CN102725300B - 蛋白酶体抑制剂及其制备、纯化、和应用的方法 - Google Patents
蛋白酶体抑制剂及其制备、纯化、和应用的方法 Download PDFInfo
- Publication number
- CN102725300B CN102725300B CN201080058991.9A CN201080058991A CN102725300B CN 102725300 B CN102725300 B CN 102725300B CN 201080058991 A CN201080058991 A CN 201080058991A CN 102725300 B CN102725300 B CN 102725300B
- Authority
- CN
- China
- Prior art keywords
- formula
- optionally substituted
- compound
- ester
- boronate
- 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.)
- Expired - Fee Related
Links
- 0 CC(C)CC(B(O)O)NC(*NC(*)=O)=O Chemical compound CC(C)CC(B(O)O)NC(*NC(*)=O)=O 0.000 description 11
- UJKGIGHYNZUUKG-UHFFFAOYSA-N CC(C)C=C([B]12OC(C)C[NH+]1CC(C)O2)NC(C(C(C)=O)NC(c1cccc(-c2ccccc2)n1)=O)=O Chemical compound CC(C)C=C([B]12OC(C)C[NH+]1CC(C)O2)NC(C(C(C)=O)NC(c1cccc(-c2ccccc2)n1)=O)=O UJKGIGHYNZUUKG-UHFFFAOYSA-N 0.000 description 1
- MLVUAYQJFGNDCY-GMAHTHKFSA-N CCC[N]1(C)CCO[B]1([C@H](CC(C)C)NC([C@H](Cc1ccccc1)NC(c1nccnc1)=O)=O)O Chemical compound CCC[N]1(C)CCO[B]1([C@H](CC(C)C)NC([C@H](Cc1ccccc1)NC(c1nccnc1)=O)=O)O MLVUAYQJFGNDCY-GMAHTHKFSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28895709P | 2009-12-22 | 2009-12-22 | |
| US61/288,957 | 2009-12-22 | ||
| PCT/US2010/061695 WO2011087822A1 (en) | 2009-12-22 | 2010-12-22 | Proteasome inhibitors and processes for their preparation, purification and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102725300A CN102725300A (zh) | 2012-10-10 |
| CN102725300B true CN102725300B (zh) | 2015-03-11 |
Family
ID=43530797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201080058991.9A Expired - Fee Related CN102725300B (zh) | 2009-12-22 | 2010-12-22 | 蛋白酶体抑制剂及其制备、纯化、和应用的方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8541590B2 (https=) |
| EP (1) | EP2516449A1 (https=) |
| JP (1) | JP5783659B2 (https=) |
| CN (1) | CN102725300B (https=) |
| AU (1) | AU2010341530B2 (https=) |
| CA (1) | CA2785300A1 (https=) |
| IL (1) | IL220190A0 (https=) |
| MX (1) | MX2012007341A (https=) |
| NZ (1) | NZ600786A (https=) |
| WO (1) | WO2011087822A1 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150067175A (ko) | 2012-09-11 | 2015-06-17 | 시플라 리미티드 | 보르테조밉을 제조하기 위한 방법 |
| CN103897027A (zh) * | 2012-12-29 | 2014-07-02 | 曹亚英 | 关键中间体晶型,制备方法及其在硼替佐米合成中的运用 |
| CN103897026A (zh) * | 2012-12-29 | 2014-07-02 | 朱继东 | 硼替佐米关键中间体的晶型,制备方法及其运用 |
| IN2013MU01431A (https=) | 2013-04-16 | 2015-06-26 | Cipla Ltd | |
| CZ2015233A3 (cs) | 2015-04-03 | 2016-10-12 | Zentiva, K.S. | Způsob přípravy Ixazomib citrátu |
| CZ2015253A3 (cs) | 2015-04-15 | 2016-10-26 | Zentiva, K.S. | Nové formy Ixazomib citrátu |
| US10144761B2 (en) | 2015-06-19 | 2018-12-04 | Hanlin Scientific Inc. | Chiral specific boron-containing compounds and their use in treating cancer or amyloidosis |
| CZ2016204A3 (cs) | 2016-04-08 | 2017-11-01 | Zentiva, K.S. | Formulace Ixazomib citrátu formy 3 |
| EP3583110A1 (en) | 2017-02-17 | 2019-12-25 | Fresenius Kabi Oncology Ltd | An improved process for the preparation of boronic acid esters |
| JP7086987B2 (ja) * | 2017-03-21 | 2022-06-20 | ザ スクリプス リサーチ インスティテュート | 銅およびニッケル触媒による脱炭酸ホウ素化反応 |
