Acyclic Nitrogen Bonded Directly To A -c(=x)- Group, Wherein X Is Chalcogen Patents (Class 546/309)
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Patent number: 5700817Abstract: The present invention describes novel cyclic diol derivatives represented by formula I and II: ##STR1## in which Y represents O, S, SO, SO.sub.2, (CH.sub.2).sub.m wherein m is zero or an integer of 1 to 5, or NR.sup.2 group wherein R.sup.a is hydrogen, lower alkyl, lower alkoxycarbonyl, aryl, arylalkyl or acyl;R.sup.1 represents an alkyl or alkylcarbamoyl group;R.sup.2 represents a group having formula T--(CH.sub.2).sub.n --V (X.sup.-)q, wherein T refers to a simple covalent bond, a CO, PO.sub.3.sup.-, C(O)O, or CONR.sup.b group wherein R.sup.b is hydrogen, lower alkyl or acyl;n refers to an integer of from 1 to 10;V represents either (i) the group indicated by formula --.sup.+ NR.sup.5 R.sup.6 R.sup.7 wherein R.sup.5, R.sup.6 and R.sup.7 stands for identical or different lower alkyl group, or two or three of R.sup.5, R.sup.6 and R.sup.7 taken together with the adjacent nitrogen form heterocyclic ammonio group, or (ii) the group indicated by the formula ##STR2## wherein R.sup.Type: GrantFiled: November 6, 1995Date of Patent: December 23, 1997Assignees: Pohang Iron & Steel Co., Ltd., Research Institute of Industrial Science & TechnologyInventors: Soon Hyung Woo, Sung Kee Chung, Soo Ho Ban, Byoung Eog Kim, Si Hwan Kim
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Patent number: 5691366Abstract: A new nitro compound of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each lower alkyl or lower alkoxy(lower)-alkyl, or ##STR2## is cyclized to form ##STR3## X is --O--, --S-- or --NH--, m is an integer 0 or 1, andR.sup.3 is carbamoyl, lower alkylcarbamoyl, lower alkanoyl, di-lower alkylaminosulfonyl, lower alkylsulfonyl, oxamoyl or a group of the formula: --(Y).sub.n --R.sup.4 wherein Y is --CO--, --SO.sub.2 --, --COCH.sub.2 -- or ##STR4## n is an integer of 0 or 1, and R.sup.4 is heterocyclic group which is optionally substituted with one or more substituents selected from lower alkyl, lower alkoxy, phenyl, carbamoyl, halogen, amino, lower alkylthio, hydroxy, lower alkylsulfonylamino and carbamoylmethyl, and pharmaceutically acceptable salt thereof, which are useful as vasodilators.Type: GrantFiled: October 31, 1995Date of Patent: November 25, 1997Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Masayuki Kato, Shigetaka Nishino, Mitsuko Hamano, Hisashi Takasugi
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Patent number: 5688817Abstract: Di(aromatic) compounds corresponding to the following formula: ##STR1## in which: Ar represents either ##STR2## n=1 or 2 or: ##STR3## X represents a divalent radical, Z represents O, S or a divalent radical, and R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent a hydrogen atom or various organic radicals, and the salts of the compounds of formula (I) when R.sub.1 is a carboxylic acid function.Use in human and veterinary medicine and in cosmetics.Type: GrantFiled: April 28, 1995Date of Patent: November 18, 1997Assignee: Centre Int'l. De Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, William Robert Pilgrim
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Patent number: 5684198Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof,which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the aides and pharmaceutical compositions containing them.Type: GrantFiled: August 23, 1996Date of Patent: November 4, 1997Assignee: Imperial Chemical Industries, PLCInventors: Keith Russell, Cyrus John Ohnmacht, Keith Hopkinson Gibson
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Patent number: 5656634Abstract: Compounds of the formula ##STR1## the pharmaceutically acceptable salts thereof, wherein Q and R.sup.1 are as defined below, and novel carboxylic acid and acid halide intermediates used in the synthesis of such compounds. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.Type: GrantFiled: May 31, 1994Date of Patent: August 12, 1997Assignee: Pfizer Inc.Inventors: George Chang, Ernest S. Hamanaka, Peter A. McCarthy, Thien V. Truong, Frederick J. Walker
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Patent number: 5654429Abstract: A process for the preparation of a 3-amino-2-chloro-4-alkylpyridine of the formula: ##STR1## wherein R1 is a linear, branched or cyclic hydrocarbon of from one to eight carbon atoms, optionally substituted with one or more electron stabilizing groups,an intermediate in the preparation of certain 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine compounds useful in the prevention and treatment of HIV infection.Type: GrantFiled: June 7, 1995Date of Patent: August 5, 1997Inventor: Laurence John Nummy
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Patent number: 5631206Abstract: Compounds of formula (D having herbicidal utility are disclosed; ##STR1## wherein Q is a variety of heteroaromatic groups; X is a single bond; O; S; or NR.sup.4 ; R.sup.1 is C.sub.1 -C.sub.5 alkyl optionally substituted with C.sub.1 -C.sub.2 alkoxy, OH, 1-3 halogens, or C.sub.1 -C.sub.2 alkylthio; CH.sub.2 (C.sub.3 -C.sub.4 cycloalkyl); C.sub.3 -C.sub.4 cycloalkyl optionally substituted with 1-3 methyl groups; C.sub.2 -C.sub.4 alkenyl; or C.sub.2 -C.sub.4 haloalkenyl; R.sup.2 is H; chlorine; bromine; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; C.sub.1 -C.sub.2 alkylthio; C.sub.2 -C.sub.3 alkoxyalkyl; C.sub.1 -C.sub.2 alkylthioalkyl; cyano; nitro; NH(C.sub.1 -C.sub.2 alkyl); or N(C.sub.1 -C.sub.2 alkyl).sub.2 ; R.sup.4 is H; CH.sub.3 ; or OCH.sub.3 ; and agriculturally suitable salts thereof.Type: GrantFiled: April 1, 1996Date of Patent: May 20, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Lucian R. Denes
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Patent number: 5614634Abstract: Leukotriene-B.sub.4 analogs of formula I ##STR1## in which R.sup.1 means radical COOR.sup.2 with R.sup.2 meaning a hydrogen atom or a (C.sub.1 -C.sub.4)-alkyl group or R.sup.1 means radical CH.sub.2 OH,B means an alkylene group with 1-3 C atoms in the chain, a radical ##STR2## or a radical ##STR3## with R.sup.3 meaning a hydrogen atom, a carboxy or methoxycarbonyl group, A means groups ##STR4## --NH--CO--, --CO--NH--, --OCH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --COCH.sub.2 -- or --CHOH--CH.sub.2 --,X means N or CH,D means groups or ##STR5## and . . . . . means a single or double bond, as well as optionally their salts with physiologically harmless bases, process for their production and their pharmaceutical use.Type: GrantFiled: June 5, 1995Date of Patent: March 25, 1997Assignee: Schering AktiengesellschaftInventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
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Patent number: 5605912Abstract: A compound of the formula: ##STR1## where Q is phenyl or naphthyl optionally substituted by (a) C.sub.1-6 hydrocarbyl, C.sub.1-6 alkoxy or methylenedioxy, which in turn is optionally substituted by one to five halogen atoms; or(b) halo, cyano, nitro; or(c) a group S(O).sub.n R.sub.7 wherein n=0, 1, or 2 and R.sub.7 is C.sub.1-6 alkyl optionally substituted by halogen, or R.sub.7 is amino optionally substituted by one or two C.sub.1-6 alkyl groups; or a group NR.sub.8 R.sub.9 where R.sub.8 and R.sub.9 are independently selected from hydrogen, C.sub.1-6 alkyl or a group COR.sub.12 where R.sub.12 is C.sub.1-6 alkyl or C.sub.1-6 alkoxy;Q.sub.1 is a 1,2-cyclopropyl ring optionally substituted by a group selected from C.sub.1-13 alkyl, halo, C.sub.1-3 haloalkyl or C.sub.1-13 alkynyl or cyano;R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are the same or different with at least one being hydrogen and the others being independently selected from the group consisting of hydrogen, halo, C.sub.1-4, alkyl or C.sub.Type: GrantFiled: October 14, 1994Date of Patent: February 25, 1997Assignee: Roussel UclafInventors: George S. Cockerill, David A. Pulman, Robert J. Blade, Malcom H. Black
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Patent number: 5602119Abstract: Succinoylamino hydroxyethylamino sulfamic acid derivative compounds which are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: January 31, 1995Date of Patent: February 11, 1997Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel P. Getman, Gary A. DeCrescenzo, Eric T. Sun
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Patent number: 5597836Abstract: N-(4-Pyridyl) arylacetamides, for example N-((3-chloro-2-ethyl)-4-pyridyl)(4-(4-chlorophenoxy)phenyl)-acetamide, and 4-(aralkyoxy or aralkylamino)pyridines, for example 4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]pyridine, are active against nematodes, insects, mites, and plant pathogens.Type: GrantFiled: February 7, 1995Date of Patent: January 28, 1997Assignee: DowElancoInventors: Ronald E. Hackler, Peter L. Johnson
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Patent number: 5587387Abstract: The present invention is concerned with antiretroviral (e.g. anti-HIV-1)compounds having the formula ##STR1## wherein R.sup.1 and R.sup.2 each independently are halo or methyl; R.sup.3 is hydrogen, halo, nitro or trifiuoromethyl; R.sup.4 is trifiuoromethyl or methylcarbonyl; or a radical --C(.dbd.X)--NR.sup.5 R.sup.6 wherein X is O or S, and R.sup.5 and R.sup.6 each independently are hydrogen or C.sub.1-4 alkyl; or a radical -Alk-R.sup.7, wherein Alk is C.sub.1-4 alkanediyl; and R.sup.7 is hydrogen or hydroxy; Het is a heterocyclic radical of formula: ##STR2## Pharmaceutical compositions containing said compounds of formula (I) and processes of preparing said compounds and compositions.Type: GrantFiled: May 2, 1995Date of Patent: December 24, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5585390Abstract: Compounds of the general formula: ##STR1## wherein m, X, Y, A, R.sub.2 and R.sub.3 are defined in the description, and medicaments containing the same.Type: GrantFiled: May 9, 1995Date of Patent: December 17, 1996Assignee: Adir Et CompagnieInventors: Muriel Duflos, Sylvie Robert-Piessard, Lucien Welin, Guillaume Le Baut, Daniel-Henri Caignard, Pierre Renard, G erard Adam
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Patent number: 5583147Abstract: This invention provides amide compounds as inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.Type: GrantFiled: March 23, 1994Date of Patent: December 10, 1996Assignee: The Dupont Merck Pharmaceutical CompanyInventors: Soo S. Ko, Richard G. Wilde, Indawati DeLucca, Hui-Yin Li, Hollis S. Kezar, III, George A. Boswell, Anurag S. Srivastava
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Patent number: 5583132Abstract: Sulfonylalkanoylamino hydroxyethylamino sulfamic acid compounds which are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: February 2, 1995Date of Patent: December 10, 1996Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel P. Getman, Gary A. DeCrescenzo, Eric T. Sun
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Patent number: 5569765Abstract: A process for controlling pests in which the pests or the plants threatened by attack with pests are treated with a 2-anilinopyridine of the formula I ##STR1## where the substituents have the following meanings: R.sup.1 is alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl, substituted cycloalkyl, alkoxy, haloalkoxy, substituted alkyl, alkenyloxy, alkynyloxy, halogen, CN, SCN, formyl, CH.dbd.NOR.sub.5, CH.dbd.NR.sub.6, CH.sub.2 NHR.sub.6R.sup.5 is hydrogen, unsubstituted or substituted alkyl, alkenyl, alkynyl, COR.sup.7 or unsubstituted or substituted phenyl,R.sup.6 is hydrogen, alkyl, unsubstituted or substituted cycloalkyl, alkenyl, alkynyl or unsubstituted or substituted phenyl,R.sup.2 is alkyl, alkenyl, alkynyl, haloalkyl or cycloalkylR.sup.3 is hydrogen, CN, S(O).sub.n R.sup.8 or COR.sup.9,R.sup.8 is alkyl or substituted phenyl,R.sup.9 is hydrogen, alkyl, haloalkyl, cycloalkyl, phenyl or benzyl,R.sup.Type: GrantFiled: April 17, 1995Date of Patent: October 29, 1996Assignee: BASF AktiengesellschaftInventors: Oliver Wagner, Karl Eicken, Eberhard Ammermann, Gisela Lorenz
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Patent number: 5567723Abstract: Compounds having the structural formula ##STR1## wherein R is C.sub.1 -C.sub.6 alkoxy or C.sub.1 -C.sub.6 alkyl; R.sup.1 is fluorenyl, thienyl, pyridyl or thiazolyl, unsubstituted or substituted by one or more substituents selected from C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.1 -C.sub.4 haloalkyl and nitro; and R.sup.2 is C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkoxyalkyl. The compounds of this invention are effective for controlling mites and nematodes.Type: GrantFiled: July 5, 1995Date of Patent: October 22, 1996Assignees: Uniroyal Chemical Company, Inc., Uniroyal Chemical Ltd./LteeInventors: Mark A. Dekeyser, Derek J. McPhee, Paul T. McDonald
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Patent number: 5565477Abstract: Amides having formula I: ##STR1## wherein E, X, R.sup.2 and R.sup.3 have the meanings given in the specification, and pharmaceutically acceptable salts and pharmaceutically acceptable in vivo hydrolysable esters thereof, which are useful in the treatment of urinary incontinence. Further provided are processes for preparing the amides and pharmaceutical compositions containing them.Type: GrantFiled: June 7, 1995Date of Patent: October 15, 1996Assignee: Imperial Chemical Industries PLCInventors: Keith Russell, Cyrus J. Ohnmacht, Keith H. Gibson
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Patent number: 5547966Abstract: Compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein X is a single bond, O, CO, S, NH or N(lower alkyl); Y is O, S or NCN; and R.sup.1 to R.sup.5' are as defined herein. These compounds have potassium channel activating activity and are useful, therefore for example, as cardiovascular agents.Type: GrantFiled: October 7, 1993Date of Patent: August 20, 1996Assignee: Bristol-Myers Squibb CompanyInventors: Karnail S. Atwal, Francis N. Ferrara, Charles Z. Ding
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Patent number: 5548077Abstract: 2-Aminopyridine derivatives having a bifunctional or unifunctional structure and capable of serving as reactants in synthetically converting organic compounds, such as carbohydrates, proteins, lipids or polymer resins, to desired conjugated structures suited for various purposes and detectable by fluorescence spectrometry with high sensitivity, a fluorescent labeling agent comprising the same, and methods of their production are disclosed.Type: GrantFiled: September 23, 1994Date of Patent: August 20, 1996Assignee: Seikagaku Kogyo Kabushiki KaishaInventors: Shoichi Kusumoto, Koichi Fukase, Sumihiro Hase
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Patent number: 5532259Abstract: Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides, pharmaceuticals containing these compounds and their useIsoxazole-4-carboxamide derivatives and hydroxyalkylidene-cyanoacetamide derivatives are suitable for the treatment of carcinoses. These compounds can be prepared by known processes. Some of the compounds are novel and are additionally suitable for the treatment of rheumatic disorders.Type: GrantFiled: June 7, 1995Date of Patent: July 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Robert R. Bartlett, Friedrich-Johannes Kammerer
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Patent number: 5532245Abstract: The compounds of the formula: ##STR1## wherein R.sub.1 is hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, alkanoyl, alkylsulfonyl, aroyl, arylalkenoyl, arylsulfonyl, arylalkanoyl or arylalkylsulfonyl; R.sub.2 is hydrogen, straight or branched chain alkyl or cyclic or bicyclic alkyl; A is selected from the following: ##STR2## wherein R.sub.9 is hydrogen, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, mono- or dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano, carboxyl, chloro, bromo, fluoro or iodo; n is an integer from 0 to 6; R.sub.3 and R.sub.4, independent from each other, are hydrogen, straight or branched chain alkyl, cyclic or bicyclic alkyl, perfluoroalkyl, hydroxyalkyl, alkoxyalkyl, fluoro, or, when taken together, form a spirocyclic ring; R.sub.5 and R.sub.Type: GrantFiled: June 7, 1995Date of Patent: July 2, 1996Assignee: American Home Products CorporationInventors: John A. Butera, Schuyler A. Antane, Bradford H. Hirth
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Patent number: 5512585Abstract: The compound of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are, independent from each other, hydrogen, C.sub.1-10 straight chain alkyl, C.sub.1-10 branched alkyl, or C.sub.3-10 cyclic or bicyclic alkyl;R.sub.3 is an acyl substituent selected from the group consisting of formyl, alkanoyl of 2 to 7 carbon atoms, alkenoyl of 3 to 7 carbon atoms, alkylsulfonyl of 1 to 7 carbon atoms, aroyl of 7 to 12 carbon atoms, arylalkenoyl of 9 to 20 carbon atoms, arylsulfonyl of 6 to 12 carbon atoms, arylalkanoyl of 8 to 12 carbon atoms or arylalkylsulfonyl of 7 to 12 carbon atoms;A is selected from the group consisting of: ##STR2## wherein: R.sub.4 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 perfluoroalkyl, C.sub.1-6 alkoxy, C.sub.1-6 perfluoroalkoxy, amino, C.sub.1-6 alkylamino, C.sub.2-12 dialkylamino, C.sub.1-6 alkylsulfonamido, alkylcarboxamido containing 2 to 7 carbon atoms, nitro, cyano or carboxyl;or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.Type: GrantFiled: June 2, 1995Date of Patent: April 30, 1996Assignee: American Home Products CorporationInventors: Madelene M. Antane, John A. Butera, Bradford H. Hirth, Schuyler A. Antane
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Patent number: 5508293Abstract: Disclosed are pyridinecarboximidamides having a vasodilating effect (hypotensive activity or antianginal activity), and acid adduct salts thereof. ##STR1## wherein when R.sup.1 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl group, R.sup.2 represents a hydrogen atom and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group; andwhen R.sup.1 represents a hydrogen atom, R.sup.2 represents an alkyl, hydroxyalkyl, carboxyl, amino, acylamino, alkylamino, dialkylamino, aralkylamino, alkylsulfonamide, bisalkylsulfonylamino or hydroxyl group and R.sup.3 represents a nitroxyl, 2-chlorophenyl or phenyl group.There is also disclosed the use of the compounds represented by the formula (I) for antihypertensive or antianginal purpose.Type: GrantFiled: September 27, 1994Date of Patent: April 16, 1996Assignee: Kirin Beer Kabushiki KaishaInventors: Hideki Okawara, Tatsuo Nakajima, Nobuyuki Ogawa, Tomoko Kashiwabara, Soichiro Kaneta
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Patent number: 5500424Abstract: The present invention relates to a compound represented by the general formula (I): ##STR1## [wherein R.sup.1 is a lower alkyl group or the like, R.sup.2 is a lower alkyl group or the like, R.sup.3 and R.sup.4, which may be the same or different, are halogen atoms or the like, R.sup.5, R.sup.6 and R.sup.7, which may be the same or different, are halogen atoms or the like, and X is .dbd.N-- or .dbd.CH--] or a pharmacologically acceptable salt thereof, which has inhibitory effect on acyl-CoA:cholesterol O-acyltransferase (ACAT), a process for producing said compound, and uses of said compound.Type: GrantFiled: August 12, 1994Date of Patent: March 19, 1996Assignee: Nihon Nohyaku Co., Ltd.Inventors: Masashi Nagamine, Kenji Yamamoto, Kenji Horiuchi, Yoshimitsu Matsui, Masanori Yoshida
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Patent number: 5480997Type: GrantFiled: May 12, 1994Date of Patent: January 2, 1996Assignee: Janssen Pharmaceutica N.V.Inventors: Marcel A. C. Janssen, Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Marc G. C. Verdonck, Paul A. J. Janssen
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Patent number: 5476863Abstract: A glycerin derivative having the following formula (I) or (I') and a pharmacologically acceptable salt thereof are useful to treat diseases caused by the platelet activating factor.Type: GrantFiled: September 30, 1993Date of Patent: December 19, 1995Assignee: Eisai Co., Ltd.Inventors: Kazuo Okano, Osamu Asano, Naoyuki Shimomura, Tetsuya Kawahara, Shinya Abe, Shuhei Miyazawa, Mitsuaki Miyamoto, Hiroyuki Yoshimura, Koukichi Harada, Junsaku Nagaoka, Tsutomu Kawata, Tsutomu Yoshimura, Hiromasa Suzuki, Shigeru Souda, Yoshimasa Machida, Kouichi Katayama, Isao Yamatsu
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Patent number: 5476864Abstract: A glycerin derivative having the following formula (I) or (I') and a pharmacologically acceptable salt thereof are useful to treat diseases caused by the platelet activating factor.Type: GrantFiled: November 10, 1993Date of Patent: December 19, 1995Assignee: Eisai Co., Ltd.Inventors: Kazuo Okano, Osamu Asano, Naoyuki Shimomura, Tetsuya Kawahara, Shinya Abe, Shuhei Miyazawa, Mitsuaki Miyamoto, Hiroyuki Yoshimura, Koukichi Harada, Junsaku Nagaoka, Tsutomu Kawata, Tsutomu Yoshimura, Hiromasa Suzuki, Shigeru Souda, Yoshimasa Machida, Kouichi Katayama, Isao Yamatsu
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Patent number: 5453512Abstract: A 2-amino-3-nitro-5-halogenopyridine is formed from a 2-acylaminopyridine by way of a 2-acylamino-5-halogenopyridine. The 2-acetamido-5-bromopyridine may be formed from the 2-acylaminopyridine by way of a 2-acylaminopyridinium-HBr.sub.3 salt.Type: GrantFiled: December 17, 1993Date of Patent: September 26, 1995Assignee: Ichikawa Gosei Chemical Co., Ltd.Inventors: Yoshio Igarashi, Makoto Shimoyamada, Motoki Takashima, Tetsuya Suzuki
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Patent number: 5446065Abstract: Compounds of the formula I ##STR1## in which R.sub.1 signifies an aryl, aralkyl or an aralkenyl group, the aryl radical of which can, in each case, be substituted one or more times by halogen, cyano, alkyl, trifluoromethyl, alkoxy, alkylthio, trifluoromethoxy, hydroxyl or carboxyl, m a whole number from 1 to 3, n a whole number from 1 to 5, R.sub.2 hydrogen, an alkyl, aralkyl or acyl group, Q a bond or an oxygen atom, R.sub.3 hydrogen or a lower alkyl radical which is possibly terminally substituted by carboxyl or by a hydroxyl group and R.sub.4 hydrogen, a lower alkyl group with 1-4 C-atoms, which is possibly terminally substituted by carboxyl or hydroxyl, a possibly substituted phenyl, heteroaryl, cycloalkyl or acyl group or a group ##STR2## in which R.sub.Type: GrantFiled: June 21, 1993Date of Patent: August 29, 1995Assignee: Boehringer Mannheim GmbHInventors: Ernst-Christian Witte, Hansjorg Beckh, Karlheinz Stegmeier, Liesel Doerge
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Leukotriene-B.sub.4 derivatives, process for their production and their use as pharmaceutical agents
Patent number: 5440044Abstract: The present invention relates to a leukotriene-B.sub.4 analog according to formula I ##STR1## in which R.sup.1 is a COOR.sup.2 group, wherein R.sup.2 is a C.sub.2-4 -alkyl group;B is a C.sub.1-3 -alkylene group, a radical ##STR2## wherein R.sup.3 is a hydrogen atom or a carboxy or methoxycarbonyl group; ##STR3## . . . is a single or double bond; or optionally, their salts with physiologically compatible bases. The present invention also relates to the production of the latter leukotriene-B.sub.4 analogs and their use as pharmacological agents.Type: GrantFiled: December 3, 1993Date of Patent: August 8, 1995Assignee: Schering AktiengesellschaftInventors: Josef Heindl, Werner Skuballa, Bernd Buchmann, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen -
Patent number: 5438059Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is optionally substituted aryl or optionally substituted heteroaryl; Y is oxygen, sulphur or NR.sup.4 ; R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, are hydrogen, C.sub.1-4 alkyl or C.sub.2-4 alkenyl; X is halogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.1-4 alkoxy, nitro or cyano; and n is 0 or an integer of 1 to 4; provided that when Y is oxygen, n is 0 and R.sup.1 is unsubstituted phenyl at least one of R.sup.2 and R.sup.3 is other than hydrogen or methyl.Type: GrantFiled: July 6, 1993Date of Patent: August 1, 1995Assignee: Zeneca LimitedInventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Michael G. Hutchings, Vivienne M. Anthony
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Patent number: 5420145Abstract: Carboxylic acid derivatives having potent retinoid-type pharmacological activities are disclosed. The compounds disclosed are represented by the following formula: ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 independently represent a hydrogen atom or an alkyl group with the exception that all of R.sup.1, R.sup.2, and R.sup.3 do not simultaneously represent hydrogen atoms and R.sup.1 together with R.sup.2 optionally represent a cyclic structure formed by the combination thereof; R.sup.4 represents a hydrogen atom or an alkyl group; X represents a nitrogen atom or C--OH; and A represents --CO--NH-- or --NH--CO--.Type: GrantFiled: March 23, 1993Date of Patent: May 30, 1995Assignees: Koichi Shudo, Shionogi Pharmaceutical Co., Ltd.Inventor: Koichi Shudo
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Patent number: 5418244Abstract: Compounds of the formula ##STR1## wherein the variables are defined in the specification. The compounds and their salts are soft anticholinergic/antisecretory agents especially useful as mydriatics and as antiperspirants.Type: GrantFiled: August 11, 1993Date of Patent: May 23, 1995Assignee: University of FloridaInventors: Richard H. Hammer, Nicholas S. Bodor
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Patent number: 5418245Abstract: Methods of inhibiting cell proliferation in a patient suffering from such disorder comprising the use of a styryl-substituted heteroaryl compound wherein the heteroaryl group is a monocyclic ring with 1 or 2 heteroatoms, or a bicyclic ring with 1 to about 4 heteroatoms, said compound optionally substituted or polysubstituted, with the proviso that when said ring is polysubstituted, the substituents do not have a common point of attachment to said ring, and those compounds wherein no substituent on the heteroaryl group is a carboxy group or an ester group, and pharmaceutical compositions comprising such compounds.Type: GrantFiled: March 17, 1994Date of Patent: May 23, 1995Assignee: Rhone-Poulenc Rorer International (Holdings) Inc.Inventors: Alfred P. Spada, Paul E. Persons
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Patent number: 5403845Abstract: Substituted 1,4,5,6 -tetrahydropyrimidine compositions, substituted 1,2,3,6 -tetrahydropyrimidine compositions and substituted 3,4,5,6 -tetrahydropyridine compositions are disclosed. They are useful for stimulating muscarinic receptors including, for example, treating the symptoms of cognitive disorders, especially impaired memory, which are associated with decreased acetylcholine synthesis and cholinergic cell degeneration.Type: GrantFiled: April 7, 1994Date of Patent: April 4, 1995Assignee: University of ToledoInventors: Philip G. Dunbar, Graham J. Durant, Wayne P. Hoss, William S. Messer, Jr.
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Patent number: 5399564Abstract: N-(4-Pyridyl or 4-quinolinyl) arylacetamides, for example N-((3-chloro-2-ethyl)-4-pyridyl)(4-(4-chlorophenoxy) phenyl)-acetamide, and 4-(aralkyoxy or aralkylamino)pyridines, for example 4-[2-[4-(2,2,2-trifluoroethoxy)phenyl]ethoxy]pyridine, are active against nematodes, insects, mites, and plant pathogens.Type: GrantFiled: August 19, 1992Date of Patent: March 21, 1995Assignee: DowElancoInventors: Ronald E. Hackler, Glen P. Jourdan, Peter L. Johnson, Brian R. Thoreen, Jack G. Samaritoni
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Patent number: 5386033Abstract: 2-Aminopyridine derivatives having a bifunctional or unifunctional structure and capable of serving as reactants in synthetically converting organic compounds, such as carbohydrates, proteins, lipids or polymer resins, to desired conjugated structures suited for various purposes and detectable by fluorescence spectrometry with high sensitivity, a fluorescent labeling agent comprising the same, and methods of their production are disclosed.Type: GrantFiled: March 15, 1993Date of Patent: January 31, 1995Assignee: Seikagaku Kogyo Kabushiki Kaisha (Seikagaku Corporation)Inventors: Shoichi Kusumoto, Sumihiro Hase, Koichi Fukase
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Patent number: 5384425Abstract: Diurea derivatives are provided which can be represented by the following general formula and salts thereof: ##STR1## wherein, R.sup.1 and R.sup.2 are the same or different, and each represents C.sup.1 -10 alkyl group, a C.sup.3 -18 cycloalkyl group, or a lower alkyl group substituted by cycloalkyl radical(s);R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different, and each represents a hydrogen atom, a lower alkyl group, a cycloalkyl group, hydrocarbyl aralkyl group, a pyridyl group, or an unsubstituted or substituted phenyl group, the substituents of the phenyl group being selected from a group consisting of lower alkyl radical, halogen atom-substituted lower alkyl radical, halogen atom, nitro radical, amino radical, mono- or di-lower alkylamino radical, lower acylamino radical, hydroxyl radical, lower alkoxy radical and lower acyloxy radical;X represents an oxygen atom or a sulfur atom, and n.sup.1 and n.sup.2 represent an integer of 1 to 6; and wherein at least one of R.sup.3 -R.sup.Type: GrantFiled: October 7, 1993Date of Patent: January 24, 1995Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Noriki Ito, Tomoyuki Yasunaga, Yuichi Iizumi, Tomio Araki
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Patent number: 5380733Abstract: Compounds of the formula:Q(CH.sub.2).sub.a (O).sub.b Q.sub.1 CR.sub.2 .dbd.CR.sub.3 CR.sub.4 .dbd.CR.sub.5 CX.sub.1 NHR.sub.1wherein the terms Q, Q.sub.1, R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, X.sub.1 and the integers a and b are defined in the specification, or salts thereof. Said compounds are useful as pesticides.Type: GrantFiled: December 16, 1992Date of Patent: January 10, 1995Assignee: Roussel UclafInventors: George S. Cockerill, David A. Pulman, Robert J. Blade, Malcom H. Black
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Patent number: 5374733Abstract: The present invention relates to a novel sweetening agent and to its method of preparation. This novel sweetening agent is a 2-substituted acyl derivative of L-aspartic or L-glutamic acid and has the general formula ##STR1## R being an acyl group of the formula ##STR2## and R' being a group of the formula ##STR3## R.sub.1, R.sub.2, R.sub.3, X, Y and Z being variously defined. This novel sweetening agent is essentially characterized by a high sweetening potency and a high stability compatible with the conditions of industrial use, and is applied especially for sweetening soft drinks.Type: GrantFiled: January 11, 1993Date of Patent: December 20, 1994Inventors: Claude Nofre, Jean-Marie Tinti
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Patent number: 5373023Abstract: The invention provides compounds which are tetrahydronaphthalene derivatives of the formula (I) ##STR1## wherein R.sub.1 represents a halogen atom, a cyano group, a nitro group, an unbranched (C.sub.1 -C.sub.6) alkoxy group, a (C.sub.1 -C.sub.6 cycloalkyl) (C.sub.1 -C.sub.2 alkoxy) group or an aryl (C.sub.1 -C.sub.2 alkoxy) group,R.sub.2 represents a (C.sub.1 -C.sub.4) alkyl group, an aryl group optionally substituted with at least one methoxy group, a pyridyl group or a benzodioxanyl group,R.sub.3 represents a hydrogen atom or a (C.sub.1 -C.sub.2) alkyl group, and n=0 to 3, or are addition salts with pharmaceutically acceptable acids. The compounds of the invention have anti-ischaemic activity.Type: GrantFiled: August 4, 1993Date of Patent: December 13, 1994Assignee: SYNTHELABOInventors: Paul Howard Williams, Christian Hoornaert, Jean Claude Muller
