JP2016172739A5 - - Google Patents
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- Publication number
- JP2016172739A5 JP2016172739A5 JP2016073172A JP2016073172A JP2016172739A5 JP 2016172739 A5 JP2016172739 A5 JP 2016172739A5 JP 2016073172 A JP2016073172 A JP 2016073172A JP 2016073172 A JP2016073172 A JP 2016073172A JP 2016172739 A5 JP2016172739 A5 JP 2016172739A5
- Authority
- JP
- Japan
- Prior art keywords
- diazaspiro
- thioxo
- octane
- phenyl
- oxo
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 49
- -1 pyrrolidin-2-one-yl Chemical group 0.000 claims 35
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 150000001204 N-oxides Chemical class 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 16
- 206010028980 Neoplasm Diseases 0.000 claims 14
- 201000011510 cancer Diseases 0.000 claims 14
- 239000002552 dosage form Substances 0.000 claims 12
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 8
- 239000006186 oral dosage form Substances 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 5
- 125000006747 (C2-C10) heterocycloalkyl group Chemical group 0.000 claims 4
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 230000037396 body weight Effects 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 230000001419 dependent effect Effects 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229940088597 hormone Drugs 0.000 claims 4
- 239000005556 hormone Substances 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 3
- LVWAAWKJSFHDLD-UHFFFAOYSA-N 3-methyl-5-[5-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=C(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C)C(C#N)=NC=2)C=C1 LVWAAWKJSFHDLD-UHFFFAOYSA-N 0.000 claims 3
- FMYJSGCAKSIFEE-UHFFFAOYSA-N 5-[5-[2-fluoro-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCOC(C=C1F)=CC=C1N1C2(CCC2)C(=O)N(C=2C=C(C(C#N)=NC=2)C(F)(F)F)C1=S FMYJSGCAKSIFEE-UHFFFAOYSA-N 0.000 claims 3
- FOCHZLGBEJVMIG-UHFFFAOYSA-N 5-[5-[3-fluoro-4-(3-morpholin-4-ylpropoxy)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound FC1=CC(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)=CC=C1OCCCN1CCOCC1 FOCHZLGBEJVMIG-UHFFFAOYSA-N 0.000 claims 3
- RBSHCUVYELMIBG-UHFFFAOYSA-N 5-[5-[3-fluoro-4-(3-pyrrolidin-1-ylpropoxy)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound FC1=CC(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)=CC=C1OCCCN1CCCC1 RBSHCUVYELMIBG-UHFFFAOYSA-N 0.000 claims 3
- QYTWADPOXANMJX-UHFFFAOYSA-N 5-[5-[4-fluoro-3-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCCOC1=CC(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)=CC=C1F QYTWADPOXANMJX-UHFFFAOYSA-N 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- WHYHOPOYOMDCND-UHFFFAOYSA-N 3-methyl-5-[5-[4-(oxan-4-yloxy)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]pyridine-2-carbonitrile Chemical compound N1=C(C#N)C(C)=CC(N2C(C3(CCC3)N(C=3C=CC(OC4CCOCC4)=CC=3)C2=S)=O)=C1 WHYHOPOYOMDCND-UHFFFAOYSA-N 0.000 claims 2
- PBPWDARAEUASIQ-UHFFFAOYSA-N 5-[5-[2-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCCOC(C=C1F)=CC=C1N1C2(CCC2)C(=O)N(C=2C=C(C(C#N)=NC=2)C(F)(F)F)C1=S PBPWDARAEUASIQ-UHFFFAOYSA-N 0.000 claims 2
- HVVRFIVGBXLFMK-UHFFFAOYSA-N 5-[5-[3-fluoro-4-(2-morpholin-4-ylethoxy)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound FC1=CC(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)=CC=C1OCCN1CCOCC1 HVVRFIVGBXLFMK-UHFFFAOYSA-N 0.000 claims 2
- ZZVWEKVZWXQPTE-UHFFFAOYSA-N 5-[5-[3-fluoro-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-methylpyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=C(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C)C(C#N)=NC=2)C=C1F ZZVWEKVZWXQPTE-UHFFFAOYSA-N 0.000 claims 2
- NWZHJVULIKUIBK-UHFFFAOYSA-N 5-[5-[3-fluoro-4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCCOC1=CC=C(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)C=C1F NWZHJVULIKUIBK-UHFFFAOYSA-N 0.000 claims 2
- DANLBLHNDJGDKM-UHFFFAOYSA-N 5-[5-[4-fluoro-3-(2-morpholin-4-ylethoxy)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound FC1=CC=C(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)C=C1OCCN1CCOCC1 DANLBLHNDJGDKM-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- RDEFTHKSTLWCEU-UHFFFAOYSA-N 3-(trifluoromethyl)pyridine-2-carbonitrile Chemical group FC(F)(F)C1=CC=CN=C1C#N RDEFTHKSTLWCEU-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- ZRVHHWOBMQBXSK-UHFFFAOYSA-N 5-[5-[3-fluoro-4-(2-piperazin-1-ylethoxy)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound FC1=CC(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)=CC=C1OCCN1CCNCC1 ZRVHHWOBMQBXSK-UHFFFAOYSA-N 0.000 claims 1
- LFTPCKCORZZBKJ-UHFFFAOYSA-N 5-[5-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound FC1=CC(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)=CC=C1OCCN1CCCC1 LFTPCKCORZZBKJ-UHFFFAOYSA-N 0.000 claims 1
- KRFVGLPKICDNDQ-UHFFFAOYSA-N 5-[5-[3-fluoro-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=C(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)C=C1F KRFVGLPKICDNDQ-UHFFFAOYSA-N 0.000 claims 1
- GDINBDLWXJOGEW-UHFFFAOYSA-N 5-[5-[4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC=C(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)C=C1 GDINBDLWXJOGEW-UHFFFAOYSA-N 0.000 claims 1
- NIVRTVOACSMZEF-UHFFFAOYSA-N 5-[5-[4-fluoro-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound C1CN(C)CCN1CCOC1=CC(N2C3(CCC3)C(=O)N(C2=S)C=2C=C(C(C#N)=NC=2)C(F)(F)F)=CC=C1F NIVRTVOACSMZEF-UHFFFAOYSA-N 0.000 claims 1
- QZISHJOPEUFEBM-UHFFFAOYSA-N C1CCN(C1)CCOC2=C(C=C(C=C2)N3C(=S)NC(=O)C34CCC4)F Chemical compound C1CCN(C1)CCOC2=C(C=C(C=C2)N3C(=S)NC(=O)C34CCC4)F QZISHJOPEUFEBM-UHFFFAOYSA-N 0.000 claims 1
- WJSJOZROBWTJTJ-UHFFFAOYSA-N CN1CCN(CC1)CCOC2=C(C=CC(=C2)N3C(=S)NC(=O)C34CCC4)F Chemical compound CN1CCN(CC1)CCOC2=C(C=CC(=C2)N3C(=S)NC(=O)C34CCC4)F WJSJOZROBWTJTJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30508210P | 2010-02-16 | 2010-02-16 | |
| US61/305,082 | 2010-02-16 | ||
| US32902310P | 2010-04-28 | 2010-04-28 | |
| US61/329,023 | 2010-04-28 | ||
| US38845710P | 2010-09-30 | 2010-09-30 | |
| US61/388,457 | 2010-09-30 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012554001A Division JP5918147B2 (ja) | 2010-02-16 | 2011-02-16 | アンドロゲン受容体モジュレーターおよびその使用 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017091441A Division JP6391076B2 (ja) | 2010-02-16 | 2017-05-01 | アンドロゲン受容体モジュレーターおよびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016172739A JP2016172739A (ja) | 2016-09-29 |
| JP2016172739A5 true JP2016172739A5 (enExample) | 2017-04-27 |
| JP6141484B2 JP6141484B2 (ja) | 2017-06-07 |
Family
ID=44483553
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012554001A Expired - Fee Related JP5918147B2 (ja) | 2010-02-16 | 2011-02-16 | アンドロゲン受容体モジュレーターおよびその使用 |
| JP2016073172A Expired - Fee Related JP6141484B2 (ja) | 2010-02-16 | 2016-03-31 | アンドロゲン受容体モジュレーターおよびその使用 |
| JP2017091441A Expired - Fee Related JP6391076B2 (ja) | 2010-02-16 | 2017-05-01 | アンドロゲン受容体モジュレーターおよびその使用 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012554001A Expired - Fee Related JP5918147B2 (ja) | 2010-02-16 | 2011-02-16 | アンドロゲン受容体モジュレーターおよびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017091441A Expired - Fee Related JP6391076B2 (ja) | 2010-02-16 | 2017-05-01 | アンドロゲン受容体モジュレーターおよびその使用 |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US9108944B2 (enExample) |
| EP (4) | EP3124481B1 (enExample) |
| JP (3) | JP5918147B2 (enExample) |
| KR (2) | KR101819199B1 (enExample) |
| CN (3) | CN103724322B (enExample) |
| AU (1) | AU2011218173C1 (enExample) |
| BR (1) | BR112012020558B1 (enExample) |
| CA (1) | CA2787083C (enExample) |
| CY (1) | CY1120297T1 (enExample) |
| DK (1) | DK3124481T3 (enExample) |
| EA (3) | EA023981B1 (enExample) |
| ES (1) | ES2668380T3 (enExample) |
| HR (1) | HRP20180848T1 (enExample) |
| HU (1) | HUE037389T2 (enExample) |
