Cyclopentyl (e.g., Prostoglandins, Etc.) Patents (Class 562/503)
  • Patent number: 4343949
    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
  • Patent number: 4338252
    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.
    Type: Grant
    Filed: February 26, 1981
    Date of Patent: July 6, 1982
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4338332
    Abstract: 16-Fluro-13, 14-dehydro-PG.sub.2 series compounds have been prepared.
    Type: Grant
    Filed: September 21, 1978
    Date of Patent: July 6, 1982
    Assignee: Farmitalia Carlo Erba
    Inventors: Renato Pellegata, Carmelo Gandolfi
  • Patent number: 4331608
    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.
    Type: Grant
    Filed: June 2, 1980
    Date of Patent: May 25, 1982
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Keiji Kawamoto, Toshihiro Yoshioka
  • Patent number: 4328358
    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
  • Patent number: 4328359
    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.
    Type: Grant
    Filed: February 10, 1981
    Date of Patent: May 4, 1982
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4322546
    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.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: March 30, 1982
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4321405
    Abstract: This disclosure describes novel erythro 15,16-dioxy prostenoic acids and esters useful as bronchodilators, hypotensives and gastric acid secretion inhibitors.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: March 23, 1982
    Assignee: American Cyanamid Company
    Inventor: Martin J. Weiss
  • Patent number: 4320143
    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.
    Type: Grant
    Filed: February 2, 1979
    Date of Patent: March 16, 1982
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Renato Pellegata, Carmelo Gandolfi
  • Patent number: 4315032
    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.
    Type: Grant
    Filed: May 14, 1980
    Date of Patent: February 9, 1982
    Assignee: Teitin Limited
    Inventors: Ryoji Noyori, Masaaki Suzuki, Seizi Kurozumi
  • Patent number: 4313954
    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.
    Type: Grant
    Filed: February 19, 1980
    Date of Patent: February 2, 1982
    Assignee: Ono Pharmaceutical Co. Ltd.
    Inventors: Hirohisa Wakatsuka, Masaki Hayashi, Yoshitaka Konishi
  • Patent number: 4312994
    Abstract: .alpha. Diene 16-hydroxy prostanoic acid derivatives displaying valuable pharmacological properties, e.g., gastric antisecretory, are described herein.
    Type: Grant
    Filed: March 25, 1981
    Date of Patent: January 26, 1982
    Assignee: G. D. Searle & Co.
    Inventor: Paul W. Collins
  • Patent number: 4310709
    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.
    Type: Grant
    Filed: April 23, 1980
    Date of Patent: January 12, 1982
    Assignee: BASF Aktiengesellschaft
    Inventor: Walter Rebafka
  • Patent number: 4309351
    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.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: January 5, 1982
    Assignee: The University of Chicago
    Inventor: Josef Fried
  • Patent number: 4306078
    Abstract: The 16-substituted-15-keto-11deoxy prostalglandins are useful as anti secretary blood pressure lowering, anti-ulcerogenic and antihypertensive agents.
    Type: Grant
    Filed: November 26, 1980
    Date of Patent: December 15, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Perry Rosen
  • Patent number: 4302596
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: November 24, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4298754
    Abstract: 15-Deoxy-16-hydroxy-16-(1 halovinyl) prostaglandins have been prepared.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: November 3, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4296249
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 20, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4296250
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 20, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4296246
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 20, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4296247
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 20, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4296121
    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
  • Patent number: 4296248
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 20, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4294849
    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.
    Type: Grant
    Filed: January 24, 1980
    Date of Patent: October 13, 1981
    Assignee: Warner-Lambert Company
    Inventors: Masaki Hayashi, Sadahiko Iguchi, Takanori Okada, Akiyoshi Kawasaki
  • Patent number: 4294984
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4294978
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4294981
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4294983
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4294979
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4294982
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4294980
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 13, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4293708
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4293710
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4293711
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4293712
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4293709
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: October 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4292443
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 29, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4292440
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 29, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4292441
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 29, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4292442
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 29, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4292438
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 29, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4292439
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 29, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4291172
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 22, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4291173
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 22, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4289898
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4289902
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4289900
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4289899
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4289901
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 15, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4288617
    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.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: September 8, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih