Oxy In Acid Moiety Patents (Class 560/53)
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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: 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: 4209444Abstract: Compounds of formula ##STR1## their mirror images and racemic mixtures, and the physiologically acceptable salts thereof,wherein A and D each are ketalized carbonyl groups; B is --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 CH.sub.2 --, --CH(CH.sub.3)CH.sub.2 ----C(CH.sub.3).sub.2 CH.sub.2 -- or --CH.sub.2 O--; R.sup.1 is H or alkyl of 1-4 C-atoms; and R.sup.2 is alkyl of 3 to 5 C-atoms, phenyl or phenyl substituted one to three times by F, Cl, CF.sub.3, OH, OCH.sub.3, OC.sub.2 H.sub.5 or alkyl of 1 to 3 C-atoms inhibit aggregation and/or adhesion of thrombocytes.Type: GrantFiled: November 29, 1977Date of Patent: June 24, 1980Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Manfred Baumgarth, Dieter Orth, Hans-Eckart Radunz, Reinhard Lissner, Jurgen Maisenbacher
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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: 4195183Abstract: PGF.sub..alpha. compounds are disclosed having as the lower side chain ##STR1## in which one of R.sub.4 and R.sub.5 hydroxyl and the other is alkoxy R.sub.6 is hydrogen or alkyl, m is 0-3, E represents oxygen or sulphur and R is hydrogen, halogen, alkyl, alkoxy or trihaloalkyl.Type: GrantFiled: May 2, 1978Date of Patent: March 25, 1980Assignee: Farmitalia Certo Erba S.p.A.Inventors: Carmelo Gandolfi, Franco Faustini, Walter Moretti, Mario M. Usardi, Roberto Ceserani
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Patent number: 4190602Abstract: Monoacetals of aromatic diketones in which the acetal group is derived from primary mono- or dialkohols are useful as sensitizers in the photochemical polymerization or photochemical crosslinking of polymers. They are prepared from the diketones (benzils) by reaction with sulfites. The sulfites and the benzils may be formed immediately before the reaction in the same vessel without isolating these compounds. Most of the benzil monoacetals are new compounds.Type: GrantFiled: June 22, 1978Date of Patent: February 26, 1980Assignee: Ciba-Geigy CorporationInventors: Jean Brunisholz, Rudolf Kirchmayr
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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: 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: 4172205Abstract: Compounds wherein a phenylalkanoic acid is substituted by a 2-nitro-3-phenylbenzofuran group which are active as antimicrobial agents, processes for their use and intermediates therefor are described.Type: GrantFiled: December 20, 1978Date of Patent: October 23, 1979Assignee: Riker Laboratories, Inc.Inventors: Walton J. Hammar, Mark A. Rustad
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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: 4163859Abstract: The present invention encompasses compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently an alkyl radical containing from 1 to 2 carbon atoms and R.sup.3 is hydrogen or an alkyl radical containing from 1 to 7 carbon atoms, sodium, potassium, or ammonium cation. The compounds of the present invention are prepared by the condensation of alkyl(4-formylphenoxy)-2,2-dialkylacetate with acetophenone in basic medium. These compounds are potent hypolipemic agents as well as antifungal and antibacterial agents.Type: GrantFiled: July 18, 1977Date of Patent: August 7, 1979Assignee: G. D. Searle & Co.Inventor: William K. Sprenger, deceased
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Patent number: 4163016Abstract: 16-Substituted prostaglandins 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: GrantFiled: July 5, 1977Date of Patent: July 31, 1979Assignee: Hoffmann-La Roche Inc.Inventors: George W. Holland, Perry Rosen
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Patent number: 4161606Abstract: 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 17, 1979Assignee: The Upjohn CompanyInventor: Ernest W. Yankee
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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: 4160105Abstract: 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: July 3, 1979Assignee: The Upjohn CompanyInventor: Herman W. Smith
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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: 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: 4160101Abstract: 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: July 3, 1979Assignee: The Upjohn CompanyInventor: Herman W. Smith
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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: 4157341Abstract: 11-Desoxy-16-aryloxy-.omega.-tetranorprostaglandins are disclosed. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins but they exhibit a greater tissue specificity of action.Type: GrantFiled: November 9, 1977Date of Patent: June 5, 1979Assignee: Pfizer Inc.Inventors: Jasjit S. Bindra, James F. Eggler, Michael R. Johnson, Thomas K. Schaaf
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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: 4156089Abstract: This invention comprises certain analogs of the prostagladins 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: 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: 4154952Abstract: Substituted cyclopropane derivatives are prepared in one step by interreacting an aldehyde, an active methylene compound, a sulfoxonium or sulfonium bromide or iodide, and a strong base in a reaction-inert organic solvent.Type: GrantFiled: January 31, 1977Date of Patent: May 15, 1979Inventor: Harry W. Schultz
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Patent number: 4154950Abstract: Prostaglandin E-, F.sub..alpha. -, F.sub..beta. -, A-, and B-type compounds are disclosed with intermediates and with processes for making them. These compounds differ from the prostaglandins in that they are substituted at C-16 with a phenoxy or substituted phenoxy, and have a lower alkyl group in place of the hydrogen at C-15 and/or a lower alkoxy group in place of the hydroxy group at C-15. These compounds are useful for a variety of pharmacological purposes, including antiulcer, inhibition of platelet aggregation, increase in nasal patency, labor induction at term, and wound healing.Type: GrantFiled: August 16, 1976Date of Patent: May 15, 1979Assignee: The Upjohn CompanyInventor: Norman A. Nelson
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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: 4152527Abstract: The 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: December 27, 1973Date of Patent: May 1, 1979Assignee: Pfizer Inc.Inventors: Hans-Jurgen E. Hess, Thomas K. Schaaf
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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: 4150236Abstract: Tricyclic aromatic compounds of the formula ##STR1## including those wherein: (A) R.sub.1 is H, R.sub.2 is carbomethoxy, and R.sub.3 is methyl;(b) R.sub.1 is acetyl, R.sub.2 is carbomethoxy, and R.sub.3 is methyl;(c) R.sub.1 and R.sub.3 are methyl and R.sub.2 is carbomethoxy;(d) R.sub.1, R.sub.2, and R.sub.3 are hydrogen; and(e) R.sub.1 and R.sub.3 are methyl and R.sub.2 is hydrogenAre intermediates for the total synthesis of steroids.Type: GrantFiled: July 19, 1977Date of Patent: April 17, 1979Assignee: The United States of America as represented by the Department of Health, Education and WelfareInventors: Ulrich Weiss, Kenner C. Rice
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Patent number: 4150032Abstract: Improved processes for preparing 2'-alkoxy-2,5-di-substituted-9-oxo-6,7-benzomorphans from benz[e]indolines and synthesis of the benz[e]indoline intermediates are described. A representative example involves synthesis of 9b-allyl-8-methoxy-3-methyl-5,9b-dihydrobenz[e]indoline and bromination thereof to 9b-allyl-4-bromo-8-methoxy-2,4,5,9b-tetrahydro-1H-benz[e]indole methylbromide which is then hydrolyzed with a weak base such as ammonium bicarbonate to provide 5-allyl-2'-methoxy-2-methyl-9-oxo-6,7-benzomorphan.Type: GrantFiled: January 18, 1978Date of Patent: April 17, 1979Assignee: Bristol-Myers CompanyInventor: Gerry Kavadias
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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: 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: 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