Patents Represented by Attorney William C. Martens, Jr.
  • Patent number: 4008230
    Abstract: 3-Hydroxycephalosporins are prepared by treating a 3-hydroxy-4-bromo-2-(2-formylthio-4-oxo-3-amido or imido-1-azetidinyl)-2-butenoate ester with mercuric acetate and contacting the resulting reaction mixture with a mercuric ion precipitator.
    Type: Grant
    Filed: October 29, 1975
    Date of Patent: February 15, 1977
    Assignee: Eli Lilly and Company
    Inventor: Gary A. Koppel
  • Patent number: 4006161
    Abstract: Thio-substituted 2-oxoindolines have the formula ##SPC1##In which one of R or R.sub.1 is hydrogen and the other is R.sub.2 --S--, in which R.sub.2 is C.sub.1 -C.sub.3 alkyl, benzyl, halobenzyl, nitrobenzyl, C.sub.1 -C.sub.3 alkylbenzyl, or phenyl. These compounds are active in relieving a condition associated with anxiety, tension, or like emotional disturbances.
    Type: Grant
    Filed: December 26, 1973
    Date of Patent: February 1, 1977
    Assignee: Eli Lilly and Company
    Inventors: Richard E. Holmes, Glen P. Jourdan
  • Patent number: 4005074
    Abstract: The amic acid group of a 7-(amic acid) cephalosporin or 6-(amic acid) penicillin is cleaved by dehydration to the corresponding novel 7-isoimidocephalosporin or 6-isoimido-penicillin, and cleavage of the 7-isoimidocephalosporin or 6-isoimidopenicillin to the corresponding 7-aminocephalosporin or 6-aminopenicillin or to a corresponding 7-acylamidocephalosporin or 6-acylamidopenicillin.
    Type: Grant
    Filed: June 18, 1973
    Date of Patent: January 25, 1977
    Assignee: Eli Lilly and Company
    Inventors: Stjepan P. Kukolja, Steven R. Lammert
  • Patent number: 4001239
    Abstract: A 7-(amic acid) cephalosporin is cleaved by conversion to the corresponding mixed anhydride and cleavage of the mixed anhydride to the corresponding 7-aminocephalosporin or to a corresponding 7-acylamidocephalosporin.
    Type: Grant
    Filed: June 13, 1975
    Date of Patent: January 4, 1977
    Assignee: Eli Lilly and Company
    Inventors: Stjepan P. Kukolja, Steven R. Lammert
  • Patent number: 3994888
    Abstract: A 7-(amic acid) cephalosporin is cleaved by conversion to the corresponding mixed anhydride and cleavage of the mixed anhydride to the corresponding 7-aminocephalosporin or to a corresponding 7-acylamidocephalosporin.
    Type: Grant
    Filed: June 13, 1975
    Date of Patent: November 30, 1976
    Assignee: Eli Lilly and Company
    Inventors: Stjepan P. Kukolja, Steven R. Lammert
  • Patent number: 3972774
    Abstract: Cephalosporin p-nitrobenzyl esters are de-esterified via an esterase enzyme derived from the genus Bacillus.
    Type: Grant
    Filed: July 28, 1975
    Date of Patent: August 3, 1976
    Assignee: Eli Lilly and Company
    Inventor: Donald Ray Brannon
  • Patent number: 3968108
    Abstract: A 3.alpha.-methyl-3.beta.-halocepham compound and/or a 2.alpha.-methyl-2.beta.-halomethylpenam compound is converted to a mixture comprising a 3-methyl-3-cephem (desacetoxycephalosporin), a 3.alpha.-methyl-3.beta.-acyloxycepham, and a 2.alpha.-methyl-2.beta.-acyloxymethylpenam by reaction of said 3-halocepham compound and/or said 2-halomethylpenam compound with a silver salt of a lower alkyl carboxylic acid or a cycloalkyl carboxylic acid.
    Type: Grant
    Filed: March 27, 1974
    Date of Patent: July 6, 1976
    Assignee: Eli Lilly and Company
    Inventors: Stjepan P. Kukolja, Steven R. Lammert
  • Patent number: 3962272
    Abstract: Novel 1H-tetrazole-1-acetate esters and acids are prepared by reacting azidoacetate esters and acids with certain acyl cyanides or cyanoformates. The products of the process are useful as intermediates in the preparation of 1H-tetrazole-1-acetic acids which have utility in preparing certain cephalosporin and penicillin antibiotics.
    Type: Grant
    Filed: August 5, 1974
    Date of Patent: June 8, 1976
    Assignee: Eli Lilly and Company
    Inventor: Allen S. Katner
  • Patent number: 3962226
    Abstract: A 3.alpha.-methyl-3.beta.-halocepham compound and/or a 2.alpha.-methyl-2.beta.-halomethylpenam compound is converted to a mixture comprising a 3-methyl-3-cephem (desacetoxycephalosporin), a 3.alpha. -methyl-3.beta.-nitrooxycepham, and a 2.alpha.-methyl-2.beta.-nitrooxymethylpenam by reaction of said halocepham compound and/or said halomethylpenam compound with silver nitrate. The novel 3-nitrooxycepham compound upon heating is converted to a desacetoxycephalosporin.
    Type: Grant
    Filed: March 27, 1974
    Date of Patent: June 8, 1976
    Assignee: Eli Lilly and Company
    Inventors: Stjepan P. Kukolja, Steven R. Lammert
  • Patent number: 3962276
    Abstract: 5-Epi-penicillin esters and acids, the acids being useful as inhibitors of .beta.-lactamase type enzymes, a process for preparing such compounds by reacting an ester of a 2-halo-.alpha.-(1'-halothio-1'-methylethyl)-4-oxo-3-imido-1-azetidineaceta te with (a) zinc in acid or (b) stannous chloride in an organic liquid medium at 0.degree. to 100.degree.C., and some new 2-halo-.alpha.-(1'-cyanodithia- or 1'-mercapto-1'-methylethyl)-4-oxo-3-imido-2-azetidineacetate which are useful as intermediates in preparing the 5-epi-penicillins.
