Patents Examined by David E. Wheeler
  • Patent number: 4156726
    Abstract: There are described compounds of formula I, ##STR1## in which R.sub.5 to R.sub.8 may be a variety of substituents, OR AN ADJACENT PAIR OF R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a chain --COCH.dbd.C(COOH)NRh--,Or one of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 form a group of formula II, ##STR2## in which Ra, Rb and Rc have the same significances as R.sub.5, R.sub.6, R.sub.7 and R.sub.8,X is an optionally interrupted or substituted hydrocarbon chain,Rg and Rh, which may be the same or different are each alkyl, alkenyl, phenyl-alkyl, alkanoyl, benzoyl or phenylalkanoyl,Or Rg and R.sub.8 and/or Rh and Rc in formula II, together form a chain --(CH.sub.2).sub.n --, and n is 2, 3 or 4.There are also described processes for making the compounds and pharmaceutical, e.g. anti-allergic, compositions containing the compounds.
    Type: Grant
    Filed: November 26, 1975
    Date of Patent: May 29, 1979
    Assignee: Fisons Limited
    Inventors: Roger C. Brown, Hugh Cairns, Anthony R. Payne
  • Patent number: 4155911
    Abstract: A new process is disclosed for the preparation of compounds of structure: ##STR1## and are as defined herein characterized in that a compound of structure ##STR2## where R and R.sup.1 have the meanings given herein, is reacted in a suitable solvent with a haloamide in the presence of a metal oxide or a haloamide in the presence of a free radical initiator under the influence of light or heat or alternatively with a halogen in the presence of a metal oxide, to give a compound of structure: ##STR3## where R and R.sup.
    Type: Grant
    Filed: August 1, 1977
    Date of Patent: May 22, 1979
    Assignee: Farmitalia Carlo Erba S.p.A.
    Inventors: Maurizio Foglio, Antonino Suarato, Paolo Masi, Giovanni Franceschi, Giorgio Palamidessi, Luigi Bernardi
  • Patent number: 4154831
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 denotes optionally substituted phenyl, thienyl, furyl or 1,4-cyclohexadienyl, R.sub.2 represents a free carboxyl group or an esterified carboxyl group which can be split physiologically, R.sub.3 represents hydrogen, lower alkoxy or an optionally substituted methyl group and B represents an optionally substituted six-membered ring with 1 to 3 ring nitrogen atoms, which is bonded to the carbonyl group --C(.dbd.O)-- by one of its carbon atoms, the nitrogen atoms of a monocyclic six-membered ring having 2 nitrogen atoms being either adjacent or separated by two ring carbon atoms, and the salts of such compounds which have a salt-forming group, including the inner salts, for example the 7.beta.-[D(-)-.alpha.-(3,5-Dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-c arboxamido)-phenylacetamido]-cephalosporanic acid, have antibiotic activity.
    Type: Grant
    Filed: April 20, 1977
    Date of Patent: May 15, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Karoly Kocsis, Heinrich Peter, Hans Bickel
  • Patent number: 4154927
    Abstract: Compounds of the formula ##STR1## wherein A is ##STR2## R is hydrogen, lower alkyl, benzyl, p-methoxybenzyl, p-nitrobenzyl, diphenylmethyl, tri(lower alkyl)silyl, lower alkoxymethyl, 2,2,2-trichloroethyl, ##STR3## Y is halogen or lower alkoxy; R.sub.1 is lower alkyl, phenyl, or substituted phenyl; and X is hydrogen, lower alkanoyloxy, ##STR4## or certain heterothio groups; R.sub.4 is hydrogen or lower alkyl; R.sub.5 is lower alkyl; are disclosed. These compounds, particularly the free acids, possess the useful pharmacological property of inhibiting .beta.-lactamase enzymes as well as being useful as intermediates, particularly where R is a readily cleavable ester, in the preparation of antibacterially active 6.alpha.-methoxy penicillins and 7.alpha.-methoxy cephalosporins.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: May 15, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Eric M. Gordon
  • Patent number: 4154741
    Abstract: A new process for the manufacture of pyrono-condensed coumarin compounds by reacting an anil derivative of a heterocyclic compound with a cyanoacetic acid derivative in the presence of a base and a strong polar aprotic solvent is described.
