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: 5245064Abstract: 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: GrantFiled: August 14, 1992Date of Patent: September 14, 1993Inventors: Paul G. Gassman, John R. Sowa, John W. Mickelson
-
Patent number: 5208353Abstract: 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: GrantFiled: July 15, 1992Date of Patent: May 4, 1993Assignee: SmithKline Beecham Corp.Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
-
Patent number: 5110959Abstract: 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: GrantFiled: June 14, 1989Date of Patent: May 5, 1992Assignee: Smithkline Beckman Corp.Inventors: Joseph R. Flisak, Paul G. Gassman, Ivan Lantos, Wilford L. Mendelson
-
Patent number: 4847392Abstract: 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: GrantFiled: March 17, 1987Date of Patent: July 11, 1989Assignee: Regents of the University of MinnesotaInventors: Paul G. Gassman, Daniel A. Singleton
-
Patent number: 4699987Abstract: 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: GrantFiled: June 3, 1986Date of Patent: October 13, 1987Assignee: Regents of the University of MinnesotaInventors: Paul G. Gassman, Charles H. Winter
-
Patent number: 4582578Abstract: 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: GrantFiled: August 2, 1985Date of Patent: April 15, 1986Assignee: Regents of the University of MinnesotaInventors: Paul G. Gassman, James W. Hershberger
-
Patent number: 4252723Abstract: 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: GrantFiled: January 12, 1979Date of Patent: February 24, 1981Assignee: Regents of the University of MinnesotaInventor: Paul G. Gassman
-
Patent number: 4188325Abstract: 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: GrantFiled: August 21, 1978Date of Patent: February 12, 1980Assignee: Regents of University of MinnesotaInventors: Paul G. Gassman, Berkeley W. Cue, Jr.
-
Patent number: 4186132Abstract: 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: GrantFiled: April 15, 1977Date of Patent: January 29, 1980Assignee: The Regents of the University of MinnesotaInventors: Paul G. Gassman, Berkeley W. Cue
-
Patent number: 4101583Abstract: 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: GrantFiled: August 9, 1976Date of Patent: July 18, 1978Assignee: The Ohio State University Research FoundationInventor: Paul G. Gassman
-
Patent number: 4080341Abstract: 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: GrantFiled: August 9, 1976Date of Patent: March 21, 1978Assignee: The Ohio State University Research FoundationInventor: Paul G. Gassman
-
Patent number: 4067875Abstract: 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: GrantFiled: August 9, 1976Date of Patent: January 10, 1978Assignee: The Ohio State University Research FoundationInventor: Paul G. Gassman
-
Patent number: 4056569Abstract: 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: GrantFiled: June 17, 1976Date of Patent: November 1, 1977Assignee: The Ohio State University Research FoundationInventor: Paul G. Gassman
-
Patent number: 4035375Abstract: 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: GrantFiled: May 14, 1976Date of Patent: July 12, 1977Assignee: The Ohio State University Research FoundationInventors: Paul G. Gassman, Gordon D. Gruetzmacher
-
Patent number: 3996264Abstract: 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: GrantFiled: March 31, 1975Date of Patent: December 7, 1976Assignee: The Ohio State University Research FoundationInventor: Paul G. Gassman
-
Patent number: 3992392Abstract: 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: GrantFiled: April 30, 1975Date of Patent: November 16, 1976Assignee: The Ohio State University Research FoundationInventor: Paul G. Gassman
-
Patent number: 3985756Abstract: 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: GrantFiled: February 27, 1975Date of Patent: October 12, 1976Assignee: The Ohio State University Research FoundationInventors: Paul G. Gassman, Gordon D. Gruetzmacher
-
Patent number: 3972894Abstract: 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: GrantFiled: February 27, 1975Date of Patent: August 3, 1976Assignee: The Ohio State University Research FoundationInventor: Paul G. Gassman
-
Patent number: 3960926Abstract: 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: GrantFiled: April 30, 1975Date of Patent: June 1, 1976Assignee: The Ohio State University Research FoundationInventors: Paul G. Gassman, Gordon D. Gruetzmacher
-
Patent number: RE29882Abstract: 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: GrantFiled: May 2, 1977Date of Patent: January 16, 1979Assignee: Ohio State University Research FoundationInventor: Paul G. Gassman