|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:||Jul 06, 2010|
|Claims:||1. A compound represented by the following structural formula: ##STR00032## the enantiomer of the compound, a salt of the compound, or a salt of the enantiomer, wherein: 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; R.sub.4 is O or H.sub.2; and R.sub.5 is a substituted or unsubstituted aromatic group. |
2. The compound of claim 1 wherein: R.sub.1 and R.sub.5 are independently a substituted or unsubstituted phenyl group; and R.sub.2 and R.sub.3 are independently --H, an unsubstituted C1-C5 alkyl group or, taken together with the nitrogen atom to which they are bonded, are an unsubstituted C3-C10 non-aromatic heterocyclic ring.
3. The compound of claim 2 wherein R.sub.5 is a phenyl group.
4. The compound of claim 3 wherein R.sub.2 and R.sub.3 taken together with the nitrogen atom to which they are bonded, are pyrrolidinyl, piperazinyl, azetidinyl, morpholinyl, thiomorpholinyl, azacycloheptyl, piperidinyl or N-phenylpiperazinyl.
5. A compound represented by the following structural formula: ##STR00033## the enantiomer of the compound, a salt of the compound, or a salt of the enantiomer, wherein R.sub.1 is a substituted or unsubstituted phenyl group and R.sub.4 is H.sub.2 or O.
6. The compound of claim 5 wherein the phenyl group represented by R.sub.1 is substituted with --OCH.sub.2O--, --OCH.sub.2CH.sub.2O--, halo, --O(lower alkyl), --OH, lower alkyl thiol, --O(phenyl), --OCH.sub.2(phenyl), --O--CH.sub.2-- (phenyl), lower alkyl, amino, lower alkyl amino or lower dialkyl amino.
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