Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation
AssigneeGlenmark Pharmaceuticals S.A.
InventorsMeyyappan Muthuppalaniappan, Gopalan Balasubramanian, Srinivas Gullapalli, Neelima Khairatkar Joshi, Shridhar Narayanan
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel cannabinoid receptor modulators, in particular cannabinoid 1 (CB1) or cannabinoid 2 (CB2) receptor modulators, and uses thereof for treating diseases, conditions and/or disorders modulated by a cannabinoid receptor (such as pain, neurodegenerative disorders, eating disorders, weight loss or control, and obesity).
Claims40
A compound of Formula 1A
- an analog thereof, pharmaceutically acceptable salt thereof, pharmaceutically acceptable ester thereof, tautomer thereof, stereoisomer thereof, enantiomer thereof, or diastereomer thereof, wherein
- each occurrence of R is independently substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
- R1 is hydrogen;
- R2 is substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted heteroarylalkyl, or NR3R4;
- or R1 and R2 may be joined together to form an optionally substituted piperidinyl;
- R3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted cycloalkyl and R4 is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted cycloalkyl;
- or R3 and R4 may be joined together to form an optionally substituted 3 to 7 membered saturated or unsaturated cyclic ring, which may optionally include at least two heteroatoms selected from O, NR3 or S;
- p is 1;
- and
- A is
- wherein
- each of the dotted lines in A independently represents an optional bond, and each occurrence of R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 is the same or different and selected from hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted aryl;
- with the proviso that the compound does not have the formula:
- wherein R1 and R2 are as defined above.
A compound selected from:
- N(7)-Piperidino-5-(2-bromophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Benzyl-5-(2-bromophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Morpholino-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(3-Pyridylmethyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(4-Pyridylmethyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Cyclohexyl-5-(4-chloroyhenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(N-cyclohexyl-N-methylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Cyclohexylmethyl-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(Adamantan-1-yl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(1S,2endo-1,3,3-Trimethyl-bicyclo[2.2.1]hept-2-yl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(2-Chlorobenzyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(4-Chlorobenzyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(4-Fluorobenzyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(2,4-Difluorobenzyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2,6-Difluorobenzyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(4-Trifluoromethylbenzyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-((S)-1-Phenylethyl))-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-((R)-1-Phenylethyl))-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.1 3,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(1-Methyl-1-phenylethyl))-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2-Pyridylmethyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(N′-phenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(N′-phenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide hydrochloride,
- N(7)-(2-Chlorophenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2-Chlorophenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide, hydrochloride,
- N(7)-[(4-chlorophenyl)amino)]-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2,4-Dichlorophenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide.
- N(7)-[(2,4-Dichlorophenyl-N′-methylamino]-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-[(2,4-Dichlorophenyl-N′-methylamino]-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide hydrochloride,
- N(7)-(2,4-Dichlorophenyl-N′-cyclohexylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(4-Fluorophenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(4-Fluorophenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide hydrochloride,
- N(7)-(2,4-Difluorophenylamino]-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(3-fluorophenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(3-Chloro-2-pyridylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(5-Chloro-2-pyridylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2-Phenylethyl)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(N′,N′-Diphenylamino)-5-(4-chlorophenyl)-5,6-diazatetracyclo[7.3.1.1 3,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N7-[1-(2-Chlorophenyl)ethyl]-5-(4-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Benzyl-5-(4′-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-Piperidino-5-(4′-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- 7-(4′-Chlorophenyl)-6,7-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-5-dien-5-yl-piperidinomethanone,
- N(7)-Phenyl-5-(4′-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-Piperidino-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(Adamantan-1-yl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(1S,2endo-1,3,3-Trimethyl-bicyclo[2.2.1]hept-2-yl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(S-1-phenylethyl))-5-(2,4-difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(R-1-phenylethyl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(1-Methyl-1-phenylethyl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2-Chlorobenzyl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2,4-Dichlorophenylamino)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-[1-(2-Chlorophenyl)ethyl]-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-[(S)-1-Phenylpropyl]-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N7-[1-(2-Chlorophenyl)-1-methylethyl]-5-(2,4-difluorophenyl)-5,6-diazatetracyclo[7.3.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- Methyl(2R)-2-[7-(2,4-difluorophenyl)-6,7-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),5-dien-5-ylcarboxamido]-2-phenylethanoate,
- Methyl(2S)-2-[7-(2,4-difluorophenyl)-6,7-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),5-dien-5-ylcarboxamido]-2-phenylethanoate,
- N7-(3-Hydroxyadamantan-1-yl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(1-Methyl-1-phenylethyl]-5-(4-fluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(Adamantan-1-yl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N7-(Adamantan-2-yl)-5-(4-fluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N7-(1,3,3-Trimethyl bicyclo[2.2.1]hept-2-yl)-5-(4-fluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Piperidino-5-(4-methylphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2,4-Dichlorophenylamino)-5-(4-methylphenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2-Chlorobenzyl)-5-(4-methylphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Piperidino-5-(4-methoxyphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N7-(2-Chlorobenzyl)-5-(4-methoxyphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2,4-Dichlorophenylamino)-5-(4-methoxyphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Piperidino-5-[(2-chlorophenyl)phenyl]-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-[(2,4-Dichlorophenyl)amino]-5-phenyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-phenyl-5-phenyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide;
- N(7)-piperidino-5-phenyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-Benzyl-5-phenyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide;
- 7-phenyl-6,7-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-5-dien-5-yl-piperidinomethanone;
- N(7)-(4-Fluorobenzyl)-5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Phenylamino-5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8), 6-diene-7-carboxamide,
- N(7)-(2-Chlorophenylamino)-5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2,4-Dichlorophenylamino)-5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2-Bromophenylamino)-5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(N′,N′-Diphenylamino)-5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2-Phenylethyl)-5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7. 3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Benzyl-5-(2′,4′-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-piperidino-5-(2′,4′-dichlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-(2,4-Dichlorophenylamino)-5-(2-chlorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Benzyl-5-(2′-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-cyclohexyl-5-(2′-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-piperidino-5-(2′-chlorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N7-(2-Chlorobenzyl)-5-(5-chloro-2-pyridyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-Benzyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-piperidino-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- 6,7-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-5-dien-5-yl-piperidinomethanone;
- N(7)-piperidino-6-methyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-piperidino-5-methyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-(1-methyl-1-phenylethyl)-6-pentyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4,7-diene-7-carboxamide,
- N(7)-(1-methyl-1-phenylethyl)-5-pentyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxamide,
- N(7)-[(1R)-2-Hydroxy-1-phenylethyl]-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.048]tetradeca-4(8),6-diene-7-carboxamide,
- N(7)-[(1S)-2-Hydroxy-1-phenylethyl]-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- N(3)-Piperidino-1-phenyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexyl-1-phenyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Benzyl-1-phenyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenylamino-1-phenyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Piperidino-1-(2-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexyl-1-(2-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Benzyl-1-(2-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenylamino-1-(2-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Piperidino-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- 1-(4-Chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazol-3-yl piperidino methanone,
- N(3)-Cyclohexyl-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclopentyl-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(N-Cyclohexyl-N-methyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenyl-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(3-Chlorophenyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Chlorophenyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(3-Bromophenyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-Methoxyphenyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-tert-Butylphenyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Benzyl-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-Chlorobenzyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Chlorobenzyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2,4-Dichlorobenzyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-Bromobenzyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Bromobenzyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Fluorobenzyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Trifluoromethylbenzyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenylamino-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(4-Chlorophenyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2,4-Dichlorophenyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(3,4-Dichlorophenyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Fluorophenyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(3-Fluorophenyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(4-Fluorophenyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2,4-Difluorophenyl)amino]-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(N′,N′-Diphenylamino-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexyl-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexylmethyl-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(N,N-Dicyclohexylamino)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4H-1,2,4-triazol-4-yl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(1,3,3-Trimethyl bicyclo[2.2.1]hept-2-yl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(Adamantan-1yl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenyl-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2,4-Difluorophenyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-Fluorobenzyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Fluorobenzyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2,4-Difluorobenzyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2,6-Difluorobenzyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-Chlorobenzyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Chlorobenzyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2,4-Dichlorobenzyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[S-(1-phenylethyl)]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[R-(1-phenylethyl)]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-phenylethyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[2-(4-fluorophenyl)ethyl]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenylamino-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Chlorophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[N-(2-Chlorophenyl)-N-methylamino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(4-Chlorophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2,4-Dichlorophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2,4-dichlorophenyl)-N-methylamino]-1-(2,4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(3,4-Dichlorophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Bromophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Fluorophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2,4-Difluorophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(3-Fluorophenyl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(3-chloropyridin-2-yl)amino]-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(5)-piperidino-3-(2′,4′-dichlorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N(5)-benzyl-3-(2′,4′-dichlorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N(3)-Piperidino-1-(2-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexyl-1-(2-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Benzyl-1-(2-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenylamino-1-(2-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Piperidino-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexyl-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Benzyl-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenylamino-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Fluorophenyl)amino]-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexyl-1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Benzyl-1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N5-(Adamantan-2-yl)-3-(4-fluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(1-Methyl-1-phenylethyl)-3-(4-fluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(Adamantan-1-yl)-3-(4-fluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N(3)-Phenylamino-1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Phenylamino-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Chlorophenyl)amino]-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-bromophenyl)amino]-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Fluorophenyl)amino]-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Piperidino-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclohexyl-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(Cyclohexylmethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[S-(1-Phenylethyl)]-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(R-1-phenylethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(1-Methyl-1-phenylethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N5-[1-(2-Chlorophenyl)-1-methylethyl]-3-(2,4-difluorophenyl)-3,4-diazatricyclo [5.2.1.02.6]deca-2(6),4-diene-5-carboxamide,
- N(3)-(1,3,3-Trimethylbicyclo[2.2.1]hept-2-yl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N5-(2-Chlorobenzyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(4-Chlorobenzyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(1-Ethyl-1-phenylpropyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-[(1S)-1-Phenylpropyl]-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- Methyl(2S)-2-[5-(2,4-difluorophenyl)-4,5-diazatricyclo[5.2.1.02,6]deca-2(6),3-dien-3-ylcarboxamido]-2-phenylethanoate,
- N5-[(1S)-2-Hydroxy-1-phenylethyl]-3-(2,4-difluorophenyl)-3,4-diazatricyclo [5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- (4R,7S)-N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- (4S,7R)—N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N5-n-Pentyl-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(2,4-Dichlorobenzyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(1-phenylcyclopropyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(2-Adamantyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N5-(2-Methyl-2-adamantyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxamide,
