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
- ZCXYSAFXKURHRR-UHFFFAOYSA-N methyl 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]acetate Chemical compound COC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 ZCXYSAFXKURHRR-UHFFFAOYSA-N 0.000 claims description 3
- GFDBTBCGLGOXPN-UHFFFAOYSA-N propan-2-yl 2-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]acetate Chemical compound CC(C)OC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 GFDBTBCGLGOXPN-UHFFFAOYSA-N 0.000 claims description 3
- 206010046766 uterine cancer Diseases 0.000 claims description 3
- WIMGSLYWEGLEOG-JTQLQIEISA-N (2s)-2-[4-cyano-n-(cyclopropylmethyl)-3-(trifluoromethyl)anilino]-n-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1N([C@@H](C)C(=O)NC)CC1CC1 WIMGSLYWEGLEOG-JTQLQIEISA-N 0.000 claims description 2
- KKCBTEPPADXAGK-UHFFFAOYSA-N methyl 2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]acetate Chemical compound COC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 KKCBTEPPADXAGK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 130
- 238000005160 1H NMR spectroscopy Methods 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 58
- 239000000203 mixture Substances 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 28
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 27
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 229910001868 water Inorganic materials 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 230000000694 effects Effects 0.000 description 23
- 239000007787 solid Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 18
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 210000001519 tissue Anatomy 0.000 description 16
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 15
- 239000003098 androgen Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 239000007832 Na2SO4 Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 125000001188 haloalkyl group Chemical group 0.000 description 13
- 239000003446 ligand Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- 238000002560 therapeutic procedure Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000872 buffer Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 102100032187 Androgen receptor Human genes 0.000 description 11
- 229940030486 androgens Drugs 0.000 description 11
- 239000005557 antagonist Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- 102000006255 nuclear receptors Human genes 0.000 description 11
- 108020004017 nuclear receptors Proteins 0.000 description 11
- 210000002307 prostate Anatomy 0.000 description 11
- 239000003981 vehicle Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 10
- 230000000670 limiting effect Effects 0.000 description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 9
- 244000257039 Duranta repens Species 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 239000000556 agonist Substances 0.000 description 9
- 230000001195 anabolic effect Effects 0.000 description 9
- 150000001448 anilines Chemical class 0.000 description 9
- 210000004027 cell Anatomy 0.000 description 9
- 238000002875 fluorescence polarization Methods 0.000 description 9
- 238000012216 screening Methods 0.000 description 9
- 230000001568 sexual effect Effects 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 230000001133 acceleration Effects 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 210000003205 muscle Anatomy 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 229960003604 testosterone Drugs 0.000 description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 7
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 7
- 239000004471 Glycine Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229940088597 hormone Drugs 0.000 description 7
- 239000005556 hormone Substances 0.000 description 7
- 238000012423 maintenance Methods 0.000 description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
- 239000000186 progesterone Substances 0.000 description 7
- 229960003387 progesterone Drugs 0.000 description 7
- 102000003998 progesterone receptors Human genes 0.000 description 7
- 108090000468 progesterone receptors Proteins 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- 208000011580 syndromic disease Diseases 0.000 description 7
- OZXROABYKJYFLD-VIFPVBQESA-N (2s)-2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]propanoic acid Chemical compound C=1C=C(C#N)C(Cl)=CC=1N([C@@H](C)C(O)=O)CC1CC1 OZXROABYKJYFLD-VIFPVBQESA-N 0.000 description 6
- ICHVCHDTYGVRMY-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]acetic acid Chemical compound OC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 ICHVCHDTYGVRMY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000001404 mediated effect Effects 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- CVAWKJKISIPBOD-UHFFFAOYSA-N tert-butyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OC(C)(C)C CVAWKJKISIPBOD-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 5
- CXNZOASBTDDPLB-UHFFFAOYSA-N 2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]acetic acid Chemical compound OC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 CXNZOASBTDDPLB-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- YPGBQGXTLYATJL-UHFFFAOYSA-N 4-(2,2,2-trifluoroethylamino)benzene-1,2-dicarbonitrile Chemical compound FC(F)(F)CNC1=CC=C(C#N)C(C#N)=C1 YPGBQGXTLYATJL-UHFFFAOYSA-N 0.000 description 5
- 201000001880 Sexual dysfunction Diseases 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 230000001548 androgenic effect Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 210000000988 bone and bone Anatomy 0.000 description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 description 5
- 125000005587 carbonate group Chemical group 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 201000001881 impotence Diseases 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 231100000872 sexual dysfunction Toxicity 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 238000013456 study Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
- MIJKSQLCZMJAME-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]butanoic acid Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(C(CC)C(O)=O)CC1CC1 MIJKSQLCZMJAME-UHFFFAOYSA-N 0.000 description 4
- BYONAWDUHBWSRQ-UHFFFAOYSA-N 2-chloro-4-(2,2,2-trifluoroethylamino)benzonitrile Chemical compound FC(F)(F)CNC1=CC=C(C#N)C(Cl)=C1 BYONAWDUHBWSRQ-UHFFFAOYSA-N 0.000 description 4
- RCAGIPBDDXZHCL-UHFFFAOYSA-N 2-chloro-4-(cyclopropylmethylamino)benzonitrile Chemical compound C1=C(C#N)C(Cl)=CC(NCC2CC2)=C1 RCAGIPBDDXZHCL-UHFFFAOYSA-N 0.000 description 4
- 208000002874 Acne Vulgaris Diseases 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 206010006895 Cachexia Diseases 0.000 description 4
- 208000014311 Cushing syndrome Diseases 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 206010020112 Hirsutism Diseases 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 206010000496 acne Diseases 0.000 description 4
- 235000010419 agar Nutrition 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 229940124325 anabolic agent Drugs 0.000 description 4
- 239000003263 anabolic agent Substances 0.000 description 4
- 210000000436 anus Anatomy 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000035876 healing Effects 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 230000008439 repair process Effects 0.000 description 4
- 208000021070 secondary pulmonary alveolar proteinosis Diseases 0.000 description 4
- 210000001625 seminal vesicle Anatomy 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 230000003637 steroidlike Effects 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- YXPGRTWUYFHYMI-LBPRGKRZSA-N tert-butyl (2s)-2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]propanoate Chemical compound C=1C=C(C#N)C(Cl)=CC=1N([C@@H](C)C(=O)OC(C)(C)C)CC1CC1 YXPGRTWUYFHYMI-LBPRGKRZSA-N 0.000 description 4
- XSVUFCKWQFXULD-UHFFFAOYSA-N tert-butyl 2-[4-cyano-3-(trifluoromethyl)-n-(3,3,3-trifluoropropyl)anilino]acetate Chemical compound CC(C)(C)OC(=O)CN(CCC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 XSVUFCKWQFXULD-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 201000010653 vesiculitis Diseases 0.000 description 4
- IXIXYGRQUCUKAG-NSHDSACASA-N (2s)-2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]-n-ethylpropanamide Chemical compound C=1C=C(C#N)C(Cl)=CC=1N([C@@H](C)C(=O)NCC)CC1CC1 IXIXYGRQUCUKAG-NSHDSACASA-N 0.000 description 3
- ZXOHWQIMOWWRGM-QMMMGPOBSA-N (2s)-2-[4-cyano-3-(trifluoromethyl)-n-(3,3,3-trifluoropropyl)anilino]propanoic acid Chemical compound FC(F)(F)CCN([C@@H](C)C(O)=O)C1=CC=C(C#N)C(C(F)(F)F)=C1 ZXOHWQIMOWWRGM-QMMMGPOBSA-N 0.000 description 3
- 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 description 3
- GTLLERAHZGRNKQ-UHFFFAOYSA-N 2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]butanoic acid Chemical compound CCC(C(O)=O)N(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 GTLLERAHZGRNKQ-UHFFFAOYSA-N 0.000 description 3
- AAWQUNDMNRKWKW-UHFFFAOYSA-N 2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]butanoic acid Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(C(CC)C(O)=O)CC1CC1 AAWQUNDMNRKWKW-UHFFFAOYSA-N 0.000 description 3
- FUVIDWIMUPLGDE-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]butanoic acid Chemical compound CCC(C(O)=O)N(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 FUVIDWIMUPLGDE-UHFFFAOYSA-N 0.000 description 3
- JFIBVAVATAXXRW-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]-n-methylacetamide Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(CC(=O)NC)CC1CC1 JFIBVAVATAXXRW-UHFFFAOYSA-N 0.000 description 3
- COLGRIVKZIFHHF-UHFFFAOYSA-N 2-[4-cyano-n-(2,2-dimethylpropyl)-3-(trifluoromethyl)anilino]acetic acid Chemical compound CC(C)(C)CN(CC(O)=O)C1=CC=C(C#N)C(C(F)(F)F)=C1 COLGRIVKZIFHHF-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- BSGKYPNMMSTSSE-UHFFFAOYSA-N 4-(cyclopropylmethylamino)benzene-1,2-dicarbonitrile Chemical compound C1=C(C#N)C(C#N)=CC=C1NCC1CC1 BSGKYPNMMSTSSE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 102000040945 Transcription factor Human genes 0.000 description 3
- 108091023040 Transcription factor Proteins 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 229960003473 androstanolone Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 230000003920 cognitive function Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical group NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 3
- 239000007884 disintegrant Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000004064 dysfunction Effects 0.000 description 3
- 230000002357 endometrial effect Effects 0.000 description 3
- 210000004696 endometrium Anatomy 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 206010016256 fatigue Diseases 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 230000001976 improved effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000036651 mood Effects 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000004031 partial agonist Substances 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000583 progesterone congener Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 210000004706 scrotum Anatomy 0.000 description 3
- 239000000849 selective androgen receptor modulator Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- YMVOZFAAHLTMFJ-UHFFFAOYSA-N tert-butyl 2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]acetate Chemical compound CC(C)(C)OC(=O)CN(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 YMVOZFAAHLTMFJ-UHFFFAOYSA-N 0.000 description 3
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 3
- RIUJWUWLGXBICR-UHFFFAOYSA-N tert-butyl 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC(C)(C)C RIUJWUWLGXBICR-UHFFFAOYSA-N 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- VGJWVEYTYIBXIA-UHFFFAOYSA-N 2,2,2-trifluoroethane-1,1-diol Chemical compound OC(O)C(F)(F)F VGJWVEYTYIBXIA-UHFFFAOYSA-N 0.000 description 2
- WDBXEQHYRUUHHW-UHFFFAOYSA-N 2-(trifluoromethyl)-4-(1,1,1-trifluoropropan-2-ylamino)benzonitrile Chemical compound FC(F)(F)C(C)NC1=CC=C(C#N)C(C(F)(F)F)=C1 WDBXEQHYRUUHHW-UHFFFAOYSA-N 0.000 description 2
- FWHWLWRUKBBJOP-UHFFFAOYSA-N 2-[4-cyano-n-(2,2-dimethylpropyl)-3-(trifluoromethyl)anilino]acetamide Chemical compound CC(C)(C)CN(CC(N)=O)C1=CC=C(C#N)C(C(F)(F)F)=C1 FWHWLWRUKBBJOP-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- FFBUPXJDPVGVJR-UHFFFAOYSA-N 3-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-2-methylpropanamide Chemical compound NC(=O)C(C)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 FFBUPXJDPVGVJR-UHFFFAOYSA-N 0.000 description 2
- AGVBSNSRXAXIMV-UHFFFAOYSA-N 4-(1,1,1-trifluorobutan-2-ylamino)-2-(trifluoromethyl)benzonitrile Chemical compound CCC(C(F)(F)F)NC1=CC=C(C#N)C(C(F)(F)F)=C1 AGVBSNSRXAXIMV-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- MSYBDURWPBOULG-UHFFFAOYSA-N 4-[2-cyanopropyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound N#CC(C)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 MSYBDURWPBOULG-UHFFFAOYSA-N 0.000 description 2
- GRAMBXOGWUNDOZ-UHFFFAOYSA-N 4-[2-oxoethyl(1,1,1-trifluorobutan-2-yl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCC(C(F)(F)F)N(CC=O)C1=CC=C(C#N)C(C(F)(F)F)=C1 GRAMBXOGWUNDOZ-UHFFFAOYSA-N 0.000 description 2
- MATPMRZIKQBLEV-UHFFFAOYSA-N 4-[prop-2-enyl(1,1,1-trifluoropropan-2-yl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C(C)N(CC=C)C1=CC=C(C#N)C(C(F)(F)F)=C1 MATPMRZIKQBLEV-UHFFFAOYSA-N 0.000 description 2
- LCCPQUYXMFXCAC-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)benzonitrile Chemical compound FC1=CC=C(C#N)C(C(F)(F)F)=C1 LCCPQUYXMFXCAC-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 208000030507 AIDS Diseases 0.000 description 2
- 208000003200 Adenoma Diseases 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 2
- 208000010392 Bone Fractures Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 2
- 230000004568 DNA-binding Effects 0.000 description 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 2
- 206010013774 Dry eye Diseases 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 208000030814 Eating disease Diseases 0.000 description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 description 2
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 description 2
- 102000005720 Glutathione transferase Human genes 0.000 description 2
- 108010070675 Glutathione transferase Proteins 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 208000037171 Hypercorticoidism Diseases 0.000 description 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 2
- 206010020880 Hypertrophy Diseases 0.000 description 2
- 206010058359 Hypogonadism Diseases 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- 102000009151 Luteinizing Hormone Human genes 0.000 description 2
- 108010073521 Luteinizing Hormone Proteins 0.000 description 2
