ES2182484T3 - Nuevo procedimiento de acilacion selectiva de 10-desacetilbacatina iii en la posicion c-10. - Google Patents
Nuevo procedimiento de acilacion selectiva de 10-desacetilbacatina iii en la posicion c-10.Info
- Publication number
- ES2182484T3 ES2182484T3 ES99904208T ES99904208T ES2182484T3 ES 2182484 T3 ES2182484 T3 ES 2182484T3 ES 99904208 T ES99904208 T ES 99904208T ES 99904208 T ES99904208 T ES 99904208T ES 2182484 T3 ES2182484 T3 ES 2182484T3
- Authority
- ES
- Spain
- Prior art keywords
- iii
- solution
- baccatin
- deacetilbacatine
- acilation
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract 2
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 abstract 4
- OVMSOCFBDVBLFW-VHLOTGQHSA-N (-)-Baccatin III Natural products O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 229930014667 baccatin III Natural products 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 abstract 2
- 229930190007 Baccatin Natural products 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 125000003834 baccatin III group Chemical group 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910003002 lithium salt Inorganic materials 0.000 abstract 1
- 159000000002 lithium salts Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000005270 trialkylamine group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Compounds Of Unknown Constitution (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Steroid Compounds (AREA)
- Peptides Or Proteins (AREA)
- Paper (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Procedimiento de acilación de la 10- desacetilbacatina III en una posición C-10 sobre una posición hidroxilo C-7 de la misma, que comprende las etapas siguientes: (a) disolución de una cantidad seleccionada de 10- desacetilbacatina III en un solvente etérico aceptable, para formar una primera solución; (b) mezcla de una solución que contiene una sal de litio en la primera solución, para formar una segunda solución. (c) adición de una base seleccionada de una base trialquilamina y piridina a la segunda solución, para formar de este modo una tercera solución; y (d) combinación de la tercera solución con un agente acilante para formar una cuarta solución, de tal modo que la bacatina III se forme en la cuarta solución.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/010,285 US5914411A (en) | 1998-01-21 | 1998-01-21 | Alternate method for acylating 10-deacetylbaccatin III selectively at the C-10 position |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2182484T3 true ES2182484T3 (es) | 2003-03-01 |
Family
ID=21745026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99904208T Expired - Lifetime ES2182484T3 (es) | 1998-01-21 | 1999-01-21 | Nuevo procedimiento de acilacion selectiva de 10-desacetilbacatina iii en la posicion c-10. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5914411A (es) |
| EP (1) | EP1056736B1 (es) |
| JP (1) | JP2002501060A (es) |
| KR (1) | KR20010034082A (es) |
| CN (1) | CN1288463A (es) |
| AT (1) | ATE223394T1 (es) |
| AU (1) | AU741516B2 (es) |
| BR (1) | BR9907160A (es) |
| CA (1) | CA2312350A1 (es) |
| DE (1) | DE69902757T2 (es) |
| DK (1) | DK1056736T3 (es) |
| EA (1) | EA002576B1 (es) |
| ES (1) | ES2182484T3 (es) |
| GE (1) | GEP20022800B (es) |
| IL (1) | IL136043A0 (es) |
| NO (1) | NO20002923L (es) |
| NZ (1) | NZ505117A (es) |
| PT (1) | PT1056736E (es) |
| TR (1) | TR200001821T2 (es) |
| WO (1) | WO1999037632A1 (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7288665B1 (en) | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
| DE69918300T2 (de) | 1998-05-01 | 2005-06-30 | Napro Biotherapeutics, Inc., Boulder | Verfahren und verwendbare zwischenprodukte für paclitaxel synthese von c-7,c-10 di-cbz baccatin iii |
| US6281368B1 (en) | 2000-03-16 | 2001-08-28 | Napro Biotherapeutics, Inc. | Simple and efficient hydrazinolysis of C-10 and C-13 ester functionalities of taxanes to obtain 10-DAB III |
| US6495705B2 (en) | 2000-03-16 | 2002-12-17 | Napro Biotherapeutics, Inc. | Efficient process for the production of 10-DAB III by selective hydrazinolysis of various taxanes |
| US6358996B1 (en) | 2000-06-09 | 2002-03-19 | Napro Biotherapeutics, Inc. | Stable isotope labeling of paclitaxel |
| AU2003273671A1 (en) * | 2002-10-09 | 2004-05-04 | Phytogen Life Sciences, Inc. | Novel taxanes and methods related to use and preparation thereof |
| US7202370B2 (en) * | 2003-10-27 | 2007-04-10 | Conor Medsystems, Inc. | Semi-synthesis of taxane intermediates from 9-dihydro-13-acetylbaccatin III |
| WO2005113528A1 (en) * | 2004-05-14 | 2005-12-01 | Immunogen, Inc. | A facile method for synthesizing baccatin iii compounds |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5229526A (en) * | 1991-09-23 | 1993-07-20 | Florida State University | Metal alkoxides |
| US5440057A (en) * | 1993-08-20 | 1995-08-08 | The Scripps Research Institute | Access to taxol analogs |
| US5750736A (en) * | 1996-07-11 | 1998-05-12 | Napro Biotherapeutics, Inc. | Method for acylating 10-deacetylbaccatin III selectively at the c-10 position |
-
1998
- 1998-01-21 US US09/010,285 patent/US5914411A/en not_active Expired - Fee Related
-
1999
- 1999-01-21 KR KR1020007007691A patent/KR20010034082A/ko not_active Withdrawn
- 1999-01-21 CN CN99802200A patent/CN1288463A/zh active Pending
- 1999-01-21 DE DE69902757T patent/DE69902757T2/de not_active Expired - Fee Related
- 1999-01-21 DK DK99904208T patent/DK1056736T3/da active
- 1999-01-21 BR BR9907160-6A patent/BR9907160A/pt not_active IP Right Cessation
- 1999-01-21 EA EA200000782A patent/EA002576B1/ru not_active IP Right Cessation
- 1999-01-21 IL IL13604399A patent/IL136043A0/xx unknown
- 1999-01-21 EP EP99904208A patent/EP1056736B1/en not_active Expired - Lifetime
- 1999-01-21 CA CA002312350A patent/CA2312350A1/en not_active Abandoned
- 1999-01-21 JP JP2000528555A patent/JP2002501060A/ja active Pending
- 1999-01-21 AT AT99904208T patent/ATE223394T1/de not_active IP Right Cessation
- 1999-01-21 ES ES99904208T patent/ES2182484T3/es not_active Expired - Lifetime
- 1999-01-21 GE GEAP19995525A patent/GEP20022800B/en unknown
- 1999-01-21 WO PCT/US1999/001384 patent/WO1999037632A1/en not_active Ceased
- 1999-01-21 PT PT99904208T patent/PT1056736E/pt unknown
- 1999-01-21 AU AU24657/99A patent/AU741516B2/en not_active Ceased
- 1999-01-21 NZ NZ505117A patent/NZ505117A/xx unknown
- 1999-01-21 TR TR2000/01821T patent/TR200001821T2/xx unknown
-
2000
- 2000-06-08 NO NO20002923A patent/NO20002923L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL136043A0 (en) | 2001-05-20 |
| AU2465799A (en) | 1999-08-09 |
| DE69902757D1 (de) | 2002-10-10 |
| NZ505117A (en) | 2002-11-26 |
| NO20002923D0 (no) | 2000-06-08 |
| AU741516B2 (en) | 2001-12-06 |
| CN1288463A (zh) | 2001-03-21 |
| WO1999037632A1 (en) | 1999-07-29 |
| NO20002923L (no) | 2000-09-11 |
| EA002576B1 (ru) | 2002-06-27 |
| EA200000782A1 (ru) | 2000-12-25 |
| ATE223394T1 (de) | 2002-09-15 |
| DE69902757T2 (de) | 2003-01-09 |
| CA2312350A1 (en) | 1999-07-29 |
| TR200001821T2 (tr) | 2001-01-22 |
| PT1056736E (pt) | 2002-12-31 |
| US5914411A (en) | 1999-06-22 |
| DK1056736T3 (da) | 2002-12-30 |
| JP2002501060A (ja) | 2002-01-15 |
| GEP20022800B (en) | 2002-09-25 |
| KR20010034082A (ko) | 2001-04-25 |
| BR9907160A (pt) | 2000-10-24 |
| EP1056736A1 (en) | 2000-12-06 |
| EP1056736B1 (en) | 2002-09-04 |
| EP1056736A4 (en) | 2001-04-11 |
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