Patents by Inventor Paul G. Gassman

Paul G. Gassman 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: 5245064
    Abstract: The present invention provides a compound of the formula: ##STR1## wherein R.sup.1 is (C.sub.1 -C.sub.5)perfluoroalkyl, R.sup.2 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.3 is (C.sub.1 -C.sub.5)perfluoroalkyl or (C.sub.1 -C.sub.5)alkyl, R.sup.4 is (C.sub.1 -C.sub.5)alkyl and R.sup.5 is (C.sub.1 -C.sub.5)alkyl, with the proviso that no more than two of R.sup.1, R.sup.2 and R.sup.3 can be (C.sub.1 -C.sub.5)perfluoroalkyl; and transition metal complexes thereof.
    Type: Grant
    Filed: August 14, 1992
    Date of Patent: September 14, 1993
    Inventors: Paul G. Gassman, John R. Sowa, John W. Mickelson
  • Patent number: 5208353
    Abstract: This invention relates to a process for preparing epoxy esters, and intermediates prepared by this process, in particular, to a process which produces non-racemic epoxy esters which are of use as intermediates in the preparation of pharmaceutical compounds.
    Type: Grant
    Filed: July 15, 1992
    Date of Patent: May 4, 1993
    Assignee: SmithKline Beecham Corp.
    Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
  • Patent number: 5110959
    Abstract: This invention relates to a process for preparing epoxy esters, and intermediates prepared by this process, in particular, to a process which produces non-racemic epoxy esters which are of use as intermediates in the preparation of pharmaceutical compounds.
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: May 5, 1992
    Assignee: Smithkline Beckman Corp.
    Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
  • Patent number: 4847392
    Abstract: A method of conducting a Diels-Alder reaction is provided comprising reacting a Diels-Alder diene comprising a 1,3-conjugated diene with a dienophile comprising an alpha,beta-unsaturated acetal or ketal in the presence of a protonating acid to yield a [4+2] cycloadduct.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: July 11, 1989
    Assignee: Regents of the University of Minnesota
    Inventors: Paul G. Gassman, Daniel A. Singleton
  • Patent number: 4699987
    Abstract: Perfluoroalkylcyclopentadienylthallium compounds of the general formula: ##STR1## wherein n=1-5 are disclosed which are useful to modify the properties of transition metal complexes by the introduction of an electron-withdrawing perfluoroalkylcyclopentadienyl moiety thereinto.
    Type: Grant
    Filed: June 3, 1986
    Date of Patent: October 13, 1987
    Assignee: Regents of the University of Minnesota
    Inventors: Paul G. Gassman, Charles H. Winter
  • Patent number: 4582578
    Abstract: A method based on a cyclic single electron transfer mechanism has been developed for the electrochemical initiation and interruption of the exothermic quadricyclane to norbornadiene conversion.
    Type: Grant
    Filed: August 2, 1985
    Date of Patent: April 15, 1986
    Assignee: Regents of the University of Minnesota
    Inventors: Paul G. Gassman, James W. Hershberger
  • Patent number: 4252723
    Abstract: An aniline is converted to a 3-lower hydrocarbonthiooxindole by processes already known in the art and then air oxidized in an inert liquid vehicle in the presence of a base. The inert liquid vehicle advantageously is aprotic and the base is non-nucleophilic. Also, the aprotic liquid vehicle is desirably solvent for the starting 3-lower hydrocarbonthiooxindole and the non-nucleophilic base.
    Type: Grant
    Filed: January 12, 1979
    Date of Patent: February 24, 1981
    Assignee: Regents of the University of Minnesota
    Inventor: Paul G. Gassman
  • Patent number: 4188325
    Abstract: An aniline is converted to a 3-lower hydrocarbonthiooxindole by processes already known in the art, the product converted to a 3-halo-3-lower hydrocarbonthiooxindole by oxidative halogenation, and the product subjected to hydrolysis to form the desired isatins.
    Type: Grant
    Filed: August 21, 1978
    Date of Patent: February 12, 1980
    Assignee: Regents of University of Minnesota
    Inventors: Paul G. Gassman, Berkeley W. Cue, Jr.
  • Patent number: 4186132
    Abstract: An aniline is converted to a 3-lower hydrocarbonthiooxindole by processes already known in the art, the product converted to a 3-halo-3-lower hydrocarbonthiooxindole by oxidative halogenation, and the product subjected to hydrolysis to form the desired isatins.
    Type: Grant
    Filed: April 15, 1977
    Date of Patent: January 29, 1980
    Assignee: The Regents of the University of Minnesota
    Inventors: Paul G. Gassman, Berkeley W. Cue
  • Patent number: 4101583
    Abstract: Preparing indoles and intermediates therefor by reacting an N-haloaniline with a .beta.-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the .beta.-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an .alpha.-ethyl-.beta.-carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures.
    Type: Grant
    Filed: August 9, 1976
    Date of Patent: July 18, 1978
    Assignee: The Ohio State University Research Foundation
    Inventor: Paul G. Gassman
  • Patent number: 4080341
    Abstract: Preparing indoles and intermediates therefor by reacting an N-haloaniline with a .beta.-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the .beta.-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an .alpha.-ethyl-.beta.-carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures.
    Type: Grant
    Filed: August 9, 1976
    Date of Patent: March 21, 1978
    Assignee: The Ohio State University Research Foundation
    Inventor: Paul G. Gassman
  • Patent number: 4067875
    Abstract: Preparing indoles and intermediates therefor by reacting an N-haloaniline with a .beta.-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the .beta.-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an .alpha.-ethyl-.beta.-carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures.
    Type: Grant
    Filed: August 9, 1976
    Date of Patent: January 10, 1978
    Assignee: The Ohio State University Research Foundation
    Inventor: Paul G. Gassman
  • Patent number: 4056569
    Abstract: Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with .beta.-thio esters or .beta.-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho-[thioether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thioether (aminocarbonyl) alkyl]aniline, reacting the orthosubstituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.
    Type: Grant
    Filed: June 17, 1976
    Date of Patent: November 1, 1977
    Assignee: The Ohio State University Research Foundation
    Inventor: Paul G. Gassman
  • Patent number: 4035375
    Abstract: Preparing ortho-substituted anilines by reacting an N-chloroaniline with a non-carbonylic di-hydrocarbon sulfide to form an azasulfonium chloride, reacting the azasulfonium chloride with a strong base to form an aniline substituted in the 2-position with a hydrocarbon-S-hydrocarbyl thio-ether group. The ortho-substituted thio-ether compounds can be reduced with a de-sulfurizing reducing agent such as Raney nickel or the like to form the orthoalkylated aniline. The analine may be an amino-pyridine. The azasulfonium salt and thio-ether intermediate products can be isolated and recovered. If desired, the thio-ether compounds can be reduced to form ortho-alkylated aniline products which are useful as intermediates for a wide variety of purposes, including their uses in making dyes, herbicides, and the like.
    Type: Grant
    Filed: May 14, 1976
    Date of Patent: July 12, 1977
    Assignee: The Ohio State University Research Foundation
    Inventors: Paul G. Gassman, Gordon D. Gruetzmacher
  • Patent number: 3996264
    Abstract: Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with .beta.-thio esters or .beta.-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho-[thio-ether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thio-ether (aminocarbonyl) alkyl]aniline, reacting the ortho-substituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.
    Type: Grant
    Filed: March 31, 1975
    Date of Patent: December 7, 1976
    Assignee: The Ohio State University Research Foundation
    Inventor: Paul G. Gassman
  • Patent number: 3992392
    Abstract: Preparing indoles and intermediates therefor by reacting an N-haloaniline with a .beta.-carbonylic hydrocarbon sulfide to form an azasulfonium halide, reacting the azasulfonium halide with a strong base to form a thio-ether indole derivative, and then reducing the thio-ether indole, e.g. with Raney nickel, to form the indole compound. When an acetal or ketal of the .beta.-carbonyl hydrocarbon sulfide is used, the azasulfonium salt is treated with a base, and then with an acid to form the thio-ether indole derivative. When an .alpha.-ethyl-.beta. -carbonylic hydrocarbon sulfide is used, the resulting azosulfonium salt reacts with strong base to form a thio-ether indolenine derivative, which on reduction with Raney nickel or complex metal hydrides yields 3-substituted indoles. The aniline may be an aminopyridine to form an aza-indole compound in the process. The azasulfonium salts and thio-ether indole or thio-ether indolenine derivatives can be isolated and recovered from their respective reaction mixtures.
    Type: Grant
    Filed: April 30, 1975
    Date of Patent: November 16, 1976
    Assignee: The Ohio State University Research Foundation
    Inventor: Paul G. Gassman
  • Patent number: 3985756
    Abstract: Preparing ortho-substituted anilines by reacting an N-chloroaniline with a non-carbonylic di-hydrocarbon sulfide to form an azasulfonium chloride, reacting the azasulfonium chloride with a strong base to form an aniline substituted in the 2-position with a hydrocarbon-S-hydrocarbyl thio-ether group. The ortho-substituted thio-ether compounds can be reduced with a de-sulfurizing reducing agent such as Raney nickel or the like to form the ortho-alkylated aniline. The aniline may be an amino-pyridine. The azasulfonium salt and thio-ether intermediate products can be isolated and recovered. If desired, the thio-ether compounds can be reduced to form ortho-alkylated aniline products which are useful as intermediates for a wide variety of purposes, including their uses in making dyes, herbicides, and the like.
    Type: Grant
    Filed: February 27, 1975
    Date of Patent: October 12, 1976
    Assignee: The Ohio State University Research Foundation
    Inventors: Paul G. Gassman, Gordon D. Gruetzmacher
  • Patent number: 3972894
    Abstract: Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with .beta.-thio esters or .beta.-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho-[thio-ether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thio-ether (aminocarbonyl) alkyl]aniline, reacting the orthosubstituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.
    Type: Grant
    Filed: February 27, 1975
    Date of Patent: August 3, 1976
    Assignee: The Ohio State University Research Foundation
    Inventor: Paul G. Gassman
  • Patent number: 3960926
    Abstract: Preparing azasulfonium halide salt derivatives of an aniline by reacting a halogen with a non-carbonylic dihydrocarbon sulfide, a beta-carbonylic hydrocarbon sulfide, or a .beta.-thio ester or amide to form a halogen: sulfur compound complex and then reacting the complex with an aniline to form the azasulfonium halide salts. The azasulfonium halide salts are useful as intermediates in processes for making ortho-alkylated anilines, indoles, and 2-oxindoles which have a variety of known uses.
    Type: Grant
    Filed: April 30, 1975
    Date of Patent: June 1, 1976
    Assignee: The Ohio State University Research Foundation
    Inventors: Paul G. Gassman, Gordon D. Gruetzmacher
  • Patent number: RE29882
    Abstract: Preparing oxindoles and intermediates therefor by reacting an N-haloaniline with .beta.-thio ester or .beta.-thio amides to form an azasulfonium halide, reacting the azasulfonium halide with a base to form an ortho[thio-ether (hydrocarbonoxycarbonyl) alkyl]aniline, or a [thio-ether (aminocarbonyl) alkyl]aniline, reacting the ortho-substituted aniline with an acid to form a 3-thio-ether-2-oxindole, and then reducing the 3-thio-ether-2-oxindole with Raney Nickel to form the 2-oxindole.
    Type: Grant
    Filed: May 2, 1977
    Date of Patent: January 16, 1979
    Assignee: Ohio State University Research Foundation
    Inventor: Paul G. Gassman