Oxy Patents (Class 562/463)
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Patent number: 4233454Abstract: 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: GrantFiled: September 10, 1979Date of Patent: November 11, 1980Assignee: Imperial Chemical Industries LimitedInventor: Keith B. Mallion
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Patent number: 4231965Abstract: 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: GrantFiled: March 5, 1979Date of Patent: November 4, 1980Assignee: Riker Laboratories, Inc.Inventors: Robert A. Scherrer, Richard M. Stern
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Patent number: 4229585Abstract: 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: GrantFiled: April 27, 1979Date of Patent: October 21, 1980Assignee: Farmitalia Carlo ErbaInventors: Renato Pellegata, Carmelo Gandolfi
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Patent number: 4226985Abstract: 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: GrantFiled: April 2, 1979Date of Patent: October 7, 1980Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4227015Abstract: 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: GrantFiled: February 14, 1979Date of Patent: October 7, 1980Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
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Patent number: 4219662Abstract: 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: GrantFiled: February 28, 1977Date of Patent: August 26, 1980Assignee: The Upjohn CompanyInventors: Gordon L. Bundy, Norman A. Nelson
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Patent number: 4219668Abstract: Compounds of metabolites of 3-(4-biphenylylcarbonyl)propionic acid useful as anti-inflammatory and anti-platelet aggregation agents.Type: GrantFiled: July 5, 1979Date of Patent: August 26, 1980Assignee: American Cyanamid CompanyInventor: Fortunato S. Chiccarelli
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Patent number: 4218378Abstract: 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: GrantFiled: May 1, 1979Date of Patent: August 19, 1980Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4216336Abstract: 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: GrantFiled: June 22, 1979Date of Patent: August 5, 1980Assignee: The Upjohn CompanyInventor: Roy A. Johnson
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Patent number: 4215222Abstract: 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: GrantFiled: November 9, 1978Date of Patent: July 29, 1980Assignee: The Upjohn CompanyInventor: Udo F. Axen
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Patent number: 4215142Abstract: 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: GrantFiled: September 8, 1978Date of Patent: July 29, 1980Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masaki Hayashi, Katsuichi Shimoji, Yoshinobu Arai
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Patent number: 4212985Abstract: 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: GrantFiled: April 28, 1978Date of Patent: July 15, 1980Assignee: The Upjohn CompanyInventor: Barney J. Magerlein
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Patent number: 4211879Abstract: 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: GrantFiled: June 14, 1979Date of Patent: July 8, 1980Assignee: The Upjohn CompanyInventor: John C. Sih
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Patent number: 4209633Abstract: 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: GrantFiled: April 17, 1978Date of Patent: June 24, 1980Assignee: Riker Laboratories, Inc.Inventor: Walton J. Hammar
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Patent number: 4208428Abstract: 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: GrantFiled: July 13, 1978Date of Patent: June 17, 1980Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masayasu Kurono, Nobuyuki Hamanaka, Shigeru Sakuyama, Takeshi Chiba, Hisao Nakai
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Patent number: 4207419Abstract: 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: GrantFiled: January 13, 1977Date of Patent: June 10, 1980Assignee: American Home Products CorporationInventor: Wenling Kao
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Patent number: 4202988Abstract: 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: GrantFiled: March 30, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4198430Abstract: Optionally active 13,14-dehydro-11-deoxy prostaglandins useful in inhibiting gastric secretions and as anti-asmthmatic agents are disclosed.Type: GrantFiled: March 8, 1976Date of Patent: April 15, 1980Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Carmelo Gandolfi, Renato Pellegate, Franco Faustini, Angelo Fumagalli
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Patent number: 4195182Abstract: 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: GrantFiled: August 12, 1977Date of Patent: March 25, 1980Assignee: Ono Pharmaceutical Co. Ltd.Inventors: Masaki Hayashi, Seiji Kori, Takanori Okada
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Patent number: 4190671Abstract: 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: GrantFiled: March 3, 1978Date of Patent: February 26, 1980Assignee: Biorex Laboratories LimitedInventors: Anthony E. Vanstone, Graham K. Maile
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Patent number: 4189596Abstract: 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: GrantFiled: May 2, 1977Date of Patent: February 19, 1980Assignee: The Upjohn CompanyInventor: Verlan H. VanRheenen
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Patent number: 4189594Abstract: 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: GrantFiled: August 1, 1978Date of Patent: February 19, 1980Assignee: Klingepharma GmbH & Co.Inventors: Helmut Grill, Roland Loser, Josef Wagner, Rainer H. Zschocke
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Patent number: 4187381Abstract: 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: GrantFiled: November 2, 1977Date of Patent: February 5, 1980Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Jane L. Jernow, Perry Rosen
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Patent number: 4178461Abstract: 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: GrantFiled: March 16, 1977Date of Patent: December 11, 1979Assignee: American Cyanamid CompanyInventors: Robert E. Schaub, Martin J. Weiss
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Patent number: 4178454Abstract: The degradation of prostaglandins E is prevented or minimized by combining prostaglandins E with methylhesperidin.Type: GrantFiled: October 11, 1978Date of Patent: December 11, 1979Assignee: Toray Industries, Inc.Inventors: Masanobu Naruto, Kiyotaka Ohno, Norio Naruse
