Nitrogen Attached Directly To The Piperidine Ring By Nonionic Bonding Patents (Class 546/244)
  • Patent number: 4605743
    Abstract: 2,2,6,6-tetraalkyl-4-piperidylamines are produced by reacting an amine with a 2,2,6,6-tetraalkyl-4-piperidone in the presence of a palladium catalyst.
    Type: Grant
    Filed: April 16, 1985
    Date of Patent: August 12, 1986
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell E. Malz, Jr., Harold Greenfield
  • Patent number: 4599338
    Abstract: Xanthine compounds of the formula: ##STR1## in which: R.sub.1 is hydrogen or (C.sub.1 -C.sub.5) alkyl;R.sub.2 is hydrogen, (C.sub.1 -C.sub.5) alkyl optionally having a double bond, or benzyl;R.sub.3 is hydrogen or methyl;A is (CH.sub.2).sub.n, in which n is an integer from 1 to 4, optionally substituted, when n is higher than 1, by hydroxy;X is nitrogen or ##STR2## and the substituents R are each (C.sub.1 -C.sub.5) alkyl or they form together a polymethylene chain from C.sub.4 to C.sub.6, optionally containing an oxygen or a sulfur atom.These compounds and physiologically tolerable acid addition salts thereof may be used as medicines especially in the treatment of migraine and asthenia.
    Type: Grant
    Filed: January 16, 1985
    Date of Patent: July 8, 1986
    Assignee: Adir, S.A.R.L.
    Inventors: Gilbert Regnier, Claude Guillonneau, Jacques Duhault, Francois Roman
  • Patent number: 4588734
    Abstract: Compounds of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen, alkyl, alkenyl, alkynyl, phenyl-alkyl, or cycloalkyl,n is an integer from 0 to 4 inclusive,M is heterocyclic or heterocyclic alkyl,Y is hydroxy, alkoxy, amino, or substituted amino, amino-alkanoyl, aryloxy, aminoalkoxy, or hydroxyalkoxy, andR.sub.7 is hydrogen, alkanoyl, carboxylalkanoyl, hydroxyalkanoyl, amino-alkanoyl, cyano, amidino, carbalkoxy, ZS, or ##STR2## wherein Z is hydrogen, alkyl, hydroxyalkyl, aminoalkyl or the radical ##STR3## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, n, M and Y are as described above; and where Y is hydroxy their nontoxic, pharmaceutically acceptable alkali metal, alkaline earth metal, and amine salts.These compounds possess antihypertensive and angiotensin converting enzyme inhibitory activity.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: May 13, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventors: John T. Suh, Jerry W. Skiles, Bruce E. Williams, Alfred Schwab
  • Patent number: 4564677
    Abstract: Disclosed is a method of preparing N-amino compounds from corresponding secondary amines by reacting a secondary amine with nitrous acid and zinc in a neutral pH reaction media to form the corresponding N-amine.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: January 14, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventor: Martin L. Kantor
  • Patent number: 4544654
    Abstract: Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: October 1, 1985
    Assignee: Schering A.G.
    Inventors: David D. Davey, William C. Lumma, Jr., Ronald A. Wohl
  • Patent number: 4529437
    Abstract: Thiocarbamoyl-guanidine derivatives having herbicide activity are disclosed.The process for their preparation and their use as herbicides are disclosed too.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: July 16, 1985
    Assignee: Montedison S.p.A.
    Inventors: Roberto Colle, Franco Gozzo, Ciro Preziuso, Antony G. M. Barrett, Derek H. R. Barton
  • Patent number: 4528374
    Abstract: Novel oligomer or polymer polyamine-1,3,5-triazines containing at least one polyalkylpiperidine radical, for example that of the formula ##STR1## processes for their production, their use for stabilizing organic material, and the organic material protected therewith against oxidative and light-induced degradation.
    Type: Grant
    Filed: November 9, 1981
    Date of Patent: July 9, 1985
    Assignee: Ciba-Geigy Corporation
    Inventor: Erwin Nikles
  • Patent number: 4496542
    Abstract: Compounds of the formula ##STR1## wherein R and R.sub.9 are independently hydroxy and lower alkoxy,R.sub.1 and R.sub.2 are independently hydrogen, lower alkyl, aryl-lower alkyl having from 7 to 12 carbon atoms, or heterocyclic-lower alkyl having from 6 to 12 carbon atoms,R.sub.3, R.sub.4, R.sub.5, R.sub.7 and R.sub.8 are hydrogen or lower alkyl,R.sub.6 is heterocyclic and their pharmaceutically acceptable, nontoxic acid addition salts and where R or R.sub.9 or both are hydroxy, their pharmaceutically acceptable, nontoxic basic salts, possess antihypertensive activity.
    Type: Grant
    Filed: April 13, 1983
    Date of Patent: January 29, 1985
    Assignee: USV Pharmaceutical Corporation
    Inventors: Jerry W. Skiles, Raymond D. Youssefyeh, John T. Suh, Howard Jones
  • Patent number: 4487887
    Abstract: Polymers of diallyl amino-4-(2,2,6,6-tetramethyl piperidyl) carboxylic acid esters and amides are provided, having a molecular weight within the range from about 800 to about 20,000, and derived from a monomer having the formula: ##STR1## wherein: R is alkylene or alkyleneoxy having from one to about six carbon atoms and m is 0 or 1;R.sub.1 is selected from the group consisting of hydrogen; oxyl; alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; alkylaryl having from seven to about eighteen carbon atoms; epoxy alkyl having from three to about eighteen carbon atoms; and acyl having from two to about eighteen carbon atoms; andY is selected from the group consisting of ##STR2## where R.sub.2 and R.sub.3 are hydrogen or alkyl having from one to about eight carbon atoms and n is 0 or 1;Z is selected from the group consisting of ##STR3## in which R.sub.4, R.sub.5 and R.sub.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: December 11, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Ryoji Kimura
  • Patent number: 4487900
    Abstract: Polymers of diallyl 4-(2,2,6,6-tetramethyl piperidyl) amines are provided, having a molecular weight within the range from about 800 to about 20,000, and derived from the monomer ##STR1## wherein: R is selected from the group consisting of hydrogen, oxyl, alkyl and hydroxyalkyl having from one to about eighteen carbon atoms; alkylaryl having from seven to about eighteen carbon atoms; epoxy alkyl having from three to about eighteen carbon atoms and acyl having from two to about eighteen carbon atoms, as well as stabilized synthetic resin compositions having an improved resistance to deterioration by light and containing such a polymer.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: December 11, 1984
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Yutaka Nakahara, Ryoji Kimura
  • Patent number: 4468403
    Abstract: Pharmaceutical compounds of the general formula (1) have been prepared ##STR1## and non-toxic pharmaceutically acceptable salts thereof, wherein R.sub.1 is a lower alkyl, phenyl lower alkyl, amino substituted phenyl lower alkyl, nitro substituted phenyl lower alkyl, cycloalkyl lower alkyl or a lower alkenyl substituent, R.sub.2 is a member selected from the group consisting of a cyano, pyridylsulfonyl, lower alkyl substituted sulfonyl, phenylsulfonyl, lower alkyl substituted phenylsulfonyl, lower alkoxy substituted phenylsulfonyl, halogen substituted phenylsulfonyl, nitro substituted phenylsulfonyl, amino substituted phenylsulfonyl and lower alkyl amido substituted phenylsulfonyl; R.sub.3 is a hydrogen or halogen atom; and R.sub.4 is a hydrogen, lower alkyl or lower alkoxy substituent, lower denoting a straight or branched chain having from 1-4 carbon atoms. These compounds exhibit analgesic agonist activity or analgesic agonist-antagonist activities.
    Type: Grant
    Filed: July 20, 1982
    Date of Patent: August 28, 1984
    Assignee: Canadian Patents & Development Limited
    Inventors: Edward E. Knaus, Brent K. Warren, Theodore A. Ondrus
  • Patent number: 4448975
    Abstract: Amidines are one of the strongest organic bases and find application where this property is needed, such as in phase transfer catalysis in the form of their substituted derivatives. Their use, however, has been hampered by their expensive nature due to only mediocre yields in their preparation. The present invention provides a process for the preparation of substituted amidines in essentially quantitative yields.
