At 2-position Patents (Class 544/330)
  • Patent number: 5153200
    Abstract: Compounds of the formula ##STR1## in which: R.sub.1 and R.sub.2 independently of one anther are hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; R.sub.3 is hydrogen; C.sub.1 -C.sub.4 alkyl; or C.sub.1 -C.sub.4 alkyl substituted by halogen, hydroxy or by cyano; cyclopropyl; or cyclopropyl mono- to tri-substituted by methyl and/or by halogen; and R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by methyl and/or by halogen, have valuable microbicidal and insecticidal properties. The novel active ingredients can be used in plant protection for preventing an attack on cultivated plants by phytopathogenic microorganisms or by harmful insects, and for controlling these pests.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: October 6, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Adolf Hubele
  • Patent number: 5136080
    Abstract: A class of substituted phenylpyrimidine compounds are disclosed which are potent inhibitors of the excitatory amino acid, glutamate. Such compounds are useful in the treatment or prevention of a range of CNS disorders including cerebral ischaemic damage and epilepsy.
    Type: Grant
    Filed: June 5, 1990
    Date of Patent: August 4, 1992
    Assignee: Burroughs Wellcome Co.
    Inventors: Alistair A. Miller, Malcolm S. Nobbs, Richard M. Hyde, Michael John
  • Patent number: 5110986
    Abstract: This application relates to a process for preparing a N-t-alkyl-1,2-diacylhydrazine by reacting a 1,3,4-oxadiazole with a tertiary alkyl cation precursor in the presence of a strong acid catalyst. Preferably, the 1,3,4-oxadiazole is a 2,5-disubstituted-1,3,4-oxadiazole and more preferably a 2,5-diaryl-1,3,4-oxadiazole. The strong acid catalyst is preferably a sulfur containing acid and more preferably sulfuric acid.
    Type: Grant
    Filed: April 26, 1988
    Date of Patent: May 5, 1992
    Assignee: Rohm and Haas Company
    Inventor: Martha J. Kelly
  • Patent number: 5100897
    Abstract: Novel substituted pyrimidinones of formula (I) which are useful as angiotensin II antagonists, are disclosed.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: March 31, 1992
    Assignee: Merck & Co., Inc.
    Inventors: Eric E. Allen, William J. Greenlee, Prasun K. Chakravarty, Arthur A. Patchett, Thomas F. Walsh
  • Patent number: 5098905
    Abstract: The present invention is various 7-deazaguanines having activity as immunomodulators. Also included are pharmaceutical compositions and methods of use thereof.
    Type: Grant
    Filed: November 15, 1990
    Date of Patent: March 24, 1992
    Assignee: Warner-Lambert Company
    Inventors: Thomas C. Malone, Jagadish C. Sircar
  • 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: 5059598
    Abstract: Disclosed are compounds of the formula ##STR1## wherein: R.sup.1 is a lower alkyl group;R.sup.2 and R.sup.3 are each hydrogen or lower alkyl or R.sup.2 and R.sup.3 taken together may form --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.dbd.CH--;.alpha. is a 5- or 6-membered heretoaromatic ring group containing 1 to 3 hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur, or a pyrazine-N-oxide ring, pyridazine-N-oxide ring or pyrimidine -N-oxide ring group, wherein each of these heteroaromatic ring groups may optionally have 1 to 3 substituents selected from the group consisting of a lower alkyl halogen, phenyl, lower alkoxycarbonyl, amino, lower alkoxy and hydroxy-lower alkyl, with the proviso that said 5- or 6-membered heteroaromatic ring group is not thiazolyl, isothiazolyl, pyridyl or 1,3,5-triazinyl group; or salts thereof. These compounds and salts thereof have anti-inflammatory activity and lipoxygenase-inhibitory activity.
    Type: Grant
    Filed: September 19, 1989
    Date of Patent: October 22, 1991
    Assignee: Otsuka Pharmaceutical Factory, Inc.
    Inventors: Kenichi Kanai, Kiyoto Goto, Kinji Hashimoto
  • Patent number: 5043443
    Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4- (4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.
