Patents by Inventor Joseph M. Muchowski

Joseph M. Muchowski 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: 4454326
    Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen, lower alkyl, chloro or bromo; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl;are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: June 12, 1984
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse
  • Patent number: 4410534
    Abstract: Novel 3-substituted-5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-8-carboxylic acid and 3-substituted-6,7,8,9-tetrahydro[1,2-a]azepine-9-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, n is the integer selected from the integers 1 or 2 and Ar is a 6- or 5-member ring. These compounds are useful as anti-inflammatory, analgesic and antipyretic agents, platelet aggregation inhibitors, and as smooth muscle relaxants.
    Type: Grant
    Filed: March 13, 1981
    Date of Patent: October 18, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Arthur F. Kluge
  • Patent number: 4410526
    Abstract: Compounds of the formula: ##STR1## and the pharmaceutically acceptable, non-toxic salts and esters (alkyl, 1-6C) thereof, wherein:X is O or S;R.sup.1 is selected from the group consisting of:(a) alkyl or cycloalkyl of 3-8 carbons, ##STR2## R.sup.2 is hydrogen or methyl; exhibit prostaglandin-like activity and are, thus, useful as platelet aggregation inhibitors.
    Type: Grant
    Filed: November 20, 1981
    Date of Patent: October 18, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Angel Guzman
  • Patent number: 4347186
    Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen or lower alkyl; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl;are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: August 31, 1982
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse
  • Patent number: 4347187
    Abstract: 5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein: X is hydrogen, lower alkyl, chloro or bromo; Ar is a moiety selected from the group consisting of ##STR2## in which: Y is oxygen or sulfur;R is hydrogen, methyl, chloro, or bromo, the R substitution being at the 3, 4 or 5 position of the ring;R.sup.1 is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, lower alkylcarbonyl, fluoro, chloro or bromo, the R.sup.1 substitution being at any available position in the ring;R.sup.2 is hydrogen or lower alkyl; are prepared by .beta.-decarboxylation of the corresponding dialkyl-1,1-dicarboxylates. Certain substituted pyrroles are useful as intermediates for preparing the compounds of formula I.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: August 31, 1982
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse
  • Patent number: 4347185
    Abstract: 5-benzoyl-7-halo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, represented by the formula ##STR1## and the pharmaceutically acceptable non-toxic esters and salts thereof, wherein:R is hydrogen or lower alkyl;X is hydrogen, lower alkyl, lower alkoxyl, lower alkoxycarbonyl, carboxyl, lower alkylcarbonyl, sulfonic acid, sulfonic acid alkyl ester, fluoro, chloro, or bromo; and Y is chloro or bromo, which are novel, and 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids which are represented by the formula ##STR2## wherein X and R are as above defined except that X cannot be chloro or bromo, are prepared by decarboxylation of the corresponding 1,1 dicarboxylates. Intermediates in said preparation are also disclosed.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: August 31, 1982
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Robert Greenhouse
  • Patent number: 4344943
    Abstract: Novel 5-aroyl-6-chloro- or 6-bromo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-7-carboxylic acids represented by the formula ##STR1## and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein Y is chloro or bromo and Ar is an optionally substituted phenyl, 2-furyl, or 2-thienyl ring or a 3-furyl, 3-thienyl, 2-pyrrolyl or 1-alkyl-2-pyrrolyl ring. These compounds are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: August 17, 1982
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Joseph M. Muchowski
  • Patent number: 4296042
    Abstract: This process relates to the synthesis of unsaturated aliphatic esters useful as insect sex attractants, including gossyplure, the insect sex pheromone of the pink bollworm moth, Pectinophora gossypiella, and intermediates therefor. The process utilizes a cyclic phosphonium (Wittig) reagent.
    Type: Grant
    Filed: June 18, 1980
    Date of Patent: October 20, 1981
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Michael C. Venuti
  • Patent number: 4232038
    Abstract: Novel 5-alkylsulfinylbenzoyl- and 5-alkylsulfonylbenzoyl,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 n is 1 or 2, R is hydrogen or a lower alkyl group containing from 1-4 carbon atoms and R.sup.1 is a lower alkyl group having from 1-4 carbon atoms at the ortho, meta or para postions of the benzoyl group and process for the production of such compounds. These compounds are useful as anti-inflammatory, analgesic and antipyretic agents and as smooth muscle relaxants.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: November 4, 1980
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Arthur F. Kluge, Joseph M. Muchowski
  • 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: 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: 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: 4055574
    Abstract: Novel thioesters of 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetic acid, (dl) 2-(6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)propionic acid and the individual (d) isomers of the latter, and processes for making the same.
