JP2007512354A5 - - Google Patents
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- Publication number
- JP2007512354A5 JP2007512354A5 JP2006541502A JP2006541502A JP2007512354A5 JP 2007512354 A5 JP2007512354 A5 JP 2007512354A5 JP 2006541502 A JP2006541502 A JP 2006541502A JP 2006541502 A JP2006541502 A JP 2006541502A JP 2007512354 A5 JP2007512354 A5 JP 2007512354A5
- Authority
- JP
- Japan
- Prior art keywords
- rosuvastatin
- degradation product
- product
- lactone
- calcium
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
- 229960000672 rosuvastatin Drugs 0.000 claims description 36
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 claims description 36
- 239000007857 degradation product Substances 0.000 claims description 34
- 150000002596 lactones Chemical class 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 159000000007 calcium salts Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 239000011575 calcium Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims 24
- 239000000047 product Substances 0.000 claims 14
- 239000000243 solution Substances 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 230000001678 irradiating effect Effects 0.000 claims 5
- 238000000354 decomposition reaction Methods 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- SOEGVMSNJOCVHT-VEUZHWNKSA-N Rosuvastatin lactone Chemical compound C(\[C@H]1OC(=O)C[C@H](O)C1)=C/C=1C(C(C)C)=NC(N(C)S(C)(=O)=O)=NC=1C1=CC=C(F)C=C1 SOEGVMSNJOCVHT-VEUZHWNKSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000004587 chromatography analysis Methods 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- LALFOYNTGMUKGG-BGRFNVSISA-L rosuvastatin calcium Chemical compound [Ca+2].CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O.CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O LALFOYNTGMUKGG-BGRFNVSISA-L 0.000 claims 2
- 229960004796 rosuvastatin calcium Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- -1 alkaline earth metal salt Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- 238000011208 chromatographic data Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 239000003550 marker Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000004809 thin layer chromatography Methods 0.000 claims 1
Images
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52644903P | 2003-12-02 | 2003-12-02 | |
| US60/526,449 | 2003-12-02 | ||
| PCT/US2004/040329 WO2005056534A1 (en) | 2003-12-02 | 2004-12-02 | Reference standard for characterization of rosuvastatin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007512354A JP2007512354A (ja) | 2007-05-17 |
| JP2007512354A5 true JP2007512354A5 (https=) | 2009-10-08 |
| JP4733047B2 JP4733047B2 (ja) | 2011-07-27 |
Family
ID=34676616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006541502A Expired - Fee Related JP4733047B2 (ja) | 2003-12-02 | 2004-12-02 | ロスバスタチンの特性評価のためのリファレンス・スタンダード |
Country Status (13)
| Country | Link |
|---|---|
| US (6) | US7244844B2 (https=) |
| EP (1) | EP1689723B1 (https=) |
| JP (1) | JP4733047B2 (https=) |
| KR (1) | KR100887264B1 (https=) |
| CN (1) | CN1894221B (https=) |
| AT (1) | ATE507209T1 (https=) |
| CA (1) | CA2546894C (https=) |
| DE (1) | DE602004032465D1 (https=) |
| ES (1) | ES2364143T3 (https=) |
| IL (1) | IL175511A (https=) |
| PT (1) | PT1689723E (https=) |
| TW (1) | TWI351958B (https=) |
| WO (1) | WO2005056534A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| CN1894221B (zh) * | 2003-12-02 | 2012-08-08 | 特瓦制药工业有限公司 | 用于表征罗苏伐他汀的参照标准品 |
| US7851624B2 (en) | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
| US7612203B2 (en) * | 2005-02-22 | 2009-11-03 | Teva Pharmaceutical Industries Ltd. | Rosuvastatin and salts thereof free of rosuvastatin alkylether and a process for the preparation thereof |
| WO2007071357A2 (en) * | 2005-12-20 | 2007-06-28 | Lek Pharmaceuticals D.D. | Pharmaceutical composition comprising (e) -7- [4- (4-fluorophenyl) -6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin-5 -yl- (3r, 5s) -3, 5-dihydr0xyhept-6-en0ic acid |
| JP5330225B2 (ja) * | 2007-03-13 | 2013-10-30 | テバ ファーマシューティカル インダストリーズ リミティド | トリオール型ロスバスタチン |
| EP2189456A1 (en) * | 2008-11-14 | 2010-05-26 | LEK Pharmaceuticals d.d. | New compounds prepared from omeprazole |
| TWI461410B (zh) | 2008-12-30 | 2014-11-21 | Arqule Inc | 經取代之５，６－二氫－６－苯基苯並〔f〕異喹啉－２－胺化合物類 |
| CN103454352B (zh) * | 2013-07-30 | 2015-07-15 | 广东先强药业有限公司 | 一种hplc法测定瑞舒伐他汀钙的含量及其有关物质的方法 |
| CN103776939A (zh) * | 2014-02-11 | 2014-05-07 | 润泽制药(苏州)有限公司 | 瑞舒伐他汀钙制剂有关物质的制备检测方法 |
| CN108398501A (zh) * | 2018-03-02 | 2018-08-14 | 海南通用三洋药业有限公司 | 一种检测瑞舒伐他汀钙有关物质的方法 |
| CN109020902B (zh) * | 2018-07-23 | 2020-06-02 | 唯智医药科技（北京）有限公司 | 一种瑞舒伐他汀钙杂质及其制备方法与用途 |
| CN114280181B (zh) * | 2021-12-23 | 2024-06-18 | 浙江海翔川南药业有限公司 | 一种瑞舒伐他汀中间体及其有关物质的检测方法 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US37314A (en) * | 1863-01-06 | Improved composition for lemonade | ||
| US633198A (en) * | 1899-02-08 | 1899-09-19 | Wilhelm Magnus Hoekerstedt | Automatic-lighting torch. |
| US4231938A (en) | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| US4444784A (en) | 1980-08-05 | 1984-04-24 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| DK149080C (da) | 1980-06-06 | 1986-07-28 | Sankyo Co | Fremgangsmaade til fremstilling af derivater af ml-236b-carboxylsyre |
| US4739073A (en) | 1983-11-04 | 1988-04-19 | Sandoz Pharmaceuticals Corp. | Intermediates in the synthesis of indole analogs of mevalonolactone and derivatives thereof |
| NO177005C (no) | 1988-01-20 | 1995-07-05 | Bayer Ag | Analogifremgangsmåte for fremstilling av substituerte pyridiner, samt mellomprodukter til bruk ved fremstillingen |
| US5177080A (en) | 1990-12-14 | 1993-01-05 | Bayer Aktiengesellschaft | Substituted pyridyl-dihydroxy-heptenoic acid and its salts |
| JP3233403B2 (ja) | 1991-06-19 | 2001-11-26 | 塩野義製薬株式会社 | 光学活性な中間体および該製造法 |
| JP2648897B2 (ja) | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| GB9626746D0 (en) | 1996-12-23 | 1997-02-12 | Knoll Ag | Process |
| GB9812413D0 (en) | 1998-06-10 | 1998-08-05 | Glaxo Group Ltd | Compound and its use |
| SI20070A (sl) | 1998-09-18 | 2000-04-30 | LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. | Nove soli inhibitorjev HMG-CoA reduktaze |
| GB9903472D0 (en) | 1999-02-17 | 1999-04-07 | Zeneca Ltd | Chemical process |
| GB0001621D0 (en) | 2000-01-26 | 2000-03-15 | Astrazeneca Ab | Pharmaceutical compositions |
| GB0003305D0 (en) | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| GB0028429D0 (en) | 2000-11-22 | 2001-01-10 | Astrazeneca Ab | Therapy |
| KR20040026705A (ko) | 2001-08-16 | 2004-03-31 | 테바 파마슈티컬 인더스트리즈 리미티드 | 스타틴의 칼슘 염 형태의 제조 방법 |
| AU2002324715B2 (en) * | 2001-08-16 | 2009-03-12 | Teva Pharmaceutical Industries Ltd. | Processes for preparing calcium salt forms of statins |
| SE0103509D0 (sv) | 2001-10-19 | 2001-10-19 | Astrazeneca Ab | Rosuvastatin in pre demented states |
| KR100511533B1 (ko) | 2002-04-09 | 2005-08-31 | 임광민 | 키랄 중간체, 그의 제조방법 및 그를 이용한 HMG-CoA환원저해제의 제조방법 |
| EA200401533A1 (ru) | 2002-05-21 | 2005-06-30 | Ранбакси Лабораторис Лимитед | Способ получения росувастатина |
| GB0218781D0 (en) * | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| DK1578733T3 (da) | 2002-12-10 | 2011-06-14 | Ranbaxy Lab Ltd | Fremgangsmåde til fremstilling af rosuvastatin |
| WO2005021511A1 (en) | 2003-08-27 | 2005-03-10 | Hetero Drugs Limited | A novel process for amorphous rosuvastatin calcium |
| EP1678148A1 (en) | 2003-10-22 | 2006-07-12 | Ranbaxy Laboratories Limited | Process for the preparation of amorphous rosuvastatin calcium |
| CA2546701C (en) | 2003-11-24 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
| CN1894221B (zh) * | 2003-12-02 | 2012-08-08 | 特瓦制药工业有限公司 | 用于表征罗苏伐他汀的参照标准品 |
| EP1797046A2 (en) | 2004-09-27 | 2007-06-20 | Ranbaxy Laboratories Limited | Novel processes for preparing amorphous rosuvastatin calcium and a novel polymorphic form of rosuvastatin sodium |
| WO2006079611A1 (en) | 2005-01-31 | 2006-08-03 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of rosuvastatin calcium salt |
| WO2006100689A1 (en) | 2005-03-22 | 2006-09-28 | Unichem Laboratories Limited | Process for preparation of rosuvastatin |
| WO2006106526A1 (en) | 2005-04-04 | 2006-10-12 | Unichem Laboratories Limited | Process for preparation of calcium salt of rosuvastatin |
| WO2006136408A2 (en) | 2005-06-24 | 2006-12-28 | Lek Pharmaceuticals D.D. | Process for preparing pure amorphous rosuvastatin calcium |
| CA2612587C (en) | 2005-06-24 | 2013-02-19 | Lek Pharmaceuticals D.D. | Process for preparing amorphous rosuvastatin calcium free of impurities |
| GB0514078D0 (en) | 2005-07-08 | 2005-08-17 | Astrazeneca Uk Ltd | Chemical process |
-
2004
- 2004-12-02 CN CN2004800359220A patent/CN1894221B/zh not_active Expired - Fee Related
- 2004-12-02 KR KR1020067013302A patent/KR100887264B1/ko not_active Expired - Fee Related
- 2004-12-02 ES ES04812772T patent/ES2364143T3/es not_active Expired - Lifetime
- 2004-12-02 CA CA002546894A patent/CA2546894C/en not_active Expired - Fee Related
- 2004-12-02 PT PT04812772T patent/PT1689723E/pt unknown
- 2004-12-02 US US11/001,912 patent/US7244844B2/en not_active Expired - Lifetime
- 2004-12-02 AT AT04812772T patent/ATE507209T1/de not_active IP Right Cessation
- 2004-12-02 TW TW093137210A patent/TWI351958B/zh not_active IP Right Cessation
- 2004-12-02 DE DE602004032465T patent/DE602004032465D1/de not_active Expired - Lifetime
- 2004-12-02 EP EP04812772A patent/EP1689723B1/en not_active Revoked
- 2004-12-02 WO PCT/US2004/040329 patent/WO2005056534A1/en not_active Ceased
- 2004-12-02 JP JP2006541502A patent/JP4733047B2/ja not_active Expired - Fee Related
-
2006
- 2006-05-09 IL IL175511A patent/IL175511A/en active IP Right Grant
-
2007
- 2007-06-25 US US11/821,968 patent/US7692008B2/en not_active Expired - Fee Related
- 2007-06-25 US US11/823,019 patent/US7692009B2/en not_active Expired - Fee Related
- 2007-06-25 US US11/823,045 patent/US7692010B2/en not_active Expired - Fee Related
- 2007-06-25 US US11/823,013 patent/US7741482B2/en not_active Expired - Fee Related
-
2009
- 2009-01-27 US US12/322,042 patent/US8487097B2/en not_active Expired - Fee Related
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