- N7-(3-Hydroxyadamantan-1-yl)-5-(2,4-difluorophenyl)-5,6-diazatetracyclo [7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxamide,
- 4-[5-(2,4-Difluorophenyl)-4,5-diazatricyclo[5.2.1.02,6]deca-2(6), 3-dien-3-ylcarboxamido]morpholine,
- N(3)-(tert-Pentyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclopropanmethyl-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclobutyl-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(Tetrahydro-2H-4-pyranmethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-Cyclopropyl-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-methylpiperazino)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- Methyl (2R)-2-[5-(2,4-difluorophenyl)-4,5-diazatricyclo[5.2.1.02,6]deca-2(6),3-dien-3-ylcarboxamido]-2-phenylethanoate,
- N(3)-[(1R)-2-Hydroxy-1-phenylethyl]-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-Butyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(Tetrahydro-2-furanylmethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-Butyl)-1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-Butyl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-Butyl)-1-(3,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- Methyl(2S)-2-[5-(2,4-difluorophenyl)-4,5-diazatricyclo[5.2.1.02,6]deca-2(6),3-dien-3-ylcarboxamido]-2-(4-fluorophenyl)ethanoate,
- N(3)-(tert-Butyl)-1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(4-Hydroxyphenyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-Butyl)-1-(2-ethoxy,4-fluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-furylmethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-thiophenemethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(1S)-2-Hydroxy-1-(4-fluorophenyl)ethyl]-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- Methyl-(2S)-2-[5-(2,4-difluorophenyl)-4,5-diazatricyclo[5.2.1.02,6]deca-2(6), 3-dien-3-ylcarboxamido]-4-methylpentanoate,
- N(3)-(Adamantan-1-yl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-butyl)-1-(4-fluorobenzyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-butyl)-2-(4-fluorobenzyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-butyl)-1-(4-methylbenzyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(2-hydroxyethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(Thienylethyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(Isopropyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(1S)-2-Methoxy-1-phenylethyl]-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(tert-butyl)-2-(4-methylbenzyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- N(3)-Phenyl-1-(2,4-dichlorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2-Fluorophenyl)amino]-1-(2,4-Dichlorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(2,4-Difluorophenyl)amino]-1-(2,4-Dichlorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-[(3-chloropyridin-2-yl)amino]-1-(2,4-Dichlorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(Adamantan-1-yl)-1-(2,4-difluorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(1,3,3-Trimethylbicyclo[2.2.1]hept-2-yl)-1-(2,4-difluorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-(1-Methyl-1-phenylethyl))-1-(2,4-difluorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- (4R,7S)—N(3)-tert-Butyl-1-(2,4-difluorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-methano-indazole-3-carboxamide,
- Methyl (2R)-2-[1-(2,4-difluorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamido]-2-phenylethanoate,
- N(3)-[(1R)-2-Hydroxy-1-phenylethyl]-1-(2,4-difluorophenyl)-7,8,8-trimethyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide,
- N(3)-pentyl-1-(2,4-difluorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-methano-indazole-3-carboxamide,
- (4S,7R)—N(3)-tert-Butyl-1-(2,4-difluorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-methano-indazole-3-carboxamide,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- N(12)-Benzyl-10-(2,4-dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N(12)-Piperidino-10-(2,4-dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N(12)-Piperidino-10-(2,4-dichlorophenyl)-10,11-diazatetracyclo [6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide, hydrochloride.
- N(12)-[(N′-Cyclohexyl-N′-methyl)amino]-10-(2,4-dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N(12)-{N′-[(2,4-Dichlorophenyl)-N′-methyl]amino}-10-(2,4-dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N(12)-(Adamantan-1-yl)-10-(2,4-dichlorophenyl)-10,11-diazatetracyclo [6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N12-(1,3,3-Trimethylbicyclo[2.2.1]hept-2-yl)-10-(2,4-dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2(7),3,5,9(13),11-pentaene-12-carboxamide,
- N12-(1-Methyl-1-phenylethyl)-10-(2,4,dichlorophenyl)-10,11-diazatetracyclo [6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N12-(1-Methyl-1-phenylethyl)-10-(2,4-difluorophenyl)-10,11-diazatetracyclo [6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- N(12)-Benzyl-16-(4-chlorophenyl)-10-(2,4-dichlorophenyl)-15,17-dioxo-10,11,16-triazapentacyclo[6.5.5.02,7.09,13.014,18]octadeca-2,4,6,9(13),11-pentaene-12-carboxamide or
- N(12)-Piperidino-16-(4-chlorophenyl)-10-(2,4-dichlorophenyl)-15,17-dioxo-10,11,16-triazapentacyclo[6.5.5.02,7.09,13.014,18]octadeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- N(12)-Benzyl-10-(2,4-difluorophenyl)-10,11-diazatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N(12)-(1-Methyl-1-phenylethyl)-10-(2,4-difluorophenyl)-10,11-diazatetracyclo [6.5.1.02,7.09,13]tetradeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- N(12)-tert-Butyl-10(2,4-difluorophenyl)-10,11-diazatetracyclo [6.5.1.02,7.09,13]tetradeca-2,4,6,9(13),11-pentaene-12-carboxamide,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- N5-(tert-Butyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.2.02,6]undeca-2(6), 4-diene-5-carboxamide,
- N(5)-(tert-Pentyl)-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.2.02,6]undeca-2(6),4-diene-5-carboxamide,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- 5-(2-bromophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(4-chlorophenyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(2,4-Difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(4-Fluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(4-methylphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(4-Methoxyphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-phenyl-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(2-chlorophenyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5-(5-chloropyridyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 5,6-diazatetracyclo[7,3,1.13,11,04,8]tetradeca-4(8),6-diene-7-carboxylic acid,
- 6-Pentyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4,7-diene-7-carboxylic acid,
- 5-Pentyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxylic acid,
- 1-Phenyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(2-Chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(4-Chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(2,4-Dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(2-Bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(4-Bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(4-Fluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(2,4-Difluorophenyl)-4, 5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- (R or S) 1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- (S or R) 1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 1-(2,4-Dichlorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- 3-(2,4-difluorophenyl)-1,10,10-trimethyl-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylic acid,
- 10-(2,4-dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxylic acid,
- 10-(2,4-difluorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxylic acid,
- 13Endo,14endo-16-(4-chlorophenyl)-15,17-dioxo-10-(2,4-dichlorophenyl)-10,11,16-triazapentacyclo[6.5.5.02,7.09.13.014,18]octadeca-2,4,6,9(13),11-pentaene-12-carboxylic acid,
- 10-(2,4-Difluorophenyl)-10,11-diazatetracyclo[6. 5.1.02,7.09,13]tetradeca-2,4,6,9(13),11-pentaene-12-carboxylic acid,
- 3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.2.02,6]undeca-2(6),4-diene-5-carboxylic acid,
- 3-(3,4-dichlorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylic acid,
- 3-(2-ethoxy-4-fluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylic acid.
- 2-(4-Methylbenzyl)-4,5,6,7-tetrahydro-2H-4,7-methano-indazole-3-carboxylic acid,
- 3-(4-methylbenzyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylic acid,
- 2-(4-Fluorobenzyl)-4,5,6,7-tetrahydro-2H-4,7-methano-indazole-3-carboxylic acid,
- 1-(4-Fluorobenzyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylic acid,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- Ethyl 5-(2-bromophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(4-chlorophenyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(2,4-Difluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(4-Fluorophenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(4-methylphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(4-Methoxyphenyl)-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-phenyl-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(2,4-dichlorophenyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(2-chorophenyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-(5-chloropyridyl)-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 6-methyl-5,6-diazatetracyclo[7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 5-methyl-5,6-diazatetracyclo [7,3,1.13,11.04,8]tetradeca-4(8),6-diene-7-carboxylate,
- Ethyl 6-pentyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4,7-diene-7-carboxylate,
- Ethyl 5-pentyl-5,6-diazatetracyclo[7.3.1.13,11.04,8]tetradeca-4(8)-6-diene-7-carboxylate,
- Ethyl 1-phenyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(2-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(2,4-dichlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(2-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(4-fluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(2,4-dichlorophenyl)-7,8,8-trimethyl-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 3-(2,4-difluorophenyl)-1,10,10-trimethyl-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylate,
- Ethyl 10-(2,4-dichlorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxylate,
- Ethyl 10-(2,4-difluorophenyl)-10,11-diazatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6,9(13),11-pentaene-12-carboxylate,
- Ethyl 13endo, 14endo-16-(4-chlorophenyl)-15,17-dioxo-10-(2,4-dichlorophenyl)-10,11,16-triazapentacyclo[6.5.5.02,7.09,13.014,18]octadeca-2,4,6,9(13),11-pentaene-12-carboxylate,
- Ethyl 10-(2,4-difluorophenyl)-10,11-diazatetracyclo[6.5.1.02,7.09,13]tetradeca-2,4,6,9(13),11-pentaene-12-carboxylate,
- Ethyl-3-(2,4-difluorophenyl)-3,4-diazatricyclo[5.2.2.02,6]undeca-2(6),4-diene-5-carboxylate,
- Ethyl 3-(3,4-dichlorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylate,
- Ethyl 3-(2-ethoxy-4-fluorophenyl)-3,4-diazatricyclo[5.2.1.02,6]deca-2(6),4-diene-5-carboxylate,
- Ethyl 4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 2-(4-methylbenzyl)-4,5,6,7-tetrahydro-2H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(4-methylbenzyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- Ethyl 2-(4-fluorobenzyl)-4,5,6,7-tetrahydro-2H-4,7-methano-indazole-3-carboxylate,
- Ethyl 1-(4-fluorobenzyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxylate,
- and pharmaceutically acceptable salts thereof.
A compound selected from:
- Ethyl 2-oxo-(5-oxotricyclo[4.3.1.13,8]undec-4-yl)acetate,
- Ethyl 2-oxo-2(3-oxobicyclo[2.2.1]hept-2-yl)acetate,
- Ethyl 2-(3-hydroxy-4,7,7-trimethyl bicyclo[2.2.1]hept-2-en-2-yl-2-oxoacetate,
- Ethyl 2-oxo-2-(10-oxotricyclo[6.2.2.02,7]dodeca-2,4,6-trien-9-yl)acetate,
- Ethyl 9endo,13endo-2-[11-(4-chlorophenyl)-10,12,15-trioxo-11-azatetracyclo [6.5.2.02,7.09,13]pentadeca-2,4,6-trien-14-yl]-2-oxoacetate,
- Ethyl 2-oxo-2-(10-oxotricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-9-yl)acetate,
- Ethyl 2-hydroxy-2-(3-oxabicyclo[2.2.2]octa-2-yliden)acetate,
- 9-Endo,13-endo-11-(4-chlorophenyl)-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-10,12,14-trione,
- and pharmaceutically acceptable salts thereof.
A selective CB2 agonist having the formula:
- wherein
- each occurrence of R is independently substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl;
- R1 is hydrogen;
- R2 is substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted heteroarylalkyl, or NR3R4;
- or R1 and R2 may be joined together to form an unsubstituted piperidinyl;
- R3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted cycloalkyl and R4 is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted cycloalkyl;
- or R3 and R4, when bound to a common atom, may be joined together to form an optionally substituted 3 to 7 membered saturated or unsaturated cyclic ring, which may optionally include at least two heteroatoms selected from O, NR3 or S.
A compound of the formula (Ib):
- an analog thereof, a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable ester thereof, a stereoisomer thereof,
- wherein
- R is 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2-bromophenyl, 4-bromophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 4-methylphenyl, 4-methoxyphenyl, or 2-(4-chlorophenyl)phenyl;
- R1 is hydrogen;
- and
- R2 is t-butyl, n-pentyl, cyclopentyl, cyclohexyl, adamantan-1-yl, 2-methyladamantan-2-yl, 3-hydroxyadamantan-1-yl, 1,3,3-trimethylbicyclo[2.2.1]hept-2-yl, 1-phenylcyclopropyl, cyclohexylmethyl, phenyl, 3-chlorophenyl, 4-chlorophenyl, 3-bromophenyl, 2-methoxyphenyl, 4-tert-butylphenyl, 2,4-difluorophenyl, benzyl, 2-chlorobenzyl, 4-chlorobenzyl, 2,4-dichlorobenzyl, 2-fluorobenzyl, 4-fluorobenzyl, 2,4-difluorobenzyl, 2,6-difluorobenzyl, 2-bromobenzyl, 4-bromobenzyl, 4-trifluoromethylbenzyl, 1-phenylethyl, 1-methyl-1-phenylethyl, 2-phenylethyl, 1-(2-chlorophenyl)ethyl, 2-(4-fluorophenyl)ethyl, 1-phenylpropyl, 1-ethyl-1-phenylpropyl, 1-(2-chlorophenyl)-1-methylethyl, methylphenylethanoate, 2-hydroxy-1-phenylethyl, piperidinyl, morpholinyl, pyridinyl, 1,2,4-triazol-4-yl, 2-pyridylmethyl, 3-pyridylmethyl, or 4-pyridylmethyl.
N(3)-(tert-Butyl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
N(3)-(tert-Butyl)-1-(4-bromophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide.
N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide.
(4S,7R)N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
(4S,7R)N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide.
N(3)-(tert-Butyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide or a pharmaceutically acceptable salt thereof.
N(3)-(tert-Butyl)-1-(4-chlorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide.
A compound (4S,7R) N(3)-(tert-Butyl)-1-(2,4-difluorophenyl)-4,5,6,7-tetrahydro-1H-4,7-methano-indazole-3-carboxamide, wherein said compound possesses an enantiomeric excess(e.e.) of at least 90%.
Dependencies are inferred from the claim text.