# US 7,745,650 B2 · 9,10-α,α-OH-taxane analogs and methods for production thereof

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 7,745,650 B2
- Document ID: US7745650B2
- Status: Granted
- Kind: B2
- Application number: 10/951,555
- Filed: 2004-09-27
- Published: 2005-07-07
- Granted: 2010-06-29
- Earliest claimed: 2003-09-25
- Assignees: Tapestry Pharmaceuticals, Inc.
- Inventors: Jan Zygmunt; James Ferrara; James D. McChesney
- Web page: https://patentgrep.com/patent/US7745650B2

## CPC

- A61K 31/337: having four-membered rings, e.g. taxol
- A61K 31/357: having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- C07D 305/14: condensed with carbocyclic rings or ring systems
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 493/08: Bridged systems
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The present invention relates to taxane analogs for the treatment of cancer having the general formula: wherein R1 and R2 are each selected from H, an alkyl group, an olefinic group, an aromatic group, an O-alkyl group, an O-olefinic group, or an O-aromatic group; R3 is hydroxyl or OP1; R4 and R5 are each hydroxyl or R7COO; R6 is hydroxyl, OP2, R7COO, or an ether functionality; R7 is an alkyl group, an olefinic group, or an aromatic group; P1 and P2 are each hydroxyl protecting groups; R8 and R9 are each selected from H, alkyl group, olefinic or aromatic group. The present invention is also directed to production methods and intermediates useful in the formation of these new taxane analogs. The methods may begin with a starting compound, such as paclitaxel or docetaxel, which is converted into a taxane analog through various intermediate compounds.

## Claims

### Claim 1

A method for producing taxane analogs and compounds comprising treating a compound represented by either Formula G′ or Formula M′ with a compound of generalized formula R8R9C(OCH3)2 and an acid selected from the group consisting of camphor sulfonic acid (CSA), p-toluene sulfonic acid (PTSA), hydrochloric acid (HCl) and acetic acid (AcOH):
wherein:
R1 and R2 are each selected from H, an alkyl group, an olefinic group, an aromatic group, an O-alkyl group, an O-olefinic group, or an O-aromatic group; R7 is an alkyl group, an olefinic group, or an aromatic group; P1 is a hydroxyl protecting group; P5 is H or an acid labile protecting group at the 7-O position;
R8 is: H, alkyl group, olefinic or aromatic group; and

### Claim 2 (depends on 1)

A compound produced by the method according to claim 1.