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US 2006/0135522 A1Published application
Tricyclic delta-opioid modulators
OwnerJohn Carson, Scott Dax +4inventors
InventorsJohn Carson, Scott Dax, Bart DeCorte, Li Liu, Mark McDonnell, James McNally
Life of this patent
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Abstract
The invention is directed to delta opioid receptor modulators. More specifically, the invention relates to tricyclic δ-opioid modulators. Pharmaceutical and veterinary compositions and methods of treating mild to severe pain and various diseases using compounds of the invention are also described.
Claims81
A compound of Formula (I):
- wherein:
- G is —C(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 benzo[1,3]dioxolyl, 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 —(CH2)3-5—, —O(CH2)2-4—, —(CH2)2-4O—, and —O(CH2)1-3O—;
- 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 —(CH2)3-5—, —O(CH2)2-4—, —(CH2)2-4O—, —O(CH2)1-3O—, or —S—C(NH2)═N—;
- 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.
73 more elements
A compound of Formula (I):
- wherein:
- G is independently selected from-C(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(C1-8)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 benzo[1,3]dioxolyl, 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 —O(CH2)1-3O—;
- 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.
57 more elements
A compound of Formula (I):
- wherein:
- G is selected from-C(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 benzo[1,3]dioxolyl, 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.
14 more elements
A compound of Formula (I):
- wherein:
- G is selected from-C(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-[1,2,4]thiadiazol-5-oxo-3-yl, [1,2,3,5]oxathiadiazol-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 benzo[1,3]dioxolyl, 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.
13 more elements
A compound of Formula (I):
- wherein:
- G is —C(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.
11 more elements
A compound of Formula (I):
- wherein:
- G is N,N-diethylaminocarbonyl, 3-(N,N-diethylaminocarbonyl)-phenyl, 2-methylcarbonylaminophenyl, N-N-diethylamidino, pyridin-3-yl, 3-(S)-hydroxypyrrolidin-1ylcarbonyl, 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 0;
- and
- enantiomers, diastereomers, tautomers, solvates, and pharmaceutically acceptable salts thereof.
10 more elements
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-piperid in-4-yl)-9H-xanthen-3-yl]-phenyl}-acetamide;
- 6-Pyridin-4-yl-9-(1-pyridin-2-ylmethyl-piperid in-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-piperid in-4-yl)-9H-thioxanthen-4-ol;
- 9-Piperid in-4-yl-6-pyridin-4-yl-9H-thioxanthen-4-ol;
- 5-Hydroxy-9-piperid in-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-piperid in-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-piperid in-4-yl-9H-thioxanthen-3-yl)-pyridine;
- 9-(1-Benzyl-piperid in-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-piperid in-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-piperid in-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-Piperid in-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-piperid in-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-piperid in-4-yl)-9H-xanthen-3-yl]-pyridine;
- 3-(5-Methoxy-9-piperid in-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-Piperid in-4-yl-9H-xanthen-3-yl)-4H-[1,2,4]oxadiazol-5-one;
- N-[2-(5-Methoxy-9-piperid in-4-yl-9H-xanthen-3-yl)-phenyl]-acetamide;
- 4-[3-(1H-Tetrazol-5-yl)-9H-xanthen-9-yl]-piperidine;
- 3-[9-(1-Benzyl-piperid in-4-yl)-9H-xanthen-3-yl]-pyridine;
- 4-[9-(1-Furan-3-ylmethyl-piperid in-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-piperid in-4-yl)-9H-xanthene-3-carboxylic acid diethylamide;
- 4-[9-(1-Pyridin-2-ylmethyl-piperid in-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-piperid in-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-piperid in-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)-piperid in-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-[1,2,4]oxadiazol-5-one;
- 9-Piperid in-4-yl-6-pyridin-4-yl-9H-xanthen-4-ol;
- 3-[9-(1-Furan-3-ylmethyl-piperid in-4-yl)-9H-xanthen-3-yl]-4H-[1,2,4]oxadiazol-5-one;
- N,N-Diethyl-9-(1-phenethyl-piperid in-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-piperid in-4-yl-9H-xanthene-3-carboxamidine;
- or
- 5-Hydroxy-9-(1-pyridin-2-ylmethyl-piperid in-4-yl)-9H-xanthene-3-carbonitrile.
65 more elements
A compound that is:
- N-{2-[5-Hydroxy-9-(1-pyridin-2-ylmethyl-piperid in-4-yl)-9H-xanthen-3-yl]-phenyl}-acetamide;
- N-{2-[5-Hydroxy-9-(1-thiophen-2-ylmethyl-piperid in-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-piperid in-4-yl)-9H-thioxanthen-3-yl]-phenyl}-acetamide;
- N-[2-(5-Hydroxy-9-piperidin-4-yl-9H-thioxanthen-3-yl)-phenyl]-acetamide;
- 9-Piperid in-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-piperid in-4-yl-9H-xanthene-3-carboxylic acid diethylamide;
- or
- 9-Piperid in-4-yl-6-(1H-tetrazol-5-yl)-9H-xanthen-4-ol.
8 more elements
Dependencies are inferred from the claim text.