Abstract: This disclosure describes 2-substituted-3,4-epoxycyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones useful as intermediates for the preparation of certain 11-hydroxy- and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives which possess bronchodilator, hypotensive, and anti-ulcer activity.
Type:
Grant
Filed:
October 12, 1979
Date of Patent:
August 10, 1982
Assignee:
American Cyanamid Company
Inventors:
Karel F. Bernady, Middleton B. Floyd, Jr., John F. Poletto, Robert E. Schaub, Martin J. Weiss
Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.
Abstract: Unsaturated compounds having at least 4 carbon atoms, including unsaturated alicyclic compounds having at least 4 carbon atoms, unsaturated aliphatic compounds having at least one carbon-carbon unsaturated bond and having at least 4 carbon atoms and unsaturated aromatic compounds having at least one carbon-carbon unsaturated bond in the branched chain thereof and (ii) aldehydes or ketones having at least 4 carbon atoms are catalytically co-oxidized with an oxygen-containing gas in a liquid phase to form a cleaveged product or products of unsaturated bond of the unsaturated compounds at a high yield. This co-oxidation reaction is carried out in the presence of a heavy metal containing iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum, copper, silver, chromium, molybdenum, tungsten, manganese and rhenium and the compounds thereof.
Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.
Type:
Grant
Filed:
September 26, 1979
Date of Patent:
May 4, 1982
Assignee:
American Cyanamid Company
Inventors:
Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
Abstract: The invention disclosed herein relates to pharmacologically active prostaglandin derivatives of the E and F series wherein C-16 is substituted with hydrogen, methyl, vinyl or ethynyl and C-19 substituted with chloro and the .beta.-chain consists of 7 carbon atoms.
Abstract: This invention disclosed herein relates to pharmacologically active 15-deoxy-16-hydroxy prostaglandin derivatives of the E and F series wherein C.sub.16 is substituted with allenyl.These compounds are active as hypotensives, antisecretory, bronchodilating and fertility control agents.
Abstract: This disclosure describes novel erythro 15,16-dioxy prostenoic acids and esters useful as bronchodilators, hypotensives and gastric acid secretion inhibitors.
Abstract: Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-13-14-dehydro-16(S,R)-fluoro-PGF.sub.2.alpha ..The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.
Abstract: A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.
Abstract: Prostaglandin I.sub.2 analogues of the general formula ##STR1## [wherein R.sup.1 represents a hydrogen atom, an alkyl group containing from 1 to 12 carbon atoms, an aralkyl group containing from 7 to 13 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms unsubstituted or substituted by at least one alkyl group containing from 1 to 4 carbon atoms, a phenyl group unsubstituted or substituted by at least one halogen atom, trifluoromethyl or phenyl group, or by at least one alkyl, alkoxy or alkylthio group containing from 1 to 4 carbon atoms, or represents a group --C.sub.m H.sub.2m COOR.sup.6, --C.sub.n H.sub.2n OR.sup.7 or ##STR2## in which m represents an integer of 1 to 12, n represents an integer of 2 to 12, R.sup.6, R.sup.8 and R.sup.9, which may be the same or different, each represent an alkyl group containing from 1 to 4 carbon atoms, and R.sup.7 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms, R.sup.
Abstract: The process for the manufacture of but-2-en-1-ol compounds by isomerizing but-3-en-1-ol compounds in the presence of a palladium catalyst and of hydrogen is improved by modifying the palladium catalyst with selenium or tellurium.The but-2-en-1-ols manufactured according to the invention are either solvents or valuable starting materials for the manufacture of solvents, dyes, surface coatings, paints and pesticides.
Abstract: This invention relates to compounds of the formulae ##STR1## wherein n is an integer from 2 to 5; M is H, acyl, lower alkyl, or lower alkoxy alkyl; Q is H or lower alkyl; R is alkyl, alkenyl or analkyl; A is H; Y is OH, acyloxy or alkoxy, and when taken together, Y and A is oxo (O.dbd.), and to novel intermediates therefore.
Abstract: The 16-substituted-15-keto-11deoxy prostalglandins are useful as anti secretary blood pressure lowering, anti-ulcerogenic and antihypertensive agents.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-9-deoxy-9-methylene-19-oxo-PGF.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-9-deoxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-9-deoxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-11-hydroxymethyl-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-11-hydroxymethyl-9-deoxy-9-methylene-19-oxo-PGF.sub .1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: What is disclosed are compounds of the formula ##STR1## which are structurally related to natural prostaglandins and a process for their manufacture. The compounds have valuable pharamacological properties and, therefore, they can be used as medicaments.
Type:
Grant
Filed:
August 2, 1979
Date of Patent:
October 20, 1981
Assignee:
Hoechst Aktiengesellschaft
Inventors:
Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch, Elmar Konz
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-11-hydroxymethyl-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: Prostaglandin analogues of the formula:- ##STR1## (wherein R represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, the wavy line indicates attachment in .alpha.- or .beta.-configuration or a mixture thereof, and the double bonds between C.sub.2 -C.sub.3 and C.sub.13 -C.sub.14 are trans), and cyclodextrin clathrates of such acids and esters, and when R represents a hydrogen atom, non-toxic salts of such acids, possess hypotensive activity, inhibitory activity on blood platelet aggregation and vasodilator activity, and weak diarrhoea-producing activity.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-11-hydroxymethyl-9-deoxy-9-methylene-19-oxo-PGF.s ub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-19-oxo-PGF.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-9-deoxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-11-hydroxymethyl-19-oxo-PGE.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-11-hydroxymethyl-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-11-hydroxymethyl-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-11-hydroxymethyl-19-oxo-PGF.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel inter-oxa-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel inter-oxa-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-9-deoxy-9-methylene-19-oxo-PGF.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-11-hydroxymethyl-19-oxo-PGE.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-9-deoxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-11-hydroxymethyl-9-deoxy-9-methylene-19-oxo-PGF.s ub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-19-oxo-PGF.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-9-deoxy-9-methylene-19-oxo-PGF.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-inter-oxa-11-deoxy-11-hydroxymethyl-9-deoxy-9-methylene-19-o xo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-inter-oxa-11-deoxy-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-inter-oxa-11-deoxy-9-deoxy-9-methylene-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-19-oxo-PGE.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-19-oxo-PGE.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-11-deoxy-19-oxo-PGE.sub.2 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-19-oxo-PGE.sub.1 analogs, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-dihydro-11-deoxy-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
Abstract: The present invention provides novel 13,14-didehydro-19-oxo-PGF.sub.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.