Patents Assigned to Armour Pharmaceutical Company
  • Patent number: 4055524
    Abstract: Resin peptides useful in the preparation of peptides having biological activity, and particularly such resin peptides containing R-CH.sub.2 -Phe-Glu at one end of an amino acid chain, R being the resin and Phe and Glu being the residues of the amino acids phenylalanine and glutamic acid; and processes for the preparation of such resin peptides. Resin peptides are disclosed which contain amino acid chains identical with the amino acid chains of natural peptides having biological activity. Other resin peptides are disclosed which contain amino acid chains in which the amino acid residues differ in kind and sequence from amino acid chains of natural biologically active peptides but from which peptides having biological activity may be derived.
    Type: Grant
    Filed: August 11, 1975
    Date of Patent: October 25, 1977
    Assignee: Armour Pharmaceutical Company
    Inventors: Robert L. Colescott, Emil Kaiser, Charles D. Bossinger, Paul I. Cook
  • Patent number: 4055664
    Abstract: Preparations containing 4-biphenylyl butylamines or pharmaceutically acceptable salts thereof and methods of using the same whereby a host, including man, to whom such preparations are administered, is provided with anti-inflammatory, antipyretic and analgesic relief while avoiding the unwanted side effects of steroid therapy.The preparations of this invention contain compounds having the structure ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen and lower alkyls having from one to four carbon atoms; and R.sub.2 is selected from the group consisting of hydrogen and lower alkyls having from one to four carbon atoms. The pharmaceutically acceptable salts are formed on the same basis structure as shown.
    Type: Grant
    Filed: September 23, 1976
    Date of Patent: October 25, 1977
    Assignee: Armour Pharmaceutical Company
    Inventor: Martin O. Skibbe
  • Patent number: 4033940
    Abstract: The synthesis of a disulfide cyclic peptide by preparing an intermediate peptide containing an amino terminal cystine residue and a cysteine residue located in a position within the amino acid sequence, to give a desired peptide, and placing such intermediate peptide in a solution substantially free of oxygen at a pH of from about 5 to 10 until rearrangement takes place to yield a cyclic disulfide peptide and to displace a molecule of cysteine from the amino terminal cysteine residue. The disclosure also embraces said intermediate peptides as new compounds and the processes by which they are prepared.
    Type: Grant
    Filed: November 12, 1975
    Date of Patent: July 5, 1977
    Assignee: Armour Pharmaceutical Company
    Inventors: John L. Hughes, Jay K. Seyler, Robert C. Liu
  • Patent number: 4028390
    Abstract: Basic zirconium gels may be used to form complexes with conventional aluminum and/or zirconium antiperspirant systems. The freshly prepared basic zirconium gels provide both a buffer for the highly acidic aluminum-zirconium complexes and an additional source of zirconium as an active ingredient in the antiperspirant. The preferred basic zirconium gels are basic zirconium-amino acid compounds, particularly basic zirconium glycinates, and the compounds are preferably added to aluminum-zirconium systems in the form of a wet gel. The preferred basic zirconium glycinate is formed by first reacting sodium carbonate with glycine, and then reacting the resulting sodium glycinate with a zirconium oxy or zirconium hydroxy compound to precipitate out the zirconium basic glycinate gel. The various complexes of the invention may be used in conventional antiperspirant forms, including aqueous solutions, aerosol sprays, powder-in-oil aerosol sprays, creams, lotions, cream sticks, etc.
    Type: Grant
    Filed: March 26, 1975
    Date of Patent: June 7, 1977
    Assignee: Armour Pharmaceutical Company
    Inventors: Andrew M. Rubino, John L. Jones, Edward S. Bretschneider
  • Patent number: 4025615
    Abstract: Alkali metal and ammonium zirconyl carbonates (AZC) may be used as active antiperspirant ingredients when converted to complexes with various acidic antiperspirant agents, including particularly the highly acidic zirconium compounds. The acidic antiperspirant agent activates the zirconium in the zirconyl carbonate to an acidic, active antiperspirant species. The zirconyl carbonate comprises about 2 to 35 weight percent of the complex, and the antiperspirant activating agent is present in such an amount that the pH of a 5 to 20 weight percent aqueous solution of the complex will be about 3 to 6. Potassium and ammonium zirconyl carbonates are preferred, but sodium may also be used if the complex is kept in solution. The acidic, antiperspirant activating agent is preferably a zirconium oxy salt or zirconium hydroxy salt, such as a zirconium hydroxy halide. However, other water soluble, polyvalent metal salts of strong acids may be used, particularly aluminum halides and basic aluminum compounds.
    Type: Grant
    Filed: February 25, 1975
    Date of Patent: May 24, 1977
    Assignee: Armour Pharmaceutical Company
    Inventor: Andrew M. Rubino
  • Patent number: 4021398
    Abstract: Staining and discoloration of painted wood surfaces, as a result of bleeding into the top or finish coat of soluble coloring matter and tannins naturally present in the wood, is prevented by coating or impregnating the wood with a basic aluminum compound, particularly with a water soluble basic aluminum halide or derivative thereof. The basic aluminum compound may be applied in aqueous solution or non-pigmented emulsion for prefinishing building lumber, or applied in the form of a pigmented emulsion as a primer coat.The present invention relates to novel methods and compositions for application to the surfaces of woods, particularly to stain-susceptible woods, to prevent their staining or discoloring as a result of tannin and tocopherol or other waste-soluble coloring matter present in the raw wood, bleeding or migrating into a subsequently applied preservative or decorative paint film.
    Type: Grant
    Filed: April 18, 1975
    Date of Patent: May 3, 1977
    Assignee: Armour Pharmaceutical Company
    Inventors: William S. Gilman, John L. Jones, Andrew M. Rubino
  • Patent number: 4021536
    Abstract: Astringent compositions useful as antiperspirants are provided by forming a complex of a magnesium salt and an astringent zirconium compound, particularly zirconium oxy and hydroxy salts, such that the weight ratio of the zirconium content to the magnesium content in the complex expressed as the oxides will be in the range of about 30:1 to 1:1. The preferred amount of magnesium, expressed as the oxide, in an aqueous antiperspirant solution containing an effective amount of the complex will be greater than about 3 weight percent. Preferred compositions include complexes of magnesium-amino acid salts, such as magnesium glycinate, plus zirconyl hydroxy chloride in which the ratio of zirconium to magnesium is about 10:1 to 3:1 and the total content of magnesium plus zirconium is about 5 to 15 weight percent and preferably about 5 to 10 weight percent, both expressed as the oxides. Buffers such as urea, amino acids, salts of amino acids, etc.
    Type: Grant
    Filed: April 18, 1975
    Date of Patent: May 3, 1977
    Assignee: Armour Pharmaceutical Company
    Inventor: Andrew M. Rubino
  • Patent number: 4017599
    Abstract: Anti-perspirant complexes are provided which comprise a combination of a basic aluminum compound, a zirconium compound and an amino compound which may be an alkaline or hydroxy salt of an amino acid in which the number of amino groups is equal to the number of carboxyl groups in the molecule. The various components are present in the complex in amounts such that the Al/Zr mol ratio is about 10:1 to 1:10 and the pH of an aqueous solution containing 5 to 15 weight percent of the complex (based on the oxides of aluminum and zirconium) is at least about 3. The basic aluminum compound may be any of the usual basic aluminum anti-perspirant salts, particularly the basic aluminum halides, and the zirconium compound may be a zirconium oxy salt and/or zirconium hydroxy salt. The amino salts may be soluble or insoluble, and particularly preferred compounds include the alkaline and alkaline earth glycinates, aluminum dihydroxy or monohydroxy glycinates, and aluminum-magnesium-hydroxy-glycinate compounds.
    Type: Grant
    Filed: November 23, 1973
    Date of Patent: April 12, 1977
    Assignee: Armour Pharmaceutical Company
    Inventor: Andrew M. Rubino
  • Patent number: 4014934
    Abstract: Novel aromatic guanidine compounds having the formula: ##STR1## wherein: R.sub.1 is hydroxyl, methyl or hydroxymethyl and R.sub.2 is hydrogen or methyl, are found to have biological activity. The guanidine compounds and their salts are shown to be active as vasoconstrictor agents and create useful pharmaceutical preparations when deployed with a pharmaceutically acceptable carrier for administration to a host, e.g., man, requiring vasoconstrictive therapy.
    Type: Grant
    Filed: October 29, 1974
    Date of Patent: March 29, 1977
    Assignee: Armour Pharmaceutical Company
    Inventors: John Lawrence Hughes, Robert Chung-Huan Liu
  • Patent number: 4000279
    Abstract: A pharmaceutical preparation consisting of a pharmaceutical grade carrier and a therapeutically active amount of an aromatic guanidine compound having the formula: ##STR1## or a non-toxic acid addition salt thereof are found to have biologically useful activity. These guanidine preparations and salts are shown to be active as vasoconstrictor agents and obtain useful biological results when deployed with a pharmaceutically acceptable carrier for administration to a host, e.g., man, requiring vasoconstrictive therapy.
