Two Rings Only Patents (Class 562/500)
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Patent number: 4431669Abstract: There is disclosed certain cyclopropyl substituted polyenes useful for treating dermatoses such as acne, psoriasis and epithelial cancers.Type: GrantFiled: December 17, 1982Date of Patent: February 14, 1984Assignee: Schering CorporationInventor: John J. Wright
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Patent number: 4429148Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: September 25, 1981Date of Patent: January 31, 1984Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei Lai Chen
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Patent number: 4425359Abstract: Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-16(S,R)-fluoro-PGF.sub.2.alpha.. The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.Type: GrantFiled: August 14, 1981Date of Patent: January 10, 1984Assignee: Farmitalia Carlo ErbaInventors: Renato Pellegata, Carmelo Gandolfi
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Patent number: 4423066Abstract: A pentafluorobenzyl 2,2-dimethyl-3-vinylcyclopropane carboxylate of the formula ##STR1## in which R is hydrogen or halogen, andR.sup.1 is optionally substituted phenyl, orR and R.sup.1 together constitute an alkylene chain with at least two carbon atoms,which possess arthropodicidal properties.Type: GrantFiled: February 21, 1979Date of Patent: December 27, 1983Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Klaus Naumann, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer, Wilhelm Stendel
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Patent number: 4415756Abstract: New bicyclo[2.2.2]oct-5-en-2-ones of the formulae Ia and Ib in the form of pure enantiomers and processes for preparing them are described. The compounds are used for the preparation of pure enantiomers of the formula V by sensitized photoreaction or of compounds of the formula VI by unsensitized photoreaction.Type: GrantFiled: December 2, 1981Date of Patent: November 15, 1983Assignee: Studiengesellschaft Kohle mbHInventors: Martin Demuth, Kurt Schaffner
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Patent number: 4409398Abstract: (1R,cis)-Oxyimino-substituted cyclopropanecarboxylic acids are prepared via a (1R,4R,5S)-4-acetoxy-6,6-dimethyl-2-oxo-3-oxabicyclo [3.1.0]hexane intermediate.Type: GrantFiled: August 13, 1981Date of Patent: October 11, 1983Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4401601Abstract: A process for the preparation of tetrasubstituted cyclopropane compounds of the formula ##STR1## wherein Y is selected from the group consisting of --CN and --COOR, R is selected from the group consisting of hydrogen and alkyl of 1 to 6 carbon atoms and R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are individually selected from alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 or R.sub.3 and R.sub.4 together with the carbon atoms to which they are attached form a carbon homocycle of 3 to 6 carbon atoms with the 2 substituents not forming the ring being alkyl of 1 to 4 carbon atoms or R.sub.1 and R.sub.2 on the one hand and R.sub.3 and R.sub.4 on the other together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms which are useful intermediates for the preparation of insecticidal esters and novel intermediates.Type: GrantFiled: March 23, 1981Date of Patent: August 30, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
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Patent number: 4389413Abstract: The 9,11-methano-13-aza-11a-carbathrombanoic acid analogues of the general formula: ##STR1## [wherein A represents ##STR2## (in which m is an integer of 1 to 6, the double bond between the carbon atoms in positions 5 and 6 in (iv) is in cis or trans-configuration or a mixture thereof and the phenylene group in (iv) represents o-, m- or p-phenylene), R.sup.1 represents a hydrogen atom or a straight- or branched-chain alkyl group of 1 to 12 carbon atoms, two R.sup.2 both represent hydrogen atoms or methyl groups, R.sup.3 represents a hydrogen atom or a hydroxy group, R.sup.4 represents a single bond or a straight- or branched-chain alkylene group of 1 to 5 carbon atoms, R.sup.Type: GrantFiled: July 22, 1981Date of Patent: June 21, 1983Inventors: Nobuyuki Hamanaka, Shinsuke Hashimoto, Masaki Hayashi
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Patent number: 4386103Abstract: Dichloroamino acid derivatives other than .alpha.-dichloroamino acids are prepared from chlorination of corresponding amino acids, and are found to be potent germicidal and fungicidal agents.Type: GrantFiled: January 30, 1981Date of Patent: May 31, 1983Assignee: Merck & Co., Inc.Inventors: Stefano A. Pogany, Takeru Higuchi
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Patent number: 4375557Abstract: Novel compounds of the formula I ##STR1## in which each of Y.sup.1 and Y.sup.2 independently represents a fluorine, chlorine or bromine atom and each of R.sup.1 and R.sup.2 independently represents a hydrogen atom or an alkyl group having up to 10 carbon atoms, or R.sup.1 and R.sup.2 together represent an alkylene group having from 2 to 5 carbon atoms, may be converted by the action of base into the corresponding dihalovinylcyclopropane carboxylic acids.Type: GrantFiled: June 7, 1982Date of Patent: March 1, 1983Assignee: Shell Oil CompanyInventor: Petrus A. Kramer
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Patent number: 4370488Abstract: The invention includes novel alkali metal complex compounds (and processes for their preparation) which are useful, inter alia for the hydrogenation of alkali metals at room temperature or below room temperature to form hydrides or nitrides.Type: GrantFiled: June 18, 1981Date of Patent: January 25, 1983Assignee: Studiengesellschaft Kohle mbHInventor: Borislav Bogdanovic
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Patent number: 4365085Abstract: The present invention relates to novel bicyclic compounds useful as photographic silver halide developing agents, to the preparation of these compounds and to photographic products, processes and compositions employing the same. The subject compounds may be represented by the formula ##STR1## wherein R.sub.1 and R.sub.2, the same or different, each represents hydrogen, a hydrocarbon moiety, preferably an alkyl group, --COOH or --COOR.sup.1 wherein R.sup.1 is an alkyl group; R.sub.3 and R.sub.4, the same or different, each represent hydrogen or an alkyl group, R.sub.5 represents hydrogen or --COR.sup.2 wherein R.sup.2 is an alkyl group; R.sub.6 represents hydrogen when R.sub.5 is hydrogen and represents hydrogen or --OCOR.sup.3 wherein R.sup.3 is an alkyl group the same as R.sup.2 when R.sub.5 represents --COR.sup.2 ; X represents --OH, --NH.sub.2 or --NHCOR.sup.4 wherein R.sup.4 represents an alkyl group the same as R.sup.2 ; Y represents --OH or --OCOR.sup.5 wherein R.sup.Type: GrantFiled: February 5, 1979Date of Patent: December 21, 1982Assignee: Polaroid CorporationInventors: James R. Bartels-Keith, Eva R. Karger
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Patent number: 4363926Abstract: A bissilylated 1-hydroxycyclopropanecarboxylic acid of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently is a hydrogen atom or an alkyl radical, and additionally R.sup.2 and R.sup.3 can together form a 3- to 5-membered carbon bridge, andR.sup.5, R.sup.6 and R.sup.7 each independently is an alkyl radical, is produced by oxidizing with oxygen a cyclobutene-1,2-diol-bis-trialkyl-silyl ether of the formula ##STR2## The products, without isolation, may directly be hydrolyzed to remove the silyl radicals and form known intermediates for further reaction.Type: GrantFiled: September 18, 1981Date of Patent: December 14, 1982Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Hans-Joachim Knops, Uwe Priesnitz
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Patent number: 4361577Abstract: .omega.-Nor-cycloalkyl-13,14-dehydro-prostaglandin compounds, specifically 5c-9-oxo-11.alpha.,15S-dihydroxy-20,19,18-tirnor-17-cyclohexyl-prost-5-en- 13-ynoic acid, the esters and salts thereof, having antiulcer and luteolytic activity, are disclosed.Type: GrantFiled: February 2, 1979Date of Patent: November 30, 1982Assignee: Carlo Erba - S.p.A.Inventors: Carmelo Gandolfi, Renato Pellegata, Roberto Ceserani, Maria M. Usardi
