U.S. Philips Corporation

Duphar International Research Bv

Johannes M Zwagemakers

Jan Van Dijk

Jan Hartog

Volkert Claassen

Ineke Van Wijngaarden

The invention relates to new spasmolytically active tertiary amine derivatives and the salts thereof, of the formula (1) ##STR1## wherein the symbols have the following meanings: .circle.A is phenyl, or a 5- or 6-membered aromatic group containing 1 or 2 of the following hetero atoms: oxygen and/or sulphur and/or nitrogen;

Spasmolytically active tertiary amine derivatives

There is disclosed pharmaceutical preparations and a method of using same in the treatment of inflammation and/or pain, e.g., treating rheumatic affections, with novel substituted alkylidene-aminooxyalkyl carboxylic acid esters.

Novel basic substituted-alkylidenamino-oxyalkyl-carboxylic acid esters

Tertiary amines of formula 3 have a strong and prolonged spasmolytic effect, also after oral administration, on the smooth musculature of the tractus gastrointestinalis, the tractus urogenitalis and the bronchial system and have a low toxicity. The compounds can be synthetized according to methods known per se and been formulated to pharmaceutical compositions.

Spasmolytics

Novel substituted-alkylidene-aminooxyalkylcarboxylic acid esters of the formula I and their acid addition salts have a strong antiinflammatory and a potent analgetic activity and a low toxicity. The substances may be used for treating rheumatic affections. They may be synthetized and formulated into preparations by known methods.

Novel basic substituted-alkylidenamino-oxylalkyl-carboxylic-acid esters

Certain nuclear substituted benzylidene amino oxyalkyl carboxylic acids esters, amides and salts thereof have been found to have a strong anti-inflammatory activity and a potent analgetic activity. In addition, some of the compounds have an activity against Rhino virus. An example is [(4-chlorobenzylideneamino)oxy] acetic acid.

Novel benzylidene amini-oxyalkyl carboxylic acids and carboxylic acid

Novel substituted aromatic aliphatic amino carboxylic acids containing a tertiary nitrogen atom such as 3-[N-ethyl-[1-methyl-2-(4-methoxyphenyl)] ethylamino] -1-propane carboxylic acid ethyl ester or 7-[N-ethyl-[1-methyl-2-(4-methoxyphenyl)] ethylamino] -1-heptane carboxylic acid ethyl ester have been found to be useful spasmolytic agents.

Aralkylamino carboxylic acids and derivatives having spasmolytic activity

Novel benzylidene amino-oxyalkyl carboxylic acids and carboxylic acid

The novel compounds of the formula 1 and their acid addition salts have a strong antiinflammatory and a potent analgetic activity and a low toxicity. The substances may be used for treating rheumatic affections. They may be synthetized and formulated into preparations by known methods.

Novel basic substituted-alkylidenamino-oxylalkylcarboxylic-acid esters

An aralkylamino sulfone such as 4- [n-ethyl -[1-methyl-2-(4-methoxy-phenyl)] ethylamino] -butyl sulfone is useful as a spasmolytic for the smooth muscle system.

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Weesp, Netherlands

Johannes M Zwagemakers