The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Jan. 06, 1976
Filed:
Dec. 21, 1973
Other;
Abstract
New process for the preparation of trans-.DELTA..sup.2 -prostaglandins of the formula ##SPC1## (wherein A represents a grouping of the PGE, PGF or PGA type, X represents --CH.sub.2 CH.sub.2 -- or trans --CH=CH--, R.sub.1 represents an alkyl radical of 1 to 10 carbon atoms or an alkyl radical of 1 to 6 carbon atoms carrying a phenyl substituent or a cycloalkyl substituent of 5 to 7 carbon atoms, R.sub.2 represents a hydrogen atom or an alkyl radical of 1 to 4 carbon atoms) and alkyl esters thereof having 1 to 10 carbon atoms in the chain, which comprises reacting a cyclopentane derivative of the formula: ##SPC2## (where R.sub.3 represents a 2-tetrahydropyranyl group unsubstituted or substituted by at least one alkyl radical, or a 1-ethoxyethyl group) with an alkyl phosphonate of the general formula: ##EQU1## (wherein R.sub.4 represents a methyl or ethyl radical, and R.sub.5 represents an alkyl radical of 1 to 10 carbon atoms), optionally hydrolyzing the resulting trans-.DELTA..sup.2 -prostaglandin ester of the general formula: ##SPC3## To the corresponding acid, optionally converting the 9.alpha.-hydroxy radical in the ester or acid product to an oxo group, and hydrolyzing the tetrahydropyranyloxy or ethoxyethoxy groups in the resulting trans-.DELTA..sup.2 -prostaglandin compound of the formula: ##SPC4## (wherein R.sub.6 represents a hydrogen atom or an alkyl radical of 1 to 10 carbon atoms, Z represents ##EQU2## or C=O) to hydroxy radicals to obtain a trans-.DELTA..sup.2 -PGF or trans-.DELTA..sup.2 -PGE compound of the formula: ##SPC5## And, if desired, converting the PGE alicyclic ring (Z represents C=O) into that of a PGA compound. The trans-.DELTA..sup.2 -prostaglandin products, which are new compounds except for trans-.DELTA..sup.2 -PGE.sub.1, possess typical pharmacological properties of the `natural` prostaglandins.