Patents Represented by Attorney Tom M. Moran
  • Patent number: 5072006
    Abstract: Compounds of the formula ##STR1## wherein: R.sub.1 is cyano or nitro;R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl; andR.sub.4 is alkyl; alkenyl; optionally substituted phenyl or phenyl lower alkyl; --(CH.sub.2).sub.m OR.sub.2 or --(CH.sub.2).sub.m N(R.sub.2).sub.2 ; wherein m is an integer of 1-5 and R.sub.2 is as defined above;or a pharmaceutically acceptable ester thereof; are smooth muscle relaxants, particularly useful in the treatment of hypertension.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: December 10, 1991
    Assignee: Recherche Syntex France S.A.
    Inventors: Gilles Genain, Henri Pinhas
  • Patent number: 5068360
    Abstract: An improved process for the synthesis of 2-(2'-thienyl)ethylamine from suitably functionalized derivatives of 2-(2'-thienyl)ethanol employing ammonia gas in the presence of a metal salt or liquid ammonia and alkyl ketone as a solvent. The 2-(2'-thienyl)ethylamine produced by this process is advantageously converted to ticlopidine.
    Type: Grant
    Filed: January 25, 1990
    Date of Patent: November 26, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Bradley S. DeHoff
  • Patent number: 5063220
    Abstract: A pharmaceutical formulation suitable for parenteral (preferably intravenous) administration includes an effective amount of 1-diphenylmethyl-4-[(2-(4-methylphenyl)-5-methyl-1H-imidazol-4-yl)methyl]p iperazine and a suitable amount of an acid to generate a pharmaceutically acceptable salt having a pH above about 3.0 and a solubility above about 4.0 mg/ml. The intravenous formulation optionally includes a suitable tonicifier in a quantity sufficient to achieve isotonicity with body fluids. The salt is formed in situ during the formulation process. The salt of tartaric acid is preferred; suitable salts for lower concentration dosages are the citric acid and methane sulphonic acid salts.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: November 5, 1991
    Assignee: Syntex Pharmaceuticals, Ltd.
    Inventors: Alastair B. Selkirk, Michael J. Dey
  • Patent number: 5057621
    Abstract: This invention covers a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, Y is lower alkyl or ##STR2## wherein Z is hydrogen, halo, methyl, methoxy or trifluoromethyl; and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: October 15, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, John H. Fried, L. David Waterbury
  • Patent number: 5055451
    Abstract: Thiol protease inhibitors are disclosed having the formula: ##STR1## or an optical isomer thereof, or a pharmaceutically acceptable salt thereof, wherein:n is 0 or 1;m is 0, 1 or 2;X is H or an N-protecting group;each Y is independently an optionally protected .alpha.-amino acid residue;R is an optionally protected .alpha.-amino acid side chain that is H or CH.sub.3 or that is bonded to the .alpha.-carbon atom to which it is attached by a methylene, methine or phenyl radical; andR' is optionally substituted aryl.
    Type: Grant
    Filed: December 7, 1987
    Date of Patent: October 8, 1991
    Assignee: Syntex Inc.
    Inventors: Alexander Krantz, Heinz W. Pauls, Roger A. Smith, Robin W. Spencer
  • Patent number: 5049386
    Abstract: This invention relates to compounds of the formula ##STR1## or an optical isomer thereof wherein R.sup.1 and R.sup.2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R.sup.3, R.sup.4 and R.sup.5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R.sup.3, R.sup.4, and R.sup.5 are taken together to form quinuclidino, piperidino, pyrrolidino, or morpholino; n is 1 to 8; and X is a pharmaceutically acceptable anion.
    Type: Grant
    Filed: May 15, 1990
    Date of Patent: September 17, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Deborah A. Eppstein, Philip L. Felgner, Thomas R. Gadek, Gordon H. Jones, Richard B. Roman
  • Patent number: 5049497
    Abstract: The enantiomers of formulas ##STR1## are prepared in a sequence starting from the racemic compound of formula ##STR2## wherein X is hydro or bromo when Y is bromo, or X is chloro when Y is chloro. The key step of this process involves a microbial reduction of the compound of formula (3) to give a ketone and an alcohol of high enantiomeric purity.
    Type: Grant
    Filed: August 25, 1986
    Date of Patent: September 17, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Arthur F. Kluge, Dennis J. Kertesz
  • Patent number: 5043447
    Abstract: Substituted imidazolyl-alkyl-piperazine and diazepine derivatives of Formula A: ##STR1## wherein: R.sup.1 is aryl, lower alkyl, cycloalkyl or hydrogen;R.sup.2 is aryl, lower alkyl or hydrogen;R.sup.3 is lower alkyl, hydroxy, or hydrogen;R.sup.4 is aryl or hydrogen;R.sup.5 is aryl or hydrogen;m is two or three;n is zero, one or two,provided that when R.sup.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: August 27, 1991
    Assignee: Syntex Pharmaceuticals, Ltd.
    Inventors: Jean C. Pascal, Chi-Ho Lee, Brian J. Alps, Henri Pinhas, Roger L. Whiting, Calum B. Macfarlane, Serge Beranger, Robert J. Dow
  • Patent number: 5041442
    Abstract: This invention is directed to compounds of formula (I): ##STR1## wherein R.sup.1 is thiocyano, --CH.sub.2 CN, --NH.sub.2, --NHR.sup.5, or --CH.sub.2 OR.sup.5 where R.sup.5 is lower alkyl;R.sup.2 is hydrogen, halo, lower alkyl, or lower alkylthio;R.sup.3 is hydrogen, halo, lower alkyl, lower alkylthio, or thiocyano;R.sup.4 is hydrogen, halo, lower alkyl, lower alkoxy, lower alkylthio, or lower alkylsulfonyl; andY is --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.dbd.CH--, or --(CH.sub.2).sub.n -- where n is 0, 1, 2, 3 or 4;or a pharmaceutically acceptable salt thereof. These compounds are useful in treating mammals having disease-states characterized by excessive gastric acid secretion.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: August 20, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Ruth S. Romero, Fidencio Franco, Armando C. Castaneda, Joseph M. Muchowski
  • Patent number: 5035891
    Abstract: A sustained release, reservoir-type subcutaneous implant device for the sustained administration to a subject of a biologically active compound comprises:an effective amount of a biologically active compound;an amount of a solid hydrophilic polymer sufficient to cause swelling of the device by osmotic pressure after implantation;an effective amount of a solubilizing agent; anda sufficient amount of a non-porous rate-controlling membrane which completely encapsulates said biologically active compound, wherein said rate-controlling membrane is permeable to said biologically active compound, but is impermeable to said solubilizing agent. This device is particularly advantageous for the administration of growth promoting compounds to livestock.
    Type: Grant
    Filed: August 24, 1989
    Date of Patent: July 30, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Richard A. Runkel, Jung-Chung Lee
  • Patent number: 5034410
    Abstract: This invention is directed to a method for treating helminthiasis in an animal which method comprises administering to an animal in need thereof an anthelmintically effective amount of a compound of the Formula (I): ##STR1## wherein Z is oxygen or sulfur;R.sup.1 is hydrogen or lower alkyl; andR.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently hydrogen, halo, lower haloalkyl, lower alkoxy, lower haloalkoxy, nitro, cyano, halophenoxy, haloalkylphenoxy, thiocyano or isothiocyano, provided that R.sup.2 and R.sup.3 cannot simultaneously be hydrogen and that R.sup.4 and R.sup.5 cannot simultaneously be hydrogen; or a pharmaceutically acceptable salt thereof, and pharmaceutical compositions formulated therewith. This invention is also directed to novel anthelmintically active benzenepropanamides of Formula (I) wherein Z is oxygen.
    Type: Grant
    Filed: October 11, 1989
    Date of Patent: July 23, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Eric B. Sjogren, Michael A. Rider
  • Patent number: 5028430
    Abstract: An implantable polymeric delivery system for the controlled and continuous administration of an LHRH agonist which comprises a silicone elastomer matrix in which is dispersed about 30 to about 42 weight percent of water-soluble particulate phase containing an LHRH analog or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: May 8, 1987
    Date of Patent: July 2, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Lynda M. Sanders, Ramon A. Burns, Jr.
  • Patent number: 5010075
    Abstract: Substituted imidazolyl-alkyl-piperazine and diazepine derivatives of Formula A: ##STR1## wherein: R.sup.1 is aryl, lower alkyl, cycloalkyl or hydrogen;R.sup.2 is aryl, lower alkyl or hydrogen;R.sup.3 is lower alkyl, hydroxy, or hydrogen;R.sup.4 is aryl or hydrogen;R.sup.5 is aryl or hydrogen;m is two or three;n is zero, one or two, provided that when R.sup.3 is hydroxy, n is one or two; andq is zero, one, two, or three;and the pharmaceutically acceptable salts thereof, are calcium channel antagonists useful for treating mammals having a variety of disease states, such as stroke, epilepsy, hypertension, angina, migraine, arrhythmia, thrombosis, embolism and also for treatment of spinal injuries.
    Type: Grant
    Filed: April 6, 1990
    Date of Patent: April 23, 1991
    Assignee: Syntex Pharmaceuticals Ltd.
    Inventors: Jean C. Pascal, Chi-Ho Lee, Brian J. Alps, Henri Pinhas, Roger L. Whiting
  • Patent number: 5001124
    Abstract: This invention is directed to compounds of the formula (I): ##STR1## wherein R.sup.1 is --OR.sup.4 (where R.sup.4 is hydrogen, lower alkyl, lower hydroxyalkyl, phenyl, phenyl-lower-alkyl, or --(CH.sub.2).sub.n Y where n is an integer from 1 to 4 and Y is morpholino, -SR.sup.5, --C(O)OR.sup.5, --C(O)N(R.sup.6).sub.2, --N(R.sup.6).sub.2, or --N.sup.+ (R.sup.6).sub.3 X.sup.-, in which R.sup.5 is lower alkyl, each R.sup.6 is independently selected from hydrogen or lower alkyl, and X is halogen)or --SR.sup.7 (where R.sup.7 is lower alkyl, phenyl-lower-alkyl, or --(CH.sub.2).sub.n W where W is --N(R.sup.6).sub.2 or --N.sup.+ (R.sup.6).sub.3 X.sup.-, and n, R.sup.6 and X are as previously defined);R.sup.2 is lower alkyl, phenyl or phenyl-lower-alkyl;R.sup.3 is halo, hydroxy, lower alkyl, lower alkoxy, lower haloalkyl, lower haloalkoxy, or --C(O)OR.sup.5 where R.sup.5 is as previously defined; andZ is a bond, 2,5-thienyl or 2,5-furanyl; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: February 2, 1990
    Date of Patent: March 19, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John W. Patterson, Bruce H. Devens
  • Patent number: 4997823
    Abstract: Infection associated with parenteral injections of parenterally suitable compounds, especially of F.sub.2.alpha. prostaglandins, is prevented by novel compositions comprising such compounds, a locally effective amount of an antibiotic, and a pharmaceutically acceptable carrier.
    Type: Grant
    Filed: July 20, 1987
    Date of Patent: March 5, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Richard C. Herschler
  • Patent number: 4997846
    Abstract: Compounds of the formula ##STR1## wherein: R.sub.1 is cyano or nitro;R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl; andR.sub.4 is alkyl; alkenyl; optionally substituted phenyl or phenyl lower alkyl; --(CH.sub.2).sub.m OR.sub.2 or --(CH.sub.2).sub.m N(R.sub.2).sub.2 ; wherein m is an integer of 1-5 and R.sub.2 is as defined above;or a pharmaceutically acceptable ester thereof; are smooth muscle relaxants, particularly useful in the treatment of hypertension.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: March 5, 1991
    Assignee: Researche Syntex France, S.A.
    Inventors: Gilles Genain, Henri Pinhas
  • Patent number: 4997945
    Abstract: The carbamate salt of 2-(2'-thienyl)-alkylamines and particularly the ethylamine and its method of synthesis are disclosed. The carbamate salt of 2-(2'-thienyl)ethylamine is a stable, easily transportable crystalline material that can be converted to 2-(2'-thienyl)ethylamine, a useful intermediate in the synthesis of 5[(2-chlorophenyl)methyl]-4,5,6,7-tetrahydrothieno-[3,2-c]pyridine hydrochloride, also known as ticlopidine hydrochloride. The synthesis is carried out by reacting an amine of formula (I): ##STR1## with CO.sub.
    Type: Grant
    Filed: January 25, 1990
    Date of Patent: March 5, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Hiralal N. Khatri
  • Patent number: 4992467
    Abstract: The compounds and pharmaceutical compositions of Formula A, wherein Z is hydrogen or --C(O)R, Y is hydrogen or morpholinoethyl, and where R is lower alkyl or aryl, and the pharmaceutically acceptable salts thereof, are useful as immunosuppressive agents, particularly for treatment of allograft rejection, especially including cardiac allograft rejection, pancreatic allograft rejection and renal allograft rejection, and for treating autoimmune diabetes.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: February 12, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Anthony C. Allison, Elsie M. Eugui, Peter H. Nelson, Chee-Liang L. Gu, William A. Lee
  • Patent number: 4983627
    Abstract: Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): ##STR1## wherein: A is --C.tbd.C--, trans --HC.dbd.CH--, trans --CH.dbd.CHCH.sub.2 -- or --CH.sub.2 CH.sub.2 --;X is lower alkyl of 1-6 carbon atoms;Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl);n is an integer from 2-4;R.sub.1 is --CH.sub.2 OH, --CHO, --CO.sub.2 R or --CO.sub.2 H, and the olefin formed by the R.sub.1 (CH.sub.2).sub.n CH.dbd. moiety is either (E) or (Z);R.sub.2 is hydrogen or methyl, or optionally --CH.dbd.CH.sub.2 when A is trans --CH.dbd.CHCH.sub.2 --; andR.sub.3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, ##STR2## --(CH.sub.2).sub.m -phenyl or CH.sub.2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: January 8, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Counde O'Yang, Walter Kurz, Keith A. M. Walker, Helen Y. Wu
  • Patent number: 4973591
    Abstract: A pharmaceutical formulation suitable for parenteral (preferably intravenous) adminstration includes an effective amount of 1-diphenylmethyl-4-[(2-(4-methylphenyl)-5-methyl-1H-imidazol-4-yl)methyl]p iperazine and a suitable amount of an acid to generate a pharmaceutically acceptable salt having a pH above about 3.0 and a solubility above about 4.0 mg/ml. The intravenous formulation optionally includes a suitable tonicifier in a quantity sufficient to achieve isotonicity with body fluids. The salt is formed in situ during the formulation process. The slat of tartaric acid is preferred; suitable salts for lower concentration dosages are the citric acid and methane sulphonic acid salts.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: November 27, 1990
    Assignee: Syntex Pharmaceuticals, Ltd.
    Inventors: Alastair B. Selkirk, Michael J. Dey