Patents Represented by Attorney Derek P. Freyberg
  • Patent number: 5091182
    Abstract: A dispensing unit for a ketorolac topical gel formulation is disclosed, wherein the dispensing unit comprises a ketorolac topical gel formulation and a gas-impermeable multi-layered container wherein the container is comprised of a polyolefin inner layer and a metal foil outer layer.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: February 25, 1992
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John T. H. Ong, Jean S. Fujiki, Wei-Cheng Liaw
  • Patent number: 5082950
    Abstract: 5-Aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates of the formula ##STR1## are prepared from 2-aroylpyrroles. Hydrolysis and mono-decarboxylation of these compounds affords ketorolac and related compounds.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: January 21, 1992
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, In-Seop Cho
  • Patent number: 5082951
    Abstract: 5-Aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylates of the formula ##STR1## are prepared from 2-aroylpyrroles. Hydrolysis and mono-decarboxylation of these compounds affords ketorolac and related compounds.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: January 21, 1992
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, In-Seop Cho
  • 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: 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: 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: 4988822
    Abstract: 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylates of the formula ##STR1## are prepared from 2-halopyrroles. Hydrolysis and .beta.-decarboxylation of these compounds affords ketorolac and related compounds.
    Type: Grant
    Filed: July 27, 1989
    Date of Patent: January 29, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse
  • Patent number: 4983595
    Abstract: A non-stinging aqueous anti-inflammatory steroid formulation suitable for intranasal administration comprises: an anti-inflammatory steroid in an amount between about 0.01% and about 0.05% (w/v); propylene glycol in an amount between about 2% and about 10% (w/v); PEG 400 in an amount between about 10% and about 25% (w/v); polysorbate 20 in an amount between about 1% and about 4% (w/v); an effective amount of a preservative; an effective amount of a stabilizer; an effective amount of an antioxidant; water; and pH buffering agent sufficient to adjust the pH of the resulting solution to between about 3.5 and about 7.
    Type: Grant
    Filed: September 20, 1988
    Date of Patent: January 8, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Eric Benjamin, Shabbir Anik, Ya-Yun T. Lin
  • Patent number: 4943635
    Abstract: Chiral 1,3,2-oxazaborolidines and tetrahydro-1,3,2-oxazaborines are effective catalysts for the borane reduction of prochiral ketones to optically active alcohols.
    Type: Grant
    Filed: July 29, 1988
    Date of Patent: July 24, 1990
    Assignee: President & Fellows of Harvard College
    Inventor: Elias J. Corey
  • Patent number: 4937368
    Abstract: 2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylates of the formula, ##STR1## in which each R is independently H or lower alkyl, are prepared from from di(lower alkyl) 1,3-acetone-dicarboxylates.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: June 26, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Hiralal N. Khatri, Michael P. Fleming, George C. Schloemer
  • Patent number: 4933179
    Abstract: A vaccine for immunizing animals against Feline Leukemia Virus (FeLV) infections contains an FeLV antigen emulsified with a polyoxypropylene-polyoxyethylene block polymer, a glycol ether-based surfactant, an immunopotentiating amount of an immunostimulating glycopeptide, and, optionally, a metabolizable non-toxic oil.
    Type: Grant
    Filed: February 21, 1985
    Date of Patent: June 12, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Anthony C. Allison, Noelene E. Byars
  • Patent number: 4929740
    Abstract: Compounds of the formula ##STR1## where R.sup.1 and R.sup.2 are hydrogen or an ether-forming group and X is hydrogen, halo, trifluoromethyl, lower alkyl, or lower akoxy, are useful intermediates for making PGE and PGF derivatives having an allenic function.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: May 29, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Gary F. Cooper
  • Patent number: 4912235
    Abstract: This invention relates to a process for making a compound of formula I ##STR1## in the form of a stereoisomer or mixture thereof, wherein R is hydrogen, lower alkyl; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta., or a pharmaceutically acceptable, non-toxic salt of the compound wherein R is hydrogen; novel intermediates useful for preparing these compounds; processes for making the intermediates; and a stereoisomer of the compound of formula I wherein R is methyl and X is hydrogen and a process for making same.
    Type: Grant
    Filed: June 7, 1988
    Date of Patent: March 27, 1990
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Douglas L. Wren, Albert R. Van Horn, Tsung-Tee Li, Colin C. Beard
  • Patent number: 4889866
    Abstract: Novel arylsulfonyl-dihydropyridine derivatives which are useful as calcium entry-blocker cardiovascular agents have the formula: ##STR1## or a pharmaceutically acceptable salt thereof, wherein R.sup.1 is hydrogen, lower alkyl, or lower alkoxyalkyl;R.sup.2 is hydrogen or chloro; andR.sup.3 is hydrogen, lower alkyl, or lower alkoxyethyl.A novel process using chiral sulfoxide reagents efficiently produces single isomers of these and other sulfonyl dihydropyridines.
    Type: Grant
    Filed: June 11, 1987
    Date of Patent: December 26, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Jurg R. Pfister, Roman Davis, Chi-Ho Lee
  • Patent number: 4874871
    Abstract: 2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid compounds of the formula, ##STR1## in which Y is OH;O.sup.- M.sup.+, wherein M is an alkali metal; orNRR', wherein R is lower alkyl and R' is lower alkyl or aryl, or NRR' is the residue of a saturated cyclic amine,are prepared from pyrrole.
    Type: Grant
    Filed: March 25, 1987
    Date of Patent: October 17, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Michael P. Fleming, George C. Schloemer, Hiralal N. Khatri
  • Patent number: 4874872
    Abstract: 2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylates of the formula, ##STR1## in which each R is independently H or lower alkyl, are prepared from di(lower alkyl) 1,3-acetonedicarboxylates.
    Type: Grant
    Filed: October 11, 1988
    Date of Patent: October 17, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Michael P. Fleming, Hiralal N. Khatri, George C. Schloemer
  • Patent number: 4873340
    Abstract: 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylates of the formula ##STR1## are prepared from 2-halopyrroles. Hydrolysis and .beta.-decarboxylation of these compounds affords ketorolac and related compounds.
    Type: Grant
    Filed: May 29, 1986
    Date of Patent: October 10, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse
  • Patent number: 4857318
    Abstract: A vaccine derived from Bordetalla bronchiseptica effective against Bordetella pertussis infection is disclosed herein.
    Type: Grant
    Filed: March 25, 1985
    Date of Patent: August 15, 1989
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Simon W. Lee