Cyclopentane derivatives

Details Cyclopentane derivatives Cyclopentane derivatives

1974-09-03

1976-01-27

Hines, Robert V.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603458, 2603459, 260464, 260468D, 260469, 260488R, 2605011, 260514D, 260544R, 260557H, 260586R, 260598, 424298, 424316, 424317, 424320, C07C10200, C07C10337

Patent

active

039352617

ABSTRACT:
Cyclopentane derivatives of the prostaglandin type of the formula: ##SPC1##
(wherein R.sup.1 represents hydrogen or lower alkyl, R.sup.2 represents alkyl of 1 to 10 carbon atoms, the symbols R.sup.3 are the same and represent hydrogen, lower alkyl, lower alkenyl, phenyl(lower)alkyl or lower alkanoyl, R.sup.4 represents a carboxy or alkoxycarbonyl group, or an amido group unsubstituted or substituted on the nitrogen atom, X represents vinylene, ethylene, epoxyethylene or cyclopropylene, and n represents an integer of 5 to 8), which possess pharmacological properties in particular the production of hypotension, bronchodilation, inhibition of gastric acid secretion and stimulation of uterine contraction are prepared by a new six-stage process involving initially the reaction of an enamine of a cyclopentanone with an aldehyde to form a 2-hydroxyalkyl-2-cyclopenten-1-one, reacting the cyclopentenone with a source of hydrogen cyanide to form a hydroxyalkyl-3-oxocyclopentane-carbonitrile, reducing the carbonitrile to a 3-hydroxy-2-hydroxyalkyl-cyclopentanecarbaldehyde, reacting the carbaldehyde with an alkanoylmethylenephosphorane to convert the formyl group to ------CH=CH --CO--R.sup.2, oxidising the terminal hydroxymethyl group in the 2-position substituent to carboxy and the ring hydroxy group to oxo, and reducing the two oxo groups in the resulting cyclopentanonealkanoic acid to yield a 2-hydroxy-5-(3-hydroxyalkenyl)cyclopentyl-alkanoic acid, and optionally converting the product into another compound of the foregoing formula.

REFERENCES:
patent: 3432541 (1969-03-01), Bagli et al.
patent: 3455992 (1969-07-01), Bagli et al.
patent: 3501525 (1970-03-01), Lapidus et al.
patent: 3504019 (1970-03-01), Lapidus et al.
patent: 3505386 (1970-04-01), Babcock et al.
patent: 3505387 (1970-04-01), Beal et al.
patent: 3751463 (1973-08-01), Caton et al.
patent: 3880883 (1975-04-01), Caton et al.

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