JP2007500245A5 - - Google Patents
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- JP2007500245A5 JP2007500245A5 JP2006533629A JP2006533629A JP2007500245A5 JP 2007500245 A5 JP2007500245 A5 JP 2007500245A5 JP 2006533629 A JP2006533629 A JP 2006533629A JP 2006533629 A JP2006533629 A JP 2006533629A JP 2007500245 A5 JP2007500245 A5 JP 2007500245A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- amino
- benzonitrile
- nitro
- trifluoroethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 38
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 125000001188 haloalkyl group Chemical group 0.000 claims 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims 17
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000000304 alkynyl group Chemical group 0.000 claims 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- -1 isobutenyl Chemical group 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000010428 Muscle Weakness Diseases 0.000 claims 2
- 206010028372 Muscular weakness Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 2
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 102000001307 androgen receptors Human genes 0.000 claims 2
- 108010080146 androgen receptors Proteins 0.000 claims 2
- 210000003433 aortic smooth muscle cell Anatomy 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 201000010260 leiomyoma Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 201000004240 prostatic hypertrophy Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 206010046766 uterine cancer Diseases 0.000 claims 2
- 208000010579 uterine corpus leiomyoma Diseases 0.000 claims 2
- 201000007954 uterine fibroid Diseases 0.000 claims 2
- 230000001457 vasomotor Effects 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- KUYJOMYEFQWKRX-UHFFFAOYSA-N 1-[4-[cyclopropylmethyl(propyl)amino]-2-(trifluoromethyl)phenyl]ethanone Chemical compound C=1C=C(C(C)=O)C(C(F)(F)F)=CC=1N(CCC)CC1CC1 KUYJOMYEFQWKRX-UHFFFAOYSA-N 0.000 claims 1
- FLHHGZUDLSQCMI-UHFFFAOYSA-N 2-(trifluoromethyl)-4-(3,3,3-trifluoropropylamino)benzonitrile Chemical compound FC(F)(F)CCNC1=CC=C(C#N)C(C(F)(F)F)=C1 FLHHGZUDLSQCMI-UHFFFAOYSA-N 0.000 claims 1
- IDQIMQPZIBIQRF-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]ethyl-diazonioazanide Chemical compound [N-]=[N+]=NCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 IDQIMQPZIBIQRF-UHFFFAOYSA-N 0.000 claims 1
- QBJFPKOVBFQYIU-UHFFFAOYSA-N 2-[n-(cyclopropylmethyl)-4-nitro-3-(trifluoromethyl)anilino]ethanol Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1N(CCO)CC1CC1 QBJFPKOVBFQYIU-UHFFFAOYSA-N 0.000 claims 1
- JWOSFAKJXZFDHV-UHFFFAOYSA-N 2-chloro-4-(dibutylamino)benzonitrile Chemical compound CCCCN(CCCC)C1=CC=C(C#N)C(Cl)=C1 JWOSFAKJXZFDHV-UHFFFAOYSA-N 0.000 claims 1
- PHSDEYLHNVLWHD-UHFFFAOYSA-N 2-chloro-4-(dipropylamino)benzonitrile Chemical compound CCCN(CCC)C1=CC=C(C#N)C(Cl)=C1 PHSDEYLHNVLWHD-UHFFFAOYSA-N 0.000 claims 1
- OVJADYJPTSFGTG-UHFFFAOYSA-N 2-chloro-4-[2-(dimethylamino)ethyl-methylamino]benzonitrile Chemical compound CN(C)CCN(C)C1=CC=C(C#N)C(Cl)=C1 OVJADYJPTSFGTG-UHFFFAOYSA-N 0.000 claims 1
- GJTBSBNYWWIVKW-UHFFFAOYSA-N 2-chloro-4-[2-methoxyethyl(propyl)amino]benzonitrile Chemical compound COCCN(CCC)C1=CC=C(C#N)C(Cl)=C1 GJTBSBNYWWIVKW-UHFFFAOYSA-N 0.000 claims 1
- MOJLNYMTTQWIIY-UHFFFAOYSA-N 2-chloro-4-[cyclopropylmethyl(propyl)amino]benzonitrile Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(CCC)CC1CC1 MOJLNYMTTQWIIY-UHFFFAOYSA-N 0.000 claims 1
- USXYPRWSALDBLL-UHFFFAOYSA-N 2-chloro-4-[ethyl(2-methylprop-2-enyl)amino]benzonitrile Chemical compound CC(=C)CN(CC)C1=CC=C(C#N)C(Cl)=C1 USXYPRWSALDBLL-UHFFFAOYSA-N 0.000 claims 1
- CRRPJMGQJLYCIU-UHFFFAOYSA-N 2-chloro-n-(2-methoxyethyl)-n-methyl-4-nitroaniline Chemical compound COCCN(C)C1=CC=C([N+]([O-])=O)C=C1Cl CRRPJMGQJLYCIU-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- OULQLZUXDBHSNY-UHFFFAOYSA-N 3-[4-nitro-3-(trifluoromethyl)anilino]propan-1-ol Chemical compound OCCCNC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 OULQLZUXDBHSNY-UHFFFAOYSA-N 0.000 claims 1
- JRWIAAQCEWQNRV-UHFFFAOYSA-N 3-[n-(cyclopropylmethyl)-4-nitro-3-(trifluoromethyl)anilino]propan-1-ol Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1N(CCCO)CC1CC1 JRWIAAQCEWQNRV-UHFFFAOYSA-N 0.000 claims 1
- KQUPPWDMEUESIQ-UHFFFAOYSA-N 3-methyl-4-nitro-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=C([N+]([O-])=O)C(C)=C1 KQUPPWDMEUESIQ-UHFFFAOYSA-N 0.000 claims 1
- TZSMPTXLVIVJNZ-UHFFFAOYSA-N 4-(1,3-dihydroxypropan-2-ylamino)-2-(trifluoromethyl)benzonitrile Chemical compound OCC(CO)NC1=CC=C(C#N)C(C(F)(F)F)=C1 TZSMPTXLVIVJNZ-UHFFFAOYSA-N 0.000 claims 1
- CQWJTHHMEBRYFE-UHFFFAOYSA-N 4-(1-cyclopropylethylamino)-2-(trifluoromethyl)benzonitrile Chemical compound C1CC1C(C)NC1=CC=C(C#N)C(C(F)(F)F)=C1 CQWJTHHMEBRYFE-UHFFFAOYSA-N 0.000 claims 1
- YAWAZFSEGWXUAI-UHFFFAOYSA-N 4-(2,2,2-trifluoroethylamino)-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)CNC1=CC=C(C#N)C(C(F)(F)F)=C1 YAWAZFSEGWXUAI-UHFFFAOYSA-N 0.000 claims 1
- VVLDRTJYBABIAO-UHFFFAOYSA-N 4-(2,2-dimethylpropylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)(C)CNC1=CC=C(C#N)C(C(F)(F)F)=C1 VVLDRTJYBABIAO-UHFFFAOYSA-N 0.000 claims 1
- TWOYKCIRMLLBDY-UHFFFAOYSA-N 4-(3-hydroxypropylamino)-2-(trifluoromethyl)benzonitrile Chemical compound OCCCNC1=CC=C(C#N)C(C(F)(F)F)=C1 TWOYKCIRMLLBDY-UHFFFAOYSA-N 0.000 claims 1
- YJTJAAIIWZCRAR-UHFFFAOYSA-N 4-(cyclopropylmethylamino)-2-(trifluoromethyl)benzonitrile Chemical compound C1=C(C#N)C(C(F)(F)F)=CC(NCC2CC2)=C1 YJTJAAIIWZCRAR-UHFFFAOYSA-N 0.000 claims 1
- UMQZFTNEKQVHHK-UHFFFAOYSA-N 4-(cyclopropylmethylamino)-3-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC(C#N)=CC=C1NCC1CC1 UMQZFTNEKQVHHK-UHFFFAOYSA-N 0.000 claims 1
- DROJJNYRJOQECY-UHFFFAOYSA-N 4-(dibutylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CCCCN(CCCC)C1=CC=C(C#N)C(C(F)(F)F)=C1 DROJJNYRJOQECY-UHFFFAOYSA-N 0.000 claims 1
- RJJVBSQKXPHNMP-UHFFFAOYSA-N 4-(diethylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CCN(CC)C1=CC=C(C#N)C(C(F)(F)F)=C1 RJJVBSQKXPHNMP-UHFFFAOYSA-N 0.000 claims 1
- HTHPHSCHVAJUNX-UHFFFAOYSA-N 4-(dimethylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CN(C)C1=CC=C(C#N)C(C(F)(F)F)=C1 HTHPHSCHVAJUNX-UHFFFAOYSA-N 0.000 claims 1
- CWCXIQXIWKTNGA-UHFFFAOYSA-N 4-(dipentylamino)-2-nitrobenzonitrile Chemical compound CCCCCN(CCCCC)C1=CC=C(C#N)C([N+]([O-])=O)=C1 CWCXIQXIWKTNGA-UHFFFAOYSA-N 0.000 claims 1
- WSVSGOSYQRPOIU-UHFFFAOYSA-N 4-(dipropylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CCCN(CCC)C1=CC=C(C#N)C(C(F)(F)F)=C1 WSVSGOSYQRPOIU-UHFFFAOYSA-N 0.000 claims 1
- SRRWJAWCXZKTEA-UHFFFAOYSA-N 4-(dipropylamino)-2-nitrobenzonitrile Chemical compound CCCN(CCC)C1=CC=C(C#N)C([N+]([O-])=O)=C1 SRRWJAWCXZKTEA-UHFFFAOYSA-N 0.000 claims 1
- CKKTWUMLNRZSTO-UHFFFAOYSA-N 4-(dipropylamino)benzene-1,2-dicarbonitrile Chemical compound CCCN(CCC)C1=CC=C(C#N)C(C#N)=C1 CKKTWUMLNRZSTO-UHFFFAOYSA-N 0.000 claims 1
- PYBOHBWNACIEDV-UHFFFAOYSA-N 4-(dipropylamino)benzonitrile Chemical compound CCCN(CCC)C1=CC=C(C#N)C=C1 PYBOHBWNACIEDV-UHFFFAOYSA-N 0.000 claims 1
- UBZLJHZRVUQKNA-UHFFFAOYSA-N 4-(propylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CCCNC1=CC=C(C#N)C(C(F)(F)F)=C1 UBZLJHZRVUQKNA-UHFFFAOYSA-N 0.000 claims 1
- KWGGYJYWOVMYFM-UHFFFAOYSA-N 4-(tert-butylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)(C)NC1=CC=C(C#N)C(C(F)(F)F)=C1 KWGGYJYWOVMYFM-UHFFFAOYSA-N 0.000 claims 1
- JHXSNLRWDBBNDW-UHFFFAOYSA-N 4-[2,2-difluoroethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 JHXSNLRWDBBNDW-UHFFFAOYSA-N 0.000 claims 1
- XQVFDBDPFUHJBA-UHFFFAOYSA-N 4-[2,2-dimethylpropyl(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)(C)CN(CCO)C1=CC=C(C#N)C(C(F)(F)F)=C1 XQVFDBDPFUHJBA-UHFFFAOYSA-N 0.000 claims 1
- MPKNIFAJTWFTGP-UHFFFAOYSA-N 4-[2,2-dimethylpropyl(2-oxoethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)(C)CN(CC=O)C1=CC=C(C#N)C(C(F)(F)F)=C1 MPKNIFAJTWFTGP-UHFFFAOYSA-N 0.000 claims 1
- UHUDGGLNTBZWRW-UHFFFAOYSA-N 4-[2,2-dimethylpropyl(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound OCCCN(CC(C)(C)C)C1=CC=C(C#N)C(C(F)(F)F)=C1 UHUDGGLNTBZWRW-UHFFFAOYSA-N 0.000 claims 1
- GNPTZVORGLBBIO-UHFFFAOYSA-N 4-[2,2-dimethylpropyl(prop-2-enyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)(C)CN(CC=C)C1=CC=C(C#N)C(C(F)(F)F)=C1 GNPTZVORGLBBIO-UHFFFAOYSA-N 0.000 claims 1
- SJZUCOPGUKYHDJ-UHFFFAOYSA-N 4-[2,2-dimethylpropyl(propyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCCN(CC(C)(C)C)C1=CC=C(C#N)C(C(F)(F)F)=C1 SJZUCOPGUKYHDJ-UHFFFAOYSA-N 0.000 claims 1
- QLVULFHGXQWXDI-UHFFFAOYSA-N 4-[2,3-dihydroxypropyl(2,2-dimethylpropyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound OCC(O)CN(CC(C)(C)C)C1=CC=C(C#N)C(C(F)(F)F)=C1 QLVULFHGXQWXDI-UHFFFAOYSA-N 0.000 claims 1
- RYGBIZUEEOYXFX-UHFFFAOYSA-N 4-[2-(2,2,2-trifluoroethoxy)ethyl-(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)COCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 RYGBIZUEEOYXFX-UHFFFAOYSA-N 0.000 claims 1
- CLIGUVMKKUWDMD-UHFFFAOYSA-N 4-[2-ethoxyethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCOCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 CLIGUVMKKUWDMD-UHFFFAOYSA-N 0.000 claims 1
- CRIRVBCRTPIJOW-UHFFFAOYSA-N 4-[2-fluoroethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 CRIRVBCRTPIJOW-UHFFFAOYSA-N 0.000 claims 1
