Patents Represented by Attorney Alan M. Krubiner
  • Patent number: 4207241
    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, antipyretic 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 27, 1978
    Date of Patent: June 10, 1980
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison
  • Patent number: 4178457
    Abstract: Novel 16-phenoxy and 16-(o, m or p)-substituted phenoxy derivatives of (dl)-9-keto-11.alpha.,15.alpha.-dihydroxy-17,18,19,20-tetranorprosta-4,5,1 3-trans-trienoic acid, the pharmaceutically acceptable, non-toxic lower alkyl esters and salts thereof and processes for the production of such compounds. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretion; and as agents for the control of asthmatic attack, because of their bronchodilating activity.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: December 11, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Albert R. Van Horn, Gabriel Garay, John A. Edwards
  • Patent number: 4174399
    Abstract: 6-(N-vinylureido)penicillanic acids and salts thereof; and processes for preparing such compounds are disclosed. The compounds are useful as inhibitors of lactic acidosis in ruminants.
    Type: Grant
    Filed: July 10, 1978
    Date of Patent: November 13, 1979
    Assignee: Syntex (USA) Inc.
    Inventors: Arthur F. Kluge, Ian T. Harrison
  • Patent number: 4172949
    Abstract: Compounds of the formula ##STR1## wherein R is hydrogen or methyl; R.sup.1 is hydrogen, C.sub.1 to C.sub.8 linear or branched alkyl or C.sub.1 to C.sub.8 linear or branched alkanoyl; X is oxygen or sulfur; R.sup.2 is selected from the group hydrogen, C.sub.1 to C.sub.18 linear or branched alkyl and the radicals --(CH.sub.2).sub.n --NR.sup.3 R.sup.4, --CH.sub.2 --CH(OH)--CH.sub.2 --OH or a ketal thereof formed from the aldehyde or ketone R.sup.5 R.sup.6 CO, wherein R.sup.3 and R.sup.4 are each independently C.sub.1 to C.sub.6 linear or branched alkyl or R.sup.3 and R.sup.4 taken together with the nitrogen atom of the first radical are attached to form a 5- or 6-membered heterocyclic ring, R.sup.5 and R.sup.6 are each independently hydrogen, C.sub.1 to C.sub.6 linear or branched alkyl, phenyl or benzyl or R.sup.5 and R.sup.
    Type: Grant
    Filed: June 28, 1978
    Date of Patent: October 30, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: James P. Dunn, Peter H. Nelson, Karl G. Untch
  • Patent number: 4172141
    Abstract: Compounds of the formula ##STR1## wherein R is alkyl, benzyl, substituted benzyl, phenyl or substituted phenyl, said substituted benzyl and substituted phenyl substituted on the phenyl ring with from one to three substituents independently selected from the group consisting of halo, lower alkyl and trifluoromethyl; X is oxygen or sulfur; and the pharmaceutically acceptable acid addition salts thereof are CNS-active agents, inhibitors of gastric secretion and antifungal, antibacterial and antiprotozoal agents.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: October 23, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Keith A. M. Walker
  • Patent number: 4172204
    Abstract: A method for preparing 4,5-dihydro-2-alkoxycarbonylamino-5-carbocyclic aryl imidazoles and substituted aryl derivatives thereof is disclosed. The compounds are prepared by treating a 1-(carbocyclic aryl)-2-(2',3'-bis-carboalkoxyguanidino) ethane of the formula ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, R' is phenyl optionally substituted with the radical methylenedioxy or at least one hydroxy, halo, trifluoromethyl, C.sub.1 to C.sub.6 linear or branched alkoxy, or 1-naphthyl or 2-naphthyl and X is halo, mesyloxy or tosyloxy with a protic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide. 1-(Optionally substituted carbocyclic aryl)-2-(carboalkoxyguanidino) ethanes are also disclosed herein, such prepared by treating the above bis-carboalkoxyguanadino ethane with an aprotic solvent solution or dispersion of an alkali metal or alkaline earth metal hydroxide, carbonate or alkoxide.
