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Production of dozoan intermediate

An amination reaction and compound technology, which is applied in the field of preparation of dorzolamide intermediates, can solve the problems of high chiral synthesis cost, high requirements on optical purity of intermediates, inconspicuous stereoselectivity and the like

Inactive Publication Date: 2007-04-04
北京德众万全医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this method is: this route requires higher to the optical purity of intermediate (III), when 6 carbon atoms are racemate, the stereoselectivity of reaction is not obvious, and the chirality of intermediate (III) Higher synthesis costs and therefore higher cost of the final product

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0023] Add 10 grams (0.038mol) of 5,6-dihydro-4H-6-methyl-thiophene[2,3b]thiopyran-4-carbonyl-2-sulfonamide-7,7-diox into 200 Add 3 g of Pd / C (10%) to a saturated methanol solution of one milliliter of ethylamine, perform catalytic hydrogenation in a 0.4 Mpa autoclave, react at room temperature for 24 hours, and then filter. The filtrate was concentrated to dryness, 100 ml of ethyl acetate and 50 ml of water were added, stirred and separated, the aqueous phase was extracted twice with ethyl acetate, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to dryness to obtain White solid (trans:cis 90:10), the solid was recrystallized from ethyl acetate to give 7.4 g of trans(4S,6S / 4R,6R)-4-(ethylamino)-5,6-dihydro-6- Methyl-4H-thiophene[2,3b]thiopyran-2-sulfonamide-7,7-dioxo, yield 60%.

Embodiment 2

[0025] Add 20 grams (0.076mol) of 5,6-dihydro-4H-6-methyl-thiophene[2,3b]thiopyran-4-carbonyl-2-sulfonamide-7,7-diox into 400 Add 6 g of Pd / C (10%) to a saturated ethanol solution of ethylamine in milliliters, perform catalytic hydrogenation in a 0.4 Mpa autoclave, react at room temperature for 24 hours, and filter. The filtrate was concentrated to dryness, 200 ml of ethyl acetate and 100 ml of water were added, stirred and separated, the aqueous phase was extracted twice with ethyl acetate, the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to dryness to obtain White solid (trans:cis 95:5), the solid was recrystallized from ethyl acetate to give 16.4 g of trans(4S,6S / 4R,6R)-4-(ethylamino)-5,6-dihydro-6- Methyl-4H-thiophene[2,3b]thiopyran-2-sulfonamide-7,7-dioxo, yield 68%.

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Abstract

Production of multizoan intermediate is cheap and convenient. The compound can be used to treat glaucoma.

Description

field of invention [0001] The invention relates to the preparation of a dorzolamide intermediate, which can be used to prepare the dorzolamide medicine for treating glaucoma. Background of the invention [0002] Dorzolamide, (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thiophene[2,3b]thiopyran-2-sulfonamide-7,7 - Dioxygen having the formula: [0003] [0004] Dorzolamide [0005] It is generally believed that the control of the onset and development of glaucoma is achieved through the elevation of intraocular pressure, and dorzolamide is an aromatic sulfonamide compound useful in the treatment of elevated intraocular pressure. Most of the current methods for synthesizing dorzolamide pass through key intermediates (such as compounds of formula (II)) or derivatives thereof. The disclosed method for preparing dorzolamide is as follows: [0006] Patent US4797413 (1993) first discloses the synthetic method of dorzolamide: the carbonyl compound is r...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D333/00C07D335/00
Inventor 马金勇曲峰刘昆
Owner 北京德众万全医药科技有限公司
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