RU2767257C2 - Производные бисфенола и их применение в качестве модуляторов активности рецептора андрогена - Google Patents
Производные бисфенола и их применение в качестве модуляторов активности рецептора андрогена Download PDFInfo
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- RU2767257C2 RU2767257C2 RU2018140071A RU2018140071A RU2767257C2 RU 2767257 C2 RU2767257 C2 RU 2767257C2 RU 2018140071 A RU2018140071 A RU 2018140071A RU 2018140071 A RU2018140071 A RU 2018140071A RU 2767257 C2 RU2767257 C2 RU 2767257C2
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- propan
- chloro
- phenoxy
- phenyl
- dichloro
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- VGIAPECDMYQBKZ-DNQXCXABSA-N [(2R)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]propan-2-yl]phenoxy]-3-propan-2-yloxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)OC(C)=O)Cl)COC(C)C VGIAPECDMYQBKZ-DNQXCXABSA-N 0.000 description 1
- MUXNTTIHDJVIFQ-FGZHOGPDSA-N [(2R)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]propan-2-yl]-2-chlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)C(C)(C)C1=CC(=C(C=C1)OC[C@H](CS(=O)(=O)CC)OC(C)=O)Cl)Cl)CCl MUXNTTIHDJVIFQ-FGZHOGPDSA-N 0.000 description 1
- UQPDULWNWFTCGX-DHIUTWEWSA-N [(2R)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]propan-2-yl]-2-chlorophenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)C(C)(C)C1=CC(=C(C=C1)OC[C@@H](CN1C=NC=C1)OC(C)=O)Cl)Cl)CCl UQPDULWNWFTCGX-DHIUTWEWSA-N 0.000 description 1
- BNFSMGZRZPXMDS-NHCUHLMSSA-N [(2R)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]propan-2-yl]-2-chlorophenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)C(C)(C)C1=CC(=C(C=C1)OC[C@@H](CCl)OC(C)=O)Cl)Cl)COC BNFSMGZRZPXMDS-NHCUHLMSSA-N 0.000 description 1
- DMUZDKFKLJLMEU-DHIUTWEWSA-N [(2R)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]phenyl]propan-2-yl]-2,6-dichlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl DMUZDKFKLJLMEU-DHIUTWEWSA-N 0.000 description 1
- VPSAKJIFGWRYPL-UNMCSNQZSA-N [(2R)-1-[4-[2-[4-[(2S)-3-[acetyl(methylsulfonyl)amino]-2-hydroxypropoxy]phenyl]propan-2-yl]-2,6-dichlorophenoxy]-3-chloropropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CN(C(C)=O)S(=O)(=O)C)O)Cl VPSAKJIFGWRYPL-UNMCSNQZSA-N 0.000 description 1
- JCNLJJVZCOAUCL-QGZVFWFLSA-N [(2R)-1-[4-[3,5-dichloro-4-(3-chloropropoxy)phenyl]sulfonylphenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OCCCCl)Cl)CS(=O)(=O)CC JCNLJJVZCOAUCL-QGZVFWFLSA-N 0.000 description 1
- LKTARLYDQJFOOC-RBUKOAKNSA-N [(2R)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl LKTARLYDQJFOOC-RBUKOAKNSA-N 0.000 description 1
- JIXYMDLSACOFOY-VQTJNVASSA-N [(2R)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@@H](CN1C=NC=C1)OC(C)=O)Cl)CCl JIXYMDLSACOFOY-VQTJNVASSA-N 0.000 description 1
- FDZUGDRVMFCJTP-ZWKOTPCHSA-N [(2R)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@H](CCl)OC(C)=O)Cl)COC FDZUGDRVMFCJTP-ZWKOTPCHSA-N 0.000 description 1
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- VBKFSGAGQIGCBL-RBUKOAKNSA-N [(2R)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@@H](CN1C=NC=C1)OC(C)=O)Cl)Cl)CCl VBKFSGAGQIGCBL-RBUKOAKNSA-N 0.000 description 1
- MZQUMRKMZWRLIN-DLBZAZTESA-N [(2R)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@H](CCl)OC(C)=O)Cl)Cl)COC MZQUMRKMZWRLIN-DLBZAZTESA-N 0.000 description 1
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- FDZUGDRVMFCJTP-QZTJIDSGSA-N [(2R)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)OC(C)=O)Cl)COC FDZUGDRVMFCJTP-QZTJIDSGSA-N 0.000 description 1
- NBUHJKDOJRTQGY-NHCUHLMSSA-N [(2R)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-morpholin-4-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)OC(C)=O)Cl)CN1CCOCC1 NBUHJKDOJRTQGY-NHCUHLMSSA-N 0.000 description 1
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- VBKFSGAGQIGCBL-RTBURBONSA-N [(2R)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@@H](CN1C=NC=C1)OC(C)=O)Cl)Cl)CCl VBKFSGAGQIGCBL-RTBURBONSA-N 0.000 description 1
- MZQUMRKMZWRLIN-IAGOWNOFSA-N [(2R)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@@H](CCl)OC(C)=O)Cl)Cl)COC MZQUMRKMZWRLIN-IAGOWNOFSA-N 0.000 description 1
- DRKOEMRCGUXQQE-RTBURBONSA-N [(2R)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]phenyl]sulfonyl-2,6-dichlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl DRKOEMRCGUXQQE-RTBURBONSA-N 0.000 description 1
- HNSISWAAVPAJLL-RBBKRZOGSA-N [(2R)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[3,5-dichloro-4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@H](CCl)O)Cl)CN(C(C)=O)S(=O)(=O)C HNSISWAAVPAJLL-RBBKRZOGSA-N 0.000 description 1
- HNSISWAAVPAJLL-IFMALSPDSA-N [(2R)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[3,5-dichloro-4-[(2S)-3-chloro-2-hydroxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)O)Cl)CN(C(C)=O)S(=O)(=O)C HNSISWAAVPAJLL-IFMALSPDSA-N 0.000 description 1
- RLYDYXUGXJCAPI-BJKOFHAPSA-N [(2R)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl RLYDYXUGXJCAPI-BJKOFHAPSA-N 0.000 description 1
- RLYDYXUGXJCAPI-DNQXCXABSA-N [(2R)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl RLYDYXUGXJCAPI-DNQXCXABSA-N 0.000 description 1
- YHGMKLPSXIIMMI-VQTJNVASSA-N [(2R)-1-[acetyl(methylsulfonyl)amino]-3-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl YHGMKLPSXIIMMI-VQTJNVASSA-N 0.000 description 1
- YHGMKLPSXIIMMI-WOJBJXKFSA-N [(2R)-1-[acetyl(methylsulfonyl)amino]-3-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl YHGMKLPSXIIMMI-WOJBJXKFSA-N 0.000 description 1
- NSVAEVMIGROZND-QUCCMNQESA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-(methanesulfonamido)propoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CNS(=O)(=O)C)O)Cl NSVAEVMIGROZND-QUCCMNQESA-N 0.000 description 1
- QTHYVGJQHPTBEQ-IRLDBZIGSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-imidazol-1-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CN1C=NC=C1)O)Cl QTHYVGJQHPTBEQ-IRLDBZIGSA-N 0.000 description 1
- LNDOWZREAHHRMP-QUCCMNQESA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-methoxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](COC)O)Cl LNDOWZREAHHRMP-QUCCMNQESA-N 0.000 description 1
- NSGSMGNRHCHCFD-GGAORHGYSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-morpholin-4-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CN1CCOCC1)O)Cl NSGSMGNRHCHCFD-GGAORHGYSA-N 0.000 description 1
- ZXRUXFDNSUNBEV-IRLDBZIGSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-propan-2-yloxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](COC(C)C)O)Cl ZXRUXFDNSUNBEV-IRLDBZIGSA-N 0.000 description 1
- LVISSFWAYFSPGH-HKUYNNGSSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2,3-dihydroxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CO)O)Cl LVISSFWAYFSPGH-HKUYNNGSSA-N 0.000 description 1
- NSVAEVMIGROZND-ICSRJNTNSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-(methanesulfonamido)propoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CNS(=O)(=O)C)O)Cl NSVAEVMIGROZND-ICSRJNTNSA-N 0.000 description 1
- QTHYVGJQHPTBEQ-UNMCSNQZSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-imidazol-1-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CN1C=NC=C1)O)Cl QTHYVGJQHPTBEQ-UNMCSNQZSA-N 0.000 description 1
- LNDOWZREAHHRMP-ICSRJNTNSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-methoxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](COC)O)Cl LNDOWZREAHHRMP-ICSRJNTNSA-N 0.000 description 1
- NSGSMGNRHCHCFD-GMAHTHKFSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-morpholin-4-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CN1CCOCC1)O)Cl NSGSMGNRHCHCFD-GMAHTHKFSA-N 0.000 description 1
- ZXRUXFDNSUNBEV-UNMCSNQZSA-N [(2R)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-propan-2-yloxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](COC(C)C)O)Cl ZXRUXFDNSUNBEV-UNMCSNQZSA-N 0.000 description 1
- UUFRCTNYBJNQSH-NRFANRHFSA-N [(2R)-2-acetyloxy-3-[2,6-dichloro-4-[2-[4-(3-chloropropoxy)phenyl]propan-2-yl]phenoxy]propyl] acetate Chemical compound C(C)(=O)OC[C@@H](COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OCCCCl)Cl)OC(C)=O UUFRCTNYBJNQSH-NRFANRHFSA-N 0.000 description 1
- ZEEJWQSTYQZJTG-KRWDZBQOSA-N [(2R)-2-acetyloxy-3-[2,6-dichloro-4-[4-(3-chloropropoxy)phenyl]sulfonylphenoxy]propyl] acetate Chemical compound C(C)(=O)OC[C@@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OCCCCl)Cl)OC(C)=O ZEEJWQSTYQZJTG-KRWDZBQOSA-N 0.000 description 1
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- RKESBOCPJWAWJP-FPOVZHCZSA-N [(2R)-2-acetyloxy-3-[4-[2-[3,5-dichloro-4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]propan-2-yl]phenoxy]propyl] acetate Chemical compound CC(=O)OC[C@@H](COc1ccc(cc1)C(C)(C)c1cc(Cl)c(OC[C@@H](O)CCl)c(Cl)c1)OC(C)=O RKESBOCPJWAWJP-FPOVZHCZSA-N 0.000 description 1
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- RESAZKQTKZMDLF-YADHBBJMSA-N [(2S)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]propan-2-yl]phenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)OC(C)=O)Cl)COC RESAZKQTKZMDLF-YADHBBJMSA-N 0.000 description 1
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- VGIAPECDMYQBKZ-RPWUZVMVSA-N [(2S)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]propan-2-yl]phenoxy]-3-propan-2-yloxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)OC(C)=O)Cl)COC(C)C VGIAPECDMYQBKZ-RPWUZVMVSA-N 0.000 description 1
- MUXNTTIHDJVIFQ-YADHBBJMSA-N [(2S)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]propan-2-yl]-2-chlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)C(C)(C)C1=CC(=C(C=C1)OC[C@@H](CS(=O)(=O)CC)OC(C)=O)Cl)Cl)CCl MUXNTTIHDJVIFQ-YADHBBJMSA-N 0.000 description 1
- UQPDULWNWFTCGX-PKTZIBPZSA-N [(2S)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]propan-2-yl]-2-chlorophenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)C(C)(C)C1=CC(=C(C=C1)OC[C@H](CN1C=NC=C1)OC(C)=O)Cl)Cl)CCl UQPDULWNWFTCGX-PKTZIBPZSA-N 0.000 description 1
- BNFSMGZRZPXMDS-RTWAWAEBSA-N [(2S)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]propan-2-yl]-2-chlorophenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1)C(C)(C)C1=CC(=C(C=C1)OC[C@@H](CCl)OC(C)=O)Cl)Cl)COC BNFSMGZRZPXMDS-RTWAWAEBSA-N 0.000 description 1
- DMUZDKFKLJLMEU-PKTZIBPZSA-N [(2S)-1-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]phenyl]propan-2-yl]-2,6-dichlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl DMUZDKFKLJLMEU-PKTZIBPZSA-N 0.000 description 1
- VPSAKJIFGWRYPL-RBBKRZOGSA-N [(2S)-1-[4-[2-[4-[(2S)-3-[acetyl(methylsulfonyl)amino]-2-hydroxypropoxy]phenyl]propan-2-yl]-2,6-dichlorophenoxy]-3-chloropropan-2-yl] acetate Chemical compound CC(=O)O[C@H](CCl)COC1=C(Cl)C=C(C=C1Cl)C(C)(C)C1=CC=C(OC[C@@H](O)CN(C(C)=O)S(C)(=O)=O)C=C1 VPSAKJIFGWRYPL-RBBKRZOGSA-N 0.000 description 1
- JCNLJJVZCOAUCL-KRWDZBQOSA-N [(2S)-1-[4-[3,5-dichloro-4-(3-chloropropoxy)phenyl]sulfonylphenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OCCCCl)Cl)CS(=O)(=O)CC JCNLJJVZCOAUCL-KRWDZBQOSA-N 0.000 description 1
- LKTARLYDQJFOOC-OALUTQOASA-N [(2S)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl LKTARLYDQJFOOC-OALUTQOASA-N 0.000 description 1
- JIXYMDLSACOFOY-PMACEKPBSA-N [(2S)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound CC(=O)O[C@@H](CCl)COc1c(Cl)cc(cc1Cl)S(=O)(=O)c1ccc(OC[C@H](Cn2ccnc2)OC(C)=O)cc1 JIXYMDLSACOFOY-PMACEKPBSA-N 0.000 description 1
- FDZUGDRVMFCJTP-ROUUACIJSA-N [(2S)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@H](CCl)OC(C)=O)Cl)COC FDZUGDRVMFCJTP-ROUUACIJSA-N 0.000 description 1
- NBUHJKDOJRTQGY-SFTDATJTSA-N [(2S)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-morpholin-4-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@H](CCl)OC(C)=O)Cl)CN1CCOCC1 NBUHJKDOJRTQGY-SFTDATJTSA-N 0.000 description 1
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- MZQUMRKMZWRLIN-IRXDYDNUSA-N [(2S)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@H](CCl)OC(C)=O)Cl)Cl)COC MZQUMRKMZWRLIN-IRXDYDNUSA-N 0.000 description 1
- DRKOEMRCGUXQQE-OALUTQOASA-N [(2S)-1-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]phenyl]sulfonyl-2,6-dichlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl DRKOEMRCGUXQQE-OALUTQOASA-N 0.000 description 1
- LKTARLYDQJFOOC-MOPGFXCFSA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl LKTARLYDQJFOOC-MOPGFXCFSA-N 0.000 description 1
- JIXYMDLSACOFOY-UXHICEINSA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@H](CN1C=NC=C1)OC(C)=O)Cl)CCl JIXYMDLSACOFOY-UXHICEINSA-N 0.000 description 1
- FDZUGDRVMFCJTP-MSOLQXFVSA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)OC(C)=O)Cl)COC FDZUGDRVMFCJTP-MSOLQXFVSA-N 0.000 description 1
- NBUHJKDOJRTQGY-RTWAWAEBSA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]-3-morpholin-4-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)OC(C)=O)Cl)CN1CCOCC1 NBUHJKDOJRTQGY-RTWAWAEBSA-N 0.000 description 1
- DKWJQXBCOLHOMM-MSOLQXFVSA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@@H](CS(=O)(=O)CC)OC(C)=O)Cl)Cl)CCl DKWJQXBCOLHOMM-MSOLQXFVSA-N 0.000 description 1
- VBKFSGAGQIGCBL-MOPGFXCFSA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-imidazol-1-ylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@H](CN1C=NC=C1)OC(C)=O)Cl)Cl)CCl VBKFSGAGQIGCBL-MOPGFXCFSA-N 0.000 description 1
- MZQUMRKMZWRLIN-SJORKVTESA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3-chlorophenyl]sulfonyl-2-chlorophenoxy]-3-methoxypropan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1)S(=O)(=O)C1=CC(=C(C=C1)OC[C@@H](CCl)OC(C)=O)Cl)Cl)COC MZQUMRKMZWRLIN-SJORKVTESA-N 0.000 description 1
- DRKOEMRCGUXQQE-MOPGFXCFSA-N [(2S)-1-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]phenyl]sulfonyl-2,6-dichlorophenoxy]-3-ethylsulfonylpropan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=CC=C(C=C1)S(=O)(=O)C1=CC(=C(C(=C1)Cl)OC[C@@H](CS(=O)(=O)CC)OC(C)=O)Cl)CCl DRKOEMRCGUXQQE-MOPGFXCFSA-N 0.000 description 1
