Plural Rings In Substituent Q Patents (Class 564/171)
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Patent number: 4855086Abstract: The specification describes and claims methods of controlling acarine pests by application of a compound of Formula (I), methods of controlling arthropod pests by application of a compound of Formula (IA), compounds of Formula (IA) per se, pesticidal compositions comprising a compound of Formula (IA), and processes for preparing a compound of Formula (IA).Type: GrantFiled: October 11, 1983Date of Patent: August 8, 1989Assignee: Burroughs Wellcome Co.Inventors: Malcolm H. Black, Robert J. Blade
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Patent number: 4845264Abstract: A novel phenoxycarboxylic acid of formula (I) is disclosed. The compound is effective as herbicide for eradicating broad-leaved weeds. A combination of the phenoxycarboxylic acid and a N-phosphonomethylglycine or a glufosinate which is known as a herbicide is very effective for eradicating both broad-leaved weeds and narrow-leaved weeds.Type: GrantFiled: March 1, 1988Date of Patent: July 4, 1989Assignee: Teijin LimitedInventors: Shizuo Azuma, Toshiyuki Hiramatsu, Koji Nakagawa, Yataro Ichikawa
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Patent number: 4808750Abstract: Novel fluorophenoxyphenoxypropionates and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops. Preemergent and postemergent applications are contemplated.Type: GrantFiled: July 14, 1986Date of Patent: February 28, 1989Assignee: The Dow Chemical CompanyInventors: Richard B. Rogers, B. Clifford Gerwick, III
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Patent number: 4806570Abstract: Compounds of formula I ##STR1## in which R.sub.1 is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-7 cycloalkyl, cycloalkylalkyl or optionally substituted phenyl; R.sub.2 is H or C.sub.1-3 alkyl; R.sub.3 and/or R.sub.4 are H, formyl, C.sub.1-3 alkyl, C.sub.3-6 alkenyl, C.sub.3-6 alkynyl, C.sub.3-7 cycloalkyl or R.sub.3 and R.sub.4 together with the nitrogen atom form a heterocyclic ring system; R.sub.5 and/or R.sub.6 are H, halo, CF.sub.3, C.sub.1-3 alkyl, C.sub.1-3 alkoxy, C.sub.1-3 alkylthio or R.sub.5 and R.sub.6 together with the carbon atoms to which they are attached form a second benzene ring show therapeutic activity in the treatment of depression. Pharmaceutical compositions and processes for preparing compounds of formula I are disclosed.Type: GrantFiled: December 23, 1985Date of Patent: February 21, 1989Assignee: The Boots Company plcInventors: James E. Jeffery, Antonin Kozlik, Eric C. Wilmhurst
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Patent number: 4764619Abstract: An optically active compound having the formula: ##STR1## wherein each of Z and Z' is a single bond, --COO--, --OCO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 -- or --CH.sub.2 O--, R is an alkyl group having from 1 to 12 carbon atoms, an alkoxyl group having from 1 to 12 carbon atoms, a cyano group or a halogen atom, each of rings A and B is a 1,4-di-substituted phenylene group or a trans-1,4-di-substituted cyclohexylene group, n is 0 or 1, X is ##STR2## wherein * indicates an optical center, and R' is an alkyl group having from 2 to 12 carbon atoms or ##STR3## where R" is a hydrogen atom, an alkyl or alkoxy group having from 1 to 12 carbon atoms, provided that when X is ##STR4## R is the alkyl group or the alkoxy group.Type: GrantFiled: March 21, 1986Date of Patent: August 16, 1988Assignee: Asahi Glass Company Ltd.Inventors: Tomoki Gunjima, Ryutaro Takei, Eriko Aoyama
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Patent number: 4761501Abstract: This application discloses certain substituted phenylacetamides of the formula: ##STR1## in which the dotted line represents optional unsaturation, R.sub.1 is alkyl;R.sub.2 is alkyl;R.sub.4 is hydrogen or alkyl; R.sub.5 and R.sub.6, one of which may be hydrogen, are independently, hydroxyl, alkyl, alkoxy, aralkoxy, alkanoyloxy, alkylmercapto, N-protected amino, halo or trifluoromethyl;R.sub.7 is hydrogen or alkyl; andn is one of the integers 0, 1, 2, 3 or 4;which are useful in the production of antidepressant agents.Type: GrantFiled: May 22, 1985Date of Patent: August 2, 1988Assignee: American Home Products CorporationInventors: G. E. Morris Husbands, John P. Yardley, Eric A. Muth
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Patent number: 4760161Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit lipoxygenase, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: April 25, 1983Date of Patent: July 26, 1988Assignee: Merck & Co., Inc.Inventors: Philippe L. Durette, Timothy F. Gallagher
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Patent number: 4753934Abstract: Compounds of the formula ##STR1## wherein A, B, R.sub.1, X and Q are substituents of various types, and acid addition salts thereof. The compounds are useful as fungicides.Type: GrantFiled: September 29, 1986Date of Patent: June 28, 1988Assignee: Celamerck GmbH & Co. KGInventors: Josef Nickl, Helmut Pieper, Jurgen Curtze, Christo Drandarevski, Sigmund Lust
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Patent number: 4754052Abstract: A process of recycling nitrated by-products formed during the manufacture of the compound of the formula ##STR1## and salts thereof wherein J is ##STR2## and further wherein: R.sup.1 is fluorine, chlorine, bromine, or iodine or a trifluoromethyl group;R.sup.2 is a hydrogen atom, a fluorine, chlorine, bromine or iodine atom or a trifluoromethyl group;R.sup.3 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a trifluoromethyl group, a cyano group or a fluorine, chlorine, bromine or iodine group; X is ##STR3## R.sup.4 is R.sup.5 or an acyl radical of the formula ##STR4## wherein Alk is a C.sub.1-6 alkyl group; R.sup.5 is a hydrogen atom or a C.sub.1-6 alkyl group optionally substituted with either one or more halogen atoms or a phenyl group;B is a C.sub.1-10 alkyl, OR.sup.7 or SR.sup.7 ;y is 1 to 4;R.sup.6 is a hydrogen atom or a C.sub.1-2 alkyl group;R.sup.7 is hydrogen, or a C.sub.1-8 alkyl group, a C.sub.Type: GrantFiled: November 7, 1986Date of Patent: June 28, 1988Assignee: ICI Americas Inc.Inventors: William W. Brand, John F. Stephen
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Patent number: 4743703Abstract: The 4-fluoroalkyl-4'-nitrodiphenyl ethers comprise a class of compounds that are highly effective herbicides.Type: GrantFiled: September 19, 1983Date of Patent: May 10, 1988Assignee: Rohm and Haas CompanyInventor: Colin Swithenbank
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Patent number: 4725683Abstract: Novel intermediates useful in the preparation of fluorophenoxyphenoxypropionates and derivatives thereof which possess herbicidal activity selectively in the presence of broadleaf crops.Type: GrantFiled: August 12, 1985Date of Patent: February 16, 1988Assignee: The Dow Chemical CompanyInventors: Richard B. Rogers, B. Clifford Gerwick, III
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Patent number: 4713470Abstract: There is disclosed a process for the racemization of amino acids and derivatives thereof. The racemization process of the present invention uses an aromatic aldehyde-containing polymer made from the reaction of a hydroxy-aromatic aldehyde with a chloromethylated vinylbenzene polymer under reaction conditions to form an aromatic aldehyde-containing polymer wherein the aldehydic moiety is linked to the polymer through an ether linkage. There is also disclosed a process for the production of the racemization catalyst. Another embodiment of the invention comprises a process for the promotion of the racemization reaction wherein a tertiary amine-containing resin is used as a promoting agent.Type: GrantFiled: May 22, 1985Date of Patent: December 15, 1987Assignee: Stauffer Chemical CompanyInventor: Stanley B. Mirviss
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Patent number: 4683330Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: July 28, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4668814Abstract: A compound of the formula ##STR1## and intermediates useful in preparing same.Type: GrantFiled: January 11, 1985Date of Patent: May 26, 1987Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4661505Abstract: This invention provides novel alkane derivatives which are leukotriene antagonists, formulations of those derivatives, and a method of using those derivatives for the treatment of conditions characterized by an excessive release of leukotrienes.Type: GrantFiled: November 3, 1982Date of Patent: April 28, 1987Assignee: Eli Lilly and CompanyInventors: Winston S. Marshall, John P. Verge
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Patent number: 4652635Abstract: A method for converting ether groups such as alkyl or aryl ether groups including hydroquinone ether groups to hydroxyl groups and ester groups such as alkyl or aryl ester groups to carboxylic acid groups which comprises reacting a compound including at least one ether and/or ester group with a 2-halo-1,3,2-benzodioxaborole to form an intermediate and hydrolyzing the intermediate such as by quenching it into water to form the desired final product.Type: GrantFiled: June 15, 1984Date of Patent: March 24, 1987Assignee: Polaroid CorporationInventor: Patrick F. King
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Patent number: 4649212Abstract: The invention relates to novel phenoxyphenylamino acid derivatives of the formula I ##STR1## wherein X is hydrogen, chlorine, fluorine or bromine,R.sup.1 is hydrogen, nitroso, or C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkylcarbonyl or C.sub.2 -C.sub.4 alkenylcarbonyl, each of which is unsubstituted or substituted by one or more halogen atoms,Q is a straight chain or branched aliphatic radical of 1 to 5 carbon atoms ##STR2## in which A', E', G', L' and M' are hydrogen or C.sub.1 -C.sub.4 alkyl, or two adjacent substituents A', E', G', L' and M' together are also a bond between the two carbon atoms to which they are attached; A, E, G, L and M are hydrogen or one or two of A, E, G, L and M are also --OR.sup.2, --SR.sup.3, --COOR.sup.4, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl substituted by --OR.sup.5, --SR.sup.6 or --COOR.sup.7, where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are hydrogen or C.sub.1 -C.sub.4 alkyl; a, b, c and d are 0 or 1; or R.sup.Type: GrantFiled: April 4, 1985Date of Patent: March 10, 1987Assignee: Ciba-Geigy CorporationInventor: Dieter Durr
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Patent number: 4609758Abstract: This invention provides a group of hydroxycycloalkanephenoxyethylamine antidepressant derivatives of the following structural formula: ##STR1## in which R.sub.1 is hydrogen or alkyl of 1 to 6 carbon atoms;R.sub.2 is alkyl of 1 to 6 carbon atoms;R.sub.3 and R.sub.4 are independently hydrogen, hydroxyl, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkanoyloxy of 2 to 7 carbon atoms, halo or trifluoromethyl;R.sub.5 is hydrogen, alkyl of 1 to 6 carbon atoms or alkanoyl of 2 to 7 carbon atoms;and n is one of the integers 0, 1, 2 or 3;or a pharmaceutically acceptable salt thereof.Type: GrantFiled: May 9, 1985Date of Patent: September 2, 1986Assignee: American Home Products CorporationInventor: George E. M. Husbands
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Patent number: 4607119Abstract: A process for the preparation of certain cyano substituted esters and optical isomers thereof useful as insecticides by dehydration of the precursor carboxamido esters. Intermediates for the preparation of such compounds, e.g., racemic methyl 3-phenoxymandelate, methyl (S)-3-phenoxymandelate and methyl (R)-3-phenoxymandelate are also disclosed.Type: GrantFiled: December 26, 1984Date of Patent: August 19, 1986Assignee: Imperial Chemical Industries PLCInventor: Thomas Leigh
