AR039836A1 - Proceso para la preparacion de un aldehido de pirimidina util para la preparacion de rosuvastatina - Google Patents
Proceso para la preparacion de un aldehido de pirimidina util para la preparacion de rosuvastatinaInfo
- Publication number
- AR039836A1 AR039836A1 ARP030101769A ARP030101769A AR039836A1 AR 039836 A1 AR039836 A1 AR 039836A1 AR P030101769 A ARP030101769 A AR P030101769A AR P030101769 A ARP030101769 A AR P030101769A AR 039836 A1 AR039836 A1 AR 039836A1
- Authority
- AR
- Argentina
- Prior art keywords
- structural formula
- derivative
- preparation
- pyrimidine
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 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 title abstract 2
- 229960000672 rosuvastatin Drugs 0.000 title abstract 2
- -1 N-methyl-N-methylsulfonylamino Chemical group 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- PWGLCBCNZAZIIE-UHFFFAOYSA-N 1-methyl-2h-pyrimidine Chemical class CN1CN=CC=C1 PWGLCBCNZAZIIE-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 150000001336 alkenes Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- UHNHTTIUNATJKL-UHFFFAOYSA-N n-methylmethanesulfonamide Chemical class CNS(C)(=O)=O UHNHTTIUNATJKL-UHFFFAOYSA-N 0.000 abstract 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 abstract 1
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical class C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 abstract 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 abstract 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 abstract 1
- 230000000326 anti-hypercholesterolaemic effect Effects 0.000 abstract 1
- 238000005899 aromatization reaction Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229910052748 manganese Inorganic materials 0.000 abstract 1
- 239000011572 manganese Substances 0.000 abstract 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 abstract 1
- CCOXWRVWKFVFDG-UHFFFAOYSA-N pyrimidine-2-carbaldehyde Chemical compound O=CC1=NC=CC=N1 CCOXWRVWKFVFDG-UHFFFAOYSA-N 0.000 abstract 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La rosuvastatina es útil como antihipercolesterolémico. Reivindicación 1: Un proceso para la preparación de 4-(4-fluorofenil)-6-isopropil-2-(N-metil-N-metilsulfonilamino)pirimidina-5-il-carboxaldehido de la fórmula estructural (1) que comprende: a) la condensación de 4-fluorobenzaldehido de la fórmula estructural (2) con un compuesto de la fórmula estructural (3), en donde R1 es independientemente alquilo C2-6, cicloalquilo C1-6 o aralquilo, para obtener una olefina de la fórmula estructural (4); b) la reacción de la olefina con isotiourea de la fórmula estructural (5), en donde R2 es independientemente alquilo C2-6, cicloalquilo C1-6, o aralquilo, para obtener un derivado dihidropirimidínico cíclico de la fórmula estructural (6); c) la aromatización del derivado de dihidropirimidina con dióxido de manganeso-g para obtener un compuesto de pirimidina de la fórmula estructural (7); d) la oxidación del compuesto de pirimidina para obtener un derivado sulfonilo de la fórmula estructural (8); e) la reacción del derivado de sulfonilo con metilamina para obtener un derivado de N-metilpirimidina de la fórmula estructural (9); f) la reacción del derivado de N-metilo pirimidina con cloruro de metanosulfonilo para obtener un derivado de N-metilo metanosulfonamida de la fórmula estructural (10); g) la reducción del derivado de N-metilo metanosulfonamida con hidruro de diisobutilaluminio (DIBAL) en tolueno para obtener un compuesto alcohólico de la fórmula estructural (11); y h) la oxidación del compuesto alcohólico para obtener un aldehido de pirimidina de la fórmula estructural (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN575DE2002 | 2002-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR039836A1 true AR039836A1 (es) | 2005-03-02 |
Family
ID=29434392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP030101769A AR039836A1 (es) | 2002-05-21 | 2003-05-21 | Proceso para la preparacion de un aldehido de pirimidina util para la preparacion de rosuvastatina |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20050222415A1 (es) |
| EP (1) | EP1585736A2 (es) |
| AR (1) | AR039836A1 (es) |
| AU (1) | AU2003228010A1 (es) |
| BR (1) | BR0311195A (es) |
| EA (1) | EA200401533A1 (es) |
| WO (1) | WO2003097614A2 (es) |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL159741A0 (en) | 2001-07-13 | 2004-06-20 | Astrazeneca Uk Ltd | Preparation of aminopyrimidine compounds |
| GB0218781D0 (en) | 2002-08-13 | 2002-09-18 | Astrazeneca Ab | Chemical process |
| GB0312896D0 (en) | 2003-06-05 | 2003-07-09 | Astrazeneca Ab | Chemical process |
| AU2003269478A1 (en) * | 2003-08-27 | 2005-03-16 | Hetero Drugs Limited | A novel process for amorphous rosuvastatin calcium |
| EP1562912A2 (en) * | 2003-08-28 | 2005-08-17 | Teva Pharmaceutical Industries Limited | Process for preparation of rosuvastatin calcium |
| EP1816126A1 (en) * | 2003-08-28 | 2007-08-08 | Teva Pharmaceutical Industries Limited | Process for preparation of rosuvastatin calcium |
| UY28501A1 (es) | 2003-09-10 | 2005-04-29 | Astrazeneca Uk Ltd | Compuestos químicos |
| GB0324791D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Chemical process |
| TW200526596A (en) | 2003-11-24 | 2005-08-16 | Teva Pharma | Crystalline ammonium salts of rosuvastatin |
| CA2546894C (en) | 2003-12-02 | 2009-09-08 | Teva Pharmaceutical Industries Ltd. | Reference standard for characterization of rosuvastatin |
| US7851624B2 (en) | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
| CA2573857A1 (en) * | 2004-07-13 | 2006-02-16 | Teva Pharmaceutical Industries Ltd. | A process for the preparation of rosuvastatin involving a tempo-mediated oxidation step |
| CZ298330B6 (cs) * | 2004-07-19 | 2007-08-29 | Zentiva, A. S. | Zpusob výroby 4-(4-fluorfenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)-5-pyrimidinkarbaldehydu a jeho použití |
| KR100622494B1 (ko) * | 2004-09-06 | 2006-09-19 | 현대자동차주식회사 | 조향 휠의 조립 구조 |
| CN1763015B (zh) * | 2004-10-22 | 2011-06-22 | 四川抗菌素工业研究所有限公司 | 一种罗舒伐他汀及其药用盐的制备方法及中间体 |
| CN100351240C (zh) * | 2005-01-19 | 2007-11-28 | 安徽省庆云医药化工有限公司 | 瑞舒伐他汀钙的合成方法 |
| US20070037979A1 (en) * | 2005-02-22 | 2007-02-15 | Valerie Niddam-Hildesheim | Preparation of rosuvastatin |
| JP2008526781A (ja) | 2005-02-22 | 2008-07-24 | 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 | ロスバスタチンの製造 |
| US20070167625A1 (en) * | 2005-02-22 | 2007-07-19 | Anna Balanov | Preparation of rosuvastatin |
| CN101119975A (zh) * | 2005-02-22 | 2008-02-06 | 特瓦制药工业有限公司 | 罗舒伐他汀的制备 |
| US20090124803A1 (en) * | 2005-03-22 | 2009-05-14 | Pandurang Balwant Deshpande | Process for preparation of rosuvastatin |
| WO2006106526A1 (en) * | 2005-04-04 | 2006-10-12 | Unichem Laboratories Limited | Process for preparation of calcium salt of rosuvastatin |
| WO2006128954A1 (en) * | 2005-06-01 | 2006-12-07 | Fermion Oy | Process for the preparation of n-[4-(4-fluorophenyl)-5-formyl-6-isopropyl-pyrimidin-2-yl]-n-methylmethanesulfonamide |
| EP2508514B1 (en) | 2005-06-24 | 2017-10-18 | LEK Pharmaceuticals d.d. | Process for preparing amorphous rosuvastatin calcium free of impurities |
| KR20070062996A (ko) * | 2005-08-16 | 2007-06-18 | 테바 파마슈티컬 인더스트리즈 리미티드 | 결정성 로수바스타틴 중간체 |
| WO2007022366A2 (en) * | 2005-08-16 | 2007-02-22 | Teva Pharmaceutical Industries Ltd. | Rosuvastatin calcium with a low salt by-product content |
| CN100436428C (zh) * | 2005-08-22 | 2008-11-26 | 鲁南制药集团股份有限公司 | 瑞舒伐他汀及其盐的制备方法 |
| CA2624801A1 (en) * | 2005-10-03 | 2007-04-12 | Teva Pharmaceutical Industries Ltd. | Diastereomeric purification of rosuvastatin |
| WO2007074391A2 (en) * | 2005-12-28 | 2007-07-05 | Bakulesh Mafatlal Khamar | Preparation of a key intermediate in the synthesis of rosuvastatin |
| WO2007125547A2 (en) | 2006-05-03 | 2007-11-08 | Manne Satyanarayana Reddy | Novel process for statins and its pharmaceutically acceptable salts thereof |
| WO2008036286A1 (en) * | 2006-09-18 | 2008-03-27 | Teva Pharmaceutical Industries Ltd. | Crystalline rosuvastatin calcium |
| SI2086945T1 (sl) | 2006-10-09 | 2016-05-31 | Msn Laboratories Private Limited | Novi postopek za pripravo statinov in njihovih farmacevtsko sprejemljivih soli |
| EP2079712A2 (en) | 2006-10-31 | 2009-07-22 | Aurobindo Pharma Limited | An improved process for preparing rosuvastatin calcium |
| US8212034B2 (en) * | 2006-12-13 | 2012-07-03 | Aurobindo Pharma Ltd. | Process for preparing rosuvastatin calcium |
| WO2008093205A2 (en) * | 2007-01-31 | 2008-08-07 | Orchid Chemicals & Pharmaceuticals Limited | A method for the purification of rosuvastatin intermediate |
| EP2125754B1 (en) | 2007-02-08 | 2012-04-11 | Aurobindo Pharma Limited | Process for preparation of rosuvastatin calcium |
| PL2172471T3 (pl) | 2007-04-18 | 2013-08-30 | Teva Pharma | Sposób otrzymywania produktów pośrednich inhibitorów reduktazy HMG-CoA |
| CN101323597B (zh) * | 2007-06-11 | 2012-09-05 | 安徽省庆云医药化工有限公司 | 4-(4-氟苯基)-6-异丙基-2-(n-甲基-n-甲磺酰氨基)嘧啶-5-甲醛的制备方法 |
| US20090069563A1 (en) | 2007-07-12 | 2009-03-12 | Valerie Niddam-Hildesheim | Rosuvastatin intermediates and their preparation |
| EP2022784A1 (en) | 2007-08-08 | 2009-02-11 | LEK Pharmaceuticals D.D. | Process for the preparation of methyl ester of rosuvastatin |
| EA201000214A1 (ru) | 2007-08-28 | 2010-10-29 | Рациофарм Гмбх | Способ получения производных пентадикарбоновой кислоты |
| CA2725052C (en) | 2008-05-27 | 2014-09-16 | Changzhou Pharmaceutical Factory Co., Ltd. | Preparation method of rosuvastatin calcium and its intermediates |
| EP2350025A1 (en) * | 2008-09-30 | 2011-08-03 | Aurobindo Pharma Limited | An improved process for preparing pyrimidine propenaldehyde |
| SI2752407T1 (sl) | 2009-01-14 | 2016-07-29 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Kristalni kalcijev rosuvastatin trihidrat |
