Chalcogen Of -c(=x)x-, Wherein The X's Are The Same Or Diverse Chalcogens, Bonded Directly To The Carbocyclic Ring Of The Bicyclo Ring System Patents (Class 549/470)
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Patent number: 4778805Abstract: 4,7-Benzofurandione derivatives of Formula I, pharmaceutical compositions, and methods of treatment are disclosed. These compounds are useful as inhibitors of mammalian leukotriene biosynthesis. As such, these compounds are useful therapeutic agents for treating allergic conditions, asthma, cardiovascular disorders, inflammation, psoriasis and allergic conjunctivitis. The compounds are also useful as analgesics and as cytoprotective agents. Also disclosed are novel intermediates useful for the preparation of the 4,7-benzofurandiones of this invention.Type: GrantFiled: June 18, 1987Date of Patent: October 18, 1988Assignee: Merck Frosst CanadaInventors: Julian Adams, Yvan Guindon, Patrice C. Belanger, Michel L. Belley, Joshua Rokach
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Patent number: 4775679Abstract: Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.Type: GrantFiled: May 4, 1987Date of Patent: October 4, 1988Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, David A. Boulton, Kathryn L. Thompson
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Patent number: 4772730Abstract: Benzofurans of the formula ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetamido, R.sup.2 is at least one of halo, cyano, alkyl(C.sub.1 -C.sub.8), cycloalkyl(C.sub.3 -C.sub.8), hydroxy, alkoxy(C.sub.1 -C.sub.8), acyl(C.sub.1 -C.sub.8), acyloxy(C.sub.1 -C.sub.8), alkoxy(C.sub.1 -C.sub.8)carbonyl, alkoxy(C.sub.1 -C.sub.8)carbonylalkyl(C.sub.1 -C.sub.8), phenyl, phenyloxy, trifluoromethyl or dialkyl(C.sub.1 -C.sub.8)amino, m is 0-3, and at least one of the carbon atoms of the benzene ring of said benzofuran is substituted. The compounds are intermediates in the preparation of pyrazoline insecticides.Type: GrantFiled: September 8, 1987Date of Patent: September 20, 1988Assignee: FMC CorporationInventors: David E. Seelye, Ernest L. Plummer
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Patent number: 4758676Abstract: The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and analogues thereof, which have demonstrated antiatherosclerotic activity.Type: GrantFiled: August 29, 1986Date of Patent: July 19, 1988Assignee: The Upjohn CompanyInventor: Ayako Yamashita
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Patent number: 4738981Abstract: Substituted trans-1,2-diaminocyclohexyl amide compounds demonstrating selective opioid receptor binding possess utility as analgesic, diuretic, and psychotherapeutic agents. A method of preparing the compounds, pharmaceutical compositions employing the compounds, and a method of alleviating pain employing the compounds are also disclosed.Type: GrantFiled: November 10, 1986Date of Patent: April 19, 1988Assignee: Warner-LambertInventor: David Horwell
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Patent number: 4730062Abstract: Tetrafluorobenzofurans of the formula ##STR1## are prepared by contacting, at elevated temperature in an aprotic solvent, an ether of the formula ##STR2## with a catalytic mixture of metallic cooper and a polydentate or other ligand, wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetylimido, R.sup.2 is at least one of hydrogen, halo, cyano, alkyl, hydroxy, alkoxy, acyl, acyloxy, alkoxycarbonyl, alkoxycarbonylalkyl, phenyl, phenyloxy, trifluoromethyl or dialkylamino. The products are intermediates in the preparation of pyrazoline insecticides.Type: GrantFiled: April 19, 1985Date of Patent: March 8, 1988Assignee: FMC CorporationInventors: David E. Seelye, Ernest L. Plummer
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Patent number: 4713393Abstract: Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.Type: GrantFiled: April 25, 1985Date of Patent: December 15, 1987Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Kathryn L. Thompson, David A. Boulton
