Cyclopentyl (e.g., Prostoglandins, Etc.) Patents (Class 562/503)
  • Patent number: 4281160
    Abstract: The present invention provides novel 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: July 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4281156
    Abstract: The present invention provides novel 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: July 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4281162
    Abstract: The present invention provides novel 9-deoxy-9-methylene-11-deoxy-11-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: July 28, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4278806
    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: June 7, 1979
    Date of Patent: July 14, 1981
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner
  • Patent number: 4278688
    Abstract: Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-virylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing 1 to 12 carbon atoms, an aralkyl group containing from 7 to 12 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 6 carbon atoms, a phenyl group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group, alkyl group containing from 1 to 4 carbon atoms or phenyl group, a--C.sub.m H.sub.2m COOR.sup.5 group (wherein m represents an integer of from 1 to 12 and R.sup.5 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms ), a --C.sub.n H.sub.2n OR.sup.6 group (wherein R.sup.6 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n represents an integer of from 2 to 12), or a ##STR2## group (wherein R.sup.7 and R.sup.
    Type: Grant
    Filed: January 16, 1980
    Date of Patent: July 14, 1981
    Assignee: Ono Pharmaceutical Co.
    Inventors: Masaki Hayashi, Katsuichi Shimoji, Yoshinobu Arai
  • Patent number: 4277615
    Abstract: The present invention provides novel 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: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4277616
    Abstract: The present invention provides novel 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: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4277614
    Abstract: The present invention provides novel 11-Deoxy-11-hydroxymethyl-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: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4277613
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-6-oxo-PGF.sub.1 intermediates for preparing prostacyclin analogs which are useful for pharmacological purposes, e.g., anti-asthmatic indications.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4276427
    Abstract: The present invention provides novel 19,20-didehydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: June 30, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4276428
    Abstract: The present invention provides novel 19,20-didehydro-13,14-dihydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: June 30, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4275233
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-13,14-dihydro-PG.sub.2 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: June 23, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4275232
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-inter-oxa-13,14-dihydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.CROSS REFERENCE TO RELATED APPLICATIONSThe present application is a division of Ser. No. 025,878, filed Apr. 2, 1979, now abandoned.PRIOR ARTProstaglandin analogs exhibiting hydroxylation in the 19-position are known in the art. See, for example, U.S. Pat. No. 4,127,612, Sih, J.C., Prostaglandins 13:831 (1977) and U.S. Pat. Nos. 3,657,316, 3,878,046, and 3,922,297. See also the additional references cited in U.S. Ser. No. 025,878.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: June 23, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4275231
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-13,14-dihydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: June 23, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4271313
    Abstract: The present invention provides novel 19-hydroxy-cis-4,5-didehydro-13,14-dihydro-PG.sub.1 Analogs methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: June 2, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4271314
    Abstract: 4,5-Unsaturated 16-hydroxy prostanoic acid derivatives displaying valuable pharmacological properties, e.g. gastric antisecretory, are described herein.
    Type: Grant
    Filed: November 28, 1979
    Date of Patent: June 2, 1981
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Raphael Pappo
  • Patent number: 4269996
    Abstract: The present invention provides novel 19-hydroxy-cis-4,5-didehydro-PG.sub.1 analogs methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: May 26, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4268522
    Abstract: The invention discloses certain novel 13,14-dihydro-15-alkenyl prostaglandins and 13,14-dihydro-15-alkynyl prostaglandins and analogs of each as well as the novel intermediates employed in their preparation. The 9-oxo compounds of this novel series demonstrate selective bronchodilator activity, certain of these are also useful as antisecretory agents.
    Type: Grant
    Filed: October 18, 1979
    Date of Patent: May 19, 1981
    Assignee: Pfizer Inc.
    Inventors: James F. Eggler, Hans-Jurgen E. Hess
  • Patent number: 4267368
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-cis-4,5-didehydro-13,14-dihydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: May 12, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4267369
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-trans-2,3-didehydro-13,14-dihydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: May 12, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4267370
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-inter-oxa-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: May 12, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4267367
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-trans-2,3-didehydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: May 12, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4267361
    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: September 27, 1979
    Date of Patent: May 12, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4260805
    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: September 27, 1979
    Date of Patent: April 7, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4260819
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-cis-4,5-didehydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: March 24, 1980
    Date of Patent: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260818
    Abstract: The 16-substituted 15-hydroxy prostaglandins which are saturated at the 13-position and the 16-substituted-15-keto prostaglandins, said prostaglandins being useful as antisecretory agents, blood pressure lowering agents, anti-ulcerogenic agents and antihypertensive agents.
    Type: Grant
    Filed: December 3, 1979
    Date of Patent: April 7, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Perry Rosen
  • Patent number: 4260807
    Abstract: The present invention provides novel 19-hydroxy-inter-oxa-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259515
    Abstract: The present invention provides novel 19-hydroxy-6-oxo-PGF.sub.1 intermediates for preparing prostacyclin analogs which are useful for pharmacological purposes, e.g., anti-asthmatic indications.
    Type: Grant
    Filed: March 3, 1980
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259514
    Abstract: The present invention provides novel 19-hydroxy-13,14-dihydro-PG.sub.2 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259523
    Abstract: This invention provides new mono-deuterated prostaglandins having prolonged uterotonic activity.
    Type: Grant
    Filed: May 11, 1979
    Date of Patent: March 31, 1981
    Assignee: Sandoz Ltd.
    Inventors: Pietro Bollingen, Manfred Krieger
  • Patent number: 4259517
    Abstract: The present invention provides novel 19-hydroxy-trans-2,3-didehydro-13,14-dihydro-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259516
    Abstract: The present invention provides novel 19-hydroxy-inter-oxa-13,14-dihydro-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259513
    Abstract: The present invention provides novel 19-hydroxy-13,14-dihydro-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4258057
    Abstract: The present invention relates to novel prostaglandin derivatives of the formula I ##STR1## which are structurally related to the naturally occurring prostaglandins and in which R.sup.1 denotes (a) hydrogen or a straight-chain or branched, saturated or unsaturated aliphatic or cycloaliphatic hydrocarbon radical having up to ten carbon atoms or (b) a physiologically acceptable metal or NH.sub.4 ion or an ammonium ion which is derived from a primary, secondary or tertiary amine and R.sup.2 denotes a straight-chain, aliphatic hydrocarbon radical having up to six carbon atoms and to a process for their manufacture.The compounds of the invention are distinguished in particular by gastric acid secretion-inhibiting and ulcer-protective properties.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: March 24, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch, Martin Bickel
  • Patent number: 4257971
    Abstract: The present invention provides novel 19-hydroxy PG.sub.2 analogs, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: March 24, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4256906
    Abstract: The present invention provides novel 19-hydroxy-trans-2,3-didehydro-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 26, 1979
    Date of Patent: March 17, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4254275
    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: September 27, 1979
    Date of Patent: March 3, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4254278
    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: September 27, 1979
    Date of Patent: March 3, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4251669
    Abstract: The present invention relates to new analogues which do not occur naturally of prostanoic acids of the formula I ##STR1## The compounds of the invention have spasmogenic, bronchodilatant and hypotensive properties. Therefore, they can be used as medicaments.This invention also relates to a process for preparing the compounds of the invention.
    Type: Grant
    Filed: January 19, 1978
    Date of Patent: February 17, 1981
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Beck, Wilhelm Bartmann, Ulrich Lerch, Bernward Schokens
  • Patent number: 4250323
    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: September 27, 1979
    Date of Patent: February 10, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4250321
    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: September 27, 1979
    Date of Patent: February 10, 1981
    Assignee: American Cyanamid Company
    Inventor: Middleton B. Floyd, Jr.
