JP2010518145A5 - - Google Patents
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- Publication number
- JP2010518145A5 JP2010518145A5 JP2009549413A JP2009549413A JP2010518145A5 JP 2010518145 A5 JP2010518145 A5 JP 2010518145A5 JP 2009549413 A JP2009549413 A JP 2009549413A JP 2009549413 A JP2009549413 A JP 2009549413A JP 2010518145 A5 JP2010518145 A5 JP 2010518145A5
- Authority
- JP
- Japan
- Prior art keywords
- salt
- solvent
- acid
- vinflunine
- ether
- 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.)
- Pending
Links
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical class C([C@@](C1=C(C2=CC=CC=C2N1)C1)(C2=C(OC)C=C3N(C)[C@@H]4[C@@]5(C3=C2)CCN2CC=C[C@]([C@@H]52)([C@H]([C@]4(O)C(=O)OC)OC(C)=O)CC)C(=O)OC)[C@H]2C[C@@H](C(C)(F)F)CN1C2 NMDYYWFGPIMTKO-HBVLKOHWSA-N 0.000 claims 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- 238000004519 manufacturing process Methods 0.000 claims 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- 239000011877 solvent mixture Substances 0.000 claims 4
- 229960000922 vinflunine Drugs 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 230000032683 aging Effects 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 150000007522 mineralic acids Chemical class 0.000 claims 3
- 150000007524 organic acids Chemical class 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- 239000003208 petroleum Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 claims 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 229960004365 benzoic acid Drugs 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 230000003902 lesion Effects 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 230000003595 spectral effect Effects 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0753211A FR2912406B1 (fr) | 2007-02-13 | 2007-02-13 | Sels cristalins anhydres de vinflunine, procede de preparation et utilisation en tant que medicament et moyen de purification de la vinflunine. |
| US89412707P | 2007-03-09 | 2007-03-09 | |
| PCT/EP2008/051755 WO2008098970A1 (en) | 2007-02-13 | 2008-02-13 | Anhydrous crystalline vinflunine salts, method of preparation and use thereof as a drug and means of vinflunine purification |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010518145A JP2010518145A (ja) | 2010-05-27 |
| JP2010518145A5 true JP2010518145A5 (enExample) | 2011-03-31 |
Family
ID=38577387
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009549413A Pending JP2010518145A (ja) | 2007-02-13 | 2008-02-13 | 無水結晶ビンフルニン塩、その製造方法ならびに薬物およびビンフルニン精製手段としてのその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8343991B2 (enExample) |
| EP (1) | EP2121708A1 (enExample) |
| JP (1) | JP2010518145A (enExample) |
| CN (1) | CN101652374B (enExample) |
| CA (1) | CA2677269C (enExample) |
| FR (1) | FR2912406B1 (enExample) |
| RU (1) | RU2456291C2 (enExample) |
| WO (1) | WO2008098970A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101607968A (zh) * | 2008-06-17 | 2009-12-23 | 江苏豪森药业股份有限公司 | 长春氟宁盐、其制备方法及其药物组合物 |
| CN103607891A (zh) * | 2011-04-12 | 2014-02-26 | 恩多塞特公司 | 固体药用组合物 |
| CN105121447B (zh) * | 2013-04-19 | 2018-02-02 | 暨南大学 | 长春碱类衍生物及其制备方法和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL4066C (enExample) | 1920-04-02 | |||
| FR2707988B1 (fr) * | 1993-07-21 | 1995-10-13 | Pf Medicament | Nouveaux dérivés antimitotiques des alcaloïdes binaires du catharantus rosesus, leur procédé de préparation et les compositions pharmaceutiques les comprenant. |
| FR2761990B1 (fr) * | 1997-04-10 | 1999-06-25 | Pf Medicament | Derives halogenes antimitotiques d'alcaloides de vinca |
| AR024852A1 (es) * | 2000-01-12 | 2002-10-30 | Eriochem Sa | Procedimiento para la produccion de ditartrato de 5'-nor-anhidrovinblastina a partir de especies vegetales del genero catharanthus y procedimiento a escala industrial. |
| FR2863891B1 (fr) * | 2003-12-23 | 2006-03-24 | Pf Medicament | Composition pharmaceutique de vinflunine destinee a une administration parentale, procede de preparation et utilisation |
| FR2894966B1 (fr) * | 2005-12-20 | 2008-03-14 | Pierre Fabre Medicament Sa | Nouvelle forme cristalline de la vinflunine |
-
2007
- 2007-02-13 FR FR0753211A patent/FR2912406B1/fr active Active
-
2008
- 2008-02-13 EP EP08716836A patent/EP2121708A1/en not_active Withdrawn
- 2008-02-13 JP JP2009549413A patent/JP2010518145A/ja active Pending
- 2008-02-13 CN CN2008800082409A patent/CN101652374B/zh not_active Expired - Fee Related
- 2008-02-13 CA CA2677269A patent/CA2677269C/en not_active Expired - Fee Related
- 2008-02-13 US US12/524,898 patent/US8343991B2/en not_active Expired - Fee Related
- 2008-02-13 RU RU2009133244/04A patent/RU2456291C2/ru not_active IP Right Cessation
- 2008-02-13 WO PCT/EP2008/051755 patent/WO2008098970A1/en not_active Ceased
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