# US 8,569,362 B2 · Polyketide molecules as anticancer agents

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- Number: US 8,569,362 B2
- Document ID: US8569362B2
- Status: Granted
- Kind: B2
- Application number: 13/504,797
- Filed: 2010-10-28
- Published: 2012-10-04
- Granted: 2013-10-29
- Earliest claimed: 2009-10-28
- Assignees: Pierre Fabre Medicament; Centre National de la Recherche Scientifique (CNRS); Institut de Recherche pour le Development (IRD)
- Applicants: Isabelle Carletti; Georges Massiot; Cécile Debitus
- Inventors: Isabelle Carletti; Georges Massiot; Cécile Debitus
- Web page: https://patentgrep.com/patent/US8569362B2

## CPC

- C07D 407/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 35/00: Antineoplastic agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to a polyketide molecule of the following formula (I): or a pharmaceutically acceptable salt thereof, where R1 is a hydrogen atom or a (C1-C7) alkyl group, as well as the method of preparation and use thereof, in particular as an anticancer agent.

## Claims

### Claim 1

A compound of following formula (I):
or a phatmaceutically acceptable salt thereof,
where R1 is a hydrogen atom or a (C1-C7) alkyl group.

### Claim 2 (depends on 1)

The compound according to claim 1, selected from the following compounds:

### Claim 3 (depends on 1)

A pharmaceutical composition comprising at least one compound according to claim 1 and at least one pharmaceutically acceptable excipient.

### Claim 4 (depends on 1)

A method of synthesizing a compound according to claim 1, comprising the following successive steps:
(i) maceration of lyophilisate of Hemimycale sp. sponge with chloroform then with a hydro-ethanolic solution, followed by filtration to give a filtrate, then concentration of said filtrate to give an extract,
(ii) partition of the extract obtained at the preceding step (i) between water and dichloromethane and separation of the resulting aqueous and organic phases, extraction of the aqueous phase with ethyl acetate and separation of the new resulting aqueous and organic phases, combination of the two organic phases thereby obtained and concentration to give a desalinated extract,
(iii) taking up the desalinated extract obtained at the preceding step (ii) with a hydro-methanolic solution and hexane, recovery and concentration of the methanolic phase to give a methanolic extract,
(iv) isolation of the compound of formula (I) with R1=H from the methanolic extract obtained at the preceding step (iii), and
(v) optionally esterification of the carboxylic acid at C-(1) to give a compound of formula (I) with R1 =(C1-C7) alkyl and/or salification of the compound obtained at the preceding step (iv), and isolation of the compound thereby obtained from the reaction mixture.

### Claim 5 (depends on 4)

The method of synthesizing according to claim 4, wherein the sponge Hemimycale sp. originates from the Torres archipelago, Vanuatu.

### Claim 6 (depends on 1)

A method of synthesizing a compound according to claim 1 with R1 representing a (C1-C7) alkyl group from a compound according to claim 1 with R1=H, comprising the following successive steps:
(a) esterification of the carboxylic acid at C-(1) to give a compound of formula (I) with R1=(C1-C7) alkyl,
(b) optionally salification of the compound obtained at the preceding step (a), and
(c) isolation of the compound obtained at the preceding step (a) or (b) from the reaction mixture.