Claims
- 1. A compound of formula I:
- 2. The compound of claim 1, wherein anion X- is chloride, bromide, mesylate, tosylate, brosylate, mesitylene sulfonate, fumarate, maleate or acetate.
- 3. The compound of claim 1 wherein:
RW and RY are independently hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, CH3C(O)NH—, fluoroalkyl, perfluoroaryl, or hydroxyalkyl or, together with their ring carbon atoms form a fused 6-membered aromatic or heteroaromatic ring; R1 and R2 are methyl; aryl is a C6 or C10 aromatic ring, optionally substituted as set forth below, or a 5- or 6-membered heteroaromatic (heteroaryl) ring containing at least one and up to three atoms of N for the 6-membered heteroaryl ring and from one to three atoms of N or one atom of O or S and zero to two atoms of N for the 5-membered heteroaryl ring; each heteroaromatic ring can be substituted with up to two amino-, dialkylamino-, pyrrolidin-1-yl, piperidin-1-yl, morpholin-4-yl, thiamorpholin-4-yl, 4-(aryl)piperidin-1-yl, 4-(aryl)piperazin-1-yl- (said aryl group being C6 or C10 and optionally substituted as described below), halo or fused to a substituted benzene ring, and wherein said heteroaromatic rings can be additionally substituted; said C6 or C10 aromatic rings can be additionally substituted with acylamino, acyloxyalkyl, alkanoyl, alkanoylalkyl, alkenyl, alkoxy, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylamino, (C1-C3)-alkylenedioxy, alkylsulfonyl, alkylthio, allyl, amino, benzoyl, carboxy, carboxyalkyl, cycloalkyl, dialkylamino, halo, fluoromethyl, difluoromethyl, trifluoromethyl, hydroxy, (C2-C6)-hydroxyalkyl, mercapto, nitro, phenoxy, phenyl, phenylalkyl, sulfamoyl, sulfo, aminosulfonyl, phenylsulfonyl, or phenylsulfinyl; said heteroaromatic rings can be additionally substituted with acylamino, alkanoyl, alkoxy, alkoxycarbonyl, alkoxycarbonylalkyl, alkyl, alkylamino, alkylsulfonyl, alkylthio, amino, arylsulfonyl, benzoyl, carboxy, dialkylamino, halo, fluoralkyl, hydroxy, mercapto, nitro, phenyl, phenoxy, pyrrolidin-1-yl, piperidin-1-yl, 4-arylpiperidin-1-yl, morpholin-4-yl, 4-arylpiperazin-1-yl, sulfamoyl, fluoromethyl, difluoromethyl or trifluoromethyl; and the halo atoms are fluoro, chloro or bromo.
- 4. The compound of claim 3, wherein:
W and Y are CRW and CRY, respectively; Z is S, and the compounds are thiazolium salts; and RY is acetamido, hydrogen, methyl, amino, alkylthio, fluoromethyl, difluoromethyl or trifluoromethyl.
- 5. The compound of claim 3, wherein:
W is N and Y is CRY; Z is S, and the compounds are [1,3,4]-thiadiazolium salts; RY is hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, fluoroalkyl, perfluoroaryl, or hydroxyalkyl; and R4 is acetamido, hydrogen, methyl, amino, alkylthio, fluoromethyl, difluoromethyl or trifluoromethyl.
- 6. The compound of claim 3, wherein:
R4 is hydrogen, methyl, amino, alkylthio, fluoromethyl or difluoromethyl.
- 7. The compound of claim 6, wherein Q is —C(O)CH2—.
- 8. The compound of claim 7, wherein:
W is N and Y is CRY; and Z is O and the compounds are [1,3,4]-oxadiazolium salts; and RY is hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, fluoroalkyl, perfluoroaryl, or hydroxyalkyl.
- 9. The compound of claim 7, wherein:
W is N and Y is CRY; Z is NRZ and the compounds are [1,2,4]-triazolium salts; and RY is hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, fluoroalkyl, perfluoroaryl, or hydroxyalkyl.
- 10. The compound of claim 7, wherein
W and Y are CRW and CRY, respectively; and Z is NRZ, and the compounds are imidazolium salts.
