Patents by Inventor John H. Fried

John H. Fried has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 5057621
    Abstract: This invention covers a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, Y is lower alkyl or ##STR2## wherein Z is hydrogen, halo, methyl, methoxy or trifluoromethyl; and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..
    Type: Grant
    Filed: April 16, 1987
    Date of Patent: October 15, 1991
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, John H. Fried, L. David Waterbury
  • Patent number: 4792617
    Abstract: This invention covers a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, Y is lower alkyl or ##STR2## wherein Z is hydrogen, halo, methyl, methoxy or trifluoromethyl; and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..
    Type: Grant
    Filed: February 27, 1987
    Date of Patent: December 20, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, John H. Fried, L. David Waterbury
  • Patent number: 4761416
    Abstract: Pharmaceutical compositions comprising, or compositions consisting essentially of, compounds according to the formula ##STR1## or an optical isomer thereof are disclosed, wherein the substituents A, Z and R.sup.1 are defined herein. The invention is also directed to certain compounds of the above class. The compounds of Formula I are cyclic AMP phosphodiesterase inhibitors useful as antithrombotic and inotropic agents and the like in mammals.
    Type: Grant
    Filed: July 25, 1986
    Date of Patent: August 2, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John H. Fried, Michael C. Venuti
  • Patent number: 4690925
    Abstract: Compounds according to the formula ##STR1## , its optical isomers, or a pharmaceutically acceptable salt thereof wherein:m and n are integers of 1 to 6;R.sub.1 is hydrogen or alkyl of 1 to 4 carbons;R.sub.2 is hydrogen or R.sub.1 and R.sub.2 are combined to form an oxo group;R.sub.3 is hydrogen, alkyl of 1 to 6 carbons, phenyl, benzyl, hydroxy lower alkyl and its aliphatic acylates of 1 to 6 carbon atoms or aryl acylates of 7 to 12 carbon atoms, carbamoyl alkyl, carboxyalkyl, alkoxycarbonylalkyl or .alpha.-amino acid side chains;R.sub.4 is hydrogen, alkyl of 1 to 6 carbons, benzyl, or hydroxy lower alkyl;R.sub.5 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms or cycloalkyl lower alkyl of 4 to 12 carbon atoms wherein the cycloalkyl ring is unsubstituted or substituted with a lower alkyl, lower alkoxy, --OH, --OCOR.sub.6, halo, --NH.sub.2, --N(R.sub.6).sub.2, --NHCOR.sub.6, --COOH, or --COO(R.sub.6) group wherein R.sub.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: September 1, 1987
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John H. Fried, Michael C. Venuti
  • Patent number: 4323564
    Abstract: The 17-butyrate, 17-benzoate, 17,21-methyl orthobutyrate, 17,21-methyl orthobenzoate, and 17,21-dibutyrate esters of cloprednol (6-chloro-11.beta., 17.alpha., 21-trihydroxy-pregna-1,4,6-triene-3,20-dione) are useful as topical, anti-inflammatory steroids.
    Type: Grant
    Filed: March 9, 1978
    Date of Patent: April 6, 1982
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: John H. Fried, Denis J. Kertesz, Michael Marx
  • 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: 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: 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: 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: 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: 4046801
    Abstract: 13-Cis prostaglandin derivatives; cis-octenol ether copper.sup.(I) lithium reagents and methods of making such reagents and using the reagents to prepare the 13-cis prostaglandin derivatives. The 13-cis prostaglandin derivatives exhibit prostaglandin-like pharmacological properties and are further useful as intermediates for the corresponding prostaglandin isomers having the normal 13-trans configuration.
    Type: Grant
    Filed: December 9, 1974
    Date of Patent: September 6, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Arthur F. Kluge, Karl G. Untch, John H. Fried
  • 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: 4031234
    Abstract: This application relates to 1,5(6)-disubstituted benzimidazole-2-carbamate derivatives represented by the following formula: ##STR1## where R is lower alkyl having 1 to 4 carbon atoms; R.sup.1 is --SOR.sup.2, --SR.sup.5, --OR.sup.5 or M'(CH.sub.2).sub.n MR.sup.7 ; 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; R.sup.5 is lower alkenyl, lower alkynyl or aralkyl; R.sup.7 is lower alkyl having 1 to 4 carbon atom, or aryl; M and M' are independently O, S, ##STR2## n is 1-4; and R.sup.8 is lower alkyl having 1 to 12 carbon atoms optionally substituted with a --COOR group where R is lower alkyl having 1 to 4 carbon atoms, aryl 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: June 18, 1976
    Date of Patent: June 21, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 4011320
    Abstract: 7(8)-substituted triazinobenzimidazoles represented by the formula: ##STR1## where R is a lower alkyl group having 1 to 4 carbon atoms; R' is diloweralkylaminoalkyl (C.sub.2-6) or alkyl having 1 to 18 carbon atoms; R.sup.2 is phenylsulfinyl, phenoxyethoxy, benzyloxyethoxy, methoxyethylsulfinyl, or 3-chloroprop-1-ylsulfinyl; the R.sup.2 -substitution being at the 7(8)-position; or a pharmaceutically acceptable salt thereof.The compounds are useful as pesticides, particularly as antifungal and anthelmintic agents.
    Type: Grant
    Filed: March 8, 1976
    Date of Patent: March 8, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 4009197
    Abstract: 2-(6'-Substituted-2'-naphthyl)acetic acid derivatives substituted at the 2-position of the acetic acid moiety with methyl, methylene or halomethylene and the salts and esters thereof have anti-inflammatory, analgesic and anti-pyretic activities.
    Type: Grant
    Filed: May 1, 1975
    Date of Patent: February 22, 1977
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison
  • Patent number: 4005202
    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 a heterocyclic ring having 1-4 hetero atoms; and M is O, S, or ##STR2## The R.sup.1 M-substitution is at the 5(6)-position. The compounds are useful as pesticides, particularly as anthelmintic and antifungal agents.
    Type: Grant
    Filed: September 22, 1975
    Date of Patent: January 25, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 4002640
    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; and R.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: November 3, 1975
    Date of Patent: January 11, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Colin C. Beard, John A. Edwards, John H. Fried
  • Patent number: 4001295
    Abstract: Novel racemic and antimeric prostaglandin analogs having a difluoromethylene group attached to the C-11,12 positions of the molecule, and oxygenated functions at C-9 and C-15, which may be further substituted at C-15 by a methyl group and processes for the production of such compounds. Also included are the lower alkyl esters of the carboxylic acid function and pharmaceutically acceptable salts thereof. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals, where prostaglandins are indicated.
    Type: Grant
    Filed: June 23, 1975
    Date of Patent: January 4, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowki, John H. Fried
  • Patent number: 4001301
    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 17, 1975
    Date of Patent: January 4, 1977
    Assignee: Syntex Corporation
    Inventors: John H. Fried, Ian T. Harrison