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Compositions and methods for treatment of renin-angiotensin aldosterone system (raas)-related disorders

A compound and drug technology, used in the field of compounds for treating a nephrogenin-angiotensin-aldosterone system-related disorder

Inactive Publication Date: 2011-11-23
INVASC THERAPEUTICS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Indeed, to date, alpha-lipoic acid (ALA) has not been effectively conjugated to an angiotensin-converting enzyme (ACE) inhibitor, which confers the beneficial properties of said alpha-lipoic acid (ALA) And the beneficial properties of angiotensin-converting enzyme (ACE) inhibitors can be integrated into a single compound, which can display various diseases and their related pathways with minimal toxicity. different multifunctional therapeutic effects

Method used

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  • Compositions and methods for treatment of renin-angiotensin aldosterone system (raas)-related disorders
  • Compositions and methods for treatment of renin-angiotensin aldosterone system (raas)-related disorders
  • Compositions and methods for treatment of renin-angiotensin aldosterone system (raas)-related disorders

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Experimental program
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Effect test

Embodiment 1

[0226] Example 1 - Exemplary Compound Synthesis Scheme

[0227] To synthesize the compounds described in the present invention, a general synthetic approach is utilized, wherein the synthetic approach includes three basic steps. In the first step, a coupling reaction is performed to link a nitrogen-containing pyrrolidine ring structure with the carboxyl group of lipoic acid to form an inert amide bond. Suitable coupling reagents that can be used in this step of the described procedure include: EDCI (N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride); DCC (dicyclohexylcarbodiimide); and CDMT (2-chloro-4,6-dimethoxy-1,3,5-triazine). Also, in this first step, the base used may include dimethylaminopyridine, triethylamine; and pyridine. Suitable chlorinated organic solvents that can be used in the first step include: methylene chloride (methylene chloride), chloroform, carbon tetrachloride, dichloroethane, and tetrachloroethane.

[0228] Briefly, said first step in...

Embodiment 2

[0231] Embodiment 2——1-(6,8-dimercaptooctanoyl) pyrrolidine-2-carboxylic acid synthesis

[0232] The synthesis of the 1-(6,8-dimercaptooctanoyl)pyrrolidine-2-carboxylic acid is achieved through a three-step operation in which optically active L-proline methyl ester and alpha lipoic acid as the starting point. as in the attached figure 1 L-prolyl methyl ester lipoic acid was synthesized by coupling L-prolyl methyl ester to lipoic acid using a suitable coupling reagent as shown in . Briefly, the first steps involved in the described reactions were carried out under a nitrogen atmosphere. First mix 0.206 g (1 mmol) of lipoic acid, 0.166 g (1 mmol) of L-proline methyl ester hydrochloride, and 1 equivalent of dimethylaminopyridine (DMAP) in a 100 ml round bottom flask. 0.122 g (1 mmol), and 0.101 g (0.140 ml) of triethylamine. The contents of the flask were dissolved in methylene chloride (40 mL) and stirred thoroughly at room temperature for 10 minutes. Add 0.287 g (1.5 mmo...

Embodiment 3

[0238] Embodiment 3——1-(6,8-dimercaptooctanoyl) piperidine-2-carboxylic acid synthesis

[0239] The synthesis of the described 1-(6,8-dimercaptooctanoyl)piperidine-2-carboxylic acid is realized through a three-step operation process, wherein the operation process is obtained from the The synthesis of (DL)-piperidinecarboylmethyl lipoic acid started with (DL)-piperidinecarboylmethyl ester and (DL)-α-lipoic acid. Briefly, as in the attached Figure 9 As shown in , (DL)-piperidinecarboxymethyl ester sulfide is accomplished by mixing (DL)-piperidinecarboxylate with (DL)-α-lipoic acid using a suitable coupling reagent. Caprylic acid synthesis. The first steps involved in the described reactions were carried out under nitrogen atmosphere. In a 100 ml round bottom flask, 0.206 g (1 mmol) of (DL)-α-lipoic acid, 0.166 g (1 mmol) of (DL)-methyl piperidinecarboxylate hydrochloride, dimethyl Aminopyridine 0.122 g (1 mmol), and triethylamine 0.101 g (1 mmol, 0.140 mL) were dissolved ...

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Abstract

Compounds are provided which can be useful in reducing the activity of an angiotensin-converting enzyme and thus be used to treat or prevent a renin-angiotensin aldosterone system-related disorder. These compounds include lipoic acid derivatives such as prolyl lipoic acid and pipecolinyl lipoic acid, and other compounds, and these compounds are useful in treating hypertension, stroke, or other renin-angiotensin aldosterone system-related disorders in human or animal patients. Pharmaceutical compositions prepared using these compounds and methods of treatment using these compounds are also provided.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Provisional Application Serial No. 61 / 196417 filed October 17, 2008, the entire disclosure of which is hereby incorporated by reference in its entirety. field of invention [0003] The presently disclosed subject matter relates to compounds and methods for treating a disorder associated with the renakin-angiotensin-aldosterone system (RAAS). In particular, the presently disclosed subject matter relates to compounds including prolyl lipoic acid and piperidine carboxyl lipoic acid amide and derivatives thereof, and other compounds wherein said other compounds can be It is used to reduce the activity of angiotensin-converting enzyme and can therefore be effectively used in the treatment of disorders related to the renakin-angiotensin-aldosterone system (RAAS) System (RAAS)-associated disorders are, for example, hypertension, stroke, diabetes, arteriosclerosis, and other cardiovas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/12C07D207/16C07D207/08A61K31/4015A61P9/12A61P25/28
CPCC07D211/60C07D217/24C07D409/12C07D409/14A61K31/4015C07D209/52C07D207/08C07D207/16A61P13/12A61P25/28A61P29/00A61P43/00A61P9/00A61P9/10A61P9/12A61P3/10C07D409/06A61K31/40
Inventor D·拉杰哥帕尔
Owner INVASC THERAPEUTICS INC
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