Patents Represented by Attorney Theodore C. Miller
  • Patent number: 4032527
    Abstract: Substituted 3,3-diphenylphthalides, useful as color precursors, particularly in the art of pressure-sensitive duplicating systems, are prepared by condensing substituted 2-benzoylbenzoic acids with substituted anilines.
    Type: Grant
    Filed: November 27, 1974
    Date of Patent: June 28, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Nathan N. Crounse, Paul J. Schmidt
  • Patent number: 4031246
    Abstract: Aryloxyalkyl diketones and keto-esters, useful as pesticidal and anti-viral agents, are prepared from an aryloxyalkyl halide and an alkali metal enolate salt of a diketone or keto-ester, or from a haloalkyl-diketone and an alkali metal salt of a phenol.
    Type: Grant
    Filed: May 12, 1975
    Date of Patent: June 21, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Joseph C. Collins, Guy D. Diana
  • Patent number: 4022789
    Abstract: 6-X-11-Y-3-(2,2-Dichlorocyclopropyl)methyl-1,2,3,4,5,6-hexahydro-2,6-methan o-3-benzazocin-8-ols wherein X is hydrogen, methyl, ethyl, propyl, allyl or phenyl and Y is hydrogen, methyl or ethyl, are prepared by N-alkylation, N-acylation-reduction or O-demethylation and are useful as strong analgesics and narcotic antagonists.
    Type: Grant
    Filed: November 20, 1975
    Date of Patent: May 10, 1977
    Assignee: Sterling Drug Inc.
    Inventor: Noel F. Albertson
  • Patent number: 4022833
    Abstract: N,N'-Bridged-bis[(O and/or N-substituted)-2-alkyl-2-hydroxyethylamines] of the formula ##STR1## are prepared by condensing an epoxide of the formula ##STR2## and a diamine of the formula R'NH-X-NHR'. The products and dicarbanilates, acid-addition salts, N,N'-dioxides and N,N'-diammonium quaternary salts derived therefrom have antibacterial activity in vitro and are useful as antibacterial agents.
    Type: Grant
    Filed: June 2, 1975
    Date of Patent: May 10, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Guy D. Diana, Royal A. Cutler
  • Patent number: 4022792
    Abstract: 1,2,3,4,4a,5,10,10a-Octahydro-5-(Y.sup.3)-5-(Y.sup.4)-benzo[g]quinolines and 1,2,3,4,4a,9b-hexahydro-5-(Y.sup.3)-5-(Y.sup.4)-5H-indeno[1,2,b]pyridi nes wherein Y.sup.3 and Y.sup.4 are hydrogen, alkyl or phenyl, which are useful as antagonists of strong analgesics, are obtained by cyclizing derivatives of 2-(phenyl or benzyl)-.alpha.-(Y.sup.3)-.alpha.-(Y.sup.4)-3-piperidinemethanols. The latter are obtained from corresponding 3-piperidinecarboxylic acids.
    Type: Grant
    Filed: May 27, 1976
    Date of Patent: May 10, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Noel F. Albertson, William F. Michne
  • Patent number: 4009170
    Abstract: 1-(2-Substituted-hydrazino)-3,4-dihydroisoquinolines, prepared in one process by alkylating the corresponding 3,4-dihydroisocarbostyrils, hydrazinolyzing the resulting 1-alkoxy-3,4-dihydroisoquinolines and condensing the resulting 1-hydrazIno-3,4-dihydroisoquinolines with aldehydes or ketones, and 1,1'-azinobis(1,2,3,4-tetrahydroisoquinolines), prepared by condensing corresponding 1-alkoxy-3,4-dihydroisoquinolines and 1-hydrazino-3,4-dihydroisoquinolines, are useful as antihypertensive agents and/or as antiinflammatory agents.
    Type: Grant
    Filed: August 1, 1972
    Date of Patent: February 22, 1977
    Assignee: Sterling Drug Inc.
    Inventor: Guy D. Diana
  • Patent number: 4009171
    Abstract: 11-Oxygenated-2,6-methano-3-benzazocines N-alkylated by alkylmethyl, haloalkenylmethyl, alkynylmethyl, cycloalkylmethyl, cycloalkenylmethyl, cycloalkyl or 2-cycloalkenyl are prepared directly by N-alkylation of the corresponding N-H intermediates or indirectly by N-acylation of the corresponding N-H intermediates followed by reduction of the resulting N-acylated intermediates and are useful as antagonists of narcotic analgesics.
    Type: Grant
    Filed: February 21, 1974
    Date of Patent: February 22, 1977
    Assignee: Sterling Drug Inc.
    Inventor: Noel F. Albertson
  • Patent number: 4009163
    Abstract: Antibacterial and antifungal mono- and disubstituted amidinoureas and amidinothioureas are obtained by interaction of quanidines and isocyanates or isothiocyanates.
    Type: Grant
    Filed: June 9, 1975
    Date of Patent: February 22, 1977
    Assignee: Sterling Drug Inc.
    Inventors: Royal A. Cutler, Samuel Schalit
  • Patent number: 3988370
    Abstract: Antibacterial and antifungal mono- and disubstituted amidinoureas and amidinothioureas are obtained by interaction of guanidines and isocyanates or isothiocyanates.
    Type: Grant
    Filed: August 24, 1973
    Date of Patent: October 26, 1976
    Assignee: Sterling Drug Inc.
    Inventors: Royal A. Cutler, Samuel Schalit
  • Patent number: 3976653
    Abstract: 1,2,3,4,4a,5,10,10a-octahydro-5-(Y.sup.3)-5-(Y.sup.4)-benzo[g]quinolines and 1,2,3,4,4a,9b-hexahydro-5-(Y.sup.3)-5-(Y.sup.4)-5H-indeno[1,2,b]pyridi nes wherein Y.sup.3 and Y.sup.4 are hydrogen, alkyl or phenyl, which are useful as antagonists of strong analgesics, are obtained by cyclizing derivatives of 2-(phenyl or benzyl)-.alpha.-(Y.sup.3)-.alpha.-(Y.sup.4)-3-piperidinemethanols. The latter are obtained from corresponding 3-piperidinecarboxylic acids.
    Type: Grant
    Filed: December 16, 1974
    Date of Patent: August 24, 1976
    Assignee: Sterling Drug Inc.
    Inventors: Noel F. Albertson, William F. Michne
  • Patent number: 3968114
    Abstract: N-Alkylated-8-aminated-2,6-methano-3-benzazocines, useful as strong analgesics, are prepared by one route comprising reduction of 8-nitro intermediates or by another route comprising Birch type reduction of 8-methoxy intermediates followed by dehydration-rearrangement of the oximes of the resulting 8-oxo intermediates.
    Type: Grant
    Filed: September 20, 1974
    Date of Patent: July 6, 1976
    Assignee: Sterling Drug Inc.
    Inventor: Noel F. Albertson
  • Patent number: 3957793
    Abstract: N-Alkylated-8-aminated-2,6-methano-3-benzazocines, useful as strong analgesics, are prepared by one route comprising reduction of 8-nitro intermediates or by another route comprising Birch type reduction of 8-methoxy intermediates followed by dehydration-rearrangement of the oximes of the resulting 8-oxo intermediates.
    Type: Grant
    Filed: September 20, 1974
    Date of Patent: May 18, 1976
    Assignee: Sterling Drug Inc.
    Inventors: Mark P. Wentland, Noel F. Albertson
  • Patent number: 3940441
    Abstract: Alkylenediamine derivatives substituted on each nitrogen atom by 4-(4'-nitrophenoxy)benzyl or 4-(4'-aminophenoxy)benzyl, optionally substituted additionally on each nitrogen by lower-alkyl, phenylcarbamyl or dihaloacetyl and optionally interrupted in alkylene by cycloalkylene, phenylene, alkylated-phenylene, pyridylene, furylene and thiazolylene. The compounds, which have antibacterial activity, are prepared stepwise by reacting an alkylenediamine with two molar equivalents of 4-(4'-nitrophenoxy)benzaldehyde and reducing the resulting bis(benzal)alkanediamines.
    Type: Grant
    Filed: July 15, 1974
    Date of Patent: February 24, 1976
    Assignee: Sterling Drug Inc.
    Inventor: Alexander R. Surrey
  • Patent number: 3936462
    Abstract: 1,2,3,4,5,6-Hexahydro-1-oxo-3-(hydrocarbon or substituted hydrocarbon)-8-(H or OH)-6-(H or alkyl)-11-(H or alkyl)-2,6-methano-3-benzazocines and 1-hydroxy secondary and tertiary alcohols obtainable therefrom by reduction and by Grignard reactions, and esters of the same, are useful as central nervous system depressants, particularly as analgesics and as analgesic antagonists. The 3-substituent is introduced by alkylation, directly or by N-acylation followed by reduction of the resulting amides, of the corresponding >NH compounds either before or after introduction of the 1-oxo group into the compounds having two hydrogens at the 1-position by chromium (VI) oxidation. Various intermediates and derivatives are also descibed, including 3a,4,5,9b-tetrahydro-3,5-ethanonaphth[2,1-d]oxazol-2(3H)-ones obtained by interacting 1,2,3,4,5,6-hexahydro-1-hydroxy-2,6-methano-3-benzazocines with phosgene or by heating 1,2,3,4,5,6-hexahydro-1-hydroxy-3-carbalkoxy-2,6-methano-3-benzazocines with alkoxide ion.
    Type: Grant
    Filed: June 14, 1973
    Date of Patent: February 3, 1976
    Assignee: Sterling Drug Inc.
    Inventor: Noel F. Albertson