- HFACRWFIGZPRFJ-UHFFFAOYSA-N 4-[2-hydroxyethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound OCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 HFACRWFIGZPRFJ-UHFFFAOYSA-N 0.000 claims 1
- MNXBVHNXEWDKRI-UHFFFAOYSA-N 4-[2-methoxyethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound COCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 MNXBVHNXEWDKRI-UHFFFAOYSA-N 0.000 claims 1
- WZQFRZUXXYLIKL-UHFFFAOYSA-N 4-[2-methoxyethyl(methyl)amino]-3-(trifluoromethyl)benzonitrile Chemical compound COCCN(C)C1=CC=C(C#N)C=C1C(F)(F)F WZQFRZUXXYLIKL-UHFFFAOYSA-N 0.000 claims 1
- MSRZRBFKGFEZOS-UHFFFAOYSA-N 4-[2-methoxyethyl(propyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound COCCN(CCC)C1=CC=C(C#N)C(C(F)(F)F)=C1 MSRZRBFKGFEZOS-UHFFFAOYSA-N 0.000 claims 1
- AILXETAWEPMKMF-UHFFFAOYSA-N 4-[2-methoxyethyl(propyl)amino]-2-nitrobenzonitrile Chemical compound COCCN(CCC)C1=CC=C(C#N)C([N+]([O-])=O)=C1 AILXETAWEPMKMF-UHFFFAOYSA-N 0.000 claims 1
- JYFGJMOFBXQEGF-UHFFFAOYSA-N 4-[2-methylprop-2-enyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(=C)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 JYFGJMOFBXQEGF-UHFFFAOYSA-N 0.000 claims 1
- RSYWRNUSDRPZJN-UHFFFAOYSA-N 4-[2-methylpropyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 RSYWRNUSDRPZJN-UHFFFAOYSA-N 0.000 claims 1
- RUOGQYMDGAFJJD-UHFFFAOYSA-N 4-[2-methylsulfanylethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CSCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 RUOGQYMDGAFJJD-UHFFFAOYSA-N 0.000 claims 1
- IQDMFSFZDXHAMW-UHFFFAOYSA-N 4-[3-hydroxypropyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound OCCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 IQDMFSFZDXHAMW-UHFFFAOYSA-N 0.000 claims 1
- ZJXJRIKFHUWSIE-UHFFFAOYSA-N 4-[3-hydroxypropyl(2,2,2-trifluoroethyl)amino]-3-(trifluoromethyl)benzonitrile Chemical compound OCCCN(CC(F)(F)F)C1=CC=C(C#N)C=C1C(F)(F)F ZJXJRIKFHUWSIE-UHFFFAOYSA-N 0.000 claims 1
- URJKIZXERKWKPD-UHFFFAOYSA-N 4-[3-methylbut-2-enyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)=CCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 URJKIZXERKWKPD-UHFFFAOYSA-N 0.000 claims 1
- UIJKWZKEIGDFCL-UHFFFAOYSA-N 4-[3-methylbutyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)CCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 UIJKWZKEIGDFCL-UHFFFAOYSA-N 0.000 claims 1
- HXLMUYQMZSEDDY-NSHDSACASA-N 4-[[(2s)-butan-2-yl]-(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound OCCCN([C@@H](C)CC)C1=CC=C(C#N)C(C(F)(F)F)=C1 HXLMUYQMZSEDDY-NSHDSACASA-N 0.000 claims 1
- OYFKBNSLEHOXOG-UHFFFAOYSA-N 4-[bis(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 OYFKBNSLEHOXOG-UHFFFAOYSA-N 0.000 claims 1
- MAWKJIAIDYKBOM-UHFFFAOYSA-N 4-[bis(2-ethoxyethyl)amino]-3-chlorobenzonitrile Chemical compound CCOCCN(CCOCC)C1=CC=C(C#N)C=C1Cl MAWKJIAIDYKBOM-UHFFFAOYSA-N 0.000 claims 1
- HFTTZUZIIUMTRK-UHFFFAOYSA-N 4-[bis(2-fluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FCCN(CCF)C1=CC=C(C#N)C(C(F)(F)F)=C1 HFTTZUZIIUMTRK-UHFFFAOYSA-N 0.000 claims 1