    Type: Grant
    Filed: December 27, 1977
    Date of Patent: May 15, 1979
    Assignee: Ciba-Geigy Corporation
    Inventors: Erich Ziegler, Otto Wolfbeis
  • Patent number: 4154943
    Abstract: The invention relates to the preparation of vincadifformine.Tetrahydro-.beta.-carboline (II) is reacted with benzoyl chloride to provide 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido-[3,4b]-indole (III). Then compound (III) is reduced to give 2-benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4b]-indole (IV). Thereafter, compound (IV) is transformed by t-butyl hypochlorite into chloroindolenine derivative (V) which is immediately treated with thallium t-butyl methyl malonate to give t-butyl methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VI). Compound (VI) is then partly decarboxylated into methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (VII). Compound (VII) is hydrogenated to give methyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5-carboxylate (IX). In an alternative embodiment, compound (VI) can be hydrogenated to methyl t-butyl 1,2,3,4,5,6-hexahydroazepino-[4,5b]-indole-5,5-dicarboxylate (VIII) which is then decarboxylated into compound (IX).
    Type: Grant
    Filed: December 29, 1977
    Date of Patent: May 15, 1979
    Assignee: University of Vermont
    Inventor: Martin E. Kuehne
  • Patent number: 4153711
    Abstract: .beta.-[2-[(DIALKYLAMINO)METHYL]-1H-indol-3-yl]-.alpha.,.alpha.-diphenylpro pionitriles and 4-[[2-[(dialkylamino)methyl]-1H-indol-3-yl]methyl]-2,4-dihydro-5-lower alkyl-2-phenyl-3H-pyrazol-3-ones and acid addition salts thereof which are useful pharmacological agents, especially as central nervous system depressants, are disclosed. The compounds can be produced by reacting an anion of an acetonitrile or a pyrazol-3-one with the appropriate quatenary salt of 2-alkyl-1,2,3,4-tetrahydropyrrolo[3,4-b]indole.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: May 8, 1979
    Assignee: Warner-Lambert Company
    Inventors: Harold Zinnes, Neil A. Lindo
  • Patent number: 4153707
    Abstract: A compound of the formula: ##STR1## wherein X is a member selected from the group consisting of hydrogen, alkyl of from 1 to 3 carbon atoms, inclusive, chlorine or bromine; Y is a member selected from the group consisting of hydrogen, chlorine or bromine and R is a member selected from the group consisting of hydrogen or lower alkyl of from 1 to 3 carbon atoms.The compounds can be applied to seeds, plants, animals, objects, or places for preventing damage due to fungi. General methods for preparing the active compounds, compositions and methods of use are shown.
    Type: Grant
    Filed: November 10, 1977
    Date of Patent: May 8, 1979
    Assignee: The Upjohn Company
    Inventor: Malcolm W. Moon
  • Patent number: 4153697
    Abstract: 8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline-8-N-glucuronide and its preparation as well as its use in medicaments, especially for the treatment of psychic disorders, are described.
    Type: Grant
    Filed: May 23, 1978
    Date of Patent: May 8, 1979
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ingolf Hornke, Hans-Wolfram Fehlhaber, Michael Uihlein
  • Patent number: 4152433
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is (C.sub.1 to C.sub.6) alkyl,R.sup.2 is a carboxy or a protected carboxy group,R.sup.3 is amino or a protected amino group andA is hydroxyimino (C.sub.1 to C.sub.6) alkylene or (C.sub.1 to C.sub.6)-alkoxyimino (C.sub.1 to C.sub.6)alkylene,And pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: September 26, 1977
    Date of Patent: May 1, 1979
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takashi Kamiya, Takao Takaya
  • Patent number: 4152519
    Abstract: This invention relates to novel aspidospermidines being useful in synthesis and also exhibiting interesting physiological properties. A process for the preparation of the novel compounds is described and exemplified and examples of pharmaceutical compositions containing the novel compounds are given. Pharmacological test data are presented for a novel compound according to the invention.
    Type: Grant
    Filed: July 7, 1977
    Date of Patent: May 1, 1979
    Assignee: Parcor
    Inventor: Alain Heymes
  • Patent number: 4152432
    Abstract: Compounds of the formula ##STR1## wherein R is selected from the group consisting of hydrogen and groups easily removable by acid hydrolysis or hydrogenolysis, R' is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms, alkenyl and alkynyl of 2 to 4 carbon atoms and groups easily removable by acid hydrolysis or hydrogenolysis, A is selected from the group consisting of hydrogen, alkali metal and equivalents of an alkaline earth metal or magnesium and an organic amine base with the proviso that when R' is a group easily removable by acid hydrolysis or hydrogenolysis, R is also and when R' is hydrogen, R also is hydrogen and the wavy line means the OR' group may be in either one of the two possible syn or anti positions having antibiotic activity and process for their preparation.
    Type: Grant
    Filed: July 19, 1977
    Date of Patent: May 1, 1979
    Assignee: Roussel Uclaf
    Inventors: Rene Heymes, Andre Lutz
  • Patent number: 4150135
    Abstract: 4A-Aryl-cis-decahydroisoquinolines, such as N-phenethyl-4a-(m-hydroxyphenyl)-cis-decahydroisoquinoline, useful as analgesics.
