US 2006/0079519 A1Published application

Anti-cytokine heterocyclic compounds

AssigneeBoehringer Ingelheim Pharmaceuticals, Inc.

InventorsDerek Cogan, Ming-Hong Hao, Victor Kamhi, Matthew Netherton, Alan Swinamer, Craig Miller

Life of this patent

Estimating the term…

Abstract

Disclosed compounds of formula (I) which inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

Claims20

Dependent claims

A compound of the formula (I)

wherein:
Ar1 is chosen from (i), (ii) and (iii) below:
(i) a carbocycle substituted by R1, R2 and Rx,
wherein one of E or F is nitrogen and the other is carbon, R1 is covalently attached to either E or F, and when nitrogen is N—R1 the double bond between E and F is not present;
wherein c is a benzo ring fused to ring d which is a 5-7 membered heterocyclic ring optionally substituted by an oxo (═O) group and one to two R groups each independently being H or C1-3 alkyl;
R1 is chosen from hydrogen, NO2, —N(Rc)2, J-C(O)—N(Rc)—, J-S(O)m—N(Rc)—, C1-6 alkylS(O)m—,
or R1 is chosen from C1-6 alkyl, C3-7 cylcoalkyl, C1-5 alkoxyl or C3-7 cycloalkoxyl, C1-5 alkylthiol or C3-7 cycloalkylthiol, C1-5 acyl, C1-5 alkoxycarbonyl, C1-5 acyloxy, C1-5 acylamino, C2-5 alkenyl, C2-5 alkynyl, heterocycle, heterocycleC1-6 alkyl, heteroaryl, heteroarylC1-6 alkyl and nitrile;
each of the aforementioned where possible are optionally partially or fully halogenated or are optionally further substituted with alkylsulfonylamino, aminocarboxyl, alkoxyl, amino, alkylamino, dialkylamino, hydroxyl, oxo, nitro or nitrile;
R2 is chosen from:
hydrogen, halogen, nitrile, C1-5 alkylS(O)m—, arylS(O)m, J-O—C(O)—O—, N(Rc)2—C(O)—(CH2)n—, C1-6 acetyl, aroyl, C1-6alkoxycarbonyl, C1-6 alkyl, C3-7cycloalkyl, C1-6 alkoxy, C3-5cycloalkoxy, C1-5 alkylC1-5 alkoxy, hydroxy, hydroxy C1-5 alkyl, and amino optionally mono- or di-substituted by C1-5 alkyl, aryl or aryl C1-5 alkyl;
each of the aforementioned where possible are optionally partially or fully halogenated or are optionally further substituted with C1-3 alkyl, alkylsulfonylamino, alkoxyl, amino, alkylamino, dialkylamino, hydroxyl, oxo, nitro or nitrile;
each Rx is chosen from C1-6 alkyl or C3-7 cycloalkyl each being optionally substituted by C1-3 alkyl and optionally partially or fully halogenated, C1-4 acyl, aroyl, C1-4 alkoxy, C1-5alkylS(O)m—, each may optionally be partially or fully halogenated, halogen, C1-6 alkoxycarbonyl, carbocyclesulfonyl;
each Rc is independently hydrogen or C1-5 alkyl;
D, A and B in
of the formula (I) are each independently chosen from N or CH wherein the hydrogen atom is optionally replaced by R6;
Het is a heterocyclic or heteroaryl ring wherein Het is optionally substituted by one to three R5;
m is 0,1 or 2;
J is chosen from C1-10 alkyl and C3-7cycloalkyl each optionally substituted by Rb;
R3, R4, R6, R7 and R8 are each independently chosen from hydrogen, halogen, C1-5 alkyl, C1-5 alkoxy, C1-5 alkylC1-5 alkoxy, hydroxy, hydroxy C1-5 alkyl or amino optionally mono- or di-substituted by C1-5 alkyl, aryl or aryl C1-5 alkyl;
R5 is:
Ra, —O—Ra, —S(O)m—Ra, —N(Ra)2, —C(O)—Ra, —NH(CR7R8)n—Ra, N(Ra)2—(CH2)1-2— —(CR7R8)n—Ra, —O(CR7R8)n—Ra, —C(O)—O(CR7R8)n—Ra, —C(O)(CR7R8)n—Ra —C(O)C(O)Ra, —C(O)C(O)ORa, —C(O)NHRa, or —C(O)NH(CR7R8)n—, each optionally substituted by C1-3 alkyl, halogen or hydroxy,
wherein n is 1-5;
or R5 is aryl, heteroaryl or heterocyclyl each optionally substituted by Ra;
Ra and Rb are each independently chosen from hydrogen, C1-6 alkyl, hydroxyC1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, carbocycle, carbocycleC0-2 alkyl, aryl, heterocycle, heteroaryl, C1-5 alkoxy, C1-5 alkylthio, amino, C1-5 alkylamino, C1-5 dialkylamino, arylamino, aryl C1-5 alkylamino, diarylamino, C1-5 acyl, C1-5 alkoxycarbonyl, C1-5 acyloxy, C1-5 acylamino, each of the aforementioned are optionally partially or fully halogenated, or Ra and Rb are chosen from C1-5 alkylsulphonylamino, hydroxy, oxo, halogen, —CF3, —CH2—CF3, nitro and nitrile, wherein each carbocycle, heterocycle or heteroaryl for Ra and Rb is optionally substituted by amino, C1-3 alkyl, halogen or hydroxy;
and
X is O or S
or the pharmaceutically acceptable salts thereof.

24 more elements

A compound chosen from

[2-(4-{1-[5-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-1,2,3-triazol-4-yl}-2-phenyl-2H-pyrazol-3-yl)-ethyl]-carbamic acid benzyl ester
3-[4-(1-Benzyl-2-ethyl-1H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(1-Cyclopropyl-5-ethyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(1-Isopropyl-5-methyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(1-tert-Butyl-5-methyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(2-Acetyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(2-Benzenesulfonyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(2-Benzoyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(2-Benzoyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(2-Benzyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(2-Benzyloxymethyl-3-methyl-3H-imidazol-4-yl)-[1,2,3]triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(2-Cyclobutyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(2-Cyclopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(2-Cyclopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[5-(2-hydroxy-1,1-dimethyl-ethyl)-3-methanesulfonylamino-2-methoxy-phenyl]-4-methyl-benzamide
3-[4-(2-Isopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(2-tert-Butyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(3-Benzyl-2-ethyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(3-tert-Butyl-2-cyclopropyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(3-tert-Butyl-2-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(3-tert-Butyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-[4-(3-tert-Butyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-N-(2-methoxy-5-trifluoromethyl-phenyl)-4-methyl-benzamide
3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-N-(3-methanesulfonylamino-2-methoxy-5-trifluoromethyl-phenyl)-4-methyl-benzamide
3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(5-Ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-[4-(6-Amino-pyridin-3-yl)-1,2,3-triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-{4-[1-(1-Benzyl-piperidin-4-yl)-5-methyl-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-{4-[2-(1-Benzyloxy-cyclopropyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-{4-[2-(2-Benzyloxy-1,1-dimethyl-ethyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-{4-[2-(4-Benzyl-piperazin-1-yl)-1-methyl-1H-imidazol-4-yl]-1,2,3-triazol-1-yl}-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-{4-[2-(4-Benzyl-piperazin-1-yl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
3-{4-[2-(Hydroxy-phenyl-methyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-N-[3-methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-benzamide
3-{4-[5-(2-Amino-ethyl)-1-phenyl-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide
4-(4-{1-[5-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-1,2,3-triazol-4-yl}-2-cyclopropyl-2H-pyrazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester
N-(5-tert-Butyl-2-methanesulfinyl-phenyl)-3-[4-(2-cyclopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-2-methanesulfinyl-phenyl)-3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-2-methanesulfinyl-phenyl)-3-{4-[6-(cyclopropylmethyl-amino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-cyclopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-2-methyl-pyridin-3-yl)-3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-2-methyl-pyridin-3-yl)-3-{4-[6-(cyclopropylmethyl-amino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-{[(2-dimethylamino-ethyl)-methyl-amino]-methyl}-2-methoxy-phenyl)-4-methyl-3-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-cyano-2-methoxy-phenyl)-3-[4-(2-cyclopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-cyano-2-methoxy-phenyl)-3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-cyano-2-methoxy-phenyl)-3-{4-[6-(cyclopropylmethyl-amino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-(4-furan-3-yl-1,2,3-triazol-1-yl)-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3,4-dimethyl-5-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-cyclopropyl-5-methyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-cyclohexyl-5-methyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-cyclohexyl-5-ethyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-isopropyl-5-methyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-tert-butyl-5-methyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-cyclopropyl-5-isopropyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-cyclopropyl-5-ethyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-isopropyl-5-methyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-cyclopropyl-5-pyridin-2-yl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1-cyclopropyl-5-piperidin-4-yl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1,5-dimethyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1,2-diethyl-1H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(1,5-diisopropyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-ethyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-isopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-tert-butyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-cyclopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-cyclopropyl-1-methyl-1H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-cyclopropyl-3-isopropyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-dimethylamino-1-methyl-1H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-methanesulfonyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-methanesulfinyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-tert-butylsulfanyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-hydroxymethyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-formyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-cyclobutyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2-dimethylamino-3-methyl-3H-imidazol-4-yl)-[1,2,3]triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2,3-diethyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(2,3-dihydro-imidazo[2,1-b]thiazol-5-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(3-cyclopropyl-2-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(3-isopropyl-2-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(3-cyclopropyl-2-isopropyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(3-tert-butyl-2-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(3-ethyl-2-phenyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-methoxy-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-ethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-ethyl-1-isopropyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-cyclopropyl-1-isopropyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-isopropyl-1-phenyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-cyclopropyl-1-phenyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(5,5-dimethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-[1,2,3]triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(6-chloro-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(6-methoxy-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(6-dimethylamino-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(6-cyclopropylamino-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-[4-(7,7-dimethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[1-(4-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[1-(4-fluoro-phenyl)-5-methyl-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[1-(1-tert-butyl-piperidin-4-yl)-5-methyl-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-cyclopropyl-3-(2,2,2-trifluoro-ethyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(hydroxy-phenyl-methyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(2,2-dimethyl-propionyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(1-hydroxy-2,2-dimethyl-propyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(1-hydroxy-1-methyl-ethyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(2-hydroxy-1,1-dimethyl-ethyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(1-hydroxy-cyclopropyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(1-hydroxy-ethyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[2-(cyclopropyl-hydroxy-methyl)-3-methyl-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[5-(2-dimethylamino-ethyl)-1-phenyl-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[6-(2-dimethylamino-ethyl)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[6-(cyclopropylmethyl-amino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[6-(2-dimethylamino-ethylamino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-{4-[6-(cyclopropylmethyl-amino)-5-methoxy-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-3-fluoro-4-methyl-5-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-chloro-3-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-fluoro-3-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-pyridin-3-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(6-methyl-pyridin-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(6-morpholin-4-ylmethyl-pyridin-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(2-methyl-pyridin-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(6-methylamino-pyridin-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-thiazol-5-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-pyrimidin-5-yl-1,2,3-triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(6-trifluoromethyl-pyridin-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(tetrahydro-furan-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(4-methyl-pyridin-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-2-phenylsulfanyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[5-methyl-1-(1-methyl-piperidin-4-yl)-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[2-methyl-3-(2,2,2-trifluoro-ethyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(5-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(2-morpholin-4-yl-thiazol-5-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[6-(2-methylamino-ethyl)-pyridin-3-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[6-(2-morpholin-4-yl-ethyl)-pyridin-3-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-3H-imidazol-4-yl)-pyrazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-2-pyridin-4-yl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(5-methyl-1-piperidin-4-yl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-pyridin-4-yl-[1,2,3]triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-(4-pyridin-2-yl-[1,2,3]triazol-1-yl)-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(5,6,7,8-tetrahydro-imidazo[1,2-a]pyridin-3-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-2-phenyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[5-(2-morpholin-4-yl-ethyl)-1-phenyl-1H-pyrazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(1-phenyl-5-trifluoromethyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(1-methyl-2-piperazin-1-yl-1H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-2-piperazin-1-yl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-[spiro(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl-5-cyclohexane)]-[1,2,3]triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[3-methyl-2-(1-methyl-cyclopropyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-2-morpholin-4-yl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-[spiro(6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-3-yl-5-(2′-methyl-cycloproane))]-[1,2,3]triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-[4-(3-methyl-2-methylsulfanyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[3-methyl-2-(1-methyl-1-phenyl-ethyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-3-{4-[3-methyl-2-(2-methyl-propane-2-sulfonyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methyl-phenyl)-3-[4-(2-cyclopropyl-3-methyl-3H-imidazol-4-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-(5-tert-Butyl-3-methanesulfonylamino-2-methyl-phenyl)-3-[4-(5-ethyl-1-phenyl-1H-pyrazol-4-yl)-imidazol-1-yl]-4-methyl-benzamide
N-[3-Methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-3-[4-(5-methoxy-pyridin-3-yl)-1,2,3-triazol-1-yl]-4-methyl-benzamide
N-[3-Methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-3-[4-(5-methyl-1-phenyl-1H-pyrazol-4-yl)-1,2,3-triazol-1-yl]-benzamide
N-[3-Methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-3-{4-[3-methyl-2-(1-methyl-cyclopropyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
N-[3-Methanesulfonylamino-2-methoxy-5-(1-methyl-cyclopropyl)-phenyl]-4-methyl-3-{4-[3-methyl-2-(1-methyl-1-phenyl-ethyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-benzamide and
N-[5-(2-Hydroxy-1,1-dimethyl-ethyl)-3-methanesulfonylamino-2-methoxy-phenyl]-4-methyl-3-{4-[3-methyl-2-(1-methyl-cyclopropyl)-3H-imidazol-4-yl]-1,2,3-triazol-1-yl}-benzamide
or the pharmaceutically acceptable salts thereof.

162 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/074,354Filed 7 Mar 2005
Priority: 9 Mar 2004
Published: 13 Apr 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification33 codes

C07D 417/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid

Family

Application60/551,445Us provisional application · filed 9 Mar 2004
US 7,214,802 B2Related patent
US 2006/0079519 A1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of the formula (I)

wherein:
Ar1 is chosen from (i), (ii) and (iii) below:
(i) a carbocycle substituted by R1, R2 and Rx,
wherein one of E or F is nitrogen and the other is carbon, R1 is covalently attached to either E or F, and when nitrogen is N—R1 the double bond between E and F is not present;
wherein c is a benzo ring fused to ring d which is a 5-7 membered heterocyclic ring optionally substituted by an oxo (═O) group and one to two R groups each independently being H or C1-3 alkyl;
R1 is chosen from hydrogen, NO2, —N(Rc)2, J-C(O)—N(Rc)—, J-S(O)m—N(Rc)—, C1-6 alkylS(O)m—,
or R1 is chosen from C1-6 alkyl, C3-7 cylcoalkyl, C1-5 alkoxyl or C3-7 cycloalkoxyl, C1-5 alkylthiol or C3-7 cycloalkylthiol, C1-5 acyl, C1-5 alkoxycarbonyl, C1-5 acyloxy, C1-5 acylamino, C2-5 alkenyl, C2-5 alkynyl, heterocycle, heterocycleC1-6 alkyl, heteroaryl, heteroarylC1-6 alkyl and nitrile;
each of the aforementioned where possible are optionally partially or fully halogenated or are optionally further substituted with alkylsulfonylamino, aminocarboxyl, alkoxyl, amino, alkylamino, dialkylamino, hydroxyl, oxo, nitro or nitrile;
R2 is chosen from:
hydrogen, halogen, nitrile, C1-5 alkylS(O)m—, arylS(O)m, J-O—C(O)—O—, N(Rc)2—C(O)—(CH2)n—, C1-6 acetyl, aroyl, C1-6alkoxycarbonyl, C1-6 alkyl, C3-7cycloalkyl, C1-6 alkoxy, C3-5cycloalkoxy, C1-5 alkylC1-5 alkoxy, hydroxy, hydroxy C1-5 alkyl, and amino optionally mono- or di-substituted by C1-5 alkyl, aryl or aryl C1-5 alkyl;
each of the aforementioned where possible are optionally partially or fully halogenated or are optionally further substituted with C1-3 alkyl, alkylsulfonylamino, alkoxyl, amino, alkylamino, dialkylamino, hydroxyl, oxo, nitro or nitrile;
