Patents Examined by Robert V. Hines
  • Patent number: 4261842
    Abstract: A semi-synthetic lubricant for high temperature applications, particularly adapted for use on relatively movable metallic surfaces during the shearing of molten glass, and consisting of an aqueous solution of a formulation comprising a non-drying vegetable oil, such as coconut oil, alkanolamine, the phosphate ester of an ethylene oxide adduct of a linear primary alcohol, an emulsifier, preferably the ethoxylated sorbitol hexaoleate, the fatty nitrogen derivative of distilled coconut oil primary amine, and a wetting agent. The wetting agent is preferably the methyl ester of a 50:50 mixture of methyl palmitate and methyl oleate.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: April 14, 1981
    Assignee: Fremont Industries, Inc.
    Inventors: Bruce D. Busch, Dennis J. Yeavello
  • Patent number: 4260825
    Abstract: The present invention provides novel 2-decarboxy-2-aminomethyl-19-keto-PG compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.
    Type: Grant
    Filed: March 20, 1980
    Date of Patent: April 7, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4260760
    Abstract: Novel diphenyl and loweralkyl substituted diphenyl polyamines are useful antimicrobial agents, as well as algae inhibitors. They are especially useful because of their low toxicity, and as such are advantageously included as the active agent in surgical scrubs, antibacterial soaps, as preservatives in cosmetic preparations, and the like. They also can be used for topical treatment of dermatological conditions having a bacterial origin or implication such as Acne vulgaris.
    Type: Grant
    Filed: March 12, 1979
    Date of Patent: April 7, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Richard A. Dybas, Nathaniel Grier, Bruce E. Witzel
  • Patent number: 4259526
    Abstract: The instant invention is directed to a process for the preparation of mixtures of polyamines of the polyamino-polyaryl-polymethylene type whereby the proportion or the ortho-substituted products are substantially increased. This increase is brought about by adding the acid catalyst to the aromatic amine/formaldehyde reaction mixture in two or more stages.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: March 31, 1981
    Assignees: Bayer Aktiengesellschaft, Mobay Chemical Corporation
    Inventors: Kenneth L. Dunlap, Hartmut Knofel
  • Patent number: 4259257
    Abstract: The invention relates to novel 1-phenyl-2-amino-1,3-propanediol-N-alkyl derivatives having the general formula I ##STR1## wherein R.sub.1 is hydrogen, alkyl having from 1 to 8 carbon atoms or phenoxymethyl, andR.sub.2 is hydrogen, alkyl having from 1 to 8 carbon atoms or 2,2-diphenylethyl,with the proviso that if R.sub.1 is phenoxymethyl then R.sub.2 may stand only for methyl, and if R.sub.2 is 2,2-diphenylethyl then R.sub.1 may stand only for hydrogen, and its isomers and pharmaceutically acceptable salts. Furthermore, the invention relates to a process for preparing these compounds.The novel 1-phenyl-2-amino-1,3-propanediol-N-alkyl derivatives having the general formula I possess significant anti-anginose activity and show several other biological activities.
    Type: Grant
    Filed: September 7, 1979
    Date of Patent: March 31, 1981
    Assignee: Egyt Gyogyszervegyeszeti Gyar
    Inventors: Laszlo Levai, Gabor Fazekas, Lujza Petocz, Katalin Grasser
  • Patent number: 4258211
    Abstract: This invention concerns 2,3,5,6-dibenzobicyclo[5.1.0]octanes which may be substituted at the 4-position by either halogen, ketonic oxygen or hydroxyl. These compounds are prepared from 5H-dibenzo[a,d]cyclohepten-5-one by reaction with ethyl trichloroacetate in the presence of sodium methoxide to give 8,8-dichloro-2,3,5,6-dibenzobicyclo[5.1.0]octan-4-one which is reduced to the corresponding 4-hydroxy compound. The resulting 4-hydroxy compound is dehalogenated and converted to the corresponding 4-chloro or 4-keto compound. The 4-substituted compounds are useful in preparing other compounds of our invention.4-Dialkylaminopropylidenedibenzobicyclo[5.1.0]octane compounds and 4-dialkylaminopropyldibenzobicyclo[5.1.0]octane compounds, useful as antidepressant agents, are prepared from, respectively, dibenzobicyclo[5.1.0]octan-4-one by reaction with a dialkylaminopropyl Grignard reagent followed by dehydration of the resulting carbinol or by reaction of a 4-halo-2,3,5,6-dibenzobicyclo[5.1.
    Type: Grant
    Filed: November 28, 1972
    Date of Patent: March 24, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Edward L. Engelhardt, David C. Remy
  • Patent number: 4252824
    Abstract: New compounds of the formula ##STR1## are disclosed wherein R.sub.1 =H, linear or branched alkyl-radical with from 1 to 6 carbon atoms, cycloalkyl radical with from 3 to 6 carbon atoms, alkylphenyl radical where the phenyl group may be in turn substituted with a hydroxy or methoxy group;R.sub.2 =hydroxy, hydromethylR.sub.3 =H, alkyl with 1-4 carbon atoms, formyl, carboalkyl where the alkyl groups have 1-3 carbon atoms, carbomido group simple or mono- or di-substituted on the nitrogen atom with alkyl radicals containing 1-3 carbon atoms.The new compounds are useful in the treatment of bronchial affections. They are endowed with unique properties in that they provide the desired bronchial dilation effect without any concomitant cardiac stimulation.
    Type: Grant
    Filed: November 10, 1976
    Date of Patent: February 24, 1981
    Assignee: Valeas S.R.L., Industria Chimica e Farmaceutica
    Inventors: Virgilio Bernareggi, Giuseppe Crespi, Giuseppe Bugada
  • Patent number: 4252984
    Abstract: The invention provides phenol ethers of the formula: ##STR1## wherein R is branched C.sub.3-4 alkyl, C.sub.3-4 cycloalkyl, branched cyano(C.sub.3-4 alkyl), phenyl(C.sub.2-3 alkyl), halophenyl(C.sub.2-3 alkyl), (C.sub.1-4 alkoxy)phenyl(C.sub.2-4 alkyl), or (C.sub.1-4 acyl)amino(C.sub.1-4 alkyl),alk is C.sub.1-4 alkyl substituted by a 3 to 6 membered cycloalkyl group,X is --O--, --S-- or --SO.sub.2 --; andR.sub.1 is --C.sub.1-4 alkyl- or --C.sub.1-4 alkoxy-,in their racemic and optically active forms, and their addition salts with pharmaceutically acceptable acids. These compounds are useful in therapy as .beta.-adrenergic blocking agents. Intermediates are also provided.
    Type: Grant
    Filed: October 20, 1976
    Date of Patent: February 24, 1981
    Assignee: Synthelabo
    Inventors: Philippe M. J. Manoury, Icilio A. G. Cavero, Henry Najer, Don Pierre R. L. Giudicelli
  • Patent number: 4252744
    Abstract: A process for the preparation of racemic phenylethylamine which comprises contacting an optical antipode therefore, e.g., L(-) or D(+)-1-phenylethylamine with sodium amide or sodium hydride.
    Type: Grant
    Filed: June 15, 1976
    Date of Patent: February 24, 1981
    Assignee: Dynamit Nobel Aktiengesellschaft
    Inventors: Gunter Bison, Kurt Breideneichen, Walter Heinzelmann, Wolfgang Wolfes
  • Patent number: 4250114
    Abstract: An arylamine such as aniline is condensed with formaldehyde in the presence of aqueous hydrochloric acid to form a mass containing the hydrogen chloride salt of a polyarylpolyamine. The mass is contacted with additional aniline thereby forming an organic phase and an aqueous phase, the 4,4'-polyarylpolyamine overwhelmingly being liberated from its salt form in the aqueous phase and being transferred to the organic phase. High recoveries of the 4,4'-diamino polycondensate are achieved.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: February 10, 1981
    Inventor: Efim Biller
  • Patent number: 4246201
    Abstract: Compound of formula: ##STR1## wherein R represents hydrogen or an alkyl group having from 1 to 4 carbon atoms; R', R", R'" and R"", equal or different from each other represent hydrogen atoms or OH groups, with the limitation that when R', R", R'" and R"" are all hydrogen atoms R cannot be an hydrogen atom and their salts with organic and inorganic pharmaceutically acceptable salts.The process for the preparation of the compounds of the above general formula are disclosed.The compounds show a good pharmacological activity and can be used as antiulcer, antispastic spasmolytic drugs.The compounds can be administered as different pharmaceutical preparations containing an effective dose of the compound in combination or in admixture with excipients suitable for oral or parenteral administration or for topical use.
