Patents Represented by Attorney Nancy J. Harrison

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  • 2-N-Acylated and 2-N-alkylated derivatives of 4-O-substituted-2-deoxystreptamine aminoglycosides and process
    Patent number: 4424344
    Abstract: Nickel salts are used to effect the regio-selective acylation and alkylation of the 2'-amino group of 4-O-substituted-2-deoxystreptamine containing aminoglycosides. The 2'-N-substituted derivatives of apramycin, certain .alpha. or .beta.-(lower alkyl)aprosaminides and certain .alpha. or .beta.-(substituted lower alkyl)aprosaminides are new. The 2'-N-substituted-4-O-substituted-2-deoxystreptamine aminoglycosides produced by the process of this invention are antibacterial agents.
    Type: Grant
    Filed: September 21, 1981
    Date of Patent: January 3, 1984
    Assignee: Eli Lilly and Company
    Inventors: Herbert A. Kirst, Brenda A. Truedell
  • Process for producing 20-dihydro-20-deoxy-23-de(mycinosyloxy)tylosin
    Patent number: 4423148
    Abstract: 20-Dihydro-20-deoxy-23-de(mycinosyloxy)tylosin (20-deoxo-DMOT), specified 2'-acyl ester derivatives, and their acid addition salts are useful intermediates and antibacterial agents. Methods of preparing 20-deoxo-DMOT and 5-O-mycaminosyltylactone by fermentation of Streptomyces fradiae ATCC 31733 are included.
    Type: Grant
    Filed: July 2, 1982
    Date of Patent: December 27, 1983
    Assignee: Eli Lilly and Company
    Inventor: Gene M. Wild
  • Fermentation process for producing demycinosyltylosin
    Patent number: 4419447
    Abstract: 23-Demycinosyltylosin (DMT) which has the formula: ##STR1## 20-dihydro-DMT, specified acyl ester derivatives, and their acid addition salts are useful antibacterial agents. Improved methods of making 5-O-mycaminosyltylonolide (OMT) and 20-dihydro-OMT by mild acid hydrolysis of DMT and 20-dihydro-DMT, respectively, are included.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: December 6, 1983
    Assignee: Eli Lilly and Company
    Inventors: Richard H. Baltz, Gene M. Wild, Eugene T. Seno
  • 20-Dihydro-20-deoxy-23-demycinosyltylosin and process for its production
    Patent number: 4419508
    Abstract: 20-Dihydro-20-deoxy-23-demycinosyltylosin (DH-DO-DMT), 20-dihydro-20-deoxy-5-O-mycaminosyltylonolide (DH-DO-OMT), specified acyl ester derivatives, and their acid addition salts are useful intermediates and antibacterial agents. Methods of preparing DH-DO-DMT and DH-DO-OMT by fermentation of Streptomyces fradiae and the microorganism S. fradiae ATCC 31733 are included.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: December 6, 1983
    Assignee: Eli Lilly and Company
    Inventors: Richard H. Baltz, Herbert A. Kirst, Gene M. Wild, Eugene T. Seno
  • Ester derivatives of 5-O-mycaminosyl tylonolide and method of using same
    Patent number: 4401660
    Abstract: Ester derivatives of 5-O-mycaminosyl tylonolide (OMT) of the formula ##STR1## wherein R and R.sup.1 are selected from hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl, or phenylpropionyl; R.sup.2 is hydrogen or an acyl group selected from: ##STR2## p is 0 or 1; m and n are integers from 0 to 4; R.sup.3 is hydrogen, halo, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, phenyl, C.sub.5 -C.sub.8 -cycloalkenyl, naphthyl, indenyl, tetralinyl, decalinyl, adamantyl, cinnoxacinyl, a monocyclic heterocyclic ring system comprising 3 to 8 atoms in the ring or a bicyclic heterocylic ring system comprising 6 to 11 atoms, provided that at least 1 atom of the ring system is carbon and at least 1 atom of the ring system is a heteroatom selected from O, N, and S; and wherein R.sup.3 and the connecting alkyl groups--(CH.sub.2).sub.m -- and --(CH.sub.2).sub.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: August 30, 1983
    Assignee: Eli Lilly and Company
    Inventor: Herbert A. Kirst
  • Purification of syn-7-[[(2-amino-4-thiazolyl)(methoxyimino) acetyl]amino]-3-methyl-3-cephem-4-carboxylic acid
    Patent number: 4400503
    Abstract: Crystalline cephalosporin hydrochloride salt represented by the formula ##STR1## wherein the oxime is in the syn configuration, is a useful pharmaceutical form of, and tool for purification of, the corresponding antibiotic free base; processes for its preparation are provided.
    Type: Grant
    Filed: October 30, 1981
    Date of Patent: August 23, 1983
    Assignee: Eli Lilly and Company
    Inventor: Kuo S. Yang
  • Derivatives of A-21978C cyclic peptides
    Patent number: 4399067
    Abstract: A-21978C cyclic peptide derivatives of the formula ##STR1## wherein R is a substituted benzoyl group of the formula ##STR2## R.sup.2 is C.sub.8 -C.sub.15 alkyl; X is hydrogen, chloro, bromo, iodo, nitro, C.sub.1 -C.sub.3 alkyl, hydroxy, C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkylthio; and R.sup.1 is hydrogen or an amino-protecting group; and the salts thereof, are useful new semisynthetic antibacterial agents or intermediates to such agents.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: August 16, 1983
    Assignee: Eli Lilly and Company
    Inventor: Manuel Debono
  • 23-Ester derivatives of DMT and method of using same
    Patent number: 4396613
    Abstract: 23-Ester derivatives of demycinosyltylosin (DMT) of the formula: ##STR1## wherein R is selected from hydrogen, optionally substituted C.sub.1 -C.sub.5 -alkanoyl or optionally substituted benzoyl, phenylacetyl, or phenylpropionyl; and R.sup.1 is an acyl group selected from: ##STR2## p is 0 or 1; m and n are integers from 0 to 4; R.sup.2 is hydrogen, halo, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, phenyl, C.sub.5 -C.sub.8 -cycloalkenyl, naphthyl, indenyl, tetralinyl, decalinyl, adamantyl, cinnoxacinyl, a monocyclic heterocyclic ring system comprising 3 to 8 atoms or a bicyclic heterocyclic ring system comprising 6 to 11 atoms, provided that at least 1 atom of the ring system is carbon and at least 1 atom of the ring system is a heteroatom selected from O, N, and S; and wherein R.sup.2 and the connecting alkyl groups --(CH.sub.2).sub.m -- and --(CH.sub.2).sub.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: August 2, 1983
    Assignee: Eli Lilly and Company
    Inventor: Herbert A. Kirst
  • Derivatives of A-21978C cyclic peptides
    Patent number: 4396543
    Abstract: A-21978C cyclic peptide derivatives of the formula ##STR1## wherein R is hydrogen, a specified aminoacyl or N-alkanoylaminoacyl group, 8-methyldecanoyl, 10-methyldodecanoyl, 10-methylundecanoyl, the specific C.sub.10 -alkanoyl group of A-21978C.sub.0 or the specific C.sub.12 -alkanoyl groups of A-21978C factors C.sub.4 and C.sub.5 or an amino-protecting group; and R.sup.1 is hydrogen, an amino-protecting group, or a specified aminoacyl or N-alkanoylaminoacyl group; provided that, when R is other than aminoacyl or N-alkanoylaminoacyl, R.sup.1 must be aminoacyl or N-alkanoylaminoacyl; and, when R.sup.1 is an amino-protecting group, R must be aminoacyl or N-alkanoylaminoacyl; and the salts thereof, are useful as antibacterial agents or as intermediates to antibacterial agents.
    Type: Grant
    Filed: May 21, 1982
    Date of Patent: August 2, 1983
    Assignee: Eli Lilly and Company
    Inventor: Manuel Debono
  • Demethylmacrocin and process for its production
    Patent number: 4385116
    Abstract: 2'"-O-demethylmacrocin (DOMM) which has the formula: ##STR1## 20-dihydro-DOMM, 2'"-O-demethyllactenocin (DOML), 20-dihydro-DOML, specified acyl ester derivatives, and their acid addition salts are useful antibacterial agents.
    Type: Grant
    Filed: July 15, 1980
    Date of Patent: May 24, 1983
    Assignee: Eli Lilly and Company
    Inventors: Richard H. Baltz, Gene M. Wild, Eugene T. Seno
  • 6"-(Substituted)-apramycin antibiotic derivatives and intermediates and starting materials therefor
    Patent number: 4379917
    Abstract: Apramycin derivatives substituted at the 6"-position with a variety of substituents are claimed as broad spectrum antibiotics. Also claimed are starting materials and intermediates in the synthesis of the above apramycin derivatives.
    Type: Grant
    Filed: December 24, 1981
    Date of Patent: April 12, 1983
    Assignee: Eli Lilly and Company
    Inventor: Herbert A. Kirst
  • Process for preparing tylactone
    Patent number: 4366247
    Abstract: A process for preparing tylactone (20-dihydro-20,23-dideoxytylonolide), which has the formula: ##STR1## by submerged aerobic fermentation of Streptomyces fradiae NRRL 12188 or a tylactone-producing mutant or recombinant thereof is provided.
