Patents Examined by Alton D. Rollins
  • Patent number: 4490539
    Abstract: A process for the preparation of 1,2,4-triazole by reacting hydrazine, formic acid and formamide and/or ammonia in a molar ratio of 1 mole of hydrazine to 1 to 3 moles of formic acid to 1 to 2 moles of formamide and/or ammonia at a temperature of 140.degree. to 220.degree. C. The main advantage of the process of the invention resides in obtaining 1,2,4-triazole with an improved yield and purity.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: December 25, 1984
    Assignee: Nehezvegyipari Kutato Intezet
    Inventors: Janos Besan, Miklos Kovacs, Laszlo Kulcsar, Ferenc Maier, Jozsef Pernyeszi
  • Patent number: 4487776
    Abstract: The invention relates to azolyl-phenoxy-tetrahydrofuran-2-ylidene-methanes defined herein under formula (I). Also included in the invention are compositions containing said compounds of formula (I) and methods for the use of such compounds and compositions as antimycotic agents. The invention further includes methods for the manufacture of the compounds of formula (I).
    Type: Grant
    Filed: January 27, 1983
    Date of Patent: December 11, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Ludwig Elbe, Manfred Jautelat, Karl H. Buchel, Klaus Schaller, Manfred Plempel
  • Patent number: 4486218
    Abstract: 1-Vinyltriazole compounds of the formula ##STR1## wherein R.sup.1 is alkyl, substituted alkyl, cycloalkyl, aryl or substituted aryl;R.sup.2 is alkyl;R.sup.3 is alkyl, cycloalkyl, cycloalkenyl, substituted cycloalkenyl, alkenyl, aryl or substituted aryl; orR.sup.2 and R.sup.3, together with the carbon to which they are bonded, represent cycloalkenyl, substituted cycloalkenyl, cycloalkyl or substituted cycloalkyl;X is the group ##STR2## or, alternatively, X may represent a keto group provided that when X is a keto group, R.sup.1 is alkyl, substituted alkyl, cycloalkyl, or substituted cycloalkyl;R.sup.4 is hydrogen, alkyl, aralkyl, substituted aralkyl, acyl, carbamoyl or substituted carbamoyl;R.sup.5 is hydrogen, alkyl, aralkyl or substituted aralkyl;and acid addition salts and metal salt complexes thereof; are outstandingly effective plant growth regulants and as fungicides.
    Type: Grant
    Filed: August 20, 1981
    Date of Patent: December 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
  • Patent number: 4483862
    Abstract: Compounds of the formula ##STR1## or a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein m and n are independently 0, 1, 2, 3 or 4; method for their use in combatting fungal infections in plants, seeds and animals, including humans; and pharmaceutical and agricultural compositions containing said compounds or salts.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: November 20, 1984
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4483863
    Abstract: Compounds of the general formula: ##STR1## wherein Ar is dichlorophenyl and Het is 1-methyltetrazol-5-yl, 1,2,4-triazol-3-yl, 1-methyl-1,2,4-triazol-3-yl, 2-methyl-1,2,4-triazol-3-yl, 4-methyl-1,2,4-triazol-3-yl, imidazol-2-yl or 1-methylimidazol-2-yl and their pharmaceutically acceptable acid addition salts are antifungal agents in humans and other animals.
    Type: Grant
    Filed: January 20, 1984
    Date of Patent: November 20, 1984
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Geoffrey Gymer
  • Patent number: 4482493
    Abstract: A method for preparing a benzoquinone represented by the general formula: ##STR1## where each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is a hydrogen atom, an alkyl group or an aryl group, which comprises reacting a phenol represented by the general formula: ##STR2## where R.sup.1, R.sup.2 R.sup.3 and R.sup.4 are as defined above, with hydrogen peroxide in the presence of a ruthenium catalyst.
    Type: Grant
    Filed: October 18, 1983
    Date of Patent: November 13, 1984
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Matsumoto, Satoru Ito
  • Patent number: 4482558
    Abstract: Compounds of the general formula ##STR1## or a pharmaceutically acceptable acid addition salt thereof, wherein R is naphthyl, biphenylyl, phenyl or substituted phenyl; and R.sup.1 is ##STR2## where X is O or S, R.sup.2 is H, or C.sub.1 -C.sub.4 alkyl and R.sup.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, optionally mono- or disubstituted phenyl, benzyl or Het and Het is pyridyl, pyrimidinyl or pyrazinyl; said substituents being halo, CF.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or hydroxy, or R.sup.2 and R.sup.3 taken together complete a 1-pyrrolidinyl or piperidino ring; methods for their use in combatting fungal infections in plants and animals, including humans; pharmaceutical and agricultural compositions containing them and intermediates useful in their preparation.
    Type: Grant
    Filed: June 3, 1983
    Date of Patent: November 13, 1984
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4482547
    Abstract: This invention relates to substituted-1,3,4-benzotriazepines of the formula ##STR1## wherein X and Y are each independently hydrogen, lower alkyl, halogen, lower alkoxy, nitro and hydroxyl; R.sub.1 and R.sub.3 are each independently hydrogen or alkyl; R.sub.2 is hydrogen, lower alkyl, cycloalkyl lower alkyl, phenyl, Ar lower alkyl, hydroxyl and sulfhydryl; m and n are each independently integers of 0 or 1 and when m is 0, n is 1 and vice-versa; and p and q are independently integers of 1 or 2. Also included in the invention are the substituted-1,3,4-benzotriazepine derivatives of tautomeric form when the substituent for R.sub.1 and/or R.sub.3 in the above formula is hydrogen. The compound of this invention may be used as antihypertensive agents.
    Type: Grant
    Filed: August 26, 1982
    Date of Patent: November 13, 1984
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Lawrence L. Martin, Linda L. Setescak
  • Patent number: 4482564
    Abstract: Disclosed are triazolyl-substituted propane derivatives useful in the treatment of fungal diseases of humans and animals. Also disclosed are the processes for preparing the compounds, pharmaceutical compositions containing them, and the method of treating fungal diseases with said compounds.
    Type: Grant
    Filed: June 3, 1983
    Date of Patent: November 13, 1984
    Assignee: Schering Corporation
    Inventors: John J. Wright, Alan B. Cooper
  • Patent number: 4481218
    Abstract: The novel compound according to the invention 3-(2,2,2-trimethylhydrazinium)-propionate has the general formula:(CH.sub.3).sub.3 NNHCH.sub.2 CH.sub.2 COO.2H.sub.2 O.The method for preparing this novel compound comprises passing a solution of 3-(2,2,2-grimethylhydrazinium) alkylpropionate of the formula:X.sup.- (CH.sub.3).sub.3 N.sup.+ NHCH.sub.2 CH.sub.2 COORwherein X is Cl, Br, I, CH.sub.3 SO.sub.4, R is a loawer alkyl, through a column with a strongly-basic anion exchange resin, followed by isolation of the desired product. The growth stimulator for animals and fowl contains the novel compound, i.e. 3-(2,2,2-trimethylhydrazinium)-propionate as the active principle.
    Type: Grant
    Filed: July 8, 1982
    Date of Patent: November 6, 1984
    Assignee: Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi SSR
    Inventors: Anatoly Eremeev, Ivars Y. Kalvinsh, Valentina G. Semenikhina, Edvards E. Liepinsh, Yan Y. Latvietis, Paul P. Anderson, Elena B. Astapenok, Yazep Y. Spruzh, Petr T. Trapentsiers, Gennady I. Podoprigora, Solomon A. Giller, deceased
  • Patent number: 4481356
    Abstract: A novel reagent useful for preparing adducts of diene so that the diene may be assayed by gas liquid chromatography utilizing an electron capture detection system.
    Type: Grant
    Filed: April 28, 1982
    Date of Patent: November 6, 1984
    Assignee: The Upjohn Company
    Inventor: Terry J. Gilbertson
  • Patent number: 4480105
    Abstract: Novel compounds of the formula II ##STR1## are described, in which M.sub.1 and M.sub.2 individually are --OH or together are --O--, X is --NO.sub.2, --OR', --SR' or SO.sub.2 R' and the (R')s independently of one another are C.sub.1-20 -alkyl, C.sub.3-5 -alkenyl, C.sub.3-5 -alkynyl, C.sub.2-4 -monohydroxyalkyl, C.sub.1-12 -halogenoalkyl, benzyl, C.sub.5-12 -cycloalkyl, phenyl, carboxyphenyl, halogenophenyl, nitrophenyl, alkyl- or alkoxy-phenyl each having 1-4 C atoms in the alkyl or alkoxy moieties, or acetylaminophenyl, such as for example 3-n-butylthio-5-nitrophthalic anhydride. The compounds (II) in which M.sub.1 and M.sub.2 together are --O-- are suitable as sensitizers for photo-crosslinkable polymers or as initiators for the photopolymerization of ethylenically unsaturated compounds or for the photochemical crosslinking of polyolefins, and those where M.sub.1 and M.sub.2 are --OH are useful intermediates for those wherein M.sub.1 and M.sub.2 together are --O--.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: October 30, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Fischer, Vratislav Kvita, Hans Zweifel
  • Patent number: 4478750
    Abstract: A 1,2,3,4,5,6-hexahydro-6-phenyl-azepino[4,5-b]indole, or a pharmaceutically acceptable acid addition salt thereof is a useful neuroleptic, anti-depressant and anti-allergic agent.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: October 23, 1984
    Assignee: Sandoz Ltd.
    Inventor: Fulvio Gadient
  • Patent number: 4477675
    Abstract: The process of preparing a compound of the formula: ##STR1## wherein, Y and Z are each H, alkyl, halo, alkoxy, trifluoromethyl, hydroxy, alkanoyloxy, or alkanoylamino;X is F, Cl, Br, or NR.sub.1 R.sub.2 wherein R.sub.1 and R.sub.2 are each hydrogen, alkyl, alkynyl, alkenyl, cycloalkyl, aryl or aralkyl; andR is H, alkyl, cycloalkyl, or aralkyl; which comprises the step of oxidation of the corresponding 3-desoxy compound.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: October 16, 1984
    Assignee: USV Pharmaceutical Corporation
    Inventors: Joseph Auerbach, Frederick A. Golec, Jr.
  • Patent number: 4477676
    Abstract: Mono-, bis- and tris-indolyl-substituted furanones useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared respectively by: the interaction of an indole with mucochloric acid; the interaction of an indole with a 4-mono(indolyl)-substituted 4-oxo-2-butenoic acid; and by the interaction of an indole with a 2,4-bis(indolyl)-substituted 4-oxobutanoic acid or with a 3,5-bis(indolyl)-substituted furanone.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: October 16, 1984
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4477459
    Abstract: Compounds of the formula: ##STR1## wherein R is lower alkyl or lower alkenyl are fungicidal.
    Type: Grant
    Filed: July 29, 1983
    Date of Patent: October 16, 1984
    Assignee: Chevron Research Company
    Inventor: Edward I. Aoyagi
  • Patent number: 4477463
    Abstract: Antiinflammatory and/or analgesic 1-alkyl-4,5-diaryl-2-fluoroalkyl-1H-pyrroles, such as 4,5-bis(4-methoxyphenyl)-1-methyl-2-trifluoromethyl-1H-pyrrole, useful for treating arthritis and related diseases and/or relieving pain.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: October 16, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Saul C. Cherkofsky
  • Patent number: 4476133
    Abstract: 4,1-Benzoxazepines of the following formula are novel central nervous system: ##STR1## wherein R is hydrogen or C.sub.1 to C.sub.5 alkyl;X is hydrogen, halogen, or nitro;Y is phenyl, 2-halophenyl, 4-halophenyl, 2-trifluoromethylphenyl, or pyridyl;and ##STR2## is a group of the formula: ##STR3## (wherein Q is oxygen, sulfur, or hydrazono, with a proviso that, when Y is phenyl or 2-halophenyl and R is hydrogen, Q is neither oxygen nor sulfur;R.sup.1 is hydrogen, halogen, C.sub.1 to C.sub.5 alkyl, C.sub.1 to C.sub.5 alkylthio, 5- or 6-membered heterocycle or C.sub.1 to C.sub.5 alkyl substituted by a substituent selected from the group consisting of halogen, hydroxy, mercapto, C.sub.1 to C.sub.5 alkoxy, C.sub.1 to C.sub.5 alkanoyloxy, C.sub.1 to C.sub.5 alkylthio, C.sub.7 to C.sub.9 aralkyldithio, C.sub.2 to C.sub.10 dialkylamino, C.sub.3 to C.sub.15 dialkylaminoalkoxy, C.sub.3 to C.sub.15 dialkylaminoalkylthio, and 5- or 6-membered heterocycle;R.sup.2 is C.sub.1 to C.sub.5 alkyl;and R.sup.3 is C.sub.1 to C.sub.
    Type: Grant
    Filed: July 13, 1982
    Date of Patent: October 9, 1984
    Assignee: Shionogi & Co., Ltd.
    Inventors: Kentaro Hirai, Shigeru Matsutani, Itsuo Makino, Teruyuki Ishiba
  • Patent number: 4476311
    Abstract: Analgesic and anti-inflammatory compounds are provided. These compounds possess the following general formula: ##STR1## wherein R=--COOR.sub.5, --CH.sub.2 CO.sub.2 H, ##STR2## wherein A and B=hydrogen, lower alkyl, hydroxy alkyl, lower alkyl amine, substituted lower alkyl amine, aminoalkyl, substituted aminoalkyl;R.sub.5 =lower alkyl;R.sub.1 =aryl, substituted aryl, aralkyl, alkyl, hydrogen, substituted aralkyl and heterocycle;R.sub.2 =aryl, substituted aryl, aralkyl, alkyl, substituted aralkyl, heterocycle, substituted heterocycle, biphenyl, substituted biphenyl, naphthyl, and substituted naphthyl;R.sub.3 =aryl, substituted aryl, hydrogen, aralkyl, substituted aralkyl, alkyl, heterocycle and substituted heterocycle;R.sub.2 and R.sub.3 together form a ring;R.sub.4 =hydrogen, phenyl, substituted phenyl, heterocycle; alkyl, substituted alkyl; or, R.sub.1 and R.sub.4 may form a ring;X=>C.dbd.O, --CH.sub.2 --;Y=--S--CHR.sub.4 --, --O--OHR.sub.4 --, --CHR.sub.4 --, --CR.sub.6 R.sub.7 --CHR.sub.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: October 9, 1984
    Assignee: The Purdue Frederick Company
    Inventors: Bola V. Shetty, Arthur McFadden, Peter Hofer
  • Patent number: 4474699
    Abstract: An improved process for preparing a 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepine product, e.g., adinazolam, directly from the corresponding 1-hydrogen-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepine starting material, e.g., from estazolam, by conducting the reaction between the estazolam-type compound and the dimethylaminomethylene salt in the selected solvent in the presence of an alkali metal carbonate, and thereafter extracting the 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a]-[1,4]benzodiazepine from an aqueous organic solvent mixture thereof into a halogenated C.sub.1 to C.sub.3 -alkane solvent while maintaining the pH of the aqueous phase between pH 3.0 and 4.0, and thereafter recovering the product from the halogenated alkane solvent.
    Type: Grant
    Filed: May 25, 1983
    Date of Patent: October 2, 1984
    Assignee: The Upjohn Company
    Inventors: Donald J. Cram, Martin Gall, Michael F. Lipton