Patents Represented by Attorney Alan M. Krubiner
  • 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: 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: 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: 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
  • Patent number: 4054579
    Abstract: 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids, and esters and salts thereof, are prepared by solvolysis of nitrile or amide intermediates, or of ketal-protected nitrile, amide, acid, ester or salt intermediates.
    Type: Grant
    Filed: June 21, 1976
    Date of Patent: October 18, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch, James P. Dunn
  • Patent number: 4051260
    Abstract: 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where one of R.sup.2 and R.sup.3 is hydrogen, and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene; and R' and R.sup.4 are alkoxy, or together R' and R.sup.4 are .dbd.O, .dbd.NOH, .dbd.NNHCONH.sub.2, or alkylenedioxy of the formula --O--CH.sub.2 --(CR.sup.5.sub.2).sub.n --CH.sub.2 --O-- where n.sub.5 is O-2, R.sup.5 is hydrogen or methyl when n is 1, and R.sup.5 is hydrogen when n is 2, or one of R' and R.sup.4 is --OH and the other is (SO.sub.3 Y) where Y is sodium or potassium. The compounds have anti-inflammatory, analgesic and anti-pyretic activities and, accordingly, are useful in the treatment of inflammation, pain and pyrexia.
    Type: Grant
    Filed: April 8, 1976
    Date of Patent: September 27, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch
  • Patent number: 4051233
    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: May 10, 1976
    Date of Patent: September 27, 1977
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison
  • Patent number: 4048330
    Abstract: Compositions containing 2-(6'-substituted-2'-naphthyl)acetic acid derivatives substituted at the 2-position of the acetic acid moiety with methyl, ethyl, difluoromethyl, or methylene, and the salts and esters thereof, having anti-inflammatory, analgesic and anti-pyretic activities, and methods for the use thereof in the treatment of inflammation, pain and pyrexia.
    Type: Grant
    Filed: August 18, 1975
    Date of Patent: September 13, 1977
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison
  • Patent number: 4046877
    Abstract: Human serum prealbumin is shown to possess thymus hormone-like properties of increasing immunologic competence. Pharmaceutical compositions containing this material, useful for increasing immunologic competence, are described.
    Type: Grant
    Filed: February 17, 1976
    Date of Patent: September 6, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Abraham White, Pamela M. Burton
  • Patent number: 4045568
    Abstract: Compounds of the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is 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; the other of R.sup.1 and R.sup.2 is alkyl, cyclohexyl, cyclohexyl lower alkyl or cyclohexyl substituted with from 1 to 3 lower alkyl groups; 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: March 8, 1976
    Date of Patent: August 30, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Keith A. M. Walker
  • Patent number: 4045485
    Abstract: 2-(2'-Naphthyl) acetaldehyde derivatives optionally substituted at the 2 position and/or positions C-1',4',5',7' or 8'; and/or position C-6' or positions C-5' and 7' exhibit anti-inflammatory, analgesic, antipyretic and anti-pruritic activity.
    Type: Grant
    Filed: November 5, 1976
    Date of Patent: August 30, 1977
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison
  • Patent number: 4038299
    Abstract: 2-Substituted-5-oxo-5H-dibenzo [a,d] cycloheptenes represented by the following formula: ##STR1## where one of R.sup.2 and R.sup.3 is hydrogen, and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene; the dotted line represents an optional, additional bond between the carbon atoms at the 10- and 11-positions; and the pharmaceutically acceptable esters and ethers thereof. The compounds have anti-inflammatory, analgesic, and antipyretic activities and, accordingly, are useful in the treatment of inflammation, pain and pyrexia.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: July 26, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch
  • Patent number: 4036970
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently benzyl substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R.sup.2 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: July 19, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Keith A. M. Walker, Michael Marx
  • Patent number: 4036975
    Abstract: Compounds of the formula ##STR1## wherein R is alkyl, cycloalkyl, cycloalkyl lower alkyl, phenyl or phenyl lower alkyl, said phenyl and phenyl lower alkyl optionally substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; and X is oxygen or sulfur with the proviso that X is not oxygen when R is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: July 19, 1977
    Assignee: Xyntex (U.S.A) Inc.
    Inventors: Keith A. M. Walker, Stefan Howard Unger
  • Patent number: 4036974
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are independently alkyl or the group ##STR2## IN WHICH N IS 0 TO 3; X and Y are independently oxygen or sulfur; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: July 19, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Keith A. M. Walker, Michael Marx
  • Patent number: 4036973
    Abstract: Compounds of the formula ##STR1## wherein one of R.sup.1 and R.sup.2 is alkyl or the group ##STR2## IN WHICH N IS 0 TO 3 AND THE OTHER OF R.sup.1 and R.sup.2 is benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with one or more substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X and Y are independently oxygen or sulfur with the proviso that Y is not oxygen when R.sup.2 is phenyl or substituted phenyl; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: July 19, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Keith A. M. Walker, Michael Marx
  • Patent number: 4035509
    Abstract: 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR2## where n is an integer from 2 to 4, inclusive, and R.sup.4 and R.sup.5 are independently lower alkyl having 1 to 6 carbon atoms or together R.sup.4 and R.sup.5 and the nitrogen atom to which they are attached form a heterocyclic ring having 5 or 6 total ring atoms; and the pharmaceutically acceptable salts thereof. The compounds are useful in the treatment of auto-immune diseases and allergic reactions.
    Type: Grant
    Filed: March 31, 1975
    Date of Patent: July 12, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch
  • Patent number: 4033978
    Abstract: 3-Carboxy-5-substituted-thiacycl[2.2.2]azines of the formula: ##STR1## wherein R is phenyl or phenyl monosubstituted in the meta or para position with fluoro, chloro, lower alkyl of from 1 to 4 carbon atoms or lower alkoxy of from 1 to 4 carbon atoms, and the pharmaceutically acceptable salts thereof.These compounds are useful as anticomplimentary agents, specifically for the treatment of inflammatory conditions, auto-immune diseases, allergic reactions and vascular diseases.
    Type: Grant
    Filed: August 15, 1975
    Date of Patent: July 5, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Karl G. Untch, John O. Gardner
  • Patent number: 4020094
    Abstract: 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where R' is hydrogen, alkyl having 1 to 12 carbon atoms, or ##STR2## where n is an integer from 2 to 4, inclusive, and R.sup.4 and R.sup.5 are independently lower alkyl having 1 to 6 carbon atoms or together R.sup.4 and R.sup.5 and the nitrogen atom to which they are attached form a heterocyclic ring having 5 or 6 total ring atoms; one of R.sup.2 and R.sup.3 is hydrogen and the other is hydrogen, methyl, or ethyl, or together R.sup.2 and R.sup.3 are methylene; and the pharmaceutically acceptable salts thereof. The compounds have anti-inflammatory, analgesic, and antipyretic activities and, accordingly, are useful in the treatment of inflammation, pain and/or pyrexia.
    Type: Grant
    Filed: March 24, 1975
    Date of Patent: April 26, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch
  • Patent number: 4011243
    Abstract: 2-(5H-Dibenzo[a,d]cyclohepten-5-on-2-yl)acetic, propionic and butyric acids are prepared by oxidation of the corresponding 5-oxo- or ketal-protected oxoalcohols and aldehydes. The acid products exhibit anti-inflammatory, analgesic and anti-pyretic activity.
    Type: Grant
    Filed: September 8, 1975
    Date of Patent: March 8, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch