Nitrogen Attached Indirectly To The Six-membered Hetero Ring By Nonionic Bonding Patents (Class 546/329)
  • Patent number: 5424437
    Abstract: A 2-Chloro-5-aminomethylpyridine is prepared in one step by reacting 2-chloro-5-trichloromethylpyridine with an amine and hydrogen in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: June 13, 1995
    Assignee: Koei Chemical Co., Ltd.
    Inventors: Katsuhiro Ieno, Yoshihiro Kawanami
  • Patent number: 5418244
    Abstract: Compounds of the formula ##STR1## wherein the variables are defined in the specification. The compounds and their salts are soft anticholinergic/antisecretory agents especially useful as mydriatics and as antiperspirants.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: May 23, 1995
    Assignee: University of Florida
    Inventors: Richard H. Hammer, Nicholas S. Bodor
  • Patent number: 5414122
    Abstract: There is disclosed an efficient process for producing .alpha.-ketoacetamide of the formula: ##STR1## which is useful as an intermediate for the production of various alkoxyiminoacetamide compounds to be used for agricultural fungicides. In this process, a corresponding acid halide is condensed with isocyanide to produce the .alpha.-ketoacetamide.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: May 9, 1995
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
  • Patent number: 5411936
    Abstract: Cyclohexenone oxime ethers of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is substituted or unsubstituted C.sub.4 -alkylene or C.sub.4 -alkenylene,x is nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl and/or phenyl,n is from 0 to 3 or from 1 to 5 when X is halogen,R.sup.2 is C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: May 2, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5391772
    Abstract: Described is a process for converting an alcohol to an azide with S.sub.N 2 inversion using a phosphoryl azide, e.g. diphenylphosphoryl azide (DPPA). Good yields of azide in high enantiomeric excess can be achieved specifically for benzylic alcohols and alpha-hydroxy alkyl esters. The process is carried at preferably room temperature in an inert dry aprotic solvent, e.g. toluene, and in the presence of a proton acceptor, e.g. 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford high yields of high enantiomeric purities.
    Type: Grant
    Filed: July 8, 1993
    Date of Patent: February 21, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Andrew S. Thompson, Edward J. J. Grabowski
  • Patent number: 5382671
    Abstract: The invention relates to a new process for the preparation of 2-chloro-5-alkylaminomethyl-pyridines of the formula (I) ##STR1## in which R represents alkyl. In this process, 2-chloro-5-aminomethyl-pyridine is reacted with formic acid at temperatures between 20.degree. C. and 200.degree. C., if appropriate in the presence of a diluent, the 2-chloro-5-formylaminomethyl-pyridine which has been formed in this process is reacted without intermediate isolation (in situ) with alkylating agents at temperatures between 0.degree. C. and 100.degree. C., if appropriate in the presence of an acid acceptor, if appropriate in the presence of a diluent, and, finally, the 2-chloro-5-(N-alkyl-N-formyl-aminomethyl)-pyridines thus formed of the general formula (V) ##STR2## in which R has the abovementioned meaning,are reacted with aqueous alkali metal hydroxide solution at temperatures between 20.degree. C. and reflux temperature, if appropriate after volatile components have been distilled off.
    Type: Grant
    Filed: February 9, 1993
    Date of Patent: January 17, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Diehr
  • Patent number: 5374724
    Abstract: A process for the preparation of a substituted acetic acid of the Formula (2): ##STR1## wherein --X--Z is an optionally substituted aromatic or heteroaromatic optionally substituted amino radical; by reacting a compound of the Formula (7):Z--Y--H Formula 7with glyoxylic acid. The compounds of Formula (2) are useful as intermediates in the preparation of polycyclic dyes.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: December 20, 1994
    Assignee: Zeneca, Limited
    Inventors: Nigel Hall, Nigel Hughes, Prakash Patel
  • Patent number: 5366982
    Abstract: This invention relates to compounds having selective LTB.sub.4 antagonist properties, compositions comprising said compounds and methods for the treatment of disorders involving LTB.sub.4 agonist-mediated activity utilizing said compositions wherein the compounds are described by the general formula ##STR1## and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: February 17, 1993
    Date of Patent: November 22, 1994
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventors: Norbert Dereu, Wolfram Hendel, Richard Labaudiniere
  • Patent number: 5364989
    Abstract: Methods for the production of 1,1,1-trihalogeno-2-nitroethanes from 1,1-dihalogenoethylene by using nitric acid or its salt and hydrogen chloride or hydrogen bromide or its salt, and for the production of .alpha.-unsaturated amines from the 1,1,1-trihalogeno-2-nitroethanes which are useful as insecticides.
    Type: Grant
    Filed: July 6, 1992
    Date of Patent: November 15, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Isao Aoki, Takanori Tabuchi, Isao Minamida
  • Patent number: 5352794
    Abstract: The present invention relates to a new process for the preparation of N-(2-chloro-pyridin-5-yl-methyl)-ethylenediamine.The process is characterised in that 6-chloronicotinaldehyde is reacted with 1,2-ethylenediamine and a reducing agent at temperatures between -30.degree. C. and +50.degree. C.The reducing agents employed are preferably metal hydride complexes and, in particular, sodium borohydride.N-(2-Chloro-pyridin-5-yl-methyl)-ethylenediamine, which is to be prepared by the process according to the invention, can be used as intermediate for the preparation of insecticides.
    Type: Grant
    Filed: November 3, 1992
    Date of Patent: October 4, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventor: Reinhard Lantzsch
  • Patent number: 5314901
    Abstract: Compounds of formula (I) or a pharmaceutically acceptable salt thereof, wherein R.sub.1 represents a 1,2,5,6-tetrahydropyridin-3-yl group N-substituted by R.sub.10 wherein R.sub.10 represents hydrogen, C.sub.1-2 alkyl, prop-2-enyl, prop-2-ynyl or cyclopropyl, R.sub.2 is a group OR.sub.4, where R.sub.4 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, a group OCOR.sub.5 where R.sub.5 is hydrogen or R.sub.4, or a group NHR.sub.6, or NR.sub.7 R.sub.8 where R.sub.6, R.sub.7 and R.sub.8 are independently C.sub.1-2 alkyl; and R.sub.3 is chloro, fluoro, bromo, methoxy, C.sub.1-3 alkyl substituted by one, two or three halogen atoms, or R.sub.3 is a group (CH.sub.2).sub.n R.sub.9 where R.sub.9 is --CN, --SH or --SCH.sub.3 and n is 0 or 1, with the proviso that when n is 0, R.sub.9 is not --SH; enhance acetylcholine function via an action at muscarinic receptors within the central nervous system and are therefore of potential use in the treatment and/or prophylaxis of dementia in mammals.
    Type: Grant
    Filed: February 23, 1993
    Date of Patent: May 24, 1994
    Assignee: Beecham Group p.l.c.
    Inventors: Steven M. Bromidge, Barry S. Orlek, Steven Dabbs
  • Patent number: 5306821
    Abstract: This invention relates to a novel process for the preparation of tertiary carbinamines by double addition of organolanthanide reagents, especially organocerium reagents, to nitriles. It further relates to the preparation of such amines by the addition of organolanthanide reagents to imines.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: April 26, 1994
    Assignee: The Du Pont Merck Pharmaceutical Company
    Inventor: Engelbert Ciganek
  • Patent number: 5306728
    Abstract: Substituted amine derivatives represented by the general formula ##STR1## wherein Q is -C-D-E- F-G-M- or -N-H-I-J-K-L- [C, D, E, F, G, H, I, J, K and L are each O, S, a carbonyl group, -CHR.sup.2 -, -R.sup.b = or -NR.sup.c - (R.sup.a, R.sup.b and R.sup.c are each H or a lower alkyl group), M and N are each an aromatic ring of 5-6 members optionally having a halogen, OH, LN, a lower alkyl group or a lower alkoxy group, provided that L is not O, S, or -NR.sup.c -]; R is a heterocyclic ring of 5-6 members; R.sup.1 is H, a lower alkyl group, a lower haloalkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group; R.sup.2, R.sup.3, R.sup.4, R.sup.5 R.sup.6 and R.sup.7 are each H, a halogen or a lower alkyl group or two of them denote a single bond; R.sup.8 and R.sup.9 are each F, CF.sub.3 or a lower alkyl group or are a cycloalkane in combination thereof; and R.sup.10 is H, F, CF.sub. 3 an acetoxy group, a lower alkyl group or a lower alkoxy group.
    Type: Grant
    Filed: March 4, 1993
    Date of Patent: April 26, 1994
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Yoshimi Tsuchiya, Takashi Nomoto, Masahiro Hayashi, Yoshikazu Iwasawa, Hitoshi Masaki, Mitsuru Ohkubo, Yumiko Sakuma, Yasufumi Nagata, Toshihiko Satoh, Toshio Kamei
  • Patent number: 5304566
    Abstract: The present invention relates to a compound having the formula below which has an excellent inseciticidal activity: ##STR1## wherein R.sub.1 represents an optionally substituted 5-6 membered aromatic hetero ring containing nitrogen atom, except a non-substituted 2-pyridyl; x represents an optionally substituted C.sub.1-3 alkyleneR.sub.2 represents a hydrogen, a carbamoyl, a mono or di C.sub.1-5 alkyl carbamoyl, a thiocarbamoyl, a mono or di C.sub.1-5 alkylthiocarbamoyl, a sulfamoyl, a mono or di C.sub.1-5 alkylsulfamoyl, an optionally substituted C.sub.1-5 alkyl, an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.sub.2-5 alkynyl, an optionally substituted C.sub.3-8 cycloalkyl, an optionally substituted C.sub.3-8 cycloalkenyl, an optionally substituted aryl or --Y--R.sub.5 ;Y represents O, S(O).sub.n, CO, CS or CO.sub.2 ;n represents 0, 1 or 2;R.sub.5 represents a hydrogen, an optionally substituted C.sub.1-5 alkyl, an optionally substituted C.sub.2-5 alkenyl, an optionally substituted C.
    Type: Grant
    Filed: July 9, 1991
    Date of Patent: April 19, 1994
    Assignee: Nippon Soda Co., Ltd
    Inventors: Keiichi Ishimitsu, Junji Suzuki, Haruhito Ohishi, Tomio Yamada, Renpei Hatano, Nobuo Takakusha, Jun Mitsui
  • Patent number: 5300650
    Abstract: A process for producing an aminomethylpyridine having a chlorine atom at the .alpha.-position, for example, 2-chloro-5-aminomethylpyridine by subjecting a cyanopyridine having a chlorine atom at the .alpha.-position, for example, 2-chloro-5-cyanopyridine, to a catalytic reduction in the presence of a tertiary amine in a non-aqueous reaction system.With the process, the removal of the chlorine atom bonding to the .alpha.-position can be depressed and an aminomethylpyridine having a chlorine atom at the .alpha.-position can be produced at a high yield.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: April 5, 1994
    Assignee: Koei Chemical Co., Ltd.
    Inventor: Toshinari Nabata
  • Patent number: 5292760
    Abstract: Novel 4,5-dihydro-4-heteroaryl-3H-1,3-benzodiazepines, intermediates, processes for the preparation thereof, and methods for treating depression, inhibiting convulsions and treating anxiety utilizing compounds and compositions thereof are disclosed.
    Type: Grant
    Filed: April 22, 1992
    Date of Patent: March 8, 1994
    Assignee: Hoechst-Roussel Pharmaceuticals Inc.
    Inventors: Lawrence L. Martin, Joseph F. Payack, Salvatore M. Brucato
  • Patent number: 5286893
    Abstract: Alkenoic acid compounds are described. The compounds which are dehydropeptidase inactivators contain a ##STR1## moiety which is substituted with a halomethylene or a cyano moiety as R.sub.3. The enzyme deprotonates the alpha --CH.sub.2 group and then the intermediate compound forms a covalent bond with enzymic residue in the active site, resulting in irreversible inactivation of the enzyme. The compounds are particularly inactivators of renal dipeptidases.
    Type: Grant
    Filed: January 28, 1992
    Date of Patent: February 15, 1994
    Assignee: Board of Governors of Wayne State University
    Inventor: Shahriar Mobashery
  • Patent number: 5273977
    Abstract: Substituted tetrahydropyridines and hydroxypiperidines and derivatives thereof are described, as well as methods for the preparation and pharmaceutical composition of the same, which are useful as central nervous system agents and are particularly useful as dopaminergic, antipsychotic, and antihypertensive agents as well as for treating hyperprolactinaemia-related conditions and central nervous system disorders.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: December 28, 1993
    Assignee: Warner-Lambert Company
    Inventors: Shelly Glase, Juan C. Jaen, Sarah J. Smith, Lawrence D. Wise
  • Patent number: 5258551
    Abstract: There is disclosed an efficient process for producing .alpha.-ketoacetamide of the formula: ##STR1## which is useful as an intermediate for the production of various alkoxyiminoacetamide compounds to be used for agricultural fungicides. In this process, a corresponding acid halide is condensed with isocyanide to produced the .alpha.-ketoacetamide.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: November 2, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Murabayashi, Hideyuki Takenaka, Hiroyuki Kai
  • Patent number: 5252741
    Abstract: Imines are synthesized by the hydrogenation of pyridinecarbonitriles with amines in the presence of a rhodium-loaded catalyst. The resulting imines are stable and may be transiminated and then hydrogenated to form selected secondary amine products or may be hydrolyzed to aldehydes.Further, a very useful class of unsymmetrical secondary amines represented by the formula RCH.sub.2 NHAr (in which R is not aliphatic and Ar is aromatic and not attached to R), which has heretofore been accessible only with some difficulty, can be synthesized by processes herein disclosed utilizing the reductive intermolecular coupling of nitriles and primary aromatic amines.
    Type: Grant
    Filed: April 20, 1992
    Date of Patent: October 12, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Gerald L. Goe, James G. Keay, Eric F. V. Scriven, Michael L. Prunier, Steven J. Quimby
  • Patent number: 5250550
    Abstract: There are disclosed novel complexes of nitric oxide and polyamines which are useful in treating cardiovascular disorders, including hypertension. The disclosed compounds release nitric oxide (endothelium-derived relaxing factor) under physiological conditions in a sustained and controllable fashion, and possess long mechanisms of action.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: October 5, 1993
    Assignee: The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Larry K. Keefer, Joseph A. Hrabie
  • Patent number: 5245030
    Abstract: An IR-ray absorptive compound represented by the formula (1) or (2): ##STR1## and an optical recording medium having a substrate and an organic dye thin film, comprising the formulae (1) and/or (2).
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: September 14, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Tetsuro Fukui, Yoshihiro Oguchi, Hiroyuki Sugata, Kyo Miura
  • Patent number: 5243051
    Abstract: The present invention relates to tetrahydropyridine derivatives which have high affinity and specificity to .sigma. receptors, whereby these compounds are thought to be effective for treatment of some psychoses.
    Type: Grant
    Filed: June 26, 1992
    Date of Patent: September 7, 1993
    Assignee: Shionigi & Co., Ltd.
    Inventors: Hiromu Matsumura, Toshisada Yano, Hiroshi Hashizume, Akira Matsushita, Masami Eigyo
  • Patent number: 5223626
    Abstract: Compounds of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are each independently of the others hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or C.sub.1 -C.sub.4 alkanoylamino,R is hydrogen or unsubstituted or C.sub.1 -C.sub.4 alkoxy substituted C.sub.1 -C.sub.12 alkyl or an --(alk)--NA.sup..sym. X.sup..crclbar. radical or,R forms together with an R.sub.1 in the ortho-position relative to the amino group a partially hydrogenated, substituted or unsubstituted 5- to 7-membered heterocyclic ring which may contain additional N, S or O atoms as ring members, (alk) is a substituted or unsubstituted C.sub.1 -C.sub.6 alkylene radical,--NA.sup..sym. is the radical of an amino compound of formula ##STR2## where R.sub.4, R.sub.5 and R.sub.6 are each independently of the others substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, substituted or unsubstituted C.sub.7 -C.sub.12 aralkyl or substituted or unsubstituted aryl, R.sub.8 and R.sub.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: June 29, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Janos Vincze, Wilfried Herter
  • Patent number: 5216170
    Abstract: A compound for promoting livestock production and for controlling obesity in humans and animals, of the formula ##STR1## in which A represents .dbd.CH-- or .dbd.N--,R.sup.0 represents hydrogen or methyl,R.sup.1 and R.sup.3 each independently represents hydrogen, hydroxyl, halogen, cyano, alkyl, halogenoalkyl, hydroxyalkyl, alkoxycarbonyl, aminocarbonyl, mono- and dialkylaminocarbonyl, alkoxy, halogenoalkoxy, halogenoalkylthio, NHSO.sub.2 -alkyl,R.sup.2 represents hydrogen, hydroxyl, alkoxy or the radical --NR.sup.5 R.sup.6,R.sup.4 represents hydrogen, C.sub.1 -C.sub.10 -alkyl which is optionally substituted by hydroxyl, halogen, alkoxy, acyloxy or the radical --NR.sup.7 R.sup.8, or represents the radical COR.sup.9 or the radical --O--Z--R.sup.10,Z represents C.sub.1 -C.sub.10 -alkylene, -alkenylene or alkynylene,R.sup.5 represents hydrogen or alkyl,R.sup.6 represents hydrogen, alkyl, halogenoalkyl or acyl, or R.sup.5 and R.sup.
    Type: Grant
    Filed: March 28, 1991
    Date of Patent: June 1, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Lindel, Werner Hallenbach, Friedrich Berschauer, Heinrich A. Greife, Gernot Klotz
  • Patent number: 5202326
    Abstract: The invention concerns a heterocyclic ether of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl or (2-4 C)alkanoyl, or optionally substituted benzoyl;R.sup.2 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl; andR.sup.3 is substituted (1-4C)alkyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: April 13, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Jean-Marc M. M. Girodeau
  • Patent number: 5200561
    Abstract: Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: April 6, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Naoto Konya, Yukio Yoneyoshi, Yoji Sakito, Shinji Nishii, Gohfu Suzukamo, Hiroko Sakane
  • Patent number: 5196433
    Abstract: Compounds of the Formula ##STR1## where R is alkyl or cycloalkyl,X,Y,Z are hydrogen, halogen, alkyl, alkoxy, alkoximino, haloalkyl, cyano, niro or substituted or unsubstituted phenyl or phenoxy,W is a single bond or one of the groups --CH.sub.2 --, --CH(CH.sub.3)-- or --CH.sub.2 CH.sub.2 -- andn is 0 or 1, andplant-tolerated acid addition salts thereof, and fungicides containing these compounds.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: March 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Zierke, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5196454
    Abstract: The invention relates to novel 2,5-diaminotetralines of the formula: ##STR1## wherein R1, R2, R3 and R4 are defined herein, processes for preparing them and their use in pharmaceutical compositions. The novel 2,5-diaminotetralines are useful in treating diseases caused by disorders of the dopaminergic systems.
    Type: Grant
    Filed: June 15, 1990
    Date of Patent: March 23, 1993
    Assignee: Boehringer Ingelheim KG
    Inventors: Matthias Grauert, Herbert Merz, Joachim Mierau, Gunter Schingnitz, Claus Schneider
  • Patent number: 5194984
    Abstract: 4'-Dimethylamino-4-methylstilbazolium methanesulfonate is prepared by the reaction of methyl methanesulfonate with 4-picoline followed by condensation with p-dimethylaminobenzaldehyde. Its hydrated form has second harmonic generation optical properties, but this is not true of the anhydrous form. Thus, the hydrated form is useful in the production of optical waveguides, spatial light modulators and the like.
    Type: Grant
    Filed: June 10, 1991
    Date of Patent: March 16, 1993
    Assignee: General Electric Company
    Inventors: Eugene P. Boden, Peter D. Phelps, Christopher P. Yakymyshyn, Kevin R. Stewart
  • Patent number: 5180822
    Abstract: Described are preferred monomers including a vinylbenzyl moiety N-bonded to an alkylaminopyridinyl or pyridylimidazolyl function. Also described are preferred acid salts of such monomers. Additionally, preferred processes involving and resins formed from these preferred monomers are described. The preferred resins are highly selective for valuable heavy metal ions such as copper and demonstrate superior iron rejection values.
    Type: Grant
    Filed: August 27, 1991
    Date of Patent: January 19, 1993
    Assignee: Reilly Industries, Inc.
    Inventors: Donald W. McQuigg, Edward E. Sowers
  • Patent number: 5180827
    Abstract: The invention relates to the 2-(3-pyridyl)-propanenitrile intermediates of formula (V): ##STR1## in which: R denotesa lower alkyl radical, optionally substituted with one or more substituents chosen from halogen, and preferably chlorine, fluorine or bromine, atoms, a lower alkoxy radical and a radical --(CH.sub.2).sub.x Si R.sub.1 R.sub.2 R.sub.3, x=0 or 1 and R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, being lower alkyl, lower alkoxy, aryl (in particular phenyl) or aralkyl (in particular benzyl);an alkenyl, and preferably allyl, radical, optionally substituted as when R denotes alkyl or with a C.sub.1 to C.sub.3 alkyl group;Hal denotes a halogen atom;Z denotes a lower alkyl or lower alkoxy radical; andm denotes 0, 1 or 2, the groups Z being identical or different when m is 2.
    Type: Grant
    Filed: December 31, 1990
    Date of Patent: January 19, 1993
    Assignee: Rhone-Poulenc Agrochimie
    Inventors: Alain Gadras, Regis Pepin
  • Patent number: 5175301
    Abstract: .alpha.-Unsaturated amines of the formula: ##STR1## wherein X.sup.1 and X.sup.2 are such that one is an electron-attracting group with the other being a hydrogen atom or an electron-attracting group; R.sup.1 is a group attached through a nitrogen atom; R.sup.2 is a hydrogen atom or a group attached through a carbon, nitrogen or oxygen atom; n is an integer equal to 0, 1 or 2; A is a heterocyclic group or a cyclic hydrocarbon group, and salts thereof and their agrochemical use as insecticidal and/or miticidal agents are described.
    Type: Grant
    Filed: September 13, 1989
    Date of Patent: December 29, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Isao Minamida, Koichi Iwanaga, Tetsuo Okauchi
  • Patent number: 5175167
    Abstract: Hetarylalkenes of the general formula I ##STR1## where Ar is hetaryl,A is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl or unsubstituted or monosubstituted, disubstituted or trisubstituted aryl or aralkyl, ##STR2## Z is whereR is hydrogen, C.sub.2 -C.sub.4 -acyl, unsubstituted or substituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, unsubstituted or C.sub.1 -C.sub.4 -alkyl-substituted phenylsulfonyl or a radical R.sup.1,R.sup.1 is C.sub.1 -C.sub.4 -alkyl or unsubstituted or substituted phenyl or benzyland Hal is fluorine, chlorine, bromine or iodine,and B is unsubstituted or substituted mononuclear or dinuclear aryl, aralkyl or hetaryl,and their N-oxides and addition salts, the preparation of these substances, intermediates for this purpose and the preparation thereof, fungicides containing hetarylalkenes and a corresponding method for controlling harmful fungi.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: December 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Zipperer, Manfred Lauer, Norbert Goetz, Thomas Zierke, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5171859
    Abstract: This invention relates to novel substituted imidazo[1,5-a]pyridines, most especially novel 8-phenylimidazo[1,5-a]pyridines. It also relates to novel intermediates and to a novel process for the preparation of certain of these compounds. The compounds of the invention have been found to have significant cardiotonic, antiarrhythmic, hypotensive, CNS stimulant, and other pharmacological effects.
    Type: Grant
    Filed: April 18, 1991
    Date of Patent: December 15, 1992
    Assignee: Schering A.G.
    Inventor: David D. Davey
  • Patent number: 5164508
    Abstract: The present invention relates to a new process for the preparation of N-(2-chloro-pyridin-5-yl-methyl)-ethylene-diamine of the formula (I) ##STR1## in a technically simple manner in high yield and in very good quality. The new process is characterized in that N-(2-chloro-pyridin-5-yl-methyl)-aminoacetonitrile of the formula (II) ##STR2## is reacted with hydrogen in the presence of ammonia and in the presence of a catalyst and also in the presence of a diluent, at temperatures between 0.degree. C. and 100.degree. C. and a pressure between 1 bar and 100 bar.N-(2-Chloro-pyridin-5-yl-methyl)-ethylenediamine (I) can be used as an intermediate for the preparation of insecticides.
    Type: Grant
    Filed: August 28, 1991
    Date of Patent: November 17, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Diehr
  • Patent number: 5164499
    Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
    Type: Grant
    Filed: January 2, 1990
    Date of Patent: November 17, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thaliyil V. Rajanbabu
  • Patent number: 5151428
    Abstract: A pyridine derivative of the formula: ##STR1## wherein R.sup.1 is, the same or different, each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.1 -C.sub.4 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy gorup, a C.sub.1 -C.sub.3 haloalkoxy group, a cyano group or a nitro group; R.sup.2 is, the same or different, each a hydrogen atom, a halogen atom or a methyl group; R.sup.3 is a halogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sub.4 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group; R.sup.5 is, the same or different, each a halogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 haloalkyl group, a C.sub.1 -C.sub.3 alkoxy group or a C.sub.1 -C.sub.3 haloalkoxy group; X is an oxygen atom, a sulfur atom, a carbonyl group, a sulfinyl group, a sulfonyl group, an imino group or a methylene group; Y is an oxygen atom or a sulfur atom; l is an integer of 1 to 5; m is an integer of 1 to 3; and n is an integer of 1 to 4, which is useful for control of insect pest.
    Type: Grant
    Filed: May 24, 1991
    Date of Patent: September 29, 1992
    Inventors: Noriyasu Sakamoto, Hirosi Kisida, Hiroaki Fujimoto, Kimitoshi Umeda, Noritada Matsuo
  • Patent number: 5149817
    Abstract: The present invention relates to tetrahydropyridine derivatives which have high affinity and specificity to .sigma. receptors, whereby these compounds are thought to be effective for treatment of some psychoses.
    Type: Grant
    Filed: February 15, 1991
    Date of Patent: September 22, 1992
    Assignee: Shionogi & Co., Ltd.
    Inventors: Hiromu Matsumura, Toshisada Yano, Hiroshi Hashizume, Akira Matsushita, Masami Eigyo
  • Patent number: 5137923
    Abstract: Lipophilic quaternary ammonium salicylate, characterized in that it corresponds to the formula: ##STR1## in which: (i) R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, denote an alkyl or alkylcycloalkyl radical, optionally substituted or interrupted;(ii) R.sub.3 and/or R.sub.4 denote(s) a group:R.sub.8 --OC.sub.2 H.sub.3 R.sub.7 ].sub.n [OCH.sub.2 CHOH--CH.sub.2 ].sub.pin which: 0.ltoreq.n.ltoreq.4 and p denotes 0 or 1; R.sub.8 denotes H or an alkyl, alkenyl, alkylcycloalkyl or alkylaryl radical;(iii) R.sub.4 denotes an alkylphenyl radical;(iv), (v) R.sub.1 and R.sub.2 can form a saturated or unsaturated aromatic or non-aromatic heterocycle;(vi) R.sub.1, R.sub.2 and R.sub.3 form polycyclic derivatives with the nitrogen atoms; R.sub.5 denotes a group corresponding to the formula: ##STR2## in which n is an integer varying between 0 and 10.
    Type: Grant
    Filed: June 21, 1990
    Date of Patent: August 11, 1992
    Assignee: L'Oreal
    Inventors: Michel Philippe, Henri Sebag, Michel Hocquaux, Bernard Jacquet, Jean P. Laugier
  • Patent number: 5138062
    Abstract: This invention provides a class of nicotine analogs which as therapeutic agents exhibit tranquilizing effects in mammals.Illustrative of an invention nicotine analog is 3-[N-methyl-N-(3-aminopropyl)]aminomethylpyridine ##STR1## the nicotine analogs can exist in the form of acid addition salts.
    Type: Grant
    Filed: November 28, 1990
    Date of Patent: August 11, 1992
    Assignees: Philip Morris Incorporated, Philip Morris Products Inc.
    Inventors: Thomas S. Osdene, Henry V. Secor, Jeffrey I. Seeman
  • Patent number: 5134167
    Abstract: 1-Azabutadienes of the formula ##STR1## where R.sup.1 and R.sup.2 are each phenyl, biphenyl, naphthyl or pyridyl, and these radicals may be substituted, or are each alkyl which is unsubstituted or substituted, R.sup.3 is substituted or unsubstituted phenyl or a radical OR.sup.4, where R.sup.4 is hydrogen, alkyl or an aromatic or aliphatic acyl group, or R.sup.3 is a radical NHR.sup.5, where R.sup.5 is hydrogen, substituted or unsubstituted phenyl, or the carbamide group, and fungicidal agents containing these compounds.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: July 28, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Lauer, Bernhard Zipperer, Norbert Goetz, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5134151
    Abstract: The present invention relates to novel 2-picolylamine derivatives of general formula I ##STR1## wherein R.sub.1 represents an alkyl or phenylalkyl radical; R.sub.2 is hydrogen, C.sub.1 -C.sub.4 acyl or C.sub.1 -C.sub.4 alkoxycarbonyl; R.sub.3 is either an electron pair, in which case t means nothing and q is 0, or R.sub.3 is hydrogen or C.sub.1 -C.sub.4, in which case t is (+) and q=1; Z is oxygen or an aminocarboniloxy group; X is O or S; m and n are 2-6; p is 0-3; A.sup.- is a pharmaceutically acceptable ion. These compounds are PAF antagonists and, consequently, useful in the treatment of the diseases in which this substance is involved.
    Type: Grant
    Filed: March 2, 1990
    Date of Patent: July 28, 1992
    Assignee: J. Uriach & Cia
    Inventors: Javier Bartroli, Manuel Anguita, Elena Carceller
  • Patent number: 5130313
    Abstract: This invention relates to compounds of formula: ##STR1## in which R.sub.1 denotesa 1,2,3,6-tetrahydro-1-pyridyl radical substituted in the 4-position by an optionally substituted phenyl, optionally substituted 3-indolyl or 3-(5-hydroxyindolyl) radical,a 1-piperazinyl radical substituted in the 4-position by an optionally substituted phenyl, 1,2-benzisothiazol-3-yl, 1,2-benzisoxazol-3-yl or 2-pyridyl radical,a piperidino radical substituted in the 4-position by an optionally substituted phenyl, bis(4-fluorophenyl)methylene, 4-fluorobenzoyl, optionally substituted 2-oxo-1-benzimidazolinyl, optionally substituted 3-indolyl or 3-(5-hydroxyindolyl) radical, by two phenyl radicals or a hydroxyl radical and an optionally substituted phenyl radicalR.sub.2 denotes a radical SO.sub.2 R.sub.4 in which R.sub.4 denotes an alkyl or phenyl radical,R.sub.3 denotes a phenyl or naphthyl radical,or else R.sub.2 and R.sub.
    Type: Grant
    Filed: December 13, 1990
    Date of Patent: July 14, 1992
    Assignee: Rhone-Poulenc Sante
    Inventors: Marie-Therese Comte, Claude Gueremy, Jean-Luc Malleron, Jean-Francois Peyronel, Alain Truchon
  • Patent number: 5128348
    Abstract: Certain hexane and heptane amines including geometric and stereoisomers, agricultural compositions containing them and their use as fungicides.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: July 7, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Gregory S. Basarab
  • Patent number: 5125930
    Abstract: Polymeric cationic dyes wherein the same or different monomer components represented by the following formula (1) are linked at the terminal amino groups by a crosslinking agent:H.sub.2 N--A--CH.dbd.CH--B (1)in which A represents a substituted or unsubstituted benzene ring and B represents the radical of a quaternized methylene active compound. The dyes are used in particular for dyeing paper.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: June 30, 1992
    Assignee: Nippon Chemical Works Co., Ltd.
    Inventor: Koichi Taniguchi
  • Patent number: 5118674
    Abstract: The invention relates to 3-(N-methyl-N-alkyl)-amino 2-methoxymethylene propan 1-ol derivatives of the formula ##STR1## wherein R stands for an alkyl chain, A stands for: ##STR2## and Y represents various quaternary ammonia, to a preparation process of said compounds and to therapeutic compositions containing the same.
    Type: Grant
    Filed: November 27, 1990
    Date of Patent: June 2, 1992
    Assignee: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)
    Inventors: Pierre Braquet, Colette Broquet, Benedicte Vandamme, Paola Principe-Nicolas
  • Patent number: 5112860
    Abstract: Thiocarboxylic esters of the formula I ##STR1## where the substituents have the following meanings: X is oxygen, sulfur, oxymethylene, methyleneoxy, thiomethylene, methylenethio, ethylene, ethenylene or ethynylene,Y, Z are each sulfur or oxygen, but Y and Z are not simultaneously oxygen,R is alkyl, mononuclear, dinuclear or trinuclear aryl or hetaryl, where aryl and hetaryl may be substituted,and fungicidal agents containing these compounds.
    Type: Grant
    Filed: November 2, 1990
    Date of Patent: May 12, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Hubert Sauter, Siegbert Brand, Bernd Wenderoth, Gisela Lorenz, Eberhard Ammermann
  • Patent number: 5110831
    Abstract: The present invention relates to vinylogous hydroxamic acids, processes for their manufacture, pharmaceutical preparations containing them, and their use in the treatment of various disorders.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: May 5, 1992
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventors: Ronald L. Magolda, Stephen W. Wright
  • Patent number: 5103060
    Abstract: The novel compounds of the general formula I ##STR1## where X is straight-chain or branched alkanediyl having from 1 to 20 carbon atoms orX is straight-chain or branched alkanediyl having from 2 to 20 carbon atoms, whose carbon chain is interrupted by --O--, --S-- and/or --NR--,R is hydrogen, straight-chain or branched alkyl having from 1 to 6 carbon atoms or cycloalkyl, andY is a non-centrosymmetric radical containing an easily polarized conjugated .pi.-electron system and at least one terminal electron-acceptor group,having nonlinear optical properties, are highly suitable as nonlinear optical materials for nonlinear optical arrangements and for the preparation of polymers having nonlinear optical properties. In particular, they can be used to prepare organopolysiloxanes having nonlinear optical properties and containing side groups of the general formula Ia ##STR2## in which the variables are as defined above.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: April 7, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Brox, Dirk Funhoff, Ulrike Licht, Harald Fuchs, Wolfgang Schrepp