Title:
SYNTHESIS OF 2-ALKYLCYSTEINES, 2-(HYDROXYLATED PHENYL)-4-ALKYLTHIAZOLINE-4-CARBOXYLIC ACIDS AND DERIVATIVES THEREOF
Document Type and Number:
WIPO Patent Application WO2003097622
Kind Code:
A3
Abstract:
The present invention provides methods of preparing 2-alkylcysteine derivatives, many of which can be performed stereoselectively. The present invention also discloses a method of preparing a class of iron chelating agents related to desferrithiocin, all of which contain a thiazoline ring. An example of these iron chelating agents are 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-alkyl-thiazole-4-carboxylic acids, such as 4,5-dihydro-2-(2,4-dihydroxyphenyl)-4-methyl-thiazole-4-carboxylic acid.
Inventors:
CHANDA BHANU M (IN)
CHERIAN JOSEPH (IN)
CHORGHADE MUKUND S (US)
GIMI RAYOMAND H (US)
GURJAR MUKUND K (IN)
MCDONNELL PETER D (GB)
MHASKAR SUNIL V (US)
MOHAPATRA DEDENDARA K (IN)
WOLSTENHOME-HOGG PAUL (GB)
CHERIAN JOSEPH (IN)
CHORGHADE MUKUND S (US)
GIMI RAYOMAND H (US)
GURJAR MUKUND K (IN)
MCDONNELL PETER D (GB)
MHASKAR SUNIL V (US)
MOHAPATRA DEDENDARA K (IN)
WOLSTENHOME-HOGG PAUL (GB)
Application Number:
PCT/US2003/015553
Publication Date:
April 08, 2004
Filing Date:
May 15, 2003
Export Citation:
Assignee:
GENZYME CORP (US)
CHANDA BHANU M (IN)
CHERIAN JOSEPH (IN)
CHORGHADE MUKUND S (US)
GIMI RAYOMAND H (US)
GURJAR MUKUND K (IN)
MCDONNELL PETER D (GB)
MHASKAR SUNIL V (US)
MOHAPATRA DEDENDARA K (IN)
WOLSTENHOME-HOGG PAUL (GB)
CHANDA BHANU M (IN)
CHERIAN JOSEPH (IN)
CHORGHADE MUKUND S (US)
GIMI RAYOMAND H (US)
GURJAR MUKUND K (IN)
MCDONNELL PETER D (GB)
MHASKAR SUNIL V (US)
MOHAPATRA DEDENDARA K (IN)
WOLSTENHOME-HOGG PAUL (GB)
International Classes:
C07D233/64; A61K31/426; A61P7/02; A61P11/06; A61P29/00; A61P31/12; C07B53/00; C07B55/00; C07B61/00; C07C217/46; C07C227/18; C07C229/06; C07C229/42; C07C249/02; C07C253/00; C07C255/53; C07C255/54; C07C257/08; C07C319/02; C07C319/06; C07C319/12; C07C319/20; C07C323/00; C07C323/25; C07C323/35; C07C323/52; C07C323/56; C07C323/58; C07D213/55; C07D233/16; C07D237/02; C07D277/04; C07D277/08; C07D277/12; C07D277/14; C07D277/18; C07D277/56; C07D303/24; (IPC1-7): C07D277/56; C07C319/02; C07C319/12; C07C323/58
Foreign References:
| US5554753A | 1996-09-10 | |||
| EP1302467A2 | 2003-04-16 |
Other References:
EHRLER J ET AL: "TOTAL SYNTHESIS OF THIANGAZOLE", SYNLETT, THIEME VERLAG, STUTTGART, DE, September 1994 (1994-09-01), pages 702 - 704, XP001119497, ISSN: 0936-5214
KISHORE V ET AL: "SYNTHESIS OF ALPHA-POLY-ÄNEPSILON-(2-ARYL-DELTA2-THIAZOLINE-4-CARBONY L)-L- LYSINESÜ WITH ANTIVIRAL ACTIVITY", INDIAN JOURNAL OF CHEMISTRY, JODHPUR, IN, vol. 15B, March 1977 (1977-03-01), pages 255 - 257, XP001022528
A. ZAMRI ET AL.: "An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia.", TETRAHEDRON, vol. 56, 2000, pages 249 - 256, XP002252917
MULQUEEN G C ET AL: "SYNTHESIS OF THE THIAZOLINE-BASED SIDEROPHORE (S)-DESFERRITHIOCIN", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 49, no. 24, 1993, pages 5359 - 5364, XP001119496, ISSN: 0040-4020
BERGERON RAYMOND J ET AL: "Effects of C-4 Stereochemistry and C-4' Hydroxylation on the Iron Clearing Efficiency and Toxicity of Desferrithiocin Analogues", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 42, 1999, pages 2432 - 2440, XP002182656, ISSN: 0022-2623
O'DONNELL M J ET AL: "ALPHA-METHYL AMINO ACIDS BY CATALYTIC PHASE-TRANSFER ALKYLATIONS", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 23, no. 41, 1982, pages 4259 - 4262, XP009016508, ISSN: 0040-4039
KISHORE V ET AL: "SYNTHESIS OF ALPHA-POLY-ÄNEPSILON-(2-ARYL-DELTA2-THIAZOLINE-4-CARBONY L)-L- LYSINESÜ WITH ANTIVIRAL ACTIVITY", INDIAN JOURNAL OF CHEMISTRY, JODHPUR, IN, vol. 15B, March 1977 (1977-03-01), pages 255 - 257, XP001022528
A. ZAMRI ET AL.: "An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia.", TETRAHEDRON, vol. 56, 2000, pages 249 - 256, XP002252917
MULQUEEN G C ET AL: "SYNTHESIS OF THE THIAZOLINE-BASED SIDEROPHORE (S)-DESFERRITHIOCIN", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 49, no. 24, 1993, pages 5359 - 5364, XP001119496, ISSN: 0040-4020
BERGERON RAYMOND J ET AL: "Effects of C-4 Stereochemistry and C-4' Hydroxylation on the Iron Clearing Efficiency and Toxicity of Desferrithiocin Analogues", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 42, 1999, pages 2432 - 2440, XP002182656, ISSN: 0022-2623
O'DONNELL M J ET AL: "ALPHA-METHYL AMINO ACIDS BY CATALYTIC PHASE-TRANSFER ALKYLATIONS", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 23, no. 41, 1982, pages 4259 - 4262, XP009016508, ISSN: 0040-4039
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