Patents Examined by Donald G. Daus
  • Method for the preparation of an N-vinyl compound
    Patent number: 5708167
    Abstract: Proposed is a novel and very efficient method for the preparation of an N-vinyl compound such as N-vinyl-2-pyrrolidone and N-vinyl-N-ethyl acetamide by the thermal decomposition of an N-(.alpha.-acyloxyethyl) compound which is a novel compound obtained by the addition reaction between an NH group-containing compound such as 2-pyrrolidone and N-ethyl acetamide and a vinyl carboxylate, e.g., vinyl acetate, in the presence of an alkali, e.g. alkali metal hydroxide. The reaction mixture after completion of this addition reaction as such, i.e. without isolating the N-(.alpha.-acyloxyethyl) compound, such as N-(.alpha.-acetoxyethyl)-2-pyrrolidone and N-(.alpha.-acetoxyethyl)-N-ethyl acetamide, is heated to effect in situ formation of the desired N-vinyl compound which can then be isolated by distillation under reduced pressure in a very high overall yield.
    Type: Grant
    Filed: August 23, 1995
    Date of Patent: January 13, 1998
    Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.
    Inventors: Yoshihiro Honma, Shozo Tanaka, Mitsuyoshi Oshima, Soji Tanioka, Fumiaki Kawamoto
  • Dihydrodibenzisoquinolinediones
    Patent number: 5703089
    Abstract: Novel bis-1,2-dihydro-3H-dibenzisoquinoline-1,3-diones and their salts, processes for their preparation, pharmaceutical compositions containing them and methods of using them to treat malignancies, mainly human solid tumor carcinomas.
    Type: Grant
    Filed: August 19, 1996
    Date of Patent: December 30, 1997
    Assignee: Knoll Aktiengesellschaft
    Inventors: Miguel Fernandez Brana, Jose Maria Castellano Berlanga, Cynthia Romerdahl
  • 3-aminoindolyl derivatives
    Patent number: 5703107
    Abstract: The present invention is directed to a new class of 3-amido and 3-sulfamido-indolyl NMDA antagonists and their use in the treatment of a number of disease states.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: December 30, 1997
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Francesco G. Salituro, Bruce M. Baron
  • Process of separating the diastereomers of (6R,6S) -5,6,7,8-tetrahydrofolic acid derivatives
    Patent number: 5698693
    Abstract: A method for resolving 5,6,7,8-tetrahydrofolic acid derivatives into diastereomerically pure 6R and 6S forms. The method comprises (1) alpha esterification of the tetrahydrofolic acid derivative; (2) resolution of the alpha monoester into pure diastereomer; and (3) deprotecting the resolved alpha monoester to thereby produce the pure diastereomer of the original 5,6,7,8 tetrahydrofolic acid derivative. The resolution step can be carried out by any conventional means including chromatography or fractional crystallization. The method results in absolute diastereomeric purity even when an achiral stationary phase is used for the resolution.
    Type: Grant
    Filed: November 16, 1992
    Date of Patent: December 16, 1997
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Anthony L. Fitzhugh, Rhone K. Akee
  • Methotrexate analogs and methods of using same
    Patent number: 5698556
    Abstract: The present invention provides methotrexate analogs having the formula: ##STR1## wherein R is methyl or hydro, X is halo or hydro, and D.sub.1 is --NR.sub.1 R.sub.2 wherein either both R.sub.1 and R.sub.2 are hydrogen, or one is hydrogen and the other is C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 haloalkyl, cyano C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 hydroxyalkyl, alkoxyalkyl wherein the alkoxy and the alkyl have 1-5 carbon atoms, carboxy C.sub.1 -C.sub.5 alkyl, phenyl, C.sub.1 -C.sub.5 alkyl phenyl, C(.dbd.O)R' wherein R' is hydrogen, C.sub.1 -C.sub.5 alkyl, phenyl, or C.sub.1 -C.sub.5 alkyl phenyl, C(.dbd.O)OR" wherein R" is hydrogen, C.sub.1 -C.sub.5 alkyl, phenyl, or C.sub.1 -C.sub.5 alkyl phenyl, amino, C(.dbd.NH)NH.sub.2, C(.dbd.O)NH.sub.2, or C(.dbd.S)NH.sub.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 16, 1997
    Inventor: Carcy L. Chan
  • Process for the stereoselective reduction of steroid enelactams
    Patent number: 5696266
    Abstract: The novel process of this invention involves the reduction of certain .DELTA.-5 steroidal alkenes to selectively produce either the 5.alpha. or 5.beta. reduction products. Particularly, this invention involves reduction of .DELTA.-5 steroidal alkenes using a rhodium based catalyst in the presence of hydrogen to selectively yield 5.alpha. steroids or alternatively reduction of .DELTA.-5 steroidal alkenes in an ionizing medium with a trialkylsilane to selectively yield 5.beta. steroids.
