ES2222588T3 - Derivados halogenados antimitoticos de los alcanoides de vinca. - Google Patents
Derivados halogenados antimitoticos de los alcanoides de vinca.Info
- Publication number
- ES2222588T3 ES2222588T3 ES98920607T ES98920607T ES2222588T3 ES 2222588 T3 ES2222588 T3 ES 2222588T3 ES 98920607 T ES98920607 T ES 98920607T ES 98920607 T ES98920607 T ES 98920607T ES 2222588 T3 ES2222588 T3 ES 2222588T3
- Authority
- ES
- Spain
- Prior art keywords
- general formula
- compounds
- compound
- acid
- chloro
- 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 - Lifetime
Links
- 230000002927 anti-mitotic effect Effects 0.000 title claims description 3
- 241000863480 Vinca Species 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 claims description 5
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 claims description 4
- 229930013930 alkaloid Natural products 0.000 claims description 4
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- -1 silver tetrafluoroborate Chemical compound 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 abstract description 5
- 229960003048 vinblastine Drugs 0.000 abstract description 5
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 abstract description 5
- 229960002066 vinorelbine Drugs 0.000 abstract description 3
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 abstract description 3
- 239000000460 chlorine Substances 0.000 description 14
- 229940073584 methylene chloride Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229940122803 Vinca alkaloid Drugs 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000002512 chemotherapy Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- FFRFGVHNKJYNOV-DOVUUNBWSA-N 3',4'-Anhydrovinblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C=C(C2)CC)N2CCC2=C1NC1=CC=CC=C21 FFRFGVHNKJYNOV-DOVUUNBWSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000003930 superacid Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 240000001829 Catharanthus roseus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 101150062821 chlP gene Proteins 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 1
- ZEOVXNVKXIPWMS-UHFFFAOYSA-N 2,2-dichloropropane Chemical compound CC(C)(Cl)Cl ZEOVXNVKXIPWMS-UHFFFAOYSA-N 0.000 description 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- WVTGEXAIVZDLCR-UHFFFAOYSA-N Vindoline Natural products CC1C2CN3CCCC14CCC5Nc6ccccc6C25C34 WVTGEXAIVZDLCR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- CXBGOBGJHGGWIE-IYJDUVQVSA-N vindoline Chemical compound CN([C@H]1[C@](O)([C@@H]2OC(C)=O)C(=O)OC)C3=CC(OC)=CC=C3[C@]11CCN3CC=C[C@]2(CC)[C@@H]13 CXBGOBGJHGGWIE-IYJDUVQVSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9704398A FR2761990B1 (fr) | 1997-04-10 | 1997-04-10 | Derives halogenes antimitotiques d'alcaloides de vinca |
| FR9704398 | 1997-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2222588T3 true ES2222588T3 (es) | 2005-02-01 |
Family
ID=9505731
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98920607T Expired - Lifetime ES2222588T3 (es) | 1997-04-10 | 1998-04-10 | Derivados halogenados antimitoticos de los alcanoides de vinca. |
| ES06124480T Expired - Lifetime ES2347878T3 (es) | 1997-04-10 | 1998-04-10 | Derivados halogenados antimitoticos de los alcaloides de vinca. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES06124480T Expired - Lifetime ES2347878T3 (es) | 1997-04-10 | 1998-04-10 | Derivados halogenados antimitoticos de los alcaloides de vinca. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6127377A (enExample) |
| EP (3) | EP1764368B1 (enExample) |
| JP (3) | JP4401440B2 (enExample) |
| AT (2) | ATE473987T1 (enExample) |
| AU (1) | AU737549C (enExample) |
| BR (2) | BR9816177B1 (enExample) |
| CA (3) | CA2665949C (enExample) |
| CY (2) | CY1111476T1 (enExample) |
| DE (3) | DE69824840T2 (enExample) |
| DK (2) | DK0975640T3 (enExample) |
| ES (2) | ES2222588T3 (enExample) |
| FR (2) | FR2761990B1 (enExample) |
| LU (1) | LU91769I2 (enExample) |
| PT (2) | PT1764368E (enExample) |
| WO (1) | WO1998045301A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2761990B1 (fr) * | 1997-04-10 | 1999-06-25 | Pf Medicament | Derives halogenes antimitotiques d'alcaloides de vinca |