    Type: Grant
    Filed: July 24, 1990
    Date of Patent: August 27, 1991
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
  • Patent number: 5021413
    Abstract: Analgesic compounds are of the general formula (I): ##STR1## in which, R.sup.1 and R.sup.2 each represents hydrogen or C.sub.1 -C.sub.6 alkyl, or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a heterocycle; E represents methylene, sulfur, oxygen or imino group optionally substituted with C.sub.1 -C.sub.6 alkyl or aralkyl; ring A is aryl or heteroaryl ring, optionally substituted; R.sup.3 is hydrogen or C.sub.1 -C.sub.6 alkyl and R.sup.4 is hydrogen or R.sup.3 and R.sup.4 together represent a group of formula (IV):--(CR.sup.a R.sup.a).sub.m --C(.dbd.Y)-- (IV)(wherein R.sup.a and R.sup.a is C.sub.1 -C.sub.6 alkyl or hydrogen, up to a maximum of 3 alkyl groups, m is 1, 2, or 3, and Y is two hydrogens or oxygen); provided that when E represents a methylene group, then R.sup.3 is a C.sub.1 -C.sub.6 alkyl group or R.sup.3 and R.sup.4 together represent a group of the formula (IV).
    Type: Grant
    Filed: August 22, 1989
    Date of Patent: June 4, 1991
    Assignee: Sankyo Company Limited
    Inventors: Atsusuke Terada, Yoshio Iizuka, Kazuyuki Wachi, Kenji Fujibayashi
  • Patent number: 5010082
    Abstract: Compounds of formula ##STR1## wherein: R.sub.1 is phenyl, naphthyl, phenyl substituted from one to five times by R.sub.6, or naphthyl substituted from one to five times by R.sub.6 ; R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl substituted at least once by halogen, C.sub.1 -C.sub.3 alkoxy and/or by C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkoxycarbonyl, phenyl, phenyl mono- to tri-substituted by halogen, C.sub.1 -C.sub.3 alkoxy and/or by C.sub.1 -C.sub.3 alkyl, benzyl, or benzyl mono- to tri-substituted by halogen, C.sub.1 -C.sub.3 alkoxy and/or by C.sub.1 -C.sub.3 alkyl; R.sub.3 is hydrogen, C.sub.1 -C.sub.6 alkyl or the radical CO-R.sub.7 ; R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by halogen and/or by methyl, C.sub.1 -C.sub.4 alkyl substituted at least once by halogen, hydroxy and/or by cyano, C.sub.2 -C.sub.5 alkynyl, C.sub.1 -C.sub.4 alkylthio or the radical CH.sub.2 XR.sub.8 ; R.sub.5 is hydrogen, C.sub.
    Type: Grant
    Filed: September 22, 1989
    Date of Patent: April 23, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Riebli
  • Patent number: 5003069
    Abstract: 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: Grant
    Filed: July 26, 1989
    Date of Patent: March 26, 1991
    Assignee: Reilly Industries, Inc.
    Inventors: Charles K. McGill, James J. Sutor
  • Patent number: 4996319
    Abstract: The present invention is various 7-deazaguanines having activity as immunomodulators. Also included are pharmaceutical compositions and methods of use thereof.
    Type: Grant
    Filed: February 1, 1990
    Date of Patent: February 26, 1991
    Assignee: Warner-Lambert Company
    Inventors: Thomas C. Malone, Jagadish C. Sircar
  • Patent number: 4994460
    Abstract: A series of 5-halopyrimidin-2-ylpiperazinylalkyl derivatives having useful anti-ischemic properties for treatment and prevention of dirorders resulting from brain and/or spinal cord anoxia.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: February 19, 1991
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Pierre Dextraze, Joseph P. Yevich
  • Patent number: 4992438
    Abstract: Disclosed are pyrimidine derivatives represented by general formula (I) ##STR1## wherein X represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group or a cyano group; Y.sup.1 represents an alkyl group, a cyanoalkyl group, an alkoxy group, an alkenyl group substituted with a hydroxy group and a halogen atom, an alkynyl group which may be substituted with a hydroxy group, a methylamino group, an alkoxyalkyloxy group, an alkylthioalkyl group or a group of the formula --CH.sub.2 OR.sup.1 where R.sup.1 represents a hydrogen atom, an alkyl group, an alkenyl group or an alkynyl group; Y.sup.2 represents a halogen atom, an alkyl group or a haloalkyl group; R represents a hydrogen atom, an alkyl group, a nitroso group, an alkoxyalkyl group, an alkoxyalkyloxyalkyl group, an alkenyl group, an alkynyl group, a formyl group or an alkylthioalkyl group, with the proviso that (a) when Y.sup.1 represents an alkynyl grop or when Y.sup.1 represents an alkoxy group and Y.sup.
    Type: Grant
    Filed: April 20, 1990
    Date of Patent: February 12, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Shigekazu Ito, Katsumi Masuda, Shoji Kasano, Toshihiro Nagata, Yoshiyuki Kojima, Nobumitsu Sawai, Shinichiro Maeno
  • Patent number: 4988704
    Abstract: Disclosed are pyrimidine derivatives represented by general formula ##STR1## wherein Z.sup.1 represents an alkynyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, or an alkynyloxy group which may be substituted with a halogen atom, and Z.sup.2 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a group of the formula ##STR2## where Z.sup.3 represents a hydrogen atom or a methyl group; or its salt, and processes for preparing same. Also, agricultural or horticultural compositions containing the pyrimidine derivatives as active ingredient are disclosed, which show high controlling activities for cucumber gray mold (Botrytis cinerea), cucumber downey mildew (Pseudoperonospora cubensis), Alternaria sooty spot of Chinese mustard (Alternaria brassicicola), rice blast (Pyricularia oryzae), etc.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: January 29, 1991
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Shigekazu Ito, Katsumi Masuda, Shoji Kusano, Toshihiro Nagata, Yoshiyuki Kojima, Nobumitsu Sawai, Shin-ichiro Maeno
  • Patent number: 4973592
    Abstract: New pharmacologically active heterocyclic derivatives as muscarinic receptor blocking agents, useful for the treatment of gastrointestinal disorders, of the following formula ##STR1## wherein the substituents are defined hereinbelow.
    Type: Grant
    Filed: September 13, 1988
    Date of Patent: November 27, 1990
    Assignee: Istituto de Angeli
    Inventors: Massimo Nicola, Arturo Donetti, Enzo Cereda, Marco Turconi, Giovanni B. Schiavi, Rosamaria Micheletti
  • Patent number: 4970307
    Abstract: A process for formation of a base from a base precursor, which comprises decomposing the base precursor in the presence of a catalyst. The base precursor has the following formula (I) or (II):(R.sup.1 --C.tbd.C--CO.sub.2 H).sub.x .multidot.B (I)R.sup.2 (--C.tbd.C--CO.sub.2 H).sub.2 .multidot.B.sub.y (II)wherein R.sup.1 is a monovalent group selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an aralkyl group, an acyl group, an alkoxycarbonyl group, carbamoyl, --CO.sub.2 M (M is an alkali metal) and --CO.sub.2 H.B, each of which may have one or more substituent groups; R.sup.
    Type: Grant
    Filed: August 13, 1987
    Date of Patent: November 13, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keiji Takeda, Jiro Tsukahara, Kozo Sato
  • Patent number: 4966622
    Abstract: The present invention relates to novel N-phenyl-N-pyrimidin-2-ylureas having a herbicidal and plant growth-regulating activity, to agrochemical compositions containing those substances as active ingredients, to the use of the novel ureas for controlling weeds or for regulating plant growth, and to processes for the preparation of the novel compounds. The invention also relates to novel intermediates and to processes for the preparation thereof.The novel compounds correspond to formula I ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 are each, independently of the others, hydrogen; halogen; C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 alkoxy; C.sub.1 -C.sub.4 haloalkyl; C.sub.1 -C.sub.4 haloalkoxy; C.sub.1 -C.sub.4 alkyl-S(O).sub.n -; nitro; cyano; C.sub.1 -C.sub.4 alkoxycarbonyl; C.sub.1 -C.sub.4 alkylcarbonyl; di-(C.sub.1 -C.sub.4 alkylamino)-carbonyl; mono-(C.sub.1 -C.sub.4 alkylamino)carbonyl; carbamoyl; C.sub.1 -C.sub.4 haloalkyl-S(O).sub.n -; or -PO[O-(C.sub.1 -C.sub.4)-alkyl].sub.2 ;R.sup.4 is C.sub.1 -C.
    Type: Grant
    Filed: April 3, 1989
    Date of Patent: October 30, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Hermann Rempfler, Dieter Durr, Rudolf C. Thummel
  • Patent number: 4962109
    Abstract: This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;R.sup.2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy;R.sup.3 is selected from hydrogen and halogen;R.sup.4 is the residue of an alcohol of formula R.sup.4 --OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; andX is selected from oxygen and sulphur.
    Type: Grant
    Filed: June 13, 1988
    Date of Patent: October 9, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventors: Edward McDonald, Roger Salmon, Alan J. Whittle
  • Patent number: 4952679
    Abstract: Reactive dyes suitable for dyeing and printing cellulosic fiber materials by the cold pad-batch process having the formula ##STR1## wherein Fa is a monoazo or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye radical, X.sub.1 is halogen, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl, a sulfonic acid or phosphoric acid group or a quaternized ammonium group, X.sub.2 independently has the meaning of X.sub.1 or is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 alkoxy, R is hydrogen or C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen, hydroxy, cyano, carboxyl, sulfo, sulfato, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.1 -C.sub.4 -alkoxy, and r is 1 or 2.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: August 28, 1990
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Hoegerle
  • Patent number: 4943675
    Abstract: Anilinopyrimidine derivatives of the formula: ##STR1## wherein R is --CH.sub.2 C(O)CH.sub.3 or --CH.dbd.C(Cl)CH.sub.3, are useful as intermediates in the production of anilinopyrimidine fungicides.
    Type: Grant
    Filed: June 15, 1989
    Date of Patent: July 24, 1990
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Takahiro Kimoto, Hideo Ohi, Toshihisa Watanabe, Tadashi Nakayama
  • Patent number: 4942234
    Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each, independently, hydrogen, lower alkyl, aryl or halo, or R.sup.1 and R.sup.2 taken together represent ##STR2## where the dotted lines represent optional double bonds; R.sup.3, R.sup.4 and R.sup.5 are each, independently, hydrogen, lower alkyl, aryl or halo;R.sup.6 is 2-pyridinyl, 2-pyrazinyl, 2-quinolyl, 2-quinoxalinyl or any of the foregoing R.sup.6 moieties substituted by lower alkyl, lower alkoxy, trifluoromethyl, cyano, nitro or halo; or ##STR3## wherein R.sup.7 is phenyl, 2-pyridinyl, 2-pyrimidinyl, 3-pyridazinyl or 2-pyrazinyl or any of the foregoing R.sup.7 moieties substituted by lower alkyl, lower alkoxy, halo, cyano, trifluoromethyl or nitro;Z is ##STR4## X is lower alkylene, vinylene, O or NH; m is 1-5;n is 0-4;p is 1-4;q is 1-2;and the pharmaceutically acceptable salts thereof, and their use as antipsychotic/anxiolytic agents having a low liability for extrapyramidal side effects.
    Type: Grant
    Filed: February 28, 1989
    Date of Patent: July 17, 1990
    Assignee: American Home Products Corporation
    Inventors: Magid A. Abou-Gharbia, Guy A. Schiehser, Usha R. Patel
  • Patent number: 4940792
    Abstract: Novel substituted N-sulfonyl-N'-pyrimidinylureas or N-sulfonyl-N'-triazinylureas of the formula I ##STR1## have good pre- and postemergence selective herbicidal and growth regulating properties.In this formulaE is nitrogen or --CH.dbd.,the group ##STR2## is a phenyl, naphthyl, furyl, thiophenyl, pyrrole or pyridinyl radical which is substituted in accordance with the definitions ofR.sup.1 and R.sup.2,R.sup.3 and R.sup.4 are hydrogen, lower alkyl or lower alkoxy, or one of R.sup.3 and R.sup.4 may also be halogen, lower alkenyl, lower haloalkenyl, lower haloalkoxy, amino, lower alkylamino, --CH(OCH.sub.3).sub.2, a cyclized ketal group or a saturated 5- or 7-membered heterocycle which is bound through the nitrogen atom,R.sup.5 is hydrogen, lower alkyl, lower haloalkyl, or an unsubstituted or substituted phenyl, benzyl or naphthyl radical, andR.sup.
    Type: Grant
    Filed: December 4, 1987
    Date of Patent: July 10, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Topfl, Willy Meyer, Hans-Dieter Schneider
  • Patent number: 4929621
    Abstract: A compound which is a pyrimidinylamino derivative of piperidine of formula (I) ##STR1## in which: X is a (CH.sub.2).sub.2, CH.dbd.CH or CH.sub.2 --CO group;Y is a CH.dbd.CH group or sulphur;n is 2, 3 or 4;R.sub.1 is hydrogen or a halogen;R.sub.2 is hydrogen or a (C.sub.1-4) alkyl group; andR.sub.3 is hydrogen or a hydroxy group;or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: August 29, 1989
    Date of Patent: May 29, 1990
    Assignee: Synthelabo
    Inventors: Philippe Manoury, Alfred Saarmets
  • Patent number: 4929729
    Abstract: The present invention relates to an industrially advantageous process for producing 2-amino-4,6-dichloropyrimidine, which comprises reacting 2-amino-4,6-dihydroxypyrimidine or its salt with phosphorus oxychloride at a temperature of from 50.degree. to 100.degree. C. in the presence of a solvent and an acid removing agent. Further, the yield of 2-amino-4,6-dichloropyrimidine can be improved by hydrolyzing 4,6-dichloro-2-pyrimidinylphosphoramidic dichloride produced as a by-product of the chlorination reaction to form 2-amino-4,6-dichloropyrimidine. The 2-amino-4,6-dichloropyrimidine produced by the process of the present invention is useful as an intermediate for medicines and agricultural chemicals.
    Type: Grant
    Filed: January 31, 1989
    Date of Patent: May 29, 1990
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Takahiro Haga, Yasuhiro Tsujii, Tatsuo Isogai, Shigeo Murai, Toshihiro Tanaka
  • Patent number: 4921858
    Abstract: The present invention is various 7-deazaguanines having activity as immunomodulators. Also included are pharmaceutical compositions and methods of use thereof.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: May 1, 1990
    Assignee: Warner-Lambert Company
    Inventors: Thomas C. Malone, Jagadish C. Sircar
  • Patent number: 4921632
    Abstract: Liquid Crystal compounds represented by the following formula are disclosed. ##STR1## wherein R and R' are independently selected from alkyl groups containing 1.about.20 carbon atoms; X is --O--, --O--CO--O-- or direct bond; A.sub.1 and A.sub.2 are independently cyclic groups (such as phenylene and biphenylene), said cyclic groups may be substituted with 1.about.4 fluorine, chlorine or bromine atoms, or 1 or 2 substituent groups selected from the group consisting of cyano, nitro and trifluoromethyl groups; Y is --CO--O--, --O--CO--, --C.tbd.C--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --CH.sub.2 S--, --SCH.sub.2 -- or direct bond; and * represents asymmetric atom providing optical activity.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: May 1, 1990
    Assignees: NEC Corporation, Sanyo Chemical Industries, Ltd.
    Inventors: Toyokazu Nakamura, Yuzi Kato, Shohei Naemura, Chizuka Tani, Masahiro Satoh, Kunikiyo Yoshio, Hiroshi Kishiki, Hiroshi Hoshino
  • Patent number: 4908446
    Abstract: The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. Suitable agents contain an active nitrogen-containing group, such as a hydrazine group. Particular agents comprise aminoguanidine derivatives. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.
    Type: Grant
    Filed: November 13, 1987
    Date of Patent: March 13, 1990
    Assignee: The Rockefeller University
    Inventors: Peter C. Ulrich, Anthony Cerami
  • Patent number: 4892871
    Abstract: The invention is directed to azido-substituted octopamine agonists and the radiolabeled derivatives thereof. The invention also relates to past controlling compositions comprising the azido-substituted octopamine agonists of the invention.The invention also relates to methods of controlling invertebrate pests by bringing the pest into contact with an invertebrate pest-controlling composition of the invention and to an apparatus for controlling invertebrate pests utilizing the pest-controlling compositions of the invention. The pest-controlling compositions may be used alone or in conjunction with ultraviolet light.The invention also relates to methods for the isolation of octopamine receptor proteins utilizing the radiolabeled azido-substituted octopamine agonists of the invention.
    Type: Grant
    Filed: April 12, 1988
    Date of Patent: January 9, 1990
    Assignee: The General Hospital Corporation
    Inventor: James A. Nathanson
  • Patent number: 4880932
    Abstract: A plant growth regulating compound of the formula ##STR1## in which R.sup.2 is an optionally substituted nitrogen heterocyclic radical,R.sup.3 is hydrogen, alkyl, cycloalkyl, alkenyl, alkinyl or aralkyl, andR.sup.4 is hydrogen, or if R.sup.3 is not hydrogen R.sup.4 may be hydroxyl or a variety of radicals, orR.sup.3 and R.sup.4 together may form a ring,or an acid adduct thereof.
    Type: Grant
    Filed: April 29, 1987
    Date of Patent: November 14, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Koichi Moriya, Theodor Pfister, Hans-Jochem Riebel, Ludwig Eue, Robert R. Schmidt, Klaus Lurrsen
  • Patent number: 4880824
    Abstract: Heterocyclic compounds of formulae (I) and (II): ##STR1## where R.sup.1 and R.sup.2 are alkyl, R.sup.3 is H or alkyl, m is 2-5 and Het is a hetercycle such as thiazole, benzothiazole, substituted benzothiazole, pyrazine, triazine, thiadiazole, substituted thiadiazole, pyrimidine or substituted pyrimidine. The compounds are calcium channel blockers useful in the treatment of cardiovascular conditions such as hypertension or angina.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: November 14, 1989
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Jeffery B. Press, Maud Urbanski
  • Patent number: 4876252
    Abstract: This disclosure describes novel 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines having antiasthmatic activity.
    Type: Grant
    Filed: May 17, 1988
    Date of Patent: October 24, 1989
    Assignee: American Cyanamid Company
    Inventors: Lawrence W. Torley, Bernard D. Johnson, John P. Dusza
  • Patent number: 4859679
    Abstract: Quaternary 8-(alkyldithio)-1-(2-pyrimidyl)-quinolinium salts, inhibitors of the H.sup.30 /K.sup.+ ATPase enzyme, are useful in the treatment of ulcers.
    Type: Grant
    Filed: July 19, 1988
    Date of Patent: August 22, 1989
    Assignee: Pfizer Inc.
    Inventor: Conrad Santini
  • Patent number: 4853387
    Abstract: A compound which is a piperidine derivative of formula (I) ##STR1## in which: n is 1, 2, 3 or 4,R is hydrogen or a halogen,R', which is identical to R, is hydrogen or a halogen,either R.sub.1 is H or OH and R.sub.2 is H, or R.sub.1 and R.sub.2 together denote a bond,R.sub.3 is hydrogen or (C.sub.1-4) alkyl, andR.sub.4 is H or OH,including tautomeric forms thereof, or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: July 22, 1988
    Date of Patent: August 1, 1989
    Assignee: Synthelabo
    Inventors: Philippe Manoury, Jean Binet, Elisabeth Dewitte
  • Patent number: 4833143
    Abstract: Compounds of formula I ##STR1## in which R.sub.1 is a heterocyclic ring containing one or more heteroatoms selected from N, O and S;in which R.sub.2 is H, a straight or branched chain alkyl group containing 1 to 4 carbon atoms, an alkenyl group containing 3 to 6 carbon atoms, an alkynyl group containing 3 to 6 carbon atoms or a cycloalkyl group containing 3 to 7 carbon atoms;in which R.sub.3, is H, a straight chain alkyl group containing 1 to 3 carbon atoms or a formyl groupin which R.sub.4, R.sub.5 and R.sub.6 which may be the same or different, are H, halo, trifluoromethyl, hydroxy, an alkyl group containing 1 to 3 carbon atoms, an alkoxy group containing 1 to 3 carbon atoms, phenyl or R.sub.4 and R.sub.5, together with the carbon atoms to which they are attached, form an optionally substituted second benzene ring;and their pharmaceutically acceptable salts have utility in the treatment of depression. Pharmaceutical compositions and processes for the preparation of compounds of formula I are disclosed.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: May 23, 1989
    Assignee: The Boots Company PLC
    Inventors: Bernard J. Armitage, John R. Housley, James E. Jeffery, David N. Johnston
  • Patent number: 4820710
    Abstract: Benzimidazole derivatives corresponding to the formula (1) ##STR1## in which X is CH or N,R.sub.1 is either a hydrogen atom, or a benzyl radical which can bear 1 to 3 substituents chosen from halogen atoms and trifluoromethyl, (C.sub.1-4)alkyl, (C.sub.1-4)alkoxy, cyano, methylthio, methylsulphinyl and methylsulphonyl radicals, or a methyl radical bearing a heterocyclic substituent in which the heterocyclic system can be a pyridyl, thienyl or furyl radical and can bear one or more substituents, R.sub.2 is a hydrogen atom or a (C.sub.1-4)alkyl radical, R.sub.3 is a hydrogen atom or a hydroxy radical, and R.sub.4 is a hydrogen atom or a (C.sub.1-4)alkyl radical, where appropriate, in tautomeric form when R.sub.3 is OH.The compounds may be used in treating allergy and histamine-induced inflammation.
    Type: Grant
    Filed: September 10, 1986
    Date of Patent: April 11, 1989
    Assignee: Synthelabo
    Inventors: Philippe Manoury, Jean Binet, Gerard Defosse
  • Patent number: 4818277
    Abstract: This invention relates to alkyl sulfones which are useful as herbicides and plant growth regulants.
    Type: Grant
    Filed: July 12, 1982
    Date of Patent: April 4, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Levitt George
  • Patent number: 4814338
    Abstract: Disclosed are pyrimidine derivatives represented by general formula ##STR1## wherein Z.sup.1 represents an alkynyl group, an alkenyl group, an alkoxy group, an alkenyloxy group, or an alkynyloxy group which may be substituted with a halogen atom, and Z.sup.2 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, or a group of the formula ##STR2## where Z.sup.3 represents a hydrogen atom or a methyl group; or its salt; and processes for preparing same. Also, agricultural or horticultural compositions containing the pyrimidine derivatives as active ingredient are disclosed, which show high controlling activities for cucumber gray mold (Botrytis cinerea), cucumber downey mildew (Pseudoperonospora cubensis), Alternaria sooty spot of Chinese mustard (Alternaria brassicicola), rice blast (Pyricularia oryzae), etc.
    Type: Grant
    Filed: October 29, 1986
    Date of Patent: March 21, 1989
    Assignees: Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
    Inventors: Shigekazu Ito, Katsumi Masuda, Shoji Kusano, Toshihiro Nagata, Yoshiyuki Kojima, Nobumitsu Sawai, Shin-ichiro Maeno
  • Patent number: 4808621
    Abstract: Certain trans-6-[2-(N-heteroaryl-3,5-disubstituted)pyrazol-4-yl)ethyl]- or ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-ones and the corresponding ring-opened acids derived therefrom which are potent inhibitors of the enzyme 3-hydroxy-3-methylglutarylcoenzyme A reductase (HMG CoA reductase) and are thus useful hypolipidemic or hypocholesterolemic agents. Pharmaceutical compositions containing such compounds, and a method of inhibiting the biosynthesis of cholesterol employing such pharmaceutical compositions are also disclosed.
    Type: Grant
    Filed: May 18, 1987
    Date of Patent: February 28, 1989
    Assignee: Warner-Lambert Company
    Inventors: Bruce D. Roth, Drago R. Sliskovic
  • Patent number: 4798894
    Abstract: Compounds containing at least one N,N-dialkylatable amino or amido group (e.g., aniline, dodecylamine, acetamide) are converted in a highly efficient manner into gem cyclodialkylated compounds by reaction with an unstrained cyclic ether (e.g., tetrahydrofuran) or a polyol (e.g., 1,4-butane diol) cyclizable to an unstrained ether using titanium dioxide catalysts that have prior to use:(1) a surface area of at least 70 square meters per gram (as determined by the BET method), and(2) the capability of chemically adsorbing at 100.degree. C. at least 35.times.10.sup.4 millimoles of gaseous ammonia per square meter of surface area.
    Type: Grant
    Filed: May 11, 1987
    Date of Patent: January 17, 1989
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • 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: 4795812
    Abstract: This invention describes the synthesis and anti-neoplastic use of 4-aziridyl-5-substituted/unsubstituted 6-aryl-pyrimidine compounds of Formula IA ##STR1## as well as N'-[2-(1-aziridyl)ethyl]-6-aryl-2,4-pyrimidinediamines of Formula IB ##STR2## and 4-chloro or bromo-5-substituted/unstubstituted-6-aryl-pyrimidines.
    Type: Grant
    Filed: September 22, 1986
    Date of Patent: January 3, 1989
    Assignee: The Upjohn Company
    Inventors: Wendell Wierenga, Harvey I. Skulnick
  • Patent number: 4788195
    Abstract: This disclosure describes novel 4,5,6-substituted-N-(substituted-phenyl)-2-pyrimidinamines having anti-asthmatic activity.
