1,3-thiazines Patents (Class 544/53)
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Patent number: 4614798Abstract: In the preparation of 2,6-dimethylphenylisothiocyanate by reacting N-(2,6-dimethylphenyl)acetamide with sodium hydride in an organic solvent to form the corresponding anion of said amide, then reacting carbon disulfide with said anion to form said 2,6-dimethylphenylisothiocyanate, unexpectedly high yields are obtained by using as the organic solvent tetrahydrofuran or a mixture of N,N-dimethylacetamide and toluene. 2,6-Dimethylphenylisothiocyanate is an intermediate in the preparation of xylazine useful, for instance, as a sedative, an analgesic and muscle relaxant.Type: GrantFiled: April 9, 1985Date of Patent: September 30, 1986Assignee: VetamixInventors: Richard L. Elliott, Paul H. Ruehle
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Patent number: 4468395Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is a prostaglandin or prostacyclin residue;Y is oxygen, sulfur, imino, or N-(C.sub.1 -C.sub.4 -alkyl) imino;Q is (CR.sub.6 R.sub.7).sub.p wherein p is an integer of 0 to 3;R.sub.2 is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; C.sub.1 -C.sub.4 -alkoxycarbonyl; benzyloxycarbonyl; cyano; or di-C.sub.1 -C.sub.4 -alkylaminocarbonyl;R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 each independently is hydrogen; alkyl of 1-6 carbon atoms optionally substituted by hydroxy or amino; or aryl; andR.sub.3 and R.sub.4 together form a trimethylene, tetramethylene, or 1,3-butadienylene group when R.sub.2 and R.sub.5 together represent a direct bond;have valuable pharmacological properties, e.g., as blood-pressure-lowering or abortive agents.Type: GrantFiled: May 20, 1982Date of Patent: August 28, 1984Assignee: Schering, AktiengesellschaftInventors: VorbruHelmut, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
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Patent number: 4414211Abstract: 5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.Type: GrantFiled: March 14, 1980Date of Patent: November 8, 1983Assignee: McNeilab, Inc.Inventor: Chris R. Rasmussen
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Patent number: 4391814Abstract: Compounds of Formula I ##STR1## wherein R.sub.1 is the residue of an antiphlogistically effective carboxylic acid of the formula R.sub.1 COOH,n is an integer 1, 2, or 3, andX is oxygen, sulfur, or optionally alkylated nitrogenhave valuable antiinflammatory activity.Type: GrantFiled: December 23, 1981Date of Patent: July 5, 1983Assignee: Schering AktiengesellschaftInventor: Helmut Vorbruggen
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Aqueous solution of cationic organosilicon compounds and process for the production of the solutions
Patent number: 4390712Abstract: There are prepared aqueous solutions of cationic organosilicon compounds which are produced by reacting an alkoxysilylalkyl halide of the formula (RO).sub.3-n R.sub.n.sup.1 --Si--R.sup.2 --X (I) where R is C.sub.1 to C.sub.5 alkyl, methoxy, ethoxy, phenyl, or C.sub.5 to C.sub.8 cycloalkyl; R.sup.1 is C.sub.1 to C.sub.5 alkyl, phenyl, tolyl, benzyl, or C.sub.5 to C.sub.8 cycloalkyl; R.sup.2 is a divalent ethylenic double bond free hydrocarbon group having 3 to 8 carbon atoms, n is zero, 1 or 2 and X is chlorine, bromine, or iodine with a tertiary amine of the formula R.sup.3 NR.sup.4 R.sup.5 (II) where R.sup.3, R.sup.4, and R.sup.5 are the same or different and each is an alkyl group or benzyl in which the number of carbon atoms of the alkyl group or the alkyl groups together is up to 30 or R.sup.4 and .sup.Type: GrantFiled: August 31, 1981Date of Patent: June 28, 1983Assignee: Degussa AGInventors: Alfons Karl, Wolfgang Buder, Peter Kleinschmit -
Patent number: 4347372Abstract: A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxime derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts and the like), as desired, can be treated with these oxime derivatives, which are used as a dressing.Type: GrantFiled: August 28, 1979Date of Patent: August 31, 1982Assignee: Ciba-Geigy CorporationInventors: Alfons Lukaszczyk, Henry Martin, Peter J. Diel, Werner Fory, Karl Gatzi, Haukur Kristinsson, Beat Muller, Rene Muntwyler, Johannes P. Pachlatko, Hermann Rempfler, Rolf Schurter, Henry Szczepanski
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Patent number: 4339444Abstract: Novel acyclic and heterocyclic oxime phosphate compounds have been found to exhibit insecticidal, miticidal and nematocidal activity.Type: GrantFiled: April 1, 1981Date of Patent: July 13, 1982Assignee: Union Carbide CorporationInventors: Themistocles D. J. D'Silva, Leonard E. Hodakowski
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Patent number: 4333929Abstract: A compound of formula (II) or a pharmaceutically acceptable acid addition salt thereof ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represents C.sub.1-6 alkyl; R.sup.5 represents hydrogen or C.sub.1-6 alkyl; R.sup.6 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.5 and R.sup.6 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.1-6 alkoxycarbonyl; and R.sup.7 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.Type: GrantFiled: January 19, 1981Date of Patent: June 8, 1982Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
