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Process for the preparation of (R)-(+)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide.

Disclosed herein is an improved process for the preparation of (R)-(+)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide (Brinzolamide) and novel intermediates thereof.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Sulfonamides useful as carbonic anhydrase inhibitors

Sulfonamides and pharmaceutical compositions containing the compounds useful in controlling intraocular pressure are disclosed. Methods for controlling intraocular pressure through administration of the compositions are also disclosed.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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IMPROVED PROCESS FOR THE PREPARATION OF (R)-(+)-4-(ETHYIAMINO)-3,4-DIHYDRO-2-(3- METHOXYPROPYL)-2H-THIENO[3,2-E]-L,2-THIAZINE-6-SULFONAMIDE-L,L-DIOXIDE

Disclosed herein is an improved process for the preparation of (R)-(+)-4- (Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6- sulfonamide- 1,1 -dioxide (Brinzolamide) and novel intermediates thereof.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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PROCESS FOR PREPARING BRINZOLAMIDE

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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IMPROVED PROCESS FOR THE PREPARATION OF (R)-(+)-4-(ETHYIAMINO)-3,4-DIHYDRO-2-(3- METHOXYPROPYL)-2H-THIENO[3,2-E]-L,2-THIAZINE-6-SULFONAMIDE-L,L-DIOXIDE

Disclosed herein is an improved process for the preparation of (R)-(+)-4- (Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6- sulfonamide- 1,1 -dioxide (Brinzolamide) and novel intermediates thereof.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Enantioselective synthesis of brinzolamide (AL-4862), a new topical carbonic anhydrase inhibitor. The “DCAT Route” to thiophenesulfonamides

A large scale synthesis of the topical carbonic anhydrase inhibitors AL-4623A (13a-HCl) and AL-4862 (13b) from 3-acetyl-2,5-dichlorothiophene (“DCAT”, 1) is described. Reaction of 1 with NaSBn gave thioether 2, which was converted via sulfenyl chloride 3 and sulfenamide 5 to sulfonamide 6. Bromination of 6 gave bromo ketone 7, which upon reduction with (+)-B-chlorodiisopinocampheylborane and cyclization of the resulting bromohydrin produced S thieno[3,2-e]-1,2-thiazine 8a (96% ee) after chromatography. Treatment of 8a in THF with -BuLi at -70 C resulted in Li-Cl exchange. Reaction of the thienyllithium with SO2 and hydroxylamine O-sulfonic acid afforded bis-sulfonamide 11a. Protection of lia as the acetimidate 12a, followed by tosylation and animation, gave R amine 13a. The synthesis of 13b proceeded via primary sulfonamide 16, which was brominated, reduced, and cyclized to give S thieno[3,2-e]-1,2-thiazine 18 (>98% ee). By virtue of the ionizable NH, 18 was separable from reduction byproducts by base extraction. Alkylation of 18 with 3-bromopropyl methyl ether afforded 8b, which was converted as above, via lib, to AL-4862 (13b). These procedures provided multihundred gram lots of 13a and 13b.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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The present invention refers to the preparation and purification of brinzolamide as well as to novel compounds useful in such processes.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Sulfonamides useful as carbonic anhydrase inhibitors

Sulfonamides and pharmaceutical compositions containing the compounds useful in controlling intraocular pressure are disclosed. Methods for controlling intraocular pressure through administration of the compositions are also disclosed.

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Breene assists the amine and intermediate preparation method (by machine translation)

The invention discloses breene assists the amine and intermediate preparation method. If the compound of the present invention C breene assists the amine intermediates shown in preparation method comprises the following steps: under anhydrous conditions, in an organic solvent, in the presence of a tertiary amine, the compound B with the original acid ester compound for 70 – 80 C condensation under reaction, can be; wherein said original ester compound as the original b acid tri methyl ester, the original acetic acid triethyl and original benzoic acid methyl ester in one of three or more. Preparation method of this invention using a tertiary amine as catalyst condensation reaction, thereby greatly shortening the amino protection step of reaction time, reduces the reagent consumption, reduce the reaction temperature, and improves product yield and purity; and post-treatment process for use in the acid-base consumption is reduced, to reduce the product residue on ignition, the operation is simplified, is more suitable for industrial production. (by machine translation)

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Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem

 

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Breene assists the amine and intermediate preparation method (by machine translation)

The invention discloses breene assists the amine and intermediate preparation method. If the compound of the present invention C breene assists the amine intermediates shown in preparation method comprises the following steps: under anhydrous conditions, in an organic solvent, in the presence of a tertiary amine, the compound B with the original acid ester compound for 70 – 80 C condensation under reaction, can be; wherein said original ester compound as the original b acid tri methyl ester, the original acetic acid triethyl and original benzoic acid methyl ester in one of three or more. Preparation method of this invention using a tertiary amine as catalyst condensation reaction, thereby greatly shortening the amino protection step of reaction time, reduces the reagent consumption, reduce the reaction temperature, and improves product yield and purity; and post-treatment process for use in the acid-base consumption is reduced, to reduce the product residue on ignition, the operation is simplified, is more suitable for industrial production. (by machine translation)

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Reference£º
Thiazine – an overview | ScienceDirect Topics,
Thiazine | C4H5NS – PubChem