Carbonyl Containing (e.g., Ketone Containing, Etc.) Patents (Class 568/31)
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Patent number: 5283349Abstract: A 2,6,7-trisubstituted-3-methylenebicyclo-[3.3.0]octane of formula (I) or an enantiomer thereof, or a mixture of these in an arbitrary ratio. The compound is a key intermediate for preparation of isocarbacyclins which are useful as medicines for the circulatory system such as an antithrombotic agent, an antilipidemic agent, a hypotensive agent or an antiarterosclerotic agent.Type: GrantFiled: September 11, 1986Date of Patent: February 1, 1994Assignee: Teijin LimitedInventors: Toshio Tanaka, Kiyoshi Bannai, Seizi Kurozumi
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Patent number: 5274172Abstract: There is disclosed a process for preparing granular esters in one step by the reaction of an alcohol with acid chloride in an aqueous alkaline medium with moderate shear agitation and optionally in the presence of a surfactant.Type: GrantFiled: June 24, 1992Date of Patent: December 28, 1993Assignee: Monsanto CompanyInventors: Yueting Chou, David A. Martin
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Patent number: 5272178Abstract: The present invention relates to compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and independently represent tert-alkyl, phenyl, or hydrogen; R.sup.3 represents hydrogen or alkyl; X represents O, S or (CH.sub.2).sub.m wherein m is 1 or 2; A represents O or S(O).sub.n wherein n is 0, 1, or 2; p is an integer from 0 to 4; and R represents alkyl; OH; OR.sup.4 wherein R.sup.4 is alkyl; or NR.sup.5 R.sup.6 wherein R.sup.5 is hydrogen or alkyl, and R.sup.6 is hydrogen, alkyl, heterocyclealkyl, substituted heterocyclealkyl, cycloalkyl, substituted cycloalkyl, phenyl, substituted phenyl, phenylalkyl, or substituted phenylalkyl, or NR.sup.5 R.sup.6 together form a heterocyclic ring which may optionally be substituted; or (CH.sub.2).sub.t COOR.sup.7 wherein t is an integer from 1 to 4 and R.sup.7 is hydrogen or alkyl; and the pharmaceutically acceptable salts thereof. The compounds are inhibitors or stimulators of superoxide generation.Type: GrantFiled: April 8, 1993Date of Patent: December 21, 1993Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 5260489Abstract: A process for purifying a halogenated aromatic sulfone or ketone compound comprises contacting the compound with a mixture containing a solvent having a normal boiling point less than about 225.degree. C. and water to form a second mixture, heating the second mixture at a temperature sufficient to substantially dissolve the halogenated compound to form a third mixture, cooling the third mixture to purify and recrystallize the compound, and recovering the purified, recrystallized compound. A second embodiment of the invention comprises repeating the purification process steps at least once to further purify the halogenated aromatic sulfone or ketone compound.Type: GrantFiled: September 30, 1992Date of Patent: November 9, 1993Assignee: Phillips Petroleum CompanyInventors: Rex L. Robsein, Jimmie J. Straw, Darryl R. Fahey
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Patent number: 5237102Abstract: Provided is a novel process for readily producing .beta.-carotene in which a sulfone compound represented by the general formula (1), (2) or (3) is reacted with an alkali, ##STR1## wherein R represents a phenyl group which may be substituted, R' a protecting group of acetal type and X a halogen atom.Type: GrantFiled: August 31, 1992Date of Patent: August 17, 1993Assignee: Kuraray Company Ltd.Inventors: Toshiki Mori, Hiroshi Fujii, Takashi Onishi, Kazuo Yamamoto
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Patent number: 5210258Abstract: Optically active naphthyl alpha-substituted alkyl ketones, are a class of ketones useful as intermediates in the production of optically active alpha-naphthylalkanoic acids which exhibit anti-inflammatory, analgesic and anti-pyretic activity.Type: GrantFiled: April 29, 1992Date of Patent: May 11, 1993Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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Patent number: 5206440Abstract: A process for production of fluorinated sulfones from fluorinated organic sulfides by oxidation of the sulfides with an oxidizing reagent made from fluorine, water and acetonitrile. The sulfones are useful as second order nonlinear optical dyes.Type: GrantFiled: July 28, 1992Date of Patent: April 27, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard Beckerbauer, Shlomo Rozen
