Oxy Patents (Class 562/463)
  • Patent number: 4233454
    Abstract: The disclosure relates to a novel sequence of reactions for manufacturing known prostaglandin intermediates, and to novel chemical intermediates obtained in the course of the novel reaction sequence, for example methyl 5.beta.-chloro-2.beta.-dimethoxymethyl-3.alpha.-hydroxycyclopent-1.alpha.- ylacetate.
    Type: Grant
    Filed: September 10, 1979
    Date of Patent: November 11, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventor: Keith B. Mallion
  • Patent number: 4231965
    Abstract: 2-Nitrobenzofurans in which the furan ring is either fused to or substituted by a fused bicyclic system, which are active as antimicrobial agents, processes for their use and intermediates therefor are described.
    Type: Grant
    Filed: March 5, 1979
    Date of Patent: November 4, 1980
    Assignee: Riker Laboratories, Inc.
    Inventors: Robert A. Scherrer, Richard M. Stern
  • Patent number: 4229585
    Abstract: 16-fluoro-substituted prostaglandin analogs of the formula: ##STR1## in which R is hydrogen, a C.sub.1 -C.sub.12 alkyl group or a cation of a pharmaceutically acceptable base; one of R.sub.1 and R.sub.2 is hydrogen and the other is hydroxy or acyloxy or R.sub.1 and R.sub.2 take together, form a oxo group; one of R.sub.4 and R.sub.5 is hydroxy and the other is hydrogen; R.sub.6 is hydrogen, methyl or fluorine; n is zero or an integer of 1 to 6; and R.sub.7 is phenyl or phenyl substituted by at least one of halogen C.sub.1 -C.sub.6 alkoxy or trihalomethyl.
    Type: Grant
    Filed: April 27, 1979
    Date of Patent: October 21, 1980
    Assignee: Farmitalia Carlo Erba
    Inventors: Renato Pellegata, Carmelo Gandolfi
  • Patent number: 4226985
    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: October 7, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
  • Patent number: 4227015
    Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: October 7, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4219662
    Abstract: This invention comprises 11-deoxy-17-phenyl-18,19,20-trinor-prostaglandin-type compounds which exhibit prostaglandin-type pharmacological activity, such as lowering blood pressure, inhibiting gastric secretion, regulating the reproductive cycle, and the like.
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: August 26, 1980
    Assignee: The Upjohn Company
    Inventors: Gordon L. Bundy, Norman A. Nelson
  • Patent number: 4219668
    Abstract: Compounds of metabolites of 3-(4-biphenylylcarbonyl)propionic acid useful as anti-inflammatory and anti-platelet aggregation agents.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: August 26, 1980
    Assignee: American Cyanamid Company
    Inventor: Fortunato S. Chiccarelli
  • Patent number: 4218378
    Abstract: The present invention provides novel 11a-methano-TXA compounds and intermediates and processs for their preparation. Further provided are methods for using these novel TXA analogs as inhibitors of thromboxane synthetase, rendering these analogs useful for a variety of pharmacological purposes. These pharmacological uses include anti-inflammatory, anti-thromobitc, and anti-asthma indications.
    Type: Grant
    Filed: May 1, 1979
    Date of Patent: August 19, 1980
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4216336
    Abstract: Prostaglandin F.sub.1 .alpha. (PGF.sub.1 .alpha.) derivatives having a 5-keto feature, for example ##STR1## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
    Type: Grant
    Filed: June 22, 1979
    Date of Patent: August 5, 1980
    Assignee: The Upjohn Company
    Inventor: Roy A. Johnson
  • Patent number: 4215222
    Abstract: Prostaglandin (PG.sub.1) derivatives having (1) a 6-keto feature, for example ##STR1## or (2) a 9-deoxy-6,9-epoxy feature together with a 5-halo or 6-hydroxy feature, for example ##STR2## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
    Type: Grant
    Filed: November 9, 1978
    Date of Patent: July 29, 1980
    Assignee: The Upjohn Company
    Inventor: Udo F. Axen
  • Patent number: 4215142
    Abstract: Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-vinylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing from 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.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: July 29, 1980
    Assignee: Ono Pharmaceutical Co. Ltd.
