Patents Assigned to Syntex (U.S.A.)
  • Patent number: 3998966
    Abstract: 2-Naphthyl acetic acid derivatives and the corresponding amides, esters, hydroxamic acids and addition salts thereof, optionally substituted at the .alpha.-position on the acetic acid moiety and/or at position 6 and/or at positions 1, 4, 7 or 8 on the naphthyl ring and optionally saturated at positions 3 and 4, are anti-inflammatory, analgesic, anti-pyretic and anti-pruritic agents. A pharmaceutical method of effecting treatment of inflammation, pain, pyrexia and pruritus by the administration of naphthyl acetic acid derivatives. A pharmaceutical composition for use in the treatment of the above maladies comprising a naphthyl acetic acid derivative.
    Type: Grant
    Filed: March 17, 1975
    Date of Patent: December 21, 1976
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison
  • Patent number: 3997587
    Abstract: d1- and 8R-9-fluoro-11,15.alpha.-dihydroxyprosta-5-cis,13-trans-dienoic acid, d1- and 8R-9-fluoro-11,15.alpha.-dihydroxy-15.beta.-methyl-prosta-5-cis,13-trans-d ienoic acid and d1- and 8R-9-fluoro-11,15.beta.-dihydroxy-15.alpha.-methylprosta-5-cis,13-trans-di enoic acid, the pharmaceutically acceptable, nontoxic lower alkyl esters and salts thereof and process for the production of such compounds. 8R-9.beta.-fluoro-11.alpha.,15.alpha.-dihydroxyprosta-5-cis,13-trans-dieno ic acid is a representative compound of the class. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as luteolytic agents in female mammals and as bronchodilators.
    Type: Grant
    Filed: June 26, 1975
    Date of Patent: December 14, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Esperanza V. Velarde
  • Patent number: 3996358
    Abstract: 21-Esters of 21-aldehyde hydrates and 21-aldehyde hemiacetals of steroids of the corticoid series are prepared from the corresponding 21-hydroxy steroids and have utility as antiinflammatory agents.
    Type: Grant
    Filed: July 7, 1975
    Date of Patent: December 7, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Michael Marx, Denis John Kertesz
  • Patent number: 3995158
    Abstract: Means for supporting an object, or a portion thereof, during radiographic analysis comprising a hollow reservoir adapted to receive and hold a constant volume of fluid material within the interior thereof, said reservoir having a pouch-like flexible member forming all or a portion of one wall thereof, said pouch-like flexible member being adapted to receive and support the object undergoing analysis during radiographic exposure thereof, a second flexible member forming all or a portion of a second wall thereof, and means operatively connected to said second flexible member for moving said second flexible member so as to cause a corresponding movement of said pouch-like flexible member. During use, the second flexible member is moved in such a manner as to cause an enlargement of the pouch-like deformation of the pouch-like flexible member.
    Type: Grant
    Filed: October 15, 1975
    Date of Patent: November 30, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Samuel Thomas Workman
  • Patent number: 3994968
    Abstract: New compounds, 2-(6'-methoxynaphth-2'-yl)-propylene oxide, 2-(6'-methoxynaphth-2'-yl)proppionaldoxime, 2-hydroxy-2-(6'-methoxynaphth-2'-yl)-propionitrile, 2-(6'-methoxynaphth-2'-yl)acrylonitrile, 2-(6'-methoxynaphth-2'-yl)acrylic acid, the corresponding 5'-halo compounds and 2-(5'-halo-6'-methoxynaphth-2'-yl)propionaldehyde are useful intermediates in producing 2-(6'-methoxynaphth-2'-yl)propionic acid and the corresponding 5'-halo acids from 6-methoxy-2-acetylnaphthalene and the corresponding 5-halo compounds. The 2-propionic acids are anti-inflammatory, analgesic, anti-pyretic and anti-pruritic agents. The 2-propionaldehydes, obtained from the 2-acetyl compounds by way of the 2-propylene oxide, can be converted directly to the 2-propionic acids by way of the 2-propionaldoximes and the 2-priopionitriles or more directly by Jones oxidation.
    Type: Grant
    Filed: January 12, 1976
    Date of Patent: November 30, 1976
    Assignee: Syntex Corporation
    Inventor: Francisco Sanchez Alvarez
  • Patent number: 3993669
    Abstract: Novel C-2 mono- and C-2,3-disubstituted 1.4-benzopyrone-6-carboxylic acids and derivatives thereof which are useful as bronchiodilators. Methods for preparing these compounds are also disclosed.
    Type: Grant
    Filed: April 17, 1975
    Date of Patent: November 23, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Jurg R. Pfister
  • Patent number: 3993746
    Abstract: Feeds, medicaments, and baits for inducing exploratory feeding behavior in fish and crustacea which comprise monosodium glutamate and alkali metal aspartate in combination with conventional fish or crustacea food or with a medicament or, in the case of baits, with a non-toxic bulk material.
    Type: Grant
    Filed: April 10, 1975
    Date of Patent: November 23, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Myron A. Beigler, Ronald J. Amen
  • Patent number: 3993768
    Abstract: This application describes further species embraced by the following generic formula: ##SPC1##Where R is a lower alkyl group having 1 to 4 carbon atoms; R.sup.1 is --SOR.sup.2, --SO.sub.2 R.sup.2, --SCN, --SR.sup.5, --OR.sup.5 or M'(CH.sub.2).sub.n MR.sup.7 where M and M' are independently ##EQU1## R.sup.7 is lower alkyl having 1 to 4 carbon atoms or aryl, and n is 1-4; R.sup.2 is lower alkyl having from 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, or aralkyl or aryl; R.sup.5 is lower alkenyl, lower alkynyl, or aralkyl; and the R.sup.1 substitution is at the 5(6)-position. The above compounds can also be substituted at the 1-position.
    Type: Grant
    Filed: August 13, 1975
    Date of Patent: November 23, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 3993769
    Abstract: This application relates to 1,5(6)-disubstituted benzimidazole-2-carbamate derivatives represented by the following formula: ##SPC1##Where R is lower alkyl having 1 to 4 carbon atoms; R.sup.1 is --SOR.sup.2, --SR.sup.5, --OR.sup.5 or M'(CH.sub.2).sub.n MR.sup.7 ; R.sup.2 is lower alkyl having from 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, or aralkyl or aryl; R.sup.5 is lower alkenyl, lower alkynyl or aralkyl; R.sup.7 is lower alkyl having 1 to 4 carbon atoms or aryl;M and M' are independently ##EQU1## n is 1-4; AND R.sup.8 is lower alkyl having 1 to 12 carbon atoms optionally substituted with a --COOR group where R is lower alkyl having 1 to 4 carbon atoms, aryl or aralkyl. The R.sup.1 substitution is at the 5(6)-position.The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.
    Type: Grant
    Filed: August 18, 1975
    Date of Patent: November 23, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 3992541
    Abstract: This application describes analgesic formulations including d 2-(6-methoxy-2-naphthyl)propionic acid, or a pharmaceutically acceptable salt or ester thereof, in combination with at least one central nervous system active analgesic compound. Analgesic activity of the combination is greater than that obtained with either of the components alone, thus demonstrating enhanced analgesia which can be obtained therewith.
    Type: Grant
    Filed: August 4, 1975
    Date of Patent: November 16, 1976
    Assignee: Syntex Corporation
    Inventor: Martin Katz
  • Patent number: 3991750
    Abstract: Dromostanolone propionate has been found to result in a surprisingly large increase in weight in animals when administered as a pellet implant. In female animals, e.g. heifers, estrus is also suppressed. A particularly effective implant pellet exhibits a substantially constant rate of drug delivery over a first time period and an abrupt termination of drug delivery at the end of said time period, thus eliminating the need to surgically remove the implanted pellet to stop administration of the drug to the animal.
    Type: Grant
    Filed: April 28, 1975
    Date of Patent: November 16, 1976
    Assignee: Syntex Corporation
    Inventor: Brian H. Vickery
  • Patent number: 3992630
    Abstract: Means for supporting an object, or a portion thereof, during radiographic analysis comprising a hollow reservoir adapted to receive and hold a constant volume of fluid material within the interior thereof, said reservoir having a pouch-like flexible member forming all or a portion of one wall thereof, said pouch-like flexible member being adapted to receive and support the object undergoing analysis during radiographic exposure thereof, a second flexible member forming all or a portion of a second wall thereof, and means operatively connected to said second flexible member for moving said second flexible member so as to cause a corresponding movement of said pouch-like flexible member. During use, the second flexible member is moved in such a manner as to cause an enlargement of the pouch-like deformation of the pouch-like flexible member.
