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Dual alanyl-aminopeptidase and dipeptidyl-peptidase iv inhibitors

A compound, fused technology, applied in the field of preparation of novel dual inhibitors of DPIV and APN, which can solve problems such as weakening

Inactive Publication Date: 2012-03-14
INSTITUT FUR MEDIZINTECH MAGDEBURG IMTM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Administration of a single known inhibitor alone results in attenuated effect

Method used

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  • Dual alanyl-aminopeptidase and dipeptidyl-peptidase iv inhibitors
  • Dual alanyl-aminopeptidase and dipeptidyl-peptidase iv inhibitors
  • Dual alanyl-aminopeptidase and dipeptidyl-peptidase iv inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0225] Preparation of compounds of general formula (I)

[0226] For the preparation of compounds of general formula (I), the following synthetic routes of Schemes 1 to 17 were selected; the reaction conditions for selected steps are shown in the following schemes:

[0227] plan 1:

[0228]

[0229] Reagents and conditions: a) 1. LiAlH 4 , THF, rfl. (reflux); 2.NaOH / H 2 O, Boc 2 O, DCM, RT; b) 1, (COCl) 2 , DMSO, DCM, -78°C to >-10°C; 2. Vinyl-magnesium bromide, DCM, THF, RT; c) Ac 2 O, pyridine, DCM, 0°C to >RT; d) NaIO 4 , cat. (catalytic amount) RuCl 3 , CH3CN, EtOAc, H 2 O; e) DCC, HOBt, DCM, 17,0°C to > RT; f) LiOH, MeOH, H 2 O; g) aq. (aq.) HCl (37%), EtOH.

[0230] Scenario 2:

[0231]

[0232] Reagents and conditions: a) H 2 , Pd / C, MeOH; b) NaH, NaI, PMB-Cl, THF; c) LiOH, MeOH, H 2 O; d) n-C 7 h 13 COCl, TEA, DMAP, DCM, RT; e) f)

[0233] Option 3:

[0234]

[0235] Reagents and conditions: a) RCOCl, TEA, DMAP, DCM; b) LiOH, MeOH, H 2 O; c) RO...

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PUM

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Abstract

The invention relates to compounds of the general formula (I) or the acid addition salts thereof with organic and / or inorganic acids; as well as to the use of the compounds of the general formula (1) in the medical field, specifically for use in the suppression of DNA synthesis and inflammatory cytokine production as well as in the stimulation of anti-inflammatory cytokine production in vitro and in vivo. The invention also relates to pharmaceutically effective compositions comprising at least one compound of the general formula (I), optionally together with one or more pharmaceutically acceptable carrier(s), auxiliary substance(s) and / or adjuvant(s) or cosmetically effective compositions comprising at least one compound of the general formula (I), optionally in combination with one or more cosmetically acceptable carrier(s), auxiliary substance(s) and / or adjuvant(s).

Description

technical field [0001] The present invention relates to novel chemical compounds. Furthermore, the present invention relates to said novel chemical compounds capable of synergistically inhibiting the extracellular enzyme dipeptidyl peptidase IV (DPIV) via direct action with the active site and / or via a newly defined functionally associated enzyme binding site and alanine aminopeptidase N (APN) ("dual inhibitor") [European Patent Application No. 10156805.3, filed 17 March 2010]. The novel compounds have an effect on extracellular enzymes that exhibit an enzymatic action similar to dipeptidyl peptidase IV (DPIV) ("DPIV-like enzymatic action") and / or on extracellular enzymes that exhibit an enzymatic action similar to that of alanine aminopeptidase N (APN )-like enzymatic action ("APN-like enzymatic action") extracellular enzymes have an action. [0002] Furthermore, the present invention relates to methods for the preparation of novel dual inhibitors of DPIV and APN. [0003]...

Claims

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Application Information

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IPC IPC(8): C07D473/00C07D209/20C07D209/08C07C237/20C07C311/35C07D213/30C07D239/26C07D277/04C07C271/22C07D271/12C07C311/32C07C311/46C07F7/18C07D213/56A61K31/52A61K31/405A61K31/165A61K31/18A61K31/4406A61K31/505A61K31/4409A61K31/426A61K31/167A61K31/27A61K31/4245A61K31/695A61P29/00A61P37/02A61P9/10A61P25/00A61P17/00A61P35/00A61P37/06A61P31/12A61P31/04A61P1/04A61P3/10A61P19/04A61P35/04A61P17/06A61P17/10A61P11/06A61P37/08A61P11/00
CPCC07C237/20C07C237/22C07C237/34C07C271/22C07C311/47C07D209/08C07D209/20C07D213/55C07D213/56C07D239/20C07D239/26C07D271/12C07D277/04C07D417/12C07D473/00A61P1/00A61P1/04A61P11/00A61P11/06A61P17/00A61P17/02A61P17/06A61P17/10A61P19/00A61P19/02A61P19/04A61P21/02A61P25/00A61P25/14A61P25/16A61P25/28A61P29/00A61P31/04A61P31/12A61P31/14A61P33/06A61P35/00A61P35/04A61P37/00A61P37/02A61P37/06A61P37/08A61P43/00A61P9/00A61P9/10A61P3/10
Inventor S·安佐格U·班克A·亨堡H·尤利乌斯K·诺德霍夫M·特格尔
Owner INSTITUT FUR MEDIZINTECH MAGDEBURG IMTM
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