    Type: Grant
    Filed: March 4, 1977
    Date of Patent: April 17, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William C. Ripka
  • Patent number: 4150224
    Abstract: Novel cephalosporin compounds useful as antibiotics having the following formula and pharmaceutically useful salts thereof: ##STR1##
    Type: Grant
    Filed: October 4, 1977
    Date of Patent: April 17, 1979
    Assignee: Yeda Research and Development Co., Ltd.
    Inventors: Abraham Nudelman, Abraham Patchornik
  • Patent number: 4148806
    Abstract: This invention relates to a novel process for preparing a group of novel substituted indolopyrones.
    Type: Grant
    Filed: December 14, 1977
    Date of Patent: April 10, 1979
    Assignee: Warner-Lambert Company
    Inventors: Richard E. Brown, Paul C. Unangst, Frank Fontsere, Arthur C. Fabian
  • Patent number: 4148794
    Abstract: Lower-alkyl 1-R.sub.1 -3-R.sub.5 CO-4a.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '"-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylat es, useful as intermediates for the preparation of 3-R.sub.1 -6(eq)-R.sub.4 -7-R.sub.2 "-8-R.sub.2 -9-R.sub.2 '-10-R.sub.2 '"-11(ax)-R.sub.3 -11(eq)-CH.sub.2 CH.sub.2 COR.sub.5 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared by acylation of an appropriate lower-alkyl 1-R.sub.1 -4a.alpha.-R.sub.3 -5.alpha.C-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '"-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carboxylat e or carboxylation of an appropriate 1-R.sub.1 -3-COR.sub.5 "-4.alpha.-R.sub.3 -5.alpha.-R.sub.4 -6-R.sub.2 "-7-R.sub.2 -8-R.sub.2 '-9-R.sub.2 '"-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline.
    Type: Grant
    Filed: February 16, 1978
    Date of Patent: April 10, 1979
    Assignee: Sterling Drug Inc.
    Inventors: Thomas R. Lewis, William F. Michne
  • Patent number: 4147788
    Abstract: 1-Difluoromethyl-6,7-methylenedioxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and certain of its alkylaminoalkyl esters, useful in treating bacterial infections in mammals.
    Type: Grant
    Filed: January 14, 1977
    Date of Patent: April 3, 1979
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Kyu T. Lee
  • Patent number: 4145418
    Abstract: Thienopyridine derivatives of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is hydrogen, an alkyl, an aryl, an aralkyl or a halogen; R.sup.1 and R.sup.2 may, taken together, represent an alkylene group; X is hydrogen or an alkyl; Y is oxygen or sulfur; Z is phenyl which may optionally be substituted; R.sup.3 is hydrogen or an alkoxy; and R is a group of the formula: ##STR2## or of the formula: ##STR3## (wherein R.sup.4 is hydrogen, an acyloxy or a nucleophilic compound residue) or a pharmaceutically acceptable salt thereof are found to have activity against a broad spectrum of gram-positive and gram-negative bacteria, particularly against bacteria of the genus Pseudomonas .
    Type: Grant
    Filed: December 29, 1976
    Date of Patent: March 20, 1979
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yutaka Kuwada, Kanji Meguro
  • Patent number: 4144237
    Abstract: Novel 3',4'-dehydro- and 4'-deoxo-vincristine and vinblastine compounds are obtained by coupling an indole unit of the catharanthine series and a dihydroindole unit of the vindoline series. Representative compounds of this series showed superior results when tested for activity against L1210 and P388 mouse leukemia.
    Type: Grant
    Filed: June 13, 1977
    Date of Patent: March 13, 1979
    Assignee: The United States of America as represented by the Department of Health, Education and Welfare
    Inventor: James P. Kutney
  • Patent number: 4143166
    Abstract: The new 7-(.alpha.,.alpha.-disubstituted-acetamido)-3-substituted-3-cephem-4-carbo xylic acid of the present invention is represented by the following formula: ##STR1## wherein R.sup.1 is hydrogen, halogen, hydroxy, nitro, lower alkoxy or acylamino, R.sup.2 is hydrogen or acyl andR.sup.3 is lower alkanoyloxy, carbamoyloxy which may have lower alkyl, aryl or protective group for amino, or a heterocyclicthio which may have lower alkyl, aryl or protective group for amino, or a hetero- which may have lower alkyl.
    Type: Grant
    Filed: February 3, 1976
    Date of Patent: March 6, 1979
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Takao Takaya, Takashi Masugi, Hisashi Takasugi, Hiromu Kochi