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Last Updated: March 28, 2024

Claims for Patent: 4,277,479


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Summary for Patent: 4,277,479
Title: Tetrazolylalkoxycarbostyril derivatives and pharmaceutical compositions containing them
Abstract:Novel tetrazolylalkoxycarbostyril derivative of the formula (I): ##STR1## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a low alkenyl group, a lower alkanoyl group, a benzoyl group or phenylalkyl group; R.sup.2 is a hydrogen atom, a lower alkyl group or a group of the formula ##STR2## R.sup.3 is a lower alkyl group, a cycloalkyl group, a cycloalkylalkyl group, a phenyl group or a phenylalkyl group; A is a lower alkylene group; the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton is either single or double bond; and the substituted position of a group of the formula, ##STR3## in the carbostyril skeleton is either 4-, 5-, 6-, 7- or 8-position provided that the only one such group of the formula can be substituted in the whole carbostyril skeleton, thus when R.sup.2 in 4-position is a group of the formula ##STR4## then 5-, 6-, 7- or 8-position will have no such substituted group; furthermore, the phenyl group in the above-mentioned benzoyl group, phenylalkyl group or phenyl group may have substituted group(s). The above-mentioned novel tetrazolylalkoxycarbostyril derivatives have pharmacological activities such as platelet aggregation inhibitory action, antiinflammatory action, antiulcer action, vasodilatory action and phosphodiesterase inhibitory action and are useful as anti-thrombosis agent, cerebral blood flow improving agent, antiinflammatory agent, antiulcer agent, anti-hypertensive agent and anti-asthmatic agent.
Inventor(s): Nishi; Takao (Tokushima, JP), Nakagawa; Kazuyuki (Tokushima, JP)
Assignee: Otsuka Pharmaceutical Co., Ltd. (Tokyo, JP)
Application Number:06/070,710
Patent Claims: 1. A compound of the general formula, ##STR15## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkanoyl group, a benzoyl group or a phenyl-C.sub.1-4 alkyl group; R.sup.2 is a hydrogen atom, a lower alkyl group or a group of the formula ##STR16## R.sup.3 is a lower alkyl group, a C.sub.3-8 cycloalkyl group, a C.sub.3-8 cycloalkyl-C.sub.1-4 alkyl group, a phenyl group or a phenyl-C.sub.1-4 alkyl group; A is a lower alkylene group; the carbon-carbon bond between 3- and 4-positions in the carbostyril skeleton is either single or double bond; and the substituted position of the group represented by the formula, ##STR17## in the carbostyril skeleton is either 4-, 5-, 6-, 7- or 8-position provided that only one such group of the formula can be substituted in the whole carbostyril skeleton, thus when R.sup.2 in 4-position is ##STR18## then 5-, 6-, 7- or 8-position will have no such substituted group; furthermore, the phenyl group in the above-mentioned benzoyl group, phenyl-C.sub.1-4 alkyl group or phenyl group may have substituted group(s) selected from the group consisting of lower alkoxy, lower alkyl, halogen, di-lower alkylamino, nitro, and lower alkenedioxy.

2. A compound of the general formula (I) according to claim 1, wherein the substituted position of the group of the formula ##STR19## is 5-position of the carbostyril skeleton.

3. A compound of the general formula (I) according to claim 2, wherein R.sup.3 is a C.sub.3-8 cycloalkyl group or a C.sub.3-8 cycloalkyl-C.sub.1-4 alkyl group.

4. A compound of the general formula (I) according to claim 2, wherein R.sup.3 is a phenyl-C.sub.1-4 alkyl group which may have substituted group(s) selected from the group consisting of lower alkoxy, lower alkyl, halogen, di-lower alkylamino, nitro, and lower alkenedioxy, a phenyl group which may have substituted group(s) selected from the group consisting of lower alkoxy, lower alkyl, halogen, di-lower alkylamino, nitro, and lower alkenedioxy or a lower alkyl group.

5. A compound of the general formula (I) according to claim 1, wherein the substituted position of the group of the formula ##STR20## is 6-position of the carbostyril skeleton.

6. A compound of the general formula (I) according to claim 5, wherein R.sup.3 is a C.sub.3-8 cycloalkyl group or a C.sub.3-8 cycloalkyl-C.sub.1-4 alkyl group.

7. A compound of the general formula (I) according to claim 5, where R.sup.3 is a phenyl-C.sub.1-4 alkyl group which may have substituted group(s) selected from the group consisting of lower alkoxy, lower alkyl, halogen, di-lower alkylamino, nitro, and lower alkenedioxy, a phenyl group which may have substituted group(s) selected from the group consisting of lower alkoxy, lower alkyl, halogen, di-lower alkylamino, nitro, and lower alkenedioxy, or a lower alkyl group.

8. A compound of the general formula (I) according to claim 1, wherein the substituted position of the group of the formula ##STR21## is 4-, 7- or 8-position of the carbostyril skeleton.

9. A compound of the general formula (I) according to claim 8, wherein R.sup.3 is a C.sub.3-8 cycloalkyl group or a C.sub.3-8 cycloalkyl-C.sub.1-4 alkyl group.

10. A compound of the general formula (I) according to claim 8, where R.sup.3 is a phenyl-C.sub.1-4 alkyl group which may have substituted group(s) selected from the group consisting of lower alkoxy, lower alkyl, halogen, di-lower alkylamino, nitro, and lower alkenedioxy, a phenyl group which may have substituted group(s) selected from the group consisting of lower alkoxy, lower alkyl, halogen, di-lower alkylamino, nitro, and lower alkenedioxy or a lower alkyl group.

11. 6-[3-(1-Cyclohexyltetrazol-5-yl)propoxy]carbostyril.

12. 6-[3-(1-Benzyltetrazol-5-yl)propoxy]carbostyril.

13. 5-[3-(1-Cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril.

14. 6-[3-(1-Phenyltetrazol-5-yl)propoxy]carbostyril.

15. 4-Methyl-6-[3-(1-cyclohexyltetrazol-5-yl)-propoxy]carbostyril.

16. 6-[3-(1-Cyclohexylmethyltetrazol-5-yl)propoxy]-carbostyril.

17. 6-[3-(1-Cyclooctyltetrazol-5-yl)propoxy]-carbostyril.

18. 6-[3-(1-Cyclopentyltetrazol-5-yl)propoxy]-carbostyril.

19. 6-[4-(1-Cyclohexyltetrazol-5-yl)butoxy]carbostyril.

20. 6-[3-(1-Cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril.

21. 6-[3-(1-Cyclohexylmethyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril.

22. 7-[3-(1-Cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril.

23. 8-[3-(1-Cyclohexyltetrazol-5-yl)propoxy]-3,4-dihydrocarbostyril.

24. 4-[3-(1-Cyclohexyltetrazol-5-yl)propoxy]-carbostyril.

25. A platelet aggregation inhibitor composition containing as an active ingredient a pharmacologically effective amount of a compound of the formula (I) of claim 1 and a pharmaceutically acceptable carrier.

26. A phosphodiesterase inhibitor composition containing as an active ingredient a pharmacologically effective amount of a compound of the formula (I) of claim 1 and a pharmaceutically acceptable carrier.

27. A cerebral blood flow improver composition containing as an active ingredient a pharmacologically effective amount of a compound of the formula (I) of claim 1 and a pharmaceutically acceptable carrier.

28. An anti-hypertensive agent composition containing as an active ingredient a pharmacologically effective amount of a compound of the formula (I) of claim 1 and a pharmaceutically acceptable carrier.

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