USRE40120E1 - Process for the preparation of taxanes from 10-deacetylbaccatin III - Google Patents
Process for the preparation of taxanes from 10-deacetylbaccatin III Download PDFInfo
- Publication number
- USRE40120E1 USRE40120E1 US11/025,830 US2583000A USRE40120E US RE40120 E1 USRE40120 E1 US RE40120E1 US 2583000 A US2583000 A US 2583000A US RE40120 E USRE40120 E US RE40120E
- Authority
- US
- United States
- Prior art keywords
- group
- esterified
- iii
- deacetylbaccatin iii
- protected
- 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
- 0 *N1C(C2=CC=C(OC)C=C2)O[C@@H](C(=O)O)[C@@H]1[1*] Chemical compound *N1C(C2=CC=C(OC)C=C2)O[C@@H](C(=O)O)[C@@H]1[1*] 0.000 description 6
- ONRUCCGCQAXQGF-GXRIANEASA-N C.[H][C@]12[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](O)C(C)=C([C@@H](OOC(Cl)(Cl)ClC)C(=O)[C@]1(C)[C@@H](OC(=O)C(Cl)(Cl)Cl)C[C@H]1OC[C@]12OC(C)=O)C3(C)C Chemical compound C.[H][C@]12[C@H](OC(=O)C3=CC=CC=C3)[C@]3(O)C[C@H](O)C(C)=C([C@@H](OOC(Cl)(Cl)ClC)C(=O)[C@]1(C)[C@@H](OC(=O)C(Cl)(Cl)Cl)C[C@H]1OC[C@]12OC(C)=O)C3(C)C ONRUCCGCQAXQGF-GXRIANEASA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- 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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
-
- 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
Definitions
- the present invention relates to a process for the preparation of taxanes from 10-deacetylbaccatin III.
- the present invention relates to a process for the preparation of taxanes from 10-deacetylbaccatin III.
- Paclitaxel is a known antitumor drug with taxane structure, whose industrial preparation is particularly complex.
- Paclitaxel was first isolated by extraction from the trunk barks of Taxus brevifolia, and it is at present synthesized starting from 10-deacetylbaccatin III, an intermediate present in the leaves of different species of taxus, particularly in those of Taxus baccata L., thereby overcoming the environmental problems connected with the availability of bark of T. brevifolia.
- U.S. Pat. No. Re. 34,277 discloses the. semi-synthesis of Paclitaxel starting from 10-deacetylbaccatin III protected at the C-7 hydroxyl group with a trialkylsilyl group, in particular triethylsilyl, and at the 10-position with an acetyl group.
- WO 98/08832 the protection of the C-7 hydroxyl group is carried out using a trichloroacetyl group.
- baccatin III derivative is reacted with acetyl bromide and, subsequently, with the suitable phenylisoserine derivative to obtain Paclitaxel, following deprotection of the hydroxyl groups at 7 and 2′ and benzoylation of the amine.
- Paclitaxel is prepared by reacting a beta-lactam-type compound with 7-triethylsilyl-baccatin III. The desired product is obtained by deprotection in acid medium.
- U.S. Pat. No. 5,621,121 and U.S. Pat. No. 5,637,723 disclose the synthesis of taxanes, including Paclitaxel, by reacting suitably protected baccatin III or 10-deacetylbaccatin III with oxazolidine-5-carboxylic acids bearing at the 2-position a phenyl group substituted with alkoxy groups (U.S. Pat. No. 5,621,121) or with trihaloalkyl groups, in particular trichloromethyl (U.S. Pat. No. 5,637,723), followed by deprotection by opening of the oxazolidine ring.
- taxanes including Paclitaxel
- the protective groups considered particularly suitable comprise silyl, 2,2,2-trichloroethoxycarbonyl or 2-(2 (trichloromethyl)propoxy)carbonyl groups.
- the process of the invention differs from those of the prior art in the that the reaction sequence used provides a simpler route than those processes cited above and a remarkable improvement in the obtained yields.
- the process of the invention differs from those of the prior art in that the reaction sequence used provides a simpler route than the known processes cited above and a remarkable improvement in the obtained yields.
- Step a) is conventionally effected with trichloroacetic anhydride in suitable solvents and in the presence of bases such as pyridine, triethylamine and the like.
