CN105037331A - 瑞舒伐他汀中间体的制备方法 - Google Patents
瑞舒伐他汀中间体的制备方法 Download PDFInfo
- Publication number
- CN105037331A CN105037331A CN201510339081.2A CN201510339081A CN105037331A CN 105037331 A CN105037331 A CN 105037331A CN 201510339081 A CN201510339081 A CN 201510339081A CN 105037331 A CN105037331 A CN 105037331A
- Authority
- CN
- China
- Prior art keywords
- methyl
- fluorophenyl
- pyrimidine
- oxo
- heptenoic acid
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 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 description 5
- 229960000672 rosuvastatin Drugs 0.000 title abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 10
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 abstract description 16
- -1 1,1-dimethylethyl ester Chemical class 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 abstract description 2
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 238000013019 agitation Methods 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- HNNFDXWDCFCVDM-UHFFFAOYSA-N methyl 4-methyl-3-oxopentanoate Chemical compound COC(=O)CC(=O)C(C)C HNNFDXWDCFCVDM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510339081.2A CN105037331B (zh) | 2015-06-17 | 2015-06-17 | 瑞舒伐他汀中间体的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510339081.2A CN105037331B (zh) | 2015-06-17 | 2015-06-17 | 瑞舒伐他汀中间体的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105037331A true CN105037331A (zh) | 2015-11-11 |
CN105037331B CN105037331B (zh) | 2018-02-09 |
Family
ID=54444364
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510339081.2A Active CN105037331B (zh) | 2015-06-17 | 2015-06-17 | 瑞舒伐他汀中间体的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105037331B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108997324A (zh) * | 2018-08-21 | 2018-12-14 | 南京欧信医药技术有限公司 | 瑞舒伐他汀钙中间体的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1878752A (zh) * | 2003-11-14 | 2006-12-13 | 巴斯福股份公司 | 缩氨基脲化合物的顺-反异构化 |
EP1978020A1 (en) * | 2007-04-03 | 2008-10-08 | LEK Pharmaceuticals D.D. | Processes for the preparation of statins, particularly rosuvastatin, and intermediates for the preparation thereof |
CN101376647A (zh) * | 2007-08-31 | 2009-03-04 | 中山奕安泰医药科技有限公司 | 一种用于合成瑞舒伐他汀中间体及瑞舒伐他汀的合成方法 |
CN103113356A (zh) * | 2013-03-07 | 2013-05-22 | 上海现代制药股份有限公司 | 一种罗苏伐他汀钙的中间体的制备方法 |
WO2014108795A2 (en) * | 2013-01-10 | 2014-07-17 | Aurobindo Pharma Limited | An improved process for the preparation of chiral diol sulfones and statins |
-
2015
- 2015-06-17 CN CN201510339081.2A patent/CN105037331B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1878752A (zh) * | 2003-11-14 | 2006-12-13 | 巴斯福股份公司 | 缩氨基脲化合物的顺-反异构化 |
EP1978020A1 (en) * | 2007-04-03 | 2008-10-08 | LEK Pharmaceuticals D.D. | Processes for the preparation of statins, particularly rosuvastatin, and intermediates for the preparation thereof |
CN101376647A (zh) * | 2007-08-31 | 2009-03-04 | 中山奕安泰医药科技有限公司 | 一种用于合成瑞舒伐他汀中间体及瑞舒伐他汀的合成方法 |
WO2014108795A2 (en) * | 2013-01-10 | 2014-07-17 | Aurobindo Pharma Limited | An improved process for the preparation of chiral diol sulfones and statins |
CN103113356A (zh) * | 2013-03-07 | 2013-05-22 | 上海现代制药股份有限公司 | 一种罗苏伐他汀钙的中间体的制备方法 |
Non-Patent Citations (3)
Title |
---|
JAN FABRIS,等: "Conformational analysis of E/Z-isomeric pairs of rosuvastatin and its lactonized analogues", 《TETRAHEDRON》 * |
汪东风: "《高级食品化学》", 31 March 2009, 化学工业出版社 * |
胡宏纹,等: "《有机化学》", 31 May 2006, 高等教育出版社 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108997324A (zh) * | 2018-08-21 | 2018-12-14 | 南京欧信医药技术有限公司 | 瑞舒伐他汀钙中间体的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN105037331B (zh) | 2018-02-09 |
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GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180917 Address after: 315700 112 yuan Road, Xiangshan Industrial Park, Ningbo, Zhejiang Patentee after: Ningbo Yihe Medical Technology Co., Ltd. Address before: 310023 No. 318, Liu He road, Hangzhou, Zhejiang Patentee before: Zhejiang University of Science and Technology |
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TR01 | Transfer of patent right |
Effective date of registration: 20181129 Address after: 318000 29 Binhai Road, Jiaojiang District, Taizhou, Zhejiang Patentee after: Zhejiang Le Pu pharmaceutical Limited by Share Ltd Address before: 315700 112 yuan Road, Xiangshan Industrial Park, Ningbo, Zhejiang Patentee before: Ningbo Yihe Medical Technology Co., Ltd. |
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TR01 | Transfer of patent right |