The Nitrogen Bonded Additionally Only To Hydrogen Patents (Class 546/311)
  • Patent number: 4847382
    Abstract: R.sup.2 represents hydrogen or halogen,R.sup.3 represents hydrogen or, together with R.sup.2, represents .dbd.0,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen, alkyl, halogenoalkyl or aryl,R.sup.7 represents alkyl,R.sup.8 represents alkyl, cyloalkyl, aralkyl, aryl or heterocyclyl, which can optionally be substituted,R.sup.9 represents acyl or hydrogen and Hal represents halogen.Compounds III are new. Compounds I are known as yield-promoting agents in animal feeds.
    Type: Grant
    Filed: February 29, 1988
    Date of Patent: July 11, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Hallenbach, Hans Lindel
  • Patent number: 4831148
    Abstract: In accordance with a novel process, 2,3-difluoropyridines of formula I ##STR1## wherein X is halogen or trifluoromethyl, are prepared by diazotising a 3-amino-2-halopyridine of formula II ##STR2## wherein X is as defined for formula I and Y is bromine, chlorine or fluorine, in the presence of hydrogen fluroide, to give a 3-fluoro-2-halopyridine of formula III ##STR3## wherein X and Y are as defined for formula II, and treating resultant 3-fluoro-2-halopyridines of formula III, wherein Y is bromine or chlorine, with a fluorinating agent.The 2,3-difluoropyridines prepared by the novel process are valuable intermediates for the preparation of 2-[4-(3-fluoropyridin-2-yloxy)-phenoxy]propionic acid derivatives which are known as herbicides.
    Type: Grant
    Filed: October 4, 1985
    Date of Patent: May 16, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Schurter, Urs Siegrist, Hermann Rempfler, Peter Baumeister
  • Patent number: 4826531
    Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: May 2, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 4818273
    Abstract: Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonamides, e.g., 5,7-dimethyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulf onamide and their agriculturally acceptable salts are prepared. These compounds and compositions containing them are useful for the control of unwanted vegetation. Novel substituted triazolo[1,5-a]pyrimidine-2-sulfonyl chlorides and substituted anilines and their use as intermediates are also described.
    Type: Grant
    Filed: December 10, 1986
    Date of Patent: April 4, 1989
    Assignee: The Dow Chemical Company
    Inventors: William A. Kleschick, Robert J. Ehr, Mark J. Costales, Ben C. Gerwick, III, Richard W. Meikle, deceased, William T. Monte, Pearson, Norman R.
  • Patent number: 4816457
    Abstract: Heterocyclic aminoethanols of the formula:Het--CHOH--CH.sub.2 --NH-aralkylwhere Het is a 6-10 membered N-heterocycle are disclosed. The compounds are useful as pharmaceuticals.
    Type: Grant
    Filed: June 30, 1987
    Date of Patent: March 28, 1989
    Inventors: John J. Baldwin, Joseph Atkinson, David E. McClure
  • Patent number: 4797490
    Abstract: 6-Fluoro-7-pyridylquinolone carboxylic esters and acids having antibacterial activity are prepared by coupling of a 2-fluorophenyl-metallic compound with a pyridyl bromide or iodide in the presence of a transition metal catalyst, nitrating and hydrogenating the pyridyl-2-fluorophenyl compound formed, introducing a substituent on the nitrogen of the amine formed, and cyclizing after reacting with a dialkyl or dibenzyl ethoxymethylene malonate to form a 6-fluoro-7-pyridyl-1,4-dihydroquinol-4-one 3-carboxylate, and hydrolyzing to the corresponding acid.
    Type: Grant
    Filed: September 15, 1986
    Date of Patent: January 10, 1989
    Assignee: Pfizer Inc.
    Inventors: Paul J. Gilligan, Paul R. McGuirk, Michael J. Witty
  • Patent number: 4772611
    Abstract: Novel cardioactive compounds of the formula ##STR1## in which R.sup.1 is alkyl, aryl or heterocyclic, preferably substituted phenyl,R.sup.2 is alkyl, preferably methyl,R.sup.3 is hydrogen, halogen, acyloxy or alkyl, preferably hydrogen, andR.sup.4 is phenyl, carbalkoxy or together with R.sup.3 forms a ring, preferably carbalkoxy,are produced by reducing the corresponding nitro compounds.
    Type: Grant
    Filed: April 28, 1987
    Date of Patent: September 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Stoltefuss, Fred R. Heiker, Martin Bechem, Rainer Gross, Michael Kayser, Matthias Schramm, Gunter Thomas
  • Patent number: 4762928
    Abstract: A novel amino-trifluoromethylpyridine compound selected from the group consisting of 3-amino-5-trifluoromethylpyridine, 2-amino-4-trifluoromethylpyridine, and 2-amino-4,6-bis(trifluoromethyl)pyridine, and, a process for preparing the same by reacting a halogeno-trifluoromethylpyridine compound with ammonia at a temperature of 50.degree. to 200.degree. C. The compound is useful as an intermediate from which a compound effective in controlling various harmful organisms or an effective component compound of medicines can be easily derived.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: August 9, 1988
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Yasuhiro Tsujii, Tatsuo Isogai, Takao Awazu, Hisayoshi Jyonishi, Tokiya Kimura
  • Patent number: 4761481
    Abstract: It is disclosed that aryl-substituted 2,6-bis[N,N-di(carboxyalkyl)aminoalkyl] pyridines in which the aryl groups are substituted with one or more electron-releasing groups are an advantageous ligand for forming fluorescent chelates with rare earth metals. The pyridine moieties can be linked to target molecules, especially biologically active target molecules to provide fluorescent tagging for use in fluoroassay techniques. The pyridine moieties are disclosed as tetraacids, as salts and as esters. Preparation processes and precursors including the corresponding aryl-substituted 2,6-dicarboxypyridines as acids, salts and esters, are disclosed as well.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: August 2, 1988
    Assignee: Baxter Travenol Laboratories, Inc.
    Inventors: Ron L. Hale, Dennis W. Solas
  • Patent number: 4756739
    Abstract: The compounds of the formula I ##STR1## in which A denotes N or N.fwdarw.O, Z denotes O or NH, R denotes H, (halo)alkyl, (halo)alkenyl, (halo)alkynyl or alkoxycarbonyl, R.sup.1 denotes hydrogen, halogen, amino, --NHOH, hydroxyl, (substituted) phenylazo or a radical of the formulae Y=C=N--, Y.sup.1 Y.sup.2 C.dbd.N--, Y.sup.3 NH-- or ##STR2## K denotes 0 or 1, and m and n, independently of one another, denote a number from 1 to 4, with the proviso that, when Z-R denotes OH or NH.sub.2, (R.sup.1).sub.n denotes at least one radical of the formula ##STR3## or represents two radicals, in the 5 or 6 position of the heterocyclic ring, which, in the 5 position, denote halogen and, in the 6 position, denote a radical of the group comprising halogen, amino, hydroxyl or phenylazo, which may be substituted as specified above, are valuable intermediates in the synthesis of plant protection agents.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: July 12, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Fuss, Volker Koch
  • Patent number: 4757147
    Abstract: This invention relates to novel highly branched amines and to a process of preparing same which comprises:(1) the preparation of a vinylimine from branched aldehydes and ammonia;(2) the dimerization and intermolecular condensation of such vinylimines to cyclic diamines; and(3) hydrolysis of such cyclic diamines to other diamines.
    Type: Grant
    Filed: September 5, 1985
    Date of Patent: July 12, 1988
    Assignee: Petrolite Corporation
    Inventors: Benjamin T. Outlaw, Bernardus A. Oude Alink
  • Patent number: 4725602
    Abstract: Acetylenes of the following formula (I): ##STR1## wherein Y, m, R.sup.1, R.sup.2, R.sup.3, n and R.sup.4 are defined herein and R.sup.5 is hydrogen, alkyl, cycloalkyl or substituted alkyl are useful vasodilators and antihypertensives.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: February 16, 1988
    Assignee: McNeilab, Inc.
    Inventor: John R. Carson
  • Patent number: 4699983
    Abstract: 2-Amino-4-trichloromethylpyridine of the formula I ##STR1## The compound is an effective nitrification inhibitor.
