JP2008531545A5 - - Google Patents
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- Publication number
- JP2008531545A5 JP2008531545A5 JP2007556688A JP2007556688A JP2008531545A5 JP 2008531545 A5 JP2008531545 A5 JP 2008531545A5 JP 2007556688 A JP2007556688 A JP 2007556688A JP 2007556688 A JP2007556688 A JP 2007556688A JP 2008531545 A5 JP2008531545 A5 JP 2008531545A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropanecarboxylic acid
- ethyl ester
- ethoxy
- ester
- composition
- 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
- -1 heterocycle alkyl Chemical group 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 5
- 239000008103 glucose Substances 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 4
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- RZVSTEQRCQKJIC-UHFFFAOYSA-N cyclopropanecarbothioic s-acid Chemical compound SC(=O)C1CC1 RZVSTEQRCQKJIC-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- AYEGPMGNMOIHDL-QWWZWVQMSA-N (1r,2r)-2-methylcyclopropane-1-carboxylic acid Chemical compound C[C@@H]1C[C@H]1C(O)=O AYEGPMGNMOIHDL-QWWZWVQMSA-N 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- KSJBHWGZQXGMNL-UHFFFAOYSA-N 1,2,2,3-tetramethylcyclopropane-1-carboxylic acid Chemical compound CC1C(C)(C)C1(C)C(O)=O KSJBHWGZQXGMNL-UHFFFAOYSA-N 0.000 claims 1
- WCPFQQHADRJANG-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclopropane-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C(O)=O)CC1 WCPFQQHADRJANG-UHFFFAOYSA-N 0.000 claims 1
- DIZKLZKLNKQFGB-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1 DIZKLZKLNKQFGB-UHFFFAOYSA-N 0.000 claims 1
- IWWCCNVRNHTGLV-UHFFFAOYSA-N 1-phenylcyclopropane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CC1 IWWCCNVRNHTGLV-UHFFFAOYSA-N 0.000 claims 1
- BIUUWIKPBYWKEQ-UHFFFAOYSA-N 2,2-dichloro-1-methylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1(Cl)Cl BIUUWIKPBYWKEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- CIIAULPBUWPDFS-UHFFFAOYSA-N 2-morpholin-4-ylethyl cyclopropanecarboxylate Chemical compound C1CC1C(=O)OCCN1CCOCC1 CIIAULPBUWPDFS-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 1
- 210000004102 animal cell Anatomy 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 210000004413 cardiac myocyte Anatomy 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 208000006443 lactic acidosis Diseases 0.000 claims 1
- AZHHPQTUXCDCDB-UHFFFAOYSA-N methyl 2-(cyclopropanecarbonylsulfanyl)acetate Chemical compound COC(=O)CSC(=O)C1CC1 AZHHPQTUXCDCDB-UHFFFAOYSA-N 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000004962 physiological condition Effects 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/064,713 US7524885B2 (en) | 2002-04-01 | 2005-02-23 | Compounds that stimulate glucose utilization and methods of use |
| US11/064,713 | 2005-02-23 | ||
| PCT/IB2006/001587 WO2006117686A2 (en) | 2005-02-23 | 2006-02-23 | Compounds that stimulate glucose utilization and methods of use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010047058A Division JP2010180218A (ja) | 2005-02-23 | 2010-03-03 | グルコース利用を刺激する化合物および使用方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008531545A JP2008531545A (ja) | 2008-08-14 |
| JP2008531545A5 true JP2008531545A5 (OSRAM) | 2009-04-09 |
| JP4764888B2 JP4764888B2 (ja) | 2011-09-07 |
Family
ID=37308363
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007556688A Expired - Fee Related JP4764888B2 (ja) | 2005-02-23 | 2006-02-23 | グルコース利用を刺激する化合物および使用方法 |
| JP2010047058A Withdrawn JP2010180218A (ja) | 2005-02-23 | 2010-03-03 | グルコース利用を刺激する化合物および使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010047058A Withdrawn JP2010180218A (ja) | 2005-02-23 | 2010-03-03 | グルコース利用を刺激する化合物および使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7524885B2 (OSRAM) |
| EP (1) | EP1868982B1 (OSRAM) |
| JP (2) | JP4764888B2 (OSRAM) |
| KR (1) | KR20070107133A (OSRAM) |
| CN (1) | CN101142167A (OSRAM) |
| AU (1) | AU2006242936A1 (OSRAM) |
| CA (1) | CA2598595C (OSRAM) |
| WO (1) | WO2006117686A2 (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7268179B2 (en) * | 1997-02-03 | 2007-09-11 | Cytonix Corporation | Hydrophobic coating compositions, articles coated with said compositions, and processes for manufacturing same |
| US7524885B2 (en) * | 2002-04-01 | 2009-04-28 | The Governors Of The University Of Alberta | Compounds that stimulate glucose utilization and methods of use |
| IL283725B2 (en) | 2017-06-20 | 2024-04-01 | Imbria Pharmaceuticals Inc | Compositions and methods for increasing efficiency of cardiac metabolism |
| WO2020081361A1 (en) | 2018-10-17 | 2020-04-23 | Imbria Pharmaceuticals, Inc. | Methods of treating rheumatic diseases using trimetazidine-based compounds |
| US11780811B2 (en) | 2020-06-30 | 2023-10-10 | Imbria Pharmaceuticals, Inc. | Methods of synthesizing 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
| US11530184B2 (en) | 2020-06-30 | 2022-12-20 | Imbria Pharmaceuticals, Inc. | Crystal forms of 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
| US11883396B2 (en) | 2021-05-03 | 2024-01-30 | Imbria Pharmaceuticals, Inc. | Methods of treating kidney conditions using modified forms of trimetazidine |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2674615A (en) * | 1952-06-28 | 1954-04-06 | Abbott Lab | 1-arylcycloalkane 1-thiocar-boxylates |
| US3306727A (en) | 1962-03-16 | 1967-02-28 | Gulf Oil Corp | Weed control method and compositions therefor |
| US3438993A (en) * | 1966-03-23 | 1969-04-15 | Nepera Chem Co Inc | Pyridine esters of cyclopropanecarboxylic acid |
| GB1323183A (en) * | 1971-01-14 | 1973-07-11 | Bdh Pharmaceuticals Ltd | Cyclopropane esters and acids thereof |
| US3975849A (en) * | 1973-09-17 | 1976-08-24 | Tuleja Anthony Z | Reflecting triangular warning devices |
| JPS5071646A (OSRAM) * | 1973-11-05 | 1975-06-13 | ||
| US3926860A (en) * | 1974-01-28 | 1975-12-16 | Int Flavors & Fragrances Inc | Fragrance materials containing cis-2-n-pentyl cyclopropane-1-carboxylic acid |
| US3957849A (en) | 1974-09-09 | 1976-05-18 | Zoecon Corporation | Cyclopropane esters |
| US4000315A (en) | 1974-09-09 | 1976-12-28 | Zoecon Corporation | Cyclopropane esters for the control of mites |
| DE2951939A1 (de) * | 1979-12-22 | 1981-07-16 | Degussa Ag, 6000 Frankfurt | Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung |
| US4935422A (en) * | 1988-12-15 | 1990-06-19 | E. I. Du Pont De Nemours And Company | Acyloxypropanolamines |
| US5652273A (en) * | 1995-11-30 | 1997-07-29 | Henry; James | Reduction of hair growth |
| GB9804648D0 (en) * | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
| ES2487897T3 (es) * | 2000-01-21 | 2014-08-25 | Novartis Ag | Combinaciones que consisten de inhibidores de la dipeptidilpeptidasa-IV y agentes antidiabéticos |
| JP2001294572A (ja) * | 2000-02-09 | 2001-10-23 | Dai Ichi Seiyaku Co Ltd | 新規スルホニル誘導体 |
| US7084173B2 (en) * | 2001-03-30 | 2006-08-01 | The Governors Of The Univerity Of Alberta | Compounds that stimulate glucose utilization and methods of use |
| US7074828B2 (en) * | 2002-12-05 | 2006-07-11 | The Governors Of The University Of Alberta | Compounds that stimulate glucose utilization and methods of use |
| US20030089885A1 (en) | 2001-04-25 | 2003-05-15 | Senomyx, Inc. | Use of low molecular weight acetal, alcohol, acylated alcohol and ester compounds to block or reduce odor of carboxylic acids |
| US7524885B2 (en) * | 2002-04-01 | 2009-04-28 | The Governors Of The University Of Alberta | Compounds that stimulate glucose utilization and methods of use |
| JP4674046B2 (ja) * | 2002-04-01 | 2011-04-20 | ザ ガバナーズ オブ ザ ユニバーシティ オブ アルバータ | グルコース利用を刺激する化合物および使用方法 |
| CN1735603A (zh) * | 2002-12-06 | 2006-02-15 | 东丽株式会社 | 苯并吗啉衍生物 |
| KR20050098250A (ko) * | 2003-01-17 | 2005-10-11 | 쓰레솔드 파마슈티컬스, 인코포레이티드 | 에너골리틱제를 사용한 양성 전립선 비대증의 치료 방법 |
-
2005
- 2005-02-23 US US11/064,713 patent/US7524885B2/en not_active Expired - Lifetime
-
2006
- 2006-02-23 JP JP2007556688A patent/JP4764888B2/ja not_active Expired - Fee Related
- 2006-02-23 CN CNA2006800084195A patent/CN101142167A/zh active Pending
- 2006-02-23 AU AU2006242936A patent/AU2006242936A1/en not_active Abandoned
- 2006-02-23 CA CA2598595A patent/CA2598595C/en active Active
- 2006-02-23 KR KR1020077021514A patent/KR20070107133A/ko not_active Withdrawn
- 2006-02-23 WO PCT/IB2006/001587 patent/WO2006117686A2/en not_active Ceased
- 2006-02-23 EP EP06765523.3A patent/EP1868982B1/en active Active
-
2009
- 2009-03-12 US US12/403,143 patent/US8202901B2/en not_active Expired - Fee Related
-
2010
- 2010-03-03 JP JP2010047058A patent/JP2010180218A/ja not_active Withdrawn
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