Diastereoselective synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors

• US 7,041,831 B2
• Filed: 11/23/2004
• Issued: 05/09/2006
• Est. Priority Date: 11/26/2001
• Status: Active Grant

• Current Assignee: Genzyme Corporation (Sanofi )
• Original Assignee: Genzyme Corporation (Sanofi )
• Inventors: Hirth, Bradford H.
• Primary Examiner(s): Wilson, James O.
• Assistant Examiner(s): Tucker, Zachary C.
• Application Number:
  US10/997,474
• Publication Number:
  US 20050075381A1
• Time in Patent Office: 532 Days
• Field of Search: 548/237, 548/546
• US Class Current: 548/237
• CPC Class Codes: C07D 263/16 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 295/185 from aliphatic carboxylic acids
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond

Abstract

Disclosed is a method of preparing a composition comprising a compound represented Structural Formula (I):
The method comprises the step of reacting an aldehyde compound R₁₀CHO with an isonitrile compound represented by Structural Formula (II):

Claims

1. A compound represented by Structural Formula (VI):

the enantiomer of the compound, a mixture of the compound and the enantiomer, or a salt thereof, wherein R₁₁ is a substituted or unsubstituted phenyl group.

2. The compound, enantiomer, mixture and salts of claim 1 wherein the phenyl group represented by R₁₁ is substituted with —

OCH₂O—

, —

OCH₂CH₂O—

, halo, —

O (lower alkyl), lower alkyl thiol,—

OH, —

O(phenyl), —

O—

CH₂—

(phenyl), lower alkyl, amino, lower alkyl amino and lower dialkyl amino.

3. A compound represented by the following structural formula:

the enantiomer of the compound, a mixture of the compound and the enantiomer, or a salt thereof.

4. A compound represented by Structural Formula (VII):

the enantiomer of the compound, a mixture of the compound and the enantiomer, or a salt thereof, wherein R₁₂ is a phenyl group substituted with —

OCH₂CH₂O—

, halo, —

O(lower alkyl), lower alkyl thiol, —

O(phenyl), —

OCH₂—

(phenyl), lower alkyl, amino, lower alkyl amino and lower dialkyl amino.

5. A compound represented by the following structural formula:

the enantiomer of the compound, a mixture of the compound and the enantiomer, or a salt thereof.

6. A compound represented by the following structural formula:

the enantiomer of the compound, a mixture of the compound and the enantiomer, or a salt thereof.