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Patent number: 4351846Abstract: Prostaglandin analogues of the formula: ##STR1## [wherein R.sup.1 represents hydrogen or alkyl of 1 to 12 carbon atoms, R.sup.2 represents a single bond or alkylene of from 1 to 5 carbon atoms, R.sup.3 represents hydrogen, alkyl or alkoxy of 1 to 8 carbon atoms, cycloalkyl or cycloalkyloxy of 4 to 7 carbon atoms unsubstituted or substituted by alkyl of 1 to 8 carbon atoms, or phenyl or phenoxy unsubstituted or substituted by halogen, trifluoromethyl or alkyl of 1 to 4 carbon atoms, one of R.sup.4 and R.sup.5 represents hydrogen and the other represents hydroxy or R.sup.4 and R.sup.5 together represent oxo, R.sup.6 represents hydrogen or a hydroxy-protecting group which may be removed under acidic conditions, the double bond between the carbon atoms in positions 13 and 14 is trans, the wavy line attached to the carbon atom in position 15 represents .alpha.- or .beta.- configuration or a mixture thereof and, when one of R.sup.4 and R.sup.Type: GrantFiled: May 8, 1981Date of Patent: September 28, 1982Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Kimiichiro Matsumoto, Hajimu Miyake, Hisashi Suga
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Patent number: 4351949Abstract: New organopalladium reactions involving the addition of pi-allylpalladium compounds to strained bicyclic alkenes, and subsequent chain extension reactions employing the chemistry of organopalladium compounds are disclosed. By these techniques a large number of bicyclic prostaglandin analogs are prepared, which are useful as inhibitors of arachidonic acid induced platelet aggregation, and are specific inhibitors of thromboxane synthetase.Type: GrantFiled: February 5, 1981Date of Patent: September 28, 1982Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4349690Abstract: The present invention provides novel 9-deoxy-9-methylene-6-keto-PGE derivatives which are useful for platelet aggregation inhibition and gastric cyctoprotection.Type: GrantFiled: April 23, 1981Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Gordon L. Bundy
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Patent number: 4347379Abstract: Numerous alpha-carboxylic acids are prepared in a liquid medium by the reaction of an organic compound having at least one reactive hydroxyl or thiol group, with a monoketone, and a haloform, in the presence of a phase transfer catalyst and an alkali metal hydroxide. The term "alpha-alkoxycarboxylic acids" includes alpha-phenoxycarboxylic acids, alpha-thioalkoxycarboxylic acids and alpha-thiophenoxycarboxylic acids. Specific substituents on the beta carbon atom of an alpha-alkoxycarboxylic (or "2-alkoxycarboxylic") acid reaction product formed in this novel synthesis, are introduced by appropriate choice of the ketone reactant; alkoxy and phenoxy substituents on the alpha carbon atom of a 2-alkoxycarboxylic acid are introduced by appropriate choice of the organic compound having a hydroxyl or thiol group. De-alkoxylation of the 2-alkoxycarboxylic acid yields alpha-beta monoolefinically unsaturated carboxylic acids which are necessarily alpha substituted, and may also be beta-substituted.Type: GrantFiled: March 10, 1980Date of Patent: August 31, 1982Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4334091Abstract: This invention relates to new compositions particularly suited for producing insecticidal intermediates.Type: GrantFiled: August 14, 1978Date of Patent: June 8, 1982Assignee: Air Products and Chemicals, Inc.Inventor: Robert J. Tedeschi
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Patent number: 4324902Abstract: 7-[5-oxo-3-hydroxy-2-(3-substituted)-3-hydroxypropyl)-1-cyclopentene]-hepta noic acids having the following general formula ##STR1## wherein X is oxygen or hydroxyl, R.sub.1 and R.sub.3 are independently hydrogen or methyl, and R.sub.2 is --(CH.sub.2)n-Y where n is an integer from 0 through 4 inclusive, and Y is phenyl, or a cycloalkyl group having 4 to 6 carbon atoms. Said acids as well as certain derivatives thereof are useful as nasal decongestants, inhibitors of gastric secretion, inhibitors of platelet aggregation, blood additives, smooth muscle stimulators, hypotensive agents, labor inducers, and in controlling ovulation.Type: GrantFiled: April 16, 1981Date of Patent: April 13, 1982Assignee: G. D. Searle & Co.Inventors: Masateru Miyano, Clifford R. Dorn
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Patent number: 4320143Abstract: Fluoro-prostaglandin compounds are disclosed, such as, for instance, 18,19,20-trinor-17-cyclohexyl-13-14-dehydro-16(S,R)-fluoro-PGF.sub.2.alpha ..The fluoro-prostaglandins of the present invention have the same therapeutical uses as natural prostaglandins, but have the advantage of being resistant to the enzyme 15-prostaglandin dehydrogenase, and also exhibit a more selective therapeutical action. Certain of the compounds of the present invention exhibit very favorable luteolytic and antiulcer activity.Type: GrantFiled: February 2, 1979Date of Patent: March 16, 1982Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Renato Pellegata, Carmelo Gandolfi
