Novel heterocyclidene acetamide derivative

A technology of heterocyclic and hydrocarbon groups, applied in the field of new heterocyclic acetamide derivatives, can solve the problems of difficult oral administration, arrhythmia, low metabolic stability, etc.

Active Publication Date: 2008-07-23
MOCHIDA PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, these compounds have low metabolic stability and oral administration of these compounds is difficult; these compounds show inhibitory activity on human ether-a-go-go (hERG) channel, which may lead to cardiac arrhythmia, and the drug of these compounds Kinetic properties are not satisfactory

Method used

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  • Novel heterocyclidene acetamide derivative
  • Novel heterocyclidene acetamide derivative
  • Novel heterocyclidene acetamide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0041] [1] The first embodiment of the present invention

[0042] The first embodiment of the present invention provides a TRPV1 receptor antagonist comprising at least one compound represented by formula (I), its pharmaceutically acceptable salt and its solvate as an active ingredient:

[0043] [Ch.1]

[0044]

[0045] (wherein m, n and p each independently represent an integer of 0-2; q represents an integer of 0 or 1; R 1 Represents a group selected from the following groups: halogen atom, substituted or unsubstituted hydrocarbon group, substituted or unsubstituted heterocyclic group, substituted or unsubstituted C 1-6 Alkoxy, substituted or unsubstituted C 1-6 Alkoxycarbonyl, C which may be substituted or unsubstituted 1-6 Alkyl mono- or di-substituted amino, protected or unprotected hydroxyl, protected or unprotected carboxy, optionally substituted or unsubstituted C 1-6 Alkyl mono- or di-substituted carbamoyl, C 1-6 Alkanoyl, C 1-6 Alkylthio, C 1-6 Alkylsulfiny...

Embodiment approach 1-8-c

[0179] The groups of the specific examples of Q described in the embodiments [1-8-c] and [1-8-c] may each have no additional substituents, or may be further replaced by 1-3 selected from [1-1 - substituents in the categories (a-1)-(g-1) described in -a], or any substituents in specific examples can be exchanged. Among the groups listed in (a-1)-(g-1) above, "particularly preferred groups" include such substituents: such as C 1-6 Alkyl, C 2-6 Alkenyl, C 2-6 Alkynyl, halogen atom, halogenated C 1-6 Alkyl, cyano, amino, hydroxyl, carbamoyl, C 1-6 Alkoxy, C 2-6 Alkenyloxy, C 2-6 Alkynyloxy, C 1-6 Alkylthio, C 1-6 Alkylsulfinyl, C 1-6 Alkylsulfonyl, one / two C 1-6 Alkylamino, C 1-6 Alkoxycarbonyl, C 2-6 Alkanoyl, C 2-6 Alkanoylamino, Hydroxy-C 1-6 Alkyl, C 1-6 Alkoxy-C 1-6 Alkyl, carboxy-C 1-6 Alkyl, C 1-6 Alkoxycarbonyl-C 1-6 Alkyl, carbamoyl-C 1-6 Alkyl, N-C 1-6 Alkylcarbamoyl-C 1-6 Alkyl, N, N-diC 1-6 Alkylcarbamoyl-C 1-6 Alkyl, phenyl, phenoxy, phenylthio,...

Embodiment 102

[0337] (E)-2-(7-trifluoromethyl-2,3-dihydro-1-(cyclopentylacetyl)quinoline-4(1H)-ylidene)-N-(quinoline-7- base) acetamide (Example 102);

[0338] (E)-2-(7-trifluoromethyl-2,3-dihydro-1-cyclopentanecarbonylquinoline-4(1H)-ylidene)-N-(7-hydroxyl-5,6, 7,8-tetrahydronaphthalen-1-yl)acetamide (Example 105);

[0339] (E)-2-(7-trifluoromethyl-2,3-dihydroquinoline-4(1H)-ylidene)-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalene -1-yl)acetamide (Example 106);

[0340](E)-2-(7-trifluoromethyl-2,3-dihydro-1-pentanoylquinoline-4(1H)-ylidene)-N-(3,4-dihydro-3-hydroxy (1H)quinolin-2-on-5-yl)acetamide (Example 107);

[0341] (E)-2-(7-trifluoromethyl-2,3-dihydro-1-pentanoylquinoline-4(1H)-ylidene)-N-(3-hydroxyl-1,2,3, 4-tetrahydroquinolin-5-yl)acetamide (Example 108);

[0342] (E)-2-(7-trifluoromethyl-2,3-dihydro-1-((2,2-dimethylcyclopropane)carbonyl)quinoline-4(1H)-ylidene)-N -(7-Hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)acetamide (Example 109);

[0343] (E)-2-(7-trifluoromethyl-2,3-dihydro...

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Abstract

Disclosed are a compound represented by the formula (I') below, a salt thereof, and a solvate of any of them. Also disclosed are a pharmaceutical composition containing such a compound as an active ingredient, and a TRPV 1 (Transient Receptor Potential Type I) receptor antagonist. [Chemical formula 1] (I') (In the formula, m, n and p respectively represent 0-2; q represents 0-1; R1 represents ahalogen, a hydrocarbon group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, a sulfamoyl group, a CN group, an NO2 group or the like; R2 represents a halogen, an amino, a hydrocarbon group, an aromatic heterocyclic group or an oxo group; X1 represents O, -NR3- or -S(O)r-; X2 represents a methylene group, O, -NR3- or -S(O)r-; Q' represents a heteroaryl group, a heteroarylalkyl group, a substituted aryl group or aralkyl group; the cycle moiety represents an aryl ring or a heteroaryl ring; and the wavy line represents an E-form or a Z-form.).

Description

technical field [0001] The present invention relates to drugs, especially compounds with transient receptor potential type 1 receptor (hereinafter referred to as "TRPV1 receptor") antagonism, in particular to acetamide derivatives with heterocyclic subunit skeletons, including the derivatives as TRPV1 receptor antagonists as active ingredients and active agents for preventing or treating diseases causing pain in which TRPV1 receptors are involved, preventive or therapeutic active agents comprising the derivatives as active ingredients. Background technique [0002] In a study related to the mechanism of pain production, the receptor for capsaicin (8-methyl-N-vanillyl-6-nonenamide), the main pungent odor component of chili pepper (chilipepper), was cloned in 1997 (TRPV1 receptor) (Caterina MJ, Schumacher MA, Tomonaga M, Rosen TA, Levine JD and Julius D. Nature, Vol. 389, 816-824, 1997). The TRPV1 receptor is a receptor that recognizes capsaicin and is normally expressed in p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38A61K31/4155A61K31/416A61K31/427A61K31/428A61K31/433A61K31/435A61K31/437A61K31/4709A61K31/4725A61K31/498A61K31/5377A61K31/538A61P1/04A61P3/04A61P9/00A61P9/10A61P11/00A61P11/06A61P13/12
Inventor 内田秀春小菅直人佐藤勉堀田大道神野智之前田能崇天野贤一赤田安繁
Owner MOCHIDA PHARM CO LTD
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