BRPI0907999A2 - processo de preparação de combretastatina - Google Patents
processo de preparação de combretastatinaInfo
- Publication number
- BRPI0907999A2 BRPI0907999A2 BRPI0907999A BRPI0907999A BRPI0907999A2 BR PI0907999 A2 BRPI0907999 A2 BR PI0907999A2 BR PI0907999 A BRPI0907999 A BR PI0907999A BR PI0907999 A BRPI0907999 A BR PI0907999A BR PI0907999 A2 BRPI0907999 A2 BR PI0907999A2
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- combretastatin
- salt
- compound
- base
- Prior art date
Links
- LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 title abstract 5
- LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000006242 amine protecting group Chemical group 0.000 abstract 1
- -1 amino compound Chemical class 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
processo de preparação de combretastatina a presente invenção refere-se a um processo de preparação de uma combretastatina (a): fórmula (i) sob a forma de base ou de um sal de adição com um ácido, que consiste em acoplar em presença de uma base e de t3p o sal do composto (z)-amino de fórmula (11) com um derivado da lserina duplamente protegido de fórmula (111) no qual pg designa um grupo protetor da função amina de modo a obter o composto de fórmula (z)-(ib):fórmula (iv) e depois em desproteger e abrir o ciclo de (z)-(ib) em presença de um ácido de modo a obter a combretastatina (a) sob a forma de sal; e eventualmente em acrescentar uma base de modo a obter a combretastatina (a) sob a forma de base, o sal do composto (z)-amino tendo sido obtido por um enriquecimento do sal do composto amino de fórmula (v) em isômero (z).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0801092A FR2928148B1 (fr) | 2008-02-28 | 2008-02-28 | Procede de preparation de combretastatine |
| PCT/FR2009/000215 WO2009118474A1 (fr) | 2008-02-28 | 2009-02-27 | Procede de preparation de combretastatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0907999A2 true BRPI0907999A2 (pt) | 2019-01-15 |
Family
ID=39816950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0907999A BRPI0907999A2 (pt) | 2008-02-28 | 2009-02-27 | processo de preparação de combretastatina |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20110124899A1 (pt) |
| EP (2) | EP2562154A1 (pt) |
| JP (1) | JP2011513286A (pt) |
| KR (1) | KR20100116644A (pt) |
| CN (1) | CN102015620A (pt) |
| AR (1) | AR072772A1 (pt) |
| AU (1) | AU2009229027A1 (pt) |
| BR (1) | BRPI0907999A2 (pt) |
| CA (1) | CA2716541A1 (pt) |
| CL (3) | CL2009000463A1 (pt) |
| CO (1) | CO6241150A2 (pt) |
| CR (1) | CR11635A (pt) |
| DO (1) | DOP2010000250A (pt) |
| EA (2) | EA201300249A1 (pt) |
| EC (1) | ECSP10010421A (pt) |
| FR (1) | FR2928148B1 (pt) |
| HN (1) | HN2010001700A (pt) |
| IL (2) | IL207754A0 (pt) |
| MA (1) | MA32193B1 (pt) |
| MX (1) | MX2010009514A (pt) |
| NI (1) | NI201000144A (pt) |
| NZ (1) | NZ587505A (pt) |
| PE (1) | PE20091559A1 (pt) |
| SG (1) | SG183658A1 (pt) |
| TW (1) | TW200948753A (pt) |
| UY (1) | UY31681A1 (pt) |
| WO (1) | WO2009118474A1 (pt) |
| ZA (1) | ZA201006137B (pt) |
Families Citing this family (7)
| 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 |
| 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 |
| 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 |
| WO2018144910A1 (en) | 2017-02-02 | 2018-08-09 | Bioventures, Llc | Methods of protecting against neurodegeneration |
Family Cites Families (11)
| 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 |
