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US 6,673,968 B1Granted
Method of producing n-(4,5-bis-methanesulfonyl-2-methyl-benzoyl)-guanidine, the hydrochloride thereof
AssigneeMerck Patent GmbH
InventorsRolf Gericke, Manfred Baumgarth, Hans Markus Bender, Bernhard Ladstetter
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Abstract
The present invention relates to an NHE-1 selective Na+/H+ antiporter inhibitor N-(4,5-bismethanesulfonyl-2-methylbenzoyl)guanidine, hydrochloride, to its hydrochloride hydrate, and to a process for the preparation.
Claims5
N-(4,5-Bismethanesulfonyl-2-methylbenzoyl)guanidine, hydrochloride hydrate.
A process for the preparation of N-(4,5-bismethanesulfonyl-2-methylbenzoyl)guanidine, hydrochloride of the formula I,
- in which Me is methyl, and of the hydrochloride hydrate, which is characterised in that
- firstly, by reaction of the starting compound of the formula II
- in which
- Me is a methyl group, and Q is fluorine or chlorine,
- with a methanesulfinate in a nucleophilic substitution, the 4-methanesulfonyl group is introduced in a one-step reaction,
- then, in the second step, the compound of the formula III
- is converted into the acid chloride and reacted with guanidine to give N-(4,5-bismethanesulfonyl-2-methylbenzoyl)guanidine,
- and, in the third step, converted into the hydrochloride of the formula I and/or the hydrochloride hydrate by reaction in aqueous HCl.
5 more elements
Dependencies are inferred from the claim text.