8-[3-amino-piperidin-1-yl]-xanthines, the preparation thereof and their use as pharmaceutical compositions

Patent metadata

Field	Value
Publication number	US-2018291025-A1
Application number	US-201816008582-A
Country	US
Kind code	A1
Filing date	Jun 14, 2018
Priority date	Aug 21, 2002
Publication date	Oct 11, 2018
Grant date	—

Abstract

The present invention relates to substituted xanthines of general formula

wherein R 1 to R 3 are as defined herein, the tautomers, the stereoisomers, the mixtures, the prodrugs thereof and the salts thereof which have valuable pharmacological properties, particularly an inhibiting effect on the activity of the enzyme dipeptidylpeptidase-IV (DPP-IV).

First claim

What is claimed is:

1 . A method of preparing a compound of formula I

wherein
R 1 is 4-methyl-2-quinazolinylmethyl,
R 2 is methyl, and
R 3 is 2-butyn-1-yl;
the method comprising:
reacting 3-aminopiperidine, an enantiomer thereof or a salt thereof with a compound of formula (II)

wherein
Z 1 denotes a leaving group selected from the group consisting of a halogen atom, a substituted hydroxy, mercapto, sulphinyl, sulphonyl or sulphonyloxy group,
to provide the compound of formula I.

2 . The method according to claim 1 , wherein the amino group of the 3-aminopiperidine, an enantiomer thereof or a salt thereof, is protected during the reaction by a protecting group which is cleaved after the reaction.

3 . The method according to claim 2 , wherein the protecting group is tert-butoxycarbonyl.

4 . The method of claim 1 , wherein Z 1 is chlorine, bromine, methanesulphonyl or methanesulphonyloxy.

5 . A compound of formula (II)

wherein
R 1 is 4-methyl-2-quinazolinylmethyl,
R 2 is methyl,
R 3 is 2-butyn-1-yl, and
Z 1 is a leaving group selected from the group consisting of a halogen atom, a substituted hydroxy, mercapto, sulphinyl, sulphonyl or sulphonyloxy group.

6 . The compound of claim 4 , wherein Z 1 is chlorine, bromine, methanesulphonyl or methanesulphonyloxy.

Assignees

• Boehringer Ingelheim Int

Inventors

• Himmelsbach Frank
• Langkopf Elke
• Eckhardt Matthias
• Maier Roland

Classifications

• A61P3/10

  for hyperglycaemia, e.g. antidiabetics · CPC title

• A61P25/02

  for peripheral neuropathies · CPC title

• A61P3/04

  Anorexiants; Antiobesity agents · CPC title

• A61P27/02

  Ophthalmic agents · CPC title

• C07D473/04 Primary

  two oxygen atoms · CPC title