| TW325458B (en) | 1993-09-08 | 1998-01-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions comprising the same for anti-cancer |
| US5731353A (en) | 1993-09-08 | 1998-03-24 | Ajinomoto Co., Inc. | Stilbene derivatives and pharmaceutical compositions containing them |
| 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 |
| ES2281374T3 (es) * | 1999-12-21 | 2007-10-01 | Teva Pharmaceutical Industries Ltd. | Nuevos polimorfos de hidrocloruro de sertralina, procedimientos para su preparacion, composiciones que los contienen y metodos para su utilizacion. |
| 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 |
-
2008
- 2008-02-28 FR FR0801092A patent/FR2928148B1/fr not_active Expired - Fee Related
-
2009
- 2009-02-26 AR ARP090100655A patent/AR072772A1/es not_active Application Discontinuation
- 2009-02-26 TW TW098106229A patent/TW200948753A/zh unknown
- 2009-02-26 PE PE2009000296A patent/PE20091559A1/es not_active Application Discontinuation
- 2009-02-27 UY UY031681A patent/UY31681A1/es not_active Application Discontinuation
- 2009-02-27 EP EP12172410A patent/EP2562154A1/fr not_active Withdrawn
- 2009-02-27 WO PCT/FR2009/000215 patent/WO2009118474A1/fr not_active Ceased
- 2009-02-27 NZ NZ587505A patent/NZ587505A/en not_active IP Right Cessation
- 2009-02-27 EA EA201300249A patent/EA201300249A1/ru unknown
- 2009-02-27 EP EP09725421A patent/EP2252572A1/fr not_active Withdrawn
- 2009-02-27 SG SG2012055521A patent/SG183658A1/en unknown
- 2009-02-27 CA CA2716541A patent/CA2716541A1/fr not_active Abandoned
- 2009-02-27 CL CL2009000463A patent/CL2009000463A1/es unknown
- 2009-02-27 MX MX2010009514A patent/MX2010009514A/es not_active Application Discontinuation
- 2009-02-27 EA EA201071001A patent/EA201071001A1/ru unknown
- 2009-02-27 CN CN2009801150963A patent/CN102015620A/zh active Pending
- 2009-02-27 KR KR1020107019132A patent/KR20100116644A/ko not_active Withdrawn
- 2009-02-27 BR BRPI0907999A patent/BRPI0907999A2/pt not_active IP Right Cessation
- 2009-02-27 JP JP2010548144A patent/JP2011513286A/ja active Pending
- 2009-02-27 AU AU2009229027A patent/AU2009229027A1/en not_active Abandoned
-
2010
- 2010-08-12 DO DO2010000250A patent/DOP2010000250A/es unknown
- 2010-08-16 CR CR11635A patent/CR11635A/es not_active Application Discontinuation
- 2010-08-23 IL IL207754A patent/IL207754A0/en unknown
- 2010-08-24 EC EC2010010421A patent/ECSP10010421A/es unknown
- 2010-08-26 HN HN2010001700A patent/HN2010001700A/es unknown
- 2010-08-26 CO CO10105393A patent/CO6241150A2/es not_active Application Discontinuation
- 2010-08-27 NI NI201000144A patent/NI201000144A/es unknown
- 2010-08-27 ZA ZA2010/06137A patent/ZA201006137B/en unknown
- 2010-08-27 US US12/869,997 patent/US20110124899A1/en not_active Abandoned
- 2010-09-13 MA MA33176A patent/MA32193B1/fr unknown
-
2012
- 2012-06-25 CL CL2012001744A patent/CL2012001744A1/es unknown
- 2012-06-25 CL CL2012001742A patent/CL2012001742A1/es unknown
-
2013
- 2013-04-15 IL IL225776A patent/IL225776A0/en unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE AS 6A, 7A, 8A, 9A E 10A ANUIDADES. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: EM VIRTUDE DO ARQUIVAMENTO PUBLICADO NA RPI 2507 DE 22-01-2019 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDO O ARQUIVAMENTO DO PEDIDO DE PATENTE, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013. |
|
| B350 | Update of information on the portal [chapter 15.35 patent gazette] |