| IL (3) | IL220703A (enExample) |
| LT (1) | LT3124481T (enExample) |
| MX (2) | MX355915B (enExample) |
| PH (3) | PH12012501652A1 (enExample) |
| PL (1) | PL3124481T3 (enExample) |
| PT (1) | PT3124481T (enExample) |
| RS (1) | RS57309B1 (enExample) |
| SG (3) | SG183302A1 (enExample) |
| SI (1) | SI3124481T1 (enExample) |
| SM (1) | SMT201800277T1 (enExample) |
| WO (1) | WO2011103202A2 (enExample) |
| ZA (2) | ZA201507865B (enExample) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE037389T2 (hu) | 2010-02-16 | 2018-08-28 | Aragon Pharmaceuticals Inc | Androgén receptor modulátorok és alkalmazásaik |
| WO2012119559A1 (en) | 2011-03-10 | 2012-09-13 | Suzhou Kintor Pharmaceuticals,Inc. | Androgen receptor antagonists and uses thereof |
| WO2013056547A1 (zh) * | 2011-10-22 | 2013-04-25 | Chen Degui | 一组乙内酰脲衍生物的合成及其应用 |
| EA201490897A1 (ru) | 2011-12-16 | 2015-03-31 | Олема Фармасьютикалс, Инк. | Новые бензопирановые соединения, композиции и их применение |
| TWI635080B (zh) | 2012-01-13 | 2018-09-11 | 阿蘭達製藥有限公司 | 具抗雄激素性質新雜芳醯胺衍生物及其用途 |
| UY34646A (es) | 2012-03-02 | 2013-10-31 | Novartis Ag | Compuestos de espirohidantoína y su uso como moduladores selectivos del receptor de andrógenos |
| EP3922629A1 (en) * | 2012-06-07 | 2021-12-15 | Aragon Pharmaceuticals, Inc. | Crystalline forms of an androgen receptor modulator |
| ES2836424T3 (es) | 2012-09-26 | 2021-06-25 | Aragon Pharmaceuticals Inc | Antiandrógenos para tratar el cáncer de próstata no metastásico y resistente a la castración |
| US9175291B2 (en) | 2012-10-11 | 2015-11-03 | Isis Pharmaceuticals Inc. | Modulation of androgen receptor expression |
| WO2014075387A1 (zh) * | 2012-11-14 | 2014-05-22 | 上海医药集团股份有限公司 | 一类二芳基乙内酰脲衍生物、其制备方法、药物组合物和应用 |
| CA3105575A1 (en) | 2013-01-15 | 2014-07-24 | Aragon Pharmaceuticals, Inc. | Androgen receptor modulator and uses thereof |
| CA2908326C (en) | 2013-05-29 | 2017-09-12 | Hinova Pharmaceuticals Inc. | Imidazolidinedione compounds and their uses |
| WO2015018356A1 (zh) * | 2013-08-08 | 2015-02-12 | 上海医药集团股份有限公司 | 二芳基乙内酰脲衍生物、其制备方法、药物组合物和应用 |
| CN103601671B (zh) * | 2013-10-22 | 2016-08-17 | 上海泰坦科技股份有限公司 | 碘代三氟甲基吡啶的制备方法 |
| US9682960B2 (en) | 2013-12-19 | 2017-06-20 | Endorecherche, Inc. | Non-steroidal antiandrogens and selective androgen receptor modulators with a pyridyl moiety |
| CN103694243B (zh) * | 2013-12-20 | 2015-09-09 | 中国农业大学 | 2-取代吡啶基-1,2,4-三唑并[1,2-a]哒嗪化合物 |
| WO2015116696A1 (en) | 2014-01-28 | 2015-08-06 | Massachusetts Institute Of Technology | Combination therapies and methods of use thereof for treating cancer |
| EP3102183A1 (en) * | 2014-02-05 | 2016-12-14 | LEK Pharmaceuticals d.d. | Solid pharmaceutical compositions of androgen receptor antagonists |
| CN104844520B (zh) * | 2014-02-13 | 2017-09-05 | 成都伊诺达博医药科技有限公司 | 一种合成恩杂鲁胺的方法 |
| CN104844521B (zh) * | 2014-02-13 | 2017-08-15 | 成都伊诺达博医药科技有限公司 | 抗前列腺癌药物恩杂鲁胺的合成方法 |
| RU2557235C1 (ru) * | 2014-07-08 | 2015-07-20 | Александр Васильевич Иващенко | Замещенные 2-тиоксо-имидазолидин-4-оны и их спироаналоги, противораковый активный компонент, фармацевтическая композиция, лекарственный препарат, способ лечения рака простаты |
| MX381829B (es) | 2014-12-05 | 2025-03-13 | Aragon Pharmaceuticals Inc | Composiciones anticancerígenas. |
| ES2839128T3 (es) * | 2014-12-05 | 2021-07-05 | Aragon Pharmaceuticals Inc | Composiciones anticancerosas |
| RS66323B1 (sr) | 2014-12-05 | 2025-01-31 | Aragon Pharmaceuticals Inc | Sastavi protiv raka |
| ME03420B (me) * | 2014-12-19 | 2020-01-20 | Aragon Pharmaceuticals Inc | Postupak za pripremu jedinjenja diariltiohidantoina |
| EP3233823B1 (en) * | 2014-12-19 | 2019-01-30 | Aragon Pharmaceuticals, Inc. | Processes for the preparation of a diarylthiohydantoin compound |
| US12312316B2 (en) | 2015-01-20 | 2025-05-27 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
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