1,3-thiazines Patents (Class 544/53)
  • Patent number: 4614798
    Abstract: 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: Grant
    Filed: April 9, 1985
    Date of Patent: September 30, 1986
    Assignee: Vetamix
    Inventors: Richard L. Elliott, Paul H. Ruehle
  • Patent number: 4468395
    Abstract: 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: Grant
    Filed: May 20, 1982
    Date of Patent: August 28, 1984
    Assignee: Schering, Aktiengesellschaft
    Inventors: VorbruHelmut, Walter Elger, Michael-Harold Town, Ekkehard Schillinger
  • Patent number: 4414211
    Abstract: 5-Membered, 6-membered and 7-membered heterocyclic derivatives of guanidine having hypoglycemic activity.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: November 8, 1983
    Assignee: McNeilab, Inc.
    Inventor: Chris R. Rasmussen
  • Patent number: 4391814
    Abstract: 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: Grant
    Filed: December 23, 1981
    Date of Patent: July 5, 1983
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Vorbruggen
  • Patent number: 4390712
    Abstract: 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: Grant
    Filed: August 31, 1981
    Date of Patent: June 28, 1983
    Assignee: Degussa AG
    Inventors: Alfons Karl, Wolfgang Buder, Peter Kleinschmit
  • Patent number: 4347372
    Abstract: 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: Grant
    Filed: August 28, 1979
    Date of Patent: August 31, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: 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
  • Patent number: 4339444
    Abstract: Novel acyclic and heterocyclic oxime phosphate compounds have been found to exhibit insecticidal, miticidal and nematocidal activity.
    Type: Grant
    Filed: April 1, 1981
    Date of Patent: July 13, 1982
    Assignee: Union Carbide Corporation
    Inventors: Themistocles D. J. D'Silva, Leonard E. Hodakowski
  • Patent number: 4333929
    Abstract: 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: Grant
    Filed: January 19, 1981
    Date of Patent: June 8, 1982
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4315019
    Abstract: 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: Grant
    Filed: August 18, 1980
    Date of Patent: February 9, 1982
    Assignee: Science Union et Cie
    Inventors: Charles Malen, Pierre Roger, Michel Laubie
  • Patent number: 4298613
    Abstract: 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: Grant
    Filed: May 5, 1980
    Date of Patent: November 3, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Gerald E. Lepone
  • Patent number: 4282356
    Abstract: 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: Grant
    Filed: June 10, 1980
    Date of Patent: August 4, 1981
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4267345
    Abstract: 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: Grant
    Filed: April 19, 1979
    Date of Patent: May 12, 1981
    Assignee: Science Union et Cie
    Inventors: Charles E. Malen, Pierre Roger, Michel Laubie
  • Patent number: 4258181
    Abstract: 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: Grant
    Filed: May 7, 1979
    Date of Patent: March 24, 1981
    Assignee: American Cyanamid Company
    Inventors: Keith C. Murdock, Frederick E. Durr
  • Patent number: 4250173
    Abstract: 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: Grant
    Filed: November 14, 1979
    Date of Patent: February 10, 1981
    Assignee: Beecham Group Limited
    Inventor: Barrie C. C. Cantello
  • Patent number: 4232025
    Abstract: Reaction products of tetrahydro-2-(nitromethylene)-2H-1,3-thiazine and certain oxidized polysaccharides, useful as insecticides.
    Type: Grant
    Filed: May 7, 1979
    Date of Patent: November 4, 1980
    Assignee: Shell Oil Company
    Inventors: James R. Sanborn, Charles H. Tieman
  • Patent number: 4210545
    Abstract: 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: Grant
    Filed: March 30, 1979
    Date of Patent: July 1, 1980
    Assignee: Standard Oil Company (Indiana)
    Inventors: Richard J. Lee, Eugene E. Richardson
  • Patent number: 4208327
    Abstract: 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: Grant
    Filed: April 3, 1979
    Date of Patent: June 17, 1980
    Assignee: G. D. Searle & Co.
    Inventor: Peter K. Yonan
  • Patent number: 4105657
    Abstract: 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: Grant
    Filed: April 8, 1977
    Date of Patent: August 8, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Toni Dockner, Herbert Toussaint, Martin Decker
  • Patent number: 4102890
    Abstract: 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: Grant
    Filed: August 11, 1976
    Date of Patent: July 25, 1978
    Assignee: Science-Union et Cie, Societe Francaise de Recherche Medicale
    Inventors: Charles Malen, Monique Desnos, Michel Laubie, Jean-Claude Poignant
  • Patent number: 4099000
    Abstract: 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: Grant
    Filed: March 30, 1976
    Date of Patent: July 4, 1978
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe
  • Patent number: 4079179
    Abstract: 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: Grant
    Filed: March 30, 1976
    Date of Patent: March 14, 1978
    Assignee: Merck & Co., Inc.
    Inventors: Burton G. Christensen, Ronald W. Ratcliffe
  • Patent number: 4061749
    Abstract: 5,6-Dihydro-4H-1,3-thiazine-2-carboxaldehyde oxime useful as an insecticide.
    Type: Grant
    Filed: July 6, 1976
    Date of Patent: December 6, 1977
    Assignee: Shell Oil Company
    Inventor: James E. Powell
  • Patent number: 4061631
    Abstract: 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: Grant
    Filed: January 22, 1976
    Date of Patent: December 6, 1977
    Assignee: Ciba-Geigy Corporation
    Inventor: Jean Rody
  • Patent number: 4061854
    Abstract: 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: Grant
    Filed: June 4, 1976
    Date of Patent: December 6, 1977
    Assignee: Shionogi & Co., Ltd.
    Inventor: Masayuki Narisada
  • Patent number: 4054652
    Abstract: Dihydro- and tetrahydro-iminothiazines are inhibitors of indoleamine-N-methyl transferase in vivo.
    Type: Grant
    Filed: June 15, 1976
    Date of Patent: October 18, 1977
    Assignee: Merck & Co., Inc.
    Inventors: Clarence S. Rooney, Joshua Rokach, Edward J. Cragoe, Jr.
  • Patent number: 4049807
    Abstract: 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: Grant
    Filed: May 28, 1975
    Date of Patent: September 20, 1977
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilfried Paulus, Hans Scheinpflug, Hermann Genth