One Double Bond Between Ring Members Of The Five-membered Hetero Ring (i.e., Pyrrolines) Patents (Class 548/565)
  • 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: 5077423
    Abstract: S-(N-alkoxycarbonyl, N-substituted)amino methyl isothiourea derivative, which is a useful intermediate for the production of 1,3,5-thiadiazine-4-one derivative, is disclosed. The above compound can be produced by reacting the carbamate compound of the formula(II) with the thiourea compound of the formula(III).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: December 31, 1991
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Dae-Whang Kim, Sung-Yeap Hong, Jae-Wook Ryu, Jae-Chun Woo
  • Patent number: 5051409
    Abstract: 2-Aminodecalin derivatives of the formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are H or methyl,A is H, OH, O-alkylcarbonyl, O-benzoyl or O-CH.sub.3,R.sup.4 is H, cyclopropyl, alkyl, alkenyl, or alkynyl,R.sup.5 is alkyl, alkenyl or alkynyl which is substituted or unsubstituted,cycloalkyl or cycloalkenyl whic is substituted or unsubstituted, substituted phenylalkyl, substituted cycloalkyl-alkyl, substituted 5-membered heterocyclic ring, bicycloalkyl-alkyl orR.sup.4 and R.sup.5, together with the nitrogen atom, are a substituted or unsubstituted, saturated or unsaturated piperidine radical,their plant-tolerated salts and N-oxides, and fungicides containing these compounds.
    Type: Grant
    Filed: November 1, 1989
    Date of Patent: September 24, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Zipplies, Bernhard Zipperer, Hubert Sauter, Norbert Goetz, Franz Roehl, Eberhard Ammermann, Gisela Lorenz
  • 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: 5032600
    Abstract: The invention refers to new diamines of the Formula I ##STR1## wherein R stands for ##STR2## or --NH--COA.sup.1 --R.sup.4 or ##STR3## wherein A stands for C.sub.1-5 alkylene which can be substituted by hydroxyl,X stands for a single or double bond,R.sup.2 stands for aryl or heteroaryl optionally substituted by halogen, C.sub.1-4 alkoxy or acylamino,R.sup.3 stands for hydrogen or C.sub.1-4 alkyl,A.sup.1 stands for a single bond or C.sub.1-5 alkyl optionally substituted by hydroxyl or thioalkylene or oxyalkylene,R.sup.4 stands for a 5- or 6- membered aromatic or heteroaromatic ring which can be substituted by one or more hydroxyl, C.sub.1-4 alkyl and/or C.sub.1-4 alkoxy and/or halogen or methylenedioxy and the alkyl group can be unsaturated as well,Q stands for a 6-membered ring which can be partially hydrogenated, andR.sup.1 stands for C.sub.1-4 alkyl.The new compounds are antiarrhythmic agents.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: July 16, 1991
    Assignee: Alkaloida Vegyeszeti Gyar
    Inventors: Kalman Hideg, Olga H. Hankovszky, Laszlo Frank, Ilona Bodi, Jozsef Csak
  • Patent number: 5028609
    Abstract: The invention refers to new diamines of the Formula I ##STR1## wherein R stands for ##STR2## wherein A stands for C.sub.1-5 alkylene which can be substituted by hydroxyl,X stands for a single or double bond,R.sup.2 stands for aryl or heteroaryl optionally substituted by halogen, C.sub.1-4 alkoxy or acylamino,R.sup.3 stands for hydrogen or C.sub.1-4 alkyl,A.sup.1 stands for a single bond or C.sub.1-5 alkyl optionally substituted by hydroxyl or thioalkylene or oxyalkylene,R.sup.4 stands for a 5- or 6- membered aromatic or heteroaromatic ring which can be substituted by one or more hydroxyl, C.sub.1-4 alkyl and/or C.sub.1-4 alkoxy and/or halogen or methylenedioxy and the alkyl group can be unsaturated as well,Q stands for a 6-membered ring which can be partially hydrogenated, andR.sup.1 stands for C.sub.1-4 alkyl.The new compounds are antiarrhythmic agents.
    Type: Grant
    Filed: November 27, 1989
    Date of Patent: July 2, 1991
    Assignee: Alkaloida Vegyeszeti Gyar
    Inventors: Kalman Hideg, Olga H. Hankovszky, Laszlo Frank, Ilona Bodi, Jozsef Csak
  • Patent number: 5006548
    Abstract: Compounds of the general formula: ##STR1## wherein R.sup.1 is heterocyclic group other than pyridyl and which is unsubstituted or substituted with lower alkyl or lower alkoxycarbonyl, R.sup.2 is hydrogen, halogen, or nitro, and R.sup.3 is carboxy group or its functional derivative, with the proviso that when R.sup.1 is an unsubstituted furyl, or furyl mono- or polysubstituted with alkyl and R.sup.2 is hydrogen, then R.sup.3 is functional derivative of carboxy and, where applicable, pharmaceutically acceptable salts thereof are hyaluronidase inhibitors and useful as anti-allergic agent.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: April 9, 1991
    Assignee: Sawai Pharmaceutical Co., Ltd.
    Inventors: Toshio Satoh, Hitoshi Matsumoto, Hisao Kakegawa, Yoshiko Kato, Juichi Riku, Junji Yoshinaga, Yoshifumi Kanamoto
  • Patent number: 5001233
    Abstract: The subject invention relates to a method of synthesizing hydroxylamines from secondary amines. This method uses a dioxirane compound such as dimethyldioxirane (DMD, which is relatively stable and simple to synthesize), as the oxidizing agent. The reaction proceeds as follows: ##STR1## This method provides a simple, one-step reaction with high yields. It can be performed in acetone solution, and the transferral of an oxygen atom from dimethyldioxirane to the secondary amine converts the dioxirane into acetone, the solvent, permitting simple workup and purification. This method can be used with a wide variety of secondary amines, including aliphatic, aromatic, cyclic, and heterocyclic secondary amines, to create a corresponding variety of hydroxylamines.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: March 19, 1991
    Assignee: The Curators of the University of Missouri
    Inventors: Robert W. Murray, Megh Singh
  • Patent number: 4987130
    Abstract: Substituted amino derivatives represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 each stand for an acyclic hydrocarbon residue or an alicyclic hydrocarbon residue; R.sup.3 and R.sup.4 each stand for hydrogen or a hydrocarbon residue optionally containing hetero-atom(s); A stands for a carbon chain having two or more carbon atoms optionally containing ether linkage or sulfide linkage, which may be substituted and which may per se form a ring; X.sup.1 and X.sup.2 each stand for oxygen atom or sulfur atom; and Y stands for amino group or an organic residue bonded through nitrogen atom, which may form a ring by combining with a carbon atom constituting A; and their salts have anti-arrhythmic activity and are useful for prevention and treatment of a variety of arrhythmias.
    Type: Grant
    Filed: December 22, 1989
    Date of Patent: January 22, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Susumu Tsushima, Muneo Takatani, Minoru Hirata
  • Patent number: 4897413
    Abstract: The invention refers to new diamines of the Formula I ##STR1## wherein stands for ##STR2## wherein A stands for C.sub.1-5 alkylene which can be substituted by hydroxyl,X stands for a single or double bond,R.sup.2 stands for aryl or heteroaryl optionally substituted by halogen, C.sub.1-4 alkoxy or acylamino,R.sup.3 stands for hydrogen or C.sub.1-4 alkyl,A.sup.1 stands for a single bond or C.sub.1-5 alkyl optionally substituted by hydroxyl or thioalkylene or oxyalkylene,R.sup.4 stands for a 5- or 6- membered aromatic or heteroaromatic ring which can be substituted by one or more hydroxyl, C.sub.1-4 alkyl and/or C.sub.1-4 alkoxy and/or halogen or methylenedioxy and the alkyl group can be unsaturated as well,Q stands for a 6-membered ring which can be partially hydrogenated, andR.sup.1 stands for C.sub.1-4 alkyl.The new compounds are antiarrhythmic agents.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: January 30, 1990
    Assignee: Alkaloida Vegyeszeti Gyar
    Inventors: Kalman Hideg, Olga H. Hankovszky, Laszlo Frank, Ilona Bodi, Jozsef Csak
  • Patent number: 4857539
    Abstract: Compounds of the formula ##STR1## wherein: Y is an alkylene bridge of 3-9 carbon atoms;Z is N or HC;R is hydrogen or lower-alkyl of 1-5 carbon atoms, with the proviso that when Z is N, R is lower-alkyl;R.sub.1 and R.sub.2 are hydrogen, halogen, lower-alkyl, lower-alkoxy, nitro, lower-alkoxycarbonyl or trifluoromethyl; andHet is selected from specified heterocyclic groups,are useful and antiviral agents, particularly against picornaviruses, including numerous strains of rhinovirus.
    Type: Grant
    Filed: June 16, 1987
    Date of Patent: August 15, 1989
    Assignee: Sterling Drug Inc.
    Inventors: Guy D. Diana, Philip M. Carabateas
  • Patent number: 4845090
    Abstract: Diagnostic media suitable for NMR diagnoses contain compounds of Formula I ##STR1## wherein is a single bond or a double bond, X is the grouping --(CH.sub.2).sub.n -- or, if is a single bond, also the grouping --NHCO(CH.sub.2).sub.n -- wherein n means 0 to 4,m means the numbers 0, 1, or 2,R.sub.1 is an alkyl residue substituted by hydroxy groups, acyloxy groups and/or alkylidenedioxy groups,R.sub.2 has the same meanings as R.sub.1 or is a hydrogen atom or an alkyl residue,R.sub.3 and R.sub.4 are alkyl residues, andR.sub.5 and R.sub.6 are alkyl residues optionally substituted by hydroxy groups.
    Type: Grant
    Filed: September 24, 1985
    Date of Patent: July 4, 1989
    Assignee: Schering Aktiengesellschaft
    Inventors: Heinz Gries, Ulrich Niedballa, Hanns-Joachim Weinmann
  • Patent number: 4804753
    Abstract: A process for the preparation of Schiff's bases which contain amino groups, of the formula ##STR1## wherein n is 3 to 12,by reacting cyclic lactams of the formula ##STR2## wherein n is 3 to 12,or of their ring-opened polymers of the formula ##STR3## wherein n is 3 to 12 andm is 1 to 100,000,with inorganic bases at elevated temperature, the reaction being carried out in the presence of inert, high-boiling suspending agents.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: February 14, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Helmut Schwarz
  • Patent number: 4778901
    Abstract: Intermediates for the production of microbicidal pyrrolines of the formula ##STR1## in which R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 14 C.sub.6 -haloalkyl, and n is 0, 1 or 2, and a method of converting the pyrrolines to phytofungicidal pyrroles by oxidation with bromine or oxygen. Catalysts are provided for the oxidation with oxygen.
    Type: Grant
    Filed: June 3, 1987
    Date of Patent: October 18, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Pierre Martin
  • Patent number: 4749701
    Abstract: Disclosed are an aminostyryl compound represented by Formula I: ##STR1## wherein A represents a linking group having 3 to 4 chain members; B represents an unsubstituted or substituted 5 to 6-membered monocyclic type heterocyclic residue containing 1 to 2 hetero atoms, an unsubstituted or substituted condensed heterocyclic residue which contains 5 to 6-membered monocyclic type heterocycle containing 1 to 2 hetero atoms, a naphthyl group or an alkyl group having 5 to 7 carbon atoms,a composition having leukotriene antagonism which contains an aminostyryl compound represented by Formula I as the effective ingredient, and a method of antagonizing SRS based on leukotriene antagonistic activity by employing the same.
    Type: Grant
    Filed: December 15, 1986
    Date of Patent: June 7, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Yoshio Hayashi, Tomei Oguri, Masaki Shinoda, Kazuo Takahashi
  • Patent number: 4748174
    Abstract: The water soluble acid addition salts of an NSAID, such as acetylsalicylic acid, fenbufen, diflunisal, piroxicam, naproxen, or the like, with either glucamine or meglumine (N-methylglucamine) are useful anti-inflammatory and analgesic drugs, well adopted for parenteral, oral, rectal or topical administration.
    Type: Grant
    Filed: January 5, 1987
    Date of Patent: May 31, 1988
    Assignee: Therapicon s.r.l.
    Inventor: Paolo A. Veronesi
  • Patent number: 4747965
    Abstract: Disclosed are additives which are useful as dispersants in lubricating oils, gasolines, marine crankcase oils and hydraulic oils. In particular, disclosed are multiply adducted alkenyl or alkyl succinimides which contain carbamate functionalities.
    Type: Grant
    Filed: August 15, 1986
    Date of Patent: May 31, 1988
    Assignee: Chevron Research Company
    Inventors: Robert H. Wollenberg, Frank Plavac
  • Patent number: 4746446
    Abstract: Disclosed are additives which are useful as dispersants in lubricating oils, gasolines, marine crankcase oils and hydraulic oils. In particular, disclosed are polyamino alkenyl or alkyl succinimides which contain carbamate functionalities.
    Type: Grant
    Filed: August 27, 1987
    Date of Patent: May 24, 1988
    Assignee: Chevron Research Company
    Inventors: Robert H. Wollenberg, Frank Plavac, Timothy R. Erdman
  • Patent number: 4727142
    Abstract: The invention relates to a process for the preparation of compounds of the formula I and salts or acid addition compounds thereof ##STR1## in which R denotes hydrogen, (halogenated) alkyl with the exception of CF.sub.3, a (substituted) aromatic radical, (substituted) heteroaryl, (substituted) phenoxy, (substituted) phenylthio, (substituted) phenylamino, halogen, hydroxyl, alkoxy, mercapto, (halogenated) cycloalkyl, alkylmercapto, amino, monoalkylamino or dialkylamino,R.sup.1 denotes (substituted alkyl, (substituted) phenyl or naphthyl, alkenyl, alkinyl, cycloalkyl, (substituted) benzyl or heteroaryl, and X denotes oxygen or sulfur, which comprises reacting a nitrile of the formula II with a compound of the formula IIIR--C.tbd.N (II)R.sup.
    Type: Grant
    Filed: April 18, 1986
    Date of Patent: February 23, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Fuss, Gunter Siegemund
  • Patent number: 4703056
    Abstract: The invention relates to new anti-arrhythmic compounds of the formula (I) ##STR1## wherein A is C1 to C5 alkylene which can be substituted by hydroxyl;X is a single or a double bond; andQ is a 6-membered carbocyclic moiety fused to each of the adjacent carbonyl carbon atoms, and which is either fully hydrogenated, partially hydrogenated, or aromatic, or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: September 20, 1984
    Date of Patent: October 27, 1987
    Assignee: Alkaloida Vegyeszeti Gyar
    Inventors: Kalman Hideg, Olga H. Hankovszky, Laszlo Frank, Ilona Bodi, Jozsef Csak
  • Patent number: 4695391
    Abstract: Disclosed are additives which are useful as dispersants in marine crankcase oils, hydraulic oils, and lubricating oils. In particular, disclosed are polyamino alkenyl or alkyl succinimides modified by reaction with a compound of the formula: ##STR1## wherein R.sub.4 is selected from the group consisting of a divalent hydrocarbyl group of from 2 to 30 carbon atoms with the proviso that the hydrocarbyl carbon atom bound to one ##STR2## group is not also bound to the other ##STR3## group and --R.sub.5 --OR.sub.5 --.sub.p wherein R.sub.5 is alkylene of from 2 to 5 carbon atoms and p is an integer of from 1 to 100; X is selected from the group consisting of bromo, chloro and --OR.sub.6 wherein R.sub.6 is selected from the group consisting of alkyl of from 1 to 6 carbon atoms, phenyl and phenyl substituted with 1 to 2 substituents selected from the group consisting of chloro, bromo, nitro, alkyl of from 1 to 6 carbon atoms and trifluoromethyl; and m is independently an integer of from 0 to 1.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: September 22, 1987
    Assignee: Chevron Research Company
    Inventor: Thomas F. Buckley
  • Patent number: 4687861
    Abstract: There are described novel microbicides and the production thereof, which correspond to the formula I ##STR1## in which R is halogen, C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.6 -haloalkyl, and n is 0, 1 or 2. The novel compounds are valuable active substances, particularly for controlling phytopathogenic fungi and bacteria. The compounds are suitable for protecting cultivated plants and seed, and can be advantageously used for the protection of stored stocks and provisions.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: August 18, 1987
    Assignee: Ciba-Geigy Corporation
    Inventor: Pierre Martin
  • Patent number: 4680413
    Abstract: A process for the production of a compound having the formula: ##STR1## which comprises a reaction of a compound having the formula: ##STR2## with a compound having the formulaR.sup.2 SO.sub.2 CH.sub.2 NCwhereinX is same or different substituent(s) selected from the group consisting of halogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, C.sub.1-6 alkylamino, C.sub.1-6 alkoxy, nitro, cyano and methylenedioxy;COOR.sup.1 is carboxylic acid or ester;R.sup.2 is C.sub.1-10 cyclic hydrocarbon which may be substituted by substituent(s) not giving negative effects to said reaction;n is 0, 1 or 2.
    Type: Grant
    Filed: December 30, 1985
    Date of Patent: July 14, 1987
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Yoshikazu Genda, Hiroyuki Muro, Kiyoharu Nakayama, Yoshiaki Miyazaki, Yoshiji Sugita
  • Patent number: 4647413
    Abstract: Perfluoropolyether oligomers or block polymers, having a backbone with one or a plurality of perfluoropolyether segments each consisting essentially of (1) at least one perfluoroisopropyleneoxy unit, (2) a bis(perfluoromethyleneoxy-terminated) unit, and (3) a perfluoroethylidene unit terminating each segment, the backbone of the perfluoropolyether being terminated with COF and/or a functional or nonfunctional derivative thereof, said perfluoropolyethers being made by reacting a perfluoroaliphatic diacid fluoride with hexafluoropropylene epoxide to produce an acid fluoride-terminated perfluoropolyether adduct or oligomer which then can be photopolymerized to yield an acid fluoride-terminated perfluoropolyether block polymer. These oligomers and block polymers are useful as high temperature lubricants, hydraulic fluids, gaskets, adhesives and coatings as well as co-reactants wtih urethane in forming propellant binders.
    Type: Grant
    Filed: January 20, 1984
    Date of Patent: March 3, 1987
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Patricia M. Savu
  • Patent number: 4645661
    Abstract: A method for alleviating cisplatin compound-induced nephrotoxicity in animals comprising administering to the animal an effective amount of a polar dithiocarbamate compound. The polar dithiocarbamate compounds have the formula: ##STR1## In the above formula, R.sup.1 and R.sup.2 are hydrocarbon groups and R.sup.1, R.sup.2, or both R.sup.1 and R.sup.2 contain a polar group substituted thereon. M is a pharmaceutically acceptable cation and n is an integer of from 1 to 3.Novel polar dithiocarbamate compounds are disclosed as well.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: February 24, 1987
    Assignee: St. Jude Children's Research Hospital
    Inventor: Gregory R. Schonbaum
  • Patent number: 4632935
    Abstract: OMEGA-(Hydroxy, ether and ester) alkyl-2-Amino-Cycloalkenyl and -cycloalkyl amide compounds of the formula: ##STR1## where the wavy line bonds, m, n, p, A, R, R.sub.1, R.sub.2, X, Y and Z are as defined in the specification, e.g., 3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-3-(3-acetyloxypropyl)cyclohexe nyl]benzamide, and pharmacologically acceptable salts thereof, are useful as analgesic drug compounds having low physical dependence liability, compared to morphine and methadone. Pharmaceutical compositions and methods for using these compounds and compositions as analgesics are disclosed. Processes for preparing this class of compounds are also disclosed.
