Nitrogen Attached Directly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/289)
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Patent number: 5272272Abstract: The present invention relates to novel sweetening agents. These sweetening agents have the general formula ##STR1## in which R is a 5,6,7,8-tetrahydro-1-naphthoyl or 1-naphthoyl radical, R' is a 2-cyanopyrid-5-yl radical and n is equal to 2. These novel sweetening agents are characterized by an extremely high sweetening potency and a very high stability compatible with all the conditions of industrial use.Type: GrantFiled: April 21, 1992Date of Patent: December 21, 1993Inventors: Claude Nofre, Jean-Marie Tinti
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Patent number: 5262415Abstract: An aminopyridine compound represented by the formula: ##STR1## wherein n represents 0 or 1; Z represents .dbd.S, .dbd.O, .dbd.NCN or .dbd.CHNO.sub.2 ; R.sub.1 represents --CN, --NR.sub.3 R.sub.4, --CONR.sub.3 R.sub.4, --NHNR.sub.3 R.sub.4, --NHCONHR.sub.3, --NHSO.sub.2 R.sub.3 or --SR.sub.3 ; R.sub.2 represents H, or substituted or unsubstituted alkyl; R.sub.3 and R.sub.4, which may be the same or different, represent H, substituted or unsubstituted alkyl, aryl, substituted or unsubstituted acyl or alkoxycarbonyl group; and R.sub.3 and R.sub.4 may form a heterocyclic ring together with a nitrogen atom to which R.sub.3 and R.sub.4 are bound, through another heteroatom or without it; or an acid salt thereof, which is excellent in pharmacological effect and repressed in side effects as a drug for circulatory diseases.Type: GrantFiled: March 13, 1992Date of Patent: November 16, 1993Assignee: The Green Cross CorporationInventors: Tadahiro Takemoto, Masahiro Eda, Mitsuyoshi Hihara, Takehiro Okada, Hiroshi Sakashita, Miyuki Eiraku, Chikara Fukaya, Norifumi Nakamura, Masanori Sugiura, Sumio Matzno, Maki Goda, Yasumi Uchida
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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: 5223520Abstract: Compounds of formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl and R.sub.4 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl or --CH.sub.2 CH.sub.2 COOR.sub.7, or R.sub.3 and R.sub.4 together are --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, ##STR2## --CH.sub.2 OCH.sub.3, --CN, --COOR.sub.7 or ##STR3## R.sub.6 is hydrogen, chlorine, methyl or nitro, R.sub.7 and R.sub.8 are each methyl or ethyl, A is an unsubstituted or mono- to tetra-substituted, aromatic or non-aromatic, monocyclic or bicyclic, heterocyclic radical, one or two substituents being selected from the group consisting of C.sub.1 -C.sub.3 haloalkyl, cyclopropyl, halocyclopropy, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl, C.sub.2 -C.sub.3 haloalkynyl, C.sub.1 -C.sub.3 haloalkoxy, C.sub.Type: GrantFiled: March 27, 1992Date of Patent: June 29, 1993Assignee: Ciba-Geigy CorporationInventors: Odd Kristiansen, Laurenz Gsell, Peter Maienfisch
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Patent number: 5212310Abstract: The present invention encompasses structures of the formula: ##STR1## and the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## and W, X, A, B, C, D, E, R.sub.3, R.sub.4 are variables. These compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs thereof and are useful in the diagnosis and treatment of anxiety, sleep, and seizure disorders, overdose with benzodiazepine drugs, and enhancement of memory.Type: GrantFiled: December 19, 1991Date of Patent: May 18, 1993Assignee: Neurogen CorporationInventors: Andrew Thurkauf, Alan Hutchison, Pamela Albaugh
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Patent number: 5196521Abstract: The dyes of the formula ##STR1## in which R.sub.1 is hydrogen, halogen or CF.sub.3 and R.sub.2 is substituted or unsubstituted alkyl, where R.sub.2 must not be ethoxycarbonylethyl if R.sub.1 is hydrogen are suitable for the dyeing of polyester material in red hues having very good lightfastness.Type: GrantFiled: June 24, 1991Date of Patent: March 23, 1993Assignee: Ciba-Geigy CorporationInventors: Visvanathan Ramanathan, Angelo D. Casa
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Patent number: 5187176Abstract: Phenyl substituted heterocyclic compounds having insecticidal activity have the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted pyridone, thiopyridone, pyrimidinthione, pyrimidinone, pyrazole, imidazole or triazole group; R.sup.2 is hydrogen, halogen, haloalkyl, nitro, cyano or a group --CX--NY.sup.1 Y.sup.2 ; R.sup.3 and R.sup.5 are hydrogen, halogen, alkyl or cycloalkyl; R.sup.4 is halogen, haloalkyl, haloalkoxy or S(O).sub.n R.sup.6 ; and Y.sup.1 and Y.sup.2 are independently selected from hydrogen, nitro, amino or optionally substituted alkyl or Y.sup.1 and Y.sup.2 together with the nitrogen to which they are attached form an aliphatic heterocyclic group or form the group .dbd.CHY.sup.3 or Y.sup.1 is hydrogen and Y.sup.2 is alkoxycarbonyl, alkylcarbonyl, optionally substituted aralkyl or --S(O).sub.n R.sup.6.Type: GrantFiled: October 9, 1991Date of Patent: February 16, 1993Assignee: Imperial Chemical Industries PLCInventors: Roger Salmon, Raymond L. Sunley, Alan J. Whittle
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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: 5177089Abstract: A butenoic or propenoic acid derivative having the following formula in which G is an aryl or a heterocyclic ring, R11 and R12 are hydroben or an alkyl, X is sulfur or oxygen, R2 and R3 are hydrogen, an substituent such as an alkyl and J is pyridyl or phenyl having substituents and a heterocyclic ring may be formed between R2, R3 and J is provided here and is useful in the pharmacological field.Type: GrantFiled: July 25, 1990Date of Patent: January 5, 1993Assignee: Eisai Co., Ltd.Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
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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: 5114954Abstract: Benzylselenobenzamides of formula I ##STR1## with inflammation-inhibiting characteristics and used in pharmaceutical preparations.Type: GrantFiled: November 8, 1990Date of Patent: May 19, 1992Assignee: A. Nattermann & Cie. GmbHInventors: Jurgen Biedermann, Michel Evers, Rolf Terlinden, Sigurd Leyck, Erich Graf
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Patent number: 5112386Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur, A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 --S(O).sub.n R.sup.3 groups; any two of the groups, A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.Type: GrantFiled: December 30, 1988Date of Patent: May 12, 1992Assignee: Imperial Chemical Industries PLCInventors: Anthony Vivienne, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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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: 5081133Abstract: 2-Anilinocyanopyridines of the formula ##STR1## where X is NO.sub.2, CN, halogen, SO.sub.2 -alkyl, alkyl, cycloalkyl, haloalkyl, alkoxy, or phenoxy or phenylthio which is unsubstituted or substituted in the phenyl,m is an integer from 1 to 3,R.sup.1 is hydrogen, halogen, alkoxy, haloalkyl, haloalkoxy, or phenoxy or phenylthio which is unsubstituted or substituted in the phenyl,R.sup.2 and R.sup.3 are hydrogen, NO.sub.2, halogen, CN, alkyl, SO.sub.2 -alkyl, haloalkyl, SO.sub.2 NR.sup.5 R.sup.6, haloalkoxy, COOR.sup.5 or CONR.sup.5 R.sup.6,R.sup.4 is hydrogen, COOR.sup.7, CONR.sup.5 R.sup.6, CHO, COR.sup.7, SO.sub.2 R.sup.7, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl,and salts of these 2-anilinocyanopyridines of the formula I in which R.sup.4 is hydrogen with plant-tolerated cations, and fungicides containing these compounds.Type: GrantFiled: January 25, 1990Date of Patent: January 14, 1992Assignee: BASF AktiengesellschaftInventors: Juergen Schubert, Jochen Wild, Albrecht Harreus, Thomas Kuekenhoehner, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
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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: 5076830Abstract: The present invention provides indan-1,3-dione derivatives, including derivatives represented by the following formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents a group represented by ##STR2## wherein E represents a (substituted) phenyl group or a (substituted) pyridyl group; Y represents a hydroxyl group; and Z represents a halogen atom, a (substituted) alkylsulfonyloxy group or a (substituted) phenylsulfonyloxy group, or Y and Z are bonded to represent --O--; and A represents a (substituted) 1,3-butadienylene group or a (substituted) 1,3-azabutadienylene group, and a herbicidal composition containing the same as an active ingredient.The compound of the formula (I) shows high herbicidal activity against gramineous weeds, cyperaceous weeds, etc. but shows markedly low phytotoxicity against crops.Type: GrantFiled: May 15, 1990Date of Patent: December 31, 1991Assignee: Mitsubishi Kasei CorporationInventors: Tetsuo Jikihara, Toyohiko Shike, Manabu Katsurada, Hisao Watanabe, Osamu Ikeda
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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: 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: 4997667Abstract: Sweetening agents of the formula: ##STR1## wherein R is an heterocyclic group which, in a preferred embodiment, is a 2-cyanopyrid-5-yl or 2-cyanopyrimidin-5-yl group, A is O, NH or NCN, NH being able to be satisfied in hydrochloride form, n is 1 or 2 and B is COOH or a sodium, potassium, ammonium, calcium or magnesium salt.Type: GrantFiled: December 16, 1988Date of Patent: March 5, 1991Assignee: Universite Claude BernardInventors: Claude Nofre, Jean M. Tinti, Farroudja O. Chatzopoulos
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Patent number: 4997837Abstract: Certain trans-6-[[(substituted)pyridin-3-yl]-alkyl- and alkenyl]tetrahydro-4-hydroxypyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reductase) and are useful as hypocholesterolemic and hypolipidemic agents.Type: GrantFiled: October 6, 1989Date of Patent: March 5, 1991Assignee: Warner-Lambert CompanyInventors: Alexander W. Chucholowski, Mark W. Creswell, Bruce D. Roth, Drago R. Sliskovic
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Patent number: 4985449Abstract: A benzoylurea compound having the formula: ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom or a methyl group, provided that X.sub.1 and X.sub.2 are not simultanously hydrogen atoms, Y is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, a --CO.sub.2 R.sub.1 group wherein R.sub.1 is a hydrogen atom, a cation or an alkyl group, or a --OR.sub.1 group wherein R.sub.1 is as defined above, A.sub.1 is .dbd.N-- or ##STR2## wherein Y is as defined above, W is an oxygen atom, a sulfur atom or ##STR3## wherein R.sub.1 is as defined above, k is an integer of from 1 to 3, l is 0 or 1, and Ar is ##STR4## wherein Z is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, an alkoxy group which may be substituted by halogen, a nitro group, a cyano group or a --S(O).sub.n R.sub.2 group wherein R.sub.2 is an alkyl group which may be substituted by halogen and n is 0, 1 or 2, A.sub.Type: GrantFiled: June 13, 1989Date of Patent: January 15, 1991Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
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Patent number: 4980469Abstract: A process for the preparation of an oxyguanidine of the formula ##STR1## in which R.sup.1 is an organic radical,R.sup.2, R.sup.3 and R.sup.4 each is hydrogen or an organic or inorganic substituent,X is N or CH,Y is N or CR.sup.3, andZ is N or CR.sup.4,comprising reacting ##STR2## in which R.sup.5 is optionally substituted alkyl or aralkyl, or its hydrogen halide, with a hydroxylamine derivative of the formulaH.sub.2 N--O--R.sup.1 (III)at a temperature between about 0.degree. C. and 150.degree. C. New isothioureas of the formula ##STR3## are also shown.Type: GrantFiled: August 30, 1989Date of Patent: December 25, 1990Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Klaus-Helmut Muller
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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: 4935517Abstract: Sweetening agents of the general formula: ##STR1## wherein R is a saturated or unsaturated, acyclic, cyclic or mixed hydrocarbon group having 5 to 13 carbon atoms, wherein R' is, in a preferred embodiment, a 4-cyanophenyl or 2-cyanopyrid-5-yl group, and wherein n is equal to 1 or 2.Type: GrantFiled: April 21, 1989Date of Patent: June 19, 1990Assignee: Universite Claude BernardInventors: Claude Nofre, Jean M. Tinti
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Patent number: 4927828Abstract: The diastereoisomeric forms of N-(4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]-pyrimidin-6-yl) ethyl]benzoyl)-L-glutamic acid are antineoplastic agents.The compounds are prepared by separation of the diastereoisomeric form of the correspondingly protected glutamic derivatives and hydrolytic or hydrogenolytic removal of carboxylic acid and/or amino protecting groups.Typical embodiments are the (R,S) and (S,S) forms of N-(4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)e thyl]benzoyl)-L-glutamic acid.Type: GrantFiled: June 28, 1988Date of Patent: May 22, 1990Assignee: The Trustees of Princeton UniversityInventors: Edward C. Taylor, George P. Beardsley, Chuan Shih, Stephen R. Fletcher
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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: 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: 4918086Abstract: 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 akylthio, 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: July 27, 1988Date of Patent: April 17, 1990Assignee: Ciba-Geigy CorporationInventor: Laurenz Gsell
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Patent number: 4906288Abstract: Certain N-[(pyridyl or pyrimidyl)aminocarbonyl]arylsulfonamides, such as the compound methyl 2-[[N-(3-cyano-4,6-dimethylpyridin-2-yl)aminocarbonyl]aminosulfonyl]benzoa te, possess herbicidal activity.Type: GrantFiled: November 4, 1987Date of Patent: March 6, 1990Assignee: E. I. Du Pont de Nemours and CompanyInventors: Caleb W. Holyoke, Jr., Chi-Ping Tseng, William T. Zimmerman
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Patent number: 4897487Abstract: Processes for preparing bicyclic compounds useful as anti-allergic, anti-inflammatory and/or cytoprotective agents are described, together with a process for preparing intermediates thereof.Type: GrantFiled: April 6, 1988Date of Patent: January 30, 1990Assignee: Schering CorporationInventors: Dinesh Gala, Martin Steinman, Ashit Ganguly
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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: 4882341Abstract: The invention relates to amino substituted propenoates and their use against fungi.Type: GrantFiled: September 9, 1988Date of Patent: November 21, 1989Assignee: Imperial Chemical Industries PLCInventors: John M. Clough, Ian T. Kay
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Patent number: 4868181Abstract: 1,4-Dihydropyridine derivatives which combine both calcium agonist and alpha.sub.1 -antagonist activity are useful in treating congestive heart failure. These derivatives are compounds having the formula: ##STR1## wherein Ar, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are defined in the specification.Type: GrantFiled: June 30, 1987Date of Patent: September 19, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Alexander L. Johnson, Philip Ma, Petrus B. M. W. M. Timmermans, Ruth R. Wexler
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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: 4861799Abstract: A benzoylurea compound having the formula: ##STR1## wherein each of X.sub.1 and X.sub.2 is a hydrogen atom, a halogen atom or a methyl group, provided that X.sub.1 and X.sub.2 are not simultaneously hydrogen atoms, Y is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, a --CO.sub.2 R.sub.1 group wherein R.sub.1 is a hydrogen atom, a cation or an alkyl group, or a --OR.sub.1 group wherein R.sub.1 is as defined above, A.sub.1 is .dbd.N--or ##STR2## wherein Y is as defined above, W is an oxygen atom, a sulfur atom or ##STR3## wherein R.sub.1 is as defined above, k is an integer of from 1 to 3, l is 0 or 1, and Ar is ##STR4## wherein Z is independently a hydrogen atom, a halogen atom, an alkyl group which may be substituted by halogen, an alkoxy group which may be substituted by halogen, a nitro group, a cyano group or a --S(O).sub.n R.sub.2 group wherein R.sub.2 is an alkyl group which may be substituted by halogen and n is 0, 1 or 2, A.sub.Type: GrantFiled: September 30, 1987Date of Patent: August 29, 1989Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
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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: 4826531Abstract: Acrylic acid derivatives having the formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, R.sup.1 and R.sup.2 are alkyl or fluoroalkyl groups, and Z is oxygen or sulphur; A, B, D and E are hydrogen, halogen, hydroxy or optionally substituted alkyl, alkoxy, aralkyl, arylalkoxy, alkenyl, alkynyl, aryl, aryloxy, arylthio, heteroaryloxy, heteroarylthio, acyloxy, amino, arylazo or acylamino, nitro, cyano, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --CR.sup.3 .dbd.NR.sup.4, --N.dbd.CR.sup.3 R.sup.4 or --S(O).sub.n R.sup.3 groups; any two of the groups A, B, D and E, when they are in adjacent positions on the ring, optionally join to form a fused ring, n is 0, 1 or 2; and R.sup.3 and R.sup.4 are hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl or optionally substituted aryl or aralkyl; and metal complexes thereof. These compounds are useful as fungicides, insecticides, nematicides or plant growth regulators.Type: GrantFiled: April 17, 1987Date of Patent: May 2, 1989Assignee: Imperial Chemical Industries PLCInventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
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Patent number: 4826987Abstract: The present invention relates to compounds of formula I ##STR1## in which formula I X stands for O, S, ##STR2## R.sub.1 and R.sub.2 which can be the same or different stand for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.8 -alkyl, or for ar-C.sub.1 -C.sub.4 -alkyl, aryl and ar being unsubstituted or substituted phenyl; R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are the same or different and stand for hydrogen, halogen, pseudo halogen, cyano, nitro, amino, carboxy, hydroxy, alkyl, alkoxy; or R.sub.5 and R.sub.6 form an aromatic ring which is fused to the pyridyl ring, and which aromatic ring may substituted; provided that R.sub.1 and R.sub.2 cannot be hydrogen at the same time, and provided that when R.sub.5 and R.sub.6 both are chlorine and R.sub.1 is hydrogen, then R.sub.2 cannot be n-propyl; and salts and bioreversible derivatives thereof.Type: GrantFiled: February 28, 1986Date of Patent: May 2, 1989Assignee: Leo Pharmaceutical Products Ltd.Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
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Patent number: 4816468Abstract: The title compounds are provided as well as a method for their production, pharmaceutical compositions comprising the compounds, and methods of treatment using the compounds in dosage form. The compounds of the invention have pharmacological properties and are useful cytostatic agents and cell growth inhibiting agents.Type: GrantFiled: June 11, 1986Date of Patent: March 28, 1989Assignee: The University of AlabamaInventor: David C. Baker
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Patent number: 4798893Abstract: A method for the synthesis of the 2-propanone (I) is described starting from alkoxide (II) through the lactone (IV). ##STR1## Excellent control of the location of the substitution on the phenyl ring is achieved and the reaction proceeds in high yield.Type: GrantFiled: September 21, 1987Date of Patent: January 17, 1989Assignee: McNeilab, Inc.Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
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Patent number: 4775763Abstract: Metal values are extracted from aqueous solutions of metal salts containing halide or pseudo halide ions by pyridine derivatives containing the substituent --(COX).sub.A where X is the group --OR.sub.1 or --NR.sub.2 R.sub.3 and n is 1, 2 or 3. R.sub.1 is a hydrocarbyl group containing from 5 to 36 carbon atoms and R.sub.2 and R.sub.3 are hydrogen or a hydrocarbyl group wherein R.sub.2 and R.sub.3 together contain from 5 to 36 carbon atoms. The process is especially useful for the recovery of metals from leach solutions derived from sulphur-containing ores such as chalcopyrite.Type: GrantFiled: March 27, 1985Date of Patent: October 4, 1988Assignee: Imperial Chemical IndustriesInventors: Raymond F. Dalton, Raymond Price, Peter M. Quan, David Stewart
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Patent number: 4766213Abstract: Compounds of the formula ##STR1## are disclosed wherein the variables are herein described. These compounds are intermediates to compounds which influence the influx of calcium into the cell.Type: GrantFiled: January 16, 1987Date of Patent: August 23, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Horst Juraszyk, Rolf Gericke, Inge Lues, Rolf Bergmann, Claus J. Schmitges
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Patent number: 4739070Abstract: 2- and 4-(Dichloromethyl)pyridines containing electron withdrawing substituents on the ring are prepared by the reaction of the corresponding 2- or 4-halopyridines with excess chloroform in the presence of a strong base in a medium containing a dipolar aprotic solvent or a phase transfer catalyst. 3-Chloro-5-(trifluoromethyl)-2-(dichloromethyl)pyridine, for example, is prepared by the reaction of 2,3-dichloro-5-(trifluoromethyl)pyridine with chloroform in the presence of sodium hydroxide and N-methylpyrrolidone. Substituted 2-(dichloromethyl)pyridines are useful as agricultural pesticides and as intermediates for the preparation of agricultural pesticides.Type: GrantFiled: April 23, 1986Date of Patent: April 19, 1988Assignee: The Dow Chemical CompanyInventor: Jon A. Orvik
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Patent number: 4684734Abstract: Organic fluorine compounds such as pentafluorobenzonitrile, tetrafluorophthalonitriles, and pentafluoropyridine are produced by a method which comprises causing a chloro- or bromo-organic compound to react with a fluorinating agent such as an alkali metal fluoride in benzonitrile as a solvent at temperatures in the range of 190.degree. to 400.degree. C. under at least spontaneously generated pressure.Type: GrantFiled: September 13, 1985Date of Patent: August 4, 1987Assignee: Nippon Shokubai KK Co., Ltd.Inventors: Osamu Kaieda, Masaru Awashima, Isao Okitaka, Toshiaki Nakamura
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Patent number: 4666506Abstract: Aryl and heteroaryl sulfonimidamides which also contain a pyrimidine or triazine heterocycle are useful as general or selective preemergent and postemergent herbicides.Type: GrantFiled: July 11, 1985Date of Patent: May 19, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Craig L. Hillemann
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Patent number: 4652650Abstract: Pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.Type: GrantFiled: August 5, 1985Date of Patent: March 24, 1987Assignee: Smith Kline & French Laboratories LimitedInventor: Robert J. Ife