AR039198A1 - Procedimientos de preparacion de combretastatinas - Google Patents
Procedimientos de preparacion de combretastatinasInfo
- Publication number
- AR039198A1 AR039198A1 ARP030101111A ARP030101111A AR039198A1 AR 039198 A1 AR039198 A1 AR 039198A1 AR P030101111 A ARP030101111 A AR P030101111A AR P030101111 A ARP030101111 A AR P030101111A AR 039198 A1 AR039198 A1 AR 039198A1
- Authority
- AR
- Argentina
- Prior art keywords
- nitro
- wittig
- combretastatins
- trimethoxy
- benzaldehyde
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 150000004814 combretastatins Chemical class 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- -1 nitromethoxybenzyl Chemical group 0.000 abstract 2
- 150000004714 phosphonium salts Chemical class 0.000 abstract 2
- UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 abstract 1
- BLODNUUIZXWVIA-UHFFFAOYSA-N 2-(nitromethoxy)benzaldehyde Chemical compound [O-][N+](=O)COC1=CC=CC=C1C=O BLODNUUIZXWVIA-UHFFFAOYSA-N 0.000 abstract 1
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 abstract 1
- YTCRQCGRYCKYNO-UHFFFAOYSA-N 4-methoxy-3-nitrobenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1[N+]([O-])=O YTCRQCGRYCKYNO-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001701 trimethoxybenzyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- 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
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Magnetic Ceramics (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Detergent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente se refiere a procedimientos de preparación de combretastatinas por condensación de Wittig entre el nitrometoxi-benzaldehído y una sal de fosfonio del trimetoxi-bencilo, o la inversa, una sal de fosfonio del nitrometoxi-bencilo con el trimetoxi-benzaldehído o también una reacción de Wittig sobre los mismos derivados cuya función nitro ha sido reducida a un grupo amino. Reivindicación 1: Procedimiento de preparación de combretastatinas de la fórmula general (1): en la que A representa un grupo amino, caracterizado porque después de la condensación de Wittig en presencia de bromuro o cloruro de (3,4,5-trimetoxi-bencil)-trifenilfosfonio y del 3-nitro-4-metoxi-benzaldehído o del 3,4,5-trimetoxi-benzaldehído con una sal de (4-metoxi-3-nitro-bencil)-trifenifosfonio se realiza la reducción del grupo nitro en presencia de hierro.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0204499A FR2838437B1 (fr) | 2002-04-11 | 2002-04-11 | Procedes de preparation de combretastatines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR039198A1 true AR039198A1 (es) | 2005-02-09 |
Family
ID=28459732
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP030101111A AR039198A1 (es) | 2002-04-11 | 2003-03-28 | Procedimientos de preparacion de combretastatinas |
| ARP110102854A AR082581A2 (es) | 2002-04-11 | 2011-08-05 | Procedimientos de preparacion de combretastatinas |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110102854A AR082581A2 (es) | 2002-04-11 | 2011-08-05 | Procedimientos de preparacion de combretastatinas |
Country Status (27)
| Country | Link |
|---|---|
| EP (3) | EP1497255A2 (es) |
| JP (1) | JP4299677B2 (es) |
| KR (1) | KR101018983B1 (es) |
| CN (1) | CN1291970C (es) |
| AR (2) | AR039198A1 (es) |
| AU (1) | AU2003260026B2 (es) |
| BR (1) | BR0309087A (es) |
| CA (1) | CA2481742C (es) |
| CR (1) | CR7481A (es) |
| EA (1) | EA007965B1 (es) |
| EC (1) | ECSP045348A (es) |
| FR (1) | FR2838437B1 (es) |
| HR (1) | HRP20040935A2 (es) |
| IL (1) | IL164247A0 (es) |
| MA (1) | MA26407A1 (es) |
| ME (1) | MEP91508A (es) |
| MX (1) | MXPA04009112A (es) |
| NO (2) | NO329701B1 (es) |
| NZ (1) | NZ535318A (es) |
| OA (1) | OA12804A (es) |
| PL (3) | PL214129B1 (es) |
| RS (3) | RS52331B (es) |
| TN (1) | TNSN04201A1 (es) |
| TW (1) | TWI262179B (es) |
| UA (1) | UA76079C2 (es) |
| WO (1) | WO2003084919A2 (es) |
| ZA (1) | ZA200407417B (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235688B1 (en) | 2004-11-04 | 2007-06-26 | University Of Notre Dame Du Lac | Process for preparing histone deacetylase inhibitors and intermediates thereof |
| FR2928148B1 (fr) * | 2008-02-28 | 2013-01-18 | Sanofi Aventis | Procede de preparation de combretastatine |
| FR2939665B1 (fr) | 2008-12-12 | 2011-10-07 | Sanofi Aventis | Combinaison antitumorale associant l'ave8062a et le docetaxel |
| FR2945210B1 (fr) | 2009-05-07 | 2011-07-01 | Sanofi Aventis | Combinaison antitumorale comprenant l'ave8062 et le sorafenib |
| FR2953518B1 (fr) * | 2009-12-03 | 2012-01-20 | Sanofi Aventis | Procede de preparation d'un derive de combretastatine |
| EP2481404A1 (en) | 2010-11-15 | 2012-08-01 | Sanofi | An antitumoral combination comprising ombrabulin, a taxane derivative and a platinum derivative |
| EP2397135A1 (en) | 2010-06-18 | 2011-12-21 | Sanofi | An antitumoral combination comprising ombrabulin, a taxane derivative and a platinum derivative |
| CN103140224A (zh) | 2010-06-18 | 2013-06-05 | 赛诺菲 | 包含奥瑞布林、紫杉烷衍生物和铂衍生物的抗肿瘤组合 |
| EP2407161A1 (en) | 2010-07-13 | 2012-01-18 | Sanofi | An antitumoral combination comprising ombrabulin and bevacizumab |
| FR2968557A1 (fr) | 2010-12-09 | 2012-06-15 | Sanofi Aventis | Combinaison antitumorale comprenant un derive de la famille des combretastatines et le cetuximab |
| FR2978662A1 (fr) | 2011-08-01 | 2013-02-08 | Sanofi Sa | Combinaison antitumorale comprenant l'ombrabuline et le cisplatine, associee a la radiotherapie |
| FR2978663A1 (fr) | 2011-08-01 | 2013-02-08 | Sanofi Sa | Combinaison antitumorale comprenant l'ombrabuline et le cetuximab, associee a la radiotherapie |
| CN103012248B (zh) * | 2013-01-11 | 2014-11-05 | 浙江大德药业集团有限公司 | 氨基康普立停衍生物的合成及其作为口服抗肿瘤药物的应用 |
| 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 |
| EP4079327A1 (en) | 2021-04-22 | 2022-10-26 | Centaurus Polytherapeutics | Payloads for drug-conjugates and their use for treating cancer |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4996237A (en) | 1987-01-06 | 1991-02-26 | Arizona Board Of Regents | Combretastatin A-4 |
| UA18265A (uk) * | 1988-02-24 | 1997-12-25 | Ф.Хоффманн-Ля Рош Аг | Спосіб одержаhhя похідhих стильбеhу |
| NZ232897A (en) * | 1989-04-03 | 1992-12-23 | Squibb & Sons Inc | Interphenylene 7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogues, preparation and pharmaceutical compositions thereof |
| 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 |
| CN1053658C (zh) * | 1994-04-06 | 2000-06-21 | 日本新药株式会社 | 氨基芪唑衍生物和药 |
| TW334418B (en) * | 1995-03-07 | 1998-06-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions |
| JP4551514B2 (ja) * | 1999-07-23 | 2010-09-29 | 住友化学株式会社 | 不飽和炭化水素残基置換アニリン類の製造方法 |
| GB9918912D0 (en) | 1999-08-12 | 1999-10-13 | Angiogene Pharm Ltd | New stilbenes with vascular damaging activity |
-
2002
- 2002-04-11 FR FR0204499A patent/FR2838437B1/fr not_active Expired - Fee Related
-
2003
- 2003-03-28 AR ARP030101111A patent/AR039198A1/es active IP Right Grant
- 2003-04-09 RS YU86504A patent/RS52331B/sr unknown
- 2003-04-09 PL PL394821A patent/PL214129B1/pl not_active IP Right Cessation
- 2003-04-09 WO PCT/FR2003/001117 patent/WO2003084919A2/fr not_active Ceased
- 2003-04-09 CN CNB038075660A patent/CN1291970C/zh not_active Expired - Fee Related
- 2003-04-09 KR KR1020047016132A patent/KR101018983B1/ko not_active Expired - Fee Related
- 2003-04-09 NZ NZ535318A patent/NZ535318A/en not_active IP Right Cessation
- 2003-04-09 CA CA2481742A patent/CA2481742C/fr not_active Expired - Fee Related
- 2003-04-09 HR HR20040935A patent/HRP20040935A2/hr not_active Application Discontinuation
- 2003-04-09 AU AU2003260026A patent/AU2003260026B2/en not_active Ceased
- 2003-04-09 IL IL16424703A patent/IL164247A0/xx not_active IP Right Cessation
- 2003-04-09 BR BR0309087-6A patent/BR0309087A/pt not_active IP Right Cessation
- 2003-04-09 MX MXPA04009112A patent/MXPA04009112A/es active IP Right Grant
- 2003-04-09 EP EP03740582A patent/EP1497255A2/fr not_active Withdrawn
- 2003-04-09 PL PL371629A patent/PL213708B1/pl not_active IP Right Cessation
- 2003-04-09 JP JP2003582118A patent/JP4299677B2/ja not_active Expired - Fee Related
- 2003-04-09 RS RS20110562A patent/RS20110562A3/en unknown
- 2003-04-09 PL PL394820A patent/PL213967B1/pl not_active IP Right Cessation
- 2003-04-09 EA EA200401350A patent/EA007965B1/ru not_active IP Right Cessation
- 2003-04-09 EP EP10183135A patent/EP2354118A1/fr not_active Withdrawn
- 2003-04-09 ME MEP-915/08A patent/MEP91508A/xx unknown
- 2003-04-09 EP EP10183123A patent/EP2348012A1/fr not_active Withdrawn
- 2003-04-09 RS RS20110561A patent/RS20110561A3/en unknown
- 2003-04-09 OA OA1200400275A patent/OA12804A/fr unknown
- 2003-04-10 TW TW092108184A patent/TWI262179B/zh not_active IP Right Cessation
- 2003-09-04 UA UA20041109227A patent/UA76079C2/uk unknown
-
2004
- 2004-09-14 CR CR7481A patent/CR7481A/es unknown
- 2004-09-15 ZA ZA200407417A patent/ZA200407417B/en unknown
- 2004-09-20 MA MA27868A patent/MA26407A1/fr unknown
- 2004-10-08 EC EC2004005348A patent/ECSP045348A/es unknown
- 2004-10-08 TN TNP2004000201A patent/TNSN04201A1/fr unknown
- 2004-11-05 NO NO20044814A patent/NO329701B1/no not_active IP Right Cessation
-
2010
- 2010-09-01 NO NO20101215A patent/NO331372B1/no not_active IP Right Cessation
-
2011
- 2011-08-05 AR ARP110102854A patent/AR082581A2/es unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |