US 5,859,025 AGranted

Fluoroalkyl- and fluoroalkoxy-substituted heterocyclic bradykinin antagonists, process for their preparation, and their use

AssigneeHoechst Aktiengesellschaft

InventorsAdalbert Wagner, Holger Heitsch, Gerhard Nolken, Klaus Wirth, Bernward Scholkens

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Abstract

Fluoroalkyl- and fluoroalkoxy-substituted heterocyclic bradykinin antagonists, process or their preparation, and their use Heterocyclic fluoroalkyl derivatives and fluoroalkoxy derivatives of the formula (I) having bradykinin-antagonistic action ##STR1## in which X.sub.1 -X.sub.3 are N or CR.sup.5, R.sup.1 and R.sup.2 are H or halogen, R.sup.3 and R.sup.4 are H, halogen, alkyl or alkenyl, R.sup.5 is H, halogen, (substituted) alkyl, O--R.sup.6, S--R.sup.6, NHR.sup.6, (substituted) aryl, (substituted)aryl-alkyl, --C(O)--OR.sup.6 or --C(O)--H, R.sup.6 and R.sup.8 H, alkyl, alkenyl or aryl-alkyl, R.sup.7 is (substituted) alkyl or (substituted) alkoxy, B is an aminocarboxylic acid, D is alkenediyl, alkanediyl or --(CH.sub.2).sub.n --Y.sub.p --(CH.sub.2).sub.m --, E is oxygen or sulfur, Y is oxygen, sulfur or NR.sup.8, n and m are a number 0-3, o is a number 1-3 and p is 0 or 1, and their physiologically tolerable salts and a process for their preparation are described.

Claims35

Dependent claims

A heterocyclic fluoroalkyl compound or fluoroalkoxy compound of the formula (I) ##STR42## in which the symbols have the following meaning:

a) X.sub.1 -X.sub.3 are CR.sup.5 ;
b) R.sup.1 and R.sup.2, identically or differently, are
(1) H
(2) halogen;
c) R.sup.3 and R.sup.4, identically or differently, are
(1) H
(2) halogen
(3) (C.sub.1 -C.sub.5)-alkyl
(4) (C.sub.2 -C.sub.5)-alkenyl;
d) R.sup.5 is
(1) H
(2) halogen
(3) (C.sub.1 -C.sub.6)-alkyl
(4) O--R.sup.6
(5) S--R.sup.6
(6) NHR.sup.6
(7) (C.sub.6 -C.sub.12)-aryl
(8) (C.sub.6 -C.sub.12)-aryl-(C.sub.1 -C.sub.3)-alkyl
(9) --C(O)--OR.sup.6
(10) --C(O)--H;
where (3), (7), and (8) can optionally be substituted by one or more groups OR.sup.6, SR.sup.6, NO.sub.2, CN, NHR.sup.6 or halogen;
e) R.sup.6 and R.sup.8, identically or differently, are
(1) H
(2) (C.sub.1 -C.sub.5)-alkyl
(3) (C.sub.3 -C.sub.5)-alkenyl
(4) (C.sub.6 -C.sub.12)-aryl-(C.sub.1 -C.sub.3)-alkyl;
f) R.sup.7 is
(1) (C.sub.1 -C.sub.5)-alkyl, where hydrogen is partially or completely replaced by fluorine or chlorine
(2) (C.sub.1 -C.sub.5)-alkoxy, where hydrogen is partially or completely replaced by fluorine or chlorine;
g) B is an aminocarboxylic acid;
h) D is
(1) (C.sub.2 -C.sub.5)-alkenediyl
(2) (C.sub.1 -C.sub.5)-alkanediyl
(3) --(CH.sub.2).sub.n --Y.sub.p --(CH.sub.2).sub.m --;
i) E is
(1) O
(2) S;
j) Y is
(1) O
(2) S
(3) NR.sup.8 ;
k) n and m, identically or differently, are a number from 0 to 3;
l) o is a number from 1 to 3;
m) p is 0 or 1;
a physiologically tolerated salt thereof.

42 more elements

Dependencies are inferred from the claim text.