CA2550873A1 - Inhibitors of methionine aminopeptidase-2 and uses thereof - Google Patents
Inhibitors of methionine aminopeptidase-2 and uses thereof Download PDFInfo
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- CA2550873A1 CA2550873A1 CA002550873A CA2550873A CA2550873A1 CA 2550873 A1 CA2550873 A1 CA 2550873A1 CA 002550873 A CA002550873 A CA 002550873A CA 2550873 A CA2550873 A CA 2550873A CA 2550873 A1 CA2550873 A1 CA 2550873A1
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- C—CHEMISTRY; METALLURGY
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- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Veterinary Medicine (AREA)
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- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53343103P | 2003-12-29 | 2003-12-29 | |
| US60/533,431 | 2003-12-29 | ||
| PCT/US2004/043586 WO2005066197A2 (en) | 2003-12-29 | 2004-12-29 | Inhibitors of methionine aminopeptidase-2 and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2550873A1 true CA2550873A1 (en) | 2005-07-21 |
Family
ID=34748901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002550873A Abandoned CA2550873A1 (en) | 2003-12-29 | 2004-12-29 | Inhibitors of methionine aminopeptidase-2 and uses thereof |
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| Country | Link |
|---|---|
| US (1) | US20050239878A1 (enExample) |
| EP (1) | EP1699812A2 (enExample) |
| JP (1) | JP2007537147A (enExample) |
| KR (1) | KR20060130077A (enExample) |
| CN (1) | CN1902215A (enExample) |
| AU (1) | AU2004312512A1 (enExample) |
| CA (1) | CA2550873A1 (enExample) |
| NO (1) | NO20062812L (enExample) |
| WO (1) | WO2005066197A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2398381T3 (es) * | 2002-04-11 | 2013-03-15 | Children's Medical Center Corporation | Conjugados del copolímero de ácido metacrílico-hpma-tnp-470 y sus usos |
| WO2003086178A2 (en) * | 2002-04-11 | 2003-10-23 | Children's Medical Center Corporation | Methods for inhibiting vascular hyperpermeability |
| US20070254843A1 (en) * | 2006-04-18 | 2007-11-01 | Praecis Pharmaceuticals Incorporated | Methods for treating bone associated diseases by the use of methionine aminopeptidase-2 inhibitors |
| WO2008066641A2 (en) * | 2006-11-06 | 2008-06-05 | Praecis Pharmaceuticals Incorporated | Methods for treating mitf associated diseases by the use of methionine aminopeptidase-2 inhibitors |
| EP2170402B1 (en) * | 2007-06-26 | 2015-03-25 | Children's Medical Center Corporation | Metap-2 inhibitor polymersomes for therapeutic administration |
| CA2731020A1 (en) | 2008-07-18 | 2010-01-21 | Zafgen, Inc. | Use of antiangiogenic fumagillins in the treatment of obesity |
| US20120004162A1 (en) | 2008-12-04 | 2012-01-05 | Vath James E | Methods of Treating an Overweight or Obese Subject |
| WO2010065883A2 (en) | 2008-12-04 | 2010-06-10 | Zafgen Corporation | Method of treating an overweight or obese subject |
| KR20120083905A (ko) | 2009-10-09 | 2012-07-26 | 자프겐 코포레이션 | 비만의 치료에 사용하기 위한 설폰 화합물 |
| WO2011085198A1 (en) | 2010-01-08 | 2011-07-14 | Zafgen Corporation | Metap-2 inhibitor for use in treating benign prostatic hypertrophy (bph) |
| CA2786603C (en) | 2010-01-08 | 2018-02-20 | James E. Vath | Fumagillol type compounds and methods of making and using same |
| US20130023513A1 (en) | 2010-01-12 | 2013-01-24 | Hughes Thomas E | Methods and Compositions for Treating Cardiovascular Disorders |
| WO2011127304A2 (en) | 2010-04-07 | 2011-10-13 | Zafgen Corporation | Methods of treating an overweight subject |
| KR20130043207A (ko) | 2010-07-22 | 2013-04-29 | 자프겐 인크. | 트리시클릭 화합물 및 이의 제조 및 사용 방법 |
| PH12013500934A1 (en) | 2010-11-09 | 2022-10-24 | Zafgen Inc | Crystalline solids of a metap-2 inhibitor and methods of making and using same |
| US20140073691A1 (en) * | 2010-11-10 | 2014-03-13 | Zafgen, Inc. | Methods and composition for Treating Thyroid Hormone Related Disorders |
| CA2819251A1 (en) | 2010-11-29 | 2012-06-07 | Zafgen Corporation | Treatment of obesity using non-daily administration of 6 - 0 - (4 - dimethylaminoethoxy) cinnamoyl fumagillol |
| WO2012074968A1 (en) | 2010-11-29 | 2012-06-07 | Zafgen Corporation | Methods of reducing risk of hepatobiliary dysfunction during rapid weight loss with metap-2 inhibitors |
| US9189078B2 (en) | 2010-12-20 | 2015-11-17 | Apple Inc. | Enhancing keycap legend visibility with optical components |
| CA2825408A1 (en) | 2011-01-26 | 2012-08-02 | Zafgen, Inc. | Tetrazole compounds and methods of making and using same |
| JP5876513B2 (ja) * | 2011-03-08 | 2016-03-02 | ザフゲン，インコーポレイテッド | オキサスピロ［２．５］オクタン誘導体および類似体 |
| BR112013028665A2 (pt) | 2011-05-06 | 2016-09-06 | Zafgen Inc | compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| BR112013028666A2 (pt) | 2011-05-06 | 2017-08-08 | Zafgen Inc | compostos de pirazolo sulfonamida tricícilos e métodos para fazer e usar o mesmo |
| KR101979039B1 (ko) | 2011-05-06 | 2019-05-15 | 자프겐 인크. | 부분 포화된 삼환식 화합물 및 그리고 그의 제조방법 및 그를 이용하는 방법 |
| EP2763671A2 (en) | 2011-10-03 | 2014-08-13 | Zafgen, Inc. | Methods of treating age related disorders |
| BR112014017673A8 (pt) | 2012-01-18 | 2017-07-11 | Zafgen Inc | Compostos de sulfonamida tricíclicos e métodos para fazer e usar os mesmos |
| EP2804856B1 (en) | 2012-01-18 | 2017-03-15 | Zafgen, Inc. | Tricyclic sulfone compounds and methods of making and using same |
| EP2847176A1 (en) | 2012-05-07 | 2015-03-18 | Zafgen, Inc. | Polymorphic salt of the oxalate salt of 6 - o - ( 4 - dimethylaminoethoxy) cinnarnoyl fumagillol and methods of making and using same |
| BR112014028041A2 (pt) | 2012-05-08 | 2017-06-27 | Zafgen Inc | tratamento de obesidade hipotalâmica com inibidores de metap2 |
| CA2873574A1 (en) | 2012-05-09 | 2013-11-14 | Zafgen, Inc. | Fumagillol type compounds and methods of making and using same |
| CN104918615B (zh) | 2012-11-05 | 2018-10-12 | 扎夫根股份有限公司 | 治疗肝病的方法 |
| BR112015010225A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | compostos tricíclicos e seus métodos de produção e utilização |
| US9868717B2 (en) | 2012-11-05 | 2018-01-16 | Zafgen, Inc. | Tricyclic sulphonamide compounds and methods of making and using same |
| AU2014236528A1 (en) | 2013-03-14 | 2015-09-24 | Zafgen, Inc. | Methods of treating renal disease and other disorders |
| AR105671A1 (es) | 2015-08-11 | 2017-10-25 | Zafgen Inc | Compuestos heterocíclicos de fumagillol y sus métodos de elaboración y uso |
| CN106432255A (zh) | 2015-08-11 | 2017-02-22 | 扎夫根公司 | 烟曲霉素醇螺环化合物和制备和使用其的方法 |
| US20200003759A1 (en) * | 2017-02-10 | 2020-01-02 | Zafgen, Inc. | Methods for identifying metap-2 modulators |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2546163B1 (fr) * | 1983-05-16 | 1987-10-09 | Centre Nat Rech Scient | Nouveaux derives acyles hydrosolubles de peptides ou d'amino-acides, leur preparation et leur application |
| US5135919A (en) * | 1988-01-19 | 1992-08-04 | Children's Medical Center Corporation | Method and a pharmaceutical composition for the inhibition of angiogenesis |
| PH26256A (en) * | 1988-08-12 | 1992-04-01 | Fujisawa Pharmaceutical Co | Oxaspiro [2,5] octane derivative |
| US5180738A (en) * | 1988-09-01 | 1993-01-19 | Takeda Chemical Industries | Fumagillol derivatives and pharmaceutical compositions thereof |
| EP0359036B1 (en) * | 1988-09-01 | 1997-03-26 | Takeda Chemical Industries, Ltd. | Fumagillol derivatives |
| US5290807A (en) * | 1989-08-10 | 1994-03-01 | Children's Medical Center Corporation | Method for regressing angiogenesis using o-substituted fumagillol derivatives |
| US6017954A (en) * | 1989-08-10 | 2000-01-25 | Children's Medical Center Corp. | Method of treating tumors using O-substituted fumagillol derivatives |
| EP0415294A3 (en) * | 1989-08-31 | 1991-06-12 | Takeda Chemical Industries, Ltd. | Cyclohexanol derivatives, production and use thereof |
| JPH06157344A (ja) * | 1992-02-07 | 1994-06-03 | Childrens Medical Center Corp:The | 血管新生阻害のための医薬製剤及び血管新生阻害方法 |
| EP0602586B1 (en) * | 1992-12-16 | 1997-06-04 | Takeda Chemical Industries, Ltd. | Stable pharmaceutical composition of fumagillol derivatives |
| FR2733498B1 (fr) * | 1995-04-27 | 1997-05-30 | Adir | Nouveaux composes cyclohexaniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6207704B1 (en) * | 1997-06-09 | 2001-03-27 | Massachusetts Institute Of Technology | Type 2 methionine aminopeptidase [MetAP2] inhibitors and uses thereof |
| US6919307B2 (en) * | 2000-11-01 | 2005-07-19 | Praecis Pharmaceuticals, Inc. | Therapeutic agents and methods of use thereof for the modulation of angiogenesis |
| US6548477B1 (en) * | 2000-11-01 | 2003-04-15 | Praecis Pharmaceuticals Inc. | Therapeutic agents and methods of use thereof for the modulation of angiogenesis |
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2004
- 2004-12-29 CA CA002550873A patent/CA2550873A1/en not_active Abandoned
- 2004-12-29 US US11/025,568 patent/US20050239878A1/en not_active Abandoned
- 2004-12-29 EP EP04815618A patent/EP1699812A2/en not_active Withdrawn
- 2004-12-29 AU AU2004312512A patent/AU2004312512A1/en not_active Abandoned
- 2004-12-29 KR KR1020067012422A patent/KR20060130077A/ko not_active Withdrawn
- 2004-12-29 JP JP2006547452A patent/JP2007537147A/ja active Pending
- 2004-12-29 WO PCT/US2004/043586 patent/WO2005066197A2/en not_active Ceased
- 2004-12-29 CN CNA2004800393912A patent/CN1902215A/zh active Pending
-
2006
- 2006-06-15 NO NO20062812A patent/NO20062812L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20050239878A1 (en) | 2005-10-27 |
| AU2004312512A1 (en) | 2005-07-21 |
| KR20060130077A (ko) | 2006-12-18 |
| JP2007537147A (ja) | 2007-12-20 |
| WO2005066197A3 (en) | 2006-01-26 |
| WO2005066197A2 (en) | 2005-07-21 |
| CN1902215A (zh) | 2007-01-24 |
| NO20062812L (no) | 2006-07-21 |
| EP1699812A2 (en) | 2006-09-13 |
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| FZDE | Discontinued |