    Type: Grant
    Filed: July 16, 1975
    Date of Patent: December 28, 1976
    Assignee: Armour Pharmaceutical Company
    Inventors: John Lawrence Hughes, Robert Chung-Huan Liu
  • Patent number: 3998788
    Abstract: Unusually effective anti-perspirant compositions are provided by forming an astringent complex of a basic aluminum compound, a zirconium compound and a trace amount of an alkaline earth metal salt. The alkaline earth metal may be either calcium or magnesium or both, but preferably magnesium, and may be added as any of the usual salts such as halides, carbonate, oxide, hydroxide, etc. The basic aluminum compounds may be any of the usual basic aluminum anti-perspirant salts, particularly basic aluminum halides, and the zirconium compound may be a zirconium oxy salt and/or zirconium hydroxy salt. The complex should have an Al/Zr mole ratio of about 10:1 to 1:10, and preferably about 4:1 to 1:1, and the pH of an aqueous solution containing 5 to 15 weight percent of the complex (based on the oxides of aluminum and zirconium) should be at least about 3.
    Type: Grant
    Filed: July 17, 1974
    Date of Patent: December 21, 1976
    Assignee: Armour Pharmaceutical Company
    Inventor: Andrew M. Rubino
  • Patent number: 3994891
    Abstract: Tetrahydroisoquinoline compounds represented by the formula: ##SPC1##In whichX is a hydroxy group,Y is a hydroxy group orY taken with X is --O--CH.sub.2 --O--,Z is hydrogen or a hydroxy group,R.sub.1 is hydrogen or an alkyl group of one to four carbon atoms,R.sub.2 is hydrogen, an alkyl group of one to four carbon atoms or phenyl, pyrrolidinomethyl, piperidinomethyl, or morpholinomethyl,R.sub.3 and R.sub.4 each is an alkyl group of one to four carbon atoms or R.sub.3 taken with R.sub.4 and N is pyrrolidinyl, piperidino, morpholino, or 2-(1,2,3,4-tetrahydroisoquinolyl), andn is one or zero,Which compounds are effective as vasodilators, processes for the preparation of these compounds, and intermediate compounds useful in the preparation of such compounds.
    Type: Grant
    Filed: December 20, 1974
    Date of Patent: November 30, 1976
    Assignee: Armour Pharmaceutical Company
    Inventors: John Lawrence Hughes, Jay Kenneth Seyler
  • Patent number: 3991176
    Abstract: Anti-perspirant complexes are provided which comprise a combination of a basic aluminum compound, a zirconium compound and a hydroxy carboxylic compound which may be a non-toxic salt of a hydroxy carboxylic acid, a non-toxic salt of an aluminum chelate of a hydroxy carboxylic acid, a codried mixture of aluminum hydroxide with a non-toxic salt of an aluminum chelate of a hydroxy carboxylic acid, or mixtures thereof. The various components are present in the complex in amounts such that the Al/Zr mol ratio is about 10:1 to 1:10 and the pH of an aqueous solution containing 5 to 15 weight percent of the complex (based on the oxides of aluminum and zirconium) is at least about 3. The complexes may be used in conventional anti-perspirant forms, including aqueous solutions, aerosol sprays (including powder-in-oil aerosol sprays), as well as creams, lotions and cream sticks.
    Type: Grant
    Filed: January 16, 1974
    Date of Patent: November 9, 1976
    Assignee: Armour Pharmaceutical Company
    Inventor: Andrew M. Rubino
  • Patent number: 3986927
    Abstract: Methods of sterilizing biologicals in which the biologicals are acidified to a pH of not higher than about 1.0, preferably 0.75 to about 0.5, and the acidified biologicals are stored at cold temperatures for a perod of time sufficient to inactivate microbial flora contained therein but not the biological itself, for example, in the range of about 0.degree. to about 10.degree. C for 1-24 hours or longer. Precipitates formed during the storing are clarified and the biologicals are then neutralized, preferably to a pH of from about 7.0 to about 8.0, or that pH at which the biological is best stored, e.g., trypsin at pH 3-4. The methods include clarifying biologicals of precipitates formed within the first two to three hours and then continuing the storing and again clarifying the biologicals of precipitates.Microbial flora and numerous contaminated proteins contained in the biologicals are removed resulting in completely sterilized biologicals retaining initial activity or titer.
    Type: Grant
    Filed: April 28, 1975
    Date of Patent: October 19, 1976
    Assignee: Armour Pharmaceutical Company
    Inventors: Joseph L. Melnick, Craig Wallis
  • Patent number: 3981986
    Abstract: Water soluble anti-perspirant complexes are provided which comprise a combination of a basic aluminum-polyol compound, a zirconium compound and an organic buffer which may be urea, an amino acid in which the number of amino groups is equal to the number of carboxyl groups in the molecule, an alkaline or hydroxy salt of such amino acid, or mixtures thereof. The various components are present in the complex in amounts such that the Al/Zr mol ratio is about 10:1 to 1:10 and the pH of an aqueous solution containing 5 to 15 weight percent of the complex (based on the oxides of aluminum and zirconium) is at least about 3. The basic aluminum-polyol compounds may be those described in U.S. Pat. Nos. 3,359,169; 3,420,932; 3,405,153 and 3,555,146, particularly basic aluminum chloride-propylene glycol complex. The zirconium compound may be a zirconium oxy (zirconyl) salt and/or zirconium hydroxy salt. Preferred amino acid buffers include glycine and .beta.
    Type: Grant
    Filed: January 8, 1974
    Date of Patent: September 21, 1976
    Assignee: Armour Pharmaceutical Company
    Inventor: Andrew M. Rubino
  • Patent number: 3979510
    Abstract: Anti-perspirant complexes are provided which comprise a combination of a basic aluminum compound, a zirconium compound and a complex aluminum buffering compound containing in addition to aluminum two or more of the following: magnesium, calcium, sodium, carbonate, sulfate, hydroxyl and water. The various components are present in the complex in amounts such that the Al/Zr mole ratio is about 10:1 to 1:10 and the pH of an aqueous solution containing 5 to 15 weight percent of the complex (based on the oxides of aluminum and zirconium) is at least about 3. The basic aluminum compound may be any of the usual basic aluminum anti-perspirant salts, particularly the basic aluminum halides, and the zirconium compound may be a zirconium oxy salt and/or zirconium hydroxy salt. The complex aluminum buffer preferably contains among the additional groups or elements magnesium and/or carbonate.
    Type: Grant
    Filed: June 7, 1974
    Date of Patent: September 7, 1976
    Assignee: Armour Pharmaceutical Company
    Inventor: Andrew M. Rubino
  • Patent number: 3976787
    Abstract: Pharmaceutical preparations and methods of using the same to treat a host having a condition requiring vasoconstrictive therapy. The preparations comprise a pharmaceutically acceptable carrier and a guanidine compound, or non-toxic acid addition salt thereof, having the structural notation: ##SPC1##Wherein: R.sub.1 is hydrogen or alkyl having 1-4 carbon atoms; R.sub.2 is hydrogen, hydroxy, chloro, fluoro or bromo; and R.sub.3 is hydrogen or the same as R.sub.2 when R.sub.2 is chloro, bromo or fluoro.
    Type: Grant
    Filed: March 6, 1975
    Date of Patent: August 24, 1976
    Assignee: Armour Pharmaceutical Company
    Inventors: John Lawrence Hughes, Robert Chung-Huan Liu, Takashi Enkoji, James Winslow Bastian
  • Patent number: 3966724
    Abstract: Compounds having the structure: ##SPC1##In which R.sub.1 and R.sub.2 are alkoxy groups of one to four carbon atoms, R.sub.3 and R.sub.4 each is hydrogen or an alkoxy group of one to four carbon atoms, and R.sub.5 and R.sub.6 each is an alkyl group of one to four carbon atoms or an arylalkyl group such as benzyl or R.sub.5 taken with R.sub.6 and N are pyrrolidinyl, piperidino, or morpholino groups and the pharmaceutically acceptable salts thereof and processes for preparing these compounds. These compounds are useful as vasodilators.
    Type: Grant
    Filed: December 20, 1974
    Date of Patent: June 29, 1976
    Assignee: Armour Pharmaceutical Company
    Inventors: John Lawrence Hughes, Jay Kenneth Seyler, Carroll M. Smith
  • Patent number: 3947455
    Abstract: A novel aromatic guanidine compound having the formula: ##SPC1##Is found to have biological activity. This guanidine compound and its salts are shown to be active as vasoconstrictor agents and create useful pharmaceutical preparations when deployed with a pharmaceutically acceptable carrier for administration to a host, e.g., man, requiring vasoconstrictive therapy.
    Type: Grant
    Filed: October 29, 1974
    Date of Patent: March 30, 1976
    Assignee: Armour Pharmaceutical Company
    Inventors: John Lawrence Hughes, Robert Chung-Huan Liu
  • Patent number: 3947556
    Abstract: Alcohol soluble complexes of basic aluminum chlorides may be prepared by adding zinc bromide or chloride, or zirconyl bromide or hydroxybromide, or zinc or zirconyl mixtures of the above to an aqueous solution of five-sixths basic aluminum chloride, and drying the resulting mixture to a substantially friable solid. The complexes preferably have an Al/Zn or Al/Zr mol ratio of about 3:1 to 20:1, and the complex solids preferably contain about 12 to 30 weight percent water by Karl Fischer analysis. Such complex solids have a high degree of solubility in anhydrous alcohol and a high compatibility with halogenated hydrocarbons, thus making the complexes suitable for aerosol formulations and particularly antiperspirant compositions.
    Type: Grant
    Filed: June 3, 1975
    Date of Patent: March 30, 1976
    Assignee: Armour Pharmaceutical Company
    Inventors: John L. Jones, Andrew M. Rubino, Charles B. Lindahl