Pyridylaminoacetic acid compound

A kind of technology of pyridylamino, pyridylamino, applied in the field of pyridylamino acetic acid compounds, can solve the problems such as no specific disclosure of sulfonamide compounds, and achieve the effect of excellent toxicity

Active Publication Date: 2014-06-25
UBE IND LTD
View PDF15 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is not specifically described that the compounds described in these Patent Documents 1 to 4 have a bronchodilation effect caused by EP2 agonism, and in addition, there is no specific disclosure in any of the above-mentioned documents that the compounds of the present invention have the properties of pyridylaminoacetic acid and Its ester is a partial structure of sulfonamide compound

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Pyridylaminoacetic acid compound
  • Pyridylaminoacetic acid compound
  • Pyridylaminoacetic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0747] The present invention will be described in more detail below with examples, reference examples, and test examples, but the scope of the present invention is not limited thereto.

[0748] [Example 1]

[0749] {6-[(6-phenylpyridazin-3-ylmethyl)(pyridin-3-ylsulfonyl)aminomethyl] Pyridin-2-ylamino}acetic acid hydrochloride (Exemplary Compound No. 1397)

[0750] 1-(a) ({5-bromo-6-[(6-phenylpyridazin-3-ylmethyl)(pyridin-3-ylsulfonate Acyl)aminomethyl]pyridin-2-yl}tert-butoxycarbonylamino)tert-butyl acetate

[0751] 1.75 ml of N,N-dimethylformamide of 114 mg (0.349 mmol) of N-(6-phenylpyridazin-3-ylmethyl)pyridin-3-ylsulfonamide obtained in Reference Example 2-(d) In the solution, add [(5-bromo-6-bromomethylpyridin-2-yl) tert-butoxycarbonylamino] tert-butyl acetate 233mg (containing 0.35mmol in terms of pure components) obtained in Reference Example 1-(c). ) and potassium carbonate 98.0mg (0.709mmol), stirred at room temperature for 20 hours. After the reaction, 5.3 ...

Embodiment 2

[0764] (6-{(pyridin-3-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl} Pyridin-2-ylamino)acetic acid (Exemplary Compound No. 985)

[0765] 2-(a) [tert-butoxycarbonyl(6-{(pyridin-3-ylsulfonyl)[4-(thiazole-2 -yl)benzyl]aminomethyl}pyridin-2-yl)amino]tert-butyl acetate

[0766] In the tetrahydrofuran 20ml solution of the N-[4-(thiazol-2-yl) benzyl]pyridin-3-yl sulfonamide 686mg (2.07mmol) obtained in the reference example 4-(e), add the reference example 3-(b ) obtained in [tert-butoxycarbonyl (6-hydroxymethylpyridin-2-yl) amino] tert-butyl acetate 743mg (2.20mmol), tri-n-butylphosphine 980μl (3.92mmol) and N, N, N 562 mg (3.26 mmol) of ', N'-tetramethylazodicarbonamide was stirred at room temperature for 11 hours. After the reaction was completed, saturated aqueous sodium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer after liquid separation was washed with a saturated aqueous sodium chloride solution, dr...

Embodiment 3

[0777] (6-{(pyridin-2-ylsulfonyl)[4-(thiazol-2-yl)benzyl]aminomethyl} Pyridin-2-ylamino)acetic acid (Exemplary Compound No. 977)

[0778] 3-(a) [tert-butoxycarbonyl(6-{(pyridin-2-ylsulfonyl)[4-(thiazole-2 -yl)benzyl]aminomethyl}pyridin-2-yl)amino]tert-butyl acetate

[0779] In addition to using 279 mg (0.824 mmol) of [tert-butoxycarbonyl (6-hydroxymethylpyridin-2-yl) amino] tert-butyl acetate obtained in Reference Example 3-(b), and using tert-butyl acetate obtained in Reference Example 5 N-[4-(thiazol-2-yl)benzyl]pyridin-2-ylsulfonamide 275mg (0.830mmol) instead of N-[4-(thiazol-2-yl)benzyl]pyridin-3-ylsulfonamide, The reaction and post-treatment were carried out according to Example 2-(a), to obtain 496 mg of the title compound in the form of white foam. (yield is 92%)

[0780] Mass spectrum (FAB, m / z): 652 (M + +1).

[0781] 1 H-NMR spectrum (CDCl 3 , δppm): 8.60 (ddd, J = 4.7, 1.7, 0.9Hz, 1H), 7.85 (d, J = 3.1Hz, 1H), 7.85-7.81 (m, 3H), 7.77 (ddd, J = 7.7, 7....

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The present invention provides a novel pyridylaminoacetic acid compound represented by the following formula (1): (wherein R 1 , R 2 , R 3 , Y and Z are as defined in the description and claims), or a pharmacologically acceptable salt thereof. The pyridylaminoacetic acid compound has EP2 agonistic action and is therefore useful as a therapeutic and / or prophylactic agent for respiratory diseases such as asthma or chronic obstructive pulmonary disease.

Description

technical field [0001] The present invention relates to novel pyridylglycine compounds or pharmacologically acceptable salts thereof useful as pharmaceuticals. More specifically, the pyridylglycine compound of the present invention is useful as a therapeutic and / or preventive drug for respiratory diseases such as asthma and chronic obstructive pulmonary disease (hereinafter abbreviated as COPD) due to its EP2 agonistic effect. . Background technique [0002] Inhaled prostaglandin E has been reported to 2 (Hereafter abbreviated as PGE 2 ) can suppress immediate and delayed asthmatic responses (refer to Non-Patent Document 1). It is also known that PGE 2 It has an agonist action on receptors such as EP1, EP2, EP3, and EP4, and it is taught that the agonist action on the EP2 receptor is largely related to the bronchodilation action (see Non-Patent Document 2). [0003] It is known that sulfonamide compounds having structures similar to those of the compounds of the present...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/74A61K31/4439A61K31/444A61K31/501A61K31/506A61P11/00A61P11/06A61P43/00C07D401/14C07D405/14C07D409/14C07D417/12C07D417/14
CPCC07D401/14C07D405/14C07D213/74C07D417/14C07D417/12C07D409/14A61K9/0053A61K9/2018A61K9/4858A61P11/00A61P11/06A61P19/00A61P43/00A61K31/443C07D405/12
Inventor 岩村亮田中正幸胜部哲嗣重富学冈成荣治德永裕仁藤原宽
Owner UBE IND LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap