Ortho Fused Patents (Class 560/28)
  • Patent number: 4925971
    Abstract: A method for producing aliphatic O-arylurethanes by the reaction of an aliphatic primary amine with an aromatic hydroxyl compound and urea. Ammonia produced as a by-product in the reaction is removed during the reaction so that the ammonia concentration of the reaction solution is maintained at 2 wt % or less.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: May 15, 1990
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Toshiya Aoki, Hiroshi Ishida, Shinsuke Fukuoka
  • Patent number: 4914128
    Abstract: Acrylates of the general formula ##STR1## where R.sup.1 and R.sup.2 independently of one another are each C.sub.1 -C.sub.8 -alkyl, X is hydrogen, C.sub.1 -C.sub.4 -alkyl, halogen, C.sub.1 -C.sub.4 -alkoxy, haloalkyl, cyano or nitro, W is unsubstituted or alkyl-substituted, saturated or unsaturated C.sub.1 -C.sub.10 -alkylene, Y is hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, aralkyl, aryl, aryloxy, halogen, an unsubstituted or substituted C.sub.4 H.sub.4 chain which is fused to the benzene radical, alkoxy, haloalkoxy, alkylthio, thiocyanato, cyano, NO.sub.2, ##STR2## where R' and R" independently of one another are each hydrogen, alkyl, alkoxy, alkylthio or cycloalkyl, or are phenyl which is unsubstituted or substituted by alkyl, halogen or alkoxy, m is 0 or 1, n is from 1 to 4 and Z is oxygen, sulfur, SO or SO.sub.2, and fungicides containing them.
    Type: Grant
    Filed: October 11, 1988
    Date of Patent: April 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schirmer, Stefan Karbach, Ernst-Heinrich Pommer, Eberhard Ammermann, Wolfgang Steglich, Barbara A. M. Schwalge, Timm Anke
  • Patent number: 4883907
    Abstract: The present invention relates to new carbazates of the formula (I) ##STR1## wherein A is C.sub.3 to C.sub.10 alkenyl, C.sub.2 to C.sub.10 haloalkyl, trifluoromethyl, phenyl-C.sub.1 to C.sub.3 alkyl, phenyl-C.sub.2 to C.sub.3 alkenyl, naphthyl-C.sub.1 to C.sub.3 alkyl, C.sub.3 to C.sub.7 cycloalkyl-C.sub.1 to C.sub.3 alkyl, furyl which can be nitro-substituted, diphenyl-hydroxymethyl or indazolyl which can be substituted by one or more C.sub.1 to C.sub.4 alkoxy groups; andR is C.sub.1 to C.sub.4 alkyl,and acid addition salts thereof, a process for the preparation thereof and feed additives comprising the same.The compounds of formula (I) may be used in animal husbandry due to their weight-gain increasing and fodder utilization improving effect.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: November 28, 1989
    Assignee: Egis Gyogyszergyar
    Inventors: Ildiko Ratz nee Simonek, Pal Benko, Edit Berenyi nee Foldermann, Karoly Magyar
  • Patent number: 4879410
    Abstract: A process is disclosed for the preparation of aralkyl mono- and diurethanes or ureas by carbamylmethylation, or acid-catalyzed addition at a temperature of 40.degree. C. to about 100.degree. C. of formaldehyde and esters of carbamic acid to aromatic hydrocarbons. Aralkyl carbamates and ureas formed by this process can be cracked directly to produce aralkyl diisocyanates, or hydrogenated and then cracked to produce aliphatic diisocyanates, or reacted directly with polyols to produce polyurethanes by functioning as blocked isocyanates.
    Type: Grant
    Filed: November 3, 1986
    Date of Patent: November 7, 1989
    Assignee: American Cyanamid Company
    Inventors: Balwant Singh, Laurence W. Chang, William A. Henderson, Jr.
  • Patent number: 4843062
    Abstract: Disclosed herein are N-acyl-N-napthoylglycines and methods of their preparation. The N-acyl-N-napthoylglycines are novel aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: June 27, 1989
    Assignee: American Home Products Corporation
    Inventors: Kazimir Sestanj, Jay E. Wrobel, Joseph M. Kelly
  • Patent number: 4837305
    Abstract: Molecular structures of .beta.-adrenergic antagonists are modified to produce biologically active compounds. The .beta.-antagonists are modified to form molecules of the general structure: ##STR1## wherein R is most generally R"--OCH.sub.2 --, and in some instances is R"--, and R"=an aryl or substituted aryl moiety; R'=--H, --CH.sub.3, or a short chain alkyl moiety; and Y=--OH, or more usually, --OAX or --NHAX, where A=an alkyl, aryl, or aralkyl moiety, and X=a terminal grouping, such as --CH.sub.3, --CF.sub.3 or --(CH.sub.2).sub.n COOH; or AX may be a carrier moiety consisting of a defined peptide or protein.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: June 6, 1989
    Assignee: The Regents of the University of California
    Inventors: Murray Goodman, Debra Marr-Leisy, Roberto P. Rosenkranz, Kenneth L. Melmon, Michael S. Verlander
  • Patent number: 4824670
    Abstract: The present invention relates to new carbazates of the general formula (I), ##STR1## wherein A is C.sub.3-10 alkyl, C.sub.3-10 alkenyl, C.sub.2-10 haloalkyl, trifluoromethyl, phenyl-C.sub.1-3 alkyl, phenyl-C.sub.2-3 -alkenyl, naphthyl-C.sub.1-3 alkyl; phenyl optionally substituted by one or more identical or different substituent(s) selected from C.sub.1-4 alkyl, halogen, C.sub.1-4 alkoxy and hydroxy; C.sub.3-7 cycloalkyl-C.sub.1-3 alkyl; optionally nitro-substituted furyl; diphenyl-hydroxy-methyl or indazolyl optionally substituted by one or more C.sub.1-4 alkoxy group(s) andR represents C.sub.1-4 alkyl,with the proviso that if R stands for ethyl, A is other than tertiary butyl, and acid addition salts thereof, a process for the preparation thereof and feed-additives comprising the same.The compounds of the general formula (I) may be used in animal husbandry due to their weight-gain increasing and fodder utilization improving effect.
    Type: Grant
    Filed: December 11, 1985
    Date of Patent: April 25, 1989
    Assignee: Egis Gyogyszergyar
    Inventors: Ildiko Ratz nee Simonek, Pal Benko, Edit Bernenyi nee Poldermann, Karoly Magyar
  • Patent number: 4820727
    Abstract: Disclosed herein are N-acyl-N-naphthoylglycines and methods of their preparation. The N-acyl-N-naphthoylglycines are novel aldose reductase inhibitors useful for the treatment or prevention of diabetic complications.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: April 11, 1989
    Assignee: American Home Products Corporation
    Inventors: Jay E. Wrobel, Kazimir Sestanj
  • Patent number: 4782175
    Abstract: The molecule of the new urethanes contains an aliphatic fluoroalcohol, an isocyanate and an aromatic dihydroxy, diamino, aminohydroxy, aminocarboxy or hydroxycarboxy compound. They are prepared by reacting an aliphatic fluoroalcohol with a diisocyanate or triisocyanate to give the fluoroalcohol/isocyanate adduct and by reacting this adduct with said aromatic compound to give the desired urethanes composed of an aliphatic fluoroalcohol, an isocyanate and the bifunctional aromatic compound mentioned, and also be reacting a urethane of this type which also carries an active hydrogen atom on the bifunctional aromatic compound, with an isocyanate compound containing one or more isocyanate groups. The new urethanes are preferably used for imparting an oleophobic and hydrophobic finish to textiles and leather.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: November 1, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Frank Wehowsky, Rolf Kleber, Lothar Jaeckel
  • Patent number: 4758661
    Abstract: (+)-trans-1a,2,3,4a,5,6-Hexahydro-9-hydroxy-4-propyl-4H-naphth[1,2-b]-1,4-o xazine is elaborated by a series of process steps that retain the enantiomeric purity of the starting material, D-aspartic acid. The product is a direct acting dopaminergic agent, useful in the treatment of Parkinson's disease.
    Type: Grant
    Filed: June 24, 1986
    Date of Patent: July 19, 1988
    Assignee: Merck & Co., Inc.
    Inventors: David G. Melillo, David J. Mathre, Robert D. Larsen
  • Patent number: 4749806
    Abstract: The present invention relates to a process for the synthesis of isocyanates and of isocyanate derivatives. Isocyanates are obtained by reacting an organic halide with a metal cyanate in an organic medium in the presence of a catalyst consisting of a complex of nickel with at least one organic ligand, in which complex the nickel is in the zero oxidation state.A carbamate or a urea, respectively, are obtained by a subsequent reaction with a hydroxy compound or a primary or secondary amine.Isocyanates and their derivatives are used especially either as refined synthesis agents for the production of pesticides and medications, or as monomers or comonomers for the preparation of many macromolecular compounds.
    Type: Grant
    Filed: August 25, 1987
    Date of Patent: June 7, 1988
    Assignee: Societe Nationale des Poudres et Explosifs
    Inventors: Igor Tkatchenko, Rabih Jaouhari, Michel Bonnet, Gordon Dawkins, Serge Lecolier
  • Patent number: 4687872
    Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a catalyst comprising rhodium, as a metal or compound, is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a rhodium catalyst comprising a polyamino ligand having at least two tertiary amino groups capable of coordinating with rhodium.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: August 18, 1987
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm
  • Patent number: 4687873
    Abstract: Molecular structures of .beta.-adrenergic antagonists are modified to produce biologically active compounds. The .beta.-antagonists are modified to form molecules of the general structure: ##STR1## wherein R is most generally R"--OCH.sub.2 --, and in some instances is R"--, and R"=an aryl or substituted aryl moiety; R'=--H, --CH.sub.3, or a short chain alkyl moiety; and Y=--OH, or more usually, --OAX or --NHAX, where A=an alkyl, aryl, or aralkyl moiety, and X=a terminal grouping, such as --CH.sub.3, --CF.sub.3 or --(CH.sub.2).sub.n COOH; or AX may be a carrier moiety consisting of a defined peptide or protein.
    Type: Grant
    Filed: May 10, 1985
    Date of Patent: August 18, 1987
    Assignee: The Regents of the University of California
    Inventors: Murray Goodman, Debra Marr-Leisy, Roberto P. Rosenkranz, Kenneth L. Melmon, Michael S. Verlander
  • Patent number: 4683325
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: October 17, 1984
    Date of Patent: July 28, 1987
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Richard Frenette, Joshua Rokach, Masatoshi Kakushima, Robert N. Young
  • Patent number: 4678856
    Abstract: The present invention relates to a method of manufacturing aromatic urethane, an aromatic mononitro-compound, an aromatic primary amine, and carbon monoxide being reacted using a catalyst containing a platinum group metal-containing compound as a major constituent to prepare N,N'-di-substituted urea. The resultant N,N'-di-substituted urea is reacted with a hydroxyl group-containing organic compound to prepare an aromatic primary amine and aromatic urethane, and the aromatic primary amine is separated to obtain aromatic urethane.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: July 7, 1987
    Assignee: Nippon Kokan Kabushiki Kaisha
    Inventors: Takao Ikariya, Masanori Itagaki, Masatsugu Mizuguchi, Itaru Sakai, Osamu Tajima
  • Patent number: 4629804
    Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst. The selectivity of this process is increased by the use of methanol instead of various other alkanols, e.g. ethanol. Preferably the catalyst is a halide-free ruthenium catalyst, e.g. a ruthenium carbonyl complex.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: December 16, 1986
    Assignee: Catalytica Associates
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
  • Patent number: 4621149
    Abstract: A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising:(a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and(b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules,in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80.degree. C. to about 300.degree. C. under a pressure of from about 1 Kg/cm.sup.2 to about 500 Kg/cm.sup.2.
    Type: Grant
    Filed: December 10, 1984
    Date of Patent: November 4, 1986
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Shinsuke Fukuoka, Masazumi Chono
  • Patent number: 4610985
    Abstract: Allophanate derivatives of the formula ##STR1## in which R.sup.1 and R.sup.2 can be identical or different and represent an aliphatic, cycloaliphatic, araliphatic or aromatic radical each of which is optionally monosubstituted or polysubstituted by identical or different substituents andR.sup.3 represents the radical --XR.sup.4 or --NR.sup.5 R.sup.6,whereinR.sup.4 represents alkyl, alkoxyalkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, X represents oxygen or sulphur andR.sup.5 and R.sup.6 are identical or different and represent hydrogen, alkyl, or aryl which is optionally monosubstituted or polysubstituted by identical or different substituents, orR.sup.5 and R.sup.6, together with the nitrogen atom on which they stand, form a saturated heterocyclic radical which is optionally monosubstituted or polysubstituted by identical or different substituents and can be interrupted by further hetero-atoms,which possess fungicidal activity.
    Type: Grant
    Filed: April 10, 1985
    Date of Patent: September 9, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Fuhrer, Engelbert Kuhle, Gerd Hanssler
  • Patent number: 4603216
    Abstract: This invention relates to a process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a ruthenium catalyst comprising a bis phosphine ligand.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: July 29, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine, Jr.
  • Patent number: 4600793
    Abstract: A process for preparing urethanes by reacting a solution of a nitrogen-containing organic compound and a hydroxyl-containing organic compound with carbon monoxide in the presence of a halide-free ruthenium catalyst is disclosed. In the process of this invention, the rate of conversion and selectivity to urethane is increased by providing a primary amine in the reaction solution.
    Type: Grant
    Filed: September 16, 1983
    Date of Patent: July 15, 1986
    Assignees: Catalytica Associates, Haldor Topsoe A/S
    Inventors: John H. Grate, David R. Hamm, Donald H. Valentine
  • Patent number: 4593116
    Abstract: Urethanes are made by reacting an organic nitro compound with an organic compound containing at least one hydroxyl group in the presence of carbon monoxide, hydrogen and a catalyst system. The carbon monoxide and hydrogen are used in quantities such that the molar ratio of CO to H.sub.2 is from 0.3:1 to 3:1. The catalyst system is made up of at least one noble metal or compound of a noble metal from Group VIIIB of the Periodic System of Elements, at least one organic nitrogen base and a co-catalyst combination of iron or copper oxidic or hydroxidic compound and a chloride compound. The product urethanes are useful in the production of isocyanates and pesticides.
    Type: Grant
    Filed: June 13, 1984
    Date of Patent: June 3, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Stammann, Johann Grolig, Robert Becker, Helmut Waldmann
  • Patent number: 4570002
    Abstract: The invention relates to new carbazic acid derivatives, a process for the preparation thereof and compositions--particularly feed additives and animal feeds--containing the same.The new compounds according to the invention correspond to the formula (I)R.sup.1 .dbd.N--NH--COOR.sup.3 (I)whereinR.sup.1 stands for a C.sub.7-12 cycloalkylidene group, an indanylidene group or a group of the formula (IX) ##STR1## wherein A represents a phenyl group optionally carrying one or more identical or different substituents selected from the group consisting of halo nitro, hydroxy, C.sub.1-14 alkoxy, C.sub.1-4 alkyl, amino or C.sub.1-4 alkoxycarbonylhydrazino; phenyl-(C.sub.1-4 alkyl), C.sub.1-16 alkyl, C.sub.3-7 cycloalkyl or indolyl or a C.sub.3 -C.sub.6 cycloalkyl group substituted by a C.sub.3 -C.sub.6 cycloalkyl group;R.sup.2 denotes a hydrogen atom, a C.sub.1-16 alkyl or a C.sub.3-7 cycloalkyl group; andR.sup.3 represents a C.sub.1-4 alkyl group.
    Type: Grant
    Filed: January 24, 1984
    Date of Patent: February 11, 1986
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Zoltan Budai, Pal Benko, Ildiko Ratz nee Simonek, Eva Rakoczy nee Pinter, Karoly Magyar, Jozsef Kelemen, Attila Mandi
  • Patent number: 4569689
    Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1 is alkoxy, alkylthio, unsubstituted or substituted cycloalkoxy or the radical --NR.sup.2 R.sup.3, X is --CH.sub.2 --, --CH(OH)-- or --CO--, A is an unsubstituted or substituted alkylene chain, B is unsubstituted or substituted methylene or dimethylene, Z is hydrogen, halogen, alkyl, alkoxy, haloalkyl or haloalkoxy, and n is 1, 2 or 3, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: June 14, 1984
    Date of Patent: February 11, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schirmer, Norbert Goetz, Bruno Wuerzer
  • Patent number: 4570012
    Abstract: Production of tertiary aralkyl urethanes, such as tetramethyl xylylene diurethanes, by addition of corresponding diols and carbamic acid esters at moderate temperatures and in the presence of acid catalyst.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: February 11, 1986
    Assignee: American Cyanamid Co.
    Inventors: Balwant Singh, Peter S. Forgione, Laurence W. Chang
  • Patent number: 4568763
    Abstract: N-acyl-acyloxy aromatic amines, e.g. 4-acetoxyacetanilide (AAA), are prepared by reacting a hydroxy aromatic ketone, e.g. 4-hydroxyacetophenone, with hydroxylamine or a hydroxylamine salt and a base to obtain the ketoxime of the ketone, e.g. 4-hydroxyacetophenone oxime, and then subjecting the ketoxime to a Beckmann rearrangement and accompanying acylation by contacting the ketoxime with a carboxylic acid anhydride and a Beckmann rearrangement catalyst to form the N-acyl-acyloxy aromatic amine.
    Type: Grant
    Filed: July 3, 1984
    Date of Patent: February 4, 1986
    Assignee: Celanese Corporation
    Inventors: Kenneth G. Davenport, Charles B. Hilton
  • Patent number: 4568684
    Abstract: N-substituted 2-methylnaphthylamides of the general formula I ##STR1## where R is an unsubstituted or substituted furyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,5-thiadiazol-3-yl, 1,3,4-thiadiazol-2-yl or C.sub.1 -C.sub.5 -alkyl radical, or the group --CH.sub.2 --Y--R.sup.1, where Y is oxygen or sulfur and R.sup.1 is C.sub.1 -C.sub.6 -alkoxyethyl or C.sub.1 -C.sub.6 -alkoxyethoxyethyl, or R is C.sub.2 -C.sub.5 -alkenyl, C.sub.2 -C.sub.5 -alkynyl, C.sub.1 -C.sub.5 -alkoxy, C.sub.1 -C.sub.5 -alkoxycarbonyl or C.sub.3 -C.sub.7 -cycloalkyl, and fungicides containing these compounds.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: February 4, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Karl Eicken, Hans Theobald, Bernd Zeeh, Ernst-Heinrich Pommer, Eberhard Ammermann
  • Patent number: 4566900
    Abstract: Aniline derivatives of the formula ##STR1## where R.sup.1, Y, A, Z and n have the meanings given in the description, are used for controlling undesirable plant growth.
    Type: Grant
    Filed: December 1, 1982
    Date of Patent: January 28, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Plath, Ulrich Schirmer, Gernot Reissenweber, Bruno Wuerzer, Guenter Retzlaff
  • Patent number: 4536598
    Abstract: A new color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor in a photographic material and process enables formation of a dye image by means of cross-oxidation without the need for a coupling reaction. The color-forming 4-(4'-secondary or tertiary-amino)anilino-1-carboxamidonaphthalene dye precursor is useful in a photographic silver halide material for producing (i) a dye image, or (ii) a dye image and silver image. The exposed photographic material is processed to produce (a) a positive dye image, (b) a negative dye and negative silver image, (c) a negative dye image or (d) a positive dye image and a positive silver image. New naphthoquinoneimide dyes are also described.
    Type: Grant
    Filed: March 10, 1983
    Date of Patent: August 20, 1985
    Assignee: Eastman Kodak Company
    Inventors: James E. Klijanowicz, Csaba A. Kovacs
  • Patent number: 4533675
    Abstract: The present invention consists of derivatives of colchicine and thiocolchicine which are carbamates of the same and are illustrated by the formula below: ##STR1## where either X.sub.1 or X.sub.2 is a hydroxy group and the other a lower alkoxy group and R.sub.1 can be H or an alkyl, R.sub.2 an alkyl, alkenyl or aryl which may be substituted and R.sub.3 is either OCH.sub.3 or SCH.sub.3 ; alkyl and alkoxy=C.sub.1 -C.sub.6 ; aryl=monoaryl.These compounds are not only new but have exhibited antitumor activity binding to tubulin protein and tests against P388 lymphocytic leukemia and also active against gouty arthritis. Further, they are far less toxic than colchicine.
    Type: Grant
    Filed: April 17, 1984
    Date of Patent: August 6, 1985
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Arnold Brossi, Peter Kerekes
  • Patent number: 4533745
    Abstract: Amino ketone enantiomers and their direct preparation are disclosed. The ketone may be reduced to yield carbinol enantiomer which has pharmaceutical activity.
    Type: Grant
    Filed: December 8, 1980
    Date of Patent: August 6, 1985
    Assignee: Merck & Co., inc.
    Inventor: David E. McClure
  • Patent number: 4502994
    Abstract: A novel enantiomeric synthesis from ascorbic acid of (3S,4S)-3-amino-4-carbamoyloxymethyl-2-azetidinone-1-sulfate, an intermediate for an antibiotic compound.
    Type: Grant
    Filed: December 9, 1982
    Date of Patent: March 5, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Chung-Chen Wei, Manfred Weigele
  • Patent number: 4496755
    Abstract: A manufacturing method is described for the preparation of optically active 1-(6-methoxy-2-naphthyl)-2-(alkoxycarbonyl)amino-1-propanone, its derivatives and their halo analogs. The optically active 1-(6-methoxy-2-naphthyl)-2-(alkoxycarbonyl)amino-1-propanone, its derivatives and their halo analogs are useful intermediates in the preparation of 2-(6-methoxy-2-naphthyl)propionic acid, which is useful as pharmaceutical, e.g. antiinflammatory, analgesic and anti-pyretic agents.
    Type: Grant
    Filed: March 28, 1983
    Date of Patent: January 29, 1985
    Assignee: Sagami Chemical Research Center
    Inventors: Genichi Tsuchihashi, Shuichi Mitamura, Koji Kitajima, Kumi Kobayashi
  • Patent number: 4490551
    Abstract: A process for producing urethanes by reacting aromatic amino compounds with aliphatic, cycloaliphatic or araliphatic alcohols and carbon monoxide under conditions of elevated temperature and pressure characterized in that the reaction takes place in the presence of(a) selenium, selenium compounds, sulfur and/or sulfur compounds,(b) aromatic nitro compounds,(c) tertiary organic amines and/or alkali metal salts of weak acids,(d) oxidizing agents of a specified group and, optionally(e) ammonia and/or aliphatic, araliphatic, cycloaliphatic or heterocyclic amines containing at least one hydrogen atom bound to an amine nitrogen.
    Type: Grant
    Filed: February 27, 1980
    Date of Patent: December 25, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Scholl, Armin Zenner
  • Patent number: 4486598
    Abstract: Novel compounds of the following general formula: ##STR1##
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: December 4, 1984
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4474807
    Abstract: This invention is directed to novel antimicrobial agents. More particularly, this invention is directed to 2-(3-iodo-2-propynyloxy)-ethyl carbamates of the formula ##STR1## wherein R is hydrogen, linear or branched alkyl of from 1 to 12 carbon atoms, cycloalkyl of from 4 to 8 carbon atoms, aryl, substituted aryl, aralkyl, or arylsulfonyl;R.sup.1 and R.sup.2, which may be the same or different, each are hydrogen, linear or branched alkyl or alkenyl of from 1 to 6 carbon atoms, or cycloalkyl of from 5 to 7 carbon atoms, or R.sup.1 and R.sup.2, taken together, represent --(CH.sub.2).sub.m --, in which m is an integer of from 4 to 6; andR.sup.3, R.sup.4, R.sup.5, and R.sup.6, which may be the same or different, each represent hydrogen, alkyl of from 1 to 4 carbon atoms, or aryl, or CCl.sub.3, or R.sup.3 and R.sup.5 or R.sup.4 and R.sup.6, taken together, represent --(CH.sub.2).sub.n --, in which n is an integer of from 3 to 5,as well as a process for their preparation and their use as antimicrobial agents.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: October 2, 1984
    Assignees: Henkel Kommandigesellschaft auf Aktien, Montedison S.p.A.
    Inventors: Werner Gerhardt, Rudolf Lehmann
  • Patent number: 4474806
    Abstract: Sulfonyl or carbonyl derivatives of inositols are found to be effective phospholipase C inhibitors and thereby potent anti-inflammatory and analgesic agents. These inositol derivatives are prepared by condensation of a protected inositol with a substituted sulfonic or carboxylic acid derivative followed by removal of protecting groups.
    Type: Grant
    Filed: May 10, 1982
    Date of Patent: October 2, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Thomas R. Beattie, Shu S. Yang
  • Patent number: 4439616
    Abstract: Production of tertiary aralkyl isocyanates, such as tetramethyl xylylene diisocyanates, by thermal cracking of corresponding urethanes formed by addition of corresponding olefins and carbamic acid esters at moderate temperatures and in the presence of acid catalyst.
