Patents by Inventor Richard F. Shuman

Richard F. Shuman 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: 6641705
    Abstract: A charged particle beam uniformly removes material, particularly crystalline material, from an area of a target by compensating for or altering the crystal orientation or structure of the material to be removed. The invention is particularly suited for FIB micromachining of copper-based crystalline structures. Uniformity of material removal can be improved, for example, by passing incoming ions through a sacrificial layer formed on the surface of the material to be removed. The sacrificial layer is removed along with the material being milled. Uniformity of removal can also be improved by changing the morphology of the material to be removed, for example, by disrupting its crystal structure or by altering its topography.
    Type: Grant
    Filed: March 27, 2001
    Date of Patent: November 4, 2003
    Assignee: FEI Company
    Inventors: Michael Phaneuf, Jian Li, Richard F. Shuman, Kathryn Noll, J. David Casey, Jr.
  • Publication number: 20010053605
    Abstract: A charged particle beam uniformly removes material, particularly crystalline material, from an area of a target by compensating for or altering the crystal orientation or structure of the material to be removed. The invention is particularly suited for FIB micromachining of copper-based crystalline structures. Uniformity of material removal can be improved, for example, by passing incoming ions through a sacrificial layer formed on the surface of the material to be removed. The sacrificial layer is removed along with the material being milled. Uniformity of removal can also be improved by changing the morphology of the material to be removed, for example, by disrupting its crystal structure or by altering its topography.
    Type: Application
    Filed: March 27, 2001
    Publication date: December 20, 2001
    Inventors: Michael Phaneuf, Jian Li, Richard F. Shuman, Kathryn Noll, J. David Casey
  • Patent number: 6322672
    Abstract: A method of enhancing charged particle beam etching particularly suitable for copper interconnects, includes milling at non-contiguous locations to prevent the formation or propagation of an etch-resistant region within the rastered area. Two or more milling boxes are typically performed, one or more of the boxes having pixel spacing greater than the spot size, with the last box using a conventional pixel spacing (default mill) smaller than the spot size to produce a uniform, planar floor of the etched area.
    Type: Grant
    Filed: March 10, 2000
    Date of Patent: November 27, 2001
    Assignee: FEI Company
    Inventors: Richard F. Shuman, Kathryn Noll, J. David Casey, Jr.
  • Patent number: 5777105
    Abstract: Imidazolmethyloxy-substituted tricyclo-macrolide immunosuppressants are prepared by reacting a tricyclo-macrolide with an imidazolmethyl trichloroacetimidate in the presence of an acid. The invention further provides a crystalline salt of imidazolmethyloxy-substituted tricyclo-macrolide, as well as novel compounds useful in the process of the present invention.
    Type: Grant
    Filed: July 23, 1996
    Date of Patent: July 7, 1998
    Assignee: Merck & Co., Inc.
    Inventors: David J. Mathre, Richard F. Shuman, Paul Sohar, Zhiguo Song
  • Patent number: 5693805
    Abstract: A process for the manufacture of oxytocin receptor antagonists of the following formula (I) ##STR1## and their crystalline salts is disclosed.
    Type: Grant
    Filed: September 12, 1995
    Date of Patent: December 2, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Anthony M. DeMarco, Edward J.J. Grabowski, Guo-Jie Ho, David J. Mathre, Khateeta M. Emerson, Richard F. Shuman, Paul Sohar
  • Patent number: 5187278
    Abstract: A novel single-pot trialkylsilyl trifluoromethanesulfonate (R.sub.3 Si-OTf) mediated process produces derivatives of 4-aza 3-keto steroids at the .alpha.-methylenic carbon through electrophilic substitution. These derivatives are useful in the preparation, through elimination of the substituent on the .alpha.-methylene carbon, of .DELTA.-1 olefin 4-aza 3-keto steroids which are potent inhibitors of 5-.alpha. reductase.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: February 16, 1993
    Assignee: Merck & Co., Inc.
    Inventors: Anthony O. King, Kevin Anderson, Sandor Karady, Alan W. Douglas, Newton L. Abramson, Richard F. Shuman
  • Patent number: 5120847
    Abstract: A novel, facile, and specific process for .alpha.-iodinating or .alpha.-brominating the .alpha.-methylenic carbon of a straight chain, branched chain, or cyclic secondary amide, such as a lactam or an azasteroid, comprises reacting the amide with trialkylsilyl-X (R.sub.3 Si--X), where X is Br, I, or Cl, and R is methyl, ethyl, or n-propyl, in the presence of I.sub.2 or Br.sub.2. The .alpha.-iodo- or .alpha.-bromo-amide is useful for making the .alpha.,.beta.-unsaturated amide through dehydrohalogenation.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: June 9, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Anthony O. King, Sandor Karady, Kevin Anderson, Newton L. Abramson, Richard F. Shuman
  • Patent number: 5091534
    Abstract: A novel single-pot trialkylsilyl trifluoromethanesulfonate (R.sub.3 Si--OTf) mediated process produces derivatives of 4-aza 3-keto steroids at the .alpha.-methylenic carbon through electrophilic substitution. These derivatives are useful in the preparation, through elimination of the substituent on the .alpha.-methylene carbon, of .DELTA.-1 olefin 4-aza 3-keto steroids which are potent inhibitors of 5-.alpha. reductase.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: February 25, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Anthony O. P. King, Sandor Karady, Kevin Anderson, Alan W. Douglas, Newton L. Abramson, Richard F. Shuman
  • Patent number: 5039814
    Abstract: A process utilizes the tetrazole functional group to direct lithiation at the ortho position of a phenyltetrazole and generate a nucleophilic aryllithium species which then undergoes reaction with an electrophile to generate a 2-substituted 1-(tetrazol-5-yl)benzene. The process is useful in the production of intermediates in the synthesis of angiotensin II antagonists. This novel process is a more cost effective and versatile route for the large-scale preparation of these key intermediates.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: August 13, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Richard F. Shuman, Anthony O. King, Robert K. Anderson
  • Patent number: 4880928
    Abstract: There is disclosed an improved process for the preparation of 3-[(4-bromo-2-fluorophenyl)-methyl]-3,4-dihydro-4-oxo-1-phthalazineacetic acid. The process is significantly improved over the prior art process in preparing the product in a one-step process where the prior art required three steps. The instant process directly alkylates a phthalazine ring nitrogen in the presence of the acetic acid moiety without the necessity of protecting the carboxylic acid group as was necessary in the prior art preferred process. The product is useful for treating the progressive deterioration resulting from diabetes.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: November 14, 1989
    Assignee: Merck & Co., Inc.
    Inventor: Richard F. Shuman
  • Patent number: 4510083
    Abstract: A process for producing polypeptides is disclosed wherein potassium, rubidium, or cesium serves as the counterion for both the carbonate buffer system and the amino acid or peptide salts employed.
    Type: Grant
    Filed: May 31, 1983
    Date of Patent: April 9, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Thomas J. Blacklock, Richard F. Shuman
  • Patent number: 4216317
    Abstract: Adenine is prepared by heating hydrogen chloride and hydrogen cyanide in a mixture of phosphorus oxychloride and dichlorophosphoric acid as solvent in a sealed vessel or by heating N-dichloromethylformamidine hydrochloride or triazine hydrochloride in a mixture of phosphorus oxychloride and dichlorophorphoric acid.
    Type: Grant
    Filed: February 12, 1979
    Date of Patent: August 5, 1980
    Assignee: Merck & Co., Inc.
    Inventors: Richard F. Shuman, Roger J. Tull
  • Patent number: 3970693
    Abstract: Process for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indene-3-acetic acid by reacting fluorobenzene with an acid halide, to form an indanone, reaction of the indanone with a methylthio (or methylsulfinyl) benzyl compound to form 5-fluoro-2-methyl-1-(p-methylthiobenzyl) or (p-methylsulfinylbenzyl)-indene and reacting said indene with a glyoxylic acid.This invention relates to new processes for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indene-3-acetic acid, to intermediates thereof and processes for said intermediates.
    Type: Grant
    Filed: July 5, 1974
    Date of Patent: July 20, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Roger J. Tull, Robert F. Czaja, Richard F. Shuman, Seemon H. Pines
  • Patent number: 3953490
    Abstract: A method for preparing 2-acetamidoethyl (3-trifluoromethylphenoxy)(4-chlorophenyl)acetate which comprises treating (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile with 2-acetamidoethanol in the presence of an acid to form an imino intermediate which, upon treatment with an aqueous solution, affords the desired product. 2-Acetamidoethyl (3-trifluoromethylphenoxy)(4-chlorophenyl)acetate is a hypocholesterolemic and hypolipemic agent which effectively reduces the concentration of cholesterol, triglycerides and other lipids in blood serum.
    Type: Grant
    Filed: November 12, 1974
    Date of Patent: April 27, 1976
    Assignee: Merck & Co., Inc.
    Inventor: Richard F. Shuman
  • Patent number: 3944600
    Abstract: Process for preparing 5-fluoro-2-methyl-1-(p-methylsulfinylbenzylidene)-indene-3-acetic acid by reacting fluorobenzene with an acid halide, to form an indanone, reaction of the indanone with a methylthio (or methylsulfinyl)benzyl compound to form 5-fluoro-2-methyl-1-(p-methylthiobenzyl) or (p-methylsulfinylbenzyl)-indene and reacting said indene with a glyoxylic acid. The invention also relates to intermediates thereof and processes for said intermediates.
    Type: Grant
    Filed: September 30, 1974
    Date of Patent: March 16, 1976
    Assignee: Merck & Co., Inc.
    Inventors: Roger J. Tull, Robert F. Czaja, Richard F. Shuman, Seemon H. Pines