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Patent number: 4312994Abstract: .alpha. Diene 16-hydroxy prostanoic acid derivatives displaying valuable pharmacological properties, e.g., gastric antisecretory, are described herein.Type: GrantFiled: March 25, 1981Date of Patent: January 26, 1982Assignee: G. D. Searle & Co.Inventor: Paul W. Collins
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Patent number: 4308396Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an --OH group.Type: GrantFiled: March 12, 1979Date of Patent: December 29, 1981Assignee: Research CorporationInventors: Kyriacos C. Nicolaou, Ronald L. Magolda
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Patent number: 4299967Abstract: There is described a new process for the preparation of optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids substituted in the 3 position, and derivatives thereof. A racemate of certain cyclobutanones is reacted with a sulfurous acid salt of an optically active base to obtain a mixture of diastereomeric 4-2-(2',2',2'-trihalogenoethyl)-cyclobutane-1-sulfonic acid salts; this mixture is then separated into the pure diastereomeric sulfonic acid salts. Either the pure diastereomeric sulfonic acid salts are converted directly to the desired optically active products, or the optically active cyclobutanones obtained from the pure diastereomeric sulfonic acids salts by decomposition is converted, in the presence of a base to the desired product. Optionally, the product, optically active 2-(2',2'-dihalogenovinyl)-cyclopropane-1-carboxylic acids can be converted to their 1',2'-dibromo derivatives.Type: GrantFiled: December 17, 1979Date of Patent: November 10, 1981Assignee: Ciba-Geigy CorporationInventors: John G. Dingwall, Hans Greuter, Pierre Martin, Peter Ackermann, Laurenz Gsell
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Patent number: 4297366Abstract: 2,2-Dimethyl-3-(2-fluoroalkyl-2-oxy-vinyl)-cyclopropane-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is fluoroalkyl,R.sup.2 is an optionally substituted alkyl, cycloalkyl, aralkyl or aryl radical, andR.sup.3 is a radical customary in the alcohol component of pyrethroidswhich possess arthropodicidal properties. New intermediates therefor are also shown.Type: GrantFiled: April 23, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
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Patent number: 4296121Abstract: What is disclosed are compounds of the formula ##STR1## which are structurally related to natural prostaglandins and a process for their manufacture. The compounds have valuable pharamacological properties and, therefore, they can be used as medicaments.Type: GrantFiled: August 2, 1979Date of Patent: October 20, 1981Assignee: Hoechst AktiengesellschaftInventors: Wilhelm Bartmann, Gerhard Beck, Ulrich Lerch, Elmar Konz
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Patent number: 4284646Abstract: Prostanoic acid derivatives of the formula ##STR1## wherein R.sub.1 is an acid, ester, amide or hydroxyalkylene group; R.sub.2 and R.sub.3 are H or alkyl; R.sub.4 and R.sub.5 are both CH.sub.3 or one is Cl and the other is CH.sub.3 ; A is CH.sub.2 CH.sub.2 or --CH.dbd.CH; B is CH.sub.2 CH.sub.2, trans-CH.dbd.CH, --C.tbd.C--or ##STR2## W is free or functionally modified hydroxyalkylene or carbonyl; Z is free or functionally modified hydroxymethylene or carbonyl; X Y is either ##STR3## or, when Z is free or functionally modified hydroxymethylene, ##STR4## or, when Z is free or functionally modified carbonyl, --CH.dbd.CH--, R.sub.12 being H, CH.sub.3, CN or free or functionally modified hydroxy; and physiologically acceptable salts thereof when R.sub.1 is an acid group, possess pharmacological activity, including abortion triggering activity.Type: GrantFiled: August 24, 1979Date of Patent: August 18, 1981Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4283550Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: August 11, 1981Assignee: American CyanamidInventor: Middleton B. Floyd, Jr.
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Patent number: 4282249Abstract: (1R,cis)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein X is chlorine, bromine or OR in whichR is hydrogen, a salt-forming cation, an alkyl group or residues of certain other alcohols; andR.sup.1 is hydrogen, or certain optionally halogenated hydrocarbyl groups,are highly active pesticides or intermediates therefore.Type: GrantFiled: February 21, 1979Date of Patent: August 4, 1981Assignee: Shell Oil CompanyInventors: Steven A. Roman, Samuel B. Soloway
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Patent number: 4281153Abstract: This disclosure describes novel 15-deoxy-16-hydroxy-16-substituted prostanoic acids and congeners thereof having utility as bronchodilators as hypotensive agents, and as agents for the control of excessive gastric secretion.Type: GrantFiled: January 17, 1980Date of Patent: July 28, 1981Assignee: American CyanamidInventors: Middleton B. Floyd, Jr., Martin J. Weiss, Charles V. Grudzinskas, Sow-Mei Lai Chen
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Patent number: 4281183Abstract: New cyclopropane compounds have the formula ##STR1## wherein X is chlorine, bromine or OR in whichR is hydrogen, a salt-forming cation, an alkyl group or residues of certain other alcohols; andW is thienyl, furfuryl, --CO.sub.2 R.sup.1, --CONR.sup.1 R.sup.2, --SO.sub.3 R.sup.1, --SO.sub.2 NR.sup.1 R.sup.2, --PO.sub.3 H, --PO(OR.sup.1).sub.2, --NO.sub.2, --CN, --OR.sup.1, --SR.sup.1, --S(O)R.sup.1, --S(O).sub.2 R.sup.1, --NR.sup.1 R.sup.2, --N(O)R.sup.1 R.sup.2, or --(OCH.sub.2 CH.sub.2).sub.q --OR.sup.1 in which R.sup.1 and R.sup.2 are H or certain optionally-substituted hydrocarbyl groups, q is 1-4, p is 1 or 2 and when p is 1 then W.sup.1 is alkyl or when p is 2 then W.sup.1 is H. The compounds are pesticides or intermediates therefore.Type: GrantFiled: June 5, 1980Date of Patent: July 28, 1981Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4278688Abstract: Prostaglandin E.sub.1 analogues of the general formula: ##STR1## [wherein Y represents ethylene or trans-virylene, Z represents ethylene or trans-vinylene, R.sup.1 represents a hydrogen atom, an alkyl group containing 1 to 12 carbon atoms, an aralkyl group containing from 7 to 12 carbon atoms, a cycloalkyl group containing from 4 to 7 carbon atoms and unsubstituted or substituted by at least one alkyl group containing from 1 to 6 carbon atoms, a phenyl group unsubstituted or substituted by at least one chlorine atom, trifluoromethyl group, alkyl group containing from 1 to 4 carbon atoms or phenyl group, a--C.sub.m H.sub.2m COOR.sup.5 group (wherein m represents an integer of from 1 to 12 and R.sup.5 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms ), a --C.sub.n H.sub.2n OR.sup.6 group (wherein R.sup.6 represents a hydrogen atom or an alkyl group containing from 1 to 4 carbon atoms and n represents an integer of from 2 to 12), or a ##STR2## group (wherein R.sup.7 and R.sup.Type: GrantFiled: January 16, 1980Date of Patent: July 14, 1981Assignee: Ono Pharmaceutical Co.Inventors: Masaki Hayashi, Katsuichi Shimoji, Yoshinobu Arai
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Patent number: 4275224Abstract: Analogues of PGE.sub.1 having the structural formula, ##STR1## in which J is R-hydroxymethylene or S-hydroxymethylene; R.sub.1 is hydrogen; R.sub.2 is hydrogen or together with R.sub.4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R.sub.3 is hydrogen or methyl, or together with R.sub.4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R.sub.4 is bicycloalkyl or bicycloalkenyl moiety having the formula: ##STR2## such that a bicycloalkyl or bicycloalkenyl compound is formed, wherein m and n are integers having a value from 0 to 3, p is an integer having a value from 0 to 4 and q is an integer having a value of from 1 to 4 and wherein the double bond of such bicycloalkenyl is in the m, n, p, or q bridge; R.sub.4 is hydrogen or methyl or together with R.sub.2 or R.sub.Type: GrantFiled: December 26, 1978Date of Patent: June 23, 1981Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Warren D. Woessner, William G. Biddlecom
