JP2005526097A5 - - Google Patents
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- Publication number
- JP2005526097A5 JP2005526097A5 JP2003577875A JP2003577875A JP2005526097A5 JP 2005526097 A5 JP2005526097 A5 JP 2005526097A5 JP 2003577875 A JP2003577875 A JP 2003577875A JP 2003577875 A JP2003577875 A JP 2003577875A JP 2005526097 A5 JP2005526097 A5 JP 2005526097A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydro
- oxo
- trifluoromethyl
- fluoro
- chloro
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- -1 5-chloro-2-methoxy-phenyl Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- 125000004185 ester group Chemical group 0.000 claims 4
- 231100000252 nontoxic Toxicity 0.000 claims 4
- 230000003000 nontoxic effect Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- CWIOUIVULUFRSB-INIZCTEOSA-N [(3s)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indol-1-yl]methyl dihydrogen phosphate Chemical compound COC1=CC=C(Cl)C=C1[C@@]1(F)C2=CC=C(C(F)(F)F)C=C2N(COP(O)(O)=O)C1=O CWIOUIVULUFRSB-INIZCTEOSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- HNLLHFDPAMMLNM-SFHVURJKSA-N 2-phosphonooxyethyl (3s)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indole-1-carboxylate Chemical compound COC1=CC=C(Cl)C=C1[C@@]1(F)C2=CC=C(C(F)(F)F)C=C2N(C(=O)OCCOP(O)(O)=O)C1=O HNLLHFDPAMMLNM-SFHVURJKSA-N 0.000 claims 1
- FBOONKKJAFGFGT-JLNKLDRZSA-N 2-phosphonooxypropyl (3s)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indole-1-carboxylate Chemical compound COC1=CC=C(Cl)C=C1[C@@]1(F)C2=CC=C(C(F)(F)F)C=C2N(C(=O)OCC(C)OP(O)(O)=O)C1=O FBOONKKJAFGFGT-JLNKLDRZSA-N 0.000 claims 1
- 208000001408 Carbon monoxide poisoning Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 102000016469 Large-Conductance Calcium-Activated Potassium Channels Human genes 0.000 claims 1
- 108010092555 Large-Conductance Calcium-Activated Potassium Channels Proteins 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 206010036790 Productive cough Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- CWIOUIVULUFRSB-MRXNPFEDSA-N [(3r)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indol-1-yl]methyl dihydrogen phosphate Chemical compound COC1=CC=C(Cl)C=C1[C@]1(F)C2=CC=C(C(F)(F)F)C=C2N(COP(O)(O)=O)C1=O CWIOUIVULUFRSB-MRXNPFEDSA-N 0.000 claims 1
- VOWFZWMTQQCJHH-SFHVURJKSA-N [(3s)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indol-1-yl]methyl 2-phosphonooxyacetate Chemical compound COC1=CC=C(Cl)C=C1[C@@]1(F)C2=CC=C(C(F)(F)F)C=C2N(COC(=O)COP(O)(O)=O)C1=O VOWFZWMTQQCJHH-SFHVURJKSA-N 0.000 claims 1
- UTIHTXLQUMTDIC-IBGZPJMESA-N [(3s)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indol-1-yl]methyl 3-phosphonooxypropanoate Chemical compound COC1=CC=C(Cl)C=C1[C@@]1(F)C2=CC=C(C(F)(F)F)C=C2N(COC(=O)CCOP(O)(O)=O)C1=O UTIHTXLQUMTDIC-IBGZPJMESA-N 0.000 claims 1
- RWCHRIFSGHWHPF-IBGZPJMESA-N [(3s)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indol-1-yl]methyl n-(2-phosphonooxyethyl)carbamate Chemical compound COC1=CC=C(Cl)C=C1[C@@]1(F)C2=CC=C(C(F)(F)F)C=C2N(COC(=O)NCCOP(O)(O)=O)C1=O RWCHRIFSGHWHPF-IBGZPJMESA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000036461 convulsion Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000007917 intracranial administration Methods 0.000 claims 1
- 201000009941 intracranial hypertension Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- WWWUKRCWVLBVPH-KRWDZBQOSA-N phosphonooxymethyl (3s)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-2-oxo-6-(trifluoromethyl)indole-1-carboxylate Chemical compound COC1=CC=C(Cl)C=C1[C@@]1(F)C2=CC=C(C(F)(F)F)C=C2N(C(=O)OCOP(O)(O)=O)C1=O WWWUKRCWVLBVPH-KRWDZBQOSA-N 0.000 claims 1
- 239000004036 potassium channel stimulating agent Substances 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 210000003802 sputum Anatomy 0.000 claims 1
- 208000024794 sputum Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36601002P | 2002-03-20 | 2002-03-20 | |
| PCT/US2003/008613 WO2003080047A1 (en) | 2002-03-20 | 2003-03-20 | Phosphate prodrugs of fluorooxindoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005526097A JP2005526097A (ja) | 2005-09-02 |
| JP2005526097A5 true JP2005526097A5 (enExample) | 2006-04-27 |
| JP4359150B2 JP4359150B2 (ja) | 2009-11-04 |
Family
ID=28454740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003577875A Expired - Fee Related JP4359150B2 (ja) | 2002-03-20 | 2003-03-20 | フルオロオキシインドールのホスフェートプロドラッグ |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6930100B2 (enExample) |
| EP (1) | EP1485085A4 (enExample) |
| JP (1) | JP4359150B2 (enExample) |
| KR (1) | KR100951499B1 (enExample) |
| CN (1) | CN100384820C (enExample) |
| BR (1) | BR0308737A (enExample) |
| CA (1) | CA2479256A1 (enExample) |
| CO (1) | CO5611143A2 (enExample) |
| GE (1) | GEP20074230B (enExample) |
| HR (1) | HRP20040853A2 (enExample) |
| IL (2) | IL164022A0 (enExample) |
| IS (1) | IS7456A (enExample) |
| MX (1) | MXPA04008999A (enExample) |
| NO (1) | NO20044442L (enExample) |
| NZ (1) | NZ535365A (enExample) |
| PL (1) | PL372413A1 (enExample) |
| RS (1) | RS81904A (enExample) |
| RU (1) | RU2312857C2 (enExample) |
| UA (1) | UA77296C2 (enExample) |
| WO (1) | WO2003080047A1 (enExample) |
| ZA (1) | ZA200407337B (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| HRP20050089B1 (hr) | 2002-07-29 | 2015-06-19 | Rigel Pharmaceuticals | Upotreba 2,4 pirimidindiaminskog spoja za proizvodnju lijeka za lijeäśenje ili sprjeäśavanje autoimunosne bolesti |
| US6916937B2 (en) * | 2003-02-03 | 2005-07-12 | Bristol-Myers Squibb Company | Carbohydrate prodrugs of fluorooxindoles |
| JP4886511B2 (ja) | 2003-07-30 | 2012-02-29 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
| US7169803B2 (en) * | 2004-03-15 | 2007-01-30 | Bristol-Myers Squibb Company | N-substituted prodrugs of fluorooxindoles |
| US7253167B2 (en) | 2004-06-30 | 2007-08-07 | Bristol-Myers Squibb Company | Tricyclic-heteroaryl compounds useful as kinase inhibitors |
| CN101115761B (zh) | 2005-01-19 | 2012-07-18 | 里格尔药品股份有限公司 | 2,4-嘧啶二胺化合物的前药及其应用 |
| US8227455B2 (en) | 2005-04-18 | 2012-07-24 | Rigel Pharmaceuticals, Inc. | Methods of treating cell proliferative disorders |
| US20090114877A1 (en) * | 2005-09-13 | 2009-05-07 | Eisai R&D Management Co., Ltd. | Composition Containing Stability-Improved Chloromethyl Phosphate Derivatve and Process for Producing Same |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| TW200841879A (en) * | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| US8513287B2 (en) * | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| WO2009100090A1 (en) * | 2008-02-05 | 2009-08-13 | Merck & Co., Inc. | Prodrugs of cgrp receptor antagonist |
| US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| AU2010266018B2 (en) * | 2009-06-25 | 2014-01-09 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| US8686009B2 (en) * | 2009-06-25 | 2014-04-01 | Alkermes Pharma Ireland Limited | Prodrugs of NH-acidic compounds |
| CA2802733C (en) * | 2010-06-24 | 2017-11-21 | Alkermes Pharma Ireland Limited | Prodrugs of nh-acidic compounds: ester, carbonate, carbamate and phosphonate derivatives |
| RS58639B1 (sr) | 2015-07-06 | 2019-05-31 | Gilead Sciences Inc | Cot modulatori i postupci za njihovu upotrebu |
| KR20200121800A (ko) | 2018-01-05 | 2020-10-26 | 싸이브렉사 1, 인크. | 산성 또는 저산소성 질환에 걸린 조직에 관련된 질환의 치료를 위한 화합물, 조성물 및 방법 |
| WO2019173230A1 (en) | 2018-03-05 | 2019-09-12 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| IL277144B2 (en) * | 2018-03-05 | 2024-06-01 | Teon Therapeutics Inc | Adenosine receptor antagonists and uses thereof |
| TWI770527B (zh) | 2019-06-14 | 2022-07-11 | 美商基利科學股份有限公司 | Cot 調節劑及其使用方法 |
| MY209459A (en) | 2019-07-10 | 2025-07-09 | Cybrexa 3 Inc | Peptide conjugates of microtubule-targeting agents as therapeutics |
| CA3146560A1 (en) | 2019-07-10 | 2021-01-14 | Cybrexa 2, Inc. | Peptide conjugates of cytotoxins as therapeutics |
| KR102924836B1 (ko) | 2020-03-30 | 2026-02-09 | 길리애드 사이언시즈, 인코포레이티드 | Cot 억제제 화합물, (S)-6-(((1-(바이사이클로[1.1.1]펜탄-1-일)-1H-1,2,3-트라이아졸-4-일)2-메틸-1-옥소-1,2-다이하이드로아이소퀴놀린-5-일)메틸)))아미노8-클로로-(네오펜틸아미노)퀴놀린-3-카르보니트릴의 고체 형태 |
| WO2021202688A1 (en) | 2020-04-02 | 2021-10-07 | Gilead Sciences, Inc. | Process for preparing a cot inhibitor compound |
| EP3912625A1 (en) | 2020-05-20 | 2021-11-24 | Kaerus Bioscience Limited | Novel maxi-k potassium channel openers for the treatment of fragile x associated disorders |
| WO2025233532A1 (en) | 2024-05-10 | 2025-11-13 | Les Laboratoires Servier | Maxi-k potassium channel openers and therapeutic applications thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU749063A1 (ru) * | 1979-01-29 | 1996-09-10 | Военно-медицинская академия им.С.М.Кирова | 3-(4-карбэтокси)-фенилимино-2-оксоиндолин, повышающий устойчивость организма к повторной черепно-мозговой травме |
| US5234947A (en) | 1991-11-07 | 1993-08-10 | New York University | Potassium channel activating compounds and methods of use thereof |
| US5187173A (en) * | 1991-12-27 | 1993-02-16 | Sterling Winthrop Inc. | 2-saccharinylmethyl and 4,5,6,7-tetrahydro-2-saccharinylmethyl phosphates, phosphonates and phosphinates useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
| US5565483A (en) * | 1995-06-07 | 1996-10-15 | Bristol-Myers Squibb Company | 3-substituted oxindole derivatives as potassium channel modulators |
| JP2001527083A (ja) | 1997-12-31 | 2001-12-25 | ザ・ユニバーシティ・オブ・カンザス | 第二級および第三級アミン含有薬剤の水溶性プロドラッグおよびその製造方法 |
| DK1056754T3 (da) * | 1998-01-29 | 2004-02-16 | Bristol Myers Squibb Co | Phosphatderivater af diaryl-1,3,4-oxadiazolon |
-
2003
- 2003-03-20 CA CA002479256A patent/CA2479256A1/en not_active Abandoned
- 2003-03-20 MX MXPA04008999A patent/MXPA04008999A/es active IP Right Grant
- 2003-03-20 NZ NZ535365A patent/NZ535365A/en not_active IP Right Cessation
- 2003-03-20 RU RU2004131201/04A patent/RU2312857C2/ru not_active IP Right Cessation
- 2003-03-20 GE GEAP8458A patent/GEP20074230B/en unknown
- 2003-03-20 JP JP2003577875A patent/JP4359150B2/ja not_active Expired - Fee Related
- 2003-03-20 KR KR1020047014626A patent/KR100951499B1/ko not_active Expired - Fee Related
- 2003-03-20 BR BR0308737-9A patent/BR0308737A/pt not_active IP Right Cessation
- 2003-03-20 CN CNB038109778A patent/CN100384820C/zh not_active Expired - Fee Related
- 2003-03-20 WO PCT/US2003/008613 patent/WO2003080047A1/en not_active Ceased
- 2003-03-20 UA UA20041109513A patent/UA77296C2/uk unknown
- 2003-03-20 RS YUP-819/04A patent/RS81904A/sr unknown
- 2003-03-20 EP EP03711659A patent/EP1485085A4/en not_active Withdrawn
- 2003-03-20 HR HRP20040853 patent/HRP20040853A2/xx not_active Application Discontinuation
- 2003-03-20 PL PL03372413A patent/PL372413A1/xx not_active Application Discontinuation
- 2003-03-20 IL IL16402203A patent/IL164022A0/xx active IP Right Grant
- 2003-03-20 US US10/393,031 patent/US6930100B2/en not_active Expired - Lifetime
-
2004
- 2004-09-12 IL IL164022A patent/IL164022A/en not_active IP Right Cessation
- 2004-09-13 ZA ZA200407337A patent/ZA200407337B/en unknown
- 2004-09-17 IS IS7456A patent/IS7456A/is unknown
- 2004-09-20 CO CO04093294A patent/CO5611143A2/es not_active Application Discontinuation
- 2004-10-19 NO NO20044442A patent/NO20044442L/no not_active Application Discontinuation