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Patent number: 4315019Abstract: This invention relates to novel substituted aryl lower alkamine and more precisely to arylmethylamine, the methyl group of which is substituted with one more polyfluoromethyl radicals.This invention also relates to the process for producing said compounds.The resulting compounds have pharmacological utility and may be used as a drug in human and veterinary medicine.Type: GrantFiled: August 18, 1980Date of Patent: February 9, 1982Assignee: Science Union et CieInventors: Charles Malen, Pierre Roger, Michel Laubie
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Patent number: 4298613Abstract: Heterocyclic sulfenamides, such as N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-trifluoromethyl)ph enyl]-3-nitro-2-pyridinesulfenamide, are useful as miticides, insecticides, fungicides and ovicides.Type: GrantFiled: May 5, 1980Date of Patent: November 3, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Gerald E. Lepone
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Patent number: 4282356Abstract: A compound, with hypoglycaemic activity, having formula (II) or a pharmaceutically acceptable quaternary ammonium or acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur;n represents zero or 1;R.sup.7 represents hydrogen or C.sub.1-6 alkyl;R.sup.1 and R.sup.2 are the same or different and represent hydrogen, C.sub.1-6 alkyl, phenyl, benzyl, or C.sub.3-6 cycloalkyl;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.1-6 alkoxycarbonyl; andR.sup.Type: GrantFiled: June 10, 1980Date of Patent: August 4, 1981Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
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Patent number: 4267345Abstract: Certain arylmethyl amines have been prepared wherein the "methyl" carbon is substituted with a polyfluoroalkyl radical. The compounds form acid addition salts, exist in resolvable stereoisomeric forms, and are useful for treating hypertension. Formulations for human and veterinary medicine are described, as well as methods of use.Type: GrantFiled: April 19, 1979Date of Patent: May 12, 1981Assignee: Science Union et CieInventors: Charles E. Malen, Pierre Roger, Michel Laubie
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Patent number: 4258181Abstract: This disclosure describes anthracene-9,10-bis-carbonyl-hydrazones and derivatives thereof useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers.Type: GrantFiled: May 7, 1979Date of Patent: March 24, 1981Assignee: American Cyanamid CompanyInventors: Keith C. Murdock, Frederick E. Durr
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Patent number: 4250173Abstract: A compound, with hypolgycaemic activity, having formula (II) or a pharmaceutically acceptable quaternary ammonium or acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur; n.sub.7 represents zero or 1;R.sup.7 represents hydrogen or C.sub.1-6 alkyl;R.sup.1 and R.sup.2 are the same or different and represent hydrogen, C.sub.1-6 alkyl, phenyl, benzyl, or C.sub.3-6 cycloalkyl;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.Type: GrantFiled: November 14, 1979Date of Patent: February 10, 1981Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
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Patent number: 4232025Abstract: Reaction products of tetrahydro-2-(nitromethylene)-2H-1,3-thiazine and certain oxidized polysaccharides, useful as insecticides.Type: GrantFiled: May 7, 1979Date of Patent: November 4, 1980Assignee: Shell Oil CompanyInventors: James R. Sanborn, Charles H. Tieman
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Patent number: 4210545Abstract: Lubricant additives imparting oxidation inhibiting properties to lubricant compositions, are synthesized by reacting thioxamide, saturated aliphatic aldehyde of from 1 to about 20 carbon atoms, and an olefin of at least 8 carbon atoms, in the presence of a boron trifluoride catalyst.Type: GrantFiled: March 30, 1979Date of Patent: July 1, 1980Assignee: Standard Oil Company (Indiana)Inventors: Richard J. Lee, Eugene E. Richardson
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Patent number: 4208327Abstract: 5-Aryl-1-(2-oxazolin-2-yl)-1H-1,4-benzodiazepines and related compounds having the formula ##STR1## wherein A is methylene or carbonyl; Z is oxygen, imino or thio; R.sup.1, R.sup.2, and R.sup.3 independently are hydrogen, halogen, trifluoromethyl or nitro; R.sup.4 is hydrogen or hydroxy; and n is positive integer from 1 to 3 inclusive are disclosed. These compounds are useful because of their central nervous system activity.Type: GrantFiled: April 3, 1979Date of Patent: June 17, 1980Assignee: G. D. Searle & Co.Inventor: Peter K. Yonan
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Patent number: 4105657Abstract: Production of N-alkylated cyclic alkylenimines by reaction of cyclic alkylenimines with an alcohol or ether in the gas phase in the presence of a high-area SiO.sub.2 /P.sub.2 O.sub.5 catalyst.Type: GrantFiled: April 8, 1977Date of Patent: August 8, 1978Assignee: BASF AktiengesellschaftInventors: Toni Dockner, Herbert Toussaint, Martin Decker
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Patent number: 4102890Abstract: Cyclopropylmethylamines which are substituted on the 2-position of nitrogen heterocycles so as to provide new compounds of the formula ##STR1## wherein A is oxygen, sulfur, or nitrogen; the other "R" variables in general are hydrogen, lower-alkyl, cyclopropyl, or lower-alkyl substituted cyclopropyl; and the n's are the numbers 0 to 3, inclusive, and acid addition salts thereof, are disclosed. The compounds are cardiovascular agents, which are depressive of the central nervous system. Their effects include hypnosis, analgesia, and neuro-modulation. They can be used as anti-hypertensive agents.Type: GrantFiled: August 11, 1976Date of Patent: July 25, 1978Assignee: Science-Union et Cie, Societe Francaise de Recherche MedicaleInventors: Charles Malen, Monique Desnos, Michel Laubie, Jean-Claude Poignant
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Patent number: 4099000Abstract: A novel total synthesis process is provided, yielding cephalosporin or penicillin compounds. The process uses as starting material a glycine ester, which first is reacted to yield a dihydrothiazine, and subsequently condensed with azidoacetyl chloride to form the cepham nucleus, then dehydrated to yield the desired 3-unsaturation. Subsequent reduction and acylation steps are analogous to known chemistry. The end products are antibacterial agents.Type: GrantFiled: March 30, 1976Date of Patent: July 4, 1978Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Ronald W. Ratcliffe
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Patent number: 4079179Abstract: Cephalosporin compounds having a loweralkoxy or loweralkylthio substituent in the 6-position are prepared by a multi-step total synthesis route using as starting material a glycine ester, which first is reacted to yield a dihydrothiazine, and subsequently condensed with azidoacetyl chloride to form the cepham nucleus, then dehydrated to yield the desired 3-unsaturation. Subsequent reduction and acylation steps are analogous to known chemistry, and yield the novel 6-loweralkoxy- or loweralkylthio-7-amino intermediates and the antibacterially active 6-loweralkoxy or loweralkylthio-7-acylamido end products.Type: GrantFiled: March 30, 1976Date of Patent: March 14, 1978Assignee: Merck & Co., Inc.Inventors: Burton G. Christensen, Ronald W. Ratcliffe
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Patent number: 4061749Abstract: 5,6-Dihydro-4H-1,3-thiazine-2-carboxaldehyde oxime useful as an insecticide.Type: GrantFiled: July 6, 1976Date of Patent: December 6, 1977Assignee: Shell Oil CompanyInventor: James E. Powell
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Patent number: 4061631Abstract: New 1-aza-4-thiacyclohexane-4,4-dioxide derivatives are used alone or in combination with other stabilizers for stabilizing organic materials. The new compounds are prepared by reacting substituted diallylsulfides with ammonia, amines or hydrazines.Type: GrantFiled: January 22, 1976Date of Patent: December 6, 1977Assignee: Ciba-Geigy CorporationInventor: Jean Rody
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Patent number: 4061854Abstract: Dihydroethanoanthracene derivatives of the formula: ##STR1## [wherein R represents a hydrogen or C.sub.1 -C.sub.4 alkyl; R.sup.1 represents a group ##STR2## (in which A represents a C.sub.2 -C.sub.4 alkylene optionally substituted by one or two C.sub.1 14 C.sub.4 alkyls or by a phenyl; and Y represents an oxygen, sulfur, or imino) or group--COO--A--NH.sub.2(in which A is as defined above)]and their pharmaceutically acceptable acid addition salts, are useful as antidepressants or synthetic intermediates therefor.Type: GrantFiled: June 4, 1976Date of Patent: December 6, 1977Assignee: Shionogi & Co., Ltd.Inventor: Masayuki Narisada
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Patent number: 4054652Abstract: Dihydro- and tetrahydro-iminothiazines are inhibitors of indoleamine-N-methyl transferase in vivo.Type: GrantFiled: June 15, 1976Date of Patent: October 18, 1977Assignee: Merck & Co., Inc.Inventors: Clarence S. Rooney, Joshua Rokach, Edward J. Cragoe, Jr.
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Patent number: 4049807Abstract: 2-AMINO-1,3-THIAZINES HAVING THE FORMULA ##STR1## wherein R.sup.1 is optionally substituted carbocyclic or heterocyclic aromatic andR.sup.2 is hydrogen, alkyl, alkenyl or optionally substituted substituted carbocyclic aromatic.The 2-amino-1,3-thiazines are useful for combatting fungi and bacteria, for example, in plant protection for combatting archimycetes, phycomycetes and the like, are prepared by reacting beta-halogeno-ethyl-ketone having the formulaR.sup.1 --CO--CH.sub.2 --CH.sub.2 --HalwhereinHal is halogen andR.sup.1 is as defined above, with thiourea of the general formula ##STR2## wherein R.sup.2 is as defined above.Type: GrantFiled: May 28, 1975Date of Patent: September 20, 1977Assignee: Bayer AktiengesellschaftInventors: Wilfried Paulus, Hans Scheinpflug, Hermann Genth