At 3-position Patents (Class 546/315)
  • Patent number: 4731449
    Abstract: TCNQ complexes with organic pyridinium ions, which may be kept in a molten condition for a relatively long time without the electrical conductivity thereof being substantially reduced after cooling.
    Type: Grant
    Filed: March 3, 1986
    Date of Patent: March 15, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Friedrich Jonas, Jurgen Hocker
  • Patent number: 4727151
    Abstract: Labile quaternary ammonium salts of the following formula (I) and (II) are provided: ##STR1## wherein N represents a tertiary aliphatic amine; wherein N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.8 open chain or cyclo alkyl group, a C.sub.1 -C.sub.8 alkoxyalkyl group, a C.sub.1 -C.sub.8 acyloxyalkyl group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.1 -C.sub.8 carboxyalkyl group, a C.sub.2 -C.sub.8 alkenylphenyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O-lower alkyl (C.sub.1 -C.sub.4) group, an O-acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 which may be the same or different, represents any member defined by R above with the proviso that R.sub.
    Type: Grant
    Filed: November 22, 1978
    Date of Patent: February 23, 1988
    Assignee: INTERx Research Corporation
    Inventor: Nicolae S. Bodor
  • Patent number: 4701447
    Abstract: This invention relates to organic acid-substituted guanidine compounds. Also disclosed are methods for preparing the compounds, compositions containing them, and methods for their use as anthelmintics.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: October 20, 1987
    Assignee: Schering Corporation
    Inventors: Dhiru B. Vashi, Jeffrey N. Clark, Neil A. Lindo
  • Patent number: 4692184
    Abstract: There are disclosed novel 2,6-substituted-3,5-pyridinedicarboxylic acids, esters, salts, amides, halides, and cyano compounds useful as herbicides, and as intermediates which provide herbicides.
    Type: Grant
    Filed: April 24, 1984
    Date of Patent: September 8, 1987
    Assignee: Monsanto Company
    Inventor: Len F. Lee
  • Patent number: 4675328
    Abstract: Polycyclic salts of the formulaA-XN+CH.sub.2 --(Y).sub.n --(CH.sub.2).sub.p --(Z).sub.q --L--(T).sub.r --M IwhereinA.sup.- is the anion of a strong organic or inorganic acid;XN.sup.+ is pyridinium, pyrimidinium, thiazolium or imidazolium substituted by R.sup.1, R.sup.2 and R.sup.3 ;n, q and r individually are the integer 1 or 0 and p is an integer from 1 to 15;Y is CH.sub.2, C(H,OH) or C(O):Z is O, S, CH.sub.2, C(O), NQ.sup.1, SO.sub.2, C(O)O, OC(O), C(O)N(Q.sup.1) or N(Q.sup.1)C(O);L is p-phenylene substituted by R.sup.4 ; andM is phenyl substituted by R.sup.5 and R.sup.6,T has one of the meanings given above, for Z or is C(CH.sub.3).sub.2, C.sub.2 H.sub.4, C(Q.sup.2).dbd.C(Q.sup.3), C.tbd.C, CH.sub.2 C(O), C(O)CH.sub.2, CH.sub.2 O or OCH.sub.2,R.sup.1 is a group Ar, Ar-C.sub.1-4 -alkyl, ArO or ArC(O),Ar is phenyl substituted by R.sup.7, R.sup.8 and R.sup.9 ;R.sup.2 and R.sup.3 individually are H, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy or C.sub.6 H.sub.
    Type: Grant
    Filed: January 15, 1986
    Date of Patent: June 23, 1987
    Assignee: Hoffmann-LaRoche Inc.
    Inventors: Jean-Marie Cassal, Albrecht Edenhofer, Henri Ramuz
  • Patent number: 4675320
    Abstract: Antimicrobial 2-nitro-3-phenylbenzofurans wherein the benzo or the 3-phenyl portion of the molecule is bonded to an alkylene or an oxyalkylene group which is in turn bonded to a basic nitrogen atom or to the nitrogen atom of an (N-lower alkanoyl)amino group.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: June 23, 1987
    Assignee: Riker Laboratories, Inc.
    Inventors: Robert A. Scherrer, Richard M. Stern, Walton J. Hammar
  • Patent number: 4636575
    Abstract: Compounds of formula II and X ##STR1## wherein X is O, S, SO.sub.2, methylene, isopropylidene or NCOR.sub.7 where R.sub.7 is alkyl or phenyl, Y is a direct bond or methylene, n is 1 or 2, R.sub.4 is alkyl, phenyl, naphthyl, cycloalkyl, aralkyl, camphoryl, CF.sub.3, CCl.sub.3, F or NH.sub.2 ; or is alkylene, phenylene or naphthylene, R.sub.5 is hydrogen or halogen, R.sub.6 is hydrogen, alkyl, phenyl or cyano, R.sub.8 is substituted phenyl, substituted naphthyl, anthryl or phenanthryl, R.sub.9 is alkyl R.sub.10 is alkyl or substituted phenyl, and R.sub.11 is alkyl, substituted phenyl, naphthyl, camphoryl, alkylene, phenylene or naphthylene, are latent curing catalysts for acid-curable stoving lacquers. They are distinguished by satisfactory solubility in the acid-curable resin systems, can be stored virtually indefinitely in the dark and, when exposed to shortwave light, make it possible to cure the resins by acid catalysts at a relatively low temperature.
    Type: Grant
    Filed: December 17, 1984
    Date of Patent: January 13, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Rudolf Kirchmayr
  • Patent number: 4631081
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: Z is selected from oxygen and the group --YAn wherein Y is selected from C.sub.1 to C.sub.6 alkyl and benzyl and An is an anion;k is zero or the integer 1;n is an integer selected from 3 and 4;X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, amino, substituted amino and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; andR.sup.
    Type: Grant
    Filed: September 27, 1983
    Date of Patent: December 23, 1986
    Assignee: ICI Australia Limited
    Inventors: Keith G. Watson, Graham J. Bird, Graeme J. Farquharson, Richard J. Conway, Peter G. Tucker
  • Patent number: 4619944
    Abstract: Provided are antihypertensive compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl, and may be the same or different,m is an integer from 0 to 2 inclusive,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl.Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl, heterocyclic, --CO--SR, --CS--SR, ##STR2## CH.sub.2 CO.sub.2 R, --CHM--CO.sub.2 R, --CH.sub.2 --CO--SR, --CN, ##STR3## --CO--NH--CH.sub.2 CO.sub.2 R, ##STR4## or --CO--CO.sub.
    Type: Grant
    Filed: February 19, 1985
    Date of Patent: October 28, 1986
    Assignee: USV Pharmaceutical Corporation
    Inventors: Raymond D. Youssefyeh, Howard Jones
  • Patent number: 4614833
    Abstract: 2-Halo-pyridines of the general formula I ##STR1## wherein X is Cl or Br; A is .dbd.0 or ##STR2## Ar is phenyl or substituted phenyl of the general formula ##STR3## in which n is 0, 1, 2 or 3; R is alkyl C.sub.1-4, alkoxy C.sub.1-4, phenoxy, alkylthio C.sub.1-4, halogen especially F and Cl, OH or C.sub.6 H.sub.5 ; and their salts, addition compounds and precursors (prodrugs).Furthermore the invention is directed to the production of these compounds and pharmaceuticals containing them.
    Type: Grant
    Filed: January 14, 1981
    Date of Patent: September 30, 1986
    Assignee: Lacer, S.A.
    Inventors: Ricardo D. Matas, Jose M. Codina Puigmarti, Jose M. Repolles, Jorge S. Sera
  • Patent number: 4602023
    Abstract: The present invention provides various novel diphenic acid monoamide compounds, novel pharmaceutical compositions and methods of use thereof, as well as novel methods of synthesis therefor. The novel diphenic acid monoamides of the present invention are leukotriene antagonists, 5-lipoxygenase inhibitors, and mediator release inhibitors providing activity useful for treating asthma, allergies, cardiovascular diseases, migraines, and immunoinflammatory conditions.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: July 22, 1986
    Assignee: Warner-Lambert Company
    Inventors: John S. Kiely, Suchin Huang
  • Patent number: 4590200
    Abstract: A novel series of carboxy-substituted naphthalenes and carboxy-substituted benzo-fused heterocycles, such as carboxy-substituted derivatives of indole, benzofuran and benzothiophene, has been prepared, including their pharmaceutically acceptable salts. These particular compounds are useful in therapy for the treatment of thrombosis, ischaemic heart disease, stroke, transient ischaemic attack, migraine, peripheral vascular disease, the vascular complications of diabetes and endotoxic shock. Preferred member compounds include 2-(1-imidazolylmethyl)-3-methylbenzo[b]thiophene-5-carboxylic acid and 3-methyl-2-(3-pyridylmethyl)benzo[b]thiophene-5-carboxylic acid, respectively. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: May 20, 1986
    Assignee: Pfizer Inc.
    Inventors: Peter E. Cross, Roger P. Dickinson
  • Patent number: 4556661
    Abstract: Novel pyridine and pyrazine derivatives of the formula ##STR1## wherein R.sup.4 is 3-pyridyl, 3-pyridyl-1-oxide, 2-pyrazinyl, 2-pyrazinyl-1-oxide, 2-pyrazinyl-4-oxide or 2-pyrazinyl-1,4-dioxide, and R, R.sup.1, R.sup.2 and R.sup.3 are as hereinafter set forth, processes for their preparation, fungicidal compositions containing said compounds, and methods for the use of such compounds or compositions for combatting fungi in agriculture and in horticulture are disclosed. Novel starting materials and fungicidal active substances of the formula ##STR2## wherein R.sup.4' is 3-pyridyl or 2-pyrazinyl, and R and R.sup.1" as hereinafter set forth, which are used for the preparation of the compounds of formula I, and their N-oxides, as well as fungicidal compositions containing these compounds as the active substance, are also described.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: December 3, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Franz Dorn, Francois Montavon, Milos Suchy
  • Patent number: 4542140
    Abstract: .alpha.-Cyanoacrylic acid lower alkyl esters, and their corresponding amides, characterized by having a heterocyclic containing mercapto radical as one .beta.-substituent and an alkylthio, alkenylthio or a heterocyclic containing mercapto radical as another .beta.-substituent are useful for treating ulcers and for suppressing gastric acid secretion.
    Type: Grant
    Filed: October 20, 1983
    Date of Patent: September 17, 1985
    Assignee: American Home Products Corporation
    Inventors: Jehan Bagli, Tibor Bogri, Bozidar Palameta, Luis E. Borella
  • Patent number: 4535086
    Abstract: Heterocyclic compounds of the formula ##STR1## wherein X is --CH.dbd.CH--, --O-- or --S--; R.sup.1 is a group Ar--R.sup.2 or --CH.dbd.CH--C(CH.sub.3).dbd.CH--R.sup.21 ; Ar is phenyl, pyridyl, furyl or thienyl; R.sup.2 is a group --CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3, lower-alkylsulphonyl or formyl; R.sup.21 is a group--CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3 or formyl; R.sup.3 is hydrogen or lower-alkyl and R.sup.4 is hydrogen, hydroxy, amino, lower alkylamino, di-(lower alkyl)amino or lower-alkyl; at least one ring of the molecule being heterocyclic, salts thereof, processes for their preparation, rodenticidal compositions containing these compounds as the active ingredient and methods of use of the rodenticidal compositions are disclosed.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: August 13, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Harald Weiser
  • Patent number: 4532136
    Abstract: 4,4,4-trichloro-(x-pyridyl)-but-2-ene-1-one, wherein x is 2, 3 and 4, and a process for making the same. The compounds are effective fungicides used singly or in combination.
    Type: Grant
    Filed: January 12, 1984
    Date of Patent: July 30, 1985
    Assignee: Consortium Fur Elektrochemische Industriegesellschaft GmbH
    Inventors: Wilhelm Sittenthaler, Fritz Sauter, Peter Stanetty
  • Patent number: 4526896
    Abstract: Antimicrobial 2-nitro-3-phenylbenzofurans wherein the benzo or the 3-phenyl portion of the molecule is bonded to an alkylene or an oxyalkylene group which is in turn bonded to a basic nitrogen atom or to the nitrogen atom of an (N-lower alkanoyl)amino group.
    Type: Grant
    Filed: March 5, 1981
    Date of Patent: July 2, 1985
    Assignee: Riker Laboratories, Inc.
    Inventors: Robert A. Scherrer, Richard M. Stern, Walton J. Hammar
  • Patent number: 4523018
    Abstract: Chromogenic compounds of colorless or lightly colored form are disclosed having the following structural formula: ##STR1## wherein X represents an optionally substituted aminophenyl, indolyl, julolidinyl, kairolyl, piperidinophenyl, pyrrolidinophenyl, morpholinyl, carbazolyl or indolizinyl radical. The compounds of this invention are eligible for use in pressure-sensitive and heat-sensitive record materials and manifold marking systems.
    Type: Grant
    Filed: October 21, 1982
    Date of Patent: June 11, 1985
    Assignee: Yamamoto Kagaku Gosei Co., Ltd.
    Inventors: Yojiro Kumagae, Yasuhisa Iwasaki
  • Patent number: 4507316
    Abstract: Provided are antihypertensive compounds of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl, and may be the same or different,m is an integer from 0 to 2 inclusive,n is an integer from 0 to 4 inclusive,M is alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, polycycloalkyl, polycycloalkyl-alkyl, aryl, aralkyl, heteroaryl, heteroaryl-alkyl, hetero-cycloalkyl, hetero-cycloalkyl-alkyl, fused aryl-cycloalkyl, fused aryl-cycloalkyl-alkyl, fused heteroaryl-cycloalkyl, fused heteroaryl-cycloalkyl-alkyl, alkoxyalkyl, alkylthioalkyl, alkylamino-alkyl, or dialkylaminoalkyl.Y is hydroxy, alkoxy, amino, or substituted amino, aminoalkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, heterocyclic, ##STR2## wherein R is hydrogen, alkyl, or aryl, and where Y is hydroxy, their pharmaceutically acceptable, nontoxic alkali metal, alkaline earth metal, and amine salts.
    Type: Grant
    Filed: June 1, 1981
    Date of Patent: March 26, 1985
    Assignee: USV Pharmaceutical Corporation
    Inventors: Raymond D. Youssefyeh, Howard Jones
  • Patent number: 4495354
    Abstract: The preparation of bicyclic diketones of the formula ##STR1## wherein R.sub.1 is lower alkyl or ar-lower alkyl from a compound of the formula ##STR2## wherein R.sub.1 is as previously described or a salt thereof, and a di-lower alkyl malonate is described. The reactants are combined in a reaction sequence consisting of Michael addition, cyclization, hydrolysis, and decarboxylation. The preparation of the compounds of formula II is also described.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: January 22, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: David L. Coffen, Urs O. Hengartner
  • Patent number: 4487934
    Abstract: A method of preparing substituted acylbenzenes is disclosed. The method comprises reacting selected acylhalides or equivalents with a selected poly-substituted benzene in the presence of an acylating catalyst comprising a perfluoro sulfonic acid polymer.
    Type: Grant
    Filed: June 6, 1980
    Date of Patent: December 11, 1984
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Gregory M. Shutske, Linda L. Setescak
  • Patent number: 4443456
    Abstract: This invention relates to a novel class of amidinourea and amidinothiourea compounds wherein the urea nitrogen atom is substituted by a heterocyclic alkylene group, and their use in pharmaceutical preparations which are useful for producing anti-ulcerogenic, antisecretory, antispasmodic, antihypertensive, anesthetic, anti-arrhythmic, antidiarrheal and antiparasitic action.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: April 17, 1984
    Assignee: William H. Rorer, Inc.
    Inventors: George H. Douglas, William L. Studt, Stuart A. Dodson, Harry K. Zimmerman
  • Patent number: 4417053
    Abstract: A process for preparing substituted glyoxylic acid derivatives by oxidizing with a molecular oxygen containing gas an amide or ester of a hydroxy acid in the presence of a catalytic amount of a cobalt compound.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: November 22, 1983
    Assignee: Stamicarbon B.V.
    Inventors: Antonius Corvers, Cornelis W. van den Broek, Geertrudes H. Suverkropp
  • Patent number: 4414217
    Abstract: 3,5-Di(t-butyl)-4-hydroxyphenyl and 3,5-di(t-butyl)-4-hydroxybenzoyl-substituted pyridines have pharmacological activity as antiinflammatory agents.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: November 8, 1983
    Assignee: Riker Laboratories, Inc.
    Inventor: George G. I. Moore
  • 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: 4380464
    Abstract: Disclosure is made of certain optionally substituted N,N-diacylaminoperfluoroalkanesulfonanilides and agriculturally acceptable salts thereof which are useful as herbicides and plant growth regulators.
    Type: Grant
    Filed: February 4, 1982
    Date of Patent: April 19, 1983
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Ezzat A. Mikhail
  • Patent number: 4369206
    Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: January 18, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wofram Mayer, Hans Rudolph, Eckhard de Cleur, Manfred Schonfelder
  • Patent number: 4338446
    Abstract: 2-R-4-R'-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as intermediates and some as cardiotonics, are prepared by reacting di-(lower-alkyl) hydroxy[2-oxo-2-PY-ethyl]propanedioate (II) with a hydrazine salt of the formula RNHNH.sub.2.nH.sub.x An (III) to produce lower-alkyl 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylate (Ia where R' is lower-carbalkoxy) and reacting Ia with hydrazine hydrate or anhydrous hydrazine to produce 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (Ib where R' is aminocarbamyl), where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, R' is carbamyl, carboxy, aminocarbamyl or lower-carbalkoxy, n is 1 or 2, x is 1, 2 or 3, and An is an anion of a strong inorganic acid or an organic sulfonic acid. Also shown are: the preparation of II from PY-COCH.sub.
    Type: Grant
    Filed: February 26, 1981
    Date of Patent: July 6, 1982
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, William B. Dickinson
  • Patent number: 4337253
    Abstract: 2-R-4,5-dihydro-4-R'-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as cardiotonics, where R is lower-alkyl or lower-hydroxyalkyl, R' is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, are prepared by reacting 4-oxo-4-PY-2-R'-butanenitrile with an N-R-hydrazine salt of a strong inorganic acid or organic sulfonic acid or by reacting a lower-alkyl 4-oxo-4-PY-2-R'-butanoate or lower-alkyl 4-(BN)-4-cyano-4-PY-2-R'-butanoate with N-R-hydrazine where BN is 4-morpholinyl, 1-piperidinyl or 1-pyrrolidinyl. Also shown are: (a) cardiotonic compositions and a method for increasing cardiac contractility using said compounds or salts where R is lower-alkyl (b) the use of I as intermediates in preparing the corresponding 2-R-4-R'-6-PY-3(2H)-pyridazinones; and, (c) the preparation of said lower-alkyl 4-(BN)-4-cyano-4-PY-2-R'-butanoates.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: June 29, 1982
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, William B. Dickinson
  • Patent number: 4331597
    Abstract: Penicillin compounds and methods for the production thereof are described, said penicillin compounds being represented by the formula (I) ##STR1## wherein R.sub.1, R.sub.2, and R.sub.3 each represents hydrogen, a lower alkyl group, a halogen atom, a lower alkoxy group, a hydroxyl group, or a substituted or unsubstituted phenylalkoxy group except that R.sub.1, R.sub.2, and R.sub.3 cannot all represent hydrogen simultaneously; R.sub.4 represents hydrogen or a lower alkyl group; and R.sub.5 represents hydrogen or a hydroxyl group.
    Type: Grant
    Filed: October 2, 1980
    Date of Patent: May 25, 1982
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Osamu Makabe, Yasushi Murai, Tuneo Okonogi, Masahiro Onodera, Takashi Yoshida, Shunzo Fukatsu
  • Patent number: 4322537
    Abstract: Tertiary amines in which at least one group bonded directly to the nitrogen atom is alkyl of 2 to 20 carbon atoms or in which two or more groups bonded directly to the nitrogen atom together are alkylene of 4 to 7 carbon atoms, are oxidized by trihaloacetyl anhydride or trihaloacetyl halide to mono- and di-trihaloacetylated alpha, beta-enamines.
    Type: Grant
    Filed: June 2, 1980
    Date of Patent: March 30, 1982
    Assignee: President and Fellows of Harvard College
    Inventor: Stuart L. Schreiber
  • Patent number: 4322536
    Abstract: A new improved process for producing pyridinaldehydes and hydrazone derivatives thereof, for example, pyridinaldehyde-phenylhydrazones, is described. This comprises reacting an aminomethylpyridine with an aldehyde or a ketone to give a compound of the formula ##STR1## isomerizing the compound (III), in the presence of suitable catalysts, to a compound of the formula ##STR2## and converting the compound (V), in the presence of an acid and optionally in the presence of a hydrazine, into a pyridinaldehyde or a pyridinaldehyde-hydrazone. It is possible to produce by the process according to the invention pyridinaldehydes and pyridinaldehyde-hydrazones in a simple manner, under mild ecologically favorable conditions and in good to very good yields.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: March 30, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Bader, Dieter Reinehr
  • Patent number: 4305943
    Abstract: 4-Amino-2-R-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as cardiotonics, where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents are prepared by: (a) reaction of 2-R-6-PY-3(2H)-pyridazinone (II) with hydrazine; (b) conversion from 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxamide (III); or, (c) conversion form 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (IV). Also shown are: the use of I or salts as cardiotonic agents; and, the preparation of intermediates.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: December 15, 1981
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, William B. Dickinson, Baldev Singh
  • Patent number: 4304937
    Abstract: A process of preparing a carboxylic acid amide which comprises reacting (a) an aldehyde with (b) at least one compound selected from the group consisting of ammonia, a primary amine and a secondary amine in the presence of a molecular oxygen-containing gas and palladium metal or platinum metal as the catalyst.
    Type: Grant
    Filed: November 13, 1979
    Date of Patent: December 8, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nishikido Joji, Tamura Nobuhiro, Fukuoka Yohei
  • Patent number: 4304775
    Abstract: 3-Hydrazino-6-PY-pyridazine or pharmaceutically-acceptable acid-addition salt thereof is useful as a cardiotonic agent, where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substitutents. 6-PY-3-pyridazinol is prepared by reacting 6-PY-3-pyridazinol with a chlorinating agent to produce 3-chloro-6-PY-pyridazine and reacting said 3-chloro compound with hydrazine to produce said 3-hydrazino compound. 3-Hydrazino-6-PY-pyridazine or pharmaceutically-acceptable acid-addition salt thereof is disclosed as the active component in cardiotonic compositions for increasing cardiac contractility and in the method for increasing cardiac contractility in a patient requiring such treatment. The novel intermediate 3-chloro-6-PY-pyridazine is prepared as noted above.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: December 8, 1981
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, William B. Dickinson
  • Patent number: 4304776
    Abstract: 2-R-4-R'-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as intermediates and some as cardiotonics, are prepared by reacting di-(lower-alkyl) hydroxy[2-oxo-2-PY-ethyl]propanedioate (II) with a hydrazine salt of the formula RNHNH.sub.2.nH.sub.x An (III) to produce lower-alkyl 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylate (Ia where R' is lower-carbalkoxy) and reacting Ia with hydrazine hydrate or anhydrous hydrazine to produce 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (Ib where R' is aminocarbamyl), where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, R' is carbamyl, carboxy, aminocarbamyl or lower-carbalkoxy, n is 1 or 2, x is 1, 2 or 3, and An is an anion of a strong inorganic acid or an organic sulfonic acid. Also shown are: the preparation of II from PY--COCH.sub.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: December 8, 1981
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, William B. Dickinson
  • Patent number: 4304941
    Abstract: A method of preparing substituted acylbenzenes is disclosed. The method comprises reacting selected acylhalides or equivalents with a selected poly-substituted benzene in the presence of an acylating catalyst comprising a clay.
    Type: Grant
    Filed: August 1, 1980
    Date of Patent: December 8, 1981
    Assignee: Hoechst Roussel Pharmaceuticals, Inc.
    Inventors: Thomas B. K. Lee, Gregory M. Jobin
  • Patent number: 4302591
    Abstract: Iminobenzyl dihydropyridines of the formula ##STR1## wherein, each R is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, sulfonamido, halogen, alkoxy, alkenyloxy, alkynyloxy, cyano, hydroxy, acyloxy, nitro, amino, alkylmercapto, alkylamino, alkanoylamino, carbalkoxyamino, carboxy, methanesulfonyl, carbalkoxy or trifluoromethyl;each R.sub.4 is lower alkoxy;each R.sub.2 is lower alkyl;and R.sub.3 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic or ##STR2## wherein R is as previously defined; have anti-hypertensive activity.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: November 24, 1981
    Assignee: USV Pharmaceutical Corporation
    Inventors: James R. Shroff, Bernard Loev
  • Patent number: 4301186
    Abstract: This invention relates to new ammonium salts of .alpha.-ketocarboxylic acids, to their use for the production of amines in situ by photochemical decomposition and to photochemically hardenable coating compositions containing these ammonium salts.
    Type: Grant
    Filed: June 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Mayer, Hans Rudolph, Eckhard De Cleur, Manfred Schonfelder
  • Patent number: 4288441
    Abstract: A compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 each represents a member selected from the group consisting of hydrogen and nicotinoyl, with the proviso that R.sub.1, R.sub.2 and R.sub.3 do not all simultaneously represent hydrogen, and the nontoxic acid addition salts thereof.
    Type: Grant
    Filed: July 30, 1980
    Date of Patent: September 8, 1981
    Assignee: Daiichi Seiyaku Co., Ltd.
    Inventors: Tosaku Miki, Akashi Eriguchi, Yasushi Abiko, Kinya Kameda
  • Patent number: 4252814
    Abstract: There are provided novel cyanomethyl thioester compounds useful as ovicidal and larvicidal agents effective for the control of insects.
    Type: Grant
    Filed: July 5, 1979
    Date of Patent: February 24, 1981
    Assignee: American Cyanamid Company
    Inventors: Peter J. Wepplo, Donald P. Wright, Jr.
  • Patent number: 4252956
    Abstract: The present invention relates to compounds which are derivatives of 1,4-dihydropyridine-3-carbothiol acids of the formula: ##STR1## wherein R is hydrogen, an alkyl, aryl, heteryl;R' is a lower alkyl, aralkyl;R" is an alkoxy, alkylthio, aralkylthio;R"' is methyl;R'"+R" is phenylene (ortho-).The compounds of the present invention reveal a coronarodilating activity, and are useful in medicine.
    Type: Grant
    Filed: March 19, 1979
    Date of Patent: February 24, 1981
    Inventors: Brigita A. Vigante, Yan-Voldemar Y. Ozol, Rasma O. Vitolin, Gunta O. Silenietse, Agris A. Kimenis, Gunar Y. Dubur
  • Patent number: 4245099
    Abstract: A 2-acyl-6-aminomethylphenol derivative having the formula (I): ##STR1## wherein R.sup.1 represents a straight chain or branched chain alkyl group of 1 to 6 carbon atoms unsubstituted or substituted with 1 to 3 halogen atoms; a hydrogen atom or a group having the formula (II):--C.sub.n H.sub.2n --R.sup.7 (II)wherein n represents 0 or an integer of 1 to 6; R.sup.7 represents a cycloalkyl group of 3 to 8 carbon atoms unsubstituted or substituted with at least one lower alkyl group; a phenyl group unsubstituted or substituted with at least one lower alkyl group, a halogen atom, a lower alkoxy group or a lower alkylthio group; a lower alkoxy group; a lower alkylthio group; a lower alkylsulfinyl group; a lower alkylsulfonyl group; an N-lower alkylamino group; an N,N-di-lower alkylamino group; or a pyridyl, furyl or thienyl group; R.sup.
    Type: Grant
    Filed: July 24, 1979
    Date of Patent: January 13, 1981
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Hiroyuki Itoh, Mitoshi Konno, Takao Tokuhiro, Sadahiko Iguchi, Masaki Hayashi
  • Patent number: 4238492
    Abstract: Arylcarbonylphenoxyalkylcarboxylic acids, and alkyl esters and salts thereof, are described. The compounds may be formulated into therapeutic compositions and administered to animals, including humans, for the treament of hyperlipidaemia and related diseases.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: December 9, 1980
    Assignee: Societe de Recherches Industrielles S.O.R.I.
    Inventor: Bernard Majoie
  • Patent number: 4237275
    Abstract: An improved process for producing pyridinaldehydes and hydrazone derivatives thereof, for example, pyridinaldehyde-phenylhydrazones, is described. This comprises reacting a aminomethylpyridine with an aldehyde or a ketone to give a compound of the formula ##STR1## isomerizing the compound (III), in the presence of suitable catalysts, to a compound of the formula ##STR2## and converting the compound (V), in the presence of an acid and optionally in the presence of a hydrazine, into a pyridinaldehyde or a pyridinaldehyde-hydrazone. It is possible to produce by the process according to the invention pyridinaldehydes and pyridinaldehyde-hydrazones in a simple manner, under mild ecologically favorable conditions and in good to very good yields.
    Type: Grant
    Filed: May 29, 1979
    Date of Patent: December 2, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Rolf Bader, Dieter Reinehr
  • Patent number: 4232016
    Abstract: 3-Fluoro-2,3-dihydro-1H-1,4-benzodiazepin-2-ones of the formula ##STR1## wherein R.sup.1 is H, alkyl or fluorinated alkyl of 1-4 carbon atoms and up to 9 fluorine atoms or cycloalkylalkyl of 4-8 carbon atoms; R.sup.2 is phenyl; monohalophenyl or pyridyl; R.sup.3 is F, Cl, Br or NO.sub.2, and physiologically acceptable acid addition salts thereof, are central nervous system depressants.
    Type: Grant
    Filed: December 9, 1975
    Date of Patent: November 4, 1980
    Assignee: Merck Patent Gesellschaft mit beschraenkter Haftung
    Inventors: Eike Poetsch, Jurgen Uhl, Dieter Marx, Wighard Strehlow, Helmut Muller-Calgan, Giuliano Dolce
  • Patent number: 4225716
    Abstract: The process for the manufacture of a compound of the formula ##STR1## comprising reacting in the presence of a basic nitrogen compound at elevated temperature phosphorus oxychloride with a compound of the formula ##STR2## in the molar ratio of phosphorus oxychloride to hydroxypyridine of 1:1 to 1.3:1 whereinR.sup.1 is hydrogen, alkyl having 1 to 8 carbon atoms, phenyl, carbalkoxy having 2 to 5 total carbon atoms, carbalkoxymethyl having 3 to 6 total carbon atoms or substituted phenyl having a substituent selected from the group consisting of chloro, bromo, methyl, ethyl, methoxy, ethoxy, cyano and nitro and R.sup.2 is hydrogen, cyano, nitro or acetyl.
    Type: Grant
    Filed: January 31, 1979
    Date of Patent: September 30, 1980
    Assignee: Cassella Aktiengesellschaft
    Inventors: Ulrich Buhler, Ernst Heinrich
  • Patent number: 4211872
    Abstract: Substituted furopyridinones and furopyrazinones which are useful as color formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting diphenylamines with substituted benzoyl (or 3-indolylcarbonyl)pyridinecarboxylic acids and substituted benzoyl (or 3-indolylcarbonyl)pyrazinecarboxylic acids, respectively.
    Type: Grant
    Filed: December 11, 1978
    Date of Patent: July 8, 1980
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4204064
    Abstract: A method, composition and compounds useful in said compositions for treating the skin and scalp characterized by an excessive secretion of sebum to improve the condition thereof by reducing said excessive secretion of sebum includes topically applying to a human having skin and/or a scalp so characterized a cosmetic composition containing as an active ingredient a derivative of cysteine or cysteamine. The composition contains about 0.1-5 weight percent of said derivative and also contains as a carrier for the active ingredient, water, a mixture of water and a lower alkanol, a lower alkanol, a mixture of a lower alkanol and a cosmetic resin, a reducing agent, a neutralizing agent or a vegetable oil.
    Type: Grant
    Filed: January 24, 1978
    Date of Patent: May 20, 1980
    Assignee: L'Oreal
    Inventor: Gregoire Kalopissis