Two Rings Only In Acid Moiety Patents (Class 560/118)
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Patent number: 4433182Abstract: 2,2'-Bridged[1,1'-biphenyl]-3-ylmethyl cyclopropanecarboxylates and insecticidal compositions containing these esters are useful for the control of a broad range of insects and acarids.Type: GrantFiled: December 17, 1981Date of Patent: February 21, 1984Assignee: FMC CorporationInventor: Ernest L. Plummer
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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: 4431668Abstract: Cyclopropane carboxylic acid ester derivatives and optical and geometrical isomers thereof expressed by the general formula: ##STR1## wherein R.sub.1 represents hydrogen atom or methyl group, R.sub.2 represents alkyl group, alkenyl group, haloalkyl group, haloalkenyl group having 1-6 carbon atoms and a group selected from the groups of the general formulae (II), (III) and (IV): ##STR2## in which n is an integer of 2-5, R.sub.4 represents methyl group, chlorine atom or methoxy group, and R.sub.3 represents a group selected from the groups of the general formulae (V), (VI), (VII), (VIII), (IX) and (X): ##STR3## in which X represents oxygen atom or vinylene group, R.sub.5 represents allyl group, propargyl group, benzyl group, phenoxy group or 2,2-dichlorovinyloxy group, R.sub.6 represents hydrogen atom, methyl group or halogen atom, R.sub.7 represents hydrogen atom, cyano group, ethynyl group or trifluoromethyl group and m is an integer of 1-2, R.sub.Type: GrantFiled: November 14, 1978Date of Patent: February 14, 1984Assignee: Dainippon Jochugiku Kabushiki KaishaInventors: Yoshio Katsuda, Yoshihiro Minamite
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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: 4424374Abstract: Compounds of the general formula: ##STR1## wherein R.sup.1 represents a straight- or branched-chain alkyl group containing from 1 to 6 carbon atoms or a phenoxy or benzyl group, and pharmaceutically acceptable salts and esters thereof, possess pharmacological properties of use in the fields of mammalian reproduction and cardiovascular disease.Type: GrantFiled: March 13, 1981Date of Patent: January 3, 1984Assignee: May & Baker LimitedInventors: Michael P. L. Caton, Keith A. J. Stuttle
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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: 4422870Abstract: 2-Aryl-1, 3-cyclohexanedione enol ester compounds exhibit outstanding miticidal,mite ovicidal and herbicidal activity.Type: GrantFiled: March 28, 1977Date of Patent: December 27, 1983Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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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: 4406829Abstract: Novel esters of all possible isomers and mixtures thereof of compounds of the formula ##STR1## wherein n is a number of 2,3 or 4 and R is selected from the group consisting of (a) alkyl of 1 to 12 carbon atoms optionally substituted with a member of the group consisting of cycloalkyl of 3 to 6 carbon atoms and a hydrocarbon chain of 2 to 8 carbon atoms optionally interrupted by an oxygen atom or a ketone group, (b) alkenyl and alkynyl of 3 to 8 carbon atoms, (c) cycloalkyl of 3 to 12 carbon atoms optionally containing at least one double bond and optionally substituted with at least one alkyl of 1 to 5 carbon atoms and (d) aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and --CF.sub.3 having perfume and insecticidal properties.Type: GrantFiled: November 5, 1981Date of Patent: September 27, 1983Assignee: Roussel UclafInventors: Jacques Martel, Jean Buendia, Francois Nezot
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Patent number: 4402973Abstract: [1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.Type: GrantFiled: May 21, 1981Date of Patent: September 6, 1983Assignee: FMC CorporationInventor: Ernest L. Plummer
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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: 4400061Abstract: Novel liquid crystal ester compounds exhibiting a low or negative dielectric anisotropy have a structural formula: ##STR1## where R.sub.1 is an alkyl group, R.sub.2 is an alkyl or alkoxy group, ##STR2## is a 1,4-disubstituted bicyclo(2,2,2) octane ring and ##STR3## is a 1,4-disubstituted ring selected from the following: (i) a 1,4-disubstituted bicyclo(2,2,2) octane ring;(ii) a trans-1,4-disubstituted cyclohexane ring;(iii) a laterally substituted benzene ring ##STR4## where of the two groups Y and Z one is a halogen or a cyano group and the other is hydrogen or a halogen or a cyano group such that Y is the same as Z.These esters may be used in a number of known applications including liquid crystal materials for multiplexed twisted nematic devices.The esters may be made by preparative methods involving known steps.Type: GrantFiled: January 30, 1981Date of Patent: August 23, 1983Assignee: Her Majesty's Government of the UK.Inventors: Neil Carr, George W. Gray, Stephen M. Kelly