    Type: Grant
    Filed: June 11, 1979
    Date of Patent: January 20, 1981
    Assignee: Alfa Farmaceutici, S.p.A.
    Inventor: Valerio Borzatta
  • Patent number: 4246424
    Abstract: A method for racemization of optically active amines which comprises contacting an optically active amine of the formula: ##STR1## wherein C* is an asymmetric carbon atom, R.sub.1 is alkyl, aralkyl or aryl and R.sub.2 is aryl or alkoxycarbonyl, the aryl or aralkyl moiety bearing optionally one or more alkyl or alkoxy groups on the aromatic ring, provided that R.sub.1 and R.sub.2 are always different from each other, with a catalyst comprising an alkali metal and a polycyclic aromatic hydrocarbon until a sufficient amount of the optically active amine is racemized.
    Type: Grant
    Filed: May 14, 1976
    Date of Patent: January 20, 1981
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tsuneyuki Nagase, Gohu Suzukamo, Yoshio Suzuki
  • Patent number: 4244969
    Abstract: This invention relates to novel compounds of the general formula ##STR1## Representative compounds within the scope of the invention are ##STR2## The compounds are disclosed as being useful for treating symptoms and signs of cardiac failure by stimulating the .beta.-receptors of the heart. Methods of treatment using these compounds are discussed.
    Type: Grant
    Filed: February 13, 1975
    Date of Patent: January 13, 1981
    Assignee: Aktiebolaget Hassle
    Inventors: Enar I. Carlsson, Nils H. A. Persson, Gustav B. R. Samuelsson, Kjell I. L. Wetterlin
  • Patent number: 4235820
    Abstract: This invention relates to a process for the preparation of 5H-dibenzo[a,d]cycloheptene compounds and derivatives having aminoalkyl substituents at the 5-position by reducing the corresponding 5-aminoalkyl-5-hydroxy compounds with an alkali metal borohydride in trifluoroacetic acid.
    Type: Grant
    Filed: August 10, 1976
    Date of Patent: November 25, 1980
    Assignee: Merck & Co., Inc.
    Inventor: Ben E. Evans
  • Patent number: 4224344
    Abstract: Novel 9-aminoalkyl-methanoanthracenes of the formula: ##STR1## wherein A is C.sub.1 -C.sub.4 alkylene or C.sub.3 -C.sub.4 alkenylene and R.sub.1 and R.sub.2 are each hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 cycloalkyl(C.sub.1 -C.sub.3)alkyl, ar(C.sub.1 -C.sub.3)alkyl or polyhalo(C.sub.2 -C.sub.4)alkyl or, when taken together with the adjacent nitrogen atom, they may form a 5 to 7-membered nitrogen-containing heterocyclic ring which may contain an additional hetero atom, and their non-toxic salts, which are useful as anti-anxiety, anti-depressant, major tranquilizer, anti-histamine and anti-allergy drugs and can be prepared through a novel key intermediate, i.e., 9-formyl-9,10-dihydro-9,10-methanoanthracene, by various methods.
    Type: Grant
    Filed: December 11, 1975
    Date of Patent: September 23, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Sunagawa, Hiromi Sato, Junki Katsube, Hisao Yamamoto
  • Patent number: 4224246
    Abstract: A process for the synthesis and separation of the threo and erythro isomers of 2-amino-1-phenyl-1-propanol comprising the steps of catalytically reducing 2-nitro-1-phenyl-1-propanol to form the acetate salt of the racemic mixture of 2-amino-1-phenyl-1-propanol and separating the isomers by fractional crystallization.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: September 23, 1980
    Assignee: International Minerals and Chemical Corporation
    Inventor: Edward B. Hodge
  • Patent number: 4221739
    Abstract: Compounds of the formula (I), ##STR1## wherein R.sub.1 and R.sub.2 each is saturated or unsaturated, straight-chained or branched alkyl phenyl, alkylphenyl or saturated or unsaturated cycloalkyl;but when R.sub.1 is methyl, R.sub.2 is a group other than methyl, are prepared by reacting a compound of the formula (II), ##STR2## wherein X is halogen, with a secondary amine of the formula (III),R.sub.1 --NH--R.sub.2 (III)The new compounds of the formula (I), as well as their pharmaceutically acceptable acid addition salts are active primarily in the induction of liver microsomal enzyme, but also possess antipyretic activity.
    Type: Grant
    Filed: August 12, 1975
    Date of Patent: September 9, 1980
    Assignee: Richter Gedeon Vegyeszeti Gyar R.T.
    Inventors: Edit Toth, Jozsef Torley, Eva Palosi, Szabolos Szeberenyi, Laszlo Szporny, Sandor Gorog, Csilla Meszaros
  • Patent number: 4219502
    Abstract: An improvement in the process for alkylating the nucleus of an aromatic amine which contains small amounts of a nickel compound by reaction with an olefin in the presence of an aluminum anilide-type catalyst whereby hydrogen sulfide or a sulfide generating compound (e.g. thioacetamide) is added to the aromatic amine to reduce the rate inhibiting effect of the nickel compound.
    Type: Grant
    Filed: June 1, 1979
    Date of Patent: August 26, 1980
    Assignee: Ethyl Corporation
    Inventors: Kryn G. Ihrman, Manuel Brandt
  • Patent number: 4218472
    Abstract: New geminally disubstituted indenes are of general formula I ##STR1## wherein each of R.sup.1 and R.sup.2 is hydrogen or R.sup.1 and R.sup.2 together form a direct bond or an alkylene group --(CH.sub.2).sub.n --, in which n is an integer from 1 to 4, R.sup.3 is hydrogen, C.sub.1-3 -alkoxy or halogen, and each of R.sup.4 and R.sup.5 is hydrogen or C.sub.1-4 -lower alkyl, or R.sup.4 and R.sup.5 together form an alkylene group --(CH.sub.2).sub.m --, in which m is an integer from 3 to 6; and the corresponding amine oxides, quaternary ammonium compounds and salts with physiologically acceptable acids.The indenes find use in treating incontinence, as a mucous membrane decongestant, as a blood pressure reducing agent, as vasocostrictor or as an anti-reserpine agent.The indenes may be prepared by processes known per se involving(a) synthesing the side chain --CH(OH)CH.sub.2 NR.sup.4 R.sup.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: August 19, 1980
    Assignee: AB Kabi
    Inventors: Aake N. Joensson, Tomas G. Kempe, Lembit Mikiver, Bengt A. Sparf
  • Patent number: 4217307
    Abstract: The catalytic hydrogenation of o-nitro-chlorobenzene in aqueous alkali metal hydroxide solution with addition of an aromatic non-watermiscible solvent at an elevated temperature and under pressure using a noble metal catalyst and a polycyclic quinone as a co-catalyst leads to high and well-reproducible yields of 2,2'-dichloro-hydrazobenzene when the quinone is a derivative of anthraquinone, especially a hydroxy-anthraquinone. The product is obtained in so high a quality that it can be transformed without isolation or purification into 3,3'-dichlorobenzidine.
    Type: Grant
    Filed: July 25, 1978
    Date of Patent: August 12, 1980
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Planker, Konrad Baessler, Otto Fuchs