Chalcogen Attached Directly To The Five-membered Hetero Ring By Nonionic Bonding (e.g., 3-pyrrolidinols, Etc.) Patents (Class 548/541)
  • Patent number: 5210304
    Abstract: A continuous process for the hydrocarbylthiation of aromatic amines is disclosed. The process involves forming an admixture of aromatic amine, hydrocarbyl disulfide and an effective amount of a Lewis acid catalyst and subsequently allowing such admixture to flow as a thin film along a column. An inert gas is passed in a counter-current manner through the admixture.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: May 11, 1993
    Assignee: Ethyl Corporation
    Inventors: John F. Balhoff, Donald E. Balhoff
  • Patent number: 5204341
    Abstract: 1-arylsulphonyl-2-pyrrolidone derivatives for treating spasmodic disorders in gastro-enterology, in gynaecology, in obstetrics, in urology; intermediates in the preparation of such products; methods for preparing such products and pharmaceutical preparations containing such products.
    Type: Grant
    Filed: December 11, 1991
    Date of Patent: April 20, 1993
    Assignee: Roussel Uclaf
    Inventors: Emilio Toja, Carla Bonetti, Fernando Barzaghi, Giulio Galliani
  • Patent number: 5179212
    Abstract: 3-Pyrrolidinol or its salt is economically produced by cyclizing an aminobutanol derivative of the formula: ##STR1## wherein R is an alkyl or a substituted or unsubstituted phenyl group, or its salt.
    Type: Grant
    Filed: November 30, 1990
    Date of Patent: January 12, 1993
    Assignee: Kanegafuchi Chemical Industry Co., Ltd.
    Inventors: Satomi Takahashi, Shigeo Hayashi, Naoaki Taoka, Noboru Ueyama
  • Patent number: 5173484
    Abstract: An antibacterially active quinolone or naphthyridonecarboxylic acid derivative of the formula ##STR1## in which R.sup.1 stands for various organic radical,R.sup.2 stands for hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl,R.sup.3 stands for hydrogen or amino,R.sup.4 stands for a radical of the formula ##STR2## A stands for N or C-R.sup.5, whereinR.sup.5 stands for hydrogen, halogen methyl, cyano or nitro or else together with R.sup.1 can form a bridge of the structure ##STR3## or a pharmaceutically utilizable hydrate, acid addition salt, alkali metal salt, alkaline earth metal salt, silver salt or guanidinium salt of the carboxylic acid when R.sup.2 is hydrogen.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: December 22, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Thomas Schenke, Klaus Grohe, Michael Schriewer, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5164388
    Abstract: A renin inhibiting compound of the formula ##STR1## wherein X is N, O or CH; R.sub.1 is absent or a functional group; A and L are independently selected from absent, C.dbd.O, SO.sub.2 and CH.sub.2 ; D is C.dbd.O, SO.sub.2 or CH.sub.2 ; Y is N or CH; R.sub.2 is hydrogen, loweralkyl or substituted alkyl; Z is a functional group; R.sub.3 is loweralkyl or substituted alkyl; n is 0 or 1; and T is a mimic of the Leu-Val cleavage site of angiotensinogen; or a pharmaceutically acceptable salt, ester or prodrug thereof.
    Type: Grant
    Filed: April 18, 1991
    Date of Patent: November 17, 1992
    Assignee: Abbott Laboratories
    Inventors: Biswanath De, Thomas N. Zydowsky, William R. Baker, Joseph F. Dellaria, Saul H. Rosenberg, Hwan S. Jae
  • Patent number: 5162473
    Abstract: This invention relates to electrically conductive and non-conductive forms of poly(heterocyclic vinylenes) and to solutions of same. Another aspect of this invention relates to novel precursor polymers which can be converted into the poly(heterocyclic vinylenes) of this invention.