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Patent number: 4602097Abstract: Photoinitiators of the formulaG--O--(CH.sub.2 CH.sub.2 O).sub.n --CH.sub.2 --CH.sub.2 --O--Qwherein G is a photoinitiator moiety, R is hydrogen or lower alkyl, n has a value of at least 10, and Q is G or a lower alkyl are soluble in water and common organic solvents and are useful in polymerization systems employed in coatings used in screen printing.Type: GrantFiled: June 11, 1984Date of Patent: July 22, 1986Assignee: Ulano CorporationInventor: John R. Curtis
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Patent number: 4596680Abstract: A asymmetrical aryl ether of the formulaX--Ar--O--Ar'--Y,wherein Ar and Ar' are each a divalent aromatic radical, X and Y are electron attracting atoms or groups which differ from each other or have different positions on the corresponding aromatic radicals, is produced by heating together, in the presence of a basic catalyst, equimolecular amounts of two aryl carbonates of the formulas:X--Ar--O--CO--O--Ar--X,andY--Ar'--O--CO--O--Ar'--YType: GrantFiled: April 8, 1983Date of Patent: June 24, 1986Assignees: Institut Francais du Petrole, Centre National de la Recherche Scientifique (CNRS)Inventors: Philippe Jost, Pierre Le Perchec, Bernard Sillion
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Patent number: 4560786Abstract: .DELTA..sup.8,9 -Prostane derivatives of Formula I ##STR1## wherein R.sub.1 is CH.sub.2 OH or ##STR2## wherein R.sub.2 is hydrogen, alkyl, cycloalkyl, aryl, or a heterocyclic residue; or R.sub.1 is ##STR3## wherein R.sub.3 is an acid residue or R.sub.2 ; A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH;B is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH-- or --C.tbd.C--W is a free or functionally modified hydroxymethylene group or free or functionally modified ##STR4## wherein the OH--group can be in the .alpha.-- or .beta.-- position; D and E jointly are a direct bond orD is straight chain or branched alkylene or alkenylene of 1-10 carbon atoms which can optionally be substituted by fluorine atoms, and E is oxygen, sulfur, a direct bond, --C.tbd.C-- or --CR.sub.6 .dbd.CR.sub.7 --, wherein R.sub.6 and R.sub.7 differ from each other and each is hydrogen, chlorine or alkyl;R.sub.4 is free or functionally modified hydroxy andR.sub.Type: GrantFiled: June 24, 1982Date of Patent: December 24, 1985Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Norbert Schwarz, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Michael-Harold Town
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Patent number: 4550192Abstract: Novel fluorophenoxyphenoxypropionates and derivatives thereof possess herbicidal activity selectively in the presence of broadleaf crops. Preemergent and postemergent applications are contemplated.Type: GrantFiled: September 1, 1983Date of Patent: October 29, 1985Assignee: The Dow Chemical CompanyInventors: Richard B. Rogers, B. Clifford Gerwick, III
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Patent number: 4542237Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.Type: GrantFiled: June 7, 1983Date of Patent: September 17, 1985Assignee: Syntex Pharmaceuticals International LimitedInventor: George C. Schloemer
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Patent number: 4539414Abstract: Substantially pure compounds having the general formula ##STR1## wherein (1) ##STR2## R.sup.2 is .beta.-hydroxy and R.sup.3 and R.sup.4 together form an oxygen bridge, or (2) ##STR3## R.sup.2 and R.sup.3 together form an additional carbon-carbon bond, and R.sup.4 is hydroxy, are disclosed. These compounds exhibit antileukemic activity against P388 lymphocytic leukemia in CDF.sub.1 mice and inhibitory activity in vitro against cells derived from human epidermoid carcinoma of the nasopharynx(KB) cells.Type: GrantFiled: October 14, 1983Date of Patent: September 3, 1985Inventors: Ming L. King, Chin-Chih Chiang, Han-Chin Ling, Masahito Ochiai, Eiichi Fujita, Andrew T. McPhail
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Patent number: 4532343Abstract: Aromatic retinoic acid analogues of the formula ##STR1## where X is hydrogen or fluorine, Y is hydrogen, halogen of atomic number 9 or 17, hydroxy, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms and R is hydroxy, alkoxy, aroxy, or NR.sup.1 R.sup.2 where R.sup.1 is hydrogen, alkyl, or aryl and R.sup.2 is alkyl or aryl, with the proviso that when Y is hydrogen, X is fluorine. These retinoids are useful as chemopreventive agents for inhibiting tumor promotion in epithelial cells and for treating nonmalignant skin disorders.Type: GrantFiled: November 19, 1982Date of Patent: July 30, 1985Assignee: SRI InternationalInventors: Marcia I. Dawson, Peter D. Hobbs
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Patent number: 4529556Abstract: The invention bis((aryl)vinyl)benzenes wherein the aryl and benzene moieties may be substituted, and the vinyl carbon alpha to the central benzene ring may be further substituted with an aliphatic group.Type: GrantFiled: August 19, 1983Date of Patent: July 16, 1985Assignee: The Dow Chemical CompanyInventor: Kenneth J. Bruza
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Patent number: 4478836Abstract: The present invention concerns new derivatives of 1-aryl 2-aminomethyl cyclopropane carboxamides (Z) of general formula I: ##STR1## in which: R represents a hydrogen or halogen atom, a lower alkyl group, a lower alkoxy group, or a hydroxy. nitro or amino group;n represents the value 1 or 2;R.sub.1 and R.sub.2 represent a hydrogen atom, a lower alkyl group, an aryl or lower alkaryl group, possibly substituted, preferably in para position, by a halogen atom, preferably a chlorine atom;R.sub.1 and R.sub.2 may also form a heterocycle having 5 or 6 members with the adjacent nitrogen atom;R.sub.3 and R.sub.4 represent a hydrogen atom or a lower alkyl group;R.sub.3 and R.sub.Type: GrantFiled: June 22, 1982Date of Patent: October 23, 1984Assignee: Pierre Fabre S.A.Inventors: Gilbert Mouzin, Henri Cousse, Bernard Bonnaud, Michel Morre, Antoine Stenger
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Patent number: 4456768Abstract: Prostaglandin and prostacyclin compounds which are fluorine substituted in any one or more of the following positions 4,4; 7,7; 10,10; and 5.Type: GrantFiled: May 1, 1981Date of Patent: June 26, 1984Assignee: The University of ChicagoInventor: Josef Fried
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Patent number: 4448991Abstract: Cyclohexenes of the formula ##STR1## wherein R.sup.1 is hydroxy or lower alkoxy; n is 1 or 2; R.sup.2 is lower alkyl; and R.sup.3 is hydrogen, lower alkyl, lower alkenyl or lower cycloalkylmethyl,and their pharmaceutically acceptable acid addition salts are disclosed. The compounds of formula I have analgesic activity and are useful for the control of pains.Type: GrantFiled: March 24, 1982Date of Patent: May 15, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Hans Bruderer, Albert E. Fischli, Rudolf Pfister
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Patent number: 4444788Abstract: Compounds of the formula ##STR1## wherein the 9-chlorine atom can be in the .alpha.- or .beta.-position,R.sub.1 is OR.sub.2, or NHR.sub.3 wherein R.sub.3 is H or the acyl group ofa C.sub.1-15 hydrocarbon carboxylic or sulfonic acid;A is --CH.sub.2 --CH.sub.2 -- or cis--CH.dbd.CH--,B is --CH.sub.2 --CH.sub.2 --,trans--CH.dbd.CH--, or --C.tbd.C--, ##STR2## wherein the OH-group in each case can be in the .alpha.- or .beta.-position, and can be etherified or esterified by tetrahydropyranyl, tetrahydrofuranyl, .alpha.-ethoxyethyl, trimethylsilyl dimethyl, tert-butylsilyl, tribenzylsilyl, acetyl, propionyl, butyryl or benzoyl;D and E together represent a direct bond orD is a straight-chain or branched alkylene group of 1-10 carbon atoms, optionally substituted by fluorine, andE is oxygen or sulfur or a direct bond, andR.sub.4 is hydroxy or hydroxy etherified or esterified as defined for W above;R.sub.5 is a C.sub.1-10 hydrocarbon aliphatic group; a C.sub.Type: GrantFiled: June 10, 1982Date of Patent: April 24, 1984Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Ekkehard Schillinger
