2-bicyclobenzimidazoles, processes for their preparation and med

Details 2-bicyclobenzimidazoles, processes for their preparation and med 2-bicyclobenzimidazoles, processes for their preparation and med

1992-04-14

1995-05-09

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546157, 546 18, C07D215227, C07D23518, A61K 31415, A61K 3147

Patent

active

054140889

DESCRIPTION:

BRIEF SUMMARY
The present invention concerns compounds of the general formula I ##STR2## in which R.sup.1 signifies a hydrogen atom, a C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or a C.sub.3 -C.sub.7 -cycloalkyl group, R.sup.2 signifies a C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or cyano group, a carbonyl group substituted by a hydroxyl, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, amino, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino or hydrazino group or R.sup.1 and R.sup.2 together represent a C.sub.2 -C.sub.6 -alkylidene or C.sub.3 -C.sub.6 -cycloalkylidene group or R.sup.1 and R.sup.2, together with the carbon atom to which they are attached, form a C.sub.3 -C.sub.7 -spirocycle, n can be equal to 0 or 1, R.sup.3 signifies a hydrogen atom, a C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, C.sub.3 -C.sub.7 -cycloalkyl, benzyl, carboxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyloxycarbonyl-C.sub.1 -C.sub.6 -alkyl or di-C.sub.1 -C.sub.6 -alkyloxophosphinyl-C.sub.1 -C.sub.6 -alkyl group, R.sup.4, R.sup.5, R.sup.6 can be the same or different and each can be hydrogen, a C.sub.1 -C.sub.7 -alkanesulphonyloxy, trifluoromethanesulphonyloxy, C.sub.1 -C.sub.7 -alkanesulphonylamino, trifluoromethanesulphonylamino, N-C.sub.1 -C.sub.7 -alkyl-C.sub.1 -C.sub.7 -alkanesulphonylamino, phenylsulphonylamino, C.sub.1 -C.sub.7 -alkylsulphenylmethyl, C.sub.1 -C.sub.7 -alkylsulphinylmethyl or C.sub.1 -C.sub.7 -alkylsulphonylmethyl group, a carbonyl group substituted by a hydroxyl, C.sub.1 -C.sub.7 -alkoxy, C.sub.1 -C.sub.7 -alkyl, amino, C.sub.1 -C.sub.7 -alkylamino or di-C.sub.1 -C.sub.7 -alkylamino group, a sulphonyl group substituted by an amino, C.sub.1 -C.sub.7 -alkylamino, di-C.sub.1 -C.sub.7 -alkylamino, morphoino, thiomorpholino, pyrrolidino, piperidino or hexamethyleneimino group, a C.sub.1 -C.sub.7 -alkylcarbonylamino, C.sub.1 -C.sub.7 -alkylcarbonyloxy, aminocarbonylamino or C.sub.1 -C.sub.7 -alkylaminocarbonylamino group, a C.sub.1 -C.sub.7 -alkylmercapto, C.sub.1 -C.sub.7 -alkylsulphinyl or C.sub.1 -C.sub.7 -alkylsulphonyl group, a nitro, amino, hydroxyl, benzyloxy, C.sub.1 -C.sub.7 -alkoxy, C.sub.1 -C.sub.7 -alkyl, C.sub.2 -C.sub.7 -alkenyl, C.sub.2 -C.sub.7 -alkenyloxy, C.sub.2 -C.sub.7 -alkynyloxy, cyano-C.sub.1 -C.sub.7 -alkoxy, carboxy-C.sub.1 -C.sub.7 -alkoxy, phenyl-C.sub.1 -C.sub.7 -alkoxy, C.sub.1 -C.sub.7 -alkoxycarbonyl-C.sub.1 -C.sub.7 -alkoxy, C.sub.1 -C.sub.7 -alkylamino, di-C.sub.1 -C.sub.7 -alkylamino, trifluoromethyl, cyano, halogen or imidazolyl group or two ortho-positioned substituents R.sup.4, R.sup.5, together with the C-atoms to which they are attached, form a 5- or 6-membered heterocyclic ring with 1-2 heteroatoms, such as oxygen, nitrogen or sulphur, whereby, in the case of n=0, the benzimidazole ring can be attached in the 4-, 5-, 6- or 7-position with the 2,3-dihydroindol-2-one or, in the case of n=1, the linkage takes place in the 5-, 7-, 8-position or, if R.sup.3 does not signify a hydrogen atom, also in the 6-position with the 1,2,3,4-tetrahydroquinolin-2-one, or their physiologically compatible salts and optical isomers, processes for their preparation, as well as medicaments containing these compounds.
The compounds of the general formula I inhibit or reduce not only the erythrocyte aggregation but also the thrombocyte aggregation in low concentrations. On the basis of these properties, these substances are suitable for the treatment of diseases in which, in the pathogenesis, the erythrocyte and thrombocyte aggregation play an important part, such as for example peripheral and cerebral circulatory disturbances, shock states, degenerative blood vessel diseases, rheumatic diseases, various types of ulcers, necrotic processes in tumours, degenerative disturbances of the retina, nerves and muscles or of various skin diseases. In particular, there come into question the treatment of arterial occlusive diseases, ischaemic conditions, venous insufficiency or diabetes mellitus.
Compounds of similar structure as those of the gener

REFERENCES:
patent: 4898872 (1990-02-01), Campbell et al.
Chemical Abstracts 110(17) 154319n, 1989.

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