Patents Represented by Attorney B. Woodrow Wyatt
  • Patent number: 4595762
    Abstract: 3-Q-4-R.sub.2 -5-(2-Q'-5-R.sub.3 -4-thiazolyl)-6-R.sub.1 -2(1H)-pyridinones (I), where R.sub.1 is alkyl having from one to four carbon atoms, R.sub.2 is hydrogen or methyl, R.sub.3 is hydrogen or alkyl having from one to three carbon atoms, Q is amino, carbamyl, carboxy, cyano or hydrogen, and Q' is alkyl having from one to four carbon atoms, amino or R.sub.4 NH where R.sub.4 is alkyl having from one to four carbon atoms, or acid-addition salts thereof where at least one of Q and Q' is amino or Q' is R.sub.4 NH, are useful as cardiotonics (I where Q is amino, cyano or hydrogen) and/or as intermediates (I where Q is cyano, carbamyl or carboxy). Also shown as intermediates are 1,2-dihydro-4-R.sub.2 -5-[R.sub.3 CH(Br)CO]-6-R.sub.1 -2-oxo-3-pyridinecarbonitriles (II), and, also, processes for preparing I and II.
    Type: Grant
    Filed: February 13, 1985
    Date of Patent: June 17, 1986
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4590194
    Abstract: 3-(NB)-4-Q-6-PY-pyridazines (I) or salts thereof, which are useful as cardiotonics, are prepared by reacting a 3-halo-4-Q-6-PY-pyridazine with an amine, H-NB, to produce I, where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents and Q is cyano when NB is NHCH.sub.3 or N(CH.sub.3).sub.2, or Q is carbamyl when NB is NHCH.sub.3, or Q is hydrogen when NB is N(CH.sub.3).sub.2. Cardiotonic use of said 3-(NB)-4-Q-6-PY-pyridazines or salts is shown.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: May 20, 1986
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, William B. Dickinson
  • Patent number: 4590183
    Abstract: The method of providing cytoprotection of the gastric mucosa in a mammal receiving aspirin perorally which comprises orally administering either prior to or in combination with aspirin a cytoprotectively effective amount of sodium thiosulfate alone or in combination with a pharmaceutically acceptable carrier. Also shown is a composition for providing cytoprotection of the gastric mucosa in a mammal receiving aspirin perorally which comprises aspirin in combination with a cytoprotectively effective amount of sodium thiosulfate.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: May 20, 1986
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4585764
    Abstract: The method of providing cytoprotection of the gastric mucosa in a mammal receiving aspirin (ASA) perorally which comprises orally administering either prior to or in combination with ASA a cytoprotectively effective amount of 3,3'-thiobis[propanoic acid] (TBPA) or in combination with a pharmaceutically acceptable carrier. Also shown is a composition for providing cytoprotection of the gastric mucosa in a mammal receiving ASA perorally which comprises ASA in combination with a cytoprotectively effective amount of TBPA.
    Type: Grant
    Filed: April 22, 1985
    Date of Patent: April 29, 1986
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4585445
    Abstract: Hypodermic syringe holders for use in combination with disposable medicament-containing ampoules are adapted to immobilize the ampoules within the syringe holder so as to provide manual aspirating capability.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: April 29, 1986
    Assignee: Sterling Drug Inc.
    Inventor: Frederick B. Hadtke
  • Patent number: 4581354
    Abstract: 3-Arylcarbonyl- and 3-cycloalkylcarbonyl-1-aminoalkyl-1H-indoles, useful as analgesic, anti-rheumatic and anti-inflammatory agents, are prepared by reacting a 3-arylcarbonyl- or 3-cycloalkylcarbonylindole with an aminoalkyl halide in the presence of an acid-acceptor; by reacting a 1-aminoalkyl-1H-indole with an arylcarboxylic acid halide or a cycloalkanecarboxylic acid halide in the presence of a Lewis acid; or by reacting a 3-arylcarbonyl- or 3-cycloalkanecarbonyl-1-tosyloxyalky- or haloalkyl-1H-indole with an amine.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: April 8, 1986
    Assignee: Sterling Drug Inc.
    Inventor: Malcolm R. Bell
  • Patent number: 4576729
    Abstract: Stable liquid disinfectant laundry detergent compositions, having germicidal, cleaning, fabric brightening and anti-soil redeposition properties, contain a non-ionic surfactant, a cryptoanionic surfactant and a quaternary ammonium germicide and, optionally, minor amounts of other non-essential ingredients.
    Type: Grant
    Filed: July 24, 1984
    Date of Patent: March 18, 1986
    Assignee: Sterling Drug Inc.
    Inventors: Leon E. Paszek, Barbara Gebbia
  • Patent number: 4570171
    Abstract: 5-[N-(RCO)-N-R.sup.1 -amino] or (RCOO)-9-(N-R.sup.2 -N-R.sup.3 -amino)-12-(RCO)benzo[a]phenoxazines useful as color formers, particularly in electrochromic recording systems, are prepared by the interaction of the corresponding 5-(N-R.sup.1 -amino)-9-(N-R.sup.2 -N-R.sup.3 -amino)benzo[a]phenoxazinium halide or 9-(N-R.sup.2 -N-R.sup.3 -amino)benzo[a]phenoxazin-5-one with a reducing agent to obtain the corresponding leuco compound and subsequently interacting the leuco compound with at least two molecular proportions of an acylating agent.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: February 11, 1986
    Assignee: The Hilton-Davis Chemical Co.
    Inventor: William M. Hung
  • Patent number: 4567186
    Abstract: 3-Z-5-Q-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where Z is hydrogen or cyano, and Q is 2(or 3)-furanyl, 2(or 3)-thienyl, 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two methyl substituents, are useful as cardiotonic agents and corresponding compounds where Z is carboxy are useful as intermediates. Also shown as intermediates are 5-(Q-CO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Q is defined as above. Processes for preparing said compounds (I and II) are shown.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: January 28, 1986
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4565308
    Abstract: This invention relates to powder dispensers of the squeeze bottle type which are so constructed that a small child would be unable to manipulate the dispensing action and would thus be protected from ingestion or inhalation of the dispenser contents.
    Type: Grant
    Filed: September 1, 1983
    Date of Patent: January 21, 1986
    Assignee: Sterling Drug Inc.
    Inventor: Edward J. Yuhl, Jr.
  • Patent number: 4562024
    Abstract: An improved wet granulation process for preparing compressed tablets, particularly those containing a poorly compressible medicament, e.g., paracetamol and derivatives thereof, the improvement which comprises homogenizing part only of particulate solid material including active matter and tabletting aids with at least 90% by weight of a predetermined quantity of granulating fluid, so as to form a substantially homogenous slurry wherein the percentage of weight of solids, both dissolved and undissolved, in the slurry is at least about 25% w/w; and then moistening the remaining part of the particulate solid material in the manner of wet granulation but with the slurry resultant from above (and thereafter with the balance of the granulating fluid, if any) so as thus to form a desired substantially uniform, moist, coherent, non-pasty mass ready for granulation. Said mass is then granulated and dried, and the dried granules compressed and compacted into tablets.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: December 31, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Alan G. Rogerson
  • Patent number: 4560746
    Abstract: The disodium salt of 1-[(6-methoxy-4-sulfo-3-methylphenyl)azo]-2-naphthol-6-sulfonic acid (FD and C Red 40), the disodium salt of 1-[(4-sulfophenyl)azo]-2-naphthol-6-sulfonic acid (FD and C Yellow 6), the trisodium salt of 1-[1-(4-sulfonaphthyl)azo]-2-naphthol-3,6-disulfonic acid (FD and C Red 2), the disodium salt of 2-[1-(4-sulfonaphthyl)azo]-1-naphthol-4-sulfonic acid (Carmoisine) and the sodium salt of 2-(2-quinolyl)-1,3-indanedione-sulfonic acid (D and C Yellow 10) are prepared and purified in high yield and in a high state of purity by subjecting their aqueous reaction mixtures to ultrafiltration through a membrane of such structure and under such conditions that the impurities are separated from the reaction mixtures, and the products are concentrated in high purity concentrates from which the products can be isolated directly by evaporation of the solvent.
