JP2012524708A5 - - Google Patents
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- Publication number
- JP2012524708A5 JP2012524708A5 JP2011526487A JP2011526487A JP2012524708A5 JP 2012524708 A5 JP2012524708 A5 JP 2012524708A5 JP 2011526487 A JP2011526487 A JP 2011526487A JP 2011526487 A JP2011526487 A JP 2011526487A JP 2012524708 A5 JP2012524708 A5 JP 2012524708A5
- Authority
- JP
- Japan
- Prior art keywords
- dioxo
- methyl
- hydroxymethyl
- trifluoromethylbenzonitrile
- pharmaceutically acceptable
- 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 22
- 150000003839 salts Chemical class 0.000 claims 17
- 125000001475 halogen functional group Chemical group 0.000 claims 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 150000001408 amides Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- -1 nitro, hydroxyl Chemical group 0.000 claims 3
- 239000000556 agonist Substances 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- DYJMIXAXRWXZKP-QGZVFWFLSA-N (5s)-3-(3,4-dichlorophenyl)-5-(hydroxymethyl)-1-methyl-5-phenylimidazolidine-2,4-dione Chemical compound C1([C@]2(CO)C(=O)N(C(=O)N2C)C=2C=C(Cl)C(Cl)=CC=2)=CC=CC=C1 DYJMIXAXRWXZKP-QGZVFWFLSA-N 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- DYJMIXAXRWXZKP-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5-(hydroxymethyl)-1-methyl-5-phenylimidazolidine-2,4-dione Chemical compound CN1C(=O)N(C=2C=C(Cl)C(Cl)=CC=2)C(=O)C1(CO)C1=CC=CC=C1 DYJMIXAXRWXZKP-UHFFFAOYSA-N 0.000 claims 1
- VAJGULUVTFDTAS-SFHVURJKSA-N 4-[(4r)-4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1([C@@]2(CO)C(=O)N(C(=O)N2C)C=2C=C(C(C#N)=CC=2)C(F)(F)F)=CC=CC=C1 VAJGULUVTFDTAS-SFHVURJKSA-N 0.000 claims 1
- VAJGULUVTFDTAS-GOSISDBHSA-N 4-[(4s)-4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1([C@]2(CO)C(=O)N(C(=O)N2C)C=2C=C(C(C#N)=CC=2)C(F)(F)F)=CC=CC=C1 VAJGULUVTFDTAS-GOSISDBHSA-N 0.000 claims 1
- ZTRDVSMRQISNQC-UHFFFAOYSA-N 4-[1-[4-cyano-3-(trifluoromethyl)phenyl]-3-methyl-2,5-dioxo-4-phenylimidazolidin-4-yl]-2-methoxy-4-oxobutanoic acid Chemical compound C(#N)C1=C(C=C(C=C1)N1C(N(C(C1=O)(C1=CC=CC=C1)C(CC(C(=O)O)OC)=O)C)=O)C(F)(F)F ZTRDVSMRQISNQC-UHFFFAOYSA-N 0.000 claims 1
- PTJJQSYSALILPG-UHFFFAOYSA-N 4-[3-(cyanomethyl)-4-(hydroxymethyl)-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound O=C1C(CO)(C=2C=CC=CC=2)N(CC#N)C(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 PTJJQSYSALILPG-UHFFFAOYSA-N 0.000 claims 1
- HRMVEKRBHVOXMN-UHFFFAOYSA-N 4-[3-ethyl-4-(hydroxymethyl)-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CCN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=CC=C1 HRMVEKRBHVOXMN-UHFFFAOYSA-N 0.000 claims 1
- YNTJLGNYYPSIGY-UHFFFAOYSA-N 4-[4-(1-hydroxyethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound O=C1C(C(O)C)(C=2C=CC=CC=2)N(C)C(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 YNTJLGNYYPSIGY-UHFFFAOYSA-N 0.000 claims 1
- RRNASESHVQVXMZ-UHFFFAOYSA-N 4-[4-(1-hydroxypropyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound O=C1C(C(O)CC)(C=2C=CC=CC=2)N(C)C(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 RRNASESHVQVXMZ-UHFFFAOYSA-N 0.000 claims 1
- BXIDOXHJFZHDFC-UHFFFAOYSA-N 4-[4-(3-cyanophenyl)-4-(hydroxymethyl)-3-methyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=CC(C#N)=C1 BXIDOXHJFZHDFC-UHFFFAOYSA-N 0.000 claims 1
- JTPNDBFMZCAXJM-UHFFFAOYSA-N 4-[4-(4-cyanophenyl)-4-(hydroxymethyl)-3-methyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=C(C#N)C=C1 JTPNDBFMZCAXJM-UHFFFAOYSA-N 0.000 claims 1
- WKRBBSSMYAQKNG-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-4-(hydroxymethyl)-2,5-dioxo-3-prop-2-ynylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound O=C1C(CO)(C=2C=CC(F)=CC=2)N(CC#C)C(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 WKRBBSSMYAQKNG-UHFFFAOYSA-N 0.000 claims 1
- PUJHVJGPYXFNSZ-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-4-(hydroxymethyl)-3-methyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=C(F)C=C1 PUJHVJGPYXFNSZ-UHFFFAOYSA-N 0.000 claims 1
- YZZZYXRBSVQHJP-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-2,5-dioxo-4-phenyl-3-prop-1-ynylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC#CN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=CC=C1 YZZZYXRBSVQHJP-UHFFFAOYSA-N 0.000 claims 1
- KLOBYTIYOMGQRT-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-2,5-dioxo-4-phenyl-3-propan-2-ylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC(C)N1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=CC=C1 KLOBYTIYOMGQRT-UHFFFAOYSA-N 0.000 claims 1
- GMPDDOUUFBOTOI-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound O=C1C(CO)(C=2C=CC=CC=2)NC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 GMPDDOUUFBOTOI-UHFFFAOYSA-N 0.000 claims 1
- OLOVCEAMPCAMQA-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-[3-(trifluoromethyl)phenyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=CC(C(F)(F)F)=C1 OLOVCEAMPCAMQA-UHFFFAOYSA-N 0.000 claims 1
- VAJGULUVTFDTAS-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=CC=C1 VAJGULUVTFDTAS-UHFFFAOYSA-N 0.000 claims 1
- VPWAPLDLNVXBCR-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-methoxybenzonitrile Chemical compound C1=C(C#N)C(OC)=CC(N2C(C(CO)(N(C)C2=O)C=2C=CC=CC=2)=O)=C1 VPWAPLDLNVXBCR-UHFFFAOYSA-N 0.000 claims 1
- PONWCDNXABYQOR-UHFFFAOYSA-N 4-[4-(hydroxymethyl)-3-methyl-4-(3-methylphenyl)-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CN1C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C1(CO)C1=CC=CC(C)=C1 PONWCDNXABYQOR-UHFFFAOYSA-N 0.000 claims 1
- NSQGHQGNZIHEOZ-JOCHJYFZSA-N 4-[[(4s)-1-[4-cyano-3-(trifluoromethyl)phenyl]-3-methyl-2,5-dioxo-4-phenylimidazolidin-4-yl]methoxy]-4-oxobutanoic acid Chemical compound C1([C@]2(COC(=O)CCC(O)=O)C(=O)N(C(=O)N2C)C=2C=C(C(C#N)=CC=2)C(F)(F)F)=CC=CC=C1 NSQGHQGNZIHEOZ-JOCHJYFZSA-N 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- SGGIBFOETRIEQE-VYLXPPGNSA-N [(2s)-1-[[1-[4-cyano-3-(trifluoromethyl)phenyl]-3-methyl-2,5-dioxo-4-phenylimidazolidin-4-yl]methoxy]-3-methyl-1-oxobutan-2-yl]azanium;chloride Chemical compound [Cl-].O=C1C(COC(=O)[C@@H]([NH3+])C(C)C)(C=2C=CC=CC=2)N(C)C(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 SGGIBFOETRIEQE-VYLXPPGNSA-N 0.000 claims 1
- QDLDKEQDFNJDSH-UHFFFAOYSA-N [1-[4-cyano-3-(trifluoromethyl)phenyl]-3-methyl-2,5-dioxo-4-phenylimidazolidin-4-yl] methyl hydrogen phosphate Chemical compound CN1C(=O)N(C(=O)C1(C2=CC=CC=C2)OP(=O)(O)OC)C3=CC(=C(C=C3)C#N)C(F)(F)F QDLDKEQDFNJDSH-UHFFFAOYSA-N 0.000 claims 1
- 239000003098 androgen Substances 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 208000001076 sarcopenia Diseases 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19191808P | 2008-09-11 | 2008-09-11 | |
| US61/191,918 | 2008-09-11 | ||
| GB0900333.6A GB2463514C (en) | 2008-09-11 | 2009-01-09 | Imidazolidine compounds and uses therefor |
| GB0900333.6 | 2009-01-09 | ||
| PCT/EP2009/061733 WO2010029119A1 (en) | 2008-09-11 | 2009-09-10 | Novel imidazolidine compounds as androgen receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012524708A JP2012524708A (ja) | 2012-10-18 |
| JP2012524708A5 true JP2012524708A5 (enExample) | 2012-11-29 |
| JP5595402B2 JP5595402B2 (ja) | 2014-09-24 |
Family
ID=40379370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011526487A Expired - Fee Related JP5595402B2 (ja) | 2008-09-11 | 2009-09-10 | アンドロゲン受容体モジュレーターとしての新規イミダゾリジン化合物 |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7968581B2 (enExample) |
| EP (1) | EP2344460B1 (enExample) |
| JP (1) | JP5595402B2 (enExample) |
| KR (1) | KR101705157B1 (enExample) |
| CN (1) | CN102149687B (enExample) |
| AR (1) | AR073282A1 (enExample) |
| AU (1) | AU2009290849B2 (enExample) |
| BR (1) | BRPI0919290A2 (enExample) |
| CA (1) | CA2736364C (enExample) |
| CO (1) | CO6382130A2 (enExample) |
| ES (1) | ES2552684T3 (enExample) |
| GB (1) | GB2463514C (enExample) |
| IL (1) | IL211277A (enExample) |
| MX (1) | MX2011002374A (enExample) |
| NZ (1) | NZ591374A (enExample) |
| RU (1) | RU2488584C2 (enExample) |
| TW (1) | TWI449698B (enExample) |
| WO (1) | WO2010029119A1 (enExample) |
| ZA (1) | ZA201101707B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8168667B2 (en) * | 2006-05-31 | 2012-05-01 | Galapagos Nv | Imidazolidine derivatives, uses therefor, preparation thereof and compositions comprising such |
| AU2012225038B2 (en) | 2011-03-10 | 2016-03-10 | Suzhou Kintor Pharmaceuticals, Inc. | Androgen receptor antagonists and uses thereof |
| GB201311107D0 (en) * | 2013-06-21 | 2013-08-07 | Univ Edinburgh | Bioorthogonal methods and compounds |
| ES2934319T3 (es) * | 2013-07-18 | 2023-02-21 | Baylor College Medicine | Métodos y composiciones para el tratamiento de la atrofia muscular, la debilidad muscular y/o la caquexia |
| MX2016005287A (es) * | 2013-10-25 | 2017-02-22 | D Bush Ernest | Metodos para el tratamiento de distrofias musculares. |
| CN106573921B (zh) * | 2013-12-31 | 2019-05-07 | 博福-益普生（天津）制药有限公司 | 咪唑烷-2,4-二酮衍生物 |
| US11662606B2 (en) * | 2017-12-06 | 2023-05-30 | Eyebright Medical Technology (Beijing) Co., Ltd. | Orthokeratology lens and method for making orthokeratology lenses |
| US11026905B2 (en) | 2018-04-19 | 2021-06-08 | Tvardi Therapeutics, Inc. | STAT3 inhibitors |
| BR112020021329A2 (pt) | 2018-04-19 | 2021-04-27 | Tvardi Therapeutics, Inc. | inibidores de stat3 |
| MX2022008914A (es) | 2020-01-24 | 2022-08-16 | Tvardi Therapeutics Inc | Compuestos terapeuticos, formulaciones y usos de los mismos. |
| CN113024513A (zh) * | 2021-03-22 | 2021-06-25 | 中国药科大学 | 新型雄激素受体降解剂、制备方法和医药用途 |
| CN113801064A (zh) * | 2021-09-26 | 2021-12-17 | 甘肃省化工研究院有限责任公司 | 一种[3+2]环加成反应构建苯基乙内酰脲的方法 |
| AU2023292912A1 (en) | 2022-06-15 | 2025-01-16 | Tvardi Therapeutics, Inc. | Prodrugs of stat3 inhibitors |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5136332B1 (enExample) * | 1970-12-09 | 1976-10-07 | ||
| GB1601310A (en) * | 1978-05-23 | 1981-10-28 | Lilly Industries Ltd | Aryl hydantoins |
| DE2855770A1 (de) | 1978-12-22 | 1980-07-10 | Bayer Ag | Hydantoine |
| US4753957A (en) * | 1981-09-28 | 1988-06-28 | Rohm And Haas Company | Substituted 2,4-imidazolidinediones and fungicidal compositions |
| EP0091596B1 (de) | 1982-04-08 | 1991-09-11 | Shell Internationale Researchmaatschappij B.V. | Neue Hydantoine, ihre Herstellung und Verwendung |
| FR2619381B1 (fr) * | 1987-08-13 | 1989-12-08 | Roussel Uclaf | Nouvelles imidazolidines substituees par un radical hydroxymethyle et un radical phenyl substitue, leur procede de preparation, leur application comme medicaments, les compositions pharmaceutiques les renfermant et un intermediaire pour leur preparation |
| JP2566792B2 (ja) | 1987-09-30 | 1996-12-25 | 株式会社資生堂 | 発毛、養毛促進剤 |
| JPH0219363A (ja) | 1988-07-06 | 1990-01-23 | Fujisawa Pharmaceut Co Ltd | イミダゾリジン誘導体 |
| US4992443A (en) * | 1990-03-12 | 1991-02-12 | William Chelen | Method of treating motion sickness |
| US5346913A (en) | 1992-05-26 | 1994-09-13 | Rohm And Haas Company | N-iodopropargyl hydantoin compounds, compositions, preparation, and use as antimicrobial agents |
| JP3137430B2 (ja) | 1992-06-10 | 2001-02-19 | 鐘淵化学工業株式会社 | ５，５−二置換ヒダントインの製造法 |
| US6846525B2 (en) * | 1993-03-19 | 2005-01-25 | Xerox Corporation | Recording sheets containing purine, pyrimidine, benzimidazole, imidazolidine, urazole, pyrazole, triazole, benzotriazole, tetrazole, and pyrazine compounds |
| TW521073B (en) * | 1994-01-05 | 2003-02-21 | Hoechst Marion Roussel Inc | New optionally substituted phenylimidazolidines, their preparation process, their use as anti-androgenic agent and the pharmaceutical compositions containing them |
| FR2715402B1 (fr) * | 1994-01-05 | 1996-10-04 | Roussel Uclaf | Nouvelles phénylimidazolines éventuellement substituées, leur procédé et des intermédiaires de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant. |
| AU1884595A (en) | 1994-04-29 | 1995-11-29 | Pfizer Inc. | Novel acyclic and cyclic amides as neurotransmitter release enhancers |
| EP0760239A3 (en) | 1995-09-01 | 1999-04-14 | Pfizer Inc. | Therapeutic agents for use in cancer therapy |
| FR2741342B1 (fr) * | 1995-11-22 | 1998-02-06 | Roussel Uclaf | Nouvelles phenylimidazolidines fluorees ou hydroxylees, procede, intermediaires de preparation, application comme medicaments, nouvelle utilisation et compositions pharmaceutiques |
| WO1998039303A1 (en) * | 1997-03-03 | 1998-09-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Small molecules useful in the treatment of inflammatory disease |
| US6355664B1 (en) * | 1997-03-03 | 2002-03-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Phenylpyrrolidines, phenylimidazolidines, 3-phenyl-1,3-oxizolidines and 3-phenyl-1,3-thiazolidines and their use in the treatment of inflammatory disease |
| UA57081C2 (uk) | 1997-06-16 | 2003-06-16 | Пфайзер Продактс Інк. | Фармацевтична композиція для лікування раку або доброякісних проліферативних хвороб у ссавців, спосіб лікування, фармацевтична композиція для інгібування ненормального росту клітин у ссавців та спосіб інгібування |
| US6492553B1 (en) | 1998-01-29 | 2002-12-10 | Aventis Pharamaceuticals Inc. | Methods for preparing N-[(aliphatic or aromatic)carbonyl)]-2-aminoaetamide compounds and for cyclizing such compounds |
| DE19912383A1 (de) | 1998-03-27 | 1999-09-30 | Degussa | Verfahren zur Herstellung von cyclischen 4-Oxoamidinen |
| MXPA02011079A (es) | 2000-05-11 | 2004-08-19 | Consejo Superior Investigacion | Inhibidores heterociclicos de quinasa de sintasa de glucogeno gsk3. |
| US6846643B2 (en) | 2000-08-14 | 2005-01-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Methods and molecules useful for identifying molecules that bind LFA-1 and for determining receptor occupancy |
| EP1791821B1 (en) * | 2004-09-10 | 2013-06-05 | Janssen Pharmaceutica NV | Novel imidazolidin-2-one derivatives as selective androgen receptor modulators (sarms) |
| JP2009513576A (ja) | 2005-10-11 | 2009-04-02 | インターミューン・インコーポレーテッド | ウィルス複製のインヒビター |
| GB0610765D0 (en) * | 2006-05-31 | 2006-07-12 | Proskelia Sas | Imidazolidine derivatives, uses therefor, preparation thereof and compositions comprising such |
-
2009
- 2009-01-09 GB GB0900333.6A patent/GB2463514C/en not_active Expired - Fee Related
- 2009-09-09 AR ARP090103461A patent/AR073282A1/es unknown
- 2009-09-10 CN CN200980135475.9A patent/CN102149687B/zh not_active Expired - Fee Related
- 2009-09-10 EP EP09782854.5A patent/EP2344460B1/en active Active
- 2009-09-10 US US12/557,368 patent/US7968581B2/en active Active
- 2009-09-10 KR KR1020117007686A patent/KR101705157B1/ko not_active Expired - Fee Related
- 2009-09-10 RU RU2011113749/04A patent/RU2488584C2/ru not_active IP Right Cessation
- 2009-09-10 MX MX2011002374A patent/MX2011002374A/es active IP Right Grant
- 2009-09-10 NZ NZ591374A patent/NZ591374A/en not_active IP Right Cessation
- 2009-09-10 ES ES09782854.5T patent/ES2552684T3/es active Active
- 2009-09-10 JP JP2011526487A patent/JP5595402B2/ja not_active Expired - Fee Related
- 2009-09-10 AU AU2009290849A patent/AU2009290849B2/en not_active Ceased
- 2009-09-10 BR BRPI0919290-5A patent/BRPI0919290A2/pt not_active Application Discontinuation
- 2009-09-10 WO PCT/EP2009/061733 patent/WO2010029119A1/en not_active Ceased
- 2009-09-10 CA CA2736364A patent/CA2736364C/en not_active Expired - Fee Related
- 2009-09-11 TW TW098130825A patent/TWI449698B/zh not_active IP Right Cessation
-
2011
- 2011-02-17 IL IL211277A patent/IL211277A/en not_active IP Right Cessation
- 2011-03-04 ZA ZA2011/01707A patent/ZA201101707B/en unknown
- 2011-04-08 CO CO11043783A patent/CO6382130A2/es not_active Application Discontinuation
- 2011-06-23 US US13/167,682 patent/US8383608B2/en not_active Expired - Fee Related
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