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Patent number: 5366982Abstract: This invention relates to compounds having selective LTB.sub.4 antagonist properties, compositions comprising said compounds and methods for the treatment of disorders involving LTB.sub.4 agonist-mediated activity utilizing said compositions wherein the compounds are described by the general formula ##STR1## and pharmaceutically acceptable salts thereof.Type: GrantFiled: February 17, 1993Date of Patent: November 22, 1994Assignee: Rhone-Poulenc Rorer S.A.Inventors: Norbert Dereu, Wolfram Hendel, Richard Labaudiniere
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Patent number: 5367081Abstract: 1,4-dihydropyridine derivatives and optically active 1,4-dihydropyridine derivatives with the following formula, having vasodilating activity based on calcium antagonism, and PAF antaognism, and methods of producing the same are disclosed: ##STR1## wherein (*) indicates a chiral center in the case of the optically active 1,4-dihydropyridine derivatives.Type: GrantFiled: November 29, 1991Date of Patent: November 22, 1994Assignee: Fujirebio Inc.Inventors: Hiroshi Ikawa, Akiyoshi Kadoiri, Yasuko Konagai, Tetsuaki Yamaura, Noriko Kase
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Patent number: 5364943Abstract: Substituted piperidines and related compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are herein defined are disclosed.Type: GrantFiled: November 27, 1991Date of Patent: November 15, 1994Assignee: Pfizer Inc.Inventors: Terry J. Rosen, Dennis M. Godek, Sally Gut, Lewin Wint
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Patent number: 5364855Abstract: The invention relates to new 4-cinnolinyl- and 4-naphthyridinyl-dihydropyridines of the general formula I ##STR1## in which R.sup.1 to R.sup.5 have the meaning given in the description, to processes for their preparation and to their use in medicaments, in particular in compositions having positively inotropic action.Type: GrantFiled: January 21, 1993Date of Patent: November 15, 1994Assignee: Bayer AktiengesellschaftInventors: Alexander Straub, Jurgen Stoltefuss, Siegfried Goldmann, Rainer Gross, Martin Bechem, Siegbert Hebisch, Joachim Hutter, Howard-Paul Rounding
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Patent number: 5362878Abstract: Compounds of the formula ##STR1## wherein R.sup.21 and R.sup.22 are as defined in the specification which are intermediates useful in the preparation of compounds of the formula ##STR2## and the pharmaceutically acceptable salts thereof, wherein Q and R.sup.1 are as defined in the specification. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.Type: GrantFiled: July 20, 1992Date of Patent: November 8, 1994Assignee: Pfizer Inc.Inventors: George Chang, Ernest S. Hamanaka, Peter A. McCarthy, Thien Truong, Frederick J. Walker
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Patent number: 5356909Abstract: The invention relates to substituted pyridine-2,4-dicarboxylic acid derivatives of the formula I ##STR1## in which R.sup.1 and R.sup.2 have the meanings given. The invention also relates to a process for the preparation of the abovementioned compounds and to their use as medicaments, in particular as fibrosuppressants and immunosuppressants.Type: GrantFiled: June 25, 1992Date of Patent: October 18, 1994Assignee: Hoechst AktiengesellschaftInventors: Ekkehard Baader, Martin Bickel, Dietrich Brocks, Volkmar Gunzler, Stephan Henke, Hartmut Hanauske-Abel
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Patent number: 5354763Abstract: The compounds of the formula: ##STR1## wherein: R.sub.1 and R.sub.2 are, independently, hydrogen, straight or branched chain alkyl or mono- or bi-cyclic alkyl;A is an N-heterocycle which may be substituted by alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, alkylsulfonamido, alkylcarboxamido, nitro, cyano or carboxyl;or, A is a substituted phenyl group containing one or two substituents selected from cyano, nitro, alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, amino, alkylamino, dialkylamino, sulfamyl, alkylsulfonamido, arylsulfonamido, alkylcarboxamido, arylcarboxamido, alkylsulfone, perfluoroalkylsulfone, arylsulfone, chloro, bromo, fluoro, iodo, 1-imidazolyl or carboxyl;or a pharmaceutically acceptable salt thereof, are smooth muscle relaxants.Type: GrantFiled: November 17, 1993Date of Patent: October 11, 1994Assignee: American Home Products CorporationInventors: John A. Butera, Schuyler A. Antane
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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