Claims
- 1. A compound of the formula ##STR11## wherein each of the benzenoid substituents R.sub.1, R.sub.2 and R.sub.3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R.sub.1, R.sub.2 and R.sub.3 are bulky branched chain alkyl or branched chain alkoxy groups and when two of said R.sub.1, R.sub.2 and R.sub.3 are bulky groups they are located on non-adjacent positions;
- R.sub.2 and R.sub.3 when taken together are selected from the group consisting of 1,3-butadienyl and alkylenedioxy of 1 to 2 carbon atoms;
- R.sub.4 is selected from the group consisting of chloro, bromo and OR.sub.4 ' wherein OR.sub.4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms;
- R.sub.5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms;
- and the pharmaceutically-acceptable cationic salts of those compounds wherein R.sub.5 is hydroxy.
- 2. A compound according to claim 1 wherein each of R.sub.1, R.sub.2 and R.sub.3 is selected from the group consisting of hydrogen, alkoxy, fluoro and alkyl;
- R.sub.5 is selected from the group consisting of hydroxy and alkoxy;
- R.sub.4 is OR.sub.4 ' wherein OR.sub.4 ' is alkoxy;
- and the pharmaceutically-acceptable cationic salts of those compounds wherein R.sub.5 is hydroxy.
- 3. A compound according to claim 1 wherein each of R.sub.1, R.sub.2 and R.sub.3 is selected from the group consisting of hydrogen, alkoxy, fluoro and alkyl;
- R.sub.5 is selected from the group consisting of hydroxy and alkoxy;
- R.sub.4 is selected from the group consisting of chloro and bromo; and the pharmaceutically-acceptable cationic salts of those compounds wherein R.sub.5 is hydroxy.
- 4. A compound according to claim 2 wherein each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; R.sub.5 is alkoxy; and R.sub.4 is methoxy.
- 5. A compound according to claim 2 wherein each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; R.sub.5 is hydroxy; and R.sub.4 is alkoxy.
- 6. A compound according to claim 2 wherein at least one and not more than two of the benzenoid substituents R.sub.1, R.sub.2 and R.sub.3 is alkoxy, the remaining benzenoid substituents being hydrogen; R.sub.5 is alkoxy and R.sub.4 is methoxy.
- 7. A compound according to claim 2 wherein R.sub.1 is hydrogen, R.sub.2 is 8-alkoxy, R.sub.3 is 9-alkoxy, R.sub.5 is alkoxy and R.sub.4 is methoxy.
- 8. A compound according to claim 1 wherein R.sub.2 and R.sub.3 when taken together are alkylenedioxy; R.sub.1 is hydrogen; R.sub.5 is alkoxy and R.sub.4 is methoxy.
- 9. The compound according to claim 4 wherein R.sub.5 is ethoxy.
- 10. The compound according to claim 5 wherein R.sub.4 is methoxy.
- 11. The compound according to claim 5 wherein R.sub.4 is ethoxy.
- 12. The compound according to claim 6 wherein R.sub.2 is 8-methoxy; each of R.sub.1 and R.sub.3 is hydrogen; and R.sub.5 is ethoxy.
- 13. The compound according to claim 8 wherein R.sub.2 and R.sub.3 when taken together are 8,9-methylenedioxy; and R.sub.5 is ethoxy.
- 14. The method of treating bronchial asthma in a mammalian subject requiring such treatment which comprises administering to said subject an anti-bronchial effective amount of a compound having the formula ##STR12## wherein each of the benzenoid substituents R.sub.1, R.sub.2 and R.sub.3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R.sub.1, R.sub.2 and R.sub.3 are bulky branched chain alkyl or branched chain alkoxy groups and when two of said R.sub.1, R.sub.2 and R.sub.3 are bulky groups they are located on non-adjacent positions;
- R.sub.2 and R.sub.3 when taken together are selected from the group consisting of 1,3-butadienyl and alkylenedioxy of 1 to 2 carbon atoms;
- R.sub.4 is selected from the group consisting of chloro, bromo and OR.sub.4 ' wherein OR.sub.4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms;
- R.sub.5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms;
- and the pharmaceutically-acceptable cationic salts of those compounds wherein R.sub.5 is hydroxy.
- 15. The method according to claim 14 wherein each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; R.sub.5 is alkoxy; and R.sub.4 is methoxy.
- 16. The method according to claim 14 wherein each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; R.sub.5 is hydroxy; and R.sub.4 is alkoxy.
- 17. The method according to claim 14 wherein at least one and not more than two of the benzenoid substituents R.sub.1, R.sub.2 and R.sub.3 is alkoxy, the remaining benzenoid substituents being hydrogen; R.sub.5 is hydroxy; and R.sub.4 is methoxy.
- 18. The method according to claim 15 wherein R.sub.5 is ethoxy.
- 19. The method according to claim 16 wherein R.sub.4 is methoxy.
- 20. The method according to claim 17 wherein R.sub.3 is 9-methoxy; and each of R.sub.1 and R.sub.2 is hydrogen.
- 21. A pharmaceutical composition useful in treating bronchial asthma in a mammalian subject requiring such treatment which comprises a pharmaceutically-acceptable carrier and a compound of the formula ##STR13## wherein each of the benzenoid substituents R.sub.1, R.sub.2 and R.sub.3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R.sub.1, R.sub.2 and R.sub.3 are bulky branched chain alkyl or branched chain alkoxy groups, and when two of said R.sub.1, R.sub.2 and R.sub.3 are bulky groups they are located on nonadjacent positions;
- R.sub.2 and R.sub.3 when taken together are selected from the group consisting of 1,3-butanediol and alkylenedioxy of 1 to 2 carbon atoms;
- R.sub.5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms; and hydroxy substituted alkoxy having from 2 to 5 carbon atoms;
- R.sub.4 is selected from the group consisting of chloro, bromo and OR.sub.4 ' wherein OR.sub.4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms;
- and the pharmaceutically-acceptable cationic salts of those compounds wherein R.sub.5 is hydroxy.
- 22. A composition according to claim 21 wherein each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; R.sub.5 is alkoxy and R.sub.4 is methoxy.
- 23. A composition according to claim 21 wherein each of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; R.sub.5 is hydroxy and R.sub.4 is alkoxy.
- 24. A composition according to claim 21 wherein R.sub.5 is alkoxy; R.sub.4 is methoxy; and at least one and not more than two of the benzenoid substituents R.sub.1, R.sub.z and R.sub.3 is alkoxy, the remaining benzenoid substituents being hydrogen.
- 25. A pharmaceutical composition as claimed in claim 21 in a form suitable for administration by inhalation.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of U.S. patent applications Ser. No. 554,966, filed Mar. 3, 1975 and now abandoned; Ser. No. 547,227, filed Feb. 5, 1975 and now abandoned; and Ser. No. 456,797, filed Apr. 1, 1974, and now abandoned.
US Referenced Citations (3)
Non-Patent Literature Citations (2)
Entry |
Gupta et al., Indian J. Chem., vol. 9, No. 3, 201-206 (1971). |
Richardson et al., J. Med. Chem. 15, 1203-1206 (1972). |
Related Publications (2)
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Number |
Date |
Country |
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547227 |
Feb 1975 |
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456797 |
Apr 1974 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
554966 |
Mar 1975 |
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