- 11. The compound of claim 7, wherein:
W is CRW and Y is N; Z is S and the compounds are [1,2,4]-thiadiazolium salts; and RW is hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, fluoroalkyl, perfluoroaryl, or hydroxyalkyl.
- 12. The compound of claim, wherein Q is —CH2—.
- 13. The compound of claim 12, wherein:
W is N and Y is CRY; Z is O and the compounds are [1,3,4]-oxadiazolium salts; and RY is hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, fluoroalkyl, perfluoroaryl, or hydroxyalkyl.
- 14. The compound of claim 12, wherein:
W is N and Y is CRY; Z is NRZ and the compounds are [1,2,4]-triazolium salts; and RY is hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, fluoroalkyl, perfluoroaryl, or hydroxyalkyl.
- 15. The compound of claim 12, wherein:
W and Y are CRW and CRY, respectively; and Z is NRZ, and the compounds are imidazolium salts.
- 16. The compound of claim 12, wherein:
W is CRW and Y is N; Z is S and the compounds are [1,2,4]-thiadiazolium salts; and RW is hydrogen, alkyl, aryloxy, arylthio, amino, alkylamino, dialkylamino, fluoroalkyl, perfluoroaryl, or hydroxyalkyl.
- 17. The compound of claim 1, wherein:
Q is —C(O)—CH2— and: W and Y are C(CH3); Z is S; each of R1, R2, and R3 is CH3, or R1 and R3 are CH3 and R2 is H; and R4 is H or CH3.
- 18. The compound of claim 1, wherein:
Q is —C(O)—CH2— and: W is N, Y is C(CH3); Z is S; each of R1, R2, and R3 is CH3, or R1 and R3 are CH3 and R2 is H; and R4 is H or CH3.
- 19. The compound of claim 1, wherein
Q is —C(O)CH2— and: W is N and Y is C(CH3); Z is N—C6H5; each of R1, R2, and R3 is CH3, or R1 and R3 are CH3 and R2 is H; and R4 is H.
- 20. The compound of claim 1, wherein:
Q is —C(O)—CH2— and: W is N and Y is C(CH3); Z is N—CH3; R1 and R3 are CH3 and R2 is H; and R4 is H.
- 21. The compound of claim 1, wherein
Q is —CH2— and: W and Y are C(CH3); Z is S; each of R1, R2, and R3 is CH3, or R1 and R3 are CH3 and R2 is H; and R4 is H or CH3.
- 22. The compound of claim 1, wherein
Q is —CH2— and: W is N, Y is C(CH3); Z is S; each of R1, R2, and R3 is CH3, or R1 and R3 are CH3 and R2 is H; and R4 is H or CH3.
- 23. The compound of claim 1, wherein
Q is —CH2— and: W is N and Y is C(CH3); Z is N—C6H5; each of R1, R2, and R3 is CH3, or R1 and R3 are CH3 and R2 is H; R4 is H.
- 24. A compound having the formula:
- 25. The compound of claim 24, wherein:
RW and RY are each alkyl; R1 and R2 are each, alkyl; and R4 is hydrogen.
- 26. The compound of claim 25, wherein RW, RY, R1 and R2 are each, methyl.
- 27. A method of decreasing intraocular pressure in an animal, including a human, comprising administering an intraocular pressure decreasing amount of a compound having the formula:
- 28. The method of claim 27, wherein anion X- is chloride, bromide, mesylate, tosylate, brosylate, mesitylene sulfonate, fumarate, maleate or acetate.
- 29. The method of claim 27, wherein RW and RY are methyl.
- 30. The method of claim 29, wherein X- is chloride.
Parent Case Info
[0001] This application is a continuation of U.S. patent application Ser. No. 10/158,685, filed May 30, 2002, which claims priority to Provisional Patent Applciation Serial No. 60/294,409, filed May 30, 2001.
Provisional Applications (1)
|
Number |
Date |
Country |
|
60294409 |
May 2001 |
US |
Continuations (1)
|
Number |
Date |
Country |
Parent |
10158685 |
May 2002 |
US |
Child |
10671107 |
Sep 2003 |
US |