JP7323876B2 - クロピドグレル硫酸塩のｉ型結晶の製造方法 - Google Patents
クロピドグレル硫酸塩のｉ型結晶の製造方法 Download PDFInfo
- Publication number
- JP7323876B2 JP7323876B2 JP2020530274A JP2020530274A JP7323876B2 JP 7323876 B2 JP7323876 B2 JP 7323876B2 JP 2020530274 A JP2020530274 A JP 2020530274A JP 2020530274 A JP2020530274 A JP 2020530274A JP 7323876 B2 JP7323876 B2 JP 7323876B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- crystals
- clopidogrel
- butanol
- methyl
- 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.)
- Active
Links
- 229960003009 clopidogrel Drugs 0.000 title claims description 108
- 239000013078 crystal Substances 0.000 title claims description 88
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 title claims description 52
- 238000004519 manufacturing process Methods 0.000 title claims description 43
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 242
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 67
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 53
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 32
- 239000012458 free base Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000001035 drying Methods 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- FDEODCTUSIWGLK-RSAXXLAASA-N clopidogrel sulfate Chemical compound [H+].OS([O-])(=O)=O.C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl FDEODCTUSIWGLK-RSAXXLAASA-N 0.000 description 56
- 229940126214 compound 3 Drugs 0.000 description 24
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 229940125782 compound 2 Drugs 0.000 description 14
- 238000001914 filtration Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- ZTHQBROSBNNGPU-UHFFFAOYSA-N Butyl hydrogen sulfate Chemical compound CCCCOS(O)(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 3
- 238000009423 ventilation Methods 0.000 description 3
- PNJGTZKNMFFNPI-UQKRIMTDSA-N COS(O)(=O)=O.C1([C@H](N2CC=3C=CSC=3CC2)C(=O)O)=CC=CC=C1Cl Chemical compound COS(O)(=O)=O.C1([C@H](N2CC=3C=CSC=3CC2)C(=O)O)=CC=CC=C1Cl PNJGTZKNMFFNPI-UQKRIMTDSA-N 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- -1 for example Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2018132101 | 2018-07-12 | ||
| JP2018132101 | 2018-07-12 | ||
| PCT/JP2019/027621 WO2020013305A1 (ja) | 2018-07-12 | 2019-07-12 | クロピドグレル硫酸塩のｉ型結晶の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPWO2020013305A1 JPWO2020013305A1 (ja) | 2021-07-15 |
| JPWO2020013305A5 JPWO2020013305A5 (https=) | 2022-07-12 |
| JP7323876B2 true JP7323876B2 (ja) | 2023-08-09 |
Family
ID=69143064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020530274A Active JP7323876B2 (ja) | 2018-07-12 | 2019-07-12 | クロピドグレル硫酸塩のｉ型結晶の製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP7323876B2 (https=) |
| CN (1) | CN112399969B (https=) |
| WO (1) | WO2020013305A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117447485A (zh) * | 2023-10-23 | 2024-01-26 | 苏州正济药业有限公司 | 硫酸氢氯吡格雷的纯化方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040132765A1 (en) | 2002-10-21 | 2004-07-08 | Dinamite Dipharma S.P.A. | Clopidogrel salts with alkyl-sulphuric acids |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005514387A (ja) * | 2001-12-18 | 2005-05-19 | 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 | クロピドグレル硫酸水素塩の多型体 |
| US6767913B2 (en) * | 2001-12-18 | 2004-07-27 | Teva Pharmaceutical Industries Ltd. | Crystal forms iii, iv, v, and novel amorphous form of clopidogrel hydrogensulfate, processes for their preparation, processes for the preparation of form i, compositions containing the new forms and methods of administering the new forms |
| PL382055A1 (pl) * | 2007-03-23 | 2008-09-29 | Koźluk Tomasz Nobilus Ent | Sposób wytwarzania formy krystalicznej 1 wodorosiarczanu klopidogrelu |
| WO2011042804A2 (en) * | 2009-10-08 | 2011-04-14 | Jubliant Life Sciences Limited | An improved process for the preparation of clopidogrel hydrogen sulfate form i |
-
2019
- 2019-07-12 WO PCT/JP2019/027621 patent/WO2020013305A1/ja not_active Ceased
- 2019-07-12 JP JP2020530274A patent/JP7323876B2/ja active Active
- 2019-07-12 CN CN201980046516.0A patent/CN112399969B/zh not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040132765A1 (en) | 2002-10-21 | 2004-07-08 | Dinamite Dipharma S.P.A. | Clopidogrel salts with alkyl-sulphuric acids |
Non-Patent Citations (1)
| Title |
|---|
| RENOU, Ludovic et al.，Synthesis and X-ray structural studies of the dextro-rotatory enantiomer of methyl a-5(4,5,6,7-tetra，Journal of Molecular Structure，2007年，Vol.827，pp.108-113 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112399969A (zh) | 2021-02-23 |
| WO2020013305A1 (ja) | 2020-01-16 |
| CN112399969B (zh) | 2023-10-27 |
| JPWO2020013305A1 (ja) | 2021-07-15 |
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