1. A compound of Formula (I):
wherein:
G is \u2014C(Z)N(R1)R2, C6-10aryl, or a heterocycle selected from the group consisting of imidazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, oxathiadiazolyl, imidazolinyl, tetrahydropyrimidinyl, thienyl, pyrazolyl, pyrimidinyl, triazinyl, furyl, indazolyl, indolyl, indolinyl, isothiazolyl, isoxazolyl, oxazolyl, isoxadiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, and pyridinyl; wherein aryl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, C2-8alkenyl, C2-8alkynyl, C1-8alkanyloxy, hydroxy(C1-8)alkanyl, carboxy(C1-8)alkanyl, C1-8alkanylcarbonylamino, halogen, hydroxy, cyano, nitro, oxo, thioxo, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-8alkanylthio, C1-8alkanylsulfonyl, C1-8alkanylsulfonylamino, aminocarbonyl, aminothiocarbonyl, aminocarbonylamino, aminothiocarbonylamino, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, and C1-6alkanyloxycarbonylamino;
R1 is a substituent selected from the group consisting of hydrogen, C1-8alkanyl, C2-8alkenyl, and C2-8alkynyl;
R2 is a substituent selected from the group consisting of hydrogen; C1-8alkanyl; C2-8alkenyl; C2-8alkynyl; C6-10aryl; and
C1-8cycloalkanyl;
wherein C1-8alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-6alkanyloxy, thioC1-6alkanyloxy, hydroxy, fluoro, chloro, cyano, aminocarbonyl, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, C1-6alkanyloxycarbonyl, and aryloxy; and wherein any aryl-containing substituents and C1-8cycloalkanyl substituents of R2 are optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, C2-8alkenyl, C2-8alkynyl, C1-8alkanyloxy, trifluoromethyl, trifluoromethoxy, phenyl, halogen, cyano, hydroxy, C1-8alkanylthio, C1-8alkanylsulfonyl, and C1-8alkanylsulfonylamino; or R1 and R2 taken together with the nitrogen to which they are attached form a 5-7 membered cycloheteroalkyl optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, hydroxy(C1-8)alkanyl, hydroxy, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, and halogen;
R3 is a substituent selected from the group consisting of hydrogen, C1-8alkanyl, halo1-3(C1-8)alkanyl, C2-8alkenyl, C2-8alkynyl, C3-8cycloalkanyl, cycloalkanyl(C1-8)alkanyl, C1-8alkanyloxy(C1-8)alkanyl, C1-8alkanylthio(C1-8)alkanyl, hydroxyC1-8alkanyl, C1-8alkanyloxycarbonyl, halo1-3(C1-8)alkanylcarbonyl, formyl, thioformyl, carbamimidoyl, phenylimino(C1-8)alkanyl, phenyl(C1-8)alkanyl, phenyl(C1-8)alkenyl, phenyl(C1-8)alkynyl, naphthyl(C1-8)alkanyl and heteroaryl(C1-8)alkanyl wherein the heteroaryl is selected from the group consisting of benzo1,3dioxolyl, imidazolyl, furanyl, pyridinyl, thienyl, indazolyl, indolyl, indolinyl, isoindolinyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrimidinyl, pyrrolyl, quinolinyl, isoquinolinyl, tetrazolyl, thiazolyl; wherein phenyl, naphthyl, and heteroaryl are optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyl, C2-6alkenyl, C1-6alkanyloxy, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-6alkanylcarbonyl, C1-6alkanylcarbonyloxy, C1-6alkanylcarbonylamino, C1-6alkanylthio, C1-6alkanylsulfonyl, halogen, hydroxy, cyano, fluoro(C1-6)alkanyl, thioureido, and fluoro(C1-6)alkanyloxy; alternatively, when phenyl and heteroaryl are optionally substituted with alkanyl or alkanyloxy substituents attached to adjacent carbon atoms, the two substituents can together form a fused cyclic alkanyl or cycloheteroalkanyl selected from the group consisting of \u2014(CH2)3-5\u2014, \u2014O(CH2)2-4\u2014(CH2)2-4O\u2014, and \u2014O(CH2)1-3O\u2014;
R4 is one to three substituents independently selected from the group consisting of hydrogen; C1-6alkanyl; C2-6alkenyl; C2-6alkynyl; aryl(C2-6)alkynyl; C1-6alkanyloxy; amino; C1-6alkanylamino; di(C1-6alkanyl)amino; C6-10arylamino wherein C6-10aryl is optionally substituted with one to three substitutents independently selected from the group consisting of C1-6alkanyl, C1-6alkoxy, halogen, and hydroxy; formylamino; pyridinylamino; C1-6alkanylcarbonyl; C1-6alkanylcarbonyloxy; C1-6alkanyloxycarbonyl; aminocarbonyl; C1-6alkanylaminocarbonyl; di(C1-6alkanyl)aminocarbonyl; C1-6alkanylcarbonylamino; C1-6alkanylthio; C1-6alkanylsulfonyl; halogen; hydroxy; cyano; hydroxycarbonyl; C6-10aryl; chromanyl; chromenyl; furanyl; imidazolyl; indazolyl; indolyl; indolinyl; isoindolinyl; isoquinolinyl; isothiazolyl; isoxazolyl; naphthyridinyl; oxazolyl; pyrazinyl; pyrazolyl; pyridazinyl; pyridinyl; pyrimidinyl; pyrrolyl; quinazolinyl; quinolinyl; quinolizinyl; quinoxalinyl; tetrazolyl; thiazolyl; thienyl; fluoroalkanyl and fluoroalkanyloxy; or optionally, when R4 is two substituents attached to adjacent carbon atoms, the two substituents together form a single fused moiety; wherein the fused moiety is \u2014(CH2)3-5\u2014, \u2014O(CH2)2-4\u2014(CH2)2-4O\u2014, \u2014O(CH2)1-3O\u2014, or \u2014S\u2014C(NH2)\u2550N\u2014;
R5 is one to two substituents independently selected from the group consisting of hydrogen, C1-6alkanyl, C2-6alkenyl, C1-6alkanyloxy, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-6alkanylcarbonyl, C1-6alkanylcarbonyloxy, C1-6alkanyloxycarbonyl, C1-6alkanylaminocarbonyl, C1-6alkanylcarbonylamino, C1-6alkanylthio, C1-6alkanylsulfonyl, halogen, hydroxy, cyano, fluoro(C1-6)alkanyl and fluoro(C1-6)alkanyloxy;
R6 is one to four substituents independently selected from the group consisting of hydrogen, C1-6alkanyl, C2-6alkenyl, C1-6alkanyloxy, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-6alkanylcarbonyl, C1-6alkanylcarbonyloxy, C1-6alkanyloxycarbonyl, C1-6alkanylaminocarbonyl, C1-6alkanylcarbonylamino, C1-6alkanylthio, C1-6alkanylsulfonyl, halogen, hydroxy, cyano, fluoro(C1-6)alkanyl and fluoro(C1-6)alkanyloxy;
Y is O or S;
Z is O, S, NH, N(C1-6alkanyl), N(OH), N(OC1-6alkanyl), or N(phenyl); and enantiomers, diastereomers, tautomers, solvates, or pharmaceutically acceptable salts thereof.
