ES2523017T3 - Derivados de anilina como moduladores selectivos de los receptores de andrógenos - Google Patents
Derivados de anilina como moduladores selectivos de los receptores de andrógenos Download PDFInfo
- Publication number
- ES2523017T3 ES2523017T3 ES05730067.5T ES05730067T ES2523017T3 ES 2523017 T3 ES2523017 T3 ES 2523017T3 ES 05730067 T ES05730067 T ES 05730067T ES 2523017 T3 ES2523017 T3 ES 2523017T3
- Authority
- ES
- Spain
- Prior art keywords
- trifluoroethyl
- trifluoromethyl
- cyano
- phenyl
- cyclopropylmethyl
- 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.)
- Expired - Lifetime
Links
- 108010080146 androgen receptors Proteins 0.000 title description 16
- 102000001307 androgen receptors Human genes 0.000 title description 5
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title description 5
- -1 phenoxy, benzyloxy Chemical group 0.000 claims abstract description 199
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 23
- 229910052736 halogen Chemical group 0.000 claims abstract description 22
- 150000002367 halogens Chemical group 0.000 claims abstract description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 239000012453 solvate Substances 0.000 claims abstract description 18
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 107
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 87
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 59
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 59
- HQMLIDZJXVVKCW-REOHCLBHSA-N L-alaninamide Chemical compound C[C@H](N)C(N)=O HQMLIDZJXVVKCW-REOHCLBHSA-N 0.000 claims description 41
- 101000655609 Streptomyces azureus Thiostrepton Proteins 0.000 claims description 41
- 238000011282 treatment Methods 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims description 15
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 15
- ZADNMVIJDXDDFB-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]acetic acid Chemical compound OC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 ZADNMVIJDXDDFB-UHFFFAOYSA-N 0.000 claims description 12
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 12
- 208000001132 Osteoporosis Diseases 0.000 claims description 12
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 12
- 201000009273 Endometriosis Diseases 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- WFVFLPMYLPLILA-ZETCQYMHSA-N (2s)-2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]propanoic acid Chemical compound OC(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 WFVFLPMYLPLILA-ZETCQYMHSA-N 0.000 claims description 8
- MWSIUVUSXYWZBR-VIFPVBQESA-N (2s)-2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]propanoic acid Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N([C@@H](C)C(O)=O)CC1CC1 MWSIUVUSXYWZBR-VIFPVBQESA-N 0.000 claims description 8
- 206010046798 Uterine leiomyoma Diseases 0.000 claims description 8
- 201000010260 leiomyoma Diseases 0.000 claims description 8
- 208000010579 uterine corpus leiomyoma Diseases 0.000 claims description 8
- 201000007954 uterine fibroid Diseases 0.000 claims description 8
- JFLGJKFJGCWVRY-ZETCQYMHSA-N (2s)-2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]propanoic acid Chemical compound OC(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 JFLGJKFJGCWVRY-ZETCQYMHSA-N 0.000 claims description 7
- YXZGAOUZXGBKPQ-UHFFFAOYSA-N 2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]acetic acid Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(CC(=O)O)CC1CC1 YXZGAOUZXGBKPQ-UHFFFAOYSA-N 0.000 claims description 7
- HDYHSUPGDKAXBO-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]butanoic acid Chemical compound CCC(C(O)=O)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 HDYHSUPGDKAXBO-UHFFFAOYSA-N 0.000 claims description 7
- 206010046543 Urinary incontinence Diseases 0.000 claims description 7
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 claims description 7
- 235000004279 alanine Nutrition 0.000 claims description 7
- 230000001457 vasomotor Effects 0.000 claims description 7
- FRFJHZBKTLWIDX-JTQLQIEISA-N (2s)-2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]propanoic acid Chemical compound C=1C=C(C#N)C(C#N)=CC=1N([C@@H](C)C(O)=O)CC1CC1 FRFJHZBKTLWIDX-JTQLQIEISA-N 0.000 claims description 6
- MABXZIQSWRHEEL-UHFFFAOYSA-N 2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]acetic acid Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CC(=O)O)CC1CC1 MABXZIQSWRHEEL-UHFFFAOYSA-N 0.000 claims description 6
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 6
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 201000008752 progressive muscular atrophy Diseases 0.000 claims description 6
- 230000035755 proliferation Effects 0.000 claims description 6
- 208000002320 spinal muscular atrophy Diseases 0.000 claims description 6
- UHCVVHRKOPNPLW-QMMMGPOBSA-N (2s)-2-[4-cyano-3-(trifluoromethyl)-n-(3,3,3-trifluoropropyl)anilino]propanamide Chemical compound FC(F)(F)CCN([C@@H](C)C(N)=O)C1=CC=C(C#N)C(C(F)(F)F)=C1 UHCVVHRKOPNPLW-QMMMGPOBSA-N 0.000 claims description 5
- SOWCSRMUNHSDBP-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]acetic acid Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(CC(=O)O)CC1CC1 SOWCSRMUNHSDBP-UHFFFAOYSA-N 0.000 claims description 5
- ZDYGKWOTFUOWOA-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]acetamide Chemical compound NC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 ZDYGKWOTFUOWOA-UHFFFAOYSA-N 0.000 claims description 5
- VCYIZIOVCCDXLA-UHFFFAOYSA-N 3-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 VCYIZIOVCCDXLA-UHFFFAOYSA-N 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
- 206010024421 Libido increased Diseases 0.000 claims description 5
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- ZJHDDNUFOMXEEH-QMMMGPOBSA-N methyl (2s)-2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]propanoate Chemical compound COC(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 ZJHDDNUFOMXEEH-QMMMGPOBSA-N 0.000 claims description 5
- CSOJRMXWNWBXMP-UHFFFAOYSA-N tert-butyl 2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 CSOJRMXWNWBXMP-UHFFFAOYSA-N 0.000 claims description 5
- WBJAGFPPIBWZBE-UHFFFAOYSA-N tert-butyl 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]acetate Chemical compound CC(C)(C)OC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 WBJAGFPPIBWZBE-UHFFFAOYSA-N 0.000 claims description 5
- NOWODQXXTQLIMY-UHFFFAOYSA-N tert-butyl 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 NOWODQXXTQLIMY-UHFFFAOYSA-N 0.000 claims description 5
- WASBWMOLSAIWMT-UHFFFAOYSA-N tert-butyl 2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]acetate Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CC(=O)OC(C)(C)C)CC1CC1 WASBWMOLSAIWMT-UHFFFAOYSA-N 0.000 claims description 5
- YPDZHXCDKWXRPX-LBPRGKRZSA-N (2s)-2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]-n-ethylpropanamide Chemical compound C=1C=C(C#N)C(C#N)=CC=1N([C@@H](C)C(=O)NCC)CC1CC1 YPDZHXCDKWXRPX-LBPRGKRZSA-N 0.000 claims description 4
- IHJPCHNBZJBZHJ-NSHDSACASA-N (2s)-2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]-n-methylpropanamide Chemical compound C=1C=C(C#N)C(C#N)=CC=1N([C@@H](C)C(=O)NC)CC1CC1 IHJPCHNBZJBZHJ-NSHDSACASA-N 0.000 claims description 4
- PUAOMZMVKUSJIS-VIFPVBQESA-N (2s)-2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]-n-ethylpropanamide Chemical compound CCNC(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 PUAOMZMVKUSJIS-VIFPVBQESA-N 0.000 claims description 4
- RJBFHUBWKFJQKG-JTQLQIEISA-N (2s)-2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]-n-methylpropanamide Chemical compound C=1C=C(C#N)C(Cl)=CC=1N([C@@H](C)C(=O)NC)CC1CC1 RJBFHUBWKFJQKG-JTQLQIEISA-N 0.000 claims description 4
- BEFAEFLFXOZVJY-VIFPVBQESA-N (2s)-2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n,n-dimethylpropanamide Chemical compound CN(C)C(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 BEFAEFLFXOZVJY-VIFPVBQESA-N 0.000 claims description 4
- JBKYBMHKZGNTCQ-VIFPVBQESA-N (2s)-2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n-ethylpropanamide Chemical compound CCNC(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 JBKYBMHKZGNTCQ-VIFPVBQESA-N 0.000 claims description 4
- PQQFOHRTQZXRPI-NSHDSACASA-N (2s)-2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]-n,n-dimethylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N([C@@H](C)C(=O)N(C)C)CC1CC1 PQQFOHRTQZXRPI-NSHDSACASA-N 0.000 claims description 4
- JHGHCLFSCXWWRA-NSHDSACASA-N (2s)-2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]-n-ethylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N([C@@H](C)C(=O)NCC)CC1CC1 JHGHCLFSCXWWRA-NSHDSACASA-N 0.000 claims description 4
- HSMCGFFYRXCNOC-UHFFFAOYSA-N 2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]-n-ethylacetamide Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(CC(=O)NCC)CC1CC1 HSMCGFFYRXCNOC-UHFFFAOYSA-N 0.000 claims description 4
- BWZZZRRYYPOMGW-UHFFFAOYSA-N 2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]-n-ethylbutanamide Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(C(CC)C(=O)NCC)CC1CC1 BWZZZRRYYPOMGW-UHFFFAOYSA-N 0.000 claims description 4
- JVGZSGIGNDVOLH-UHFFFAOYSA-N 2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]-n-methylacetamide Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(CC(=O)NC)CC1CC1 JVGZSGIGNDVOLH-UHFFFAOYSA-N 0.000 claims description 4
- MNHFEQLQPSHKIL-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]-n-ethylacetamide Chemical compound CCNC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 MNHFEQLQPSHKIL-UHFFFAOYSA-N 0.000 claims description 4
- UJMXDSOXHYGFDH-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]-n-ethylacetamide Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(CC(=O)NCC)CC1CC1 UJMXDSOXHYGFDH-UHFFFAOYSA-N 0.000 claims description 4
- CAWFAAOTFJQIOM-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n,n-dimethylbutanamide Chemical compound CN(C)C(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 CAWFAAOTFJQIOM-UHFFFAOYSA-N 0.000 claims description 4
- LHDSMXQMLPRIJR-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n-cyclohexylacetamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CC(F)(F)F)CC(=O)NC1CCCCC1 LHDSMXQMLPRIJR-UHFFFAOYSA-N 0.000 claims description 4
- PWQASRSFEOJUJH-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n-ethylbutanamide Chemical compound CCNC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 PWQASRSFEOJUJH-UHFFFAOYSA-N 0.000 claims description 4
- BUDTZNINOFGMHC-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n-methylbutanamide Chemical compound CNC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 BUDTZNINOFGMHC-UHFFFAOYSA-N 0.000 claims description 4
- SDUXCSMCYLRIRT-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]butanamide Chemical compound CCC(C(N)=O)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 SDUXCSMCYLRIRT-UHFFFAOYSA-N 0.000 claims description 4
- CFWYBGXYNZGMCB-UHFFFAOYSA-N 2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]-n-ethylacetamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CC(=O)NCC)CC1CC1 CFWYBGXYNZGMCB-UHFFFAOYSA-N 0.000 claims description 4
- JMYQJFHVOANXSO-UHFFFAOYSA-N 2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]acetamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CC(=O)N)CC1CC1 JMYQJFHVOANXSO-UHFFFAOYSA-N 0.000 claims description 4
- CJVOMGNJXVEWNO-UHFFFAOYSA-N 2-chloro-4-[cyanomethyl(cyclopropylmethyl)amino]benzonitrile Chemical compound C1=C(C#N)C(Cl)=CC(N(CC#N)CC2CC2)=C1 CJVOMGNJXVEWNO-UHFFFAOYSA-N 0.000 claims description 4