    Type: Grant
    Filed: July 28, 1995
    Date of Patent: December 9, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Guy R. Humphrey, Ross A. Miller
  • 17 .beta.-carboxanilides of 4-aza-5.alpha.-androstan-3-ones as 5.alpha.-reductase inhibitors
    Patent number: 5693810
    Abstract: Described are new 17.beta.-carboxanilides of 4-aza-5.alpha.-androstan-3-ones and related compounds of structural formula I: ##STR1## and the use of such compounds as 5.alpha.-reductase inhibitors for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: December 2, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Gary H. Rasmusson, Raman K. Bakshi, Gool F. Patel
  • Substituted 4-aza-5.alpha.-androstan-ones as 5.alpha.-reductase inhibitors
    Patent number: 5693809
    Abstract: Described are new 16-substituted and 7,16-disubstituted 4-aza-5.alpha.-androstan-3-ones and related compounds as 5.alpha.-reductase inhibitors.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: December 2, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Philippe L. Durette, William Hagmann, Gary H. Rasmusson, Richard L. Tolman, Ihor E. Kopka, Soumya P. Sahoo, Craig K. Esser, Nathan G. Steinberg, Donald W. Graham, Bruce E. Witzel
  • Substituted oxazolidine calpain and/or cathepsin B inhibitors
    Patent number: 5691368
    Abstract: This invention relates to oxazolidine inhibitors of calpain and/or cathepsin B and to compositions containing them. As inhibitors of calpain and/or cathepsin B, the compounds are useful in the treatment of patients afflicted with acute or chronic neurodegenerative disorders.
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: November 25, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Norton P. Peet, Shujaath Mehdi, Matthew D. Linnik, Michael R. Angelastro, Hwa-Ok Kim
  • Methods for the preparation of Benzotriazole herbicidal agents
    Patent number: 5686617
    Abstract: This invention is directed to certain substituted aryloxy benzotriazole compounds which are herbicidal agents. The invention is further directed to methods for the preparation of the aryloxy benzotriazole compounds.
    Type: Grant
    Filed: April 5, 1995
    Date of Patent: November 11, 1997
    Assignee: American Cyanamid Company
    Inventor: Thomas Andrew Lies
  • Benzofuranyl -and benzothienyloxazolidinones
    Patent number: 5684023
    Abstract: The present invention relates to benzofuranyl- and benzothienyloxazolidinones, processes for their preparation and their use as medicaments, in particular as antibacterial medicaments.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: November 4, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Riedl, Dieter Habich, Andreas Stolle, Hanno Wild, Rainer Endermann, Klaus Dieter Bremm, Hein-Peter Kroll, Harald Labischinski, Klaus Schaller, Hans-Otto Werling
  • Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1, 2, 3, 4, -tetrahydroquinolinyl group having retinoid-like activity
    Patent number: 5677323
    Abstract: Retinoid-like activity is exhibited by compounds of the formula ##STR1## where X is S, O; R.sub.1, R.sub.2 and R.sub.3 are hydrogen or lower alkyl; R.sub.4 and R.sub.5 are hydrogen or lower alkyl with the proviso that R.sub.4 and R.sub.5 cannot both be hydrogen, A is, oxazolyl; n is 0-5, and B is H, --COOH or a pharmaceutically acceptable salt, ester or amide thereof, --CH.sub.2 OH or an ether or ester derivative, or --CHO or an acetal derivative, or --COR.sub.1 or a ketal derivative where R.sub.1 is --(CH.sub.2).sub.m CH.sub.3 where m is 0-4, or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: October 29, 1996
    Date of Patent: October 14, 1997
    Assignee: Allergan
    Inventor: Roshantha A. S. Chandraratna
  • 3-amidoindolyl derivatives
    Patent number: 5675018
    Abstract: The present invention is directed to a new class of 3-amido and 3-sulfamido-indolyl NMDA antagonists and their use in the treatment of a number of disease states.
    Type: Grant
    Filed: November 6, 1995
    Date of Patent: October 7, 1997
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Francesco G. Salituro, Bruce M. Baron
  • 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz ?cd! indoles
    Patent number: 5674884
    Abstract: 6-thiazolyl-4-amino-1,3,4,5-tetrahydrobenz?cd!indoles are provided which are useful in modifying the function of serotonin in mammals.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: October 7, 1997
    Assignee: Eli Lilly and Company
    Inventors: Richard N. Booher, David E. Lawhorn, Charles J. Paget, Jr., John M. Schaus
  • Lactone stable formulation of 7-ethyl 10-hydroxy camptothecin and methods for uses thereof
    Patent number: 5674874
    Abstract: 7-ethyl-10-hydroxy camptothecin (HECPT), an active metabolite of the camptothecin analog CPT-11 which is used as an anticancer drug, is poorly soluble in water. Because of its poor water solubility, HECPT has not been directly administered by parenteral or oral routes in human patients for the purpose of inhibiting the growth of cancer cells. There is also unpredictable interpatient variability in the metabolic production of HECPT from CPT-11 which limits the utility of CPT-11. This invention overcomes these limitations by teaching novel pharmaceutically acceptable lactone stable HECPT formulations for the direct administration of lactone stable HECPT formulations orally or parenterally to patients with various forms of cancer.
    Type: Grant
    Filed: September 1, 1995
    Date of Patent: October 7, 1997
    Assignee: BioNumerik Pharmaceuticals, Inc.
    Inventors: Frederick H. Hausheer, Kochat Haridas
  • 9-aminoacridine derivatives possessing psychotropic, antiamnestic and lipid-regulative activity
    Patent number: 5672707
    Abstract: "Derivatives of 9-aminoacridine characterized by psychothropic, antiamnestic and lipid-regulating activities".New chemical compounds derived of 9-aminoacridine with a general formula are presented: ##STR1## where R=H or CH.sub.3 R.sup.1 =H, CH.sub.3, or BrR.sup.2 =H, CH.sub.3R.sup.3 =--C.sub.1 -C.sub.5 alkyl phenylmethyl, substituted phenylmethyl or diethylaminoethylX=C=O, or CHOH, Y=CH.sub.2 orX+Y=CH=CHand their salts with organic and inorganic acids.The target compounds were obtained by a reaction of substituted nitriles of anthranilic acid with dimedone and subsequent cyclization of intermediate enaminonitriles to the corresponding 9-amino-3,4-dihydroacridine-1(2H)-ones. The reduction of the compounds or their alkylated or aralkylated at 9-aminogroupe derivatives results in corresponding alkanols, which on dehydratation give 9-amino-3,4-dihydroacridines.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: September 30, 1997
    Assignee: Vserossiisky Nauchny Tsentr Po Bezopasnosti Biologicheski Aktivnykh veschestv (Vntsbav)
    Inventors: Yury Valentinovich Burov, Sergei Borisovich Goncharenko, Tatyana Nikolaevna Robakidze, Jury Nikolaevich Portnov, Ljubov Vladislavovna Kadysheva, Ilmar Kharievich Penke, Eduard Maximovich Peganov, Svetlana Alexeevna Sukhanova, Galina Vasilievna Tananova, Anatoly Evgenievich Voronin, Anatoly Alexeevich Kotlobai, Yanis Fritsevich Oshis, Lidia Evgenievna Pchelintseva
  • Water soluble camptothecin analogs
    Patent number: 5670500
    Abstract: The present invention provides water soluble camptothecin analogs of Formula I: ##STR1## which are particularly useful as antineoplastic agents; pharmaceutical compositions thereof; and a method of treating cancer in an animal in need thereof, including human beings, comprising inhibition of the growth of tumor cells in said animal by administration of an effective amount of a compound of Formula I.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: September 23, 1997
    Assignee: SmithKline Beecham Corporation
    Inventors: David A. Berges, John J. Taggart
  • 2,6-diaryl pyridazinones with immunosuppressant activity
    Patent number: 5670504
    Abstract: A class of 2,6-diarylpyridazinones of general structural formula I have been identified that exhibit exhibit immunosuppressant activity with human T-lymphocytes, and are useful as an immunosuppressants.
    Type: Grant
    Filed: February 23, 1995
    Date of Patent: September 23, 1997
    Assignee: Merck & Co. Inc.
    Inventors: Richard J. Bochis, Andrew Kotliar, William H. Parsons, Kathleen Rupprecht
  • Total synthesis of northebaine, normophine, noroxymorphone enantiomers and derivatives via N-Nor intermediates
    Patent number: 5668285
    Abstract: The invention involves a method of making key intermediates useful in the synthesis of many opiate narcotics and antagonists and agonists; and the non-opiate enantiomers thereof which have potent antitussive properties. The synthesis starts from either the natural or unnatural enantiomer of nordihydrocodeinone and produces 8, 14-dihydronorthebaine, the diketal of 7-bromonordihydrocodeinone, northebaine, norcodeinone diketal and 14-hydroxynorcodeinone intermediates without the necessity of leaving the N-nor structure. The syntheses have fewer steps than previous methods, and also have high yields.
    Type: Grant
    Filed: March 12, 1992
    Date of Patent: September 16, 1997
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Kenner C. Rice, Amy H. Newman
  • 6-Heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD] indoles
    Patent number: 5665758
    Abstract: 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: September 9, 1997
    Assignee: Eli Lilly and Company
    Inventors: Richard N. Booher, David E. Lawhorn, Charles J. Paget, Jr., John M. Schaus