- 102100021316 Mineralocorticoid receptor Human genes 0.000 description 2
- 208000000112 Myalgia Diseases 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 206010029216 Nervousness Diseases 0.000 description 2
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 208000010191 Osteitis Deformans Diseases 0.000 description 2
- 208000004286 Osteochondrodysplasias Diseases 0.000 description 2
- 208000027868 Paget disease Diseases 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 206010036049 Polycystic ovaries Diseases 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 description 2
- 229940123788 Progesterone receptor antagonist Drugs 0.000 description 2
- 206010039792 Seborrhoea Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 206010041925 Staphylococcal infections Diseases 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 201000005255 adrenal gland hyperfunction Diseases 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000008484 agonism Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 201000002996 androgenic alopecia Diseases 0.000 description 2
- 208000007502 anemia Diseases 0.000 description 2
- 208000022531 anorexia Diseases 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000011882 arthroplasty Methods 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 238000009739 binding Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- YOPDMGNERLFFAW-UHFFFAOYSA-N bromo butanoate Chemical compound CCCC(=O)OBr YOPDMGNERLFFAW-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 235000014632 disordered eating Nutrition 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229940011871 estrogen Drugs 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229940028334 follicle stimulating hormone Drugs 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000008717 functional decline Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229960001731 gluceptate Drugs 0.000 description 2
- KWMLJOLKUYYJFJ-VFUOTHLCSA-N glucoheptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-VFUOTHLCSA-N 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000011132 hemopoiesis Effects 0.000 description 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 2
- 230000003284 homeostatic effect Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 2
- 201000008980 hyperinsulinism Diseases 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000037903 inflammatory enteropathy Diseases 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 108020001756 ligand binding domains Proteins 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 229940040129 luteinizing hormone Drugs 0.000 description 2
- 230000001926 lymphatic effect Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 208000027202 mammary Paget disease Diseases 0.000 description 2
- 230000003340 mental effect Effects 0.000 description 2
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- 229960003248 mifepristone Drugs 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 230000003387 muscular Effects 0.000 description 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000009826 neoplastic cell growth Effects 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 230000011164 ossification Effects 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 210000001672 ovary Anatomy 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 208000028169 periodontal disease Diseases 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 201000011461 pre-eclampsia Diseases 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 208000001076 sarcopenia Diseases 0.000 description 2
- 208000008742 seborrheic dermatitis Diseases 0.000 description 2
- 230000037152 sensory function Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 102000005969 steroid hormone receptors Human genes 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- AVNYCGDQCVOKCA-NSHDSACASA-N tert-butyl (2s)-2-[4-cyano-3-(trifluoromethyl)-n-(3,3,3-trifluoropropyl)anilino]propanoate Chemical compound CC(C)(C)OC(=O)[C@H](C)N(CCC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 AVNYCGDQCVOKCA-NSHDSACASA-N 0.000 description 2
- YHZXPFDSZJJVCW-UHFFFAOYSA-N tert-butyl 2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]butanoate Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(C(CC)C(=O)OC(C)(C)C)CC1CC1 YHZXPFDSZJJVCW-UHFFFAOYSA-N 0.000 description 2
- STQGZBYQNRKFOV-UHFFFAOYSA-N tert-butyl 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]acetate Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(CC(=O)OC(C)(C)C)CC1CC1 STQGZBYQNRKFOV-UHFFFAOYSA-N 0.000 description 2
- 206010043554 thrombocytopenia Diseases 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000001890 transfection Methods 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 239000002691 unilamellar liposome Substances 0.000 description 2
- 210000003932 urinary bladder Anatomy 0.000 description 2