2. The compound according to claim 1 wherein G is \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of imidazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, oxathiadiazolyl, imidazolinyl, tetrahydropyrimidinyl, thienyl, pyrazolyl, pyrimidinyl, triazinyl, isothiazolyl, isoxazolyl, oxazolyl, isoxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, C1-8alkanyloxy, hydroxy(C1-8)alkanyl, carboxy(C1-8)alkanyl, C1-8alkanylcarbonylamino, halogen, hydroxy, cyano, oxo, thioxo, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-8alkanylthio, aminocarbonyl, aminothiocarbonyl, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, and C1-6alkanyloxycarbonylamino.
3. The compound according to claim 1 wherein G is \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of imidazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, oxathiadiazolyl, imidazolinyl, thienyl, pyrazolyl, pyrimidinyl, triazinyl, isothiazolyl, isoxazolyl, oxazolyl, isoxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-4alkanyl, C1-4alkanyloxy, hydroxy(C1-4)alkanyl, carboxy(C1-4)alkanyl, C1-4alkanylcarbonylamino, hydroxy, cyano, oxo, thioxo, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-8alkanylthio, aminocarbonyl, aminothiocarbonyl, C1-8alkanylaminocarbonyl, and di(C1-8alkanyl)aminocarbonyl.
4. The compound according to claim 1 wherein G is \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of imidazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, oxathiadiazolyl, thienyl, isothiazolyl, isoxazolyl, isoxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-4alkanyl, C1-4alkanyloxy, hydroxy(C1-4)alkanyl, C1-4alkanylcarbonylamino, hydroxy, cyano, oxo, thioxo, and aminocarbonyl.
5. The compound according to claim 1 wherein G is \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of tetrazolyl, oxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-4alkanylcarbonylamino and oxo.
6. The compound according to claim 1 wherein G is N,N-diethylaminocarbonyl, 3-(N,N-diethylaminocarbonyl)-phenyl, 2-methylcarbonylaminophenyl, N\u2014N-diethylamidino, pyridin-3-yl, 3-(S)hydroxypyrrolidin-1-ylcarbonyl, N-ethylaminocarbonyl, 1H-tetrazol-4-yl, pyridine-4-yl, or 4H-1,2,4-oxadiazol-5-oxo-3-yl.
7. The compound according to claim 1 wherein R1 is a substituent selected from the group consisting of hydrogen and C1-4alkanyl.
8. The compound according to claim 1 wherein R1 is selected from the group consisting of hydrogen, methyl, ethyl, and propyl.
9. The compound according to claim 1 wherein R1 is selected from the group consisting of hydrogen, methyl, and ethyl.
10. The compound according to claim 1 wherein R1 is selected from the group consisting of hydrogen and ethyl.
11. The compound according to claim 1 wherein R2 is selected from the group consisting of hydrogen; C1-4alkanyl; phenyl; and C1-6cycloalkanyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-4alkanyloxy, hydroxy, fluoro, chloro, cyano, aminocarbonyl, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, and phenoxy; and wherein any phenyl-containing substituents and C1-6cycloalkanyl substituents of R2 are optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, C1-8alkanyloxy, trifluoromethyl, phenyl, fluoro, hydroxy, C1-8alkanylthio, C1-8alkanylsulfonyl, and C1-8alkanylsulfonylamino; or R1 and R2 taken together with the nitrogen to which they are attached form a 5-7 membered cycloheteroalkyl optionally substituted with one to three substituents independently selected from the group consisting of C1-4alkanyl, hydroxy(C1-4)alkanyl, hydroxy, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, and fluoro.
12. The compound according to claim 1 wherein R2 is selected from the group consisting of hydrogen, C1-4alkanyl, phenyl, and C1-6cycloalkanyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, C1-4alkanyloxy, hydroxy, fluoro, aminocarbonyl, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, and phenoxy; and wherein any phenyl-containing substituent of R2 is optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyl, C1-6alkanyloxy, fluoro, hydroxy, and C1-6alkanylthio; or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl or piperidinyl ring wherein said pyrrolidinyl or piperidinyl is optionally substituted with a substituent selected from the group consisting of C1-4alkanyl and hydroxy.
13. The compound according to claim 1 wherein R2 is selected from the group consisting of hydrogen, C1-4alkanyl and phenyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, C1-4alkanyloxy, hydroxy, fluoro, and phenoxy; and wherein any phenyl-containing substituent of R2 is optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyl, C1-6alkanyloxy, fluoro, and hydroxy; or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl or piperidinyl ring wherein said pyrrolidinyl or piperidinyl is optionally substituted with a substituent selected from the group consisting of C1-3alkanyl and hydroxy.
14. The compound according to claim 1 wherein R2 is selected from the group consisting of hydrogen and C1-4alkanyl, or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl ring optionally substituted with hydroxy.
15. The compound according to claim 1 wherein R2 is hydrogen or ethyl, or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl ring optionally substituted with hydroxy.
16. The compound according to claim 1 wherein R3 is selected from the group consisting of hydrogen, C1-8alkanyl, C2-8alkenyl, C2-8alkynyl, C1-8alkanyloxy(C1-8)alkanyl, C1-8alkanylthio(C1-8)alkanyl, hydroxyC1-8alkanyl, thioformyl, phenylimino(C1-8)alkanyl, phenyl(C1-8)alkanyl, and heteroaryl(C1-8)alkanyl wherein heteroaryl is selected from the group consisting of benzo1,3dioxolyl, imidazolyl, furanyl, pyridinyl, thienyl, indolyl, indolinyl, isoquinolinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrimidinyl, pyrrolyl, quinolinyl, isoquinolinyl, tetrazolyl; wherein phenyl and heteroaryl are optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyloxy and hydroxy; or optionally, when phenyl and heteroaryl are optionally substituted with two substituents attached to adjacent carbon atoms, the two substituents together form a single fused moiety; wherein the moiety is selected from \u2014O(CH2)1-3O\u2014.
