Oxy Patents (Class 562/463)
  • Patent number: 4290974
    Abstract: The invention relates to oxybenzylidenebornanones which correspond to the general formula: ##STR1## in which Z and Z' denote hydrogen or a radical SO.sub.3 H, at least one of the two radicals Z and Z' denoting hydrogen, R.sub.1 denotes hydrogen, an alkyl radical having 2 to 18 carbon atoms, an alkenyl radical having 3 to 18 carbon atoms, a radical --(CH.sub.2 CH.sub.2 O).sub.n H, ##STR2## --(CH.sub.2).sub.m CO.sub.2 R, in which R denotes H or an alkyl radical, --(CH.sub.2).sub.3 SO.sub.3 H or a divalent radical --(CH.sub.2).sub.m or --CH.sub.2 --CHOH--CH.sub.2, m having the values 1 to 10, n having the values 1 to 20 and p having the values 1 to 6, and R.sub.3 and R.sub.4 representing hydrogen or an optionally branched or hydroxylic alkyl radical, or forming an aminoaliphatic heterocyclic ring with the nitrogen atom, R.sub.2 denotes a hydrogen atom, an alkoxy radical or a divalent radical --O-- bonded to the radical R.sub.1 if the latter is also divalent, and q denotes 1 or 2; if q has the value 2, R.sub.
    Type: Grant
    Filed: July 10, 1979
    Date of Patent: September 22, 1981
    Assignee: L'Oreal
    Inventors: Claude Bouillon, Charles Vayssie
  • Patent number: 4284792
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-inter-phenylene-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: August 18, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4283550
    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: August 11, 1981
    Assignee: American Cyanamid
    Inventor: Middleton B. Floyd, Jr.
  • 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: 4277619
    Abstract: The present invention provides novel 19-hydroxy-19-methyl-inter-phenylene-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: July 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4277611
    Abstract: The present invention provides novel 11-deoxy-11-hydroxymethyl-inter-phenylene-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 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: 4275221
    Abstract: Compounds wherein 2-nitrobenzofuran is substituted by one or two phenyl groups and certain other substituents which are active as antimicrobial agents, processes for their use and intermediates therefor.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: June 23, 1981
    Assignee: Riker Laboratories, Inc.
    Inventors: Walton J. Hammar, Mark A. Rustad
  • Patent number: 4273784
    Abstract: The present invention concerns prostaglandins having a cyclopropane ring in the 2,3 position.
    Type: Grant
    Filed: March 28, 1979
    Date of Patent: June 16, 1981
    Assignee: Sandoz Ltd.
    Inventor: Pietro Bollinger
  • Patent number: 4269994
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-19-o xo-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: 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: 4267357
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-11-h ydroxymethyl-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: May 12, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4266072
    Abstract: The present invention provides novel 11-deoxy-inter-phenylene-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: May 5, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4263445
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: April 21, 1981
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4263212
    Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: April 21, 1981
    Assignee: Rikagaku Kenkyusho
    Inventors: Pangbu Hong, Hiroshi Yamazaki
  • Patent number: 4262131
    Abstract: The present invention provides novel 19-hydroxy-inter-phenylene-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 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4262134
    Abstract: The present invention provides novel 11-deoxy-11-hydroxymethyl-inter-phenylene-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: April 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4262133
    Abstract: The present invention provides novel 13,14-didehydro-interphenylene-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: April 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4262132
    Abstract: The present invention provides novel 13,14-didehydro-interphenylene-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: April 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4262135
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-19-oxo-PGE.su b.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: April 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4262136
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene4,5,6-trinor-3-oxa-11-deoxy-11-hy droxymethy-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: April 14, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260797
    Abstract: The present invention provides novel 9-deoxy-9-methylene-11-deoxy-11-hydroxymethyl-inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260789
    Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260791
    Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-11-deoxy-9-deoxy-9-methylene-19-oxo-PGF.su b.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260783
    Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-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 26, 1979
    Date of Patent: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260800
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-9-de oxy-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260787
    Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260786
    Abstract: The present invention provides novel 13,14-didehydro-interphenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260792
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-19-oxo-PGF.su b.1 compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260785
    Abstract: The present invention provides novel 13,14-didehydro-interphenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • 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: 4260794
    Abstract: The present invention provides novel 11-deoxy-inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260796
    Abstract: The present invention provides novel inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260784
    Abstract: The present invention provides novel 9-deoxy-9-methylene-11-deoxy-inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260799
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-11-h ydroxymethyl-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260788
    Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260795
    Abstract: The present invention provides novel inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260801
    Abstract: The present invention provides novel 13,14-dihydro-inter-3,7-inter-m-phenylene-4,5,6-trinor-3-oxa-11-deoxy-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260790
    Abstract: The present invention provides novel 13,14-didehydro-inter-phenylene-11-deoxy-11-hydroxymethyl-9-deoxy-9-methyl ene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260793
    Abstract: The present invention provides novel 9-deoxy-9-methylene-inter-phenylene-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: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259250
    Abstract: The present invention provides novel thromboxane analogs and intermediates. Particularly, the present invention provides novel 11a-homo-PG intermediates for preparing 11a-methano TXA.sub.2 compounds.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • 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: 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: 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: 4249016
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: February 3, 1981
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • 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: 4238623
    Abstract: Disclosed are prostaglandin analogues having the structural formula, ##STR1## in which: T is selected from the group consisting of carboxyl, alkoxycarbonyl or cyano;M is selected from the group consisting of carbonyl, R-hydroxymethylene or S-hydroxymethylene;L is selected from the group consisting of methylene or methine, provided L is methine only if J is methine;J is selected from the group consisting of methylene, ethylene, R-hydroxymethylene, S-hydroxymethylene or methine, provided J is methine only if L is methine;W is selected from the group consisting of ##STR2## T.sub.1 and T.sub.2 are attached to adjacent carbon atoms; T.sub.1 is selected from the group consisting of hydrogen or phenyl, provided T.sub.1 is phenyl only if T.sub.2 is lower alkyl;T.sub.2 is selected from the group consisting of n-pentyl or lower alkyl, provided T.sub.2 is lower alkyl only if T.sub.1 is phenyl; orT.sub.1 and T.sub.2 are joined together to form an alkylene group of 4 or 6 carbon atoms.
    Type: Grant
    Filed: March 29, 1976
    Date of Patent: December 9, 1980
    Assignee: Miles Laboratories, Inc.
    Inventor: Robert T. Buckler