Patents Represented by Attorney B. Woodrow Wyatt
  • Patent number: 4504482
    Abstract: N-R-N'-R'-N-[4(or 5)-PY-2-pyrimidinyl]ureas (I) or salts thereof, where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R' is hydrogen or methyl and R is methyl or ethyl when PY is attached to the 4-position of the pyrimidine ring or R is hydrogen, ethyl or n-butyl when PY is attached to the 5-position of the pyrimidine ring are useful as cardiotonic agents. The preparations of I and their cardiotonic use are shown.
    Type: Grant
    Filed: July 28, 1983
    Date of Patent: March 12, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4503228
    Abstract: 8-Q-2-PY-9H-purin-6-amines (II), salts thereof, their preparation via 2-PY-4,5,6-pyrimidinetriamine and cardiotonic use are shown, where PY is 4-pyridinyl or 4-pyridinyl having one or two lower-alkyl substituents, and Q is methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, methylthio and ethylthio. Also shown as intermediates for the compounds where Q is methylthio or ethylthio are the corresponding 6-amino-2-PY-9H-purin-8-thiols.
    Type: Grant
    Filed: May 21, 1984
    Date of Patent: March 5, 1985
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4502891
    Abstract: Alkaline paint stripper compositions contain either a fibrous material or a combination of a xanthan gum and hectorite clay so as to provide a pellable skin over a painted surface.
    Type: Grant
    Filed: October 6, 1983
    Date of Patent: March 5, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Peter Brocklehurst, Angus S. Ferguson
  • Patent number: 4499091
    Abstract: Novel 1-R-1,4-dihydro-4-oxo-6-fluoro-7-(Z.dbd.N--)-quinolinecarboxylic acids and esters thereof, where R is amino, lower-alkylamino, 2-propenylamino or di-lower-alkylamino, R" is hydrogen or lower-alkyl, and Z.dbd.N is a heterocyclic group, useful as antibacterial agents, are prepared by reacting the corresponding 7-chloroquinoline derivatives with the appropriate heterocyclic compound, Z.dbd.NH. A preferred group of compounds are those where Z.dbd.N is 1-piperazinyl or 4-lower-alkyl-1-piperazinyl.
    Type: Grant
    Filed: February 14, 1983
    Date of Patent: February 12, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Mark P. Wentland, Denis M. Bailey
  • Patent number: 4496590
    Abstract: Novel hydroxyphenylaminobenzenealkanols, useful as antiasthmatic agents, 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 Y is C.sub.n H.sub.2n wherein n is 1-2. The compounds are prepared by de-etherification of the corresponding phenol alkyl or benzyl ethers; by reduction of the corresponding benzoic acids or esters thereof; or by reduction of ketones wherein --Y--OH is replaced by --COCH.sub.3.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: January 29, 1985
    Assignee: Sterling Drug Inc.
    Inventors: Donald C. Schlegel, Malcolm R. Bell
  • Patent number: 4494989
    Abstract: Mono and bis substituted (arylsulfonyl)alkanes useful as color formers, particularly in carbonless duplicating and thermal marking systems, are prepared by the interaction of the appropriate aldehyde or dialdehyde with the appropriate aryl or heterocyclic moiety and the appropriate phenylsulfinic acid in the presence of a catalyst.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: January 22, 1985
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4495353
    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: June 13, 1983
    Date of Patent: January 22, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4486431
    Abstract: 4,5-Dihydro-4-R-6-(4-pyridinyl)-3(2H)-pyridazinone (IA) or pharmaceutically-acceptable acid-addition salt thereof, where R is hydrogen or methyl, is shown as the active component in cardiotonic composition and method for increasing cardiac contractility in a patient requiring such treatment. Also shown is the preparation of IA by reacting a lower-alkyl 2-R-4-(BN)-4-cyano-4-(4-pyridinyl)butanoate with hydrazine, where R is hydrogen or methyl, and BN is 4-morpholinyl, 1-piperidinyl or 1-pyrrolidinyl.
    Type: Grant
    Filed: March 18, 1981
    Date of Patent: December 4, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, William B. Dickinson
  • Patent number: 4485242
    Abstract: 3-[(Alkoxy)(aryl or heteroaryl)methyl]-1H-indoles which are useful as color formers in pressure-sensitive carbonless duplicating systems and thermal marking systems are prepared by reacting 3-[(arylsulfonyl)(aryl or heteroaryl)methyl]-1H-indoles with alcohols in the presence of a base.
    Type: Grant
    Filed: July 30, 1981
    Date of Patent: November 27, 1984
    Assignee: Sterling Drug Inc.
    Inventors: Paul J. Schmidt, William M. Hung
  • Patent number: 4482495
    Abstract: N-acetyl-para-aminophenyl N'-acetylaminothioalkanoates I are new analgesic compounds with greatly reduced hepatotoxic effects, when taken in overdose, relative to N-acetyl-para-aminophenol. They are prepared by reacting an N-acetylaminothioalkanoic acid IV with a reactive organic chloride V to form a mixed anhydride II and then reacting the latter with N-acetyl-para-aminophenol. The mixed anhydrides II are new and useful intermediates. Alternatively the derivatives I may be prepared by reacting the acid IV with bis-(4-nitrophenyl) sulfite to form a para-nitrophenyl N-acetylaminothioalkanoic acid ester VIII, reducing the latter to a para-aminophenyl N-acetylaminothioalkanoate VII, and acetylating this product. The esters VII and VIII are new and useful intermediates. Both reactions may pass through S-blocked intermediates, which are also new. Pharmaceutical compositions containing the derivatives I are disclosed, and also analgesic methods using them.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: November 13, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Margetts, Roderic S. Andrews, Jean Legros
  • Patent number: 4477676
    Abstract: Mono-, bis- and tris-indolyl-substituted furanones useful as color formers, particularly in carbonless duplicating and thermal marking systems, which are prepared respectively by: the interaction of an indole with mucochloric acid; the interaction of an indole with a 4-mono(indolyl)-substituted 4-oxo-2-butenoic acid; and by the interaction of an indole with a 2,4-bis(indolyl)-substituted 4-oxobutanoic acid or with a 3,5-bis(indolyl)-substituted furanone.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: October 16, 1984
    Assignee: The Hilton-Davis Chemical Co.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4474121
    Abstract: A method for controlling two-stage combustion furnaces having a first stage operated with sub-stoichiometric airflow and a second stage operated with excess air, whereby the first stage airflow is controlled such that the ratio of first stage airflow to total airflow is maintained less than ##EQU1## where N lies between zero and unity.
    Type: Grant
    Filed: December 21, 1981
    Date of Patent: October 2, 1984
    Assignee: Sterling Drug Inc.
    Inventor: Frederick M. Lewis
  • Patent number: 4473571
    Abstract: 8-Q-2-PY-9H-purin-6-amines (II), salts thereof, their preparation and cardiotonic use are shown, where PY is 4-pyridinyl or 4-pyridinyl having one or two lower-alkyl substituents, and Q is methyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, methylthio and ethylthio. Also shown as intermediates for the compounds where Q is methylthio or ethylthio are the corresponding 6-amino-2-PY-9H-purin-8-thiols.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: September 25, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4472305
    Abstract: N-Terminal L-prolyl or D-prolyl hexapeptide amides useful as Substance P agonists and/or antagonists and as analgesics and/or antihypertensives and a process for preparing them are disclosed.
    Type: Grant
    Filed: May 17, 1983
    Date of Patent: September 18, 1984
    Assignee: Sterling Drug Inc.
    Inventors: Philip E. Hansen, Barry A. Morgan
  • Patent number: 4469699
    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: August 25, 1982
    Date of Patent: September 4, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Baldev Singh
  • Patent number: 4469871
    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 or 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)nicotinamides which comprises reacting a pyridinylmethyl lower-alkyl ketone with tri-(lower-alkyl) orthoformate, acetic anhydride and acetic acid to produce 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketone reacting the latter 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 reside in the intermediate 2-(lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones, their salts and their two step conversion, as described above, to 1,2-dihydro-6-(lower-alkyl)-2-oxo-5-(pyridinyl)-nicotinonitriles or corresponding nicotinamides.
    Type: Grant
    Filed: March 3, 1983
    Date of Patent: September 4, 1984
    Assignee: Sterling Drug Inc.
    Inventor: Karl O. Gelotte
  • Patent number: 4465686
    Abstract: Disclosed and claimed is the cardiotonic use of 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (II), where R.sub.1 is hydrogen, lower-alkyl or lower-hydroxyalkyl, R is lower-alkyl or hydrogen, and, R' and R" are each hydrogen, amino or hydroxy, at least one of R' or R" being other than hydrogen, or where R' is nitro when R" is hydroxy, or pharmaceutically acceptable acid-addition salts thereof where at least one of R' and R" is amino. Also disclosed and claimed are 1-R.sub.1 -5-(3-R'-4-R"-phenyl)-6-R-2(1H)-pyridinones (I), where R.sub.1, R' and R" are defined as above and R is lower-alkyl and acid-addition salts thereof where at least one of R' and R" is amino. Also shown and claimed is the process which comprises reacting 1-R.sub.1 -1,2-dihydro-2-oxo-5-(3-R'-4-R"-phenyl)-6-R-nicotinonitrile, where R.sub.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: August 14, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Chester J. Opalka, Jr., Donald F. Page, Ruthann M. McGarry
  • Patent number: 4463008
    Abstract: 2-(R.sub.1 O)-3-Q-5-PY-6-R-pyridine (I) or pharmaceutically acceptable acid-addition salts thereof are useful cardiotonics, where R.sub.1 is methyl or ethyl, R is hydrogen or lower-alkyl, PY is 4(or 3)-pyridinyl or 4(or 3)-pyridinyl having one or two lower-alkyl substituents, and Q is hydrogen, chloro or COOR' where R' is lower-alkyl, or Q is cyano only when R is hydrogen. The preparation of I and their cardiotonic use are shown.
    Type: Grant
    Filed: November 10, 1982
    Date of Patent: July 31, 1984
    Assignee: Sterling Drug Inc.
    Inventors: George Y. Lesher, Chester J. Opalka, Jr., Baldev Singh
  • Patent number: 4461743
    Abstract: An apparatus for injecting a mixture of pure oxygen or oxygen-enriched air (at least 25 percent oxygen) and purge water into a wet oxidation reactor operating at elevated temperature and pressure. An annular space between the oxygen carrying pipe and a second, larger pipe is filled with heat transfer resisting material, either maintained static or passed through the annular space to remove heat therefrom. The temperature of the oxygen and purge water is maintained at less than 250.degree. F., preferably less than 150.degree. F. to minimize evaporation of the purge water. Thus, backflow of organic matter into the oxygen pipe is prevented; plugging of the oxygen pipe by salts is also prevented.
    Type: Grant
    Filed: February 8, 1982
    Date of Patent: July 24, 1984
    Assignee: Sterling Drug Inc.
    Inventors: Ajit K. Chowdhury, Gerald L. Bauer, Richard W. Lehmann
  • Patent number: 4454120
    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-Q-NR.sub.4 R.sub.5 wherein Q is Met, Met(O), Gln or Ser, R.sub.1 and R.sub.2 are each hydrogen or alkyl, R.sub.4 is phenylalkyl or substituted-phenylalkyl and R.sub.5 is hydrogen, alkyl, phenylalkyl, substituted-phenylalkyl or X-alkyl wherein X is an electronegative group 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: June 12, 1984
    Assignee: Sterling Drug Inc.
    Inventor: Barry A. Morgan