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US 2009/0264455 A9Published application
Androgen Receptor Modulator Compounds and Methods
AssigneeLigand Pharmaceuticals Incorporated
InventorsBijan Pedram, Cornelis Arjan Van Oeveren, Lin Zhi, Shuo Zhao, Yixing Shen
Life of this patent
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Abstract
Provided herein are compounds that bind to androgen receptors and/or modulate activity of androgen receptors, and to methods for making and using such compounds. Also provided are compositions including such compounds and methods for making and using such compositions.
Claims26
A compound of Formula I or Formula II:
- wherein:
- R1 and R3 each independently is selected from among hydrogen, optionally substituted C1-C4 alkyl, C1-C4 heteroalkyl, C1-C4 haloalkyl, optionally substituted heteroaryl, and optionally substituted aryl;
- or
- R1 and R3 taken together form a C3-C8 carbocyclic ring;
- R2 and R4 are each hydrogen;
- or
- R2 and R4 taken together form a bond;
- R5 is selected from among hydrogen, C1-C8 alkyl, C1-C8 haloalkyl, C1-C8 heteroalkyl, C7-C10 arylalkyl, and C2-C8 heteroarylalkyl;
- R6 is hydrogen or F;
- R7 is selected from among hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, optionally substituted heteroaryl, and optionally substituted aryl;
- R8 and R9 each independently is selected from among hydrogen, F, and hydroxyl;
- and
- R10 is selected from among hydroxyl, Cl, Br, C1-C3 fluoroalkyl, C1-C3 heteroalkyl, C2-C4 alkenyl, and C2-C4 alkynyl;
- and pharmaceutically acceptable salts and prodrugs thereof.
11 more elements
A compound of Formula II:
- R2 and R4 are each hydrogen;
- or
- R2 and R4 taken together form a bond;
- R7 is selected from among hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, optionally substituted heteroaryl, and optionally substituted aryl;
- R8 and R9 each independently is selected from among hydrogen, F, and hydroxyl;
- and
- R10 is selected from among hydroxyl, Cl, Br, C1-C3 fluoroalkyl, optionally substituted C1-C5 heteroalkyl, C2-C4 alkenyl and C2-C4 alkynyl, wherein if R10 is a C2-C4 alkynyl, then R8 and R9 do not exist;
- and pharmaceutically acceptable salts and prodrugs thereof.
5 more elements
A compound of Formula III:
- wherein:
- R11 is C1-C4 alkyl;
- R12 is selected from among hydrogen, C1-C4 alkyl, C1-C4 haloalkyl, hydroxymethyl, optionally substituted heteroaryl, and optionally substituted aryl;
- or
- R11 and R12 taken together form a C3-C8 carbocyclic ring, wherein if R11 and R12 taken together form a C3-C8 carbocyclic ring, then R16 is not Cl or F;
- R14 is selected from among hydrogen, F, hydroxyl and C1-C3 alkyl;
- R15 is selected from among hydrogen, F, hydroxyl and C1-C3 alkyl;
- R13 is hydrogen;
- or
- R13 and R16 taken together form a bond, wherein if R13 and R16 taken together form a bond, then R14 and R15 are each C1-C4 alkyl;
- R16 is selected from among hydroxyl, Cl, F, Br, C1-C3 fluoroalkyl, C1-C3 heteroalkyl, C2-C4 alkenyl, and C2-C4 alkynyl;
- wherein if R13 is F, then R12 is hydroxymethyl or C1-C4 haloalkyl;
- n is 0 or 1, wherein if n is 0, then R16 is C2-C4 alkenyl or C2-C4 alkynyl;
- and pharmaceutically acceptable salts and prodrugs thereof.
