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).
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Patent number: 4775751Abstract: 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: GrantFiled: June 3, 1985Date of Patent: October 4, 1988Assignee: Eli Lilly & CompanyInventor: Lawrence J. McShane
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Patent number: 4704156Abstract: 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: GrantFiled: May 7, 1986Date of Patent: November 3, 1987Assignee: Eli Lilly and CompanyInventor: Lawrence J. McShane
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Patent number: 4558123Abstract: 3-Acetoxymethylcephalosporins are converted to 3-exomethylene cephalosporins by reaction with a metal and a bound proton source.Type: GrantFiled: July 22, 1983Date of Patent: December 10, 1985Assignee: Eli Lilly and CompanyInventor: Lawrence J. McShane
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Patent number: 4515719Abstract: 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: GrantFiled: July 22, 1983Date of Patent: May 7, 1985Assignee: Eli Lilly and CompanyInventor: Lawrence J. McShane
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Patent number: 4243587Abstract: 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: GrantFiled: May 21, 1979Date of Patent: January 6, 1981Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
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Patent number: 4226767Abstract: 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: GrantFiled: May 21, 1979Date of Patent: October 7, 1980Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
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Patent number: 4207343Abstract: 1-Phenyl-3-(optionally substituted phenoxy)-propylamines, inhibitors of norepinephrine uptake.Type: GrantFiled: June 22, 1978Date of Patent: June 10, 1980Assignee: Eli Lilly and CompanyInventors: Edward R. Lavagnino, Lawrence J. McShane, Bryan B. Molloy
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Patent number: 4180507Abstract: 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: GrantFiled: August 15, 1978Date of Patent: December 25, 1979Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
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Patent number: 4127568Abstract: 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: GrantFiled: March 7, 1977Date of Patent: November 28, 1978Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Gary A. Koppel, Lawrence J. McShane
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Patent number: 4075219Abstract: 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: GrantFiled: March 31, 1977Date of Patent: February 21, 1978Assignee: Eli Lilly and CompanyInventor: Lawrence J. McShane