Halogen Or Nitrogen Attached Directly To Diazine Ring Carbon By Nonionic Bonding Patents (Class 544/356)
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Patent number: 6001832Abstract: The present invention relates to [1,2,4]triazolo[4,3-a]quinoxalinone compounds of the formula ##STR1## wherein R.sup.1 is POX'X" or alkyl substituted with COX' or POX'X", and X' and X" independently are hydroxy or alkoxy, and R.sup.7 is trifluoromethyl, and R.sup.6, R.sup.8 and R.sup.9 independently are piperidino, piperazinyl, morpholino, or thiomorpholino, which rings are optionally substituted with one or more of phenyl or C.sub.1-6 -alkyl and phenyl optionally being substituted with C.sub.1-6 -alkoxy; and pharmaceutically acceptable salts thereof. The compounds of the present invention are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.Type: GrantFiled: March 7, 1997Date of Patent: December 14, 1999Assignee: Novo NordiskalsInventor: Flemming Elmelund Nielsen
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Patent number: 5977113Abstract: Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. the compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. Depot derivatives of the compounds are useful for providing long acting effects of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.Type: GrantFiled: June 6, 1995Date of Patent: November 2, 1999Assignee: Hoechst Marion Roussel, Inc.Inventors: Edward J. Glamkowski, Yulin Chiang, Joseph T. Strupczewski, Kenneth J. Bordeau, Peter A. Nemoto, John J. Tegeler
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Patent number: 5962455Abstract: This invention encompasses compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof wherein X.sub.1, X.sub.2, X.sub.3 represent organic or inorganic substituents, n is 1, 2, or 3, m is 2, 3, or 4, R.sub.1 -R.sub.4 are hydrogen or organic substituents, and B is nitrogen, carbon, sulfur or oxygen, useful in the diagnosis and treatment of feeding disorders such as obesity and bulimia and cardiovascular diseases such as essential hypertension and congestive heart failure due to the binding of these compounds to mammalian Neuropeptide Y1 receptors.Type: GrantFiled: July 18, 1997Date of Patent: October 5, 1999Assignee: Neurogen CorporationInventors: Charles A. Blum, Alan Hutchison, John M. Peterson
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Patent number: 5922708Abstract: The invention relates to novel heteroaryl-oxazolidinones of the general formula (I): ##STR1## in which the substituents are as defined in the description, to processes for their preparation and to their use as drugs, especially as antibacterial drugs.Type: GrantFiled: February 3, 1997Date of Patent: July 13, 1999Assignee: Bayer AktiengesellschaftInventors: Bernd Riedl, Dieter Habich, Andreas Stolle, Martin Ruppelt, Stephan Bartel, Walter Guarnieri, Rainer Endermann, Hein-Peter Kroll
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Patent number: 5922711Abstract: A compound of the formula: ##STR1## wherein --X.sup.3 .dbd.X.sup.2 --X.sup.1 .dbd.N-- is a group of the formula: ##STR2## R.sup.1 is hydrogen or halogen, R.sup.2 is halogen,R.sup.3 is hydrogen, nitro, amino optionally having at least one substituent or a heterocyclic group optionally having at least one substituent,R.sup.4 and R.sup.5 are each hydrogen, or halogen,R.sup.6 and R.sup.8 are each hydrogen, halogen, lower alkyl, hydroxy, lower alkylthio, amino optionally substituted with lower alkyl, or lower alkoxy optionally substituted with a substituent selected from the group consisting of hydroxy, lower alkoxy, amino, lower alkylamino and aryl optionally substituted with lower alkoxy,R.sup.7 is hydrogen or lower alkyl,A is lower alkylene, andQ is O or N--R.sup.9 is hydrogen or acyl,provided that R.sup.3 is not hydrogen when X.sup.1 is C--R.sup.6, in which R.sup.6 is hydrogen, andpharmaceutically acceptable salts thereof.Type: GrantFiled: September 19, 1997Date of Patent: July 13, 1999Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Teruo Oku, Hiroshi Kayakiri, Shigeki Satoh, Yoshito Abe, Yuki Sawada, Takayuki Inoue, Hirokazu Tanaka
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Patent number: 5880135Abstract: A compound, as well as its stereoisomers and addition salts, possssing antagonist activity with respect to corticotropin releasing hormone (CRF) has the formula: ##STR1## in which R.sub.1, and R.sub.21 which are identical or different, are independently selected from a halogen atom; a (C.sub.1 -C.sub.5)hydroxyalkyl radical; a (C.sub.1 -C.sub.5)alkyl; a (C.sub.7 -C.sub.10)aralkyl; a (C.sub.1 -C.sub.5)alkoxy; a trifluoromethyl; a nitro; a nitrile; an --SR group in which R is selected from hydrogen, a (C.sub.1 -C.sub.5)alkyl radical and a (C.sub.7 -C.sub.10)aralkyl radical; an --S--CO--R group in which R is selected from a (C.sub.1 -C.sub.5)alkyl radical and an aralkyl radical in which the aryl part is (C.sub.6 -C.sub.8) and the alkyl part is (C.sub.1 -C.sub.4); a --COOR' group in which R' is selected from hydrogen and a (C.sub.1 -C.sub.Type: GrantFiled: December 22, 1997Date of Patent: March 9, 1999Assignee: SanofiInventors: Danielle Gully, Pierre Roger, Camille Georges Wermuth
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Patent number: 5852016Abstract: Compounds of formula (I), wherein A represents N or CH; R.sup.1 and R.sup.2 independently represent C.sup.1-4 alkyl, halo or CF.sub.3 ; R.sup.3 represents C.sub.1-4 alkyl (optionally substituted), C.sub.3-7 cycloalkyl, CF.sub.3 or aryl; R.sup.4 represents H, C.sub.3-7 cycloalkyl or C.sub.1-6 alkyl (optionally substituted); and their pharmaceutically acceptable derivatives; are useful in the treatment of, inter alia, neurodogenerative disorders.Type: GrantFiled: March 21, 1997Date of Patent: December 22, 1998Assignee: Pfizer Inc.Inventors: Michael Jonathan Fray, Charles Eric Mowbray, Alan Stobie
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Patent number: 5849742Abstract: The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction and particularly KDR/FLK-1 receptor signal transduction in order to regulate and/or modulate vasculogenesis and angiogenesis. The invention is based, in part, on the demonstration that KDR/FLK-1 tyrosine kinase receptor expression is associated with endothelial cells and the identification of vascular endothelial growth factor (VEGF) as the high affinity ligand of FLK-1. These results indicate a major role for KDR/FLX-1 in the signaling system during vasculogenesis and angiogenesis. Engineering of host cells that express FLK-1 and the uses of expressed FLK-1 to evaluate and screen for drugs and analogs of VEGF involved in FLK-1 modulation by either agonist or antagonist activities is also described.Type: GrantFiled: May 9, 1997Date of Patent: December 15, 1998Assignees: Sugen Inc., Yissum Research Development Co. of The Hebrew Universuty of JerusalemInventors: Harald App, Gerald M. McMahon, Peng Cho Tang, Aviv Gazit, Alexander Levitzki
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Patent number: 5792771Abstract: The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction and particularly KDR/FLK-1 receptor signal transduction in order to regulate and/or modulate vasculogenesis and angiogenesis. The invention is based, in part, on the demonstration that KDR/FLK-1 tyrosine kinase receptor expression is associated with endothelial cells and the identification of vascular endothelial growth factor (VEGF) as the high affinity ligand of FLK-1. These results indicate a major role for KDR/FLK-1 in the signaling system during vasculogenesis and angiogenesis. Engineering of host cells that express FLK-1 and the uses of expressed FLK-1 to evaluate and screen for drugs and analogs of VEGF involved in FLK-1 modulation by either agonist or antagonist activities is also described.Type: GrantFiled: June 5, 1995Date of Patent: August 11, 1998Assignees: Sugen, Inc., Yissum Research Development Co. of the Hebrew University of JerusalemInventors: Harald App, Gerald M. McMahon, Peng Cho Tang, Aviv Gazit, Alexander Levitzki
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Patent number: 5777119Abstract: Quinoxalines are prepared by reaction of oxalic acid with an o-phenylenediamine, halogenation in the presence of a solvent and oxidation to a quinoxaline carboxylic acid derivative.Type: GrantFiled: November 21, 1995Date of Patent: July 7, 1998Assignee: Bayer AktiengesellschaftInventors: Jens Uwe Zarnack, Bernd Diesselkamper, Wolfgang Lorenz, Jorg-Michael Borchers
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Patent number: 5739134Abstract: N-(3-hydroxy-4-piperidinyl)(dihydrobenzofuran, dihydro-2H-benzopyran or dihydrobenzodioxin)carboxamide derivatives, their N-oxide forms and pharmaceutically acceptable salts having gastrointestinal motility stimulating properties, compositions containing these compounds as active ingredient and methods of treating warm-blooded animals suffering from the decreased peristalsis of the gastrointestinal system.Type: GrantFiled: April 13, 1995Date of Patent: April 14, 1998Assignee: Janssen Pharmacetuica N.V.Inventors: Georges H.P. Van Daele, deceased, Frans M.A. Van den Keybus, Marie L. Hendrickx, heiress, Kurt G.C.E. Van Daele, heir, Peter J.V. Van Daele, heir, Glenn K.L. Van Daele, heir
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Patent number: 5723462Abstract: Disclosed are compounds of formula I: ##STR1## wherein R.sub.8 and R.sub.9 independently represent hydrogen or organic substituents;W represents optionally substituted thiazolyl or quinoxalinyl;X is hydrogen, hydroxy or lower alkyl; andT is hydrogen, halogen, hydroxy, nitro, amino or alkyl,which compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptor. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.Type: GrantFiled: April 26, 1996Date of Patent: March 3, 1998Assignee: Neurogen CorporationInventors: Pamela Albaugh, Gang Liu, Alan Hutchison
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Patent number: 5723613Abstract: Methyl aromatic compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 have the meaning given in the description,can be reacted in an advantageous manner using free-radicals to give the associated trichloromethyl or tribromomethyl aromatic compounds, if the reaction is carried out in the presence of one or more chlorides or bromides of the heavy alkali metals.Type: GrantFiled: October 2, 1992Date of Patent: March 3, 1998Assignee: Bayer AktiengesellschaftInventor: Guido Steffan
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Patent number: 5716446Abstract: Novel isoindoline pigments of the formula (I): ##STR1## in which R.sup.1 is --CN;R.sup.2 is --CN or a saturated or unsaturated, aromatic or non-aromatic, 5- to 7-membered heterocyclic ring system which can be modified by fusion or bridging with other heterocyclic or isocyclic ring systems, the heteroatoms being N, O and/or S;or a group --CO--NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 are identical or different and are hydrogen or C.sub.1 -C.sub.4 -alkyl;or a group --CO--NR.sup.6 R.sup.8, in which R.sup.8 is a saturated or unsaturated, aromatic or non-aromatic, 5- to 7-membered isocyclic or heterocyclic ring which is unsubstituted or substituted by one to 5 of the following radicals: C.sub.1 -C.sub.4 -alkyl, halogen, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, carbomethoxy, carbethoxy, carboxamide, carboxamide substituted by a C.sub.1 -C.sub.4 -alkyl or phenyl group, nitro, C.sub.1 -C.sub.Type: GrantFiled: May 6, 1996Date of Patent: February 10, 1998Assignee: Hoechst AktiengesellschaftInventors: Frank Alfter, Rudiger Jung, Gustav Kapaun
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Patent number: 5714488Abstract: Compounds having the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein W is selected from the group consisting of optionally substituted quinolyl, optionally substituted benzothiazolyl, optionally substituted benzoxazolyl, optionally substituted benzimidazolyl, optionally substituted quinoxalyl, optionally substituted pyridyl, optionally substituted pyrimidyl, and optionally substituted thiazolyl; R.sup.1 and R.sup.2 are one or more groups independently selected from hydrogen, alkyl, halolalkyl, alkoxy, and halogen; Z is selected from the group consisting of N--OH, N--O--A--COM, CH--COM, and CH--CH.dbd.N--0--A--COM wherein A is selected from the group consisting of alkylene, alkenylene, cycloalkylene, and optionally substituted alkylphenyl wherein the alkyl portion is of one to six carbon atoms, and M is selected from the group consisting of a pharmaceutically acceptable, metabolically clearable group, --OR.sup.3, and --NR.sup.4 R.sup.Type: GrantFiled: September 17, 1996Date of Patent: February 3, 1998Assignee: Abbott LaboratoriesInventors: Clint D. W. Brooks, Pramila Bhatia, Teodozyj Kolasa
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Patent number: 5712395Abstract: The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction and particularly KDR/FLK-1 receptor signal transduction in order to regulate and/or modulate vasculogenesis and angiogenesis. The invention is based, in part, on the demonstration that KDR/FLK-1 tyrosine kinase receptor expression is associated with endothelial cells and the identification of vascular endothelial growth factor (VEGF) as the high affinity ligand of FLK-1. These results indicate a major role for KDR/FLK-1 in the signaling system during vasculogenesis and angiogenesis. Engineering of host cells that express FLK-1 and the uses of expressed FLK-1 to evaluate and screen for drugs and analogs of VEGF involved in FLK-1 modulation by either agonist or antagonist activities is also described.Type: GrantFiled: February 9, 1995Date of Patent: January 27, 1998Assignees: Yissum Research Development Corp., SugenInventors: Harald App, Gerald M. McMahon, Peng Cho Tang, Aviv Gazit, Alexander Levitzki
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Patent number: 5677305Abstract: An oxopyridinylquinoxaline derivative represented by the following Formula I or pharmaceutically acceptable salts thereof: ##STR1## wherein R.sup.1 is hydrogen, halogen, nitro, or trihalomethyl; R.sup.2 is hydrogen, halogen, nitro, cyano, trihalomethyl, carbamoyl, carbamoyl substituted with lower alkyl, sulfamoyl, or sulfamoyl substituted with lower alkyl; R.sup.3 is hydrogen, nitro, or halogen; R.sup.4 is hydrogen, lower alkyl, substituted lower alkyl, lower cycloalkyl, or substituted lower cycloalkyl; R.sup.5 's are substituents independently selected from the group consisting of halogen, nitro, cyano, lower alkyl, carbamoyl, and carbamoyl substituted with lower alkyl; and n is an integer of 0 to 4. The derivative works as an antagonistic agent against both the NMDA receptors and the AMPA receptors, so that it is effective as a therapeutic agent for neurological disorders caused by excitatory amino acids binding to the receptors.Type: GrantFiled: April 7, 1995Date of Patent: October 14, 1997Assignee: Shionogi & Co., Ltd.Inventors: Susumu Takada, Nobuo Chomei, Makoto Adachi, Masami Eigyo, Kazuo Kawasaki
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Patent number: 5629322Abstract: Disclosed herein are compounds of Formula I ##STR1## and pharmaceutically acceptable salts thereof which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders, including neurodegenerative disorders, disorders of gastrointestinal motility and inflammation. These disease and disorders include hypotension, septic shock, toxic shock syndrom, hemodialysis, IL-2 therapy such as in cancer patients, cachexia, immunosuppression such as in transplant therapy, autoimmune and/or inflammatory indications including sunburn or psoriasis and respiratory conditions such as bronchitis, asthma, and acure respiratory distress (ARDS), myocarditis, heart failure, atherosclerosis, arthritis, rheumatoid arthritis, chronic or inflammatory bowel disease, ulcerative colitis, Crohn's disease, systemic lupus erythematosis (SLE), ocular conditions such as ocular hypertension and uveitis, type 1 diabetes, insulin-dependent diabetes mellitus and cystic fibrosis.Type: GrantFiled: June 6, 1995Date of Patent: May 13, 1997Assignee: Merck & Co., Inc.Inventors: Ravindra N. Guthikonda, Stephan K. Grant, Malcolm Maccoss, Shrenik K. Shah, Kothandaraman Shankaran, Charles G. Caldwell, Philippe L. Durette
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Patent number: 5627181Abstract: The invention relates to 6-membered nitrogen-containing heteroaryloxazolidinones, processes for their preparation and their use as medicaments, in particular as antibacterial medicaments.Type: GrantFiled: July 17, 1995Date of Patent: May 6, 1997Assignee: Bayer AktiengesellschaftInventors: Bernd Riedl, Dieter H abich, Andreas Stolle, Hanno Wild, Rainer Endermann, Klaus D. Bremm, Hein-Peter Kroll, Harald Labischinski, Klaus Schaller, Hans-Otto Werling
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Patent number: 5583227Abstract: This invention relates to a novel compound which is useful as a drug in preventing and/or treating peptic ulcer-related diseases, to a production process thereof and to a pharmaceutical composition containing the same.Particularly, it provides a compound which has a specified substituted alkynylpyrazine nucleus or a specified substituted alkynylquinoxaline nucleus, represented by the following formula (I) ##STR1## wherein A is represented by the following formula (II) or (III) ##STR2## and R.sup.1 is represented by the following formula (IV), ##STR3## and the salts thereof, a production process thereof and a pharmaceutical composition containing the same.The inventive compound is useful as a drug in preventing and/or treating peptic ulcer-related diseases.Type: GrantFiled: June 2, 1995Date of Patent: December 10, 1996Assignees: Mochida Pharmaceutical Co. Ltd., Hodogaya Chemical Co. Ltd.Inventors: Takeshi Niho, Ichiro Yamamoto, Hidenori Mochizuki, Ikuo Kimura, Akihiro Imai, Tetsuyuki Nakase
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Patent number: 5576432Abstract: A process of preparing a dihydropyrimidine compound of the structure (I): ##STR1## wherein R.sup.1 and R.sup.2 are bonded together to form an aromatic or heterocyclic ring, which may be substituted or unsubstituted, or are individually selected from the group consisting of hydrogen, or a substituted or unsubstituted aliphatic, carbocyclic, or heterocyclic group;R.sup.3, R.sup.4 and R.sup.5 are individually selected from the group consisting of hydrogen or a substituted or unsubstituted aliphatic, carbocyclic or heterocyclic group; andX represents the atoms necessary to form a 5 or 6 membered heterocyclic ring, and is selected from the group consisting of oxygen, sulfur, selenium, ##STR2## wherein R.sup.6, R.sup.7, and R.sup.8 are individually selected from the group consisting of a substituted or unsubstituted aliphatic, carbocyclic or heterocyclic group; comprising combining a compound (A) of the structure: ##STR3## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, and R.sup.Type: GrantFiled: December 23, 1994Date of Patent: November 19, 1996Assignee: Eastman Kodak CompanyInventors: Roger Lok, Antony J. Williams
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Patent number: 5559106Abstract: Quinoxaline compounds of the general formula ##STR1## wherein R.sup.1 is COX', POX'X" or alkyl substituted with COX' or POX'X", and X' and X" independently are hydroxy or alkoxy, and R.sup.6, R.sup.7, R.sup.8 and R.sup.9 independently are hydrogen, alkyl, halogen, NH.sub.2, NO.sub.2, CN, CF.sub.3, SO.sub.2 NY'Y" or COZ' wherein Z' is NY'Y" or alkyl and Y' and Y" independently are hydrogen or alkyl, triazolyl, imidazolyl, imidazolyl substituted with phenyl or alkyl, or R.sup.6 and R.sup.7, or R.sup.8 and R.sup.9, together form a further fused ring, are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.Type: GrantFiled: December 7, 1994Date of Patent: September 24, 1996Assignee: Novo Nordisk A/SInventors: Poul Jacobsen, Flemming E. Nielsen, Lone Jeppesen
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Patent number: 5529999Abstract: This invention provides certain sulfonamidoquinoxaline derivatives and methods for using them in the treatment of susceptible neoplasms in mammals. Also provided are certain novel pharmaceutical formulations employing these sulfonamidoquinoxaline derivatives, in combination with a carrier, diluent or excipient.Type: GrantFiled: March 4, 1994Date of Patent: June 25, 1996Assignee: Eli Lilly and CompanyInventors: James E. Ray, John E. Toth
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Patent number: 5519022Abstract: The invention concerns .alpha.,.alpha.-dialkylbenzyl derivatives of the formula I ##STR1## wherein Ar.sup.1 is phenyl or naphthyl, or a 10-membered bicyclic heterocyclic moiety containing one or two nitrogen heteroatoms and optionally containing a further heteroatom selected from nitrogen, oxygen and sulphur;A.sup.1 is a direct link to X.sup.1 or is (1-3C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;the phenylene group may optionally bear one or two substituents R.sup.3 ;each of R.sup.1 and R.sup.2, which may be the same or different is (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, fluoro-(1-4C)alkyl, phenyl or phenyl-(1-4C)alkyl, provided that both of R.sup.1 and R.sup.2 are not methyl or fluoromethyl; andQ is cyano, amino, nitro, formyl, (1-4C)alkoxy, thiazolyl or (2-4C)alkanoyl;or a pharmaceutically-acceptable salt thereof;processes for their manufacture; pharmaceutical compositions containing them and their use as 5-lipoxygenase inhibitors.Type: GrantFiled: November 10, 1993Date of Patent: May 21, 1996Assignees: Imperial Chemical Industries Plc, ICI PharmaInventors: Philip N. Edwards, David Waterson
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Patent number: 5480883Abstract: This invention relates to bis mono- and/or bicyclic aryl and/or heteroaryl compounds exhibiting protein tyrosine kinase inhibition activity. More specifically, it relates to the method of inhibiting abnormal cell proliferation in a patient suffering from a disorder characterized by such proliferation comprising the administration thereto of an EGF and/or PDGF receptor inhibiting effective amount of said bis mono- and/or bicyclic aryl and/or heteroaryl compound and to the preparation of said compounds and their use in pharmaceutical compositions used in this method.Type: GrantFiled: December 10, 1993Date of Patent: January 2, 1996Assignee: Rhone-Poulenc Rorer Pharmaceuticals Inc.Inventors: Alfred P. Spada, Michael R. Myers, Martin P. Maguire, Paul E. Persons
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Patent number: 5438144Abstract: The invention relates to the use of 1,4-dihydropyridines having calcium antagonistic action, in particular of nimodipine, for the preparation of medicaments for controlling damage to peripheral nerves which is caused by diabetes.Type: GrantFiled: July 9, 1993Date of Patent: August 1, 1995Assignee: Troponwerke GmbH & Co. KGInventors: Jorg Traber, Willem H. Gispen
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Patent number: 5405843Abstract: Heterocyclic compounds useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells are disclosed, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.Type: GrantFiled: September 9, 1993Date of Patent: April 11, 1995Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Nobuyuki Fukazawa, Makoto Odate, Tsuneji Suzuki, Kengo Otsuka, Takashi Tsuruo, Wakao Sato
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Patent number: 5399693Abstract: Compounds of the general formula ##STR1## wherein X is a C.sub.1 -C.sub.6, straight chain saturated or unsaturated hydrocarbyl group, the group R.sup.4 and the group Y are situated in any position in this chain and wherein at least one of the hydrogen atoms in X can be a heavy isotope of hydrogen;R.sup.4 is hydrogen or an alkyl, alkoxy, hydroxy, aryl, aryloxy, aralkyl, aralkoxy, aralkylamino, or morpholino group wherein the alkyl or aryl part of any one of said groups may be substituted by one or more halogeno groups; or R.sup.4, together with at least one carbon atom of the group X, forms a carbocyclic or heterocyclic ring of 5 to 6 ring atoms;Y is an acidic or related group giving rise to one or more electronegative sites in the group; or R.sup.4 --X--Y represents a carboxylic acyl group;R is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl;R.sup.1 is hydrogen or an alkyl, haloalkyl, aryl, haloaryl, aralkyl or haloaralkyl group;R.sup.2 R.sup.3 and R.sup.Type: GrantFiled: January 23, 1990Date of Patent: March 21, 1995Assignee: British Technology Group LimitedInventors: Jeffrey C. Watkins, Arwel W. Jones
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Patent number: 5380719Abstract: Angiotensin II inhibition is exhibited by ##STR1## wherein: X is --CH.sub.2 -- or O;R is hydrogen, alkyl, aryl, cycloalkyl, aralkyl, or cycloalkylalkyl;R.sup.1 and R.sup.2 are each independently O or absent;R.sup.3 is hydrogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, aralkyl, cycloalkylalkyl, halo, haloalkyl, or haloalkoxy;R.sup.4 is hydrogen, alkyl, alkenyl, alkoxy, aryl, cycloalkyl, aralkyl, cycloalkylalkyl, --R.sup.8 --OH, or --R.sup.8 CO.sub.2 R.sup.9 ;and the remaining symbols are as defined in the specification.Type: GrantFiled: April 28, 1992Date of Patent: January 10, 1995Assignee: E. R. Squibb & Sons, Inc.Inventor: Kyoung S. Kim
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Patent number: 5346902Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein Y is a specified small group or single atom and R.sup.1 and R.sup.2 are selected from a wide range of specified substituents.Type: GrantFiled: May 11, 1993Date of Patent: September 13, 1994Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine
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Patent number: 5312820Abstract: Carbamoyl and oxycarbonyl derivatives of biphenylmethylamines of structure I are angiotensin-II antagonists with balanced AT.sub.1 and AT.sub.2 activity useful in the treatment of hypertension and related disorders and ocular hypertension. ##STR1## where X is --O-- or --N(R.sup.7)--.Type: GrantFiled: July 17, 1992Date of Patent: May 17, 1994Assignee: Merck & Co., Inc.Inventors: Wallace T. Ashton, Linda L. Chang, William J. Greenlee, Steven M. Hutchins, Ralph A. Rivero
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Patent number: 5302594Abstract: The invention concerns a heterocyclic derivative of the formula I ##STR1## wherein Q is an optionally substituted quinoxalinyl or a hydrogenated derivative thereofX.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl or (3-6C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.Type: GrantFiled: February 8, 1993Date of Patent: April 12, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Philip N. Edwards
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Patent number: 5286750Abstract: Unsaturated phenylacetic acid derivatives of the general formula ##STR1## where U is .dbd.O, .dbd.CH--OCH.sub.3, .dbd.N--OCH.sub.3, .dbd.N--NH--CH.sub.3, .dbd.CH.sub.2, .dbd.CH--CH.sub.3, .dbd.CH--CH.sub.2 --CH.sub.3 or .dbd.CH--S--CH.sub.3 andZ.sup.1 and Z.sup.2 are hydrogen, halogen, trifluoromethyl, cyanide, NO.sub.2 or unsubstituted or substituted alkyl, alkenyl, aryl, alkynyl, alkoxy, aryloxy, arylalkoxy, acyloxy, hetaryl, --CO.sub.2 R.sup.1, --CONR.sup.2 R.sup.3, COR.sup.4 or NR.sup.5 R.sup.6, and Z.sup.1 and Z.sup.2 may also form a ring,A is meta or para and is (CH.sub.2).sub.n, CH.dbd.CH, O--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO, CH.sub.2 --O--CO--(CH.sub.2).sub.n, CO--O--(CH.sub.2).sub.n, O--CO--(CH.sub.2).sub.n, O--(CH.sub.2).sub.n --CO--O, O--(CH.sub.2).sub.n+2 --O, CH.sub.2 O--(CH.sub.2).sub.n, CH.sub.2 --S--(CH.sub.2).sub.n CH.sub.2 --NR.sup.7 --(CH.sub.2).sub.n, CH(CN)--O--CO--(CH.sub.2).sub.n, CH.dbd.N--(CH.sub.2).sub.n or CH.dbd.N--O--(CH.sub.2).sub.n.Type: GrantFiled: March 15, 1993Date of Patent: February 15, 1994Assignee: BASF AktiengesellschaftInventors: Bernd Mueller, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz, Franz Roehl
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Patent number: 5280009Abstract: Pyrimidine derivatives of the Formula Ia or Ib ##STR1## where the substituents have the following meanings: R.sup.1 is hydrogen or alkyl;A is a substituted or unsubstituted bi- or tricyclic carbo- or heterocyclic radical which may contain one or several double bonds;R.sup.5 is H or alkyl;X is halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio; and addition salts thereof with organic or inorganic acids and the use of said pyrimidine derivative to control undesirable plant growth.Type: GrantFiled: July 16, 1992Date of Patent: January 18, 1994Assignee: BASF AktiengesellschaftInventors: Gerhard Hamprecht, Klaus Ditrich, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
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Patent number: 5236919Abstract: The invention concerns a heterocycle of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents orAr is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl;and R.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.Type: GrantFiled: May 11, 1992Date of Patent: August 17, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Philip N. Edwards, Jean-Marc M. M. Girodeau
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Patent number: 5223517Abstract: Heterocyclically substituted cycloalkano[b]-indolesulphonamides can be prepared by reaction of appropriate N-unsubstituted indoles with acrylonitrile, followed by hydrolysis, esterification or amidation, or by reaction of heterocyclically substituted hydrazines with cycloalkanones or by subsequent introduction of the heterocyclic group into appropriate indole derivatives. The heterocyclically substituted cycloalkano[b]-indolesulphonamides can be employed for the treatment of thromboembolic disorders, ischaemias, arteriosclerosis, asthma, allergies and for the prophylaxis of myocardial infarcts.Type: GrantFiled: August 23, 1991Date of Patent: June 29, 1993Assignee: Bayer AktiengesellschaftInventors: Ulrich E. Muller, Ulrich Niewohner, Elisabeth Perzborn, Erwin Bischoff, Hans-Georg Dellweg
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Patent number: 5182386Abstract: This invention encompasses compounds of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 are variables;X and Y represent hydrogen, halogen, hydroxy or amino substituents, with the proviso that when Y is a hydrogen, halogen, or amino substituent, X is hydroxy; andW represent aryl groups unsubstituted or substituted with halogen, hydroxy, alkyl, alkoxy or amino groups.These compounds or prodrugs thereof are highly selective agonists, antagonists or inverse agonists or GaBAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorder, overdose with benzodiazepine drugs, and enchancement of memory.Type: GrantFiled: August 27, 1991Date of Patent: January 26, 1993Assignee: Neurogen CorporationInventors: Pamela Albaugh, Alan J. Hutchinson
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Patent number: 5180725Abstract: Non-peptidyl compounds characterized generally as quinoxalinyl/qunioxalinylalkyl-N-terminal amino hydroxy .beta.-amino acid derivatives are useful as renin inhibitors for treatment of hypertension. Compounds of particular interest are of the formula ##STR1## wherein R.sub.1 is selected from ##STR2## wherein each of Y and Z is independently selected from hydrido, chloro, fluoro, methoxy and dimethylamino; wherein n is a number selected from zero through four, inclusive; wherein each of R.sub.2 and R.sub.4 is independently selected from hydrido and methyl; wherein R.sub.3 is methyl or ethyl; wherein R.sub.5 is cyclohexylmethyl; wherein R.sub.6 is hydroxy; and wherein R.sub.7 is isobutyl or ethyl; or a pharmaceutically-acceptable salt thereof.Type: GrantFiled: August 2, 1991Date of Patent: January 19, 1993Assignee: G. D. Searle & Co.Inventors: Gunnar J. Hanson, John S. Baran, Dave Weissing, Mark Russell
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Patent number: 5151421Abstract: (1H-azol-1-ylmethyl)substituted quinoxaline derivatives, compositions containing the same, and methods of treating mammals suffering from disorders which are characterized by an increased proliferation and/or abnormal differentiation of epithelial tissues.Type: GrantFiled: March 20, 1991Date of Patent: September 29, 1992Assignee: Janssen Pharmaceutica N.V.Inventors: Marc G. Venet, Gerard C. Sanz, Alfons H. M. Raeymaekers, Eddy J. E. Freyne
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Patent number: 5130312Abstract: N-(3-hydroxy-4-piperidinyl)substituted benzamides, their N-oxide forms and pharmaceutically acceptable acid-addition salts having gastro-intestinal motility stimulating properties, compositions containing the same, and methods of treating warm blooded animals suffering from a decreased peristalsis of the gastrointestinal system.Type: GrantFiled: January 23, 1990Date of Patent: July 14, 1992Assignee: Janssen Pharmaceutica N.V.Inventors: Georges H. P. Van Daele, Freddy F. Vlaeminck, Karel J. Van Loon
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Patent number: 5116405Abstract: A pyridinesulfonamide derivative of the formula (I) and a salt thereof: ##STR1## wherein R.sup.1 is a halogen atom, a trifluoromethyl group, a C.sub.1 -C.sub.6 alkoxycarbonyl group, a C.sub.1 -C.sub.6 mono- or di-alkylaminocarbonyl group, a C.sub.1 -C.sub.6 alkxoy group, a C.sub.1 -C.sub.6 alkylsulfonyl group, a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.6 alkyl group substituted by a C.sub.1 -C.sub.6 alkoxy group, a C.sub.1 -C.sub.6 alkyl group substituted by a C.sub.1 -C.sub.6 mono- or poly-halogenoalkoxy group, a C.sub.1 -C.sub.6 mono- or poly-halogenoalkoxy group, a C.sub.1 -C.sub.6 mono- or di-alkylaminosulfonyl group, a C.sub.1 -C.sub.6 alkoxyaminosulfonyl group substituted by a C.sub.1 -C.sub.6 alkyl group, a nitro group, a C.sub.1 -C.sub.6 alkyl group substituted by a C.sub.1 -C.sub.6 alkylthio group, a C.sub.1 -C.sub.5 alkyl group substituted by a C.sub.1 -C.sub.6 alkylsulfonyl group, or a C.sub.1 -C.sub.6 alkyl group substituted by a C.sub.1 -C.sub.6 alkoxycarbonyl group;R.sup.Type: GrantFiled: October 31, 1990Date of Patent: May 26, 1992Assignee: Nissan Chemical Industries Ltd.Inventors: Kenzi Makino, Katsushi Morimoto, Shigeaki Akiyama, Hideaki Suzuki, Takeshi Nagaoka, Koichi Suzuki, Tsutomu Nawamaki, Shigeomi Watanabe
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Patent number: 5114940Abstract: Compound of the formula (I) are disclosedArQQ.sup.1 C(.dbd.X)NHR.sup.1 (I)or a salt thereof, wherein Ar is an optionally substituted polycyclic ring system containing n rings, where n is the integer 2 or 3, at least n-1 rings being aromatic and containing one to three ring nitrogen atoms and optionally containing one or more additional heteroatoms; Q is an alkyl chain containing 1 to 12 carbon atoms and optionally containing a sulphur or one or two oxygen atoms; Q.sup.1 is a group (C(R.sup.2).dbd.C(R.sup.3)).sub.a --(C(R.sup.4).dbd.C(R.sup.5)) wherein a is 0 or 1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different, at least two being hydrogen and the other two being independently selected from hydrogen, halo, C.sub.1-4 haloalkyl; X is oxygen or sulphur; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy are described which have activity particularly against arthropod pests.Type: GrantFiled: May 22, 1989Date of Patent: May 19, 1992Inventors: Robert J. Blade, Robert J. Peek, George S. Cockerill
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Patent number: 5112817Abstract: Novel heterocyclic compounds, which are represented by the following general formula, useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.Type: GrantFiled: October 6, 1992Date of Patent: May 12, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Nobuyuki Fukazawa, Makoto Odate, Tsuneji Suzuki, Kengo Otsuka, Takashi Tsuruo, Wakao Sato