- BVWXEPFONUDRTO-NSHDSACASA-N tert-butyl (2s)-2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]propanoate Chemical compound CC(C)(C)OC(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 BVWXEPFONUDRTO-NSHDSACASA-N 0.000 claims description 4
- ASVHEXRLSRTVCE-JTQLQIEISA-N tert-butyl (2s)-2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]propanoate Chemical compound CC(C)(C)OC(=O)[C@H](C)N(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 ASVHEXRLSRTVCE-JTQLQIEISA-N 0.000 claims description 4
- RGDKZGMIGYFPNC-LBPRGKRZSA-N tert-butyl (2s)-2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]propanoate Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N([C@@H](C)C(=O)OC(C)(C)C)CC1CC1 RGDKZGMIGYFPNC-LBPRGKRZSA-N 0.000 claims description 4
- CFBXJABPUFRALG-UHFFFAOYSA-N tert-butyl 2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 CFBXJABPUFRALG-UHFFFAOYSA-N 0.000 claims description 4
- SAWSVJBJGMFBBE-UHFFFAOYSA-N tert-butyl 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]butanoate Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(C(CC)C(=O)OC(C)(C)C)CC1CC1 SAWSVJBJGMFBBE-UHFFFAOYSA-N 0.000 claims description 4
- OPQURCDOZVEMJL-UHFFFAOYSA-N 2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]-n-ethylacetamide Chemical compound CCNC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 OPQURCDOZVEMJL-UHFFFAOYSA-N 0.000 claims description 3
- RIEPEDGPEIBPLT-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n',n'-dimethylacetohydrazide Chemical compound CN(C)NC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 RIEPEDGPEIBPLT-UHFFFAOYSA-N 0.000 claims description 3
- LGJOARQBHMKXNR-UHFFFAOYSA-N 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-n-methylacetohydrazide Chemical compound CN(N)C(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 LGJOARQBHMKXNR-UHFFFAOYSA-N 0.000 claims description 3
- ACYRAWJAOVKYKO-UHFFFAOYSA-N 2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]-n-methylacetamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N(CC(=O)NC)CC1CC1 ACYRAWJAOVKYKO-UHFFFAOYSA-N 0.000 claims description 3
- 206010002261 Androgen deficiency Diseases 0.000 claims description 3
- 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
- 210000003433 aortic smooth muscle cell Anatomy 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
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Classifications
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- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Obesity (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Hematology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
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| US54979404P | 2004-03-03 | 2004-03-03 | |
| US549794P | 2004-03-03 | ||
| PCT/US2005/007245 WO2005085185A1 (en) | 2004-03-03 | 2005-03-03 | Aniline derivatives as selective androgen receptor modulators |
Publications (1)
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| ES2523017T3 true ES2523017T3 (es) | 2014-11-20 |
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| US (2) | US7514470B2 (enExample) |
| EP (1) | EP1725522B1 (enExample) |
| JP (1) | JP4805909B2 (enExample) |
| ES (1) | ES2523017T3 (enExample) |
| WO (1) | WO2005085185A1 (enExample) |
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| EP1636167A2 (en) * | 2003-06-10 | 2006-03-22 | SmithKline Beecham Corporation | 1-aminonaphthalenes as modulators of androgen, glucocorticoid, mineralocorticoid and progesterone receptors |
| JP2007500245A (ja) * | 2003-06-10 | 2007-01-11 | スミスクライン ビーチャム コーポレーション | 化合物 |
| US20080194536A1 (en) * | 2005-04-15 | 2008-08-14 | Marlys Hammond | Cyanoarylamines |
| JP2009518313A (ja) * | 2005-11-30 | 2009-05-07 | スミスクライン・ビーチャム・コーポレイション | ピロリジンアニリン |
| JP5102985B2 (ja) * | 2006-07-18 | 2012-12-19 | 東ソ−・エフテック株式会社 | 含フッ素２級アミン化合物の製造方法 |
| US20100210706A1 (en) | 2006-08-09 | 2010-08-19 | Smithkline Beecham Corporation | Pyrrolidinone anilines as progesterone receptor modulators |
| JP5204438B2 (ja) * | 2007-07-31 | 2013-06-05 | 東ソ−・エフテック株式会社 | 含フッ素アミン化合物の製造方法 |
| MX2010009162A (es) | 2008-02-22 | 2010-12-21 | Radius Health Inc | Moduladores selectivos del receptor de androgeno. |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| JP2011516486A (ja) * | 2008-03-31 | 2011-05-26 | ザ・トラスティーズ・オブ・コロンビア・ユニバーシティ・イン・ザ・シティ・オブ・ニューヨーク | 骨質量疾患の診断、予防、及び治療方法 |
| WO2009136629A1 (ja) * | 2008-05-09 | 2009-11-12 | あすか製薬株式会社 | 生活習慣病予防・治療剤 |
| AT509045B1 (de) | 2010-01-29 | 2011-06-15 | Planta Naturstoffe Vertriebsges M B H | Verbindungen zur behandlung von asthma bronchiale |
| EP2531029B1 (en) | 2010-02-04 | 2016-10-19 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2011143469A1 (en) | 2010-05-12 | 2011-11-17 | Radius Health,Inc | Therapeutic regimens |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| BR112013007685B1 (pt) | 2010-09-28 | 2021-11-09 | Radius Pharmaceuticals, Inc | Compostos moduladores de receptor andrógeno seletivos, composição farmacêutica compreendendo os referidos compostos, método de identificação de um composto capaz de modular um receptor andrógeno, usos de um composto ou da composição e processo para a preparação de um composto |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| FI3834824T3 (fi) | 2014-03-28 | 2025-12-05 | Univ Duke | Estrogeenireseptoripositiivisen rintasyövän hoito selektiivisellä estrogeenireseptorin modulaattorilla |
| MX2017004819A (es) * | 2014-10-16 | 2018-06-12 | Gtx Inc | Metodos de tratamiento de transtornos urológicos usando sarm. |
| JP7221699B2 (ja) | 2016-06-22 | 2023-02-14 | エリプセス ファーマ エルティーディー | Ａｒ＋乳癌の治療方法 |
| KR102881465B1 (ko) | 2017-01-05 | 2025-11-04 | 래디어스 파마슈티컬스, 인코포레이티드 | Rad1901-2hcl의 다형 형태 |
| EA202092436A1 (ru) | 2018-05-14 | 2021-05-04 | Нувейшн Био Инк. | Противораковые соединения, нацеливающие на ядерные гормональные рецепторы |
| SG11202013177WA (en) | 2018-07-04 | 2021-01-28 | Radius Pharmaceuticals Inc | Polymorphic forms of rad 1901-2hcl |
| KR20210127961A (ko) | 2019-02-12 | 2021-10-25 | 래디어스 파마슈티컬스, 인코포레이티드 | 방법 및 화합물 |
| CA3138197A1 (en) | 2019-05-14 | 2020-11-19 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| US11952349B2 (en) | 2019-11-13 | 2024-04-09 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| IL306010A (en) | 2021-03-23 | 2023-11-01 | Nuvation Bio Inc | Anticancer compounds against the nuclear hormone receptor |
| 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 (7)
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| JP2001519769A (ja) | 1996-11-22 | 2001-10-23 | エラン・ファーマシューティカルズ・インコーポレイテッド | Ｎ―（アリール／ヘテロアリール）アミノ酸誘導体、その医薬組成物および該化合物を用いたβ―アミロイドペプチドの放出および／またはその合成を阻害する方法 |
| JP2001508408A (ja) * | 1996-11-22 | 2001-06-26 | エラン・ファーマシューティカルズ・インコーポレイテッド | Ｎ―（アリール／ヘテロアリール）アミノ酸エステル、医薬組成物およびベータ―アミロイドペプチドの放出および／またはその合成を阻害する方法 |
| US6506782B1 (en) * | 1998-02-27 | 2003-01-14 | Athena Neurosciences, Inc. | Heterocyclic compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds |
| MXPA02010503A (es) * | 2000-06-06 | 2003-03-10 | Warner Lambert Co | Ciclohexilaminas biciclicas y su uso como antagonistas del receptor nmda. |
| ES2321933T3 (es) | 2000-08-24 | 2009-06-15 | University Of Tennessee Research Foundation | Moduladores selectivos del receptor de androgeno y metodos de uso de los mismos. |
| CN1176905C (zh) * | 2002-03-22 | 2004-11-24 | 清华大学 | 甘氨酸乙酯邻苯二腈及其合成方法与应用 |
| JP2007500245A (ja) * | 2003-06-10 | 2007-01-11 | スミスクライン ビーチャム コーポレーション | 化合物 |
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| US7723385B2 (en) | 2010-05-25 |
| US20070191479A1 (en) | 2007-08-16 |
| EP1725522B1 (en) | 2014-09-10 |
| WO2005085185A1 (en) | 2005-09-15 |
| EP1725522A1 (en) | 2006-11-29 |
| US7514470B2 (en) | 2009-04-07 |
| JP2007526336A (ja) | 2007-09-13 |
| US20090163588A1 (en) | 2009-06-25 |
| JP4805909B2 (ja) | 2011-11-02 |
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