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6-Monoacetylmorphine derivatives useful in immunoassay

Inactive Publication Date: 2007-06-21
ROCHE DIAGNOSTICS OPERATIONS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0005] It is against the above background that the present invention provides certain unobvious advantages and advancements over the p

Problems solved by technology

The problem presently unsolved by the prior art is the unavailability of antibodies which will allow detection of 6-MAM or 6-MAC as markers of heroin abuse without interference from other opiates such as morphine or codeine which may derive from legitimate medical prescriptions, e.g., cough syrup, or even diet, e.g., poppy seeds.

Method used

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  • 6-Monoacetylmorphine derivatives useful in immunoassay
  • 6-Monoacetylmorphine derivatives useful in immunoassay
  • 6-Monoacetylmorphine derivatives useful in immunoassay

Examples

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specific embodiments

[0054] In the examples that follow, boldface numbers refer to the corresponding structure in the drawings.

example 1

Preparation of Dihydrocodeine (2)

[0055] To 1.2 g (4.0 mmol) of codeine in 40 mL of methanol was added 100 mg of 10% Pd-C. The resulting reaction mixture was hydrogenated under pressure of 50 psi. The solution was filtered through CELITE (Celite Corporation), and the filtrate was concentrated to give 1.12 g (3.7 mmol, 93%) of dihydrocodeinone as a white solid. ES (+) m / z 301.

example 2

Preparation of Dihydrocodeinone (3)

[0056] To a mixture of 1.25 g (11.1 mmol) of potassium-t-butoxide in 50 mL of benzene were added 6.78 g (37 mmol) of benzophenone and 1.12 g (3.7 mmol) of dihydrocodeine, which was allowed to reflux for 2 hours. The reaction mixture turned yellow. The reaction mixture was allowed to cool to room temperature, and 50 mL of 2N HCl was added. The resulting reaction mixture was allowed to stir for 10 minutes. The organic layer was separated and extracted with 3×40 mL of 2N HCl. The organic layer was discarded, and the aqueous layer was again extracted with 3×20 mL of dichloromethane. The aqueous layer was basified with aqueous potassium hydroxide solution to pH 12 and extracted with 5×60 mL of dichloromethane. The organic layers were combined and dried over MgSO4 and filtered. The filtrate was concentrated to give 691 mg (2.3 mmol, 55%) of 3 as a yellow solid.

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Abstract

Analogs of 6-monoacetyl morphine (6-MAM) are described. These include analogs derivatized at either the C-3 position, the C-6 position, or the nor position of the molecule. These analogs allow for elaboration with linkers terminated by a functional group such as an activated ester, the functional groups being useful for attaching the molecule to other entities such as proteins, polysaccharides, and reporter groups.

Description

FIELD OF THE INVENTION [0001] The present invention pertains to the field of drug monitoring, and in particular, to the field of detecting drugs of abuse in biological samples via immunoassay. More particularly, the present invention relates to chemical analogs of morphine useful in development of antibodies that recognize 6-monoacetyl morphine (6-MAM) and 6-monoacetyl codeine (6-MAC) and in production of conjugates useful in immunoassay methods for detection of 6-MAM and 6-MAC. BACKGROUND OF THE INVENTION [0002] Heroin (diacetylmorphine) is an opioid developed as an antitussive agent during the late nineteenth century. Heroin abuse soon became a problem and continues to be so now, more than a century later. Following ingestion, heroin is quickly metabolized to 6-monoacetyl morphine (6-MAM) and then to morphine, which in turn undergoes extensive metabolism. [0003] Acetylcodeine is a synthetic byproduct present in street heroin but not in pharmaceutical diacetylmorphine, which is us...

Claims

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Application Information

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IPC IPC(8): C07K14/80C07K14/765
CPCA61K47/48038A61K47/4833C07D489/02C07K16/44Y10S530/807A61K47/542A61K47/646
Inventor GHOSHAL, MITALISIGLER, GERALD F.ROOT, RICHARD TERRY
Owner ROCHE DIAGNOSTICS OPERATIONS INC
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