- 230000029663 wound healing Effects 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- QBVHMPFSDVNFAY-UHFFFAOYSA-N 1,1,1-trifluorobutan-2-one Chemical compound CCC(=O)C(F)(F)F QBVHMPFSDVNFAY-UHFFFAOYSA-N 0.000 description 1
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 description 1
- JTLAIKFGRHDNQM-UHFFFAOYSA-N 1-bromo-2-fluoroethane Chemical compound FCCBr JTLAIKFGRHDNQM-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
- SOZGHDCEWOLLHV-UHFFFAOYSA-N 2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC=C1C#N SOZGHDCEWOLLHV-UHFFFAOYSA-N 0.000 description 1
- DVTFAROAXUYYGK-UHFFFAOYSA-N 2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]-n-ethylbutanamide Chemical compound CCNC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 DVTFAROAXUYYGK-UHFFFAOYSA-N 0.000 description 1
- KAHPABHFGVGHIU-UHFFFAOYSA-N 2-[3,4-dicyano-n-(2,2,2-trifluoroethyl)anilino]-n-methylbutanamide Chemical compound CNC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(C#N)=C1 KAHPABHFGVGHIU-UHFFFAOYSA-N 0.000 description 1
- ZMUWTWQNVWCPAQ-UHFFFAOYSA-N 2-[3,4-dicyano-n-(cyclopropylmethyl)anilino]-n-methylbutanamide Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(C(CC)C(=O)NC)CC1CC1 ZMUWTWQNVWCPAQ-UHFFFAOYSA-N 0.000 description 1
- BIOILYDIZOEUNF-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]-n-ethylbutanamide Chemical compound CCNC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 BIOILYDIZOEUNF-UHFFFAOYSA-N 0.000 description 1
- LNEPCRPBYVBKLP-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(2,2,2-trifluoroethyl)anilino]-n-methylbutanamide Chemical compound CNC(=O)C(CC)N(CC(F)(F)F)C1=CC=C(C#N)C(Cl)=C1 LNEPCRPBYVBKLP-UHFFFAOYSA-N 0.000 description 1
- KHHKQNYFZPVTTP-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]-n-ethylbutanamide Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(C(CC)C(=O)NCC)CC1CC1 KHHKQNYFZPVTTP-UHFFFAOYSA-N 0.000 description 1
- CQVZMXMEAJWMQW-UHFFFAOYSA-N 2-[3-chloro-4-cyano-n-(cyclopropylmethyl)anilino]-n-methylbutanamide Chemical compound C=1C=C(C#N)C(Cl)=CC=1N(C(CC)C(=O)NC)CC1CC1 CQVZMXMEAJWMQW-UHFFFAOYSA-N 0.000 description 1
- PGKPNNMOFHNZJX-UHFFFAOYSA-N 2-chloro-4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C(Cl)=C1 PGKPNNMOFHNZJX-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- IGOPOYHPIKTQSS-UHFFFAOYSA-N 3,3,3-trifluoropropan-1-amine;hydrochloride Chemical compound [Cl-].[NH3+]CCC(F)(F)F IGOPOYHPIKTQSS-UHFFFAOYSA-N 0.000 description 1
- UMCMPZBLKLEWAF-BCTGSCMUSA-N 3-[(3-cholamidopropyl)dimethylammonio]propane-1-sulfonate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCC[N+](C)(C)CCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 UMCMPZBLKLEWAF-BCTGSCMUSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical class OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- POERRGSFZLNURV-UHFFFAOYSA-N 4-[1-cyanoethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound N#CC(C)N(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 POERRGSFZLNURV-UHFFFAOYSA-N 0.000 description 1
- ZHPKHLZEHZDDHM-UHFFFAOYSA-N 4-[2-oxoethyl(1,1,1-trifluoropropan-2-yl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C(C)N(CC=O)C1=CC=C(C#N)C(C(F)(F)F)=C1 ZHPKHLZEHZDDHM-UHFFFAOYSA-N 0.000 description 1
- HKUYBADXDLZCHP-UHFFFAOYSA-N 4-[cyanomethyl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)CN(CC#N)C1=CC=C(C#N)C(C(F)(F)F)=C1 HKUYBADXDLZCHP-UHFFFAOYSA-N 0.000 description 1
- AOCSCLTZZWYSHP-UHFFFAOYSA-N 4-[cyanomethyl(3,3,3-trifluoropropyl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)CCN(CC#N)C1=CC=C(C#N)C(C(F)(F)F)=C1 AOCSCLTZZWYSHP-UHFFFAOYSA-N 0.000 description 1
- ZQBVKSAEUSRAME-UHFFFAOYSA-N 4-[cyanomethyl(cyclopropylmethyl)amino]benzene-1,2-dicarbonitrile Chemical compound C=1C=C(C#N)C(C#N)=CC=1N(CC#N)CC1CC1 ZQBVKSAEUSRAME-UHFFFAOYSA-N 0.000 description 1
- DXYIQGVRFUZCGU-UHFFFAOYSA-N 4-[prop-2-enyl(1,1,1-trifluorobutan-2-yl)amino]-2-(trifluoromethyl)benzonitrile Chemical compound CCC(C(F)(F)F)N(CC=C)C1=CC=C(C#N)C(C(F)(F)F)=C1 DXYIQGVRFUZCGU-UHFFFAOYSA-N 0.000 description 1
- PMDYLCUKSLBUHO-UHFFFAOYSA-N 4-amino-2-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C#N)C(C(F)(F)F)=C1 PMDYLCUKSLBUHO-UHFFFAOYSA-N 0.000 description 1
- ZFBKYGFPUCUYIF-UHFFFAOYSA-N 4-amino-2-chlorobenzonitrile Chemical compound NC1=CC=C(C#N)C(Cl)=C1 ZFBKYGFPUCUYIF-UHFFFAOYSA-N 0.000 description 1
- RRCAJFYQXKPXOJ-UHFFFAOYSA-N 4-aminobenzene-1,2-dicarbonitrile Chemical compound NC1=CC=C(C#N)C(C#N)=C1 RRCAJFYQXKPXOJ-UHFFFAOYSA-N 0.000 description 1
- QQEKYCCJLSRLEC-UHFFFAOYSA-N 4-fluorobenzene-1,2-dicarbonitrile Chemical compound FC1=CC=C(C#N)C(C#N)=C1 QQEKYCCJLSRLEC-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 239000002677 5-alpha reductase inhibitor Substances 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 229940123407 Androgen receptor antagonist Drugs 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010003694 Atrophy Diseases 0.000 description 1
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229940122361 Bisphosphonate Drugs 0.000 description 1
- 208000006386 Bone Resorption Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical class [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 101100149678 Caenorhabditis elegans snr-3 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical class [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical class [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Chemical class OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 101100440699 Drosophila melanogaster corto gene Proteins 0.000 description 1
- 102100038595 Estrogen receptor Human genes 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- NMJREATYWWNIKX-UHFFFAOYSA-N GnRH Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CC(C)C)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 NMJREATYWWNIKX-UHFFFAOYSA-N 0.000 description 1
- 102000018997 Growth Hormone Human genes 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- 239000000095 Growth Hormone-Releasing Hormone Substances 0.000 description 1
- 102000038461 Growth Hormone-Releasing Hormone Human genes 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 101000926939 Homo sapiens Glucocorticoid receptor Proteins 0.000 description 1
- 229940127517 Hormone Receptor Modulators Drugs 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000589902 Leptospira Species 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 108060001084 Luciferase Proteins 0.000 description 1
- 239000005089 Luciferase Substances 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 102000003979 Mineralocorticoid Receptors Human genes 0.000 description 1
- 241000713333 Mouse mammary tumor virus Species 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102000003982 Parathyroid hormone Human genes 0.000 description 1
- 108090000445 Parathyroid hormone Proteins 0.000 description 1
- 208000008601 Polycythemia Diseases 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- 229940083324 Selective androgen receptor modulator Drugs 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 101710142969 Somatoliberin Proteins 0.000 description 1
- 102000013275 Somatomedins Human genes 0.000 description 1
- 102000005157 Somatostatin Human genes 0.000 description 1
- 108010056088 Somatostatin Proteins 0.000 description 1
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 108010085012 Steroid Receptors Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000000695 adrenergic alpha-agonist Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229940083712 aldosterone antagonist Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 229940062331 androgel Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000000883 anti-obesity agent Substances 0.000 description 1
- 230000003262 anti-osteoporosis Effects 0.000 description 1
- 230000000123 anti-resoprtive effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003529 anticholesteremic agent Substances 0.000 description 1
- 229940127226 anticholesterol agent Drugs 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940125710 antiobesity agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 101150010487 are gene Proteins 0.000 description 1
- 239000003886 aromatase inhibitor Substances 0.000 description 1
- 229940046844 aromatase inhibitors Drugs 0.000 description 1
- 238000009246 art therapy Methods 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 150000004663 bisphosphonates Chemical class 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000037182 bone density Effects 0.000 description 1
- 230000024279 bone resorption Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940092727 claro Drugs 0.000 description 1
- 229940090805 clavulanate Drugs 0.000 description 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical class OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- 229940110767 coenzyme Q10 Drugs 0.000 description 1
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229960003624 creatine Drugs 0.000 description 1
- 239000006046 creatine Substances 0.000 description 1
- 230000009260 cross reactivity Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical class [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940009662 edetate Drugs 0.000 description 1
- 229950008913 edisilate Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229950005627 embonate Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000006274 endogenous ligand Substances 0.000 description 1
- 239000007920 enema Substances 0.000 description 1
- 229940079360 enema for constipation Drugs 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 108010038795 estrogen receptors Proteins 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
- 229960005420 etoposide Drugs 0.000 description 1
- 230000005713 exacerbation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000005454 flavour additive Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 108010074605 gamma-Globulins Proteins 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000003324 growth hormone secretagogue Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical class OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 102000027411 intracellular receptors Human genes 0.000 description 1
- 108091008582 intracellular receptors Proteins 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960002725 isoflurane Drugs 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229940043355 kinase inhibitor Drugs 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 230000009021 linear effect Effects 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000003670 luciferase enzyme activity assay Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000013160 medical therapy Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 230000005184 men's health Effects 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- VGNTYNWETLNKOG-UHFFFAOYSA-N methyl 2-[[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]methyl]prop-2-enoate Chemical compound COC(=O)C(=C)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 VGNTYNWETLNKOG-UHFFFAOYSA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- QNCGOOWEAQSHDO-UHFFFAOYSA-N methyl 3-[4-cyano-n-(2,2,2-trifluoroethyl)-3-(trifluoromethyl)anilino]-2-methylpropanoate Chemical compound COC(=O)C(C)CN(CC(F)(F)F)C1=CC=C(C#N)C(C(F)(F)F)=C1 QNCGOOWEAQSHDO-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 239000002395 mineralocorticoid Substances 0.000 description 1
- 239000002394 mineralocorticoid antagonist Substances 0.000 description 1
- 238000007479 molecular analysis Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 230000020763 muscle atrophy Effects 0.000 description 1
- 201000000585 muscular atrophy Diseases 0.000 description 1
- 210000002346 musculoskeletal system Anatomy 0.000 description 1
- HDCXQTPVTAIPNZ-UHFFFAOYSA-N n-({[4-(aminosulfonyl)phenyl]amino}carbonyl)-4-methylbenzenesulfonamide Chemical group C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 HDCXQTPVTAIPNZ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000199 parathyroid hormone Substances 0.000 description 1
- 229960001319 parathyroid hormone Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000008105 phosphatidylcholines Chemical class 0.000 description 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920002721 polycyanoacrylate Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- QPMDWIOUHQWKHV-ODZAUARKSA-M potassium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound [K+].OC(=O)\C=C/C([O-])=O QPMDWIOUHQWKHV-ODZAUARKSA-M 0.000 description 1
- 230000003334 potential effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 229940075993 receptor modulator Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000333 selective estrogen receptor modulator Substances 0.000 description 1
- 229940095743 selective estrogen receptor modulator Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 210000004999 sex organ Anatomy 0.000 description 1
- 230000036301 sexual development Effects 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 201000002859 sleep apnea Diseases 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 208000020685 sleep-wake disease Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 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
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 108020003113 steroid hormone receptors Proteins 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229950002757 teoclate Drugs 0.000 description 1
- 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
- 230000002381 testicular Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 229960000103 thrombolytic agent Drugs 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 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
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 238000003146 transient transfection Methods 0.000 description 1
- 238000012384 transportation and delivery Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 210000001177 vas deferen Anatomy 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (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 (https=) |
| EP (1) | EP1725522B1 (https=) |
| JP (1) | JP4805909B2 (https=) |
| ES (1) | ES2523017T3 (https=) |
| WO (1) | WO2005085185A1 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2004110978A2 (en) * | 2003-06-10 | 2004-12-23 | Smithkline Beecham Corporation | 1-aminonaphthalenes as modulators of androgen, glucocorticoid, mineralocorticoid and progesterone receptors |
| 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 |
| EP1954133A4 (en) * | 2005-11-30 | 2010-11-24 | Glaxosmithkline Llc | PYRROLIDINANILINE |
| 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 |
| MX2009001442A (es) | 2006-08-09 | 2009-02-18 | Smithkline Beecham Corp | Pirrolidinona anilinas como moduladores del receptor de progesterona. |
| 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 |
| CA2716320C (en) | 2008-02-22 | 2014-01-28 | Radius Health, Inc. | Selective androgen receptor modulators |
| AU2009231892A1 (en) * | 2008-03-31 | 2009-10-08 | The Trustees Of Columbia University In The City Of New York | Methods of diagnosing, preventing and treating bone mass diseases |
| JPWO2009136629A1 (ja) * | 2008-05-09 | 2011-09-08 | 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 |
| AU2011212813B2 (en) | 2010-02-04 | 2014-10-23 | Radius Health, Inc. | Selective androgen receptor modulators |
| HUE030072T2 (en) | 2010-05-12 | 2017-04-28 | Radius Health Inc | Therapeutic prescriptions |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9133182B2 (en) | 2010-09-28 | 2015-09-15 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| ES3055185T3 (en) | 2014-03-28 | 2026-02-10 | Univ Duke | Treatment of an estrogen receptor positive breast cancer using a selective estrogen receptor modulator |
| AU2015331756A1 (en) * | 2014-10-16 | 2017-05-04 | Gtx, Inc. | Methods of treating urological disorders using SARMs |
| MX389702B (es) | 2016-06-22 | 2025-03-20 | Ellipses Pharma Ltd | Compuestos para usarse en el tratamiento de cancer de mama que expresa el receptor de androgenos (ar+). |
| JP7481115B2 (ja) | 2017-01-05 | 2024-05-10 | ラジウス ファーマシューティカルズ，インコーポレイテッド | Ｒａｄ１９０１－２ｈｃｌの多形性形態 |
| CA3099155A1 (en) | 2018-05-14 | 2019-11-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| MX2020013713A (es) | 2018-07-04 | 2021-03-02 | Radius Pharmaceuticals Inc | Formas polimorficas de rad1901-2hcl. |
| EP3924328A1 (en) | 2019-02-12 | 2021-12-22 | Radius Pharmaceuticals, Inc. | Processes and compounds |
| CA3138197A1 (en) | 2019-05-14 | 2020-11-19 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| EP4058464A1 (en) | 2019-11-13 | 2022-09-21 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
| MX2023011241A (es) | 2021-03-23 | 2023-10-03 | Nuvation Bio Inc | Compuestos dirigidos a receptores de hormonas nucleares contra el cancer. |
| JP2024516024A (ja) | 2021-05-03 | 2024-04-11 | ニューベイション・バイオ・インコーポレイテッド | 抗がん核内ホルモン受容体標的化化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2272433A1 (en) * | 1996-11-22 | 1998-05-28 | James E. Audia | N-(aryl/heteroaryl) amino acid esters, pharmaceutical compositions, and methods for inhibiting beta-amyloid peptide release and/or its synthesis |
| TR199901132T2 (xx) * | 1996-11-22 | 1999-08-23 | Elan Pharmaceuticals, Inc. | N-(aril/heteoaril) amino asit t�revleri, bunlar� i�eren farmas�tik bile�imler ve b�yle bile�ikler kullan�larak �-amiloid peptidinin sal�nmas�n� ve/veya sentezini inhibe etmek i�in y�ntemler. |
| 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 |
| AU2001263130A1 (en) * | 2000-06-06 | 2001-12-17 | Warner Lambert Company | Bicyclic cyclohexylamines and their use as nmda receptor antagonists |
| DE60137728D1 (de) * | 2000-08-24 | 2009-04-02 | Univ Tennessee Res Foundation | Selektive Modulatoren des Androgenrezeptors und Methoden zu deren Verwendung |
| 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 |
-
2005
- 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 WO PCT/US2005/007245 patent/WO2005085185A1/en not_active Ceased
- 2005-03-03 JP JP2007502061A patent/JP4805909B2/ja not_active Expired - Lifetime
- 2005-03-03 ES ES05730067.5T patent/ES2523017T3/es not_active Expired - Lifetime
-
2009
- 2009-02-25 US US12/392,687 patent/US7723385B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1725522A1 (en) | 2006-11-29 |
| JP4805909B2 (ja) | 2011-11-02 |
| EP1725522B1 (en) | 2014-09-10 |
| US20090163588A1 (en) | 2009-06-25 |
| WO2005085185A1 (en) | 2005-09-15 |
| JP2007526336A (ja) | 2007-09-13 |
| US7514470B2 (en) | 2009-04-07 |
| US7723385B2 (en) | 2010-05-25 |
| US20070191479A1 (en) | 2007-08-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2523017T3 (es) | Derivados de anilina como moduladores selectivos de los receptores de andrógenos | |
| US7834063B2 (en) | Benzonitryl and nitrobenzyl derivatives that modulate androgen receptors | |
| EP1636167A2 (en) | 1-aminonaphthalenes as modulators of androgen, glucocorticoid, mineralocorticoid and progesterone receptors | |
| JP2024028458A (ja) | プロスタサイクリン（ｐｇｉ２）受容体に関連する障害の処置に有用なｐｇｉ２受容体の調節因子 | |
| WO2005000795A2 (en) | Aniline derivatived androgen-, glucocorticoid-, mineralcorticoid- and progesterone- receptor modulators | |
| ES2712048T3 (es) | Derivado de alquilamina | |
| JP2011515396A5 (https=) | ||
| ES2340664T3 (es) | Derivados de sulfonamidas. | |
| KR102127939B1 (ko) | 선택적인 안드로겐 수용체 조절제로서의 인돌카르보니트릴 | |
| CN103391920A (zh) | 钙敏感受体激活化合物 | |
| JP2014508103A (ja) | カルシウム感知受容体活性化合物 | |
| FR3066761A1 (fr) | Nouveaux composes inhibiteurs des canaux ioniques | |
| CN108239073A (zh) | 化合物、医药组成物及其用途 | |
| HK1208867B (en) | Indolecarbonitriles as selective androgen receptor modulators | |
| UA112898C2 (uk) | Індолкарбонітрили як селективні модулятори андрогенного рецептора |