17. The compound according to claim 1 wherein R3 is selected from the group consisting of hydrogen, methyl, allyl, 2-methyl-allyl, propynyl, hydroxyethyl, methylthioethyl, methoxyethyl, thioformyl, phenyliminomethyl, phenethyl, and heteroaryl(C1-8)alkanyl wherein the heteroaryl is selected from the group consisting of benzo1,3dioxolyl, imidazolyl, furanyl, pyridinyl, thienyl, pyrimidinyl, pyrrolyl, quinolinyl, isoquinolinyl, tetrazolyl; wherein the phenyl in any phenyl-containing substituent is optionally substituted with one hydroxyl group.
18. The compound according to claim 1 wherein R3 is hydrogen, C1-8alkanyl, C2-8alkenyl, C3-8cycloalkanyl, phenyl(C1-8)alkanyl, or heteroaryl(C1-8)alkanyl wherein the heteroaryl is imidazolyl, furanyl, pyridinyl, or thienyl.
19. The compound according to claim 1 wherein R3 is hydrogen, methyl, allyl, or heteroarylmethyl wherein heteroaryl is selected from the group consisting of benzo1,3dioxolyl, imidazolyl, furanyl, pyridinyl, and thienyl.
20. The compound according to claim 1 wherein R3 is hydrogen, methyl, ethyl, propenyl, cyclopropylmethyl, benzyl, phenethyl, or heteroarylmethyl wherein the heteroaryl is furanyl, imidazolyl, pyridinyl, or thienyl.
21. The compound according to claim 1 wherein R4 is one to three substituents independently selected from the group consisting of hydrogen; C1-6alkanyl; C1-6alkanyloxy; C6-10arylamino wherein C6-10aryl is optionally substituted with one to three substitutents independently selected from the group consisting of C1-6alkanyl, C1-6alkoxy, halogen, and hydroxy; formylamino; pyridinylamino; aminocarbonyl; C1-6alkanylaminocarbonyl; C1-6alkanylcarbonylamino; halogen; hydroxy; C6-10aryl; chromanyl; chromenyl; furanyl; imidazolyl; indazolyl; indolyl; indolinyl; isoindolinyl; isoquinolinyl; isothiazolyl; isoxazolyl; naphthyridinyl; oxazolyl; pyrazinyl; pyrazolyl; pyridazinyl; pyridinyl; pyrimidinyl; pyrrolyl; quinazolinyl; quinolinyl; quinolizinyl; quinoxalinyl; tetrazolyl; thiazolyl; and thienyl.
22. The compound according to claim 1 wherein R4 is one to two substituents independently selected from the group consisting of hydrogen, C1-4alkanyl, C1-4alkanyloxy, halogen, phenyl, furanyl, imidazolyl, indazolyl, indolyl, indolinyl, isoindolinyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinyl, tetrazolyl, thiazolyl, thienyl, and hydroxy.
23. The compound according to claim 1 wherein R4 is one to two substituents independently selected from the group consisting of hydrogen, methyl, methoxy, bromo, fluoro, \u03b1\u2032- or \u03b2\u2032-phenyl, \u03b1\u2032- or \u03b2\u2032-pyridinyl, \u03b1\u2032- or \u03b2\u2032-furanyl, and hydroxy.
24. The compound according to claim 1 wherein R4 is one substituent selected from the group consisting of hydrogen, methoxy, chloro, and hydroxy.
25. The compound according to claim 1 wherein R4 is one substituent and is hydrogen or hydroxy.
26. The compound according to claim 1 wherein R5 is one to two substituents independently selected from the group consisting of hydrogen and halogen.
27. The compound according to claim 1 wherein R5 is hydrogen.
28. The compound according to claim 1 wherein R6 is one to four substituents independently selected from the group consisting of hydrogen, C1-6alkanyl, C2-6alkenyl, C1-6alkanyloxy, halogen, hydroxy, fluoro(C1-6)alkanyl and fluoro(C1-6)alkanyloxy.
29. The compound according to claim 1 wherein R6 is one to two substituents independently selected from the group consisting of hydrogen and C1-4alkanyl.
30. The compound according to claim 1 wherein R6 is one to two substituents independently selected from the group consisting of hydrogen and methyl.
