Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof
Patent
1978-10-26
1980-05-27
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acids and salts thereof
2604381, 26050117, 424305, 424317, 560121, 435 63, 435886, C07C17700
Patent
active
RE0302872
ABSTRACT:
Novel 18 -, 19 - and 20 -hydroxy-prostaglandin derivatives of the formula I ##STR1## wherein the dotted line in the position 8-12 indicates the optional presence of a double bond, the waved lines in position 15 indicate that the hydroxyl group and the group R.sub.4 are either in .alpha.- or .beta.-position and Z represents a --CH.sub.2 CH.sub.2 -- or a cis --CH.dbd.CH-- group, and wherein R represents one of the groups: ##STR2## (wherein the waved lines indicate that the hydroxyl groups are either in .alpha.- or .beta.-position and R.sub.1 represents a hydrogen atom, a methyl or ethyl group), R.sub.2 represents either an oxygen atom or a hydrogen atom and an .alpha.- or .beta.-hydroxyl group, R.sub.3 represents a hydrogen atom or a hydroxyl group and R.sub.4 represents a hydrogen atom or a methyl group, with the proviso that when simultaneously, R.sub.1, R.sub.3 and R.sub.4 each represents a hydrogen atom, R.sub.2 represents an oxygen atom, a double bond is in 8-12 position and the 15-hydroxyl group is in position .alpha., R does not represent the group (b), but that when in addition to these conditions, Z represents a cis --CH.dbd.CH-- group and the 8-12 position is saturated, R either represents the groups (b) or (c); and the pharmaceutically acceptable salts and esters thereof, novel process for their preparation by selective microbiological hydroxylation of compounds of formula II ##STR3## wherein the dotted line in the position 10-11 indicates the optional presence of a double bond in case the 8-12 position is saturated and the other symbols are as defined hereinabove, by means of microorganisms of the Division of Eumycota or, as far as the introduction of a hydroxyl group in the 18- or 19-position is concerned, of the Family of Streptomycetaceae, and, if desired, conversion of the 18- 19- and 20-hydroxy-prostaglandin derivatives thus obtained into pharmaceutically acceptable salts and esters thereof, and pharmaceutical compositions containing at least one of the novel hydroxy-prostaglandin derivatives of formula I.
REFERENCES:
patent: 3878046 (1975-04-01), Marscheck
patent: 3903143 (1975-09-01), Muellen
Taylor et al., Nature 250, 665 (1974).
Jonsson et al., Science, 187, 1093 (1975).
Doodewaard Jean
Marx Arthur F.
Adams Bruce L.
Burns Robert E.
Gerstl Robert
Gist-Brocades N.V.
Lobato Emmanuel J.
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