11 more elements
A compound selected from among:
- 9-Chloro-1,2-dimethyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 105);
- 9-Chloro-2-ethyl-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 106);
- 9-Chloro-1,2-trimethylene-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 107);
- 9-Chloro-1-methyl-2-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 108);
- 9-Chloro-2-methyl-1-ethyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 109);
- 9-Chloro-1-methyl-2-phenyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 110);
- 9-Chloro-1-methyl-7-oxo-6,7-dihydro-3H-pyrrolo[3,2-f]quinoline-2-carboxylic acid ethyl ester (Compound 111);
- 9-Chloro-2-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 112);
- 9-Chloro-1,2-tetramethylene-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 113);
- 9-Chloro-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 114);
- 9-Chloro-2-(4-methoxy-phenyl)-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 115);
- 9-Chloro-2-(4-fluorophenyl)-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 116);
- 9-Chloro-2-(2,4-difluorophenyl)-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 117);
- 9-Chloro-2-(4-chlorophenyl)-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 118);
- 9-Chloro-2-(2-fluorophenyl)-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 119);
- 9-Chloro-1 methyl-2-thien-2-yl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 120);
- 2-Acetyl-9-chloro-1-methyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 121);
- (9-Chloro-2-methyl-7-oxo-6,7-dihydro-3H-pyrrolo[3,2-f]quinolin-1-yl)-acetic acid (Compound 122);
- 9-Chloro-1-ethyl-2-thien-2-yl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 123);
- 9-Chloro-2-methyl-1-propyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 124);
- 9-Chloro-1-ethyl-2-phenyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 125);
- (±)-9-Chloro-3-(2,2,2-trifluoroethyl)-1,2-trimethylene-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 126);
- (±)-9-Chloro-1,2-dimethyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 127);
- (±)-9-Chloro-2-ethyl-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 128);
- (±)-9-Chloro-1-ethyl-2-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 129)
- (±)-9-Chloro-1-methyl-2-phenyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 130);
- (±)-9-Chloro-2-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 131);
- (±)-9-Chloro-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydropyrrolo[3,2-f]-quinolin-7-one (Compound 132);
- (±)-9-Chloro-1,2-tetramethylene-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 133);
- (±)-9-Chloro-3-ethyl-1-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 134);
- (±)-9-Chloro-1,2-dimethyl-3-ethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 135);
- (±)-9-Chloro-1,2,3-trimethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 136);
- (±)-9-Chloro-1,2-dimethyl-3-propyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 137);
- (±)-9-Chloro-3-(2-chloro-2,2-difluoro-ethyl)-1,2-dimethyl-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 138);
- (±)-9-Chloro-1,2-dimethyl-3-(2-hydroxyethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 139);
- (±)-9-Chloro-1,2-dimethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 140);
- (±)-9-Chloro-1,2-dimethyl-3-(2,2-dimethylpropyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 141);
- (±)-9-Chloro-1,2-dimethyl-3-(2-thien-2-yl-ethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 142);
- (±)-9-Chloro-3-(2,2-difluoroethyl)-1,2-dimethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 143);
- (±)-9-Chloro-1,2-dimethyl-3-phenylmethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 144);
- (±)-9-Chloro-1,2-dimethyl-3-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 145);
- (±)-9-Chloro-2-(3-chlorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 146);
- (±)-9-Chloro-1-methyl-2-(4-trifluoromethyl-phenyl)-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 147);
- (±)-9-Chloro-2-(4-methoxy-phenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 148);
- (±)-9-Chloro-2-(4-fluoro-phenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 149);
- (±)-9-Chloro-2-(2,4-difluorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 150);
- (±)-9-Chloro-1,2-dimethyl-5-fluoro-3-(2,2,2-trifluoro-ethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 151);
- (±)-9-Chloro-2-(4-chlorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 152);
- (±)-2-(3-Bromophenyl)-9-chloro-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 153);
- (±)-9-Chloro-1-methyl-2-(3-nitrophenyl)-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 154);
- (±)-9-Chloro-2-(4-hydroxyphenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 155);
- (±)-9-Chloro-2-(2-fluorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 156);
- (±)-9-Chloro-2-(3,4-dichlorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 157);
- (±)-9-Chloro-2-(3,5-bis(trifluoromethyl)phenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 158);
- (±)-9-Chloro-1-methyl-3-(2,2,2-trifluoroethyl)-2-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 159);
- (±)-9-Chloro-1-ethyl-2-phenyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 160);
- (±)-9-Chloro-1-methyl-2-(thien-2-yl)-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 161);
- (+)-9-Chloro-3-(2,2,2-trifluoro-ethyl)-1,2-trimethylene-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 162);
- (−)-9-Chloro-3-(2,2,2-trifluoro-ethyl)-1,2-trimethylene-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 163);
- (±)-9-Chloro-1-ethyl-2-(thien-2-yl)-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydropyrrolo-[3,2-f]quinolin-7-one (Compound 164);
- (±)-9-Chloro-2-methyl-1-propyl-3-(2,2,2-trifluoroethyl)-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 165);
- (±)-9-Chloro-2,3-diethyl-1-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 166);
- (±)-9-Chloro-1,2-dimethyl-3-(2,2,3,3,3-pentafluoropropyl)-1,2,3,6-tetrahydropyrrolo-[3,2-f]quinolin-7-one (Compound 167);
- (±)-9-Chloro-1,2-dimethyl-3-(2,2,3,3,4,4,4-heptafluorobutyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 168);
- (±)-9-Chloro-1-methyl-2-phenyl-3-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 169);
- (±)-9-Chloro-2-ethyl-1-methyl-3-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydropyrrolo-[3,2-f]-quinolin-7-one (Compound 170);
- (±)-9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-phenyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 171);
- (±)-9-Chloro-1-methyl-2-phenyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 172);
- (±)-1,2-Dimethyl-3-(2,2,3,3,3-pentafluoropropyl)-9-trifluoromethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 173);
- (±)-1,2-Dimethyl-9-trifluoromethyl-3-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 174);
- (±)-3-(2-Chloro-2,2-difluoroethyl)-1,2-dimethyl-9-trifluoromethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 175);
- (±)-9-Chloro-3-(2-Chloro-2,2-difluoroethyl)-2-ethyl-1-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 176);
- (±)-9-Chloro-2-ethyl-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 177);
- (±)-3-(2-Chloro-2,2-difluoroethyl)-2-ethyl-1-methyl-9-trifluoromethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 178);
- (±)-2-Ethyl-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-9-trifluoromethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 179);
- (±)-2-Ethyl-1-methyl-9-trifluoromethyl-3-(3,3,3-trifluoropropyl)-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 180);
- (±)-2-Ethyl-1-methyl-3-(4,4,4-trifluorobutyl)-9-trifluoromethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 181);
- (±)-1,2-Dimethyl-3-(4,4,4-trifluorobutyl)-9-trifluoromethyl-1,2,3,6-tetrahydro-pyrrolo[3,2-f]quinolin-7-one (Compound 182);
- 9-Chloro-2-ethyl-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 183);
- 9-Chloro-1,2-dimethyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 184);
- 9-Chloro-1-ethyl-2-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 185);
- 9-Chloro-2-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 186);
- 9-Chloro-1-methyl-2-phenyl-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 187);
- 3-Benzyl-9-chloro-2-methyl-7-oxo-6,7-dihydro-3H-pyrrolo[3,2-f]quinoline-1-carbaldehyde (Compound 188);
- 9-Chloro-1,2-dimethyl-3-(2-thien-2-yl-ethyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 189);
- 9-Chloro-3-(2-hydroxy-ethyl)-1,2-dimethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 190);
- 9-Chloro-3-(2,2-difluoroethyl)-1,2-dimethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 191);
- 9-Chloro-3-(2-hydroxy-ethyl)-2-methyl-7-oxo-6,7-dihydro-3H-pyrrolo[3,2-f]-quinoline-1-carbaldehyde (Compound 192);
- 9-Chloro-3-ethyl-1-methyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 193);
- 9-Chloro-2-(4-fluorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 194);
- 9-Chloro-1,2-dimethyl-5-fluoro-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 195);
- 9-Chloro-1,2-dimethyl-3-ethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 196);
- 9-Chloro-2-(4-methoxyphenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]quinolin-7-one (Compound 197);
- 2-(3-Bromophenyl)-9-Chloro-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 198);
- 9-Chloro-2-(2-fluorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 199);
- 9-Chloro-2-(2,4-difluorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]quinolin-7-one (Compound 200);
- 9-Chloro-1-methyl-2-(3-trifluoromethylphenyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 201);
- 9-Chloro-1-methyl-2-(4-trifluoromethylphenyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 202);
- 9-Chloro-1-ethyl-2-phenyl-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 203);
- 9-Chloro-1-methyl-2-(4-methylphenyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 204);
- 9-Chloro-1-methyl-2-(3-nitrophenyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 205);
- 9-Chloro-2(4-chlorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 206);
- 9-Chloro-1-methyl-2-thien-2-yl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 207);
- 9-Chloro-1,2,3-trimethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 208);
- 9-Chloro-1-ethyl-2-thien-2-yl-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 209);
- 9-Chloro-2-methyl-1-propyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 210);
- 9-Chloro-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 211);
- 9-Chloro-3-(2-chloro-2,2-difluoroethyl)-1,2-dimethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 212);
- 9-Chloro-1,2-dimethyl-3-(3,3,3-trifluoropropyl)-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 213);
- 9-Chloro-1,2-dimethyl-3-(2,2,3,3,4,4,4-heptafluorobutyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 214);
- 9-Chloro-1,2-dimethyl-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 215);
- 9-Chloro-2-ethyl-1-methyl-3-(3,3,3-trifluoropropyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 216);
- 9-Chloro-1-methyl-2-phenyl-3-(3,3,3-trifluoropropyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 217);
- 9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-phenyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 218);
- 1,2-Dimethyl-3-(2,2,3,3,3-pentafluoropropyl)-9-trifluoromethyl-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 219);
- 1,2-Dimethyl-3-(2-chloro-2,2-difluoroethyl)-9-trifluoromethyl-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 220);
- 1,2-Dimethyl-9-trifluoromethyl-3-(3,3,3-trifluoropropyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 221);
- 9-Chloro-3-(2-chloro-2,2-difluoroethyl)-2-ethyl-1-methyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 222);
- 9-Chloro-2-ethyl-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 223);
- 3-(2-Chloro-2,2-difluoroethyl)-2-ethyl-1-methyl-9-trifluoromethyl-3,6-dihydropyrrolo-[3,2-f]quinolin-7-one (Compound 224);
- 2-Ethyl-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-9-trifluoromethyl-3,6-dihydropyrrolo-[3,2-f]quinolin-7-one (Compound 225);
- 2-Ethyl-1-methyl-9-trifluoromethyl-3-(3,3,3-trifluoropropyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 226);
- 1,2-Dimethyl-3-(4,4,4-trifluorobutyl)-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 227);
- 2-Ethyl-1-methyl-3-(4,4,4-trifluorobutyl)-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 228);
- 9-Chloro-1-methyl-3-(2,2,2-trifluoro-ethyl)-2-trifluoromethyl-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 229);
- 9-Chloro-2-hydroxymethyl-1-methyl-3-(2,2,2-trifluoro-ethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 230);
- (±)-9-Chloro-1,2-dimethyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 231);
- (±)-9-Chloro-2-ethyl-1-methyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 232);
- (±)-9-Chloro-1-methyl-3-(3,3,3-trifluoro-2-hydroxypropyl)-2-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 233);
- 1-Methyl-3-(2,2,2-trifluoro-ethyl)-2,9-bis-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 234);
- 2-Hydroxymethyl-1-methyl-3-(2,2,2-trifluoro-ethyl)-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 235);
- 3-Allyl-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 236);
- 1,2-Dimethyl-3-(2-methyl-allyl)-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 237);
- 1,2-Dimethyl-3-(2-methylprop-1-enyl)-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 238);
- 3-(3-Hydroxy-3-methyl-butyl)-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 239);
- 1,2-Dimethyl-3-(2-hydroxyethyl)-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 240);
- 3-(2-Acetoxyethyl)-1,2-Dimethyl-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 241);
- 1,2-Dimethyl-3-(prop-2-ynyl)-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]quinolin-7-one (Compound 242);
- (±)-1,2-Dimethyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 243);
- (+)-1,2-Dimethyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 244);
- (−)-1,2-Dimethyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 245);
- (±)-3-(3,3,3-Trifluoro-2-hydroxy-propyl)-9-trifluoromethyl-1,2-trimethylene-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 246);
- (±)-2-Ethyl-1-methyl-3-(3,3,3-Trifluoro-2-hydroxy-propyl)-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 247);
- 1,2-Dimethyl-3-(3-fluoropropyl)-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 248);
- 1,2-Dimethyl-3-(3-hydroxypropyl)-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 249);
- 3-(3-Acetoxypropyl)-1,2-dimethyl-9-trifluoromethyl-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 250);
- and a pharmaceutically acceptable salt or a prodrug of any of these compounds.
144 more elements
A compound selected from among:
- 9-Chloro-2-(3-fluorophenyl)-1-methyl-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 251);
- 9-Chloro-1-methyl-2-(1,3-thiazol-2-yl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 252);
- 9-Chloro-1-methyl-2-(3-pyridyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 253);
- 9-Chloro-1-methyl-2-(4-pyridyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 254);
- 9-Chloro-1-methyl-2-(pentafluoroethyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 255);
- 9-Chloro-1-methyl-2-(5-methyl-2-furyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 256);
- 9-Chloro-1-methyl-2-(2-oxazolyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 257);
- 9-Chloro-1-methyl-2-(5-methyl-2-thiophenyl)-3-(2,2,2-trifluoroethyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 258);
- 9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-thiophen-2-yl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 259);
- 9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-(trifluoromethyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 260);
- 9-Chloro-1-methyl-2-(2-furyl)-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydropyrrolo[3,2-f]-quinolin-7-one (Compound 261);
- 9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-(1,3-thiazol-2-yl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 262);
- 9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-(4-pyridyl)-3,6-dihydropyrrolo-[3,2-f]quinolin-7-one (Compound 263);
- 9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-(3-pyridyl)-3,6-dihydropyrrolo-[3,2-f]quinolin-7-one (Compound 264);
- 9-Chloro-1-methyl-3-(2,2,3,3,3-pentafluoropropyl)-2-(2-pyridyl)-3,6-dihydropyrrolo-[3,2-f]quinolin-7-one (Compound 265);
- 9-Chloro-1-methyl-2-(oxazol-2-yl)-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 266);
- 9-Chloro-1-methyl-2-(5-methylfuran-2-yl)-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 267);
- 9-Chloro-1-methyl-2-(5-methylthiophen-2-yl)-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 268);
- 9-Chloro-1-(3-chloropropyl)-2-methyl-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 269);
- 9-Chloro-1-(3-iodopropyl)-2-methyl-3-(2,2,3,3,3-pentafluoropropyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 270);
- (S)-9-Chloro-1-methyl-2-phenyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 271);
- (S)-9-Chloro-1-methyl-2-thiophen-2-yl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 272);
- (S)-9-Chloro-1-methyl-2-(4-pyridyl)-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 273);
- (S)-9-Chloro-1-methyl-2-(3-pyridyl)-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 274);
- (S)-9-Chloro-1-methyl-2-(2-pyridyl)-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 275);
- (S)-9-Chloro-1-methyl-2-(1,3-thiazol-2-yl)-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 276);
- (S)-9-Chloro-2-(2-furyl)-1-methyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 277);
- (R)-9-Chloro-1,2-dimethyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 278);
- rac-9-Chloro-1,2-dimethyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydropyrrolo-[3,2-f]-quinolin-7-one (Compound 279);
- 9-Chloro-1-methyl-2-phenyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 280);
- (R)-9-Chloro-2-ethyl-1-methyl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 281);
- (R)-9-Chloro-1-methyl-2-thiophen-2-yl-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 282);
- (R)-9-Chloro-1-methyl-2-(4-pyridyl)-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 283);
- (R)-9-Chloro-1-methyl-2-(5-methylfuran-2-yl)-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 284);
- (R)-9-Chloro-1-methyl-2-(5-methylthiophen-2-yl)-3-(3,3,3-trifluoro-2-hydroxy-propyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 285);
- 2-Ethyl-3-(3-hydroxypropyl)-1-methyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 286);
- 9-Chloro-1,2-dimethyl-3-(3-hydroxypropyl)-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 287);
- 3-(3-Bromopropyl)-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 288);
- 1,2-Dimethyl-3-[3-(2-hydroxy-ethylamino)-propyl]-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 289);
- 9-Chloro-3-(2,3-dihydroxypropyl)-1,2-dimethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 290);
- (S)-9-Chloro-3-(2,3-dihydroxypropyl)-1,2-dimethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 291);
- (R)-9-Chloro-3-(2,3-dihydroxypropyl)-1,2-dimethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 292);
- 3-(2,3-dihydroxypropyl)-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 293);
- 3-(3-chloro-2-hydroxypropyl)-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 294);
- (S)-3-(2,3-dihydroxypropyl)-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 295);
- (R)-3-(2,3-dihydroxypropyl)-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 296);
- 9-Chloro-3-(2,3-dihydroxypropyl)-2-ethyl-1-methyl-3,6-dihydro-pyrrolo[3,2-f]-quinolin-7-one (Compound 297);
- 3-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethyl}-1,2-dimethyl-9-trifluoromethyl-3,6-dihydro-pyrrolo[3,2-f]quinolin-7-one (Compound 298);
- and
- a pharmaceutically acceptable salt or a prodrug of any of these compounds.
47 more elements
-27. (canceled)
Dependencies are inferred from the claim text.