    Type: Grant
    Filed: October 15, 1981
    Date of Patent: May 15, 1984
    Assignee: General Electric Company
    Inventor: Victor Mark
  • Patent number: 4429157
    Abstract: Primary amines and/or diamines can be prepared from oxo compounds, optionally containing additional reducible groups, by a process comprising:(1) reacting the oxo compound with ammonia in the presence of an imine-forming catalyst, preferably an ion exchanger loaded with ammonia ions, at a temperature of 10.degree. to 120.degree. C. and a pressure of 1 to 300 bar, whereby a Schiff base is formed; and(2) reducing the Schiff base by reaction with ammonia and hydrogen in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: June 10, 1981
    Date of Patent: January 31, 1984
    Inventors: Josef Disteldorf, Werner Hubel, Lothar Broschinski
  • Patent number: 4412021
    Abstract: Polyalkylpiperidyl-ureas of the formula I ##STR1## in which m is 1-4, X, R.sup.2 and R.sup.3 are monovalent substituents and R.sup.1 is a m-valent radical, can be prepared from the corresponding 4-aminopiperidines by reaction with carbamoyl chlorides. They are outstanding stabilizers for plastics, and especially for polyolefins, to protect them against degradation by the action of light.
    Type: Grant
    Filed: February 23, 1982
    Date of Patent: October 25, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Friedrich Karrer
  • Patent number: 4409228
    Abstract: The present invention relates to novel 4-amino-1-(2-pyridyl)piperidines with anorexiant action, of formula: ##STR1## in which R represents hydrogen, a halogen, a methyl group, a trifluoromethyl group, a lower alkoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a lower alkylthio group, a trifluoromethylthio group, a possibly substituted phenoxy group or a possibly substituted phenylthio group; to salts thereof; to a process for preparation thereof; to drugs containing same; and to intermediate products in the synthesis thereof.
    Type: Grant
    Filed: December 3, 1981
    Date of Patent: October 11, 1983
    Assignee: Sanofi
    Inventors: Dino Nisato, Paolo Carminati
  • Patent number: 4409220
    Abstract: Compounds of the formula ##STR1## wherein A and B, which may be the same or different, each represent methylene, (alkyl of 1 to 3 carbon atoms)-methylene, ethylene or (alkyl of 1 to 3 carbon atoms)-ethylene;R.sub.1 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 3 to 6 carbon atoms, phenyl-(alkyl of 1 to 3 carbon atoms), halophenyl-(alkyl of 1 to 3 carbon atoms), alkanoyl of 1 to 3 carbon atoms, phenyl-(alkanoyl of 1 to 3 carbon atoms), halophenyl-(alkanoyl of 1 to 3 carbon atoms), alkoxycarbonyl of 2 to 4 carbon atoms, aralkoxycarbonyl of 8 to 10 carbon atoms or phenyl;one of R.sub.2 and R.sub.3 is amino and the other is hydrogen, chlorine, bromine, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms, phenyl or halophenyl;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as bradycardiacs.
    Type: Grant
    Filed: August 27, 1981
    Date of Patent: October 11, 1983
    Assignee: Dr. Karl Thomae Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Hurnaus, Gerhart Griss, Robert Sauter, Wolfgang Grell, Walter Kobinger, Ludwig Pichler
  • Patent number: 4377687
    Abstract: This invention relates to compounds having the formula: ##STR1## wherein R.sub.1 and R.sub.2 are selected from the group consisting of hydrogen, acyl, trifluoroacetyl, straight chained and branched alkyl groups with up to 6 carbon atoms, such alkyl groups with up to 3 substituents selected from the group consisting of OH, OSO.sub.2 CH.sub.3, COOH, COOR, CONH.sub.2 and Hal, where R is an alkyl group with up to 6 carbon atoms, and R.sub.1 and R.sub.2 together form a heterocyclic ring containing 4 to 6 carbon atoms and optionally further heteroatoms and such rings with up to 3 substituents selected from the group consisting of lower alkyl, OH, COOH, COOR, CONH.sub.2, where R has the above meaning, the chloroethyl nitrosoureido group and Hal, and Hal is selected from the group consisting of chlorine and fluorine, which heterocyclic ring is not the para-methyl piperazine group, said nitroso ureas having a tumor inhibiting effect.
    Type: Grant
    Filed: April 22, 1981
    Date of Patent: March 22, 1983
    Assignee: Stiftung Deutsches Krebsforschungszentrum
    Inventor: Gerhard Eisenbrand
  • Patent number: 4348406
    Abstract: Compounds of the formula: ##STR1## and their pharmaceutically acceptable acid addition salts, useful as anthelmintics are disclosed.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: September 7, 1982
    Assignee: Schering Corporation
    Inventor: M. Mehdi Nafissi-Varchei
  • Patent number: 4341795
    Abstract: Asymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
    Type: Grant
    Filed: December 1, 1975
    Date of Patent: July 27, 1982
    Assignee: Union Carbide Corporation
    Inventor: Wei C. Liang
  • Patent number: 4303588
    Abstract: Novel farnesylacetic acid amide compounds represented by general formula ##STR1## wherein A is alkylene of at least 2 carbon atoms, R.sup.1 is H or lower alkyl, and R.sup.2 and R.sup.3 are each independently H, alkyl, cycloalkyl, alkenyl, aryl or aralkyl, or either one of R.sup.2 and R.sup.3 is such a group that forms, together with A, a piperidine or pyrrolidine ring which contains as constituent thereof the nitrogen atom lying therebetween, or R.sup.2 and R.sup.3 combinedly represent a group which forms, together with the nitrogen atom to which they are bonded, a piperidine, pyrrolidine or piperazine ring; and salts thereof have antiulcerogenic and antibacterial activities.
    Type: Grant
    Filed: March 21, 1980
    Date of Patent: December 1, 1981
    Assignee: Kuraray Co., Ltd.
    Inventors: Susumu Okabe, Yoshiaki Omura, Yoichi Ninagawa, Yoshiji Fujita
  • Patent number: 4296033
    Abstract: 1-Mercaptoacyl proline having an azido group in the 4-position inhibits the conversion of angiotensin I to angiotensin II in mammals and is useful for the treatment of hypertension.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: October 20, 1981
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Edward W. Petrillo, Jr., Frank L. Weisenborn
  • Patent number: 4256800
    Abstract: The antistatic composition for application to flat fibrous articles such as textiles, carpets, fabrics and the like which comprises a salt of a polymeric acid with an amine of the general formula ##STR1## wherein A=H, --OR.sub.2, ##STR2## R.sub.1 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.2 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.3 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.
    Type: Grant
    Filed: January 18, 1978
    Date of Patent: March 17, 1981
    Assignee: Chemische Fabrik Stockhausen & Cie
    Inventors: Dolf Stockhausen, Reinmar Peppmoller
  • Patent number: 4244963
    Abstract: 1-[2-(Alkyl and arylsulfonyl)-2-propenyl and propyl] substituted piperidines of the formula: ##STR1## where A is ##STR2## and R.sub.1 -R.sub.5 are various substituents, are useful as antimicrobial and anti-inflammatory agents.
    Type: Grant
    Filed: September 27, 1979
    Date of Patent: January 13, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Nathaniel Grier, Richard A. Dybas, Bruce E. Witzel
  • Patent number: 4242347
    Abstract: 1-(Indolyl-3-alkyl)-3 or 4-(ureido or guanidino)-piperidines, e.g. those of the formula ##STR1## R=H; alkyl; free, etherified or esterified OH or SH; CF.sub.3, NO.sub.2 or NH.sub.2m=1-4;n=2 or 3;X=O, S or NHacyl derivatives and salts thereof are antihypertensive agents.
    Type: Grant
    Filed: June 18, 1979
    Date of Patent: December 30, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Charles F. Huebner
  • Patent number: 4223147
    Abstract: The invention relates to new methylol derivatives of 2,2,6,6-tetraalkylpiperidines, to their production and to their use as chemically attached stabilizers for polymers containing reactive OH- and NH-groups.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: September 16, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Harald Oertel, Paul Uhrhan, Reinhard Lantzsch, Ernst Roos, Hans Schroer, Dieter Arlt
  • Patent number: 4177279
    Abstract: The invention provides compounds of general formula I ##STR1## and pharmaceutically acceptable acid addition and quaternary ammonium salts thereof, wherein R represents hydrogen or lower alkyl, R.sup.1 represents hydrogen or lower alkyl, R.sup.2 represents hydrogen or lower alkyl, R.sup.3 represents hydrogen, halogen, lower alkoxy, hydroxy, or lower alkyl, R.sup.4 represents hydrogen, lower alkyl, cycloalkyl of 5 to 7 carbon atoms, thienyl, furyl, phenyl; phenyl mono- or disubstituted by halogen, lower alkyl, lower alkoxy, hydroxy or trifluoromethyl; or benzoyl, halobenzoyl, lower alkanoyl, cycloalkanoyl of 6 to 8 carbon atoms, or thienoyl, A represents an alkylene, mono- or diketo- or hydroxy-alkylene radical having from 1 to 5 carbon atoms and X is oxygen or sulphur.The compounds exhibit action on the cardiovascular system particularly hypotensive and/or anti-hypertensive activity.
    Type: Grant
    Filed: July 21, 1975
    Date of Patent: December 4, 1979
    Assignee: John Wyeth & Brother Ltd.
    Inventors: John L. Archibald, John L. Jackson
  • Patent number: 4176135
    Abstract: Hydrazodicarbonamide is prepared by reacting a compound represented by ##STR1## with urea while the former is being continuously or intermittently introduced into the reaction system and while the carbonyl compound and ammonia produced as by-products are being withdrawn from the system.
    Type: Grant
    Filed: January 23, 1978
    Date of Patent: November 27, 1979
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventors: Shigeaki Ohno, Toshiyuki Kazuta, Takeshi Iwata
  • Patent number: 4166813
    Abstract: New polyalkylated 4-aminopiperidine derivatives contain in their molecule two or three piperidine rings, each having two alkyl substituents at both the 2- and the 6- positions, optionally having substituents at the 1- and 3- positions and having an amino substituent at the 4- position. The piperidine rings are joined together by attachment of the 4-amino substituents through, where there are two piperidine rings, a polyalkylene, polyether or polyester chain, or through, where there are three piperidine rings, an isocyanurate or glycerol system. These compounds and their acid addition salts are useful as stabilizers for synthetic polymers.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: September 4, 1979
    Assignee: Sankyo Company Ltd.
    Inventors: Nobuo Soma, Syoji Morimura, Takao Yoshioka, Tomoyuki Kurumada
  • Patent number: 4154934
    Abstract: New mercaptoacyl derivatives of heterocyclic carboxylic acids which have the general formula ##STR1## are useful as angiotensin converting enzyme inhibitors.
    Type: Grant
    Filed: August 11, 1978
    Date of Patent: May 15, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Jack Bernstein, Kathryn A. Losee
  • Patent number: 4145512
    Abstract: According to the invention there are obtained modified polyurethanes which have a durable, wash-fast, acid-resistant, cleaning-resistant and solvent-resistant stabilization on the basis of 2,2,6,6-tetraalkyl-piperidine light protective agents. The stabilizers are integral constituents of the polyurethanes, that is to say they are built into the polyurethane chain by a chain lengthening reaction in which two H-active reactive groups (preferably from the series of primary or secondary amino groups, carboxylic acid hydrazide, carbazic ester or semicarbazide groups) of a 2,2,6,6-tetraalkyl piperidine derivative react with isocyanate groups of polyisocyanates or isocyanate prepolymers, optionally in the presence of the usual chain lengthening agents.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: March 20, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Paul Uhrhan, Harald Oertel, Reinhard Lantzsch, Ernst Roos, Dieter Arlt