Chemie Linz Aktiengesellschaft

Clarion Pharmaceuticals Inc.

Cl Pharma Aktiengesellschaft

Clarion Pharmaceutical, Inc.

Rudolf Franzmair

Albin Hermetter

Friedrich Paltauf

Haridasan K Nair

Andrew C Peterson

Kurt Menzl

Heteroaryl-substituted deoxy glycerols represented by the general Formulas Ia, Ib and Ic: ##STR1## wherein: X is oxygen (--O--) or sulfur (--S--); R is substituted or unsubstituted straight or branched chain C.sub.1-30 alkyl or alkenyl, provided that a double bond of the alkenyl does not originate at the carbon atom bound to the X substituent; Het is a 5- to 9-membered heteroaryl mono- or bicyclic ring system having no more than 1 carbonyl carbon in the ring system, with 1 to 4 nitrogen atoms as the sole heteroatoms, one of which nitrogens is bonded to the glycero carbon; and Y is hydroxyl (--OH) or thiol (--SH), pharmaceutical compositions containing the same, and methods of using the compounds, are disclosed. The compounds exhibit antiviral and antibacterial activities.

Heteroaryl-substituted deoxy glycerols and antibacterial and antiviral

Therapeutically active, heteroaryl-substituted deoxy glycero-phosphoethanolamines are disclosed having the general Formula I: ##STR1## wherein one of X, Y or Z is a fatty ether substituent, one is a heteroaryl ring substituent with 1-4 nitrogens as the only heteroatoms, one of which is bonded to a carbon of the glyceryl backbone, and one is a phosphoethanolamine substituent substituted at the nitrogen, provided that each of X, Y and Z is a different substituent, and the pharmaceutical compositions comprising the therapeutically active compounds and methods of using the therapetically active compounds to treat cancerous tumors, psoriasis and inflammation are also disclosed.

Heteroaryl-substituted deoxy glycero-phosphoethanolamines

The present invention relates to novel, therapeutically active fatty alkyl and alkenyl ether glycerophospholipids bearing a 3-(2-imidazolinyl)-2-imidazolinyl or 2-imidazolinyl substituent on the ethanolamine nitrogen, methods of using the compounds and pharmaceutically acceptable salts thereof, and pharmaceutical compositions containing same. The novel, therapeutically active compounds and salts of the invention possess anti-tumor, anti-psoriatic, anti-inflammatory, and anti-asthma activities.

N-substituted glycerophosphoethanolamines

Novel (o-acyl-p-N-acylamino-phenyl)-O-phosphoethanolamines and pharmaceutically acceptable salts thereof having anti-inflammatory activity, and pharmaceutical compositions containing same are disclosed. Certain novel intermediates are also disclosed.

(o-Acyl-p-N-acylamino-phenyl)-O-phosphoethanolamines

Single-stage process for preparing mixed-substituted enantiomerically pure 1,2-diacyl-sn-glycero-3-phosphocholines of general formula I ##STR1## in which R.sub.1 and R.sub.2 are different and independently of each other denote a substituted or unsubstituted C.sub.1 to C.sub.24 -alkyl or C.sub.3 to C.sub.24 -alkenyl radical, by reacting 1-0-triphenylmethyl-2-acyl-sn-glycero-3-phosphocholine of the general formula ##STR2## in which T denotes a substituted or unsubstituted triphenylmethyl group and R.sub.2 is as defined above, with a reactive carboxylic acid derivative of the general formula

Single-stage process for preparing mixed-substituted

The invention relates to a process for the preparation of .beta.-methyldigoxin by the selective methylation of digoxin with dimethyl sulfate in the presence of a basic strontium compound and, if appropriate, of an inert inorganic adsorbent. Strontium hydroxide octahydrate, strontium methylate or strontium hydroxymethylate is used as the basic strontium compound, and an oxide, silicate or phosphate of magnesium, calcium, aluminum, silicon or titanium, with a water content in the range of 0 to 20% by weight, is used as the inorganic adsorbent. The reaction is carried out at temperatures of -15.degree. to 15.degree. C. in the presence of 3 to 24 moles of water per mole of digoxin, the water being introduced in the reaction mixture by the water content of strontium hydroxide octahydrate and/or the inorganic adsorbent used and purification of the methylation product so formed by column chromatography on SiO.sub.2 with a mixture of chlorohydrocarbon and a lower aliphatic alcohol.

Process for the preparation of .beta.-methyldigoxin

Compounds of the formula ##STR1## in which R.sub.1 and R.sub.2 are hydrogen, halogen, methyl or methoxy and R.sub.3, R.sub.4 and R.sub.5 are hydrogen, methyl or an electronegative substituent from the group consisting of halogen, C.sub.1 to C.sub.4 -alkoxy, cyano, nitro or methylsulfonyl, with the proviso that one of the radicals R.sub.3 to R.sub.5 is always the electronegative substituent of said group, and pharmaceutically acceptable acid addition salts thereof; the compounds as well as the salts are useful as analgesics.

Substituted 1-benzoyl-2-phenyliminoimidazolidine derivatives

3-Methoxy-4-(4'-aminobenzenesulphonamido)-1,2,5-thiadiazole is prepared by reaction of 3-methoxy-4-chloro-1,2,5-thiadiazole with sulfanilamide in dimethylsulfoxide as solvent and in the presence of alkali hydroxides or carbonates using a reaction temperature of from ambient temperature to 95.degree. C., whereby per mole of thiadiazole-compound from 1.2 to 1.5 mole of sulfanilamide and from 1.5 to 3 moles of the alkali hydroxide or carbonate are used, whereafter the reaction product is obtained by acidification.

Process for preparing

Novel Arylaminoimidazoline derivatives of the formula ##STR1## in which R.sub.1 and R.sub.2 are chlorine, bromine or an alkyl group with 1 to 4 C atoms, R.sub.3 is hydrogen or an alkyl radical with 1 - 4 C atoms and n and m each represent an integer from 1 to 3, the sum of n + m being an integer from 2 to 5 inclusive, and their salts. This novel compounds have a pronounced analgesic action.

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Linz, Austria

Rudolf Franzmair