At 4- Or 6-position Patents (Class 544/326)
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Patent number: 5342837Abstract: Fungicidal compounds having the formula (I): ##STR1## and stereoisomers thereof, wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted heterocyclyloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted aryloxy, optionally substituted heterocyclyloxy, nitro halo cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.sup.3).sub.Type: GrantFiled: January 22, 1993Date of Patent: August 30, 1994Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Paul J. de Fraine, Ian R. Matthews
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Patent number: 5340827Type: GrantFiled: June 14, 1993Date of Patent: August 23, 1994Assignee: Celltech, LimitedInventors: Nigel R. A. Beeley, Thomas A. Millican
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Patent number: 5336677Abstract: This invention relates to substituted 4-aminopyrimidines, which by virtue of their ability to antagonize angiotensin II are useful for the treatment of hypertension, congestive heart failure, and restenosis. The compounds are also useful for reducing lipid levels in the blood plasma and are thus useful for treating hyperlipidemia and hypercholesterolemia. Also disclosed are processes for the production of said compounds and pharmaceutical compositions containing said compounds.Type: GrantFiled: June 18, 1992Date of Patent: August 9, 1994Assignee: American Home Products CorporationInventors: Dimitri Sarantakis, James J. Bicksler, John W. Ellingboe, Madelene Nikaido
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Patent number: 5330989Abstract: Biphenyl derivatives of cyclobutene-1,2-dione of formula 1 are angiotensin II antagonists and are useful for the treatment of hypertension and congestive heart failure ##STR1## wherein: Y is O, NR.sup.7, NCOR.sup.7 ; or R.sup.5 and Y taken together represent a linking chain of N.dbd.CR.sup.8 N; or R.sup.5 and Y taken together represent a linking chain of (CR.sup.9 R.sup.10).sub.n CON where n=1,2,3,4, or 5;X is N, CR.sup.7 ;Z is N, CR.sup.7 ;R.sup.1 is H, alkyl, benzyl, alkoxyalkyl, phenyl;R.sup.2 is H, alkyl, benzyl, alkoxyalkyl, phenyl, alkoxy, alkyl-OH, perfluoroalkyl, F, Cl, Br, I, NR.sup.7 R.sup.8 ;R.sup.3 is H, alkyl, benzyl, alkoxyalkyl, phenyl, alkoxy, alkyl-OH, perfluoroalkyl, F, Cl, Br, I, NR.sup.7 R.sup.8 ;R.sup.4 is H, NR.sup.7 R.sup.8, OR.sup.1, CN, F, Cl, I, Br, perfluoroalkyl, alkyl, phenyl, alkoxy, alkyl-OH, alkoxyalkyl, --(CH.sub.2).sub.n CO.sub.2 R.sup.1, --(CH.sub.2).sub.n CONR.sup.7 R.sup.8 where n=1, 2, 3, 4, or 5;R.sup.5, R.sup.Type: GrantFiled: September 11, 1992Date of Patent: July 19, 1994Assignee: American Home Products CorporationInventors: Richard M. Soll, William A. Kinney
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Patent number: 5324837Abstract: 3,4-Diaryl-4,5-dihydro-1H-pyrazole compounds having a selected 5- or 6-membered aromatic heterocyclic moiety in the 4-position and an optionally substituted phenyl moiety in the 3-position, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazo le were prepared as intermediates in the preparation of insecticidal 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds. The 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds can be prepared from appropriate 1,2-diarylethanone compounds by successive treatments with N,N,N',N'-tetramethyldiaminomethane in dichloromethane in the presence of acetic anhydride (to form a Mannich adduct) and hydrazine in the presence of a catalytic amount of trifluoroacetic acid.Type: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Assignee: DowElancoInventors: James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
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Patent number: 5312919Abstract: This invention relates to novel photooxidation products, and derivatives thereof, of Merocyanine 540, their preparation and their uses as anticancer and antiviral agents.Type: GrantFiled: June 12, 1992Date of Patent: May 17, 1994Assignee: Baylor Research InstituteInventors: Kirpal S. Gulliya, Burchard Franck, J. Lester Matthews, Udo Schneider
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Patent number: 5304647Abstract: A method of preparation of substituted halogenodiazines which are useful as intermediates in the synthesis of novel unfused heterobicyclic compounds, and the products thereof.The reaction consists of the addition of an organolithium reagent with subsequent dehydrogenation of the addition product. The reaction takes place in one reaction vessel, without isolation of the substituted halogenodihydrodiazine intermediate. The reactions proceed at moderate temperature and in a short amount of time, which decreases the probability of side reactions and increases yield. Furthermore, the workup step is conducted under two-phase conditions to prevent hydrolysis of the substituted halogenodiazine to a substituted hydroxydiazine. The method is easy, efficient and results in a high yield of product.Type: GrantFiled: August 24, 1990Date of Patent: April 19, 1994Assignee: Georgia State University Foundation, Inc.Inventors: Lucjan Strekowski, Maria Mokrosz, Donald B. Harden
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Patent number: 5304565Abstract: Nitrogen-containing heterocyclic compounds of the formula (I): ##STR1## wherein Y is N or CH; R.sup.1, which may be optionally bound through a hetero atom, is a hydrocarbon residue which may be substituted; R.sup.2 and R.sup.3 which may be same or different, are each independently hydrogen, cyano, nitro, optionally substituted lower alkyl, or --COD wherein D is alkoxy, hydroxy, halogen, or optionally substituted amino: or R.sup.2 and R.sup.3 are taken together to form a benzene ring which may be substituted; the dotted line is a chemical bond; Z is bound to a hetero nitrogen atom and is a group having the formula: ##STR2## wherein R.sup.4 is hydrogen, halogen or nitro, and R.sup.Type: GrantFiled: March 7, 1991Date of Patent: April 19, 1994Assignee: Takeda Chemical Industries, Ltd.Inventors: Akira Morimoto, Kohei Nishikawa
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Patent number: 5300656Abstract: Coumarin deviatives of the formula ##STR1## in which R.sup.1 denotes cyano,R.sup.2 represents phenyl or thiazolyl bonded in the 2-, 4-, or 5-position,R.sup.3 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl andR.sup.4 represents hydrogen, C.sub.1 -C.sub.4 -alkyl or phenylsulphonyl, where C.sub.1 -C.sub.4 -alkyl can be substituted by hydroxyl, amino, carboxyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl and phenyl can be monosubstituted or disubstituted by chlorine, bromine or C.sub.1 -C.sub.4 -alkyl, where furthermore R.sup.3 and R.sup.4, together with the N atom which they substitute, can denote a morpholine ring, a piperazine ring or a triazole ring which can carry one or two substituents from the group comprising methyl, ethyl and phenyl, andwhere furthermore one of the radicals R.sup.2, R.sup.3 and R.sup.4 denotes or carries a primary or secondary amino group, the hydroxyl group, the carboxyl group or the C.sub.1 -C.sub.Type: GrantFiled: July 16, 1992Date of Patent: April 5, 1994Assignee: Bayer AktiengesellschaftInventors: Eberhard Kuckert, Gunther Beck, Florin Seng, Antonius Lobberding
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Patent number: 5290931Abstract: Water-insoluble naphthalic acid imide dyestuffs of the following formula: ##STR1## wherein D is ##STR2## wherein R.sup.1 is C.sub.1 -C.sub.8 alkyl which may be substituted, R.sup.2 is hydrogen, halogen, lower alkyl, lower alkoxy or cyano, X is oxygen or sulfur, and m is 0 or 1; A is phenylene, alkylene, aralkylene or --C.sub.2 H.sub.4 OC.sub.2 H.sub.4 --; B is oxygen, sulfur or ##STR3## wherein R.sup.3 is hydrogen or lower alkyl; Y is a 6-membered nitrogen-containing heterocyclic ring having at least one active halogen atom; and n is 0 or 1.Type: GrantFiled: September 4, 1992Date of Patent: March 1, 1994Assignee: Hoechst Mitsubishi Kasei Co., Ltd.Inventors: Kiyoshi Himeno, Toshio Hihara
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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: 5280025Abstract: Disclosed are an aralkylaminopyrimidine compound represented by the following formula: ##STR1## wherein R.sup.1 represents a halogen atom, a lower acyloxy group, a hydroxyl group, a lower alkoxy group or a lower alkylthio group; R.sup.2 represents a lower alkyl group, a hydrogen atom or a cycloalkyl group; R.sup.3 may be the same or different and represents a lower haloalkoxy group, a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a lower alkylthio group, a nitro group, a lower haloalkyl group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a lower haloalkylthio group or a hydroxyl group; a carbon atom to which * is attached represents an asymmetric carbon atom provided that the case where R.sup.2 is a hydrogen atom is excluded; and n represents an integer of 1 to 5.a method for preparing the same and a chemical for controlling noxious organisms which contains the same as an active ingredient.Type: GrantFiled: November 17, 1992Date of Patent: January 18, 1994Assignee: Ube Industries, Ltd.Inventors: Tokio Obata, Katsutoshi Fujii, Kiyoshi Tsutsumiuchi, Yasushi Nakamoto
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Patent number: 5262385Abstract: A compounds represented by the formula ##STR1## wherein X represents a fluorine atom,W represents an oxygen atom, sulfur atom or group --OCH.sub.2 --,Z.sup.1 and Z .sup.2 each represent a nitrogen atom or group CH, but when Z.sup.1 is a nitrogen atom, Z.sup.2 represents a nitrogen atom or group CH and when Z.sup.1 is a group CH, Z.sup.2 represents a nitrogen atom,R.sup.1 and R.sup.2 each independently represent either a hydrogen atom, halogen atom or mono- or dilower alkyl-substituted amino, or a lower alkyl, lower alkoxy or lower alkylthio each of which may be substituted with a halogen atom,R.sup.3 and R.sup.4 form together with the carbon atoms to which they bind respectively a 5- to 8-membered carbon ring.Type: GrantFiled: July 23, 1991Date of Patent: November 16, 1993Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Atsushi Goh, Sachio Kudo, Yorio Kumamoto, Michi Watanabe, Takako Takahashi, Takako Aoki, Norishige Toshima, Keiji Endo, Hideshi Mukaida, Shinji Kawaguchi, Rika Higurashi
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Patent number: 5254555Abstract: Compounds of the formula (I) or pharmaceutically acceptable salts thereof ##STR1## where R.sub.2 -R.sub.7, Y, a and b are as defined, are useful in the treatment of hypertension and respiratory tract disorders.Type: GrantFiled: March 19, 1992Date of Patent: October 19, 1993Assignee: Beecham Group p.l.c.Inventors: Geoffrey Stemp, John M. Evans, Gordon Burrell
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Patent number: 5252567Abstract: This invention concerns compounds of the formula I: ##STR1## wherein R.sup.1 is (1-10C)alkyl, (3-8C)cycloalkyl, (3-8C)cycloalkyl-(1-4C)-alkyl, phenyl or phenyl(1-4C)alkyl, the phenyl moiety of the latter two optionally bearing one or more substituents; R.sup.2 is hydrogen, (1-4C)alkyl, amino or (1-4C)alkylamino; R.sup.6 is (1-4C)alkyl, amino or (1-4C)alkylamino; Q is a group of formula II, in which case R.sup.3 and R.sup.4 are independently hydrogen, (1-4C)alkyl, phenyl or benzyl the phenyl moiety of the latter two optionally bearing one or two substituents; R.sup.5 is hydrogen, (1-4C)alkyl or (2-4C)alkenyl; A and B are independently ethylene or trimethylene; Z is a direct bond between A and B, or an oxy, thio, carbonyl, methylene, ethylenedioxymethylene, ethylidene, or isopropylidene link, or Z is a group of the formula .dbd.N.Type: GrantFiled: December 18, 1990Date of Patent: October 12, 1993Assignee: Imperial Chemical Industries PLCInventors: Stuart D. Mills, Rodney B. Hargreaves, Bernard J. McLoughlin
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Patent number: 5238907Abstract: The invention relates to new 2-pyrimidinyl- and 2-triazinylacetic acid derivatives of general formula I ##STR1## in which A, R.sup.2-5 and X have the meanings given in the description, processes for their preparation and their use as herbicides, fungicides and plant growth regulants.Type: GrantFiled: January 9, 1992Date of Patent: August 24, 1993Assignee: Schering AktiengesellschaftInventors: Gabriele Kruger, Christoph Harde, Nikolaus Heinrich, Anita Kruger, Erhard Nordhoff, Gerhard Tarara, Peter Wegner, Clemens Kotter, Gerhard Johann, Richard Rees, Graham P. Jones
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Patent number: 5236923Abstract: New substituted pyrimidylamide oximes of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, A and Ar have the meanings given in the description, new intermediates for their preparation, and their use for combating pests.The new compounds of the formula (I) can be prepared by analogous processes, for example by reacting suitable pyrimidylamide oximes with suitable alkylating agents. The starting compounds which are also new, namely the pyrimidylamide oximes of the formula (II) in which --A--Ar represents hydrogen, can be prepared from suitable cynaopyrimidines with hydroxylamine or its acid adducts.Type: GrantFiled: November 26, 1991Date of Patent: August 17, 1993Assignee: Bayer AktiengesellschaftInventors: Rolf Kirsten, Hilmar Wolf, Gerd Hanssler, Heinz-Wilhelm Dehne, Stefan Dutzmann
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Patent number: 5231097Abstract: There are described new pyrimidyl-substituted acrylic esters of the general formula (I) ##STR1## in which Py, X, R.sup.1 and R.sup.2 have the meaning given in the description, a process for their preparation, and new intermediates.The compounds of the formula (I) are used as pesticides.Type: GrantFiled: August 2, 1991Date of Patent: July 27, 1993Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Peter C. Knuppel, Heinz-Wilhelm Dehne, Stefan Dutzmann
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Patent number: 5223505Abstract: This invention concerns novel aminopyrimidinium salts of the formula I: ##STR1## in which R.sup.1 is alkyl, alkenyl, cycloalkyl, phenyl, phenylalkyl or cycloalkyl-alkyl; one of R.sup.2 and R.sup.6 is a basic group selected from amino, alkylamino, dialkylamino of up to eight carbon atoms, pyrrolidino, piperidino and morpholino; and the other of R.sup.2 and R.sup.6 is hydrogen, alkyl, alkenyl, alkoxyalkyl, phenyl, phenylalkyl, cycloalkyl or cycloalkyl-alkyl; or both of R.sup.2 and R.sup.6 are basic groups as mentioned above; and R.sup.5 is hydrogen, (1-4C)alkyl or (3-6C)alkenyl; or R.sup.2 is a basic group as mentioned above, and R.sup.5 and R.sup.6 together form alkylene or, together with the appendant carbon atoms of the pyrimidine ring, complete a benzene ring; R.sup.4 is hydrogen, alkyl, cycloalkyl-alkyl, alkenyl, alkynyl or phenylalkyl; or R.sup.4 is an optionally substitutued alkylene or alkenylene linked to the nitrogen atom of the group Q.A.Type: GrantFiled: April 20, 1990Date of Patent: June 29, 1993Assignee: Imperial Chemical Industries PlcInventors: Rodney B. Hargreaves, Paul W. Marshall, Bernard J. McLoughlin, Stuart D. Mills
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Patent number: 5217973Abstract: The present invention relates to the derivatives of formula: ##STR1## as well as to their addition salts and to their use in therapy, in particular for the treatment of cardiovascular diseases, especially for the treatment of hypertension, cardiac insufficiency and diseases of the arterial wall.Type: GrantFiled: August 7, 1991Date of Patent: June 8, 1993Assignee: Laboratoires UPSAInventors: Nicole Bru-Magniez, Eric Nicolai, Jean-Marie Teulon
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Patent number: 5198547Abstract: Intermediates and a process for the synthesis of 6-monosubstituted tetrahydropteridine C6-stereoisomers, including (6S)-tetrahydrofolic acid. The intermediates are shown in their two enantiomeric forms as follows: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and represent hydrogen, methyl, hydroxy, amino, alkyl or dialkylamino, alkoxy, benzyloxy, or benzylthio; R.sub.3 represents an alkene, alkyne, cycloalkyl, benzyl, alkyl (substituted with hydroxy, acetoxy, benzyloxy, alkoxy, alkylthio, amino, carboxy, oxo, or phosphate), a protected aldehyde, or ##STR2## wherein n=1 or 2, R.sub.4 is hydrogen, formyl, methyl, or propargyl, and ZZ represents an amino acid or amino acid polymer. Also, a process for tetrahydropteridine N5-formylation for the preparation of, for example, N5-formyl-(6S)-tetrahydrofolic acid.Type: GrantFiled: March 16, 1992Date of Patent: March 30, 1993Assignee: South Alabama Medical Science Foundation, USAInventors: Steven W. Bailey, June E. Ayling
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Patent number: 5196419Abstract: The invention concerns a heterocyclic cyclic ether 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 or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 and R.sup.2 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the oxygen atom to which A.sup.2 is attached and with the carbon atom to which A.sup.3 is attached, defines a ring having 5 to 7 ring atoms, wherein A.sup.2 and A.sup.3 each is (1-3C)alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino, and which ring may bear one, two or three substituents; andR.sup.Type: GrantFiled: November 4, 1991Date of Patent: March 23, 1993Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Graham C. Crawley, Annie Hamon
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Patent number: 5179204Abstract: This invention relates to N-heteroaryl-4-pyrimidinamines of the formula ##STR1## where R.sub.1 is hydrogen, loweralkyl, aryl, or arylloweralkyl; R.sub.2 and R.sub.3 are independently hydrogen or loweralkyl, or R.sub.2 and R.sub.3 taken together are aryl; R.sub.4 and R.sub.5 are independently hydrogen or loweralkyl, or R.sub.4 and R.sub.5 taken together are aryl; X is hydrogen, halogen, cyano, nitro, amino, loweralkyl, loweralkoxy, trifluoromethyl or ##STR2## where Y is hydrogen, halogen or loweralkyl; m is an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometrical and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as memory enhancing agents and as analgesic agents.Type: GrantFiled: September 18, 1990Date of Patent: January 12, 1993Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventors: Richard C. Effland, Joseph T. Klein, Larry Davis, Gordon E. Olsen
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Patent number: 5175292Abstract: A therapeutic method is provided, employing an antiviral compound of the general formula: ##STR1## wherein Z is H, OR' or N(R) .sub.2, wherein R' is H, (C.sub.1 -C.sub.4)alkyl, aryl, CHO, (C.sub.1 -C.sub.16)alkanoyl or O.dbd.P(OH) .sub.2, Y is CH or N, and X is selected from the group consisting of H, N(R) .sub.2, SR, OR' or halogen, wherein R is H, lower (C.sub.1 -C.sub.4)alkyl, aryl or mixtures thereof, and the pharmaceutically acceptable salts thereof.Type: GrantFiled: June 5, 1991Date of Patent: December 29, 1992Assignee: Regents of the University of MinnesotaInventors: Robert Vince, Mei Hua
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Patent number: 5169856Abstract: The present invention relates to unsaturated carboxylic acid amide derivatives of the formula ##STR1## wherein ring A stands for an optionally substituted aromatic ring; R.sup.1 stands for a hydrogen atom or an optionally substituted hydrocarbon residue or forms an optionally substituted carbocyclic ring with the adjacent group --CH.dbd.C-- together with two carbon atoms constituting the ring A; R.sup.2 stands for a hydrogen atom, an optionally substituted hydrocarbon residue or an optionally substituted acyl group; R.sup.3 stands for an optionally substituted hydrocarbon residue; and n denotes an integer ranging from 2 to 6, and salts thereof, as well as the production thereof.The compounds of the present invention act on the central nervous system of mammals and has a strong anti-cholinesterase activity, which can be used for the prophylaxis and therapy of, for example, senile dementia, Alzheimer's diseases, Huntington's chorea, et., and are useful as medicines.Type: GrantFiled: February 6, 1989Date of Patent: December 8, 1992Assignee: Takeda Chemical Industries, Inc.Inventors: Giichi Goto, Akinobu Nagaoka
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Patent number: 5166206Abstract: Substituted pyrimidines, pyrimidinones and pyridopyrimidines of formula (I) are as angiotensin II antagonists useful in the treatment of hypertension, ocular hypertension and certain CNS ailments: ##STR1## wherein K is --N(R.sup.8a)--C(.dbd.M) or --N.dbd.C(R.sup.8b) where M is O or NR.sup.22.Type: GrantFiled: March 27, 1991Date of Patent: November 24, 1992Assignee: Merck & Co., Inc.Inventors: Eric E. Allen, William J. Greenlee, Malcolm MacCoss, Arthur A. Patchett
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Patent number: 5145967Abstract: The present invention is directed to a method for preparing a 4-alkoxyalkyl-4-phenylaminopiperidine compound which comprises the steps of (a) reacting an N-substituted-4-piperidone compound with an aniline compound to form a Schiff base compound, (b) reacting the Schiff base compound with an anionic reagent having an anion stabilizing group to form an amine compound, and (c) reducing the amine compound in step (b) with a reducing agent to displace the anion stabilizing group.The anionic reagent in step (b) above has the general formula:X--CYM--Zwherein X is an anion stabilizing group, Y is hydrogen or lower-alkyl, Z is lower-alkoxy or phenylmethoxy, M is an alkali or alkaline earth metal, and C is a carbon atom.Type: GrantFiled: November 2, 1990Date of Patent: September 8, 1992Assignee: Anaquest, Inc.Inventors: Bor-Sheng Lin, H. Kenneth Spencer, Joseph W. Scheblein
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Patent number: 5141941Abstract: Disclosed are a compound of the formula (I) or an acid addition salt thereof: ##STR1## wherein Q represents R.sup.1 , R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, n and z are defined as in the specification, preparation method thereof and fungicides containing the same.Type: GrantFiled: November 15, 1989Date of Patent: August 25, 1992Assignee: Ube Industries, Ltd.Inventors: Katsutoshi Fujii, Toshinobu Tanaka, Yasuhisa Fukuda
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Patent number: 5137564Abstract: Herbicidal benzylpyrimidine and benzyltriazine derivatives of the formula: ##STR1## and salts thereof, where: X is --CH.dbd. or --N.dbd.;R.sup.1 represents a substituted or unsubstituted phenyl group;R.sup.2 represents hydrogen, or a substituted or unsubstituted alkyl or aralkyl group;R.sup.3 represents cyano or a group --COOR or --CONRR', where R and R', which may be the same or different, each represent hydrogen, alkyl, alkenyl, alkynyl or aralkyl; andR.sup.4 and R.sup.5, which may be the same or different, each represent hydrogen, alkyl, alkoxy, amino or halogen,processes for their preparation, and compositions containing them.Type: GrantFiled: July 25, 1990Date of Patent: August 11, 1992Assignee: Schering Agrochemicals LimitedInventor: Graham P. Jones
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Patent number: 5138058Abstract: Pyrimidine derivatives of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the indicated meanings, the salts thereof, and a process for the preparation thereof are described. Because of their sorbitol-accumulating activity, they are suitable as a tool in a pharmacological screening model for aldose reductase inhibitors.Type: GrantFiled: February 20, 1990Date of Patent: August 11, 1992Assignee: Hoechst AktiengesellschaftInventors: Karl Geisen, Hans-Jochen Lang, Hildegard Nimmesgern, Klaus Weidmann
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Patent number: 5110986Abstract: This application relates to a process for preparing a N-t-alkyl-1,2-diacylhydrazine by reacting a 1,3,4-oxadiazole with a tertiary alkyl cation precursor in the presence of a strong acid catalyst. Preferably, the 1,3,4-oxadiazole is a 2,5-disubstituted-1,3,4-oxadiazole and more preferably a 2,5-diaryl-1,3,4-oxadiazole. The strong acid catalyst is preferably a sulfur containing acid and more preferably sulfuric acid.Type: GrantFiled: April 26, 1988Date of Patent: May 5, 1992Assignee: Rohm and Haas CompanyInventor: Martha J. Kelly
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Patent number: 5110818Abstract: The invention relates to novel 9H-purine derivatives, especially to the novel substituted 9-benzyl-9H-purines of the general formula ##STR1## in which Ph is a phenyl radical substituted by halogen, R.sub.1 is hydrogen or a free amino group or an amino group that is substituted aliphatically, cycloaliphatically, cycloaliphatically-aliphatically and/or by acyl, and R.sub.2 is halogen, lower alkoxy, lower alkyl, a free amino group, or an amino group that is substituted aliphatically, cycloaliphatically, cycloaliphatically-aliphatically and/or by acyl, with the proviso that R.sub.2 is other than halogen when Ph is 2-fluorophenyl or 2,5- or 2,6-difluorophenyl and R.sub.1 is a radical of the formula --N(R.sub.11)(R.sub.12) (Ia) in which either R.sub.11 is hydrogen, methyl or ethyl and R.sub.12 is hydrogen, methyl, hydroxymethyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopenthyl or cyclopropylmethyl, or R.sub.11 is hydrogen and R.sub.12 is methoxymethyl, and with the further proviso that R.sub.Type: GrantFiled: December 19, 1990Date of Patent: May 5, 1992Assignee: Ciba-Geigy CorporationInventor: Hans Allgeier
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Patent number: 5102893Abstract: Certain trans-6-[2-(N-heteroaryl-3,5-disubstituted) pyrazol-4-yl)ethyl]- or ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones and the corresponding ring-opened acids, esters and N-oxides derived therefrom which are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG CoA reductase) and are thus useful hydrolipidemic or hypocholesterolemic agents. Pharmaceutical compositions containing such compounds, and a method of inhibiting the biosynthesis of cholesterol employing such pharmaceutical compositions are also disclosed.Type: GrantFiled: June 19, 1990Date of Patent: April 7, 1992Assignee: Warner-Lambert CompanyInventors: Joseph A. Picard, Bruce D. Roth, Drago R. Sliskovic
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Patent number: 5098904Abstract: A series of pyprimidinyl compounds of formulae I, II and III; ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from hydrogen and hydroxy;R.sup.3 is selected from hydrogen, hydroxy, or oxo, with the proviso that R.sup.3 can only be oxo when R.sup.1 and R.sup.2 are hydrogen, and further that R.sup.1, R.sup.2, and R.sup.3 cannot all be hydrogen or hydroxy at the same time; andthe solid and dotted lines refer to either a double covalent bond or a single covalent bond with another hydrogen atom covalently bonded to the carbon terminus end.The compounds of this invention possess cognition and memory enhancing activity.Type: GrantFiled: June 27, 1990Date of Patent: March 24, 1992Assignee: Bristol-Myers Squibb CompanyInventors: Ronald J. Mattson, Robert Mayol, Michael E. Brady
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Patent number: 5084459Abstract: There is provided a pest control composition containing a compound represented by the formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and independently mean a hydrogen atom, a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted and X means an electron attracting group or a salt thereof.The compounds are of minimal toxicity to man, domestic animals and fish and selectively display remarkable control effect on pests.Type: GrantFiled: October 25, 1989Date of Patent: January 28, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideki Uneme, Isao Minamida, Tetsuo Okauchi, Noriko Higuchi
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Patent number: 5059598Abstract: Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 is a lower alkyl group;R.sup.2 and R.sup.3 are each hydrogen or lower alkyl or R.sup.2 and R.sup.3 taken together may form --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.dbd.CH--;.alpha. is a 5- or 6-membered heretoaromatic ring group containing 1 to 3 hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur, or a pyrazine-N-oxide ring, pyridazine-N-oxide ring or pyrimidine -N-oxide ring group, wherein each of these heteroaromatic ring groups may optionally have 1 to 3 substituents selected from the group consisting of a lower alkyl halogen, phenyl, lower alkoxycarbonyl, amino, lower alkoxy and hydroxy-lower alkyl, with the proviso that said 5- or 6-membered heteroaromatic ring group is not thiazolyl, isothiazolyl, pyridyl or 1,3,5-triazinyl group; or salts thereof. These compounds and salts thereof have anti-inflammatory activity and lipoxygenase-inhibitory activity.Type: GrantFiled: September 19, 1989Date of Patent: October 22, 1991Assignee: Otsuka Pharmaceutical Factory, Inc.Inventors: Kenichi Kanai, Kiyoto Goto, Kinji Hashimoto
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Patent number: 5051501Abstract: Novel reactive dyestuffs of the formula ##STR1## wherein Pc=radical of a Cu- or Ni-phthalocyanine,R.sub.1, R.sub.2 =H, C.sub.1 -C.sub.4 -alkyl optionally substituted with --OH, --COOH, --OSO.sub.3 H or --SO.sub.3 H, or together C.sub.2 -alkylene,B=C.sub.2 -C.sub.6 -alkylene or phenylene optionally substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, cyano, COOH, SO.sub.3 H, carboxanide, sulphonamide, C.sub.1 -C.sub.4 -alkylcarbonylamino or --NHCONH.sub.2,R.sub.3, R.sub.4 =H, C.sub.1 -C.sub.4 -alkyl optionally substituted with OH, --COOH, --OSO.sub.3 H or --SO.sub.3 H, or optionally sulphur- or carboxyl-substituted phenyl, or together C.sub.2 -alkylene,a=1.0 to 2.7,b=0.8 to 1.2, andc=0.5 to 1.5, where a+b+c=3 to 4.Type: GrantFiled: November 6, 1989Date of Patent: September 24, 1991Assignee: Bayer AktiengesellschaftInventors: Karl H. Schundehutte, Manfred Groll, Josef W. Stawitz
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Patent number: 5043443Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4- (4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.Type: GrantFiled: July 24, 1990Date of Patent: August 27, 1991Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
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Patent number: 5037982Abstract: A method of purifying 2-methyl-4-amino-5-aminomethylpyrimidine by heating the carbonate thereof. Preferably the heating is carried out in water or a specified solvent.Type: GrantFiled: September 18, 1989Date of Patent: August 6, 1991Assignee: Ube Industries, Ltd.Inventors: Keigo Nishihira, Masayoshi Yamashita, Hiroshi Yoshida
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Patent number: 5023259Abstract: The invention relates to novel nitroenamines of formula I ##STR1## wherein R.sub.1 is dialkylamino, alkoxy, alkenyloxy, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylamino, aralkoxy, 2-thiazolyl, or an unsubstituted or substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl and heteroarylalkyl, R.sub.2 is nitro, cyano, hydroxy, or an unsubstituted or substituted radical from the series alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, alkoxycarbonyl, amino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylamino, alkoxycarbonylamino, alkylcarbonyloxy and pyridinylmethyl, R.sub.3 is alkyl, cycloalkyl, or an unsubstituted or substituted pyridinylmethyl radical, and R.sub.4 is alkyl or cycloalkyl, including the salts of compounds of formula I, to a process for the preparation of these compounds, and to compositions containing these active ingredients and their use in pest control, especially for the control of insects.Type: GrantFiled: December 14, 1989Date of Patent: June 11, 1991Assignee: Ciba-Geigy CorporationInventor: Laurenz Gsell
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Patent number: 5003069Abstract: In a Chichibabin amination of a nitrogen-containing heterocyclic base by sodamide in an organic solvent, the improvement comprising conducting the reaction under pressure of at least about 50 psi in the gas phase above the reaction mixture and adding ammonia to the mixture sufficient to produce a partial pressure of ammonia of at least about 5 psi in the gas phase. Preferred temperature and pressure ranges are disclosed, as are catalysts and other preferred steps for practicing the reaction. Significant results are obtained including improved and changed yields from those classically expected in Chichibabin aminations, including new compositions of matter in at least three cases.Type: GrantFiled: July 26, 1989Date of Patent: March 26, 1991Assignee: Reilly Industries, Inc.Inventors: Charles K. McGill, James J. Sutor
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Patent number: 4990506Abstract: A compound which is a 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivative of formula (I) ##STR1## in which R.sub.1 denotes hydrogen; linear or branched C.sub.1 -C.sub.4 alkyl; or benzyl;R.sub.2 denotes linear or branched C.sub.1 -C.sub.6 alkyl; cyclohexyl; trichloromethyl; 1-propenyl; allyl; phenyl; 4-chlorophenyl; or benzyl:or R.sub.1 and R.sub.2 together denote a C.sub.3 -C.sub.5 aliphatic chain:X denotes halogen; C.sub.1 -C.sub.3 alkyl; methylthio; trifluoromethyl; optionally esterified carboxy of formula --COOR in which R denotes hydrogen or C.sub.1 -C.sub.6 alkyl; cyano; optionally mono- or dialkylated aminocarbonyl of formula --CONR.sub.3 R.sub.4 in which R.sub.3 and R.sub.4 independently denote hydrogen or C.sub.1 -C.sub.4 alkyl or together denote a chain of formula --(CH.sub.2).sub.2 --Z--(CH.sub.2).sub.2 -- in which Z denotes a direct bond, oxygen, sulphur, or a divalent group of formula --CH.sub.2 --, --NH-- or --N(C.sub.1 -C.sub.4 alkyl)--; alkylamino of formula NHR.sub.5 in which R.sub.Type: GrantFiled: October 24, 1989Date of Patent: February 5, 1991Assignee: SynthelaboInventors: Pascal George, Claudie Giron, Jacques Froissant
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Patent number: 4988704Abstract: Disclosed are pyrimidine derivatives represented by general formula ##STR1## wherein Z.sup.1 represents an alkynyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, or an alkynyloxy group which may be substituted with a halogen atom, and Z.sup.2 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a group of the formula ##STR2## where Z.sup.3 represents a hydrogen atom or a methyl group; or its salt, and processes for preparing same. Also, agricultural or horticultural compositions containing the pyrimidine derivatives as active ingredient are disclosed, which show high controlling activities for cucumber gray mold (Botrytis cinerea), cucumber downey mildew (Pseudoperonospora cubensis), Alternaria sooty spot of Chinese mustard (Alternaria brassicicola), rice blast (Pyricularia oryzae), etc.Type: GrantFiled: March 20, 1989Date of Patent: January 29, 1991Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.Inventors: Shigekazu Ito, Katsumi Masuda, Shoji Kusano, Toshihiro Nagata, Yoshiyuki Kojima, Nobumitsu Sawai, Shin-ichiro Maeno
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Patent number: 4985426Abstract: There is disclosed a compound represented by the formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a lower alkyl group; R.sub.2 and R.sub.3 each independently represent a halogen atom or a lower alkyl group; R.sub.Type: GrantFiled: November 13, 1989Date of Patent: January 15, 1991Assignees: UBE Industries, Ltd., The Institute of Physical and Chemical ResearchInventors: Hirosuke Yoshioka, Tokio Obata, Katsutoshi Fujii, Kiyoshi Tsutsumiuchi, Haruo Yoshiya
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Patent number: 4983608Abstract: This invention relates to N-heteroaryl-4-pyrimidinamines of the formula ##STR1## where R.sub.1 is hydrogen, loweralkyl, aryl, or arylloweralkyl; R.sub.2 and R.sub.3 are independently hydrogen or loweralkyl, or R.sub.2 and R.sub.3 taken together are aryl; R.sub.4 and R.sub.5 are independently hydrogen or lowealkyl, or R.sub.4 and R.sub.5 taken together are aryl; X is hydrogen, halogen, cyano, nitro, amino, loweralkyl, loweralkoxy, trifluoromethyl or ##STR2## where Y is hydrogen, halogen or loweralkyl; m is an integer of 1 to 3; and the pharmaceutically acceptable acid addition salts thereof and where applicable the geometrical and optical isomers and racemic mixtures thereof. The compounds of this invention display utility as memory enhancing agents and as analgesic agents.Type: GrantFiled: September 5, 1989Date of Patent: January 8, 1991Assignee: Hoechst-Roussell Pharmaceuticals, Inc.Inventors: Richard C. Effland, Joseph T. Klein, Larry Davis, Gordon E. Olsen
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Patent number: 4968781Abstract: A reactive dye of the formula ##STR1## in which Fa is the radical of an organic dye of the monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide series, T is a negative substituent, one X is a detachable substituent and the other X is a group of the formula ##STR2## A is arylene, V is hydrogen, a substituted or unsubstituted C.sub.1 -C.sub.4 alkyl radical or a radical of the formula --(CH.sub.2).sub.q --SO.sub.2 --Z, Z is a --CH.dbd.CH.sub.2 or CH.sub.2 --Y radical and Y is an inorganic or organic radical which is detachable under alkaline conditions, q, m and n are independently of one another an integral number from 2 to 6, R and R' are independently of one another hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 alkyl, and r is 1 or 2.Type: GrantFiled: March 28, 1988Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventors: Karl Seitz, Karl Hoegerle
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Patent number: 4962191Abstract: Dyes suitable for dyeing a wide range of textile and non-textile materials, in particular for dyeing leather and pelts, having, in the form of the free acid, the formula ##STR1## wherein D.sub.1 and D.sub.2 are each independently of the other the radical of a diazo component of the benzene or naphthalene series which carries a hydroxy or carboxy in ortho-position to the azo group and which may or may not be further substituted,K is the radical of a coupling component of the benzene or naphthalene series or of the heterocyclic series which carries the group X in ortho-position to the azo group and which may or may not be further substituted,Me is chromium or cobalt,Q is an unsubstituted or substituted phenyl or naphthyl radical or an unsubstituted or substituted aromatic-heterocyclic radical,R.sub.1 is unsubstituted or substituted C.sub.1 -C.sub.6 alkyl or unsubstituted or substituted phenyl,R.sub.2 is hydrogen or independently has the meaning of R.sub.1, X is --O-- or --NR.sub.3,R.sub.3 is hydrogen or C.sub.Type: GrantFiled: August 28, 1989Date of Patent: October 9, 1990Assignee: Ciba-Geigy CorporationInventors: Alois Puntener, Kurt Burdeska
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Patent number: 4946956Abstract: Disclosed are novel 2,4,6 substituted pyrimidines where the substituents may be the same or different groups. At least one substituent must be N-alkyl parphenylenediamino, and the other substituents may be various radicals containing sulfur, oxygen or nitrogen or hydrogen or alkyl groups. The compounds are useful as antioxidants and antiozonants for unsaturated compounds and polymers.Type: GrantFiled: September 21, 1988Date of Patent: August 7, 1990Assignee: Uniroyal Chemical Company, Inc.Inventors: Edward L. Wheeler, Franklin H. Barrows, Robert J. Franko
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Patent number: 4931455Abstract: There are described an alkylaminopyrimidine derivative represented by the formula: ##STR1## wherein R.sub.1 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cycloalkyl group having 3 to 6 carbon atoms, a halogenated lower alkyl group or a substituted or unsubstituted phenyl group; R.sub.2 represents a halogen atom; R.sub.3 represents a hydrogen atom, a lower alkyl group or a cycloalkyl group having 3 to 6 carbon atoms; and R.sub.4 represents a straight or branched alkyl group having 1 to 20 carbon atoms which may have substituents,or an acid addition salt thereof, a process for preparing the same and an insecticide, an acaricide or a fungicide containing the compound as an active ingredient.Type: GrantFiled: December 22, 1988Date of Patent: June 5, 1990Assignees: Ube Industries, Ltd., Rikagaku KenkyushoInventors: Hirosuke Yoshioka, Tokio Obata, Katsutoshi Fujii, Haruo Yoshiya, Kiyoshi Tsutsumiuchi, Shoji Shikita
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Patent number: 4918191Abstract: In an improved process for the preparation of 2-n-propyl-4-amino-5-methoxymethyl-pyrimidine of the formula I ##STR1## by reacting butyramidine II ##STR2## with .alpha.-methoxymethyl-.beta.-methoxyacrylonitrile III ##STR3## the butyramidine II is reacted with a 0.4-5 molar excess of .alpha.-methoxymethyl-.beta.-methoxyacrylonitrile III at from -10.degree. to +20.degree. C.Type: GrantFiled: August 15, 1989Date of Patent: April 17, 1990Assignee: BASF AktinegesellschaftInventors: Joachim Paust, Hansgeorg Ernst