RS20110561A3 - Methods for preparing combretastatin - Google Patents
Methods for preparing combretastatinInfo
- Publication number
- RS20110561A3 RS20110561A3 RS20110561A RSP56111A RS20110561A3 RS 20110561 A3 RS20110561 A3 RS 20110561A3 RS 20110561 A RS20110561 A RS 20110561A RS P56111 A RSP56111 A RS P56111A RS 20110561 A3 RS20110561 A3 RS 20110561A3
- Authority
- RS
- Serbia
- Prior art keywords
- methoxy
- nitro
- triphenyl phosphonium
- benzaldehyde
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 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 1
- 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 1
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 abstract 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- ILRGHSDEFNGNFX-UHFFFAOYSA-N (4-methoxy-3-nitrophenyl)methyl-triphenylphosphanium Chemical class C1=C([N+]([O-])=O)C(OC)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ILRGHSDEFNGNFX-UHFFFAOYSA-N 0.000 abstract 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- DFQCYFWOOKHMQB-UHFFFAOYSA-M triphenyl-[(3,4,5-trimethoxyphenyl)methyl]phosphanium;bromide Chemical compound [Br-].COC1=C(OC)C(OC)=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 DFQCYFWOOKHMQB-UHFFFAOYSA-M 0.000 abstract 2
- UQNRTPFLTRZEIM-UHFFFAOYSA-N 2-amino-3-hydroxy-n-[2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]propanamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)C(N)CO)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 UQNRTPFLTRZEIM-UHFFFAOYSA-N 0.000 abstract 1
- -1 9-fluorenylmethyloxy carbonyl Chemical group 0.000 abstract 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 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
- 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
- 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
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Magnetic Ceramics (AREA)
- Detergent Compositions (AREA)
Abstract
Preparation of combrestatins (I) by a Wittig condensation of (3,4,5-trimethoxybenzyl) triphenyl phosphonium bromide or chloride with 3-nitro-4-methoxy benzaldehyde, or of 3,4,5-trimethoxy benzaldehyde with a (4-methoxy-3-nitrobenzyl) triphenyl phosphonium salt, followed by reduction of the nitro group on the product in the presence of iron. Preparation of combrestatins (I) by a Wittig condensation of (3,4,5-trimethoxybenzyl) triphenyl phosphonium bromide or chloride with 3-nitro-4-methoxy benzaldehyde, or of 3,4,5-trimethoxy benzaldehyde with a (4-methoxy-3-nitrobenzyl) triphenyl phosphonium salt, followed by reduction of the nitro group on the product in the presence of iron. [Image] A' : an amino group. Independent claims are included for (1) the process as described but in which the nitro group in the starting material is replaced by an amino group; (2) preparation of 2-amino-3-hydroxy-N-{2-methoxy-5-[2-(3,4,5-trimet hoxy-phenyl)-vinyl]-phenyl}-propionamide hydrochloride salt of formula (IV) by reacting (I; A = NH 2) with a protected cyclic derivative of serine of formula (IIb), to give an intermediate (III) followed by removal of the protecting group PG; (3) intermediates of formula (III). [Image] [Image] PG : a protecting group such as tert. butoxycarbonyl, benzyloxy carbonyl, or 9-fluorenylmethyloxy carbonyl. - ACTIVITY : Cytostatic. - MECHANISM OF ACTION : Not given in source material.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0204499A FR2838437B1 (en) | 2002-04-11 | 2002-04-11 | PROCESSES FOR THE PREPARATION OF COMBRETASTATINS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RS20110561A2 RS20110561A2 (en) | 2012-10-31 |
