Ring Oxygen In The Bicyclo Ring System Patents (Class 546/115)
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Patent number: 5594004Abstract: A compound represented by the general formula (I) and a pharmaceutically acceptable salt and solvate thereof having an effect for inhibiting the agglutination of platelets is disclosed: ##STR1## wherein R.sup.1 represents a group --W--(CH.sub.2).sub.i --COOR.sup.3,R.sup.2 represents a hydrogen atom or a group --W--(CH.sub.2).sub.i --COOR.sup.3 or --OR.sup.4,X represents --CH.dbd. or --N.dbd.,Y represents(i) a group --(CO).sub.k --N(R.sup.5)--Z--, wherein Z represents a bond or a group --(CH.sub.2).sub.m --CO-- or a group --(CH.sub.2).sub.m --CHR.sup.6 --,(ii) a group --(CH.sub.2).sub.m --N(R.sup.5)--(CO).sub.k --, or(iii) a group --(CO).sub.k -Het, wherein Het represents a five- or six-membered heterocyclic ring comprising a nitrogen atom,A represents(i) the following groups (III) or (IV) ##STR2## B represents a bond, C.sub.1-6 alkylene or C.sub.2-6 alkenylen.Type: GrantFiled: January 30, 1995Date of Patent: January 14, 1997Assignee: Meiji Seika Kabushiki KaishaInventors: Kiyoaki Katano, Shokichi Ohuchi, Eiki Shitara, Masaro Shimizu, Kazue Yaegashi, Tomoaki Miura, Yasuko Isomura, Hiroyuki Iida, Midori Ishikawa, Kenji Asai, Emiko Hatsushiba, Mami Kawaguchi, Takashi Tsuruoka
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Patent number: 5585385Abstract: A novel compound represented by the formula: ##STR1## wherein Ring A and Ring B respectively stands for an optionally substituted homo- or hetero-cyclic ring, and at least one of them stands for an optionally substituted heterocyclic ring stand; Ring C stands for an optionally substituted benzene ring; R stands for a hydrogen atom or an optionally substituted hydrocarbon residue; one of X and Y stands for --NR.sup.1 -- (R.sup.1 stands for a hydrogen atom or an optionally substituted hydrocarbon residue) or --O--, and the other stands for--CO-- or --CS--, or one of them stands for --N.dbd. and the other stands for .dbd.CR.sup.2 -- (R.sup.2 stands for a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon residue, an optionally substituted amino group or an optionally substituted hydroxyl group); n denotes 1 or 2 or salts thereof which have an excellent tachykinin receptor antagonistic action and inhibitory action on plasma extravasation.Type: GrantFiled: November 10, 1994Date of Patent: December 17, 1996Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideaki Natsugari, Takenori Ishimaru, Takayuki Doi
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Patent number: 5571773Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: June 2, 1995Date of Patent: November 5, 1996Assignee: American Cyanamid CompanyInventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson
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Patent number: 5563113Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: June 2, 1995Date of Patent: October 8, 1996Assignee: American Cyanamid CompanyInventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson
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Patent number: 5554579Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: June 2, 1995Date of Patent: September 10, 1996Assignee: American Cyanamid Co.Inventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson
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Patent number: 5554631Abstract: The present invention relates to a novel compound 5-pyrrolyl-6-halogeno-2-pyridylmethylsulfinylbenzimidazole derivative having the following formula (I): ##STR1## or a pharmaceutically acceptable salt thereof, in which X represents S, SO or SO.sub.2,Y represents halogen,R.sub.1 and R.sub.2 independently from each other represent hydrogen or methyl,R.sub.3 represents hydrogen, C.sub.1 -C.sub.8 alkyl, --SR.sub.6, --N(R.sub.7).sub.2, or a group of formula --OR.sub.6 or --O(CH.sub.2).sub.m --Z, whereinR.sub.6 represents C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.3 -C.sub.10 cycloalkyl optionally substituted with C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.5 fluoroalkyl, phenyl optionally substituted with C.sub.1 -C.sub.4 alkyl or benzyl optionally substituted with C.sub.1 -C.sub.4 alkyl,R.sub.7 represents hydrogen or C.sub.1 -C.sub.5 alkyl,Z represents a group of formula --O(CH.sub.2).sub.q --R.sub.9 whereinq denotes an integer of 1 to 3, and R.sub.Type: GrantFiled: March 21, 1995Date of Patent: September 10, 1996Assignee: Il-Yang Pharm. Co., Ltd.Inventors: Su U. Kim, Dong Y. Kim, Gi J. Chung, Sung K. Hong, Sung J. Park, Sang H. Nam, Seung M. Lee
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Patent number: 5545646Abstract: The invention relates to new 4-bicyclically substituted dihydropyridines of the general formula (I) ##STR1## in which R.sub.1 to R.sub.5 have the meaning given in the description, processes for their preparation and their use in medicaments, in particular in agents for the treatment of cardiovascular diseases.Type: GrantFiled: June 17, 1994Date of Patent: August 13, 1996Assignee: Bayer AktiengesellschaftInventors: Alexander Straub, Siegfried Goldmann, J urgen Stoltefuss, Martin Bechem, Klaus Dembowsky, Rainer Gross, Siegbert Hebisch, Joachim H utter, Howard-Paul Rounding
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Patent number: 5536839Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: June 2, 1995Date of Patent: July 16, 1996Assignee: American Cyanamid CompanyInventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson
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Patent number: 5534485Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: June 2, 1995Date of Patent: July 9, 1996Assignee: American Cyanamid CompanyInventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson
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Patent number: 5518588Abstract: The present invention relates to a method for preparing 3-aminopyridines from 3-nitropyridines, in which the nitropyridines are reduced electrochemically in acidic solution.Type: GrantFiled: September 30, 1994Date of Patent: May 21, 1996Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Ulrich Fechtel, Karlheinz Wembacher, Heinz-Hermann Bokel
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Patent number: 5512579Abstract: To provide a compound which exhibits a serotonin antagonism and an acetylcholine release accelerating activity at a well-balanced activity ratio. An aminobenzoic acid derivative represented by the general formula (I) or (II) or a pharmacologically acceptable salt thereof: ##STR1## wherein R.sup.1 represents a group represented by the formula: ##STR2## {wherein A represents a group represented by formula --CH.sub.2 --X--CH.sub.2 -- (wherein X represents O, >N--R.sup.6 or >CHR.sup.7 (wherein R.sup.6 represents lower alkyl and R.sup.7 represents hydrogen or lower alkoxy)), etc.; D and E each represents a group represented by formula --(CH.sub.2).sub.3 --, etc., and R.sup.2 represents lower alkyl. etc.}; R.sup.9 represents alkynyl; R.sup.10 represents amino, etc.; R.sup.11 represents halogen; R.sup.12 and R.sup.13 each represent lower alkyl; a is an integer of 1 to 5; and b is an integer of 0 to 5!.Type: GrantFiled: July 18, 1994Date of Patent: April 30, 1996Assignee: Eisai Co., Ltd.Inventors: Shuhei Miyazawa, Yorohisa Hoshino, Hisashi Shibata, Kazuo Hirota, Takaaki Kameyama, Shinya Abe, Takashi Yamanaka
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Patent number: 5508406Abstract: The invention relates to new 4-quinolyl-dihydropyridine esters of the general formula (I) ##STR1## in which R.sub.1 to R.sub.6 have the meaning given in the description, to processes for their preparation and to their use in medicaments, especially in agents for the treatment of cardiac circulatory disorders.Type: GrantFiled: April 20, 1994Date of Patent: April 16, 1996Assignee: Bayer AktiengesellschaftInventors: Jurgen Stoltefuss, Siegfried Goldmann, Alexander Straub, Martin Bechem, Rainer Gross, Siegbert Hebisch, Joachim Hutter, Howard-Paul Rounding
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Patent number: 5502220Abstract: A process for preparing compounds of the formula ##STR1## where a, b d, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined herein including condensation of a phenol of formula ##STR2## with an acetal of formula ##STR3## in the presence of a catalytic amount of a tertiary amine. The compounds of formula I are intermediates useful in the preparation of pyranyl cyanoguanidine derivatives.Type: GrantFiled: December 23, 1994Date of Patent: March 26, 1996Assignee: Bristol-Myers Squibb CompanyInventor: Jeffrey T. North