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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: 4368135Abstract: Anisotropic compounds with negative or positive DCA and .DELTA.n.ltoreq.0.2 have the formula (1) ##STR1## in which R.sup.1 and R.sup.2 l are independently hydrogen, alkyl, alkoxy having 1 to 12 carbon atoms respectively, or one of R.sup.1 and R.sup.2 can represent cyclical fragment of formulae (1a) or (1b); ##STR2## the bridges Z.sup.1, Z.sup.2 and Z.sup.3 are identical or different and means covalent bonds or carboxyl or oxycarbonyl groups; R.sup.3 is hydrogen, alkyl or alkoxy group having 1 to 12 carbon atoms, respectively; X.sup.1 and X.sup.4 are independently hydrogen, halogen, nitrile or nitro, wherein at least one of X.sup.1 and X.sup.4 is not hydrogen when R.sup.2 represents a cyclical fragment of formula (1a) or (1b) and Z.sup.2 is a carboxyl group or Z.sup.3 is an oxycarbonyl group, respectively. Liquid crystal compositions are also disclosed.Type: GrantFiled: June 30, 1980Date of Patent: January 11, 1983Assignee: BBC, Brown, Boveri & Company, Ltd.Inventor: Maged A. Osman
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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: 4363817Abstract: Disclosed are C-9 enol acylate analogs of E.sub.1 and E.sub.2 prostaglandins which are variously useful as bronchodilators, gastric anti-secretory agents and cyto-protective agents.Type: GrantFiled: August 27, 1981Date of Patent: December 14, 1982Assignee: Miles Laboratories, Inc.Inventor: William G. Biddlecom
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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: 4356187Abstract: Novel esters of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN, R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, halogen, alkenyl of 2 to 3 carbon atoms and alkyl of 1 to 3 carbon atoms, Y' is selected from the group consisting of ##STR2## R.sub.4 ' and R.sub.5 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, fluorine, bromine, chlorine and R.sub.4 ' and R.sub.Type: GrantFiled: April 17, 1980Date of Patent: October 26, 1982Assignee: Roussel UclafInventors: Jacques Martel, Jean Tessier, Andre Teche
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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: 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: 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: 4340498Abstract: New halogenated ester derivatives and liquid crystal compositions containing the same are provided. The derivatives are expressed by the general formula ##STR1## wherein X is ##STR2## R is 1-15C alkyl group or alkoxy group; and Y is carboxyl group. The derivatives are useful as component(s) of liquid crystal compositions which have higher mesomorphic temperature ranges, nevertheless have lower viscosities; and also have lower absolute values of dielectric anisotropy, nevertheless can be driven at lower voltages.Type: GrantFiled: January 23, 1981Date of Patent: July 20, 1982Assignee: Chisso CorporationInventor: Shigeru Sugimori
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Patent number: 4336398Abstract: The yield of compounds having the general formula: ##EQU1## wherein R represents ##STR1## in the process comprising reacting a substituted hydroxycyclohexanecarboxylic acid with an aminoisopropyl chloride, is highly improved by heating the reaction mixture to 160.degree. to 240.degree. C. for at least 3 hours, and distilling under reduced pressure the resulting product. Thus the content of the undesired isomer is reduced to less than 1-1.5%.Type: GrantFiled: November 23, 1979Date of Patent: June 22, 1982Assignee: Laboratorio Guidotti & C. S.p.A.Inventor: Giorgio Sagramora
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Patent number: 4332815Abstract: 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 1, 1980Date of Patent: June 1, 1982Assignee: FMC CorporationInventor: John F. Engel
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Patent number: 4330482Abstract: In the process for the production of a halogenoalkene of the formula ##STR1## in which R.sup.1 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aralkyl, aralkenyl or aryl radical or an optionally substituted heterocyclic radical,R.sup.2 represents a halogen atom, a cyano group, an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkenyl, aryl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl or aminocarbonyl radical or an optionally substituted heterocyclic radical, andX is a halogen atom,in which an .alpha.-hydroxy-phosphonic acid ester of the formula ##STR2## in which R.sup.3 each independently is an alkyl or phenyl radical, or the two radicals R.sup.3 together are an alkanediyl (alkylene) radical,is reacted with a phosphorus-containing olefinating agent of the formula ##STR3## in which Z.sup.1 is the phosphorus-containing radical ##STR4## R.sup.4 and R.sup.5 each independently is an alkyl, phenyl, alkoxy or phenoxy radical or together are an alkanedioxy radical, andR.Type: GrantFiled: December 18, 1980Date of Patent: May 18, 1982Assignee: Bayer AktiengesellschaftInventor: Hellmut Hoffmann
