CN105237517A - 结晶的雷迪帕韦化合物及其制备方法 - Google Patents
结晶的雷迪帕韦化合物及其制备方法 Download PDFInfo
- Publication number
- CN105237517A CN105237517A CN201510732832.7A CN201510732832A CN105237517A CN 105237517 A CN105237517 A CN 105237517A CN 201510732832 A CN201510732832 A CN 201510732832A CN 105237517 A CN105237517 A CN 105237517A
- Authority
- CN
- China
- Prior art keywords
- lei dipawei
- acetone
- preparation
- compound
- dipawei
- 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
- -1 Ledipasvir compound Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 229960002461 ledipasvir Drugs 0.000 title abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 100
- 239000012453 solvate Substances 0.000 claims description 22
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 239000013078 crystal Substances 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 7
- 230000008025 crystallization Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 208000006454 hepatitis Diseases 0.000 abstract 1
- 231100000283 hepatitis Toxicity 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 14
- 238000001514 detection method Methods 0.000 description 9
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 206010013786 Dry skin Diseases 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 241000711549 Hepacivirus C Species 0.000 description 3
- 208000005176 Hepatitis C Diseases 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229940126656 GS-4224 Drugs 0.000 description 2
- 102000014150 Interferons Human genes 0.000 description 2
- 108010050904 Interferons Proteins 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229940029169 harvoni Drugs 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229940079322 interferon Drugs 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 206010013654 Drug abuse Diseases 0.000 description 1
- 206010019799 Hepatitis viral Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- ZIQPQYFSSSHQBP-UHFFFAOYSA-N acetyl 2,3-dihydroxypropanoate Chemical compound CC(=O)OC(=O)C(O)CO ZIQPQYFSSSHQBP-UHFFFAOYSA-N 0.000 description 1
- 238000001467 acupuncture Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- VRTWBAAJJOHBQU-KMWAZVGDSA-N ledipasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N([C@@H](C1)C=2NC(=CN=2)C=2C=C3C(F)(F)C4=CC(=CC=C4C3=CC=2)C=2C=C3NC(=NC3=CC=2)[C@H]2N([C@@H]3CC[C@H]2C3)C(=O)[C@@H](NC(=O)OC)C(C)C)CC21CC2 VRTWBAAJJOHBQU-KMWAZVGDSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 229960002063 sofosbuvir Drugs 0.000 description 1
- TTZHDVOVKQGIBA-IQWMDFIBSA-N sofosbuvir Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@]2(F)C)O)CO[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)OC=2C=CC=CC=2)C=CC(=O)NC1=O TTZHDVOVKQGIBA-IQWMDFIBSA-N 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
时间 | 一丙酮物(丙酮含量) | 半丙酮物(丙酮含量) |
1h | 5.1% | 3.2% |
2h | 3.8% | 3.1% |
4h | 2.7% | 3.0% |
8h | 1.1% | 2.9% |
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510732832.7A CN105237517B (zh) | 2015-10-30 | 2015-10-30 | 结晶的雷迪帕韦化合物及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510732832.7A CN105237517B (zh) | 2015-10-30 | 2015-10-30 | 结晶的雷迪帕韦化合物及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105237517A true CN105237517A (zh) | 2016-01-13 |
CN105237517B CN105237517B (zh) | 2017-10-27 |
Family
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Family Applications (1)
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---|---|---|---|
CN201510732832.7A Expired - Fee Related CN105237517B (zh) | 2015-10-30 | 2015-10-30 | 结晶的雷迪帕韦化合物及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105237517B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016145269A1 (en) | 2015-03-12 | 2016-09-15 | Teva Pharmaceuticals International Gmbh | Solid state forms ledipasvir and processes for preparation of ledipasvir |
US11655201B2 (en) * | 2017-05-24 | 2023-05-23 | Biomedical Analysis Center, Academy Of Military Medical Sciences | Method for preparing 2-tert-butyl-4-methoxyphenol and new crystal form thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011156757A1 (en) * | 2010-06-10 | 2011-12-15 | Gilead Sciences, Inc. | Combination of anti-hcv compounds with ribavirin for the treatment of hcv |
CN104379584A (zh) * | 2012-06-05 | 2015-02-25 | 吉利德法莫赛特有限责任公司 | 抗病毒化合物的固体形式 |
CN104961733A (zh) * | 2015-07-06 | 2015-10-07 | 上海众强药业有限公司 | 雷迪帕韦新晶型及其制备方法 |
-
2015
- 2015-10-30 CN CN201510732832.7A patent/CN105237517B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011156757A1 (en) * | 2010-06-10 | 2011-12-15 | Gilead Sciences, Inc. | Combination of anti-hcv compounds with ribavirin for the treatment of hcv |
CN104379584A (zh) * | 2012-06-05 | 2015-02-25 | 吉利德法莫赛特有限责任公司 | 抗病毒化合物的固体形式 |
CN104961733A (zh) * | 2015-07-06 | 2015-10-07 | 上海众强药业有限公司 | 雷迪帕韦新晶型及其制备方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016145269A1 (en) | 2015-03-12 | 2016-09-15 | Teva Pharmaceuticals International Gmbh | Solid state forms ledipasvir and processes for preparation of ledipasvir |
US11655201B2 (en) * | 2017-05-24 | 2023-05-23 | Biomedical Analysis Center, Academy Of Military Medical Sciences | Method for preparing 2-tert-butyl-4-methoxyphenol and new crystal form thereof |
Also Published As
Publication number | Publication date |
---|---|
CN105237517B (zh) | 2017-10-27 |
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Address after: 210038 9 Hui Ou Road, Nanjing economic and Technological Development Zone, Jiangsu Co-patentee after: SUZHOU LANXITE BIOTECHNOLOGY Co.,Ltd. Patentee after: NANJING CHIA TAI TIANQING PHARMACEUTICAL Co.,Ltd. Address before: 210038 9 Hui Ou Road, Nanjing economic and Technological Development Zone, Jiangsu Co-patentee before: SUZHOU LANGKE BIOLOGICAL PHARMACEUTICAL CO.,LTD. Patentee before: NANJING CHIA TAI TIANQING PHARMACEUTICAL Co.,Ltd. |
|
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: 20171027 |