AR072772A1 - Procedimiento de preparacion de combretastatina y uso del mismo - Google Patents

Procedimiento de preparacion de combretastatina y uso del mismo

Info

Publication number
AR072772A1
AR072772A1 ARP090100655A ARP090100655A AR072772A1 AR 072772 A1 AR072772 A1 AR 072772A1 AR P090100655 A ARP090100655 A AR P090100655A AR P090100655 A ARP090100655 A AR P090100655A AR 072772 A1 AR072772 A1 AR 072772A1
Authority
AR
Argentina
Prior art keywords
formula
compound
amino
salt
designates
Prior art date
Application number
ARP090100655A
Other languages
English (en)
Inventor
Joel Malpart
Stephane Mutti
Marc Frederic
Sylviane Lutz
Philippe Masson
Original Assignee
Sanofi Aventis
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=39816950&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR072772(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Sanofi Aventis filed Critical Sanofi Aventis
Publication of AR072772A1 publication Critical patent/AR072772A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • 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
    • 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
    • C07B2200/07—Optical isomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Reivindicacion 1: Procedimiento de preparacion de una combretastatina de formula (1) en forma de base o de una sal de adicion con un ácido, que consiste en: acoplar en presencia de una base y de T3P de formula (2) el compuesto (Z)-amino de formula (3) o la sal del compuesto (Z)-amino de formula (4), donde B- designa un contra-anion, con un derivado de la L-serina doblemente protegido de formula (5) en la cual PG designa un grupo protector de la funcion amina de manera que se obtenga el compuesto de formula (6); luego, en desproteger y abrir el ciclo del compuesto de formula (6) en presencia de un ácido de manera que se obtiene la combretastatina de formula (1) en forma de sal; y, eventualmente, en anadir una base de manera que se obtiene la combretastatina de formula (1) en forma de base, habiendo sido obtenida la sal del compuesto (Z)-amino mediante un enriquecimiento de la sal del compuesto amino de formula (7) en isomero (Z), en donde B- designa un contra-anion, que consiste: en anadir alcohol bencílico a una suspension de una mezcla de las sales de los compuestos (Z)- y (E)-amino en acetonitrilo y después, en separar mecánicamente la sal del compuesto amino enriquecido en isomero (Z). Reivindicacion 14: Uso de T3P de formula (2) para realizar el acoplamiento entre el compuesto (Z)-amino de formula (3) o la sal del compuesto (Z)-amino de formula (4), donde B-designa un contra-anion, con un derivado de la L-serina doblemente protegida de formula (5) en la cual PG designa un grupo protector de la funcion amina.
ARP090100655A 2008-02-28 2009-02-26 Procedimiento de preparacion de combretastatina y uso del mismo AR072772A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0801092A FR2928148B1 (fr) 2008-02-28 2008-02-28 Procede de preparation de combretastatine

Publications (1)

Publication Number Publication Date
AR072772A1 true AR072772A1 (es) 2010-09-22

Family

ID=39816950

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP090100655A AR072772A1 (es) 2008-02-28 2009-02-26 Procedimiento de preparacion de combretastatina y uso del mismo

Country Status (28)

Country Link
US (1) US20110124899A1 (es)
EP (2) EP2252572A1 (es)
JP (1) JP2011513286A (es)
KR (1) KR20100116644A (es)
CN (1) CN102015620A (es)
AR (1) AR072772A1 (es)
AU (1) AU2009229027A1 (es)
BR (1) BRPI0907999A2 (es)
CA (1) CA2716541A1 (es)
CL (3) CL2009000463A1 (es)
CO (1) CO6241150A2 (es)
CR (1) CR11635A (es)
DO (1) DOP2010000250A (es)
EA (2) EA201300249A1 (es)
EC (1) ECSP10010421A (es)
FR (1) FR2928148B1 (es)
HN (1) HN2010001700A (es)
IL (2) IL207754A0 (es)
MA (1) MA32193B1 (es)
MX (1) MX2010009514A (es)
NI (1) NI201000144A (es)
NZ (1) NZ587505A (es)
PE (1) PE20091559A1 (es)
SG (1) SG183658A1 (es)
TW (1) TW200948753A (es)
UY (1) UY31681A1 (es)
WO (1) WO2009118474A1 (es)
ZA (1) ZA201006137B (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2953518B1 (fr) 2009-12-03 2012-01-20 Sanofi Aventis Procede de preparation d'un derive de combretastatine
WO2013084150A1 (en) * 2011-12-06 2013-06-13 Sanofi Novel crystal form of (2s)-2-amino-3-hydroxy-n-[2-methoxy-2-[(1z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]propanamide and method of preparation thereof
EP2805705B1 (en) 2013-05-23 2016-11-09 IP Gesellschaft für Management mbH Packaging with one or more administration units comprising a sodium salt of (R)-3-[6-amino-pyridin-3-yl]-2-(1-cyclohexyl-1 H-imidazol-4-yl)-propionic acid
CN104447598B (zh) * 2013-09-18 2017-09-22 浙江大德药业集团有限公司 Ca‑4的大环多胺衍生物及其抗肿瘤特性
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
CN104892668B (zh) * 2015-05-12 2017-03-29 上海大学 考布他汀类似物水溶性前‑前药及其制备方法

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1217500A (en) * 1967-05-24 1970-12-31 Ici Ltd Separation of trans-trans enriched salts of 4,4'-diaminodicyclohexylmethane
US5731353A (en) 1993-09-08 1998-03-24 Ajinomoto Co., Inc. Stilbene derivatives and pharmaceutical compositions containing them
TW325458B (en) 1993-09-08 1998-01-21 Ajinomoto Kk Stilbene derivatives and pharmaceutical compositions comprising the same for anti-cancer
US5561122A (en) 1994-12-22 1996-10-01 Arizona Board Of Regents Acting On Behalf Of Arizona State University Combretastatin A-4 prodrug
TW334418B (en) * 1995-03-07 1998-06-21 Ajinomoto Kk Stilbene derivatives and pharmaceutical compositions
JPH08272028A (ja) * 1995-03-30 1996-10-18 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料およびその製造方法
JP2000239274A (ja) * 1998-12-16 2000-09-05 Nippon Kayaku Co Ltd 新規ナフチリジン誘導体の製造法
PT1248605E (pt) * 1999-12-21 2007-03-30 Teva Pharma Novos polimorfos de cloridrato de sertralina, processos para a sua preparação, composições que os contêm e métodos para a sua utilização
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
DE10333042B4 (de) * 2003-07-21 2005-09-29 Clariant Gmbh Verfahren zur Herstellung von cyclischen Phosphonsäureanhydriden und deren Verwendung

Also Published As

Publication number Publication date
EA201300249A1 (ru) 2013-08-30
EP2252572A1 (fr) 2010-11-24
CO6241150A2 (es) 2011-01-20
NZ587505A (en) 2012-06-29
SG183658A1 (en) 2012-09-27
IL207754A0 (en) 2010-12-30
PE20091559A1 (es) 2009-10-30
WO2009118474A8 (fr) 2010-09-10
UY31681A1 (es) 2009-09-30
KR20100116644A (ko) 2010-11-01
ZA201006137B (en) 2011-11-30
CL2012001742A1 (es) 2012-11-16
IL225776A0 (en) 2013-06-27
DOP2010000250A (es) 2010-09-30
ECSP10010421A (es) 2010-09-30
MX2010009514A (es) 2010-12-15
CL2012001744A1 (es) 2012-10-12
US20110124899A1 (en) 2011-05-26
MA32193B1 (fr) 2011-04-01
FR2928148A1 (fr) 2009-09-04
JP2011513286A (ja) 2011-04-28
FR2928148B1 (fr) 2013-01-18
CR11635A (es) 2011-02-04
NI201000144A (es) 2011-03-09
CN102015620A (zh) 2011-04-13
BRPI0907999A2 (pt) 2019-01-15
CL2009000463A1 (es) 2010-12-03
TW200948753A (en) 2009-12-01
AU2009229027A1 (en) 2009-10-01
EA201071001A1 (ru) 2011-02-28
HN2010001700A (es) 2013-06-17
EP2562154A1 (fr) 2013-02-27
CA2716541A1 (fr) 2009-10-01
WO2009118474A1 (fr) 2009-10-01

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