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Process for the preparation of morphinane compounds

A compound, the technology of morphinane, which is applied in the field of pharmaceuticals, can solve the problems of different degradation degrees of substrates, product yield and quality decline, etc.

Inactive Publication Date: 2020-02-07
SANECA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] A common feature of the above-mentioned methods is the varying degree of degradation of the starting substrate during the ongoing O-demethylation, which leads to a decrease in the yield and quality of the product

Method used

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  • Process for the preparation of morphinane compounds
  • Process for the preparation of morphinane compounds
  • Process for the preparation of morphinane compounds

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Experimental program
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Embodiment Construction

[0018] The invention is defined in the appended claims.

[0019] The method for preparing morphinane compound (2) by morphinane compound (1) or its salt is carried out according to the following scheme:

[0020]

[0021] Wherein R in the morphinane compounds 1 and 2 is hydrogen, a hydrocarbon group or a substituted hydrocarbon group, such as methyl, ethyl, propyl, allyl, cyclopropylmethyl, cyclobutylmethyl, wherein the morphinane compound 1 can be The following compounds: 4,5α-epoxy-14-hydroxy-3-methoxymorphinan-6-one (noroxycodone) or 4,5α-epoxy-14-hydroxy-3-methoxy- 17-Methylmorphinan-6-one (oxycodone) or 4,5α-epoxy-14-hydroxy-3-methoxy-17-ethylmorphinan-6-one or 4,5α-epoxy -14-Hydroxy-3-methoxy-17-propylmorphinan-6-one or 4,5α-epoxy-14-hydroxy-3-methoxy-17-allylmorphinan-6-one (3-methoxynaloxone) or 4,5α-epoxy-14-hydroxy-3-methoxy-17-cyclopropylmethylmorphinan-6-one (3-methoxynaltrexone ) or 4,5α-epoxy-14-hydroxy-3-methoxy-17-cyclobutylmethylmorphinan-6-one (3-methoxy...

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Abstract

The invention describes the process of catalytic O-demethylation of 3-methoxy-morphinane compounds using boron tribromide. Addition of catalysts reduces the reaction time, improves reacting the substrate to give the product in very good purity and yield. The said approach can be used, for example, for the preparation of oxymorphone, naltrexone, naloxone and nalbuphine from their respective O-methyl derivatives.

Description

technical field [0001] The invention belongs to the field of pharmacy. It concerns the preparation of intermediates or final active substances (APIs) based on morphinane compounds. The present invention relates to the synthesis of 3-hydroxymorphinane compounds by O-demethylation of 3-methoxymorphinane compounds according to the following scheme: [0002] [0003] These derivatives affect receptors in the central nervous system and are therefore useful as drugs for the treatment of pain and for the relief of psychological dependence in drug-addicted patients. The most commonly used morphinane derivatives in this field include, for example, oxycodone, oxymorphone, naloxone, naltrexone and nalbuphine. Background technique [0004] As described in the literature, the most commonly used O-demethylating agents for the preparation of 3-hydroxymorphinane derivatives include hydrobromic acid, boron tribromide, and the methanesulfonic acid / methionine system. The yields of these ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D489/02
CPCC07D489/02C07D489/08A61K31/485B01J27/08B01J31/18B01J31/0239B01J31/0268B01J2231/641B01J2531/002
Inventor J·加斯帕尔R·赫赛克M·卡瓦拉
Owner SANECA PHARMA