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A kind of preparation method of gliquidone intermediate

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

Active Publication Date: 2022-03-18
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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  • A kind of preparation method of gliquidone intermediate
  • A kind of preparation method of gliquidone intermediate
  • A kind of preparation method of gliquidone intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 210g of compound II, 200g of compound III and 1200ml of water into the autoclave, seal it, stir, heat to 160°C for 8 hours, take a sample through the sampling valve, HPLC detects that the residual amount of compound III is 0.17%, stop heating, and continue stirring. When cooling to 25°C, gradually open the exhaust valve. After the air pressure was balanced, the feed liquid was directly filtered to obtain a pale yellow crude product, which was washed with water and dried at 60°C to obtain 359 g of intermediate I with a yield of 96.0%. The area-normalized purity was 99.7% by HPLC detection.

Embodiment 2

[0035] Add 210g of compound II, 196g of compound III and 1200ml of n-propanol into the autoclave, seal it, stir, heat to 155°C for 8 hours, take a sample through the sampling valve, HPLC detects that the residual amount of compound III is 0.86%, stop heating, and continue stirring. When cooling to 30°C, gradually open the exhaust valve. After the air pressure was balanced, 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, with a yield of 90.1%. The area-normalized purity was 99.3% by HPLC detection.

Embodiment 3

[0037] Add 210g of compound II, 210g of compound III and 1300ml of acetonitrile into the autoclave, seal it, stir, heat to 150°C and react for 8 hours, take a sample through the sampling valve, HPLC detects that the residual amount of compound III is 0.06%, stop heating, and continue stirring. When cooling to 20°C, gradually open the exhaust valve. After the air pressure was balanced, the feed liquid was directly filtered to obtain a white product, washed with acetonitrile, and dried at 60°C to obtain 347 g of intermediate I, with a yield of 92.8%. The area-normalized purity was 99.6% by HPLC detection.

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Abstract

The invention belongs to the technical field of pharmaceutical synthesis chemistry, and in particular relates to a method for preparing a gliquidone intermediate. The technical scheme of the present invention is: step 1. join compound II and compound III in the reactor by certain molar ratio, add the hydrophilic solvent of 5-10 times of compound II quality, airtight, reaction temperature is 150~170 °C; step 2. After the reaction material in step 1 was cooled to room temperature, the air valve was gradually opened, the reaction material liquid was centrifuged, washed with a reaction solvent, and dried at 60 °C to obtain gliquidone intermediate I. The invention provides an energy-saving and safe preparation method of gliquidone intermediate I.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis chemistry, and in particular relates to a method for preparing a gliquidone intermediate. Background technique [0002] Gliquidone (chemical name: 3-cyclohexyl-1-[4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxy -2-(1H)-isoquinolyl)ethyl]phenyl]sulfonylurea is a second-generation sulfonylurea oral hypoglycemic drug developed by Boehringer Ingelheim, and is a highly active pro-islet β-cell agent. Binding to specific receptors on the islet β-cell membrane, it can induce the production of an appropriate amount of insulin to reduce blood sugar concentration. It was launched in Germany in 1975. It is suitable for type II diabetes that is ineffective in simple diet therapy, and is the first-line drug for treating diabetes. [0003] Formula I compound, chemical name: 4-[2-(3,4-dihydro-7-methoxy-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonate Amides are important intermediates fo...

Claims

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Application Information

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Patent Type & Authority Patents(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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