CN101892276B - 一种阿托伐他汀钙化合物及其新方法 - Google Patents
一种阿托伐他汀钙化合物及其新方法 Download PDFInfo
- Publication number
- CN101892276B CN101892276B CN2010101984620A CN201010198462A CN101892276B CN 101892276 B CN101892276 B CN 101892276B CN 2010101984620 A CN2010101984620 A CN 2010101984620A CN 201010198462 A CN201010198462 A CN 201010198462A CN 101892276 B CN101892276 B CN 101892276B
- Authority
- CN
- China
- Prior art keywords
- midbody
- atorvastatincalcuim
- reaction
- solution
- iii
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- OJRHUICOVVSGSY-RXMQYKEDSA-N (2s)-2-chloro-3-methylbutan-1-ol Chemical compound CC(C)[C@H](Cl)CO OJRHUICOVVSGSY-RXMQYKEDSA-N 0.000 title claims abstract description 11
- 229960001770 atorvastatin calcium Drugs 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims abstract description 9
- 239000001639 calcium acetate Substances 0.000 claims abstract description 9
- 229960005147 calcium acetate Drugs 0.000 claims abstract description 9
- 235000011092 calcium acetate Nutrition 0.000 claims abstract description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000020477 pH reduction Effects 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000001291 vacuum drying Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- ALQNUOMIEBHXQG-CRCLSJGQSA-N 2-deoxy-D-ribose 5-phosphate Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)CC=O ALQNUOMIEBHXQG-CRCLSJGQSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 6
- -1 amino propionic aldehyde Glycol Acetal Chemical class 0.000 claims description 6
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000000967 suction filtration Methods 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Natural products CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- 239000008363 phosphate buffer Substances 0.000 claims description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 3
- 230000001143 conditioned effect Effects 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 3
- 239000011259 mixed solution Substances 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000007858 starting material Substances 0.000 abstract 2
- PCXDJQZLDDHMGX-UHFFFAOYSA-N 3-aminopropanal Chemical compound NCCC=O PCXDJQZLDDHMGX-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 230000007547 defect Effects 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 229960005370 atorvastatin Drugs 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- OUCSEDFVYPBLLF-KAYWLYCHSA-N 5-(4-fluorophenyl)-1-[2-[(2r,4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-n,4-diphenyl-2-propan-2-ylpyrrole-3-carboxamide Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@H]2OC(=O)C[C@H](O)C2)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 OUCSEDFVYPBLLF-KAYWLYCHSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- BJGBAZAEWKCPHZ-MQSFZEHASA-N (3r,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1.C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 BJGBAZAEWKCPHZ-MQSFZEHASA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- VZVOJBSCPTXOCN-GORYFVAVSA-N CC(C)c1c(C(Nc2ccccc2)=O)c(-c2ccccc2)c(-c(cc2)ccc2F)[n]1CC[C@H](C[C@H](C1)O)OC1O Chemical compound CC(C)c1c(C(Nc2ccccc2)=O)c(-c2ccccc2)c(-c(cc2)ccc2F)[n]1CC[C@H](C[C@H](C1)O)OC1O VZVOJBSCPTXOCN-GORYFVAVSA-N 0.000 description 1
- 0 CC(C)c1c(C(Nc2ccccc2)=O)c(-c2ccccc2)c(-c(cc2)ccc2F)[n]1CC[C@](C[C@@](*)C1)OC1=O Chemical compound CC(C)c1c(C(Nc2ccccc2)=O)c(-c2ccccc2)c(-c(cc2)ccc2F)[n]1CC[C@](C[C@@](*)C1)OC1=O 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 208000031288 Combined hyperlipidaemia Diseases 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 1
- 108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010101984620A CN101892276B (zh) | 2010-06-12 | 2010-06-12 | 一种阿托伐他汀钙化合物及其新方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2010101984620A CN101892276B (zh) | 2010-06-12 | 2010-06-12 | 一种阿托伐他汀钙化合物及其新方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101892276A CN101892276A (zh) | 2010-11-24 |
