JP2007500245A - 化合物 - Google Patents
化合物 Download PDFInfo
- Publication number
- JP2007500245A JP2007500245A JP2006533629A JP2006533629A JP2007500245A JP 2007500245 A JP2007500245 A JP 2007500245A JP 2006533629 A JP2006533629 A JP 2006533629A JP 2006533629 A JP2006533629 A JP 2006533629A JP 2007500245 A JP2007500245 A JP 2007500245A
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 188
- 238000000034 method Methods 0.000 claims abstract description 45
- 102000001307 androgen receptors Human genes 0.000 claims abstract description 19
- 108010080146 androgen receptors Proteins 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 230000002265 prevention Effects 0.000 claims description 53
- 125000001188 haloalkyl group Chemical group 0.000 claims description 49
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- -1 isobutenyl Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 208000001132 Osteoporosis Diseases 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 14
- 201000009273 Endometriosis Diseases 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 206010046798 Uterine leiomyoma Diseases 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 201000010260 leiomyoma Diseases 0.000 claims description 12
- 208000010579 uterine corpus leiomyoma Diseases 0.000 claims description 12
- 201000007954 uterine fibroid Diseases 0.000 claims description 12
- 208000010428 Muscle Weakness Diseases 0.000 claims description 11
- 206010028372 Muscular weakness Diseases 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 230000001457 vasomotor Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 9
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
- 206010046543 Urinary incontinence Diseases 0.000 claims description 9
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 9
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 8
- 206010060862 Prostate cancer Diseases 0.000 claims description 8
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 8
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 8
- 210000003433 aortic smooth muscle cell Anatomy 0.000 claims description 8
- 201000004240 prostatic hypertrophy Diseases 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- IPKMVOJFFBKQIL-UHFFFAOYSA-N 4-bromo-n,n-bis(2,2,2-trifluoroethyl)-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)CN(CC(F)(F)F)C1=CC=C(Br)C(C(F)(F)F)=C1 IPKMVOJFFBKQIL-UHFFFAOYSA-N 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 230000035755 proliferation Effects 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 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 description 6
- DNVVWMKQNFSNMF-UHFFFAOYSA-N 4-[cyclopropylmethyl(propyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CCC)CC1CC1 DNVVWMKQNFSNMF-UHFFFAOYSA-N 0.000 claims description 6
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 206010046766 uterine cancer Diseases 0.000 claims description 6
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- UIBDORUTMBOAMQ-UHFFFAOYSA-N 4-[methyl(octyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCCCCCCCN(C)C1=CC=C(C#N)C(C(F)(F)F)=C1 UIBDORUTMBOAMQ-UHFFFAOYSA-N 0.000 claims description 5
- IFVORMTZDCZTRE-UHFFFAOYSA-N 4-[propyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 IFVORMTZDCZTRE-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 230000004663 cell proliferation Effects 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- DPQBTLQUQQQGQZ-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-nitro-3-(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C([N+](=O)[O-])=CC=C1NCC1CC1 DPQBTLQUQQQGQZ-UHFFFAOYSA-N 0.000 claims description 5
- DYOQAJQBUBFBQI-UHFFFAOYSA-N n-[2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]ethyl]acetamide Chemical compound CC(=O)NCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 DYOQAJQBUBFBQI-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- RZMLRVOAIWFIOX-UHFFFAOYSA-N 4-[cyclopropylmethyl(2-hydroxyethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CCO)CC1CC1 RZMLRVOAIWFIOX-UHFFFAOYSA-N 0.000 claims description 4
- BANDTTHHASZHGM-UHFFFAOYSA-N 4-[cyclopropylmethyl(3-hydroxypropyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CCCO)CC1CC1 BANDTTHHASZHGM-UHFFFAOYSA-N 0.000 claims description 4
- KZPQQMPMOYOBBW-UHFFFAOYSA-N 4-[ethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)CN(CC)C1=CC=C(C#N)C(C(F)(F)F)=C1 KZPQQMPMOYOBBW-UHFFFAOYSA-N 0.000 claims description 4
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- PNNVBOGLMLOZEI-UHFFFAOYSA-N 4-[methyl(2-methylpropyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)CN(C)C1=CC=C(C#N)C(C(F)(F)F)=C1 PNNVBOGLMLOZEI-UHFFFAOYSA-N 0.000 claims description 4
- ZRGJFYVDECKAGV-UHFFFAOYSA-N 4-[prop-2-ynyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)CN(CC#C)C1=CC=C(C#N)C(C(F)(F)F)=C1 ZRGJFYVDECKAGV-UHFFFAOYSA-N 0.000 claims description 4
- XNCFGYAOPSGPET-UHFFFAOYSA-N 4-[tert-butyl(2-oxoethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound O=CCN(C(C)(C)C)C1=CC=C(C#N)C(C(F)(F)F)=C1 XNCFGYAOPSGPET-UHFFFAOYSA-N 0.000 claims description 4
- KZRFTSXVNWSUQX-UHFFFAOYSA-N 4-[tert-butyl(prop-2-enyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound C=CCN(C(C)(C)C)C1=CC=C(C#N)C(C(F)(F)F)=C1 KZRFTSXVNWSUQX-UHFFFAOYSA-N 0.000 claims description 4
- DVDSRFSJIYPTJD-UHFFFAOYSA-N 4-[tert-butyl(propyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCCN(C(C)(C)C)C1=CC=C(C#N)C(C(F)(F)F)=C1 DVDSRFSJIYPTJD-UHFFFAOYSA-N 0.000 claims description 4
- ATSZMTJETDOTTK-UHFFFAOYSA-N 4-nitro-n-propyl-3-(trifluoromethyl)aniline Chemical compound CCCNC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 ATSZMTJETDOTTK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- ZUTYOCKAMPSYFG-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-nitro-n-propyl-3-(trifluoromethyl)aniline Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1N(CCC)CC1CC1 ZUTYOCKAMPSYFG-UHFFFAOYSA-N 0.000 claims description 4
- YBKCWTGETXNOQS-UHFFFAOYSA-N n-[2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]ethyl]methanesulfonamide Chemical compound CS(=O)(=O)NCCN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 YBKCWTGETXNOQS-UHFFFAOYSA-N 0.000 claims description 4
- DGUJZQPCZRVPHY-UHFFFAOYSA-N n-tert-butyl-4-nitro-3-(trifluoromethyl)aniline Chemical compound CC(C)(C)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 DGUJZQPCZRVPHY-UHFFFAOYSA-N 0.000 claims description 4
- JYLMAFUTNFKNPR-UHFFFAOYSA-N n-tert-butyl-n-(cyclopropylmethyl)-4-nitro-3-(trifluoromethyl)aniline Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1N(C(C)(C)C)CC1CC1 JYLMAFUTNFKNPR-UHFFFAOYSA-N 0.000 claims description 4
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/04—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
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- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/59—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47725203P | 2003-06-10 | 2003-06-10 | |
| PCT/US2004/018252 WO2005000795A2 (en) | 2003-06-10 | 2004-06-09 | Aniline derivatived androgen-, glucocorticoid-, mineralcorticoid- and progesterone- receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007500245A true JP2007500245A (ja) | 2007-01-11 |
| JP2007500245A5 JP2007500245A5 (https=) | 2007-08-02 |
Family
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| JP2006533629A Pending JP2007500245A (ja) | 2003-06-10 | 2004-06-09 | 化合物 |
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| Country | Link |
|---|---|
| US (1) | US20060148893A1 (https=) |
| EP (1) | EP1654221A2 (https=) |
| JP (1) | JP2007500245A (https=) |
| WO (1) | WO2005000795A2 (https=) |
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| WO2009044930A1 (ja) * | 2007-10-03 | 2009-04-09 | Sumitomo Chemical Company, Limited | アミロイドβタンパク質蓄積抑制医薬組成物 |
| JP2010500366A (ja) * | 2006-08-09 | 2010-01-07 | スミスクライン・ビーチャム・コーポレイション | 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 |
| 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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| JP2008546643A (ja) * | 2005-06-06 | 2008-12-25 | スミスクライン ビーチャム コーポレーション | 4−置換アリールアミン誘導体および医薬組成物におけるその使用 |
| JP2010500366A (ja) * | 2006-08-09 | 2010-01-07 | スミスクライン・ビーチャム・コーポレイション | 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 |
| WO2009044930A1 (ja) * | 2007-10-03 | 2009-04-09 | Sumitomo Chemical Company, Limited | アミロイドβタンパク質蓄積抑制医薬組成物 |
| 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 |
| 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1654221A2 (en) | 2006-05-10 |
| US20060148893A1 (en) | 2006-07-06 |
| WO2005000795A3 (en) | 2005-03-10 |
| WO2005000795A2 (en) | 2005-01-06 |
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