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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: 4317834Abstract: Fluorine-substituted spirocarboxylic acid benzyl esters of the formula ##STR1## in which R.sup.1 represents hydrogen, cyano or alkyl, alkenyl or alkynyl, with in each case up to 4 carbon atoms,R.sup.2 represents a phenyl radical which is substituted by halogen and/or by optionally halogen-substituted phenoxy, with the proviso that the radical R.sup.2 contains in total at least one fluorine substituent, andR.sup.3, R.sup.4, R.sup.5 and R.sup.6 each represent hydrogen, halogen or alkyl, orR.sup.3 and R.sup.4, taken together, and/or R.sup.5 and R.sup.6, taken together, represent alkanediyl (alkylene) or a fused-on benzo radical,and the C atoms of the 5-member spirocyclic ring are linked to one another either by double bonds or by single bonds, which possess arthropodicidal properties.Type: GrantFiled: November 3, 1980Date of Patent: March 2, 1982Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Bernhard Homeyer, Wolfgang Behrenz, Wilhelm Stendel
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Patent number: 4313005Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.Type: GrantFiled: April 3, 1980Date of Patent: January 26, 1982Assignee: Air Products and Chemicals, Inc.Inventors: Michael E. Ford, Randall J. Daughenbaugh
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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: 4305885Abstract: A perfluoroalkane-sulphinic acid of the formula R.sub.F --SO.sub.2 H is reacted with a diene at -20.degree. to +20.degree. C. to form the new intermediate ##STR1## in which R.sup.3 -R.sup.8 are hydrogen or various organic radicals or double bonds, and that is reacted with a .beta.,.beta.-dimethyl-acrylic acid derivative of the formula ##STR2## in the presence of a base at a temperature between about -20.degree. and +30.degree. C. to produce a cyclopropane carboxylic acid derivative of the formula ##STR3## in which Z is alkoxycarbonyl or cyano and R.sup.1 and R.sup.2 are hydrogen or various organic radicals. The products are known intermediates for insecticides.Type: GrantFiled: June 27, 1980Date of Patent: December 15, 1981Assignee: Bayer AktiengesellschaftInventors: Michael Hanack, Theodor Stoll
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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: 4291057Abstract: Novel esters of halo-4-alkenoic acid compounds having pesticidal activity and methods of their preparation.Type: GrantFiled: July 2, 1979Date of Patent: September 22, 1981Assignee: Union Carbide CorporationInventor: Thomas N. Wheeler
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Patent number: 4289896Abstract: Phosphonic acids are suitable catalysts for the transesterification of alkyl esters of carboxylic acids with aliphatic or cycloaliphatic diols containing more than 3 carbon atoms.Type: GrantFiled: September 17, 1979Date of Patent: September 15, 1981Assignee: Ciba-Geigy CorporationInventor: Lothar Buxbaum
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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: 4283414Abstract: The invention concerns novel pesticidal esters of the pyrethrin or pyrethroid type in which the methylene group bonded to the ester carbonyl and/or ester oxygen bears a fluorine substituent. The compounds of the invention are active against insect pests including flies, moths, aphids and beetles and acarina pests including ticks.Type: GrantFiled: June 8, 1979Date of Patent: August 11, 1981Assignee: ICI Australia LimitedInventors: Donald W. G. Harney, Peter G. Lehman, Joseph C. Rundle
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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: 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: 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: 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: 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: 4271186Abstract: The invention relates to certain new stilbene derivatives of the general formula ##STR1## in which R, R.sup.1 and R.sup.2 have the below mentioned meaning, to a process for their preparation and to their use as arthropodicides, especially as insecticides and acaricides.Type: GrantFiled: June 29, 1979Date of Patent: June 2, 1981Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Rainer Fuchs, Ingeborg Hammann, Wilhelm Stendel
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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.