    Type: Grant
    Filed: July 22, 1982
    Date of Patent: March 27, 1984
    Assignee: American Cyanamid Company
    Inventors: Balwant Singh, Laurence W. Chang, Peter S. Forgione
  • Patent number: 4430505
    Abstract: A process for the preparation of N,O-disubstituted urethanes. Urea or polyurets, primary amines and alcohols are reacted at 120.degree.-350.degree. C. in the presence of N-substituted urethanes and/or N-mono- or N,N'-disubstituted ureas or polyureas. In a preferred embodiment, the reactants further include catalysts known to be useful in esterification of carboxylic acids. The urethanes produced in accordance with this process are particularly useful as starting materials for preparation of isocyanates.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: February 7, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitkamper, Klaus Konig, Kurt Findeisen, Rudolf Fauss, Rudolf Sundermann
  • Patent number: 4426385
    Abstract: Novel bicyclooxyphenyl ureas, such as 1-(bicyclooxyphenyl)-benzoyl ureas, are provided which exhibit pesticidal activity. The compositions are conveniently prepared by reacting an isocyanate with either an amide or a bicyclooxyaniline.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: January 17, 1984
    Assignee: Union Carbide Corporation
    Inventor: Paul A. Cain
  • Patent number: 4398036
    Abstract: An improved process for the preparation of N-monosubstituted carbamates by reacting an aromatic primary amine, urea and a monohydric aliphatic alcohol in the presence of a strongly basic tertiary amine catalyst and optionally an inert solvent.
    Type: Grant
    Filed: May 2, 1980
    Date of Patent: August 9, 1983
    Assignee: Atlantic Richfield Company
    Inventor: John J. McCoy
  • Patent number: 4395565
    Abstract: A process for the preparation of aromatic urethans by reaction between aromatic amines and alkyl carbonates, said reaction being carried out in the presence of a catalyst composed of an alcoholate of an alkali metal or an alkaline earth metal. The reaction is caused to take place at a temperature which is variable from +50.degree. C. and +150.degree. C., in the liquid phase and with a molar ratio of the carbonate to the amine of from 10:1 to 1:10.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: July 26, 1983
    Assignee: Anic S.p.A.
    Inventors: Ugo Romano, Giancarlo Fornasari, Sandro Di Gioacchino
  • Patent number: 4388238
    Abstract: A process for the preparation of N,O-disubstituted urethanes. Primary amines and alcohols are reacted with organic compounds having carbonyl groups at 120.degree. to 350.degree. C. Suitable carbonyl-containing compounds include N-unsubstituted urethanes. N-mono-substituted, N,N'-disubstituted ureas, or polyureas may be used in combination with the N-unsubstituted urethane. The product urethanes are particularly suitable for the preparation of isocyanates.
    Type: Grant
    Filed: October 15, 1980
    Date of Patent: June 14, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Heitkamper, Klaus Konig, Rudolf Fauss, Kurt Findeisen
  • Patent number: 4381403
    Abstract: A process for the preparation of N-monosubstituted carbamic acid esters by reacting an unsubstituted carbamic acid ester and an aromatic primary amine at a suitable pressure and reaction temperature in the presence of a monohydric aliphatic alcohol and preferably in the presence of a strongly basic tertiary amine as catalyst. Optionally an inert co-solvent in addition to the alcohol may be employed.
    Type: Grant
    Filed: March 31, 1980
    Date of Patent: April 26, 1983
    Assignee: Atlantic Richfield Company
    Inventors: Samuel J. Falcone, John J. McCoy
  • Patent number: 4376783
    Abstract: The novel acylated guanidines, ureas and substituted ureas correspond to the general formula: ##STR1## in which R.sub.1 repesents a substituted or unsubstituted aromatic ring, R.sub.2 represents an alkyl, aryl, or arylalkyl group, R.sub.4 repesents hydrogen or a variously substituted aryl group, X is oxygen or an imine group: NH and Y represent an alkyl aryl alkyloxy or aryloxy group or a hydrogen atom when X represents oxygen or the group COR.sub.3 with R.sub.3 representing an aromatic group, an aryloxy, aralkyloxy or alkyloxy group when X represents the NH group. They are prepared by heating an appropriate compound under reflux with an oxyaminoalcohol, in a suitable solvent. The products are useful as medicaments for the treatment of arterial hypertension, ischemica diseases of the heart and rhythmic disorders of the latter.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: March 15, 1983
    Assignee: Compagnie Francaise de Sucerie
    Inventors: Jesus Anatol, deceased, by Marie-Francoise Anatol, legal representative, by Andre-Manuel Anatol, legal representative, Jean Berecoechea, Pierre Duchene-Marullaz, Alain Eschalier
  • Patent number: 4375000
    Abstract: A process for the preparation of an aryl mono-, di-, and/or polyurethane comprising the steps of A. reacting a primary aromatic mono-, di-, and/or polyamine with an O-alkyl carbamate in the presence of an alcohol at temperatures greater than 160.degree. C., andB. separating the ammonia and other by-products from the aryl mono-, di-, and/or polyurethane.The reaction is preferably carried out in the presence of urea. The aryl mono-, di-, and/or polyurethanes produced are valuable end and intermediate products. They can be transferred into the corresponding isocyanates which can then be used for the preparation of polyurethanes.
    Type: Grant
    Filed: March 31, 1980
    Date of Patent: February 22, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Merger, Friedrich Towae, Wolfgang Harder
  • Patent number: 4373105
    Abstract: New m-anilide-urethanes, processes for their manufacture, herbicides containing these compounds, and processes for controlling unwanted plant growth with these compounds.
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: February 8, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Rohr, Ulrich Schirmer, Bruno Wuerzer
  • Patent number: 4362888
    Abstract: Dimethacrylates are provided having the following chemical structure: ##STR1## where ##STR2##is a saturated, 6 membered, monocyclic, hydrocarbyl ring system;R.sub.1, R.sub.2 and R.sub.3 are the same or different and are hydrogen or alkyl or alkoxy groups having 1 to 12 carbon atoms; andR.sub.4 and R.sub.5 are the same or different and are hydrogen or groups of the formula: ##STR3## where R.sub.6 is an aliphatic, aromatic or cycloaliphatic group having 1 to 14 carbon atoms, provided that at least one of the groups R.sub.4 and R.sub.5 is a group of the formula: ##STR4## These compounds are useful in dental material which cures to form polymers having high mechanical strength, low water sorption, resistance to staining, good color stability when exposed to short-wave radiation (e.g., sunlight) and good chemical resistance to the oral environment. Also provided are a method for polymerizing this compound in situ on teeth and a tooth comprising a polymer of this compound.
    Type: Grant
    Filed: September 15, 1980
    Date of Patent: December 7, 1982
    Assignee: Scientific Pharmaceuticals, Inc.
    Inventors: Jan A. Orlowski, David V. Butler, Patrick D. Kidd
  • Patent number: 4355036
    Abstract: Antihistamines of the formula ##STR1## wherein ##STR2## is a 5 or 6 membered ring which is phenyl or heterocyclic; ##STR3## is a six membered ring which is 2,3 or 4 pyridyl or is phenyl or substituted phenyl, with the proviso that is ##STR4## is a nitrogen containing ring, ##STR5## must be phenyl; Z is an alkylene chain having 0 to 2 carbon atoms in the chain, said 2 carbon chain optionally having one double bond, said chain optionally having either a carbonyl oxygen, or a hydroxy group as a substituent; W is ##STR6## wherein p is 1 or 2 and n is 1 or 2, R.sup.1 is C.sub.1 to C.sub.6 alkyl, R.sup.2 is hydrogen or C.sub.1 to C.sub.6 alkyl, and the dotted line represents an optical double bond, R.sup.2 being absent if the double bond is present, and Y is substituted carboxylate or substituted sulfonyl. Said antihistamines have little or no sedative effects.
    Type: Grant
    Filed: March 16, 1981
    Date of Patent: October 19, 1982
    Assignee: Schering Corporation
    Inventor: Frank J. Villani
  • 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: 4347377
    Abstract: The invention concerns a new process for the preparation of polyhalogenphenyl carbamates of the formula (I)R.sup.2 -OCONHR.sup.1 (I)whereinR.sup.1 is alkyl, aralkyl or aryl, where the aromatic rings may optionally be substituted; andR.sup.2 is phenyl substituted with three, four or five halogens, through intermediates of the formula (IV)(R.sup.2 --O).sub.2 C.dbd.NR.sup.1 (IV)wherein R.sup.1 and R.sup.2 are as defined above.The compounds of the formula (I) are valuable acylating agents. The intermediates of the formula (IV) are new compounds, which are also encompassed by the invention.
    Type: Grant
    Filed: September 19, 1980
    Date of Patent: August 31, 1982
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara R.T.
    Inventors: Istvan Bitter, Rudolf Soos, Geza Toth, Laszlo Toke, Gabor Szabo