CN101892276B true CN101892276B (zh) | 2012-11-21 |
Family
ID=43101621
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2010101984620A Expired - Fee Related CN101892276B (zh) | 2010-06-12 | 2010-06-12 | 一种阿托伐他汀钙化合物及其新方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101892276B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103012240B (zh) * | 2012-12-11 | 2015-05-27 | 保定市龙瑞药物技术有限责任公司 | 一种阿托伐他汀钙的制备方法 |
CN113373187B (zh) * | 2021-05-26 | 2023-11-10 | 江苏阿尔法药业股份有限公司 | 一种氮杂环化合物c27h30fno6的酶催化合成方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1489587A (zh) * | 2001-01-09 | 2004-04-14 | ����-�����ع�˾ | 合成5-(4-氟苯基)-1-[2-((2r,4r)-4-羟基-6-氧代-四氢吡喃-2-基)-乙基]-2-异丙基-4-苯基-1h-吡咯-3-甲酸苯基酰胺的新方法 |
CN1692906A (zh) * | 2004-04-30 | 2005-11-09 | 鲁南制药集团股份有限公司 | 治疗高血脂症的组合物 |
CN1774421A (zh) * | 2003-04-14 | 2006-05-17 | 沃尼尔·朗伯有限责任公司 | 制备5-(4-氟苯基)-1-[2-((2r,4r)-4-羟基-6-氧代-四氢-吡喃-2-基)乙基]-2-异丙基-4-苯基-1h-吡咯-3-羧酸苯基酰胺的方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001072706A1 (en) * | 2000-03-28 | 2001-10-04 | Biocon India Limited | Synthesis of [r-(r*,r*)]-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1h-pyrrole-1-heptanoic acid hemi calcium salt (atorvastatin) |
-
2010
- 2010-06-12 CN CN2010101984620A patent/CN101892276B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1489587A (zh) * | 2001-01-09 | 2004-04-14 | ����-�����ع�˾ | 合成5-(4-氟苯基)-1-[2-((2r,4r)-4-羟基-6-氧代-四氢吡喃-2-基)-乙基]-2-异丙基-4-苯基-1h-吡咯-3-甲酸苯基酰胺的新方法 |
CN1774421A (zh) * | 2003-04-14 | 2006-05-17 | 沃尼尔·朗伯有限责任公司 | 制备5-(4-氟苯基)-1-[2-((2r,4r)-4-羟基-6-氧代-四氢-吡喃-2-基)乙基]-2-异丙基-4-苯基-1h-吡咯-3-羧酸苯基酰胺的方法 |
CN1692906A (zh) * | 2004-04-30 | 2005-11-09 | 鲁南制药集团股份有限公司 | 治疗高血脂症的组合物 |
Also Published As
Publication number | Publication date |
---|---|
CN101892276A (zh) | 2010-11-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4234429B2 (ja) | 水酸化カルシウムによる〔R(R*,R*)〕−2−(4−フルオロフェニル)−β,δ−ジヒドロキシ−5−(1−メチルエチル)−3−フェニル−4−〔(フェニルアミノ)カルボニル〕−1H−ピロール−1−ヘプタン酸エステルの加水分解 | |
CN1543468A (zh) | 制备他汀类的钙盐形式的方法 | |
CN102605034B (zh) | 一种制备光学纯(s)-5-(4-氟苯基)-5-羟基戊酸甲酯的生物酶拆分法 | |
CN1821242A (zh) | 制备二羟基酸HMG-CoA还原酶抑制剂的新方法 | |
CN101039917A (zh) | 制备替米沙坦的方法 | |
CN101386592A (zh) | 利用不对称氢化制备匹伐他汀钙原料药的方法 | |
CN1958593A (zh) | 一种用于合成瑞舒伐他汀钙的中间体的制备方法 | |
CN101892276B (zh) | 一种阿托伐他汀钙化合物及其新方法 | |
JP2017524742A (ja) | テトラヒドロキノリン誘導体の調製のための合成中間体の調製方法 | |
CN105085362A (zh) | 高纯度结晶型阿托伐他汀钙的制备方法 | |
CN101560177A (zh) | 一种阿托伐他汀钙的制备方法 | |
CN1526700A (zh) | 枸橼酸莫沙必利重要中间体的合成工艺 | |
CN1730460A (zh) | 一种一锅法制备咖啡酸酯衍生物的方法 | |
WO2019029554A1 (zh) | 磺酰胺类衍生物、其制备方法及其在医药上的用途 | |
KR20100052230A (ko) | 피타바스타틴 중간체의 제조방법 및 이를 이용한 피타바스타틴 헤미 칼슘염의 제조방법 | |
CN106854177A (zh) | 一种6‑氯‑4羟基吡啶‑3‑甲醛的制备方法 | |
KR101498802B1 (ko) | 키랄 2-아미노-4h-크로멘 유도체의 제조방법 | |
Wu et al. | CuLi2Cl4 catalysed cross-coupling strategy for the formal synthesis of the diterpenoid (+)-subersic acid from (–)-sclareol | |
WO2004092121A2 (en) | Methods for preparing 2,3,5,6-substituted 3h-pyrimidin-4-ones | |
IL206433A (en) | A method for producing a cyclopropanecarboxylic acid compound and an intermediate for it | |
JP3987942B2 (ja) | 多置換シクロブタン及び多置換シクロブテン化合物の製造方法 | |
US8859786B2 (en) | Preparation of 3,5-dioxo hexanoate ester in two steps | |
CN104447487A (zh) | 一种阿托伐他汀半钙的制备方法 | |
JPH08104686A (ja) | ラセミ脂肪族ヘテロ環カルボン酸エステル、およびラセミ脂肪族ヘテロ環カルボン酸の製造方法 | |
CN115260051A (zh) | 一种阿托伐他汀钙中间体的制备工艺 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: HAINAN MEIDA PHARMACEUTICAL CO., LTD. Free format text: FORMER OWNER: HAO ZHIYAN Effective date: 20130724 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 570125 HAIKOU, HAINAN PROVINCE TO: 570216 HAIKOU, HAINAN PROVINCE |
|
TR01 | Transfer of patent right |
Effective date of registration: 20130724 Address after: 570216 C03, Haikou Free Trade Zone, Hainan, China Patentee after: Hainan Meida Pharmaceutical Co., Ltd. Address before: The new business building No. 48 570125 Hainan city of Haikou province China World Trade Center Road, room 2601 Patentee before: Hao Zhiyan |
|
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20121121 Termination date: 20160612 |