WO2007004028A3 - Procedes de preparation de penemes et de leurs intermediaires - Google Patents
Procedes de preparation de penemes et de leurs intermediaires Download PDFInfo
- Publication number
- WO2007004028A3 WO2007004028A3 PCT/IB2006/001821 IB2006001821W WO2007004028A3 WO 2007004028 A3 WO2007004028 A3 WO 2007004028A3 IB 2006001821 W IB2006001821 W IB 2006001821W WO 2007004028 A3 WO2007004028 A3 WO 2007004028A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- preparation
- gram
- formula
- protecting group
- lactam antibiotics
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 150000002961 penems Chemical class 0.000 title 1
- OEYMQQDJCUHKQS-UHFFFAOYSA-N (4-oxoazetidin-2-yl) acetate Chemical compound CC(=O)OC1CC(=O)N1 OEYMQQDJCUHKQS-UHFFFAOYSA-N 0.000 abstract 2
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 239000002132 β-lactam antibiotic Substances 0.000 abstract 2
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract 2
- 241000894006 Bacteria Species 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002217 penem group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
La présente invention concerne un procédé de préparation de 4-acétoxy-azétidinone de formule (I), dans laquelle R2 est hydrogène ou un groupe amino-protecteur approprié et P est un groupe hydroxy-protecteur approprié, ainsi que l'utilisation de ces composés comme intermédiaires pour la préparation d'antibiotiques de β-lactame renfermant les systèmes cycliques carbapénème et pénème. La 4-acétoxy-azétidinone de formule (I) est un intermédiaire clé dans la synthèse d'antibiotiques de β-lactame, lesquels sont des agents antimicrobiens communément prescrits dont l'activité est dirigée contre un large éventail de bactéries gram-positives et gram-négatives.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN1702/DEL/2005 | 2005-06-30 | ||
IN1702DE2005 | 2005-06-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2007004028A2 WO2007004028A2 (fr) | 2007-01-11 |
WO2007004028A3 true WO2007004028A3 (fr) | 2007-03-29 |
Family
ID=37205705
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2006/001821 WO2007004028A2 (fr) | 2005-06-30 | 2006-06-30 | Procedes de preparation de penemes et de leurs intermediaires |
Country Status (1)
Country | Link |
---|---|
WO (1) | WO2007004028A2 (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8952034B2 (en) | 2009-07-27 | 2015-02-10 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US8962610B2 (en) | 2011-07-01 | 2015-02-24 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US9115096B2 (en) | 2011-05-10 | 2015-08-25 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US9193694B2 (en) | 2011-07-01 | 2015-11-24 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101265271B (zh) * | 2008-04-30 | 2013-06-05 | 寿光富康制药有限公司 | 培南类药物中间体4aa的合成方法 |
CN101747250B (zh) * | 2008-12-16 | 2012-09-05 | 上海医药工业研究院 | 一种制备4-酰氧基氮杂环丁酮类化合物的方法 |
WO2011048583A1 (fr) | 2009-10-23 | 2011-04-28 | Ranbaxy Laboratories Limited | Procédé pour la préparation de composés de carbapénème |
AU2011272787B2 (en) | 2010-07-02 | 2015-06-18 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
CN102432632A (zh) * | 2011-09-16 | 2012-05-02 | 上海悦昂化学有限公司 | 一种(3r,4r)-3-[(1r)叔丁基二甲基硅氧乙基]-4-乙酰氧基-2-氮杂环丁酮的制备方法 |
CN102827199A (zh) * | 2012-08-28 | 2012-12-19 | 三峡大学 | 青霉烯和碳青霉烯类抗生素类关键中间体4aa的合成方法 |
WO2014071565A1 (fr) * | 2012-11-07 | 2014-05-15 | 凯莱英医药集团(天津)股份有限公司 | Procédé de préparation d'un intermédiaire 4aa des médicaments à base d'imipénème |
CN102936262A (zh) * | 2012-11-07 | 2013-02-20 | 凯莱英医药集团(天津)股份有限公司 | 培南类药物中间体4aa的制备方法 |
CN103242361A (zh) * | 2013-05-23 | 2013-08-14 | 浙江海翔川南药业有限公司 | 一种培南类抗生素中间体的制备方法 |
CN109721521A (zh) * | 2018-11-26 | 2019-05-07 | 广东药科大学 | 一种光学活性黄皮酰胺酮及其衍生物的制备方法 |
CN115385950B (zh) * | 2022-10-27 | 2023-04-28 | 天津凯莱英医药科技发展有限公司 | 连续臭氧氧化制备4-乙酰氧基氮杂环丁酮的系统及方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0126587A1 (fr) * | 1983-05-09 | 1984-11-28 | Sumitomo Pharmaceuticals Company, Limited | Dérivés de carboxyle thio-pyrrolidinyle-bêta-lactame et leur préparation |
EP0367722A1 (fr) * | 1988-11-04 | 1990-05-09 | Ciba-Geigy Ag | Procédé de préparation d'acyloxyazétidinones optiquement actives |
EP0371875A2 (fr) * | 1988-11-29 | 1990-06-06 | Takasago International Corporation | Procédé de préparation d'acétoxy-4-azétidinones |
EP0528678A1 (fr) * | 1991-08-20 | 1993-02-24 | SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. | Dérivé de pyrrolidylthiocarbapénème |
WO1998007691A1 (fr) * | 1996-08-24 | 1998-02-26 | Choongwae Pharmaceutical Co., Ltd. | Procede de preparation stereoselective de trans-azetidinones |
-
2006
- 2006-06-30 WO PCT/IB2006/001821 patent/WO2007004028A2/fr active Application Filing
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0126587A1 (fr) * | 1983-05-09 | 1984-11-28 | Sumitomo Pharmaceuticals Company, Limited | Dérivés de carboxyle thio-pyrrolidinyle-bêta-lactame et leur préparation |
US4943569A (en) * | 1983-05-09 | 1990-07-24 | Sumitomo Pharmaceuticals Co., Ltd. | B-lactam compounds |
EP0367722A1 (fr) * | 1988-11-04 | 1990-05-09 | Ciba-Geigy Ag | Procédé de préparation d'acyloxyazétidinones optiquement actives |
EP0371875A2 (fr) * | 1988-11-29 | 1990-06-06 | Takasago International Corporation | Procédé de préparation d'acétoxy-4-azétidinones |
US5081239A (en) * | 1988-11-29 | 1992-01-14 | Takasago International Corporation | Ruthenium catalyzed process for preparing 4-acetoxyazetidinones |
EP0528678A1 (fr) * | 1991-08-20 | 1993-02-24 | SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. | Dérivé de pyrrolidylthiocarbapénème |
US5317016A (en) * | 1991-08-20 | 1994-05-31 | Shionogi Seiyaku Kabushiki Kaisha | Pyrrolidylthiocarbapenem derivative |
WO1998007691A1 (fr) * | 1996-08-24 | 1998-02-26 | Choongwae Pharmaceutical Co., Ltd. | Procede de preparation stereoselective de trans-azetidinones |
WO1998007690A1 (fr) * | 1996-08-24 | 1998-02-26 | Choongwae Pharmaceutical Co., Ltd. | Procede de preparation stereoselective de 4-acetoxyazetidinones |
Non-Patent Citations (6)
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8952034B2 (en) | 2009-07-27 | 2015-02-10 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US9371329B2 (en) | 2009-07-27 | 2016-06-21 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US9115096B2 (en) | 2011-05-10 | 2015-08-25 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US9403782B2 (en) | 2011-05-10 | 2016-08-02 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US8962610B2 (en) | 2011-07-01 | 2015-02-24 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
US9193694B2 (en) | 2011-07-01 | 2015-11-24 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
Also Published As
Publication number | Publication date |
---|---|
WO2007004028A2 (fr) | 2007-01-11 |
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