| BRPI1005147A2 (pt) | 2009-01-15 | 2019-09-24 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | processo de preparação de sais de rosuvastatina |
| WO2010089770A2 (en) | 2009-01-19 | 2010-08-12 | Msn Laboratories Limited | Improved process for the preparation of highly pure (3r,5s)-7-[2-cyclopropyl-4-(4-fluorophenyl) quinolin-3-yl]-3,5-dihydroxy-6(e)-heptenoic acid and pharmaceutically acceptable salts thereof |
| KR101160152B1 (ko) * | 2009-02-24 | 2012-06-27 | 한미사이언스 주식회사 | 스타틴 화합물 또는 그 염의 신규 제조방법, 및 이에 사용되는 중간체 화합물 |
| WO2011086584A2 (en) | 2010-01-18 | 2011-07-21 | Msn Laboratories Limited | Improved process for the preparation of amide intermediates and their use thereof |
| WO2011141934A1 (en) | 2010-05-13 | 2011-11-17 | Matrix Laboratories Ltd. | An improved process for the preparation of an intermediate of hmg-coa reductase inhibitors |
| WO2012011129A2 (en) * | 2010-07-22 | 2012-01-26 | Msn Laboratories Limited | Novel polymorph of bis[(e)-7-[4-(4-fluorophenyl)-6-iso-propyl-2-[methyl (methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoic acid] calcium salt |
| CN101955463B (zh) * | 2010-08-04 | 2012-01-04 | 重庆博腾制药科技股份有限公司 | 瑞舒伐他汀钙中间体的制备方法 |
| HU230987B1 (hu) | 2010-11-29 | 2019-08-28 | Egis Gyógyszergyár Nyrt. | Eljárás nagy tisztaságú gyógyszeripari intermedierek előállítására |
| JP6181063B2 (ja) | 2011-11-28 | 2017-08-16 | マイラン ラボラトリーズ リミテッドＭｙｌａｎ Ｌａｂｏｒａｔｏｒｉｅｓ Ｌｉｍｉｔｅｄ | ＨＭＧ−ＣｏＡレダクターゼ阻害剤の中間体の新規な製造方法 |
| CN103134893B (zh) * | 2013-01-25 | 2014-12-03 | 峨眉山天梁星制药有限公司 | 一种3-叔丁基二甲硅氧基戊二酸酐的高效液相色谱分析法 |
| CN111548312A (zh) * | 2020-06-01 | 2020-08-18 | 雅本化学股份有限公司 | 一种瑞舒伐他汀钙片及其制备工艺 |
| CN113754590B (zh) * | 2021-09-06 | 2023-06-13 | 浙江乐普药业股份有限公司 | 一种瑞舒伐他汀钙中间体的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2698326A (en) * | 1954-12-28 | S-aminomethylpyrimtoines | ||
| 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 |
| JP3400038B2 (ja) * | 1993-10-19 | 2003-04-28 | 塩野義製薬株式会社 | ピリミジン誘導体の製造方法 |
| DE4338866C1 (de) * | 1993-11-13 | 1995-06-14 | Wolf Gmbh Richard | Medizinisches Instrument zur Applikation von Heißgas |
| CZ298235B6 (cs) * | 1999-03-10 | 2007-08-01 | Lonza Ag | Zpusob výroby N-[5-(difenylfosfinoylmethyl)-4-(4-fluorfenyl)-6-isopropylpyrimidin-2-yl]-N-methylmethansulfonamidu |
| GB0003305D0 (en) * | 2000-02-15 | 2000-04-05 | Zeneca Ltd | Pyrimidine derivatives |
| IL160077A0 (en) * | 2001-08-16 | 2004-06-20 | Teva Pharma | Processes for preparing calcium salt forms of statins |
-
2003
- 2003-05-21 AU AU2003228010A patent/AU2003228010A1/en not_active Abandoned
- 2003-05-21 EP EP03725478A patent/EP1585736A2/en not_active Withdrawn
- 2003-05-21 AR ARP030101769A patent/AR039836A1/es unknown
- 2003-05-21 US US10/515,361 patent/US20050222415A1/en not_active Abandoned
- 2003-05-21 EA EA200401533A patent/EA200401533A1/ru unknown
- 2003-05-21 WO PCT/IB2003/001946 patent/WO2003097614A2/en not_active Ceased
- 2003-05-21 BR BR0311195-4A patent/BR0311195A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003097614A2 (en) | 2003-11-27 |
| EA200401533A1 (ru) | 2005-06-30 |
| AU2003228010A1 (en) | 2003-12-02 |
| WO2003097614A3 (en) | 2004-05-21 |
| US20050222415A1 (en) | 2005-10-06 |
| BR0311195A (pt) | 2005-02-22 |
| EP1585736A2 (en) | 2005-10-19 |
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