Patents Represented by Attorney Arthur R. Whale
  • Patent number: 4468514
    Abstract: Thiazoline azetidinones are converted in good yield to 3-bromo-3-methylcephams by treatment with a bromine source and dimethyl sulfoxide.
    Type: Grant
    Filed: December 17, 1982
    Date of Patent: August 28, 1984
    Assignee: Eli Lilly and Company
    Inventor: Robin D. G. Cooper
  • Patent number: 4468380
    Abstract: The present invention is directed to novel anticoccidial compositions and methods of employing the same to control coccidiosis in poultry. These compositions comprise a polyether antibiotic and a second component which is a selected carbanilide.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: August 28, 1984
    Assignee: Eli Lilly and Company
    Inventors: George O. P. O'Doherty, Albert J. Clinton
  • Patent number: 4468462
    Abstract: The present invention discloses selectable recombinant DNA cloning vectors for use in Streptomyces.
    Type: Grant
    Filed: December 22, 1982
    Date of Patent: August 28, 1984
    Assignee: Eli Lilly and Company
    Inventors: Nancy E. Malin, Jeffrey T. Fayerman, Michael D. Jones, James A. Mabe, Walter M. Nakatsukasa
  • Patent number: 4468511
    Abstract: C-20- and C-23-Modified macrolide derivatives of demycinosyltylocin (DMT), 5-O-mycaminosyltylonolide (OMT) 23-de(mycinosyloxy)tylosin, 23-deoxy-OMT, 20-dihydro-20-deoxy-DMT and 20-dihydro-20-deoxy-OMT are useful antibiotics or intermediates to antibiotics.
    Type: Grant
    Filed: February 28, 1983
    Date of Patent: August 28, 1984
    Assignee: Eli Lilly and Company
    Inventors: Herbert A. Kirst, John E. Toth
  • Patent number: 4463181
    Abstract: This invention discloses a process for removing a sulfonyl group from the 1-position of a benzimidazole to allow conversion of 2-amino-1,5-substituted-benzimidazole compounds into 2-amino-1,6-substituted-benzimidazole compounds. The 5-isomer is reacted with an alkali metal hydroxide or carbonate in an inert aqueous organic solvent system. The reaction is acidified to precipitate the base and form the intermediate benzimidazole tautomer. The intermediate is then reacted with a sulfonyl acylating agent or a haloalkyl isothiocyanate to form a mixture of 2-amino-1,5(6)-substituted-benzimidazole compounds. This invention also discloses the same process for removing a sulfonyl group from the 1-position of a benzimidazole to allow conversion of 2-amino-1,6-substituted-benzimidazole compounds into 2-amino-1,5-substituted-benzimidazole compounds.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: July 31, 1984
    Assignee: Eli Lilly and Company
    Inventors: Tina M. Morwick, James H. Wikel
  • Patent number: 4463092
    Abstract: Antibiotic A53868 factor A, which is N.sup.2 -glycyl-N-(2-methylene-2-phosphonoethyl)leucinamide, and the formula: ##STR1## and the salts thereof, which are useful as antibiotics or as intermediates to antibiotics; methods of preparing A53868 factor A by fermentation of Streptomyces luridus; and the microorganism S. luridus NRRL 15101.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: July 31, 1984
    Assignee: Eli Lilly and Company
    Inventors: Ronald D. Johnson, Ralph M. Kastner, Stephen H. Larsen, Earl E. Ose
  • Patent number: 4462942
    Abstract: Antibiotic A47934 is produced by submerged, aerobic fermentation of new Streptomyces toyocaensis NRRL 15009. The antibiotic is active against gram-positive bacteria in vitro and in vivo. It promotes growth in poultry and swine and serves to enhance feed efficiency in ruminant animals having a developed rumen.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: July 31, 1984
    Assignee: Eli Lilly and Company
    Inventors: Robert L. Hamill, Ralph E. Kastner
  • Patent number: 4461723
    Abstract: Glycopeptide antibiotic A-4696G is produced by culturing Actinoplanes missouriensis mutant strain ATCC 31681 under submerged aerobic fermentation conditions, and is recovered from the fermentation broth by resin adsorption and chromatographic purification. A-4696G inhibits the growth of bacteria pathogenic to man and animals and also enhances the growth of ruminants by increasing feed utilization.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: July 24, 1984
    Assignee: Eli Lilly and Company
    Inventors: Charles L. Hershberger, Kurt E. Merkel, Robert E. Weeks, Gene M. Wild
  • Patent number: 4459405
    Abstract: 7-(S)-Acylamino-3-hydroxymethyl-3-cephem sulfones are disclosed. These compounds are intermediates in the synthesis of 1-oxa .beta.-lactam antibiotics.
    Type: Grant
    Filed: November 16, 1982
    Date of Patent: July 10, 1984
    Assignee: Eli Lilly and Company
    Inventor: David A. Hall
  • Patent number: 4459290
    Abstract: C-23-Modified derivatives of 5-O-mycaminosyl-tylonolide (OMT) of the formula: ##STR1## wherein R is chloro, fluoro, --S--R.sup.4, azido, --NHR.sup.5, pyridinium, or --OSO.sub.2 CF.sub.3 ;R.sup.1 is hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl, phenylpropionyl, phenoxyacetyl or phenylthioacetyl;R.sup.2 and R.sup.3 are hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl or phenylpropionyl;R.sup.4 is hydrogen, optionally substituted C.sub.1 -C.sub.6 -alkyl, cyclohexyl, C.sub.1 -C.sub.5 alkanoyl, optionally substituted phenyl or benzyl, or an optionally substituted heteroaryl group selected from imidazolyl, pyrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, thienyl and furanyl; andR.sup.5 is hydrogen or an acyl group selected from optionally substituted C.sub.1 -C.sub.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: July 10, 1984
    Assignee: Eli Lilly and Company
    Inventors: Herbert A. Kirst, John E. Toth
  • Patent number: 4459226
    Abstract: Insulin can be recovered for processing and re-use from an insulin-protamine complex by bringing the complex into contact with an aqueous medium having a pH of from about 2 to about 5 and containing an insulin dissociating or depolymerizing agent, a cation exchanger, and a salt at a concentration of from about 0.2 M to about 0.6 M.
    Type: Grant
    Filed: February 26, 1982
    Date of Patent: July 10, 1984
    Assignee: Eli Lilly and Company
    Inventors: Denise L. Grimes, C. Stephen Hollinden
  • Patent number: 4458071
    Abstract: An azetidin-2-one-4-sulfinic acid represented by the formula ##STR1## is reacted with Pb(OAc).sub.4 in liquid SO.sub.2 containing CuII ion to provide isomeric cyclization products of the formulas ##STR2## wherein R is e.g. benzyl, phenoxymethyl, benzyloxy, diphenylmethoxy, and R.sub.1 is a carboxy-protecting group. The products of the process are useful intermediates for 1-oxa-.beta.-lactam antibacterials.
    Type: Grant
    Filed: November 16, 1982
    Date of Patent: July 3, 1984
    Assignee: Eli Lilly and Company
    Inventor: David A. Hall
  • Patent number: 4458085
    Abstract: 3-Benzothienylglycines are prepared by reaction of a benzothiophene with an .alpha.-hydroxyglycine derivative in the presence of trifluoroacetic acid.
    Type: Grant
    Filed: April 12, 1983
    Date of Patent: July 3, 1984
    Assignee: Eli Lilly and Company
    Inventor: George W. Huffman
  • Patent number: 4458065
    Abstract: Apramycin derivatives substituted at the 7'-amino group with a methyl, ethyl, n-propyl or n-butyl substituent are broad spectrum antibiotics. Also claimed are intermediates in the synthesis of these 7'-N-alkylapramycin derivatives.
    Type: Grant
    Filed: February 17, 1983
    Date of Patent: July 3, 1984
    Assignee: Eli Lilly and Company
    Inventor: Herbert A. Kirst
  • Patent number: 4452745
    Abstract: Fluorenes bearing a 9-aminoalkyl substituent are useful antiarrhythmic agents. Pharmaceutical formulations containing such compounds are provided, as well as a method of treatment.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: June 5, 1984
    Assignee: Eli Lilly and Company
    Inventors: William B. Lacefield, Richard L. Simon
  • Patent number: 4452784
    Abstract: C-23-Modified derivatives of demycinosyltylosin (DMT) of the formula: ##STR1## wherein R is iodo, bromo, chloro, fluoro, --S--R.sup.4, azido, --NHR.sup.5, pyridinium or --OSO.sub.2 CF.sub.3 ;R.sup.1 is hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl, phenylpropionyl, phenoxyacetyl or phenylthioacetyl;R.sup.2 is hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl or phenylpropionyl;R.sup.3 is hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl or phenoxyacetyl;R.sup.4 is hydrogen, optionally substituted C.sub.1 -C.sub.6 -alkyl, cyclohexyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: June 5, 1984
    Assignee: Eli Lilly and Company
    Inventors: Herbert A. Kirst, John E. Toth
  • Patent number: 4452741
    Abstract: Antibiotic A-39183 complex, comprising microbiologically active, related factors A, B, C, D, and E, is produced by submerged, aerobic fermentation of a new microorganism Streptomyces sp., NRRL 12049. The A-39183 antibiotics are closely related antibiotics. The individual A-39183 factors are separated by chromatography. The A-39183 factors are antibacterial agents which have activity against Staphylococcus and Streptococcus species that are penicillin resistant. The A-39183 factors are also active against both gram-positive and gram-negative anaerobic bacteria, and are ionophores.
    Type: Grant
    Filed: February 23, 1983
    Date of Patent: June 5, 1984
    Assignee: Eli Lilly and Company
    Inventors: Kay F. Koch, Ralph E. Kastner
  • Patent number: 4452631
    Abstract: Novel 1-(2,6-dialkoxybenzoyl)-3-(substituted phenyl)ureas are disclosed in the present invention. These compounds are useful both alone and in combination with other herbicides for controlling the growth of undesired plants.
    Type: Grant
    Filed: April 8, 1982
    Date of Patent: June 5, 1984
    Assignee: Eli Lilly and Company
    Inventors: Kenneth W. Burow, Jr., George W. Johnson
  • Patent number: 4452778
    Abstract: Antibiotic compositions comprising a 1-oxa .beta.-lactam antibiotic compound of the formula ##STR1## or pharmaceutically acceptable salts thereof and either tobramycin, amikacin or piperacillin exhibit synergistic activity against multiple-antibiotic-resistant organisms. The 1-oxa compound can be used in conjunction with tobramycin, amikacin or piperacillin in a method of treating infections caused by resistant organisms.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: June 5, 1984
    Assignee: Eli Lilly and Company
    Inventor: Gordon L. Brier
  • Patent number: 4451396
    Abstract: The discovery of this invention is a process for inhibiting undesired irreversible thiol reactions of thiol-containing peptides while preforming desirable thiol intermediates during methionyl cleavage of said peptides using CNBr by carrying out said cleavage in the presence of thiosulfate ion.
    Type: Grant
    Filed: August 1, 1983
    Date of Patent: May 29, 1984
    Assignee: Eli Lilly and Company
    Inventor: Richard D. Di Marchi