Patents by Inventor Gary M. F. Lim
Gary M. F. Lim 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: 5801241Abstract: The cephalosporin intermediates, desacetyl 7-glutaryl ACA and desacetyl cephalosporin D, are obtained in the form of a concentrated aqueous solution from an aqueous solution containing said intermediates in less concentrated form by solvent extraction using cyclohexanone followed by back-extraction into water. The concentrated aqueous solution of intermediate is in a form which can be used for economical production of 7-ACA using known procedures.Type: GrantFiled: July 18, 1997Date of Patent: September 1, 1998Assignee: Bristol-Myers Squibb CompanyInventors: Gary M. F. Lim, John M. Roubie, Vicki H. Audia
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Patent number: 5698703Abstract: The present invention provides a stable, crystalline syn-isomer of 2-(2-aminothiazol-4-yl)-2-methoxyimino acetyl chloride hydrochloride substantially free of the anti-isomer and a process for the preparation thereof which may be used in an acylation process for the preparation of useful broad-spectrum antibiotics.Type: GrantFiled: April 25, 1994Date of Patent: December 16, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Gary M. F. Lim, John M. Roubie
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Patent number: 5594131Abstract: The present invention provides a process for the preparation of stable, crystalline cephalosporin intermediates of the formula ##STR1## wherein X is HI, HCl or H.sub.2 SO.sub.4 which are substantially free of the .DELTA..sup.2 isomer, and which are convertible into broad-spectrum cephalosporin antibiotics.Type: GrantFiled: February 2, 1995Date of Patent: January 14, 1997Assignee: Bristol-Myers Squibb COmpanyInventors: Gary M. F. Lim, John M. Roubie
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Patent number: 5594129Abstract: The present invention provides an anhydrous acylation process for the preparation of antibiotic, cefepime dihydrochloride hydrate which is substantially free of the anti-isomer and the .DELTA..sup.2 isomer comprising the N-acylation of a silylated derivative of 7-amino-3-[(1-methyl-1-pyrrolidinio)-methyl]ceph-3-em-4-carboxylate with the syn-isomer of 2-(2-aminothiazol-4-yl)-2-methoxyimino acetyl chloride hydrochloride.Type: GrantFiled: December 19, 1994Date of Patent: January 14, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Gary M. F. Lim, John M. Roubie, Elizabeth A. Garofalo
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Patent number: 5594130Abstract: The present invention provides an aqueous acylation process for the preparation of antibiotic, cefepime dihydrochloride hydrate which is substantially free of the anti-isomer and the .DELTA..sup.2 isomer comprising the N-acylation of 7-amino-3-[(1-methyl-1-pyrrolidinio)-methyl]ceph-3-em-4-carboxylate with the syn-isomer of 2-(2-aminothiazol-4-yl)-2-methoxyimino acetyl chloride hydrochloride.Type: GrantFiled: February 2, 1995Date of Patent: January 14, 1997Assignee: Bristol-Myers Squibb CompanyInventors: Gary M. F. Lim, John M. Roubie
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Patent number: 5391729Abstract: The present invention relates to a new crystalline dihydrochloride dihydrate salt of the cephalosporin antibiotic, cefepime. In particular, this invention provides a temperature and moisture stable crystalline dihydrochloride dihydrate form of cefepime having enhanced stability and a specific x-ray powder diffraction pattern as described herein.Type: GrantFiled: May 28, 1993Date of Patent: February 21, 1995Assignee: Bristol-Myers Squibb CompanyInventors: Elizabeth A. Garofalo, Gary M. F. Lim, Murray A. Kaplan
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Patent number: 4374994Abstract: 5-Mercaptotetrazolyl-1-acetic acid is prepared by bromination with molecular bromine of tetrazolyl-1-acetic acid to produce 5-bromotetrazolyl-1-acetic acid which is then reacted with thiourea to displace the bromine and, after alkaline hydrolysis, to produce 5-mercaptotetrazolyl-1-acetic acid.Type: GrantFiled: July 5, 1979Date of Patent: February 22, 1983Assignee: Bristol-Myers CompanyInventors: Gary M. F. Lim, Masaki Endo
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Patent number: 4277605Abstract: 3-Hydroxy-7-oxomorphinans and 3-hydroxy-7-oxoisomorphinans, optionally substituted on the 17-nitrogen atom, are potent, orally active antidiarrheal agents.Type: GrantFiled: March 7, 1980Date of Patent: July 7, 1981Assignee: Bristol-Myers CompanyInventors: Joseph P. Buyniski, John W. Hooper, Gary M. F. Lim
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Patent number: 4243803Abstract: Ceforanide is produced by the reduction in aqueous solution of a water-soluble salt 7-(2-azido-methylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethy l)-3-cephem-4-carboxylic acid using a borane-amine complex and Raney nickel.Type: GrantFiled: July 5, 1979Date of Patent: January 6, 1981Assignee: Bristol-Myers CompanyInventors: Gary M. F. Lim, Masaki Endo
