JP2009185041A5 - - Google Patents
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- Publication number
- JP2009185041A5 JP2009185041A5 JP2009089110A JP2009089110A JP2009185041A5 JP 2009185041 A5 JP2009185041 A5 JP 2009185041A5 JP 2009089110 A JP2009089110 A JP 2009089110A JP 2009089110 A JP2009089110 A JP 2009089110A JP 2009185041 A5 JP2009185041 A5 JP 2009185041A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- represented
- producing
- diol lactone
- alkali metal
- 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 diol lactone Chemical class 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000007529 inorganic bases Chemical class 0.000 claims 3
- 150000003333 secondary alcohols Chemical class 0.000 claims 3
- 150000003509 tertiary alcohols Chemical class 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims 2
- 229960004844 lovastatin Drugs 0.000 claims 2
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 238000007273 lactonization reaction Methods 0.000 claims 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims 1
- 229960002855 simvastatin Drugs 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009089110A JP5048709B2 (ja) | 1998-12-10 | 2009-04-01 | シンバスタチンの製造方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35186598 | 1998-12-10 | ||
| JP1998351865 | 1998-12-10 | ||
| JP2009089110A JP5048709B2 (ja) | 1998-12-10 | 2009-04-01 | シンバスタチンの製造方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000586711A Division JP4440476B2 (ja) | 1998-12-10 | 1999-12-10 | シンバスタチンの製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009185041A JP2009185041A (ja) | 2009-08-20 |
| JP2009185041A5 true JP2009185041A5 (https=) | 2010-02-18 |
| JP5048709B2 JP5048709B2 (ja) | 2012-10-17 |
Family
ID=18420148
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000586711A Expired - Fee Related JP4440476B2 (ja) | 1998-12-10 | 1999-12-10 | シンバスタチンの製造方法 |
| JP2009089110A Expired - Fee Related JP5048709B2 (ja) | 1998-12-10 | 2009-04-01 | シンバスタチンの製造方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000586711A Expired - Fee Related JP4440476B2 (ja) | 1998-12-10 | 1999-12-10 | シンバスタチンの製造方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6331641B1 (https=) |
| EP (2) | EP1533308B1 (https=) |
| JP (2) | JP4440476B2 (https=) |
| KR (1) | KR100672269B1 (https=) |
| CN (2) | CN1226296C (https=) |
| AT (1) | ATE283849T1 (https=) |
| AU (1) | AU1683000A (https=) |
| CA (1) | CA2320163C (https=) |
| CZ (2) | CZ299566B6 (https=) |
| DE (1) | DE69922348T2 (https=) |
| ES (1) | ES2234323T3 (https=) |
| HU (1) | HUP0103021A3 (https=) |
| SI (1) | SI20327B (https=) |
| WO (1) | WO2000034264A1 (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6573385B1 (en) | 1999-11-11 | 2003-06-03 | Biocon India Limited | Process for manufacturing simvastatin and novel intermediates thereof |
| AU2127500A (en) | 1999-11-11 | 2001-06-06 | Biocon India Limited | Process for manufacturing simvastatin and the novel intermediates |
| GB0011120D0 (en) * | 2000-05-09 | 2000-06-28 | Avecia Ltd | Process |
| KR100361833B1 (ko) * | 2000-06-20 | 2002-11-22 | 주식회사 엘지생명과학 | 심바스타틴의 제조방법 |
| NL1015744C2 (nl) * | 2000-07-19 | 2002-01-22 | Dsm Nv | Werkwijze voor de bereiding van 2-(6-gesubstitueerde-1,3-dioxan-4-yl) azijnzuurderivaten. |
| IL159741A0 (en) | 2001-07-13 | 2004-06-20 | Astrazeneca Uk Ltd | Preparation of aminopyrimidine compounds |
| KR100435142B1 (ko) * | 2002-01-09 | 2004-06-09 | 한미약품 주식회사 | 개선된 심바스타틴의 제조방법 |
| KR100502833B1 (ko) * | 2002-03-25 | 2005-07-25 | 보령제약 주식회사 | 심바스타틴 및 이의 중간체 화합물들의 개선된 제조방법 |
| KR100502834B1 (ko) * | 2002-03-25 | 2005-07-20 | 보령제약 주식회사 | 개선된 락톤화 반응에 의한 심바스타틴의 제조방법 및이의 정제방법 |
| US6603022B1 (en) | 2002-05-10 | 2003-08-05 | Biocon India Limited | Process for manufacturing Simvastatin and novel intermediates thereof |
| EP1375493A1 (en) * | 2002-06-17 | 2004-01-02 | Dsm N.V. | Process for the preparation of an dioxane acetic acid ester |
| GB0218781D0 (en) * | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| JP4731489B2 (ja) * | 2003-10-21 | 2011-07-27 | ヴェレニウム コーポレイション | シンバスタチン及び中間体の製造方法 |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| AU2003289546A1 (en) * | 2003-12-16 | 2005-07-05 | Uk Chemipharm Co., Ltd. | Process for preparing simvastatin. |
| CN1754870A (zh) * | 2004-09-30 | 2006-04-05 | 淮北市辉克药业有限公司 | 辛伐他汀的制备方法 |
| GB0428328D0 (en) * | 2004-12-24 | 2005-02-02 | Astrazeneca Uk Ltd | Chemical process |
| GB0514078D0 (en) * | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
| US20110059493A1 (en) * | 2007-08-27 | 2011-03-10 | Brian Morgan | Methods for Making Simvastatin and Intermediates |
| JP2009114121A (ja) * | 2007-11-06 | 2009-05-28 | Kaneka Corp | シンバスタチンの製造方法 |
| CN101575328B (zh) * | 2008-05-09 | 2012-07-04 | 上海医药工业研究院 | 一种辛伐他汀中间体的合成方法 |
| CN102690254B (zh) * | 2008-05-09 | 2014-06-04 | 上海医药工业研究院 | 辛伐他汀铵盐中间体及其制备方法 |
| CN110483459A (zh) * | 2019-09-10 | 2019-11-22 | 山东罗欣药业集团恒欣药业有限公司 | 一种辛伐他汀的合成方法 |
| CN110563680A (zh) * | 2019-09-10 | 2019-12-13 | 山东罗欣药业集团恒欣药业有限公司 | 一种治疗高脂血症药物的制备方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444784A (en) * | 1980-08-05 | 1984-04-24 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| ZA81703B (en) * | 1980-02-04 | 1982-09-29 | Merck & Co Inc | New antihypercholesterolemic compounds,intermediates and processes |
| JPS58188872A (ja) * | 1982-04-26 | 1983-11-04 | Suntory Ltd | オクタヒドロナフタレン誘導体及びその製造法 |
| US4837205A (en) * | 1986-09-02 | 1989-06-06 | Merck & Co., Inc. | Prodrugs of antihypercholesterolemic compounds |
| US4916239A (en) * | 1988-07-19 | 1990-04-10 | Merck & Co., Inc. | Process for the lactonization of mevinic acids and analogs thereof |
| GB8915280D0 (en) * | 1989-07-04 | 1989-08-23 | British Bio Technology | Compounds |
| US5072002A (en) * | 1989-07-18 | 1991-12-10 | The Governors Of The University Of Alberta | Synthesis of cholesterol-lowering agents |
| US5093363A (en) * | 1989-08-22 | 1992-03-03 | Shionogi & Co., Ltd. | 2,4,6-substituted phenol derivatives |
| DE69008277D1 (de) * | 1989-08-31 | 1994-05-26 | Merck & Co Inc | 7-Subsituierte HMG-CoA-Reduktase-Inhibitoren. |
| US5393893A (en) * | 1993-11-08 | 1995-02-28 | Apotex, Inc. | Process for producing simvastatin and analogs thereof |
| AU7271696A (en) * | 1995-12-06 | 1997-06-27 | Antibiotic Co | Method of production of lovastatin |
| US5763653A (en) * | 1997-03-13 | 1998-06-09 | Ranbaxy Laboratories, Ltd. | Key intermediates in the manufacture of simvastatin |
| CA2185961A1 (en) * | 1996-09-19 | 1998-03-20 | K.S. Keshava Murthy | Process for producing simvastatin |
| SI9700202A (sl) * | 1997-01-24 | 1998-08-31 | Ranbaxy Laboratories Limited | Postopek izdelave simvastatina iz lovastatina ali mevinolinske kisline |
| US5763646A (en) * | 1997-03-13 | 1998-06-09 | Ranbaxy Laboratories, Ltd. | Process for manufacturing simvastatin from lovastatin or mevinolinic acid |
| DE69834279T2 (de) * | 1997-01-28 | 2007-01-04 | Plus Chemicals B.V. | Verfahren zu Herstellung von halb-synthetischen Statins via neue Zwischenprodukte |
| SI9800057A (sl) * | 1998-02-26 | 1999-08-31 | Krka, Tovarna Zdravil, D.D. | Postopek za pripravo simvastatina in njegovih derivatov |
| EP0940395A1 (en) * | 1998-03-05 | 1999-09-08 | Synthon B.V. | Process for producing simvastatin and/or its derivatives |
-
1999
- 1999-12-10 JP JP2000586711A patent/JP4440476B2/ja not_active Expired - Fee Related
- 1999-12-10 CZ CZ20080099A patent/CZ299566B6/cs not_active IP Right Cessation
- 1999-12-10 ES ES99959738T patent/ES2234323T3/es not_active Expired - Lifetime
- 1999-12-10 HU HU0103021A patent/HUP0103021A3/hu unknown
- 1999-12-10 CN CNB031530451A patent/CN1226296C/zh not_active Expired - Fee Related
- 1999-12-10 WO PCT/JP1999/006929 patent/WO2000034264A1/ja not_active Ceased
- 1999-12-10 CZ CZ20003149A patent/CZ299522B6/cs not_active IP Right Cessation
- 1999-12-10 CA CA002320163A patent/CA2320163C/en not_active Expired - Fee Related
- 1999-12-10 DE DE69922348T patent/DE69922348T2/de not_active Expired - Lifetime
- 1999-12-10 CN CN99802754A patent/CN1122029C/zh not_active Expired - Fee Related
- 1999-12-10 SI SI9920024A patent/SI20327B/sl active Search and Examination
- 1999-12-10 KR KR1020007008648A patent/KR100672269B1/ko not_active Expired - Fee Related
- 1999-12-10 EP EP04023298.5A patent/EP1533308B1/en not_active Expired - Lifetime
- 1999-12-10 AU AU16830/00A patent/AU1683000A/en not_active Abandoned
- 1999-12-10 EP EP99959738A patent/EP1055671B1/en not_active Expired - Lifetime
- 1999-12-10 US US09/601,794 patent/US6331641B1/en not_active Expired - Lifetime
- 1999-12-10 AT AT99959738T patent/ATE283849T1/de not_active IP Right Cessation
-
2009
- 2009-04-01 JP JP2009089110A patent/JP5048709B2/ja not_active Expired - Fee Related
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