    Type: Grant
    Filed: July 1, 1976
    Date of Patent: October 25, 1977
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Jack Ackrell, Joseph M. Muchowski
  • Patent number: 3997587
    Abstract: d1- and 8R-9-fluoro-11,15.alpha.-dihydroxyprosta-5-cis,13-trans-dienoic acid, d1- and 8R-9-fluoro-11,15.alpha.-dihydroxy-15.beta.-methyl-prosta-5-cis,13-trans-d ienoic acid and d1- and 8R-9-fluoro-11,15.beta.-dihydroxy-15.alpha.-methylprosta-5-cis,13-trans-di enoic acid, the pharmaceutically acceptable, nontoxic lower alkyl esters and salts thereof and process for the production of such compounds. 8R-9.beta.-fluoro-11.alpha.,15.alpha.-dihydroxyprosta-5-cis,13-trans-dieno ic acid is a representative compound of the class. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as luteolytic agents in female mammals and as bronchodilators.
    Type: Grant
    Filed: June 26, 1975
    Date of Patent: December 14, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Esperanza V. Velarde
  • Patent number: 3985791
    Abstract: Novel racemic and 8R-antimeric 16-phenoxy- and 16-(o, m or p)-substituted phenoxy derivatives of 9.alpha., 11.alpha.,15-trihydroxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acids, which may be further substituted at C-15 by a methyl or ethyl group, the pharmaceutically acceptable, non-toxic lower alkyl esters and salts thereof and processes for the production of such compounds. dl 9.alpha.,11.alpha.,15.alpha.-trihydroxy-16-m-trifluoromethylphenoxy-17,18, 19,20-tetranorprosta-4,5,13-trans-trienoic acid and dl 9.alpha.,11.alpha.,15 -trihydroxy-15 -methyl-16-m-trifluoromethylphenoxy-17,18,19,20-tetranorprosta-4,5,13-tran s-trienoic acid are representative compounds of the class. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as luteolytic agents in female mammals.
    Type: Grant
    Filed: December 22, 1975
    Date of Patent: October 12, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, John H. Fried
  • Patent number: 3940407
    Abstract: Novel 4-[2,3 or 4(3-amino-2-hydroxypropoxy) phenyl]- and 5-[2,3 or 4(3-amino-2-hydroxypropoxy) phenyl]-1,2,3-thiadiazole derivatives which may be further substituted at the C-5 or C-4 position of the thiadiazole ring, respectively, by a lower alkyl, phenyl, trifluoromethyl, carboxy, alkoxycarbonyl, cyano or an aminocarbonyl group, and the pharmaceutically acceptable acid addition salts thereof and processes for the production of such compounds; 4-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-1,2,3-thiadiazole and 5-[4(3-t-butylamino-2-hydroxypropoxy)phenyl]-1,2,3-thiadiazole are representative of the class. These compounds possess cardiovascular activity and are useful for the treatment of abnormal heart conditions in mammals.
    Type: Grant
    Filed: September 16, 1974
    Date of Patent: February 24, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, John H. Fried
  • Patent number: 3935241
    Abstract: Novel 8R-antimeric and racemic 11.alpha.-methylsubstituted-prosta-5-cis, 13-trans-dienoic and prost-13-trans-enoic acids having oxygenated functions at the C-9 and C-15 positions of the molecule, as well as the 15-methyl or ethyl derivatives thereof and processes for making such compounds. Also encompassed are the pharmaceutically acceptable, non-toxic alkyl esters and salts of the carboxylic acid function of these novel compounds.
    Type: Grant
    Filed: May 10, 1974
    Date of Patent: January 27, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Angel Guzman
  • Patent number: 3933791
    Abstract: Process for degrading the glycoside neriifolin and its acetate to the cardenolide digitoxigenin. Novel intermediates are also described.
    Type: Grant
    Filed: September 16, 1974
    Date of Patent: January 20, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Jose Iriarte
  • Patent number: 3931282
    Abstract: Novel process for the preparation of 11.alpha.-hydroxymethyl derivatives of natural (8R-) and racemic 9-keto-15.alpha.-hydroxy- and 9,15.alpha.-dihydroxy-prosta-5-cis,13-trans-dienoic and prost-13-transenoic acids, and the novel 15-methyl and ethyl substituted derivatives thereof, as well as the esters of the primary and secondary hydroxy groups and the non-toxic, pharmaceutically acceptable salts of the novel compounds.
    Type: Grant
    Filed: February 21, 1974
    Date of Patent: January 6, 1976
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Joseph M. Muchowski, Angel Guzman