    Type: Grant
    Filed: March 12, 1986
    Date of Patent: October 13, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, Hans Ziegler, Rolf-Dieter Kohler, Ernst-Heinrich Pommer, Jurgen Dressel
  • Patent number: 4686222
    Abstract: Heterocyclic aminoethanols of the formulaHet--CHOH--CH.sub.2 --NH--aralkylwhere het is a 6-10 membered N heterocycle are disclosed. The compounds are useful as pharmaceuticals.
    Type: Grant
    Filed: October 3, 1985
    Date of Patent: August 11, 1987
    Assignees: Merck & Co., Inc., Merck Sharp & Dohme (I.A.) Corp.
    Inventors: Joseph G. Atkinson, John J. Baldwin, David E. McClure
  • Patent number: 4672121
    Abstract: A process for preparing a 4-substituted pyridine product from a starting pyridine substituted in the 4-position by a leaving group susceptible to nucleophilic displacement when the starting pyridine is in quaternized form, comprises,quaternizing the starting pyridine under effective acidic conditions with acrylamide, N-monoalkylacrylamide or N-dialkylacrylamide,subjecting the resultant, corresponding quaternized starting pyridine, to a nucleophilic displacement reaction with a reagent which reacts with it to produce the corresponding quaternary salt of the 4-substituted pyridine product, anddequaternizing the latter under effective basic conditions to liberate the 4-substituted pyridine product.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: June 9, 1987
    Assignee: Nepera Chemical Co.
    Inventor: Laurence J. Nummy
  • Patent number: 4654349
    Abstract: The present invention concerns the pyrazolo[1,5-a]pyridine derivatives which are antiallergic agents, referred to as SRS-A release inhibitors, and useful for treatmetn of allergic diseases.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: March 31, 1987
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Irikura, Keigo Nishino, Yoshio Nagatsu
  • Patent number: 4610991
    Abstract: A series of 4-pyridinylaminobenzamides, useful as antihypertensive agents, was prepared from the corresponding 4-pyridinylaminobenzoic acids by reacting the acid chloride of the latter with ammonia or a primary or secondary amine. Alternatively the compounds were prepared by reacting an aminobenzamide with 4-chloropyridine or equivalent reagent.
    Type: Grant
    Filed: December 12, 1984
    Date of Patent: September 9, 1986
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4596869
    Abstract: A novel compound, useful as an intermediate in the production of compounds of high antimicrobial activity, of the formula: ##STR1## wherein R.sub.a.sup.1 is hydrogen, amino or a protected amino group,R.sub.b.sup.1 and R.sub.c.sup.1 are each hydrogen, halogen, lower alkoxy or arylthio,R.sup.14 is carboxy or a protected carboxy group,X is lower alkylene or a group of the formula: ##STR2## in which R.sup.6 is hydrogen or an organic residue which may have suitable substituent(s), andZ is N or CH,or a salt thereof.
    Type: Grant
    Filed: September 19, 1985
    Date of Patent: June 24, 1986
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takashi Kamiya, Tsutomu Teraji, Yoshiharu Nakai, Kazuo Sakane, Jiro Goto
  • Patent number: 4535162
    Abstract: A process is herein described for catalytically reducing nitroaromatic compounds by displacement of hydrogen from carbon monoxide and water or from synthesis gas to nitroaromatic compounds, the catalytic reduction being catalyzed by complexes of rhodium, iridium, ruthenium and osmium; said process is characterized in that the CO+H.sub.2 O system or the (CO+H.sub.2)+H.sub.2 O system is caused to react with a nitroaromatic compound of formula:Ar--(NO.sub.2).sub.x (I)wherein Ar is an aryl or hetero-aryl group, also substituted by inert groups; x is an integer from 1 to 3, in the presence of a complex catalyst of formula:[MChel(L).sub.2 ].sup.+ X.sup.- (II)or of a catalyst composed by carbonyl compounds and chelants of formula:Mz(CO).sub.y +nChel (III)wherein M=Rh, Ir, Ru, Os; "Chel" is a bidentate or tridentate aromatic nitrogen chelating compound; "L" is a molecule of carbon monoxide or of an olefin or half a molecule of a diolefin; X.sup.- is an anion selected from Cl.sup.-, Br.sup.-, I.sup.-, PF.sub.6.sup.
    Type: Grant
    Filed: June 16, 1983
    Date of Patent: August 13, 1985
    Assignee: Montedison S.p.A.
    Inventors: Giovanni Mestroni, Grazia Zassinovich, Enzo Alessio
  • Patent number: 4535163
    Abstract: The invention provides 2-(3,5-disubstituted pyridylalkyl amino)-5-pyridylmethyl-4-pyrimidone derivatives which are useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: February 2, 1984
    Date of Patent: August 13, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: George S. Sach
  • Patent number: 4526974
    Abstract: The invention provides a process for preparing 2-pyridylalkylamines by reacting an alkali metal derivative of a 2-methylpyridine with a haloalkylamine. The compounds are useful as intermediates in the preparation of compounds having histamine H.sub.1 - and H.sub.2 -antagonist activity.
    Type: Grant
    Filed: March 22, 1983
    Date of Patent: July 2, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Brian M. Adger, Antonietta R. Mastrocola
  • Patent number: 4496733
    Abstract: Procedure for producing 2-aminopyridines having general formula: ##STR1## from 2-pyridine carboxylic acid-N-oxides having the formula: ##STR2## wherein R is H or a --COOH group or an alkyl group having C.sub.1 to C.sub.8 or an aryl group, and n is a number between 1 and 4. The 2-pyridine carboxylic acid-N-oxide is converted with a lower aliphatic carboxylic acid anhydride and a tertiary amine in the presence of a carboxylic acid nitrile. The conversion product is hydrolyzed to the 2-aminopyridine compound.
    Type: Grant
    Filed: March 30, 1983
    Date of Patent: January 29, 1985
    Assignee: Lonza Ltd.
    Inventor: Daniel Quarroz
  • Patent number: 4469696
    Abstract: The invention relates to 4-,5-and 6-substituted 2-amino pyridines of Formula (I) and methods for their preparation. Also included in the invention are compositions containing said 2-amino pyridines of Formula (I) and the use of said compounds and compositions for use inter alia, as lipid absorption inhibitors.
    Type: Grant
    Filed: June 3, 1982
    Date of Patent: September 4, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Rosentreter, Walter Puls, Hilmar Bischoff
  • Patent number: 4442100
    Abstract: The invention relates to substituted 2-amino-3,4-dihydropyridine derivative compounds useful, for example as lipid absorption inhibitors.Also included in the invention are methods for the manufacture of said active compounds, compositions containing them and methods for the use of said compounds and compositions.
    Type: Grant
    Filed: November 24, 1980
    Date of Patent: April 10, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Meyer, Rudiger Sitt, Gunter Thomas, Benward Garthoff, Robertson Towart, Ulrich Rosentreter
  • Patent number: 4412856
    Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: November 1, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
  • Patent number: 4390702
    Abstract: A 3-substituted-3-fluoropyruvic acid and its ester and salt of the formula: ##STR1## wherein R is a lower alkyl group, a lower alkanoyl group, a fluorinated lower alkanoyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group and R' is a hydrogen atom, an ester-forming residue or a salt-forming residue, and their production.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: June 28, 1983
    Assignees: Daikan Kogyo Co., Ltd., Shionogi and Co., Ltd.
    Inventors: Susumu Misaki, Masahiro Suefuji, Tadahiko Tsushima, Hiroshi Tanida
  • Patent number: 4386209
    Abstract: In a Chichibabin amination of a pyridine base by sodamide in an organic solvent, the improvement comprising conducting the reaction under pressure of at least about 50 psi in the gas phase above the reaction mixture and adding ammonia to the mixture sufficient to produce a partial pressure of ammonia of at least about 5 psi in the gas phase. Preferred temperature and pressure ranges are disclosed, as are catalysts and other preferred steps for practicing the reaction. Significant results are obtained including improved and changed yields from those classically expected in Chichibabin aminations, including new compositions of matter in at least one case.
    Type: Grant
    Filed: April 8, 1982
    Date of Patent: May 31, 1983
    Assignee: Reilly Tar & Chemical Corporation
    Inventors: Charles K. McGill, James J. Sutor
  • Patent number: 4349681
    Abstract: A novel compound, 2-amino-trifluoromethyl-halogenopyridine, is provided, which is prepared by amination of a 2-halogeno-trifluoromethyl-halogenopyridine or by halogenation of 2-amino-trifluoromethylpyridine. This compound is useful as an intermediate for synthesis of agricultural chemicals and medicines.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: September 14, 1982
    Assignee: Ishihara Sangyo Kaisha, Ltd.
