Patents by Inventor Kun M. Shih

Kun M. Shih 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: 5244891
    Abstract: Crystalline sulfuric, di-nitric, mono-hydrochloric, di-hydrochloric, and di- and sesqui-orthosphosphoric acid addition salts of 7-[.alpha.-(2-aminothiazol-4-yl)-.alpha.-(Z)-methoxyiminoacetamido]-3-[(1- methyl-1-pyrrolidinio)methyl]-3-cephem-4-carboxylate are stable even at elevated temperatures. The crystalline sulfuric acid addition salt is made by forming an admixture of (a) at least one molar equivalent of sulfuric acid with (b) zwitterion in an amount so as to be present in the admixture at a concentration of greater than 25 milligrams/ml, causing crystallization, separating the crystals, washing and drying. The crystalline monohydrochloride, dihydrochloride, and orthophosphate salts are prepared by dissolving the zwitterion in the appropriate amount of acid, causing crystallization by adding acetone and isolating the crystals. Physical admixtures of the salts with certain bases in proportions to give a pH ranging from about 3.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: September 14, 1993
    Assignee: Bristol-Myers Squibb Company
    Inventors: Murray A. Kaplan, Thomas W. Hudyma, Robert A. Lipper, Kun M. Shih, Susan D. Boettger
  • Patent number: 4994451
    Abstract: Crystalline sulfuric, di-nitric, mono-hydrochloric, di-hydrochloric, and di- and sesqui-orthosphosphoric acid addition salts of 7-[.alpha.-(2-aminothiazol-4-yl)-.alpha.-(Z)-methoxyiminoacetamido]-3-[(1- methyl-1-pyrrolidinio)methyl]-3-cephem-4-carboxylate are stable even at elevated temperatures. The crystalline sulfuric acid addition salt is made by forming an admixture of (a) at least one molar equivalent of sulfuric acid with (b) zwitterion in an amount so as to be present in the admixture at a concentration of greater than 25 milligrams/ml, causing crystallization, separating the crystals, washing and drying. The crystalline monohydrochloride, dihydrochloride, and orthophosphate salts are prepared by dissolving the zwitterion in the appropriate amount of acid, causing crystallization by adding acetone and isolating the crystals. Physical admixtures of the salts with certain bases in proportions to give a pH ranging from about 3.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: February 19, 1991
    Assignee: Bristol-Myers Company
    Inventors: Murray A. Kaplan, Thomas W. Hudyma, Robert A. Lipper, Kun M. Shih, Susan D. Boettger
  • Patent number: 4910301
    Abstract: Crystalline sulfuric, di-nitric, mono-hydrochloric, di-hydrochloric, and di- and sesqui-orthosphosphoric acid addition salts of 7-[.alpha.-(2-aminothiazol-4-yl)-.alpha.-(Z)-methoxyiminoacetamido]-3-[(1- methyl-1-pyrrolidinio)methyl]-3-cephem-4-carboxylate are stable even at elevated temperatures. The crystalline sulfuric acid addition salt is made by forming an admixture of (a) at least one molar equivalent of sulfuric acid with (b) zwitterion in an amount so as to be present in the admixture at a concentration of greater than 25 milligrams/ml, causing crystallization, separating the crystals, washing and drying. The crystalline monohydrochloride, dihydrochloride, and orthophosphate salts are prepared by dissolving the zwitterion in the appropriate amount of acid, causing crystallization by adding acetone and isolating the crystals. Physical admixtures of the salts with certain bases in proportions to give a pH ranging from about 3.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: March 20, 1990
    Assignee: Bristol-Myers Company
    Inventors: Murray A. Kaplan, Thomas W. Hudyma, Robert A. Lipper, Kun M. Shih, Susan D. Boettger
  • Patent number: 4868294
    Abstract: Processes for the preparation of stable, crystalline cephalosporin intermediates of the formula ##STR1## wherein X is HI or HCl, and Nu and Nu.sup..sym. are certain N-containing heterocyclic rings attached via a sulfur atom or a ring nitrogen atom, respectively, which are substantially free of the .DELTA..sup.2 isomer; processes for intermediates in the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: September 19, 1989
    Assignee: Bristol-Myers Company
    Inventors: Steven P. Brundidge, Paul R. Brodfuehrer, Chet Sapino, Jr., Kun M. Shih, Donald G. Walker
  • Patent number: 4714760
    Abstract: Stable, crystalline cephalosporin intermediates of the formula ##STR1## wherein X is HI or HCl and Nu and Nu.sup..sym. are certain N-containing heterocyclic rings attached via a sulfur atom or a ring nitrogen atom, respectively, which are substantially free of the .DELTA..sup.2 isomer; processes for, and intermediates in, the preparation of the above compounds; and processes for the preparation of broad-spectrum cephalosporin antibiotics.
    Type: Grant
    Filed: July 11, 1986
    Date of Patent: December 22, 1987
    Assignee: Bristol-Myers Company
    Inventors: Steven P. Brundidge, Paul R. Brodfuehrer, Chet Sapino, Jr., Kun M. Shih, Donald G. Walker
  • Patent number: 4176131
    Abstract: Optionally substituted silicon isocyanates are prepared by reacting a corresponding silicon halide with an alkali metal cyanate or an alkaline earth metal cyanate in an inert solvent having a dielectric constant below about 10, in the presence of a crown ether as a catalyst.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: November 27, 1979
    Assignee: Bristol-Myers Company
    Inventors: Kun M. Shih, Derek Walker