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Patent number: 4400394Abstract: Compounds of the formula: ##STR1## in which X.sub.1, X.sub.2 and X.sub.3, which are identical or different, each represent hydrogen, halogen, methyl, or methoxy, n represents an integer from 1 to 10, and R represents hydroxyl, OM, NH.sub.2, NH(CH.sub.2).sub.3 --COOH, --NH(CH.sub.2).sub.3 --COOM, (where M represents an alkali metal atom), NH(CH.sub.2).sub.3 --COOC.sub.2 H.sub.5, NH-cycloalkyl, NH-phenyl, NH-benzyl (where the benzyl radical is unsubstituted or substituted by halogen or trifluoromethyl), NH-alkyl, N(alkyl).sub.2 and N-(alkyl)-(benzyl), the aforesaid alkyls being straight or branched and having from 1 to 4 carbon atoms and the aforesaid cycloalkyls having from 3 to 6 carbon atoms, except that when X.sub.1 and X.sub.3 are both hydrogen, n is 1 and R is OH, X.sub.2 is not chlorine in the 5-position are useful in the treatment of epilepsy by oral or parenteral administration.Type: GrantFiled: August 3, 1981Date of Patent: August 23, 1983Assignee: SynthelaboInventors: Jean-Pierre Kaplan, Naurice Jalfre, Don P. Giudicelli
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Patent number: 4387247Abstract: In the reduction of di- or polynitro aromatic compounds by gaseous H.sub.2 S over a solid catalyst, addition of CO gas promotes formation of amino groups from all nitro groups in the molecule. A preferred embodiment is reduction of 2,4- and/or 2,6-dinitrotoluene in vapor phase at 325.degree. C. over a supported iron or supported cobalt catalyst on a support comprising alumina. The amino products are useful for production of polyurethane resins.Type: GrantFiled: June 11, 1980Date of Patent: June 7, 1983Assignee: Allied CorporationInventors: Charles T. Ratcliffe, Geza Pap
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Patent number: 4384135Abstract: A method of preparing a diphenyl ether compound of the formula (II) ##STR1## wherein X is F, Cl or Br; Z is hydrogen, halogen, NO.sub.2 of CN; and W is methyl, cyano, CH.sub.3 CO--, or a group --C--OR, wherein R is --OH; --OM wherein M is a cation; OR.sup.1 wherein R.sup.1 is an optionally substituted aliphatic radical; --NR.sup.2 R.sup.3 wherein R.sup.2 and R.sup.3 are each hydrogen or an optionally substituted aliphatic radical; or --NHSO.sub.2 R.sup.4 wherein R.sup.4 is alkyl of 1 to 6 carbon atoms, which comprises reacting a 3-X-substituted-4,5-difluorobenzotrifluoride with a salt of a 3,4-W,Z-substituted phenol. The invention further comprises novel 3-X-4,5-difluorobenzotrifluorides for use in the process.Type: GrantFiled: January 19, 1981Date of Patent: May 17, 1983Assignee: Imperial Chemical Industries LimitedInventors: David Cartwright, Roger Salmon, Alfred G. Williams
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Patent number: 4359467Abstract: 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- ##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: April 22, 1981Date of Patent: November 16, 1982Assignee: Schering AktiengesellschaftInventors: Helmut Vorbruggen, Norbert Schwarz, Olaf Loge, Walter Elger
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Patent number: 4358409Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.Type: GrantFiled: April 16, 1980Date of Patent: November 9, 1982Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4350824Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or the two radicals R.sup.3 together are alkanediyl,in the presence of at least an equimolar amount of a phosphorous acid triamide of the formulaP(NR.sup.4.sub.2).sub.3in whichR.sup.4 each independently is an alkyl radical, or the two radicals R.sup.4 together are alkanediyl.Advantageously,R.sup.1 is hydrogen,R.sup.2 a C.sub.2 to C.sub.Type: GrantFiled: February 23, 1981Date of Patent: September 21, 1982Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz
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Patent number: 4350705Abstract: Derivatives of 2-substituted-cyclohexane-1,3-diones possessing antihypertensive activity.Type: GrantFiled: March 25, 1980Date of Patent: September 21, 1982Assignee: Eisai Co., Ltd.Inventors: Sachiyuki Hamano, Shinichi Kitamura, Toshiji Igarashi, Yoshikage Nakajima
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Patent number: 4349689Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.Type: GrantFiled: December 22, 1980Date of Patent: September 14, 1982Assignee: The Upjohn CompanyInventor: Paul A. Aristoff
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Patent number: 4348534Abstract: 2-Aryloxy-2-halopropionic acid compounds are prepared by reacting 2-aryloxypropionic acid compounds with N-halocarboxylic acid imides in the presence of aliphatic halohydrocarbons as solvents, and of from 0.0001 to 0.001 mole of halogen per mole of N-halocarboxylic acid imide, from 0.005 to 0.05 per cent by weight of water, based on N-halocarboxylic acid imide, and from 0.0005 to 0.005 mole of azo-bis-isobutyronitrile and/or dibenzoyl peroxide, per mole of N-halocarboxylic acid imide.The end products obtainable by the process of the invention are valuable starting materials for the preparation of drugs, crop protection agents and dyes.Type: GrantFiled: June 17, 1981Date of Patent: September 7, 1982Assignee: BASF AktiengesellschaftInventors: Gerd Husslein, Gerhard Hamprecht
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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: 4346228Abstract: 11-Oxoprostaglandin derivatives of the formula ##STR1## wherein R.sub.2 is a hydrogen atom or alkyl of 1-5 carbon atoms,R.sub.3 is alkyl of 1-5 carbon atoms, alkylaryl, cycloalkyl of 5-6 ring carbon atoms and a total of 5-10 carbon atoms; benzodioxol-2-yl, phenyl, naphthyl or phenyl or naphthyl substituted by phenyl, halogen, alkyl of 1-4 carbon atoms, chloromethyl, fluoromethyl, carboxyl or hydroxy;A is --CH.sub.2 --CH.sub.2 --, cis--CH.dbd.CH--, or trans--CH.dbd.CH--;B is --CH.sub.2 --CH.sub.2 -- or trans--CH.dbd.CH--,D and E collectively are a direct bond or D is alkylene of 1-5 carbon atoms and E is an oxygen or sulfur atom; esters thereof; readily cleavable 9,15 and 9,15 ethers thereof; methanesulfonylamides thereof, and physiologically acceptable salts thereof with bases; possess the activity of the corresponding natural prostaglandins with a surprisingly longer duration of effectiveness, greater selectivity, and better effects, and can be produced, e.g.Type: GrantFiled: April 15, 1976Date of Patent: August 24, 1982Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Raduechel, Helmut Vorbrueggen, Walter Elger, Olaf Loge, Eckehard Schillinger
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Patent number: 4336268Abstract: Cyclohexenes of the formula ##STR1## wherein R.sup.1 is hydroxy or lower alkoxy; n is 1 or 2; R.sup.2 is lower alkyl; and R.sup.3 is hydrogen, lower alkyl, lower alkenyl or lower cycloalkylmethyl, and their pharmaceutically acceptable acid addition salts are disclosed. The compounds of formula I have analgesic activity and are useful for the control of pains.Type: GrantFiled: January 27, 1981Date of Patent: June 22, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Hans Bruderer, Albert E. Fischli, Rudolf Pfister