  • Patent number: 4250183
    Abstract: N-substituted .omega.-aminoalkanoyl-.omega.-aminoalkanoic acids and their pharmacologically-acceptable salts (with a base) are useful, e.g., in pharmaceutical-composition form for the treatment or prophylaxis of diseases which are based on inadequate performance of the pancreas, the bile and/or the liver. The compounds are prepared, e.g., by reacting an N-(mono- or di-substituted) .omega.-amino-alkanoic acid with an N-(unsubstituted or monosubstituted) .omega.-aminoalkanoic acid.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: February 10, 1981
    Assignee: BYK Gulden Lomberg Chemische Fabrik GmbH
    Inventor: Walter Krastinat
  • Patent number: 4250325
    Abstract: The invention described herein relates to novel 15-deoxy-16-hydroxy-16-ethynyl or 16-(1-propynyl) prostaglandins of E, F, D and A series having on the terminal methylene carbon of the alpha chain a substituent selected from the group consisting of: ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and C.sub.1 -C.sub.6 alkyl; R.sub.15 is selected from the group consisting of C.sub.1 -C.sub.4 alkyl, di-C.sub.1 -C.sub.4 -alkylamino, phenyl and phenyl substituted with one or more substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, OR, SR, F or Cl, wherein R is an alkyl group.
    Type: Grant
    Filed: December 14, 1978
    Date of Patent: February 10, 1981
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
  • Patent number: 4246426
    Abstract: 11-Substituted prostaglandins E.sub.1, E.sub.2 and F.sub.2.alpha. useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy and a process for preparing these prostaglandins.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: January 20, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
  • Patent number: 4245111
    Abstract: An improved method for synthesizing and purifying PGB.sub.x, a mixture of lymers of prostaglandin B.sub.1. PGB.sub.x activity is assayed by measuring the minimum amount of PGB.sub.x required to restore complete phosphorylation ability to isolated rat liver mitochondria, first aged and degraded to the point where they exhibit less than 5% of the phosphorylating ability of normal mitochondria. A higher and more reproducible yield of PGB.sub.x of improved quality have been produced thereby.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: January 13, 1981
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: B. David Polis, deceased, Sara F. Kwong
  • Patent number: 4243817
    Abstract: This disclosure describes derivatives, analogs, and congeners of prostanoic acid having a terminal cyclic moiety in the .beta.-chain which possess the pharmacological activities associated with the prostaglandins.
    Type: Grant
    Filed: March 30, 1977
    Date of Patent: January 6, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
  • Patent number: 4243611
    Abstract: Prostaglandin derivatives having a 19,20-didehydro, a 19-hydroxy, or a 19-keto feature are disclosed, including processes for preparing them and the appropriate intermediates.A typical 19-hydroxy compound of this invention is 19-hydroxy-19-methyl-PGF.sub.2.alpha.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: January 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4239778
    Abstract: Novel azaprostanoic acid analogs of the formula ##STR1## wherein: R is C.sub.1 to C.sub.8 alkyl or benzyl; and a has a value of from 0 to 6 inclusive, and their pharmaceutically acceptable salts and esters. Preferred 13-aza and 15-aza compounds are active in the inhibition of arachidonic acid-induced platelet aggregation and, more specifically, are direct and specific antagonists of the activity of prostaglandin H.sub.2 and thromboxane A.sub.2.
    Type: Grant
    Filed: September 12, 1978
    Date of Patent: December 16, 1980
    Assignee: The University of Illinois Foundation
    Inventors: Duane L. Venton, Guy C. Le Breton, Steven E. Enke
  • Patent number: 4239900
    Abstract: 15-Deoxy-16-hydroxy-16-ethynyl and 16-ethynylsubstituted prostanoic acids and congeners thereof, useful as bronchodilators, hypotensive agents, and as agents for the control of excessive gastric secretion.
    Type: Grant
    Filed: September 13, 1979
    Date of Patent: December 16, 1980
    Assignee: American Cyanamid Company
    Inventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei L. Chen
  • Patent number: 4237307
    Abstract: The inventions disclosed herein relates to pharmacologically active .DELTA.19 prostaglandins of the E and F series in which C-16 is substituted with hydroxyl and methyl as well as the pharmacologically acceptable, non toxic lower alkyl esters and salts thereof, and to the intermediates and processes for producing such compounds.
    Type: Grant
    Filed: June 7, 1979
    Date of Patent: December 2, 1980
    Assignee: American Cyanamid Company
    Inventor: Allan Wissner