An improved process for the preparation of 5,6 -dihydro...

C - Chemistry – Metallurgy – 07 – D

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C07D 495/04 (2006.01)

Patent

CA 2570415

The present invention relates to resolution of (cis, trans) 5,6 -dihydro -4H-4- ethylamino-6-methylthieno[2,3-b] thiopyran-2-sulfonamide-7,7 -dioxide using dibenzoyl -L- tartaric acid monohydrate or di-p-toluoyl-L-tarrtaric acid monohydrate as a chiral resolving agent in presence of methanol to obtain hemitartarate salt, purifying it to obtain hemitartarate salt of 5,6-dihydro-4 H-4 (S) -ethyl amino-6(S) methylthieno [2,3-b] thiopyran-2-sulfonamide - 7,7 - dioxide with de of >99% , Chemical purity >99.5% with cis isomer content of <0.1 % and further converting into its pharmaceutically acceptable salts, preferably hydrochloride salt.

La présente invention concerne le dédoublement du (cis, trans)-5,6-dihydro-4H-4-éthylamino-6-méthylthiéno[2,3-b]thiopyrane-2-sulfonamide-7,7-dioxyde, en utilisant de l~acide dibenzoyl-L-tartrique monohydraté ou de l~acide di-p-toluoyl-L-tartrique monohydraté comme agent de dédoublement chiral, en présence de méthanol afin d~obtenir le sel hémitartrate. On purifie ensuite ledit sel afin d~obtenir le sel hémitartrate du 5,6-dihydro-4H-4(S) -éthylamino-6(S)-méthylthiéno[2,3-b]thiopyrane-2-sulfonamide-7,7-dioxyde à plus de 99 %, d~une pureté chimique > 99,5 % avec une teneur en isomère cis < 0,1 %, puis on le convertit en ses sels de qualité pharmaceutique, de préférence l~hydrochlorure.

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