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Patent number: 5200535Abstract: The invention provides cyclohexanone derivatives of the general formula ##STR1## in which n represents an integer from 0 to 5; each R represents a halogen atom, nitro, cyano, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl or phenyl group; R.sup.1, R.sup.2 and R.sup.3 independently represent a hydrogen atom or an alkyl group; R.sup.6 and R.sup.7 together represent a single carbon-carbon bond or an epoxy group; and R.sup.8 represents a hydrogen atom or a hydroxyl group; with the proviso that when R.sup.6 and R.sup.7 together represent an epoxy group then R.sup.8 represents a hydrogen atom; and a process for their preparation. Compounds of formula I are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: August 19, 1991Date of Patent: April 6, 1993Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 5185468Abstract: Provided is a novel process for readily producing .beta.-carotene by reacting a sulfone compound represented by the general formula (1), (2) or (3) with an alkali, ##STR1## wherein R represents a phenyl group which may be substituted, R' a protecting group of acetal type and X a halogen atom.Type: GrantFiled: May 28, 1991Date of Patent: February 9, 1993Assignee: Kuraray Company Ltd.Inventors: Toshiki Mori, Hiroshi Fujii, Takashi Onishi, Kazuo Yamamoto
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Patent number: 5169988Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- to 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.Type: GrantFiled: April 8, 1992Date of Patent: December 8, 1992Assignee: Ciba-Geigy CorporationInventor: Hans Tobler
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Patent number: 5166441Abstract: The present invention related to novel compounds useful in the manufacture of astaxanthin and to processes for their preparation. The novel intermediates have the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are C.sub.1-6 -alkyl which may be branched or phenyl, and ##STR2## wherein R' is alkyl, alkoxy, NO.sub.2, NH.sub.2 or halogen.Type: GrantFiled: December 9, 1991Date of Patent: November 24, 1992Assignee: NeuroSearch A/SInventor: Peter Moldt
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Patent number: 5157150Abstract: A process for the preparation of 2-(chloro, bromo or nitro)-4-(alkylsulfonyl)benzoic acid and to intermediates used in the process.Type: GrantFiled: January 15, 1991Date of Patent: October 20, 1992Assignee: Imperial Chemical Industries PLCInventor: Richard W. Brown
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Patent number: 5152826Abstract: An herbicide compound of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, nitro; cyano; C.sub.1 -C.sub.2 haloalkyl, or R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are alkylene having 2 to 5 carbon atoms;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.5 and R.sup.6 together are alkylene having 2 to 5 carbon atoms;R.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n --wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.Type: GrantFiled: October 16, 1991Date of Patent: October 6, 1992Assignee: Imperial Chemical Industries PLCInventor: Christopher G. Knudsen
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Patent number: 5132462Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- to 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.Type: GrantFiled: March 7, 1991Date of Patent: July 21, 1992Assignee: Ciba-Geigy CorporationInventor: Hans Tobler
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Patent number: 5131945Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.Type: GrantFiled: July 13, 1990Date of Patent: July 21, 1992Assignee: Shell Research LimitedInventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
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Patent number: 5128479Abstract: Oxidized diphenylheteroalkanes of the formula I ##STR1## where R.sup.1 to R.sup.6 and A have the meanings specified in the description, and the preparation thereof are described. The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: January 29, 1990Date of Patent: July 7, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5116869Abstract: 2-Substituted-2-cyclopentenones represented by the formula (I): ##STR1## wherein A is a hydroxyl group or ##STR2## and B is a hydrogen atom or A and B are bonded together to form one bonding arm;R.sup.1 represents a substituted or unsubstituted hydrocarbon group having 1 to 10 carbon atoms;R.sup.2 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms;R.sup.3 represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms; wherein,when R.sup.3 is a single bond bonded to the cyclopentene skeleton, X represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; andwhen R.sup.3 is a double bond bonded to the pentene skeleton, X represents a bonding arm constituting a part of said double bond; andm and n independently represent 0, 1 or 2.Type: GrantFiled: September 3, 1991Date of Patent: May 26, 1992Assignee: Teijin LimitedInventors: Satoshi Sugiura, Atsuo Hazato, Toru Minoshima, Yoshinori Kato, Yasuko Koshihara, Seizi Kurozumi
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Patent number: 5110343Abstract: The invention relates to a herbicidal composition having an inert carrier and an effective amount of a compound having the formula ##STR1## wherein X is the same or different substituent selected from the group consisting of halogen, nitro, C.sub.1-6 alkyl, halo C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio and C.sub.1-6 alkylsulfonyl;n is 1, 2, 3 or 4;R.sup.1 is C.sub.1-6 alkyl which is substituted by cyano, halogen, hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulfonyl or tetrahydropyranyloxy; C.sub.1-6 alkylthio, phenylthio, pyridyl or tetrahydropyranyl;R.sup.2 is C.sub.1-6 alkyl;l is 0, 1 or 2.Type: GrantFiled: May 24, 1990Date of Patent: May 5, 1992Assignee: Nippon Soda Co., Ltd.Inventors: Akiyoshi Ueda, Haruhito Ohishi, Toshio Aihara, Hisao Ishikawa, Kazuyuki Tomida, Hideo Hosaka
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Patent number: 5107029Abstract: This invention concerns a process for preparing diketones and keto-acids by reacting a dicarboxylic acid and an aromatic compound in the presence of an alkylsulfonic acid such as methanesulfonic acid and an organic anhydride compound such as methanesulfonic anhydride or trifluoroacetic anhydride. The diketones and keto-acids can be used to prepare polyketones which are useful as molding plastics, coatings, films, fibers, and the like.Type: GrantFiled: July 23, 1990Date of Patent: April 21, 1992Assignee: Eastman Kodak CompanyInventors: Theodore R. Walker, Jr., Winston J. Jackson, Jr., Jean C. Fleischer
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Patent number: 5106407Abstract: The present invention discloses the antimicrobial utility of certain iodonium ylide compounds. The particular iodonium ylide compounds are phenyl iodonium ylides having an ortho substituent that stabilizes the positive charge on the polyvalent iodine by a nonbonded electrostatic interaction. The polyvalent iodine is further stabilized by a cyclic 1,3-dicarbonyl anion.Type: GrantFiled: December 4, 1989Date of Patent: April 21, 1992Assignee: The Dow Chemical CompanyInventors: Attila G. Relenyi, Gerald F. Koser, Richard W. Walter, Jr., William J. Kruper, Jr., Ravi B. Shankar, Anthony P. Zelinko
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Patent number: 5100460Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.Type: GrantFiled: July 13, 1989Date of Patent: March 31, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philippe Desbordes, Michel Euvrard
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Patent number: 5101065Abstract: A process for the preparation of 2-(hydrogen, halogen or lower alkyl)-3-(hydroxy, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, --OCH.sub.2 CH.sub.2 OCH.sub.3, --OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, --OCH.sub.2 CH.sub.2 SCH.sub.3 or --OCH.sub.2 CH.sub.2 SC.sub.2 H.sub.5)-4-(alkythio or alkylsulfonyl)-acetophenones.Type: GrantFiled: February 4, 1991Date of Patent: March 31, 1992Assignee: Imperial Chemical Industries plcInventor: Richard W. Brown
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Patent number: 5097068Abstract: Novel trisubstituted benzoic acid intermediates which are useful in the preparation of certain herbicidal 2-(2,3,4-trisubstituted benzoyl)-1,3-cyclohexandediones. The intermediate benzoic acids of this invention have the following structural formula ##STR1## wherein R.sup.6 is chlorine, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio or hydroxy; n is the integer 0 or 2; and R.sup.7 is C.sub.1 -C.sub.4 alkyl.Type: GrantFiled: December 7, 1989Date of Patent: March 17, 1992Assignee: ICI Americas, Inc.Inventor: David L. Lee
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Patent number: 5095150Abstract: A formylated alkylbenzenesulfonyl halide compound represented by the following general formula (I): ##STR1## wherein R.sub.1 is an alkyl group having 1 to 5 carbon atoms; R.sub.2 and R.sub.3 are each a member selected from the group consisting of a hydrogen atom and alkyl groups having 1 to 5 carbon atoms; X is a halogen atom; the sulfonyl halide group is present at the ortho or para position while the formyl group at the para or ortho position relative to the group R.sub.1 when R.sub.2 and R.sub.3 are both a hydrogen atom, while the sulfonyl halide group and the formyl group are present at the para positions relative to the groups R.sub.1 and R.sub.2, respectively, when R.sub.2 is an alkyl group and R.sub.3 is a hydrogen atom, or the sulfonylhalide group and the formyl group are present at the para positions relative to the groups R.sub.1 and R.sub.2, respectively, when R.sub.2 and R.sub.Type: GrantFiled: March 25, 1991Date of Patent: March 10, 1992Assignee: Agency of Industrial Science & TechnologyInventors: Yoshie Souma, Jun Iyoda, Hirosi Sano
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Patent number: 5094685Abstract: A substituted benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, cyano, nitro or halogen; X.sub.2 is --L--OR.sub.1 (wherein L is C.sub.1 -C.sub.4 alkylene or C.sub.1 -C.sub.4 alkylidene, and R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl), --L--O--L--OR.sub.1 (wherein L and R.sub.1 are as defined above), --L--S(O).sub.n --R.sub.2 (wherein L is as defined above, R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl, and n is an integer of 0, 1 or 2), --L--O--COR.sub.2 (wherein L and R.sub.2 are as defined above), --L--NR.sub.1 R.sub.3 (wherein L and R.sub.1 are as defined above, and R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl), --COOR.sub.1 (wherein R.sub.1 is as defined above) or --COO--L--O--R.sub.1 (wherein L and R.sub.1 are as defined above), provided that when X.sub.Type: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Nissan Chemical Industries Ltd.Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe, Koichi Suzuki
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Patent number: 5092919Abstract: Herbicidal compounds of the structural formula ##STR1## wherein R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.4 is hydroxy, hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl (.dbd.O) with the proviso that R.sup.1, R.sup.2, R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, or C.sub.1 -C.sub.4 alkylsulfonyl, with the proviso that when R.sup.6 is C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylsulfonyl, the R.sub.3 and R.sup.4 are not together carbonyl; R.sup.7 is methyl or ethyl; and R.sup.8 is (1) halogen; (2) nitro; or (3) R.sup.b SO.sub.n -- wherein n is the integer 0 or 2, and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; and its salts.Type: GrantFiled: January 15, 1991Date of Patent: March 3, 1992Assignee: Imperial Chemical Industries plcInventor: Nhan H. Nguyen
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Method for preparing intermediates for the synthesis of steroid side chains in optically active form
Patent number: 5089647Abstract: This invention provides a novel method for the preparation of optically active arylalykylsulfone derivatives, having a chiral center in the alkyl moiety in either the (R)- or the (S)-configuration. These optically active sulfones find use in the stereospecific synthesis of steroid or vitamin D compounds having chiral center at either carbon 24 or carbon 25 of the side chain. The method comprises the steps of reacting an optically active sulfinate ester having a chiral center at sulfur with a racemic alkyl Grignard reagent to obtain a mixture of diastereomeric sulfoxides, separating the mixture of diastereomeric sulfoxides, and oxidizing separately each of the diastereomers to obtain the desired optically active sulfone.Type: GrantFiled: April 11, 1990Date of Patent: February 18, 1992Assignee: Wisconsin Alumni Research FoundationInventors: Hector F. DeLuca, Heinrich K. Schnoes, Kato L. Perlman -
Patent number: 5087743Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.Type: GrantFiled: January 23, 1990Date of Patent: February 11, 1992Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5085688Abstract: Herbicidal compounds of the formula ##STR1## wherein R.sub.3 is methoxy or ethoxy; andR.sub.4 is bromine, methylsulfonyl or ethylsulfonyland their salts.Type: GrantFiled: November 1, 1990Date of Patent: February 4, 1992Assignee: ICI Americas Inc.Inventors: William J. Michaely, Gary W. Kraatz
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Patent number: 5084478Abstract: A compound of the formula ##STR1## wherein X has the formula --CR.sup.5 .dbd.CR.sup.6 --, --C.tbd.C-- or ##STR2## wherein ring A is phenyl, naphthyl or heterocyclic; wherein R.sup.1 is hydrogen, alkyl, alkanoyl or aroyl;wherein R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each is an electron withdrawing substituent or each is hydrogen or alkyl, alkoxy or dialkylamino, provided that when ring A is phenyl or naphthyl at least one of R.sup.2, R.sup.3 and R.sup.4 is an electron-withdrawing substituent;wherein R.sup.5 and R.sup.6, each is hydrogen, halogeno or alkylwherein R.sup.7 is alkyl or halogenoalkyl; and wherein R.sup.8 has the formula --Y--Q--R.sup.9 wherein Y is straight- or branched-chain alkylene or alkenylene; wherein Q is --O--, --S--, --SO-- or --SO.sub.2 --;and wherein R.sup.9 is alkyl of up to 6 carbon atoms which contains one or more defined substituents, processes for their manufacture and pharmaceutical compositions containing them.Type: GrantFiled: April 14, 1989Date of Patent: January 28, 1992Assignee: Imperial Chemical Industries PLCInventors: Leslie R. Hughes, Howard Tucker
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Patent number: 5075339Abstract: The invention relates to benzylketone phospholipase A.sub.2 inhibitors, pharmaceutical compositions containing them, and methods of treating phospholipase A.sub.2 -mediated conditions in mammals by administration of a therapeutically effective amount of such a benzylketone phospholipase A.sub.2 inhibitor. These compounds are also intermediates in the synthesis of other PLA.sub.2 inhibitors.Type: GrantFiled: June 1, 1990Date of Patent: December 24, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventor: Wendell W. Wilkerson
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Patent number: 5055605Abstract: The process of the present invention relates to the preparation of precursor trisubstituted benzoic acid intermediates having the structural formula ##STR1## wherein R is --COOR.sup.a wherein R.sup.a is C.sub.1 -C.sub.6 alkyl; C.sub.1 -C.sub.4 alkyl; formyl or C(O)R.sup.b wherein R.sup.b is C.sub.1 -C.sub.4 alkyl;R.sup.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or trifluoromethyl;R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl --OCH.sub.2 CH.sub.2 OCH.sub.3, --OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 or a substituted methyl group andR.sup.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl.Type: GrantFiled: October 15, 1990Date of Patent: October 8, 1991Assignee: Imperial Chemical Industries plcInventor: Charles N. Ludvik
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Patent number: 5041681Abstract: Process for the preparation of herbicidally active substituted cyclohexan-1,3,5-triones which comprises either(a) reacting a compound of formula (II) ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are, for example, hydrogen or C.sub.1 -C.sub.4 alkyl with a compound of formula (III):R.sup.1 COCN (III)wherein R.sup.1 is optionally substituted aryl in the presence of a base and a Lewis acid; or(b) reacting a compound of formula (VI) ##STR2## with a compound of formula (X) ##STR3## in the presence of a Lewis acid; or (c) where R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same, reacting a compound of formula (XI) ##STR4## with a compound of formula R.sup.2 X' in the presence of a base, wherein X' is a leaving group.Type: GrantFiled: January 12, 1990Date of Patent: August 20, 1991Assignee: Imperial Chemical Industries PLCInventor: Glynn Mitchell
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Patent number: 5041600Abstract: Arylcyclobutenealkyl diethers of oligomers containing a plurality of aromatic rings at least two of which are joined by a sulfone moiety, are self-curing at temperatures above about 150.degree. C. The cured products exhibit good properties of strength and toughness.Type: GrantFiled: January 29, 1990Date of Patent: August 20, 1991Assignee: Shell Oil CompanyInventor: Pui K. Wong
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Patent number: 5015775Abstract: Alkyl aryl sulfones of the formula R--SO.sub.2 --AR--Y.sub.n, wherein Ar is an aryl compound, Y is a substituent on the aryl compound and R is alkyl or cycloalkyl, and liquid mixtures of positional isomers of the same are prepared by reacting an aryl compound of the formula Ar--Y.sub.n, with an alkyl sulfonic acid of the formula R--SO.sub.3 H and a phosphorus reagent, preferably under heat. Particularly good yields and pure products are obtained using phosphorus pentoxide. Alkyl aryl sulfones produced by this method are a liquid mixture preferably containing at least two positional isomers, wherein no isomer is present in an amount of more than about 50% of the isomer mixture.Type: GrantFiled: March 31, 1988Date of Patent: May 14, 1991Assignee: Atochem North America, Inc.Inventors: James L. Reilly, Gordon R. Leader
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Patent number: 4997473Abstract: Compunds of the formula ##STR1## wherein R is halogen, C.sub.1 -C.sub.2 alkyl, nitro, C.sub.1 C.sub.2 haloalkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio or C.sub.1 C.sub.2 alkylsulfonyl; R.sup.1 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.2 alkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.2 alkyl; and R.sup.4 and R.sup.5 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl, (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.3 C(O)- wherein R.sup.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy; or (12) --SO.sub.2 NR.sup.c R.sup.d wherein R.sup.c and R.sup.d are as defined; and (13) --N(R.Type: GrantFiled: August 24, 1989Date of Patent: March 5, 1991Assignee: ICI Americas Inc.Inventor: Nhan H. Nguyen
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Patent number: 4980509Abstract: An aromatic polycyclic compound has the formula ##STR1## wherein R represents --SO.sub.3 H, SO.sub.2 NHR.sub.3, ##STR2## --SO.sub.2 R.sub.3, --SOR.sub.3 or --SR.sub.3, R.sub.3 represents lower alkyl, monohydroxyalkyl, polyhydroxyalkyl, aminoalkyl, carboxyalkyl, aminocarboxyalkyl or alkoxyalkyl,R' represents hydrogen, lower alkyl, lower alkoxy, hydroxy, C.sub.1 -C.sub.4 acyloxy or amino,R" represents hydrogen, lower alkyl or lower alkoxy, orR' and R", taken together, form an oxo, methano or hydroxyimino radical,R.sub.1 represents hydrogen or lower alkyl,n is 0 or 1,when n=1, R.sub.2 represents hydrogen or lower alkyl, or R.sub.1 and R.sub.2, taken together form a vinylene radical, andAr represents an aromatic radical selected from ##STR3## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11 represent hydrogen or lower alkyl, at least one of R.sub.4 and/or R.sub.5 being other than hydrogen, and at least two of R.sub.8 -R.sub.Type: GrantFiled: July 1, 1988Date of Patent: December 25, 1990Assignee: Societe Anonyme dite: L'OrealInventors: Jean Maignan, Gerard Lang, Gerard Malle, Serge Restle
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Patent number: 4957538Abstract: Herbicidal compounds of the structural formula ##STR1## wherein X is oxygen or sulfur; R is chlorine or bromine; R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.4 is hydroxy, hydrogen or C.sub.1 -C.sub.4 alkyl; or R.sup.3 and R.sup.4 together are carbonyl (.dbd.0) with the proviso that R.sup.1 , R.sup.2, R.sup.5 and R.sup.6 are all C.sub.1 -C.sub.4 alkyl; R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, or C.sub.1 -C.sub.4 alkylsulfonyl, with the proviso that when R.sup.6 is C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylsulfonyl, then R.sup.3 and R.sup.4 are not together carbonyl; R.sup.7 is methyl or ethyl; and R.sup.8 is (1) halogen; (2) nitro; or (3) R.sup. b SO.sub.n --wherein n is the integer 0 or 2; and R.sup.b is (a) C.sub.1 -C.sub.3 alkyl; and their salts.Type: GrantFiled: November 18, 1988Date of Patent: September 18, 1990Assignee: ICI Americas Inc.Inventor: William J. Michaely
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Patent number: 4956109Abstract: Herein disclosed is a lubricating oil comprising at least one member selected from the group consisting of esterified products obtained by reacting: (A) a compound selected from the group consisting of alcohols represented by the following general formula (I), alcohols represented by the following general formula (II) and hydrogenated derivatives thereof; with (B) a fatty acid having not less than 6 carbon atoms or a mixture of the fatty acid with a rosin selected from the group consisting of rosin, hydrogenated rosins, disproportionated rosins and polymerized rosins: ##STR1## in the general formulas (I) and (II), X.sub.1 and X.sub.2 each independently represents a hydrogen atom or a methyl group and n is an integer ranging from 0 to 10. The lubricating oil is used as rolling mill oils, hydraulic oils cutting-grinding oils, lubricating oils for metal plastic working and those for internal combustion engines.Type: GrantFiled: May 26, 1989Date of Patent: September 11, 1990Assignees: The Nisshin Oil Mills, Ltd., Nippon Steel CorporationInventors: Keiichi Tanikawa, Higaki Yuzo
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Patent number: 4954165Abstract: An herbicidally effective benzoyl derivative having the formula: ##STR1## wherein X.sub.1 is C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2 is discosed.In addition, the herbicidally effective benzoyl derivative having the formula: ##STR2## wherein: X.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy halogen;X.sub.4 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;X.sub.5 is hydrogen or fluorine;Y.sub.1, Y.sub.2, Y.sub.3, Y.sub.4 and Y.sub.5 are independently hydrogen or C.sub.1 -C.sub.4 alkyl;R.sub.1 is C.sub.1 -C.sub.4 alkyl;R.sub.4 is C.sub.1 -C.sub.3 alkyl;n is an integer of 0, 1 or 2;L is C.sub.1 -C.sub.4 alkylene is disclosed.Type: GrantFiled: October 18, 1988Date of Patent: September 4, 1990Assignee: Nissan Chemical Industries Ltd.Inventors: Masatoshi Baba, Takuya Kakuta, Norio Tanaka, Eiichi Oya, Takashi Ikai, Tsutomu Nawamaki, Shigeomi Watanabe, Koichi Suzuki
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Patent number: 4946992Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formulas HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H or HO[--CH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H are prepared from halogenated neopentyl glycols or oxetanes and thiols of the formula R.sub.f --E--SH, amines of the formuls R.sub.f --E--NH--R, alcohols of the formula R.sub.f --E--OH or perfluoro-amides, wherein R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanated to prepare polyureas/polyurethanes; with acids or derivatives to prepare polyesters or polycarbonates are disclosed. These include polymeric, random or block urethane, and/or urea, and/or ester compositions containing the residue of at least one R.sub.Type: GrantFiled: April 14, 1989Date of Patent: August 7, 1990Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas, Michael Jacobson
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Patent number: 4937388Abstract: The invention provides insecticidally active compounds of formula I: ##STR1## wherein A is selected from oxygen and a group of formula S(O).sub.n, where n represents 0, 1 or 2; W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms, selected from alkylene and alkylenedioxy; Y represents a substituted aryl group where each substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; Z represents a fluoroalkyl group of up to two carbon atoms; and either X' represents hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and acyloxy, or X and X' together represent a second bond between the adjacent carbon atoms.The invention also provides processes and intermediates useful for the preparation of the compounds of formula I, insecticidal compositions comprising the compounds of formula I, and methods of combating and controlling pests therewith.Type: GrantFiled: October 29, 1987Date of Patent: June 26, 1990Assignee: Imperial Chemical Industries PLCInventors: Michael J. Bushell, Robin A. E. Carr
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Patent number: 4937386Abstract: The present invention relates to 4,4,5-trimethyl-2-(2-nitro-4-methylsulfonylbenzoyl) cyclohexane-1,3-dione which is useful as herbicide.Type: GrantFiled: June 30, 1989Date of Patent: June 26, 1990Assignee: Nippon Soda Co., Ltd.Inventors: Akiyoshi Ueda, Hideo Hosaka
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Patent number: 4922014Abstract: Process for the preparation of oxethylmercaptobenzaldehydes and their oxidation products of the formula (I) ##STR1## in which R denotes a hydrogen, fluorine, chlorine, bromine or iodine atom, m denotes the number 0 or 2, n denotes the number 1 or 2, and p denotes the number 0 or 1, with the proviso that p is 0 if m is 0, and the side-chain --S(0).sub.m --CH.sub.2 --CH.sub.2 --OH is in the ortho and/or para position to the aldehyde or carboxyl group, can be prepared by condensing 1 mole of a halobenzaldehyde of the general formula (II) ##STR2## in which R, X, Y and Z represent hydrogen, fluorine, chlorine, bromine or iodine atoms, with the proviso that R, X, Y and Z can be in total 1, 2 or 3 halogen atoms, where R is a halogen atom if R, X, Y and Z together represent 3 halogen atoms, in aqueous medium with about 1.0 to 1.5 moles of mercaptoethanol (per halogen atom to be exchanged) in the presence of the acid-binding agents at or about 70.degree. C. about 150.degree. C.Type: GrantFiled: September 20, 1988Date of Patent: May 1, 1990Assignee: Hoechst AktiengesellschaftInventor: Theodor Papenfuhs
