Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1987-08-31
1989-10-31
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544368, 546198, 546270, 548150, C07D27760, C07D41712
Patent
active
048778761
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to a novel indenothiazole derivative useful as a medicine having an excellent antiulcerative effect, and a process for preparing the same.
DESCRIPTION OF THE PRIOR ART
With regard to indenothiazole derivative, a process for manufacturing a 2-amino indenothiazole derivative is disclosed in Journal of the American Chemical Society, 72, 3722 (1950) and Journal of the Chemical Society 2740 (1958). Further, a process for manufacturing a 2-aminoacyl indenothiazole derivative and its potential as a medicine for curing allergic diseases are disclosed in Japanese Patent Appln. Laid-Open Gazette No. 58-55474. However, the indenothiazole derivative of this invention is neither disclosed nor suggested in any one of the aforesaid publications. Further, whether its tautomer exists is not known at all. Still further, it was of course unknown whether the indenothiazole derivative has an antiulcerative effect.
The medical treatment of digestive ucler seeks to restrain the attack factor and strengthen the defense factor. In recent years, in order to restrain the attack factor, a histamine H.sub.2 -antagonist such as cimetidine, ranitidine or famotidine plays the main role as a remedial medicine for ulcer. Nevertheless, the problem of relapse of ulcer remains unsolved. Further, omeprazole serving as an ATPase inhibitor (or a proton pump inhibitor) restrains acid secretion and has a high selectivity for internal organs. It has a stable effect over a long period, but has a problem as to its side effects.
As for reinforcing agents for the defense factor, there are plenty of medicines which have the actions of strengthening of mucous membrane resistance, promoting mucus secretion, improving minute circulations and promoting prostagrandine synthesis. Although these medicines have so minor side effects that they are safely used, they are still not appreciated to be sufficiently effective.
It is an object of this invention to provide a novel indenothiazole derivative, a tautomer thereof or their acid addition salt, which is a useful medicine having an excellent antiulcerative effect with no side actions.
It is another object to provide a process for preparing the novel indenothiazole derivative, the tautomer thereof or their acid addition salt.
DISCLOSURE OF THE INVENTION
The novel indenothiazole derivative is represented by the following formula: ##STR2## wherein X and Y are identical with, or different from, each other and are each a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group; n is an integer of 0 to 4; R.sub.1 is a hydrogen atom, lower alkyl group, unsubstituted or substituted phenyl group; R.sub.2 is a lower alkyl group, cycloalkyl group, low alkoxy group, unsubstituted or substituted phenoxy group, unsubstituted or substituted phenyl group, alkenyl group, heterocyclic group or cyclic amino group; R.sub.3 is a hydrogen atom, lower alkyl group or acyl group; R.sub.2 and R.sub.3 may be combined together to form a cyclic amino group.
Further, the tautomer is represented by the following formula: ##STR3## wherein X, Y, n, R.sub.1 and R.sub.2 are as defined above.
The compounds of the aforesaid formulas (Ia) and (Ib) are described hereinafter in more detail.
The halogen atom means a fluorine, chlorine, bromine or iodine atom. The lower alkyl group includes an alkyl group of 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert.-butyl, n-pentyl, iso-pentyl or n-hexyl group.
The cycloalkyl group includes a cycloalkyl group having 3 to 7 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl or cycloheptyl group.
The lower alkoxy group includes an alcoxy group having 1 to 6 carbon atoms such as methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy or tert.-butoxy group.
The substituent in the substituted phenyl or substituted phenoxy group includes a halogen atom, lower alkyl group (this group may further contain mono- or di-C.sub.1-6 alkylamino group as a substituent), hydroxyl group, lower alkoxy group or trif
REFERENCES:
patent: 4082773 (1978-04-01), Hauck
Aoki Testsuo
Hachiya Terumi
Ikesue Kouichi
Inoue Hisataka
Mizoguchi Takenobu
Gerstl Robert
Hisamitsu Pharmaceutical Co. Inc.
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