6-AMIDO DERIVATIVES OF 4, 5-a EPOXYMORPHINANS FOR THE TREATMENT OF PAIN

a technology of epoxymorphinans and derivatives, applied in the field of 6amido derivatives of 4, 5aepoxymorphinans, can solve the problems of life-threatening respiratory depression in patients and unwanted peripheral side effects, and achieve the effect of lessening the liability of constipation and respiratory depression

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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The compounds in this invention can be used as painkiller drugs that have reduced side effects such as constipation and respiratory depression.

Problems solved by technology

However, as there are μ opioid receptors outside the CNS, these opiates usually cause unwanted peripheral side effects.
For instance, prolonged morphine administration often causes constipation, and prolonged morphine administration ultimately causes life-threatening respiratory depression in patients.

Method used

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  • 6-AMIDO DERIVATIVES OF 4, 5-a EPOXYMORPHINANS FOR THE TREATMENT OF PAIN
  • 6-AMIDO DERIVATIVES OF 4, 5-a EPOXYMORPHINANS FOR THE TREATMENT OF PAIN
  • 6-AMIDO DERIVATIVES OF 4, 5-a EPOXYMORPHINANS FOR THE TREATMENT OF PAIN

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Embodiment Construction

[0023]Analgesic compounds of the invention fall into two primary classes: compounds of general formula II, in which R1 is cyclopropylmethyl, and compounds of general formula I, in which R1 is not cyclopropylmethyl. The compounds of general formula I include a series in which R1 is allyl and one in which R1 is cyclobutylmethyl. When R1 is —CH2-Het, Het may be tetrahydrofuranyl.

[0024]In one aspect, the invention relates to compounds of formula I:

[0025]Some embodiments of the invention can be represented by the formula:

which is a subset of formula I. In these compounds, R1 is cyclobutylmethyl or allyl;

R2 is chosen from hydrogen, (C1-C6)acyl, (C1-C6)oxaalkyl, and (C1-C6)acyloxaalky;

R3 is hydrogen or methyl;

R4 is chosen from

(a) phenyl substituted at other than 2 or 6 with from one to three substituents chosen from bromo, chloro, iodo, hydroxy, nitro, cyano, (C1-C3)alkyl, (C1-C3)haloalkyl, (C1-C3)haloalkoxy, (C1-C3)alkoxy and R10;

(b) optionally substituted naphthylene;

(c) optionally subst...

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Abstract

Compounds of formula:in which R4 is chosen from substituted phenyl, optionally substituted naphthylene, optionally substituted anthracene and optionally substituted aromatic heterocycle, are useful as analgesics.

Description

CROSS REFERENCE TO RELATED APPLICATIONS[0001]This application claims priority from U.S. provisional application 61 / 394,481, filed Oct. 19, 2010, the entire contents of which are incorporated herein by reference.FEDERALLY SPONSORED RESEARCH[0002]The following invention was made with government support under contracts numbers DA02615, DA06241 and DA00220R01 awarded by the National Institutes of Health (NIH). The Government has certain rights in this invention.FIELD OF THE INVENTION[0003]The invention relates to opioid receptor binding 6-amido derivatives of 4,5a-epoxymorphinans. The compounds are useful as analgesics.BACKGROUND OF THE INVENTION[0004]Opiates have been the subject of intense research since the isolation of morphine in 1805, and thousands of compounds having opiate or opiate-like activity have been identified. Many opioid receptor-interactive compounds, including those used for producing analgesia (e.g., morphine) and those used for treating drug addiction (e.g., methado...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D489/08
CPCC07D489/08A61K51/0455G01N33/9486A61P25/04C07D489/04A61K31/485
Inventor PASTERNAK, GAVRILMAJUMDAR, SUSRUTA
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