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Patent number: 4698438Abstract: A continuous, close-coupled method for making N-methyl carbamate pesticides which comprises contacting the methyl isocyanate in a vapor phase mixture containing methyl isocyanate and water with a selected oxime or phenol, said mixture being the reaction product formed by oxidizing monomethylformamide. An optional intermediate step for preparing the methyl isocyanate/water vapor phase reaction mixture for contact with the oxime or phenol is to remove therefrom a portion of the water without liquefying the methyl isocyanate by cooling the mixture to a temperature below the dew point of water but above the dew point of the methyl isocyanate.Type: GrantFiled: February 11, 1986Date of Patent: October 6, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Charles T. Blaisdell, Walter J. Cordes, George E. Heinsohn, John F. Kook, John R. Kosak
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Patent number: 4668806Abstract: Reacting an alkali metal cyanate salt with dimethyl sulfate in acetonitrile, heating in a steady stream of nitrogen and thereafter immediately bubbling the formed methyl isocyanate into a solution of an appropriate oxime or phenol to form an N-methylcarbamate.Type: GrantFiled: April 18, 1985Date of Patent: May 26, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Joseph J. Mrowca
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Patent number: 4666931Abstract: A benzofuran derivative having the general formula (I): ##STR1## wherein R.sup.1 is hydrogen atom, a benzyl group, unsubstituted or substituted with a halogen atom or an alkyloxy group, or an alkyl group having 1 to 3 carbon atoms, R.sup.2 is hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R.sup.3 is acetyl group, ethyl group, carboxyl group or 4-methyl-2,5-dioxoimidazolidine-4-yl group, R.sup.4 is hydrogen atom, hydroxyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, carboxymethoxy group, nitro group, acetoamino group, a benzylozy group unsubstituted or substituted with a halogen atom, nitro group or an alkyloxy group or a group having the formula: --OR.sup.6, wherein R.sup.6 is an alkenyl group having 2 to 4 carbon atoms or an alkyl group having 2 to 3 carbon atoms having a halogen atom, cyano group or oxo group, R.sup.5 is hydrogen atom or methylenedioxy group together with R.sup.Type: GrantFiled: December 27, 1985Date of Patent: May 19, 1987Assignee: Kaken Pharmaceutical Co., Ltd.Inventors: Yoshitaka Ohishi, Michiko Nagahara, Norio Kajikawa, Motoyuki Yajima, Katsumi Nogimori, Shigeki Kurokawa
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Patent number: 4664693Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: A is selected from CH and N;B is selected from oxygen, sulfur, CH.sub.2 and the group N-Z wherein Z is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, benzyl and substituted benzyl;X, which may be the same or different, and X.sup.1, which be the same or different, are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.Type: GrantFiled: April 13, 1984Date of Patent: May 12, 1987Assignee: ICI Australia LimitedInventors: Graham J. Bird, Graeme J. Farquharson, Keith G. Watson, Murray L. Whitelaw
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Patent number: 4663347Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, 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 19, 1985Date of Patent: May 5, 1987Assignee: Merck Frosst Canada, Inc.Inventors: Joseph G. Atkinson, Yvan Guindon, Cheuk K. Lau
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Patent number: 4623737Abstract: The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and analogues thereof, which have demonstrated antiatherosclerotic activity.Type: GrantFiled: December 7, 1984Date of Patent: November 18, 1986Assignee: The Upjohn CompanyInventor: Ayako Yamashita
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Patent number: 4616035Abstract: Combating pests such as insects, arachnids and nematodes with novel N-oxalyl-N-methylcarbamic acid esters of the formula ##STR1## in which R represents alkyl, alkenyl, alkinyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenalkylthio, halogen, nitro, dialkylamino, alkylsulphinyl, alkylsulphonyl, cycloalkyl or a saturated, optionally substituted heterocyclic radical with one or more hetero-atoms from the group comprising O, S and N, or forms a ring which is fused onto the phenyl radical, optionally contains one or more hetero-atoms from the group comprising O, S and N and is optionally substituted.Type: GrantFiled: October 15, 1984Date of Patent: October 7, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Heywang, Engelbert Kuhle, Bernhard Homeyer
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Patent number: 4608371Abstract: The present invention provides novel insecticidal carbamate derivatives. The invention also provides a method for the control of insects.Type: GrantFiled: March 11, 1985Date of Patent: August 26, 1986Assignee: American Cyanamid CompanyInventors: Narayana M. Mallipudi, John G. Hollingshaus
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Patent number: 4602033Abstract: Aryl N-oxalyl-N-methyl-carbamates of the general formula ##STR1## in which X represents an alkoxy, alkenoxy, alkinoxy, aryloxy, alkylthio, alkenylthio, alkinylthio or arylthio radical, each of which may be optionally substituted or represents a radical of the general formula --N R.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl or aryl radical, each of which may be optionally substituted, or the radicals R.sup.3 and R.sup.4, together with the N atom to which they are bonded, form an optionally substituted heterocyclic ring, andR.sup.1 represents an aryl radical which is optionally substituted,are novel and find use as pesticides, especially for combating insects, acarids and nematodes.Type: GrantFiled: January 3, 1985Date of Patent: July 22, 1986Assignee: Bayer AktiengesellschaftInventors: Gerhard Heywang, Engelbert Kuhle, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4595769Abstract: Carbamate-sulfenyl-carbamoyl fluoride compounds are valuable insecticidal compositions and are also useful intermediates in the production of bis-carbamate compounds.Type: GrantFiled: April 20, 1984Date of Patent: June 17, 1986Assignee: Union Carbide CorporationInventor: Themistocles D. J. D'Silva
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Patent number: 4587353Abstract: There is described a process for producing N-chlorosulfenyl compounds of the formula ##STR1## in which R.sub.1 is alkyl, alkoxycarbonyl, alkoxycarbonylalkyl or 2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl, and R.sub.2 is alkyl or alkoxycarbonylalkyl, which process is based on the reaction of an amino compound of the formula ##STR2## with sulfur dichloride. The essential feature of the process is that the reaction of the amino compound of the above formula with the sulfur dichloride is performed in excess sulfur dichloride as solvent and in the absence of a base. The formed N-chlorosulfenyl compounds of the above formula are intermediates for insecticidal and acaricidal active substances.Type: GrantFiled: August 23, 1983Date of Patent: May 6, 1986Assignee: Ciba-Geigy CorporationInventor: Hansjakob Fah
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Patent number: 4579865Abstract: Compounds of the structure; ##STR1## and pharmaceutically acceptable salts thereof, wherein:R.sub.1 is H, alkyl, alkoxy, carboxyl, alkylcarboxy, trifluoromethyl, halogen, nitro or hydroxy;X is O, N, S or C;Y is O, N or S; andR.sub.2 is H, alkyl, cycloalkyl, aryl or heteroaryl useful in the treatment of ischemic heart disease and hypertriglyceridemia.Type: GrantFiled: March 28, 1984Date of Patent: April 1, 1986Assignee: USV Pharmaceutical Corp.Inventors: John H. Musser, Charles A. Sutherland
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Patent number: 4540708Abstract: A sulfenyl carbamate derivative represented by the formula ##STR1## wherein Ar represents ##STR2## R.sup.1 represents --X--COO--R.sup.3 or --Y--CN in which X and Y is each an alkylene group having 1 to 6 carbon atoms and R.sup.3 is an alkyl group having 1 to 8 carbon atoms; R.sup.2 represents --CH.sub.2 --.sub.n O--R.sup.4 in which R.sup.4 is an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group or a benzyl group; and n is an integer or 2 to 5.Type: GrantFiled: November 2, 1983Date of Patent: September 10, 1985Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventor: Hisashi Takao
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Patent number: 4532256Abstract: N-Methyl-carbamic acid esters of the formula ##STR1## wherein R.sub.1 is unsubstituted or substituted 2,3-dihydrobenzofuranyl, phenyl, naphthyl or ##STR2## R.sub.2 is hydroxyl, halogen, --OR.sub.1, C.sub.1 -C.sub.10 -alkoxy, C.sub.2 -C.sub.10 -alkenyloxy, C.sub.1 -C.sub.10 -dialkylamino or ##STR3## R.sub.3 is hydrogen, C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.3 -alkenyl, R.sub.4 is C.sub.1 -C.sub.6 -alkyl, --SR.sub.5, ##STR4## R.sub.5 is C.sub.1 -C.sub.6 -alkyl or C.sub.2 -C.sub.3 -alkenyl, R.sub.6 and R.sub.7 are each hydrogen or C.sub.1 -C.sub.6 -alkyl, andn is zero or 1.A process for producing these compounds and their use for combating pests are described.Type: GrantFiled: December 12, 1983Date of Patent: July 30, 1985Assignee: Ciba-Geigy CorporationInventor: Jozef Drabek
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Patent number: 4532339Abstract: A process for purifying an aminosulfenylcarbamate derivative represented by the formula (I) ##STR1## wherein Ar is ##STR2## and R.sup.1 and R.sup.2 are the same or different and are each C.sub.1-8 alkyl, C.sub.3-6 cycloalkyl, benzyl which is unsubstituted or substituted with halogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxy, phenyl which is unsubstituted or substituted with halogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxy, --X--COOR.sup.3 or --Y--CN (in which X and Y are each straight-chain or branched-chain alkylene and R.sup.3 is C.sub.1-8 alkyl or C.sub.3-6 cycloalkyl), R.sup.1 and R.sup.2, when taken together, represent a 5- or 6-membered heterocyclic ring which may contain a sulphur or oxygen atom, the process comprising bringing a solution of the unreacted carbamate-containing aminosulfenylcarbamate derivative of the formula (I) in a water-insoluble organic solvent into contact with an aqueous alkali solution or a mixture of alkali, water and a water-soluble organic solvent.Type: GrantFiled: March 2, 1984Date of Patent: July 30, 1985Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventor: Hisashi Takao
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Patent number: 4511578Abstract: A composition for controlling insects, particularly for controlling insects which infest plants and animals, which composition contains, as active ingredient, a compound of the formula I ##STR1## wherein R.sub.1 and R.sub.2 are straight-chain or branched-chain C.sub.1 -C.sub.4 -alkyl or C.sub.3 -C.sub.4 -cycloalkyl; and also processes and novel starting products for producing the compounds of the formula I.Novel compounds of the formula Ia ##STR2## wherein R.sub.1 is straight-chain or branched-chain C.sub.2 -C.sub.4 -alkyl or cyclopropyl.Type: GrantFiled: March 23, 1983Date of Patent: April 16, 1985Assignee: Ciba-Geigy CorporationInventor: Jozef Drabek
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Patent number: 4507292Abstract: Aryl N-oxalyl-N-methyl-carbamates of the general formula ##STR1## in which X represents an alkoxy, alkenoxy, alkinoxy, aryloxy, alkylthio, alkenylthio, alkinylthio or arylthio radical, each of which may be optionally substituted, or represents a radical of the general formula --N R.sup.3 R.sup.4, wherein R.sup.3 and R.sup.4 are identical or different and represent a hydrogen atom or an alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl or aryl radical, each of which may be optionally substituted,or the radicals R.sup.3 and R.sup.4, together with the N atom to which they are bonded, form an optionally substituted heterocyclic ring, andR.sup.1 represents an aryl radical which is optionally substituted,are novel and find use as pesticides, especially for combating insects, acarids and nematodes.Type: GrantFiled: January 27, 1983Date of Patent: March 26, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Heywang, Engelbert Kuhle, Wolfgang Behrenz, Ingeborg Hammann, Bernhard Homeyer
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Patent number: 4503069Abstract: N-Alkylidene-imino-oxycarbonyl-N-methyl-[2,2-dimethyl-2,3-dihydrobenzofuran yl(7)]-carbamates ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are each an alkyl group, or together they are an alkylene group.A process for producing these carbamates and their use for controlling pests are described.Type: GrantFiled: May 6, 1983Date of Patent: March 5, 1985Assignee: Ciba-Geigy CorporationInventor: Jozef Drabek
