Methods for the production and isolation of D-chiro-inositol from kasugamycin and the use of D-chiro-inositol obtained therefrom

• US 6,342,645 B2
• Filed: 12/29/2000
• Issued: 01/29/2002
• Est. Priority Date: 12/30/1999
• Status: Expired due to Fees

• Current Assignee: INSMED Pharmaceuticals, Inc. (Insmed Incorporated)
• Original Assignee: INSMED Pharmaceuticals, Inc. (Insmed Incorporated)
• Inventors: Plourde, Robert Jr., Longo, Rachel K., Sleevi, Mark C.
• Primary Examiner(s): Richter, Johann
• Assistant Examiner(s): Price, Elvis O.
• Application Number:
  US09/750,193
• Publication Number:
  US 20010044560A1
• Time in Patent Office: 396 Days
• Field of Search: 568/833, 568/832
• US Class Current: 568/833
• CPC Class Codes: C07B 2200/07 Optical isomers
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 29/10 of ethers, including cyclic ethers, e.g. oxiranes
• CPC Class Codes: C07C 35/16 Inositols

Abstract

The present invention relates to methods for the production and isolation of D-chiro-inositol (DCI) from kasugamycin. More specifically, the present invention relates to a method of producing DCI by hydrolysis of kasugamycin with aqueous trifluoroacetic acid in the presence of a strongly acidic ion exchange resin. The present invention further relates to methods of isolating DCI from an aqueous mixture, such as a hydrolysis mixture, either directly or by forming an organic derivative of DCI.

Claims

1. A method for producing DCI from kasugamycin, which comprises hydrolyzing kasugamycin in an aqueous solution of trifluoroacetic acid (TFA) in the presence of a strongly acidic ion exchange resin.

2. A method for isolating DCI from a product mixture resulting from the acid hydrolysis of kasugamycin by contacting the product mixture with a reagent that reacts specifically with two or more of the hydroxy groups of DCI.