    Inventors: Isao Yokomichi, Takahiro Haga, Kuniaki Nagatani, Toshio Nakajima
  • Patent number: 4338445
    Abstract: Pharmaceutical compounds of the general formula ##STR1## and non-toxic pharmaceutically-acceptable salts thereof wherein R.sup.1 is inter alia alkyl, cycloalkyl, aralkyl, or certain pyridyl or phenyl radicals, and with provisoR.sup.2 is selected from hydrogen, lower alkyl, lower alkoxy, amino, hydroxyl, halogen, carboxyl, amido, and --CON(lower alkyl).sub.2. Methods of preparing these compounds are described. The compounds exhibit analgesic, anti-inflammatory, hyperglycemic and/or hypoglycemic activity.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: July 6, 1982
    Assignee: Canadian Patents & Development Limited
    Inventors: Edward E. Knaus, Linda A. Corleto, Kinfe Redda
  • Patent number: 4286108
    Abstract: A process is disclosed for preparing anhydrous hydrazines by reacting a tertiary hydrazinium halide with a corresponding alkali metal or alkaline earth metal amide in the presence of a non-aqueous inert carrier.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: August 25, 1981
    Inventor: Hans Osborg
  • Patent number: 4265896
    Abstract: Amidinosulphonic acid derivatives carrying an unsaturated nitrogen heterocycle-containing substituent, representative of which are N-methyl-N'[2-(5-methyl-4-imidazolylmethylthio)-ethyl] amidinosulphonic acid and N-methyl-N'-[2-(3-chloropyrid-2-ylmethylthio) ethyl] amidinosulphonic acid, are histamine H.sub.2 -receptor antagonists.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: May 5, 1981
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Rodney C. Young, Zev Tashma
  • Patent number: 4254059
    Abstract: A novel process is described for the homogeneous hydrogenation of nitriles to primary amines utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the high yield hydrogenation of nitriles to primary amines to be conducted under mild conditions of temperature and pressure with high selectivity and eliminates the need for the presence of ammonia to suppress the formation of significant amounts of secondary and tertiary amines.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: March 3, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Roger A. Grey, Guido P. Pez
  • Patent number: 4241206
    Abstract: The invention is a generalized hydroacylation reaction. The reaction involves the activation of a selected aldehyde by converting by iminization to an aldimine or an aminal. The imine group replaces the carbonyl group. The imine C-H bond is then susceptible to attack by a chosen olefin, and hydrolysis to yield the ketone. One moiety of the ketone derives from the aldehyde and the other from the olefin added later. Therefore, the ketone may be symmetrical or unsymmetrical. Both aromatic and aliphatic aldehydes may be activated according to this process.
    Type: Grant
    Filed: October 27, 1978
    Date of Patent: December 23, 1980
    Assignee: Bell Telephone Laboratories, Incorporated
    Inventor: John W. Suggs
  • Patent number: 4206216
    Abstract: A compound of the formula ##STR1## possesses antihypertensive activity. Also provided are methods for the preparation of the compounds as well as pharmaceutical formulations and methods for their use as antihypertensive agents.
    Type: Grant
    Filed: June 5, 1978
    Date of Patent: June 3, 1980
    Assignee: Merck & Co., Inc.
    Inventors: Joseph G. Atkinson, Clarence S. Rooney, Yves Girard, Edward L. Engelhardt
  • Patent number: 4198350
    Abstract: This invention relates to the intramolecular oxidation and reduction of aromatic hydrocarbons containing at least one methyl group and a nitro group ortho to the methyl group. Further, it relates to preparing methyl o-amino arylcarboxylates and aromatic amines. The process comprises reacting aromatic hydrocarbons having at least one methyl group and a nitro group ortho to the methyl group in a solvent at a temperature of about 450.degree. to 750.degree. C. When the solvent is methanol, methyl o-amino arylcarboxylates useful in anesthetics, printing inks for polyethylene, and useful in the manufacture of azo dyes are produced. Novel substituted methyl anthranilates have been produced which have the foregoing uses. When no solvent is used or the solvent is benzene, cyclohexane, toluene, hexafluorobenzene or any other non-reactive solvent, the compounds are demethylated and aromatic amines are produced.
    Type: Grant
    Filed: February 12, 1976
    Date of Patent: April 15, 1980
    Assignee: Standard Oil Company (Indiana)
    Inventor: Ellis K. Fields
  • Patent number: 4192944
    Abstract: A novel series of optionally substituted 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-N-(1H-tetrazol-5-yl)carboxamides is provided for use as inhibitors of allergic reactions. The compounds exhibit antiallergy activity by both oral and parenteral routes of administration.
    Type: Grant
    Filed: April 3, 1978
    Date of Patent: March 11, 1980
    Assignee: Bristol-Myers Company
    Inventor: Peter F. Juby
  • Patent number: 4189488
    Abstract: Amidinoformic acids and amidinosulphinic acids which are histamine H.sub.2 -antagonists. Two specific compounds of the present invention are N-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amidinoformic acid and N-methyl-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amidinosulphinic acid.
    Type: Grant
    Filed: June 12, 1978
    Date of Patent: February 19, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin, Rodney C. Young
  • Patent number: 4154835
    Abstract: Novel substituted imidazo [1,2-a] pyridine compounds are disclosed which have a high degree of anthelmintic activity. The compounds are substituted with a carbamate and a halogenated alkene group. Processes for the preparation of such compounds are also disclosed as well as compositions which use the described compounds as active ingredients for the treatment of helminthiasis.
    Type: Grant
    Filed: October 12, 1977
    Date of Patent: May 15, 1979
    Assignee: Merck & Co., Inc.
    Inventor: Richard J. Bochis
  • Patent number: 4140853
    Abstract: A process for the preparation of aminopyridines of the formula ##STR1## wherein R.sub.1 and R.sub.2 are identical or different and are hydrogen or lower alkyl or, together with the nitrogen atom to which they are attached, form a 5-, 6-, or 7-membered heterocyclic ring containing up to 2 more hetero atoms, comprises reacting 4-pyridylpyridinium chloride or a salt thereof, at an elevated temperature, with an acid amide of the formula ##STR2## wherein R.sub.1 and R.sub.2 are as above and Z is --CO--R.sub.3 wherein R.sub.3 is hydrogen, lower alkyl, ##STR3## and R.sub.4 and R.sub.5 are hydrogen or lower alkyl.
    Type: Grant
    Filed: December 6, 1977
    Date of Patent: February 20, 1979
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Vorbrueggen
  • Patent number: 4139537
    Abstract: Cardiac arrhythmias can be treated by administering an effective amount of 3-aryloxy-1-(2-or 4-iminodihydro-1-pyridyl)-2-propanol or phamaceutically acceptable acid addition compound. Many new effective compounds of this type are disclosed.
    Type: Grant
    Filed: June 29, 1976
    Date of Patent: February 13, 1979
    Assignee: Cooper Laboratories, Inc.
    Inventors: Julius Diamond, Ronald A. Wohl
  • Patent number: 4128553
    Abstract: Disclosed are pyridinecarboxylic acids and derivatives thereof which are useful as intermediates for the preparation of 1H-pyrido(2,3-c or 4,3-c) (1,2,6)thiadiazin-4(3H)-one-2,2-dioxide compounds and derivatives thereof which are useful as herbicides.
    Type: Grant
    Filed: January 20, 1978
    Date of Patent: December 5, 1978
    Assignee: The Dow Chemical Company
    Inventor: Lennon H. McKendry
  • Patent number: 4128551
    Abstract: Disclosed are pyridinecarboxylic acids and derivatives thereof which are useful as intermediates for the preparation of 1H-pyrido(2,3-c or 4,3-c) (1,2,6)thiadiazin-4(3H)-one-2,2-dioxide compounds and derivatives thereof which are useful as herbicides.
    Type: Grant
    Filed: January 20, 1978
    Date of Patent: December 5, 1978
    Assignee: The Dow Chemical Co.
    Inventor: Lennon H. McKendry