CA2307548A1 - Procede de conversion de la 9-dihydro-13-acetylbaccatine iii en taxol et ses derives - Google Patents

Procede de conversion de la 9-dihydro-13-acetylbaccatine iii en taxol et ses derives Download PDF

Info

Publication number: CA2307548A1
Authority: CA; Canada
Prior art keywords: taxol; dihydro; substituted; derivatives; converting
Prior art date: 1997-05-01
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.): Granted

Application number

CA002307548A

Other languages

English (en)

Other versions

CA2307548C (fr

Inventor

Jian Liu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ivax Research Holdings Inc

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1997-05-01

Filing date

1998-05-01

Publication date

1998-11-12

1997-05-01 Priority claimed from CA002204197A external-priority patent/CA2204197A1/fr

1998-05-01 Application filed by Individual filed Critical Individual

1998-05-01 Priority to CA002307548A priority Critical patent/CA2307548C/fr

1998-11-12 Publication of CA2307548A1 publication Critical patent/CA2307548A1/fr

2001-07-17 Application granted granted Critical

2001-07-17 Publication of CA2307548C publication Critical patent/CA2307548C/fr

2018-05-01 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

WPPPFZJNKLMYBW-FAEUQDRCSA-N 13-acetyl-9-dihydrobaccatin iii Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](OC(C)=O)[C@H](O)[C@]3(C)[C@@H](O)C[C@H]4OC[C@]4([C@H]31)OC(C)=O)C2(C)C)C)OC(=O)C)C(=O)C1=CC=CC=C1 WPPPFZJNKLMYBW-FAEUQDRCSA-N 0.000 title abstract 2
FFCWRLFQIKDRNO-UHFFFAOYSA-N 9-dihydro-13-acetyl baccatin III Natural products CC(=O)OC1C2C(O)CC(OC(=O)C)C3(CO3)C2C(OC(=O)C)C4(O)CC(OC(=O)C)C(=C(C1OC(=O)C)C4(C)C)C FFCWRLFQIKDRNO-UHFFFAOYSA-N 0.000 title abstract 2
229930012538 Paclitaxel Natural products 0.000 title abstract 2
229960001592 paclitaxel Drugs 0.000 title abstract 2
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](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)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 title abstract 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical compound O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
239000000543 intermediate Substances 0.000 abstract 2
125000002088 tosyl group Chemical class [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 abstract 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
230000001590 oxidative effect Effects 0.000 abstract 1
125000006239 protecting 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
- 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)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002307548A 1997-05-01 1998-05-01 Procede de conversion de la 9-dihydro-13-acetylbaccatine iii en taxol et ses derives Expired - Fee Related CA2307548C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002307548A CA2307548C (fr)	1997-05-01	1998-05-01	Procede de conversion de la 9-dihydro-13-acetylbaccatine iii en taxol et ses derives

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CA2,204,197		1997-05-01
CA002204197A CA2204197A1 (fr)	1997-05-01	1997-05-01	Methode pour convertir la 9-dihydro-13-acetylbaccatine iii en taxol et en ses derives
PCT/CA1998/000401 WO1998050378A1 (fr)	1997-05-01	1998-05-01	Procede de conversion de la 9-dihydro-13-acetylbaccatine iii en taxol et ses derives
CA002307548A CA2307548C (fr)	1997-05-01	1998-05-01	Procede de conversion de la 9-dihydro-13-acetylbaccatine iii en taxol et ses derives

Publications (2)

Publication Number	Publication Date
CA2307548A1 true CA2307548A1 (fr)	1998-11-12
CA2307548C CA2307548C (fr)	2001-07-17

Family

ID=25679287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002307548A Expired - Fee Related CA2307548C (fr)	1997-05-01	1998-05-01	Procede de conversion de la 9-dihydro-13-acetylbaccatine iii en taxol et ses derives

Country Status (1)

Country	Link
CA (1)	CA2307548C (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2007101335A1 (fr) *	2006-03-08	2007-09-13	6570763 Canada Inc.	Conversion de la 9-dihydro-13-acetylbaccatine iii en 10-desacetylbaccatine iii
WO2007143839A1 (fr) *	2006-06-12	2007-12-21	6570763 Canada Inc.	Voie semi-synthétique pour la préparation de paclitaxel, docétaxel et 10-désacétylbaccatine iii à partir de 9-dihydro-13-acétylbaccatine iii
US7847111B2 (en)	2006-06-19	2010-12-07	Canada Inc.	Semi-synthetic route for the preparation of paclitaxel, docetaxel, and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III

1998
- 1998-05-01 CA CA002307548A patent/CA2307548C/fr not_active Expired - Fee Related

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2007101335A1 (fr) *	2006-03-08	2007-09-13	6570763 Canada Inc.	Conversion de la 9-dihydro-13-acetylbaccatine iii en 10-desacetylbaccatine iii
WO2007143839A1 (fr) *	2006-06-12	2007-12-21	6570763 Canada Inc.	Voie semi-synthétique pour la préparation de paclitaxel, docétaxel et 10-désacétylbaccatine iii à partir de 9-dihydro-13-acétylbaccatine iii
US7847111B2 (en)	2006-06-19	2010-12-07	Canada Inc.	Semi-synthetic route for the preparation of paclitaxel, docetaxel, and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III

Also Published As

Publication number	Publication date
CA2307548C (fr)	2001-07-17

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Legal Events

Date	Code	Title	Description
2000-06-02	EEER	Examination request
2008-05-01	MKLA	Lapsed