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AssigneeCentre International de Recherches Dermatologiques Galderma (Cird Galderma)
InventorsBraham Shroot, Christopher Hensby, Jean Maignan, Gerard Lang, Serge Restle, Michel Colin
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Processes for preparing 5,8,11-eicosatriynoic acid as well as esters and amides thereof involves initially preparing the acid by reacting 1-decyne with 1,4-dihalo-2-butyne in the presence of a strong base to form 1-halo-2,5-tetradecadiyne which is then reacted with 5-hexynoic acid so as to form 5,8,11-eicosatriynoic acid. This acid can then be converted to the acid chloride form and reacted with an alcohol to form an ester or converted to a potassium salt and reacted with a halide also to form an ester, or after conversion to an acid chloride reacted with an amine in the presence of a tertiary amine to form an amide, or the acid can be reacted with carbonyldiimidazole in the presence of a solvent and excess amine to form an amide.
A process for preparing an amide of 5,8,11-eicosatriynoic acid having the formula ##STR15## wherein R.sub.1 and R.sub.2, each independently, represent hydrogen or linear or branched C.sub.1 -C.sub.8 lower alkyl, optionally interrupted by one or more hetero atoms chosen from oxygen, sulfur and nitrogen, said lower alkyl being unsubstituted or substituted with one or more hydroxyl groups, R.sub.1 and R.sub.2 not being able to denote hydrogen simultaneously, or alternatively, R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a heterocycle selected from pyrrolidino, morpholino, piperazinyl and 4-(2'-hydroxyethyl) piperazinyl, said process comprising
A process for preparing an amide of 5,8,11-eicosatriynoic acid having the formula C.sub.8 H.sub.17 --(C.tbd.C--CH.sub.2).sub.3 --CH.sub.2 CH.sub.2 COR wherein R is ##STR17## wherein R.sub.1 and R.sub.2, each independently, represent hydrogen or linear or branched C.sub.1 -C.sub.8 lower alkyl, optionally interrupted by one or more hetero atoms chosen from oxygen, sulfur and nitrogen, said lower alkyl being unsubstituted or substituted with one or more hydroxyl groups, R.sub.1 and R.sub.2 not being able to denote hydrogen simultaneously, or alternatively R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a heterocycle selected from pyrrolidino, morpholino, piperazinyl and 4-(2'-hydroxyethyl) piperazinyl, one of the radicals R.sub.1 and R.sub.2 also being able to represent, when the other is hydrogen, an aryl radical having the formula ##STR18## or alternatively ##STR19## wherein R.sub.3 and R.sub.4, each independently, represent hydrogen, C.sub.1 -C.sub.4 alkyl, hydroxyl, halogen, carboxyl or trifluoromethyl, said process comprising
A process for preparing an ester of 5,8,11-eicosatriynoic acid having the formula
A process for preparing an ester of 5,8,11-eicosatriynoic acid having the formula
A process for preparing 5,8,11-eicosatriynoic acid comprising
Dependencies are inferred from the claim text.