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Patent number: 4909835Abstract: The invention relates to novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof with herbicidal and plant growth regulating properties.The novel 2-acyl-1,3-cyclohexanediones and the oxime ethers thereof are of the formula I ##STR1## wherein A is a 2- or 7-membered alkylene bridge, or a 3- to 7-membered alkenylene bridge which may be mono- or polyunsaturated,n is 0, 1 or 2,R.sub.1 is C.sub.1 -C.sub.4 alkyl or benzyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; or is C.sub.3 -C.sub.6 cycloalkyl; or phenyl, benzyl or phenylethyl, the phenyl ring of each of which may be substituted by ahlogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, cyano or nitro,X is oxygen or a radical --NOR.sub.3, andR.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl or C.sub.3 -C.Type: GrantFiled: February 24, 1988Date of Patent: March 20, 1990Assignee: Ciba-Geigy CorporationInventor: Hans Tobler
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Patent number: 4898981Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formula HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H prepared from halogenated neopentyl glycols and thiols of the formula R.sub.f --E--SH, or amines of the formula R.sub.f --E--NH--R wherein R.sub.f is a hydrophonic, olephobic fluoroaliphatic group of up to 20 carbon atoms, E is alkylene of up to 10 carbon atoms, optionally interrupted by up to three groups including --NR, --O, --S--, --SO.sub.2 --, --O.sub.2 C, CONR, and --SO.sub.2 NR, and X is S,SO.sub.2 or NR.sub.2, where R is independently hydrogen, alkyl, or hydroxyalkyl of 1 to 6 carbon atoms are described.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanates, to prepare polyureas/polyurethanes; with acids or derivatives, to prepare polyesters or polycarbonates are disclosed.Type: GrantFiled: June 20, 1988Date of Patent: February 6, 1990Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas
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Patent number: 4883887Abstract: A process for producing carotenoids and carotenoid intermediates via reduction of sulfonyl polyenes with a dithionite in the presence of ammonia or an aliphatic amine, including novel intermediates in this process, which carotenoids are known coloring agents for foodstuffs, animal feeds, pharmaceuticals, etc.Type: GrantFiled: July 1, 1988Date of Patent: November 28, 1989Assignee: Hoffmann-La Roche Inc.Inventors: Kurt Bernhard, Stephan Jaggli, Paul Kreienbuhl, Ulrich Schwieter
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Patent number: 4877899Abstract: Sulfur-substituted alkenyl compounds, synthesis thereof, intermediates therefor, and the use of the compounds to control pests.Type: GrantFiled: November 23, 1983Date of Patent: October 31, 1989Assignee: Sandoz Ltd.Inventors: Robert L. Carney, Thomas L. Brown
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Patent number: 4869748Abstract: Herbicidal compounds of the formula ##STR1## wherein R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n - wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.3 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; andR.sup.5 and R.sup.6 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n - wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.d independently are hydrogen or C.sub.1 -C.sub.4 alkyl; (11) R.sup.e C(O)- wherein R.sup.Type: GrantFiled: December 2, 1988Date of Patent: September 26, 1989Assignee: ICI Americas Inc.Inventor: Christopher G. Knudsen
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Patent number: 4867784Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1, R.sup.2, A, m, n, x and y have the meanings given in the disclosure, a process for their manufacture, herbicidal and plant growth-regulating agents containing the novel active ingredients, and processes for combating unwanted plant growth and for regulating plant growth.Type: GrantFiled: January 14, 1987Date of Patent: September 19, 1989Assignee: BASF AktiengesellschaftInventors: Michael Keil, Wolfgang Spiegler, Dieter Jahn, Dieter Kolassa, Ulrich Schirmer, Bruno Wuerzer, Norbert Meyer, Wilhelm Rademacher, Johann Jung