Chalcogen Attached Indirectly To The Five-membered Hetero Ring By Acyclic Nonionic Bonding Patents (Class 548/570)
  • Patent number: 5470921
    Abstract: A synthetic polyamide of formula I and its salts ##STR1## in which each R.sub.1 independently is selected from hydrogen, carboxyl, amino or a group of formula .alpha.-A.sub.1 -R.sub.10 (.alpha.)where A, is a bridging group and R.sub.10 is a sterically hindered amine group;each R.sub.2 independently is hydrogen or a group of formula .alpha.A is a bridging group of the formula ##STR2## is 0 or 1; R.sub.3 is hydrogen, C.sub.1-12 alkyl or is a significance of R.sub.10 ;R.sub.5 is hydrogen or C.sub.1-12 alkylR.sub.4 is a significance of R.sub.10 or a group of formula .alpha.; andp is an integer from 5 to 200;with the proviso that the compound of formula I contains 1-400 sterically hindered amine groups.
    Type: Grant
    Filed: May 20, 1994
    Date of Patent: November 28, 1995
    Assignee: Sandoz Ltd.
    Inventors: Bansi L. Kaul, Angelos-Elie Vougioukas, Jurgen Goldmann
  • Patent number: 5430052
    Abstract: The present invention relates to a pharmaceutical composition for use in preventing or treating heart diseases in a mammal, which comprises at least one aminoalkanesulfonic acid derivative of the formula (I): ##STR1## wherein X is hydrogen or an amino acid residue; Y is hydrogen, a phenyl group or an alkyl group, which may have a hydroxy, amino, carboxy, phenyl or hydroxyphenyl group; or X and Y are joined to form a trimethylene or hydroxytrimethylene group; and at least one of X and Y is other than hydrogen;or pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: July 4, 1995
    Assignee: Nippon Zoki Pharmaceutical Co., Ltd.
    Inventors: Kunihiko Higashiura, Masao Hattori, Kazuharu Ienaga
  • Patent number: 5367073
    Abstract: The present invention relates to a process for the synthesis of chiral enantiomerically pure .beta.-amino alcohols which are extraordinarily important as therapeutic agents for the treatment of a variety of human disorders and as chiral auxiliaries in organic synthesis. The hydroboration of enamines is a versatile and convenient method for the synthesis of both racemic and enantiomerically pure .beta.-amino alcohols in high yields. This methodology enables the synthesis of virtually any .beta.-amino alcohol. Hydroboration of these enamines with chiral organic borohydrides, e.g. either mono- or diisopinocampheylborane, followed by oxidation with aqueous or solid NaOH/30% H.sub.2 O.sub.2 or Me.sub.3 NO, gives the corresponding chiral .beta.-amino alcohol. Enantiomeric excesses ranged from 60% for reactions run at 25.degree. C. to greater than 99% for reactions run at -25.degree. C.
    Type: Grant
    Filed: October 15, 1993
    Date of Patent: November 22, 1994
    Assignee: The Regents of the University of California
    Inventors: Bakthan Singaram, Gary B. Fisher, Christian T. Goralski, Lawrence W. Nicholson
  • Patent number: 5326911
    Abstract: Ortho-amides of the formula ##STR1## can be prepared by reacting salts of the formula ##STR2## with alcoholates of the formulaM.sup.1 OR.sup.1 (III)where the radicals R.sup.1 to R.sup.4, M.sup.1 and X.sup..crclbar. have the meaning given in the description. The alcoholates are employed in highly active form with an effective content of 98-100% M.sup.1 OR.sup.1.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: July 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz-Ulrich Blank, Helmut Kraus, Gerhard Marzolph, Nikolaus Muller
  • Patent number: 5302724
    Abstract: This invention provides certain sulfonamide compounds, formulations and method of use of certain sulfonamide compounds in treating susceptible neoplasms.
    Type: Grant
    Filed: April 29, 1992
    Date of Patent: April 12, 1994
    Assignee: Eli Lilly and Company
    Inventors: J. Jeffry Howbert, Fariborz Mohamadi, Michael M. Spees
  • Patent number: 5280031
    Abstract: The present invention provides anti-angina pharmaceutical compositions containing at least one compound of the formula: ##STR1## wherein n is 1 or 2, R is a hydrogen atom or an H--(C.sub.1 -C.sub.8)-alkylene, hydroxy-(C.sub.1 -C.sub.8)-alkylene, R.sup.1 R.sup.2 N--(C.sub.1 -C.sub.8)-alkylene, R.sup.1 R.sup.2 N--(C.sub.1 -C.sub.8)-alkylene-CO--, R.sup.1 R.sup.2 N--CO--NR.sup.3 --(C.sub.1 -C.sub.8)-alkylene or R.sup.1 R.sup.2 N--CO-- radical, A is a valency bond or an --NR.sup.4 --CO-- or --CO-- NR.sup.4 -- radical, R.sup.4 is a hydrogen atom or a straight-chained or branched, saturated or unsaturated or cyclic alkyl radical containing up to 6 carbon atoms and B is a valency bond or a straight-chained or branched alkylene chain containing up to 8 carbon atoms, in which a --CH.sub.2 -- group can be replaced by a cycloalkylene radical containing 3 to 7 carbon atoms.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: January 18, 1994
    Assignee: Boehringer Mannheim GmbH
    Inventors: Herbert Simon, Helmut Michel, Michael Schultz, Wolfgang Bartsch
  • Patent number: 5274114
    Abstract: This invention relates to the preparation of 3- and/or 4-substituted pyrrolidine catalysts corresponding to formula (I) ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, X.sub.1, X.sub.2, and Y have the meanings described for formula (I) and to use of such catalysts in the polyisocyanate polyaddition process.