- DEYDXSGQLHERFP-UHFFFAOYSA-N 4-[bis[3-(dimethylamino)propyl]amino]-2-(trifluoromethyl)benzonitrile Chemical compound CN(C)CCCN(CCCN(C)C)C1=CC=C(C#N)C(C(F)(F)F)=C1 DEYDXSGQLHERFP-UHFFFAOYSA-N 0.000 claims 1
- VXMULKDIJCYMLT-UHFFFAOYSA-N 4-[butan-2-yl(propyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCCN(C(C)CC)C1=CC=C(C#N)C(C(F)(F)F)=C1 VXMULKDIJCYMLT-UHFFFAOYSA-N 0.000 claims 1
- YPVIQRWDRCTFJB-UHFFFAOYSA-N 4-[butan-2-yl(propyl)amino]-2-nitrobenzonitrile Chemical compound CCCN(C(C)CC)C1=CC=C(C#N)C([N+]([O-])=O)=C1 YPVIQRWDRCTFJB-UHFFFAOYSA-N 0.000 claims 1
- HRAHKMDUEPXXSH-UHFFFAOYSA-N 4-[butyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 HRAHKMDUEPXXSH-UHFFFAOYSA-N 0.000 claims 1
- WVHPOVRZHHXCHC-UHFFFAOYSA-N 4-[butyl(ethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCCCN(CC)C1=CC=C(C#N)C(C(F)(F)F)=C1 WVHPOVRZHHXCHC-UHFFFAOYSA-N 0.000 claims 1
- KDTLZATUIAZPLS-UHFFFAOYSA-N 4-[butyl(ethyl)amino]-2-chlorobenzonitrile Chemical compound CCCCN(CC)C1=CC=C(C#N)C(Cl)=C1 KDTLZATUIAZPLS-UHFFFAOYSA-N 0.000 claims 1
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| US7514470B2 (en) * | 2004-03-03 | 2009-04-07 | Smithkline Beecham Corporation | Aniline derivatives as selective androgen receptor modulators |
| US8519158B2 (en) | 2004-03-12 | 2013-08-27 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
| MXPA06013115A (es) * | 2004-05-11 | 2007-02-28 | Pfizer Prod Inc | Derivados de benzonitrilo para tratar la fragilidad musculoesqueletica. |
| CN101119993B (zh) | 2005-01-10 | 2015-03-04 | 阿卡蒂亚药品公司 | 作为选择性雄激素受体调节剂的氨基苯基衍生物 |
| JP2008536868A (ja) * | 2005-04-15 | 2008-09-11 | スミスクライン・ビーチャム・コーポレイション | シアノアリールアミン |
| PL1891038T3 (pl) | 2005-05-13 | 2009-04-30 | Lilly Co Eli | Podstawione n-arylopirolidyny jako selektywne modulatory receptora androgenowego |
| EP1888512A2 (en) * | 2005-06-06 | 2008-02-20 | Smithkline Beecham Corporation | Chemical compounds |
| EP1954133A4 (en) * | 2005-11-30 | 2010-11-24 | Glaxosmithkline Llc | PYRROLIDINANILINE |
| WO2008012845A1 (en) * | 2006-07-26 | 2008-01-31 | Stmicroelectronics S.R.L. | Use of nitroaniline derivatives for the production of nitric oxide |
| MX2009001442A (es) * | 2006-08-09 | 2009-02-18 | Smithkline Beecham Corp | Pirrolidinona anilinas como moduladores del receptor de progesterona. |
| JP2009084254A (ja) * | 2007-10-03 | 2009-04-23 | Sumitomo Chemical Co Ltd | アミロイドβタンパク質の蓄積を抑制するための医薬組成物 |
| EP2222636B1 (en) | 2007-12-21 | 2013-04-10 | Ligand Pharmaceuticals Inc. | Selective androgen receptor modulators (sarms) and uses thereof |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| CA2716320C (en) * | 2008-02-22 | 2014-01-28 | Radius Health, Inc. | Selective androgen receptor modulators |
| AU2011212813B2 (en) | 2010-02-04 | 2014-10-23 | Radius Health, Inc. | Selective androgen receptor modulators |
| HUE030072T2 (en) | 2010-05-12 | 2017-04-28 | Radius Health Inc | Therapeutic prescriptions |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9133182B2 (en) | 2010-09-28 | 2015-09-15 | Radius Health, Inc. | Selective androgen receptor modulators |
| TW201534586A (zh) | 2013-06-11 | 2015-09-16 | Orion Corp | 新穎ｃｙｐ１７抑制劑／抗雄激素劑 |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| ES3055185T3 (en) | 2014-03-28 | 2026-02-10 | Univ Duke | Treatment of an estrogen receptor positive breast cancer using a selective estrogen receptor modulator |
| KR102145021B1 (ko) * | 2014-04-24 | 2020-08-14 | 동아에스티 주식회사 | 피리딘계 화합물 및 이를 포함하는 선택적 안드로겐 수용체 효능제 |
| KR20250152679A (ko) | 2015-04-29 | 2025-10-23 | 래디어스 파마슈티컬스, 인코포레이티드 | 암을 치료하는 방법 |
| CN105213972A (zh) * | 2015-10-19 | 2016-01-06 | 翔宇药业股份有限公司 | 一种活血通络的药物制剂及其应用 |
| CN105213973A (zh) * | 2015-10-19 | 2016-01-06 | 翔宇药业股份有限公司 | 用于缓解女性月经前症状的药物组合物 |
| MX389702B (es) | 2016-06-22 | 2025-03-20 | Ellipses Pharma Ltd | Compuestos para usarse en el tratamiento de cancer de mama que expresa el receptor de androgenos (ar+). |
| JP7481115B2 (ja) | 2017-01-05 | 2024-05-10 | ラジウス ファーマシューティカルズ，インコーポレイテッド | Ｒａｄ１９０１－２ｈｃｌの多形性形態 |
| CA3099155A1 (en) | 2018-05-14 | 2019-11-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| MX2020013713A (es) | 2018-07-04 | 2021-03-02 | Radius Pharmaceuticals Inc | Formas polimorficas de rad1901-2hcl. |
| EP3924328A1 (en) | 2019-02-12 | 2021-12-22 | Radius Pharmaceuticals, Inc. | Processes and compounds |
| WO2020214834A1 (en) | 2019-04-19 | 2020-10-22 | Ligand Pharmaceuticals Inc. | Crystalline forms and methods of producing crystalline forms of a compound |
| CA3138197A1 (en) | 2019-05-14 | 2020-11-19 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| EP4058464A1 (en) | 2019-11-13 | 2022-09-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| MX2023011241A (es) | 2021-03-23 | 2023-10-03 | Nuvation Bio Inc | Compuestos dirigidos a receptores de hormonas nucleares contra el cancer. |
| JP2024516024A (ja) | 2021-05-03 | 2024-04-11 | ニューベイション・バイオ・インコーポレイテッド | 抗がん核内ホルモン受容体標的化化合物 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3629330A (en) * | 1965-05-24 | 1971-12-21 | Clairol Inc | Components for hair dyeing compositions |
| CH490342A (de) * | 1966-10-15 | 1970-05-15 | Bayer Ag | Verfahren zur Herstellung von 2,6-Dicyan-4-nitranilin |
| US3646216A (en) * | 1967-09-01 | 1972-02-29 | Shulton Inc | N1-aminoalkyl derivatives of 2-nitro-p-phenylenediamine |
| JPS525486B2 (https=) * | 1973-02-13 | 1977-02-14 | ||
| US3843793A (en) * | 1972-07-19 | 1974-10-22 | Schering Corp | A method for the treatment of benign prostatic hypertrophy and acne |
| SE7407986L (https=) * | 1973-06-20 | 1974-12-23 | Scherico Ltd | |
| JPS6037561A (ja) * | 1983-08-11 | 1985-02-26 | Hitachi Chem Co Ltd | 電子写真感光体 |
| NZ221729A (en) * | 1986-09-15 | 1989-07-27 | Janssen Pharmaceutica Nv | Imidazolyl methyl-substituted benzimidazole derivatives and pharmaceutical compositions |
| NO179551C (no) * | 1987-11-10 | 1996-10-30 | Novo Nordisk As | Analogifremgangsmåte for fremstilling av terapeutisk virksomme kinoxalinforbindelser |
| DE3804490A1 (de) * | 1988-02-12 | 1989-08-24 | Heumann Pharma Gmbh & Co | Substituierte 6-phenyldihydro-3(2h)-pyridazinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5721356A (en) * | 1989-09-15 | 1998-02-24 | Gensia, Inc. | Orally active adenosine kinase inhibitors |