31. The compound according to claim 1 wherein R6 is hydrogen.
32. The compound according to claim 1 wherein Y is O or S.
33. The compound according to claim 1 wherein Y is O.
34. The compound according to claim 1 wherein Z is O, NH, N(C1-6alkanyl), N(OH), N(OC1-6alkanyl), or N(phenyl).
35. The compound according to claim 1 wherein Z is O, NH, or N(OH).
36. The compound according to claim 1 wherein Z is O or NH.
37. The compound according to claim 1 wherein Z is O.
38. The compound according to claim 1 wherein R4 is hydrogen and Y is O.
39. The compound according to claim 1 wherein R4 is \u03b1\u2032-hydroxy and Y is O.
40. The compound according to claim 1 wherein R4 is hydrogen and Y is S.
41. The compound according to claim 1 wherein R4 is \u03b1\u2032-hydroxy and Y is S.
42. A compound of Formula (I):
wherein:
G is independently selected from \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of imidazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, oxathiadiazolyl, imidazolinyl, tetrahydropyrimidinyl, thienyl, pyrazolyl, pyrimidinyl, triazinyl, isothiazolyl, isoxazolyl, oxazolyl, isoxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, C1-8alkanyloxy, hydroxy(C1-8)alkanyl, carboxy(C1-8)alkanyl, C1-8alkanylcarbonylamino, halogen, hydroxy, cyano, oxo, thioxo, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-8alkanylthio, aminocarbonyl, aminothiocarbonyl, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, and C1-6alkanyloxycarbonylamino; provided that when G is pyridin-3-yl or thien-3-yl and R3 is hydrogen, R4 is other than hydrogen;
R1 is hydrogen or C1-4alkanyl;
R2 is selected from the group consisting of hydrogen; C1-4alkanyl; phenyl; and C1-6cycloalkanyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-4alkanyloxy, hydroxy, fluoro, chloro, cyano, aminocarbonyl, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, and phenoxy; and wherein any phenyl-containing substituent of R2 and C1-6cycloalkanyl substituents of R2 are optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, C1-8alkanyloxy, trifluoromethyl, phenyl, fluoro, hydroxy, C1-8alkanylthio, C1-8alkanylsulfonyl, and C1-8alkanylsulfonylamino; or R1 and R2 taken together with the nitrogen to which they are attached form a 5-7 membered heterocycloalkyl wherein said heterocycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of C1-8alkanyl, hydroxy(C1-8)alkanyl, and hydroxy;
R3 is selected from the group consisting of hydrogen, C1-8alkanyl, C2-8alkenyl, C2-8alkynyl, C1-8alkanyloxy(C1-18)alkanyl, C1-8alkanylthio(C1-8)alkanyl, hydroxyC1-8alkanyl, thioformyl, phenylimino(C1-8)alkanyl, phenyl(C1-8)alkanyl, and heteroaryl(C1-8)alkanyl wherein heteroaryl is selected from the group consisting of benzo1,3dioxolyl, imidazolyl, furanyl, pyridinyl, thienyl, indolyl, indolinyl, isoquinolinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyrimidinyl, pyrrolyl, quinolinyl, isoquinolinyl, tetrazolyl; wherein phenyl and heteroaryl are optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyloxy and hydroxy; or optionally, when phenyl and heteroaryl are optionally substituted with two substituents attached to adjacent carbon atoms, the two substituents together form a single fused moiety; wherein the moiety is selected from \u2014O(CH2)1-3O\u2014;
R4 is one to three substituents independently selected from the group consisting of hydrogen; C1-6alkanyl; C1-6alkanyloxy; C6-10arylamino wherein C6-10aryl is optionally substituted with one to three substitutents independently selected from the group consisting of C1-6alkanyl, C1-6alkoxy, halogen, and hydroxy; formylamino; pyridinylamino; aminocarbonyl; C1-6alkanylaminocarbonyl; C1-6alkanylcarbonylamino; halogen; hydroxy; C6-10aryl; chromanyl; chromenyl; furanyl; imidazolyl; indazolyl; indolyl; indolinyl; isoindolinyl; isoquinolinyl; isothiazolyl; isoxazolyl; naphthyridinyl; oxazolyl; pyrazinyl; pyrazolyl; pyridazinyl; pyridinyl; pyrimidinyl; pyrrolyl; quinazolinyl; quinolinyl; quinolizinyl; quinoxalinyl; tetrazolyl; thiazolyl; and thienyl;
R5 is one to two substituents independently selected from the group consisting of hydrogen and halogen;
R6 is one to four substituents independently selected from the group consisting of hydrogen, C1-6alkanyl, C2-6alkenyl, C1-6alkanyloxy, halogen, hydroxy, fluoro(C1-6)alkanyl and fluoro(C1-6)alkanyloxy.
Y is O or S;
Z is O, NH, N(C1-6alkanyl), N(OH), N(OC1-6alkanyl), or N(phenyl); and
enantiomers, diastereomers, tautomers, solvates, and pharmaceutically acceptable salts thereof.
43. A compound of Formula (J):
wherein:
G is selected from \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of imidazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, oxathiadiazolyl, imidazolinyl, thienyl, pyrazolyl, pyrimidinyl, triazinyl, isothiazolyl, isoxazolyl, oxazolyl, isoxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-4alkanyl, C1-4alkanyloxy, hydroxy(C1-4)alkanyl, carboxy(C1-4)alkanyl, C1-4alkanylcarbonylamino, hydroxy, cyano, oxo, thioxo, amino, C1-6alkanylamino, di(C1-6alkanyl)amino, C1-8alkanylthio, aminocarbonyl, aminothiocarbonyl, C1-8alkanylaminocarbonyl, and di(C1-8alkanyl)aminocarbonyl;
R1 is selected from the group consisting of hydrogen, methyl, ethyl, and propyl;
R2 is selected from the group consisting of hydrogen, C1-4alkanyl, phenyl, and C1-6cycloalkanyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, C1-4alkanyloxy, hydroxy, fluoro, aminocarbonyl, C1-8alkanylaminocarbonyl, di(C1-8alkanyl)aminocarbonyl, and phenoxy; and wherein any phenyl-containing substituent of R2 is optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyl, C1-6alkanyloxy, fluoro, hydroxy, and C1-6alkanylthio; or R1 and R2 taken together with the nitrogen to which they are attached form pyrrolidinyl or piperidinyl ring wherein said pyrrolidinyl or piperidinyl is optionally substituted with a substituent selected from the group consisting of C1-3alkanyl and hydroxy;
R3 is selected from the group consisting of hydrogen, methyl, allyl, 2-methyl-allyl, propynyl, hydroxyethyl, methylthioethyl, methoxyethyl, thioformyl, phenyliminomethyl, phenethyl, and heteroaryl(C1-8)alkanyl wherein the heteroaryl is selected from the group consisting of benzo1,3dioxolyl, imidazolyl, furanyl, pyridinyl, thienyl, pyrimidinyl, pyrrolyl, quinolinyl, isoquinolinyl, tetrazolyl; wherein the phenyl in any phenyl-containing substituent is optionally substituted with one hydroxyl group;
R4 is one to two substituents independently selected from the group consisting of hydrogen, C1-4alkanyl, C1-4alkanyloxy, halogen, phenyl, furanyl, imidazolyl, indazolyl, indolyl, indolinyl, isoindolinyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinyl, tetrazolyl, thiazolyl, thienyl, and hydroxy;
R5 is hydrogen;
R6 is one to two substituents independently selected from the group consisting of hydrogen and C1-4alkanyl;
Y is O or S;
Z is O, NH, or N(OH); and
enantiomers, diastereomers, tautomers, solvates, and pharmaceutically acceptable salts thereof.
44. The compound according to claim 26 wherein G is \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of imidazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, oxathiadiazolyl, thienyl, isothiazolyl, isoxazolyl, isoxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-4alkanyl, C1-4alkanyloxy, hydroxy(C1-4)alkanyl, C1-4alkanylcarbonylamino, hydroxy, cyano, oxo, thioxo, and aminocarbonyl.
45. The compound according to claim 26 wherein G is \u2014C(Z)N(R1)R2, 2-methylcarbonylaminophenyl, 2-aminocarbonyl-phenyl, 1H-tetrazol-4-yl, 2-methyl-tetrazol-5-yl, 4H-1,2,4-oxadiazol-5-oxo-3-yl, 4H-1,2,4-oxadiazol-5-thioxo-3-yl, 4H-1,2,4thiadiazol-5-oxo-3-yl, 1,2,3,5oxathiadiazol-2-oxo-4-yl, or pyridin-3-yl.
46. The compound according to claim 26 wherein R2 is selected from the group consisting of hydrogen, C1-4alkanyl and phenyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, C1-4alkanyloxy, hydroxy, fluoro, and phenoxy; and wherein any phenyl-containing substituent is optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyl, C1-6alkanyloxy, fluoro, and hydroxy; or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl or piperidinyl ring wherein said pyrrolidinyl or piperidinyl is optionally substituted with a substituent selected from C1-3alkanyl or hydroxy; and R3 is a substituent selected from the group consisting of benzo1,3dioxol-5-ylmethyl, carbamimidoyl, 1-H-imidazol-4-ylmethyl, phenyliminomethyl, 1-prop-2-ynyl, thioformyl, 2-hydroxyphenyl-methyl, hydroxy-ethyl, methoxy-ethyl, 2-methyl-allyl, 2-methyl-but-2-enyl, allyl, furan-3-ylmethyl, H, Me, methylthioethyl, phenethyl, pyridin-2-yl methyl, and thiophen-2-yl methyl.
47. A compound of Formula (J):
wherein:
G is selected from \u2014C(Z)N(R1)R2, 2-methylcarbonylaminophenyl, 2-aminocarbonyl-phenyl, 1H-tetrazol-4-yl, 2-methyl-tetrazol-5-yl, 4H-1,2,4-oxadiazol-5-oxo-3-yl, 4H-1,2,4-oxadiazol-5-thioxo-3-yl, 4H-1,2,4thiadiazol-5-oxo-3-yl, 1,2,3,5oxathiadiazol-2-oxo-4-yl, or pyridin-3-yl;
R1 is hydrogen, methyl, or ethyl;
R2 is selected from the group consisting of hydrogen, C1-4alkanyl and phenyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, C1-4alkanyloxy, hydroxy, fluoro, and phenoxy; and wherein any phenyl-containing substituent of R2 is optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyl, C1-6alkanyloxy, fluoro, and hydroxy; or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl or piperidinyl ring wherein said pyrrolidinyl or piperidinyl is optionally substituted with a substituent selected from C1-3alkanyl or hydroxy;
R3 is selected from the group consisting of hydrogen, methyl, allyl, 2-methyl-allyl, propynyl, hydroxyethyl, methylthioethyl, methoxyethyl, thioformyl, phenyliminomethyl, phenethyl, and heteroaryl(C1-8)alkanyl wherein the heteroaryl is selected from the group consisting of benzo1,3dioxolyl, imidazolyl, furanyl, pyridinyl, thienyl, pyrimidinyl, pyrrolyl, quinolinyl, isoquinolinyl, tetrazolyl; wherein the phenyl in any phenyl-containing substituent is optionally substituted with one hydroxyl group;
R4 is one to three substituents independently selected from the group consisting of hydrogen, C1-4alkanyl, C1-4alkanyloxy, halogen, phenyl, furanyl, imidazolyl, indazolyl, indolyl, indolinyl, isoindolinyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinyl, tetrazolyl, thiazolyl, thienyl, and hydroxy;
R5 is hydrogen;
R6 is one to two substituents independently selected from the group consisting of hydrogen and methyl;
Y is O or S;
Z is O or NH; and
enantiomers, diastereomers, tautomers, solvates, and pharmaceutically acceptable salts thereof.
48. The compound according to claim 31 wherein R2 is a substituent selected from the group consisting of hydrogen, C1-4alkanyl and phenyl; wherein C1-4alkanyl is optionally substituted with one to three substituents independently selected from the group consisting of phenyl, C1-4alkanyloxy, hydroxy, and 2,6-dimethyl-phenoxy; and wherein any phenyl-containing substituent of R2 is optionally substituted with one to three substituents independently selected from the group consisting of C1-6alkanyl, C1-6alkanyloxy, fluoro, and hydroxy; or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl or piperidinyl ring wherein said pyrrolidinyl or piperidinyl is optionally substituted with a substituent selected from C1-3alkanyl or hydroxy.
49. The compound according to claim 31 wherein R3 is a substituent selected from the group consisting of benzo1,3dioxol-5-ylmethyl, carbamimidoyl, 1-H-imidazol-4-ylmethyl, phenyliminomethyl, 1-prop-2-ynyl, thioformyl, 2-hydroxyphenyl-methyl, hydroxy-ethyl, methoxy-ethyl, 2-methyl-allyl, 2-methyl-but-2-enyl, allyl, furan-3-ylmethyl, H, Me, methylthioethyl, phenethyl, pyridin-2-yl methyl, and thiophen-2-ylmethyl; and R4 is one to two substituents independently selected from the group consisting of hydrogen, C1-4alkanyl, C1-4alkanyloxy, halogen, phenyl, furanyl, imidazolyl, indazolyl, indolyl, indolinyl, isoindolinyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinyl, tetrazolyl, thiazolyl, thienyl, and hydroxy.
50. The compound according to claim 31 wherein R3 is a substituent selected from the group consisting of benzo1,3dioxol-5-ylmethyl, carbamimidoyl, 1-H-imidazol-4-yl methyl, phenyliminomethyl, 1-prop-2-ynyl, thioformyl, 2-hydroxyphenyl-methyl, hydroxyethyl, methoxyethyl, allyl, furan-3-yl methyl, H, Me, methylthioethyl, and phenethyl; R4 is one to two substituents independently selected from the group consisting of hydrogen, methyl, methoxy, bromo, fluoro, \u03b1\u2032- or \u03b2\u2032-phenyl, \u03b1\u2032- or \u03b2\u2032-pyridinyl, \u03b1\u2032- or \u03b2\u2032-furanyl, and hydroxy.
51. The compound according to claim 31 wherein R3 is a substituent selected from the group consisting of H, benzo1,3dioxol-5-ylmethyl, 1-H-imidazol-4-yl methyl, furan-3-ylmethyl, pyridin-2-ylmethyl, and phenyliminomethyl; and R4 is a substituent independently selected from the group consisting of hydrogen, methyl, methoxy, bromo, fluoro, \u03b1\u2032- or \u03b2\u2032-phenyl, \u03b1\u2032- or \u03b2\u2032-pyridinyl, \u03b1\u2032- or \u03b2\u2032-furanyl, and hydroxy.
52. A compound of Formula (J):
wherein:
G is \u2014C(Z)N(R1)R2, phenyl, or a heterocycle selected from the group consisting of tetrazolyl, oxadiazolyl, and pyridinyl; wherein phenyl and the heterocycles of G are optionally substituted with one to three substituents independently selected from the group consisting of C1-4alkanylcarbonylamino and oxo;
R1 is selected from the group consisting of hydrogen and ethyl;
R2 is selected from the group consisting of hydrogen and C1-4alkanyl;
or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl ring optionally substituted with hydroxy;
R3 is hydrogen, C1-8alkanyl, C2-8alkenyl, C3-8cycloalkanyl, phenyl(C1-8)alkanyl, or heteroaryl(C1-8)alkanyl wherein the heteroaryl is imidazolyl, furanyl, pyridinyl, or thienyl;
R4 is one substituent selected from the group consisting of hydrogen, methoxy, chloro, and hydroxy;
R5 is hydrogen;
R6 is hydrogen;
Y is O or S;
Z is O; and
enantiomers, diastereomers, tautomers, solvates, and pharmaceutically acceptable salts thereof.
53. A compound according to claim 52 wherein R4 is hydrogen and Y is O.
54. A compound according to claim 52 wherein R4 is \u03b1\u2032-hydroxy and Y is O.
55. A compound according to claim 52 wherein R4 is hydrogen and Y is S.
56. A compound according to claim 52 wherein R4 is \u03b1\u2032-hydroxy and Y is S.
57. A compound of Formula (I):
wherein:
G is N,N-diethylaminocarbonyl, 3-(N,N-diethylaminocarbonyl)-phenyl, 2-methylcarbonylaminophenyl, N\u2014N-diethylamidino, pyridin-3-yl, 3-(S)-hydroxypyrrolidin-1-ylcarbonyl, N-ethylaminocarbonyl, 1H-tetrazol-4-yl, pyridine-4-yl, or 4H-1,2,4-oxadiazol-5-oxo-3-yl;
R1 is selected from the group consisting of hydrogen and ethyl;
R2 is hydrogen or ethyl;
or R1 and R2 taken together with the nitrogen to which they are attached form a pyrrolidinyl ring optionally substituted with hydroxy;
R3 is hydrogen, methyl, ethyl, propenyl, cyclopropylmethyl, benzyl, phenethyl, or heteroaryl wherein the heteroaryl is furanyl, imidazolyl, pyridinyl, or thienyl;
R4 is one substituent and is hydrogen or hydroxy;
R5 is hydrogen;
R6 is hydrogen;
Y is O or S;
Z is O; and
enantiomers, diastereomers, tautomers, solvates, and pharmaceutically acceptable salts thereof.
58. A compound according to claim 57 wherein R4 is hydrogen and Y is O.
59. A compound according to claim 57 wherein R4 is \u03b1\u2032-hydroxy and Y is O.
60. A compound according to claim 57 wherein R4 is hydrogen and Y is S.
61. A compound according to claim 57 wherein R4 is \u03b1\u2032-hydroxy and Y is S.
62. A compound that is:
N-{2-5-Hydroxy-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
N-{2-5-Hydroxy-9-(1-thiophen-2-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
6-Pyridin-4-yl-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-thioxanthen-4-ol;
N-{2-5-Hydroxy-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-thioxanthen-3-yl-phenyl}-acetamide;
N-2-(5-Hydroxy-9-piperidin-4-yl-9H-thioxanthen-3-yl)-phenyl-acetamide;
9-Piperidin-4-yl-6-pyridin-3-yl-9H-thioxanthen-4-ol;
6-Pyridin-3-yl-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-thioxanthen-4-ol;
9-Piperidin-4-yl-6-pyridin-4-yl-9H-thioxanthen-4-ol;
5-Hydroxy-9-piperidin-4-yl-9H-xanthene-3-carboxylic acid diethylamide;
9-Piperidin-4-yl-6-(1H-tetrazol-5-yl)-9H-xanthen-4-ol;
9-Piperidin-4-yl-9H-xanthene-3-carboxylic acid diethylamide;
N,N-Diethyl-9-(1-furan-3-ylmethyl-piperidin-4-yl)-9H-xanthene-3-carboxamidine;
9-(1-Allyl-piperidin-4-yl)-6-pyridin-3-yl-9H-xanthen-4-ol;
N,N-Diethyl-3-(5-hydroxy-9-piperidin-4-yl-9H-xanthen-3-yl)-benzamide;
N-2-(5-Hydroxy-9-piperidin-4-yl-9H-xanthen-3-yl)-phenyl-acetamide;
N,N-Diethyl-9-piperidin-4-yl-9H-xanthene-3-carboxamidine;
4-(5-Methoxy-9-piperidin-4-yl-9H-thioxanthen-3-yl)-pyridine;
9-(1-Benzyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
3-(5-Methoxy-9-piperidin-4-yl-9H-thioxanthen-3-yl)-pyridine;
9-(1-Benzyl-piperidin-4-yl)-6-pyridin-3-yl-9H-xanthen-4-ol;
6-Pyridin-3-yl-9-(1-thiophen-2-ylmethyl-piperidin-4-yl)-9H-xanthen-4-ol;
N-{2-9-(1-Furan-3-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
9-1-(1H-Imidazol-2-ylmethyl)-piperidin-4-yl-9H-xanthene-3-carboxylic acid diethylamide;
N-2-(5-Methoxy-9-piperidin-4-yl-9H-thioxanthen-3-yl)-phenyl-acetamide;
N-{2-9-(1-Allyl-piperidin-4-yl)-5-hydroxy-9H-thioxanthen-3-yl-phenyl}-acetamide;
9-(1-Furan-3-ylmethyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
3-(9-Piperidin-4-yl-9H-xanthen-3-yl)-pyridine;
5-Hydroxy-9-piperidin-4-yl-9H-xanthene-3-carbonitrile;
N-{2-9-(1-Pyridin-2-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
9-(1-Furan-3-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-(3-(S)-hydroxy-pyrrolidin-1-yl)-methanone;
5-Hydroxy-9-piperidin-4-yl-9H-xanthene-3-carboxylic acid ethylamide;
9-Piperidin-4-yl-6-pyridin-3-yl-9H-xanthen-4-ol;
5-Chloro-9-piperidin-4-yl-9H-xanthene-3-carboxylic acid diethylamide;
5-Methoxy-9-piperidin-4-yl-9H-xanthene-3-carboxylic acid diethylamide;
3-9-(1-Furan-3-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-pyridine;
3-(5-Methoxy-9-piperidin-4-yl-9H-xanthen-3-yl)-pyridine;
(3-(S)-Hydroxy-pyrrolidin-1-yl)-(9-piperidin-4-yl-9H-xanthen-3-yl)methanone;
9-(1-Thiophen-2-ylmethyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
1-Furan-3-ylmethyl-4-3-(1H-tetrazol-5-yl)-9H-xanthen-9-yl-piperidine;
4-(5-Methoxy-9-piperidin-4-yl-9H-xanthen-3-yl)-pyridine;
3-(9-Piperidin-4-yl-9H-xanthen-3-yl)-4H-1,2,4oxadiazol-5-one;
N-2-(5-Methoxy-9-piperidin-4-yl-9H-xanthen-3-yl)-phenyl-acetamide;
4-3-(1H-Tetrazol-5-yl)-9H-xanthen-9-yl-piperidine;
3-9-(1-Benzyl-piperidin-4-yl)-9H-xanthen-3-yl-pyridine;
4-9-(1-Furan-3-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-pyridine;
N-2-(9-Piperidin-4-yl-9H-xanthen-3-yl)-phenyl-acetamide;
9-(1-Cyclopropylmethyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
N-{2-9-(1-Allyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
9-(1-Methyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
4-9-(1-Pyridin-2-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-pyridine;
9-(1-Pyridin-2-ylmethyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
3-9-(1-Phenethyl-piperidin-4-yl)-9H-xanthen-3-yl-pyridine;
9-(1-Phenethyl-piperidin-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
4-(9-Piperidin-4-yl-9H-xanthen-3-yl)-pyridine;
N-{2-9-(1-Phenethyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
(3-(S)-Hydroxy-pyrrolidin-1-yl)-9-(1-phenethyl-piperidin-4-yl)-9H-xanthen-3-yl-methanone;
9-(1-Allyl-piperidin-4-yl)-9H-xanthen-3-yl-(3-(S)-hydroxy-pyrrolidin-1-yl)methanone;
3-{9-1-(1H-Imidazol-2-ylmethyl)-piperidin-4-yl-9H-xanthen-3-yl}-pyridine;
3-9-(1-Thiophen-2-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-pyridine;
1-Phenethyl-4-3-(1H-tetrazol-5-yl)-9H-xanthen-9-yl-piperidine;
3-{9-1-(1H-Imidazol-2-ylmethyl)-piperidin-4-yl-9H-xanthen-3-yl}-4H-1,2,4oxadiazol-5-one;
9-Piperidin-4-yl-6-pyridin-4-yl-9H-xanthen-4-ol;
3-9-(1-Furan-3-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-4H-1,2,4oxadiazol-5-one;
N,N-Diethyl-9-(1-phenethyl-piperidin-4-yl)-9H-xanthene-3-carboxamidine;
N-{2-9-(1-Furan-3-ylmethyl-piperidin-4-yl)-5-hydroxy-9H-thioxanthen-3-yl-phenyl}-acetamide;
N,N-Diethyl-5-hydroxy-9-piperidin-4-yl-9H-xanthene-3-carboxamidine; or
5-Hydroxy-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-xanthene-3-carbonitrile.
63. A compound that is:
N-{2-5-Hydroxy-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
N-{2-5-Hydroxy-9-(1-thiophen-2-ylmethyl-piperidin-4-yl)-9H-xanthen-3-yl-phenyl}-acetamide;
6-Pyridin-4-yl-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-thioxanthen-4-ol;
N-{2-5-Hydroxy-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-thioxanthen-3-yl-phenyl}-acetamide;
N-2-(5-Hydroxy-9-piperidin-4-yl-9H-thioxanthen-3-yl)-phenyl-acetamide;
9-Piperidin-4-yl-6-pyridin-3-yl-9H-thioxanthen-4-ol;
6-Pyridin-3-yl-9-(1-pyridin-2-ylmethyl-piperidin-4-yl)-9H-thioxanthen-4-ol;
9-Piperidin-4-yl-6-pyridin-4-yl-9H-thioxanthen-4-ol;
5-Hydroxy-9-piperidin-4-yl-9H-xanthene-3-carboxylic acid diethylamide; or
9-Piperidin-4-yl-6-(1H-tetrazol-5-yl)-9H-xanthen-4-ol.
64. A composition comprising the dextrorotatory enantiomer of a compound of claim 1 wherein said composition is substantially free from the levorotatory isomer of said compound.
65. A composition comprising the levororotatory enantiomer of a compound of claim 1 wherein said composition is substantially free from the dextrorotatory isomer of said compound.
66. A pharmaceutical composition comprising a compound, salt or solvate according to claim 1 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
67. A veterinary composition comprising a compound, salt or solvate according to claim 1 admixed with a veterinarily acceptable carrier, excipient or diluent.
68. A pharmaceutical composition comprising a compound, salt or solvate according to claim 42 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
69. A veterinary composition comprising a compound, salt or solvate according to claim 42 admixed with a veterinarily acceptable carrier, excipient or diluent.
70. A pharmaceutical composition comprising a compound, salt or solvate according to claim 43 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
71. A veterinary composition comprising a compound, salt or solvate according to claim 43 admixed with a veterinarily acceptable carrier, excipient or diluent.
72. A pharmaceutical composition comprising a compound, salt or solvate according to claim 47 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
73. A veterinary composition comprising a compound, salt or solvate according to claim 47 admixed with a veterinarily acceptable carrier, excipient or diluent.
74. A pharmaceutical composition comprising a compound, salt or solvate according to claim 52 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
75. A veterinary composition comprising a compound, salt or solvate according to claim 52 admixed with a veterinarily acceptable carrier, excipient or diluent.
