Claims
- 1. A compound of the formula: ##STR6## wherein R.sup.1 is selected from C.sub.2 -C.sub.6 straight or branched alkyl, C.sub.3 -C.sub.6 cycloalkyl, and aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, and wherein said alkyl, cycloalkyl and aralkyl are optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- R.sup.2 is selected from O and S;
- R.sup.3 is aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, wherein said aralkyl is optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- R.sup.6 is selected from O and S; and
- R.sup.8 is selected from isopropyl, n-propyl, cyclopropyl, butyl and pentyl, said butyl and pentyl being straight branched or cyclic, or aralkyl consisting of an aryl moiety and a straight or branched C.sub.1 -C.sub.8 alkylene moiety, wherein said isopropyl, n-propyl, cyclopropyl, butyl and pentyl, straight, branched or cyclic or aralkyl are optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido,;
- provided that R.sup.2 and R.sup.6 are not both O.
- 2. A compound according to claim 1, wherein R.sup.8 is isopropyl or cyclopropyl.
- 3. A compound selected from the group consisting of 1,3-diethyl-8-cyclopropyl-2,6-dithioxanthine and 1,3-diethyl-8-(isopropyl)-6-thioxanthine.
- 4. A compound according to claim 1, wherein R.sup.1, R.sup.3 and R.sup.8 are further substituted by substituents selected from the group consisting of halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, or oxo.
- 5. A compound according to claim 1, where in R.sup.8 is a straight chain alkyl or a branched chain alkyl.
- 6. A compound according to claim 1, wherein R.sup.1 and R.sup.3 are benzyl, optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, or C.sub.3 -C.sub.7 cycloalkoxy.
- 7. A compound according to claim 1, selected from the group consisting of:
- 3-(4-chlorobenzyl)-1-ethyl-8-isopropyl-6-thioxanthine;
- 1,3-Di-(4chlorobenzyl)-8-isopropyl-6-thioxanthine; and
- 3-(3-Cyclopentyloxy-4-methoxy-benzyl)-1-ethyl-8-isopropyl-6-thioxanthine.
- 8. A pharmaceutical composition comprising a compound according to claim 1, or a salt thereof, together with a pharmaceutically acceptable carrier.
- 9. The pharmaceutical composition of claim 8, wherein the compound is selected from the group consisting of:
- 3-(4-chlorobenzyl)-1-ethyl-8-isopropyl-6-thioxanthine;
- 1,3-Di-(4chlorobenzyl)-8-isopropyl-6-thioxanthine; and
- 3-(3-Cyclopentyloxy-4-methoxy-benzyl)-1-ethyl-8-isopropyl-6-thioxanthine.
- 10. The pharmaceutical composition of claim 8 wherein said pharmaceutically acceptable carrier is suitable for oral administration topical administration, administration by suppository, administration by inhalation, administration by insufflation, or parenteral administration.
- 11. A method of effecting PDE IV inhibition which comprises administering to a patient suffering from a disease or disorder selected from the group consisting of asthma, allergies, inflammation, depression, and rhinitis, a therapeutically effective amount of a compound of the formula: ##STR7## wherein: R.sup.1 is selected from C.sub.2 -C.sub.6 straight or branched alkyl, C.sub.3 -C.sub.6 cycloalkyl, and aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, wherein said alkyl, cycloalkyl, and aralkyl are optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- R.sup.2 is selected from O and S;
- R.sup.3 is aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, wherein said aralkyl is optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- R.sup.6 is selected from O and S; and
- R.sup.8 is selected from isopropyl, n-propyl, cyclopropyl, butyl and pentyl, said butyl and pentyl being straight, branched or cyclic, or aralkyl consisting of an aryl moiety and a straight or branched C.sub.1 -C.sub.8 alkylene moiety, wherein said isopropyl, n-propyl, cyclopropyl, butyl and pentyl, straight, branched or cyclic, or aralkyl are optionally substituted wit halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- provided that R.sup.2 and R.sup.6 are not both O.
- 12. The compound of claim 1 wherein R.sup.1 is aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, and wherein said aralkyl is optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido.
- 13. The method of claim 11, wherein R.sup.8 is selected from the group consisting of isopropyl and cyclopropyl.
- 14. The method of claim 11, wherein R.sup.1, R.sup.3 and R.sup.8 are further substituted by substituents selected from the group consisting of halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, or oxo.
- 15. The method of claim 11, wherein R.sup.8 is selected from the group consisting of isopropyl, n-propyl, straight or branched butyl and straight or branched pentyl.
- 16. The compound of claim 11, wherein R.sup.1 and R.sup.3 are benzyl, optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, or C.sub.3 -C.sub.7 cycloalkoxy.
- 17. The method of claim 11, wherein said compound is selected from the group consisting of:
- 3-(4-chlorobenzyl)-1-ethyl-8-isopropyl-6-thioxanthine;
- 1,3-Di-(4-chlorobenzyl)-8-isopropyl-6-thioxanthine; and
- 3-(3-Cyclopentyloxy-4-methoxy-benzyl)-1-ethyl-8-isopropyl-6-thioxanthine.
- 18. A method of treating a patient suffering from a disease or disorder selected from the group consisting of asthma, allergies, depression, and rhinitis, comprising administering to the patient an effective amount of a compound of the formula: ##STR8## wherein R.sup.1 is selected from C.sub.2 -C.sub.6 straight or branched alkyl, C.sub.3 -C.sub.6 cycloalkyl, and aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, wherein said alkyl, cycloalkyl, and aralkyl are optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- R.sup.2 is selected from O and S;
- R.sup.3 is aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, wherein said aralkyl is optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- R.sup.6 is selected from O and S; and
- R.sup.8 is selected from isopropyl, n-propyl, cyclopropyl, butyl and pentyl, said butyl and pentyl being straight, branched or cyclic, or aralkyl consisting of an aryl moiety and a straight or branched C.sub.1 -C.sub.8 alkylene moiety, wherein said isopropyl, n-propyl, cyclopropyl, butyl and pentyl, straight, branched or cyclic, or aralkyl are optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy carbamido;
- provided that R.sup.2 and R.sup.6 are not both O.
- 19. The method of claim 18, wherein R.sup.1 and R.sup.3 of said compound are selected from the group consisting of alkyl and aralkyl.
- 20. The method of claim 18, wherein said compound is administered orally, topically, by suppository, by inhalation, by insulation, or parenterally.
- 21. The method of claim 18, wherein said compound is selected from the group consisting of:
- 3-(4-chlorobenzyl)-1-ethyl-8-isopropyl-6-thioxanthine;
- 1,3-Di-(4-chlorobenzyl)-8-isopropyl-6-thioxanthine; and
- 3-(3-Cyclopentyloxy-4-methoxy-benzyl)-1-ethyl-8-isopropyl-6-thioxanthine.
- 22. The method of claim 11 wherein R.sup.1 is aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, and wherein said aralkyl is optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy.
- 23. The method of claim 18 wherein R.sup.1 is aralkyl wherein the alkyl moiety of said aralkyl is straight or branched or is cycloalkyl, and wherein said aralkyl is optionally substituted with halogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkoxy, oxo, oximido, carbamido or hydroxy.
BACKGROUND OF THE INVENTION
This application is a continuation of application Ser. No. 08/476,262 filed Jun. 7, 1995, now abandoned, which is a continuation in part of U.S. Ser. No. 08/354,664, filed on Dec. 13, 1994, abandoned the disclosure of which is incorporated herein in its entirety.
US Referenced Citations (102)
Foreign Referenced Citations (1)
Number |
Date |
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4707193 |
Aug 1997 |
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Continuations (1)
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476262 |
Jun 1995 |
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Continuation in Parts (1)
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354664 |
Dec 1994 |
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