| US6890558B2 (en) * | 2002-05-31 | 2005-05-10 | R.P. Scherer Technologies, Inc. | Oral pharmaceutical composition for soft capsules containing vinorelbine and method of treatment |
| EP1694330A4 (en) * | 2003-12-04 | 2009-06-24 | Amr Technology Inc | DERIVATIVES OF VINORELBINE |
| NZ547370A (en) * | 2003-12-04 | 2010-09-30 | Amr Technology Inc | Vinca derivatives |
| US20110015221A1 (en) * | 2003-12-23 | 2011-01-20 | Pierre Fabre Medicament | Pharmaceutical composition of vinflunine which is intended for parenteral administration preparation method thereof and use of same |
| FR2863891B1 (fr) * | 2003-12-23 | 2006-03-24 | Pf Medicament | Composition pharmaceutique de vinflunine destinee a une administration parentale, procede de preparation et utilisation |
| CA2607940C (en) | 2005-05-18 | 2009-12-15 | Aegera Therapeutics Inc. | Bir domain binding compounds |
| FR2894966B1 (fr) * | 2005-12-20 | 2008-03-14 | Pierre Fabre Medicament Sa | Nouvelle forme cristalline de la vinflunine |
| MY159563A (en) | 2006-05-16 | 2017-01-13 | Pharmascience Inc | Iap bir domain binding compounds |
| US20080125451A1 (en) * | 2006-09-12 | 2008-05-29 | Amr Technology, Inc. | Vinorelbine derivatives |
| US8039453B2 (en) * | 2006-09-12 | 2011-10-18 | Albany Molecular Research, Inc. | Vinca derivatives |
| FR2905949B1 (fr) * | 2006-09-20 | 2008-11-21 | Pierre Fabre Medicament Sa | Derives fluores de catharanthine, leur preparation et leur utilisation comme precurseurs d'alcaloides dimeres de vinca |
| FR2910812B1 (fr) | 2006-12-29 | 2009-03-20 | Pierre Fabre Medicament Sa | Compositions pharmaceutiques injectables lyophilisees de derives hemi-synthetiques d'alcaloide de vinca stables a temperature ambiante |
| FR2912406B1 (fr) | 2007-02-13 | 2009-05-08 | Pierre Fabre Medicament Sa | Sels cristalins anhydres de vinflunine, procede de preparation et utilisation en tant que medicament et moyen de purification de la vinflunine. |
| FR2918566B1 (fr) * | 2007-07-11 | 2009-10-09 | Pierre Fabre Medicament Sa | Composition pharmaceutique stable d'un sel hydrosoluble de vinflunine. |
| FR2918567B1 (fr) * | 2007-07-11 | 2012-08-03 | Pf Medicament | Composition pharmaceutique stable d'un sel hydrosoluble de vinorelbine. |
| US20090076055A1 (en) * | 2007-09-14 | 2009-03-19 | Protia, Llc | Deuterium-enriched vinflunine |
| DE102010020994B4 (de) * | 2010-01-27 | 2022-01-27 | Interpane Entwicklungs-Und Beratungsgesellschaft Mbh | Verfahren zur Herstellung eines beschichteten Gegenstands mit Texturätzen |
| NZ602368A (en) | 2010-02-12 | 2014-10-31 | Pharmascience Inc | Iap bir domain binding compounds |
| US8940754B2 (en) | 2010-02-22 | 2015-01-27 | The Scripps Research Institute | 10′-fluorinated Vinca alkaloids provide enhanced biological activity against MDR cancer cells |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1997
- 1997-04-10 FR FR9704398A patent/FR2761990B1/fr not_active Expired - Lifetime
-
1998
- 1998-04-10 EP EP06124480A patent/EP1764368B1/fr not_active Expired - Lifetime
- 1998-04-10 DE DE69824840T patent/DE69824840T2/de not_active Expired - Lifetime
- 1998-04-10 AT AT06124480T patent/ATE473987T1/de active
- 1998-04-10 AU AU73408/98A patent/AU737549C/en not_active Expired
- 1998-04-10 US US09/402,678 patent/US6127377A/en not_active Expired - Lifetime
- 1998-04-10 EP EP20030017052 patent/EP1357125A3/fr not_active Ceased
- 1998-04-10 BR BRPI9816177-6A patent/BR9816177B1/pt not_active IP Right Cessation
- 1998-04-10 JP JP54247098A patent/JP4401440B2/ja not_active Expired - Lifetime
- 1998-04-10 CA CA2665949A patent/CA2665949C/fr not_active Expired - Lifetime
- 1998-04-10 DK DK98920607T patent/DK0975640T3/da active
- 1998-04-10 EP EP98920607A patent/EP0975640B1/fr not_active Expired - Lifetime
- 1998-04-10 DE DE69841766T patent/DE69841766D1/de not_active Expired - Lifetime
- 1998-04-10 ES ES98920607T patent/ES2222588T3/es not_active Expired - Lifetime
- 1998-04-10 PT PT06124480T patent/PT1764368E/pt unknown
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- 1998-04-10 AT AT98920607T patent/ATE270297T1/de active
- 1998-04-10 WO PCT/FR1998/000730 patent/WO1998045301A1/fr not_active Ceased
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- 1998-04-10 CA CA2455416A patent/CA2455416C/fr not_active Expired - Lifetime
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