Claims
- 1. A racemic compound of the formula ##STR25## wherein A is--C.tbd.C--R.sub.6
- R.sub.1 is hydrogen or lower alkanoyl,
- R.sub.2, R.sub.3, and r.sub.4 independently are hydrogen or lower alkyl,
- R.sub.5 is lower alkyl,
- R.sub.6 is a heteroaromatic radical selected from pyridinyl, imidazoyl, thienyl, 2-(pyridyl)thienyl, 2-(phenyl)thienyl, 2-chlorothienyl, furyl, pyrimidinyl, oxazolyl, quinolinyl, isoquinolinyl, indolyl, benzothienyl or benzofuranyl or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkyl amino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR26## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R'' hydrogen or lower alkyl,
- or an enantiomer thereof or a salt thereof.
- 2. A compound, in accordance with claim 1, wherein R.sub.1 is hydrogen, and R.sub.2 -R.sub.5 are methyl.
- 3. A compound, in accordance with claim 1, wherein R.sub.1 is hydrogen, R.sub.2 -R.sub.5 are methyl and R.sub.6 is unsubstituted phenyl, thienyl, benzothienyl or pyridinyl or substituted phenyl.
- 4. A compound, in accordance with claim 1, wherein R.sub.1 is hydrogen, and R.sub.2 -R.sub.5 are lower alkyl.
- 5. A compound, in accordance with claim 1, R-[2-(Benzo[b]thiophene-3yl)ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 6. A compound, in accordance with claim 1, S-[2-(Benzo[b]thiophene-3yl)ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol.
- 7. A compound, in accordance with claim 1, rac-[2-(Benzo[b]thiophene-3-yl)ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 8. A compound, in accordance with claim 1, R-3,4-Dihydro-2,5,7,8-tetramethyl-2[(2-thienyl)ethynyl]-2H-1-Benzopyran -6-ol.
- 9. A compound, in accordance with claim 1, S-3,4-Dihydro-2,5,7,8-tetramethyl-2[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol.
- 10. A compound, in accordance with claim 1, rac-3,4-Dihydro-2,5,7,8-tetramethyl-2[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol.
- 11. A pharmaceutical composition comprising an effective amount of a racemic compound of the formula ##STR27## wherein A is --C.tbd.C--R.sub.6,
- R.sub.1 is hydrogen or lower alkanoyl,
- R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,
- R.sub.5 is lower alkyl,
- R.sub.6 is a heteroaromatic radical selected from pyridinyl, imidazolyl, thienyl, 2-(pyridyl)thienyl, 2-(phenyl)thienyl, 2-chlorothienyl, furyl, pyrimidinyl, oxazolyl, quinolinyl, isoquinolinyl, indolyl, benzothienyl or benzofuranyl, or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radimal may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di- lower alkyl amini, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or an adjacent carbons can be ##STR28## wherein R' is hydrogen, lower alkanoyl, trifluorocetyl and R'' hydrogen or lower alkyl,
- or an enantiomer thereof or a salt thereof, and an inert carrier.
- 12. A pharmaceutical composition, in accordance with claim 11, wherein R.sub.1 is hydrogen, and R.sub.2 -R.sub.5 are methyl.
- 13. A pharmaceutical composition, in accordance with claim 11, wherein R.sub.1 is hydrogen, R.sub.2 -R.sub.5 are methyl and R.sub.6 is unsubstituted phenyl, thienyl, benzothienyl or pyridinyl or substituted phenyl.
- 14. A pharmaceutical composition, in accordance with claim 11, wherein R.sub.1 is hydrogen, and R.sub.2 -R.sub.5 are lower alkyl.
- 15. A pharmaceutical composition, in accordance with claim 11, wherein the compound of formula I is R-[2-(benzo[b]thiophene-3-yl)ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 16. A pharmaceutical composition, in accordance with claim 11, wherein the compound of formula I is S-[2-(benzo[b]thiophene-3-yl)ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol.
- 17. A pharmaceutical composition, in accordance with claim 11, wherein the compound of formula I is rac-[2-(benzo[b]thiophene-3-yl)ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol.
- 18. A pharmaceutical composition, in accordance with claim 11, wherein the compound of formula I is R-3,4-Dihydro2,5,7,8-tetramethyl-2-[(2-thienyl)ethynyl]-2H-1-benzopyran-6ol.
- 19. A pharmaceutical composition, in accordance with claim 11, wherein the compound of formula I is S-3,4-Dihydro2,5,7,8-tetramethyl-2[(2-thienyl)ethynyl]-2H-1-benzopyran-6ol
- 20. A pharmaceutical composition, in accordance with claim 11, wherein the compound of formula I is rac-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol.
- 21. A method of treating disease states caused or aggravated by excessive oxidative metabolism of arachidonic acid which comprises administering to a host requiring such treatment an effective amount of racemic compound of formula ##STR29## wherein A is --C.tbd.C--R.sub.6,
- R.sub.1 is hydrogen or lower alkanoyl,
- R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,
- R.sub.5 is lower alkyl,
- R.sub.6 is a heteroaromatic radical selected from pyridinyl, imidazolyl, thienyl, 2-(pyridyl) thienyl, 2-(phenyl)thienyl, 2-chlorothienyl, furyl, pyrimidinyl, oxazolyl, quinolinyl, isoquinolinyl, indolyl, benzothienyl or benzofuranyl, or an aromatic radial selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substitutents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di- lower alkyl amino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, amionocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR30## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R'' hydrogen or lower alkyl,
- or an enantiomer thereof or a salt thereof.
- 22. A method in accordance with claim 21, wherein R.sub.1 is hydrogen, and R.sub.2 -R.sub.5 are methyl.
- 23. A method in accordance with claim 21, wherein R.sub.1 is hydrogen, R.sub.2 -r.sub.5 are methyl and R.sub.6 is unsubstituted phenyl, thienyl, benzothienyl or pyridinyl or substituted phenyl.
- 24. A method in accordance with claim 21, wherein R.sub.1 is hydrogen, and R.sub.2 -R.sub.5 are lower alkyl.
- 25. A method in accordance with claim 21, wherein the compound of formula I is R-[2-(Benzo[b]thiophene-3-yl) ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 26. A method in accordance with claim 21, wherein the compound of formula I is S-[2-(Benzo[b]thiophene-3-yl) ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 27. A method in accordance with claim 21, wherein the compound of formula I is rac-[2-(Benzo[b]thiophene-3-yl) ethynyl]-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol.
- 28. A method in accordance with claim 21, wherein the compound of formula I is R-3,4-Dihydro-2,5,7,8-tetramethyl-2[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol.
- 29. A method in accordance with claim 21, wherein the compound of formula I is S-3,4-Dihydro-2,5,7,8-tetramethyl-2[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol.
- 30. A method in accordance with claim 21, wherein the compound of formula I is rac-3,4-Dihydro-2,5,7,8-tetramethyl -2[(2-thienyl)ethynyl]-2H-1-benzopyran-6-ol.
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation in-part of U.S. Patent application No. 230,094, filed Aug. 9, 1988 now abandoned.
US Referenced Citations (6)
Foreign Referenced Citations (7)
Number |
Date |
Country |
180190-A |
Oct 1985 |
EPX |
61148173-A |
Dec 1984 |
JPX |
61-204122-A |
Mar 1985 |
JPX |
61-267570-A |
May 1985 |
JPX |
61-267571-A |
May 1985 |
JPX |
61-210030A |
Sep 1986 |
JPX |
62-132879 |
Jun 1987 |
JPX |
Non-Patent Literature Citations (1)
Entry |
Chem. Abstracts, vol. 112 (13), 118862s (1990). |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
230094 |
Aug 1988 |
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