    Type: Grant
    Filed: February 10, 1992
    Date of Patent: December 28, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Richard Weider, Uwe Scholz, Andreas Ruckes
  • Patent number: 5254696
    Abstract: Novel pyrrolidine derivatives of the formula ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 have the meaning specified in the description,X represents hydrogen, fluorine, chlorine, bromine or optionally substituted C.sub.1 -C.sub.4 -alkyl, and m represents 1, 2 or 3.
    Type: Grant
    Filed: July 21, 1992
    Date of Patent: October 19, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Bernd Baasner, Heinz-Jurgen Bertram, Jurgen Hartwig
  • Patent number: 5218116
    Abstract: Procedure for the preparation of nitroxyl radicals of sterically hindered amines, consisting of the reaction of amines with hydrogen peroxide in the presence of a titanium containing catalyst, particularly in the presence of titanium silicalites.The catalyst can be recovered at the end of the reaction and recycled.
    Type: Grant
    Filed: November 29, 1991
    Date of Patent: June 8, 1993
    Assignee: Enichem Synthesis S.p.A.
    Inventors: Carlo Neri, Silvestro Costanzi, Rosa M. Riva, Mariangela Angaroni
  • Patent number: 5169986
    Abstract: The present invention provides an organic nonlinear optical material including a benzylidene-aniline derivative having an electron-donating substituent introduced at the 4-position and an electron-accepting substituent introduced at the 4'-position, by selecting as the conjugated .pi. electronic system a benzylidene-aniline derivative having a large molelcular hyperpolarizability and yet a dipole moment as small as those of benzene derivatives, and introducing a molecular alignment-regulating substituent. The centrosymmetry in the bulk state of the material, for example, in the crystal state, is destroyed and the molecular alignment is regulated to such a bulk structure so that the optical nonlinearity possessed by the molecule is effectively utilized. The material exhibit a large optical nonlinearity never attained by conventional techniques.the intermolecular cohesive force due to the .pi. electron interaction between the molecules in the present invention is larger than that between a benzene derivative.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: December 8, 1992
    Assignee: Toray Industries, Inc.
    Inventors: Tetsuya Tsunekawa, Tetsuya Gotoh, Keiichi Egawa
  • Patent number: 5130489
    Abstract: An improved process is provided for producing m-aminophenols comprising reacting resorcinol and an amino compound in an inert organic solvent and in the presence of an aluminosilicate catalyst.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: July 14, 1992
    Assignee: Indspec Chemical Corporation
    Inventor: Hans Dressler
  • Patent number: 5130432
    Abstract: A process for preparing a cyclic amine of Formula I ##STR1## in which R.sup.1 is phenyl, optionally substituted by 1 to 3 lower alkoxy groups;R.sup.2, R.sup.3 and R.sup.4 are independently hydrogen or lower alkyl; andn is 1 or 2,comprises(1) converting an aminoalcohol of Formula III ##STR2## to a dioxooxathiazolidine of Formula II ##STR3## in which R.sup.2, R.sup.3, R.sup.4 and n are as defined above; and (2) reacting the dioxooxathiazolidine of Formula II with an organometallic nucleophile, R.sup.1 M*, wherein R.sup.1 is as defined above, and hydrolyzing the resulting sulfamate salt.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: July 14, 1992
    Assignee: Syntex (U.S.A.) Inc.
    Inventors: Gary F. Cooper, Michael G. Martin
  • Patent number: 5117055
    Abstract: A perfluoroalkyl halogenide represented by the formula: ##STR1## wherein X stands for one element selected from the group consisting of iodine and bromine, R.sub.f for a perfluorohydrocarbon group, n for an integer in the range of 1 to 3, and m for an integer in the range of 1 to 3, provided that n and m satisfy the relationship, n.gtoreq.m, is produced by a method which consists essentially in subjecting a perfluorocarboxylic acid fluoride represented by the formula, ##STR2## wherein R.sub.f and n have the same meanings as defined above, to a thermal reaction with a lithium halogenide represented by XI, wherein X has the same meaning as defined above.
    Type: Grant
    Filed: February 22, 1990
    Date of Patent: May 26, 1992
    Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi, Haruhiko Fukaya
  • Patent number: 5106997
    Abstract: A novel squarylium derivative represented by general formula (I) and a process for preparing the same are described: ##STR1## wherein X and Z are defined in the specification. This squarylium derivative exhibits high nonlinearity and is excellent in thermal resistance, light resistance, storage stability and processability, so that it can be used for preparation of nonlinear optical elements.
    Type: Grant
    Filed: September 24, 1990
    Date of Patent: April 21, 1992
    Assignee: Fuji Xerox Co., Ltd.
    Inventor: Lyong S. Pu
  • Patent number: 5101047
    Abstract: The invention relates to novel sulfobetaine-substituted .alpha.-sulfonylcarboxylic acids of the general formula I and to processes for the preparation thereof. As organic intermediates, the compounds according to formula I represent a reactive synthesis component having the character of a sulfobetaine and can be used for further syntheses. In the case of a long-chain alkyl radical R.sub.1, polyfunctional surfactants are obtained. According to the invention, molar quantities of diallylammonium chloride are reacted with chloroacetic acid and twice the molar quantity of sodium hydrogen sulfite in the presence of a catalytic quantity of a peroxodisulfate, and the reaction solution obtained is converted, after addition of a catalytic quantity of iodide, by heating into sulfobetaine-substituted .alpha.-sulfonylacetic acids according to the general formula I.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: March 31, 1992
    Inventors: Detlef Ballschuh, Roland Ohme, Horst Seibt, Egon Grundemann
  • Patent number: 5101046
    Abstract: The invention relates to novel 3-chloromethylsulfonylmethyl-4-sulfomethyl-pyrrolidinium betaines (chloromethylsulfonyl-sulfobetaines) of the general formula I and to processes for the preparation thereof. The compounds according to the formula I can be used as organic intermediates for further syntheses or, if they contain a long-chain alkyl radical, as polyfunctional surfactants. Molar quantities of diallylammonium chloride are reacted with dichloroacetic acid and twice the molar quantity of sodium hydrogen sulfite in the presence of a catalytic quantity of a peroxodisulfate and, after the addition of a catalytic quantity of iodide, the reaction solution obtained is converted by heating to 3-chloro-methylsulfonylmethyl-4-sulfomethyl-pyrrolidinium betaines (chloromethylsulfonyl-sulfobetaines) of the general formula I.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: March 31, 1992
    Inventors: Detlef Ballschuh, Roland Ohme, Horst Seibt, Egon Grundemann
  • Patent number: 5099043
    Abstract: The invention relates to novel 3-methylsulfonylmethyl-4-sulfomethyl-pyrrolidinium betaines (methylsulfonyl-sulfobetaines) of the general formula I, which can be used as intermediates for further syntheses or, if they contain a long-chain alkyl radical, as polyfunctional surfactants or hydrotopes [sic]. Molar quantities of a diallylammonium salt are reacted together with chloroacetic acid and twice the molar quantity of sodium hydrogen sulfite in the presence of a catalytic quantity of a peroxodisulfate and the reaction solution obtained is, after addition of a catalytic quantity of iodide as well as calcium carbonate, converted to 3-methylsulfonylmethyl-4-sulfomethyl-pyrrolidinium betaines I by heating until the evolution of carbon dioxide has ceased.
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: March 24, 1992
    Inventors: Detlef Ballschuh, Roland Ohme, Horst Seibt, Egon Grundemann
  • Patent number: 5093040
    Abstract: Complex N-hydroxyimide compounds and carboxy hydroxamic acid-functional derivatives thereof are prepared from organic amines reacted with maleate esters and maleic anhydride. The compounds exhibit strong metal ion chelating properties and are useful as detergent additives to improve stain removal.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: March 3, 1992
    Assignee: American Cyanamid Company
    Inventor: Stephen F. Donovan
  • Patent number: 5071851
    Abstract: 4-substituted cyclohexylamines of the formula ##STR1## where R is the group CR.sup.1 R.sup.2 R.sup.3, where R.sup.1, R.sup.2 and R.sup.3 are hydrogen, unsubstituted or substituted alkyl, alkoxy, alkylthio or cycloalkyl, with the proviso that at most one of the substituents R.sup.1, R.sup.2 and R.sup.3 is hydrogen, X is an alkylene group which, together with the N atom, forms a substituted or unsubstituted heterocyclic ring in which up to 2 carbon atoms may be replaced by O, N or S atoms, and salts thereof, and fungicides containing these compounds.
    Type: Grant
    Filed: July 9, 1990
    Date of Patent: December 10, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Ernst Buschmann, Norbert Goetz, Bernhard Zipperer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 5068246
    Abstract: 3-Alkyl-4-arylpyrrolidine derivatives of the formula ##STR1## where R.sup.1 is alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkyl-cycloalkyl, cycloalkyl-alkyl, alkyl-cycloalkyl-alkyl, cycloalkenyl-alkyl, alkyl-cycloalkenyl, bicycloalkyl, bicycloalkylalkyl, alkyl-bicycloalkyl, heterocycloalkyl, heterocycloalkylmethyl, aryl, arylalkyl, alkylary, alkyl-aryl-alkyl,R.sup.2 is alkyl, alkoxy,R.sup.3 is alkylR.sup.4 is alkyl, alkenyl, alkynyl and phenylalkyl,X.sup.- is a plant-tolerated anion, andn is 0 or 1,their plant-tolerated salts, and fungicides containing these compounds.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: November 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Zipplies, Hubert Sauter, Walter Himmele, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 5068245
    Abstract: N-Substituted 3-arylpyrrolidine derivatives of the formula ##STR1## where R.sup.1 is 2,2-dimethylpropyl, 3,3-dimethylbutyl, 4,4-dimethylpentyl, 2,4,4-trimethylpentyl, 6-methylhept-2-yl, 3,5,5-trimethylhexyl, 6,10-dimethylundec-2-yl, 3-methylcyclohexyl, 3,3-dimethylcyclohexyl, 3,3,5-trimethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-propylcyclohexyl, 4-isopropylcyclohexyl, 4-tert.-butylcyclohexyl, trans-4-tert.-butylcyclohexyl, 4(2-methylbut-2-yl)cyclohexyl, 4(2,4,4-trimethylpent-2-yl)-cyclohexyl, cyclododecanyl, C.sub.3 -C.sub.9 -trialkylsilyl-substituted C.sub.4 -C.sub.12 -cycloalkyl, 4-hydroxycyclohexyl, 4-hydroxy-3-methylcyclohexyl, 4-hydroxy-3,5-dimethylcyclohexyl, 4-hydroxy-3,3-dimethylcyclohexyl, 4-hydroxy-3,3,5-trimethylcyclohexyl, unsubstituted or hydroxy-, C.sub.1 -C.sub.9 -alkyl-, C.sub.1 -C.sub.5 -alkoxy- or C.sub.3 -C.sub.9 -trialkylsilyl-substituted C.sub.5 -C.sub.12 -cycloalkenyl,R.sup.1 is further bicycloalkyl,R.sup.1 is further 4-tert.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: November 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Zipplies, Hubert Sauter, Franz Roehl, Walter Himmele, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 5041545
    Abstract: Hydrazide functionalized 2-hydroxybenzophenone ultraviolet light and heat stabilizers and derivatives are disclosed having the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X, Y, Z, all substituents thereof, and n are set forth in the Summary of the Invention. Y--N(R.sup.6)--Z is the hydrazide or derivative group and --X--R.sup.5 -- links the hydrazide group to an aromatic nucleus of the optionally substituted benzophenone group. Derivatives are, for example, acyl hydrazides, diacyl hydrazides (including imides), hydrazones and alkyl hydrazides. The compounds are useful as ultraviolet light absorbers and heat stabilizers for plastics.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: August 20, 1991
    Assignee: Atochem North America, Inc.
    Inventor: Terry N. Myers
  • Patent number: 5039802
    Abstract: The chiral catalyst of general structure 1, or its enantiomer ##STR1## is prepared by treating the corresponding N-carboxy anhydride of structure 2 ##STR2## with an aryl metal, especially a phenyl metal such as an aryl magnesium halide, aryl lithium, aryl zinc or aryl cesium, to form a 1,1-diaryl-methanol of structure 3 ##STR3## followed by treatment with a compound of structure, 4 ##STR4## The catalyst, wherein R is aromatic, is novel and in some cases superior to the catalyst wherein R is alkyl or aralkyl in directing the chirality of borane-dimethyl sulfide reductions of ketones to secondary alcohols.
    Type: Grant
    Filed: April 18, 1990
    Date of Patent: August 13, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Thomas J. Blacklock, Todd K. Jones, David J. Mathre, Lyndon C. Xavier
  • Patent number: 5030641
    Abstract: The present invention provides anti-angina pharmaceutical compositions containing at least one compound of the formula: ##STR1## wherein n is 1 or 2, R is a hydrogen atom or an H-(C.sub.1 -C.sub.8)-alkylene, hydroxy-(C.sub.1 -C.sub.8)-alkylene, R.sup.1 R.sup.2 N-(C.sub.1 -C.sub.8)-alkylene, R.sup.1 R.sup.2 N-(C.sub.1 -C.sub.8)-alkylene-CO--, R.sup.1 R.sup.2 N-CO-NR.sup.3 -(C.sub.1 -C.sub.8)-alkylene or R.sup.1 R.sup.2 N-CO-- radical, A is a valency bond or an --NR.sup.4 --CO-- or --CO--NR.sup.4 -- radical, R.sup.4 is a hydrogen atom or a straight-chained or branched, saturated or unsaturated of cyclic alkyl radical containing up to 6 carbon atoms and B is a valency bond or a straight-chained or branched alkylene chain containing up to 8 carbon atoms, in which a --CH.sub.2 -- group can be replaced by a cycloalkylene radical containing 3 to 7 carbon atoms.
    Type: Grant
    Filed: October 20, 1989
    Date of Patent: July 9, 1991
    Assignee: Boehringer Mannheim GmbH
    Inventors: Herbert Simon, Helmut Michel, Michael Schultz, Wolfgang Bartsch
  • Patent number: 4999361
    Abstract: The present invention provides compounds of the general formula ##STR1## wherein R.sub.1 is a hydrogen atom, a straight-chained or branched C.sub.1 -C.sub.12 -alkyl radical, a C.sub.3 -C.sub.7 -cycloalkyl radical, a straight-chained or branched C.sub.2 -C.sub.12 -alkenyl radical or an unsubstituted or substituted C.sub.3 -C.sub.7 -mono- or bicycloalkenyl radical, an unsubstituted or singly or multiple substituted monocyclic aromatic or heteroaromatic radical, R.sub.2 and R.sub.3, which can be the same or different, are straight-chained, branched, saturated or unsaturated C.sub.1 -C.sub.6 -aliphatic radicals or, together with the nitrogen atom to which they are attached, form a saturated or unsaturated ring which can contain further heteroatoms and can optionally be substituted by a lower alkyl radical, a lower alkoxy radical or an oxygen atom, R.sub.4 is an unsubstituted or singly or multiple substituted monocyclic aromatic radical, an unsubstituted or substituted five- or six-membered heteroaromatic ring, R.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: March 12, 1991
    Assignee: Boehringer Mannheim GmbH
    Inventors: Christos Tsaklakidis, Herbert Leinert, Peter Freund
  • Patent number: 4996215
    Abstract: A new piperidine compound is pharmacologically effective for treatment of the arrythmia and is defined by the formula: ##STR1## in which R.sup.1 is a lower alkyl or a tolyl, R.sup.2 is hydrogen, hydroxyl, a lower alkoxy or a lower alkyl, R.sup.3 is hydrogen, a lower alkyl, a lower alkenyl, a cycloalkyl or a cycloalkylalkyl, X is --CO--, --CH.sub.2 -- or --CHOH--, g is an integer of 1 to 3, h is an integer of 1 to 3, Y is hydrogen, a lower alkyl, a lower alkenyl, cyano, --CH.sub.2 COOR, R being hydrogen or a lower alkyl, a cycloalkyl, a cycloalkylalkyl, ##STR2## l being 1 or 2, --A--B, A being --(CH.sub.2).sub.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: February 26, 1991
    Assignee: Eisai Co., Ltd.
    Inventors: Hitoshi Oinuma, Motosuke Yamanaka, Kazutoshi Miyake, Tomonori Hoshiko, Norio Minami, Tadao Shoji, Yoshiharu Daiku, Kohei Sawada, Kenichi Nomoto
  • Patent number: 4950767
    Abstract: A process for the preparation of an optically active proline derivative of the formula ##STR1## in which R.sup.1 is alkyl, phenyl or benzyl, or an acid addition salt thereof, comprising reacting an S-proline ester of the formula ##STR2## in which R.sup.2 is alkyl with 1 to 4 carbon atoms, in a first stage with benzyl chloroformate of the formula ##STR3## in the presence of an acid-binding agent and in the presence of a diluent, thereby to produce an ester with the S-configuration on the asymmetrically substituted carbon atom, of the formula ##STR4## reacting such ester in a second stage with a Grignard compound of the formulaR.sup.1 --Mg Xin which X is chlorine, bromine or iodine, in the presence of a diluent, thereby to produce an S-proline derivative of the formula ##STR5## and reacting such S-proline derivative in a third stage with hydrogen in the presence of a catalyst, a diluent, and optionally an acid. The end product is new.
    Type: Grant
    Filed: October 31, 1988
    Date of Patent: August 21, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Udo Kraatz
  • Patent number: 4906634
    Abstract: Novel N-[4-(aminosubstituted)phenyl]methanesulfonamides and their use as cardiovascular agents, especially as antiarrhythmic agents are described. Pharmaceutical formulations containing such compounds are also discussed.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: March 6, 1990
    Assignee: Schering A.G.
    Inventors: Stanley S. Greenberg, William C. Lumma, Jr., Klaus Nickisch, Ronald A. Wohl
  • Patent number: 4897397
    Abstract: Certain aryl-alkynoic, alkenoic and alkanoic acids and derivatives and their use in treating inflammation, allergy and hyperproliferative skin disease are disclosed.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 30, 1990
    Assignee: Schering Corporation
    Inventors: Neng Y. Shih, David J. Blythin
  • Patent number: 4877885
    Abstract: Novel 3-sulfinatomethyl or 3-sulfonatomethyl-4-sulfomethyl-pyrrolidinium betaines are disclosed which have the formula ##STR1## These novel compounds are obtained by reacting diallyl-triallyl ammonium salts or their methallyl derivatives with hydrogen sulfite in the presence of peroxo disulfates alone or in a mixture with other oxidation agents with a pH-value-range from 1.5 to 6.0 in a watery solution, whereby in light of the selection of the amount of hydrogen sulfite in combination with the amount peroxo disulfate different SO.sub.2.sup.- --or SO.sub.3 .sup.- substituted sulfomethyl-pyrralidinium betaines are generated.The novel compounds are effective as specific tensides in a wide pH-range and can be extensively used as intermediary products.
    Type: Grant
    Filed: April 2, 1987
    Date of Patent: October 31, 1989
    Assignee: Akademie Der Wissenschaften Der DDR
    Inventors: Detlef Ballschuh, Horst Seibt, Roland Ohme, Jochen Rusche, Egon Gruendemann, Elke Krause
  • Patent number: 4835164
    Abstract: Novel heterocyclicmethanols are disclosed having the formula: ##STR1## wherein Z is pyrrolidinyl, piperidinyl, homopiperidinyl or pyridinyl; R.sup.1 is hydrogen, loweralkyl or carbethoxymethyl;R.sup.2 is hydrogen, loweralkyl, cycloalkyl, phenyl or phenyl-loweralkyl;R.sup.3 is 1 or 2-naphthalenyl, 2,3-dihydroinden-4 or 5-yl, phenyl or phenyl substituted by loweralkyl, loweralkoxy, halogen, trifluoromethyl, phenyl, methylenedioxy, nitro, amino, loweralkylamino, diloweralkylamino, loweracylamino;the 1-position of 2-pyrrolidinyl, 2-piperidinyl or 2-homopiperidinyl may be substituted by an R.sup.4 loweralkyl group, or R.sup.1 may form methylene or --CH.sub.2 -C(O)-bridges with R.sup.4 ;the pharmaceutically acceptable salts and diastereomers thereof, which compounds have antiarrhythmic and/or hypotensive activity in animals.
    Type: Grant
    Filed: February 20, 1987
    Date of Patent: May 30, 1989
    Assignee: A. H. Robins Company, Incorporated
    Inventors: James R. Shanklin, Jr., Christopher P. Johnson, III
  • Patent number: 4755599
    Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl,either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl,or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and(i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6 C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.
    Type: Grant
    Filed: February 3, 1987
    Date of Patent: July 5, 1988
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
  • Patent number: 4746199
    Abstract: The invention relates to novel paranitroaniline derivatives usable in non-linear optics and electrooptics, as well as to the preparation process for the same. These derivatives are in accordance with formula (I): ##STR1## in which one or more of the hydrogen atoms are optionally replaced by deuterium atoms. They are prepared by reacting one of the two pure optical isomers of 2-(hydroxymethyl)-pyrrolidine with a parahalogenonitrobenzene.The optically pure derivatives can be used in optical or optoelectronic devices.
    Type: Grant
    Filed: July 8, 1986
    Date of Patent: May 24, 1988
    Inventors: Jean-Francois Nicoud, Joseph Zyss
  • Patent number: 4746677
    Abstract: A compound of formula (I): ##STR1## or a salt thereof; wherein Z represents a heterocyclic ring and R.sup.2 and R.sup.3 are independently selected from hydrogen, nitrile, CONH.sub.2, and SO.sub.2 R.sup.4 wherein R.sup.4 is optionally substituted aryl, optionally substituted alkyl, aralkyl or cycloalkyl or R.sup.2 and R.sup.3 together form an optionally substituted methylene group or a bond, intermediates, compositions, insecticidal and nematicidal use.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: May 24, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael D. Turnbull, Ian T. Kay
  • Patent number: 4731457
    Abstract: Analgesic and anti-inflamatory compounds of the formula ##STR1## wherein n=0-1,X=Halo, lower Alkoxy, HO--, Lower Alkyl, andR= ##STR2##
    Type: Grant
    Filed: May 27, 1986
    Date of Patent: March 15, 1988
    Assignee: The Purdue Frederick Company
    Inventors: Bola V. Shetty, Arthur McFadden, Peter Hofer
  • Patent number: 4721786
    Abstract: Fungicidally active novel .beta.-naphthylalkylamines of the formula ##STR1## in which Ar represents optionally substituted .beta.-naphthyl andR.sup.1 and R.sup.2, which can be identical or different, represent alkyl or alkenyl orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, represent an optionally substituted saturated heterocyclic radical, which can contain further hetero-atoms,or plant-tolerated acid addition salts thereof.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: January 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Weissmuller, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
  • Patent number: 4719219
    Abstract: Compound of the formula ##STR1## wherein n is 1 or 2, Y is OH, R.sup.1 COO--, R.sup.2 R.sup.3 NCOO-- or R.sup.4 O whereby R.sup.1 is an alkyl group, or a possibly substituted phenyl group, R.sup.2 is an alkyl, phenethyl, or benzyl or phenyl group, R.sup.3 is H or an alkyl group and R.sup.4 is an allyl or benzyl group, and R is an alkyl, hydroxyalkyl, dimethylaminoalkyl or methylthioalkyl group or alkenyl group, processes for their preparations and methods of treatment employing such compounds. The compounds are useful for therapeutic purposes, especially for treatment of disorders in the central nervous system.
    Type: Grant
    Filed: October 1, 1984
    Date of Patent: January 12, 1988
    Assignee: Per A. E. Carlsson
    Inventors: Folke L. E. Arvidsson, Per A. E. Carlsson, Uli A. Hacksell, John S. M. Hjorth, Per L. Lindberg, John L. G. Nilsson, Domingo Sanchez, Nils U. E. Svensson, Hakan V. Wikstrom
  • Patent number: 4696926
    Abstract: A compound of formula (I): ##STR1## or a salt thereof; where Z represents a heterocyclic ring and R.sup.2 and R.sup.3 are independently selected from hydrogen, nitrile, CONH.sub.2 and SO.sub.2 R.sup.4 wherein R.sup.4 is optionally substituted aryl, optionally substituted alkyl, aralkyl or cycloalkyl or R.sup.2 and R.sup.3 together form an optionally substituted methylene group or a bond, intermediates, compositions and insecticidal and nematocidal use.
    Type: Grant
    Filed: December 12, 1986
    Date of Patent: September 29, 1987
    Assignee: Imperial Chemical Industries plc
    Inventors: Michael D. Turnbull, Ian T. Kay
  • Patent number: 4686309
    Abstract: The invention provides compounds of formula: ##STR1## in which R=H, halogen, alkyl, alkyloxy, alkythio, NH.sub.2, alkylamino, dialkylamino or CF.sub.3, R.sub.3 =H or alkyl, either R.sub.4 and R.sub.5 =H and R.sub.1 and R.sub.2 =H or alkyl, optionally substituted by alkenyl (2 to 4 C) or alternatively R.sub.1 and R.sub.2 form together a saturated heterocyclic ring containing 4 to 7 ring members and optionally containing another heteroatom such as O, S or N optionally substituted by alkyl, or R.sub.4 =H, R.sub.1 =H or alkyl and R.sub.2 and R.sub.5 together form an alkylene (3 to 4 C) radical and (i) either A=alkyl or phenyl which is unsubstituted or substituted by one or two substituents chosen from halogen, alkyl, alkyloxy, alkylthio, NH.sub.2, alkylamino, dialkylamino, NO.sub.2 or CF.sub.3 or alternatively A=pyridyl, benzyl or cycloalkyl (3 to 6C), Y=S, SO or SO.sub.2 or a radical: ##STR2## in which R.sub.6 =H or alkyl and R.sub.
    Type: Grant
    Filed: February 15, 1985
    Date of Patent: August 11, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Jean-Claude Barriere, Jean-Pierre Corbet, Claude Cotrel, Daniel Farge, Jean-Marc Paris
  • Patent number: 4665196
    Abstract: There are provided compounds which are alkyl sulfonates substituted on a 5-membered heterocyclic or cyclic ring. The hetero-substituents of the ring may be O, S, R.sub.2 N, R.sub.3 R.sub.4.sup.+ N<, ##STR1## where R.sub.2, R.sub.3 and R.sub.4 are the same or different substituted or unsubstituted, and are hydrogen, alkyl or aryl. Optionally, the hetero-substituent may be replaced by R.sub.3 R.sub.4 C. The alkyl sulfonate substituent is in the 3 position of the ring and a substituted or unsubstituted alkyl substituent is in the 4 position of the ring. The compounds may be prepared by reacting X(CH.sub.2 CH.dbd.CHR).sub.2, where X is the above mentioned hetero-substituents or R.sub.3 R.sub.4 C<, with a bisulfate salt.
    Type: Grant
    Filed: April 18, 1985
    Date of Patent: May 12, 1987
    Assignee: Mobil Oil Corporation
    Inventor: Kirk D. Schmitt
  • Patent number: 4642348
    Abstract: Novel pyrrolidine, piperidine and homopiperidinecarboxamide and thiocarboxamide compounds having the formula: ##STR1## wherein X is --S--, --S(O)-- or --S(O).sub.2 --; A is a loweralkalene chain and A.sup.1 and A.sup.2 are alkalene chains when p and d are one; R, R.sup.1 and R.sup.2 are hydrogen, loweralkyl, phenyl cycloalkyl or phenylalkyl and R.sup.1 and R.sup.2 may form a heterocyclic residue with the adjacent nitrogen atom; Q is a selected aromatic radical, and the pharmaceutically acceptable acid addition salts useful as cardiac antiarrhythmia agents are disclosed.Novel chemical intermediates, unsubstituted on pyrrolidine, piperidine and homopiperidine nitrogen but with --(A.sup.2).sub.p --X--(A.sup.2).sub.d --Q side chain are also disclosed.
    Type: Grant
    Filed: July 1, 1985
    Date of Patent: February 10, 1987
    Assignee: A. H. Robins Company, Incorporated
    Inventor: James R. Shanklin, Jr.
  • Patent number: 4626592
    Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: December 2, 1986
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis
  • Patent number: 4625038
    Abstract: Disclosed herein are novel chemical intermediates having the formula ##STR1## wherein R.sub.1 is alkyl, cycloalkyl, aryl or arylalkyl.
    Type: Grant
    Filed: December 23, 1985
    Date of Patent: November 25, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: John K. Thottathil
  • Patent number: 4622409
    Abstract: The invention relates to novel paranitroaniline derivatives usable in non-linear optics and electrooptics, as well as to the preparation process for the same. These derivatives are in accordance with formula (I): ##STR1## in which one or more of the hydrogen atoms are optionally replaced by deuterium atoms. They are prepared by reacting one of the two pure optical isomers of 2-(hydroxymethyl)-pyrrolidine with a parahalogenonitrobenzene.The optically pure derivatives can be used in optical or optoelectronic devices.
    Type: Grant
    Filed: May 13, 1985
    Date of Patent: November 11, 1986
    Inventors: Jean-Francois Nicoud, Joseph Zyss
  • Patent number: 4599419
    Abstract: (3-Aminopropoxy)bibenzyl derivatives are prepared and found useful as pharmaceutical agents, particularly as inhibitors of platelet aggregation.
    Type: Grant
    Filed: July 9, 1984
    Date of Patent: July 8, 1986
    Assignee: Mitsubishi Chemical Industries, Inc.
    Inventors: Ryoji Kikumoto, Harukazu Fukami, Hiroto Hara, Kunihiro Ninomiya, Mamoru Sugano
  • Patent number: 4594428
    Abstract: The present invention concerns compound useful as intermediates in the preparation of heterocyclic phenoxy amines of the formula ##STR1## wherein Y is hydroxyl or chlorine and R is 1-cyclohexenylmethyl.
    Type: Grant
    Filed: January 7, 1983
    Date of Patent: June 10, 1986
    Assignee: Societe d'Etudes Scientifiques et Industrielles de L'ile-de-France
    Inventors: Michel L. Thominet, Jacqueline F. Franceschini
  • Patent number: 4588819
    Abstract: 4-Substituted proline derivatives having the formula ##STR1## can be prepared by reacting the compound having the formula ##STR2## with a compound having the formula ##STR3## to obtain a compound having the formula ##STR4## (a novel intermediate), alkylating that compound to obtain a compound having the formula ##STR5## (a novel intermediate), converting that compound to a compound having the formula ##STR6## (a novel intermediate), and oxidizing that compound to yield the desired proline having the formula ##STR7## wherein R.sub.1 is alkyl, cycloalkyl, aryl or arylalkyl, R.sub.1 ' is alkyl, cycloalkenyl, aryl or arylalkyl, R.sub.2 is alkyl, aryl, arylalkyl or cycloalkyl and R.sub.3 is hydrogen, alkyl, aryl, arylalkyl or cycloalkyl.
    Type: Grant
    Filed: November 19, 1984
    Date of Patent: May 13, 1986
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: John K. Thottathil
  • Patent number: 4528383
    Abstract: There are provided compounds which are alkyl sulfonates substituted on a 5-membered heterocyclic or cyclic ring. The hetero-substituents of the ring may be O, S, R.sub.2 N, R.sub.3 R.sub.4.sup.+ N<, ##STR1## where R.sub.2, R.sub.3 and R.sub.4 are the same or different substituted or unsubstituted, and are hydrogen, alkyl or aryl. Optionally, the hetero-substituent may be replaced by R.sub.3 R.sub.4 C. The alkyl sulfonate substituent is in the 3 position of the ring and a substituted or unsubstituted alkyl substituent is in the 4 position of the ring. The compounds may be prepared by reacting X(CH.sub.2 CH.dbd.CHR).sub.2, where X is the above mentioned hetero-substituents or R.sub.3 R.sub.4 C<, with a bisulfitc salt.
    Type: Grant
    Filed: April 30, 1982
    Date of Patent: July 9, 1985
    Assignee: Mobil Oil Corporation
    Inventor: Kirk D. Schmitt
  • Patent number: 4513137
    Abstract: Mono- or bis(iodonium salts) are produced in neutral organic solvents by the reaction of an [hydroxy (organosulfonyloxy)iodo]arene with a bis(triorganosilyl)arene, a bis(trihalosilyl)arene, or with a mono- or bis(triorganosilyl)heterocyclic compound, or a mono- or bis(trihalosilyl)heterocyclic. The iodonium salts are made under conditions of regiospecific control.
    Type: Grant
    Filed: April 9, 1981
    Date of Patent: April 23, 1985
    Assignee: The University of Akron
    Inventors: Gerald F. Koser, Carol S. Carman
  • Patent number: RE32896
    Abstract: Amines and amides are N,N-cyclodialkylated by reaction with an unstrained cyclic ether in the presence of a B-subgroup metal oxide alkylation catalyst, preferably a Group IV-B metal oxide such as titanium dioxide.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: March 28, 1989
    Assignee: Ethyl Corporation
    Inventor: Duane C. Hargis