Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein

Patent metadata

Field	Value
Publication number	US-10442795-B2
Application number	US-201514805838-A
Country	US
Kind code	B2
Filing date	Jul 22, 2015
Priority date	May 10, 2005
Publication date	Oct 15, 2019
Grant date	Oct 15, 2019

Abstract

The present invention relates to processes for preparing the compounds of general formula I,

wherein the groups R 1 and R 3 are defined according to claim 1 . Furthermore this inventions relates to intermediates obtained in these processes.

First claim

The invention claimed is:

1. Process for preparing the compounds of general formula II,

wherein
R 1 denotes R-tetrahydrofuran-3-yl or S-tetrahydrofuran-3-yl; and
R 2 independently of one another denote hydrogen, (C 1-18 -alkyl)carbonyl, (C 1-18 -alkyl)oxycarbonyl, arylcarbonyl, aryl-(C 1-3 -alkyl)-carbonyl, aryl- C 1-3 -alkyl -alkyl, allyl, R a R b R c Si, or CR a R b OR c , wherein two adjacent groups R 2 may be linked with each other to form a bridging group SiR a R b , CR a R b or CR a OR b —CR a OR b ;
R a , R b , R c independently of one another denote C 1-4 -alkyl, aryl or aryl-C 1-3 -alkyl, while the alkyl groups may be mono- or polysubstituted by halogen;
L1 independently of one another are selected from among fluorine, chlorine, bromine, C 1-3 -alkyl , C 1-4 -alkoxy and nitro;
while by the aryl groups mentioned in the definition of the above groups are meant phenyl or naphthyl groups, which may be mono-or polysubstituted with L1;
said method comprised of the steps of reacting a glucose derivative of the formula XXXV

wherein R 2 is defined as hereinbefore and
Hal denotes F, Cl, Br, C 1-3 -alkylcarbonyloxy, C 1-3 -alkyloxycarbonyloxy or C 1-3 -alkyloxy;
with a metallated aglycon of the formula VI

wherein R 1 is defined as hereinbefore and M denotes a zinc moiety;
to yield the product of the formula II.

2. The process according to claim 1 , wherein R 2 independently of one another denote C 1-4 -alkylcarbonyl, C 1-4 -alkyloxycarbonyl, arylmethyl or R a R b R c Si.

Assignees

• Boehringer Ingelheim Int

Inventors

• Eckhardt Matthias
• Himmelsbach Frank
• Wang Xiao-Jun
• Tang Wenjun
• Sun Xiufeng
• Zhang Li
• Krishnamurthy Dhileepkumar
• Senanayake Christopher Hugh
• Han Zhengxu

Classifications

• C07D405/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D309/10 Primary

  Oxygen atoms · CPC title

• C07F1/02

  Lithium compounds · CPC title

• C07D307/20

  Oxygen atoms · CPC title

• C07H15/203

  Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems · CPC title