Benzothiazoline compounds

Details Benzothiazoline compounds Benzothiazoline compounds

1983-04-14

1984-10-30

Rizzo, Nicholas S.

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Bacterium or component thereof or substance produced by said...

424250, 424256, 424270, 424274, 544135, 544368, 546209, 548180, A61K 2700, A61K 31495, C07D41700

Patent

active

044799497

DESCRIPTION:

BRIEF SUMMARY
SUMMARY OF THE INVENTION

This invention relates to benzothiazoline derivatives of the formula [I] and salts thereof, ##STR3## wherein
R.sup.1 is lower alkanoyl;
R.sup.2 is one or more group(s) selected from hydrogen, lower alkyl, lower alkoxy, hydroxy, halogen, nitro, halogenolower alkyl and sulfamoyl;
R.sup.3 is ##STR4## or --COR.sup.8 ;
R.sup.4 and R.sup.5, which may be same or different, each is hydrogen, lower alkyl, cyclohexyl or substituted lower alkyl wherein the substituent(s) is/are selected from the group consisting of hydroxy, phenyl, pyridyl, piperidyl or phenylcarbonyl, and said phenyl nucleus may be resubstituted by one or more groups selected from lower alkyl, hydroxy, halogen, lower alkoxy, nitro, cyano, acetamino and lower alkylamino;
R.sup.6 is hydrogen, alkyl containing 1 to 8 carbon atoms, alkanoyl containing 2 to 8 carbon atoms, alkenoyl containing 2 to 8 carbon atoms or furylcarbonyl, each of which alkyl, alkanoyl and alkenoyl may be substituted by one or more groups selected from hydroxy, phenyl and phenylcarbonyloxy, and said phenyl nucleus may be resubstituted by one or more groups selected from lower alkyl, hydroxy, halogen, lower alkoxy, nitro, cyano, acetamino and lower-alkylamino;
R.sup.7 is hydrogen, hydroxy, phenyl-lower alkyl or benzoyl;
R.sup.8 is hydroxy, lower alkoxy, ##STR5##
Z is straight or branched alkylene containing 1 to 6 carbon atoms;
m is 0 or 1;
n is 0 or 1;
p is 4 or 5, groups having 1 to 6 carbon atoms.
The same shall be applied hereinafter.


BACKGROUND OF THE INVENTION

The compounds of this invention are novel benzothiazoline derivatives wherein the substituent at 3-position on the benzothiazoline ring is lower alkanoyl and that at 2-position is phenyl which is resubstituted by ether group at any position. 2-Phenylbenzothiazoline derivatives were reported by H. Breuer et al. (U.S. Pat. No. 3,720,683), H. D. Cossey et al. (J. Chem. Soc., 1965, 954) and P. J. Palmer et al. (J. Med. Chem., 14, 248). The U.S. Pat. of Breuer et al. relates to 2-phenylbenzothiazoline derivatives in which phenyl nucleus is substituted by alkyl, etc. but not ether group, and the pharmacological effects are for anti-inflammatory and anti-microbiral. Cossey et al. and Palmer et al. reported 2-phenylbenzothiazoline derivatives in which phenyl nucleus is substituted by ether group, but the substituent of 3-position is not lower alkanoyl but hydrogen, alkyl, benzyl, etc., and the pharmacological effect is for anti-microbiral.


DETAILED DESCRIPTION OF THE INVENTION

This invention relates to benzothiazoline derivatives of the formula [I]. ##STR6##
The compounds of this invention are benzothiazoline derivatives wherein the substituent at 3-position on the benzothiazoline ring is lower alkanoyl and that at 2-position is phenyl which is resubstituted by ether group at any position. The compounds of this invention are not only new in chemical structure but also found useful for treatment of cardiovascular diseases and such effect on cardiovascular diseases has not been found in the known benzothiazoline derivatives. Cardiovascular diseases are angina cordis, arrhythmia, thrombosis, etc., and .beta.-blocker, inhibitor of platelet aggregation, calcium antagonist, etc. are used as therapeutic agent. From the pharmacological tests, it is proved that the compounds of this invention possess a superior platelet anti-aggregation effect and calcium antagonization, so they are useful for cardiovascular diseases. Processes for preparing the compounds of this invention are summarized as follows. The reaction of the compound of the formula [II] with the compound of the formula [III], ##STR7##
wherein X is halogen (the same shall be applied hereinafter), or the reaction reversed the above reaction order, i.e., the reaction of the compound of the formula [IV] with the amine derivative, ##STR8## wherein
Y is halogen, carboxy or formyl, and Y and --OH may be jointed to form epoxy ring;
Amine derivative is ##STR9##
q is 0 or 1,
the same shall be applied hereinafter. The processes are explained in detail as

REFERENCES:
patent: 3340266 (1967-09-01), Howe et al.
patent: 3658829 (1972-04-01), Nakamura et al.
patent: 3720683 (1973-03-01), Breuer et al.
Cossey, Judd, and Stephens, "Some Anti-microbial Compounds in the Heteocyclic Series"-J. Chemical Society, 1965, pp. 954-973.
P. J. Palmer, R. B. Trigg, and J. V. Warrington, "Benzothiazolines as Antituberculous Agents"-Journal of Medicinal Chemistry, 1971, vol. 14, No. 3-pp. 248-251.

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