    Type: Grant
    Filed: October 7, 1977
    Date of Patent: October 23, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Charles A. Dvorak, Colin C. Beard
  • Patent number: 4158012
    Abstract: The tricyclic intermediate ##STR1## is prepared in a three step sequence from the bicyclic intermediate ##STR2## The key step of this process involves the addition of a Grignard reagent to a mixed anhydride. Tricyclic compound of formula (I) may be readily converted by known methods to valuable steroids.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: June 12, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Albert R. Van Horn
  • Patent number: 4150153
    Abstract: Compounds of the formula ##STR1## wherein Z is hydroxymethylene, esterified hydroxymethylene, carbonyl, or ketal-, thioketal- or hemithioketal- protected carbonyl, and the pharmaceutically acceptable acid addition salts thereof, are useful as anticonvulsant and anti-secretory agents.
    Type: Grant
    Filed: November 4, 1977
    Date of Patent: April 17, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Keith A. M. Walker
  • Patent number: 4144397
    Abstract: Valuable 2-aryl-propionic acids are prepared by the direct coupling of aryl magnesium bromides with a mixed magnesium halide complex of alpha-bromopropionic acid.
    Type: Grant
    Filed: December 19, 1977
    Date of Patent: March 13, 1979
    Assignee: Syntex Corporation
    Inventors: Gary J. Matthews, Robert A. Arnold
  • Patent number: 4123542
    Abstract: Compounds of the formula ##STR1## wherein R is lower alkyl; R.sup.1 is substituted or unsubstituted phenyl or phenyl straight chain lower alkyl; R.sup.2 is substituted or unsubstituted phenyl, phenyl straight chain lower alkyl or phenyl straight chain lower alkenyl; and wherein said substitution, solely in the phenyl ring of the aforesaid groups, comprises one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, halo and trifluoromethyl; X is oxygen or sulfur; n is an integer of from 1 to 4 with the proviso that n cannot be 1 when X is oxygen and 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 19, 1977
    Date of Patent: October 31, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Keith A. M. Walker
  • Patent number: 4120570
    Abstract: Visual defects of the human eye in the form of refractive errors such as myopia, hyperiopia, astigmatism, athakis and keratoconus are corrected by a therapeutic method which includes the step of fitting to the patient's eye a corrective contact lens fabricated from a copolymer of a polysiloxanylalkyl acrylic ester and an alkyl acrylic ester. These visual corrections are made in accordance with this method with concommitent reduction in corneal edema since lenses so used have improved oxygen permeability. According to the preferred practice of this method, the lenses utilized have improved wettability which increases wearing confort and reduces interference with corneal metabolism, thereby extending the time period during which the corrective effect of the method is achieved. The corrective effect of this method is also enhanced by the capability of the lenses utilized therein to be precisely machined and polished.
    Type: Grant
    Filed: September 6, 1977
    Date of Patent: October 17, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Norman G. Gaylord
  • Patent number: 4112114
    Abstract: Esters of 2-substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes represented by the following formula: ##STR1## where R' is --CH.sub.2 --CH.dbd.CH.sub.2, --CH.sub.2 --CH(OH)--CH.sub.2 OH, ##STR2## where Y is either O or S, or ##STR3## where R.sup.4 and R.sup.5 are independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, or benzyl, or together R.sup.4 and R.sup.5 form an alkylene bridge having 4, 5 or 6 carbon 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. 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: September 2, 1977
    Date of Patent: September 5, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch
  • Patent number: 4100174
    Abstract: 2-(5H-Dibenzo[a,d]cyclohepten-5-on-2-yl) acetic, propionic and butyric acids, are prepared from glycidonitrile intermediates.
    Type: Grant
    Filed: December 6, 1976
    Date of Patent: July 11, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Peter H. Nelson, Karl G. Untch
  • Patent number: 4097674
    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: September 27, 1976
    Date of Patent: June 27, 1978
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison
  • Patent number: 4089980
    Abstract: An NPN ruminant feed supplement having a high percentage of chemically bound urea is prepared from cellulose commodities by an efficient process involving reaction with urea and a dilute mineral acid at low pH.
    Type: Grant
    Filed: February 25, 1977
    Date of Patent: May 16, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Kenneth L. Berger, Jorge J. Nassar, William B. Benken
  • 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: 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: 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: 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