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US 2006/0148893 A1Published application
Chemical compounds
OwnerJean-Baptiste Blanc, Rodolfo Cadilla +6inventors
InventorsJean-Baptiste Blanc, Rodolfo Cadilla, David Cowan, Istvan Kaldor, Andrew Larkin, Eugene Stewart, Ryan Trump, Philip Turnbull
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Abstract
This invention relates to non-steroidal compounds that are or are believed to be modulators of androgen, glucocorticoid, mineralocorticoid, and progesterone receptors, and also to the methods for the making and use of such compounds.
Claims41
A compound of formula (I):
- including salts, solvates, and physiologically functional derivatives thereof, wherein
- R1 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, or aryl;
- R2 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, or aryl;
- R3 is cyano, nitro, halogen, haloalkyl, heterocyclyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, —C(O)2R8, —CONHR8, —C(O)R8, —S(O)nR8, —SO2N(R8)2, —NHC(O)R8, or —NHSO2R8;
- R4 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R , or aryl;
- R5 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, or aryl;
- where at least one of R1, R2, R4, and R5 is not H;
- each of R6 and R7 independently are selected from H or —(Ra)x-R9;
- Ra is a C1-C8 alkylene chain, where x is 0 or 1;
- each R8 independently is H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, aralkyl, heteroaryl, or heteroaralkyl;
- R9 is alkyl, haloalkyl, hydroxyalkyl, alkenyl, alkynyl, alkoxy, alkylthio, haloalkoxy, cycloalkyl, formyl, azido, or —NR10R11;
- R10 and R11 each independently are H, alkyl, —C(O)H, —C(O)R12, —C(O)OR12, or —SO2R12;
- and R12 is alkyl.
10 more elements
A compound selected from:
- 4-[(Cyclopropylmethyl)(propyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(cyclopropylmethyl)(propyl)amino]-2-nitrobenzonitrile
- 4-(diallylamino)-2-(trifluoromethyl)benzonitrile
- 5-[allyl(cyclopentyl)amino]-2-nitrobenzonitrile
- 4-[butyl(propyl)amino]-2-nitrobenzonitrile
- 4-[ethyl(2-methyl-2-propenyl)amino]-2-nitrobenzonitrile
- 4-[butyl(ethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-(dipropylamino)-2-(trifluoromethyl)benzonitrile
- N-butyl-N-ethyl-3-methyl-4-nitroaniline
- 5-(diallylamino)-2-nitrobenzonitrile
- 5-[(cyclopropylmethyl)(propyl)amino]-2-nitrobenzonitrile
- 4-(diallylamino)-2-nitrobenzonitrile
- 3-methyl-4-nitro-N,N-dipropylaniline
- 4-[sec-butyl(propyl)amino]-2-nitrobenzonitrile
- 5-[butyl(ethyl)amino]-2-nitrobenzonitrile
- 2-chloro-4-[(cyclopropylmethyl)(propyl)amino]benzonitrile
- 5-[butyl(propyl)amino]-2-nitrobenzonitrile
- 5-[(2-methoxyethyl)(methyl)amino]-2-nitrobenzonitrile
- 2-chloro-4-(diallylamino)benzonitrile
- 4-[(2-methoxyethyl)(propyl)amino]-2-nitrobenzonitrile
- 4-[allyl(cyclopentyl)amino]-2-nitrobenzonitrile
- 4-[ethyl(2-methyl-2-propenyl)amino]-2-(trifluoromethyl)benzonitrile
- 2-chloro-4-[[2-(dimethylamino)ethyl](methyl)amino]benzonitrile
- N-(2-methoxyethyl)-N,2-dimethyl-4-nitroaniline
- N-allyl-N-cyclopentyl-4-nitro-3-(trifluoromethyl)aniline
- 5-(dipropylamino)-2-nitrophenol
- 2-chloro-4-(dipropylamino)benzonitrile
- 5-[ethyl(2-methyl-2-propenyl)amino]-2-nitrobenzonitrile
- N,N-diallyl-4-nitro-3-(trifluoromethyl)aniline
- N,N-diallyl-2-methyl-4-nitroaniline
- 5-[(cyclopropylmethyl)(propyl)amino]-2-nitrophenol
- N-(2-methoxyethyl)-3-methyl-4-nitro-N-propylaniline
- 4-[butyl(propyl)amino]-2-chlorobenzonitrile
- N-butyl-2-chloro-N-methyl-4-nitroaniline
- 4-(dipropylamino)-2-nitrobenzonitrile
- 2-chloro-4-[(2-methoxyethyl)(propyl)amino]benzonitrile
- N,N-diallyl-3-methyl-4-nitroaniline
- N-(sec-butyl)-4-nitro-N-propyl-3-(trifluoromethyl)aniline
- 4-(dipentylamino)-2-nitrobenzonitrile
- N-(cyclopropylmethyl)-3-methyl-4-nitro-N-propylaniline
- 5-(dipropylamino)-2-nitrobenzonitrile
- N,N-dibutyl-4-nitro-3-(trifluoromethyl)aniline
- N1-(2-chloro4-nitrophenyl)-N1,N2,N2-trimethyl-1,2-ethanediamine
- 5-[sec-butyl(propyl)amino]-2-nitrobenzonitrile
- N-ethyl-N-(2-methyl-2-propenyl)-4-nitro-3-(trifluoromethyl)aniline
- N-(2-methoxyethyl)-4-nitro-N-propyl-3-(trifluoromethyl)aniline
- 4-[butyl(ethyl)amino]-2-chlorobenzonitrile
- 5-(dibutylamino)-2-nitrobenzonitrile
- 4-[butyl(ethyl)amino]-2-nitrobenzonitrile
- 4-[(2-methoxyethyl)(propyl)amino]-2-(trifluoromethyl)benzonitrile
- 5-[(2-methoxyethyl)(propyl)amino]-2-nitrobenzonitrile
- 4-[allyl(cyclopentyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[butyl(propyl)amino]-2-(trifluoromethyl)benzonitrile
- N,N-dibutyl-3-methyl4-nitroaniline
- 4-[methyl(octyl)amino]-2-nitrobenzonitrile
- 4-(dibutylamino)-2-(trifluoromethyl)benzonitrile
- N-(cyclopropylmethyl)4-nitro-N-propyl-2-(trifluoromethyl)aniline
- N-allyl-N-cyclohexyl-4-nitro-3-(trifluoromethyl)aniline
- 4-[(2-methoxyethyl)(methyl)amino]-3-(trifluoromethyl)benzonitrile
- 4-(diallylamino)-3-nitrobenzonitrile
- N-1 -(2-chloro-4-nitrophenyl)-N 1, N3, N3-trimethyl-1 ,3-propanediamine
- N,N-bis(2-methoxyethyl)-4-nitro-3-(trifluoromethyl)aniline
- 4-[sec-butyl(propyl)amino]-2-(trifluoromethyl)benzonitrile
- 2-chloro-4-[ethyl(2-methyl-2-propenyl)amino]benzonitrile
- N-cyclohexyl-N-ethyl-4-nitro-3-(trifluoromethyl)aniline
- 2-chloro-4-(dibutylamino)benzonitrile
- 4-[cyclohexyl(ethyl)amino]-2-nitrobenzonitrile
- 4-[bis(2-ethoxyethyl)amino]-3-chlorobenzonitrile
- 2-chloro-N-(2-methoxyethyl)-N-methyl-4-nitroaniline
- N-butyl-N-ethyl-4-nitro-3-(trifluoromethyl)aniline
- N-(sec-butyl)-3-methyl-4-nitro-N-propylaniline
- N-(2-methoxyethyl)-N-methyl-4-nitro-2-(trifluoromethyl)aniline
- 4-{bis[3-(dimethylamino)propyl]amino}-2-(trifluoromethyl)benzonitrile
- N-(cyclopropylmethyl)-4-nitro-N-propyl-3-(trifluoromethyl)aniline
- 4-[(methyl)(octyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-(propylamino)-2-(trifluoromethyl)benzonitrile
- 4-nitro-N-propyl-3-(trifluoromethyl)aniline
- 3-{[4-nitro-3-(trifluoromethyl)phenyl]amino}propan-1-ol
- 4-[(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-{[2-hydroxy-1-(hydroxymethyl)ethyl]amino}-2-(trifluoromethyl)benzonitrile
- 4-(dimethylamino)-2-(trifluoromethyl)benzonitrile
- 4-(diethylamino)-2-(trifluoromethyl)benzonitrile
- 4-[methyl(2-methylpropyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(cyclopropylmethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(cyclopropylmethyl)(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(cyclopropylmethyl)(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile
- N-(cyclopropylmethyl)-4-nitro-3-(trifluoromethyl)aniline
- 3-{(cyclopropylmethyl)[4-nitro-3-(trifluoromethyl)phenyl]amino}-1 -propanol
- 2-{(cyclopropylmethyl)[4-nitro-3-(trifluoromethyl)phenyl]amino}ethanol
- 4-[(cyclopropylmethyl)amino]-3-(trifluoromethyl)benzonitrile
- 1 -[4-[(cyclopropymethyl)(propyl)amino]-2-(trifluoromethyl)phenyl]ethanone
- 4-[(1 -cyclopropylethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[allyl(1-cyclopropylethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2-dimethylpropyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2-dimethylpropyl)(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2-dimethylpropyl)(2-propen-1 -yl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,3-dihydroxypropyl)(2,2-dimethylpropyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2-dimethylpropyl)(2-oxoethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2-dimethylpropyl)(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2-dimethylpropyl)(propyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(1,1 -dimethylethyl)amino]-2-(trifluoromethyl)benzonitrile
- N-(1 , 1 -dimethylethyl)-4-nitro-3-(trifluoromethyl)aniline
- N-(cyclopropylmethyl)-N-(1,1-dimethylethyl)-4-nitro-3-(trifluoromethyl)aniline
- 4-[(1,1-dimethylethyl)(2-propen-1-yl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(1,1 -dimethylethyl)(2-oxoethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(1,1 -dimethylethyl)(propyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-{(3-hydroxypropyl)[(1S)-1-methylpropyl]amino}-2-(trifluoromethyl)benzonitrile
- 2-(trifluoromethyl)-4-[(3,3,3-trifluoropropyl)amino]benzonitrile
- 4-[bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-nitro-N-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)aniline
- 4-[(3-hydroxypropyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(3-hydroxypropyl)(2,2,2-trifluoroethyl)amino]-3-(trifluoromethyl)benzonitrile
- 4-bromo-N,N-bis(2,2,2-trifluoroethyl)-3-(trifluoromethyl)aniline
- 4-[bis(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2,2-difluoroethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- bis(2,2,2-trifluoroethyl)[2-(trifluoromethyl)-4-biphenylyl]amine
- 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[[2-(methyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[[2-(ethyloxy)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-((2,2,2-trifluoroethyl)(2-[(2,2,2-trifluoroethyl)oxy]ethyl~amino)-2-(trifluoromethyl)benzonitrile
- 4-[methyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[ethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[propyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[butyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2-methylprop-2-enyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[isobutyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(3-methylbut-2-enyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[isopentyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[prop-2-ynyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2-fluoroethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[[2-(methylthio)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- 4-[(2-azidoethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile
- N-{2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl}acetamide
- methyl 2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethylcarbamate
- tert-butyl 2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethylcarbamate
- N-{2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl} methanesulfonamide;
- and
- 4-(dipropylamino)phthalonitrile.
136 more elements
A compound of formula (I):
- including salts, solvates, and physiologically functional derivatives thereof, wherein
- R1 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R , or aryl;
- R2 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, or aryl;
- R3 is cyano, nitro, halogen, haloalkyl, heterocyclyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, —C(O)2R8, —CONHR8, —C(O)R8, —S(O)nR8, —SO2N(R8)2, —NHC(O)R8, or —NHSO2R8;
- R4 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, or aryl;
- R5 is H, cyano, nitro, halogen, haloalkyl, alkyl, alkenyl, alkynyl, hydroxy, alkoxy, haloalkoxy, —OC(O)R8, or aryl;
- each of R6 and R7 independently are selected from H or —(Ra)x-R9;
- Ra is a C1-C8 alkylene chain, where x is 0 or 1;
- each R8 independently is H, alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, aryl, aralkyl, heteroaryl, or heteroaralkyl;
- R9 is alkyl, haloalkyl, hydroxyalkyl, alkenyl,-alkynyl, alkoxy, alkylthio, haloalkoxy, cycloalkyl, formyl, azido, or —NR10R11;
- R10 and R11 each independently are H, alkyl, —C(O)H, —C(O)R12, —C(O)OR12 or —SO2R12;
- and R12 is alkyl.
9 more elements
(canceled)
36-41. (canceled)
Dependencies are inferred from the claim text.