120298-38-6

Basic information

• Product Name: N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE
• Synonyms: N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE;(S,S)-trans-4-(acetylamino)-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide
• CAS NO: 120298-38-6
• Molecular Formula: C10H14N2O5S3
• Molecular Weight: 338.42356
• EINECS: 415-030-3
• Mol File: 120298-38-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.538[at 20℃]
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.647
• Water Solubility: 440mg/L at 20℃
• CAS DataBase Reference: N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE(120298-38-6)
• EPA Substance Registry System: N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE(120298-38-6)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-50/53
• Safety Statements: 24-37-60-61
• Hazardous Substances Data: 120298-38-6(Hazardous Substances Data)

Usage

Description

N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE, also known as N-[(6S)-Methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl]acetamide, is a chemical compound that serves as an intermediate in the synthesis of dorzolamide. Dorzolamide is a carbonic anhydrase inhibitor with antiglaucoma properties, making this compound significant in the development of treatments for glaucoma.

Uses

Used in Pharmaceutical Industry:
N-(5,6-DIHYDRO-6-METHYL-2-SULFAMOYL-4H-THIENO[2,3-B]THIOPYRAN-4-YL)ACETAMIDE 7,7-DIOXIDE is used as a chemical intermediate for the synthesis of dorzolamide, a carbonic anhydrase inhibitor. This application is crucial for the development of antiglaucoma medications, as dorzolamide helps in reducing intraocular pressure, a key factor in managing glaucoma.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H14N2O5S3/c1-5-3-8(12-6(2)13)7-4-9(20(11,16)17)18-10(7)19(5,14)15/h4-5,8H,3H2,1-2H3,(H,12,13)(H2,11,16,17)

Upstream product

• 154802-22-9 cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide 
• 75-05-8 acetonitrile 
• 154716-03-7 (6S)-4-oxo-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide 
• 1383784-43-7 (6S)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide 
• 1083006-59-0 (S)-6-methyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonyl chloride 
• 147086-79-1 (S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one 
• 154802-22-9 5,6-dihydro-4-hydroxy-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide 
• 1227941-27-6 5,6-dihydro-4H-4-acetylamino-6-methylthieno[2,3-b]thiopyran-2-sulfonylchloride-7,7,-dioxide 
• 148810-82-6 5,6-dihydro-(R,S)-4-acetoxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide 
• 147086-83-7 N-(5,6-dihydro-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-4-yl)acetamide 7,7-dioxide 
• 1034290-08-8 5,6-dihydro-(R,S)-4-hydroxy-(S)-6-methyl-4H-thieno<2,3-b>thiopyran 7,7-dioxide 
• 133359-79-2 methyl (S)-3-(thiophen-2-ylthio)butyrate 
• 147086-84-8 (S)-6-Methyl-6H-thieno[2,3-b]thiopyran 7,7-dioxide 
• 133359-80-5 (S)-3-(thien-2-ylthio)butyric acid 

Downstream Products

• 149249-72-9 dorzolamide 

Relevant articles and documents

Process for Preparing Enantiomerically Enriched Oxamides

The present invention relates to a chiral oxamide of formula (I) useful as an intermediate in the preparation of dorzolamide, and to the preparation thereof. The invention also relates to the preparation of dorzolamide, to the hydrochloride salt thereof, and to the active ingredient contained in a drug useful in the treatment of glaucoma, by means of the intermediate of formula (I).

PROCESS FOR PREPARING DORZOLAMIDE HYDROCHLORIDE AND ITS INTERMEDIATE

The present invention relates to an improved process for the preparation of (4S,6S)-4- (ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide hydrochloride ("Dorzolamide hydrochloride") having formula 1. Dorzolamide hydrochloride is prepared by the process of the present invention with high chemical and diastereomeric purity. The present invention also relates to novel intermediate of the formula 20 and a process for its preparation. Dorzolamide hydrochloride is useful in the treatment of ocular hypertension by inhibiting carbonic anhydrase enzyme.

PROCESS FOR PREPARING DORZOLAM IDE

There is provided a process for preparing dorzolamide and processes for preparing intermediates useful in the preparation of dorzolamide. In particular, there is provided a process for preparing an acetoamido sulfone of formula (viii) comprising oxidation of a hydroxysulfonamide of formula (vii) in the presence of an oxidizing agent selected from the group consisting of: a peracid, tert-butyl hydroperoxide, dimethyl dioxirane, selenium dioxide, m-phenanthroline di-N-oxide, nitric acid and hydrogen peroxide. There is also provided a process for preparing an acetoamidosulfone of formula (ix-a) comprising converting a hydroxysulfone of formula (viii) to the acetoamidosulfone of formula (ix-a) in the presence of acetonitrile and an acid. There is also provided a process for separating the cis- and trans-isomers of dorzolamide from a mixture of the trans-isomer of dorzolamide and the cis-isomer of dorzolamide comprising reacting the mixture of isomers with a carboxylic acid.