    Type: Grant
    Filed: October 15, 1975
    Date of Patent: November 16, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Josef E. Kercso
  • Patent number: 3989839
    Abstract: This invention relates to novel 6,11-dihydrodibenzo-[b.e.]-thiepin-11-ones, methods of preparation, compositions and uses thereof.
    Type: Grant
    Filed: August 13, 1975
    Date of Patent: November 2, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Jack Ackrell
  • Patent number: 3989721
    Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylsulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
    Type: Grant
    Filed: December 4, 1975
    Date of Patent: November 2, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Jurg R. Pfister, Ian T. Harrison, John H. Fried
  • Patent number: 3989720
    Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylsulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
    Type: Grant
    Filed: December 4, 1975
    Date of Patent: November 2, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Jurg R. Pfister, Ian T. Harrison, John H. Fried
  • Patent number: 3989731
    Abstract: Production of dimers of dicyclopentadienyl iron compounds by the reaction of a dicyclopentadienyl iron compound and a coupling agent in the presence of an acid catalyst in an organic solvent. The process involves a two-phase system wherein one phase comprises said coupling agent, a strong acid, and a polar organic solvent; and the second phase comprises said iron compound which is slightly soluble in the first phase. Dimers of dicyclopentadienyl iron compounds are excellent anti-oxidants and are also useful in controlling the rate of combustion of solid combustion mixtures.
    Type: Grant
    Filed: September 13, 1968
    Date of Patent: November 2, 1976
    Assignee: Syntex Corporation
    Inventor: Meldon L. Talbot
  • Patent number: 3988352
    Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylsulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
    Type: Grant
    Filed: December 4, 1975
    Date of Patent: October 26, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Jurg R. Pfister, Ian T. Harrison, John H. Fried
  • Patent number: 3988365
    Abstract: Resolution of mixtures of d and 1,2-(6-methoxy-2-napthyl)propionic acid with cinchonidine to yield the d-isomer is conducted by using, in combination with the cinchonidine, an inorganic base having a basicity, pKa, greater than 8 and forming a salt of 2-(6-methoxy-2-napthyl)propionic acid more soluble than the solubility of the corresponding cinchonidine salts. After the cinchonidine salt product is cleaved by treatment with a strong base at about room temperature in methanol, the methanolic solution is mixed with sufficient water to precipitate the cinchonidine in a form which is easy to filter. After removal of the precipitated cinchonidine, acidification yields a product enriched in d 2-(6-methoxy-2-napthyl)propionic acid.
    Type: Grant
    Filed: January 13, 1975
    Date of Patent: October 26, 1976
    Assignee: Syntex Corporation
    Inventor: Pasquale Gallegra
  • Patent number: 3987198
    Abstract: A method of lowering the free fatty acid content in sebum on the skin surface by topically applying a member of a certain class of fatty acid amides to the affected skin area. Oleic acid diethanolamide is illustrated as a representative of the useful class. After cleansing, rinsing and drying the skin area to be treated, the fatty acid amide formulation is applied thereto and left thereon for beneficial action to occur.
    Type: Grant
    Filed: January 17, 1975
    Date of Patent: October 19, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: John M. Young
  • Patent number: 3985791
    Abstract: Novel racemic and 8R-antimeric 16-phenoxy- and 16-(o, m or p)-substituted phenoxy derivatives of 9.alpha., 11.alpha.,15-trihydroxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acids, which may be further substituted at C-15 by a methyl or ethyl group, the pharmaceutically acceptable, non-toxic lower alkyl esters and salts thereof and processes for the production of such compounds. dl 9.alpha.,11.alpha.,15.alpha.-trihydroxy-16-m-trifluoromethylphenoxy-17,18, 19,20-tetranorprosta-4,5,13-trans-trienoic acid and dl 9.alpha.,11.alpha.,15 -trihydroxy-15 -methyl-16-m-trifluoromethylphenoxy-17,18,19,20-tetranorprosta-4,5,13-tran s-trienoic acid are representative compounds of the class. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as luteolytic agents in female mammals.
    Type: Grant
    Filed: December 22, 1975
    Date of Patent: October 12, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, John H. Fried