Patents Represented by Attorney Roger A. Williams

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  • Pharmaceutically useful meso-azacyclic amides of imidazopyridine carboxylic acids and analogs thereof
    Patent number: 5137893
    Abstract: The imidazopyridines containing meso-azacycle side chains as described herein find utility as antagonists of the serotonin 5-HT.sub.3 receptor. As such they are useful for the treatment of humans and animals wherein antagonism of 5-HT.sub.3 receptors is benefical. Therapy is indicated for, but not limited to, the treatment of anxiety, psychoses, depression (especially depression accompanied by anxiety), cognitive disorders, substance abuse dependence and/or withdrawal, gastrointestinal motility disturbances (including esophageal reflux, dyspepsia, irritable bowel syndrome), emesis caused by chemotherapeutic agents, and visceral pain. Additionally, the compounds of the present invention may find utility as enhancers of nasal absorption of bioactive compounds.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: August 11, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Daniel P. Becker, Daniel L. Flynn, Alan E. Moormann, Roger Nosal, Clara I. Villamil
  • LTB.sub.4 synthesis inhibitors
    Patent number: 5135941
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH-- or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: August 4, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • N-azabicyclo [3.3.0]octane amides of aromatic acids
    Patent number: 5126343
    Abstract: A compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein n is 0 or 1; andAr is an aromatic amide moiety, which compound exhibits prokinetic activity and is a 5-HT3 antagonist.
    Type: Grant
    Filed: October 12, 1990
    Date of Patent: June 30, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Daniel L. Zabrowski, Daniel L. Flynn
  • Leukotriene B.sub.4 antagonists
    Patent number: 5124350
    Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or cycloalkylalkyl;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl;R.sup.6 is alkyl;n is 1 to 5;p is 0 to 6;x is 0 or 2; andR.sup.4 and R.sup.5 are independently hydrogen or alkyl or together with N form a cycloalkylamine.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in treating disease conditions mediated by LTB.sub.4.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: June 23, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Stephen H. Docter, Stella S. Yu
  • PLA.sub.2 inhibitors as antiinflammatories
    Patent number: 5112864
    Abstract: This invention relates to novel compounds for treating inflammatory conditions by inhibition of phospholipase A.sub.2 activity of the formula ##STR1## wherein X is oxygen, sulfur or --CH.dbd.CH--; wherein R.sup.1 is hydrogen, alkyl of 1 to 6 carbons or a pharmaceutically acceptable cation;wherein R.sup.2 is phenoxy, alkoxy, methyl, trifluoromethyl or phenyl;wherein n is an integer from 1 to 20;compositions comprised of the novel compounds; and methods of treating inflammatory conditions with these compositions.
    Type: Grant
    Filed: May 30, 1991
    Date of Patent: May 12, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Stephen H. Docter, Richard A. Haack
  • Tetraenyl prostanoic acid derivatives as prodrugs for the treatment of peptic ulcer disease
    Patent number: 5089524
    Abstract: Tetraenyl Prostanoic Acid derivatives which are useful as prodrugs for the treatment of peptic ulcer disease and are represented by the following general formula ##STR1## are disclosed.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: February 18, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Paul W. Collins, Alan F. Gasiecki
  • LTB.sub.4 synthesis inhibitors
    Patent number: 5086067
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, --CH.dbd.CH-- or --CH.dbd.N--; wherein R.sub.1 is alkyl, alkenyl or alkynyl of about 1 to 20 carbon atoms; wherein R is --CO.sub.2 R.sup.2, tetrazole, methylsulfonamide or benzenesulfonamide, wherein R.sup.2 is hydrogen, alkyl of 1 to 6 carbon atoms or a pharmaceutically acceptable cation and R.sup.3 is hydroxyl or halogen, having utility as LTB.sub.4 synthesis inhibitors.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: February 4, 1992
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
  • Process for preparing prostaglandins
    Patent number: 5075478
    Abstract: A process for preparing prostaglandin derivatives by reacting a trans bis-tin ethylene with an organo metal compound then with a compound selected from an epoxide, aldehyde, or ketone, then, without isolation and in the same reaction vessel, reacting with an organo lithium compound, a cuprate complex and a cyclopentenone to produce a prostaglandin intermediate having an unprotected hydroxyl group on the omega side chain.
    Type: Grant
    Filed: January 17, 1991
    Date of Patent: December 24, 1991
    Assignee: G. D. Searle & Co.
    Inventors: James R. Behling, John R. Medich
  • Alkoxy-substituted dihydrobenzopyran-2-carboxylic acids and derivatives thereof
    Patent number: 5073562
    Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or (CH.sub.2).sub.m R.sup.3 whereR.sup.3 is cycloalkyl and m is 1 or 2;R.sup.1 is alkyl;R.sup.2 is hydrogen or alkyl;R.sup.4 is alkyl;n is an integer from 1 to 5;p is an integer from 0 to 6;Y is NH, oxygen or sulfur; andZ is hydrogen, alkyl, alkenoxy, NR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen or alkyl, or SR.sup.6 wherein R.sup.6 is hydrogen, benzyl or alkyl.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in the treatment of leukotriene B.sub.4 mediated conditions.
    Type: Grant
    Filed: May 10, 1990
    Date of Patent: December 17, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Thomas D. Penning, James P. Snyder
  • Process for preparing prostaglandin analogs using organozirconium compounds
    Patent number: 5055604
    Abstract: A process for preparing a prostaglandin derivative by reacting an alkyne with zirconocene chloride hydride to produce a zirconium intermediate which is reacted with an alkyllithium and a first copper reagent selected from R.sup.2 Cu(CN)Li or the mixture CuCN and R.sup.2 Li to produce a higher order cuprate complex intermediate and reacting the higher order cuprate complex intermediate with a cyclopentenone to produce the prostaglandin derivative.
    Type: Grant
    Filed: April 17, 1990
    Date of Patent: October 8, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Kevin A. Babiak, James R. Behling, John H. Dygos, John S. Ng
  • N-(6)-substituted adenosine compounds
    Patent number: 5055569
    Abstract: The present invention relates to N-(6)-substituted adenosine compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein Z is an amine and R.sub.1 and R.sub.2 are independently hydrogen, hydroxyl, halogen, alkyl, phenyl, alkoxy, morpholino, piperidino, piperazino, phenoxy, thiophenoxy or amino optionally substituted by alkyl, aralkyl or phenyl.
    Type: Grant
    Filed: October 19, 1989
    Date of Patent: October 8, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Daniel P. Becker, Paul W. Collins, Daniel L. Flynn
  • Alkoxy-substituted dihydrobenzopyran-2-carboxylic acids and derivatives thereof, compositions and use
    Patent number: 5051438
    Abstract: This invention relates to compounds of Formula I and the stereoisomers and pharmaceutically acceptable salts thereof ##STR1## wherein R is alkyl, alkenyl, alkynyl, or cycloalkylalkyl and m is 1 or 2;R.sup.1 is alkyl of 1 to 4 carbon atoms;R.sup.2 is hydrogen or alkyl of 1 to 5 carbon atoms;R.sup.4 is alkyl of 1 to 6 carbon atoms;n is an integer from 1 to 5; andY is NH or oxygen.The compounds of Formula I are leukotriene B.sub.4 antagonists and are useful as anti-inflammatory agents and in the treatment of LTB.sub.4 mediated diseases.
    Type: Grant
    Filed: May 16, 1990
    Date of Patent: September 24, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Thomas D. Penning
  • Stabilized pharmaceutical admixture composition
    Patent number: 5015481
    Abstract: A stabilized pharmaceutical composition which is an admixture of an NSAID selected from diclofenac and piroxicam, a prostaglandin and hydroxypropyl methylcellulose for maintaining the prostaglandin in a therapeutically effective amount without negatively affecting the therapeutic activity of the NSAID.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: May 14, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Michel Franz, Michel Jans, Leo K. Mathur, Kamlesh B. Shah, James E. Truelove
  • Process for preparing higher order cuprate complexes
    Patent number: 5011958
    Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as epoxide addition. The complex is formed by reacting a first cuprate complex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes derived from the reaction of a cuprate complex with 1,2-bis-tri-n-butylstannyl ethylene are particularly useful for the addition to epoxides to form vinyl tin intermediates useful for preparing omega side chains of prostaglandins.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: April 30, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Arthur L. Campbell, James R. Behling, John S. Ng, Kevin A. Babiak
  • N-azabicyclo(3.3.0)octane amides of aromatic acids, compositions, and methods of use thereof
    Patent number: 4992461
    Abstract: A compound of the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein n is 0 or 1; andAr is an aromatic amide moiety, which compound exhibits prokinetic activity and is a 5-HT3 antagonist.
    Type: Grant
    Filed: September 11, 1989
    Date of Patent: February 12, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Daniel L. Zabrowski, Daniel L. Flynn
  • Furyl, phenylene, and thienyl leukotriene B.sub.4 analogues
    Patent number: 4971997
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, or --CH.dbd.CH--;wherein Z is OR.sup.1 or --NR.sup.4 R.sup.5 ;wherein R.sup.1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation;wherein R.sup.2 is H, --CH.sub.3 or --C.sub.2 H.sub.5 ;wherein R.sup.3 is OH, H or .dbd.O;wherein R.sup.4 and R.sup.5 may independently be hydrogen, or lower alkyl having 1-6 carbon atoms, or R.sup.4 and R.sup.5 may act together with N to form a cyclic amide of the formula: ##STR2## wherein n is an integer from 4-5; and m is an integer from 0-4. More particularly, this invention relates to compounds of the above formula which have utility as LTB.sub.4 antagonists.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: November 20, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Stella S. Yu
  • Furyl, phenylene, and thienyl leukotriene B.sub.4 analogues
    Patent number: 4970234
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, or --CH.dbd.CH--;wherein Z is OR.sup.1 or --NR.sup.4 R.sup.5 ;wherein R.sup.1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation;wherein R.sup.2 is H, --CH.sub.3 or --C.sub.2 H.sub.5 ;wherein R.sup.3 is OH, H or --O;wherein R.sup.4 and R.sup.5 may independently be hydrogen, or lower alkyl having 1-6 carbon atoms, or R.sup.4 and R.sup.5 may act together with N to form a cyclic amide of the formula: ##STR2## wherein n is an integer from 4-5; and m is an integer from 0-4. More particularly, this invention relates to compounds of the above formula which have utility as LTB.sub.4 antagonists.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: November 13, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Richard A. Haack, Stella S. Yu
  • Furyl, phenylene, and thienyl leukotriene B.sub.4 analogues
    Patent number: 4970229
    Abstract: This invention relates to a compound of the formula: ##STR1## or a pharmaceutically acceptable salt thereof wherein X is oxygen, sulfur, or --CH.dbd.CH--;wherein Z is OR.sup.1 or --NR.sup.4 R.sup.5 ;wherein R.sup.1 is hydrogen, lower alkyl, or a pharmaceutically acceptable cation;wherein R.sup.2 is H, --CH.sub.3 or --C.sub.2 H.sub.5 ;wherein R.sup.3 is OH, H or .dbd.O;wherein R.sup.4 and R.sup.5 may independently be hydrogen, or lower alkyl having 1-6 carbon atoms, or R.sup.4 and R.sup.5 may act together with N to form a cyclic amide of the formula: ##STR2## wherein n is an integer from 4-5; and m is an integer from 0-4. More particularly, this invention relates to compounds of the above formula which have utility as LTB.sub.4 antagonists.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: November 13, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Steven W. Djuric, Richard A. Haack, Stella S. Yu
  • 1,3-dioxolane derivatives useful in the treatment of inflammation
    Patent number: 4954520
    Abstract: The present invention relates to compounds of the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein R is alkyl of 5 to 14 carbon atoms, alkenyl of 5 to 14 carbon atoms or alkynyl of 5 to 14 carbon atoms; R.sup.1 is lower alkylene or phenylene; and R.sup.2 is hydrogen, lower alkyl or a pharmaceutically acceptable cation.
    Type: Grant
    Filed: January 19, 1989
    Date of Patent: September 4, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Stevan W. Djuric, Thomas D. Penning
  • Cyclopenteneheptenoic acid derivatives and method of preparation thereof
    Patent number: 4952710
    Abstract: This invention relates to a novel cyclopenteneheptenoic acid derivative having the following formula ##STR1## wherein R.sub.1 is hydrogen, --COCH.sub.3, --COCF.sub.3, --CO--phenyl, or a hydroxyl protecting group such as tetrahydropyranyl, tetrahydrofuranyl, or tri-lower alkylsilyl;wherein R.sub.2 is --CH.sub.2 OR.sub.1, --COOH, --COOR, --CHO, --CH.sub.2 --OSi(R.sub.12).sub.3, ##STR2## wherein R is lower alkyl and each R.sub.12 is independently lower alkyl or aryl; andwherein Y is ethylene, cis-vinylene, trans-vinylene, or acetylene.Also disclosed is a novel process for preparation of the above-defined cyclopenteneheptenoic acid derivative. This process involves coupling of a higher order cuprate complex with a chiral cyclopentene compound. The resultant product is particularly useful as a starting compound for high yield synthesis of optically active prostaglandins.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: August 28, 1990
    Assignee: G. D. Searle & Co.
    Inventors: Kevin A. Babiak, Arthur L. Campbell