176308-95-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-methyl-4-chloro-5-methylsulphonylbenzoate is used as an intermediate in the synthesis of Rimeporide Hydrochloride (R517200) for the treatment of diseases associated with insulin resistance and beta-cell dysfunction. Its role in the synthesis process is essential, as it contributes to the development of a drug that can potentially improve the management of these conditions.
In the synthesis of Rimeporide Hydrochloride, methyl 2-methyl-4-chloro-5-methylsulphonylbenzoate serves as a key building block, allowing for the creation of a compound with specific therapeutic properties. Rimeporide Hydrochloride is designed to target and alleviate the symptoms of diseases related to insulin resistance and beta-cell dysfunction, making it a valuable asset in the pharmaceutical industry.
Overall, methyl 2-methyl-4-chloro-5-methylsulphonylbenzoate plays a significant role in the development of pharmaceutical compounds, particularly in the synthesis of Rimeporide Hydrochloride, which has potential applications in the treatment of diseases associated with insulin resistance and beta-cell dysfunction. Its unique chemical structure and reactivity make it a valuable intermediate in the pharmaceutical industry, contributing to the development of new and effective treatments for various health conditions.

Upstream product

• 213121-77-8 2-chloro-4-methyl-5-carboxybenzenesulfinic acid 
• 74-88-4 methyl iodide 
• 7499-07-2 4-chloro-2-methylbenzoic acid 
• 7757-83-7 sodium sulfite 

Downstream Products

• 176309-12-9 N-diaminomethylene-2-methyl-4-chloro-5-methylsulphonylbenzamide 
• 176309-00-5 2-methyl-4-chloro-5-methyl-sulfonylbenzoic acid 

Relevant academic research and scientific papers

Bicyclic acylguanidine Na+/H+ antiporter inhibitors

Blockade of the Na+/H+ exchange has been shown to diminish the serious consequences of myocardial ischemia. The aim of this investigation was to alter the structure of the common benzoylguanidine NHE inhibitors in such a way that the

Ortho-substituted benzoil acid derivatives

Ortho-substituted benzoic acid derivatives of the formula I STR1 in which R1, R2 and R3 have the given meanings, and Q is guanidyl, and also their physiologically harmless salts, exhibit antiarrhythmic properties and act a

(2-methyl-5-(methylsulfonyl)benzoyl)guanidine Na+/H+ antiporter inhibitors

The inhibition of the Na+/H+ exchanger during cardiac ischemia and reperfusion has been shown to be beneficial for the preservation of the cellular integrity and functional performance. The aim of the present investigation was to come up with potent and selective benzoylguanidines as NHE inhibitors for their use as an adjunctive therapy in the treatment of acute myocardial infarction. During the course of our investigations it became clear that the substitution ortho to the acylguanidine was of crucial importance for the potency of the compounds. 4-Chloro and 4-fluoro-2- methylbenzoic acids 6 and 7 were prepared using the directed ortho metalation technique with the carboxylic acid as the directing group. With the LDA/methyl iodide system the 2-methyl group could be extended to an ethyl group. 4-Alkyl groups were inserted by the palladium-catalyzed cross-coupling reaction into the 4-bromo-2-methylbenzoic acid methyl ester (20). Starting with benzoic acids 6-19, the methylsulfonyl group was introduced by a sequence of standard reactions (sulfochlorination, reduction, and methylation). 4-Aryl derivatives 6875 were synthesized by the palladium- catalyzed Suzuki reaction. A large number of nucleophilic displacement reactions in the 4-position were carried out with S-, O-, and N-nucleophiles as well as with the cyano and trifluoromethyl group. Using the ester method, acid chlorides, or Mukaiyama's procedure, the 5-(methylsulfonyl)benzoic acid derivatives were finally converted to the (5- (methylsulfonyl)benzoyl)guanidines 165-267 with excessive guanidine. In some cases nucleophilic substitutions with pyridinols and piperidine derivatives were carried out at the end of the reaction sequence with the 4-halo-N- (diaminomethylene)-5-(methylsulfonyl)benzamides. Variations in the 4-position were most reasonable, but the volume of the substituents was of crucial importance. Substitution in the 3- and particularly in the 6-position led to considerable worsening of the inhibitory effects of the Na+/H+ exchanger. The 2-methyl compounds, however, showed without exception higher in vitro activities than their respective demethyl counterparts as they are exemplified by the reference compounds 266 and 267, obviously caused by a conformational restriction of the acylguanidine chain. The development compound (2-methyl-5-(methylsulfonyl)-4-pyrrolobenzoyl)guanidine, methanesulfonate (246) is a NHE-1 subtype specific NHE inhibitor, being 27- fold more potent toward the NHE-1 than the NHE-2 isoform, 246 was found to act cardioprotectively not only when given before an experimentally induced ischemia, but also curatively after the onset of symptoms of acute myocardial infarction when given prior to the induction of reperfusion.