Patents by Inventor Karel M. J. Brands

Karel M. J. Brands 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: 7145002
    Abstract: A process for preparing a crystalline, carbapenem monosodium salt of formula IIa: characterized by the steps a) adding about 10 to 30% of an organic solvent to an aqueous solution of the carbapenem, b) cooling the resulting solution to less than ?5° C., c) adjusting the pH using a solution containing an acid in an organic solvent to give the appropriate pH for crystallization, and d) crystallizing the compound by adding methanol, and a C2-5 alcohol at between ?5 and ?25° C.
    Type: Grant
    Filed: September 20, 2002
    Date of Patent: December 5, 2006
    Assignee: Merck & Co. Inc.
    Inventors: Karel M. J. Brands, Raymond Cvetovich, Louis S. Crocker, Michael D. Ward, Amar J. Mahajan, Robert M. Wenslow, John M. Williams, Daniel R. Sidler, Charles Orella, Elizabeth S. Fisher, Ronald Jobson
  • Publication number: 20040235817
    Abstract: A process for preparing a crystalline, carbapenem monosodium salt of formula IIa: 1
    Type: Application
    Filed: January 27, 2004
    Publication date: November 25, 2004
    Inventors: Karel M. J. Brands, Raymond Cvetovich, Louis S Crocker, Michael D Ward, Amar J Mahajan, Robert M Wenslow, John M Williams, Daniel R Sidler, Charles Orella, Elizabeth S Fisher
  • Patent number: 6552239
    Abstract: The present invention relates to a process for the preparation of cyclopropaneacetylene by reacting a ketophosphonate with a diazo-transfer reagent in the presence of non-nucleophilic base in an aprotic solvent to generate a reaction mixture containing a ketodiazophosphonate compound and then reacting the reaction mixture with cyclopropanecarboxaldehyde in a non-nucleophilic base and a protic solvent to yield cyclopropaneacetylene.
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: April 22, 2003
    Assignee: Merck & Co., Inc.
    Inventor: Karel M. J. Brands
  • Patent number: 6504027
    Abstract: A process for the direct crystallization of a compound of the formula I: or a pharmaceutically acceptable salt thereof, is disclosed, wherein R1 and R2 represent H, C1-10 alkyl, aryl or heteroaryl, or substituted C1-10 alkyl, aryl or heteroaryl and X+ represents a charge balancing group, comprising extracting a solution containing a crude compound of formula I or Ia: or a pharmaceutically acceptable salt thereof, wherein each X+ is a charge balancing group, and R1 and R2 are as described above with a C4-10 alcohol, collecting and crystallizing the resulting aqueous phase to produce a crystalline compound of formula I.
    Type: Grant
    Filed: January 19, 2000
    Date of Patent: January 7, 2003
    Assignee: Merck & Co., Inc.
    Inventors: John M. Williams, Karel M. J. Brands, Renato T. Skerlj, Peter Houghton
  • Patent number: 6313364
    Abstract: The present invention relates to a process for the preparation of cyclopropaneacetylene by the two step process: (1) an alkylation of propiolic acid with a 1,3-disubstituted propane followed by a cycloalkylation to give a 3-cyclopropaneacetylene carboxylic acid; and (2) decarboxylation of 3-cyclopropaneacetylene carboxylic acid in the presence of copper catalyst.
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: November 6, 2001
    Assignee: Merck & Co., Inc.
    Inventor: Karel M. J. Brands
  • Patent number: 6180783
    Abstract: A stabilized carbapenem intermediate compound represented by the formula 1: or a salt thereof is disclosed, wherein P represents a carboxyl protecting group and X represents a charge balancing group. In addition, a process for synthesizing a compound represented by formula 2: is disclosed wherein X+ is a charge balancing group, comprising: deprotecting a compound of the formula 1 to produce a compound 2.
    Type: Grant
    Filed: June 9, 1998
    Date of Patent: January 30, 2001
    Assignee: Merck & Co., Inc.
    Inventors: John M. Williams, Renato T. Skerlj, Karel M. J. Brands, Ulf H. Dolling, Ronald B. Jobson
  • Patent number: 6063931
    Abstract: A process of synthesizing a compound of the formula 1: ##STR1## is described. A compound of the formula 2: ##STR2## is reacted with diphenylphosphinic chloride to activate the carboxylic acid group, and then reacted with methanesulfonyl chloride to produce a compound of formula 4: ##STR3## Compound 4 is then reacted with a group II metal sulfide source in water to produce a compound of formula 1.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: May 16, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Karel M. J. Brands, John M. Williams, Ulf H. Dolling, Ronald B. Jobson, Antony J. Davies, Ian F. Cottrell, Mark Cameron, Michael S. Ashwood
  • Patent number: 6060607
    Abstract: A process of synthesizing a compound of the formula 1: ##STR1## is described. A compound of the formula 2: ##STR2## is reacted with diphenylphosphinic chloride to activate the carboxylic acid group, and then reacted with methanesulfonyl chloride to produce a compound of formula 4: ##STR3## Compound 4 is then reacted with a group II metal sulfide source in water to produce a compound of formula 1.
    Type: Grant
    Filed: June 16, 1999
    Date of Patent: May 9, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Karel M. J. Brands, John M. Williams, Ulf H. Dolling, Ronald B. Jobson, Antony J. Davies, Ian F. Cottrell, Mark Cameron, Michael S. Ashwood
  • Patent number: 5965747
    Abstract: Crystalline 2S-cis-3-[[(4-mercapto-2-pyrrolidinyl) carbonyl]-amino]benzoic acid and salts and solvates thereof are disclosed. Three different crystalline types are described.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: October 12, 1999
    Assignee: Merck & Co., Inc.
    Inventors: Karel M. J. Brands, Ronald B. Jobson
  • Patent number: 5877328
    Abstract: A process for the synthesis of an N-(di-substituted phosphoryl)-trans-4-hydroxy-L-proline of the formula I: ##STR1## is disclosed, wherein R.sup.1 and R.sup.2 independently represent C.sub.1-18 alkyl, phenyl or phenyl-substituted C.sub.1-18 alkyl, or R.sup.1 and R.sup.2 are taken in combination to represent C.sub.2-4 alkylidene or phenyl. Trans-4-hydroxy-L-proline is reacted with a di-(substituted) phosphite of the formula III: ##STR2## in the presence of sodium hypochlorite and sodium hydroxide to produce a compound of formula I.
    Type: Grant
    Filed: October 2, 1997
    Date of Patent: March 2, 1999
    Assignee: Merck & Co., Inc.
    Inventor: Karel M. J. Brands
  • Patent number: 5721368
    Abstract: A process of synthesizing a compound of the formula I: ##STR1## is described. A compound of the formula II: ##STR2## is reacted with diphenylphosphinic chloride to activate the carboxylic acid group, and then reacted with methanesulfonyl chloride to produce a compound of formula IV: ##STR3## Compound IV is then reacted with Na.sub.2 S in water to produce a compound of formula I.
    Type: Grant
    Filed: January 14, 1997
    Date of Patent: February 24, 1998
    Assignee: Merck & Co. Inc.
    Inventor: Karel M. J. Brands
  • Patent number: 5648501
    Abstract: A process of synthesizing a compound of the formula I: ##STR1## is described. A compound of the formula II: ##STR2## is reacted with diphenylphosphinic chloride to activate the carboxylic acid group, and then reacted with methanesulfonyl chloride to produce a compound of formula IV: ##STR3## Compound IV is then reacted with Na.sub.2 S in water to produce a compound of formula I.
    Type: Grant
    Filed: July 22, 1996
    Date of Patent: July 15, 1997
    Assignee: Merck & Co., Inc.
    Inventor: Karel M. J. Brands
  • Patent number: RE40794
    Abstract: A process for preparing a crystalline, carbapenem monosodium salt of formula IIa: characterized by the steps a) adding about 10 to 30% of an organic solvent to an aqueous solution of the carbapenem, b) cooling the resulting solution to less than ?5° C., c) adjusting the pH using a solution containing an acid in an organic solvent to give the appropriate pH for crystallization, and d) crystallizing the compound by adding methanol, and a C2-5 alcohol at between ?5 and ?25° C.
    Type: Grant
    Filed: September 20, 2002
    Date of Patent: June 23, 2009
    Assignee: Merck & Co., Inc.
    Inventors: Karel M. J. Brands, Raymond Cvetovich, Louis S. Crocker, Michael D. Ward, Amar J. Mahajan, Robert M. Wenslow, John M. Williams, Daniel R. Sidler, Charles Orella, Elizabeth S. Fisher, Ronald Jobson