    Type: Grant
    Filed: May 30, 1984
    Date of Patent: December 30, 1986
    Assignee: The Upjohn Company
    Inventor: Lester J. Kaplan
  • Patent number: 4626546
    Abstract: The invention is concerned with partially new compounds of the general formula ##STR1## wherein R.sup.1 is a hydrogen atom or an alkyl group with up to four carbon atoms and R.sup.2 a substituted phenyl radical and the pharmacologically acceptable salts thereof.The compounds can be prepared according to known procedures and show surprisingly a cardiovascular efficacy. They are capable of decompensating cardiac insufficiencies to a large extent. In addition to the new compounds, claim is also made for pharmaceutical compositions which contain compounds according to the general formula and their application for controlling cardiac and vascular diseases.
    Type: Grant
    Filed: August 3, 1984
    Date of Patent: December 2, 1986
    Assignee: Warner-Lambert Company
    Inventors: Gerhard Satzinger, Karl Mannhardt, Johannes Hartenstein, Manfred Herrmann, Edgar Fritschi, Wolfgang Steinbrecher
  • Patent number: 4611063
    Abstract: Compounds of the formula I: ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 is, independently, (a) alkyl having from 1 to 22 carbon atoms; or(b) of the formula ##STR2## in which m is 0, 1 or 2, and each of R' and R" is independently a hydrogen atom, alkyl having from 1 to 3 carbon atoms, alkoxy having from 1 to 3 carbon atoms, or halo having an atomic weight of from about 19 to 127; and R is of an aralkyl-, phenyl- tryptophanyl- or benzocycloalkyl-type, are obtained by hydrogenating corresponding .alpha.-.beta. ethylenically-unsaturated analogs (II), which in turn are obtained by hydrogenating corresponding .alpha.-.beta. acetylenically-unsaturated analogs. Compounds I and II are useful as anti-atheroslerotic agents.
    Type: Grant
    Filed: August 25, 1983
    Date of Patent: September 9, 1986
    Assignee: Sandoz Corp.
    Inventor: Robert E. Damon, II
  • Patent number: 4598088
    Abstract: N-[2-(2,5-dihydro-1H-pyrrol-1-yl)cycloaliphatic)]benzeneacetamide and -benzamide compounds, e.g., (1.alpha.,2.beta.)-(.+-.)-3,4-dichloro-N-[2-(2,5-dihydro-1H-pyrrol-1-yl)cy clohexyl]-N-methylbenzeneacetamide, and salts thereof, have useful analgesic activity, low abuse or physical dependence liability properties. Processes for their preparation are disclosed. Pharmaceutical compositions containing such compounds and methods for their use are also disclosed.
    Type: Grant
    Filed: May 29, 1985
    Date of Patent: July 1, 1986
    Assignee: The Upjohn Company
    Inventors: Jacob Szmuszkovicz, John M. McCall, Lester J. Kaplan, Moses W. McMillan
  • Patent number: 4594429
    Abstract: The present invention relates to a novel process for producing 3-chloro-1-formyl-4-phenylpyrroles having the general formula [I] as a useful fungicidal agent in agriculture and horticulture which is manufactured from the starting material of 3-phenyl-2,2,4-trichlorobutanal having the general formula [IV] as set forth in the following reaction formulae:By means of obtaining a pyrroline derivative having the general formula [III] as the intermediate compound, its production operation is greatly simplified and its yield rate is raised in comparison with the conventional processes. ##STR1## where X denotes the same or different kinds of substituent(s) being chosen from the group consisting of halo, nitro, and trifluoromethyl and n denotes zero or an integer of 1 or 2.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: June 10, 1986
    Assignee: Nippon Soda Co. Ltd.
    Inventors: Akiyoshi Ueda, Fumihiko Nagasaki, Yutaka Takakura, Shigeru Kojima
  • Patent number: 4587296
    Abstract: Additives for rubber compositions, giving vulcanisates having improved retention of optimum physical properties, are compounds containing two or more groups of the formula --S--SO.sub.2 R linked by an organic bridging group, or polymers containing two or more groups of the formula --S--SO.sub.2 R attached to an organic polymer chain, where R represents (a) a radical OM where M is a monovalent metal, the equivalent of a multivalent metal, a monovalent in derived by the addition of a proton to a nitrogenous base, or the equivalent of a multivalent ion derived by the addition of two or more protons to a nitrogenous base, or (b) an organic radical selected from aliphatic, cycloaliphatic, aromatic and heterocyclic radicals, and radicals which are combinations of any two or more such radicals.
    Type: Grant
    Filed: April 11, 1985
    Date of Patent: May 6, 1986
    Assignee: Monsanto Europe, S.A.
    Inventor: Philippe G. Moniotte
  • Patent number: 4581463
    Abstract: Halonitroarylacetic acid esters are prepared by reacting a halonitroaromatic compound with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base. The halonitroarylacetic acid esters formed by the process can be readily converted into derivatives, such as pharmaceuticals.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: April 8, 1986
    Assignee: Ethyl Corporation
    Inventors: G. Patrick Stahly, Barbara C. Stahly
  • Patent number: 4565891
    Abstract: A process for the catalytic oxidation of nonaromatic tertiary amines to the respective amine oxides is disclosed. An aqueous solvent system containing the tertiary amine is formed with an initial pH about equal to or greater than the pKa of the tertiary amine. This aqueous system is contacted with gaseous molecular oxygen at an oxygen partial pressure of at least about 50 psi and a temperature of at least about 80.degree. C. in the presence of certain octacyanomolybdate or iron (III) salts. The resulting oxidation converts the tertiary amine to the respective amine oxide in good yield.
    Type: Grant
    Filed: July 19, 1984
    Date of Patent: January 21, 1986
    Assignee: The Procter & Gamble Company
    Inventors: Paul E. Correa, Dennis P. Riley
  • Patent number: 4564698
    Abstract: The present invention relates to new tricyclic compounds of the formula: ##STR1## having valuable CNS and cardiovascular properties.
    Type: Grant
    Filed: January 24, 1983
    Date of Patent: January 14, 1986
    Assignee: Akzo N.V.
    Inventors: Johannes H. Wieringa, Frans A. van der Vlugt
  • Patent number: 4560767
    Abstract: Amino-cycloalkenyl-amide compounds, e.g., (1.alpha.,6.beta.)-(.+-.)-3,4-dichloro-N-methyl-N-(6-(1-pyrrolidinyl)-3-cy clohexen-1-yl)benzeneacetamide, and tritiated derivatives thereof, are useful as analgesics and as radio labeled compounds for pharmacological and metabolism studies in animals.
    Type: Grant
    Filed: June 17, 1983
    Date of Patent: December 24, 1985
    Assignee: The Upjohn Company
    Inventors: John M. McCall, Robert A. Lahti
  • Patent number: 4539408
    Abstract: Quaternary sulfoalkyl or sulfoalkenyl salts of tertiary amine bases are prepared by reacting the tertiary amine bases at elevated temperatures with a hydroxy alkane sulfonic acid or a hydroxyalkene sulphonic acid.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: September 3, 1985
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Helmut Kampfer, Marie Hase, Max Glass
  • Patent number: 4525586
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), methano (C-6a,9), and an additional (olefinic) valence bond (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2', 9-methano (or 2', 9-methano)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: September 19, 1983
    Date of Patent: June 25, 1985
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4518799
    Abstract: Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: May 21, 1985
    Assignee: The Upjohn Company
    Inventor: Thomas A. Hylton
  • Patent number: 4504668
    Abstract: Tertiary amines may be quaternized by heating them with a sulfoalkylating agent of this invention to a temperature of from 100.degree. to 250.degree. C. The sulfoalkylating agents which are believed to be hydroxy alkane sulfonic acid sulfoalkyl esters are free from sultone and are prepared by heating a hydroxy alkane sulfonic acid of propane or butane or the corresponding sultone to a temperature in the region of from 80.degree. to 180.degree. C. in the presence of water in an amount of 1 to 4 moles per mole of hydroxy alkane sulfonic acid or alkane sultone.
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: March 12, 1985
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Helmut Kampfer, Marie Hase, Max Glass
  • Patent number: 4485243
    Abstract: A process is described for the catalytic gas phase reduction of 4-oxoalkanenitriles to form 2-alkylpyrroles in high yields and conversions.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: November 27, 1984
    Assignee: Stamicarbon B.V.
