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Bridged spiro[2.4]heptane ester derivatives

A compound, C1-C4 technology, applied in drug combinations, allergic diseases, cardiovascular system diseases, etc., can solve problems such as aggravating disease progression

Inactive Publication Date: 2015-06-03
IDORSIA PHARM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, ALXR may mediate the Ab42-induced pro-inflammatory response in AD brain and aggravate disease progression

Method used

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  • Bridged spiro[2.4]heptane ester derivatives
  • Bridged spiro[2.4]heptane ester derivatives
  • Bridged spiro[2.4]heptane ester derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0005] Various embodiments of the present invention are given as follows:

[0006] 1) The present invention relates to compounds of formula (I),

[0007]

[0008] in

[0009] W is for -CH 2 CH 2 -or-CH=CH-;

[0010] Y for key or (C 1 -C 2 ) alkanediyl (alkandiyl) group;

[0011] R 1 represents an aryl or heteroaryl group which is independently unsubstituted, monosubstituted, disubstituted or trisubstituted (preferably monosubstituted or disubstituted), wherein the substituents are independently selected from halogen, ( C 1 -C 4 ) Alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 2 ) Fluoroalkyl and (C 1 -C 2 ) the group consisting of fluoroalkoxy;

[0012] R 2 represent

[0013] ■(C 3 -C 6 ) cycloalkyl, which is unsubstituted or replaced by R 3 R 4 N-CH 2 - or heterocyclyl (heterocyclyl)-methyl monosubstituted; or

[0014] ■(C 2 -C 6 ) alkyl, which is

[0015] ● not replaced;

[0016] ● with -NR 3 R 4 , -C(O)NR 5 R 6 , (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) ...

Embodiment 1

[0632] (1S,2R,3R,4R)-[piperidin-4-ylmethyl 2-((6-bromopyridin-3-yl)carbamoyl)spiro[bicyclo[2.2.1]heptane-7,1 '-Cyclopropane]-3-carboxylate:

[0633] Follow the general procedure A, then D, from (5R)-N 5 -(2-Bromo-pyridin-5-yl)-(6R)-6-hydroxycarbonyl-(4S,7R)-[4,7-ethylidene-spiro[2.4]heptane]-5-carboxylamine and tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate to start.

[0634] LC-MS-Conditions FA:t R =0.63 minutes; [M+H] + =462.20.

Embodiment 2

[0636] (1S,2R,3R,4R)-[piperidin-4-yl 2-((6-bromopyridin-3-yl)carbamoyl)spiro[bicyclo[2.2.1]heptane-7,1'- Cyclopropane]-3-carboxylate]:

[0637] Follow the general procedure A, then D, from (5R)-N 5 -(2-Bromo-pyridin-5-yl)-(6R)-6-hydroxycarbonyl-(4S,7R)-[4,7-ethylidene-spiro[2.4]heptane]-5-carboxylamine and tert-Butyl 4-hydroxypiperidine-1-carboxylate to start.

[0638] LC-MS-Conditions FA:t R =0.61 minutes; [M+H] + =448.20.

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Abstract

The invention relates to a method for preparing linear polymers having an amide end or having a star architecture comprising an amide core, by means of a ring opening using lactide and glycolide monomers or a lactide monomer ring in the presence of a catalyst, wherein the method includes the steps of: (i) reacting the excess monomer(s) with an initiator in a solvent, said initiator being selected from among an amine and an amino alcohol, given that the initiator has at least one primary or secondary amine function; (ii) adding a catalyst, said catalyst being a non-nucleophilic base and including at least one neutral sp2 nitrogen atom; and (iii) neutralizing the reaction mixture. Said novel method is particularly advantageous in that it can be easily monitored and enables better modulation of the polymers, and thus of the properties thereof, than the methods of the prior art. The invention also relates to novel polymers that are obtainable by means of said method.

Description

technical field [0001] The present invention relates to bridged spiro[2.4]heptyl derivatives of formula (I) and their use as medicaments. The invention also relates to related aspects comprising processes for the preparation of the compounds, pharmaceutical compositions comprising one or more compounds of formula (I), in particular their use as ALX receptor agonists. Background technique [0002] ALXR (alias lipoxin A4 receptor, FPRL1, FPR2; disclosed in WO2003 / 082314 as nucleotide sequence SEQ ID NO: 1 and amino acid sequence SEQ ID NO: 2) is a member of the G-protein coupled receptor family. ALXR was found to regulate calcium motility in response to high concentrations of the formylmethionine-leucylphenylalanine peptide. Furthermore, it was found that lipid metabolism, lipoxin A4 (LXA4), and its analogs bind ALXR with high affinity and increase arachidonic acid production and G protein activity in ALXR-transfected cells (Chiang et al. Pharmacol. Rev., 2006, 58, 463-487)....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/22C07D213/75C07D261/08C07D401/12C07D413/12A61K31/4465A61P29/00
CPCA61P9/00A61P11/08A61P25/00A61P25/04A61P25/28A61P29/00A61P31/18A61P37/02A61P37/08C07D205/04C07D207/08C07D207/10C07D207/12C07D211/14C07D211/22C07D211/42C07D213/75C07D241/04C07D261/08C07D263/32C07D295/088C07D401/12C07D413/12C07C69/753A61K31/444
Inventor 丹尼尔·贝尔奥利维尔·康明比欧夫塞尔文·克伦科琳娜·格里索斯托米泽维尔·勒罗伊达维德·波齐西尔维娅·理查德-比尔德斯滕
Owner IDORSIA PHARM LTD
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