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Patent number: 4178456Abstract: 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: GrantFiled: March 30, 1977Date of Patent: December 11, 1979Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4178457Abstract: 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: GrantFiled: July 10, 1978Date of Patent: December 11, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: Albert R. Van Horn, Gabriel Garay, John A. Edwards
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Patent number: 4175202Abstract: 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: GrantFiled: June 29, 1978Date of Patent: November 20, 1979Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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Patent number: 4174458Abstract: 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: GrantFiled: May 3, 1978Date of Patent: November 13, 1979Assignee: Hoechst AktiengesellschaftInventors: Milos Babej, Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch
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Patent number: 4172950Abstract: 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: GrantFiled: April 28, 1978Date of Patent: October 30, 1979Assignee: The Upjohn CompanyInventor: Herman W. Smith
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Patent number: 4172949Abstract: 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: GrantFiled: June 28, 1978Date of Patent: October 30, 1979Assignee: Syntex (U.S.A.) Inc.Inventors: James P. Dunn, Peter H. Nelson, Karl G. Untch
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Patent number: 4168382Abstract: 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: GrantFiled: May 8, 1978Date of Patent: September 18, 1979Assignee: The Upjohn CompanyInventor: David C. Peterson
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Patent number: 4168384Abstract: 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: GrantFiled: May 8, 1978Date of Patent: September 18, 1979Assignee: The Upjohn CompanyInventor: David C. Peterson
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Patent number: 4161605Abstract: 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: GrantFiled: March 3, 1977Date of Patent: July 17, 1979Assignee: The Upjohn CompanyInventor: Ernest W. Yankee
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Patent number: 4160103Abstract: 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: GrantFiled: May 8, 1978Date of Patent: July 3, 1979Assignee: The Upjohn CompanyInventor: Ernest W. Yankee
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Patent number: 4160104Abstract: 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: GrantFiled: May 8, 1978Date of Patent: July 3, 1979Assignee: The Upjohn CompanyInventor: Ernest W. Yankee
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Patent number: 4160102Abstract: 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: GrantFiled: May 8, 1978Date of Patent: July 3, 1979Assignee: The Upjohn CompanyInventor: David C. Peterson
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Patent number: 4158667Abstract: 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: GrantFiled: July 28, 1977Date of Patent: June 19, 1979Assignee: The Upjohn CompanyInventor: Udo F. Axen
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Patent number: 4157448Abstract: 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: GrantFiled: May 8, 1978Date of Patent: June 5, 1979Assignee: The Upjohn CompanyInventor: David C. Peterson
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Patent number: 4156781Abstract: 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: GrantFiled: May 8, 1978Date of Patent: May 29, 1979Assignee: The Upjohn CompanyInventor: David C. Peterson
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Patent number: 4156088Abstract: 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: GrantFiled: April 28, 1978Date of Patent: May 22, 1979Assignee: The Upjohn CompanyInventor: Herman W. Smith
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Patent number: 4154949Abstract: 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: GrantFiled: January 31, 1977Date of Patent: May 15, 1979Assignee: Pfizer Inc.Inventors: Michael R. Johnson, Thomas K. Schaaf, Jasjit S. Bindra, Hans-Jurgen E. Hess, James F. Eggler
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Patent number: 4153721Abstract: 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: GrantFiled: December 19, 1977Date of Patent: May 8, 1979Assignee: Riker Laboratories, Inc.Inventors: Walton J. Hammar, Mark A. Rustad
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Patent number: 4152523Abstract: 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: GrantFiled: February 28, 1977Date of Patent: May 1, 1979Assignee: The Upjohn CompanyInventors: Gordon L. Bundy, Norman A. Nelson
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Patent number: 4152456Abstract: 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: GrantFiled: October 7, 1977Date of Patent: May 1, 1979Assignee: Ayerst, McKenna and Harrison LimitedInventors: Jehan F. Bagli, Tibor Bogri
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Patent number: 4151359Abstract: 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: GrantFiled: February 28, 1977Date of Patent: April 24, 1979Assignee: The Upjohn CompanyInventors: Gordon L. Bundy, Norman A. Nelson
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Patent number: 4150235Abstract: 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: GrantFiled: December 17, 1976Date of Patent: April 17, 1979Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., John B. Bicking
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Patent number: 4149006Abstract: 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: GrantFiled: January 24, 1977Date of Patent: April 10, 1979Assignee: G. D. Searle & Co.Inventors: Paul W. Collins, Raphael Pappo
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Patent number: 4149007Abstract: 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: GrantFiled: June 24, 1977Date of Patent: April 10, 1979Assignee: Miles Laboratories, Inc.Inventors: Robert T. Buckler, David L. Garling
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Patent number: 4145555Abstract: 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: GrantFiled: March 7, 1977Date of Patent: March 20, 1979Assignee: Ono Pharmaceutical CompanyInventors: Masaki Hayashi, Seiji Kori, Yoshinobu Arai, Takanori Okada, Yoshitaka Konishi