Patents Assigned to Sterling Drug Inc.
  • Patent number: 4540705
    Abstract: 2-(2-Naphthalenyl)alkyl-4,5-dihydro-1H-imidazoles and -tetrahydropyrimidines, the corresponding 3,4-dihydronaphthalenyl and 1,2,3,4-tetrahydronaphthalenyl compounds; and the corresponding indene and indane derivatives, useful as antidepressant or diuretic agents, are prepared by reacting the appropriate 2-(cyanoalkyl)naphthalene or -indane derivative (or the corresponding ester or imino-ether) with an alkylenediamine.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: September 10, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4539327
    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: January 16, 1984
    Date of Patent: September 3, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4539429
    Abstract: Novel lower-alkyl 2-(hydroxyphenylamino)phenyl ketones, useful as inhibitors of lipoxygenase activity, are of the formula ##STR1## wherein R is hydrogen, lower-alkyl, lower-alkoxy or halo; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and Alk is lower-alkyl. The compounds are prepared by de-etherification of the corresponding alkyl or benzyl ethers which are in turn prepared by reacting a 2-(alkoxy- or benzyloxyphenylamino)benzoic acid with an alkyllithium.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: September 3, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4533657
    Abstract: A genus of dipeptide amides including as the preferred subgenus the dipeptide amides having the structural formula HTyrD-AlaNR.sub.2 R.sub.3 wherein R.sub.2 is phenylalkyl or substituted-phenylalkyl and R.sub.3 is hydrogen, alkyl, phenylalkyl, substituted-phenylalkyl or X-alkyl wherein X is an electronegative moiety are prepared by condensing the dipeptide with the amine or the amino acid with the amino acid amide and are useful as analgesics.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: August 6, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Barry A. Morgan
  • Patent number: 4533655
    Abstract: A genus of dipeptide amides including as the preferred subgenus the dipeptide amides having the structural formula R.sub.1 TyrR.sub.2 D-AlaNHR.sub.4 wherein R.sub.1 and R.sub.2 are each hydrogen or alkyl provided that at least one of them is other than hydrogen and R.sub.4 is phenylalkyl or substituted-phenylalkyl are prepared by condensing the dipeptide with the amine or the amino acid with the amino acid amide and are useful as analgesics.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: August 6, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Barry A. Morgan
  • Patent number: 4532066
    Abstract: A stable mildly acidic aqueous polishing cleanser for removing stains from hard surfaces comprising by weight from about 8 to 20% of a polishing agent having an average particle size of about 2 to 10 microns and a particle size distribution from about 1 to 40 microns, from about 1 to 5% of a nonionic surfactant, from about 1 to 2.25% of a thickening agent comprising smectite clay and xanthan gum in a ratio of about 2:1 respectively, from about 1.25 to 6.25% of an oxalate salt selected from ammonium bioxalate or a mixture of ammonium bioxalate and ammonium oxalate, and from about 68 to 89% of water, said cleanser having a pH of about 3.0 to 4.5. Preparation of the cleanser and its properties are given.
    Type: Grant
    Filed: March 5, 1984
    Date of Patent: July 30, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Leon E. Paszek, Ernest Bernarducci
  • Patent number: 4532247
    Abstract: 4-R'-5-Q-1,6-naphthyridin-2(1H)-ones (I), where R' is hydrogen or methyl and Q is hydroxymethyl, 1-hydroxyethyl alkanoyloxymethyl or 1-alkanoyloxyethyl, are produced by first reacting 4-R'-5-acetyl(or n-propanoyl)-6-[2-(di-lower-alkylamino]-2(1H)-pyridinone [III] with hydroxylamine or salt thereof to produce 4-R'-5-Q'-1,6-naphthyridin-2(1H)-one-6-oxide (II), where R' is defined as above and Q' is methyl or ethyl; next reacting II with an alkanoic anhydride to produce I where Q is alkanoyloxymethyl or 1-alkanoyloxyethyl; and, then hydrolyzing said alkanoyloxymethyl or -ethyl compound to produce I where Q is hydroxymethyl or 1-hydroxyethyl. Also shown is the cardiotonic use of II and I where Q is hydroxymethyl, 1-hydroxyethyl or alkanoyloxymethyl.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: July 30, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4526291
    Abstract: A flexible bag is adapted to contain articles to be dispensed, and the bag has a closed first end and open second end. A collar is fixed to the open second end of the bag. A top has therein a dispensing opening and a slit connected with the dispensing opening. The top is selectively movable between a first position fitted to the collar and a second position removed from the collar. A lid is selectively movable between a first position covering at least a portion of the top and a second position removed from the top. The lid includes a first portion adapted to cover the dispensing opening when the lid is in the first position thereof and a second portion adapted to cover the slit when the lid is in the first position thereof.
    Type: Grant
    Filed: May 16, 1983
    Date of Patent: July 2, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Herman Margulies
  • Patent number: 4523679
    Abstract: This invention provides medical procedure packages comprising a pre-sterilized kit within an outer package wrap, the packages being so designed that all components of the package are sterilized using sterilization methods which are compatible with the chemical compositions of the components and their stability to such sterilization methods, and wherein the internal sterility of the package is maintained from final package sealing until the package is delivered to a sterile operating room environment.
    Type: Grant
    Filed: March 5, 1984
    Date of Patent: June 18, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Myron Paikoff, Robert W. Hain, Frederick B. Hadtke
  • Patent number: 4524149
    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: February 7, 1983
    Date of Patent: June 18, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4522302
    Abstract: This invention provides medical procedure packages comprising a pre-sterilized kit within an outer package wrap, the package being so designed that all components of the package are sterilized using sterilization methods which are compatible with the chemical compositions of the components and their stability to such sterilization methods, and wherein the internal sterility of the package is maintained from final package sealing until the package is delivered to a sterile operating room environment.
    Type: Grant
    Filed: March 5, 1984
    Date of Patent: June 11, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Myron Paikoff
  • Patent number: 4518585
    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: November 20, 1979
    Date of Patent: May 21, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Donald F. Greene, Virginia L. Urban
  • Patent number: 4517192
    Abstract: 3-Q-5-[4-(R'-X)phenyl]-6-R-2(1H)-pyridinones (I), where R and R' are each methyl or ethyl, X is sulfinyl when Q is hydrogen or cyano, or X is sulfonyl when Q is cyano, their preparation and cardiotonic use are shown. Also shown are intermediates 5-[4-(R'-thio)phenyl]-6-R-2(1H)-pyridinones (II) and also corresponding 3-cyano intermediates.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: May 14, 1985
    Assignee: Sterling Drug Inc.
    Inventor: George Y. Lesher
  • Patent number: 4517191
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or formyl; and R' and R" are hydrogen or lower-alkyl, are useful as antibacterial agents or as intermediates, and are prepared from the corresponding compounds unsubstituted in the 1-position.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: May 14, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Mark P. Wentland, Denis M. Bailey
  • Patent number: 4517190
    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: June 9, 1983
    Date of Patent: May 14, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4515980
    Abstract: Novel lower-alkyl 2-(hydroxyphenylamino)benzoates, useful as inhibitors of lipoxygenase, are of the formula ##STR1## wherein R is hydrogen, lower-alkyl or lower-alkoxy; R' is hydrogen or lower-alkyl; R" is hydrogen, lower-alkyl or halo; and Alk is lower-alkyl. The compounds are prepared by de-etherification of the corresponding alkyl or benzyl ethers.
    Type: Grant
    Filed: July 11, 1983
    Date of Patent: May 7, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Denis M. Bailey
  • Patent number: 4515797
    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: March 5, 1982
    Date of Patent: May 7, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page
  • Patent number: 4513891
    Abstract: A spray dispenser of the squeeze bottle type, for use in the administration of nasal sprays, comprises a squeeze bottle in combination with a spray dispenser head assembly consisting of a cap, and associated spray nozzle which functions as a two-way check valve and a dip tube for conveying liquid from the bottle to the spray nozzle. The head may optionally be fitted with an overcap for protecting the spray head from contamination when not in use.
    Type: Grant
    Filed: April 15, 1982
    Date of Patent: April 30, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Robert W. Hain, Frederick B. Hadtke, Myron Paikoff
  • Patent number: 4512993
    Abstract: Shown are 2-(NB)-4-PY-5-Q-pyrimidines (I) and 2-(NB')-5-PY-4-Q'-pyrimidines (II) or salts thereof, where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, Q and Q' are each hydrogen or methyl, NB is dimethylamino or N-(2-hydroxyethyl)methylamino and NB' is amino, dimethylamino, acetylamino or propionylamino; the preparation thereof; and, their cardiotonic use.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: April 23, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: D280384
    Type: Grant
    Filed: January 12, 1983
    Date of Patent: September 3, 1985
    Assignee: Sterling-Drug, Inc.
    Inventor: Albert C. G. Poore