Crystal of 6,7-unsaturated-7-carbamoyl morphinan derivative and method for producing the same

Patent metadata

Field	Value
Publication number	US-9464094-B2
Application number	US-201615071147-A
Country	US
Kind code	B2
Filing date	Mar 15, 2016
Priority date	Nov 12, 2010
Publication date	Oct 11, 2016
Grant date	Oct 11, 2016

Abstract

Stable crystalline forms of a compound represented by the formula (IA):

an acid addition salt, and/or a solvate thereof are provided by the present invention. Said crystalline forms are extremely useful as materials for preparing medicines. Novel processes for preparing 6,7-unsaturated-7-carbamoyl morphinan derivatives are also provided by the present invention.

First claim

The invention claimed is:

1. A process for preparing a compound of the formula (I):

wherein R 2 is optionally substituted lower alkyl, and R 3 is optionally substituted lower alkyl, optionally substituted cycloalkyl, substituted or non-substituted aryl or substituted or non-substituted heteroaryl,
characterized by treating with a base a compound of the formula (IIA):

wherein R 2 and R 3 are the same as defined above.

2. A process for preparing a compound of the formula (I):

characterized by treating with a base a compound of the formula (IIC):

wherein R 1c is a hydroxy-protecting group deprotectable by a base, and R 2 is optionally substituted lower alkyl, and R 3 is optionally substituted lower alkyl, optionally substituted cycloalkyl, substituted or non-substituted aryl or substituted or non-substituted heteroaryl.

3. A process for preparing a compound of the formula (IB):

wherein R 1d is a hydroxy-protecting group not deprotectable by a base or hydrogen;
characterized by treating with a base a compound of the formula (IIB):

wherein R 1b is a hydroxy-protecting group; R 2 is optionally substituted lower alkyl, and R 3 is optionally substituted lower alkyl optionally substituted cycloalkyl, substituted or non-substituted aryl or substituted or non-substituted heteroaryl.

4. The process according to claim 1 , wherein the base is an inorganic base.

5. The process according to claim 1 , wherein the base is potassium hydroxide, sodium hydroxide, lithium hydroxide, or cesium hydroxide.

6. The process according to claim 1 , wherein the reaction temperature is about 30° C.-about 100° C.

Assignees

• Shionogi & Co

Inventors

• Inagaki Masanao
• Haga Nobuhiro
• Oda Shinichi

Classifications

• A61P7/06

  Antianaemics · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P39/02

  Antidotes · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title