Patents Represented by Attorney Raymond M. Speer
  • Patent number: 4202903
    Abstract: Certain novel acyl cyanoguanidines, their preparation, pharmaceutical compositions and novel methods of treating inflammation and autoimmune diseases such as rheumatoid arthritis are disclosed.
    Type: Grant
    Filed: September 30, 1975
    Date of Patent: May 13, 1980
    Assignee: Merck & Co., Inc.
    Inventors: Tsung-Ying Shen, Howard Jones
  • Patent number: 4195023
    Abstract: Certain novel acyl saccharins and acyl 3-oxo-1,2-benzisothiazolines, their preparation, pharmaceutical compositions and novel methods of inhibiting elatase and treating emphysema are disclosed.
    Type: Grant
    Filed: August 20, 1975
    Date of Patent: March 25, 1980
    Assignee: Merck & Co., Inc.
    Inventors: Dennis Mulvey, Howard Jones, Morris Zimmerman
  • Patent number: 4191759
    Abstract: Amides of 17.beta.-carboxy-4-androsten-3-one having the formula: ##STR1## where R.sup.1 and R.sup.2 are hydrogen (only one may be hydrogen), C.sub.1-4 alkyl, cyclo C.sub.5-6 alkyl, phenyl, or together with the nitrogen are a 5 or 6 membered heterocycle with up to one other heteroatom selected from oxygen and nitrogen; R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are hydrogen or C.sub.1-3 alkyl; R.sup.7 is hydrogen or cyano; Z is oxygen, N-R.sup.8 where R.sup.8 is C.sub.1-3 alkyl, or CH--R.sup.9 where R.sup.9 is hydrogen, .alpha.-fluoro, or .alpha.-C.sub.1-3 alkyl,active as testosterone 5.alpha.-reductase inhibitors, and thus useful topically for treatment of acne, seborrhea, female hirsutism and male pattern baldness.
    Type: Grant
    Filed: April 13, 1978
    Date of Patent: March 4, 1980
    Assignee: Merck & Co., Inc.
    Inventors: David B. R. Johnston, Glen E. Arth, deceased
  • Patent number: 4183356
    Abstract: An ophthalmic applicator device for mechanically inserting solid medicaments in the form of inserts into the cul-de-sac of the eye, comprising an elongated tip of non-toxic, pliable material terminating in a groove through an end of said tip sufficient to form two flexible, opposed termini of said tip whereby said insert is releasably gripped by frictional engagement between said termini; said groove having cross-sectional conformation and dimensions sufficient to releasably grip said insert, and at least one dimension sufficiently less than the greatest dimension of said insert to result in removal of said insert from the ophthalmic applicator device by contact of said insert with the cul-de-sac of the eye; and a handle attached to said tip at the end of said tip opposite said termini, and forming an interior angle therewith of from about 30.degree. to about 120.degree..
    Type: Grant
    Filed: March 7, 1977
    Date of Patent: January 15, 1980
    Assignee: Merck & Co., Inc.
    Inventor: Neil W. Miller
  • Patent number: 4179453
    Abstract: A process for preparing 17.beta.-carboxy-4-androsten-3-ones comprising the steps of (1) reacting a 17.beta.-(1-ketoethyl)-5-androsten-3-ol, for example, pregnenolene, with pyridine and iodine to form a pyridinium iodide compound; (2) reacting the pyridinium iodide compound with alkali metal methoxide in methanol to form a methyl-5-androsten-3-ol-17.beta. carboxylate; (3) oxidizing the product of Step (2) preferably with aluminum isopropoxide to form methyl-4-androsten-3-one-17.beta.-carboxylate; and (4) hydrolyzing the product of Step (3) to the corresponding 17.beta.-carboxylic acid, salt, or ester. The 17.beta.-carboxy-4-androsten-3-ones are useful as intermediates for preparation of N-substituted-17.beta.-carbamoylandrost-4-en-3-one and 4-aza-17.beta.-substituted-5.alpha.-androstan-3-one 5.alpha. reductase inhibitors.
    Type: Grant
    Filed: April 13, 1978
    Date of Patent: December 18, 1979
    Assignee: Merck & Co., Inc.
