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. 27, 1976
Filed:
Sep. 03, 1974
Michael Peter Caton, Upminster, EN;
Edward Charles Coffee, London, EN;
Gordon Leonard Watkins, Dagenham, EN;
May & Baker Limited, , EN;
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.