RING MODIFIED CYCLIC PEPTIDE ANALOGS

WIPO Patent Application WO2000011023

A3

A method for modifying the cyclic peptide ring system of Echinocandin-type compounds to produce new analogs having antifungal activity is provided. The inventive process comprises opening the cyclic peptide ring, cleaving the terminal ornithine unit, inserting at least one new amino acid or other synthetic unit and closing the ring to produce a new cyclic peptide ring structure. The process allows one to incorporate features such as water-solubility into the cyclic peptide ring nucleus, sites for further modification, increase or decrease the number of amino acid or peptide units within the ring nucleus, and increase or decrease the total number of members within the ring. The invention further provides novel Echinocandin type compounds and their use as antifungal or anti-parasitic agents.

BORROMEO PETER STANLEY (US)
COHEN JEFFREY DANIEL (US)
GREGORY GEORGE STUART (US)
HENLE STACY KAY (US)
HITCHCOCK STEPHEN ANDREW (US)
JUNGHEIM LOUIS NICKOLAUS (US)
MAYHUGH DANIEL RAY (US)
SHEPHERD TIMOTHY ALAN (US)
TURNER WILLIAM WILSON JR (US)

PCT/US1999/018908

June 15, 2000

August 18, 1999

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LILLY CO ELI (US)
BORROMEO PETER STANLEY (US)
COHEN JEFFREY DANIEL (US)
GREGORY GEORGE STUART (US)
HENLE STACY KAY (US)
HITCHCOCK STEPHEN ANDREW (US)
JUNGHEIM LOUIS NICKOLAUS (US)
MAYHUGH DANIEL RAY (US)
SHEPHERD TIMOTHY ALAN (US)
TURNER WILLIAM WILSON JR (US)

A61K9/72; A61K38/00; A61K9/08; A61P31/10; A61P33/00; C07K1/06; C07K7/50; C07K7/54; C07K7/56; C07K7/64; (IPC1-7): C07K7/50; A61K38/12

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HENSENS E.A.: "Pneumocandins from Zalerion arboricola", JOURNAL OF ANTIBIOTICS., vol. 45, no. 12, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. TOKYO., JP, XP002126647, ISSN: 0021-8820
JAMISON E.A.: "The synthesis and antifungal activity of nitrogen containing hemiaminal ethers of LY303366", JOURNAL OF ANTIBIOTICS., vol. 51, no. 2, February 1998 (1998-02-01), JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. TOKYO., JP, pages 239 - 242, XP002126600, ISSN: 0021-8820
ZAMBIAS E.A.: "Preparation and structure-activity ewlationships of simplified analogues of the antifungal agent cilofungin: a total synthesis approach", JOURNAL OF MEDICINAL CHEMISTRY, vol. 35, no. 15, 1992, WASHINGTON US, pages 2843 - 2855, XP002126648

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