FR10C0045I1 - - Google Patents
Info
- Publication number
- FR10C0045I1 FR10C0045I1 FR10C0045C FR10C0045I1 FR 10C0045 I1 FR10C0045 I1 FR 10C0045I1 FR 10C0045 C FR10C0045 C FR 10C0045C FR 10C0045 I1 FR10C0045 I1 FR 10C0045I1
- Authority
- FR
- France
- Prior art keywords
- formula
- preparation
- sbf5
- dibromomethane
- vinflunine
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 abstract 2
- ZEOVXNVKXIPWMS-UHFFFAOYSA-N 2,2-dichloropropane Chemical compound CC(C)(Cl)Cl ZEOVXNVKXIPWMS-UHFFFAOYSA-N 0.000 abstract 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 abstract 1
- 229940122803 Vinca alkaloid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000003797 alkaloid derivatives Chemical class 0.000 abstract 1
- 230000002927 anti-mitotic effect Effects 0.000 abstract 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 abstract 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000003930 superacid Substances 0.000 abstract 1
- NMDYYWFGPIMTKO-HBVLKOHWSA-N vinflunine Chemical compound 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 abstract 1
- 229960000922 vinflunine Drugs 0.000 abstract 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
Antimitotic Vinca alkaloid derivatives of formula (I), their salts with acids, and their diastereoisomers and mixtures, and processes for their preparation are new. In formula (I), n = 1 or 2, R1 = H or F; R2 = Cl. Process for the preparation of vinflunine (I; n = 2; R1 = H; R2 = difluoro), by reaction of (II) in a superacid medium (HF + SbF5) at -45 to -35[deg]C, with a halide generator (chloroform, 2,2-dichloropropane, carbon tetrabromide, dibromomethane, or boron tribromide) is also claimed, where R3 = OH; R4 = H, or R3 and R4 together form a double bond.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9704398A FR2761990B1 (en) | 1997-04-10 | 1997-04-10 | ANTIMITOTIC HALOGEN DERIVATIVES OF VINCA ALKALOIDS |
| EP20030017052 EP1357125A3 (en) | 1997-04-10 | 1998-04-10 | Process for the preparation of halogenated derivatives of vinca alcaloids |
| EP98920607A EP0975640B1 (en) | 1997-04-10 | 1998-04-10 | Vinca alkaloid antimitotic halogenated derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR10C0045I1 true FR10C0045I1 (en) | 2010-10-29 |
| FR10C0045I2 FR10C0045I2 (en) | 2011-04-29 |
Family
ID=9505731
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9704398A Expired - Lifetime FR2761990B1 (en) | 1997-04-10 | 1997-04-10 | ANTIMITOTIC HALOGEN DERIVATIVES OF VINCA ALKALOIDS |
| FR10C0045C Active FR10C0045I2 (en) | 1997-04-10 | 2010-09-27 | HALOGEN ANTIMITOTIC DERIVATIVE OF VINCA ALKALOID |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9704398A Expired - Lifetime FR2761990B1 (en) | 1997-04-10 | 1997-04-10 | ANTIMITOTIC HALOGEN DERIVATIVES OF VINCA ALKALOIDS |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6127377A (en) |
| EP (3) | EP1764368B1 (en) |
| JP (3) | JP4401440B2 (en) |
| AT (2) | ATE270297T1 (en) |
| AU (1) | AU737549C (en) |
| BR (2) | BR9807944B1 (en) |
| CA (3) | CA2286560C (en) |
| CY (2) | CY1111476T1 (en) |
| DE (3) | DE122010000054I1 (en) |
| DK (2) | DK1764368T3 (en) |
| ES (2) | ES2347878T3 (en) |
| FR (2) | FR2761990B1 (en) |
| LU (1) | LU91769I2 (en) |
| PT (2) | PT975640E (en) |
| WO (1) | WO1998045301A1 (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2761990B1 (en) * | 1997-04-10 | 1999-06-25 | Pf Medicament | ANTIMITOTIC HALOGEN DERIVATIVES OF VINCA ALKALOIDS |
| 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 |
| WO2005055939A2 (en) * | 2003-12-04 | 2005-06-23 | Amr Technology, Inc. | Vinca derivatives |
| US7235564B2 (en) * | 2003-12-04 | 2007-06-26 | Amr Technology, Inc. | Vinorelbine 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 (en) * | 2003-12-23 | 2006-03-24 | Pf Medicament | PHARMACEUTICAL COMPOSITION OF VINFLUNIN FOR PARENTAL ADMINISTRATION, PROCESS FOR PREPARATION AND USE |
| US7772177B2 (en) | 2005-05-18 | 2010-08-10 | Aegera Therapeutics, Inc. | BIR domain binding compounds |
| FR2894966B1 (en) * | 2005-12-20 | 2008-03-14 | Pierre Fabre Medicament Sa | NEW CRYSTALLINE FORM OF VINFLUNINE |
| AU2007250443B2 (en) | 2006-05-16 | 2013-06-13 | Pharmascience Inc. | IAP BIR domain binding compounds |
| WO2008033935A2 (en) * | 2006-09-12 | 2008-03-20 | Amr Technology, Inc. | Vinorelbine derivatives |
| WO2008033930A2 (en) * | 2006-09-12 | 2008-03-20 | Amr Technology, Inc. | Vinca derivatives |
| FR2905949B1 (en) | 2006-09-20 | 2008-11-21 | Pierre Fabre Medicament Sa | FLUORINE DERIVATIVES OF CATHARANTHIN, PREPARATION THEREOF AND THEIR USE AS PRECURSORS OF ALKALOIDS DIMERES DE VINCA |
| FR2910812B1 (en) | 2006-12-29 | 2009-03-20 | Pierre Fabre Medicament Sa | LYOPHILIZED INJECTABLE PHARMACEUTICAL COMPOSITIONS OF HEMI-SYNTHETIC STABLE VINCA ALKALOID DERIVATIVES AT AMBIENT TEMPERATURE |
| FR2912406B1 (en) * | 2007-02-13 | 2009-05-08 | Pierre Fabre Medicament Sa | VINFLUNIN ANHYDROUS CRYSTAL SALTS, PROCESS FOR THEIR PREPARATION AND USE AS MEDICAMENT AND MEANS FOR PURIFYING VINFLUNIN. |
| FR2918566B1 (en) * | 2007-07-11 | 2009-10-09 | Pierre Fabre Medicament Sa | STABLE PHARMACEUTICAL COMPOSITION OF A WATER SOLUBLE SALT OF VINFLUNINE. |
| FR2918567B1 (en) * | 2007-07-11 | 2012-08-03 | Pf Medicament | STABLE PHARMACEUTICAL COMPOSITION OF A WATER SOLUBLE SALT OF VINORELBINE. |
| US20090076055A1 (en) * | 2007-09-14 | 2009-03-19 | Protia, Llc | Deuterium-enriched vinflunine |
| DE102010020994B4 (en) * | 2010-01-27 | 2022-01-27 | Interpane Entwicklungs-Und Beratungsgesellschaft Mbh | Method of making a coated article using texture etching |
| NZ602368A (en) | 2010-02-12 | 2014-10-31 | Pharmascience Inc | Iap bir domain binding compounds |
| JP5542972B2 (en) * | 2010-02-22 | 2014-07-09 | ザ スクリプス リサーチ インスティテュート | 10'-fluorinated vinca alkaloids that provide enhanced biological activity against MDR cancer cells |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2707988B1 (en) * | 1993-07-21 | 1995-10-13 | Pf Medicament | New antimitotic derivatives of binary alkaloids of catharantus rosesus, process for their preparation and pharmaceutical compositions comprising them. |
| FR2761990B1 (en) * | 1997-04-10 | 1999-06-25 | Pf Medicament | ANTIMITOTIC HALOGEN DERIVATIVES OF VINCA ALKALOIDS |
-
1997
- 1997-04-10 FR FR9704398A patent/FR2761990B1/en not_active Expired - Lifetime
-
1998
- 1998-04-10 DK DK06124480.2T patent/DK1764368T3/en active
- 1998-04-10 ES ES06124480T patent/ES2347878T3/en not_active Expired - Lifetime
- 1998-04-10 BR BRPI9807944-1A patent/BR9807944B1/en not_active IP Right Cessation
- 1998-04-10 AU AU73408/98A patent/AU737549C/en not_active Expired
- 1998-04-10 CA CA002286560A patent/CA2286560C/en not_active Expired - Lifetime
- 1998-04-10 WO PCT/FR1998/000730 patent/WO1998045301A1/en not_active Ceased
- 1998-04-10 ES ES98920607T patent/ES2222588T3/en not_active Expired - Lifetime
- 1998-04-10 DE DE122010000054C patent/DE122010000054I1/en active Pending
- 1998-04-10 DE DE69841766T patent/DE69841766D1/en not_active Expired - Lifetime
- 1998-04-10 EP EP06124480A patent/EP1764368B1/en not_active Expired - Lifetime
- 1998-04-10 AT AT98920607T patent/ATE270297T1/en active
- 1998-04-10 CA CA2455416A patent/CA2455416C/en not_active Expired - Lifetime
- 1998-04-10 DK DK98920607T patent/DK0975640T3/en active
- 1998-04-10 PT PT98920607T patent/PT975640E/en unknown
- 1998-04-10 JP JP54247098A patent/JP4401440B2/en not_active Expired - Lifetime
- 1998-04-10 US US09/402,678 patent/US6127377A/en not_active Expired - Lifetime
- 1998-04-10 CA CA2665949A patent/CA2665949C/en not_active Expired - Lifetime
- 1998-04-10 EP EP98920607A patent/EP0975640B1/en not_active Expired - Lifetime
- 1998-04-10 PT PT06124480T patent/PT1764368E/en unknown
- 1998-04-10 AT AT06124480T patent/ATE473987T1/en active
- 1998-04-10 EP EP20030017052 patent/EP1357125A3/en not_active Ceased
- 1998-04-10 DE DE69824840T patent/DE69824840T2/en not_active Expired - Lifetime
- 1998-04-10 BR BRPI9816177-6A patent/BR9816177B1/en not_active IP Right Cessation
-
2004
- 2004-03-03 JP JP2004059502A patent/JP4307292B2/en not_active Expired - Lifetime
-
2009
- 2009-03-11 JP JP2009058098A patent/JP2009167196A/en active Pending
-
2010
- 2010-09-27 FR FR10C0045C patent/FR10C0045I2/en active Active
- 2010-10-14 CY CY20101100917T patent/CY1111476T1/en unknown
- 2010-12-22 CY CY2010019C patent/CY2010019I1/en unknown
- 2010-12-22 LU LU91769C patent/LU91769I2/en unknown
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