bridgehead C atoms 1 and 5 have the cis-configuration relative to one another and the carboxyl group on C atom 3 is oriented endo to the bicyclic ring system and in which R denotes hydrogen, (C.
sub.
1 -C.
sub.
6)-alkyl, (C.
sub.
2 -C.
sub.
6)-alkenyl or (C.
sub.
6 -C.
sub.
12)-aryl-(C.
sub.
1 -C.
sub.
4)-alkyl, R.
sup.
1 denotes hydrogen, allyl, vinyl or a side chain of an optionally protected, naturally occurring .
alpha.
-amino-acid R.
sup.
1 CH(NH.
sub.
2)--COOH, R.
sup.
2 denotes hydrogen, (C.
sub.
1 -C.
sub.
6)-alkyl, (C.
sub.
2 -C.
sub.
6)-alkenyl or (C.
sub.
6 -C.
sub.
12)-aryl-(C.
sub.
1 -C.
sub.
4)-alkyl, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen, X denotes (C.
sub.
1 -C.
sub.
6)-alkyl, (C.
sub.
2 -C.
sub.
6)-alkenyl, (C.
sub.
5 -C.
sub.
9)-cycloalkyl, (C.
sub.
6 -C.
sub.
12)-aryl which can be substituted once, twice or three times by at least one member selected from the group consisting of (C.
sub.
1 -C.
sub.
4)-alkyl, (C.
sub.
1 -C.
sub.
4)-alkoxy, hydroxyl, halogen, nitro, amino, (C.
sub.
1 -C.
sub.
4)-alkylamino, di-(C.
sub.
1 -C.
sub.
4)-alkylamino and methylenedioxy, or denotes indol-3-yl, and its physiologically acceptable salts.
2.
A compound of the formula I as claimed in claim 1 in which R denotes hydrogen, R.
sup.
1 denotes methyl, the optionally acylated side chain of lysine or the O-alkylated side chain of tyrosine, R.
sup.
2 denotes hydrogen, methyl, ethyl, benzyl or tert.
-butyl, X denotes phenyl or phenyl substituted once or twice with at least one member selected from the group consisting of fluorine and chlorine, Y denotes hydrogen or hydroxyl, Z denotes hydrogen or Y and Z together denote oxygen.
3.
The compound according to claim 2 which is N-(1-S-Carboethoxy-3-phenylpropyl)-S-alanyl-cis,endo-2-azabicyclo[5.
3.
0]de cane-3-S-carboxylic acid or its physioyogically acceptable salts.
4.
The compound according to claim 2 which is N-(1-S-Carboxy-3-phenylpropyl)-S-alanyl-cis,endo-2-azabicyclo[5



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