    Inventor: David B. R. Johnston
  • Patent number: 4171417
    Abstract: Copolymers useful in making electroconductive paper which impart improved solvent holdout properties to the electroconductive paper, comprising monomer units of quaternary diallyldialkylammonium and a monomer of the formula: --CH.sub.2 .dbd.C(R.sub.1)--C(O)--O--R.sub.2, where R.sub.1 is hydrogen or methyl; R.sub.2 is an alkyl group of 2 to 12 carbon atoms, that number being designated n, substituted with fluorine atoms in number equal to from n to 2n; and for the quaternary diallyldialkylammonium monomer, the alkyl groups are independently selected from alkyl groups of one to 18 carbon atoms, and the counterion is an anion.
    Type: Grant
    Filed: October 30, 1978
    Date of Patent: October 16, 1979
    Assignee: Calgon Corporation
    Inventor: Kenneth W. Dixon
  • Patent number: 4166894
    Abstract: Novel functional ionene polymer compositions useful in a wide variety of applications, including, among others, as wet and dry strength additives, corrosion inhibitors, and electroconductive coatings.
    Type: Grant
    Filed: November 17, 1977
    Date of Patent: September 4, 1979
    Assignee: Calgon Corporation
    Inventor: Raymond J. Schaper
  • Patent number: 4166177
    Abstract: The invention relates to novel 2,2-dioxo-1,2,3-benzoxathiazines substituted in the benzene nucleus, as well as the 3,4-dihydro analogs thereof, useful as anti-inflammatory, antipyretic, analgesic agents.
    Type: Grant
    Filed: December 27, 1977
    Date of Patent: August 28, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Edward J. Cragoe, Jr., Robert L. Smith, Gerald E. Stokker
  • Patent number: 4158643
    Abstract: A carbon supported catalyst used for carbon monoxide oxidation is chemically modified by treating the activated carbon support with an oxidizing agent and/or a hydrophobic compound prior to impregnation with the catalyst mixture. The thus treated catalytic carbon is capable of oxidizing carbon monoxide in an air stream containing sulfur dioxide over an extended period of time.
    Type: Grant
    Filed: September 9, 1977
    Date of Patent: June 19, 1979
    Assignee: Calgon Corporation
    Inventor: Rabindra K. Sinha
  • Patent number: 4156005
    Abstract: Substituted 1,2-benzisoxazoles of the formula ##STR1## where: R.sup.1 and R.sup.3 =H or lower alkoxy;R.sup.2 =halo or .alpha.-branched lower alkyl;R.sup.4 =halo, halo lower alkyl, or lower alkylthio; provided, where R.sup.1 and R.sup.3 =H,R.sup.2 and R.sup.4 are other than simultaneously Cl or Br, which are active as antiinflammatory, antipyretic and analgesic agents, are derived from cyclodehydrating the corresponding salicylaldoximes with an isocyanate under extremely mild conditions.
    Type: Grant
    Filed: June 21, 1978
    Date of Patent: May 22, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Gerald E. Stokker, Edward J. Cragoe, Jr.
  • Patent number: 4154750
    Abstract: Phospholipid-containing vegetable oils, especially soya oil, are treated by an improved refining method comprising the steps of degumming the crude vegatable oil, passing the degummed oil through a bed of granular activated carbon, and finally subjecting the treated vegetable oil to steam assisted vacuum distillation deodorization. The process yields a final product acceptable in taste, odor and color and storage stable for normal shelf life periods.
    Type: Grant
    Filed: May 22, 1978
    Date of Patent: May 15, 1979
    Assignee: Calgon Corporation
    Inventors: Hal E. Moore, James B. Yeates
  • Patent number: 4150045
    Abstract: A novel impregnated activated carbon, containing from about 1.0 percent to about 15.0 percent by weight of MgO, has been found to be useful in a method of decolorizing a crude vegetable oil or a degummed vegetable oil, and removing organic acids therefrom, as well as in a process for making a refined edible vegetable oil wherein a crude vegetable oil is degummed, passed through the impregnated activated carbon, and subjected to steam distillation at reduced pressure. A novel method of preparing the MgO impregnated activated carbon has also been discovered.
