Nitrogen Attached Directly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/289)
  • Patent number: 5272272
    Abstract: 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: Grant
    Filed: April 21, 1992
    Date of Patent: December 21, 1993
    Inventors: Claude Nofre, Jean-Marie Tinti
  • Patent number: 5262415
    Abstract: 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: Grant
    Filed: March 13, 1992
    Date of Patent: November 16, 1993
    Assignee: The Green Cross Corporation
    Inventors: Tadahiro Takemoto, Masahiro Eda, Mitsuyoshi Hihara, Takehiro Okada, Hiroshi Sakashita, Miyuki Eiraku, Chikara Fukaya, Norifumi Nakamura, Masanori Sugiura, Sumio Matzno, Maki Goda, Yasumi Uchida
  • Patent number: 5238908
    Abstract: 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: Grant
    Filed: August 9, 1990
    Date of Patent: August 24, 1993
    Assignee: Rohm and Haas Company
    Inventors: Barry C. Lange, John W. Ashmore, Jane Wissinger-Cornille
  • Patent number: 5223520
    Abstract: 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: Grant
    Filed: March 27, 1992
    Date of Patent: June 29, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Odd Kristiansen, Laurenz Gsell, Peter Maienfisch
  • Patent number: 5212310
    Abstract: 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: Grant
    Filed: December 19, 1991
    Date of Patent: May 18, 1993
    Assignee: Neurogen Corporation
    Inventors: Andrew Thurkauf, Alan Hutchison, Pamela Albaugh
  • Patent number: 5196521
    Abstract: 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: Grant
    Filed: June 24, 1991
    Date of Patent: March 23, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Visvanathan Ramanathan, Angelo D. Casa
  • Patent number: 5187176
    Abstract: 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: Grant
    Filed: October 9, 1991
    Date of Patent: February 16, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Roger Salmon, Raymond L. Sunley, Alan J. Whittle
  • Patent number: 5182401
    Abstract: 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: Grant
    Filed: May 2, 1991
    Date of Patent: January 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventor: Klaus Grohe
  • Patent number: 5177089
    Abstract: 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: Grant
    Filed: July 25, 1990
    Date of Patent: January 5, 1993
    Assignee: Eisai Co., Ltd.
    Inventors: Norio Minami, Fumihiro Ozaki, Keiji Ishibashi, Yasuhiro Kabasawa, Megumi Ikemori, Toshiaki Ogawa, Takanori Kawamura
  • Patent number: 5126338
    Abstract: 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: Grant
    Filed: January 3, 1991
    Date of Patent: June 30, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Paul A. Worthington, Ian R. Matthews, David Bartholomew, Patrick J. Crowley, Don R. Baker, Karl J. Fisher
  • Patent number: 5114954
    Abstract: Benzylselenobenzamides of formula I ##STR1## with inflammation-inhibiting characteristics and used in pharmaceutical preparations.
    Type: Grant
    Filed: November 8, 1990
    Date of Patent: May 19, 1992
    Assignee: A. Nattermann & Cie. GmbH
    Inventors: Jurgen Biedermann, Michel Evers, Rolf Terlinden, Sigurd Leyck, Erich Graf
  • Patent number: 5112386
    Abstract: 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: Grant
    Filed: December 30, 1988
    Date of Patent: May 12, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Anthony Vivienne, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 5106986
    Type: Grant
    Filed: February 22, 1991
    Date of Patent: April 21, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Bernd Gallenkamp
  • Patent number: 5100460
    Abstract: 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: Grant
    Filed: July 13, 1989
    Date of Patent: March 31, 1992
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Philippe Desbordes, Michel Euvrard
  • Patent number: 5081133
    Abstract: 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: Grant
    Filed: January 25, 1990
    Date of Patent: January 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Schubert, Jochen Wild, Albrecht Harreus, Thomas Kuekenhoehner, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5079361
    Abstract: 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: Grant
    Filed: September 9, 1988
    Date of Patent: January 7, 1992
    Assignee: Celltech Limited
    Inventors: Rikki P. Alexander, Michael A. W. Eaton, Thomas A. Millican, Richard C. D. Titmas
  • Patent number: 5076830
    Abstract: 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: Grant
    Filed: May 15, 1990
    Date of Patent: December 31, 1991
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tetsuo Jikihara, Toyohiko Shike, Manabu Katsurada, Hisao Watanabe, Osamu Ikeda
  • Patent number: 5049571
    Abstract: 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: Grant
    Filed: January 24, 1990
    Date of Patent: September 17, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Laurenz Gsell
  • Patent number: 5008276
    Abstract: 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: Grant
    Filed: October 17, 1988
    Date of Patent: April 16, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 4997667
    Abstract: 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: Grant
    Filed: December 16, 1988
    Date of Patent: March 5, 1991
    Assignee: Universite Claude Bernard
    Inventors: Claude Nofre, Jean M. Tinti, Farroudja O. Chatzopoulos
  • Patent number: 4997837
    Abstract: 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: Grant
    Filed: October 6, 1989
    Date of Patent: March 5, 1991
    Assignee: Warner-Lambert Company
    Inventors: Alexander W. Chucholowski, Mark W. Creswell, Bruce D. Roth, Drago R. Sliskovic
  • Patent number: 4985449
    Abstract: 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: Grant
    Filed: June 13, 1989
    Date of Patent: January 15, 1991
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
  • Patent number: 4980469
    Abstract: 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: Grant
    Filed: August 30, 1989
    Date of Patent: December 25, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Klaus-Helmut Muller
  • Patent number: 4973429
    Abstract: 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: Grant
    Filed: February 15, 1989
    Date of Patent: November 27, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Gero Decher, Bernd Tieke, Christian Bosshard, Peter Gunter
  • Patent number: 4968796
    Abstract: 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: Grant
    Filed: August 17, 1989
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Jochem Riebel
  • Patent number: 4962113
    Abstract: 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: Grant
    Filed: July 26, 1988
    Date of Patent: October 9, 1990
    Assignee: Takeda Chemical Industries, Ltd
    Inventors: Susumu Tsushima, Muneo Takatani, Kohei Nishikawa
  • Patent number: 4959474
    Abstract: 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: Grant
    Filed: October 15, 1985
    Date of Patent: September 25, 1990
    Assignee: Burroughs Wellcome Co.
    Inventor: Eugene M. Grivsky
  • Patent number: 4935517
    Abstract: 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: Grant
    Filed: April 21, 1989
    Date of Patent: June 19, 1990
    Assignee: Universite Claude Bernard
    Inventors: Claude Nofre, Jean M. Tinti
  • Patent number: 4927828
    Abstract: 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: Grant
    Filed: June 28, 1988
    Date of Patent: May 22, 1990
    Assignee: The Trustees of Princeton University
    Inventors: Edward C. Taylor, George P. Beardsley, Chuan Shih, Stephen R. Fletcher
  • Patent number: 4920136
    Abstract: 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: Grant
    Filed: July 13, 1988
    Date of Patent: April 24, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer
  • Patent number: 4920225
    Abstract: 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: Grant
    Filed: December 22, 1986
    Date of Patent: April 24, 1990
    Assignee: Laboratoires Syntex S.A.
    Inventor: Gilles Genain
  • Patent number: 4918086
    Abstract: 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: Grant
    Filed: July 27, 1988
    Date of Patent: April 17, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Laurenz Gsell
  • Patent number: 4906288
    Abstract: 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: Grant
    Filed: November 4, 1987
    Date of Patent: March 6, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Caleb W. Holyoke, Jr., Chi-Ping Tseng, William T. Zimmerman
  • Patent number: 4897487
    Abstract: 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: Grant
    Filed: April 6, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Corporation
    Inventors: Dinesh Gala, Martin Steinman, Ashit Ganguly
  • Patent number: 4889865
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: December 26, 1989
    Assignee: Centre International de Recherches Dermatologiques C.I.R.D.
    Inventors: Braham Shroot, Gerard Lang, Jean Maignan, Serge Restle, Christopher Hensby, Michel Colin
  • Patent number: 4882341
    Abstract: The invention relates to amino substituted propenoates and their use against fungi.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: November 21, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Ian T. Kay
  • Patent number: 4868181
    Abstract: 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: Grant
    Filed: June 30, 1987
    Date of Patent: September 19, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Alexander L. Johnson, Philip Ma, Petrus B. M. W. M. Timmermans, Ruth R. Wexler
  • Patent number: 4863939
    Abstract: 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: Grant
    Filed: July 30, 1987
    Date of Patent: September 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Anno de Jong, Martin Scheer
  • Patent number: 4861799
    Abstract: 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: Grant
    Filed: September 30, 1987
    Date of Patent: August 29, 1989
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Tadaaki Toki, Toru Koyanagi, Yasuhiro Fujii, Kiyomitsu Yoshida, Osamu Imai
  • Patent number: 4859663
    Abstract: 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: Grant
    Filed: December 16, 1986
    Date of Patent: August 22, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wilfried Greve, Ulrich Elben, Karl Rudolph, Ursula Schindler
  • Patent number: 4826531
    Abstract: 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: Grant
    Filed: April 17, 1987
    Date of Patent: May 2, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Patrick J. Crowley, Kenneth Anderton
  • Patent number: 4826987
    Abstract: 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: Grant
    Filed: February 28, 1986
    Date of Patent: May 2, 1989
    Assignee: Leo Pharmaceutical Products Ltd.
    Inventors: Ole Bent Iv rmose Nielsen, Ian Ahnfelt-Ronne
  • Patent number: 4816468
    Abstract: 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: Grant
    Filed: June 11, 1986
    Date of Patent: March 28, 1989
    Assignee: The University of Alabama
    Inventor: David C. Baker
  • Patent number: 4798893
    Abstract: 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: Grant
    Filed: September 21, 1987
    Date of Patent: January 17, 1989
    Assignee: McNeilab, Inc.
    Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
  • Patent number: 4775763
    Abstract: 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: Grant
    Filed: March 27, 1985
    Date of Patent: October 4, 1988
    Assignee: Imperial Chemical Industries
    Inventors: Raymond F. Dalton, Raymond Price, Peter M. Quan, David Stewart
  • Patent number: 4766213
    Abstract: 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: Grant
    Filed: January 16, 1987
    Date of Patent: August 23, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Horst Juraszyk, Rolf Gericke, Inge Lues, Rolf Bergmann, Claus J. Schmitges
  • Patent number: 4739070
    Abstract: 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: Grant
    Filed: April 23, 1986
    Date of Patent: April 19, 1988
    Assignee: The Dow Chemical Company
    Inventor: Jon A. Orvik
  • Patent number: 4684734
    Abstract: 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: Grant
    Filed: September 13, 1985
    Date of Patent: August 4, 1987
    Assignee: Nippon Shokubai KK Co., Ltd.
    Inventors: Osamu Kaieda, Masaru Awashima, Isao Okitaka, Toshiaki Nakamura
  • Patent number: 4666506
    Abstract: Aryl and heteroaryl sulfonimidamides which also contain a pyrimidine or triazine heterocycle are useful as general or selective preemergent and postemergent herbicides.
    Type: Grant
    Filed: July 11, 1985
    Date of Patent: May 19, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Craig L. Hillemann
  • Patent number: 4652650
    Abstract: Pyridine derivatives are disclosed which are useful as histamine H.sub.1 -antagonists.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: March 24, 1987
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: Robert J. Ife