|Abstract:||The compounds are of the class of 5-aroyl-pyrrole alkanoic acids and corresponding acid derivatives thereof useful as anti-inflammatory agents and as synthetic intermediates.|
|Inventor(s):||Carson; John Robert (Norristown, PA)|
|Assignee:||McNeil Laboratories, Incorporated (Fort Washington, PA)|
|Filing Date:||Jun 17, 1974|
|Claims:||1. The process of making a loweralkyl 5-aroyl-1-R.sub.4 -4-R.sub.5 -pyrrole-2-acetate of the formula: ##SPC14## |
hydrolyzing a loweralkyl 1-R.sub.4 -4-R.sub.5 -3-loweralkoxycarbonylpyrrole-2-acetate under alkaline conditions to the di-acid, 1-R.sub.4 -4-R.sub.5 -3-carboxypyrrole-2-acetic acid,
partially re-esterifying said di-acid to loweralkyl 1-R.sub.4 -4-R.sub.5 -3-carboxypyrrole-2-acetate by treating said di-acid with an acidic solution of a lower alkanol,
decarboxylating the 3-carboxy group of said loweralkyl 1-R.sub.4 -4-R.sub.5 -3-carboxypyrrole-2-acetate to the pyrrole ester, loweralkyl 1-R.sub.4 -4-R.sub.5 -pyrrole-2-acetate, by heating said loweralkyl 1-R.sub.4 -4-R.sub.5 -3-carboxypyrrole-2-acetate to CO.sub.2 -elimination temperatures, and
acylating said loweralkyl 1-R.sub.4 -4-R.sub.5 -pyrrole-2-acetate to said loweralkyl 5-aroyl-1-R.sub.4 -4-R.sub.5 -pyrrole-2-acetate by treatment with an aroyl chloride of the formula Ar-COCl in the presence of a Lewis acid in an organic solvent suitable for Friedel-Crafts acylation reactions;
wherein the foregoing said AR--CO is a member selected from the group consisting of benzoyl, thenoyl, 5-methylthenoyl, monosubstituted benzoyl, disubstituted benzoyl and trisubstituted benzoyl, each substituent of said substituted benzoyls being a member selected from the group consisting of halo, loweralkyl, trifluoromethyl, loweralkoxy, nitro, cyano and methylthio, and said R.sub.4 and said R.sub.5 represent loweralkyl.
2. The process of claim 1 wherein said loweralkyl 1-R.sub.4 -4-R.sub.5 -3-loweralkoxycarbonyl-pyrrole-2-acetate is ethyl 1,4-dimethyl-3-ethoxy carbonyl-pyrrole-2-acetate.
Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.