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US 2009/0023773 A1Published application
Compositions and methods for modulating gated ion channels
AssigneePainCeptor Pharma Corporation
InventorsRahul VOHRA, Gilles DUBE, Chang-Qing WEI, Zhonghong GAN, Deogratias NTIRAMPEBURA, Jean-Louis BROCHU, Michel PAQUET, Aram ELAGOZ
Life of this patent
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Abstract
Disclosed are compounds that modulate the activity of the gated ion channels. Compounds that modulate these gated ion channels are useful in the treatment of diseases and disorders related to pain, inflammation, the neurological system, the gastrointestinal system and genitourinary system. Preferred compounds include compounds of the Formulae 1, 2, 3, 4, and 5.
Claims41
A compound of the Formula 1:
- and pharmaceutically acceptable salts, enantiomers, stereoisomers, rotamers, tautomers, diastereomers, or racemates thereof;
- wherein
- R1, R2 and R3 are each, independently, selected from the group consisting of hydrogen, substituted or unsubstituted amine, cyano, nitro, amide, halogen, halo-C1-6-alkyl, trihalomethyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycle, hydroxyl, C1-6-alkyl, wherein the C1-6-alkyl group may be interrupted by O, S or N(H), hydroxy-C1-6-alkyl, C1-6-alkoxy, C1-6-alkenyl, C1-6-alkynyl, sulfonyl, sulphonamide, sulfonic acid, OTBS, CN, CO2H, (CH2)0-5OX1, (CH2)0-5CO2X6N(H)(CH2)0-5OX6, and (CH2)0-5C(O)N(X6)2, wherein X6 is independently selected from the group consisting of hydrogen, C1-6-alkyl, amine, phenyl, and —CO2X1, wherein X1 selected from the group consisting of hydrogen, C1-6-alkyl, amino, and substituted or unsubstituted aryl;
- R4 is C(R11) or N;
- wherein R11 is selected from the group consisting of hydrogen, halogen, OH and C1-6-alkyl, or wherein R1 and R11 can optionally be joined to form a C5-C6-cycloalkyl or phenyl ring;
- R15 is N or C(H), wherein at least one of R4 and R15 are N;
- R5, R6, R7 and R8 are each, independently, selected from the group consisting of hydrogen, halogen, CO2H, C1-6-alkyl, C1-6-alkyl-OH, C1-6-alkenyl, and C1-6-alkynyl, or wherein any two of R5, R6, R7 and R8 can optionally be joined to form an optionally substituted C5-C6-heterocyclyl or optionally substituted phenyl ring;
- R9 and R10 are C(H), CH2, or CH2CH2, or one of R9 and R10 is C(H), CH2, or CH2CH2 and the other is N(R12) or N+(C1-6-alkyl)(R12), wherein R12 is selected from the group consisting of C1-6-alkyl, Alloc, aryl, and CH2-aryl, wherein the CH2 group is optionally substituted with C1-6-alkyl, and wherein the aryl group may be further independently substituted one or more times with halogen, C1-6-alkyl, C1-6-alkenyl, C1-6-alkynyl, CO2H, CN, aryl, hydroxyl or C1-6-alkoxy;
- and
- R13 is O, OCH2 or C(H)OR14, wherein R14 is H or C1-6-alkyl.
7 more elements
The compound of the Formula 5:
- and pharmaceutically acceptable salts, enantiomers, stereoisomers, rotamers, tautomers, diastereomers, or racemates thereof,
- wherein
- R1, R2 and R3 are each, independently, selected from the group consisting of hydrogen, substituted or unsubstituted amine, cyano, nitro, amide, halogen, halo-C1-6-alkyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycle, hydroxyl, C1-6-alkyl, wherein the C1-6-alkyl group may be interrupted by O, S or N(H), hydroxy-C1-6-alkyl, C1-6-alkoxy, C1-6-alkenyl, C1-6-alkynyl, sulfonyl, sulphonamide, sulfonic acid, OTBS, CN, (CH2)0-5OX6, (CH2)0-5CO2X6N(H)(CH2)0-5OX6, and (CH2)0-5C(O)N(X6)2, wherein X6 is independently selected from the group consisting of hydrogen, C1-6-alkyl, amine, phenyl, and —CO2X1, wherein X1 selected from the group consisting of hydrogen, C1-6-alkyl, amino, and substituted or unsubstituted aryl;
- R4 is C(R11) or N;
- wherein R11 is selected from the group consisting of hydrogen, halogen, and C1-6-alkyl;
- and
- R5 is selected from the group consisting of halo-C1-6-alkyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycle, hydroxyl, C1-6-alkyl, wherein the C1-6-alkyl group may be interrupted by O, S or N(H), hydroxy-C1-6-alkyl, C1-6-alkoxy, C1-6-alkenyl, C1-6-alkynyl, (CH2)0-5CO2X6 and (CH2)0-5C(O)N(X6)2, wherein X6 is independently selected from the group consisting of hydrogen, C1-6-alkyl, amine, and phenyl.
4 more elements
(canceled)
Dependencies are inferred from the claim text.