    Type: Grant
    Filed: November 30, 1984
    Date of Patent: December 24, 1985
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Robert W. J. Rebhahn, Wayne L. Cook
  • Patent number: 4560753
    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: October 12, 1983
    Date of Patent: December 24, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh, Stanley C. Laskowski
  • Patent number: 4561001
    Abstract: 3-(N-R.sup.2 -N-Acylamino)-7-(N-R.sup.3 -N-R.sup.4 -amino)-10-acylphenothiazines and phenoxazines useful as color formers, particularly in electrochromic recording systems, are prepared by the interaction of the corresponding 3-(N-R.sup.2 -amino)-7-(N-R.sup.3 -N-R.sup.4 -amino)phenothiazinium or phenoxazinium halide with a reducing agent to obtain the corresponding leuco compound and subsequently interacting the leuco compound with at least two molecular proportions of an acylating agent.
    Type: Grant
    Filed: July 31, 1984
    Date of Patent: December 24, 1985
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Michael B. Gunn, William M. Hung
  • Patent number: 4560691
    Abstract: 1-R-5-Ar-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is hydrogen or methyl, and Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, hydroxy, amino, acetylamino, methanesulfonylamino, bromo, chloro, fluoro, cyano or carbamyl are useful as cardiotonic agents and corresponding compounds where Ar is nitrophenyl are useful as intermediates. Also shown as intermediates, are 5-(Ar--CO)-6-[2-(di-lower-alkylamino)-ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, cyano or nitro and 5-(Ar--CO)-6-methyl-2(1H)-pyridinones (III) where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, hydroxy, cyano or nitro; said compounds (III) where Ar is phenyl or hydroxyphenyl also are useful as cardiotonic agents. Processes for preparing the compounds of formulas I, II and III are shown.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: December 24, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4559352
    Abstract: 1-R.sub.1 -3-amino-5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones or salts thereof, which are useful as cardiotonics, where R.sub.1 is hydrogen, lower-alkyl, or lower-hydroxyalkyl, R is hydrogen or lower-alkyl, and, R' and R" are each hydrogen, hydroxy or amino at least one of R' or R" being other than hydrogen, are prepared by reacting the corresponding 3-carbamyl compound with a reagent capable of converting carbamyl to amino or by first reacting the corresponding 3-carbamyl compound where R' and R" are each hydrogen, nitro or lower-alkoxy at least one of R' and R" being other than hydrogen with a reagent capable of converting carbamyl to amino and then reacting the resulting 3-amino compound where R' and/or R" are/is lower-alkoxy and/or nitro with a reagent capable of converting lower-alkoxy to hydroxy and/or with a reagent capable of converting nitro to amino. Preparation of the corresponding 3-carbamyl and 3-cyano compounds is shown, the latter including cardiotonically active novel 1-R.sub.
    Type: Grant
    Filed: July 30, 1984
    Date of Patent: December 17, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
  • Patent number: 4559347
    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: October 11, 1984
    Date of Patent: December 17, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4559151
    Abstract: Antistatic and fabric softener compositions for application to textile fabrics comprises a combination of an N,N-dialkyl-N,N-di-lower-alkyl quaternary ammonium salt either alone or in combination with an N-long-chain alkylamido-lower-alkyl-N,N-di-lower-alkyl-N-R.sub.4 '-quaternary ammonium salt and critical amounts of a lactic acid salt and the method of use of such compositions for treating textile fabrics.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: December 17, 1985
    Assignee: Sterling Drug Inc.
    Inventors: David Pregozen, John J. Hiller, Jr.
  • Patent number: 4557898
    Abstract: Aqueous acidic disinfecting and sterilizing compositions containing hydrogen peroxide, a surfactant and an aqueous alcoholic mixture of a tertiary amine and a fatty acid alkanolamide are non-irritating, have in-use stability and are effective for cold and warm sterilization.
    Type: Grant
    Filed: February 22, 1985
    Date of Patent: December 10, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Donald F. Greene, Virginia L. Urban
  • Patent number: 4550855
    Abstract: This invention relates to compact, easily transportable, moist tissue or towelette dispensers which are so designed that they maintain the tissues contained within the dispenser in moist condition for exceptionally long periods of time, thus providing long shelf life for merchants, who stock the dispensers, as well as a long life span of the dispensers for the consumer.
    Type: Grant
    Filed: September 14, 1983
    Date of Patent: November 5, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Thomas S. Harrison