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 (OSRAM) | 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 (OSRAM) |
| EP (1) | EP1485085A4 (OSRAM) |
| JP (1) | JP4359150B2 (OSRAM) |
| KR (1) | KR100951499B1 (OSRAM) |
| CN (1) | CN100384820C (OSRAM) |
| BR (1) | BR0308737A (OSRAM) |
| CA (1) | CA2479256A1 (OSRAM) |
| CO (1) | CO5611143A2 (OSRAM) |
| GE (1) | GEP20074230B (OSRAM) |
| HR (1) | HRP20040853A2 (OSRAM) |
| IL (2) | IL164022A0 (OSRAM) |
| IS (1) | IS7456A (OSRAM) |
| MX (1) | MXPA04008999A (OSRAM) |
| NO (1) | NO20044442L (OSRAM) |
| NZ (1) | NZ535365A (OSRAM) |
| PL (1) | PL372413A1 (OSRAM) |
| RS (1) | RS81904A (OSRAM) |
| RU (1) | RU2312857C2 (OSRAM) |
| UA (1) | UA77296C2 (OSRAM) |
| WO (1) | WO2003080047A1 (OSRAM) |
| ZA (1) | ZA200407337B (OSRAM) |
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 |
| RS51752B (sr) | 2002-07-29 | 2011-12-31 | Rigel Pharmaceuticals | Metode tretiranja i prevencije autoimunih oboljenja jedinjenjima 2,4-pirimidindiamina |
| US6916937B2 (en) * | 2003-02-03 | 2005-07-12 | Bristol-Myers Squibb Company | Carbohydrate prodrugs of fluorooxindoles |
| HRP20130602T1 (en) | 2003-07-30 | 2013-07-31 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds for use in the treatment or prevention of autoimmune diseases |
| 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 |
| DE602006010979D1 (de) | 2005-01-19 | 2010-01-21 | Rigel Pharmaceuticals Inc | Prodrugs aus 2,4-pyrimidindiamin-verbindungen und ihre verwendungen |
| 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 |
| SMT201700430T1 (it) | 2009-06-25 | 2018-01-11 | Alkermes Pharma Ireland Ltd | Composti eterociclici per il trattamento di disturbi neurologici e psicologici |
| NZ597108A (en) * | 2009-06-25 | 2014-04-30 | Alkermes Pharma Ireland Ltd | 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 |
| PT3191470T (pt) | 2015-07-06 | 2019-06-05 | Gilead Sciences Inc | Moduladores de cot e métodos para a sua utilização |
| CR20200334A (es) | 2018-01-05 | 2021-03-09 | Cybrexa 1 Inc | Compuestos, composiciones y métodos para tratar enfermedades que involucren tejidos con enfermedades ácidas o hipóxicas |
| EP3762386B1 (en) * | 2018-03-05 | 2024-01-24 | Teon Therapeutics, Inc. | Adenosine receptor antagonists and uses thereof |
| US11273158B2 (en) | 2018-03-05 | 2022-03-15 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| 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 |
| PH12022550039A1 (en) | 2019-07-10 | 2023-06-26 | Cybrexa 3 Inc | Peptide conjugates of cytotoxins as therapeutics |
| MX2022000450A (es) | 2019-07-10 | 2022-04-25 | Cybrexa 3 Inc | Conjugados peptídicos de agentes dirigidos a microtúbulos como terapéuticos. |
| KR20220161438A (ko) | 2020-03-30 | 2022-12-06 | 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 |
| CA2317008C (en) | 1997-12-31 | 2009-01-20 | The University Of Kansas | Water soluble prodrugs of tertiary amine containing drugs and methods of making thereof |
| WO1999038873A1 (en) * | 1998-01-29 | 1999-08-05 | Bristol-Myers Squibb Company | Phosphate derivatives of diaryl 1,3,4-oxadiazolone |
-
2003
- 2003-03-20 MX MXPA04008999A patent/MXPA04008999A/es active IP Right Grant
- 2003-03-20 WO PCT/US2003/008613 patent/WO2003080047A1/en not_active Ceased
- 2003-03-20 CN CNB038109778A patent/CN100384820C/zh not_active Expired - Fee Related
- 2003-03-20 PL PL03372413A patent/PL372413A1/xx not_active Application Discontinuation
- 2003-03-20 KR KR1020047014626A patent/KR100951499B1/ko not_active Expired - Fee Related
- 2003-03-20 CA CA002479256A patent/CA2479256A1/en not_active Abandoned
- 2003-03-20 GE GEAP8458A patent/GEP20074230B/en unknown
- 2003-03-20 HR HRP20040853 patent/HRP20040853A2/xx not_active Application Discontinuation
- 2003-03-20 BR BR0308737-9A patent/BR0308737A/pt not_active IP Right Cessation
- 2003-03-20 JP JP2003577875A patent/JP4359150B2/ja not_active Expired - Fee Related
- 2003-03-20 US US10/393,031 patent/US6930100B2/en not_active Expired - Lifetime
- 2003-03-20 NZ NZ535365A patent/NZ535365A/en not_active IP Right Cessation
- 2003-03-20 UA UA20041109513A patent/UA77296C2/uk unknown
- 2003-03-20 RS YUP-819/04A patent/RS81904A/sr unknown
- 2003-03-20 RU RU2004131201/04A patent/RU2312857C2/ru not_active IP Right Cessation
- 2003-03-20 IL IL16402203A patent/IL164022A0/xx active IP Right Grant
- 2003-03-20 EP EP03711659A patent/EP1485085A4/en not_active Withdrawn
-
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