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Novel bicyclic heterocyclic compounds, process for their preparation and compositions containing them

A compound and mixture technology, applied in the field of inflammation, or glycosidase expression-related conditions or diseases, in the field of treatment and cell proliferation, can solve the problems of ineffective curative effect and expensive treatment

Inactive Publication Date: 2008-01-16
REDDY US THERAPEUTICS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently available treatments are expensive due to frequent morbidity and these conditions are refractory to many pharmacological treatments

Method used

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  • Novel bicyclic heterocyclic compounds, process for their preparation and compositions containing them
  • Novel bicyclic heterocyclic compounds, process for their preparation and compositions containing them
  • Novel bicyclic heterocyclic compounds, process for their preparation and compositions containing them

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0768]Preparation of (3-fluoro-4-methoxy-phenyl)-[5-(4-fluoro-phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d] Pyrimidin-7-yl]-amine hydrochloride (E1)

[0769]

[0770] Step 1: Preparation of 4-(4-fluoro-benzoylamino)-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid amide (3)

[0771]

[0772] a) Preparation of 4-fluorobenzoyl chloride (2). To a solution of 4-fluorobenzoic acid (10 g, 71.42 mmol) in dry ethyl acetate (EtOAc) (100 mL) was slowly added thionyl chloride (SOCl) at 10 °C under nitrogen atmosphere 2 ) (84.9 g, 714.2 mmol). The mixture was then stirred at 85°C for 12 hours. After the reaction is complete, the excess SOCl 2 Removal by low vacuum distillation afforded the desired compound, 4-fluorobenzoyl chloride (10.8 g, 95% yield). It was used directly in the next step without further purification.

[0773] b) Preparation of 4-(4-fluoro-benzamido)-2-methyl-5-propyl-2H-pyrazole-3-carboxylic acid amide (3). Add 4-amino-2-methyl-5-propyl-2H-pyrazole-3-carboxyl...

Embodiment 2-52

[0800] Unless otherwise indicated, the following compounds appearing in Examples 2-52 were prepared by methods similar to those disclosed in Example 1, using similar starting materials for appropriate substitutions, to obtain the corresponding compounds, listed as compounds E2-E52.

Embodiment 2

[0802] Preparation of (3-chloro-4-methoxy-phenyl)-[5-(4fluoro-phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidine -7-yl]-amine-hydrochloride (E2)

[0803]

[0804] Yield: 88%; Melting point: 253.65°C; 1 H NMR (200MHz, DMSO-d6 )δ 9.12(s, D 2 O exchangeable, 1H), 8.33-8.25(m, 2H), 7.92-7.91(m, 1H), 7.75-7.70(m, 1H), 7.35-7.23(m, 3H), 4.33(s, 3H) , 3.90(s, 3H), 2.92(t, J=7.3Hz, 2H), 1.82(q, J=7.3Hz, 2H), 0.97(t, J=7.5Hz, 3H); MS: 427(M + -35,100);IR(cm -1 ): 3441, 2949, 1626.

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Abstract

The present invention provides, among other things, new bicyclo heterocyclic compounds, compositions comprising these heterocyclic compounds, methods of making the heterocyclic compounds, and methods of using these heterocyclic compounds for treating a variety of conditions and disease states associated with, for example, cellular proliferation, inflammation, glycosidase expression, or the low expression of Perlecan.

Description

field of invention [0001] The present invention relates to bicyclic heterocyclic compounds, methods and compositions for making and using the heterocyclic compounds, and methods of treating conditions or diseases associated with cell proliferation, inflammation, or glycosidase expression. Background of the invention [0002] In many drug and disease treatment areas, it is necessary to develop new compounds for new therapeutic interventions. For example, chronic and acute inflammation underlie diseases affecting entire organ systems, including but not limited to asthma, acute inflammatory disease, vasculitic disease, chronic inflammation, atherosclerosis, vascular disease, myocarditis, nephritis, Crohn's disease, arthritis, type I and II diabetes and related vascular disorders. The prevalence of these inflammatory conditions in the population as a whole is increasing, with diabetes alone affecting 16 million people. Thus, the synthesis of new compounds may enable the possib...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D231/10C07D471/04C07D205/02C07D231/04A61K31/519A61K31/415A61K31/5365A61K31/437A61K31/221
CPCC07D471/04C07D487/04A61P3/06A61P9/10A61P13/12A61P19/02A61P43/00A61K31/519
Inventor 马诺吉特·帕尔耶莱斯瓦拉普·K·拉奥伊什·K·卡恩纳纳利夫拉·K·斯瓦米文卡塔拉曼·萨布拉马尼恩文卡特斯瓦拉·R·巴丘贾夫德·伊克巴尔西瓦拉姆·皮拉赖斯蒂
Owner REDDY US THERAPEUTICS
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