- the esterification with the oxazolidine-5-carboxylic acid derivative is carried out in the presence of a condensing agent such as dicyclohexylcarboniimide or other known reagents, in an anhydrous organic solvent, preferably aliphatic, aromatic or chlorinated hydrocarbons, at temperatures ranging from room temperature to the boiling temperature of the solvent.
- a condensing agent such as dicyclohexylcarboniimide or other known reagents
- oxazolidine ester is then deprotected by removing the 7- and 10-trichloroacetyl groups by treatment with NH 4 OH/NH 4 Cl in aliphatic alcohols, preferably methanol.
- the selective acetylation of the hydroxyl at the 10-position is carried out with acetic anhydride in the presence of cerium III, scandium or ytterbium salts, in a solvent such as tetrahydrofuran, dichloromethane, ethyl acetate, at temperatures ranging from 5 to 40° C.
- oxazolidine intermediates are known or can be prepared with known methods, by reaction of an isoserine ester with 4-methoxy-benzaldehyde.
- anisic aldehyde proved to be particularly important for the formation of the oxazolidine, in that oxadolidine acid, contrary to the methods described in U.S. Pat. Nos. 5,621,121, 5,637,723 (Rhône-Poulene Rorer), and in U.S. Pat. No. 5,821,363 (UpJohn), can easily be crystallized and adjusted to a 95:5 isomer ratio, which is extremely useful and advantageous for the subsequent step. Furthermore, the oxazolidine carboxylic acid obtainable with anisic aldehyde is particularly stable during the deprotection of the trichloroacetic ester and the subsequent acetylation step.
- the reaction mixture is concentrated to small volume under vacuum, then diluted with water and the whole is extracted with ethyl acetate.
- the extract is concentrated to dryness and 10 g of this residue are dissolved in THF and added at 0° C. with 5 ml of formic acid.
- the reaction mixture is left under stirring at 0° C. for three hours, then diluted with water; formic acid is neutralized with KHCO 3 , the suspension is repeatedly extracted with ethyl acetate.
- the organic extracts are washed with water and concentrated to small volume. Upon crystallization from the same solvent, 9.2 g of Docetaxel are obtained having the same chemical, physical and spectroscopical characteristics as described in literature.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Seasonings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT1999MI000417A IT1308636B1 (it) | 1999-03-02 | 1999-03-02 | Procedimento per la preparazione di tassani da 10-desacetilbaccatinaiii. |
PCT/EP2000/001471 WO2000052003A1 (en) | 1999-03-02 | 2000-02-23 | A process for the preparation of taxanes from 10-deacetylbaccatin iii |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/913,891 Reissue US6500966B1 (en) | 1999-03-02 | 2000-02-23 | Process for the preparation of taxanes from 10-deacetylbaccatin III |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE40120E1 true USRE40120E1 (en) | 2008-02-26 |
Family
ID=11382101
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/913,891 Ceased US6500966B1 (en) | 1999-03-02 | 2000-02-23 | Process for the preparation of taxanes from 10-deacetylbaccatin III |
US11/025,830 Expired - Lifetime USRE40120E1 (en) | 1999-03-02 | 2000-02-23 | Process for the preparation of taxanes from 10-deacetylbaccatin III |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/913,891 Ceased US6500966B1 (en) | 1999-03-02 | 2000-02-23 | Process for the preparation of taxanes from 10-deacetylbaccatin III |
Country Status (23)
Country | Link |
---|---|
US (2) | US6500966B1 (no) |
EP (1) | EP1157018B1 (no) |
JP (1) | JP2002538155A (no) |
KR (1) | KR100660663B1 (no) |
CN (2) | CN1295223C (no) |
AT (1) | ATE231499T1 (no) |
AU (1) | AU759566B2 (no) |
BR (1) | BR0008633A (no) |
CA (1) | CA2361187C (no) |
CZ (1) | CZ301702B6 (no) |
DE (1) | DE60001265T2 (no) |
DK (1) | DK1157018T3 (no) |
ES (1) | ES2189747T3 (no) |
HK (2) | HK1042490A1 (no) |
HU (1) | HU229346B1 (no) |
IL (1) | IL145216A0 (no) |
IT (1) | IT1308636B1 (no) |
NO (1) | NO327909B1 (no) |
PL (1) | PL195906B1 (no) |
PT (1) | PT1157018E (no) |
RU (1) | RU2233276C2 (no) |
SK (1) | SK286880B6 (no) |
WO (1) | WO2000052003A1 (no) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080287696A1 (en) * | 2004-01-16 | 2008-11-20 | Dingning Tano | Process for the Preparation of Synthetic Taxanes |
US20100014087A1 (en) * | 2007-03-26 | 2010-01-21 | Ntn Corporation | Lubricant deterioration detector and bearing assembly equipped with such detector |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1318678B1 (it) * | 2000-08-10 | 2003-08-27 | Indena Spa | Procedimento per la preparazione di derivati della baccatina iii. |
US6900342B2 (en) * | 2002-05-10 | 2005-05-31 | Dabur India Limited | Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof |
US7446126B2 (en) * | 2004-10-08 | 2008-11-04 | Indena S.P.A. | Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel |
EP1647552A1 (en) * | 2004-10-08 | 2006-04-19 | INDENA S.p.A. | Semisynthesis process for the preparation of 10-deacetyl-n-debenzoyl-paclitaxel |
EP1712552A1 (en) * | 2005-04-11 | 2006-10-18 | INDENA S.p.A. | Semisynthesis process for the preparation of 10-deacetyl-n-debenzoyl-paclitaxel |
ITMI20050614A1 (it) * | 2005-04-12 | 2006-10-13 | Indena Spa | Processo per la purificazione della 10-deacetilbaccatina iii dalla 10-deacetil-2-debenzoil-2-pentenoilbaccatina iii |
KR101009467B1 (ko) | 2006-03-13 | 2011-01-19 | 주식회사 셀트리온화학연구소 | 도세탁셀의 합성에 유용한 탁산 유도체 및 그 제조방법 |
KR100847331B1 (ko) * | 2006-12-14 | 2008-07-21 | 한미약품 주식회사 | 도세탁셀의 제조방법 및 이에 사용되는 중간체 |
ITMI20062479A1 (it) * | 2006-12-21 | 2008-06-22 | Indena Spa | Processo per la preparazione di secotassani |
WO2011134067A1 (en) * | 2010-04-29 | 2011-11-03 | 6570763 Canada Inc. | Novel amino acid molecule and uses thereof |
WO2016098015A1 (en) * | 2014-12-16 | 2016-06-23 | Khashayar Karimian | New efficient methods for the synthesis of taxane derivatives such as docetaxel and their structural analogous, and a method for the preparation thereof |
CN107056767B (zh) * | 2015-12-04 | 2022-07-15 | 江苏恩华络康药物研发有限公司 | 用于制备水溶性紫杉烷类衍生物的方法及中间体 |
CN115232092A (zh) * | 2022-05-19 | 2022-10-25 | 无锡紫杉药业有限公司 | 一种10-乙酰多西他赛的制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE34277E (en) | 1988-04-06 | 1993-06-08 | Centre National De La Recherche Scientifique | Process for preparing taxol |
US5476954A (en) | 1990-11-23 | 1995-12-19 | Rhone-Poulenc Rorer S.A. | Process for preparing taxane derivatives, new derivatives obtained and pharmaceutical compositions containing them |
US5621121A (en) | 1992-10-05 | 1997-04-15 | Rhone-Poulenc Rorer S.A. | Process for the preparation of taxane derivatives |
US5637723A (en) | 1992-10-05 | 1997-06-10 | Rhone-Poulenc Rorer S.A. | Process for preparing taxane derivatives |
US6130336A (en) | 1996-08-27 | 2000-10-10 | Hanmi Pharm., Co. Ltd. | Process for preparing paclitaxel |
US6147234A (en) | 1993-03-05 | 2000-11-14 | Florida State University | C9 taxane derivatives |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2195844C (en) * | 1994-07-26 | 2001-10-09 | Ezio Bombardelli | Semi-synthetic taxanes with anti-tumoural activity |
JP2964475B2 (ja) * | 1994-11-17 | 1999-10-18 | 田辺製薬株式会社 | バッカチン誘導体及びその製法 |
GB9512471D0 (en) * | 1995-06-20 | 1995-08-23 | Pharmacia Spa | Method for the preparation of taxol and its derivatives |
US7288665B1 (en) * | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
-
1999
- 1999-03-02 IT IT1999MI000417A patent/IT1308636B1/it active
-
2000
- 2000-02-23 JP JP2000602230A patent/JP2002538155A/ja active Pending
- 2000-02-23 PL PL00349607A patent/PL195906B1/pl unknown
- 2000-02-23 CN CNB2003101149087A patent/CN1295223C/zh not_active Expired - Fee Related
- 2000-02-23 PT PT00916860T patent/PT1157018E/pt unknown
- 2000-02-23 EP EP00916860A patent/EP1157018B1/en not_active Expired - Lifetime
- 2000-02-23 CA CA002361187A patent/CA2361187C/en not_active Expired - Fee Related
- 2000-02-23 HU HU0302750A patent/HU229346B1/hu unknown
- 2000-02-23 CZ CZ20013146A patent/CZ301702B6/cs not_active IP Right Cessation
- 2000-02-23 WO PCT/EP2000/001471 patent/WO2000052003A1/en active IP Right Grant
- 2000-02-23 AU AU38060/00A patent/AU759566B2/en not_active Ceased
- 2000-02-23 IL IL14521600A patent/IL145216A0/xx not_active IP Right Cessation
- 2000-02-23 CN CNB008044236A patent/CN1133632C/zh not_active Expired - Fee Related
- 2000-02-23 KR KR1020017011048A patent/KR100660663B1/ko active IP Right Grant
- 2000-02-23 BR BR0008633-9A patent/BR0008633A/pt not_active Application Discontinuation
- 2000-02-23 DK DK00916860T patent/DK1157018T3/da active
- 2000-02-23 RU RU2001124274/04A patent/RU2233276C2/ru not_active IP Right Cessation
- 2000-02-23 ES ES00916860T patent/ES2189747T3/es not_active Expired - Lifetime
- 2000-02-23 AT AT00916860T patent/ATE231499T1/de active
- 2000-02-23 DE DE60001265T patent/DE60001265T2/de not_active Expired - Lifetime
- 2000-02-23 US US09/913,891 patent/US6500966B1/en not_active Ceased
- 2000-02-23 US US11/025,830 patent/USRE40120E1/en not_active Expired - Lifetime
- 2000-02-23 SK SK1226-2001A patent/SK286880B6/sk not_active IP Right Cessation
-
2001
- 2001-08-30 NO NO20014211A patent/NO327909B1/no not_active IP Right Cessation
-
2002
- 2002-05-31 HK HK02104134A patent/HK1042490A1/xx not_active IP Right Cessation
-
2004
- 2004-10-18 HK HK04108044A patent/HK1065309A1/xx not_active IP Right Cessation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USRE34277E (en) | 1988-04-06 | 1993-06-08 | Centre National De La Recherche Scientifique | Process for preparing taxol |
US5476954A (en) | 1990-11-23 | 1995-12-19 | Rhone-Poulenc Rorer S.A. | Process for preparing taxane derivatives, new derivatives obtained and pharmaceutical compositions containing them |
US5621121A (en) | 1992-10-05 | 1997-04-15 | Rhone-Poulenc Rorer S.A. | Process for the preparation of taxane derivatives |
US5637723A (en) | 1992-10-05 | 1997-06-10 | Rhone-Poulenc Rorer S.A. | Process for preparing taxane derivatives |
US6147234A (en) | 1993-03-05 | 2000-11-14 | Florida State University | C9 taxane derivatives |
US6130336A (en) | 1996-08-27 | 2000-10-10 | Hanmi Pharm., Co. Ltd. | Process for preparing paclitaxel |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080287696A1 (en) * | 2004-01-16 | 2008-11-20 | Dingning Tano | Process for the Preparation of Synthetic Taxanes |
US8314261B2 (en) * | 2004-01-16 | 2012-11-20 | Guilin Huiang Biochemistry Pharmaceutical Co. Ltd. | Process for the preparation of synthetic taxanes |
US20100014087A1 (en) * | 2007-03-26 | 2010-01-21 | Ntn Corporation | Lubricant deterioration detector and bearing assembly equipped with such detector |
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