Patents Assigned to Syntex (U.S.A.)
  • 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: 4169703
    Abstract: This invention is a composition useful for dyeing keratinous fiber red without using o-, m- or p-phenylenediamine, 2,4-diaminoanisole or nitro compounds. The composition consists essentially of .alpha.-hydroxynaphthalene, p-aminophenol, a suitable modifier, a suitable coupler and a suitable base. This composition is combined with an oxidizing agent before contacting the hair to dye hair red.
    Type: Grant
    Filed: August 3, 1978
    Date of Patent: October 2, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Najib M. Fakhouri
  • Patent number: 4169704
    Abstract: This invention is a composition useful for dyeing keratinous fiber blond without using o-, m- or p-phenylenediamine, 2,4-diaminoanisole or nitro compounds. The composition consists essentially of m-aminophenol, p-aminophenol, p-methylaminophenol or a suitable acid addition salt thereof, a suitable modifier, a suitable coupler and a suitable base. This composition is combined with an oxidizing agent before contacting the hair to dye hair blond.
    Type: Grant
    Filed: August 3, 1978
    Date of Patent: October 2, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Najib M. Fakhouri
  • 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: 4151297
    Abstract: 1-Alkylamino-3-(3- or 4-[2-(endobicyclo[3.1.0]-hex-6-yl)ethylaminocarbonyl]-1-phenoxy)-2-propano l and substituted derivatives thereof and methods for preparing such compounds are disclosed. 5-(3- Or 4-[2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]-phenoxy)methyl 3-alkyl-2-optionally substituted oxazolidine and derivatives thereof, and methods for preparing such compounds are also disclosed. These compounds exhibit cardiovascular acitivity and are useful in the treatment of abnormal heart condition as well as hypertension in mammals. The former compounds are prepared by treatment of the corresponding 1,2-epoxy-3-(3- or 4-[2-(endobicyclo[3.1.0]hex-6-yl)-ethylaminocarbonyl]phenoxy)propane with the desired alkylamine or by base or acid hydrolysis of the corresponding 5-(3- or 4-[2-(endobicyclo[3.1.0]hex-6-yl)-ethylaminocarbonyl)-3-alkyl oxazolidine. The latter compounds are prepared from the corresponding 1-alkylamino-3-(3- or 4-[2-(endobicyclo[3.1.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: April 24, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Karl G. Untch, Stefan H. Unger, Brian Lewis
  • 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: 4144841
    Abstract: This invention is a filtration and aeration apparatus which comprises (a) an elongated tubular member which is closed at its lower end, open at the opposite end, and provided at its lower portion with a plurality of passages which extend through the longitudinal wall of the tubular member and (b) an air delivery means for supplying air to the interior of said tubular member at a point at or slightly below the lowermost level of said passages so that the air is discharged parallel to the length of said tubular member in the interior of said tubular member. Another aspect of this invention is a unique air delivery means which comprises an air tube connected to and extending into a chamber designed to allow air to escape from said chamber through passages in the chamber walls so that the air is discharged through said chamber wall passages in a direction opposite from the direction said air is delivered to said chamber through said air tube.
    Type: Grant
    Filed: December 22, 1976
    Date of Patent: March 20, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: George D. Bliss, Joseph E. Kercso, Richard J. McGuire
  • Patent number: 4145443
    Abstract: 1-Alkylamino-3-(?2-(endobicyclo?3.1.0!-hex-6-yl)ethylaminocarbonyl!naphthyl oxy)-2-propanols and methods for preparing these compounds are disclosed. The compounds are useful in the treatment of hypertension and abnormal heart conditions in mammals. These compounds are prepared by the treatment of the corresponding 1,2-epoxy-3-?2-(endobicyclo?3.1.0!hex-6-yl)ethylaminocarbonyl!naphthyloxy) -propane with an alkylamine having the desired alkyl substituent or by base or acid hydrolysis of the corresponding 2-optionally substituted -3-alkyl-5-(?2-(endobicyclo?3.1.0!hex-6-yl)ethylaminocarbonyl!naphthyloxym ethyl)oxazolidine. These latter compounds can be prepared by condensing a hydroxy-substituted naphthalene with a 3-alkyl-5-tosyloxymethyloxazolidine such substituted or unsubstituted at the 2-position or alternatively, by treating the former aminopropanol compounds of the present invention with an aldehyde having the desired substituent.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: March 20, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Karl G. Untch, Stefan H. Unger
  • 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: 4140698
    Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein Y is a moiety selected from the group consisting of ##STR2## in which R is hydrogen, methyl, chloro or bromo, the R substitution being at the 3, 4 or 5 positions of the thiophene ring,R.sup.1 is hydrogen, a lower alkyl group having 1 to 4 carbon atoms, a lower alkoxy group having from 1 to 4 carbon atoms, chloro, fluoro or bromo, the R.sup.1 substitution being at the ortho, meta or para positions of the aroyl group, andR.sup.2 is hydrogen or a lower alkyl group having from 1 to 4 carbon atoms, are prepared, by hydrolysis, from their corresponding nitriles.
    Type: Grant
    Filed: May 30, 1978
    Date of Patent: February 20, 1979
    Assignee: Syntex (USA) Inc.
    Inventors: Albert R. Van Horn, Pasquale G. Gallegra
  • Patent number: 4139626
    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; ##STR2## is a 5, 6, 7 or 8 membered heterocyclic ring containing 1 to 2 hetero atoms; the ##STR3## substitution being at the 5(6)-position; and the pharmaceutically acceptable salts thereof.The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.
    Type: Grant
    Filed: January 10, 1977
    Date of Patent: February 13, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Colin Beard
  • Patent number: 4139618
    Abstract: 3-[3-(methyl-1,3,4-thiadiazol-5-ylthio)-prop-1-(t)-enyl]-7.beta.-(.alpha.-s ubstituted acetamido)-ceph-3-em-4-carboxylic acids; 3-[3-(3-methyl-1,2,4-thiadiazol-5-ylthio)-prop-1-(t)-enyl]-7.beta.-(.alpha .-substituted acetamido)-ceph-3-em-4-carboxylic acids; and 3-[3-(2-methyl-1,3,4-oxadiazol-5-ylthio)-prop-1-(t)-enyl]-7.beta.-(.alpha. -substituted acetamido)-ceph-3-em-4-carboxylic acids and derivatives and salts thereof and processes for preparing such compounds. The compounds are useful as antibacterials and are active against a wide variety of gram positive and gram negative bacteria.
    Type: Grant
    Filed: June 28, 1976
    Date of Patent: February 13, 1979
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Philip J. Beeby
  • Patent number: 4131746
    Abstract: (dl)-13-Substituted sulfinyl-prostaglandin-like [(dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-1-oxygenated cyclopentane and (dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-4-oxygenated-1-oxygenated cyclopentane] compounds exhibit prostaglandin-like biological properties and are also useful intermediates in the preparation of known prostaglandins.
    Type: Grant
    Filed: January 7, 1977
    Date of Patent: December 26, 1978
    Assignee: Syntex (USA) Inc.
    Inventors: Karl G. Untch, Gilbert J. Stork
  • Patent number: 4130654
    Abstract: This invention relates to novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids and their derivatives, wherein X is hydrogen, methoxy or chloro, methods of preparation, compositions and uses thereof.
    Type: Grant
    Filed: January 30, 1978
    Date of Patent: December 19, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Jack Ackrell
  • Patent number: 4129661
    Abstract: 4,5-Dihydro-2-lower alkoxycarbonylamino-4-phenylimidazole, and substituted phenyl derivatives thereof, and pharmaceutically acceptable salts thereof, and methods of preparing such compounds. In one method, the compounds can be prepared by treating the corresponding .beta.-amino-.beta.-(phenyl or substituted phenyl)-ethylamine with the desired 1,3-bis(alkoxycarbonyl)-S-methylisothiourea or 1-alkoxycarbonyl-S-methylisothiourea. The compounds can also be prepared by treating the corresponding 2-amino-4,5-dihydro-4-(phenyl or substituted phenyl)-imidazole with the desired dialkylcarbonate. The subject compounds are useful as psychotherapeutic agents for treating, preventing or palliating abnormal conditions, in mammals, which are related to the central nervous system.
    Type: Grant
    Filed: October 17, 1977
    Date of Patent: December 12, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Adolph P. Roszkowski, Colin C. Beard, Charles Dvorak, Klaus Weinhardt
  • Patent number: 4123614
    Abstract: The present invention relates to novel assay reagents, their composition, methods of preparation, and use in the detection and measurement of various biological systems and/or components, e.g. enzymes, antibodies, antigens, and periodate concentration. This invention in its basic form utilizes a class of compounds having, inter alia., a backbone chain, an indicator group, and vicinal oxidizable groups.
    Type: Grant
    Filed: October 18, 1976
    Date of Patent: October 31, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: David H. Rammler
  • 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: 4123550
    Abstract: 1-Alkylamino-3-([2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]thienylox y)-2-propanols and methods for preparing these compounds are disclosed. The compounds are useful in the treatment of hypertension and abnormal heart conditions in mammals. These compounds are prepared by the treatment of the corresponding 1,2-epoxy-3-[2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]heterocyclic aryloxy)propane with an alkylamine having the desired alkyl substituent or by base or acid hydrolysis of the corresponding 2-optionally substituted-3-alkyl-5-([2-(endobicyclo[3.1.0]hex-6-yl)ethylaminocarbonyl]h eterocyclic aryloxymethyl)oxazolidine. These latter compounds can be prepared by condensing a halo-substituted thiophene with a 3-alkyl-5-hydroxymethyloxazolidine such substituted or unsubstituted at the 2-position or alternatively, by treating the former aminopropanol compounds of the present invention with an aldehyde having the desired substituent.
    Type: Grant
    Filed: October 31, 1977
    Date of Patent: October 31, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Karl G. Untch, Stefan H. Unger, Brian Lewis
  • 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: 4112087
    Abstract: Compounds of the formula ##STR1## wherein R is alkyl having 1 to 4 carbon atoms, .beta.-haloethyl, allyl, propargyl, cyclopentyl or benzyl; R.sup.1 is hydrogen or an .alpha.-substituted acetamido group; R.sup.2 is hydrogen or a protecting group; and the pharmaceutically acceptable salts thereof. The 7.beta.-amino compounds are useful as intermediates for the 7.beta.-(.alpha.-substituted acetamido) compounds which are useful as antibacterials against a wide variety of gram positive and gram negative bacteria.
    Type: Grant
    Filed: November 4, 1976
    Date of Patent: September 5, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Philip J. Beeby