| RS20110561A3 true RS20110561A3 (en) | 2013-10-31 |
Family
ID=28459732
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RS20110562A RS20110562A3 (en) | 2002-04-11 | 2003-04-09 | Methods for preparing combretastatin |
| RS20110561A RS20110561A3 (en) | 2002-04-11 | 2003-04-09 | Methods for preparing combretastatin |
| YU86504A RS52331B (en) | 2002-04-11 | 2003-04-09 | PROCEDURES FOR OBTAINING COMBRETHSTATINE |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RS20110562A RS20110562A3 (en) | 2002-04-11 | 2003-04-09 | Methods for preparing combretastatin |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU86504A RS52331B (en) | 2002-04-11 | 2003-04-09 | PROCEDURES FOR OBTAINING COMBRETHSTATINE |
Country Status (27)
| Country | Link |
|---|---|
| EP (3) | EP2348012A1 (en) |
| JP (1) | JP4299677B2 (en) |
| KR (1) | KR101018983B1 (en) |
| CN (1) | CN1291970C (en) |
| AR (2) | AR039198A1 (en) |
| AU (1) | AU2003260026B2 (en) |
| BR (1) | BR0309087A (en) |
| CA (1) | CA2481742C (en) |
| CR (1) | CR7481A (en) |
| EA (1) | EA007965B1 (en) |
| EC (1) | ECSP045348A (en) |
| FR (1) | FR2838437B1 (en) |
| HR (1) | HRP20040935A2 (en) |
| IL (1) | IL164247A0 (en) |
| MA (1) | MA26407A1 (en) |
| ME (1) | MEP91508A (en) |
| MX (1) | MXPA04009112A (en) |
| NO (2) | NO329701B1 (en) |
| NZ (1) | NZ535318A (en) |
| OA (1) | OA12804A (en) |
| PL (3) | PL213967B1 (en) |
| RS (3) | RS20110562A3 (en) |
| TN (1) | TNSN04201A1 (en) |
| TW (1) | TWI262179B (en) |
| UA (1) | UA76079C2 (en) |
| WO (1) | WO2003084919A2 (en) |
| ZA (1) | ZA200407417B (en) |
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 (en) * | 2008-02-28 | 2013-01-18 | Sanofi Aventis | PROCESS FOR PREPARING COMBRETASTATIN |
| FR2939665B1 (en) | 2008-12-12 | 2011-10-07 | Sanofi Aventis | ANTITUMOR COMBINATION ASSOCIATING WITH AVE8062A AND DOCETAXEL |
| FR2945210B1 (en) | 2009-05-07 | 2011-07-01 | Sanofi Aventis | ANTITUMOR COMBINATION COMPRISING AVE8062 AND SORAFENIB |
| FR2953518B1 (en) * | 2009-12-03 | 2012-01-20 | Sanofi Aventis | PROCESS FOR PREPARING A COMBRETASTATIN DERIVATIVE |
| BR112012031917A2 (en) | 2010-06-18 | 2017-11-28 | Sanofi Sa | antitumor combination comprising ombrabulin, a taxane derivative and a platinum derivative |
| 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 |
| EP2407161A1 (en) | 2010-07-13 | 2012-01-18 | Sanofi | An antitumoral combination comprising ombrabulin and bevacizumab |
| FR2968557A1 (en) | 2010-12-09 | 2012-06-15 | Sanofi Aventis | ANTITUMOR COMBINATION COMPRISING A DRIFT OF THE COMBRETASTATIN FAMILY AND THE CETUXIMAB |
| FR2978663A1 (en) | 2011-08-01 | 2013-02-08 | Sanofi Sa | ANTITUMOR COMBINATION COMPRISING OMBRABULIN AND CETUXIMAB ASSOCIATED WITH RADIOTHERAPY |
| FR2978662A1 (en) | 2011-08-01 | 2013-02-08 | Sanofi Sa | ANTITUMOR COMBINATION COMPRISING OMBRABULIN AND CISPLATIN ASSOCIATED WITH RADIOTHERAPY |
| CN103012248B (en) * | 2013-01-11 | 2014-11-05 | 浙江大德药业集团有限公司 | Synthesis of amino combretastatin derivative and application of amino combretastatin derivative as oral antitumour drug |
| 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 |
| UA19045A (en) * | 1988-02-24 | 1997-12-25 | Ф.Хофманн - Ля Рош Аг | a process for preparation of derivatives of toluylene |
| 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 (en) * | 1994-04-06 | 2000-06-21 | 日本新药株式会社 | Aminostilbazole derivative and medicine |
| TW334418B (en) * | 1995-03-07 | 1998-06-21 | Ajinomoto Kk | Stilbene derivatives and pharmaceutical compositions |
| JP4551514B2 (en) * | 1999-07-23 | 2010-09-29 | 住友化学株式会社 | Process for producing unsaturated hydrocarbon residue-substituted anilines |
| 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/en not_active Expired - Fee Related
-
2003
- 2003-03-28 AR ARP030101111A patent/AR039198A1/en active IP Right Grant
- 2003-04-09 OA OA1200400275A patent/OA12804A/en unknown
- 2003-04-09 CA CA2481742A patent/CA2481742C/en not_active Expired - Fee Related
- 2003-04-09 MX MXPA04009112A patent/MXPA04009112A/en active IP Right Grant
- 2003-04-09 NZ NZ535318A patent/NZ535318A/en not_active IP Right Cessation
- 2003-04-09 KR KR1020047016132A patent/KR101018983B1/en not_active Expired - Fee Related
- 2003-04-09 CN CNB038075660A patent/CN1291970C/en not_active Expired - Fee Related
- 2003-04-09 EA EA200401350A patent/EA007965B1/en not_active IP Right Cessation
- 2003-04-09 RS RS20110562A patent/RS20110562A3/en unknown
- 2003-04-09 EP EP10183123A patent/EP2348012A1/en not_active Withdrawn
- 2003-04-09 EP EP03740582A patent/EP1497255A2/en not_active Withdrawn
- 2003-04-09 IL IL16424703A patent/IL164247A0/en not_active IP Right Cessation
- 2003-04-09 WO PCT/FR2003/001117 patent/WO2003084919A2/en not_active Ceased
- 2003-04-09 JP JP2003582118A patent/JP4299677B2/en not_active Expired - Fee Related
- 2003-04-09 PL PL394820A patent/PL213967B1/en not_active IP Right Cessation
- 2003-04-09 PL PL394821A patent/PL214129B1/en not_active IP Right Cessation
- 2003-04-09 RS RS20110561A patent/RS20110561A3/en unknown
- 2003-04-09 PL PL371629A patent/PL213708B1/en not_active IP Right Cessation
- 2003-04-09 ME MEP-915/08A patent/MEP91508A/en unknown
- 2003-04-09 EP EP10183135A patent/EP2354118A1/en not_active Withdrawn
- 2003-04-09 RS YU86504A patent/RS52331B/en unknown
- 2003-04-09 BR BR0309087-6A patent/BR0309087A/en not_active IP Right Cessation
- 2003-04-09 HR HR20040935A patent/HRP20040935A2/en not_active Application Discontinuation
- 2003-04-09 AU AU2003260026A patent/AU2003260026B2/en not_active Ceased
- 2003-04-10 TW TW092108184A patent/TWI262179B/en not_active IP Right Cessation
- 2003-09-04 UA UA20041109227A patent/UA76079C2/en unknown
-
2004
- 2004-09-14 CR CR7481A patent/CR7481A/en unknown
- 2004-09-15 ZA ZA200407417A patent/ZA200407417B/en unknown
- 2004-09-20 MA MA27868A patent/MA26407A1/en unknown
- 2004-10-08 TN TNP2004000201A patent/TNSN04201A1/en unknown
- 2004-10-08 EC EC2004005348A patent/ECSP045348A/en unknown
- 2004-11-05 NO NO20044814A patent/NO329701B1/en not_active IP Right Cessation
-
2010
- 2010-09-01 NO NO20101215A patent/NO331372B1/en not_active IP Right Cessation
-
2011
- 2011-08-05 AR ARP110102854A patent/AR082581A2/en unknown
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