Title:
PREPARATION OF 24 ALKYL ANALOGS OF CHOLECALCIFEROL AND NON-RACEMIC COMPOUNDS
Document Type and Number:
WIPO Patent Application WO2003087048
Kind Code:
A3
Abstract:
Disclosed is a process for the preparation of 24-alkyl analogs of cholecalcyferol of Formula (1) having a (5E) or (5Z) configuration, wherein X represents a hydrogen atom, a hydroxy group or an OR1 group, wherein R1, R2 and R3 may be the same or different and represent groups suitable for hydroxyl protection, and R4 is a C1-6 alkyl chain or a C1-6 alkyl groups, especially for calcipotriol. The invention also provides new non-racemic compounds being valuable synthones for the synthesis of pharmacologically active substances.
Inventors:
KUTNER ANDRZEJ (PL)
MARTYNOW JACEK (PL)
CHODYNSKI MICHAL (PL)
SZELEJEWSKI WIESLAW (PL)
FITAK HANNA (PL)
KRUPA MALGORZATA (PL)
MARTYNOW JACEK (PL)
CHODYNSKI MICHAL (PL)
SZELEJEWSKI WIESLAW (PL)
FITAK HANNA (PL)
KRUPA MALGORZATA (PL)
Application Number:
PCT/PL2003/000037
Publication Date:
March 18, 2004
Filing Date:
April 10, 2003
Export Citation:
Assignee:
INST FARMACEUTYCZNY (PL)
KUTNER ANDRZEJ (PL)
MARTYNOW JACEK (PL)
CHODYNSKI MICHAL (PL)
SZELEJEWSKI WIESLAW (PL)
FITAK HANNA (PL)
KRUPA MALGORZATA (PL)
KUTNER ANDRZEJ (PL)
MARTYNOW JACEK (PL)
CHODYNSKI MICHAL (PL)
SZELEJEWSKI WIESLAW (PL)
FITAK HANNA (PL)
KRUPA MALGORZATA (PL)
International Classes:
C07C31/133; C07C309/73; C07C401/00; C07F7/18; (IPC1-7): C07C401/00; C07D277/74; C07D277/76; C07C31/27; C07C309/72; C07F7/18
Domestic Patent References:
| WO1987000834A1 | 1987-02-12 | |||
| WO1999036400A1 | 1999-07-22 |
Foreign References:
| EP0578494A1 | 1994-01-12 |
Other References:
CALVERLEY M J: "SYNTHESIS OF MC 903, A BIOLOGICALLY ACTIVE VITAMIN D METABOLITE ANALOGUE", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 43, no. 20, 1987, pages 4609 - 4619, XP001147723, ISSN: 0040-4020
MAHN-JOO KIM, JOON YOUNG KIM: "Synthesis of Optically Pure (R)-2-Hydrixy Acids using D-Lactate Dehydrogenase", J. CHEM. SOC.., CHEM. COMMUN., - 1991, pages 326 - 27, XP009014245
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KIM, MAHN JOO; WHITESIDES GEORGE M.: "L-Lactatedehydrogenase: substrate specificity and use as a catalyst in the synthesis of homochiral 2-hydroxy acids", XP002259744, retrieved from STN Database accession no. AN 108:183196
U. GOERGENS, M. P. SCHNEIDER: "A Facile Chemoenzymatic Route to Enantiomerically Pure Oxiranes: Building blocks for Biologically Active Compounds", J. CHEM. COMMUN., 1991, pages 1064 - 66, XP009014237
M. J. CALVERLEY: "The Seleno-Acetal Route to the Side-Chain-Modified 1.alpha.-Hydroxy-Vitamin D Analogues: Stereoselective Synthesis of the New 22Z Isomer of MC 903 (Calcipotriol)", SYNLETT, 1990, pages 157 - 59, XP001153859
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002248813, Database accession no. BRN 2525290
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002248814, Database accession no. BRN 8264410
J. OLLIVIER ET AL.: "Rearrangement of Optically Active Cyclopropyl Allyl Esters by Lewis Acids and Palladium (0) Catalysis", TETRAHEDRON LETT., vol. 31, no. 29, pages 4135 - 38, XP009014264
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259745, Database accession no. BRN 4955870
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259746, Database accession no. Reaction ID 4248618
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259747, Database accession no. BRN 5693287
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259748, Database accession no. Reaction ID 2135845
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259749, Database accession no. Reaction ID 1849182
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259750, Database accession no. BRN 2950451
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259751, Database accession no. Reaction ID 1755833
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259752, Database accession no. BRN 1700471
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259753, Database accession no. Reaction ID 988296
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259754, Database accession no. Reaction ID 2262409
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259755, Database accession no. Reaction ID 2772099
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259756, Database accession no. Reaction ID 3380816
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259757, Database accession no. Reaction ID 195255
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259758, Database accession no. Reaction ID 3600893
MAHN-JOO KIM, JOON YOUNG KIM: "Synthesis of Optically Pure (R)-2-Hydrixy Acids using D-Lactate Dehydrogenase", J. CHEM. SOC.., CHEM. COMMUN., - 1991, pages 326 - 27, XP009014245
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KIM, MAHN JOO; WHITESIDES GEORGE M.: "L-Lactatedehydrogenase: substrate specificity and use as a catalyst in the synthesis of homochiral 2-hydroxy acids", XP002259744, retrieved from STN Database accession no. AN 108:183196
U. GOERGENS, M. P. SCHNEIDER: "A Facile Chemoenzymatic Route to Enantiomerically Pure Oxiranes: Building blocks for Biologically Active Compounds", J. CHEM. COMMUN., 1991, pages 1064 - 66, XP009014237
M. J. CALVERLEY: "The Seleno-Acetal Route to the Side-Chain-Modified 1.alpha.-Hydroxy-Vitamin D Analogues: Stereoselective Synthesis of the New 22Z Isomer of MC 903 (Calcipotriol)", SYNLETT, 1990, pages 157 - 59, XP001153859
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002248813, Database accession no. BRN 2525290
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002248814, Database accession no. BRN 8264410
J. OLLIVIER ET AL.: "Rearrangement of Optically Active Cyclopropyl Allyl Esters by Lewis Acids and Palladium (0) Catalysis", TETRAHEDRON LETT., vol. 31, no. 29, pages 4135 - 38, XP009014264
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259745, Database accession no. BRN 4955870
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259746, Database accession no. Reaction ID 4248618
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259747, Database accession no. BRN 5693287
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259748, Database accession no. Reaction ID 2135845
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259749, Database accession no. Reaction ID 1849182
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259750, Database accession no. BRN 2950451
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259751, Database accession no. Reaction ID 1755833
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259752, Database accession no. BRN 1700471
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259753, Database accession no. Reaction ID 988296
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259754, Database accession no. Reaction ID 2262409
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259755, Database accession no. Reaction ID 2772099
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259756, Database accession no. Reaction ID 3380816
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259757, Database accession no. Reaction ID 195255
DATABASE CROSSFIRE BEILSTEIN [online] Beilstein Institut zur Förderung der Chemischen Wissenschaften, Frankfurt am Main, DE; XP002259758, Database accession no. Reaction ID 3600893
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