    Type: Grant
    Filed: July 7, 1987
    Date of Patent: November 10, 1992
    Assignee: Allied-Signal
    Inventors: Kwan-Yue A. Jen, Ronald L. Elsenbaumer, Lawrence W. Shacklette
  • Patent number: 5144042
    Abstract: A process for preparing optically active 3-hydroxypyrrolidine derivatives useful as intermediates represented by formula (III): ##STR1## wherein Q represents a substituted or unsubstituted phenyl group; and * indicates an asymmetric carbon atom, comprising reacting an optically active 4-halo-3-hydroxybutane derivative represented by formula (I): ##STR2## wherein * is as defined above; R.sup.1 represents a lower alkyl group or a substituted or unsubstituted phenyl group; and X represents a halogen atom, with a benzylamine derivative represented by formula (II):H.sub.2 NCH.sub.2 Q (II)wherein Q is as defined above, is disclosed. The starting compound (I) is easily available through chemical synthesis. Any complicated procedure or use of an expensive reagent is not required.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: September 1, 1992
    Assignee: Takasago International Corporation
    Inventors: Nobuo Seido, Yoshiki Okeda, Hidenori Kumobayashi
  • Patent number: 5140033
    Abstract: Antibacterial 5-alkylquinolonecarboxylic acids of the formula ##STR1## in which R.sup.3 is C.sub.1 -C.sub.4 -alkyl,R.sup.1 is optionally substituted alkyl or cycloalkyl, alkenyl, alkoxy, amino or alkylamino or optionally substituted phenyl,R.sup.2 is hydrogen or optionally substituted alkyl,R.sup.4 is a nitrogen-containing heterocyclic radical, andA is hydrogen, halogen, methyl, cyano or nitro, or forms a bridge with R.sup.1.and hydrates and salts thereof.
    Type: Grant
    Filed: October 1, 1990
    Date of Patent: August 18, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schriewer, Klaus Grohe, Andreas Krebs, Uwe Petersen, Thomas Schenke, Ingo Haller, Karl G. Metzger, Rainer Endermann, Hans-Joachim Zeiler
  • Patent number: 5137892
    Abstract: Novel antibacterial compounds are disclosed having the formula ##STR1## as well as pharmaceutically acceptable salts, esters, amide and prodrugs thereof,wherein R.sup.1 is selected from the group consisting of (a) lower alkyl, (b) halo(lower alkyl), (c) lower alkyl(alkynyl), (d) lower cycloalkyl, (e) lower alkylamino, (f) nitrogen-containing aromatic heterocycle, (g) bicyclic alkyl and (h) phenyl;R.sup.2 is selected from the group consisting of hydrogen, lower alkyl, a pharmaceutically acceptable cation, and a prodrug ester group;R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen, halogen, amino, and lower alkyl;R.sup.5 is either a nitrogen-containing heterocycle or a nitrogen-containing spiro-bicyclic-heterocycle; andA is N or C--R.sup.6, wherein R.sup.6 is selected from the group consisting of hydrogen, halogen, lower alkyl, and lower alkoxy, or R.sup.1 and R.sup.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: August 11, 1992
    Assignee: Abbott Laboratories
    Inventors: Daniel T. Chu, Curt S. Cooper
  • Patent number: 5136053
    Abstract: A method for producing a cyclic alkyleneimine, which comprises reacting a cyclic ether with a compound of the formula NH.sub.2 R wherein R is a hydrogen atom or an alkyl group, in a vapor phase in the presence of a solid acid catalyst, wherein the reaction is conducted under a pressure of at least 0.5 kg/cm.sup.2 G as the total pressure of partial pressures of the reactants and the reaction product.
    Type: Grant
    Filed: March 2, 1990
    Date of Patent: August 4, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Hitoshi Sugiyama, Tomoyuki Mori
  • Patent number: 5112848
    Abstract: Substituted furan and pyrrole compounds which are useful in inhibiting lipoxygenase enzymes, particularly 5-lipoxygenase.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: May 12, 1992
    Assignee: Abbott Laboratories
    Inventors: Dee W. Brooks, Bruce P. Gunn, James H. Holms, James B. Summers
  • Patent number: 5103007
    Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: April 7, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
  • Patent number: 5098927
    Abstract: Pyrroline compounds of the formulae (I) and (II) are effective in the treatment of retroviral infection and lymphadenopathy.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: March 24, 1992
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Kiyoshi Takatsuki, Yohsuke Maeda, Toshio Hattori, Tsutomu Kaizu, Masanori Okamoto, Yoshiko Yokota, Katsuya Nakamura, Hiroshi Kayakiri
  • Patent number: 5086054
    Abstract: Novel arylcycloalkanepolyalkylamines useful as anti-psychotic, anti-ischemia, anti-stroke, anti-dementia and anti-convulsant agents. These arylcycloalkanepolyalkylamines are selective high-affinity ligands to the sigma binding-sites containing three basic units: arylcycloalkyl group, an amine group and an intermediate chain. Their preparation and use for treatment of psychoses, ischemia, stroke, dementia and convulsions are also disclosed.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: February 4, 1992
    Assignee: SRI International
    Inventor: Daniel W. Parish
  • Patent number: 5081245
    Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: January 14, 1992
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
  • Patent number: 5077302
    Abstract: Urea derivatives of the following formula: ##STR1## wherein R.sub.2 indicates a piperidino or pyrrolidino group which may be substituted with a hydroxy group or a lower alkyl group having 1 to 13 carbon atoms; A indicates an ethylene group, propylene group, butylene group or butenylene group; R.sub.2 indicates a straight or branched alkyl group having 1 to 20 carbon atoms, a benzyl group, or a phenyl group which may have 1 to 3 substituents such as a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 3 carbon atoms, a halogen atom, a trifluoromethyl group, an amino group, a nitro group or a methylenedioxy group; and X indicates an oxygen or sulfur atom, as well as the hydrates and pharmaceutically acceptable salts thereof are useful antiulcer agents.
    Type: Grant
    Filed: May 15, 1990
    Date of Patent: December 31, 1991
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Matsukubo, Toyomi Matsumoto, Mitsutomo Miyashita, Kyuya Okamura, Fukutaro Taga, Haruo Sekiguchi, Katsuhiro Hamada
  • Patent number: 5049673
    Abstract: The present invention discloses a new class of calcium specific fluorescent indicator dyes having visible excitation and emission wavelengths. The new fluorescent indicator dyes combine at least one tricyclic chromophore with a tetracarboxylate parent CA.sup.2+ chelating compound having the octacoordinate pattern of liganding groups characteristic of BAPTA to give a rhodamine-like or fluorescein-like fluorophore. Binding of calcium.sup.2+ increases the fluorescence of the new compounds by up to 40-fold. The calcium.sup.2+ dissociation constants are in the range 0.37-2.3 microM, so that the new indicators give better resolution of high [CA.sup.2+ ] levels than were previously obtainable with predecessor compounds such as quin-2 or fluo-2. The visible excitation wavelengths of the new compounds are more convenient for fluorescent microscopy and flow cytometry than the UV required by previous indicators.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: September 17, 1991
    Assignee: The Regents of the University of California
    Inventors: Roger Y. Tsien, Akwasi Minta
  • 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: 5041555
    Abstract: Novel derivatives of 1,4-dideoxy-1,4-imino-D-mannitol and method for their synthesis from 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol or its triflate derivative are disclosed. The novel derivatives, 6-fluoro-1,4-imino-1,4,6-trideoxy-D-mannitol and the N-butyl and N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-mannitol, have useful mannosidase inhibitory activity.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: August 20, 1991
    Assignee: Monsanto Company
    Inventors: George W. J. Fleet, Bryan Winchester, Neil M. Carpenter
  • Patent number: 5017583
    Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are leukotriene antagonists. These compounds inhibit SRS-A and leukotriene synthesis and are antagonists of SRS-A and are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: May 21, 1991
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach, Haydn R. Williams, Masatoshi Kakushima, Yvan Guindon
  • Patent number: 5015770
    Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide, in the presence of iodine, iodine monochloride, or iodine monobromide as a catalyst.
    Type: Grant
    Filed: July 16, 1990
    Date of Patent: May 14, 1991
    Assignee: Ethyl Corporation
    Inventor: Gordon G. Knapp
  • Patent number: 5003081
    Abstract: Pyrrole derivatives of the formula ##STR1## or the tautomers thereof, where R.sup.1 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, hetaryl or amino, it being possible for these radicals to be substituted,R.sup.2 is hydrogen, alkyl, benzyl, alkenyl, cycloalkyl or phenylR.sup.3 is hydrogen, alkyl, benzyl or alkenyl, or R.sup.2 and R.sup.3 together are ##STR2## where T.sup.1, T.sup.2 and T.sup.3 have the meanings mentioned in the description, or R.sup.2 and R.sup.3 together with the nitrogen connecting them are a heterocyclic radical,R.sup.4 is cyano, or carbamoyl or thiocarbamoyl, each of which can be substituted, or --C(NH.sub.2).dbd.N--OH,R.sup.5 is halogen, hydroxyl, alkanoyloxy or benzoyloxy andR.sup.6 is hydrogen, alkyl, phenyl, cyano, halogen, nitro, hydroxysulfonyl, alkanoyl, benzoyl or ##STR3## where T.sup.4 is alkyl or phenyl and T.sup.5 is the radical of an active methylene compound, hydroxyimino or the radical of a primary amine,with the proviso that R.sup.1, R.sup.2 and R.sup.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: March 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Pfister, Matthias Wiesenfeldt, Karl-Heinz Etzbach
  • Patent number: 4996329
    Abstract: Novel derivatives of 1,4-dideoxy-1,4-imino-D-mannitol and method for their synthesis from 4,5-anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol or its triflate derivative are disclosed. The novel derivatives, 6-fluoro-1,4-imino-1,4,6-trideoxy-D-mannitol and the N-butyl and N-benzyl derivatives of 1,4-dideoxy-1,4-amino-D-mannitol, have useful mannosidase inhibitory activity.
