Title:
PROCESS FOR PREPARATION OF 13,14-DIHYDRO-PGF2a DERIVATIVES
Document Type and Number:
WIPO Patent Application WO2006112742
Kind Code:
A3
Abstract:
Invention relates to the process for preparation of 13,14-dihydro-PGF2a derivatives of R or S configuration at carbon atom in omega chain substituted by hydroxyl, represented by formula (I), wherein the meaning of substituents is defined in the description. Compounds (I) are valuable biologically active substances or intermediates thereof. The invention especially relates to the process for preparation of 13,14-dihydro-15(R)-17-substituted-18,19,20-trinor-PGF2a, ie. latanoprost.
Inventors:
MARTYNOW JACEK (PL)
JOZWIK JULITA (PL)
SZELEJEWSKI WIESLAW (PL)
ACHMATOWICZ OSMAN (PL)
KUTNER ANDRZEJ (PL)
WISNIEWSKI KRZYSZTOF (PL)
WINIARSKI JERZY (PL)
ZEGROCKA-STENDEL OLIWIA (PL)
GOLEBIEWSKI PIOTR (PL)
JOZWIK JULITA (PL)
SZELEJEWSKI WIESLAW (PL)
ACHMATOWICZ OSMAN (PL)
KUTNER ANDRZEJ (PL)
WISNIEWSKI KRZYSZTOF (PL)
WINIARSKI JERZY (PL)
ZEGROCKA-STENDEL OLIWIA (PL)
GOLEBIEWSKI PIOTR (PL)
Application Number:
PCT/PL2006/000023
Publication Date:
December 28, 2006
Filing Date:
April 18, 2006
Export Citation:
Assignee:
INST FARMACEUTYCZNY (PL)
MARTYNOW JACEK (PL)
JOZWIK JULITA (PL)
SZELEJEWSKI WIESLAW (PL)
ACHMATOWICZ OSMAN (PL)
KUTNER ANDRZEJ (PL)
WISNIEWSKI KRZYSZTOF (PL)
WINIARSKI JERZY (PL)
ZEGROCKA-STENDEL OLIWIA (PL)
GOLEBIEWSKI PIOTR (PL)
MARTYNOW JACEK (PL)
JOZWIK JULITA (PL)
SZELEJEWSKI WIESLAW (PL)
ACHMATOWICZ OSMAN (PL)
KUTNER ANDRZEJ (PL)
WISNIEWSKI KRZYSZTOF (PL)
WINIARSKI JERZY (PL)
ZEGROCKA-STENDEL OLIWIA (PL)
GOLEBIEWSKI PIOTR (PL)
International Classes:
C07C405/00; C07C33/46; C07C317/18; C07D303/04; C07D327/10; C07D493/08; C07F7/18
Domestic Patent References:
| WO2002096868A2 | 2002-12-05 | |||
| WO1999002165A1 | 1999-01-21 | |||
| WO2001057015A1 | 2001-08-09 | |||
| WO2003037857A2 | 2003-05-08 | |||
| WO2002096898A2 | 2002-12-05 | |||
| WO2002090324A1 | 2002-11-14 |
Other References:
MARCZAK S ET AL: "TOTAL SYNTHESIS OF 15 OXO-13 14-DIHYDROPROSTAGLANDIN F-2-ALPHA A MAJOR METABOLITE OF PROSTAGLANDIN F-2-ALPHA", SYNTHETIC COMMUNICATIONS, vol. 19, no. 3-4, 1989, pages 633 - 640, XP008066273, ISSN: 0039-7911
KIM CHOUNG U ET AL: "Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, vol. 41, no. 14, 2 July 1998 (1998-07-02), pages 2451 - 2460, XP002389168, ISSN: 0022-2623
KITAZUME T ET AL: "THE SYNTHESIS OF OPTICALLY ACTIVE BUILDING BLOCKS CARRYING A MONOFLUOROMETHYL GROUP", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 35, 1987, pages 477 - 488, XP002938951, ISSN: 0022-1139
COREY, E. J. ET AL: "A catalytic enantioselective synthesis of chiral monosubstituted oxiranes", TETRAHEDRON LETTERS , 34(33), 5227-30 CODEN: TELEAY; ISSN: 0040-4039, 1993, XP002403466