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Patent number: 5110347Abstract: The invention relates to certain substituted fused compounds of Formula I ##STR1## which are useful as herbicides, and their agriculturally suitable compositions, as well as methods for their use as general or selective preemergent or postemergent herbicides or as plant growth regulants.Type: GrantFiled: November 26, 1990Date of Patent: May 5, 1992Assignee: E. I Du Pont de Nemours and CompanyInventor: Thomas Selby
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Patent number: 5071860Abstract: Insecticidally active substituted heteroaryl phenyl ethers of the formula ##STR1## in which Het represents an optionally substituted heteroaromatic radical,X represents O, S, --CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.sub.2 --O--, ##STR2## Y represents O, --O--CH.sub.2 -- or S, Z represents an optionally substituted aromatic or heteroaromatic radical;m represents integers from 1-4n represents 0, 1, 2, 3, 4O represents 0, 1, 2, 3, 4, provided than n and o do not simultaneously represent 0p represents integers from 1-4,R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally substituted; two radicals adjacent to one another can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring,R.sup.1 represents identical or different radicals hydrogen, halogen, CN, C.sub.1-4 -alkyl, 1-5-halogeno-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, 1-5-halogeno-C.sub.Type: GrantFiled: March 7, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
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Patent number: 5032590Abstract: Substituted hydroxylamines of the formula ##STR1## in which R.sup.1 stands for an aromatic or heterocyclic radical,are especially useful in the treatment of hyperlipoproteinaemia, lipoproteinaemia and atherosclerosis.Type: GrantFiled: March 8, 1990Date of Patent: July 16, 1991Assignee: Bayer AktiengesellschaftInventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
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Patent number: 5028606Abstract: (1H-azol-1-ylmethyl)substituted quinoxaline derivatives, compositions containing the same, and methods of treating mammals suffering from disorders which are characterized by an increased proliferation and/or abnormal differentiation of epithelial tissues.Type: GrantFiled: November 13, 1989Date of Patent: July 2, 1991Assignee: Janssen Pharmaceutica N.V.Inventors: Marc G. Venet, Gerard C. Sanz, Alfons H. M. Raeymaekers, Eddy J. E. Freyne
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Patent number: 5026418Abstract: Pyrimidine compounds useful as plant growth regulators have the formula (I): ##STR1## wherein Y is an optionally substituted secondary or tertiary alkyl group containing from 3 to 7 carbon atoms or an optionally substituted cycloalkyl or alkylcycloalkyl group containing from 3 to 7 carbon atoms; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen or a lower alkyl group; A is an optionally substituted heterocyclic group, for example thienyl or pyridyl; n is an integer which may be from 0 to 2 and is preferably 0; and R.sup.3 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, or an alkenyl or alkynyl group containing from 2 to 4 carbon atoms.Type: GrantFiled: February 20, 1990Date of Patent: June 25, 1991Assignee: Imperial Chemical Industries PLCInventor: Kevin R. Lawson
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Patent number: 4977155Abstract: Heterocyclic dihydroxyquinoxaline compounds having the formula ##STR1## wherein R.sup.2 is hydrogen, NO.sub.2, NH.sub.2, CN, halogen, or SO.sub.2 NH.sub.2 ; --X--Y--Z-- is selected from --N.dbd.N--N.sup.3 --,--NR.sup.3 --N.dbd.N--,.dbd.N--NR.sup.3 --N.dbd., wherein R.sup.3 is hydrogen, lower alkyl, or CF.sub.3.The invention also relates to a method of preparing the compounds, pharmaceutical compositions thereof, and their use.The compounds are useful in the treatment of indications caused by hyperactivity of the excitatory neurotransmitters.Type: GrantFiled: June 22, 1989Date of Patent: December 11, 1990Assignee: A/S FerrosanInventors: Poul Jacobsen, Flemming E. Nielsen, Tage Honore, Jorgen Drejer
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Patent number: RE36256Abstract: This invention relates to bis mono- and/or bicyclic aryl and/or heteroaryl compounds exhibiting protein tyrosine kinase inhibition activity. More specifically, it relates to the method of inhibiting abnormal cell proliferation in a patient suffering from a disorder characterized by such proliferation comprising the administration thereto of an EGF and/or PDGF receptor inhibiting effective amount of said bis mono- and/or bicyclic aryl and/or heteroaryl compound and to the preparation of said compounds and their use in pharmaceutical compositions used in this method.Type: GrantFiled: December 10, 1997Date of Patent: July 20, 1999Assignee: Rhone-Poulenc Rorer Pharmaceuticals, Inc.Inventors: Alfred P. Spada, Michael R. Myers, Martin P. Maguire, Paul E. Persons