    Type: Grant
    Filed: November 6, 1986
    Date of Patent: November 29, 1988
    Assignee: American Cyanamid Company
    Inventors: Lawrence W. Torley, Bernard D. Johnson, John P. Dusza
  • Patent number: 4783459
    Abstract: There are described new pyrimidine derivatives of the general formula I ##STR1## in which n is 0, 1 or 2;R.sub.1 is(a) the group --CXR.sub.5, where X is oxygen or sulphur and R.sub.5 is hydrogen, a nitrogen or sulphur containing heterocyclic group, which can contain other hetero atoms, optionally substituted alkenyl, acyl, alkoxycarbonyl, alkyl substituted by aryloxy, or optionally substituted mono- or dialkylamino; or R.sub.5 is the group --NHR.sub.6, where R.sub.6 is substituted amino, substituted carbamoyl, optionally substituted alkylsulphonyl, acyl or arylsulphonyl, and when n is 0 or when X is sulphur, R.sub.5 can also be alkyl, haloalkyl, aryl, aralkyl, alkoxycarbonylalkyl or arylamino;(b) cyano or the group --CXYR.sub.7, where X and Y are the same or different and are oxygen, sulphur or optionally substituted imino and R.sub.
    Type: Grant
    Filed: April 23, 1987
    Date of Patent: November 8, 1988
    Assignee: Schering Agrochemicals Ltd.
    Inventors: Ulrich Buhmann, Jurgen Westermann, Dietrich Baumert, Ernst Pieroh, Geoffrey R. Cliff, Ian C. Richards
  • Patent number: 4772609
    Abstract: This invention relates to antiviral organic guanidine derivatives compositions; a process of producing the antiviral compositions; and a method for inhibiting viruses utilizing the compositions. More particularly, the compositions are tubastrines derived from marine coral tubastrea aurea.
    Type: Grant
    Filed: June 26, 1986
    Date of Patent: September 20, 1988
    Assignee: Harbor Branch Oceanographic Institution, Inc.
    Inventors: Tatsuo Higa, Ryuichi Sakai
  • Patent number: 4762932
    Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: August 9, 1988
    Assignees: Imperial Chemical Industries, Ltd., ICI Americas, Inc.
    Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
  • Patent number: 4748165
    Abstract: This invention relates to amidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is hydrogen or a 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl radical, the latter three being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene or a 1-8C alkylene chain into which is optionally inserted one or two groups; and R.sup.2 and R.sup.3 are a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.
    Type: Grant
    Filed: May 11, 1982
    Date of Patent: May 31, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4725304
    Abstract: Novel herbicidally active fluoroalkoxyphenylsulphonylguanidines of the formula ##STR1## in which M is hydrogen or one equivalent of a metal,R.sup.1 is fluorine-substituted alkyl, andR.sup.2, R.sup.3 and R.sup.4 each independently is hydrogen or various organic radicals,or 1:1 adducts thereof with strong acids.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: February 16, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Diehr, Christa Fest, Rolf Kirsten, Joachim Kluth, Klaus-Helmut Muller, Theodor Pfister, Uwe Priesnitz, Hans-Jochem Riebel, Wolfgang Roy, Hans-Joachim Santel, Robert R. Schmidt
  • Patent number: 4723006
    Abstract: New compounds useful as intermediates for biologically-active compounds have the formula I ##STR1## wherein Y is a group having the formula --CH.sub.2 X in which X is F, Cl, or Br, or Y is a group having the formula ##STR2## in which R.sup.2 is F, Cl or Br and R.sup.3 is H, F, Cl, Br or a group having the formula --CR.sup.4 R.sup.5 R.sup.6, in which R.sup.4, R.sup.5 and R.sup.6, independently, are F, Cl or Br; A is H, OH, SH, F, Cl, Br or a group --OR.sup.7 or --SR.sup.7 in which R.sup.7 is C.sub.1 -C.sub.4 straight- or branched chain alkyl, C.sub.2-4 straight- or branched chain alkyl substituted with 1 to 3 F, Cl or Br atoms, or A is a group --NR.sup.8 R.sup.9 in which R.sup.8 and R.sup.9, independently, are H, C.sub.1 -C.sub.4 straight- or branched chain alkyl or C.sub.3 -C.sub.4 alkenyl, or R.sup.8 and R.sup.9 together may form a C.sub.3 -C.sub.7 polymethylene chain, which is optionally interrupted by an oxygen atom; as well as salts of compounds of formula I with acids; provided that: when Y is CH.sub.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: February 2, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert L. Bentley, Brian Tuck
  • Patent number: 4723005
    Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.
    Type: Grant
    Filed: September 10, 1984
    Date of Patent: February 2, 1988
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Tuong Huynh-Ba, Maged A. Osman