76. A pharmaceutical composition comprising a compound, salt or solvate according to claim 57 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
77. A veterinary composition comprising a compound, salt or solvate according to claim 57 admixed with a veterinarily acceptable carrier, excipient or diluent.
78. A pharmaceutical composition comprising a compound, salt or solvate according to claim 62 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
79. A veterinary composition comprising a compound, salt or solvate according to claim 62 admixed with a veterinarily acceptable carrier, excipient or diluent.
80. A pharmaceutical composition comprising a compound, salt or solvate according to claim 63 admixed with a pharmaceutically acceptable carrier, excipient or diluent.
81. A veterinary composition comprising a compound, salt or solvate according to claim 63 admixed with a veterinarily acceptable carrier, excipient or diluent.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. An oligothiophene-arylene derivative of Formula 1:
wherein
Ar is a C2-30 heteroarylene interrupted by at least one nitrogen atom which may be substituted with hydrogen, hydroxyl, amino, C1-20 linear, branched or cyclic alkyl, C1-20 alkoxyalkyl, alkylamino, ester or amido, or C1-16 linear, branched or cyclic alkoxy, alkylamino, ester or amido;
Ar1 is a C2-30 aryl group which may be interrupted by at least one heteroatom and may be substituted with C1-20 linear, branched or cyclic alkyl;
Ar2 is a C5-30 aryl group which may be interrupted by at least one heteroatom and may be substituted with hydrogen, hydroxyl, amino, C1-20 linear, branched or cyclic alkyl, C1-20 alkoxyalkyl, alkylamino, ester or amido, or C1-16 linear, branched or cyclic alkoxy, alkylamino, ester or amido;
the substituents R1 are each independently hydrogen, hydroxyl, amino, C1-20 linear, branched or cyclic alkyl, C1-20 alkoxyalkyl, alkylamino, ester, amido, or a C1-16 linear, branched or cyclic alkoxy, alkylamino, ester or amido;
n1 is 1;
n2 is an integer between 2 and 8; and
n3 is an integer between 0 and 6.
2. The oligothiophene-arylene derivative according to claim 1, wherein the oligothiophene-arylene derivative is synthesized from compounds of Formulae 2, 3, 4 and 5:
X1\u2014Ar\u2014X2\u2003\u2003(2)
wherein
Ar is as defined in Formula 1, and
X1 and X2 are each independently Br, Cl, or I;
wherein
Ar1 is as defined in Formula 1,
X3 is a trialkyltin group, a dioxaborane group, boronic acid, or the like, and
n1 is an integer between 0 and 6;
wherein
X4 is a trialkyltin group, a dioxaborane group, boronic acid, or the like, and
n2 is an integer between 2 and 8; and
wherein
Ar2 is as defined in Formula 1,
X5 is a trialkyltin group, a dioxaborane group, boronic acid, or the like, and
n3 is an integer between 0 and 6.
3. The oligothiophene-arylene derivative according to claim 1, wherein Ar is selected from the group of compounds consisting of the compounds of Formula 6:
wherein
R2, R3 and R4 are each independently hydrogen, hydroxyl, amino, C1-20 linear, branched or cyclic alkyl, C1-20 alkoxyalkyl, alkylamino, ester, amido, or C1-16 linear, branched or cyclic alkoxy, alkylamino, ester or amido.
4. The oligothiophene-arylene derivative according to claim 1, wherein Ar1 is selected from the group of compounds consisting of the compounds of Formula 7:
wherein
R5, R6, R7, R8, R9, R10, R11, R12 and R13 are each independently hydrogen, hydroxyl, amino, C1-20 linear, branched or cyclic alkyl.
5. The oligothiophene-arylene derivative according to claim 1, wherein Ar2 is selected from the group of compounds consisting of the compounds of Formula 8:
wherein
R14, R15, R16, R17, R18, R19, R20 and R21 are each independently hydrogen, hydroxyl, amino, C1-20 linear, branched or cyclic alkyl, C1-20 alkoxyalkyl, alkylamino, ester, amido, or C1-16 linear, branched or cyclic alkoxy, alkylamino, ester or amido.
6. The oligothiophene-arylene derivative according to claim 1, wherein the oligothiophene-arylene derivative is prepared by chemical condensation in the presence of a catalyst represented by the group consisting of the catalysts of Formulae 9, 10 and 11:
Pd(L)4\u2003\u2003(9)
wherein L is a ligand selected from the group consisting of triphenylphosphine, triphenylarsine, triphenylphosphite, diphenylphosphinoferrocene, diphenylphosphino butane, acetate, and dibenzylideneacetone;
Pd(L)2(X)2\u2003\u2003(10)
wherein L is as defined in Formula 9, and X is I, Br or Cl; and
Pd(L)2\u2003\u2003(11)
wherein L is as defined in Formula 9.
7. An organic thin film transistor comprising a substrate, a gate electrode, a gate insulating film, an organic active layer and source-drain electrodes wherein the organic active layer is made of the oligothiophene-arylene derivative according to claim 1.
8. The organic thin film transistor according to claim 7, wherein the organic active layer is formed into a thin film by screen printing, printing, spin coating, dipping, or ink spraying.
9. The organic thin film transistor according to claim 7, wherein the insulating layer is made of a ferroelectric insulator selected from the group consisting of Ba0.33Sr0.66TiO3, Al2O3, Ta2O5, La2O5, Y2O3, and TiO2; an inorganic insulator selected from the group consisting of PbZr0.33Ti0.66O3, Bi4Ti3O12, BaMgF4, SrBi2(TaNb)2O9, Ba(ZrTi)O3, BaTiO3, SrTiO3, Bi4Ti3O12, SiO2, SiNx, and AlON; or an organic insulator selected from the group consisting of polyimides, benzocyclobutenes, parylenes, polyacrylates, polyvinylalcohols, and polyvinylphenols.
10. The organic thin film transistor according to claim 7, wherein the substrate is made of a material selected from the group consisting of glass, polyethylenenaphthalate, polyethyleneterephthalate, polycarbonate, polyvinylalcohol, polyacrylate, polyimide, polynorbornene, and polyethersulfone.
11. The organic thin film transistor according to claim 7, wherein the gate electrode and source-drain electrodes are made of a material selected from the group consisting of gold, silver, aluminum, nickel, and indium tin oxide.