- HNSISWAAVPAJLL-UNMCSNQZSA-N [(2S)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[3,5-dichloro-4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@H](CCl)O)Cl)CN(C(C)=O)S(=O)(=O)C HNSISWAAVPAJLL-UNMCSNQZSA-N 0.000 description 1
- HNSISWAAVPAJLL-IRLDBZIGSA-N [(2S)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[3,5-dichloro-4-[(2S)-3-chloro-2-hydroxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@@H](CCl)O)Cl)CN(C(C)=O)S(=O)(=O)C HNSISWAAVPAJLL-IRLDBZIGSA-N 0.000 description 1
- RLYDYXUGXJCAPI-ZEQRLZLVSA-N [(2S)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl RLYDYXUGXJCAPI-ZEQRLZLVSA-N 0.000 description 1
- RLYDYXUGXJCAPI-RPWUZVMVSA-N [(2S)-1-[acetyl(methylsulfonyl)amino]-3-[4-[2-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl RLYDYXUGXJCAPI-RPWUZVMVSA-N 0.000 description 1
- YHGMKLPSXIIMMI-PMACEKPBSA-N [(2S)-1-[acetyl(methylsulfonyl)amino]-3-[4-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl YHGMKLPSXIIMMI-PMACEKPBSA-N 0.000 description 1
- YHGMKLPSXIIMMI-UXHICEINSA-N [(2S)-1-[acetyl(methylsulfonyl)amino]-3-[4-[4-[(2S)-2-acetyloxy-3-chloropropoxy]-3,5-dichlorophenyl]sulfonylphenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OC[C@H](CN(C(C)=O)S(=O)(=O)C)OC(C)=O)Cl)CCl YHGMKLPSXIIMMI-UXHICEINSA-N 0.000 description 1
- LVISSFWAYFSPGH-IEBWSBKVSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2,3-dihydroxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CO)O)Cl LVISSFWAYFSPGH-IEBWSBKVSA-N 0.000 description 1
- NSVAEVMIGROZND-UYAOXDASSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-(methanesulfonamido)propoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CNS(=O)(=O)C)O)Cl NSVAEVMIGROZND-UYAOXDASSA-N 0.000 description 1
- QTHYVGJQHPTBEQ-IFMALSPDSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-imidazol-1-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CN1C=NC=C1)O)Cl QTHYVGJQHPTBEQ-IFMALSPDSA-N 0.000 description 1
- NSGSMGNRHCHCFD-FYYLOGMGSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-morpholin-4-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](CN1CCOCC1)O)Cl NSGSMGNRHCHCFD-FYYLOGMGSA-N 0.000 description 1
- ZXRUXFDNSUNBEV-IFMALSPDSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2R)-2-hydroxy-3-propan-2-yloxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@@H](COC(C)C)O)Cl ZXRUXFDNSUNBEV-IFMALSPDSA-N 0.000 description 1
- LVISSFWAYFSPGH-PKOBYXMFSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2,3-dihydroxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CO)O)Cl LVISSFWAYFSPGH-PKOBYXMFSA-N 0.000 description 1
- NSVAEVMIGROZND-AZUAARDMSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-(methanesulfonamido)propoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CNS(=O)(=O)C)O)Cl NSVAEVMIGROZND-AZUAARDMSA-N 0.000 description 1
- QTHYVGJQHPTBEQ-RBBKRZOGSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-imidazol-1-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CN1C=NC=C1)O)Cl QTHYVGJQHPTBEQ-RBBKRZOGSA-N 0.000 description 1
- LNDOWZREAHHRMP-AZUAARDMSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-methoxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](COC)O)Cl LNDOWZREAHHRMP-AZUAARDMSA-N 0.000 description 1
- NSGSMGNRHCHCFD-JTHBVZDNSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-morpholin-4-ylpropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](CN1CCOCC1)O)Cl NSGSMGNRHCHCFD-JTHBVZDNSA-N 0.000 description 1
- ZXRUXFDNSUNBEV-RBBKRZOGSA-N [(2S)-1-chloro-3-[2,6-dichloro-4-[2-[4-[(2S)-2-hydroxy-3-propan-2-yloxypropoxy]phenyl]propan-2-yl]phenoxy]propan-2-yl] acetate Chemical compound C(C)(=O)O[C@H](CCl)COC1=C(C=C(C=C1Cl)C(C)(C)C1=CC=C(C=C1)OC[C@H](COC(C)C)O)Cl ZXRUXFDNSUNBEV-RBBKRZOGSA-N 0.000 description 1
- ZEEJWQSTYQZJTG-QGZVFWFLSA-N [(2S)-2-acetyloxy-3-[2,6-dichloro-4-[4-(3-chloropropoxy)phenyl]sulfonylphenoxy]propyl] acetate Chemical compound C(C)(=O)OC[C@H](COC1=C(C=C(C=C1Cl)S(=O)(=O)C1=CC=C(C=C1)OCCCCl)Cl)OC(C)=O ZEEJWQSTYQZJTG-QGZVFWFLSA-N 0.000 description 1
- YDPNYEWKKIAQEW-OAQYLSRUSA-N [(2S)-2-acetyloxy-3-[4-[2-[3,5-dichloro-4-(3-chloropropoxy)phenyl]propan-2-yl]phenoxy]propyl] acetate Chemical compound C(C)(=O)OC[C@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OCCCCl)Cl)OC(C)=O YDPNYEWKKIAQEW-OAQYLSRUSA-N 0.000 description 1
- RKESBOCPJWAWJP-PZJWPPBQSA-N [(2S)-2-acetyloxy-3-[4-[2-[3,5-dichloro-4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]propan-2-yl]phenoxy]propyl] acetate Chemical compound C(C)(=O)OC[C@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Cl)OC[C@H](CCl)O)Cl)OC(C)=O RKESBOCPJWAWJP-PZJWPPBQSA-N 0.000 description 1
- VHNQEHFMAQPDDT-XZOQPEGZSA-N [(2S)-2-acetyloxy-3-[4-[2-[4-[(2R)-2-acetyloxy-3-chloropropoxy]-3,5-dibromophenyl]propan-2-yl]phenoxy]propyl] acetate Chemical compound C(C)(=O)OC[C@H](COC1=CC=C(C=C1)C(C)(C)C1=CC(=C(C(=C1)Br)OC[C@H](CCl)OC(C)=O)Br)OC(C)=O VHNQEHFMAQPDDT-XZOQPEGZSA-N 0.000 description 1
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| US20170298033A1 (en) | 2016-04-15 | 2017-10-19 | The University Of British Columbia | Bisphenol derivatives and their use as androgen receptor activity modulators |
| WO2018045450A1 (en) * | 2016-09-09 | 2018-03-15 | British Columbia Cancer Agency Branch | Bisphenol a compounds and methods for treating drug-resistant androgen receptor mediated cancers |
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| KR20210144827A (ko) * | 2019-03-28 | 2021-11-30 | 에싸 파마 아이엔씨. | 안드로겐 수용체의 억제제를 포함하는 약제학적 조성물 및 조합물 및 그의 용도 |
| CN118085015A (zh) * | 2019-09-06 | 2024-05-28 | 江西济民可信集团有限公司 | 作为蛋白降解剂的并环类化合物及其制备方法和用途 |
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| CN113648418B (zh) * | 2021-05-08 | 2022-08-05 | 南方医科大学 | Apelin-APJ抑制剂在制备治疗血睾屏障损伤药物中的应用 |
| KR20220157096A (ko) * | 2021-05-20 | 2022-11-29 | 연세대학교 산학협력단 | 암의 예방, 개선 또는 치료용 조성물 |
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| WO2023046283A1 (en) | 2021-09-22 | 2023-03-30 | Fundació Institut De Recerca Biomèdica (Irb Barcelona) | Compounds and their use in a method for modulating ar (androgen receptor) transcriptional activity |
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| IL262338B (en) | 2022-01-01 |
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| AU2017250025A1 (en) | 2018-11-29 |
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| CA3021008A1 (en) | 2017-10-19 |
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| BR112018071183B1 (pt) | 2022-06-07 |
| KR20190011240A (ko) | 2019-02-01 |
| JP7142577B2 (ja) | 2022-09-27 |
| MX2018012619A (es) | 2019-06-24 |
| WO2017177307A1 (en) | 2017-10-19 |
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| MX392906B (es) | 2025-03-24 |
| KR102409651B1 (ko) | 2022-06-16 |
| BR112018071183A2 (pt) | 2019-02-12 |
| EP3442942A4 (en) | 2019-12-04 |
| JP2022120018A (ja) | 2022-08-17 |
| US11919874B2 (en) | 2024-03-05 |
| EP3442942B1 (en) | 2023-11-15 |
| AU2017250025B2 (en) | 2021-06-24 |
| CN109311807B (zh) | 2024-08-13 |
| EP3442942C0 (en) | 2023-11-15 |
| EP3442942A1 (en) | 2019-02-20 |
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