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Patent number: 5496826Abstract: New central nervous system agents conform to formula I: ##STR1## wherein R=H or C.sub.1-4 alkoxy;X=CH or N;Y=NH, O or S;Z=C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-3 alkenyl, NH.sub.2, C.sub.1-4 alkylamino, or C.sub.1-4 alkoxyalkyl, with the proviso that Z may not be CH.sub.3 when R=H, X=CH, and Y=NH and Z may not be CH.sub.3 when R=H, X=N and Y=NH and NHC(O)Z is in the para- position.Type: GrantFiled: September 2, 1994Date of Patent: March 5, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Brett T. Watson, Astrid A. Ortiz
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Patent number: 5489685Abstract: A process is disclosed for rapid synthesis of substituted furanyl pyridines.Type: GrantFiled: May 12, 1994Date of Patent: February 6, 1996Assignee: Merck & Co., Ltd.Inventors: Ioannis Houpis, Audrey Molina, Joseph E. Lynch, Hywyn R. O. Churchill, Ralph P. Volante, Paul J. Reider, Woo-Baeg Choi
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Patent number: 5472964Abstract: Compounds having the formula I: ##STR1## are antagonists of the actions of leukotrienes. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection.Type: GrantFiled: June 16, 1994Date of Patent: December 5, 1995Assignee: Merck Frosst Canada, Inc.Inventors: Robert N. Young, Marc Labelle, Yves Leblanc, Yi B. Xiang, Cheuk K. Lau, Claude Dufresne, Yves Gareau
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Patent number: 5459129Abstract: A novel compound of the formula: ##STR1## wherein a ring A stands for an optionally substituted 5-membered ring; B stands for an optionally substituted divalent cyclic or chain group; either one of Q.sup.1 and Q.sup.2 stands for N and the other stands for N or CH; X stands for an amino group, hydroxyl group or mercapto group; Y stands for H, halogen atom or a group bonded through C, N, 0 or S; Z stands for a straight-chain divalent group having 2 to 5 atoms constituted of optionally substituted carbon atoms or constituted of optionally substituted carbon atoms and one optionally substituted hetero-atom; COOR.sup.1 and COOR.sup.2 independently stand for an optionally esterified carboxyl group; n denotes an integer of 2 to 6; and R.sup.1 may be different in each of n repeating units, or their salts and it is useful as a therapeutic drug for tumor in mammals.Type: GrantFiled: August 27, 1993Date of Patent: October 17, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Akimoto, Kazuyoshi Aso, Koichiro Ootsu
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Patent number: 5442059Abstract: The invention provides compounds of the formula: ##STR1## wherein R, and R.sup.1 and W are defined in the specification. These compounds are useful as antibiotic agents.Type: GrantFiled: August 13, 1992Date of Patent: August 15, 1995Assignee: American Cyanamid CompanyInventors: Phaik-Eng Sum, Ving J. Lee, Raymond T. Testa
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Patent number: 5442066Abstract: Novel bleach catalysts, a method for bleaching substrates using these catalysts and detergent compositions containing same are reported. The bleaches are of the quaternary oxaziridinium salt type. Substrates such as fabrics may be bleached in an aqueous solution containing the quaternary oxaziridinium salt.Type: GrantFiled: September 2, 1994Date of Patent: August 15, 1995Assignee: Lever Brothers Company, Division of Conopco, Inc.Inventors: Stephen A. Madison, Janet L. Coope
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Patent number: 5430042Abstract: The novel compounds of the formula I ##STR1## and physiologically acceptable salts thereof, wherein R.sup.1 and R.sup.2, which are different is each H alkyl containing 1-4 carbon atoms or --C(O)--R.sup.5 ;whereinR.sup.5 is alkyl containing 1-4 carbon atoms or alkoxy containing 1-4 carbon atoms and one of R.sup.1, or R.sup.2 is always selected from the group --C(O)--R.sup.5 ;R.sup.3 and R.sup.4 are the same or different and selected from ##STR2## and --CH.sub.2 CH.sub.2 OCH.sub.3 or R.sup.3 and R.sup.4 together with the adjacent oxygen atoms atached to the pyridine ring and the carbon atoms in the pyridine ring form a ring, wherein the part constituted by R.sup.3 and R.sup.4 is --CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --; as well as intermediates, pharmaceutical compositions containing such compounds as active ingredient and the use of the compounds in medicine.Type: GrantFiled: June 20, 1991Date of Patent: July 4, 1995Assignee: Aktiebolaget AstraInventors: Per L. Lindberg, Gunnel E. Sunden
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Patent number: 5395939Abstract: Methods of making asymmetric DE ring intermediates for the synthesis of camptothecin and camptothecin analogs employ a dioxane intermediate as the immediate precursor to the DE ring intermediate. Novel intermediates are also disclosed.Type: GrantFiled: November 30, 1993Date of Patent: March 7, 1995Assignee: North Carolina State UniversityInventor: Daniel L. Comins
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Patent number: 5374635Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomemlar nephritis, hepatitis, endotoxemia, uveitis, and allograft rejection and in preventing the formation of atherosclerotic plaques.Type: GrantFiled: March 29, 1993Date of Patent: December 20, 1994Assignee: Merck Frosst Canada, Inc.Inventors: Serge Leger, John H. Hutchinson
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Patent number: 5369084Abstract: Isonicotinic acid derivatives and related furo-, thieno- and pyrrolo[3,4-c]pyridin-1(3H)-one, -thione and -imine compounds having the formula ##STR1## wherein R is ##STR2## Q is O, S or NR.sup.7 ; Y is O, S or NR.sup.8 ; L is COOR.sup.9, CONR.sup.10 R.sup.11, C(.dbd.S)NR.sup.10 R.sup.11, CN, or a radical of formula ##STR3## the acceptable addition salts, the stereochemically isomeric forms and the N-oxides thereof, having herbicidal properties, compositions containing the same and methods for controlling weeds.Type: GrantFiled: May 6, 1993Date of Patent: November 29, 1994Assignee: Janssen Pharmaceutical N.V.Inventors: Hans-Rudolf Waespe, Guy R. E. Van Lommen, Victor K. Sipido
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Patent number: 5350854Abstract: Novel 2-alkyl carbinol derivatives of deoxynojirimycin (DNJ) and the chemical synthesis of these derivatives and intermediates therefor from DNJ and their method of inhibiting lentiviruses are disclosed.Type: GrantFiled: July 12, 1993Date of Patent: September 27, 1994Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier
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Patent number: 5346912Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein A, B and E are individually selected from the group consisting of .dbd.CH-- and .dbd.N-- with at least one being .dbd.N--, R is selected from the group consisting of cycloalkyl of 3 to 6 carbon atoms, and alkenyl and alkynyl of 2 to 6 carbon atoms, R.sub.1 is hydrogen or alkyl of 1 to 3 carbon atoms, R.sub.2 and R.sub.3 together are --O--CH.sub.2 --O-- or are individually selected from the group consisting of hydrogen, halogen, --NO.sub.2, --CN, alkyl, alkylthio and alkoxy of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, --COR.sub.4, --(CH.sub.2).sub.m --CX.sub.3, --O--(CH.sub.2).sub.m --CX.sub.3, --S--(CH.sub.2).sub.m --CX.sub.3, --O--(CX.sub.2).sub.m --CX.sub.3 and --S--(CX.sub.2).sub.m --CX.sub.3, R.sub.Type: GrantFiled: December 20, 1993Date of Patent: September 13, 1994Assignee: Roussel-UclafInventor: Elizabeth A. Kuo
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Patent number: 5331096Abstract: Novel derivatives of 1-deoxynojirimycin are disclosed which have thio or sulfinyl substituents at C-2 or C-3. These compounds are useful inhibitors of lentiviruses such as visna virus and human immunodeficiency virus. Methods of chemical synthesis of these derivatives and intermediates therefor are also disclosed.Type: GrantFiled: August 2, 1993Date of Patent: July 19, 1994Assignee: G. D. Searle & Co.Inventors: Francis J. Koszyk, Richard A. Mueller
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Patent number: 5308850Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.Type: GrantFiled: September 25, 1992Date of Patent: May 3, 1994Assignee: Merck Frosst Canada, Inc.Inventors: John W. Gillard, John H. Hutchinson, Richard Frenette, Michel Therien
