- Preparation method of montelukast sodium side chain
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The invention discloses a preparation method of a montelukast sodium side chain, and high-quality montelukast sodium side chain 1- (mercaptomethyl) cyclopropylacetic acid (MLM) is obtained. Accordingto the process, 1-bromo-cyclopropylacetonitrile (MLM-5) is taken as a raw material and reacts with thioacetic acid under an alkaline condition to generate benzoic acid (1-acetonitrile cyclopropyl) methyl mercaptide (MLM-6), and an alkaline hydrolysis reaction is directly performed without treatment, so that the product 1-(mercaptomethyl) cyclopropylacetic acid (MLM) is obtained. The process is simple to operate, cheap in used materials, mild in reaction condition, low in wastewater ammonia nitrogen and easy to biochemically treat, and the product yield and purity are greatly improved.
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Paragraph 0015; 0024-0033
(2020/12/30)
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- Preparation method of 1-mercaptomethylcyclopropylacetic acid
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The invention relates to a preparation method of 1-mercaptomethylcyclopropylacetic acid, and belongs to the technical field of raw material preparation. The technical scheme comprises the steps: using 2,5-dimethyl-2,5-dihydroxy-1,4-dithiane described in a formula 1 as a starting material, preparing alpha,beta-unsaturated carboxylic acid ester shown in a formula 2 in an alkaline reagent environment, then adopting 1,2-dimethylimidazole as a basic catalyst, preparing beta,gamma-unsaturated carboxylic acid ester of a formula 3 under irradiation of ultraviolet light, then performing a Simmons-Smith reaction on the beta,gamma-unsaturated carboxylic acid ester of the formula 3 and diethylzinc and diiodomethane so as to obtain a cyclopropanation intermediate shown in a formula 4, and performing hydrolysis on the cyclopropanation intermediate of the formula 4 under an alkaline condition so as to obtain the target compound 1-mercaptomethylcyclopropylacetic acid. The defects of highly toxic products, easy combustion and easy explosion, a large amount of waste liquid and no environmental protection in the prior art are overcome.
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Paragraph 0019; 0029
(2019/10/04)
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- 1-mercapto methyl propyl process for the preparation of acetic acid
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The invention provides a preparation method of 1-mercaptomethylcyclopropyl acetic acid. The preparation method is used for solving the problems of high cost, high toxicity, low yield and heavy environmental pollution of the existing preparation method. The preparation method comprises the step of preparing the 1-mercaptomethylcyclopropyl acetic acid with 1,4-butanediol as a starting raw material which is cheap, low in toxicity and easy to obtain as a starting raw material through reactions such as etherification or esterification, oxidization, corey-chaykovsky or simmons-smith, reduction, substitution, deprotection and the like. The preparation method provided by the invention has the technical characteristics of simple and convenient operation, easy purification of product, high yield, and suitability for industrial large production.
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Paragraph 0117-0119
(2019/01/28)
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- Montelukast side chain intermediate and preparing method thereof
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The invention belongs to the field of medical chemistry, and particularly relates to a montelukast side chain intermediate and a preparing method thereof. A provided intermediate compound is 6-halogenated methyl-5,7-dioxaspiro[2,5] octane, wherein 1,1-cyclopropyl dimethyl carbinol serving as a starting material and 2-halogeno-1,1-dimethoxyethane are subjected to a transacetalation reaction under solid acid catalysis to obtain 6-halogenated methyl-5,7-dioxaspiro[2,5] octane, the intermediate is treated with organic alkali and then hydrolyzed with a water solution containing acetic acid to obtain monoacetylated protected diol. The problems that monoacetylated protected diol is poor in selectivity, and diol loss is serious are solved, the availability of the raw materials is improved, and the montelukast side chain intermediate can be synthesized economically and conveniently.
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- SYNTHESIS OF LEUKOTRIENE COMPOUNDS
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The present invention relates to the synthesis of leukotriene receptor agonist compounds and to novel intermediates employed in their preparation. Leukotriene agonists are used in the treatment of asthma, as well as other conditions mediated by leukotrienes such as inflammation and allergies. A compound of particular interest is montelukast and the present invention describes an improved process for making montelukast and similar compounds.
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Page/Page column 42; 26
(2008/06/13)
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- Process for preparation of [1-(mercaptomethyl)cyclopropyl]acetic acid and related derivatives
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The present invention provides a novel process for preparing [1-(mercaptomethyl)cyclopropyl]acetic acid with high purity and related derivatives.
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Page/Page column 9-10
(2008/06/13)
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- NOVEL PROCESS FOR PREPARING 1-(MERCAPTOMETHYL) CYCLOPROPANEACETIC ACID, A USEFUL INTERMEDIATE IN THE PREPARATION OF MONTELUKAST AND SALTS THEREOF
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The present invention provides a novel montelukast intermediate and a simple and straightforward process for preparing it. According to the present invention, by using this intermediate and the process, essentially as described herein, montelukast acid and salts thereof are obtained.
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Page/Page column 8; 13
(2008/06/13)
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- NEW TRICYCLIC DERIVATIVES AS LTD4 ANTAGONISTS
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Compounds of formula (I) and their pharmaceutically acceptable salts are provided as well as processes for the manufacture of such compounds. The compounds are useful in the treatment or prevention of inflammatory and allergic diseases.
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- Process for the preparation of 1-(mercaptomethyl)-cyclopropaneacetic acid
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A process for the preparation of highly pure 1-(mercaptomethyl)-cyclopropaneacetic acid is described. Treatment of 1-(hydroxymethyl)-cyclopropaneacetonitrile with an acid provides the corresponding imino ester and/or halo-amide, which when reacted with thiourea provide the corresponding amide-isothiuronium salt. Hydrolysis of the amide-isothiuronium salt followed by an in situ oxidation allows the facile isolation and purification of 1-[1 -(carboxymethyl)-cyclopropanemethyldisulfanylmethyl]-cyclopropaneacetic acid (also known as 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide). Reduction of the 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide under mild conditions provides the 1-(mercaptomethyl)-cyclopropaneacetic acid with high purity.
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- Process for the preparation of leukotriene anatgonists
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The present invention relates to a process for the preparation of a compound of formula (I) or a sodium salt thereof STR1 wherein HET is 7-chloroquinolin-2-yl or 6,7-difluoroquinolin-2-yl, which comprises: reacting the dilithium dianion of 1-(mercaptomethyl)cyclopropaneacetic acid with a compound of formula (II) STR2 wherein HET is as defined above and L is arylsulfonyl or alkylsulfonyl. The invention further provides the dicyclohexylamine salt of a compound of formula (I).
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