Patents Assigned to Sterling Drug Inc.
  • Patent number: 4436221
    Abstract: A package and dispensing device for a continuous roll of pre-moistened towelettes which has an outer container that holds therein the roll of pre-moistened towelettes, the roll being surrounded by a bag which prevents the roll from drying out. The towelettes are pulled away from the roll through a hole in a sealing and dispensing plate and are pulled out of the top of the container.
    Type: Grant
    Filed: October 12, 1978
    Date of Patent: March 13, 1984
    Assignee: Sterling Drug Inc.
    Inventor: Herman Margulies
  • Patent number: 4432981
    Abstract: 2-Q-6-Q'-8-R-pyrido[2,3-d]pyrimidin-5(8H)-ones (I), where Q is 4(or 3)-hydroxyphenyl, 4(or 3)-methoxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, R' is hydrogen or alkyl having one to four carbon atoms, Q is hydrogen, amino or nitro, and R is alkyl having from one to four carbon atoms, CH(C.sub.2 H.sub.5).sub.2, (CH.sub.2).sub.n .dbd.CHCH.sub.2 where n is 1 or 2, or Y-Z where Y is alkylene having from two to four carbon atoms and having its connecting linkages on different carbon atoms and Z is hydroxy, OR.sub.1 or NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are each methyl or ethyl, or acid-addition salts thereof, and their preparation are shown. Also shown is the cardiotonic use of I where Q is 4(or 3)-hydroxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents and Q' is hydrogen or amino.
    Type: Grant
    Filed: November 5, 1982
    Date of Patent: February 21, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh, Stanley C. Laskowski
  • Patent number: 4431840
    Abstract: Substituted 2-benzoylbenzoic acids, useful as intermediates for preparing valuable chromogenic phthalide compounds, are prepared by reacting certain substituted 3,3-diphenylphthalides with a lower alkanoic acid and water.
    Type: Grant
    Filed: October 22, 1982
    Date of Patent: February 14, 1984
    Assignee: Sterling Drug Inc.
    Inventors: Gordon J. Sterken, Ramamurthi Kannan, James E. Kassner
  • Patent number: 4431651
    Abstract: 3,4-Dihydro-3-R.sub.1 -4-R.sub.2 -5-Q-6-R-2(1H)-pyridinones (I), where R.sub.1 and R.sub.2 are each hydrogen or methyl, R is lower-alkyl, and Q is 4(or 3)-hydroxyphenyl, 4(or 3)-methoxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, or acid-addition salts thereof, and their preparation are shown. Also shown is the cardiotonic use of I where Q is 4(or 3)-hydroxyphenyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents.
    Type: Grant
    Filed: November 18, 1982
    Date of Patent: February 14, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh, Philip M. Carabateas
  • Patent number: 4431819
    Abstract: 3-Heteroaryl-3-(diphenylamino)phthalides useful as color formers in pressure-sensitive carbonless duplicating systems, thermal marking systems and hectographic copying systems are prepared by reacting 2-(heteroarylcarbonyl)benzoic acids with diphenylamines.
    Type: Grant
    Filed: April 28, 1980
    Date of Patent: February 14, 1984
    Assignee: Sterling Drug Inc.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4422955
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula --O--R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: December 4, 1981
    Date of Patent: December 27, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4423046
    Abstract: 1-Methyl-5-nitro-2-(2-phenylvinyl)imidazoles, having useful antibacterial and antiprotozoal activities, are prepared by chemical transformations of the cyano functional group in a corresponding 1-methyl-5-nitro-2-[2-(cyanophenyl)vinyl]imidazole.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: December 27, 1983
    Assignee: Sterling Drug Inc.
    Inventor: John A. Carlson
  • Patent number: 4420617
    Abstract: 5-PY-6-Q-pyridin-2-amines (I) or pharmaceutically acceptable acid-addition salts thereof are useful cardiotonics, where Q is hydrogen or lower-alkyl, and PY is 4-pyridinyl or 4-pyridinyl having one or two lower-alkyl substituents. Their preparation from the corresponding 5-PY-6-Q-2(1H-pyridinones via the corresponding 2-halo-5-PY-6-Q-pyridines is shown.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: December 13, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
  • Patent number: 4420484
    Abstract: Basic amino or ammonium antimicrobial agent (especially bisbiguanide, quaternary ammonium salt and bispyridine)-polyethylene glycol ester surfactant-betaine and/or amine oxide surfactant antimicrobial skin cleansing compositions and method of use thereof are disclosed.
    Type: Grant
    Filed: November 12, 1981
    Date of Patent: December 13, 1983
    Assignee: Sterling Drug Inc.
    Inventors: William G. Gorman, Karl F. Popp
  • Patent number: 4417052
    Abstract: N-{2, 3- and 4-[R.sub.1 -(phenyl)-C(.dbd.X)]-phenyl-loweralkyl} amines, useful as anti-inflammatory agents, are prepared either by reduction of 2-, 3- or 4-[R.sub.1 -(phenyl)CO]-phenyl-lower-alkanoylamines, which are also useful as anti-inflammatory agents; by benzoylating a phenyl-loweralkylamine; by reaction of a 2-, 3- or 4-lithiophenyl-loweralkylamine with a R.sub.1 -(phenyl)-carboxaldehyde, a R.sub.1 -(phenyl)-lower-alkyl ketone or a R.sub.1 -(phenyl)-carbonitrile; by reaction of a 2-, 3- or 4-[R.sub.1 -(phenyl)-CO]-phenyl-lower-alkyl tosylate with an appropriate amine; or by transformations involving manipulations of a carbonyl or carbinol group.
