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Generated: August 19, 2017

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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 12, 2004
Application Number:10/916,824
Claims:1. A method of preparing a sphingosine-like compound represented by the following structural formula: ##STR00033## said method comprising the step of debenzylating the --NHCH(--CH.sub.2OH)R.sub.5 group of an amine compound represented by the following structural formula: ##STR00034## 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; and R.sub.5 is a substituted or unsubstituted aromatic group.

2. The method of claim 1 wherein the amine compound is debenzylated by hydrogenation.

3. The method of claim 2 wherein the amine compound is debenzylated by hydrogenation under a hydrogen atmosphere with a catalytic amount of Pd(OH).sub.2.

4. The method of claim 1 further comprising the step of acylating the primary amine group of the sphingosine-like compound, thereby forming a ceramide-like compound represented by the following structural formula: ##STR00035## wherein R.sub.7 is a C1-C30 straight chained alkyl or alkenyl group.

5. The method of claim 4 wherein the sphingosine-like compound is acylated with R.sub.7COX, wherein is X is --Cl or N-hydroxysuccinimidyl.

6. The method of claim 1, wherein the sphingosine-like compound has an enantiomeric excess of at least 10%.

7. The method of claim 1, wherein the sphingosine-like compound has an enantiomeric excess of at least 90%.

8. The method of claim 1, wherein the sphingosine-like compound has an enantiomeric excess of at least 98%.

9. The method of claim 1, wherein R2 and R3 taken together with the nitrogen atom to which they are bound are pyrrolidinyl.

10. The method of claim 9, wherein R5 is a substituted or unsubstituted phenyl group.

11. The method of claim 10, wherein R1 is a phenyl group substituted in the meta/para positions with --OCH.sub.2O--, --OCH.sub.2CH.sub.2O-- or in the para position with halo, lower alkyl thiol, --OH, --O(phenyl), --OCH.sub.2(phenyl), lower alkyl, amino, lower alkyl amino, lower dialkyl amino, or --O(lower alkyl).

12. The method of claim 10, wherein R1 is a phenyl group substituted in the meta/para positions with --OCH.sub.2O-- or --OCH.sub.2CH.sub.2O--.

13. The method of claim 10, wherein R1 is a phenyl group substituted in the meta/para positions with --OCH.sub.2CH.sub.2O--.

14. The method of claim 5, wherein R1 is a phenyl substituted in the mela/para positions with --OCH.sub.2O-- or --OCH.sub.2CH.sub.2O-- or in the para position with halo, CH.sub.3O--, CH.sub.3CH.sub.2O--, CH.sub.3CH.sub.2CH.sub.2O--, CH.sub.3(CH.sub.3)CHO--, CH.sub.3--, CH.sub.3CH.sub.2--, CH.sub.3CH.sub.2CH.sub.2--, CH.sub.3(CH.sub.3)CH--, --OH or --OCH.sub.2(phenyl); and R.sub.7 is CH.sub.3(CH.sub.2).sub.n-or CH.sub.3(CH.sub.2).sub.n-2CH.dbd.CH--, wherein n is 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24.

15. The method of claim 14, wherein n of R7 is 7 or 8.

16. The method of claim 15, wherein R1 is a phenyl substituted with --OCH.sub.2CH.sub.2O--.
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