each Rx is chosen from C1-6 alkyl or C3-7 cycloalkyl each being optionally substituted by C1-3 alkyl and optionally partially or fully halogenated, C1-4 acyl, aroyl, C1-4 alkoxy, C1-5alkylS(O)m—, each may optionally be partially or fully halogenated, halogen, C1-6 alkoxycarbonyl, carbocyclesulfonyl;
each Rc is independently hydrogen or C1-5 alkyl;
D, A and B in
of the formula (I) are each independently chosen from N or CH wherein the hydrogen atom is optionally replaced by R6;
Het is a heterocyclic or heteroaryl ring wherein Het is optionally substituted by one to three R5;
m is 0,1 or 2;
J is chosen from C1-10 alkyl and C3-7cycloalkyl each optionally substituted by Rb;
R3, R4, R6, R7 and R8 are each independently chosen from hydrogen, halogen, C1-5 alkyl, C1-5 alkoxy, C1-5 alkylC1-5 alkoxy, hydroxy, hydroxy C1-5 alkyl or amino optionally mono- or di-substituted by C1-5 alkyl, aryl or aryl C1-5 alkyl;
R5 is:
Ra, —O—Ra, —S(O)m—Ra, —N(Ra)2, —C(O)—Ra, —NH(CR7R8)n—Ra, N(Ra)2—(CH2)1-2— —(CR7R8)n—Ra, —O(CR7R8)n—Ra, —C(O)—O(CR7R8)n—Ra, —C(O)(CR7R8)n—Ra —C(O)C(O)Ra, —C(O)C(O)ORa, —C(O)NHRa, or —C(O)NH(CR7R8)n—, each optionally substituted by C1-3 alkyl, halogen or hydroxy,
wherein n is 1-5;
or R5 is aryl, heteroaryl or heterocyclyl each optionally substituted by Ra;
Ra and Rb are each independently chosen from hydrogen, C1-6 alkyl, hydroxyC1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, carbocycle, carbocycleC0-2 alkyl, aryl, heterocycle, heteroaryl, C1-5 alkoxy, C1-5 alkylthio, amino, C1-5 alkylamino, C1-5 dialkylamino, arylamino, aryl C1-5 alkylamino, diarylamino, C1-5 acyl, C1-5 alkoxycarbonyl, C1-5 acyloxy, C1-5 acylamino, each of the aforementioned are optionally partially or fully halogenated, or Ra and Rb are chosen from C1-5 alkylsulphonylamino, hydroxy, oxo, halogen, —CF3, —CH2—CF3, nitro and nitrile, wherein each carbocycle, heterocycle or heteroaryl for Ra and Rb is optionally substituted by amino, C1-3 alkyl, halogen or hydroxy;
and
X is O or S
or the pharmaceutically acceptable salts thereof.

24 more elements

Facts

Application

11/074,354Filed 7 Mar 2005

Priority

9 Mar 2004

Published

13 Apr 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification33 codes

C07D 417/04
Containing two hetero rings: directly linked by a ring-member-to-ring-member bond
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid