Method for separating enantiomers of aryloxipropanolamine derivatives, and chiral solid-phase chromatography material for use in the method

• US 5,461,175 A
• Filed: 07/08/1994
• Issued: 10/24/1995
• Est. Priority Date: 11/04/1991
• Status: Expired due to Term

• Current Assignee: Bjorn Ekberg, Klaus Mosbach, Lutz Fischer, Ralf Muller
• Original Assignee: Bjorn Ekberg, Klaus Mosbach, Lutz Fischer, Ralf Muller
• Inventors: Muller, Ralf, Fischer, Lutz, Ekberg, Bjorn, Mosbach, Klaus
• Primary Examiner(s): O SULLIVAN, PETER G
• Application Number:
  US08/232,110
• Time in Patent Office: 473 Days
• Field of Search: 564/304, 564/348, 564/349, 544/134, 210/656, 524/719, 524/724
• US Class Current: 564/304
• CPC Class Codes: A61P 5/00 Drugs for disorders of the endocrine system
• CPC Class Codes: B01D 15/3833 Chiral chromatography
• CPC Class Codes: B01D 15/3852 using imprinted phases or molecular recognition; using imprinted phases
• CPC Class Codes: B01J 20/26 Synthetic macromolecular compounds
• CPC Class Codes: B01J 20/261 obtained by reactions only involving carbon to carbon unsaturated bonds macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds per se C08F
• CPC Class Codes: B01J 20/268 Polymers created by use of a template, e.g. molecularly imprinted polymers
• CPC Class Codes: B01J 20/285 based on polymers
• CPC Class Codes: B01J 20/29 Chiral phases
• CPC Class Codes: B01J 20/3057 Use of a templating or imprinting material molecularly imprinted polymers B01J20/268; filling pores of a substrate or matrix followed by the removal of the substrate or matrix
• CPC Class Codes: B01J 2220/54 Sorbents specially adapted for analytical or investigative chromatography
• CPC Class Codes: C07B 57/00 Separation of optically-active compounds
• CPC Class Codes: C07C 213/10 Separation; Purification; Stabilisation; Use of additives
• CPC Class Codes: C07C 231/20 by separation of optical isomers
• CPC Class Codes: C07D 285/10 1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
• CPC Class Codes: G01N 2600/00 Assays involving molecular imprinted polymers/polymers created around a molecular template

Abstract

A method for separating enantiomers of a derivative of an aryloxipropanolamine is disclosed, characterized in that the derivative is contacted with a chiral solid-phase chromatography material containing molecular imprints of an optically pure enantiomer of the derivative to be separated.

Claims

1. Method for separating enantiomers of a derivative of an aryloxipropanolamine comprising contacting the derivative with a chiral solid-phase chromatography material including molecular imprints of an optically pure enantiomer of the derivative to be separated.

2. The method as claimed in claim 1 wherein said chiral solid-phase chromatography material comprises a polymer which is prepared by polymerisation of a monomer in the presence of a cross-linking agent and a print molecule comprising the optically pure enantiomer of the derivative to be separated.

3. Chiral solid-phase chromatography material for use in the separation of enantiomers of derivatives of aryloxipropanolamine comprising:

a polymer prepared by polymerisation of a monomer in the presence of a cross-linking agent and

an optically pure enentiomer of the derivative to be separated, a molecular imprint of the optically pure enantiomer being formed in the polymer by non-covalent interactions between the monomer and the optically pure enantiomer.

4. The chiral solid-phase chromatography material as claimed in claim 3 wherein the derivative of aryloxipropanolamine, which is used in the formation of the molecular imprint, is timolol, propranolol, metoprolol or atenolol.

5. The chiral solid-phase chromatography material as claimed in claim 3 wherein the monomer is a carboxyl-functional monomer.

6. The chiral solid-phase chromatography material as claimed in claim 5 wherein the carboxyl-functional monomer is itaconic acid.

7. The chiral solid-phase chromatography material as claimed in claim 5 wherein the carboxyl-functional monomer is methacrylic acid.

8. The chiral solid-phase chromatography material as claimed in claim 3, wherein the cross-linking agent is ethylene glycol dimethylacrylate.

10. The chiral solid-phase chromatography material as claimed in claim 4, wherein the monomer is a carboxyl-functional monomer.

11. The chiral solid-phase chromatography material as claimed in claim 4, wherein the cross-linking agent is ethylene glycol dimethylacrylate.

12. The chiral solid-phase chromatography material as claimed in claim 5, wherein the cross-linking agent is ethylene glycol dimethylacrylate.

13. The chiral solid-phase chromatography material as claimed in claim 6, wherein the cross-linking agent is ethylene glycol dimethylacrylate.

14. The chiral solid-phase chromatography material as claimed in claim 7, wherein the cross-linking agent is ethylene glycol dimethylacrylate.

9. Method for preparing a chiral solid-phase chromatography material for use in the separation of enantiomers of a derivative of an aryloxipropanolamine comprising polymerizing a monomer in the presence of a cross-linking agent and a print molecule comprising the optically pure enantiomer of the derivative to be separated.