Synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors

• US 6,855,830 B2
• Filed: 07/16/2002
• Issued: 02/15/2005
• Est. Priority Date: 07/16/2001
• Status: Expired due to Term

• Current Assignee: Genzyme Corporation (Sanofi )
• Original Assignee: Genzyme Corporation (Sanofi )
• Inventors: Hirth, Bradford H., Siegel, Craig
• Primary Examiner(s): McKane, Joseph K.
• Assistant Examiner(s): ANDERSON, REBECCA L
• Application Number:
  US10/197,227
• Publication Number:
  US 20030050299A1
• Time in Patent Office: 945 Days
• Field of Search: 548/526
• US Class Current: 548/526
• CPC Class Codes: A61K 31/4025 not condensed and containing further heterocyclic rings, e.g. cromakalim
• CPC Class Codes: A61P 1/16 for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 7/06 Antianaemics
• CPC Class Codes: C07D 295/185 from aliphatic carboxylic acids
• CPC Class Codes: C07D 319/18 Ethylenedioxybenzenes, not substituted on the hetero ring
• CPC Class Codes: C07D 405/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 498/04 Ortho-condensed systems

Abstract

Disclosed is a novel enantiomeric synthesis cermamide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

Claims

1. A compound represented by the following structural formula:

the enantiomer of the compound, a salt of the compound, or

a salt of the enantiomer, wherein;

R₄ is H₂ or O; and

R₆ is represented by the following structural formula;

wherein phenyl ring A is substituted or unsubstituted;

or

when R₄ is H₂, R₆ can further be —

H.

2. The compound of claim 1 wherein phenyl ring A is unsubstituted.