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Patent number: 4217275Abstract: Disclosed is an improved process for esterifying carboxylic acids, particularly 3-carboxylic acid groups of penicillins and 4-carboxylic acid groups of cephalosporins, to form methoxymethyl esters. Replacement according to the present process of the conventional halomethyl methyl ether esterifying agent with methoxymethyl mesylate avoids the carcinogenicity problem of the prior art reagent while still giving good yields of high quality product.Type: GrantFiled: February 28, 1979Date of Patent: August 12, 1980Assignee: Bristol-Myers CompanyInventors: Gary M. F. Lim, Roberto D. Droghini
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Patent number: 4171439Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is halo or hydroxyl and X is acylamino. Also included in the invention are compounds of the above formula in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds. The compounds are potent antibacterial agents.Type: GrantFiled: June 22, 1978Date of Patent: October 16, 1979Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4166905Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is etherified hydroxyl and X is acylamino. Also included in the invention are compounds of the above formula in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds. The compounds are potent antibacterial agents.Type: GrantFiled: June 22, 1978Date of Patent: September 4, 1979Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4166906Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is hydroxyl esterified with a sulfonic acid residue and X is acylamino. Also included in the invention are compounds of the above formula in which the carboxyl group of the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds. The compounds are potent antibacterial agents.Type: GrantFiled: June 22, 1978Date of Patent: September 4, 1979Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4118563Abstract: A new synthetic route is provided for the production of 7-(2-aminomethylphenylacetamido)-3-(1-carboxymethyltetrazol-5-ylthiomethyl )-3-cephem-4-carboxylic acid.Type: GrantFiled: November 25, 1977Date of Patent: October 3, 1978Assignee: Bristol-Myers CompanyInventors: Gary M. F. Lim, Yvon G. Perron
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Patent number: 4112230Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.Type: GrantFiled: January 17, 1977Date of Patent: September 5, 1978Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4068078Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.Type: GrantFiled: August 19, 1976Date of Patent: January 10, 1978Assignee: Bristol-Myers CorporationInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4068075Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.Type: GrantFiled: August 19, 1976Date of Patent: January 10, 1978Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4068080Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1, 6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carbonyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.Type: GrantFiled: August 19, 1976Date of Patent: January 10, 1978Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4066832Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1,6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1##wherein Z is halo, hydroxyl, etherified hydroxyl or hydroxyl esterified with a carboxylic acid residue or a sulfonic acid residue and X is amino, azido or acylamino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.Type: GrantFiled: August 19, 1976Date of Patent: January 3, 1978Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway
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Patent number: 4011216Abstract: There is described the stereoselective total synthesis of novel .DELTA..sup.2,3 -1,4-morpholine-2-carboxylic acids possessing a fused .beta.-lactam ring in the 1, 6-position and carrying a substituent cis to carbon 5 in the 7-position of the fused ring system represented by the general formula ##STR1## wherein Z is hydroxyl esterified with a carboxylic acid residue and X is amino. Also included in the invention are compounds of formula I in which the carboxyl group at the 2-position is protected as by an easily cleavable ester group and salts of both the free acids and carboxyl-protected compounds of formula I. The compounds of formula I are potent antibacterial agents or are of use as intermediates in the preparation of such antibacterial agents.Type: GrantFiled: April 11, 1975Date of Patent: March 8, 1977Assignee: Bristol-Myers CompanyInventors: Marcel Menard, Gary M. F. Lim, Terry T. Conway