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Aminophenoxyacetamide derivatives and pharmaceutical composition containing thereof

a technology of acetamide and acetamide, which is applied in the direction of drug compositions, biocide, cardiovascular disorders, etc., can solve the problems of not being able to prevent or suppress neurodegeneration in sufficient quantities, and achieve the effect of preventing autophosphorylation of fgf receptors and simple selection methods

Inactive Publication Date: 2006-08-10
ASUBIO PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The aminophenoxyacetamide derivatives effectively induce CalbindinD-28k production, providing neuroprotective effects against intracellular Ca2+ increases, thereby improving treatment outcomes for various cerebral disorders with reduced toxicity and stability issues.

Problems solved by technology

However, these clinically used medicaments suppress only a few pathways relating to the increase of the cellular Ca2+ concentration, and therefore are not yet sufficient enough for preventing or suppressing the neurodegeneration.
However, it is very difficult and therefore it is not likely to administer the CalbindinD-28k protein directly into the desirable site in the central nervous system of a body in view of the limitations existing in the pharmacological and pharmaceutical methodology because CalbindinD-28k itself is an unstable macro molecular weight protein having 28 Kd (Kilo Dalton) of molecular weight.

Method used

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  • Aminophenoxyacetamide derivatives and pharmaceutical composition containing thereof
  • Aminophenoxyacetamide derivatives and pharmaceutical composition containing thereof
  • Aminophenoxyacetamide derivatives and pharmaceutical composition containing thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

2-(4-Amino-2,3,5,6-tetramethylphenoxy)-N-methyl-N-(4-piperidinyl)acetamide (1)

[0133] A solution of 457 mg of 2-[4-(tert-butoxycarbonylamino)-2,3,5,6-tetramethylphenoxy]acetic acid, 363 mg of 1-(tert-butoxy-carbonylamino)-4-methylaminopiperidine, 2.16 g of 25% propane phosphonic acid anhydride [Japanese Patent Kokai Showa 55-100346] in ethyl acetate solution and 985 μl of triethylamine in 5 ml of dichloromethane was stirred over night under room temperature. After the reaction, saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture and the mixture was extracted with dichloromethane. The extract was washed with saline, dried and concentrated under reduced pressure to give the residue. The obtained residue was dissolved in 8 ml of dichloromethane, and to this solution was added 2 ml of trifluoroacetic acid under ice-cooling, then the mixture was stirred for 1 hour at the room temperature. After removal of the solvent, the resultant residue was purified ...

example 2

2-(4-Amino-2,3,5,6-tetramethylphenoxy)-N-methyl-(4-piperidinyl)propanamide (2)

[0134] The title compound (2) was obtained from 2-[4-(tert-butoxycarbonylamino)-2,3,5,6-tetramethylphenoxy)propionic acid and 1-(tert-butoxycarbonylamino)-4-methylaminopiperidine by the same manner as the Example 1.

example 3

2-(4-Amino-2,3,5,6-tetramethylphenoxy)-2-methyl-N-methyl-N-(4-piperidinyl)propanamide (3)

[0135] The title compound (3) was obtained from 2-[4-(tert-butoxycarbonylamino)-2,3,5,6-tetramethylphenoxy]-2-methyl propionic acid and 1-(tert-butoxycarbonylamino)-4-methylaminopiperidine by the same manner as the Example 1.

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Abstract

The present invention relates to an amiophenoxyacetamide derivative of the formula (I): wherein R1 to R4 are, independent from each other, a hydrogen atom or an optionally substituted alkyl group; E1 is —NR4—; and E2 is an oxygen atom or —NR10—; Q is the group —X—Y-Q′, wherein X and Y are connecting bonds or X is an alkylene or alkenylene group and Y is selected from a group comprising C═O, NHC(═O), and C(═O)NH, and Q′ is a hydrogen atom or a phenyl or pyridyl group which may be substituted; and pharmaceutically acceptable salts thereof. The present invention further relates to compositions comprising compounds of the formula (I) and methods of using said compounds for treating cerebral functional disorders and cerebral organic disorders.

Description

RELATED APPLICATION DATA [0001] This application is a continuation application of U.S. patent application Ser. No. 10 / 009,566, filed Dec. 12, 2001, which is a §371 application of PCT / JP01 / 03198 filed Apr. 13, 2001, which claims priority to JP 2000-112100 filed Apr. 13, 2000. The entire contents of each of these applications is incorporated herein by reference.TECHNICAL FIELD [0002] The present invention relates to cerebral functional or organic disorders improving and treating agents containing aminophenoxyacetamide derivatives and pharmaceutically acceptable salt thereof as an active ingredient, having neuroprotective effect by inducing the production of CalbindinD-28k, one of Ca2+-binding proteins, and to the methods for selecting these neuroprotective aminophenoxyacetamide derivatives. More specifically, the present invention relates to the therapeutic and improving agents for various cerebral dysfunction due to various ischemic disorders such as cerebral infarction, intracerebra...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/454A61K31/445C07D211/56C07D401/02A61K31/4468A61K31/5377A61K45/00A61P9/00A61P9/10A61P21/02A61P25/00A61P25/16A61P25/28A61P43/00C07D211/58C07D417/04
CPCC07D211/58C07D417/04A61P21/02A61P25/00A61P25/16A61P25/28A61P43/00A61P9/00A61P9/10C07D265/30C07D417/06A61K31/445
Inventor TAKEMOTO, NAOHIROANNOURA, HIROKAZUMURAYAMA, NORIHITO
Owner ASUBIO PHARMA