- Preparation method of high-purity glimepiride
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The invention discloses a preparation method of high-purity glimepiride. The preparation method comprises the following specific steps: 1, adding 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonamide and potassium carbonate into a mixed solvent, and raising the temperature to dissolve the added substances; and 2, carrying out cooling crystallization on a solution obtained in step 1, and filtering the cooled solution to obtain 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-3-(trans-4-methylcyclohexyl)-urea. The glimepiride obtained by the preparation method has a purity of above 99.9% and a high yield, impurity research is sufficient and controllable, the crystal form is correct, and the preparation product quality is good,so the use requirements of people are met.
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- Preparation method of hypoglycemic drug-glimepiride
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The invention discloses a preparation method of a hypoglycemic drug-glimepiride. The chemical name of the hypoglycemic drug-glimepiride is 1-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-formamido)-ethyl]-benzenesulfonyl]-3-(trans-4- methyl cyclohexyl)-urea, the chemical formula of the hypoglycemic drug-glimepiride is C24H34N4O5S, and the structural formula of the hypoglycemic drug-glimepiride is described in the description. The preparation method is simple in process, short in synthetic route and high in yield, and especially increases the yield of 2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-formamido)ethyl benzene sulfonic acid greatly; the application of chlorosulfonic acid has great influence on a sulfonation effect; compared with sulfonating agents such as concentrated sulfuric acid and fuming sulfuric acid which are used in the prior art, the chlorosulfonic acid has higher sulfonating capacity, so that the production of the glimepiride is further facilitated; the preparation method iseasy in obtaining of raw materials, economical and environment-friendly, high in product yield and product purity, and beneficial to industrialization.
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- Process for synthesizing glimepiride raw material medicine
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The invention discloses a process for synthesizing a glimepiride raw material medicine. A compound A, namely 3-ethyl-4-methyl-3-pyrroline-2-ketone and a compound B, namely 2-phenethyl isocyanate are taken as start raw materials. The process is characterized in that when an intermediate 1 is synthesized, filtrate is applied mechanically, so that the loss of the intermediate 1 can be reduced, the yield can be increased, and the production efficiency can be improved; when an intermediate 2 is synthesized, hydrochloric ether is adopted as a solvent, so that isomer impurities can be greatly reduced, the content of the isomer impurities can be reduced to 0.5% or less from 8%, and later purification procedures can be simple to operate; when a glimepiride metallic salt is synthesized, acetonitrileis adopted as a solvent, sufficient reactions can be achieved, the reaction time can be greatly shortened, the residue of an intermediate 3 is reduced to 0.2% or less from 5-10%, in addition, a highsolvent recycling rate can be achieved. The process disclosed by the invention is simple and safe, low in production cost, high in yield, stable in intermediate and finished product quality and applicable to industrial large-scale production and hypoglycemic drug, namely glimepiride, synthesis processes with relatively great social, economic and environmental-friendly benefits.
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- An Efficient and Practical Process for the Synthesis of Glimepiride
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A novel and simple approach to the synthesis of glimepiride is reported. It involves the preparation of a carbamate of 3-ethyl-4-methyl-1 H -pyrrol-2(5 H)-one, followed by its reaction with 4-(2-aminoethyl)benzenesulfonamide to produce the intermediate sulfonamide. This sulfonamide, upon reaction with phenyl (trans -4-methylcyclohexyl)carbamate, gave glimepiride. This process avoids the use of phosgene, isocyanates, or chloroformates. Furthermore, sulfonation of the aryl group was eliminated, rendering the product free of the impurities reported in earlier processes.
- Tanwar, Dinesh Kumar,Surendrabhai, Vaghela Ravikumar,Gill, Manjinder Singh
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p. 2495 - 2498
(2017/10/06)
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- Method for manufacture of compounds related to the class of substituted sulfonyl urea anti-diabetics
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The present invention relates to a process for preparation of sulfonyl urea compounds in high conversion rates and purity. More specifically, this invention relates to a process for manufacture of sulfonyl urea class of anti-diabetic pharmaceutical drugs in higher purity and yield. The process may effectively and economically be used to produce anti-diabetic drugs, such as glimepiride, glipizide, gliclazide, glibenclamide, glibornuride, and glisoxepide.
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Page/Page column 6
(2008/06/13)
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- A NOVEL PROCESS FOR PREPARATION OF SUBSTANTIALLY PURE GLIMEPIRIDE
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The present invention discloses a novel process for purification of trans-4-methyl cyclohexylamine HC1 and 4-[2-(3-Ethyl-4-methyl-2-carbonyl pyrrolidine amido) ethyl] benzene sulfonamide used in the synthesis of 3-Ethyl-2,5-dihydro-4-methyl-N-[2-[4-[[[[(trans-4-methyl cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide(I), popularly known as Glimepiride. The present invention also discloses a novel purification of Glimepiride Form I (I), having the undesired cis isomer below 0.15%. Glimepiride (I) is useful in the treatment of diabetes mellitus.
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Page/Page column 7,16
(2010/11/24)
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- Method for the Manufacture of Compounds Related to the Class of Substituted Sulphonyl Urea Anti-Diabetics
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A process for the formation of high purity sulphonyl urea compounds in high throughput conditions. The sulphonyl urea compounds are preferably the pharmaceutically useful anti-diabetic drugs such as Glimepiride, Gliclazide, Glipizide, Glibenclamide, Glibornuride, Glisoxepide etc, where the purity and economy of the compound are of utmost importance.
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Page/Page column 8
(2008/06/13)
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- A PROCESS FOR PURIFICATION
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The present invention provides a process for purification of pharmaceutically active compounds selected from the group consisting of thiazolidinedione derivatives and trans-3-Ethyl-2,5-dihydro-4-methyl-N- [2-[4-[[[[(4-methylcyclohexyl)amino] carbonyl] amino]sulfonyl]phenyl]ethyl]-2-oxo-1H-pyrrole-1-carboxamide comprising extraction in a solvent comprising an alkanol (C1-C4) and ammonia.
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Page/Page column 10
(2010/02/12)
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- USE OF SUBSTITUTED 2 PHENYLBENZIMIDAZOLES AS MEDICAMENTS
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The present invention relates to the use of a substituted 2-phenylbenzimidazole of formula I wherein R1, R2, R3, R 4, R5 and m have the meanings given in the claims, for the preparation of a medicament for the treatment or prevention of diseases involving glucagon receptors, as well as new compounds of formula I wherein R1 is a group of formula
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- Combinations comprising dipeptidylpeptidase-iv inhibitor
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The invention relates to a combination which comprises a DPP-IV inhibitor and at least one further antidiabetic compound, preferably selected from the group consisting of insulin signalling pathway modulators, like inhibitors of protein tyrosine phosphatases (PTPases), non-small molecule mimetic compounds and inhibitors of glutamine-fructose-6-phosphate amidotransferase (GFAT), compounds influencing a dysregulated hepatic glucose production, like inhibitors of glucose-6-phosphatase (G6Pase), inhibitors of fructose-1,6-bisphosphatase (F-1,6-BPase), inhibitors of glycogen phosphorylase (GP), glucagon receptor antagonists and inhibitors of phosphoenolpyruvate carboxykinase (PEPCK), pyruvate dehydrogenase kinase (PDHK) inhibitors, insulin sensitivity enhancers, insulin secretion enhancers, α-glucosidase inhibitors, inhibitors of gastric emptying, insulin, and α2-adrenergic antagonists, for simultaneous, separate or sequential use in the prevention, delay of progression or treatment of conditions mediated by dipeptidylpeptidase-IV (DPP-IV), in particular diabetes, more especially type 2 diabetes mellitus, conditions of impaired glucose tolerance (IGT), conditions of impaired fasting plasma glucose, metabolic acidosis, ketosis, arthritis, obesity and osteoporosis; and the use of such combination for the cosmetic treatment of a mammal in order to effect a cosmetically beneficial loss of body weight.
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