    Type: Grant
    Filed: August 10, 1981
    Date of Patent: November 22, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Bernard L. Zenitz
  • Patent number: 4417059
    Abstract: This invention relates to 3,7-bis(disubstituted aminophenyl- or indolyl)-3,7-bis(diphenylamino)pyromellitides, 3,5-bis(disubstituted aminophenyl- or indolyl)-3,5-bis(diphenylamino)pyromellitides and mixtures thereof useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared by the interaction of 2,5-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,4-benzenedicarboxylic acids or 2,4-bis(disubstituted aminophenyl- or indolyl)carbonyl-1,5-benzenedicarboxylic acids and mixtures thereof with diphenylamines.
    Type: Grant
    Filed: August 19, 1981
    Date of Patent: November 22, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4417054
    Abstract: One aspect of the invention resides in the three step process for preparing cardiotonically active 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles (III, Q is CN) or 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinamides (III, Q is CONH.sub.2) which comprises reacting a pyridinylmethyl lower-alkyl ketone (I) with tri-(lower-alkyl) orthoformate, acetic anhydride and acetic acid to produce 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone (II), reacting II with cyanoacetamide or malonamide in the presence of a basic condensing agent and neutralizing the reaction mixture, where pyridinyl is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents. Other aspects of the invention resides in the intermediate 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones (II) and its two step conversion, as described above, to said compounds (III, Q is CN or CONH.sub.2).
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: November 22, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Karl O. Gelotte
  • Patent number: 4415547
    Abstract: A sustained-release pharmaceutical tablet consisting essentially of drug pellets encapsulated with a water-soluble film-forming substance and a water-insoluble film-forming substance and blended and compressed into tablet form with a compressible tableting mixture and a process for preparation thereof are disclosed.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: November 15, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Andrew B. C. Yu, Phillip M. John
  • Patent number: 4415580
    Abstract: 1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (I, Q is hydrogen, hydroxy, amino, cyano or carbamyl) and/or intermediates therefor (I, Q is carboxy, aminocarbamyl, hydrogen, amino, cyano or carbamyl). Also shown are 3-Q"-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where R and R' are as above and Q' is hydrogen or cyano, which are useful as cardiotonics (II, Q' is hydrogen) and/or intermediates (II, Q' is cyano or hydrogen). Processes for preparing the compounds of formulas I and II are shown.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: November 15, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4415578
    Abstract: 3-Methyl-4-(4-pyridinyl)benzeneamines, useful as cardiotonic agents, are prepared by reaction of pyridine, benzoyl chloride and an appropriate 3-methyl-N,N-di-lower-alkylbenzeneamine in the presence of copper powder and decomposing the reaction mixture with alkali and, if desired, reacting a resulting 3-methyl-4-(4-pyridinyl)-N,N-di-lower-alkylbenzeneamine with hydrogen bromide and pyridine to obtain 3-methyl-4-(4-pyridinyl)benzeneamine.
    Type: Grant
    Filed: February 8, 1982
    Date of Patent: November 15, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4414399
    Abstract: Dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'-6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans, esterified dialkylamino-substituted 2-anilino-5'/6'-carboxyfluorans, 2-amino and substituted amino-5'/6'-carboxyfluorans, 1,3-dialkyl-5'/6'-carboxyfluorans and 3,3-(corresponding-substituted-diaryl)-5/6-carboxyphthalides useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoic acids and substituted diphenylamines to produce the phthalides which are then subjected to ring closure to produce the carboxyfluorans and by the interaction of 4/5-carboxy-2-(4-dialkylamino-substituted-2-hydroxybenzoyl)benzoid acids and substituted 4-hydroxyacetanilides or alkyl phenols which are esterified with alkyl halides or dialkyl sulfates.
    Type: Grant
    Filed: April 15, 1983
    Date of Patent: November 8, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4413127
    Abstract: The invention resides in a process for preparing cardiotonically active 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles (III) which comprises reacting a pyridinylmethyl lower-alkyl ketone (I) with tri-(lower-alkyl) orthoformate, acetic anhydride and acetic acid to produce 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone (II) and then reacting II with malononitrile in a lower-alkanol, where pyridinyl is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: November 1, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Baldev Singh
  • Patent number: 4412950
    Abstract: This invention relates to novel (N-substituted sulfonamido) monoazo and disazo compounds, to acid-addition salts of said azo compounds which are useful as direct dyes particularly in the dyeing of cellulose, to novel (N-substituted sulfonamido) substituted nitrobenzene, aniline and acetanilide intermediates to said azo compounds and to methods of preparation of said azo compounds and said intermediates to said azo compounds.
    Type: Grant
    Filed: March 24, 1982
    Date of Patent: November 1, 1983
    Assignee: Sterling Drug Inc.
    Inventor: Nathan N. Crounse
  • Patent number: 4412995
    Abstract: Compounds of the formula ##STR1## where R is hydrogen, methyl, ethyl, propyl, 2-propenyl or 2-propynyl; and R' is hydrogen or fluoro possess anti-inflammatory activity. The compounds where R is H are prepared by reacting a compound of the formula ##STR2## with (1H,3H)-pyrimidine-2,4,5,6-tetrone. The compounds where R is other than hydrogen are prepared by reacting a compound where R is hydrogen with the appropriate alkylating agent.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: November 1, 1983
    Assignee: Sterling Drug Inc.
    Inventors: Malcolm R. Bell, John L. Herrmann, Jr.
  • Patent number: 4412077
    Abstract: 4-R.sub.2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R.sub.2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III, Q is CN) or corresponding 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R.sub.2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.
    Type: Grant
    Filed: March 15, 1982
    Date of Patent: October 25, 1983
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh