Having -c(=x)-, Wherein X Is Chalcogen, Bonded Directly To The Six-membered Hetero Ring Patents (Class 546/310)
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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: 5330981Abstract: This application describes 3-arylalkyl esters of 4,5-dihydro-9,10-dioxo-2-anthracenecarboxylic acid and a process for making them. Also described is a method of using the compounds in the treatment of arthritis.Type: GrantFiled: December 30, 1992Date of Patent: July 19, 1994Assignee: Istituto Gentili S.p.A.Inventors: Sergio Rosini, Maurizio Mian
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Patent number: 5317021Abstract: Amino acid compounds of the formula: ##STR1## wherein the various symbols are as hereinafter described, which have inhibiting effect on enkephalinase.Type: GrantFiled: November 4, 1992Date of Patent: May 31, 1994Assignee: ONO Pharmaceutical Co., Ltd.Inventors: Masanori Kawamura, Yoshinobu Arai, Hideki Aishita
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Patent number: 5314887Abstract: There are provided novel 1,4-dihydropyridine compounds possessing both calcium agonist and alpha.sub.1 -antagonist activity useful for treating congestive heart failure, pharmaceutical compositions containing them and methods of using these compounds to treat congestive heart failure in a mammal.Type: GrantFiled: October 30, 1992Date of Patent: May 24, 1994Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Paul E. Aldrich, Richard A. Earl, Philip Ma
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Patent number: 5310919Abstract: Fungicidal pyridyl-substituted acrylic esters of the formula ##STR1## in which R.sup.1 represents alkyl or represents optionally substituted aralkyl,R.sup.2 represents dialkylanino or represents a radical --Z--R.sup.3,X represents oxygen or sulphur or represents a radical ##STR2## and Py represents optionally substituted pyridyl, whereR.sup.3 represents alkyl or represents optionally substituted aralkyl,R.sup.4 represents hydrogen, alkyl or alkanoyl or represents in each case optionally substituted aralkyl or aryl andZ represents oxygen or sulphur, their geometric isomers and isomer mixtures.Type: GrantFiled: January 31, 1992Date of Patent: May 10, 1994Assignee: Bayer AktiengesellschaftInventors: Alexander Klausener, Gerd Kleefeld, Dieter Berg, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5248781Abstract: Substituted anilino-nicotinic acid derivatives are readily prepared from the condensation of two intermediates, 2-alkyl-3-perfluoroalkyl-anilines and alkyl 2-chloronicotinates. The 2-alkyl-3-perfluoroalkyl-aniline intermediate can be prepared via a novel three step synthesis. 3-Perfluoroalkyl-anilines are reacted with an amine directing protecting group reagent to protect the amine. The protected amine is then alkylated, and finally, the directing group is removed to form the 2-alkyl-3-perfluoroalkyl-aniline intermediate. The 2-alkyl-3-perfluoroalkyl-aniline intermediate is condensed with the alkyl 2-chloronicotinate to form the anilino-nicotinic acid derivative.Type: GrantFiled: September 21, 1992Date of Patent: September 28, 1993Assignee: The Trustees of Princeton UniversityInventor: Alexander McKillop
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Patent number: 5238908Abstract: This invention relates to glutaramic acids and derivatives exhibiting herbicidal activity having the structure ##STR1## wherein A is a carboxylic acid or a derivative thereof, D is CH or N, and R, R.sup.1, R.sup.2, T, X, Y, and Z are as defined within, compositions containing these compounds and methods of controlling weeds with these compounds.Type: GrantFiled: August 9, 1990Date of Patent: August 24, 1993Assignee: Rohm and Haas CompanyInventors: Barry C. Lange, John W. Ashmore, Jane Wissinger-Cornille
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Patent number: 5236937Abstract: The invention concerns pharmaceutically useful compounds of the formula I, in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, Rz, X and Z have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them. The novel compounds are of value in treating conditions such as hypertension and congestive heart failure. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.Type: GrantFiled: February 11, 1992Date of Patent: August 17, 1993Assignee: Imperial Chemical Industries PLCInventors: Robert H. Bradbury, Martin P. Edwards, Arnold H. Ratcliffe
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Patent number: 5204357Abstract: The invention relates to compounds of the formula I ##STR1## in which A represents a substituted thio-, sulfinyl- or sulfonyl-alkanoyl radical or a four- to eleven-membered heterocycle, B is an amino acid residue, R.sup.1 denotes hydrogen (substituted) alkyl, (substituted)cycloalkyl or aryl, R.sup.2 represents hydrogen, (substituted)alkyl or aryl, R.sup.3 denotes a radical of the formula --(CH.sub.2).sub.q --(X).sub.r --(CH.sub.2).sub.s --R.sup.6 with X denoting CF.sub.2, CO or CHR.sup.8, R.sup.6 denoting a (substituted)heteroaromatic, R.sup.8 denoting alkyl, alkoxy, alkylthio, alkylamino, hydroxyl, azide or halogen, q and s denoting 1 to 4, and r denoting 0 or 1, and R.sup.9 is hydrogen, (substituted)alkyl, alkanoyl, cycloalkanoyl, (substituted) aroyl or (substituted)aryl, and to the salts thereof. In addition, processes for the preparation of these compounds, and the use thereof as renin inhibitors are described.Type: GrantFiled: February 14, 1989Date of Patent: April 20, 1993Assignee: Hoechst AktiengesellschaftInventors: Rainer Henning, Hansjorg Urbach, Dieter Ruppert, Bernward Scholkens
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Patent number: 5196541Abstract: There is described a new process for the preparation of substituted 3-aminoacrylic esters of the general formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and n have the meaning given in the description.The 3-aminoacrylic esters of the formula (I) are obtained by reacting acetic esters of the formula (II)R.sup.1 --(X).sub.n --CH.sub.2 --COOR.sup.Type: GrantFiled: August 2, 1991Date of Patent: March 23, 1993Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Alexander Klausener, Peter C. Knuppel, Fritz Maurer
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Patent number: 5182401Abstract: A process for the preparation of a 3-amino-2-(het)aroyl-acrylic acid derivative fo the formula ##STR1## in which Y represents a nitrile, or an ester group, --COOR.sub.1, or an acetyl group, whereR.sup.1 denotes C.sub.1 -C.sub.4 -alkyl, andR denotes optionally substituted alkyl, cyclopropyl, alkoxy, phenyl or amino,A represents nitrogen or C--R.sub.2, whereR.sub.2 denotes hydrogen, methyl, halogen, nitro, methoxy or cyano,X.sub.1 and X.sub.2 are identical or different and denote halogen, andX.sub.3 denotes hydrogen, halogen or nitro andX.sub.4 denotes halogen, nitro, methoxy or methylthio, which comprises reacting a 3-dialkylamino-2-(het)aroyl-acrylic acid derivative of the formula ##STR2## in which R.sub.3 and R.sub.4 are the same or different and represent an alkyl group having 1 to 4 carbon atoms, or, together with the nitrogen atom to which they are bonded, form a ring,with a primary amine of the formula R--NH.sub.2 in the presence of at least one equivalent of an acid HX in a solvent or in excess acid.Type: GrantFiled: May 2, 1991Date of Patent: January 26, 1993Assignee: Bayer AktiengesellschaftInventor: Klaus Grohe
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Patent number: 5175166Abstract: 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 impared memory, which are associated with decreased acetylcholine synthesis and cholinergic cell degeneration.Type: GrantFiled: August 27, 1991Date of Patent: December 29, 1992Assignee: The University of ToledoInventors: Philip G. Dunbar, Graham J. Durant, Wayne P. Hoss, William S. Messer, Jr
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Patent number: 5166148Abstract: There are provided novel 1,4-dihydropyridine compounds possessing both calcium agonist and alpha.sub.1 -antagonist activity useful for treating congestive heart failure, pharmaceutical compositions containing them and methods of using these compounds to treat congestive heart failure in a mammal.Type: GrantFiled: July 9, 1990Date of Patent: November 24, 1992Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Paul E. Aldrich, Richard A. Earl, Philip Ma
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Patent number: 5166147Abstract: There are provided novel 1,4-dihydropyridine compounds, compositions containing them and methods of using them to treat congestive heart failure.Type: GrantFiled: July 9, 1990Date of Patent: November 24, 1992Assignee: The Du Pont Merck Pharmaceutical CompanyInventor: Richard A. Earl
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Patent number: 5164507Abstract: A substance represented by formula: ##STR1## and a salt thereof, which has antifungal activity and a process for producing the same utilizing a microorganism capable of producing the substance and belonging to the genus Streptomyces.Type: GrantFiled: May 21, 1991Date of Patent: November 17, 1992Assignee: Meiji Seika Kaisha Ltd.Inventors: Toru Sasaki, Akira Shimizu, Junko Yoshida, Hiroomi Watabe, Masao Koyama
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Patent number: 5138066Abstract: Antibacterial compounds of the formula ##STR1## wherein R is a mononuclear carbocyclic aromatic group, a 5-membered aromatic heterocyclic group which contains as the hetero (non-carbon) ring member(s) an oxygen or sulphur atom or an imino or lower alkylimino group and, optionally, one or two nitrogen atoms, or a 6-membered aromatic heterocyclic group which contains one to three nitrogen atoms as the hetero ring member(s); R.sup.1 is hydrogen or a 3-substituent which is usable in cephalosporin chemistry; A is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl; Q is lower alkylene or C.sub.3-7 -cycloalkylene which is optionally substituted with carboxy, carbamoyl, lower alkylcarbamoyl or di(lower alkyl)carbamoyl, or the group --NR.sup.2 -- or --NR.sup.2 NR.sup.3 --; R.sup.2 and R.sup.3 are independently hydrogen or lower alkyl; p and m are the zero or 1, n is zero, 1 or 2; R.sup.Type: GrantFiled: July 11, 1991Date of Patent: August 11, 1992Assignee: Hoffmann-La Roche, Inc.Inventor: Erwin Gotschi
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Patent number: 5126338Abstract: Compounds of having the general formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is hydrogen, halogen, C.sub.1-4 alkoxy, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, COR or cyano; R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen, halogen or methyl, provided that R.sup.2, R.sup.3 and R.sup.4 are not all hydrogen and provided that when one of them is methyl then at least one of the other two is not hydrogen; ##STR2## wherein R.sup.5 is hydrogen, C.sub.1-4 alkyl (optionally substituted by hydrogen or cyano), optionally substituted benzyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, cyano, COR, C.sub.1-4 thioalkoxy, C.sub.1-4 thiohaloalkoxy or SNR.sup.7 R.sup.8 ; R.sup.7 and R.sup.8 are independently C.sub.1-4 alkyl or CO.sub.2 R; Y is oxygen or sulphur; R.sup.6 is C.sub.1-4 alkoxy, C.sub.1-4 thioalkoxy or --NR.sup.9 R.sup.10 ; and R.sup.9 and R.sup.10 are independently hydrogen, C.sub.1-4 alkyl, aryl or aralkyl or R.sup.9 and R.sup.Type: GrantFiled: January 3, 1991Date of Patent: June 30, 1992Assignee: Imperial Chemical Industries PLCInventors: Paul A. Worthington, Ian R. Matthews, David Bartholomew, Patrick J. Crowley, Don R. Baker, Karl J. Fisher
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Patent number: 5125956Abstract: Disclosed herein are herbicidal pyridine compounds substituted at the 2- or 6-position with an OR.sub.2 moiety where R.sub.2 is hydrogen, lower alkyl, halomethyl, lower cyanoalkyl, alkenyl or alkynyl, as well as herbicidal compositions and herbicidal use of these compounds.Type: GrantFiled: February 25, 1991Date of Patent: June 30, 1992Assignee: Monsanto CompanyInventors: Donald E. Korte, Len F. Lee
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Patent number: 5106986Type: GrantFiled: February 22, 1991Date of Patent: April 21, 1992Assignee: Bayer AktiengesellschaftInventor: Bernd Gallenkamp
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Patent number: 5100460Abstract: Herbicides of formula: ##STR1## in which: n=0,1, 2f=0,1A is chosen from the groups ##STR2## in which: Ar is chosen from the groups ##STR3## B is chosen from optionally substituted C.sub.1 -C.sub.10 alkyl and C.sub.3 -C.sub.Type: GrantFiled: July 13, 1989Date of Patent: March 31, 1992Assignee: Rhone-Poulenc AgrochimieInventors: Philippe Desbordes, Michel Euvrard
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Patent number: 5086181Abstract: A pyridine derivative of the formula ##STR1## in which A stands for ##STR2## is useful in the preparation of 4-bromo-6-chloro-5-amino-2-pyridyl-ethanolamines, their physiologically tolerated salts and their N-oxides. The 4-bromo-6-chloro-5-amino-2-pyridyl-ethanolamines are useful as yield promoters in animals and as feedstuff additives to achieve higher increases in weight and improved feed utilization.Type: GrantFiled: September 13, 1990Date of Patent: February 4, 1992Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Gernot Klotz, Heinrich A. Greife
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Patent number: 5079361Abstract: Cross-linking reagents which are highly specific for sulphydryl groups and react with thiols at an excellent rate. The essential feature of the reagents is at least one vinyl group conjugated with an armoatic nitrogen heterocycle. Particular examples include vinyl pyridines, vinyl pyrimidines and vinyl triazines.Type: GrantFiled: September 9, 1988Date of Patent: January 7, 1992Assignee: Celltech LimitedInventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
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Patent number: 5077309Abstract: Novel compounds have the formula (I) ##STR1## where ##STR2## represents one of the divalent cyclic groups ##STR3## the letters a and b indicating in each case the points of attachment of the substituents R.sup.1 and CV(R.sup.2)-NV'R, respectively; R.sup.1 is a group --(CH.sub.2).sub.b --(A).sub.a --(CH.sub.2).sub.c --B--CH.sub.2 --CO.sub.2 R' in which A and B are each separately oxygen or sulphur, a is 0, b is 0 and c is an integer from 3 to 10, or a is 1, b is 0 or an integer from 1 to 7 and c is an integer from 2 to 9 with the sum of b and c being from 2 to 9, and CO.sub.2 R' is a carboxy group or an amide, ester or salt derivative thereof; V and V' either each separately is hydrogen or together are the second bond of a carbon-nitrogen double bond; R.sup.2 is hydrogen, an aliphatic hydrocarbon group or an aliphatic hydrocarbon group substituted by an aromatic group directly or through an oxygen or sulphur atom; and R is a group --OR.sup.3, --OR.sup.4, --D--R.sup.3, --N.dbd. R.sup.5 or --NW.G.Type: GrantFiled: March 28, 1990Date of Patent: December 31, 1991Assignee: National Research Development CorporationInventors: Robert L. Jones, Norman H. Wilson
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Patent number: 5075324Abstract: 1,4-dihydropyridines of formula I ##STR1## wherein X is --CO.sub.2 R.sub.1, cyano, nitro, --COCH.sub.3 ; each of R and R.sub.1, which are the same or different, is a primary, secondary or tertiary, saturated or unsaturated, linear or branched C.sub.1 -C.sub.6 alkyl group optionally substituted by one or more hydroxy, C.sub.1 -C.sub.7 -monoalkylamino, di-C.sub.1 -C.sub.7 -alkylamino, benzylamino, C.sub.1 -C.sub.6 -alkoxy, phenoxy groups which are optionally substituted; R.sub.2 is hydrogen; R.sub.3 is hydrogen or hydroxy, --OCOR.sub.5, OSO.sub.2 R.sub.6, azide, amino, --NHPO(OR.sub.7).sub.2, --NHCOR.sub.5, C.sub.1 -C.sub.4 -alkoxy or fluorine, chlorine, bromine or iodine, SH, SCOR.sub.6 or C.sub.1 -C.sub.6 -alkylthio, phenylthio or benzylthio; R.sub.4 is an optionally substituted aromatic or an optionally substituted 5- or 6-membered heteroaromatic group; Y is one or more substituents, which may be the same or different, selected from C.sub.1 -C.sub.4 -alkoxy, halogen, nitro, cyano, C.sub.1 -C.sub.Type: GrantFiled: June 22, 1989Date of Patent: December 24, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Marco Frigerio, Andrea Zaliani, Carmelo A. Gandolfi, Mauro Germini, Odoardo Tofanetti, Sergio Tognella
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Patent number: 5049571Abstract: There are disclosed novel 1-nitro-2,2-diaminoethylene derivatives of formula I ##STR1## wherein X is chlorine, fluorine, unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkyl; unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkoxy, unsubstituted or halogen-substituted C.sub.1 -C.sub.5 alkylthio, unsubstituted or halogen-substituted alkylsulfinyl, unsubstituted or halogen-substituted alkylsulfonyl; or also nitro, cyano, thiocyanato, C.sub.3 -C.sub.5 haloalkenyl, C.sub.3 -C.sub.5 haloalkynyl, hydroxy, C.sub.1 -C.sub.5 alkoxycarbonyl, amino, C.sub.1 -C.sub.4 dialkylamino, C.sub.1 -C.sub.5 alkylcarbonyl, C.sub.1 -C.sub.5 alkylcarbamoyl or C.sub.1 -C.sub.5 alkylcarbonyloxy,n is an integer from 0 to 4,R.sub.1 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.7 cycloalkyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl,R.sub.3 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.7 cycloalkyl, benzyl or pyridinylmethyl, or R.sub.2 and R.sub.Type: GrantFiled: January 24, 1990Date of Patent: September 17, 1991Assignee: Ciba-Geigy CorporationInventor: Laurenz Gsell
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Patent number: 5047414Abstract: Compounds of formula I, and pharmaceutical compositions containing compounds of formula I ##STR1## wherein: R.sub.1 is:(a) COCH.sub.3, COC.sub.6 H.sub.5, CN or NO.sub.2 ;(b) COORa wherein Ra is hydrogen, or optionally substituted C.sub.1 -C.sub.6 straight or branched alkyl;R.sub.2 is optionally substituted phenyl; pentafluorophenyl; .alpha.- or .beta.-naphthyl; a five- or six-membered heterocyclic ring; .alpha.-benzo[2,3-b]-1,4-dioxan-.alpha.-yl; or .alpha.-benzofuroxanyl;R.sub.3 is COORa;P is hydrogen, --(CH.sub.2).sub.p --W, or C.sub.1 -C.sub.8 linear or branched alkyl;N--P.sub.1 is the residue of a primary or secondary amino group wherein P.sub.1 is hydrogen, C.sub.1 -C.sub.6 lower linear or branched alkyl group, or --(CH.sub.2).sub.p --W; and P, taken together with P.sub.1 and the nitrogen atom to which P.sub.1 is linked, may form a pyrrolidine or a piperidine ring; W is hydroxymethyl, formyloxymethyl, CO.sub.2 R wherein R is hydrogen or C.sub.1 -C.sub.Type: GrantFiled: December 21, 1990Date of Patent: September 10, 1991Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Sergio Tognella
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Patent number: 5037469Abstract: Disclosed herein are 2- or 6-fluoromethyl-3-pyridinecarboxylate derivatives with 3- or 5-dialkylamino substitution which are useful as herbicides.Type: GrantFiled: December 27, 1989Date of Patent: August 6, 1991Assignee: Monsanto CompanyInventors: Shridhar G. Hegde, Len F. Lee
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Patent number: 5008276Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.Type: GrantFiled: October 17, 1988Date of Patent: April 16, 1991Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
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Patent number: 5004748Abstract: 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: March 4, 1988Date of Patent: April 2, 1991Assignee: Hoechst AktiengesellschaftInventors: Ekkehard Baader, Martin Bickel, Dietrich Brocks, Volkmar Gunzler, Stephan Henke, Hartmut Hanauske-Abel
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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: 5001137Abstract: A novel pyridine compound of the formula ##STR1## wherein each symbol is as defined in the specification, or a salt thereof which exhibit inhibitory activity or prolylendopeptidase and a pharmaceutical use thereof are disclosed.Type: GrantFiled: September 14, 1989Date of Patent: March 19, 1991Assignee: Yoshitomi Pharmaceutical Industries, Ltd.Inventors: Takanori Oe, Yuji Ono, Kazuyuki Kawasaki, Tohru Nakajima
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Patent number: 4996218Abstract: Compounds of the general formula (I) ##STR1## and physiologically acceptable salts and solvates thereof, which have .beta..sub.2 -adrenoreceptor stimulant activity. They may be used in the treatment of diseases associated with reversible airways obstruction, such as asthma and chronic bronchitis.In preferred embodiments, Q represents a chlorine atom or a trifluoromethyl group, X represents a C.sub.3-4 alkylene chain, Y a C.sub.1-5 alkylene chain, R, R.sup.1 and R.sup.2 are each preferably a hydrogen atom or a methyl group and Het represents a pyrimidinyl pyrazinyl, triazinyl, thiazolyl, quinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl or pyridyl group.Type: GrantFiled: August 10, 1988Date of Patent: February 26, 1991Assignee: Glaxo Group LimitedInventor: Lawrence H. C. Lunts
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Patent number: 4994473Abstract: Insecticides of the general formula ##STR1## wherein R.sub.1 is an optionally substituted 5- to 10-member heterocyclic moiety; R.sub.2 is an optionally substituted alkyl, cycloalkyl or alkenyl moiety; X is oxygen, sulfur or --NH--; and R.sub.3 is: (a) an optionally substituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl, 3-(pyridyloxy)phenalkyl, 3-phenylaminophenoalkyl, 3-benzylphenalkyl or 3-benzyloxyphenalkyl moiety; (b) a benzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl or tetrafluorobenzyl moiety; (d) 4-phenoxy-2-butyn-2-yl; or (e) 2-methyl-3-phenylbenzyl.Type: GrantFiled: October 31, 1988Date of Patent: February 19, 1991Assignee: ICI Americas Inc.Inventor: Michael D. Broadhurst
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Patent number: 4992451Abstract: 1,4-Dihydro-6-methyl-4-(substituted phenyl)pyridine-3,5-dicarboxylic acid esters have an amino group at the 2-position and at least one nitrooxy group in at least one of the ester groups. These compounds have a variety of valuable activities, including antihypertensive and Ca.sup.++ -blocking activities, leading to their use for the treatment of circulatory and coronary disorders. They may be prepared by condensation of appropriate substituted acetic acid esters.Type: GrantFiled: March 14, 1989Date of Patent: February 12, 1991Assignee: Sankyo Company, LimitedInventors: Hiroyuki Koike, Hiroshi Nishino, Masafumi Yoshimoto
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Patent number: 4973429Abstract: A material in the form of a film is described which contains, in an orientated arrangement which does not display point symmetry, compounds of formula I ##STR1## wherein X is .dbd.CH-- or .dbd.N--, R.sup.1 is C.sub.12 -C.sub.30 -alkyl, R.sup.2 is hydrogen or C.sub.1 -C.sub.30 -alkyl, R.sup.3 is --NO.sub.2, --CN, --CF.sub.3, --COCF.sub.3, --SO.sub.2 CH.sub.3 or --SO.sub.2 CF.sub.3, R.sup.4 is hydrogen or is defined in the same way as R.sup.3, R.sup.5 is hydrogen or --NR.sup.6 R.sup.7 and R.sup.6 and R.sup.7 independently of one another are hydrogen or C.sub.1 -C.sub.30 -alkyl, it also being possible for any of the alkyl radicals to be partially fluorinated or perfluorinated.The compounds of formula I can be arranged in Langmuir-Blodgett layer systems. Such systems can be used for example for the manufacture of opto-electronic units.Type: GrantFiled: February 15, 1989Date of Patent: November 27, 1990Assignee: Ciba-Geigy CorporationInventors: Gero Decher, Bernd Tieke, Christian Bosshard, Peter Gunter
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Patent number: 4968796Abstract: Disclosed is a process for the preparation of a sulphonylisothiourea of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, and Z are as defined herein, which comprises reacting a sulphonic acid amide of the formulaR.sup.1 --SO.sub.2 --NH.sub.2, (II)or a metal salt thereof, with an N-heteroaryl-iminodithiocarbonic acid S,S-diester of the formula ##STR2## at a temperature between about 20.degree. C. and 200.degree. C. Intermediates and a process for their preparation are also disclosed.Type: GrantFiled: August 17, 1989Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventor: Hans-Jochem Riebel
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Patent number: 4962113Abstract: Novel pyridinium derivatives represented by the formula (I): ##STR1## wherein ##STR2## is an optionally substituted pyridinium ring; R.sup.1 is a lower alkyl group or aralkyl group;R.sup.7 and R.sup.10 are independently hydrogen, a lower alkyl group, aryl group or aralkyl group;l is 0 or 1;R.sup.5 is a phenylene group or an alkylene group which may be substituted;R.sup.11 is an alkyl group or aryl group;X is a group of the formula: --CH.sub.2 OCH.sub.2 -- or a group of the formula: ##STR3## wherein R.sup.6 is hydrogen, a lower alkyl or a lower alkoxy, and m is an integer of 0 to 3;U is a group of the formula: ##STR4## wherein R.sup.Type: GrantFiled: July 26, 1988Date of Patent: October 9, 1990Assignee: Takeda Chemical Industries, LtdInventors: Susumu Tsushima, Muneo Takatani, Kohei Nishikawa
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Patent number: 4959474Abstract: A novel class of 2,4-diamino-6-(2,5-dialkoxybenzyl)-5-methyl[2,3-d]-pyrimidines is described. These compounds are antibacterial agents, active against certain Streptococcus species. They are also active antiproliferative agents.Type: GrantFiled: October 15, 1985Date of Patent: September 25, 1990Assignee: Burroughs Wellcome Co.Inventor: Eugene M. Grivsky
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Patent number: 4920225Abstract: Optically active compounds of formula 1 ##STR1## wherein R.sub.1 is H or lower alkyl;R.sub.2 and R.sub.6 are each independently lower alkyl, aryl, or arylalkyl;R.sub.3 is CN, NO.sub.2, CO.sub.2 R.sub.5, CONHR.sub.5, SO.sub.2 R.sub.5, or P(O)(OR.sub.5).sub.2, where R.sub.5 is lower alkyl, lower alkoxyalkyl, aryl, or arylalkyl;R.sub.4 is aryl, heterocyclyl, or fused-ring heterocyclyl, optionally substituted with one, two, or three halo, NO.sub.2, CN, lower alkyl, lower alkoxy, lower alkylamino, CF.sub.3, OCH.sub.2 F, or OCF.sub.3 ;are prepared by fractional crystallization from hot organic solvent and water in the presence of a suitable optically active amine base.Type: GrantFiled: December 22, 1986Date of Patent: April 24, 1990Assignee: Laboratoires Syntex S.A.Inventor: Gilles Genain
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Patent number: 4920136Abstract: For promoting livestock production, the novel substituted pyridylethanolamines of the formula ##STR1## in which R.sup.1 represents CN, --COOR.sup.8 or --CONR.sup.9 R.sup.10,R.sup.2 represents optionally substituted alkyl,R.sup.3 represents hydrogen, alkyl or alkenyl,R.sup.4 represents hydrogen or optionally substituted alkyl or alkenyl, orR.sup.3 and R.sup.4 represent, together with the nitrogen atom to which they are bonded, an optionally substituted heterocyclic radical,R.sup.5 represents OH, acyloxy or alkoxy,R.sup.6 represents hydrogen or alkyl,R.sup.7 represents hydrogen, alkyl, cycloalkyl, substituted alkyl, optionally substituted aralkyl, aryl or heterocyclyl,R.sup.6 and R.sup.7 can, together with the nitrogen atom to which they are bonded, represent an optionally substituted heterocyclic radical,R.sup.8 represents alkyl, andR.sup.9 and R.sup.Type: GrantFiled: July 13, 1988Date of Patent: April 24, 1990Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer
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Patent number: 4900749Abstract: Novel isoprenoidamine compounds (I) which show antiulcer activity are provided.Type: GrantFiled: March 10, 1986Date of Patent: February 13, 1990Assignee: Shionogi & Co., Ltd.Inventors: Saichi Matsumoto, Masami Doteuchi, Takuji Mizui, Kentaro Hirai
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Patent number: 4895950Abstract: Novel 5-halogeno-6-amino-nicotinic acid halides of the formula ##STR1## in which R represents hydrogen or alkyl,R.sup.1 represents hydrogen, alkyl or acyl orR and R.sup.1, together with the nitrogen atom to which they are bonded, represent an optionally substituted heterocyclic radical,R.sup.2 represents halogen andHal represents halogen,are prepared by halogenating the corresponding nicotinic acids. The Co Hal moiety is converted to CH.sub.3 by reaction withR.sup.3 OMgCR.sup.4 (COOR.sup.3).sub.2 (IV)in whichR.sup.3 represents C.sub.1-3 alkyl andR.sup.4 represents hydrogen or C.sub.1 -C.sub.2 -alkyl,and then hydrolyzing and decarboxylating the product.Type: GrantFiled: July 7, 1988Date of Patent: January 23, 1990Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach
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Patent number: 4889865Abstract: Mono, di and tri-esters of 1,8-dihydroxy-10-phenyl-9-anthrone or -9-anthranol have the formula ##STR1## wherein p is 0 or 1,(a) when p=0, t=1 and R.sub.2 represents hydrogen or --COR.sub.3,(b) when p=1, t=0 and R.sub.1 and R.sub.2 each independently represent hydrogen or --COR.sub.3,R.sub.3 represents linear or branched alkyl having 1-17 carbon atoms, cycloalkyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, halogen, a nitro function, --CF.sub.3 or a hydroxyl function, and mixtures of said esters. These esters are prepared by reacting 1,8-dihydroxy-10-phenyl-9-anthrone with an activated form of an acid. The esters are useful in human or veterinary medicine and in cosmetic compositions.Type: GrantFiled: February 21, 1989Date of Patent: December 26, 1989Assignee: Centre International de Recherches Dermatologiques C.I.R.D.Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
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Patent number: 4885026Abstract: Disclosed are pyridine herbicides characterized by substitution with a fluorine-containing methyl group at the 2- or 6-position, a carboxylic acid-derived group at the 3-position, and a halogen or a substituted nitrogen-containing group at the 5-position.Type: GrantFiled: May 12, 1986Date of Patent: December 5, 1989Assignee: Monsanto CompanyInventors: Len F. Lee, Mark G. Dolson
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Patent number: 4868308Abstract: A process for the preparation of N-phenyl(pyridyl)sulfonyldiamides by reacting a 2-aminobenzoic acid (nicotinic acid) derivative with sulfur trioxide, chlorosulfonic acid or an adduct of sulfur trioxide with a tertiary amine in the presence of a diluent and of a tertiary amine, and reacting the resulting sulfamate with a primary amine and a phosphorus halide, or by reacting a 2-aminobenzoic acid (nicotinic acid) derivatives with an N-alkyl(cycloalkyl)sulfamic acid or a salt of this acid in the presence of a diluent and of a phosphorus halide.Type: GrantFiled: November 6, 1987Date of Patent: September 19, 1989Assignee: BASF AktiengesellschaftInventors: Hans Merkle, Albrecht Mueller, Gerhard Hamprecht, Gernot Reissenweber
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Patent number: 4863939Abstract: The growth of livestock is promoted by the new compounds of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, halogen, halogenoalkyl, hydroxyl, cyano, alkoxycarbonyl, aminocarbonyl, mono- and dialkylaminocarbonyl, alkoxy, halogenoalkoxy, halogenoalkylthio or NHSO.sub.2 -alkyl,R.sup.2 represents hydrogen, hydroxyl, alkoxy or the --NR.sup.11 R.sup.12 radical,R.sup.3 represents the radicals mentioned in the case of R.sup.1R.sup.4 represents hydroxyl, acyloxy or alkoxy,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen or alkyl,R.sup.7 represents hydrogen or alkyl,R.sup.8 represents hydrogen or alkyl,X represents C.sub.1 -C.sub.10 -alkylene or a direct bond,Y represents oxygen or a direct bond,R.sup.9 represents hydrogen, C.sub.1 -C.sub.10 -alkyl which is optionally substituted by hydroxyl, alkoxy, acyloxy or the --NR.sup.13 R.sup.14 radical, or represents the COR.sup.15 radical or the O--Z--R.sup.16 radical,Z represents C.sub.1 -C.sub.10 -alkylene, C.sub.1 -C.sub.Type: GrantFiled: July 30, 1987Date of Patent: September 5, 1989Assignee: Bayer AktiengesellschaftInventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Anno de Jong, Martin Scheer
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Patent number: 4859663Abstract: Multiply substituted pyridine 1-oxides of the formula I ##STR1## in which R.sup.1 and R.sup.2 are, in each case, identical or different and represent alkyl having 1 to 6 carbon atoms,R.sup.3 denotes hydrogen, andR.sup.4 denotes mercaptoalkyl having up to 4 carbon atoms, orR.sup.3 and R.sup.4 form, together with the nitrogen atom in the 4-position, a five- to seven-membered saturated heterocyclic ring which has up to 2 heteroatoms, the second heteroatom being oxygen, sulfur which can carry up to two oxygen atoms, or nitrogen in the form of the NR.sup.6 group, in which R.sup.Type: GrantFiled: December 16, 1986Date of Patent: August 22, 1989Assignee: Hoechst AktiengesellschaftInventors: Wilfried Greve, Ulrich Elben, Karl Rudolph, Ursula Schindler
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Patent number: 4845113Abstract: Compounds of formula I ##STR1## wherein R is hydrogen or lower alkyl; R.sub.1 is acetyl, benzoyl, cyano, nitro, carboxy, alkoxycarbonyl or aminocarbonyl groups; R.sub.2 is an optionally substituted aryl or hetaryl residue; R.sub.3 is a carboxy or alkoxycarbonyl group; A is a cyclopropyl group or a group of formula --CH.dbd.CH-- and R.sub.4 is a phenyl or heteroaryl group, optionally mono, di or tri-substituted, are useful in radical scavenging therapy.Type: GrantFiled: July 25, 1986Date of Patent: July 4, 1989Assignee: Boehringer Biochemia Robin S.p.A.Inventors: Carmelo A. Gandolfi, Marco Frigerio, Silvano Spinelli, Odoardo Tofanetti, Ernesto Menta, Sergio Tognella
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Patent number: 4833169Abstract: Hydropyridine derivatives of the formula ##STR1## in which R.sub.1 represents carboxy, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl, R.sub.2 represents hydrogen, an optionally etherified or acylated hydroxy group or an optionally acylated amino group, and R.sub.3 represents a radical of the formula R-- (Ia), R--alk.sub.1 -- (Ib) or R'.dbd.alk.sub.2 -- (Ic) in which R represents a benzocycloalkenyl radical having a total of from 8 to 12 ring carbon atoms which is bonded via a saturated carbon atom and which is unsubstituted or is mono- or poly-substituted in the benzo moiety by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, lower alkyl and/or by trifluoromethyl, and/or subsituted in the .alpha.Type: GrantFiled: August 3, 1988Date of Patent: May 23, 1989Assignee: Ciba-Geigy CorporationInventors: Georg von Sprecher, Wolfgang Frostl, Armin Zust
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Patent number: 4833152Abstract: Novel inhibitors of angiotensin coverting enzyme having the general formula R - A - S - Z are disclosed as potent inhibitors of angiotensin converting enzyme and are useful anti-hypertensive agents.Type: GrantFiled: November 20, 1987Date of Patent: May 23, 1989Assignee: University of MiamiInventors: James W. Ryan, Alfred Chung