    Type: Grant
    Filed: April 24, 1978
    Date of Patent: April 17, 1979
    Assignee: Calgon Corporation
    Inventor: Rabindra K. Sinha
  • Patent number: 4147681
    Abstract: Self-inverting emulsion polymers and their use as drainage aids, retention aids, saveall flotation aids and process water flocculants. The polymers are copolymers and homopolymers based on acrylamide, polymerized in the presence of water, an inert hydrophobic liquid, free radical catalyst and an emulsifier having a HLB of at least 7.
    Type: Grant
    Filed: November 21, 1977
    Date of Patent: April 3, 1979
    Assignee: Calgon Corporation
    Inventors: Sim K. Lim, Arnold E. Bloomquist, Raymond J. Schaper
  • Patent number: 4145364
    Abstract: Fluorinated anilines, especially p-fluoroaniline and 2,4-difluoroaniline, are prepared by treating aromatic azides with anhydrous hydrogen fluoride. The aromatic azides, in turn, are prepared from the corresponding anilines by treatment with nitrous acid or salt thereof and an alkali metal azide in the presence of a mineral acid, and in an aqueous-nonaqueous, two-phase environment.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: March 20, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Dennis M. Mulvey, Leonard M. Weinstock
  • Patent number: 4144342
    Abstract: Mercaptoalkylpyridines carrying an ethenyl or ethynyl substituent are prepared from known pyridine compounds, principally pyridoxine, by known chemical procedures, and are useful in the treatment of rheumatoid arthritis and related inflammatory diseases.
    Type: Grant
    Filed: October 17, 1977
    Date of Patent: March 13, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Tsung-Ying Shen, Howard Jones, Conrad P. Dorn
  • Patent number: 4144341
    Abstract: 1,3-Dihydroimidazo[4,5-b]pyridin-2-ones and corresponding thiones have utility as analgesic, antipyretic and antiinflammatory agents. They are generally prepared by treatment of a 2,3-diaminopyridine with phosgene or thiosphosgene followed by further substitution if desired.
    Type: Grant
    Filed: November 22, 1977
    Date of Patent: March 13, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Robert L. Clark, Arsenio A. Pessolano, Tsung-Ying Shen
  • Patent number: 4144271
    Abstract: N-substituted mercaptomethylacetamidines are prepared, and are useful as immunoregulants for correcting an imbalance of immune homeostasis, particularly, as immunostimulants in the treatment of autoimmune and immune deficient diseases and disorders.
    Type: Grant
    Filed: October 25, 1977
    Date of Patent: March 13, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Howard Jones, Conrad P. Dorn
  • Patent number: 4140719
    Abstract: A method of preparing 2,4-difluoroaniline by reacting 2,4,5-trichloronitrobenzene with a fluorinating agent in the presence of a solid-liquid phase interface, and utilizing a phase transfer catalyst to form 2,4-difluoro-5-chloronitrobenzene, followed by hydrogenation with hydrogen in the presence of a hydrogenation catalyst to form 2,4-difluoroaniline.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: February 20, 1979
    Assignee: Merck & Co., Inc.
    Inventors: Roger J. Tull, Leonard M. Weinstock, Ichiro Shinkai
  • Patent number: 4131618
    Abstract: The invention relates to an improved method of preparing salicylic acid and derivatives from phenyl esters which comprises the step of fusing acetoxyphenyl, or derivative suitable for preparing the desired salicylic acid derivative, with M.sub.2 CO.sub.3 where M is potassium or sodium in the presence of carbon dioxide, at a temperature of from 150.degree. to 250.degree. C., and at a pressure of from atmospheric to 500 p.s.i.g.
    Type: Grant
    Filed: December 29, 1977
    Date of Patent: December 26, 1978
    Assignee: Merck & Co., Inc.
    Inventors: Leonard M. Weinstock, Arthur S. Wildman, Dennis M. Mulvey
  • Patent number: 4131677
    Abstract: The various isomers of oxazolo- and thiazolopyridines having utility as antiinflammatory, antipyretic and analgesic agents are prepared by condensation of an appropriate amino-hydroxypyridine or amino-mercaptopyridine with a carboxylic acid, halide or anhydride.
    Type: Grant
    Filed: April 27, 1977
    Date of Patent: December 26, 1978
    Assignee: Merck & Co., Inc.
    Inventors: Tsung-Ying Shen, Robert L. Clark, Arsenio A. Pessolano, Bruce E. Witzel, Thomas J. Lanza