Patent CA-1330798-C (CA)
Title: Benzo- and thieno-3,4-dihydro-pyridine derivatives
Inventor: LOESEL WALTER
IPC: C07D217/14
Filed: 1988-04-22
Granted: 1994-07-19
Abstract: Abstract Benzo- and thieno-3,4-dihydro-pyridine derivatives There is described a compound of formula I                I          [wherein A represents a benzo or thieno group;          R2 and R3 independently of each other each represent a hydrogen atom or a (C1-5)alkyl group, or together with the carbon atom to which they are bound R2 and R3 together represent a 5- or 6-mqmbered carbocyclic ring;            R11 represents a halogen atom or a (C1-4)alkyl, hydroxy, (C1-4)alkoxy, amino, thiomethyl, methane-sulphonyloxy or methanesulphonamido group, or two adjacent substituents R11 together represent -O-CH2-O-or -O-CH2-CH2-O-;   m represents 0, 1, 2 or 3 if A is a benzo group, or 0, 1 or 2 if A is a thieno group;            D represents a group of formula Ia or Ib   Ia      Ib (wherein in the group of formula Ia B represents a benzo or thieno group;            R1 represents a hydrogen atom, or a (C1-10)alkyl, phenyl, phenyl-(C1-5)alkyl, (C1-4)alkoxy or -NHCOX (wherein X is (C1-5)alkyl) group;     R5 represents a hydrogen atom, or a (C1-4)alkyl or hydroxymethyl group;       R6 and R7 independently of one another each represent a hydrogen atom or a (C1-5)alkyl group, or together with the carbon atom to which they are bound R6 and R7 together represent a 5- or 6-membered carbocyclic ring;            R12 represents a halogen atom or a (C1-4)alkyl, hydroxy, (C1-4)alkoxy, amino, thiomethyl, methane-sulphonyloxy or methanesulphonamido group, or two adjacent substituents R12 together represent -O-CH2-O-or -O-CH2-CH2-O-;   n represents 0, 1, 2 or 3 if B is a benzo group. or 0, 1 or 2 if B is a thieno group;   and in the group of formula Ib R1 is defined as for the group of formula Ia;            R'5 represents a hydrogen atom or a (C1-4)alkyl group;            R4 represents a (C1-4)alkoxy or an -NR9R10 group, wherein R9 and R10 independently of each other represent (a) hydrogen, (b) branched or unbranched (C1-12) alkyl, (C1-l2)alkenyl or (C1-l2)alkynyl (wherein the alkyl may be substituted by hydroxy, (C1-4)alkoxy, di(C1-4)alkylamino, furyl, pyrrolidinyl, morpholinyl, pyridinyl, indolyl, or the group          , (wherein R12 is as defined above; Ar is phenyl or thienyl; n' is 0, 1, 2 or 3 if Ar is phenyl, or 0, 1 or 2 if Ar is thienyl)), (c) (C3-7) cycloalkyl, (d) dimethylamino, (e) amino(C2-4)-alkyl (wherein the amino group may be unsubstituted or is mono- or di-(C1-4)alkylamino), (f) phenyl, (g) morpholinyl, or (h) pyridinyl, with the proviso that R9 and R10 cannot simultaneously represent hydrogen, dimethylamino or di(C1-4)alkylaminomethyl; or R9 and R10 together with the nitrogen atom to which they are bound together represent a pyrrolidinyl, piperidinyl, morpholinyl or piperazinyl group, the piperazinyl ring optionally being N-substituted by unsubstituted phenyl, mono- or di-(C1-4)alkoxyphenyl, pyrimidinyl or phenyl(C1-4)alkyl)] or the pharmaceutically acceptable salts thereof;   with the exception of the compound of formula I wherein D is the group Ia and R1, R2, R3, R5, R6 and R7 each represent a hydrogen atom and A and B together represent the group   ;     and with the exception of the compound of formula I wherein D is the group of formula Ib and R1, R2, R3 and R'5 represent a hydrogen atom, A represents the group   and R4 represents the group    .            Such compounds have a cardio- and/or cerebroprotective activity.