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Details for Patent: 7,763,738

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Details for Patent: 7,763,738

Title:Synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors
Abstract: Disclosed is a novel enantiomeric synthesis ceramide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.
Inventor(s): Hirth; Bradford H. (Littleton, MA), Siegel; Craig (Woburn, MA)
Assignee: Genzyme Corporation (Cambridge, MA)
Filing Date:Aug 24, 2007
Application Number:11/895,632
Claims:1. A method of preparing an acylated ceramide compound represented by the following structural formula: ##STR00032## R.sub.1 is a substituted or unsubstituted aromatic group; R.sub.2 and R.sub.3 are independently --H, a substituted or unsubstituted aliphatic group or, taken together with the nitrogen atom to which they are bonded, are a substituted or unsubstituted non-aromatic heterocyclic ring; and R.sub.7 is a substituted or unsubstituted aliphatic group; said method comprising the steps of: a) reacting an acyclic compound represented by the following structural formula: ##STR00033## with an amide reducing agent, thereby forming an amine compound represented by the following structural formula: ##STR00034## b) debenzylating the --NHCH(--CH.sub.2OH)R.sub.5 group of the amine compound, thereby forming a sphingosine-like compound represented by the following structural formula: ##STR00035## c) acylating the primary amine group of the sphingosine-like compound, thereby forming the acylated ceramide compound.

2. A method of preparing an acylated ceramide compound represented by the following structural formula: ##STR00036## R.sub.1 is para-hydroxyphenyl or ##STR00037## R.sub.7 is a C7-C10 alkyl group; said method comprising the steps of: a) reacting an acyclic compound represented by the following structural formula: ##STR00038## with an amide reducing agent, thereby forming an amine compound represented by the following structural formula: ##STR00039## b) debenzylating the --NHCH(--CH.sub.2OH)(phenyl) group of the amine compound, thereby forming a sphingosine-like compound represented by the following structural formula: ##STR00040## c) acylating the primary amine group of the sphingosine-like compound, thereby forming the acylated ceramide compound.

3. The method of claim 2, wherein the ceramide compound is represented by the following structural formula: ##STR00041## and the sphingosine-like compound is represented by the following structural formula ##STR00042##

4. The method of claim 3, wherein the sphingosine-like compound is acylated with CH.sub.3(CH.sub.2).sub.6COX, wherein X is a leaving group, thereby forming the ceramide compound.

5. The method of claim 4, wherein X is --Cl or N-hydroxysuccinimidyl.
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