US 2001/0044549 A1 · Process for the preparation of a paclitaxel C-4 methyl carbonate analog

Abstract

A process for the synthesis of a C-4 methyl carbonate paclitaxel analog from 10-deacetylbaccatin III by the selective reduction of the acetate at the C-4 position of 10-deacetylbaccatin using Red-Al.

Claims11

Dependent claims

A process for the synthesis of a C-4 methylcarbonate analog of paclitaxel from 10-deacetylbaccatin, which comprises the steps of:

(a) preparing a C-4 methylcarbonate analog of 10-deacetylbaccatin from 10-deacetylbaccatin by reductive removal of the C-4 acetate using a reducing agent followed by the addition of a methylcarbonate to the C-4 hydroxyl group;
(b) selectively protecting the C-7 hydroxyl group with a dialkyldialkyloxysilane protecting group;
(c) acetylating the C-10 hydroxyl group;
(d) coupling a paclitaxel sidechain to the C-13 hydyroxyl group;
and
(e) deprotecting said silylether protecting group at C-7.

3 more elements

Dependencies are inferred from the claim text.

Facts

Application

09/813,085Filed 20 Mar 2001

Priority

11 Aug 1999

Published

22 Nov 2001

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 305/14
Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms: condensed with carbocyclic rings or…
C07F 7/1804
Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages: compounds having Si-O-C linkages
C07D
Heterocyclic compounds
C07F
Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen

Family

Application60/148,392Us provisional application · filed 11 Aug 1999

Application09/635,553Division · filed 10 Aug 2000

Application09/813,085Division · filed 20 Mar 2001

US 6,248,908 B1Related patent

US 6,353,120 B2Related patent

US 2001/0044549 A1This patent

From the US filing history. Foreign family members aren’t listed.

Abstract

A process for the synthesis of a C-4 methyl carbonate paclitaxel analog from 10-deacetylbaccatin III by the selective reduction of the acetate at the C-4 position of 10-deacetylbaccatin using Red-Al.

Claims11

Dependent claims

A process for the synthesis of a C-4 methylcarbonate analog of paclitaxel from 10-deacetylbaccatin, which comprises the steps of:

(a) preparing a C-4 methylcarbonate analog of 10-deacetylbaccatin from 10-deacetylbaccatin by reductive removal of the C-4 acetate using a reducing agent followed by the addition of a methylcarbonate to the C-4 hydroxyl group;
(b) selectively protecting the C-7 hydroxyl group with a dialkyldialkyloxysilane protecting group;
(c) acetylating the C-10 hydroxyl group;
(d) coupling a paclitaxel sidechain to the C-13 hydyroxyl group;
and
(e) deprotecting said silylether protecting group at C-7.

3 more elements

Dependencies are inferred from the claim text.

Process for the preparation of a paclitaxel C-4 methyl carbonate analog

Life of this patent

Abstract

Claims11

Process for the preparation of a paclitaxel C-4 methyl carbonate analog

Life of this patent

Abstract

Claims11