Patents by Inventor Robin D. G. Cooper
Robin D. G. Cooper 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: 6908996Abstract: The present invention relates to novel intermediates for the preparation of 3-methylenecephams of the formula IIA. wherein: R is a carboxylic acid protecting group; R1 is a group of the formula; R10 is C1-C6 alkyl, C1-C6 polyfluoroalkyl, C3-C6 cycloalkyl, adamantyl, phenyl, substituted phenyl, phenyl(C1-C3 alkyl), diphenylmethyl, or substituted phenyl(C1-C3 alkyl), or a group of the formula Z is solid polymer support; and Z1 is one or two groups independently selected from the group consisting of hydrogen, halo, hydroxy, protected hydroxy, nitro, cyano, trifluoromethyl, C1-C4 alkyl, and C1-C4 alkoxy.Type: GrantFiled: November 12, 2003Date of Patent: June 21, 2005Assignee: Imperial College of LondonInventors: Robin D. G. Cooper, Anthony G. M. Barrett
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Publication number: 20040106790Abstract: The present invention relates to novel intermediates for the preparation of 3-methylenecephams. More specifically, the present invention relates to the intramolecular cyclization of penicillin sulfoxide derived monocyclic azetidinone as precursors to cephalosporin antibiotics.Type: ApplicationFiled: November 12, 2003Publication date: June 3, 2004Inventors: Robin D.G. Cooper, Anthony G.M. Barrett
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Patent number: 6683176Abstract: The present invention relates to novel processes for the preparation of 3-methylenecephams. More specifically, the present invention relates to the intramolecular cyclization of penicillin sulfoxide derived monocyclic azetidinone derivatives with organometallic catalysts of the formula III. MEx(H2O)y (III) wherein: M is Sc, Y, La, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, Lu, Zr, Hf, Th, Nb, Ta, U, Bi, or In; E is O[SO2(C1-C6 polyfluoroalkyl)], N[SO2(C1-C6 polyfluoroalkyl)]2, or C[SO2(C1-C6 polyfluoroalkyl)]3; x is 3; y is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.Type: GrantFiled: December 31, 2001Date of Patent: January 27, 2004Inventors: Robin D. G. Cooper, Anthony G. M. Barrett
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Patent number: 6610680Abstract: This invention provides substituted 2-(azetidinon-1-yl) acetic acid derivatives of Formula II for the antagonism of the vasopressin V1a receptor.Type: GrantFiled: December 20, 2002Date of Patent: August 26, 2003Assignee: Eli Lilly and CompanyInventors: Robert F Bruns, Jr., Robin D G Cooper, Bruce A Dressman, David C Hunden, Stephen W Kaldor, Gary A Koppel, John R Rizzo, Jeffrey J Skelton, Mitchell I Steinberg
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Publication number: 20030036650Abstract: The present invention relates to novel processes for the preparation of 3-methylenecephams. More specifically, the present invention relates in part to the intramolecular cyclization of penicillin sulfoxide derived monocyclic azetidinone derivatives either thermally or with lanthanide metal salt catalysts.Type: ApplicationFiled: December 31, 2001Publication date: February 20, 2003Inventors: Robin D.G. Cooper, Anthony G.M. Barrett
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Patent number: 6521611Abstract: This invention provides methods and 2-(azetidin-2-on-1-yl) acetic acid derivatives of Formula I for the antagonism of the vasopressin V1a receptor.Type: GrantFiled: December 8, 2000Date of Patent: February 18, 2003Assignee: Eli Lilly and CompanyInventors: Robert F Bruns, Jr., Robin D G Cooper, Bruce A Dressman, David C Hunden, Stephen W Kaldor, Gary A Koppel, John R Rizzo, Jeffrey J Skelton, Mitchell I Steinberg
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Patent number: 5977062Abstract: The present invention provides glycopeptide antibiotic derivative compounds. These derivative compounds possess antibacterial activity against a wide variety of bacteria, including activity against vancomycin-resistant isolates. Methods of making and using these glycopeptide antibiotic derivative compounds are also provided.Type: GrantFiled: April 17, 1998Date of Patent: November 2, 1999Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Bret E. Huff, Thalia I. Nicas, John T. Quatroche, Michael J. Rodriguez, Nancy J. Snyder, Michael A. Staszak, Richard C. Thompson, Stephen C. Wilkie, Mark J. Zweifel
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Patent number: 5843889Abstract: The present invention provides glycopeptide antibiotic derivative compounds. These derivative compounds possess antibacterial activity aginst a wide variety of bacteria, including activity against vancomycin-resistant isolates. Methods of making and using these glycopeptide antibiotic derivative compounds are also provided.Type: GrantFiled: March 12, 1997Date of Patent: December 1, 1998Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Bret E. Huff, Thalia I. Nicas, John T. Quatroche, Michael J. Rodriguez, Nancy J. Snyder, Michael A. Staszak, Richard C. Thompson, Stephen C. Wilkie, Mark J. Zweifel
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Patent number: 5840684Abstract: The present invention provides glycopeptide antibiotic derivative compounds. These derivative compounds possess antibacterial activity against a wide variety of bacteria, including activity against vancomycin-resistant isolates. Methods of making and using these glycopeptide antibiotic derivative compounds are also provided.Type: GrantFiled: March 24, 1995Date of Patent: November 24, 1998Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Bret E. Huff, Thalia I. Nicas, John T. Quatroche, Michael J. Rodriguez, Nancy J. Snyder, Michael A. Staszak, Richard C. Thompson, Stephen C. Wilkie, Mark J. Zweifel
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Patent number: 4772694Abstract: 2,5-Disubstituted oxazolidin-4-one-3-ylacetyl chlorides and 1,2,5-substituted imidazolidin-4-one-3-yl-acetyl chlorides function as chiral auxiliary moieties in the asymmetric cycloaddition with aldimines to provide cis-azetidinones. The azetidinones are useful intermediates in the preparation of antibiotics.Type: GrantFiled: July 24, 1986Date of Patent: September 20, 1988Assignee: Eli Lilly and CompanyInventor: Robin D. G. Cooper
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Patent number: 4734498Abstract: 3.beta.-Substituted succinimido)azetidinones represented by the formula ##STR1## wherein R and R.sub.1 are e.g. C.sub.1 -C.sub.5 alkanoyloxy, benzoyloxy, substituted benzoyloxy, or benzyloxy, or one of R and R.sub.1 is hydrogen and the other is as defined above; R.sub.2 is C.sub.1 -C.sub.4 alkoxycarbonyl or an arylvinyl group e.g. styrryl or 2-furylvinyl; and R.sub.3 is e.g. protected-carboxymethyl, or an NH protecting group; are provided via stereoselective cycloaddition of imines with chiral auxiliary 3,4-disubstituted succinimidoacetyl chlorides. The chiral auxiliary e.g., 3S,4S-dibenzoyloxy-and 3S,4S-diacetoxysuccinimidoacetyl chloride, is obtained from tartaric acid via anhydride and imide formation with retention of chirality. The chiral azetidinones obtained are useful intermediates to .beta.-lactam antibacterial compounds.Type: GrantFiled: July 10, 1986Date of Patent: March 29, 1988Assignee: Eli Lilly and CompanyInventor: Robin D. G. Cooper
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Patent number: 4587053Abstract: Oxazolino-azetidinones are prepared by reaction of a phosphorus compound with a 3-exomethylenecepham sulfoxide.Type: GrantFiled: April 26, 1984Date of Patent: May 6, 1986Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, John M. Morin, Jr., Lynn R. Peters
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Patent number: 4518531Abstract: This invention provides a novel allylic chlorination process for inserting a chlorine atom on the saturated methyl group of a 3-methyl-2-but-3-enoate group on the ring nitrogen atom of a 2-azetidinone or thiazolinoazetidinone. The chloro-substituted compounds prepared thereby are novel intermediates used in preparation of cephalosporins.Type: GrantFiled: November 14, 1983Date of Patent: May 21, 1985Assignee: Eli Lilly and CompanyInventor: Robin D. G. Cooper
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Patent number: 4490370Abstract: Naphthylglycyl and tetrahydronaphthylglycyl cephalosporins are potent antibacterial agents and are particularly useful as oral treatments for upper respiratory infections.Type: GrantFiled: April 12, 1983Date of Patent: December 25, 1984Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Larry C. Blaszczak, Jan R. Turner
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Patent number: 4482553Abstract: 7-(2-Benzothienyl)glycylamido cephalosporins have good gram positive activity and favorable pharmacokinetics and are orally effective.Type: GrantFiled: April 12, 1983Date of Patent: November 13, 1984Assignee: Eli Lilly and CompanyInventors: Robin D. G. Cooper, Bernard J. Graves, Edward R. Lavagnino
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Patent number: 4468514Abstract: Thiazoline azetidinones are converted in good yield to 3-bromo-3-methylcephams by treatment with a bromine source and dimethyl sulfoxide.Type: GrantFiled: December 17, 1982Date of Patent: August 28, 1984Assignee: Eli Lilly and CompanyInventor: Robin D. G. Cooper
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Patent number: 4430268Abstract: This invention provides a novel allylic chlorination process for inserting a chlorine atom on the saturated methyl group of a 3-methyl-2-but-3-enoate group on the ring nitrogen atom of a 2-azetidinone or thiazolinoazetidinone. The chloro-substituted compounds prepared thereby are novel intermediates used in preparation of cephalosporins.Type: GrantFiled: March 17, 1980Date of Patent: February 7, 1984Assignee: Eli Lilly and CompanyInventor: Robin D. G. Cooper
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Patent number: 4355172Abstract: Process for 4-(D-3-amino-3-carboxypropoxy)phenylglyoxylic acid oxime as an amino-protected ester comprising alkylating an amino-protected D-methionine silyl ester with an alkyl or benzyl iodide; cyclizing the alkylsulfonium iodide to an amino-protected D-homoserine lactone; hydrolyzing the lactone to an amino-protected D-homoserine in aqueous base; coupling, to form an ether, the amino-protected D-homoserine as an ester with an ester of 4-hydroxyphenylglyoxylic acid; and forming the oxime of the ether or alternatively coupling the D-homoserine ester with a protected-oxime of an esterified 4-hydroxyphenylglyoxylic acid. The product is useful in preparing the antibiotic FR 1923.Type: GrantFiled: August 17, 1977Date of Patent: October 19, 1982Assignee: Eli Lilly and CompanyInventors: Gary A. Koppel, Robin D. G. Cooper
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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