| CN110540547A (zh) * | 2018-05-28 | 2019-12-06 | 秦艳茹 | 一种肽硼酸酯类化合物的合成与用途 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002059130A1 (en) * | 2001-01-25 | 2002-08-01 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Formulation of boronic acid compounds |
| EP1312609A1 (en) * | 1994-10-28 | 2003-05-21 | Millennium Pharmaceuticals, Inc. | Boronic ester and acid compounds, synthesis and uses |
| CN1867572A (zh) * | 2003-08-14 | 2006-11-22 | 赛福伦公司 | 蛋白酶体抑制剂及其使用方法 |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3301354A1 (de) | 1983-01-18 | 1984-07-19 | Matth. Hohner Ag, 7218 Trossingen | Elektronisches musikinstrument |
| US4537773A (en) | 1983-12-05 | 1985-08-27 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid derivatives |
| US4499082A (en) | 1983-12-05 | 1985-02-12 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid peptides |
| US5242904A (en) | 1987-06-05 | 1993-09-07 | The Dupont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
| US5250720A (en) | 1987-06-05 | 1993-10-05 | The Dupont Merck Pharmaceutical Company | Intermediates for preparing peptide boronic acid inhibitors of trypsin-like proteases |
| US5187157A (en) | 1987-06-05 | 1993-02-16 | Du Pont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
| EP0315574A3 (de) | 1987-11-05 | 1990-08-22 | Hoechst Aktiengesellschaft | Renin-Inhibitoren |
| AU3418389A (en) | 1988-03-28 | 1989-10-16 | Regents Of The University Of California, The | Nerve growth factor peptides |
| US5023236A (en) | 1988-04-07 | 1991-06-11 | Corvas, Inc. | Factor VII/VIIA active site inhibitors |
| US5106948A (en) | 1988-05-27 | 1992-04-21 | Mao Foundation For Medical Education And Research | Cytotoxic boronic acid peptide analogs |
| US5159060A (en) | 1988-05-27 | 1992-10-27 | Mayo Foundation For Medical Education And Research | Cytotoxic boronic acid peptide analogs |
| US4963655A (en) | 1988-05-27 | 1990-10-16 | Mayo Foundation For Medical Education And Research | Boron analogs of amino acid/peptide protease inhibitors |
| DE3827340A1 (de) | 1988-08-12 | 1990-02-15 | Hoechst Ag | Verwendung von (alpha)-aminoboronsaeure-derivaten zur prophylaxe und behandlung von viruserkrankungen |
| AU661270B2 (en) | 1990-03-05 | 1995-07-20 | Cephalon, Inc. | Chymotrypsin-like proteases and their inhibitors |
| EP0583536B1 (en) | 1992-08-14 | 1997-03-05 | The Procter & Gamble Company | Liquid detergents containing an alpha-amino boronic acid |
| EP0684829A4 (en) | 1993-02-10 | 1997-05-21 | Harvard College | THE ROLE OF ATP-UBIQUITIN-DEPENDENT PROTEOLYSIS IN MHC-1 DEPENDENT ANTIGENT PRESENTATION AND RELATED INHIBITORS. |
| IL109319A0 (en) | 1993-04-27 | 1994-07-31 | Du Pont Merck Pharma | Amidino and guanidino substituted boronic acid compounds |
| US5658885A (en) | 1993-04-27 | 1997-08-19 | The Dupont Merck Pharmaceutical Company | Amidino and guanidino substituted boronic acid inhibitors of trypsin-like enzymes |
| US5672582A (en) | 1993-04-30 | 1997-09-30 | Merck & Co., Inc. | Thrombin inhibitors |
| DE69431718T2 (de) | 1993-04-30 | 2003-07-10 | Merck & Co., Inc. | Thrombin-inhibitoren |
| FR2707085B1 (fr) | 1993-06-30 | 1995-08-18 | Adir | Nouveaux dérivés d'alpha amino acides, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| JPH09505281A (ja) | 1993-10-01 | 1997-05-27 | メレルファーマスーティカルズ インコーポレイテッド | β−アミロイド蛋白質製造の阻害剤類 |
| IL111175A0 (en) | 1993-10-07 | 1994-12-29 | Du Pont Merck Pharma | Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them |
| GB9401483D0 (en) | 1994-01-26 | 1994-03-23 | Sandoz Ltd | Organic compounds |
| US5693617A (en) | 1994-03-15 | 1997-12-02 | Proscript, Inc. | Inhibitors of the 26s proteolytic complex and the 20s proteasome contained therein |
| US6660268B1 (en) | 1994-03-18 | 2003-12-09 | The President And Fellows Of Harvard College | Proteasome regulation of NF-KB activity |
| US5550262A (en) | 1994-11-14 | 1996-08-27 | Cephalon, Inc. | Multicatalytic protease inhibitors |
| US5614649A (en) | 1994-11-14 | 1997-03-25 | Cephalon, Inc. | Multicatalytic protease inhibitors |
| US5834487A (en) | 1996-09-24 | 1998-11-10 | Cv Therapeutics | Inhibition of 26S and 20S proteasome by indanones |
| AP1019A (en) | 1996-10-18 | 2001-10-16 | Vertex Pharma | Inhibitors of serinre proteases, particularly hepatitis C virus NS3 protease. |
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| US6096778A (en) | 1997-10-07 | 2000-08-01 | Cephalon, Inc. | α-ketoamide multicatalytic protease inhibitors |
| CN1282242A (zh) | 1997-12-16 | 2001-01-31 | 赛福伦公司 | 多相催化蛋白酶抑制剂用作抗肿瘤剂 |
| US6075150A (en) | 1998-01-26 | 2000-06-13 | Cv Therapeutics, Inc. | α-ketoamide inhibitors of 20S proteasome |
| GB9806815D0 (en) | 1998-03-30 | 1998-05-27 | Hoffmann La Roche | Amino acid derivatives |
| US6462019B1 (en) | 1998-07-10 | 2002-10-08 | Osteoscreen, Inc. | Inhibitors of proteasomal activity and production for stimulating bone growth |
| EP0995757A3 (en) | 1998-08-26 | 2002-05-22 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Bivalent inhibitors of the proteasome |
| BR9914648A (pt) | 1998-10-20 | 2001-11-27 | Millennium Pharm Inc | Processo para monitorar ação medicamentosa deinibidor de proteasoma |
| EP1053750A1 (en) | 1999-04-22 | 2000-11-22 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Use of proteasome-inhibitor for the induction of programmed cell death (apoptosis) |
| BR0010134A (pt) | 1999-04-27 | 2002-01-15 | Novartis Ag | Uso de derivados de ácido 2,4-diamino-3-hidroxicarboxìlico como inibidores de proteassoma |
| SE9901573D0 (sv) | 1999-05-03 | 1999-05-03 | Astra Ab | New compounds |
| WO2001002424A2 (en) | 1999-07-07 | 2001-01-11 | Du Pont Pharmaceuticals Company | Peptide boronic acid inhibitors of hepatitis c virus protease |
| US7122627B2 (en) | 1999-07-26 | 2006-10-17 | Bristol-Myers Squibb Company | Lactam inhibitors of Hepatitis C virus NS3 protease |
| WO2001020995A1 (en) | 1999-09-23 | 2001-03-29 | Washington University | Compounds directed against pilus biogenesis and activity in pathogenic bacteria; methods and compositions for synthesis thereof |
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| SK742003A3 (en) | 2000-07-21 | 2003-06-03 | Schering Corp | Novel peptides as NS3-serine protease inhibitors of hepatitis C virus |
| ATE338564T1 (de) | 2000-10-12 | 2006-09-15 | Viromics Gmbh | Proteasome inhibitoren zur behandlung von hepatitis-virus infektionen |
| KR20040002905A (ko) | 2001-04-09 | 2004-01-07 | 알란 크리스챤 쇼우 | 세포내 세균으로부터 단백질을 동정하는 방법 |
| US7214769B2 (en) | 2001-05-23 | 2007-05-08 | The Curators Of The University Of Missouri | Method for inverse solid phase synthesis of peptides |
| DE60209227T2 (de) | 2001-05-30 | 2006-08-17 | Novartis Ag | 2-((n-(2-amino-3-(heteroaryl- oder -aryl)propionyl)aminoacyl)amino)-alkylboronsäurederivate |
| AU2002324734A1 (en) | 2001-08-16 | 2003-03-03 | Levente Fabry-Asztalos | Borinic acid protease inhibitors |
| JPWO2003033507A1 (ja) | 2001-10-12 | 2005-02-03 | 杏林製薬株式会社 | ベンジルマロン酸誘導体およびそれを含有するプロテアソーム阻害薬 |
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| US7576206B2 (en) | 2003-08-14 | 2009-08-18 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| US7223745B2 (en) | 2003-08-14 | 2007-05-29 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| HRP20212002T1 (hr) | 2004-03-30 | 2022-04-01 | Millennium Pharmaceuticals, Inc. | Sinteza estera i spojeva borove kiseline |
| US7468383B2 (en) | 2005-02-11 | 2008-12-23 | Cephalon, Inc. | Proteasome inhibitors and methods of using the same |
| AU2007357338B2 (en) | 2007-08-06 | 2014-03-20 | Takeda Pharmaceutical Company Limited | Proteasome inhibitors |
| US7442830B1 (en) | 2007-08-06 | 2008-10-28 | Millenium Pharmaceuticals, Inc. | Proteasome inhibitors |
| EP2238973A1 (en) * | 2009-04-07 | 2010-10-13 | Cephalon France | Lyophilized preparations of proteasome inhibitors |
-
2010
- 2010-12-22 AU AU2010341530A patent/AU2010341530B2/en not_active Ceased
- 2010-12-22 CN CN201080058991.9A patent/CN102725300B/zh not_active Expired - Fee Related
- 2010-12-22 WO PCT/US2010/061695 patent/WO2011087822A1/en not_active Ceased
- 2010-12-22 EP EP10798930A patent/EP2516449A1/en not_active Withdrawn
- 2010-12-22 JP JP2012546173A patent/JP5783659B2/ja not_active Expired - Fee Related
- 2010-12-22 NZ NZ600786A patent/NZ600786A/en not_active IP Right Cessation
- 2010-12-22 MX MX2012007341A patent/MX2012007341A/es active IP Right Grant
- 2010-12-22 CA CA2785300A patent/CA2785300A1/en not_active Abandoned
-
2012
- 2012-06-05 IL IL220190A patent/IL220190A0/en not_active IP Right Cessation
- 2012-06-20 US US13/528,147 patent/US8541590B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1312609A1 (en) * | 1994-10-28 | 2003-05-21 | Millennium Pharmaceuticals, Inc. | Boronic ester and acid compounds, synthesis and uses |
| WO2002059130A1 (en) * | 2001-01-25 | 2002-08-01 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Formulation of boronic acid compounds |
| CN1867572A (zh) * | 2003-08-14 | 2006-11-22 | 赛福伦公司 | 蛋白酶体抑制剂及其使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102725300A (zh) | 2012-10-10 |
| US20120270840A1 (en) | 2012-10-25 |
| JP2013515082A (ja) | 2013-05-02 |
| AU2010341530A1 (en) | 2012-07-19 |
| AU2010341530B2 (en) | 2016-03-10 |
| WO2011087822A1 (en) | 2011-07-21 |
| MX2012007341A (es) | 2012-07-20 |
| NZ600786A (en) | 2013-12-20 |
| JP5783659B2 (ja) | 2015-09-24 |
| CA2785300A1 (en) | 2011-07-21 |
| EP2516449A1 (en) | 2012-10-31 |
| US8541590B2 (en) | 2013-09-24 |
| IL220190A0 (en) | 2012-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20150311 Termination date: 20171222 |