| CA2127689A1 (en) * | 1992-01-27 | 1993-08-05 | Marcel A. C. Janssen | Pyrroloimidazolyl and imidazopyridinyl substituted 1h-benzimidazole derivatives as aromatase inhibitors |
| US5254655A (en) * | 1992-02-05 | 1993-10-19 | Hercules Incorporated | Organosilicon polymers, and dyes, exhibiting nonlinear optical response |
| JPH05286962A (ja) * | 1992-02-14 | 1993-11-02 | Kyowa Hakko Kogyo Co Ltd | ５−アミノフラボン誘導体 |
| DE4205329A1 (de) * | 1992-02-21 | 1993-08-26 | Henkel Kgaa | P-phenylendiaminderivate als oxidationsfarbstoffvorprodukte |
| IL102495A (en) * | 1992-07-14 | 1998-06-15 | Patchornik Avraham | Universal standard reagents, method of preparing same and use thereof |
| GB9314960D0 (en) * | 1992-07-23 | 1993-09-01 | Zeneca Ltd | Chemical compounds |
| JP3258531B2 (ja) * | 1994-05-31 | 2002-02-18 | 三井化学株式会社 | ベンズイミダゾール誘導体 |
| WO1997020822A1 (en) * | 1995-12-01 | 1997-06-12 | Novartis Ag | Quinazolin-2,4-diazirines as npy receptor antagonist |
| AU4966497A (en) * | 1996-11-18 | 1998-06-10 | Yamanouchi Pharmaceutical Co., Ltd. | Novel acylamino-substituted acylanilide derivatives or pharmaceutical composition comprising the same |
| CN1129581C (zh) * | 1998-09-22 | 2003-12-03 | 山之内制药株式会社 | 氰基苯基衍生物 |
| DE19845202A1 (de) * | 1998-10-01 | 2000-04-06 | Wella Ag | Haarwuchsmittel |
| SK7692001A3 (en) * | 1998-12-09 | 2002-09-10 | Wyeth Corp | Thiourea inhibitors of herpes viruses |
| US6472415B1 (en) * | 1998-12-18 | 2002-10-29 | Biophysica, Inc. | Androgen receptor suppressors in the therapy and diagnosis of prostate cancer, alopecia and other hyper-androgenic syndromes |
| KR20020038741A (ko) * | 1999-08-27 | 2002-05-23 | 윌리암 엘. 레스페스 | 안드로겐 수용체 조절 화합물 및 방법 |
| JP2001328938A (ja) * | 2000-03-17 | 2001-11-27 | Yamanouchi Pharmaceut Co Ltd | シアノフェニル誘導体を有効成分とする医薬 |
| JP4160715B2 (ja) * | 2000-06-15 | 2008-10-08 | 太陽誘電株式会社 | 光情報記録媒体 |
| US7214690B2 (en) * | 2001-02-23 | 2007-05-08 | Ligand Pharmaceuticals Incorporated | Tricyclic quinolinone and tricyclic quinoline androgen receptor modulator compounds and methods |
| AP2002002460A0 (en) * | 2001-03-09 | 2002-06-30 | Pfizer Prod Inc | Novel benzimidazole anti-inflammatory compounds. |
| US7132438B2 (en) * | 2001-10-09 | 2006-11-07 | Amgen Inc. | Benzimidazole derivatives |
| AU2003257094A1 (en) * | 2002-08-08 | 2004-02-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted benzimidazole compounds |
| US7514470B2 (en) * | 2004-03-03 | 2009-04-07 | Smithkline Beecham Corporation | Aniline derivatives as selective androgen receptor modulators |
| JP2008536868A (ja) * | 2005-04-15 | 2008-09-11 | スミスクライン・ビーチャム・コーポレイション | シアノアリールアミン |
-
2004
- 2004-06-09 JP JP2006533629A patent/JP2007500245A/ja active Pending
- 2004-06-09 WO PCT/US2004/018252 patent/WO2005000795A2/en not_active Ceased
- 2004-06-09 US US10/560,012 patent/US20060148893A1/en not_active Abandoned
- 2004-06-09 EP EP04776383A patent/EP1654221A2/en not_active Withdrawn
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