Nitrogen Or A -c(=x)- Group, Wherein X Is Chalcogen, Attached Directly To The Bicyclo Ring System By Nonionic Bonding Patents (Class 549/57)
  • Patent number: 6340691
    Abstract: Compounds of the formula are useful in treating disease conditions mediated by TNF-&agr;, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: January 22, 2002
    Assignee: American Cyanamid Company
    Inventors: Jeremy I. Levin, Aranapakam M. Venkatesan, Derek C. Cole, James M. Chen, Jamie M. Davis, George T. Grosu
  • Patent number: 6339172
    Abstract: A method for analyzing an objective substance, comprsing reacting a labeled probe with an objective substance on a biological sample, said probe comprsing a label substance of the formula (I): wherein A1 is an aromatic group, R1 is a hydrogen or —COCH2COCnF2n+1 and n is an integer of 1-6, which is bonded to a probe selected from the group consisting of nucleic acid, nudeic acid binding potein, low molecular ligand and receptor for ligand (except antibody) to give a fluorescent complex, reacting the complex with an objective substance on a biolgical sample and assaying fluorescence of the resultant fluorescent complex, a labeled nucleic acid probe and a labeled nucleotide. According to the method of the present invention, defects such as hindrance of fluorescence due to contaminant substance, low sensitivity and the like can be resolved, thereby enabling analysis on a tissue.
    Type: Grant
    Filed: April 28, 1999
    Date of Patent: January 15, 2002
    Assignees: Toyo Boseki Kabushiki Kaisha
    Inventors: Kazuhiro Matsui, Katsunori Ikeda, Shinichi Teshima, Yoshihisa Kawamura, Kazuko Matsumoto
  • Patent number: 6331640
    Abstract: A compound of formula 1a which is useful for treating reperfusion injury, and salts, prodrugs, and related compounds.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: December 18, 2001
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Nader Fotouhi, Paul Gillespie, Robert William Guthrie, Sherrie Lynn Pietranico-Cole, Weiya Yun
  • Patent number: 6329421
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: December 11, 2001
    Assignee: Merck Frosst Canada & Co.
    Inventors: Petpiboon Prasit, Daniel Guay, Zhaoyin Wang, Serge Leger, Michel Therien
  • Patent number: 6329372
    Abstract: Phenylalanine derivatives of formula (1) are described: wherein R is a carboxylic acid or a derivative thereof; L1 is a linker atom or group; Het is an optionally substituted heteroaromatic group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of alpha4 integrins to their ligands and are of use in the prophylaxis and treatment of immune or inflammatory disorders.
    Type: Grant
    Filed: January 26, 1999
    Date of Patent: December 11, 2001
    Assignee: Celltech Therapeutics Limited
    Inventors: John Clifford Head, Sarah Catherine Archibald, Graham John Warrellow, John Robert Porter
  • Patent number: 6310074
    Abstract: The invention relates to compound of formula (I): A—G1—Cy—G2—Cy′—G3—B  (I) wherein: A represents a grouping NR1C(Q)R2, C(Q)NR2R3 or NR1C(Q)NR2R3, B represents a grouping NR1C(Q)R2, NR1C(Q)NR2R3, C(Q)NR2R3, C(Q)OR1, NR1C(Q)OR2 or NR2R3, G1 and G3 represent an optionally substituted alkylene chain, Cy and Cy′, which are different, represent a ring structure or G2 represents a chain and medicinal products containing the same are useful in treating or in preventing melatoninergic disorders.
    Type: Grant
    Filed: May 18, 2000
    Date of Patent: October 30, 2001
    Assignee: Adir et Compagnie
    Inventors: Patrick Depreux, Said Yous, Gwenael Cheve, GĂ©rald Guillaumet, Marie-Claude Viaud, Carlos Larraya, Caroline Bennejean, Philippe Delagrange, Pierre Renard, Carole Descamps-Francois
  • Publication number: 20010034454
    Abstract: Methoxy and ethoxy substituted 3-aroyl-2-arylbenzo[b]thiophenes and benzo[b]thiophene analogues are described for use in inhibiting tubulin polymerization. The compounds' use for treating tumor cells is also described.
    Type: Application
    Filed: December 15, 2000
    Publication date: October 25, 2001
    Applicant: BYLOR UNIVERSITY AND ARIZONA DESEASE CONTROL RESEARCH COMMISSION
    Inventors: Kevin G. Pinney, George R. Pettit, Vani P. Mocharla, Maria del Pilar Mejia, Anupama Shirali
  • Patent number: 6274619
    Abstract: A compound of the formula: in which R1 is hydrogen, optionally substituted lower alkylcarbamoyl(lower)alkylidene, lower alkylidene, lower alkyl, optionally substituted ar(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, protected carboxy(lower)alkyl, carboxy(lower)alkyl, hydroxy(lower)alkyl, optionally substituted lower alkylcarbamoyl(lower)alkyl, lower alkylthio(lower)alkyl, carboxy(lower)alkanoyl, protected carboxy(lower)alkanoyl, aroyl, lower alkanoyl, or optionally substituted arylcarbamoyl(lower)alkyl, R2 is hydrogen, carboxy, protected carboxy, formyl or N-(lower)alkyl-N-(lower)alkoxycarbamoyl, R3 is hydrogen or amidino-protective group, A is lower alkylene or carbonyl, X is Y is lower alkylene, —S— or —SO2—, Z is —S— or —O—, and the line: is a single bond or a double bond, or pharmaceutically acceptable salts thereof, which is useful as a medicament.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: August 14, 2001
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Akito Tanaka, Hiroaki Mizuno, Minoru Sakurai
  • Patent number: 6265428
    Abstract: Methods, compositions, and compounds for modulating the activity of an endothelin peptide are provided. The methods use compositions that contain compounds of formula (1): where X and Y are selected from groups that include O, S, and NH; and Ar1, Ar2 and Ar3 are independently selected from substituted or unsubstituted groups that include 5 to 6 membered aryl groups and heteroaryl groups that contain one or two heteroatom(s). The methods are effected by contacting endothelin receptors with one or more of the compounds or with compositions containing one or more of the compounds prior to, simultaneously with, or subsequent to contacting the receptors with an endothelin peptide.
    Type: Grant
    Filed: June 8, 1999
    Date of Patent: July 24, 2001
    Assignee: Texas Biotechnology Corporation
    Inventors: Ming Fai Chan, Vitukudi Narayanaiyengar Balaji, Rosario Silvestre Castillo, Adam Kois, Bore Gowda Raju, Chengde Wu
  • Patent number: 6262055
    Abstract: Sulfur-containing heteroaryl dioxo-butyric acid derivatives are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: July 17, 2001
    Assignee: Merck & Co., Inc.
    Inventors: Steven D. Young, John S. Wai, Mark W. Embrey, Thorsten E. Fisher
  • Patent number: 6225336
    Abstract: This invention provides novel compounds which are dual antagonistic to TXA2 and PGD2 receptors and the pharmaceutical compositions containing them. They are useful for treating, for example, systemic mastocytosis and disorder of systemic mast cell activation as well as tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, ischemic reperfusion injury, and inflammation. In detail, this invention provides a compound of the foumula (I): pharmaceutically acceptable salt thereof, or hydrate thereof.
    Type: Grant
    Filed: February 14, 2000
    Date of Patent: May 1, 2001
    Assignee: Shionogi & Co., Ltd.
    Inventor: Tsunetoshi Honma
  • Patent number: 6217642
    Abstract: A method and composition for protection against fouling of objects which come into contact with sea water or brackish water comprising a benzothiophene-2-carbomide S,S-dioxide as the essential component are described.
    Type: Grant
    Filed: March 11, 1998
    Date of Patent: April 17, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz Kunisch, Martin Kugler, Heinrich Schrage, Hans-Ludwig Elbe
  • Patent number: 6200731
    Abstract: The present invention discloses a cross-linking monomer for a photoresist polymer represented by following Chemical Formula 1: <Chemical Formula 1> wherein, V represents CH2, CH2CH2, oxygen or sulfur; Y is selected from the group consisting of straight or branched C1-10 alkyl, oxygen, and straight or branched C1-10 ether; R′ and R″ individually represent H or CH3; i is a number of 1 to 5; and n is a number of 0 to 3; and a process for preparing a photoresist copolymer comprising the same.
    Type: Grant
    Filed: December 16, 1999
    Date of Patent: March 13, 2001
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Geun Su Lee, Cha Won Koh, Jae Chang Jung, Min Ho Jung, Ki Ho Baik
  • Patent number: 6194449
    Abstract: The present invention relates to compounds of formulas (IA), (IB), and (IC): the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as allosteric adenosine receptor modulators for uses including protection against hypoxia and ischemia induced injury and treatment of adenosine-sensitive cardiac arrhythmias.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: February 27, 2001
    Assignee: Medco Corp.
    Inventor: Pier Giovanni Baraldi
  • Patent number: 6180797
    Abstract: There is provided a process for the dehalogenation of a compound of formula II via the use of a transition metal catalyst and ammonium formate at atmospheric pressure.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: January 30, 2001
    Assignee: American Cyanamid Co.
    Inventor: Thomas Walter Drabb, Jr.
  • Patent number: 6177444
    Abstract: The present invention relates to compounds of formulas (IA), (IB), and (IC): the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as allosteric adenosine receptor modulators for uses including protection against hypoxia and ischemia induced injury and treatment of adenosine-sensitive cardiac arrhythmias.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: January 23, 2001
    Assignee: Medco Corp.
    Inventor: Pier Giovanni Baraldi
  • Patent number: 6169206
    Abstract: 4-(N,N-Dialkylamino)aniline compounds of the following general formula (I): wherein R1 represents an alkyl group, an aryl group or a heterocyclic group, R2 to R5 each represent a hydrogen atom or a substituent, and R2 and R3, R1 and R2, or R4 and R5 may form a ring together; a processing composition for color photography, which contains at least one of these compounds; and a color image-forming method wherein at least one of these aniline compounds is used.
    Type: Grant
    Filed: January 24, 2000
    Date of Patent: January 2, 2001
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keizo Kimura, Shigeo Hirano, Hiroshi Kawamoto
  • Patent number: 6166251
    Abstract: Disclosed are labeling reagents containing fluorescent compounds represented by the general formula ##STR1## where R is a group capable of combining with proteins, Ar is a conjugated double bond system, and n is a whole number. These labeling reagents have high fluorescence emission intensities, give high synthesis yields, permit both solid-phase measurements and liquid-phase measurements in immunoassays, and require less measuring steps.
    Type: Grant
    Filed: December 31, 1998
    Date of Patent: December 26, 2000
    Assignees: Kazuko Matsumoto, Suzuki Motor Corporation
    Inventors: Kazuko Matsumoto, Jingli Yuan
  • Patent number: 6162930
    Abstract: Methoxy and ethoxy substituted 3-aroyl-2-arylbenzo[b]thiophenes and benzo[b]thiophene analogues are described for use in inhibiting tubulin polymerization. The compounds' use for treating tumor cells is also described.
    Type: Grant
    Filed: December 3, 1999
    Date of Patent: December 19, 2000
    Assignee: Baylor University
    Inventors: Kevin G. Pinney, George R. Pettit, Vani P. Mocharla, Maria del Pilar Mejia, Anupama Shirali
  • Patent number: 6156891
    Abstract: Carboxylic acids of formula (1): ##STR1## wherein R.sup.2 and R.sup.3 are independently hydrogen or C.sub.1 -C.sub.3 alkyl, and Q is optionally substituted phenyl, can be easily converted by ring closing into pyridazin-3-one derivatives of formula (7): ##STR2## The carboxylic acids of formula (1) can be produced by reacting hydrazone compounds of formula (5): ##STR3## wherein R.sup.3 and Q are as defined above, with malonic acid derivatives of formula (6):R.sup.2 CH(COOH).sub.2wherein R.sup.2 is as defined above in the presence of a base.
    Type: Grant
    Filed: April 9, 1999
    Date of Patent: December 5, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Takashi Furukawa
  • Patent number: 6156786
    Abstract: This invention provides methods which are useful for the inhibition of the various medical conditions associated with estrogen deprivation syndrome including osteoporosis and hyperlipidemia utilizing compounds of formula I: ##STR1##
    Type: Grant
    Filed: November 4, 1998
    Date of Patent: December 5, 2000
    Assignee: Eli Lilly and Company
    Inventor: George Joseph Cullinan
  • Patent number: 6156787
    Abstract: The present invention provides compounds of formula (I) or pharmaceutically acceptable salts thereof: ##STR1## where A is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, arylC.sub.1-6 alkyl, aryl, S(O),R.sup.1, OR.sup.1 or NR.sup.1 R.sup.6 ;R.sup.1 is hydrogen; C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl or C.sub.3-6 cycloalkenyl each of which is optionally substituted by amino, C.sub.1-6 alkylamino, di(C.sub.1-6 alkyl)amino, C.sub.1-6 alkoxy, C.sub.1-6 alkylaminocarbonyl, one, two or three hydroxy groups, one, two or three halogen atoms or a four, five or six-membered saturated heterocyclic ring containing a nitrogen atom and optionally either an oxygen atom or a further nitrogen atom which ring is optionally substituted by C.sub.1-4 alkyl on the further nitrogen atom; aryl, arylC.sub.1-6 alkyl, arylC.sub.2-6 alkenyl or arylC.sub.2-6 alkynyl optionally substituted on the aryl ring by halogen, nitro, cyano, C.sub.
    Type: Grant
    Filed: April 22, 1999
    Date of Patent: December 5, 2000
    Assignee: Merck Sharp & Dohme Limited
    Inventors: Howard Barff Broughton, Mark Stuart Chambers
  • Patent number: 6143777
    Abstract: Aminothiophenecarboxamides of the formula I ##STR1## and their physiologically acceptable salts, whereinR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, A and n have the meanings stated in claim 1, exhibit phosphodiesterase V inhibition and can be used for the treatment of diseases of the cardiovascular system and for the therapy of disturbances of potency.
    Type: Grant
    Filed: April 14, 1999
    Date of Patent: November 7, 2000
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rochus Jonas, Pierre Schelling, Franz-Werner Kluxen, Maria Christadler
  • Patent number: 6133262
    Abstract: This application relates to novel compounds of formula I (and their pharmaceutically acceptable salts), as defined herein, processes and intermediates for their preparation, pharmaceutical formulations comprising the novel compounds of formula I, and the use of the compounds of formula I as thrombin inhibitors.
    Type: Grant
    Filed: October 28, 1999
    Date of Patent: October 17, 2000
    Assignee: Eli Lilly and Company
    Inventors: Jefferson Ray McCowan, John Eldon Toth, Daniel Jon Sall
  • Patent number: 6110963
    Abstract: This invention provides compounds of Formula I having the structure ##STR1## wherein A is C or N;B is O, S, N, or CH.dbd.CH;E is ##STR2## or --X--D; D is ##STR3## or alkyl of 1-12 carbon atoms; X is CO, CH(OH), CH.sub.2, or --CH--S-2-benzothiazole;Y is hydrogen, alkyl of 1-6 carbon atoms, or halogen;Z is O, S, or N;R is hydrogen, alkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, halogen, or trifluoromethyl;R.sup.1 is alkyl of 1-12 carbon atoms, aryl of 6-10 carbon atoms, aralkyl of 7-15 carbon atoms, halogen, Het-alkyl wherein the alkyl moiety contains 1-6 carbon atoms, or aryl mono-, di- or tri-substituted with a substituent selected from the group consisting of halogen, alkyl of 1-6 carbon atoms, trifluoromethyl, and alkoxy of 1-6 carbon atoms;Het is ##STR4## G is O, S, or N; and the remaining variables are as defined in claim 1, or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin or hyperglycemia.
    Type: Grant
    Filed: May 10, 1999
    Date of Patent: August 29, 2000
    Assignee: American Home Products Corporation
    Inventor: Michael S. Malamas
  • Patent number: 6090843
    Abstract: This invention provides novel benzothiophene compounds of the formula I: ##STR1## which are useful for the treatment of the various medical conditions associated with postmenopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus, and cervix. The present invention further relates to pharmaceutical formulations of compounds of formula I.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: July 18, 2000
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Jeffrey Alan Dodge
  • Patent number: 6084108
    Abstract: Fungicides having thiophene rings may be made from the intermediate compound 3-carbomethoxy-4,5-dimethylthiophene. That compound, and related compounds, may be produced by reacting an alpha mercaptoketone, e.g., 3-mercapto-2-butanone, with an acrylate, e.g., methyl-3-methoxy acrylate, in the presence of an alkoxide base, e.g., NaOMe, to form the substituted tetrahydrothiophene, followed by conversion to the aromatic thiophene with an acid treatment. The substituted tetrahydrothiophene is a novel compound.
    Type: Grant
    Filed: October 13, 1998
    Date of Patent: July 4, 2000
    Assignee: Monsanto Company
    Inventors: Thomas L. Fevig, Patrick H. Lau, Wendell G. Phillips
  • Patent number: 6069166
    Abstract: A compound, pharmaceutically acceptable salt thereof, or hydrate thereof having a PGD.sub.2 -antagonistic activity, and an inhibitory activity against infiltration of eosinophils, useful for treating mast cell dysfunction-associated diseases, such as systemic mastocytosis and disorder of systemic mast cell activation, as well as tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, ischemic reperfusion injury, inflammation and atopic dermatitis, which is shown by the formula (I): ##STR1## is provided.
    Type: Grant
    Filed: May 28, 1999
    Date of Patent: May 30, 2000
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsunetoshi Honma, Yoshiharu Hiramatsu, Akinori Arimura
  • Patent number: 6063936
    Abstract: An aromatic carboxylic acid bicyclic sulfur compound of the following formula: ##STR1## wherein X.sup.1 is selected from the group consisting of C.sub.1 to C.sub.4 alkyl, halogen, C.sub.1 to C.sub.4 haloalkyl, C.sub.2 to C.sub.4 alkoxyalkyl, C.sub.1 to C.sub.4 alkoxy and C.sub.1 to C.sub.4 haloalkoxy; each of X.sup.2 and X.sup.3 is independently selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 haloalkyl; X.sup.4 is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl and C.sub.1 to C.sub.4 alkoxy; each of X.sup.5, X.sup.6, X.sup.7 and X.sup.8 is independently hydrogen or C.sub.1 to C.sub.4 alkyl; the bond between X.sup.2 and X.sup.5 is saturated or unsaturated; the bond between X.sup.5 and X.sup.7 is saturated or unsaturated; p is an integer of 0 or 1; and n is an integer of 0, 1 or 2; or a salt thereof.
    Type: Grant
    Filed: December 15, 1997
    Date of Patent: May 16, 2000
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Kazufumi Nakamura, Masashi Sakamoto, Ichiro Nasuno
  • Patent number: 6020531
    Abstract: A benzothiophene compound represented by a formula: ##STR1## wherein R.sup.1 represents a lower alkyl group, and R.sup.2 represents a halogen atom; a lower alkyl group; or a cycloalkyl group or cycloalkenyl group which may optionally be substituted with a lower alkyl group, a hydroxy group, an acyloxy group or an oxo group,which is a useful intermediate for synthesizing a 2-sub-stituted-3-(4-substituted benzoyl)-6-hydroxybenzo[b]-thiophene derivative having an antiestrogenic activity can be produced in an industrially advantageous manner by subjecting a compound represented by a formula: ##STR2## to a ring-closing reaction. Further, the novel compound of the formula (II) described above is a useful intermediate in the process of the present invention.
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: February 1, 2000
    Assignee: Teikoku Hormone Mfg. Co., Ltd.
    Inventors: Masafumi Shiraiwa, Shuichiro Sato, Koji Doguchi
  • Patent number: 6008377
    Abstract: The present invention is directed to chemical processes for preparing 2-aryl-6-hydroxy-3-[4-(2-aminoethoxyl)benzoyl]benzoyl]benzo[b]-thiophenes.
    Type: Grant
    Filed: August 21, 1998
    Date of Patent: December 28, 1999
    Assignee: Eli Lilly and Company
    Inventors: Charles D Jones, John M. McGill
  • Patent number: 5981570
    Abstract: The invention provides benzothiophene compounds, formulations, and methods of inhibiting bone loss or bone resorption, particularly osteoporosis, cardiovascular-related pathological conditions, including hyperlipidemia.
    Type: Grant
    Filed: September 22, 1997
    Date of Patent: November 9, 1999
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, George Joseph Cullinan, Jeffrey Alan Dodge
  • Patent number: 5965749
    Abstract: A process for the preparation of a substituted 2-benzo[b]thiophenecarboxylic acid compound or an alkali metal salt thereof, which comprises reacting a halobenzoyl derivative with mercaptoacetic acid in the presence of an alkali metal hydroxide and water. Substituted 2-benzo[b]thiophenecarboxylic acid compounds and alkali metal salts thereof are useful as intermediates for pharmaceuticals, agricultural chemicals, material preservatives, and the like.
    Type: Grant
    Filed: March 16, 1998
    Date of Patent: October 12, 1999
    Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Co./CIE.
    Inventor: Walter Gerhard Brouwer
  • Patent number: 5952345
    Abstract: Aryl-substituted and aryl and (3-oxo-1-propenly)-substituted benzopyran, benzothiopyran, 1,2-dihydroquinoline, and 5,6-dihydronaphthalene derivatives have retinoid negative hormone and/or antagonist-like biological activities. The invented RAR antagonists can be administered to mammals, including humans, for the purpose of preventing or diminishing action of RAR agonists on the bound receptor sites. Specifically, the RAR agonists are administered or coadministered with retinoid drugs to prevent or ameliorate toxicity or side effects caused by retinoids or vitamin A or vitamin A precursors. The retinoid negative hormones can be used to potentiate the activities of other retinoids and nuclear receptor agonists. For example, the retinoid negative hormone called AGN 193109 effectively increased the effectiveness of other retinoids and steroid hormones in in vitro transactivation assays. Additionally, transactivation assays can be used to identify compounds having negative hormone activity.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: September 14, 1999
    Assignee: Allergan Sales, Inc.
    Inventors: Elliot S. Klein, Alan T. Johnson, Andrew M. Standeven, Richard L. Beard, Samuel J. Gillett, Tien T. Duong, Sunil Nagpal, Vidyasagar Vuligonda, Min Teng, Roshantha A. Chandraratna
  • Patent number: 5948796
    Abstract: This invention relates to the field of pharmaceutical and organic chemistry and provides benzothiophene compounds, intermediates, formulations, and methods.
    Type: Grant
    Filed: September 3, 1997
    Date of Patent: September 7, 1999
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, Michael John Martin, Ken Matsumoto
  • Patent number: 5929107
    Abstract: Novel compound represented by the formula: ##STR1## wherein ring A, ring B and ring C each stands for an optionally substituted benzene ring; X stands for --NR-- wherein R stands for hydrogen atom or an optionally substituted hydrocarbon group, --O-- or --S--; Y stands for --(CH.sub.2)n-- wherein n denotes 1 or 2 or --NH--; and R.sup.a stands for a hydrogen atom or an optionally substituted hydrocarbon group, provided that when ring C is unsubstituted or substituted only at para-position, ring B is substituted at least at ortho-position or a salt thereof which have an excellent acyl-CoA: cholesterol acyltransferase inhibiting action and cholesterol-lowering activity, their production and medicinal use.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: July 27, 1999
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideaki Natsugari, Yasuo Sugiyama, Yoshinori Ikeura
  • Patent number: 5908859
    Abstract: The present application relates to a series of compounds, and pharmaceutical formulations thereof, of the formula ##STR1## which provide a method of inhibiting hyperlipidemia, especially hypercholesterolemia, and the pathological sequelae thereof, in mammals, including humans.
    Type: Grant
    Filed: August 4, 1998
    Date of Patent: June 1, 1999
    Assignee: Eli Lilly and Company
    Inventors: George Joseph Cullinan, Patrick Irving Eacho, Patricia Sue Foxworthy-Mason, Robert John Schmidt
  • Patent number: 5886025
    Abstract: Methoxy and ethoxy substituted 3-aroyl-2-arylbenzo?b!thiophenes and benzo?b!thiophene analogues are described for use in inhibiting tubulin polymerization. The compounds' use for treating tumor cells is also described.
    Type: Grant
    Filed: March 6, 1997
    Date of Patent: March 23, 1999
    Assignee: Baylor University
    Inventor: Kevin G. Pinney
  • Patent number: 5863936
    Abstract: Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds characterized by the following structure: ##STR1## and their pharmaceutically acceptable salts. Y is selected from the group consisting of oxygen, sulfur, sulfonyl, sulfinyl, and --NR.sub.7 --. R.sub.1 is --TR.sub.8, where T is --C(X.sub.1)-- or --SO.sub.2 --, and R.sub.8 is selected from the group consisting of --OR.sub.9, --NHNHSO.sub.2 R.sub.9, --NHNHC(X.sub.2)OR.sub.9, --NR.sub.9 R.sub.10, --NHNHC(X.sub.2)NR.sub.9 R.sub.10, --NHCR.sub.9 R.sub.10 C(X.sub.2)NR.sub.11 R.sub.12, --NHC(X.sub.2)NR.sub.9 R.sub.10, and the piperazinyl moiety shown below: ##STR2## where n is 0 or 1, and Q.sub.n, for n=1, is --SO.sub.2 --, --C(X.sub.2)-- or --C(X.sub.2)NR.sub.10 --. R.sub.2 -R.sub.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: January 26, 1999
    Assignee: Geron Corporation
    Inventors: Federico C.A. Gaeta, Adam A. Galan, Elaine C. Stracker
  • Patent number: 5859297
    Abstract: Disclosed are labeling reagents containing fluorescent compounds represented by the general formula ##STR1## where R is a group capable of combining with proteins, Ar is a conjugated double bond system, and n is a whole number. These labeling reagents have high fluorescence emission intensities, give high synthesis yields, permit both solid-phase measurements and liquid-phase measurements in immunoassays, and require less measuring steps.
    Type: Grant
    Filed: October 23, 1996
    Date of Patent: January 12, 1999
    Assignees: Kazuko Matsumoto, Suzuki Motor Corporation
    Inventors: Kazuko Matsumoto, Jingli Yuan
  • Patent number: 5843984
    Abstract: Sulfated benzothiophenes of the formula I ##STR1## wherein R.sup.1 is hydrogen, hydroxy, C.sub.1 -C.sub.4 alkoxy, --OCOO(C.sub.1 -C.sub.6 alkyl), --OCO(C.sub.1 -C.sub.6 alkyl), --OCOAr wherein Ar is phenyl or optionally substituted phenyl, --OSO.sub.2 (C.sub.4 -C.sub.6 straight chain alkyl), or --OSO.sub.3 H;R.sup.2 is R.sup.1, Cl or F; with the proviso that at least one of R.sup.1 or R.sup.2 is --OSO.sub.3 H;R.sup.3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidino, 4-morpholino, dimethylamino, diethylamino, diisopropylamino, or 1-hexamethyleneimino; andn is 2 or 3;or a pharmaceutically acceptable salt or solvate thereof.
    Type: Grant
    Filed: April 14, 1997
    Date of Patent: December 1, 1998
    Assignee: Eli Lilly and Company
    Inventors: Michael Paul Clay, Charles Alan Frolik, Charles David Jones, Terry Donald Lindstrom
  • Patent number: 5817874
    Abstract: The present invention is a process of converting a hydroxy aromatic into a 2-hydroxy-N-arylacetamide, comprising:(1) treating a reaction mixture comprising a salt of a hydroxy aromatic with an alkylating agent; and(2) treating the reaction mixture with a Smiles solvent system and raising the temperature of the reaction mixture.
    Type: Grant
    Filed: March 18, 1997
    Date of Patent: October 6, 1998
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Norton P. Peet, John J. Weidner
  • Patent number: 5808061
    Abstract: The present invention provides a novel process for preparing a compound of formula I ##STR1## wherein R.sup.1 and R.sup.2 combine to form C.sub.4 -C.sub.6 polymethylene, --CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 --, --CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; or a pharmaceutically acceptable salt or solvate thereof.Also provided intermediates of formulae II and IV ##STR2## wherein Z is a leaving group.
    Type: Grant
    Filed: July 17, 1995
    Date of Patent: September 15, 1998
    Assignee: Eli Lilly and Company
    Inventors: Jeffrey A. Dodge, Mark G. Stocksdale
  • Patent number: 5792763
    Abstract: This invention provides novel 5-HT.sub.1F agonists of formula ##STR1## where X, Y, Z,and R are defined in the specification, which are useful for the prevention and treatment of migraine and associated disorders.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: August 11, 1998
    Assignee: Eli Lilly and Company
    Inventors: James E. Fritz, Stephen W. Kaldor, Sidney Xi Liang, Upinder Singh, Yao-Chang Xu
  • Patent number: 5780498
    Abstract: The present invention provides novel compounds represented by the general formula I: ##STR1## wherein R.sub.1 is a straight or branched lower alkyl, a cycloalkyl-lower alkyl, an aryl-lower alkyl, a cycloalkyl, an aryl an aryl-cycloalkyl, lower alkoxy, an aryloxy, or a heteroaryl;R.sub.2 is hydrogen, a straight or branched lower alkyl, a cycloalkyl, or a cycloalkyl-lower alkyl;R.sub.3 and R.sub.3 ' are each the same or different and each is hydrogen atom, a straight or branched lower alkyl, a cycloalkyl, an aryl-lower alkyl, an aryl, or a heteroaryl; orR.sub.3 and R.sub.3 ' together form a ring structure;R.sub.3 " is hydrogen, lower alkyl or an aryl; orR.sub.2 and R.sub.3 " together form a lower alkylene group --(CH.sub.2).sub.n -- wherein n is an integer of 1, 2 or 3; orR.sub.2 and R.sub.3 " together form a group represented by the formula: --(CH.sub.2).sub.p --Ar-- or --Ar--(CH.sub.2).sub.p --, respectively, wherein p is zero or an integer of 1 or 2, and Ar is an arylene or heteroarylene;C(.dbd.X) is C(.dbd.
    Type: Grant
    Filed: April 30, 1996
    Date of Patent: July 14, 1998
    Assignee: Ciba-Geigy Japan Limited
    Inventors: Hideyuki Saika, Toshiki Murata, Thomas Pitterna, Thomas Fruh, Lene D. Svensson, Yoshihiro Urade, Takaki Yamamura, Toshikazu Okada
  • Patent number: 5780648
    Abstract: Benzothiophenes, and uses and formulations thereof, are provided by the present invention.
    Type: Grant
    Filed: June 25, 1997
    Date of Patent: July 14, 1998
    Assignee: Eli Lilly and Company
    Inventors: David Thompson Berg, George Joseph Cullinan, Brian William Grinnell, Mark Alan Richardson
  • Patent number: 5760030
    Abstract: The instant invention provides novel benzothiophene compounds, pharmaceutical formulations, and methods of use.
    Type: Grant
    Filed: June 30, 1997
    Date of Patent: June 2, 1998
    Assignee: Eli Lilly and Company
    Inventors: Henry Uhlman Bryant, George Joseph Cullinan, Kennan Joseph Fahey
  • Patent number: 5760063
    Abstract: The subject invention, provides arylhydrazone compounds having the Formula 1: ##STR1## wherein A and B are independently aryl or heteroaryl and A and B independently are substituted with at least one group selected from alkyl, halogen, CN, COOR.sup.7, NR.sup.7 R.sup.8, CONR.sup.7 R.sup.8, NO.sub.2, SR.sup.7, SOR.sup.7, SO.sub.2 R.sup.7, NHCOR.sup.7, NHSO.sub.2 R.sup.7, OR.sup.7, hydroxyalkyl, and aminoalkyl. The compounds of this invention are useful for treating a wide variety of bacterial infections, including diseases of the skin, e.g., acne and skin ulcers, gastroenteritis, colitis, meningitis, keratinitis, conjunctivitis, diseases of the urinary and genital tracts, etc.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: June 2, 1998
    Assignee: Scriptgen Pharmaceuticals, Inc.
    Inventors: Kelvin T. Lam, David G. Powers
  • Patent number: RE37087
    Abstract: There are provided new alkane and alkoxyalkane derivatives of the general formula I in which R1, R2, R3, R4 and A have the meanings given in the description, processes for their preparation and insecticidal and acaricidal compositions containing these compounds.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: March 6, 2001
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien, Dietrich Baumert, David Giles
  • Patent number: RE36562
    Abstract: A method of controlling Take-All disease of plants by applying a fungicide of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are C and are part of an aromatic ring which is .[.benzothiophene.]..Iadd.thiophene.Iaddend.; andA is .[.selected from.]. --C(X)-amine .[.wherein the amine is an unsubstituted, monosubstituted or disubstituted amino radical.]..Iadd.wherein the amine is a monosubstituted or a disubstituted amine, wherein one of the substituents has a cyclic moiety, said cyclic moiety which is chosen from the group consisting of thienyl, furanyl, and a non-heterocyclic substituent, wherein when the amine is disubstituted, the second substituent is a non-cyclic substituent.Iaddend., --C(O)--SR.sub.3, --NH--C(X)R.sub.4, .[.and.]. .Iadd.or .Iaddend.--C(.dbd.NR.sub.3)--XR.sub.7 ;B is --W.sub.m --Q(R.sub.2).sub.3 or selected from .[.O-tolyl.]..Iadd.o-tolyl.Iaddend., 1-naphthyl, 2-naphthyl, and 9-phenanthryl, each optionally substituted with halogen or R.sub.4 ;Q is C, Si, Ge, or Sn;W is --C(R.sub.3).sub.p H.
    Type: Grant
    Filed: March 11, 1998
    Date of Patent: February 8, 2000
    Assignee: Monsanto Company
    Inventors: Dennis P. Phillion, Diane S. Braccolino, Matthew J. Graneto, Wendell G. Phillips, Karey A. Van Sant, Daniel M. Walker, Sai C. Wong