Patents Assigned to Syntex (U.S.A.)
  • Patent number: 4082736
    Abstract: This application relates to novel immunological adjuvant compounds of the formula: ##STR1## wherein each of R and R.sup.1 are the same or different and are hydrogen or an acyl radical; R.sup.2 is an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical; R.sup.6 is an alkyl radical X is an aminoacyl moiety; and Y is D-isoasparagine or D-isoglutamine.
    Type: Grant
    Filed: April 26, 1976
    Date of Patent: April 4, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gordon H. Jones, John G. Moffatt, John J. Nestor, Jr.
  • Patent number: 4080461
    Abstract: Benzene ring substituted benzimidazole-2-carbamate derivatives represented by the formula: ##STR1## 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 O, S, ##STR2## 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; andR.sup.5 is lower alkenyl, lower alkynyl, 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: October 4, 1976
    Date of Patent: March 21, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 4078071
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl or one of the above substituted in the phenyl ring with one or more substituents independently selected from the group consisting of lower alkyl of from one to four carbon atoms, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from 1 to 8 with the proviso that n is not 1 when R.sup.1 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: March 7, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Keith A. M. Walker
  • Patent number: 4076745
    Abstract: A process for the preparation of calcium salts of .alpha.-ketocarboxylic acids comprising reacting an .alpha.-ketocarboxylic acid with an amine, to afford a salt, said salt being soluble in the reaction medium, treating said salt with a source of calcium ion to afford the calcium salt of the .alpha.-ketocarboxylic acid, said salt being substantially insoluble in said reaction medium, and isolating said calcium salt from the reaction medium. This process is especially useful for the preparation of calcium salts of .alpha.-keto analogues of essential .alpha.-amino acids.
    Type: Grant
    Filed: July 8, 1976
    Date of Patent: February 28, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Eric Lodewyk
  • Patent number: 4076657
    Abstract: Polyurethane plastics having improved smoke supression properties due to the incorporation therein of small amount of dicyclopentadienyl iron, or derivatives thereof, in chemically uncombined form. The improved polyurethane plastics are prepared by simple physical admixture of the dicyclopentadienyl iron, or derivatives thereof, in the plastic.
    Type: Grant
    Filed: March 12, 1976
    Date of Patent: February 28, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: John J. Kracklauer
  • Patent number: 4076981
    Abstract: A position sensitive detector including a curved detector housing having a hollow detector chamber therein, the housing having an elongate opening in the curved side wall thereof and an x-ray transmissive material adjacent thereto to render the detector chamber air-tight, a back cathode plane comprising a plurality of spaced cathode conductors on an insulator support and at least one curved anode wire, extending at least substantially transverse to the back cathode plane, disposed within the detector chamber in the path of x-rays entering through the elongate opening. Each anode wire, which is mechanically supported only at the ends thereof, is caused, during operation of the detector, to be supported in planar arcuate form solely by electrostatic forces. During operation of the detector, the chamber is filled with an ionizable gas and voltage is applied to the curved anode wire(s), thereby enabling detection of ionizing events occuring within the detector chamber.
    Type: Grant
    Filed: July 29, 1976
    Date of Patent: February 28, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Robert A. Sparks, George B. Rothbart, Roger N. Samdahl
  • Patent number: 4072696
    Abstract: Carbalkoxythioureidobenzene derivatives represented by the following formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; R.sup.1 is --SR.sup.2, --SOR.sup.2, --SO.sub.2 R.sup.2, --OR.sup.2, --SCN, --SC(O)NR.sup.3 R.sup.4, or --M'(CH.sub.2).sub.n MR.sup.7 where n is 1-4; R.sup.2 is lower alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, lower alkenyl or lower alkynyl having 3 to 6 carbon atoms, aralkyl or aryl, provided that when R.sup.1 is --SO.sub.2 R.sup.2, R.sup.2 is not aralkyl or phenyl; R.sup.3 and R.sup.4 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; Y is amino, nitro, acylamino where the acyl portion has 1 to 6 carbon atoms, --NHC(O) (CH.sub.2).sub.m COOH where m is 1-6, or --NHC(S)NHCOOR; M and M' are independently O, S or ##STR2## and R.sup.7 is lower alkyl having 1 to 4 carbon atoms or aryl. The R.sup.1 substitution is either at the 4- or 5-position.
    Type: Grant
    Filed: January 18, 1974
    Date of Patent: February 7, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 4070453
    Abstract: Diploid porcine embryonic cell strains, method of growing same from porcine embryonic tissue, culturing and subculturing said diploid cell strains, and preparing a virus vaccine (exemplary of the virus vaccine thus prepared is a porcine transmissible gastroenteritis virus vaccine) from said diploid cell strain cultures. A novel nutrient growth medium composition for culturing and subculturing by serial subcultivation is also disclosed.
    Type: Grant
    Filed: June 25, 1976
    Date of Patent: January 24, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Dale Emil Bordt, Phillip Clay Thomas
  • Patent number: 4066663
    Abstract: The novel compounds 6,11-dihydrodibenzo[b.e.]-thiepin-11-one-3-acetaldehyde and (dl) 2(6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)propionaldehyde, certain dialkyl- and cyclic acetals thereof, and processes and novel intermediates for making same.
    Type: Grant
    Filed: July 1, 1976
    Date of Patent: January 3, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Jack Ackrell
  • Patent number: 4064878
    Abstract: An inhalation device having an elongate housing having a passageway for the movement of air therethrough. The passageway terminates in an emptying chamber adjacent that end of the housing which is adapted for insertion into the mouth or nasal passages of a user thereof. The housing has means for receiving and opening a container holding a unit dose of powdered medicament for administration. The opening means includes first means for placing the interior of the opened capsule in communication with the atomosphere and second means for placing the interior of the opened capsule in communication with the emptying chamber via the passageway in the housing. During inhalation, air drawn through the first means causes the powdered medicament to be expelled from the container through the second means, the passageway and the emptying chamber into the nose, throat or lungs of the user where beneficial or therapeutic action of the medicament occurs.
    Type: Grant
    Filed: October 26, 1976
    Date of Patent: December 27, 1977
    Assignee: Syntex Puerto Rico, Inc.
    Inventor: Ingemar H. Lundquist
  • Patent number: 4065452
    Abstract: Novel, topically-active anti-inflammatory steroids are represented by the formula ##STR1## wherein X is fluoro, chloro or hydrogen; X.sup.1 is fluoro, chloro, bromo, or hydrogen; X.sup.2 is hydroxy or may be chloro when X.sup.1 is chloro; and X.sup.3 and X.sup.4 are independently fluoro, chloro or bromo. These steroids are prepared by formylating at the 21-position a 16.alpha.,17.beta.-isopropylidenedioxypregna-1,4,9(11)-triene-3,20-dione or the corresponding 21-fluoro compound, halogenating at the 21 position, deformylating, then reacting to add the desired components at the 9.alpha. and 11.beta. positions.
    Type: Grant
    Filed: August 2, 1976
    Date of Patent: December 27, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Tsung-tee Li, Michael Marx, Lewis J. Throop
  • Patent number: 4064135
    Abstract: Processes and intermediates for preparing 1-alkylamino-3-(5-substitutedaminocarbonylthiazol-2-yloxy)-2-propanols and 5-(5-substitutedaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine and 2-substituted oxazolidine derivatives thereof and intermediates therefore. The present processes, and intermediates, reduce the number of transformations necessary to produce these products as compared with the prior processes. The products are useful to treat abnormal heart conditions and/or hypertension in mammals. The intermediates are 2-alkylsulfinyl-5-substitutedaminocarbonylthiazoles and 2-alkylsulfonyl-5-substitutedaminocarbonylthiazoles.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Belig M. Berkoz, Brian Lewis, Joseph M. Muchowski
  • Patent number: 4064141
    Abstract: Esters of 6,11-dihydrodibenzo-[b.e.]-thiepin-11-ones of the formula: ##STR1## wherein R is hydrogen or methyl and R.sup.1 is --CH.sub.2 --CH(OH)--CH.sub.2 OH, ##STR2## where Y is either O or S, or ##STR3## where R.sup.2 and R.sup.3 are independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl or benzyl or together R.sup.2 and R.sup.3 form an alkylene bridge having 4, 5 or 6 carbon atoms, and processes for the production thereof.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Jack Ackrell
  • Patent number: 4064240
    Abstract: 21-Cyclic acetals of steroids of the corticoid series are prepared from the corresponding 21-hydroxy steroids. The products have utility as anti-inflammatory agents.
    Type: Grant
    Filed: November 17, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Michael Marx, Denis John Kertesz
  • Patent number: 4064257
    Abstract: 1-Alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-alkynylaminocarbonyl-thiazol-2-yloxymethylene)-N-alkyloxazolidine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-alkynyl-aminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives are also intermediates for the 1-alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanols. The 1-alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanols can be prepared by base or acid hydrolysis of the corresponding 5-(5-alkynylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine or derivative; or by treatment of the corresponding 3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Belig M. Berkoz, Brian Lewis, Stefan H. Unger
  • Patent number: 4064258
    Abstract: 1-Alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene-N-alkyloxazolid ine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dines and derivatives are also intermediates for the 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s. The 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s can be prepared by base or acid hydrolysis of the corresponding 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dine or derivative; or by treatment of the corresponding 3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Brian Lewis, Stefan H. Unger, Karl G. Untch
  • Patent number: 4064259
    Abstract: 1-Alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives are also intermediates for the 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols. The 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols can be prepared by base or acid hydrolysis of the corresponding 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine or derivative; or by treatment of the corresponding 3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.
    Type: Grant
    Filed: July 19, 1976
    Date of Patent: December 20, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Belig M. Berkoz, Brian Lewis, Stefan H. Unger
  • Patent number: 4059611
    Abstract: 2-(5H-Dibenzo[a,d]cyclohepten-5-on-2-yl) acetic, propionic and butyric acid, and esters and salts thereof, are prepared by oxidation of non-ketonic intermediates.
    Type: Grant
    Filed: July 6, 1976
    Date of Patent: November 22, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch
  • Patent number: 4059705
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each independently alkyl, cyclohexyl substituted with from one to three lower alkyl groups, or a group of the formula ##STR2## WHEREIN M IS AN INTEGER OF FROM 0 TO 3 AND P IS AN INTEGER OF FROM 1 TO 3; X is sulfur or oxygen; n is an integer of from 1 to 8; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: November 22, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Keith A. M. Walker
  • Patent number: 4055652
    Abstract: Novel 1-[.beta.-(R-thio)phenethyl]-imidazoles and the corresponding 1-[.beta.-(R-sulfinyl)phenethyl]imidazoles and 1-[.beta.-(R-sulfonyl)phenethyl]imidazoles wherein R is alkyl, alkenyl, aralkenyl, substituted aralkenyl, alkynyl, cycloalkyl, cycloalkyl alkyl, aralkyl, substituted aralkyl, aryl or substituted aryl; and the antimicrobial acid addition salts thereof, are useful as antifungal, anti-bacterial and anti-protozoal agents.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: October 25, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Keith A. M. Walker