Patents by Inventor Lawrence J. McShane

Lawrence J. McShane has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 4775751
    Abstract: The crystalline ethanol or methanol solvates of cephalexin hydrochloride are isolated in high yield from solutions of cephalexin hydrochloride in substantially anhydrous ethanol or methanol, respectively, by adding miscible C.sub.5 -C.sub.6 alkanes after initiating solvate crystallization. Ethanol or methanol solutions of cephalexin hydrochloride can be prepared by adding gaseous HCl to the respective alcohol slurries of cephalexin monohydrate or the novel crystalline ethanolate or desolvated ethanolate. Alternatively, the cephalexin bis-DMF solvate-derived cephalexin hydrochloride isopropanolate can be used to prepare the crystalline hydrochloride monohydrate in accordance with the disclosed improved method.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: October 4, 1988
    Assignee: Eli Lilly & Company
    Inventor: Lawrence J. McShane
  • Patent number: 4704156
    Abstract: 1,2,2-Trihalocyclopropane 1-carboxylic acids and derivatives thereof are useful in regulating the growth and flowering of plants when applied as a foliar spray or as a post emergent or pre-emergent soil treatment.
    Type: Grant
    Filed: May 7, 1986
    Date of Patent: November 3, 1987
    Assignee: Eli Lilly and Company
    Inventor: Lawrence J. McShane
  • Patent number: 4558123
    Abstract: 3-Acetoxymethylcephalosporins are converted to 3-exomethylene cephalosporins by reaction with a metal and a bound proton source.
    Type: Grant
    Filed: July 22, 1983
    Date of Patent: December 10, 1985
    Assignee: Eli Lilly and Company
    Inventor: Lawrence J. McShane
  • Patent number: 4515719
    Abstract: 3-Exomethylene cepham sulfones are converted to azetidinone sulfinic acids by reaction with activated zinc, magnesium, activated magnesium or amalgamated magnesium and a protonic acid.
    Type: Grant
    Filed: July 22, 1983
    Date of Patent: May 7, 1985
    Assignee: Eli Lilly and Company
    Inventor: Lawrence J. McShane
  • Patent number: 4243587
    Abstract: 1-[.alpha.-(Carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one esters are prepared by converting 2-acyl-3,3-dialkyl-7-oxo-.alpha.-[4-(benzyloxy)phenyl]-4-thia-2,6-diazabic yclo[3.2.0]-heptane-6-acetic acid esters with mercuric acetate in an aqueous organic solvent mixture, e.g., in aqueous methanol, to 7-oxo-3-phenyl-.alpha.-[4-(benzyloxy)phenyl]-4-oxa-2,6-diazabicyclo[3.2.0] hept-2-ene-1-acetic acid esters and the latter are reacted with PCl.sub.5 and pyridine to provide the monocyclic 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-(.alpha.-chlorobenzylidene -amino)-4-chloroazetidin-2-one esters. Reduction of the dichloro azetidin-2-one with an organo tin hydride and azobisisobutyronitrile affords the deschloro, 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-benzylideneaminoazetidin-2 -one ester. The latter is hydrolyzed and the 4-benzyloxy group is cleaved via catalytic hydrogenolysis to yield an ester of 1-[.alpha.-(carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one. The 3.beta.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: January 6, 1981
    Assignee: Eli Lilly and Company
    Inventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
  • Patent number: 4226767
    Abstract: 1-[.alpha.-(Carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one esters are prepared by converting 2-acyl-3,3-dialkyl-7-oxo-.alpha.-[4-(benzyloxy)phenyl]-4-thia-2,6-diazabic yclo[3.2.0]heptane-6-acetic acid esters with mercuric acetate in an aqueous organic solvent mixture, e.g., in aqueous methanol, to 7-oxo-3-phenyl-.alpha.-[4-(benzyloxy)phenyl]-4-oxa-2,6-diazabicyclo[3.2.0] hept-2-ene-1-acetic acid esters and the latter are reacted with PCl.sub.5 and pyridine to provide the monocyclic 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-(.alpha.-chlorobenzylidene amino)-4-chloroazetidin-2-one esters. Reduction of the dichloro azetidin-2-one with an organo tin hydride and azobisisobutyronitrile affords the deschloro, 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-benzylideneaminoazetidin-2 -one ester. The latter is hydrolyzed and the benzyloxy group is cleaved via catalytic hydrogenolysis to yield an ester of 1-[.alpha.-(carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one. The 3.beta.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: October 7, 1980
    Assignee: Eli Lilly and Company
    Inventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
  • Patent number: 4207343
    Abstract: 1-Phenyl-3-(optionally substituted phenoxy)-propylamines, inhibitors of norepinephrine uptake.
    Type: Grant
    Filed: June 22, 1978
    Date of Patent: June 10, 1980
    Assignee: Eli Lilly and Company
    Inventors: Edward R. Lavagnino, Lawrence J. McShane, Bryan B. Molloy
  • Patent number: 4180507
    Abstract: 1-[.alpha.-(Carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one esters are prepared by converting 2-acyl-3,3-dialkyl-7-oxo-.alpha.-[4-(benzyloxy)phenyl]-4-thia-2,6-diazabic yclo[3.2.0]-heptane-6-acetic acid esters with mercuric acetate in an aqueous organic solvent mixture, e.g., in aqueous methanol, to 7-oxo-3-phenyl-.alpha.-[4-benzyloxy)phenyl]-4-oxa-2,6-diazabicyclo[3.2.0]h ept-2-ene-1-acetic acid esters and the latter are reacted with PCl.sub.5 and pyridine to provide the monocyclic 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-(.alpha.-chlorobenzylidene amino)-4-chloroazetidin-2-one esters. Reduction of the dichloro azetidin-2-one with an organo tin hydride and azobisisobutyronitrile affords the deschloro, 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-benzylideneaminoazetidin-2 -one ester. The latter is hydrolyzed and the 4-benzyloxy group is cleaved via catalytic hydrogenolysis to yield an ester of 1-[.alpha.-(carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one. The 3.beta.
    Type: Grant
    Filed: August 15, 1978
    Date of Patent: December 25, 1979
    Assignee: Eli Lilly and Company
    Inventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
  • Patent number: 4127568
    Abstract: 1-[.alpha.-(Carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one esters are prepared by converting 2-acyl-3,3-dialkyl-7-oxo-.alpha.-[4-(benzyloxy)phenyl]-4-thia-2,6-diazabic yclo[3.2.0]-heptane-6-acetic acid esters with mercuric acetate in an aqueous organic solvent mixture, e.g., in aqueous methanol, to 7-oxo-3-phenyl-.alpha.-[4-(benzyloxy)phenyl]-4-oxa-2,6-diazabicyclo[3.2.0] hept-2-ene-1-acetic acid esters and the latter are reacted with PCl.sub.5 and pyridine to provide the monocyclic 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-(.alpha.-chlorobenzylidene amino)-4-chloroazetidin-2-one esters. Reduction of the dichloro azetidin-2-one with an organo tin hydride and azobisisobutyronitrile affords the deschloro, 1-[.alpha.-(carboxy)-4-benzyloxybenzyl]-3.beta.-benzylideneaminoazetidin-2 -one ester. The latter is hydrolyzed and the 4-benzyloxy group is cleaved via catalytic hydrogenolysis to yield an ester of 1-[.alpha.-(carboxy)-4-hydroxybenzyl]-3.beta.-aminoazetidin-2-one. The 3.beta.
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: November 28, 1978
    Assignee: Eli Lilly and Company
    Inventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
  • Patent number: 4075219
    Abstract: A process for preparing the compound represented by the formula ##STR1## wherein the indicated carbon has the D-configuration which comprises dissolution of the compound in the L-configuration or as a mixture of the D and L-configurations in aqueous pyridine from which the compound having the D-configuration selectively crystallizes.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: February 21, 1978
    Assignee: Eli Lilly and Company
    Inventor: Lawrence J. McShane