Trans-.DELTA..sup.2 -prostaglandins

Details Trans-.DELTA..sup.2 -prostaglandins Trans-.DELTA..sup.2 -prostaglandins

1973-12-21

1976-01-06

Gerstl, Robert

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260290R, 260209R, 260 57, 260 58, 260 59, 260468D, 260617R, 424305, 424317, C07C 6138, C07C 6974

Patent

active

039312968

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.

REFERENCES:
beerthuis et al., Rec. Trav. Chim. Pay Bus., 90,943 (1971).

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