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Patent number: 5302596Abstract: Novel tricyclic compound represented by formula ##STR1## possess a TXA.sub.2 biosynthesis inhibiting activity and/or a TXA.sub.2 receptor antagonizing activity, and are expected to have preventive and therapeutic effects on ischemic diseases, cerebro-vascular diseases, etc.Type: GrantFiled: November 23, 1992Date of Patent: April 12, 1994Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Etsuo Oshima, Hiroyuki Obase, Akira Karasawa, Kazuhiro Kubo, Ichiro Miki, Akio Ishii
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Patent number: 5270468Abstract: Novel derivatives of 1-deoxynojirimycin are disclosed which have amino or azido substituents at C-2 and/or C-3. These compounds are useful inhibitors of lentiviruses. Methods of chemical synthesis of these derivatives and intermediates therefor are also disclosed.Type: GrantFiled: January 8, 1993Date of Patent: December 14, 1993Assignee: G. D. Searle & Co.Inventors: Ish K. Khanna, Richard A. Mueller, Richard M. Weier, Michael A. Stealey
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Patent number: 5260261Abstract: Compounds having the formula ##STR1## in which: R is hydrogen, 2-halo, 2-(C.sub.1 -C.sub.4 alkyl), 2-trifluoromethyl, 2-nitro, 2-(C.sub.1 -C.sub.4 alkoxy), 4-halo, 2-halo-6-butynyloxy, or 2,6-dihalo;R.sub.1 is halo, C.sub.1 -C.sub.4 alkyl, trifluoromethyl or cyano, and if R is 2-halo, 2-methyl, 2-nitro, 2-methoxy, 2-trifluoromethyl or 2,6-dihalo then R.sub.1 may also be hydrogen;R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are independently hydrogen or methyl or R.sub.3 and R.sub.4 taken together form a bond; andX is O or S; provided that:a) if R.sub.1 is bromo, R is not 2,6-difluoro; andb) if R.sub.1 is chloro, R is not 2,6-dichloro.Type: GrantFiled: December 11, 1992Date of Patent: November 9, 1993Assignee: Imperial Chemical Industries PLCInventor: Michael P. Prisbylla
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Patent number: 5254557Abstract: A compound of formula (IA) in the form of a pharmaceutically acceptable microfine powder is disclosed.Type: GrantFiled: June 1, 1992Date of Patent: October 19, 1993Assignee: Beecham Group p.l.c.Inventors: Derek R. Buckle, David G. Smith, Frederick Cassidy
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Patent number: 5252538Abstract: There are provided novel (2-imidazolin-2-yl) fused heteropyridine compounds, and intermediate compounds for the preparation thereof, and a method for controlling a wide variety of annual and perennial plant species therewith.Type: GrantFiled: January 16, 1990Date of Patent: October 12, 1993Assignee: American Cyanamid CompanyInventors: Barrington Cross, Marinus Los, Robert F. Doehner, Jr., David W. Ladner, Jerry L. Johnson, Michael E. Jung, Victor M. Kamhi, Shin-Shyong Tseng, John M. Finn, Peter J. Wepplo
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Patent number: 5250540Abstract: Aminomethyl-substituted 2,3-dihydropyrano[2,3-b]pyridines can be prepared by alkylation of corresponding amines. The novel aminomethyl-substituted dihydropyrano[2,3-b]pyridines can be used as active ingredients in medicaments, in particular for the treatment of disorders of the central nervous system.Type: GrantFiled: June 11, 1992Date of Patent: October 5, 1993Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Hans-Georg Heine, Rudolf Schohe-Loop, Thomas Glaser, Jean M. V. De Vry
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Patent number: 5232938Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein a, b, J, Y and R.sub.2 -R.sub.8 are as defined herein are potassium channel activators, a process for their preparation and their pharmaceutical use.Type: GrantFiled: April 21, 1992Date of Patent: August 3, 1993Assignee: Beecham Group p.l.c.Inventors: Geoffrey Stemp, Gordon Burrell
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Patent number: 5221744Abstract: Arylaminocarbonyl compounds of the formula (I) ##STR1## wherein R.sub.2-6, X.sub.1, A and m are as defined in the disclosure, intermediates therefore, synthesis thereof, and the use of said compounds for the control of weeds are described.Type: GrantFiled: August 17, 1992Date of Patent: June 22, 1993Assignee: Sandoz Ltd.Inventors: Karl Seckinger, Karlheinz Milzner, Fred Kuhnen, Sasank S. Mohanty
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Patent number: 5214051Abstract: Thiazolyl and oxazolyl [5,4-c] piperidyl-substituted quinolone-carboxylic acids and related analogs thereof having antibacterial properties are disclosed.Type: GrantFiled: May 16, 1991Date of Patent: May 25, 1993Assignee: Pfizer Inc.Inventors: Katherine E. Brighty, John A. Lowe, III, Paul R. McGuirk
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Patent number: 5212301Abstract: Introduction of a fluoro substituent into an aromatic ring adjacent an electron donating group is difficult producing mixed isomers and low yields of desired products.A process for the introduction of a fluoro substituent into a substantially adjacent position to an electron-donating group into an aromatic compound in high yield is disclosed.The fluoroaromatic compounds are useful as synthetic intermediates for example in the manufacture of agrochemicals, pharmaceuticals and dyestuffs.Type: GrantFiled: May 8, 1992Date of Patent: May 18, 1993Assignee: Imperial Chemical Industries PLCInventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
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Patent number: 5189047Abstract: The present invention is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein Y, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 , a and b are as defined in the Specification, having pharmacological activity, to a process for their preparation, and to their use as pharmaceuticals.Type: GrantFiled: July 20, 1990Date of Patent: February 23, 1993Assignee: Beecham Group p.l.c.Inventors: Michael S. Hadley, Graham E. Jones
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Patent number: 5185345Abstract: The present invention deals with 4-amidino chroman and 4-amidino pyrano (3,2-c) pyridine derivatives, a process for their preparation and pharmaceutical compositions containing them. Said derivatives have antihypertensive and antiarythmic activities. They respond to formula ##STR1## in which: A+B.dbd.--CH.dbd.CH--CH.dbd.N-- ou --CH.dbd.CR.sub.4 --CR.sub.5 .dbd.CH--; X.dbd.N,N.fwdarw.O, C--Z;R.sub.1 .dbd.H, CN, NO.sub.2, C.sub.1 -C.sub.4, alkyl, OH, C.sub.1 -C.sub.4 alkoxy, CF.sub.3 CO--, CH.sub.3 --SO.sub.2 --, .rho.--SO.sub.2 --;R.sub.2 .dbd.H;R.sub.3 .dbd.OH ou OCOCH.sub.3 ou R.sub.2 +R.sub.3 .dbd.double bond.Type: GrantFiled: March 12, 1992Date of Patent: February 9, 1993Assignee: SanofiInventors: Georges Garcia, Patrick Gautier, Dino Nisato, Richard Roux
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Patent number: 5140031Abstract: Novel compounds having the formula ##STR1## wherein ##STR2## are disclosed. These compounds have potassium channel activating activity and are useful, for example, as cardiovascular agents, especially as antiischemic agents.Type: GrantFiled: February 27, 1991Date of Patent: August 18, 1992Assignee: E. R. Squibb & Sons, Inc.Inventors: Karnail Atwal, Gary J. Grover, Kyoung S. Kim
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Patent number: 5132310Abstract: Racemic Compounds of the formula ##STR1## A is --C.tbd.C--R.sub.6, --CH.sub.2 --CH.sub.2 --R.sub.7 or ##STR2## R.sub.1 is hydrogen or lower alkanoyl, R.sub.2, R.sub.3, and R.sub.4 independently are hydrogen or lower alkyl,R.sub.5 is lower alkyl,R.sub.6 is a heteroaromatic radical or an aromatic radical selected from phenyl, naphthyl or phenanthryl, which aromatic radical may optionally be substituted by one or more substituents selected from chlorine, fluorine, lower alkyl, lower alkoxy, phenyl lower alkoxy, lower alkanoyl, lower alkanoyloxy, hydroxy-lower alkyl, carboxy, lower alkoxycarbonyl, hydroxyimino lower alkyl, amino, amino lower alkyl, mono- or di-lower alkylamino, mono- or di-lower alkylamino-lower alkyl, lower alkanoylamino, aminocarbonyl, lower alkylaminocarbonyl, lower dialkylaminocarbonyl, trifluoroacetylamino, trifluoromethyl, hydroxy, pyridyl, or on adjacent carbons can be ##STR3## wherein R' is hydrogen, lower alkanoyl, trifluoroacetyl and R" hydrogen or lower alkyl,R.sub.Type: GrantFiled: December 14, 1990Date of Patent: July 21, 1992Assignee: Hoffmann-La Roche Inc.Inventor: Armin Walser
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Patent number: 5116849Abstract: The present invention deals with 4-amidino chroman and 4-amidino pyrano (3,2-c) pyridine derivatives, a process for their preparation and pharmaceutical compositions containing them. Said derivatives have antihypertensive and antiarrhythmic activities. They respond to formula ##STR1## in which: A+B=--CH.dbd.CH--CH.dbd.N--or--CH.dbd.CR.sub.4 --CR.sub.5 .dbd.CH--;X=N, N.fwdarw.O, C--Z;R.sub.1 =H, CN, NO.sub.2, C.sub.1 -C.sub.4 alkyl, OH, C.sub.1 -C.sub.4 alkoxy, CF.sub.3 CO--, CH.sub.3 --SO.sub.2 --, .phi.--SO.sub.2 --;R.sub.2 =H;R.sub.3 =OH or OCOCH.sub.3 or R.sub.2 +R.sub.3 =double bond.Type: GrantFiled: October 31, 1990Date of Patent: May 26, 1992Assignee: SanofiInventors: Georges Garcia, Patrick Gautier, Dino Nisato, Richard Roux
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Patent number: 5109008Abstract: Compounds are disclosed of formula (I) ##STR1## wherein R.sub.1 represents hydrogen, unsubstituted or substituted C.sub.1-6 alkyl, halogen, --COR.sub.4 or --CO.sub.2 R.sub.4 (where R.sub.4 represents hydrogen or unsubstituted or substituted C.sub.1-6 alkyl);R.sub.2 and R.sub.3 are the same or different and are C.sub.1-6 alkyl or C.sub.3-6 alkenyl; or --NR.sub.2 R.sub.3 forms a 5-membered (optionally containing an oxygen atom adjacent to the nitrogen) or a 6-membered ring, which ring optionally contains one unit of unsaturation and which is unsubstituted or substituted by hydroxy, C.sub.1-6 acyloxy, oxo, optionally substituted methylidene, --COR.sub.5 (where R.sub.5 represents C.sub.1-6 alkyl, OR.sub.6 or --NHR.sub.6, andR.sub.6 represents hydrogen, C.sub.1-6 alkyl, aryl or ar(C.sub.1-6)alkyl) or said ring is substituted by .dbd.NOR.sub.7 (where R.sub.7 represents C.sub.1-6 alkyl);Z represents --O-- or --S--;X represents a direct bond, --CH.sub.2 -- or --CH.sub.Type: GrantFiled: October 18, 1989Date of Patent: April 28, 1992Assignee: Glaxo Group LimitedInventors: David I. C. Scopes, Duncan B. Judd, David J. Belton
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Patent number: 5100900Abstract: Positive inotropically active 4-quinolyl-dihydropyridines of the formula ##STR1## in which R.sup.1 and R.sup.5 are identical or different and represent straight-chain or branched alkyl having up to 8 carbon atoms,R.sup.2 represents nitro or cyano, orR.sup.1 and R.sup.2 together form a lactone ring of the formula ##STR2## R.sup.3 represents a radical of the formula ##STR3## in which R.sup.6 - denotes hydrogen, halogen or straight-chain or branched alkyl or alkoxy in each case having up to 8 carbon atoms,R.sup.7 denotes aryl, thienyl or pyridyl, andR.sup.4 represents hydrogen, or optionally substituted alkyl, alkenyl, alkadienyl or alkynyl,and their physiologically acceptable salts.Type: GrantFiled: March 29, 1991Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Jurgen Stoltefuss, Horst Boshagen, Siegfried Goldmann, Alexander Straub, Rainer Gross, Joachim Hutter, Siegbert Hebisch, Martin Bechem
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Patent number: 5086170Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, alkyl and hydroxyalkyl of 1 to 5 carbon atoms and amino, n is an integer from 1 to 3, X and X.sub.1 are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms or taken together with the carbon atom to which they are attached are ##STR2## Y is --O-- or --S--, R.sub.3 is alkyl of 1 to 3 carbon atoms or aryl of 6 to 8 carbon atoms, ##STR3## is selected from the group consisting of ##STR4## R.sub.4 and R.sub.5 are individually aryl unsubstituted or substituted with at least one member of the group consisting of halogen, --NO.sub.2 and alkyl and alkoxy of 1 to 3 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof with acids and bases having cyclooxygenase inhibiting and antibiotic acitvity.Type: GrantFiled: December 24, 1990Date of Patent: February 4, 1992Assignee: Roussel UclafInventors: Abdul B. N. Luheshi, Robert K. Smalley, Peter D. Kennewell, Robert Westwood
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Patent number: 5077408Abstract: Process for the synthesis of compounds of formula (I): ##STR1## their pyridinium salts and N-oxides, in which formula: the nitrogen of the pyridine ring is situated in the .alpha.-, .beta.-, .gamma.- or .delta.-position with respect to the ring junction;R.sup.1 represents a halogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy or a nitro, substituted or unsubstituted amino, phenyl or cyano group;0.ltoreq.m.ltoreq.2;R.sup.2 represents a lower alkyl or cycloalkyl group, a 5- or 6-membered heterocycle containing 1 or 2 hetero atoms, substituted or otherwise, or an aryl group ##STR2## such that: R.sup.3 represents a halogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkoxy or a nitro, phenyl, substituted or unsubstituted sulfonyl, cyano, thioalkyl, substituted or unsubstituted amino, substituted or unsubstituted sulfinyl, mercapto, hydroxyl or ester group,0.ltoreq.n.ltoreq.Type: GrantFiled: September 17, 1990Date of Patent: December 31, 1991Assignee: Science et OrganisationInventors: Gerald Guillaumet, Christine Flouzat
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Patent number: 5075302Abstract: Mercaptoacyl aminolactam inhibitors of endopeptidases of the formula ##STR1## wherein Y is -(CHR.sup.5).sub.n (CR.sup.3 R.sup.4)- or -(CR.sup.3 R.sup.4).sub.p X(CR.sup.3 R.sup.4).sub.q -,wherein two substituents selected from the group consisting of R.sup.3, R.sup.4 and R.sup.5, can form a benzene, cyclopentane or cyclohexane ring;X is -O-, -S-, -SO- or -SO.sub.2 -;Q is hydrogen or R.sup.6 CO-;m is 1 or 2;n is 1, 2, 3 or 4;p is 1 or 2;q is 2 or 3;R.sup.1 is lower alkyl, aryl or heteroaryl;R.sup.2 is hydrogen, lower alkyl, hydroxylower alkyl, lower alkoxylower alkyl, aryllower alkyl or heteroaryllower alkyl;R.sup.3 and R.sup.4 are independently hydrogen, lower alkyl, aryllower alkyl or heteroaryllower alkyl;R.sup.5 is hydrogen, lower alkyl, aryllower alkyl, heteroaryllower alkyl, hydroxy, lower alkoxy, mercapto, or lower alkylthio; and R.sup.Type: GrantFiled: March 9, 1990Date of Patent: December 24, 1991Assignee: Schering CorporationInventor: Bernard R. Neustadt
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Patent number: 5071868Abstract: A process for the preparation of S- or R-carbazole derivatives of the general formula: ##STR1## in which R is an unsubstituted or substituted amino radical and pharmacologically acceptable salts, by either reacting R-(-)-epichlorohydrin (for the S-carbozole derivative); or reacting an S-epoxide derivative of the general formula: ##STR2## in which R.sub.1 is the residue of a substituted sulphonic acid derivative (for the R-carbazole derivative); with 4-hydroxycarbazole and then with ammonia or a substituted amine of the general formula RH, and recovering the compound or converting it to a pharmacologically acceptable salt.The new R-(+)- and S(-)-carbazole derivatives provided by the inventive process have unexpected beta blocking and vasodilatory properties and are useful in pharmaceutical compositions. R-(+)-carbazole derivatives are also useful for the treatment of glaucoma.Type: GrantFiled: January 28, 1991Date of Patent: December 10, 1991Assignee: Boehringer Mannheim GmbHInventor: Herbert Leinert
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Patent number: 5071856Abstract: Novel carbostyril derivatives and salts thereof having useful pharmacological activities such as myocardial contraction increasing activity (positive inotropic activity), coronary blood flow increasing activity, hypotensive activity, activity for inhibiting vasoconstriction induced by norepinephrine, and anti-inflammatory effect in one hand, while they do not possess activity for increasing heart beat at all substantially as well as show quite low toxicity and low side-effects in central nervous system activities.Type: GrantFiled: September 11, 1989Date of Patent: December 10, 1991Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Shigeharu Tamada, Takafumi Fujioka, Hidenori Ogawa, Shuji Teramoto, Kazumi Kondo
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Patent number: 5071871Abstract: New benz[b]pyranes and pyranopyridines of formula I, ##STR1## wherein the significances of substituents V, T, W, R.sub.3 to R.sub.5, R.sub.9, R.sub.10, m, X, Y and Z are given in claim 1 and their N-oxides and their salts and their use in the treatment of raised blood pressure in the treatment of vascular disorders and other disorders in which a reduction in tension of the smooth muscles is therapeutically useful, as well as in the treatment of hair loss and baldness. Further the compounds are useful in the treatment of asthma and obstructive disorders of the respiratory system as well as in the prophylactic treatment of obstructive or inflammatory airways disease, for example asthma, as well as novel pharmaceutical compositions comprising said K.sup.+ channel activators suitable for such use.Type: GrantFiled: July 10, 1990Date of Patent: December 10, 1991Assignee: Sandoz Ltd.Inventors: Stefan Blarer, John Morley, Ian D. Chapman