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Preparation method of gliquidone intermediate

A technology for gliquidone and intermediates, which is applied in the field of preparation of gliquidone intermediates, can solve problems such as increased operating procedures, unfriendliness, and increased consumption of thionyl chloride and triethylamine, so as to reduce consumption costs, Increase the conversion rate and reduce the effect of waste gas treatment

Active Publication Date: 2020-10-27
迪嘉药业集团股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The advantage of this method is that it does not require a high reaction temperature. The disadvantage is that the reaction is divided into two steps, which increases the operating procedures and increases the consumption of additional materials thionyl chloride and triethylamine. In addition, thionyl chloride will produce a large amount of Hydrogen chloride and triethylamine are volatile and unfriendly, which will increase the difficulty of industrial production waste gas treatment

Method used

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  • Preparation method of gliquidone intermediate
  • Preparation method of gliquidone intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 210 g of compound II, 200 g of compound III and 1200 ml of water were added to the autoclave, sealed, stirred, heated to 160° C. to react for 8 hours, sampled through a sampling valve, 0.17% of the residual amount of compound IIII was detected by HPLC, the heating was stopped, and the stirring was continued. When cooled to 25°C, gradually open the exhaust valve. After the air pressure was equilibrated, the feed liquid was directly filtered to obtain a pale yellow crude product, washed with water, dried at 60° C. to obtain 359 g of Intermediate I, the yield was 96.0%, detected by HPLC, and the area-normalized purity was 99.7%.

Embodiment 2

[0035] 210 g of compound II, 196 g of compound III and 1200 ml of n-propanol were added to the autoclave, sealed, stirred, heated to 155° C. to react for 8 hours, sampled through a sampling valve, 0.86% of the residual amount of compound IIII was detected by HPLC, the heating was stopped, and the stirring was continued. When cooled to 30°C, gradually open the exhaust valve. After air pressure equilibration, the feed liquid was directly filtered to obtain an off-white crude product, washed with n-propanol, and dried at 60° C. to obtain 337 g of Intermediate I in a yield of 90.1%, detected by HPLC, and the area-normalized purity was 99.3%.

Embodiment 3

[0037] 210 g of Compound II, 210 g of Compound III and 1300 ml of acetonitrile were added to the autoclave, sealed, stirred, heated to 150° C. to react for 8 hours, sampled through a sampling valve, 0.06% of the residual amount of Compound IIII was detected by HPLC, the heating was stopped, and the stirring was continued. When cooled to 20°C, gradually open the exhaust valve. After air pressure equilibration, the feed liquid was directly filtered to obtain a white product, washed with acetonitrile, dried at 60° C. to obtain 347 g of Intermediate I, the yield was 92.8%, detected by HPLC, and the area-normalized purity was 99.6%.

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Abstract

The invention belongs to the technical field of pharmaceutical synthetic chemistry, and particularly relates to a method for preparing a gliquidone intermediate. According to the technical scheme, themethod comprises the steps that 1, a compound II and a compound III are added into a reaction kettle according to a certain molar ratio, a hydrophilic solvent with the mass 5-10 times that of the compound II is added, the reaction kettle is sealed, and the reaction temperature is 150-170 DEG C; and 2, the reaction material in the step 1 is cooled to room temperature, an air valve is gradually opened, the reaction material liquid is centrifuged, followed by washing with a reaction solvent and drying at 60 DEG C to obtain a gliquidone intermediate I. The invention provides an energy-saving andsafe preparation method of a gliquidone intermediate I.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis chemistry, in particular to a method for preparing an intermediate of glitazone. Background technique [0002] Glictazone (chemical name: 3-cyclohexyl-1-[4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxy -2-(1H)-Isoquinolinyl)ethyl]phenyl]sulfonyl urea is the second-generation sulfonylurea oral hypoglycemic agent developed by Boehringer Ingelheim. Binding to specific receptors on the pancreatic islet β-cell membrane, it can induce the production of an appropriate amount of insulin to reduce blood glucose concentration. It was launched in Germany in 1975 and is suitable for type II diabetes that is ineffective in simple diet therapy. It is a first-line drug for the treatment of diabetes. [0003] Compound of formula I, chemical name: 4-[2-(3,4-dihydro-7-methoxy-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonic acid Amide is an important intermediate in the synthesis of gliquid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/24
CPCC07D217/24
Inventor 徐可岭吴荣贵李晶刘敏张启超门连彬肖阳
Owner 迪嘉药业集团股份有限公司
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