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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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-N sodium;2-hydroxybenzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1O ABBQHOQBGMUPJH-UHFFFAOYSA-N 0.000 description 1
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
- 229960000553 somatostatin Drugs 0.000 description 1
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- IHJYRMNGUDLBIY-ZDUSSCGKSA-N tert-butyl (2s)-2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]propanoate Chemical compound C=1C=C(C#N)C(C#N)=CC=1N([C@@H](C)C(=O)OC(C)(C)C)CC1CC1 IHJYRMNGUDLBIY-ZDUSSCGKSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
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- 210000001177 vas deferen Anatomy 0.000 description 1
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- 229940082509 xanthan gum Drugs 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Gynecology & Obstetrics (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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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)
| Publication Number | Publication Date |
|---|---|
| ES2523017T3 true ES2523017T3 (es) | 2014-11-20 |
Family
ID=34919539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES05730067.5T Expired - Lifetime ES2523017T3 (es) | 2004-03-03 | 2005-03-03 | Derivados de anilina como moduladores selectivos de los receptores de andrógenos |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US7514470B2 (enExample) |
| EP (1) | EP1725522B1 (enExample) |
| JP (1) | JP4805909B2 (enExample) |
| ES (1) | ES2523017T3 (enExample) |
| WO (1) | WO2005085185A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004110978A2 (en) * | 2003-06-10 | 2004-12-23 | Smithkline Beecham Corporation | 1-aminonaphthalenes as modulators of androgen, glucocorticoid, mineralocorticoid and progesterone receptors |
| WO2005000795A2 (en) * | 2003-06-10 | 2005-01-06 | Smithkline Beecham Corporation | Aniline derivatived androgen-, glucocorticoid-, mineralcorticoid- and progesterone- 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 |
| WO2007065093A2 (en) * | 2005-11-30 | 2007-06-07 | Smithkline Beecham Corporation | Pyrrolidineanilines |
| 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 |
| AU2007284161A1 (en) * | 2006-08-09 | 2008-02-21 | 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 |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| 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 |
| NZ588737A (en) * | 2008-03-31 | 2012-05-25 | Univ Columbia | Methods of diagnosing, preventing and treating bone mass diseases |
| 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 |
| JP5964756B2 (ja) | 2010-02-04 | 2016-08-03 | ラジウス ヘルス，インコーポレイテッド | 選択的アンドロゲン受容体モジュレーター |
| PL2568806T3 (pl) | 2010-05-12 | 2017-03-31 | Radius Health, Inc. | Schematy lecznicze |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| AU2011312490B2 (en) | 2010-09-28 | 2015-06-25 | Radius Pharmaceuticals, Inc. | Selective androgen receptor modulators |
| ES2939940T3 (es) | 2014-03-28 | 2023-04-28 | Univ Duke | Tratamiento del cáncer de mama utilizando moduladores selectivos de los receptores de estrógenos |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| KR20190077607A (ko) * | 2014-10-16 | 2019-07-03 | 지티엑스, 인코포레이티드 | Sarm을 이용하는 비뇨기 장애의 치료 방법 |
| WO2017223115A1 (en) | 2016-06-22 | 2017-12-28 | Radius Health, Inc. | Ar+ breast cancer treatment methods |
| EP3565542B1 (en) | 2017-01-05 | 2024-04-10 | Radius Pharmaceuticals, Inc. | Polymorphic forms of rad1901-2hcl |
| BR112020023136A2 (pt) | 2018-05-14 | 2021-02-09 | Nuvation Bio Inc. | compostos de alvo de receptor de hormônio nuclear anticâncer |
| SG11202013177WA (en) | 2018-07-04 | 2021-01-28 | Radius Pharmaceuticals Inc | Polymorphic forms of rad 1901-2hcl |
| US12441745B2 (en) | 2019-02-12 | 2025-10-14 | Radius Pharmaceuticals, Inc. | Processes and compounds |
| CN113811333B (zh) | 2019-05-14 | 2024-03-12 | 诺维逊生物股份有限公司 | 靶向抗癌核激素受体的化合物 |
| EP4058464A1 (en) | 2019-11-13 | 2022-09-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| EP4313991A1 (en) | 2021-03-23 | 2024-02-07 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| WO2022235585A1 (en) | 2021-05-03 | 2022-11-10 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5585198A (en) | 1996-11-22 | 1998-06-10 | Athena Pharmaceuticals, Inc. | N-(aryl/heteroaryl) amino acid esters, pharmaceutical compositions, and ethods for inhibiting beta-amyloid peptide release and/or its synthesis |
| AU5354398A (en) | 1996-11-22 | 1998-06-10 | Elan Pharmaceuticals, Inc. | N-(aryl/heteroaryl) amino acid derivatives, pharmaceutical compositions compri sing same, and methods for inhibiting beta-amyloid peptide release and/or it s synthesis by use of such compounds |
| US6569896B2 (en) * | 2000-08-24 | 2003-05-27 | The University Of Tennessee Research Corporation | Selective androgen receptor modulators and methods of use thereof |
| 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 |
| ATE301642T1 (de) * | 2000-06-06 | 2005-08-15 | Warner Lambert Co | Bicyclische cyclohexylamine und ihre verwendung als nmda-rezeptor antagonisten |
| 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 |
| WO2005000795A2 (en) * | 2003-06-10 | 2005-01-06 | Smithkline Beecham Corporation | Aniline derivatived androgen-, glucocorticoid-, mineralcorticoid- and progesterone- receptor modulators |
-
2005
- 2005-03-03 ES ES05730067.5T patent/ES2523017T3/es not_active Expired - Lifetime
- 2005-03-03 US US10/598,508 patent/US7514470B2/en not_active Expired - Lifetime
- 2005-03-03 EP EP05730067.5A patent/EP1725522B1/en not_active Expired - Lifetime
- 2005-03-03 JP JP2007502061A patent/JP4805909B2/ja not_active Expired - Lifetime
- 2005-03-03 WO PCT/US2005/007245 patent/WO2005085185A1/en not_active Ceased
-
2009
- 2009-02-25 US US12/392,687 patent/US7723385B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4805909B2 (ja) | 2011-11-02 |
| US20070191479A1 (en) | 2007-08-16 |
| US20090163588A1 (en) | 2009-06-25 |
| EP1725522B1 (en) | 2014-09-10 |
| WO2005085185A1 (en) | 2005-09-15 |
| US7723385B2 (en) | 2010-05-25 |
| EP1725522A1 (en) | 2006-11-29 |
| US7514470B2 (en) | 2009-04-07 |
| JP2007526336A (ja) | 2007-09-13 |
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