Patents Examined by Frederick W. Pepper
  • Patent number: 4411841
    Abstract: Electrochemical fluorination of a thiophene-1,1-dioxide derivative of the formula ##STR1## produces the novel perfluorinated sulphonic acid fluoride of the formula ##STR2## in which X, Y and Z each independently is F, a perfluoroalkyl group having 1 to 8 C-atoms in which one or more CF.sub.2 groups may optionally be replaced by oxygen, the oxygen atoms being separated by at least one CF.sub.2 group, optionally perfluoroalkyl-substituted cycloperfluoroalkyl group having 5 to 12 C-atoms in which one or more CF.sub.2 groups may be replaced by oxygen, orX and Y together denote an optionally perfluoroalkyl-substituted cycloperfluoroalkyl group in which one or more CF.sub.2 groups may be replaced by oxygen,R.sub.f each independently is F or a perfluoroalkyl group having 1 to 3 C-atoms, andn and m each independently is 0 or 1.The products are useful as surface active agents.
    Type: Grant
    Filed: October 28, 1981
    Date of Patent: October 25, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Geisler
  • Patent number: 4410548
    Abstract: Propanolamine derivatives of the formula: ##STR1## wherein R.sup.2 is CH.sub.3 SO or CH.sub.3 SO.sub.2 ;R.sup.3 is hydrogen, methyl or methoxy; orR.sup.2 and R.sup.3 are together --S(O).sub.m (CH.sub.2).sub.4 --when S is attached at R.sup.2 or --(CH.sub.2).sub.n S(O).sub.m -- when S is attached at R.sup.3 (where m=1 or 2 and n=3 or 4);R.sup.4 is hydrogen or alkyl C.sub.1-4 ;Z is --(CH.sub.2).sub.2 -- or ##STR2## and their non-toxic salts. Processes for the preparation and pharmaceutical compositions thereof. The compounds exhibit both .beta.-adrenoreceptor antagonist activity and vasodilator activity and are indicated for use in the treatment of hypertension.
    Type: Grant
    Filed: June 26, 1981
    Date of Patent: October 18, 1983
    Assignee: Reckitt & Colman Products Limited
    Inventors: Andrew J. G. Baxter, Malcolm Myers
  • Patent number: 4409152
    Abstract: Phenylphosphonous dichloride is prepared by the continuous reaction of monochlorobenzene, phosphorus trichloride, and elemental phosphorus at elevated pressures and temperatures.
    Type: Grant
    Filed: September 30, 1981
    Date of Patent: October 11, 1983
    Assignee: Stauffer Chemical Company
    Inventor: Lawrence F. Humphrey
  • Patent number: 4401663
    Abstract: A compound, or pharmaceutically acceptable salt thereof, having the formula: ##STR1## wherein X is ##STR2## wherein R is C.sub.3 -C.sub.12 alkyl or aralkyl, branched or unbranched, unsubstituted aryl, haloaryl, or C.sub.3 -C.sub.22 alkenyl, branched or unbranched; wherein R.sub.1 is H, OH or OCH.sub.3, and wherein R.sub.2 is OH or H, at least one of R.sub.1 and R.sub.2 being OH or OCH.sub.3. These sulfonamides have analgesic and anti-irritant activity when administered to humans and lower animals.
    Type: Grant
    Filed: March 23, 1982
    Date of Patent: August 30, 1983
    Assignee: The Procter & Gamble Company
    Inventors: Brian L. Buckwalter, Thomas R. LaHann
  • Patent number: 4390710
    Abstract: Aromatic esters of carbamic acid derivatives, e.g., p-chlorophenyl-N-methyl carbamate, are prepared by reaction of the corresponding aromatic alcohol, e.g., p-chlorophenol, and monoisocyanate, e.g., methyl isocyanate, in the presence of a catalytic amount of a combination of a 4-aminopyridine catalyst, e.g., 4-dimethylaminopyridine, and pyridine or methyl substituted pyridines. The product is substantially pure, having less than 0.80 weight percent allophanate ester by-product, e.g., p-chlorophenyl-N,N'-dimethyl allophanate, and less than 0.50 weight percent unreacted aromatic alcohol, e.g., p-chlorophenol. The reaction is readily controlled and characterized by the substantial absence of reflux. The product can be retained in the liquid state at reaction temperature for extended periods of time without significantly increasing the level of allophanate ester by-product.
    Type: Grant
    Filed: October 19, 1981
    Date of Patent: June 28, 1983
    Assignee: PPG Industries, Inc.
    Inventor: James A. Manner
  • Patent number: 4387058
    Abstract: Novel phenyl and naphthyl esters of 2-(1-oxo-alkoxy)ethyl carbamic acids are prepared. The compounds are useful as pharmacological and agricultural agents.
    Type: Grant
    Filed: October 2, 1981
    Date of Patent: June 7, 1983
    Assignee: The Dow Chemical Company
    Inventor: Chester E. Pawloski
  • Patent number: 4382142
    Abstract: A compound represented by the formula, ##STR1## wherein R.sub.1 represents a hydrogen atom, and R.sub.2 represents a lower alkyl group, an aryl group, an aralkyl group, a lower alkylthio lower alkyl group, a lower alkyl group substituted by a carboxyl or hydroxyl group, or a 3-indolymethyl group, or wherein R.sub.1 and R.sub.2 define in combination an alkylene group, or a pharmaceutically acceptable acid addition salt thereof, is an anti-tumor agent for leukemia and malignant tumors.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: May 3, 1983
    Assignee: Kowa Co., Ltd.
    Inventors: Kichitaro Takatori, Takashi Yamaguchi, Masahiko Nagakura
  • Patent number: 4381266
    Abstract: Anhydride compounds of the formula ##STR1## wherein A is an optionally substituted amino-phenyl or optionally substituted 3-indolyl radical, Hal represents halogen, Z represents hydrogen, alkyl of 1 to 4 carbon atoms or an optionally substituted phenyl radical and n is 1 to 4; these anhydrides are particularly useful as starting materials for the manufacture of halogenated 3-aryl-3-indolyl-phthalides or fluoran derivatives.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: April 26, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert Garner, Michael J. Whitehead
  • Patent number: 4379166
    Abstract: This invention relates to 5-(2-alkylamino-1-hydroxyethyl)salicylamides and 4-(2-alkylamino-1-hydroxyethyl)-2-(methylsulfinyl)phenols wherein the alkyl group is substituted by arylmethoxy, arylmethylthio, heteroarylmethoxy, or heteroarylmethylthio, pharmaceutical compositions thereof, and their use as cardiovascular agents.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: April 5, 1983
    Assignee: Schering Corporation
    Inventors: Bernard R. Neustadt, Elijah H. Gold
  • Patent number: 4378371
    Abstract: Fungicidally active N-alkyl-carbamic acid 1,1,2-trimethyl-5-substituted-indan-4-yl esters of the formula ##STR1## in which R.sup.1 is an alkyl group,R.sup.2 is an alkyl or aralkyl group,R.sup.3 is a hydrogen atom, an alkyl group or a halogen atom, andR.sup.4 is a hydrogen atom, an alkyl group, a halogen atom, or an alkoxy or alkylmercapto group.
    Type: Grant
    Filed: January 2, 1981
    Date of Patent: March 29, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Peuker, Detlef Grotkopp, Karlfried Wedemeyer, Wilhelm Brandes
  • Patent number: 4371546
    Abstract: Described are compounds of the formula ##STR1## wherein R is hydrogen, loweralkyl, aminomethyl or halo, R.sub.1 is hydroxy or NHX where X is H, loweralkyl, phenyl, substituted phenyl, acetyl, benzyl and substituted benzyl, and Y is hydrogen, loweralkyl or halo and may be the same or different, and pharmaceutically acceptable salts thereof.The compounds are effective as diuretic agents.
    Type: Grant
    Filed: October 9, 1981
    Date of Patent: February 1, 1983
    Assignee: Abbott Laboratories
    Inventors: Jacob J. Plattner, Andre G. Pernet, Anthony K. Fung
  • Patent number: 4369145
    Abstract: Fluorobenzenesulfonyl fluorides are prepared by chlorine/fluorine exchange fluorinating a chlorobenzenesulfonyl fluoride with an alkali metal fluoride, in a aprotic polar solvent and at a temperature ranging from about 100.degree. C. to about 240.degree. C.
    Type: Grant
    Filed: December 16, 1980
    Date of Patent: January 18, 1983
    Assignee: Rhone-Poulenc Industries
    Inventor: Gerard Soula
  • Patent number: 4365072
    Abstract: Biphenyl compounds of the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is hydrogen and the other is --CHO and the cyclic moiety A is a -2,5-; 2,3; or 3,4-di-OR-1-phenyl moiety wherein R is hydrogen or a hydroxy-protecting group are disclosed. The compounds are useful as intermediates in preparing redox compounds containing a phenylhydroquinone or phenylcatechol moiety.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: December 21, 1982
    Assignee: Polaroid Corporation
    Inventor: Avinash C. Mehta
  • Patent number: 4361703
    Abstract: N-acetyl-para-aminophenyl N'acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenol. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl-N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.
    Type: Grant
    Filed: March 23, 1981
    Date of Patent: November 30, 1982
    Assignee: Sterling Drug Inc.
    Inventors: George Margetts, Roderic S. Andrews, Jean Legros
  • Patent number: 4361557
    Abstract: Described are D-(threo)-1-aryl-2-acylamido-3-fluoro-1-propanol esters and salts thereof, methods for their preparation, and methods for their use as antibacterial agents.
    Type: Grant
    Filed: August 10, 1981
    Date of Patent: November 30, 1982
    Assignee: Schering Corporation
    Inventor: Tattanhalli L. Nagabhushan
  • Patent number: 4360479
    Abstract: This invention relates to a new process for the preparation of acyl cyanides of the general formulaR.sup.1 --CO--CN (I)wherein R.sup.1 is an optionally substituted alkyl radical up to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring, which process comprises reacting a carboxylic acid anhydride of the formulaR.sup.1 --CO--O--CO--R.sup.1 (II)with an alpha-hydroxynitrile of the formula ##STR1## in which R.sup.2 and R.sup.3 are identical or different and represent a hydrogen atom, an optionally substituted alkyl radical with 1 to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring.
    Type: Grant
    Filed: June 24, 1981
    Date of Patent: November 23, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Hans Kratzer, Manfred Lenthe
  • Patent number: 4353925
    Abstract: Novel substituted N-(p-aminophenyl)-N'-benzoylureas of the formula I ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -alkenyl, C.sub.3 -alkenyl substituted by a chlorine or bromine atom, or R.sub.1 is C.sub.3 -C.sub.6 -cycloalkyl, R.sub.2 and R.sub.3 are each hydrogen or halogen, R.sub.4 is methyl or halogen, R.sub.5 is hydrogen or halogen, and X is chlorine or bromine, the salts of these compounds, processes for producing these compounds, as well as compositions containing them, for use in combating pests, particularly for combating insects which infest plants and animals. The novel compounds are especially effective against larval stages and eggs of insects which damage plants by eating.
    Type: Grant
    Filed: July 9, 1981
    Date of Patent: October 12, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Josef Ehrenfreund
  • Patent number: 4349663
    Abstract: Bis(cyclic ureas) are disclosed which have the formula ##STR1## wherein R is ##STR2## and C.sub.n H.sub.2n is ethylene or 1,3-propylene each of which can be substituted by one or more inert substituents.These compounds are useful as masked diisocyanates which, on heating in the presence of a polyol and, optionally, a polyurethane catalyst, give rise to polyurethane resins. Accordingly, they are useful as a component of storage stable compositions which are convertible to polyurethanes upon heating. Such compositions are particularly useful as solvent-less coating compositions. The properties of the above compounds are distinguished in a number of respects from the known bis(cyclic ureas) in which C.sub.n H.sub.2n has 4 or more carbon atoms in the chain between the valencies. Illustratively, the above compounds are more stable on exposure to heat in the absence of catalysts but, in the presence of polyurethane catalysts, react with polyols at a significantly faster rate than the prior art compounds.
    Type: Grant
    Filed: November 10, 1980
    Date of Patent: September 14, 1982
    Assignee: The Upjohn Company
    Inventors: Edward A. Barsa, Chung-Yuan Lin, Fred A. Stuber
  • Patent number: 4349471
    Abstract: A process for the simultaneous preparation of an aromatic sulphonic acid halide and an aromatic carboxylic acid halide or the corresponding carboxylic acid is disclosed wherein an aromatic sulphonic acid or acid anhydride is reacted with an aromatic trihalogenomethyl compound in the presence of a Bronsted acid or Lewis acid at a temperature of 20.degree. to 300.degree. C., if appropriate in the presence of a solvent. Generally, at least half an equivalent of aromatic trihalogenomethyl compound is employed per equivalent of sulphonic acid.
    Type: Grant
    Filed: January 22, 1981
    Date of Patent: September 14, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Erich Wolters, Norbert Langenfeld
  • Patent number: 4348525
    Abstract: [Hydroxy(organosulfonyloxy)iodo]arenes are synthesized in neutral organic solvents by the reaction of ring-substituted [hydroxy(organosulfonyloxy)iodo]benzenes with iodoarenes via ligand transfer. The produced compounds are reacted with (triorganosilyl) arenes or (trihalosilyl)arenes in neutral organic solvents to produce diaryliodonium salts. The diaryliodonium salt synthesis proceeds in regiospecific fashion, aryliodination occurring at the point of attachment of the silicon atom in the silylarenes.
    Type: Grant
    Filed: April 9, 1981
    Date of Patent: September 7, 1982
    Assignee: The University of Akron
    Inventors: Gerald F. Koser, Richard H. Wettach