    Type: Grant
    Filed: November 14, 1974
    Date of Patent: June 8, 1976
    Assignee: Eli Lilly and Company
    Inventor: Stjepan Kukolja
  • Patent number: 3962232
    Abstract: 7.beta.-acylamido-7.alpha.-methoxycephalosporin compounds in which the acylamido group has the formula ##SPC1##In which R is carboxy, protected carboxy, phosphono, protected phosphono, sulfo, or protected sulfo. The compounds exhibit antibiotic activity, in particular against Pseudomonas and Serratia type microorganisms.
    Type: Grant
    Filed: November 5, 1973
    Date of Patent: June 8, 1976
    Assignee: Eli Lilly and Company
    Inventor: Gary A. Koppel
  • Patent number: 3960851
    Abstract: A penicillin sulfoxide ester is reacted with sulfuryl chloride at a temperature of from about 75.degree.C. to about 120.degree.C. to produce a novel 2-chlorosulfinyl-azetidin-4-one intermediate, which intermediate is treated with an alkaline reagent to produce a desaceetoxycephalosporin sulfoxide.
    Type: Grant
    Filed: July 11, 1974
    Date of Patent: June 1, 1976
    Assignee: Eli Lilly and Company
    Inventors: Stjephan P. Kukolja, Steven R. Lammert
  • Patent number: 3954745
    Abstract: Cefazolin is prepared by treating a solvate of N,N-dimethylformamide and the hydrochloride salt of 7-amino-3-(2-methyl-1,3,4-thiadiazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid with 1H-tetrazole-1-acetyl chloride in the presence of N,N-dimethylacetamide as solvent.
    Type: Grant
    Filed: September 12, 1974
    Date of Patent: May 4, 1976
    Assignee: Eli Lilly and Company
    Inventors: Billy G. Jackson, Charles W. Ryan
  • Patent number: 3947415
    Abstract: A novel crystalline derivative comprising the sodium salt of cefamandole and L(-) ethyl lactate is herein defined. This derivative can be used to purify impure amorphous cefamandole sodium by the steps of preparing the crystalline derivative, isolating it from the mixture, and regenerating cefamandole sodium therefrom.
    Type: Grant
    Filed: December 23, 1974
    Date of Patent: March 30, 1976
    Assignee: Eli Lilly and Company
    Inventor: Lowell G. Tensmeyer
  • Patent number: 3947414
    Abstract: A novel crystalline derivative comprising the sodium salt of cefamandole, 1,4-dioxane, and water is herein defined. This derivative can be used to purify impure amorphous cefamandole sodium by the steps of preparing the crystalline derivative, isolating it from the mixture, and regenerating cefamandole sodium therefrom.
    Type: Grant
    Filed: December 23, 1974
    Date of Patent: March 30, 1976
    Assignee: Eli Lilly and Company
    Inventor: Lowell G. Tensmeyer
  • Patent number: 3946002
    Abstract: An improved process for preparing antibacterially active 7-.alpha.-aminoacetamido cephalosporin-4-carboxylic acids in which a 7-aminocephalosporin-4-carboxylic acid ester is reacted with an activated form of an .alpha.-aminoacetic acid, the amino group of which is protected by a .beta.-dicarbonyl group, this amino group being removed after the acylation in the presence of a sufficient amount of a hydrazine derivative to prevent re-reaction of the .beta.-dicarbonyl protecting agent with the cephalosporin.
    Type: Grant
    Filed: July 11, 1974
    Date of Patent: March 23, 1976
    Assignee: Lilly Industries Limited
    Inventors: Michael Davison, David Binfield Frankham, Thomas William Matches Spence
  • Patent number: 3944545
    Abstract: A penicillin sulfoxide is heated in the presence of silylating agent to produce a novel silyl ester azetidine-2-sulfenate which, by treatment with acid, is converted to a desacetoxycephalosporin compound.
    Type: Grant
    Filed: April 12, 1973
    Date of Patent: March 16, 1976
    Assignee: Eli Lilly and Company
    Inventor: Ta-Sen Chou
  • Patent number: 3943126
    Abstract: A 7-aminocephalosporin is acylated to a 7-acylamidocephalosporin by reaction with the pentachlorophenyl ester of sydnone-3-acetic acid or 1-tetrazoleacetic acid.
    Type: Grant
    Filed: November 15, 1973
    Date of Patent: March 9, 1976
    Assignee: Eli Lilly and Company
    Inventors: Charles W. Ryan, William B. Blanchard
  • Patent number: 3941781
    Abstract: This invention is addressed to a new and improved method for the preparation of 3-alkylthiomethyl-7-acylamido cephalosporins in which a 3-alkanoyloxymethyl-7-acylamido cephalosporin is reacted with an alkane thiol in aqueous medium in the presence of certain inorganic salts to produce the desired 3-alkylthiomethyl product in significantly improved yields.
    Type: Grant
    Filed: October 23, 1973
    Date of Patent: March 2, 1976
    Assignee: Eli Lilly and Company
    Inventor: Ian G. Wright
  • Patent number: 3932489
    Abstract: Hydroxy- or thiol-substituted amino acids are t-butylated by reacting them with isobutylene in the presence of a catalyst comprising boron trifluoride and anhydrous phosphoric acid.
    Type: Grant
    Filed: November 16, 1973
    Date of Patent: January 13, 1976
    Assignee: Eli Lilly and Company
    Inventor: Edward L. Smithwick, Jr.