    Type: Grant
    Filed: January 8, 1990
    Date of Patent: February 26, 1991
    Assignee: Monsanto Company
    Inventors: George W. J. Fleet, Bryan Winchester, Neil M. Carpenter
  • Patent number: 4966901
    Abstract: Pyrrole derivatives of the general formula I ##STR1## wherein R denotes alkyl which is substituted by --NH.sub.2 or acylamino, R.sup.1 and R.sup.2 independently of one another denote hydrogen or alkyl having 1 to 4 carbon atoms, R.sup.3 denotes hydrogen, alkyl having 1 to 4 carbon atoms or a carboxylic acid grouping, R.sup.
    Type: Grant
    Filed: May 23, 1989
    Date of Patent: October 30, 1990
    Assignee: Cassella Aktiengesellschaft
    Inventors: Gerhard Zoller, Rudi Beyerle, Ursula Schindler
  • Patent number: 4952591
    Abstract: Urea derivatives of the following formula, ##STR1## wherein R.sub.1 indicates a piperidino group or pyrrolidino group which may be substituted with hydroxy group or lower alkyl group having 1 to 3 carbon atoms; A indicates an ethylene group, propylene group, butylene group or butenylene group; R.sub.2 indicates a straight or branched alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 6 carbon atoms, benzyl group, or phenyl group which may have 1 to 3 substituents such as lower alkyl group having 1 to 6 carbon atoms, lower alkoxy group having 1 to 3 carbon atoms, halogen atom, trifluoromethyl group, amino group, nitro group or methylenedioxy group; X indicates an oxygen or sulfur atom, the hydrates and pharmaceutically acceptable acid addition salts thereof are useful as antiulcer agents.
    Type: Grant
    Filed: July 21, 1988
    Date of Patent: August 28, 1990
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Matsukubo, Toyomi Matsumoto, Mitsutomo Miyashita, Kyuya Okamura, Fukutaro Taga, Haruo Sekiguchi, Katsuhiro Hamada
  • Patent number: 4952600
    Abstract: This disclosure describes novel 3 or 4 substituted oxotremorine derivatives having polar substituted oxygen or sulfur groups. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and processes for the production of the compounds.
    Type: Grant
    Filed: February 20, 1990
    Date of Patent: August 28, 1990
    Assignee: American Cyanamid Company
    Inventors: Eugene J. Trybulski, Richard H. Kramss, Herbert J. Brabander
  • Patent number: 4943584
    Abstract: Novel (p-phenoxyphenoxy)-methyl-five-membered heeroaromatic radicals of the formula ##STR1## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3 hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano,R.sup.4 hydrogen or C.sub.1 -C.sub.4 -alkyl, and a five-membered heteroaromatic ring, and their use for combating pests.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
  • Patent number: 4910320
    Abstract: A process for preparing 3-pyrrolidinol having the formula (II): ##STR1## or a salt thereof, which comprises reducing 4-chloro-3-hydroxybutyronitrile having the formula (I): ##STR2## to convert said 4-chloro-3-hydroxybutyronitrile (I) into said 3-pyrrolidinol (II). According to the present invention, 3-pyrrolidinol, particularly optically active 3-pyrrolidinol can be prepared economically and efficiently.
    Type: Grant
    Filed: June 21, 1989
    Date of Patent: March 20, 1990
    Inventors: Kenji Inoue, Hidetoshi Kutsuki, Junzo Hasegawa, Satomi Takahashi
  • Patent number: 4904679
    Abstract: Pyrrolophenylalkanolamines of the formula ##STR1## R.sup.1 and R.sup.2 represent hydrogen or various radicals, R.sup.3 represents hydrogen, acyl or trialkylsilyl,R.sup.4 represents hydrogen or alkyl,R.sup.5 represents hydrogen, or, together with R.sup.3, represents ##STR2## wherein R.sup.7 represents hydrogen or alkyl, andR.sup.6 represents branched or cyfclic alkyl, which is optionally substituted,and salts thereof promote the yield of animals. Many new intermediates are also shown.
    Type: Grant
    Filed: April 22, 1988
    Date of Patent: February 27, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmund Wollweber, Jurgen Stoltefuss, Friedrich Berschauer, Ann de Jong, Martin Scheer
  • Patent number: 4900839
    Abstract: A series of novel heterocyclic-substituted 2-(1H)-quinolone compounds have been prepared, including the 3,4-dihydro derivatives thereof, wherein the heterocyclic ring moiety is a pyrrolyl, imidazolyl, pyrazolyl, triazolyl or tetrazolyl group attached by a nitrogen atom of said group to the 5-, 6-, 7- or 8-positions of the quinolone ring. These particular compounds are useful in therapy as highly potent inotropic agents and therefore, are of value in the treatment of various cardiac conditions. Preferred member compounds include 6-(2,4-dimethylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, 6-(2,4-dimethyl-5-nitroimidazol-1-yl)-8-methyl-2-(1H)-quinolone, 8-methyl-6-(tetrazol-1-yl)-2-(1H)-quinolone, 8-methyl-6-(1,2,4-triazol-4-yl)-2-(1H)-quinolone, and 6-(4-cyano-2-methylimidazol-1-yl)-8-methyl-2-(1H)-quinolone, respectively. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: January 27, 1989
    Date of Patent: February 13, 1990
    Assignee: Pfizer Inc.
    Inventors: Simon F. Campbell, David A. Roberts
  • 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: 4889955
    Abstract: ar-(Hydrocarbylthio)aromatic amines, such as (alkylthio) anilines, are prepared by heating one or more other ar-(hydrocarbylthio)aromatic amines in the presence of a catalyst, such as aluminum chloride, to redistribute the hydrocarbylthio groups with little or no co-formation of secondary or tertiary amines. The amine starting material is one or more primary aromatic amines having at least one free ring position and at least one hydrocarbylthio substituent in a ring position other than a meta-position.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: December 26, 1989
    Assignee: Ethyl Corporation
    Inventor: Paul F. Ranken
  • Patent number: 4847284
    Abstract: A novel pyrrolidinol isolated from the fermentation of Aspergillus ochraceus and certain derivatives thereof are described. The compounds are broad spectrum antifungal agents.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: July 11, 1989
    Assignee: Merck & Co., Inc.
    Inventors: Robert E. Schwartz, Janet C. Onishi, Richard L. Monaghan, Jerrold M. Liesch, Otto D. Hensens
  • Patent number: 4825002
    Abstract: A Lewis acid contaminant is removed from a (hydrocarbylthio)aromatic amine by mixing a solid alkali metal hydroxide with a solution of the Lewis acid in the amine, preferably at about 110.degree.-120.degree. C., and then filtering the solids from the mixture.
    Type: Grant
    Filed: November 2, 1987
    Date of Patent: April 25, 1989
    Assignee: Ethyl Corporation
    Inventor: Robert L. Davis
  • Patent number: 4808582
    Abstract: Compounds of formula: ##STR1## wherein: Ar is an aromatic group; R and R.sub.1 are H or CH.sub.3 ; A represents a nitrogenized heterocyclic radical; B is OH or forms with the adjacent CO group, either an amido group, or a carbonyloxy group; R.sub.2 and R.sub.3 are H or alkyl; m=0 or 1; and n=0, 1, 2 or 3.These compounds are useful as drugs having stimulating, protecting and/or correcting activities of the cerebral functions.
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: February 28, 1989
    Assignee: Delalande S.A.
    Inventors: Alain Y. Platel, Guy R. Bourgery, Patrick G. Guerret
  • Patent number: 4785109
    Abstract: These is described a process for producing sulfonylureas of the formula ##STR1## wherein G is an unsubstituted or substituted furanyl, thienyl, pyrrolyl, pyridinyl or phenyl radical,X is alkyl, haloalkyl, alkoxy, alkylthio, halogen, haloalkoxy, alkylamino or dialkylamino,Y is alkyl, alkoxy or haloalkoxy,Z is a nitrogen atom or the methyne group --CH.dbd..This novel process comprises reacting a sulfonamide of the formulaG--SO.sub.2 --NH.sub.2,in the presence of a base, with a chloroformic acid ester of the formulaCl--CO--Q--T,or a sulfonyl chloride of the formulaG--SO.sub.2 Cl,in the presence of a base, with a urethane of the formulaH.sub.2 N--CO--Q--T;and converting the formed carbamate of the formulaG--SO.sub.2 --NH--CO--Q--Tby reaction with an amine of the formula ##STR2## into the sulfonylurea of the above formula. There are also described novel sulfonylcarbamates of the above formula as intermediates.
    Type: Grant
    Filed: January 30, 1987
    Date of Patent: November 15, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Willy Meyer, Werner Fory, Werner Topfl
  • Patent number: 4774340
    Abstract: A novel compound useful in detecting leukocytes, esterase and protease in a test sample. The compound has the structure ##STR1## in which: A is an acid residue, R is lower alkyl, aryl, carboxyl, carboxyl ester, amido or cyano, R* is H or lower alkyl, and X is O, S, or NR', in which R' is H, lower alkyl or aryl.
    Type: Grant
    Filed: April 25, 1986
    Date of Patent: September 27, 1988
    Assignee: Miles Inc.
    Inventors: Paul F. Corey, Frederick E. Ward, Kin F. Yip, Meitak T. Yip
  • Patent number: 4751330
    Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide, in the presence of a metal or metal halide catalyst and iodine as a promoter.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: June 14, 1988
    Assignee: Ethyl Corporation
    Inventor: Robert L. Davis
  • Patent number: 4730050
    Abstract: A derivative of a fibrinolytic enzyme in which the catalytic site on the enzyme which is responsible for fibrinolytic activity is blocked by a human protein attached thereto by way of a reversible linking group.
    Type: Grant
    Filed: April 3, 1987
    Date of Patent: March 8, 1988
    Assignee: Beecham Group p.l.c.
    Inventor: Richard A. G. Smith
  • Patent number: 4727191
    Abstract: A (hydrocarbylthio)aromatic amine, such as a methylthiosubstituted toluenediamine, is separated from corresponding aromatic amines containing fewer hydrocarbylthio groups by washing an organic solution of the amine mixture with a dilute aqueous acid having a pKa value below 7 to extract at least a portion of the corresponding aromatic amines.
    Type: Grant
    Filed: July 10, 1986
    Date of Patent: February 23, 1988
    Assignee: Ethyl Corporation
    Inventor: Christopher J. Nalepa
  • Patent number: 4705853
    Abstract: Aromatic azepinones and thiones having the formula ##STR1## wherein; A is benzene, naphthalene, quinoline or pyridine;B is oxygen or sulfur;E is oxygen, sulfur or ##STR2## n is 1, 2 or 3; Z is an amino or a heterocyclic nitrogen-containing radical;R is hydrogen, loweralkyl, cycloalkyl or phenylloweralkyl;Y is halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, loweracetylamino, trifluoromethyl, phenyl or phenyl substituted by one to three Y' radicals selected from halo, loweralkyl, loweralkoxy, diloweralkylamino, nitro, amino, loweracylamino or trifluoromethyl;and having antihistaminic utility, a process for the preparation thereof and chemical intermediates therefor are disclosed.
    Type: Grant
    Filed: March 3, 1986
    Date of Patent: November 10, 1987
    Assignee: A. H. Robins Company, Inc.
    Inventor: Albert D. Cale, Jr.
  • Patent number: 4680338
    Abstract: A selective bifunctional sequential linker has the formulaY.dbd.C.dbd.N--Q--A--C(O)--Zwherein Q is a homoaromatic or heteroaromatic ring system; A is a single bond or an unsubstituted or substituted divalent C.sub.1-30 bridging group; Y is O or S; and Z is Cl, Br, I, N.sub.3, N-succinimidyloxy, imidazolyl, 1-benzotriazolyloxy, OAr where Ar is an electron-deficient activating aryl group, or OC(O)R where R is --A--Q--N.dbd.C.dbd.Y or C.sub.4-20 tertiary-alkyl. A method for activating an amine function towards reaction with a second amine involves reacting the amine with the foregoing linker. The resultant isocyanate or isothiocyanate derivative can then be reacted with a second amine to form a urea or thiourea conjugate.The linker is useful for producing conjugates of ligands with amine-containing polymers and/or proteins, especially for forming antibody conjugates with chelators, drugs, enzymes, detectable labels and the like.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: July 14, 1987
    Assignee: Immunomedics, Inc.
    Inventor: Boby M. Sundoro
  • Patent number: 4670597
    Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic monoamine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide, in the presence of hydrogen iodide, ammonium iodide, or cuprous iodide.
    Type: Grant
    Filed: November 8, 1985
    Date of Patent: June 2, 1987
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Robert L. Davis
  • Patent number: 4670598
    Abstract: (Hydrocarbylthio)aromatic polyamines are prepared by reacting an aromatic polyamine, such as a diaminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide, in the presence of an iodide or bromide of a metal other than an alkali metal as a catalyst.
    Type: Grant
    Filed: November 8, 1985
    Date of Patent: June 2, 1987
    Assignee: Ethyl Corporation
    Inventor: Robert L. Davis
  • Patent number: 4649204
    Abstract: Dialkanolamines and nontoxic pharmaceutically-acceptable acid-addition salts of the compounds of the following formula ##STR1## wherein R.sub.1 is hydrogen lower alkyl, or fluoro; R.sub.2 is hydrogen or lower alkyl; R.sub.3 and R.sub.4 are the same or different and selected from the group consisting of hydrogen or lower alkyl or R.sub.3 and R.sub.4 together define a chemical bond directly linking the two alkanol chains so as to form a pyrrolidine ring; Ar, is phenyl or thienyl or phenyl substituted with one to three substituents selected from the group consisting of lower alkyl and halo; and Ar.sub.2 is phenyl and phenyl substituted with one to three substituents selected from the group consisting of lower alkyl and halo which have antidepressant activity.
    Type: Grant
    Filed: September 30, 1985
    Date of Patent: March 10, 1987
    Assignee: McNeilab, Inc.
    Inventor: Bruce E. Maryanoff
  • Patent number: 4645842
    Abstract: A novel compound useful in detecting leukocytes, esterase and protease in a test sample. The compound has the structure ##STR1## in which: A is an acid residue, R is lower alkyl, aryl, carboxyl, carboxyl ester, amido or cyano, R* is H or lower alkyl, and X is O, S, or NR', in which R' is H, lower alkyl or aryl.
    Type: Grant
    Filed: April 6, 1984
    Date of Patent: February 24, 1987
    Assignee: Miles Laboratories, Inc.
    Inventors: Paul F. Corey, Frederick E. Ward, Kin F. Yip, Meitak T. Yip
  • Patent number: 4643762
    Abstract: 5-Amino-3-oxo-4-(substituted-phenyl)-4-pyrroline and derivatives thereof. The compounds generally exhibit both pre-emergence and post-emergence phytotoxicity and are useful as herbicides and also plant growth regulating agents at low dosages.
    Type: Grant
    Filed: August 27, 1984
    Date of Patent: February 17, 1987
    Assignee: Chevron Research Company
    Inventor: Carl E. Ward
  • 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: 4602095
    Abstract: Novel 3-hydroxy-4-alkyloxphenyl heterocyclic aromatic carboxylate compounds particularly well suited as sweeteners in foodstuff.
    Type: Grant
    Filed: December 29, 1983
    Date of Patent: July 22, 1986
    Assignee: General Foods Corporation
    Inventors: Paul R. Zanno, Ronald E. Barnett, Jed A. Riemer
  • Patent number: 4594453
    Abstract: (Hydrocarbylthio)aromatic amines are prepared by reacting an aromatic amine, such as an aminobenzene, with a hydrocarbyl disulfide, such as an alkyl disulfide. The reaction is preferably conducted in the presence of a Lewis acid catalyst, such as aluminum chloride.
    Type: Grant
    Filed: June 11, 1984
    Date of Patent: June 10, 1986
    Assignee: Ethyl Corporation
    Inventors: Paul F. Ranken, Bonnie G. McKinnie