AR079300A1 - Procedimiento de preparacion de un derivado de combretastatina e intermediarios de reaccion - Google Patents
Procedimiento de preparacion de un derivado de combretastatina e intermediarios de reaccionInfo
- Publication number
- AR079300A1 AR079300A1 ARP100104450A ARP100104450A AR079300A1 AR 079300 A1 AR079300 A1 AR 079300A1 AR P100104450 A ARP100104450 A AR P100104450A AR P100104450 A ARP100104450 A AR P100104450A AR 079300 A1 AR079300 A1 AR 079300A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- group
- phenyl
- derivative
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
La invencion se refiere a un procedimiento de preparacion de un derivado de combretastatina (1) o (2): que comprende las etapas siguientes: - se hace reaccionar el halogenuro de triaril(3,4,5-trimetoxibencil)fosfonio (3) en la que Ar significa un grupo de arilo elegido entre fenilo o tienilo, con formula (4) o bien formula (5), con el fin de obtener, respectivamente, el compuesto (6) o bien (7): - luego, en el transcurso de una etapa de desproteccion en presencia de un ácido y/o de una base, el compuesto de formula (6) o (7) conduce, después de una etapa eventual de purificacion, al compuesto de formula (1) o (2). Reivindicacion 1: Procedimiento de preparacion de un derivado de combretastatina de formula (1) o (2): Significando A- el anion asociado a un ácido AH, que comprende las etapas siguientes: - se hace reaccionar, en presencia de una base, el halogenuro de triaril(3,4,5- trimetoxibencil)fosfonio (3) en la que Ar significa un grupo de arilo elegido entre fenilo o tienilo, sustituido eventualmente con un grupo de alquilo (C1-4), alcoxi (C1-4) o halogeno, con: - formula (4) en la que R y R' representan: - o cada uno un grupo de alquilo (C1-4); - o bien R representa un grupo de fenilo sustituido eventualmente con un grupo alcoxi (C1-4) y R' representa un átomo de hidrogeno; - o bien R y R' forman conjuntamente con el átomo de carbono al que están unidos un grupo de cicloalquilo (C3-7); - o bien de formula (5) en la que PG1 representa un grupo protector de la funcion alcohol, representando X Boc, Fmoc o CBZ, con el fin de obtener, respectivamente, el compuesto (6) o bien (7): - luego, en el transcurso de una etapa de desproteccion en presencia de un ácido y/o de una base, el compuesto de formula 6 o 7 conduce, después de una etapa eventual de purificacion, al compuesto de formula (1) o (2). Reivindicacion 7: Compuesto de formula (4): en la que R y R' representan: o cada uno un grupo de alquilo (C1-4); o bien R representa un grupo de fenilo sustituido eventualmente con un grupo alcoxi (C1-4) y R' representa un átomo de hidrogeno; o bien R y R' forman conjuntamente con el átomo de carbono al que están unidos un grupo de cicloalquilo (C3-7); y X representa Boc, Fmoc o CBZ. Reivindicacion 10: Compuesto de formula (5): en la que PG1 representa un grupo protector de la funcion alcohol, y X representa Boc, Fmoc o CBZ.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0905837A FR2953518B1 (fr) | 2009-12-03 | 2009-12-03 | Procede de preparation d'un derive de combretastatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR079300A1 true AR079300A1 (es) | 2012-01-18 |
Family
ID=42165674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP100104450A AR079300A1 (es) | 2009-12-03 | 2010-12-02 | Procedimiento de preparacion de un derivado de combretastatina e intermediarios de reaccion |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US20120302759A1 (es) |
| EP (1) | EP2507218A1 (es) |
| JP (1) | JP2013512883A (es) |
| KR (1) | KR20120104988A (es) |
| CN (1) | CN102906076A (es) |
| AR (1) | AR079300A1 (es) |
| AU (1) | AU2010326423A1 (es) |
| BR (1) | BR112012012908A2 (es) |
| CA (1) | CA2782701A1 (es) |
| FR (1) | FR2953518B1 (es) |
| IL (1) | IL220059A0 (es) |
| MX (1) | MX2012006388A (es) |
| RU (1) | RU2012127575A (es) |
| SG (1) | SG181467A1 (es) |
| TW (1) | TW201127790A (es) |
| UY (1) | UY33080A (es) |
| WO (1) | WO2011067538A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3184095A1 (en) | 2013-05-23 | 2017-06-28 | IP Gesellschaft für Management mbH | Administration units comprising polymorph 1 of 2-(2-methylamino-pyrimidin-4-yl]-1h-indole-5-carboxylic acid [(s)-1-carbamoyl-2-(phenyl-pyrimidin-2-yl-amino)-ethyl]-amide |
| CN104817519B (zh) * | 2015-05-11 | 2016-11-16 | 中国药科大学 | 一类ca-4的衍生物、其制法及其医药用途 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW325458B (en) * | 1993-09-08 | 1998-01-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions comprising the same for anti-cancer |
| TW334418B (en) * | 1995-03-07 | 1998-06-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions |
| ATE328599T1 (de) | 1998-04-03 | 2006-06-15 | Ajinomoto Kk | Antitumorale mittel |
| GB9903403D0 (en) * | 1999-02-16 | 1999-04-07 | Angiogene Pharm Ltd | Substituted stilbene compounds with vascular damaging activity |
| EP1264821B1 (en) | 2000-03-17 | 2008-05-14 | Ajinomoto Co., Inc. | Novel crystal of stilbene derivative and process for producing the same |
| US6743937B2 (en) * | 2000-07-17 | 2004-06-01 | Oxigene, Inc. | Efficient method of synthesizing combretastatin A-4 prodrugs |
| ATE489080T1 (de) | 2001-06-25 | 2010-12-15 | Ajinomoto Kk | Antitumorale mittel |
| FR2838437B1 (fr) * | 2002-04-11 | 2004-06-04 | Aventis Pharma Sa | Procedes de preparation de combretastatines |
| US6759555B2 (en) * | 2002-04-11 | 2004-07-06 | Aventis Pharma S.A. | Process for the preparation of combretastatins |
| JP2008515925A (ja) | 2004-10-08 | 2008-05-15 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | １，２，４−トリアゾリルアミノアリール（ヘテロアリール）スルホンアミド誘導体 |
| FR2928148B1 (fr) | 2008-02-28 | 2013-01-18 | Sanofi Aventis | Procede de preparation de combretastatine |
-
2009
- 2009-12-03 FR FR0905837A patent/FR2953518B1/fr not_active Expired - Fee Related
-
2010
- 2010-12-02 BR BR112012012908A patent/BR112012012908A2/pt not_active IP Right Cessation
- 2010-12-02 EP EP10801618A patent/EP2507218A1/fr not_active Withdrawn
- 2010-12-02 AR ARP100104450A patent/AR079300A1/es unknown
- 2010-12-02 AU AU2010326423A patent/AU2010326423A1/en not_active Abandoned
- 2010-12-02 CN CN2010800545408A patent/CN102906076A/zh active Pending
- 2010-12-02 KR KR1020127014273A patent/KR20120104988A/ko not_active Application Discontinuation
- 2010-12-02 MX MX2012006388A patent/MX2012006388A/es not_active Application Discontinuation
- 2010-12-02 RU RU2012127575/04A patent/RU2012127575A/ru not_active Application Discontinuation
- 2010-12-02 TW TW099141920A patent/TW201127790A/zh unknown
- 2010-12-02 CA CA2782701A patent/CA2782701A1/fr not_active Abandoned
- 2010-12-02 WO PCT/FR2010/052592 patent/WO2011067538A1/fr active Application Filing
- 2010-12-02 SG SG2012040374A patent/SG181467A1/en unknown
- 2010-12-02 JP JP2012541565A patent/JP2013512883A/ja not_active Withdrawn
- 2010-12-03 UY UY33080A patent/UY33080A/es not_active Application Discontinuation
-
2012
- 2012-05-30 IL IL220059A patent/IL220059A0/en unknown
- 2012-06-04 US US13/487,606 patent/US20120302759A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL220059A0 (en) | 2012-09-24 |
| UY33080A (es) | 2011-06-01 |
| US20120302759A1 (en) | 2012-11-29 |
| FR2953518B1 (fr) | 2012-01-20 |
| BR112012012908A2 (pt) | 2015-09-08 |
| JP2013512883A (ja) | 2013-04-18 |
| CA2782701A1 (fr) | 2011-06-09 |
| WO2011067538A1 (fr) | 2011-06-09 |
| MX2012006388A (es) | 2012-06-19 |
| KR20120104988A (ko) | 2012-09-24 |
| AU2010326423A1 (en) | 2012-06-21 |
| CN102906076A (zh) | 2013-01-30 |
| FR2953518A1 (fr) | 2011-06-10 |
| TW201127790A (en) | 2011-08-16 |
| RU2012127575A (ru) | 2014-01-10 |
| SG181467A1 (en) | 2012-07-30 |
| EP2507218A1 (fr) | 2012-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |