BINDING DRUGS OF ABUSE

• US 20090298194A1
• Filed: 03/19/2007
• Published: 12/03/2009
• Est. Priority Date: 03/17/2006
• Status: Abandoned Application

• Current Assignee: Cranfield University
• Original Assignee: Cranfield University
• Inventors: Turner, Anthony Peter Francis, Guerreiro, Antonio, Romero-Guerra, Maria, Piletsky, Olena Volodimirivna, Chianella, Iva, Piletsky, Sergey Anatoliyovich
• Application Number:
  US12/293,360
• Publication Number:
  US 20090298194A1
• Time in Patent Office: Days
• US Class Current: 436/178
• 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: G01N 30/02 Column chromatography
• CPC Class Codes: Y10T 436/255 including use of a solid sorbent, semipermeable membrane, or liquid extraction

Abstract

Drugs of abuse (e.g. cocaine) and related substances are selectively bound by an adsorbent which comprises units derived from carboxylic acids of formula A or B: (A): R₁R₂C(CF₃)—CO₂H; (B): R₃═C(CF₃)—CO₂H or derivatives thereof. The adsorbent may be a polymer, or a solid support onto which the carboxylic acid, derivative or polymer has been grafted. The preferenced acid is 2-trifluoromethyl acrylic acid. A drug can be selectively bound from a mixture, and recovered using an eluant comprising an organic acid.

Claims

1. A method of separating a target compound which is a drug of abuse or metabolite or analogue thereof from a mixture containing it by contacting the mixture with an adsorbent material that selectively binds the target compound, the adsorbent material comprising units derived from one or more fluorocarboxylic acids of formula A and/or B, or derivatives thereof:

where R₁ is selected from hydrogen, optionally-substituted alkyl or cycloalkyl, optionally-substituted aryl or heteroaryl, optionally-substituted amine, —

OR or —

SR where R is alkyl, cycloalkyl, aryl or heteroaryl and is optionally substituted;

R₂ is selected from optionally-substituted alkyl or cycloalkyl, optionally-substituted aryl or heteroaryl, optionally-substituted amine, OR or SR where R is as defined above, or is a group containing a double or triple carbon-carbon bond; and

R₃ is selected from optionally-substituted alkylene or cycloalkylene, oxygen or sulfur.

2. A method according to claim 1 wherein said adsorbent material comprises units derived from one or more carboxylic acid derivatives selected from salts, esters, thioesters, amides and nitriles.

3. A method according to claim 1 wherein said fluorocarboxylic acid is 2-trifluoromethyl acrylic acid.

4. A method according to claim 1 wherein said adsorbent material comprises a polymer prepared by polymerising a monomer having a carbon-carbon multiple bond which is employed in the polymerisation, said monomer being a fluorocarboxylic acid of formula (A) or (B) or a derivative thereof.

5. A method according to claim 4 wherein the polymerisation also involves a cross-linker.

6. A method according to claim 5 wherein the cross-linker is selected from acrylates, methacrylates, vinyl derivatives, allyl derivatives and styrene derivatives.

7. A method according to claim 6 wherein the cross-linker is one or more of ethylene glycol dimethacrylate, divinyl benzene, divinylnaphthalene and divinyl ether.

8. A method according to claim 4, wherein said polymerising step employs free radical polymerisation.

9. A method according to claim 4, wherein said polymerising step employs living polymerisation, ionic polymerisation or suspension or emulsion polymerisation.

10. A method according to claim 1 wherein said adsorbent material is prepared by grafting a carboxylic acid of formula (A) or (B), a derivative thereof, or a polymer of such a carboxylic acid or derivative thereof, onto a solid support.

11. A method according to claim 10 wherein said solid support is in the form of beads, fibres, capillaries or a membrane.

12. A method according to claim 1 wherein said adsorbent material is a molecularly imprinted polymer prepared by polymerising one or more acids of formula (A) or (B) or derivatives thereof in the presence of a target compound.

13. A method according to claim 1 wherein said adsorbent material is a porous polymer prepared in the presence of a pore-forming component.

14. A method according to claim 1 including a subsequent step of eluting the target compound from the adsorbent material to which it is bound.

15. A method according to claim 14 wherein said step (c) employs an eluant comprising an acid.

16. A method according to claim 15 wherein the eluant comprises an organic acid.

17. A method according to claim 1 wherein said target compound has cationic character.

18. A method according to claim 1 wherein said target compound has an amine functionality.

19. A method according to claim 1 wherein said target compound is selected from tetrahydrocannabinol, heroin, morphine, 6-acetyl-morphine, morphine-3-glucuronide, codeine, cocaine, benzoylecgonine, ecgonine methyl ester, amphetamine, methamphetamine, lysergic acid diethylamide, phencyclidine, barbiturates, benzodiazepines and tricyclic antidepressants.

20. A method according to claim 17 wherein said target compound is selected from heroin, morphine, 6-acetyl morphine, morphine-3-glucuronide, codeine, cocaine, benzoylecgonine, ecgonine methyl ester, amphetamine, methamphetamine and lysergic acid diethylamide.

21. A method according to claim 1 wherein the mixture containing the target compound is an aqueous solution.