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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| EP1954133A4 (en) * | 2005-11-30 | 2010-11-24 | Glaxosmithkline Llc | PYRROLIDINANILINE |
| EP2051935B1 (en) | 2006-07-26 | 2016-09-07 | STMicroelectronics Srl | Use of nitroaniline derivatives for the production of nitric oxide |
| JP5205379B2 (ja) * | 2006-08-09 | 2013-06-05 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | プロゲステロン受容体モジュレータとしてのピロリジノンアニリン |
| 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 |
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| BRPI0907844B8 (pt) * | 2008-02-22 | 2021-05-25 | Radius Health Inc | compostos e método para modular um receptor de andrógeno, processos de preparação e composição farmacêutica dos mesmos e seus usos |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| US8987319B2 (en) | 2010-02-04 | 2015-03-24 | Radius Health, Inc. | Selective androgen receptor modulators |
| PT2568806T (pt) | 2010-05-12 | 2016-08-05 | Radius Health Inc | Regimes terapêuticos |
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| WO2012047617A1 (en) | 2010-09-28 | 2012-04-12 | 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 |
| PL3122426T3 (pl) | 2014-03-28 | 2023-05-15 | Duke University | Leczenie raka sutka z zastosowaniem selektywnych modulatorów receptora estrogenowego |
| KR102145021B1 (ko) * | 2014-04-24 | 2020-08-14 | 동아에스티 주식회사 | 피리딘계 화합물 및 이를 포함하는 선택적 안드로겐 수용체 효능제 |
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| 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 |
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