Title:
PROCESS FOR THE SYNTHESIS OF INTERMEDIATES USEFUL FOR THE SYNTHESIS OF TUBULIN INHIBITORS
Document Type and Number:
WIPO Patent Application WO2004026814
Kind Code:
A3
Abstract:
The invention is a process for the preparation of compounds of the Formula (I): where R1, R2, R3, R4 and R5 are defined in the specification, which are intermediates useful for the preparation of tubulin inhibitors useful in the treatment of cancer.
More Like This:
Inventors:
WU YANZHONG (US)
MEGATI SREENIVASULU (US)
GLETSOS CONSTANTINE (US)
KENDALL JOHN THOMAS (US)
WILK BOGDAN KAZIMIERZ (US)
PADMANATHAN THURAIRAJAH (US)
RAVEENDRANATH PANOLIL (US)
MEGATI SREENIVASULU (US)
GLETSOS CONSTANTINE (US)
KENDALL JOHN THOMAS (US)
WILK BOGDAN KAZIMIERZ (US)
PADMANATHAN THURAIRAJAH (US)
RAVEENDRANATH PANOLIL (US)
Application Number:
PCT/US2003/028661
Publication Date:
August 12, 2004
Filing Date:
September 12, 2003
Export Citation:
Assignee:
WYETH CORP (US)
WU YANZHONG (US)
MEGATI SREENIVASULU (US)
GLETSOS CONSTANTINE (US)
KENDALL JOHN THOMAS (US)
WILK BOGDAN KAZIMIERZ (US)
PADMANATHAN THURAIRAJAH (US)
RAVEENDRANATH PANOLIL (US)
WU YANZHONG (US)
MEGATI SREENIVASULU (US)
GLETSOS CONSTANTINE (US)
KENDALL JOHN THOMAS (US)
WILK BOGDAN KAZIMIERZ (US)
PADMANATHAN THURAIRAJAH (US)
RAVEENDRANATH PANOLIL (US)
International Classes:
C07C45/44; C07C45/58; C07C231/18; C07C237/22; C07C269/08; C07C271/22; C07C313/06; C07K5/02; A61K38/00; (IPC1-7): C07C269/08; C07B57/00; C07C45/58; C07K5/065; C07K5/06; C07C45/44
Domestic Patent References:
| WO1999032509A2 | 1999-07-01 | |||
| WO2003072754A2 | 2003-09-04 | |||
| WO1996033211A1 | 1996-10-24 |
Other References:
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002273035
EDWIN VEDEJS ET AL.: "A total synthesis of (-)-Hemiasterlin using N-Bts methodology", JOURNAL OF ORGANIC CHEMISTRY., vol. 66, no. 22, 2001, EASTON US, pages 7355 - 7364, XP002273033
T. K. CHAKRABORTY ET AL.: "Diastereoselective strecker synthesis using alpha-phenylglycinol as chiral auxiliary", TETRAHEDRON LETTERS., vol. 32, no. 51, 1991, OXFORD GB, pages 7597 - 7600, XP002273034
CHANDRASEKHAR S ET AL: "Highly efficient cleavage of epoxides catalyzed by B(C6F5)3", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 43, no. 21, 20 May 2002 (2002-05-20), pages 3801 - 3803, XP004352410, ISSN: 0040-4039
PATENT ABSTRACTS OF JAPAN vol. 1999, no. 13 30 November 1999 (1999-11-30)
CHEMICAL ABSTRACTS, vol. 123, no. 25, 18 December 1995, Columbus, Ohio, US; abstract no. 338597b, ISHIHARA, KAZUAKI ET AL.: "Tris(pentafluorophenyl)boron as an efficient catalyst in the stereoselective rearrangment of epoxides." page 1042; column 1; XP002281134
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002281135
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002281136
N. M. WALDRON ET AL.: "The constitution of the dimers .....", JOURNAL OF THE CHEMICAL SOCIETY., 1968, LETCHWORTH GB, pages 1914 - 1917, XP001189486
CÉCILE PASCAL ET AL.: "Synthesis of Biphenyls mimicking the struture of the antimitotic rhazinilam", JOURNAL OF ORGANIC CHEMISTRY., vol. 63, no. 18, 1998, EASTON US, pages 6414 - 6420, XP002281133
J.P. BROWN ET AL.: "The chemistry of fungi.", JOURNAL OF THE CHEMICAL SOCIETY., 1949, LETCHWORTH GB, pages 859 - 867, XP001189487
NIEMAN J A ET AL: "Synthesis and Antimitotic/Cytotoxic Activity of Hemiasterlin Analogues", JOURNAL OF NATURAL PRODUCTS, vol. 66, no. 2, 2003, pages 183 - 199, XP002249342, ISSN: 0163-3864
ANDERSEN R J ET AL: "Total synthesis of (@?)-hemiasterlin, a structurally novel tripeptide that exhibits potent cytotoxic activity", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 38, no. 3, 20 January 1997 (1997-01-20), pages 317 - 320, XP004014996, ISSN: 0040-4039
EDWIN VEDEJS ET AL.: "A total synthesis of (-)-Hemiasterlin using N-Bts methodology", JOURNAL OF ORGANIC CHEMISTRY., vol. 66, no. 22, 2001, EASTON US, pages 7355 - 7364, XP002273033
T. K. CHAKRABORTY ET AL.: "Diastereoselective strecker synthesis using alpha-phenylglycinol as chiral auxiliary", TETRAHEDRON LETTERS., vol. 32, no. 51, 1991, OXFORD GB, pages 7597 - 7600, XP002273034
CHANDRASEKHAR S ET AL: "Highly efficient cleavage of epoxides catalyzed by B(C6F5)3", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 43, no. 21, 20 May 2002 (2002-05-20), pages 3801 - 3803, XP004352410, ISSN: 0040-4039
PATENT ABSTRACTS OF JAPAN vol. 1999, no. 13 30 November 1999 (1999-11-30)
CHEMICAL ABSTRACTS, vol. 123, no. 25, 18 December 1995, Columbus, Ohio, US; abstract no. 338597b, ISHIHARA, KAZUAKI ET AL.: "Tris(pentafluorophenyl)boron as an efficient catalyst in the stereoselective rearrangment of epoxides." page 1042; column 1; XP002281134
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002281135
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002281136
N. M. WALDRON ET AL.: "The constitution of the dimers .....", JOURNAL OF THE CHEMICAL SOCIETY., 1968, LETCHWORTH GB, pages 1914 - 1917, XP001189486
CÉCILE PASCAL ET AL.: "Synthesis of Biphenyls mimicking the struture of the antimitotic rhazinilam", JOURNAL OF ORGANIC CHEMISTRY., vol. 63, no. 18, 1998, EASTON US, pages 6414 - 6420, XP002281133
J.P. BROWN ET AL.: "The chemistry of fungi.", JOURNAL OF THE CHEMICAL SOCIETY., 1949, LETCHWORTH GB, pages 859 - 867, XP001189487
NIEMAN J A ET AL: "Synthesis and Antimitotic/Cytotoxic Activity of Hemiasterlin Analogues", JOURNAL OF NATURAL PRODUCTS, vol. 66, no. 2, 2003, pages 183 - 199, XP002249342, ISSN: 0163-3864
ANDERSEN R J ET AL: "Total synthesis of (@?)-hemiasterlin, a structurally novel tripeptide that exhibits potent cytotoxic activity", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 38, no. 3, 20 January 1997 (1997-01-20), pages 317 - 320, XP004014996, ISSN: 0040-4039
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