ZHAO, HE ET AL: "Chiral synthesis of yashabushiketol", CHINESE CHEMICAL LETTERS , 5(5), 367-70 CODEN: CCLEE7; ISSN: 1001-8417, 1994, XP008070209
HANZAWA Y ET AL: "KINETIC RESOLUTION OF FLUOROALKYL-E-VINYL CARBINOL DERIVATIVES BY ASYMMETRIC EPOXIDATION WITH TITANIUM-TARTRATE CATALYSTS", CHEMICAL AND PHARMACEUTICAL BULLETIN (TOKYO), vol. 35, no. 4, 1987, pages 1633 - 1636, XP002403467, ISSN: 0009-2363
DESROY N ET AL: "Stereoselective synthesis of C15@?C24 and C25@?C30 fragments of dolabelides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 44, no. 9, 24 February 2002 (2002-02-24), pages 1763 - 1766, XP004408796, ISSN: 0040-4039
DUFFIELD J J ET AL: "Synthesis of (7S,15S)- and (7R,15S)-dolatrienoic acid.", JOURNAL OF NATURAL PRODUCTS. APR 2001, vol. 64, no. 4, April 2001 (2001-04-01), pages 472 - 479, XP002403468, ISSN: 0163-3864
ALBERICO D ET AL: "Palladium-catalyzed sequential alkylation-alkenylation reactions: application towards the synthesis of polyfunctionalized fused aromatic rings", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 61, no. 26, 27 June 2005 (2005-06-27), pages 6283 - 6297, XP004923093, ISSN: 0040-4020
KIM CHOUNG U ET AL: "Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, vol. 41, no. 14, 2 July 1998 (1998-07-02), pages 2451 - 2460, XP002389168, ISSN: 0022-2623
KITAZUME T ET AL: "THE SYNTHESIS OF OPTICALLY ACTIVE BUILDING BLOCKS CARRYING A MONOFLUOROMETHYL GROUP", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 35, 1987, pages 477 - 488, XP002938951, ISSN: 0022-1139
COREY, E. J. ET AL: "A catalytic enantioselective synthesis of chiral monosubstituted oxiranes", TETRAHEDRON LETTERS , 34(33), 5227-30 CODEN: TELEAY; ISSN: 0040-4039, 1993, XP002403466
ZHAO, HE ET AL: "Chiral synthesis of yashabushiketol", CHINESE CHEMICAL LETTERS , 5(5), 367-70 CODEN: CCLEE7; ISSN: 1001-8417, 1994, XP008070209
HANZAWA Y ET AL: "KINETIC RESOLUTION OF FLUOROALKYL-E-VINYL CARBINOL DERIVATIVES BY ASYMMETRIC EPOXIDATION WITH TITANIUM-TARTRATE CATALYSTS", CHEMICAL AND PHARMACEUTICAL BULLETIN (TOKYO), vol. 35, no. 4, 1987, pages 1633 - 1636, XP002403467, ISSN: 0009-2363
DESROY N ET AL: "Stereoselective synthesis of C15@?C24 and C25@?C30 fragments of dolabelides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 44, no. 9, 24 February 2002 (2002-02-24), pages 1763 - 1766, XP004408796, ISSN: 0040-4039
DUFFIELD J J ET AL: "Synthesis of (7S,15S)- and (7R,15S)-dolatrienoic acid.", JOURNAL OF NATURAL PRODUCTS. APR 2001, vol. 64, no. 4, April 2001 (2001-04-01), pages 472 - 479, XP002403468, ISSN: 0163-3864
ALBERICO D ET AL: "Palladium-catalyzed sequential alkylation-alkenylation reactions: application towards the synthesis of polyfunctionalized fused aromatic rings", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 61, no. 26, 27 June 2005 (2005-06-27), pages 6283 - 6297, XP004923093, ISSN: 0040-4020
Download PDF: