Patents Represented by Attorney Gerard A. Blaufarb
  • 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: 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: 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: 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: 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: 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
  • Patent number: 4104280
    Abstract: Novel dibenzo[b.f]thiepin and oxepin compounds of the formula and the pharmaceutically acceptable esters and salts thereof, wherein R is hydrogen or methyl; X is oxygen or S(O).sub.n in which n is the integer 0, 1 or 2 and Z is a single or double bond, provided that when Z is a double bond X is not SO, and when R is methyl the compounds are (dl) mixtures, and methods for the production thereof.
    Type: Grant
    Filed: February 4, 1977
    Date of Patent: August 1, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Jack Ackrell
  • Patent number: 4097579
    Abstract: Novel 5-(2-pyrroyl) and 5-(N-lower alkyl-2-pyrroyl)-1,2-dihydro-3H-pyrrolo?1,2-a!pyrrole-1-carboxylic acid compounds represented by the formula: ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein each of R and R.sup.1 is independently hydrogen or a lower alkyl group having from 1 to 4 carbon atoms and process for the production of such compounds; 5-(N-methyl-2-pyrroyl)-1,2-dihydro-3H-pyrrolo?1,2-a!pyrrole-1-carboxylic acid is representative of the class. These compounds are useful as anti-inflammatory analgesic and anti-pyretic agents and as smooth muscle relaxants.
    Type: Grant
    Filed: March 31, 1977
    Date of Patent: June 27, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph Martin Muchowski, Arthur Frederick Kluge
  • Patent number: 4094978
    Abstract: 3-(3-hydroxyprop-1-(t)-enyl)-7.beta.-(.alpha.-substituted acetamido)-ceph-3-em-4-carboxylic acids; 3-(3-carbamoyloxyprop-1-(t)-enyl)-7.beta.-(.alpha.-substituted acetamido)-ceph-3-em-4-carboxylic acids; and 3-[3-(N-substituted carbamoyloxy)prop-1-(t)-enyl]-7.beta.-(.alpha.-substituted acetamido)-ceph-3-em-4-carboxylic acids and derivatives and salts thereof and process 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: July 29, 1976
    Date of Patent: June 13, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Philip J. Beeby
  • Patent number: 4089969
    Abstract: Novel 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid compounds represented by the formula ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein R is hydrogen or a lower alkyl group containing from 1 to 4 carbon atoms and R.sup.1 is hydrogen, a lower alkyl group having from 1 to 4 carbon atoms, a lower alkoxy group of 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 and process for the production of such compounds; 5-p-toluoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid is representative of the class. These compounds, as the racemic mixture or the (1)-isomer, are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
    Type: Grant
    Filed: February 23, 1977
    Date of Patent: May 16, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Arthur F. Kluge
  • Patent number: 4089865
    Abstract: 1-Amino-3-(4- or 5-substituted thiazol-2-oxy)-2-propanol and/or substituted amino derivatives thereof; 3-(4- or 5-substituted thiazol-2-oxy)-1,2-epoxypropane and 5-(4- or 5-substituted thiazol-2-oxymethylene)-oxazolidine and/or N- and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds are characterized by an aminocarbonyl or carbonylamino type substituent at the 5- or 4-position on the thiazole ring. The above 1-amino-3-(4- or 5-substituted thiazol-2-oxy)-2-propanol and derivatives exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The 3-(4- or 5-substituted thiazol-2-oxy)-1,2-epoxypropanes are useful as intermediates for the aforementioned cardiovascular agents.
    Type: Grant
    Filed: August 27, 1976
    Date of Patent: May 16, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: John A. Edwards
  • Patent number: 4087539
    Abstract: Novel 5-substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid compounds represented by the formulas ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein X is oxygen or sulphur, R is hydrogen or a lower alkyl group having from 1 to 4 carbon atoms and R.sup.1 is hydrogen, methyl, chloro or bromo, the R.sup.1 substitution being at the 3, 4 or 5 positions of the furan or thiophene ring in the compounds of Formula (A), and process for the production thereof; 5-(2-thenoyl)-1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1-carboxylic acid and 5-(3-furoyl)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid are representative of the class. These compounds, as the racemic mixture or the (1)-isomer, are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
    Type: Grant
    Filed: February 23, 1977
    Date of Patent: May 2, 1978
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Arthur F. Kluge
  • 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: 4082735
    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; 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: 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