Patents by Inventor Robert R. Chauvette
Robert R. Chauvette 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: 4334065Abstract: 7.alpha.-(Dimethylamidino)-3-cephem ester 1.alpha.-oxides represented by the formula ##STR1## wherein R is hydrogen or acetoxy and R.sub.1 is a carboxy protecting group, are prepared via DBU epimerization of the corresponding 7.beta.-isomer. When R is hydrogen the intermediates are useful in the preparation of the 7.beta.-acylamino-7.alpha.-methoxy-1-oxa-.beta.-lactam antibiotics, and when R is acetoxy the compounds are intermediates to 7.beta.-acylamino-7.alpha.-methoxy-3-exomethylenecepham compounds.Type: GrantFiled: November 24, 1980Date of Patent: June 8, 1982Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4316842Abstract: 6-Epi penicillin .alpha.-sulfoxides represented by the formula ##STR1## wherein R is a carboxy protecting group, are useful for preparing antibiotic compounds and are prepared via epimerization with an alkali metal acetate of corresponding 6.beta.-epimer.Type: GrantFiled: November 24, 1980Date of Patent: February 23, 1982Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4281117Abstract: 7-Amino-3-hydroxy-3-cephem esters react with a chlorinating agent, e.g. phosgene, thionyl chloride and preferably PCl.sub.3 -DMF to provide 7.beta.-[(dimethylaminomethylene)amino]-3-chloro-3-cephem esters which on reaction with a carboxylic acid, a percarboxylic acid, or a phenol, having a pH in water of about 2-5, afford 7.beta.-formamido-3-chloro-3-cephem esters, and corresponding 2-cephem esters. Percarboxylic acids provide 7.beta.-formamido-3-chloro-3-cephem ester 1-oxides. The 7-formamido derivatives provide the 7-amino-3-chloro-3-cephem ester on acid hydrolysis. The 7-amino-3-chloro esters are useful for preparing antibiotics.Type: GrantFiled: September 4, 1980Date of Patent: July 28, 1981Assignee: Eli Lilly and CompanyInventors: Pamela A. Chauvette, Robert R. Chauvette
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Patent number: 4281116Abstract: 7-Acylamido- and 7-amino-3-halo-3-cephem-4-carboxylic acids, esters and pharmaceutically-acceptable salts and esters thereof are new cephalosporin compounds provided by the reaction of a 7-acylamido-3-hydroxy-3-cephem-4-carboxylic acid ester or a 7-amino-3-hydroxy-3-cephem-4-carboxylic acid ester with an iodinating, fluorinating, chlorinating, or brominating reagent. For example, 7-amino-3-chloro-3-cephem-4-carboxylic acid and 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylic acid are provided. The 7-acylamido-3-halo cephalosporin acids and pharmaceutically acceptable salts and esters provided are valuable antibiotic compounds having desirable therapeutic properties.Type: GrantFiled: July 2, 1980Date of Patent: July 28, 1981Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4260745Abstract: 7-Acylamido- and 7-amino-3-halo-3-cephem-4-carboxylic acids, esters and pharmaceutically-acceptable salts and esters thereof are new cephalosporin compounds provided by the reaction of a 7-acylamido-3-hydroxy-3-cephem-4-carboxylic acid ester or a 7-amino-3-hydroxy-3-cephem-4-carboxylic acid ester with an iodinating, fluorinating, chlorinating, or brominating reagent. For example, 7-amino-3-chloro-3-cephem-4-carboxylic acid and 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylic acid are provided. The 7-acylamido-3-halo cephalosporin acids and pharmaceutically acceptable salts and esters provided are valuable antibiotic compounds having desirable therapeutic properties.Type: GrantFiled: October 12, 1979Date of Patent: April 7, 1981Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4252950Abstract: 7-Acylamido- and 7-amino-3-halo-3-cephem-4-carboxylic acids, esters and pharmaceutically-acceptable salts and esters thereof are new cephalosporin compounds provided by the reaction of a 7-acylamido-3-hydroxy-3-cephem-4-carboxylic acid ester or a 7-amino-3-hydroxy-3-cephem-4-carboxylic acid ester with an iodinating, fluorinating, chlorinating, or brominating reagent. For example, 7-amino-3-chloro-3-cephem-4-carboxylic acid and 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylic acid are provided. The 7-acylamido-3-halo cephalosporin acids and pharmaceutically acceptable salts and esters provided are valuable antibiotic compounds having desirable therapeutic properties.Type: GrantFiled: October 12, 1979Date of Patent: February 24, 1981Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4208515Abstract: 7-Acylamido- and 7-amino-3-halo-3-cephem-4-carboxylic acids, esters and pharmaceutically-acceptable salts and esters thereof are new cephalosporin compounds provided by the reaction of a 7-acylamido-3-hydroxy-3-cephem-4-carboxylic acid ester or a 7-amino-3-hydroxy-3-cephem-4-carboxylic acid ester with an iodinating, fluorinating, chlorinating, or brominating reagent. For example, 7-amino-3-chloro-3-cephem-4-carboxylic acid and 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylic acid are provided. The 7-acylamido-3-halo cephalosporin acids and pharmaceutically acceptable salts and esters provided are valuable antibiotic compounds having desirable therapeutic properties.Type: GrantFiled: April 5, 1977Date of Patent: June 17, 1980Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4064343Abstract: 7-Acylamido- and 7-amino-3-halo-3-cephem-4-carboxylic acids, esters and pharmaceutically-acceptable salts and esters thereof are new cephalosporin compounds provided by the reaction of a 7-acylamido-3-hydroxy-3-cephem-4-carboxylic acid ester or a 7-amino-3-hydroxy-3-cephem-4-carboxylic acid ester with an iodinating, fluorinating, chlorinating, or brominating reagent. For example, 7-amino-3-chloro-3-cephem-4-carboxylic acid and 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylic acid are provided. The 7-acylamido-3-halo cephalosporin acids and pharmaceutically acceptable salts and esters provided are valuable antibiotic compounds having desirable therapeutic properties.Type: GrantFiled: February 9, 1976Date of Patent: December 20, 1977Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4060688Abstract: 3-Exomethylenecepham and 3-hydroxy-3-cephem sulfoxides represented by the formulas ##STR1## wherein R is an acyl group derived from a carboxylic acid and R.sub.1 is a carboxylic acid protecting group, are useful intermediates in the synthesis of 3-alkoxy-3-cephem, 3-chloro-3-cephem and 3-methyl-3-cephem antibiotic compounds.Type: GrantFiled: June 6, 1975Date of Patent: November 29, 1977Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 4008228Abstract: 7-Acylamino-3-methyl-3-cephem-4-carboxylic acids and esters are prepared via the reductive cleavage of a 3-thio substituted 2-cephem-4-carboxylic acid or ester with hydrogen and Raney nickel or zinc in formic acid and DMF to provide reduction product mixtures of the corresponding 7-substituted 3-methyl-2-cephem-4-acid or ester (I) and 3-exomethylenecepham-4-acid or ester (II). Reduction product mixtures are separable via chromatography and individual I and II are isomerized to 3-methyl-3-cephem antibiotics.Type: GrantFiled: July 14, 1975Date of Patent: February 15, 1977Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 3992377Abstract: 7-Acylamido-3-cephem-4-carboxylic acid antibiotics directly substituted in the 3-position of the cephem ring system with a sulfur atom bonded to a 5- or 6-membered heterocyclic ring, a lower alkyl group, or a phenyl or substituted phenyl group are prepared with the corresponding 3-halo-3-cephem esters. For example, p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-chloro-3-cephem-4-carboxylate reacts with 1-methyl-1H-tetrazol-5-ylthiol to provide p-nitrobenzyl 7-[2-(2-thienyl)acetamido]-3-[(1-methyl-1H-tetrazol-5-yl)thio]-3-cephem-4- carboxylate. The p-nitrobenzyl ester group is removed by catalytic hydrogenolysis to provide the antibiotic carboxylic acid compound. Alternatively, the antibiotics are prepared by reacting a 3-alkylsulfonyloxy, or 3-arylsulfonyloxy-3-cephem, for example, 3-methanesulfonyloxy-3-cephem, or a 3-p-toluenesulfonyloxy-3-cephem with the heterocyclic thiol, the phenyl or substituted phenylthiol, or with the lower alkylthiol.Type: GrantFiled: December 13, 1974Date of Patent: November 16, 1976Assignee: Eli Lilly and CompanyInventors: Robert R. Chauvette, Gary A. Koppel
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Patent number: 3962227Abstract: 7-Acylamido- and 7-amino-3-halo-3-cephem-4-carboxylic acids, esters and pharmaceutically-acceptable salts and esters thereof are new cephalosporin compounds provided by the reaction of a 7-acylamido-3-hydroxy-3-cephem-4-carboxylic acid ester or a 7-amino-3-hydroxy-3-cephem-4-carboxylic acid ester with an iodinating, fluorinating, chlorinating, or brominating reagent. For example, 7-amino-3-chloro-3-cephem-4-carboxylic acid and 7-phenoxyacetamido-3-chloro-3-cephem-4-carboxylic acid are provided. The 7-acylamido-3-halo cephalosporin acids and pharmaceutically acceptable salts and esters provided are valuable antibiotic compounds having desirable therapeutic properties.Type: GrantFiled: April 1, 1974Date of Patent: June 8, 1976Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette
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Patent number: 3932393Abstract: 3-Methylenecepham-4-carboxylic acids and esters of the Formula I and 3-methyl-.DELTA..sup.3 -cephem-4-carboxylic acids and esters of the Formula II ##SPC1##where R is hydrogen or an organic acyl group and R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl a carboxylic acid protecting group or a pharmaceutically acceptable cation are prepared via the reductive displacement of a 3-substituted methyl cephalosporin of the Formula III ##SPC2##where R.sub.2 is an organic residue such that --SR.sub.2 constitutes a reductively displaceable moiety, and R and R.sub.1 have the same meanings as defined in Formulae I and II, reductive displacement being accomplished by catalytic hydrogenation or chemical reduction. The 3-methylene cepham compounds are isomerized in dimethylacetamide in the presence of a tertiary alkyl amine to provide 3-methyl-7-acylamido-.DELTA..sup.3 -cephem-4-carboxylic acids and esters.Type: GrantFiled: February 25, 1971Date of Patent: January 13, 1976Assignee: Eli Lilly and CompanyInventor: Robert R. Chauvette