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Patent number: 4275075Abstract: The present invention relates to prostaglandin analogues of the general formula: ##STR1## [wherein A represents a grouping of the formula: ##STR2## X represents trans-vinylene or ethylene and Y represents cis-vinylene or ethylene, R represents a group of the formula --COOR.sup.4, in which R.sup.4 represents hydrogen or straight- or branched-chain alkyl of 1 to 12 carbon atoms, or a group of the formula --CH.sub.2 OR.sup.5, in which R.sup.5 represents hydrogen or alkylcarbonyl of 2 to 5 carbon atoms and R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, each represent hydrogen, straight- or branched-chain alkyl of 1 to 12 carbon atoms, or an aryl group unsubstituted or substituted by one, two or three substituents selected from alkyl, alkoxy, alkylthio, monoalkylamino and dialkylamino groups and halogen atoms, the alkyl groups or moieties of the said groups containing from 1 to 5 carbon atoms in a straight- or branched-chain, with the proviso that at least one of the symbols R.sup.1, R.sup.Type: GrantFiled: June 14, 1978Date of Patent: June 23, 1981Assignee: ONO Pharmaceutical Co. Ltd.Inventors: Masayasu Kurono, Hisao Nakai, Shigeru Sakuyama
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Patent number: 4273784Abstract: The present invention concerns prostaglandins having a cyclopropane ring in the 2,3 position.Type: GrantFiled: March 28, 1979Date of Patent: June 16, 1981Assignee: Sandoz Ltd.Inventor: Pietro Bollinger
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Patent number: 4267361Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: May 12, 1981Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4260806Abstract: Stable biologically active thromboxane A.sub.2 analogues having the formula: ##STR1## wherein R.sup.1 is OR.sup.3, where R.sup.3 represents hydrogen or a pharmaceutically acceptable cation or lower alkyl group; orR.sup.1 is NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are the same or different substituents selected from the group consisting of hydrogen and lower alkyl group; andR.sup.2 is hydrogen or an --OH group.The thromboxane analogues are potent thrombotic agents, useful in cardiovascular treatment.Type: GrantFiled: October 24, 1979Date of Patent: April 7, 1981Assignee: Research CorporationInventors: Kyriacos C. Nicolaou, Ronald L. Magolda, David A. Claremon
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Patent number: 4260805Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: April 7, 1981Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4259523Abstract: This invention provides new mono-deuterated prostaglandins having prolonged uterotonic activity.Type: GrantFiled: May 11, 1979Date of Patent: March 31, 1981Assignee: Sandoz Ltd.Inventors: Pietro Bollingen, Manfred Krieger
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Patent number: 4258207Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an acyl group or certain optionally halo-substituted hydrocarbyl groups, and X is --CH.sub.2 CH(OCH.sub.3).sub.2, --CH.sub.2 CHO, --CH.dbd.CHOR.sup.2 in which R.sup.2 is acyl, --CHO, --C(O)Cl, --C(O)Br or --C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: March 15, 1979Date of Patent: March 24, 1981Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4254278Abstract: This disclosure describes certain 11-hydroxy and 11-deoxy-1-ketocarboxylic acid prostanoic acids and derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents or intermediates.Type: GrantFiled: September 27, 1979Date of Patent: March 3, 1981Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4254277Abstract: (1R, Trans)-cyclopropane compounds, substantially free of other stereoisomers, and having the formula ##STR1## wherein X is chlorine, bromine or OR in whichR is hydrogen, a salt-forming cation, an alkyl group or residues of certain other alcohols; andR.sup.1 is certain optionally halogenated hydrocarbyl groups, are highly active pesticides or intermediates therefore.Type: GrantFiled: December 20, 1979Date of Patent: March 3, 1981Assignee: Shell Oil CompanyInventors: Steven A. Roman, Samuel B. Soloway
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Patent number: 4245121Abstract: 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: February 4, 1980Date of Patent: January 13, 1981Assignee: American Cyanamid CompanyInventors: Allan Wissner, Martin J. Weiss, Karel F. Bernady
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Patent number: 4243677Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.Type: GrantFiled: July 30, 1979Date of Patent: January 6, 1981Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4243678Abstract: Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl;R.sup.2 is --H or lower aliphatic hydrocarbyl;R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene;R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene;or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; andn is 3, 4 or 5;and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g.Type: GrantFiled: December 15, 1978Date of Patent: January 6, 1981Assignee: Byk Gulden Lomberg Chemische Fabrik GmbHInventor: Walter Krastinat
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Patent number: 4242278Abstract: A process for the preparation of 2-(2',2',2',-trihalogenoethyl)-4-halogenocyclobutan-1-ones of the formula ##STR1## in which one of the radicals R.sub.1 and R.sub.2 is methyl and the other is hydrogen or methyl, or R.sub.1 and R.sub.2 together are an alkylene group having 2 to 4 carbon atoms, and X and Y are each chlorine or bromine, comprising reacting a 2,4,4,4-tetrahalogenobutyric acid chloride in the presence of an organic base with an ethylene compound which is disubstituted in 1-position by the radicals R.sub.1 and R.sub.Type: GrantFiled: October 3, 1978Date of Patent: December 30, 1980Assignee: Ciba-Geigy CorporationInventors: Pierre Martin, Hans Greuter, Eginhard Steiner, Daniel Bellus
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Patent number: 4242521Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is a hydrocarbyl group, W is a chlorine or bromine atom or --OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the natural terpene, 3-carene.Type: GrantFiled: January 25, 1980Date of Patent: December 30, 1980Assignee: Shell Oil CompanyInventor: James E. Powell
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Patent number: 4236027Abstract: This disclosure describes certain 11-alkoxy-9-keto- (or hydroxy)-prostenoic acid derivatives useful as anti-microbial agents, hypotensive agents, anti-ulcer agents, or as intermediates.Type: GrantFiled: October 17, 1977Date of Patent: November 25, 1980Assignee: American Cyanamid CompanyInventors: Middleton B. Floyd, Jr., Martin J. Weiss
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Patent number: 4223155Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is an optionally halo-substituted hydrocarbyl group, and X is --C(O)Cl, --C(O)Br or C(O)OR in which R is H, a salt-forming cation, an alkyl group or the residue of a pyrethroid alcohol are new pesticides or intermediates therefore. The compounds are prepared using a multi-step synthesis starting from the neutral terpene, 3-carene.Type: GrantFiled: July 26, 1979Date of Patent: September 16, 1980Assignee: Shell Oil CompanyInventor: Steven A. Roman
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Patent number: 4220795Abstract: Novel C15 cyclobutyl analogs or derivatives of prostaglandins of the E-, A- and F-classes are useful modifiers of smooth muscle activity. The compounds have valuable pharmacological properties such as platelet antiaggregating agents, gastric antisecretory agents and brochodilating agents.Type: GrantFiled: August 14, 1978Date of Patent: September 2, 1980Assignee: Miles Laboratories, Inc.Inventors: Harold C. Kluender, Henry C. Arndt