U.S. Philips Corporation

Volkert Claassen

Hendricus Bernardus Welle

Jan Van Dijk

Johannes M Zwagemakers

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

The novel compounds of formula I and salts thereof have a very powerful anti-depressive activity which for a considerable part, and in some substances even entirely, is based on serotonine potentiation. Moncamino oxidase inhibition does not contribute to the anti-depressive effect. The substances are little toxic and substantially free from side effects. The compounds can be synthesized and processed to compositions according to known methods.

Anti-depressive compounds

The compounds of the formula ##STR1## where Hal is Br or Cl and R is ethoxy, methoxymethyl, ethoxymethyl, cyano, methoxyethoxy or cyanomethyl when Hal is Cl and is cyano, methoxy or methoxyethoxy when Hal is Br and their salts have a strong anti-depressive activity resulting in a powerful potentiation of noradrenalin and in a strong serotonin potentiation. Monoamino oxidase inhibition does not provide a basis for the antidepressive activity of these compounds. The compounds are free from noxious side effects to a considerable extent, for example, broncho-constriction and stomach ulceration.

Aminoethyl oximes having anti-depressive activity

Novel 4'-trifluoromethylvalerophenone 0-(2-aminoethyl)oximes are found to exhibit a strong anti-depressive activity based on a strong serotone potentiation but with the absence of monoamino/oxidase inhibition and undesirable side effects.

Oxime ethers having anti-depressive activity

A very powerful serotonine potentiation was found of oxime ethers of the formula ##STR1## where R is methoxy, ethoxy, cyano, cyanomethyl, chlorine, methoxyethoxy or methoxymethyl and their salts which is associated with a much less strong noradrenaline potentiation. The compounds have no anti-depressive activity component based on monoamino oxidase inhibition and are substantially free from side effects.

Anti-depressive compounds of the formula ##STR1## wherein R is (CH.sub.2).sub.p CN, (CH.sub.2).sub.p O(CH.sub.2).sub.q CH.sub.3 or (CH.sub.2).sub.r O(CH.sub.2)OCH.sub.3 and p = 1, 2 or 3 q = 0 or 1 and r = 0, 1 or 2.

Novel benzylidene amino-oxyalkyl carboxylic acids and carboxylic acid

Compounds of the formula ##STR1## wherein R is alkyl of 4 to 6 carbons, benzyl, 4-ethoxybutyl, 5 ethoxypentyl, 4-cyanobutyl or 5-cyanopentyl exhibit strong serotonine potentiation with no monoamino oxidase inhibition and are substantially free of side effects.

Aminoethyl oxime ethers having anti-depressive activity

Substituted diphenyl adamantylidene methanes. Examples of substituents on the para positions of the phenyl groups are propoxy and acetyloxy. The compounds have estrogenic activities.

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Weesp, Netherlands

Volkert Claassen