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Patent number: 4503256Abstract: Novel compounds of general formula I ##STR1## wherein R is a branched or unbranched alkyl, cycloalkyl, or aralkyl group, which group optionally contains or is substituted by a halogen or oxygen function, the oxygen function optionally being in the form of an alcohol or ether moiety;R.sub.1, R.sub.2, and R.sub.3, which may be the same or different, is hydrogen, an alkyl, acyl, or benzoyl group, which group optionally contains or is substituted by a halogen or oxygen function;R.sub.4 is hydrogen, an alkyl, alkenyl preferably being an allyl or prenyl group, or aralkyl group which group optionally contains or is substituted by an alkyl, aryl, halogen or oxygen function;R.sub.5 is hydrogen, an alkyl, aralkyl, acyl, or aryl group, which group optionally contains or is substituted by an alkyl, aryl, halogen, or oxygen function;except that R.sub.4 and R.sub.5 are not both hydrogen;and except for the compounds when R.sub.Type: GrantFiled: June 21, 1982Date of Patent: March 5, 1985Assignee: Noristan LimitedInventors: Theunis G. Fourie, Theodor G. Dekker, Friedrich O. Snyckers, Cornelis J. van der Schyf
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Patent number: 4490552Abstract: A novel process for the preparation of aryl esters of organic carboxylic acids in high isomer purity by decomposing a compound of the formula ##STR1## wherein Ar is an aryl radical, X is an acyloxy of an organic carboxylic acid and Y is selected from the group consisting of an acyloxy of an organic carboxylic acid and an anion of a strong organic and mineral acid in an aqueous media in the presence of a palladium salt or in the form of a two-phase reaction, wherein the aryl thallium salt is dissolved in water and the catalytic palladium salt is dissolved in a water-immiscible organic solvent and the reaction takes place with mixing.Type: GrantFiled: December 20, 1982Date of Patent: December 25, 1984Assignee: Rutgerswerke AGInventor: Ulrich Knips
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Patent number: 4473580Abstract: This invention pertains to some new organic compounds, to a process for preparing them, and to formulations of them suitable for pesticidal use. The invention is more particularly directed to imidic acid derivatives of N-thio(methyl)carbamates.Type: GrantFiled: October 25, 1982Date of Patent: September 25, 1984Assignee: The Upjohn CompanyInventors: Fred E. Dutton, Stephen J. Nelson
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Patent number: 4469882Abstract: A process for producing aromatic carbamates in high yield is described, which comprises reacting aromatic nitro compounds, organic compounds containing a hydroxy group, and carbon monoxide in the presence of a catalyst comprising: (1) a platinum group metal or its compound, (2) metallic vanadium or its compound, (3) metallic iron or its compound, (4) a halogen atom, and (5) a tertiary amine, wherein the amount of each component used and the composition are adjusted within specific ranges.Type: GrantFiled: June 23, 1982Date of Patent: September 4, 1984Assignee: Mitsubishi Chemical Industries LimitedInventors: Tsutomu Takeuchi, Mineo Nishi, Toshio Irie, Hirotaka Ryuto
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Patent number: 4464354Abstract: Monofunctional psoralen derivatives having the general formula ##STR1## wherein R represents a hydrogen atom, a lower alkyl group having from 1 to 4 atoms, preferably a methyl radical, or a lower alkoxy radical having from 1 to 4 carbon atoms, preferably a methoxy radical are described. The derivatives are photobiologically active and are useful in photochemical therapy and in cosmetics.Type: GrantFiled: February 24, 1983Date of Patent: August 7, 1984Assignee: Institut National de la Sante et de la Recherche MedicaleInventors: Emile Bisagni, Louis Dubertret, Jacqueline Moron, Dietrich Averbeck, Dora Papadopoulo, Jocelyne Blais, Paul Vigny, Maria N. Schwencke, Ethel Moustacchi, Silvano Nocentini, Francois Zajdela
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Patent number: 4463184Abstract: A novel process is provided for the preparation of carbofuran and certain intermediate products. 1,2-Cyclohexanedione is alkylated with a beta-methallyl compound and the resulting product subjected to a Claisen rearrangement/aromatization to provide the carbofuran phenol. Reaction of the phenol with methyl isocyanate converts the phenol to the desired carbofuran.Type: GrantFiled: September 30, 1982Date of Patent: July 31, 1984Assignee: Union Carbide CorporationInventor: David A. Hunt
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Patent number: 4459420Abstract: The present invention provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof from pyrogallol. Pyrogallol is converted to 3,6,7-benzofurantriol triacetate using zinc chloride and chloracetanitrile, then catalytically reduced and deactoxylated at the 3 position to yield the corresponding 2,3-dihydrofuran. This substance is subjected to a Fries rearrangement to the corresponding diol, the phenolic hydroxyl group of which is then selectively alkylated. This yields 6-hydroxy-7-alkoxy-5-benzofuranyl methyl ketone, a known intermediate for the production of 4-desmethoxy khellin and analogs thereof. This compound is then selectively alkoxylated at the 4 position using lead tetraacetate or thallium (III) nitrate in an alkanol solvent to yield known chemical intermediates in the preparation of khellin and analogs thereof.Type: GrantFiled: May 17, 1982Date of Patent: July 10, 1984Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
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Patent number: 4421693Abstract: An aminosulfenyl chloride derivative represented by the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are defined in the specification, which is useful as an intermediate for the preparation of a carbamate derivative represented by the formula (III): ##STR2## wherein R.sup.1 and R.sup.2 are the same as defined above, the carbamate derivative having an insecticidal, miticidal or nematocidal activity, is disclosed. A process for preparing the aminosulfenyl chloride of the formula (I), and a process for preparing the carbamate derivative of the formula (III) using the aminosulfenyl chloride of the formula (I) are also disclosed.Type: GrantFiled: March 25, 1982Date of Patent: December 20, 1983Assignee: Otsuka Chemical Co., Ltd.Inventors: Takeshi Goto, Takashi Soeda, Nobuyoshi Asai, Akira Tanaka
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Patent number: 4413005Abstract: This invention relates to carbamate derivatives represented by the formula (I): ##STR1## a process for preparing the derivatives and insecticides containing the derivatives.Type: GrantFiled: February 26, 1982Date of Patent: November 1, 1983Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventors: Takeshi Goto, Hisashi Takao, Takashi Soeda, Nobuyoshi Asai, Sadahiko Iida, Mitsuyasu Kawata, Norio Osaki, Norio Yasudomi, Tadateru Murata, Akira Tanaka
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Patent number: 4412071Abstract: The present invention provides novel antiatherosclerotic furobenzoxazinones, e.g., 4,9-dimethoxy-4H-furo[3,2-g][1,3]benzoxazin-4-ones. These compounds are structurally and pharmacologically related to khellin and are useful antiatherosclerotic agents.Type: GrantFiled: May 17, 1982Date of Patent: October 25, 1983Assignee: The Upjohn CompanyInventor: Ronald B. Gammill
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Patent number: 4410543Abstract: Carboxylated oxime-carbamates of the formula ##STR1## in which R.sub.1 represents a substituted or unsubstituted phenyl, naphthyl or dihydrobenzofuranyl radical and R.sub.2 and R.sub.3 independently of one another represent hydrogen or C.sub.1 -C.sub.4 -alkyl.A process for the preparation of these carboxylated oxime-carbamates, and their use in controlling pests, are described.Type: GrantFiled: March 19, 1982Date of Patent: October 18, 1983Assignee: Ciba-Geigy CorporationInventor: Jozef Drabek
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Patent number: 4399148Abstract: This invention relates to novel hydroxyarylalkyleneaminoaryl carbamate compounds and derivatives thereof and to their preparation. This invention is also directed to insecticidal compositions comprising an acceptable carrier and an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention as well as to a method of controlling insects by subjecting them to an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention.Type: GrantFiled: March 25, 1981Date of Patent: August 16, 1983Assignee: Union Carbide CorporationInventor: Charles A. Wilson, II
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Patent number: 4394383Abstract: A novel class of chemical compounds useful as pesticides consists of N-alkoxysulfenylcarbamate esters. The preparation of these compounds, their physical properties, formulations, and use to control both household insects and crop pests are exemplified.Type: GrantFiled: September 28, 1981Date of Patent: July 19, 1983Assignee: Regents of the University of CaliforniaInventors: Mitsuyasu Kawata, Noriharu Umetsu, Tetsuo R. Fukuto
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Patent number: 4393074Abstract: Fluorinated carbamoyl sulfides, such as N,N'[thiobis[(methylimino)carbonyloxy]]bis[2,2,2-trifluoroethanimidothioic acid], dimethyl ester, useful for control of insects.Type: GrantFiled: January 11, 1982Date of Patent: July 12, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: William J. Middleton
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Patent number: 4389528Abstract: An improved process for sulfenylating carbofuran in the presence of a solvent and acid acceptor with a disubstituted aminosulfenyl halide, in which the reaction is conducted in the presence of a catalytic amount of a complex of a lower alkylamine and sulfur dioxide, is disclosed and exemplified.Type: GrantFiled: February 22, 1982Date of Patent: June 21, 1983Assignee: FMC CorporationInventors: John W. Ager, Maurice J. C. Harding, Charles E. Hatch, III
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Patent number: 4386101Abstract: Unsymmetrical bis-carbamates of the formula ##STR1## wherein R.sub.1 is a phenyl, dihydrobenzofuranyl, naphthyl, pyrimidyl, pyrazolyl, triazolyl, quinolinyl or tetrahydroquinolinyl group, andR.sub.2 is a benzyl group,processes for producing them and their use for combating pests are described.Type: GrantFiled: November 9, 1981Date of Patent: May 31, 1983Assignee: Ciba-Geigy CorporationInventors: Jozef Drabek, Manfred Boger
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Patent number: 4366102Abstract: In a process for the preparation of an aromatic chloroformic acid ester by contacting a phenol and phosgene, the improvement wherein the reaction is carried out in a homogeneous liquid phase at a temperature of 60.degree. to 180.degree. C. in the presence of organic phosphorus compound of the formulaR.sup.1 R.sup.2 R.sup.3 PR.sup.4.sub.n X.sub.nin whichR.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, alkyl, alkenyl, aralkyl, aryl or halogen and two of the said radicals together with the phosphorus atom can form a 5-membered or 6-membered phosphorus-containing saturated or unsaturated heterocyclic radical,X represents OH, homopolar-bonded halogen or an inorganic or organic acid anion,R.sup.4 denotes hydrogen or alkyl or, if X denotes halogen, can also denote halogen and n denotes 0 or 1,and in which, furthermore,R.sup.4 and X together can represent oxygen or sulfur.Type: GrantFiled: May 6, 1981Date of Patent: December 28, 1982Assignee: Bayer AktiengesellschaftInventors: Gunter Rauchschwalbe, Heinz U. Blank, Karl Mannes, Dietmar Mayer
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Patent number: 4329293Abstract: An improved process is disclosed for sulfenylating carbamates in the presence of a solvent and acid acceptor, in which the reaction between a carbamate and a sulfenyl halide is conducted in the presence of a catalytic amount of a complex of a lower alkylamine and sulfur dioxide. Several methods for preparing and utilizing the complex in the reaction are disclosed and exemplified.Type: GrantFiled: October 31, 1980Date of Patent: May 11, 1982Assignee: FMC CorporationInventors: John W. Ager, Maurice J. C. Harding, Charles E. Hatch, III