    Inventors: Masaki Hayashi, Katsuichi Shimoji, Yoshinobu Arai
  • Patent number: 4212985
    Abstract: The disclosure includes novel compounds which differ from the known prostaglandins PGF.sub.2.alpha., PGF.sub.2.beta., PGE.sub.2, PGA.sub.2, and PGB.sub.2 in that the carbon-carbon double bond in the carboxyl-terminated chain of the novel compounds is in the 4,5-position rather than in the 5,6-position, and in that there is a phenoxy or substituted phenoxy group in the other chain of the novel compounds. These novel compounds are useful for a variety of pharmacological purposes, including abortion, labor induction, and reduction of gastric secretion.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: July 15, 1980
    Assignee: The Upjohn Company
    Inventor: Barney J. Magerlein
  • Patent number: 4211879
    Abstract: Acyl-substituted phenyl esters of prostacyclin-type compounds, for example the 4-acetylphenyl ester of prostacyclin (PGI.sub.2) illustrated by the formula ##STR1## and including esters of the isomeric 6-hydroxy-PGF.sub.1 and 6-keto-PGF.sub.1.alpha. compounds, said esters having pharmacological acitivity. Processes for preparing them and the appropriate intermediates are disclosed.
    Type: Grant
    Filed: June 14, 1979
    Date of Patent: July 8, 1980
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4209633
    Abstract: The maleic acid adduct of anthracene is used as a starting material for 11-amino-12-carboalkoxy-9,10-dihydro-9,10-ethanoanthracene, which through reaction with nitrous acid in a protic solvent provides an 11-substituted-12-carboalkoxy-10,11-dihydro-5,10-methano-5H-dibenzo[a,d]cy cloheptene which is then converted into the useful intermediate 12-carboxy-10,11-dihydro-5,10-methano-5H-dibenzo[a,d]cycloheptene.
    Type: Grant
    Filed: April 17, 1978
    Date of Patent: June 24, 1980
    Assignee: Riker Laboratories, Inc.
    Inventor: Walton J. Hammar
  • Patent number: 4208428
    Abstract: The invention relates to prostaglandin analogues of the general formula: ##STR1## (wherein A represents a grouping of the formula: ##STR2## B represents an alkylene group containing from 1 to 7 carbon atoms or a group ##STR3## (wherein the group --(CH.sub.2).sub.n --may be attached to the ortho, meta or para position of the phenyl ring and m and n, which may be the same or different, each represent an integer from 1 to 5 inclusive, the sum of the integers represented by m and n being from 2 to 6 inclusive), X represents ethylene or cis-vinylene, Y represents ethylene or trans-vinylene, W represents ethylene or trans-vinylene, Z represents a halogen atom, and R.sup.1 represents a hydrogen atom or an alkyl group containing from 1 to 12 carbon atoms) and cyclodextrin clathrates of such acids and esters and, when R.sup.1 represents a hydrogen atom, non-toxic salts thereof, which possess characteristic prostaglandin-like properties.
    Type: Grant
    Filed: July 13, 1978
    Date of Patent: June 17, 1980
    Assignee: Ono Pharmaceutical Co. Ltd.
    Inventors: Masayasu Kurono, Nobuyuki Hamanaka, Shigeru Sakuyama, Takeshi Chiba, Hisao Nakai
  • Patent number: 4207419
    Abstract: Derivatives of 11-deoxy-PGE.sub.2 are prepared. These new compounds not heretofore found in nature possess various pharmacological activities, one of which is bronchodilation.
    Type: Grant
    Filed: January 13, 1977
    Date of Patent: June 10, 1980
    Assignee: American Home Products Corporation
    Inventor: Wenling Kao
  • Patent number: 4202988
    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: May 13, 1980
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
  • Patent number: 4198430
    Abstract: Optionally active 13,14-dehydro-11-deoxy prostaglandins useful in inhibiting gastric secretions and as anti-asmthmatic agents are disclosed.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: April 15, 1980
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Carmelo Gandolfi, Renato Pellegate, Franco Faustini, Angelo Fumagalli
  • Patent number: 4195182
    Abstract: This invention relates to prostaglandin analogues of the formula: ##STR1## (wherein R represents a hydrogen atom or a methyl group, 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 compounds and, when R represents a hydrogen atom, non-toxic salts thereof, which possess characteristic prostaglandin-like activity.
    Type: Grant
    Filed: August 12, 1977
    Date of Patent: March 25, 1980
    Assignee: Ono Pharmaceutical Co. Ltd.
    Inventors: Masaki Hayashi, Seiji Kori, Takanori Okada
  • Patent number: 4190671
    Abstract: The present invention provides new chalcone derivatives of the general formula: ##STR1## wherein R.sub.1 is a hydroxyl, carboxylic acid or sulphonic acid group or a carboxyalkoxy or sulphoalkoxy radical, R.sub.2 and R.sub.3, which may be the same or different, are hydrogen or halogen atoms, hydroxyl groups or alkoxy radicals and R.sub.4 is an alkyl, hydroxyalkyl, alkoxy, carboxyalkoxy, sulphoalkoxy or carboxyalkylcarbonyloxyalkyl radical or a carboxylic acid or sulphonic acid group, with the proviso that compounds of general formula (Ia) always contain at least one carboxylic acid or sulphonic acid group; and the non-toxic inorganic and organic salts of those compounds containing at least one carboxylic acid or sulphonic acid group, the compounds of the invention are useful for treating inflammatory and allergic conditions and for treating ulcerous conditions of the gastro-intestinal tract in humans.
    Type: Grant
    Filed: March 3, 1978
    Date of Patent: February 26, 1980
    Assignee: Biorex Laboratories Limited
    Inventors: Anthony E. Vanstone, Graham K. Maile
  • Patent number: 4189596
    Abstract: 2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.
    Type: Grant
    Filed: May 2, 1977
    Date of Patent: February 19, 1980
    Assignee: The Upjohn Company
    Inventor: Verlan H. VanRheenen
  • Patent number: 4189594
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is Cl, Br, CH(CH.sub.3).sub.2 or C(CH.sub.3).sub.3 ; A is a single bond, --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --; and R.sup.2 is H, the cation of a pharmaceutically acceptable salt or an alkyl of up to three carbons, are strong hypolipaemic agents.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: February 19, 1980
    Assignee: Klingepharma GmbH & Co.
    Inventors: Helmut Grill, Roland Loser, Josef Wagner, Rainer H. Zschocke
  • Patent number: 4187381
    Abstract: A process for producing optically active 16-substituted prostaglandins and new 16-substituted prostaglandins produced thereby which are useful as cardiovascular agents and as agents for inducing labor in pregnant females and for the termination of pregnancy.
    Type: Grant
    Filed: November 2, 1977
    Date of Patent: February 5, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
  • Patent number: 4178461
    Abstract: This disclosure describes novel 15-hydroxy-16,16-spirocycloalkyl prostanoic acids and derivatives and congeners thereof which are useful as bronchodilators and gastric acid secretion inhibitors.
    Type: Grant
    Filed: March 16, 1977
    Date of Patent: December 11, 1979
    Assignee: American Cyanamid Company
    Inventors: Robert E. Schaub, Martin J. Weiss
  • Patent number: 4178454
    Abstract: The degradation of prostaglandins E is prevented or minimized by combining prostaglandins E with methylhesperidin.
    Type: Grant
    Filed: October 11, 1978
    Date of Patent: December 11, 1979
    Assignee: Toray Industries, Inc.
    Inventors: Masanobu Naruto, Kiyotaka Ohno, Norio Naruse
  • Patent number: 4178456
    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: December 11, 1979
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
  • Patent number: 4178457
    Abstract: Novel 16-phenoxy and 16-(o, m or p)-substituted phenoxy derivatives of (dl)-9-keto-11.alpha.,15.alpha.-dihydroxy-17,18,19,20-tetranorprosta-4,5,1 3-trans-trienoic acid, the pharmaceutically acceptable, non-toxic lower alkyl esters and salts thereof and processes for the production of such compounds. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretion; and as agents for the control of asthmatic attack, because of their bronchodilating activity.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: December 11, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Albert R. Van Horn, Gabriel Garay, John A. Edwards
  • Patent number: 4175202
    Abstract: This invention is a group of 4,5,6-trinor-3,7-inter-m-phenylene prostaglandin-type compounds and processes for making them. These compounds are useful for a variety of pharmacological purposes, including hypotensive control and inhibition of platelet aggregation.A typical formula for a PGA.sub.
    Type: Grant
    Filed: June 29, 1978
    Date of Patent: November 20, 1979
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4174458
    Abstract: The present invention relates to novel not naturally occurring analogues of prostanoic acids of the formula ##STR1## as well as a process for their preparation. The compounds of the invention have valuable pharmacological properties similar to those of the natural prostaglandins and therefore can be used as medicaments.
    Type: Grant
    Filed: May 3, 1978
    Date of Patent: November 13, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Milos Babej, Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch
  • Patent number: 4172950
    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: October 30, 1979
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4172949
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or methyl; R.sup.1 is hydrogen, C.sub.1 to C.sub.8 linear or branched alkyl or C.sub.1 to C.sub.8 linear or branched alkanoyl; X is oxygen or sulfur; R.sup.2 is selected from the group hydrogen, C.sub.1 to C.sub.18 linear or branched alkyl and the radicals --(CH.sub.2).sub.n --NR.sup.3 R.sup.4, --CH.sub.2 --CH(OH)--CH.sub.2 --OH or a ketal thereof formed from the aldehyde or ketone R.sup.5 R.sup.6 CO, wherein R.sup.3 and R.sup.4 are each independently C.sub.1 to C.sub.6 linear or branched alkyl or R.sup.3 and R.sup.4 taken together with the nitrogen atom of the first radical are attached to form a 5- or 6-membered heterocyclic ring, R.sup.5 and R.sup.6 are each independently hydrogen, C.sub.1 to C.sub.6 linear or branched alkyl, phenyl or benzyl or R.sup.5 and R.sup.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: October 30, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: James P. Dunn, Peter H. Nelson, Karl G. Untch
  • Patent number: 4168382
    Abstract: Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: September 18, 1979
    Assignee: The Upjohn Company
    Inventor: David C. Peterson
  • Patent number: 4168384
    Abstract: Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: September 18, 1979
    Assignee: The Upjohn Company
    Inventor: David C. Peterson
  • Patent number: 4161605
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. 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 3, 1977
    Date of Patent: July 17, 1979
    Assignee: The Upjohn Company
    Inventor: Ernest W. Yankee
  • Patent number: 4160103
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. 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: May 8, 1978
    Date of Patent: July 3, 1979
    Assignee: The Upjohn Company
    Inventor: Ernest W. Yankee
  • Patent number: 4160104
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. 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: May 8, 1978
    Date of Patent: July 3, 1979
    Assignee: The Upjohn Company
    Inventor: Ernest W. Yankee
  • Patent number: 4160102
    Abstract: Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: July 3, 1979
    Assignee: The Upjohn Company
    Inventor: David C. Peterson
  • Patent number: 4158667
    Abstract: Prostaglandin (PG.sub.1) derivatives having (1) a 6-keto feature, for example ##STR1## or (2) a 9-deoxy-6,9-epoxy feature together with a 5-halo or 6-hydroxy feature, for example ##STR2## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
    Type: Grant
    Filed: July 28, 1977
    Date of Patent: June 19, 1979
    Assignee: The Upjohn Company
    Inventor: Udo F. Axen
  • Patent number: 4157448
    Abstract: Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: June 5, 1979
    Assignee: The Upjohn Company
    Inventor: David C. Peterson
  • Patent number: 4156781
    Abstract: Prostaglandin analogs with the following cyclopename ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: May 29, 1979
    Assignee: The Upjohn Company
    Inventor: David C. Peterson
  • Patent number: 4156088
    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: May 22, 1979
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4154949
    Abstract: 11-DESOXY-15-SUBSTITUTED-.omega.-PENTANORPROSTAGLANDINS AND VARIOUS INTERMEDIATES EMPLOYED IN THEIR PREPARATION. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins, but exhibit a greater tissue specificity of action.
    Type: Grant
    Filed: January 31, 1977
    Date of Patent: May 15, 1979
    Assignee: Pfizer Inc.
    Inventors: Michael R. Johnson, Thomas K. Schaaf, Jasjit S. Bindra, Hans-Jurgen E. Hess, James F. Eggler
  • Patent number: 4153721
    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: December 19, 1977
    Date of Patent: May 8, 1979
    Assignee: Riker Laboratories, Inc.
    Inventors: Walton J. Hammar, Mark A. Rustad
  • Patent number: 4152523
    Abstract: This invention comprises 11-deoxy-17-phenyl-18,19,20-trinor-prostaglandin-type compounds which exhibit prostaglandin-type pharmacological activity, such as lowering blood pressure, inhibiting gastric secretion, regulating the reproductive cycle, and the like.
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: May 1, 1979
    Assignee: The Upjohn Company
    Inventors: Gordon L. Bundy, Norman A. Nelson
  • Patent number: 4152456
    Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.
    Type: Grant
    Filed: October 7, 1977
    Date of Patent: May 1, 1979
    Assignee: Ayerst, McKenna and Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4151359
    Abstract: This invention comprises 11-deoxy-17-phenyl-18,19,20-trinor-prostaglandin-type compounds which exhibit prostaglandin-type pharmacological activity, such as lowering blood pressure, inhibiting gastric secretion, regulating the reproductive cycle, and the like.
    Type: Grant
    Filed: February 28, 1977
    Date of Patent: April 24, 1979
    Assignee: The Upjohn Company
    Inventors: Gordon L. Bundy, Norman A. Nelson
  • Patent number: 4150235
    Abstract: Novel interphenylene derivatives of 11,12-secoprostaglandins are prepared by the stepwise alkylation of the ethyl ester or the t-butyl ester of acetoacetic acid. One such method involves treatment of the t-butyl ester of acetoacetic acid with a strong base to form the anion followed by treatment with ethyl p-(3-bromopropyl)benzoate to produce ethyl 4-(4-tert-butoxycarbonyl-5-oxo-hexyl)benzoate, subsequently reacting the anion of the thus-formed benzoate with 1-chloro-4-acetoxynonane to produce ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridecyl)benzoate followed by decarboxylation and alkaline hydrolysis to produce the desired product 4-(4-acetyl-8-hydroxytridecyl)benzoic acid which is useful as pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.
    Type: Grant
    Filed: December 17, 1976
    Date of Patent: April 17, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., John B. Bicking
  • Patent number: 4149006
    Abstract: The present invention encompasses compounds of the formula: ##STR1## wherein n is 0 or 1; Y represents ethylene or vinylene; R represents hydrogen or lower alkyl having 1-7 carbon atoms; R', R", R'" each individually represent hydrogen or methyl; Ar represents phenyl, halosubstituted phenyl, alkyl substituted phenyl wherein the alkyl contains 1-4 carbon atoms, alkoxy substituted phenyl wherein the alkoxy contains 1-4 carbon atoms, trifluoromethylphenyl, or biphenyl; and the wavy line indicates R or S stereochemistry.
    Type: Grant
    Filed: January 24, 1977
    Date of Patent: April 10, 1979
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Raphael Pappo
  • Patent number: 4149007
    Abstract: Analogues of prostaglandins A, E and F in which a phenyl moiety is attached to the C.sub.14 carbon atom are disclosed. Also disclosed are methods of preparing the analogues and starting materials. The compounds have the structural formula: ##STR1## in which J is methylene, R or S-hydroxymethylene or methine; L is methylene or methine and can be methine only when J is methine; M is carbonyl, R or S-hydroxymethylene; Q is ethylene, Z-vinylene or inter-phenylene; T is an alkoxy-carbonyl having from 2 to 3 carbon atoms inclusive, or carboxyl; and B is a loweralkyl of from 1 to 5 carbon atoms.The prostaglandin analogues of the present invention exhibit a separation of pharmacological activity. The analogues can be used for platelet aggregation (and Methyl 14-Phenyl-11.alpha.,15S-dihydroxy-9-oxoprost-13E-en-1-oate can be used for antagonism for smooth muscle stimulation) without the accompanying undesirable side effects of natural prostaglandins, e.g., flush, headache, abdominal cramps and nausea.
    Type: Grant
    Filed: June 24, 1977
    Date of Patent: April 10, 1979
    Assignee: Miles Laboratories, Inc.
    Inventors: Robert T. Buckler, David L. Garling
  • Patent number: 4145555
    Abstract: The present invention relates to prostaglandin analogues of the general formula: ##STR1## ?wherein X represents cis or trans-vinylene or ethylene, Z represents ##STR2## R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 12 carbon atoms, R.sup.2 represents a hydrogen atom or a methyl group, R.sup.3 represents a straight- or branched-chain alkylene group containing from 1 to 7 carbon atoms and R.sup.4 represents a cycloalkyl group containing from 5 to 7 carbon atoms, a grouping of the formula: ##STR3## (wherein R.sup.5 and R.sup.6, which may be the same or different, each represent a hydrogen atom or halogen atom, a trifluoromethyl group or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms), or a grouping of the formula: ##STR4## (wherein R.sup.5 and R.sup.6 are as hereinbefore defined), or R.sup.3 and R.sup.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: March 20, 1979
    Assignee: Ono Pharmaceutical Company
    Inventors: Masaki Hayashi, Seiji Kori, Yoshinobu Arai, Takanori Okada, Yoshitaka Konishi