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Patent number: 4323692Abstract: This process relates to the oxidation of phenoxytoluenes to phenoxybenzoic acids utilizing a hydrogen peroxide activated, bromide promoted cobalt catalyst which can be performed at atmospheric pressure and at moderate temperatures. These phenoxybenzoic acids can then be esterified and selectively nitrated to give the corresponding 2-nitro-5-(substituted)phenoxybenzoic acid esters. Alternatively the acids can be nitrated and then esterified.Type: GrantFiled: August 4, 1978Date of Patent: April 6, 1982Assignee: Rohm and Haas CompanyInventor: Charles M. Tanger
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Patent number: 4309562Abstract: .alpha.[4-(4-Trifluoromethylphenoxy)phenoxy]alkanecarboxylic acids (the "4-trifluoromethylphenoxy group" of which may contain one chlorine atom as a substituent) and derivatives thereof useful as a herbicide, a herbicidal composition containing the compound, methods of controlling weeds and production thereof.Type: GrantFiled: April 15, 1977Date of Patent: January 5, 1982Assignee: Ishihara Sangyo Kaisha, Ltd.Inventors: Ryohei Takahashi, Kanichi Fujikawa, Isao Yokomichi, Sinzo Someya, Nobuyuki Sakashita
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Patent number: 4304936Abstract: 3-Phenoxy-.alpha.-phenoxy-alkancarboxylic acid derivatives of the formula ##STR1## are disclosed as possessing a surprising selective herbicidal activity. In the formula, Hal is a halogen atom, m is an integer 1, 2 or 3, Y is a hydrogen or halogen atom or the cyano group, Z is a halogen atom or the cyano group, R.sub.1 is hydrogen or C.sub.1 -C.sub.8 alkyl, and R is an acid function. Methods are disclosed for combatting weeds in mono- and dicotyledonous cultures such as cereals, corn, rice, soya and cotton, which comprise applying to the locus to be protected from weeds a dosage of from 0.1 to 10.0 kilograms per hectare of the above compounds.Type: GrantFiled: October 11, 1979Date of Patent: December 8, 1981Assignee: Ciba-Geigy CorporationInventors: Otto Rohr, Georg Pissiotas, Beat Bohner, Kurt Burdeska
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Patent number: 4296253Abstract: The present invention provides 2,5-inter-o-phenylene-3,4-dinor-PGF.sub.2 amides. These compounds are intermediates for preparing 2,5-inter-o-phenylene-3,4-dinor-prostacyclin analogs, which are useful for pharmacological purposes, e.g., as antithrombotic agents.Type: GrantFiled: July 3, 1980Date of Patent: October 20, 1981Assignee: The Upjohn CompanyInventors: Udo F. Axen, John C. Sih
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Patent number: 4287125Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: September 1, 1981Assignee: Rhone-Poulenc IndustriesInventor: Gerard Soula
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Patent number: 4283420Abstract: The chemical compounds of the invention are useful as the active compound in drugs because of their anticonvulsant and/or antianoxic activity. They have the general formula ##STR1## wherein Z is a hydroxyl group; a group--OM wherein M is an alkali metal atom or an equivalent atom fraction of an alkaline-earth metal or an amino group such as --NH.sub.2, and R is a linear or branched alkyl group containing from 1 to 9 carbon atoms, and optionally substituted by one or more halogen atoms; a linear or branched alkenyl or alkynyl, alkoxyalkyl, or acylalkyl group containing from 2 to 9 carbon atoms and optionally substituted by one or more halogen atoms; an aryl or arylalkyl or aryloxyalkyl group comprising at least one aromatic radical and an alkyl chain having from 1 to 4 carbon atoms.Type: GrantFiled: April 18, 1979Date of Patent: August 11, 1981Assignee: LabazInventors: Charles Pigerol, Jean-Claude Vernieres, Pierre Eymard, Jacques Simiand, Madeleine Broll, Jean-Yves Lacolle
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Patent number: 4281191Abstract: The present invention provides novel 19-hydroxy-19-methyl-PG amides and methods for their preparation and pharmacological uses for the induction of prostaglandin-like effects.Type: GrantFiled: March 24, 1980Date of Patent: July 28, 1981Assignee: The Upjohn CompanyInventor: John C. Sih