    Type: Grant
    Filed: July 2, 1980
    Date of Patent: December 28, 1982
    Assignee: Eli Lilly and Company
    Inventors: Richard H. Baltz, Eugene T. Seno
  • Antibiotic A-7413 and process for preparation thereof
    Patent number: 4366147
    Abstract: Antibiotic A-7413 complex, comprising a major microbiologically active factor A, and minor active factors B, C, and D, is produced by fermentation of Actinoplanes sp. NRRL 8122. The individual factors are isolated and separated by extraction and chromatography. The A-7413 antibiotics are antibacterial agents. The A-7413 complex and A-7413 antibiotic compounds are also useful as growth-promoting agents and in the control of dental caries and acne.
    Type: Grant
    Filed: August 18, 1978
    Date of Patent: December 28, 1982
    Assignee: Eli Lilly and Company
    Inventors: Robert L. Hamill, W. Max Stark
  • Tylactone
    Patent number: 4362881
    Abstract: Tylactone (20-dihydro-20,23-dideoxytylonolide), which has the formula: ##STR1## and specified acyl ester derivatives thereof are useful intermediates in the preparation of macrolide antibiotics.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: December 7, 1982
    Assignee: Eli Lilly and Company
    Inventors: Robert L. Hamill, Gerald L. Huff, Richard H. Baltz, Eugene T. Seno
  • Antibiotics A6888C and A6888X
    Patent number: 4358584
    Abstract: Antibiotic compounds of the formula: ##STR1## wherein R' is ##STR2## or --CH.sub.2 OH, and the non-toxic pharmaceutically acceptable acid addition salts thereof, are produced by culturing Streptomyces flocculus NRRL 11459. Techniques for isolating the compounds are also described. Cirramycin A.sub.1 and cirramycin B are coproduced.
    Type: Grant
    Filed: September 22, 1980
    Date of Patent: November 9, 1982
    Assignee: Eli Lilly and Company
    Inventors: Stephen M. Nash, Kay F. Koch, Marvin M. Hoehn
  • Methods of controlling Pasteurella infections
    Patent number: 4357325
    Abstract: Methods of controlling Pasteurella infections are provided which comprise administering to an infected or susceptible warm-blooded aninal an effective amount of a composition comprising (1) a suitable pharmaceutical vehicle and (2) a compound selected from the group consisting of desmycosin, lactenocin, cirramycin A.sub.1, 23-deoxy-5-0-mycaminosyltylonolide, antibiotic M-4365 G.sub.2, 9-dihydrodesmycosin, 9-dihydrolactenocin, 20-dihydrodesmycosin, 20-dihydrolactenocin, rosaramicin, and the pharmaceutically acceptable acid addition salts of these compounds.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: November 2, 1982
    Assignee: Eli Lilly and Company
    Inventors: Earl E. Ose, Herbert A. Kirst
  • Majusculamide C
    Patent number: 4342751
    Abstract: Majusculamide C, a novel cyclic peptide compound which inhibits fungal plant pathogens, process for its preparation from a deep-water blue-green alga, Lyngbya majuscula, and process for inhibiting fungal plant pathogens with and fungicidal compositions containing majusculamide C.
    Type: Grant
    Filed: March 9, 1981
    Date of Patent: August 3, 1982
    Assignee: Eli Lilly and Company
    Inventors: Richard E. Moore, Jon S. Mynderse
  • Method of controlling ureaplasma infections
    Patent number: 4341770
    Abstract: Method of controlling Ureaplasma infections which comprises administering to an infected or susceptible warm-blooded animal an effective amount of 5-0-mycaminosyl tylonolide or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: July 27, 1982
    Assignee: Eli Lilly and Company
    Inventors: Earl E. Ose, Herbert A. Kirst
  • Method of controlling Pasteurella infections
    Patent number: 4341771
    Abstract: Method of controlling Pasteurella infections which comprises administering to an infected or susceptible warm-blooded animal an effective amount of 5-O-mycaminosyl tylonolide or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: July 27, 1982
    Assignee: Eli Lilly and Company
    Inventors: Herbert A. Kirst, Earl E. Ose
  • A-21978 Antibiotics and process for their production
    Patent number: RE31396
    Abstract: Antibiotic A-21978 complexes, in particular the A-21978C complex, comprising microbiologically active, related factors C.sub.0, C.sub.1, C.sub.2, C.sub.3, C.sub.4, and C.sub.5. A-21978 complex and A-21978C complex are produced by submerged aerobic fermentation of Streptomyces roseosporus NRRL 11379. The individual A-29178C factors are separated and isolated by chromatography. The A-21978 and A-21978C complexes; the A-21978C factors; and pharmaceutically acceptable salts thereof are antibacterial agents and improve growth promotion in poultry.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: September 27, 1983
    Assignee: Eli Lilly and Company
    Inventors: Robert L. Hamill, Marvin M. Hoehn