Patents Examined by Raymond V. Rush
  • Patent number: 4028346
    Abstract: Organic molecules can be coupled via their selenocarbonyl derivatives. Generally, the synthesis can be described by the following reaction equation: ##STR1## where C can be a cyclic or heterocyclic organic compound and R can be alkoxy, phenoxy or phenyl, preferably CH.sub.3 O, C.sub.2 H.sub.5 O, C.sub.6 H.sub.5 O, C.sub.6 H.sub.5 and the like. The reaction is usually carried out in a refluxing solvent, the choice of the solvent being determined by the stability and by the ease of coupling of a particular substrate. Groups that tend to stabilize the selenocarbonyl require higher boiling solvents and longer refluxing times. Aromatic solvents, such as benzene or toluene are well-suited for the coupling reaction. In some cases, refluxing the substrate in the alkoxy-phosphorus base as solvent may be advantageous. This new coupling procedure permits the synthesis of the hitherto unknown compounds: tetraselenofulvalene (TSeF), the selenium analogue of tetrathiofulvalene (TTF), and diselenodithiofulvalene (DSeDTF).
    Type: Grant
    Filed: June 10, 1974
    Date of Patent: June 7, 1977
    Assignee: International Business Machines Corporation
    Inventors: Edward M. Engler, Vishnubhai V. Patel
  • Patent number: 4026902
    Abstract: Isoxazole derivatives of the formula ##STR1## wherein R is carboxy, ethoxycarbonyl or carbamoyl, are disclosed. The compounds have utility as antidiabetic agents.
    Type: Grant
    Filed: June 4, 1976
    Date of Patent: May 31, 1977
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventor: Tsutomu Irikura
  • Patent number: 4026880
    Abstract: A silicone compound of the formula, ##STR1## where R, R.sup.1, R.sup.2 and R.sup.6 are hydrocarbon radicals, B is selected from nitrogen, oxygen and sulfur, D is selected from a divalent hydrocarbon radical or oxygen, G is selected from various nitrogen radicals, and a, n, t, c and v are whole numbers. The above compound is eminently useful as a flocculent for colloidal biological wastes, as well as being useful as a glass sizing agent.
    Type: Grant
    Filed: August 5, 1971
    Date of Patent: May 31, 1977
    Assignee: General Electric Company
    Inventor: Tyrone D. Mitchell
  • Patent number: 4025636
    Abstract: 2-(Optionally substituted)phenyl-benzoxazoles having a carboxy alkyl, a tetrazolyl, or oxazolinyl group at the 5 or 6 position useful as aspirin-like non-steroidal, non-narcotic, analgesic, antipyretic and anti-inflammatory agents.
    Type: Grant
    Filed: February 4, 1976
    Date of Patent: May 24, 1977
    Assignee: Lilly Industries, Ltd.
    Inventors: David William Dunwell, Delme Evans, Terence Alan Hicks
  • Patent number: 4025521
    Abstract: The reaction of thebaine or dihydrothebaine-.phi. with potassium in liquid ammonia respectively in the absence or presence of catalyst yields .beta.-dihydrothebaine.
    Type: Grant
    Filed: October 22, 1975
    Date of Patent: May 24, 1977
    Assignee: Sharps Associates
    Inventor: David Edward Portlock
  • Patent number: 4025637
    Abstract: 5- or 6-Substituted benzoxazole propionic or acetic acid derivatives, substituted in the 2-position of the oxazole nucleus by a group of the formula AR.sup.4 wherein A is --CH.sub.2 --, --CO--, --CHOR--, or --NR--, wherein R is hydrogen, C.sub.1.sub.-6 alkyl or C.sub.2.sub.-7 acyl, and R.sup.4 is optionally substituted phenyl, useful as non-steroidal, non-narcotic, analgesic, antipyretic and anti-inflammatory agents.
    Type: Grant
    Filed: February 4, 1976
    Date of Patent: May 24, 1977
    Assignee: Lilly Industries, Ltd.
    Inventors: David William Dunwell, Delme Evans, Terence Alan Hicks
  • Patent number: 4022782
    Abstract: New 4-amino derivatives of pyrazolo[1,5-a]quinoxaline-3-carboxylic acid, esters and their salts have the formula ##STR1## R.sub.1 is hydrogen, lower alkyl or a salt forming ion; R.sub.2 and R.sub.3 each is hydrogen, lower alkyl, cyclo-lower alkyl, phenyl, substituted phenyl, phenyl-lower alkylene, di-lower alkylamino-lower alkylene or R.sub.2 and R.sub.3 together with the nitrogen form an unsubstituted or substituted 5- or 6-membered nitrogen heterocyclic in which an additional nitrogen or oxygen may be present.R.sub.4 is hydrogen, lower alkyl or halogen.The new compounds are useful as anti-inflammatory agents.
    Type: Grant
    Filed: August 18, 1976
    Date of Patent: May 10, 1977
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Uwe D. Treuner
  • Patent number: 4022779
    Abstract: New derivatives of pyrido[3,4-b]pyridine carboxylic acids and esters and their acid addition salts have the general formula ##STR1## They are useful as anti-inflammatory agents and central nervous system depressants.
    Type: Grant
    Filed: October 7, 1975
    Date of Patent: May 10, 1977
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Theodor Denzel, Hans Hoehn
  • Patent number: 4021441
    Abstract: Compounds of the formula II: ##STR1## wherein R is cyclopropyl, cyclopropylmethyl, or allyl; wherein R', R", and R.sub.1 are hydrogen or alkyl of 1 to 3 carbon atoms inclusive; and wherein R.sub.2, R.sub.3, and R.sub.4 are hydrogen, alkyl as defined above, fluoro, chloro, bromo, nitro, trifluoromethyl, or alkylthio in which alkyl is defined as above, are prepared by reacting a compound of the formula I. ##STR2## wherein R", R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are defined as above, and wherein X is chlorine or bromine, with an amine of the formula ##STR3## wherein R and R' are defined as above. The compounds of formula II and the pharmacologically acceptable acid salts thereof have tranquilizing, sedative, antianxiety, and anticonvulsant activity and can be used in animals and birds.
    Type: Grant
    Filed: April 7, 1975
    Date of Patent: May 3, 1977
    Assignee: The Upjohn Company
    Inventor: Jackson B. Hester, Jr.
  • Patent number: 4021550
    Abstract: The invention concerns hexahydroazepines of the formula ##STR1## and the pharmaceutically acceptable acid addition and quaternary ammonium salts thereof, wherein R.sup.4 is lower alkyl, R.sup.5 is lower alkyl, lower alkenyl, lower alkynyl or cyclopropylmethyl and R.sup.6 is a 1-adamantoyl group. The compounds are useful as analgesic agents.
    Type: Grant
    Filed: June 7, 1976
    Date of Patent: May 3, 1977
    Assignee: John Wyeth & Brother Limited
    Inventors: Alan Chapman White, Richard Arthur Franklin
  • Patent number: 4020079
    Abstract: 3-Alkylthioalkyl-4-optionally substituted sydnones, useful as anti-inflammatory pharmaceutical agents, are prepared.
    Type: Grant
    Filed: August 1, 1974
    Date of Patent: April 26, 1977
    Assignee: G. D. Searle & Co.
    Inventors: Richard E. Ray, Hans A. Wagner
  • Patent number: 4020081
    Abstract: Benzoxazoles having the structure ##STR1## where R is hydrogen or an alkyl group having from 1 to 20 carbon atoms, R' is hydrogen, chlorine or an alkyl group containing from 1 to 20 carbon atoms, X is H or Chlorine and the total number of carbon atoms in R and R' is 6 to 40 with the proviso that one of R and R' must be an alkyl group of at least 6 carbon atoms. The benzoxazoles are useful in a process of recovering metal values, particularly copper and nickel, from aqueous solutions thereof.
    Type: Grant
    Filed: October 25, 1974
    Date of Patent: April 26, 1977
    Assignee: General Mills Chemicals, Inc.
    Inventors: Kenneth D. MacKay, Edgar R. Rogier
  • Patent number: 4018788
    Abstract: 6-(o-halophenyl)-1-methyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines of the following formula: ##STR1## wherein the substituent "Hal" is either of the halogens having an atomic number up to 35, inclusive, i.e., fluoro, chloro or bromo, and their pharmacologically acceptable acid addition salts which are especially useful as muscle relaxing and anxiolylic agents.
    Type: Grant
    Filed: December 24, 1975
    Date of Patent: April 19, 1977
    Assignee: The Upjohn Company
    Inventor: Jackson B. Hester, Jr.
  • Patent number: 4017508
    Abstract: The invention relates to certain benzoxazole bichromophoric compounds which have been found to be effective ultraviolet stabilizers. The invention also relates to ultraviolet degradable organic compositions containing a stabilizing amount of a certain benzoxazole bichromophoric compound to prevent such degradation. These stabilizers are effective in the presence of other additives commonly employed in polymeric compositions including, for example, pigments, colorants, fillers, reinforcing agents and the like. These ultraviolet stabilizers may also be incorporated into the organic compositions such as polymers by adding to the polymer melt or dissolved in the polymer dope, coated on the exterior of the shaped or molded article, film or extruded fiber.
    Type: Grant
    Filed: July 1, 1974
    Date of Patent: April 12, 1977
    Assignee: Eastman Kodak Company
    Inventor: David Martin Pond
  • Patent number: 4016172
    Abstract: Azolindolines of the formula ##STR1## wherein Z represents hydrogen or an optionally modified aldehyde group,R.sub.1 and R.sub.2 denote alkyl or represent the remaining members of a cycloalkyl radical,R.sub.3 denotes alkyl or aralkyl,X represents oxygen, sulphur or --NR.sub.4,whereinR.sub.4 denotes hydrogen or alkyl, cycloalkyl or aralkyl, and A represents the remaining members of an aromatic radical,As well as their preparation, and, moreover, compounds of the formula ##STR2## wherein A, X, R.sub.1, R.sub.2 and R.sub.3 have the same meaning as above and R.sub.5 denotes alkyl or aralkylAs well as their preparation and their use for the dyeing of synthetic fiber materials.
    Type: Grant
    Filed: January 17, 1974
    Date of Patent: April 5, 1977
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Harnisch
  • Patent number: 4016171
    Abstract: 2-Vinyl-2-oxazolines are prepared in the novel process comprising reacting (1) an N-(2-haloalkyl)-3-halopropionamide with (2) at least 2 equivalents of an inorganic base per mole of (1). The process is conducted under substantially anhydrous conditions and in the presence of an alkylene glycol or a polyalkylene glycol.
    Type: Grant
    Filed: September 14, 1972
    Date of Patent: April 5, 1977
    Assignee: The Dow Chemical Company
    Inventors: Bruce P. Thill, Janet N. Paige
  • Patent number: 4013676
    Abstract: N-Phenylacetamidines bearing an acylamino group in the phenyl ring have anthelmintic activity and are effective against nematodes and cestodes. A representative embodiment is N-(4-carbophenoxyaminophenyl)-N',N'-dimethylacetamidine.
    Type: Grant
    Filed: May 22, 1975
    Date of Patent: March 22, 1977
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmund Wollweber, Winfried Flucke
  • Patent number: 4012411
    Abstract: Compounds of the formula: ##STR1## are disclosed wherein X is NH, O or S and the tautomers thereof when X is nitrogen, and Y is hydrogen, lower alkyl, hydroxy, lower alkoxy, chloro, bromo or aryl. These compounds are useful in the management of allergic manifestations such as bronchial asthma.
    Type: Grant
    Filed: March 3, 1975
    Date of Patent: March 15, 1977
    Assignee: Warner-Lambert Company
    Inventors: Sylvester Klutchko, John Shavel, Jr., Max Von Strandtmann
  • Patent number: 4012413
    Abstract: Compounds of the formula: ##STR1## wherein R is hydrogen, methyl, or ethyl; wherein R' and R" are hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, wherein R.sub.1 is hydrogen or methyl defined as above; wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl defined as above, halogen, nitro, trifluoromethyl, and alkoxy and alkylthio, in which the carbon chain moieties are of 1 to 3 carbon atoms, inclusive; and wherein the 5 to 6 nitrogen-carbon linkage is selected from the group consisting of double bonds and single bonds, are produced by a variety of multistep processes.The new compounds of formula X above and the pharmacologically acceptable acid addition salts thereof have oral and parenteral sedative and tranquilizing activity, and anti-depressant activity and can be employed for tranquilizing mammals as well as combating anxiety and depressions.
    Type: Grant
    Filed: February 14, 1975
    Date of Patent: March 15, 1977
    Assignee: The Upjohn Company
    Inventor: Jackson B. Hester, Jr.
  • Patent number: 4011219
    Abstract: Phthalazine derivatives represented by the formula ##STR1## and salts thereof which are useful for a luminescence immuno assay, or a process for preparing the same are disclosed.
    Type: Grant
    Filed: March 28, 1975
    Date of Patent: March 8, 1977
    Assignee: Chugai Seiyaku Kabushiki Kaisha
    Inventors: Yasuho Nishii, Shun-ichi Hata, Kiyoshige Wakabayashi, Koji Mizuno, Akio Yoshida, Minoru Shindo