    Inventors: Roland E. van der Stoel, Petrus H. J. Janssen, Cornelis G. M. van de Moesdijk
  • Patent number: 4465834
    Abstract: A class of anticholinergic drugs having the formula ##STR1## in which R.sup.1 is a carbocyclic or branched aliphatic group of 3 to 8 carbon atoms, R.sup.2 is a branched or linear aliphatic group containing 3 to 10 carbon atoms with 1 to 2 olefinic or acetylenic bonds and R.sup.3 is an alkyl or cyclic group of 4 to 12 carbon atoms containing a tertiary amino nitrogen, are described.
    Type: Grant
    Filed: September 20, 1965
    Date of Patent: August 14, 1984
    Assignee: FMC Corporation
    Inventors: Burton M. Baum, Hugo Stange
  • Patent number: 4447368
    Abstract: Aromatic aminosulphonic acids which have a reduced content of discoloring by-products are obtained when aromatic amines are reacted with a sulphonating agent in a reaction medium at least some of which consists of tetramethylene sulphone.
    Type: Grant
    Filed: March 31, 1982
    Date of Patent: May 8, 1984
    Assignee: Siemens-Allis, Inc.
    Inventors: Herbert Emde, Heinz U. Blank, Peter Schnegg
  • Patent number: 4433160
    Abstract: A process for producing an .alpha.-arylalkanoic acid ester represented by the general formula ##STR1## wherein Ar represents an aryl group which may optionally be substituted, and R.sup.1 and R.sup.2, independently from each other, represent a lower alkyl group,which comprises reacting a Grignard reagent prepared from an aryl halide of the general formulaAr--X.sup.1 (II)wherein Ar is as defined above and X.sup.1 represents a halogen atom,and magnesium, with an .alpha.-haloalkanoic acid ester of the general formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and X.sup.2 represents a halogen atom,said reaction of the Grignard reagent with the .alpha.-haloalkanoic acid ester of general formula (III) being carried out in the presence of a nickel compound.
    Type: Grant
    Filed: August 25, 1982
    Date of Patent: February 21, 1984
    Assignee: Taisho Pharmaceutical Company, Ltd.
    Inventors: Takehiro Amano, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Michihiro Ishiguro, Manzo Shiono, Yoshiji Fujita, Takashi Nishida
  • Patent number: 4421927
    Abstract: The present invention relates to a new cinnamoyl-cinnamic acid derivative selected from the group constituted by:(i) the m-cinnamoyl-cinnamic acid derivatives of formula ##STR1## in which: X.sub.o,X.sub.1,X.sub.2,X.sub.3,X.sub.4, which are identical or different, each represent an atom of hydrogen, a halogen, a lower alkyl group, a lower alkoxy group, the group NRR' (where R and R' identical or different, each represent an atom of hydrogen or a lower alkyl group), the group NO.sub.2, CF.sub.3 or OH;R.sub.1 represents an atom of hydrogen or a lower alkyl group;R.sub.2 represents an atom of hydrogen or the methyl group;Y represents a group OH, OR.sub.3 (where R.sub.3 is a lower alkyl group), NRR' (where R and R' are defined as hereinabove) or the group O(CH.sub.2).sub.n NR.sub.4 R.sub.5 (where n is an integer of value 1 to 5--and preferably 2 or 3)--; and R.sub.4 and R.sub.
    Type: Grant
    Filed: October 22, 1981
    Date of Patent: December 20, 1983
    Assignee: Societe de Recherches Industrielles (S.O.R.I.)
    Inventor: Francois Picart
  • Patent number: 4420614
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein A, B, D and E are chosen from hydrogen, halogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl and C.sub.1 to C.sub.6 alkoxy and Z is a tertiary or quaternary amino group.The compounds are useful intermediates for the preparation of pyrethroids. In further embodiments the invention provides processes for the preparation of the compounds of formula I and processes for the synthesis of pyrethroids utilizing the compounds of formula I.
    Type: Grant
    Filed: September 8, 1981
    Date of Patent: December 13, 1983
    Assignee: ICI Australia Limited
    Inventors: Colin Wilshire, Rene Jongen
  • Patent number: 4405624
    Abstract: 2,3-Unsaturated nitrogen-containing heterocyclic compounds with a 3-nitro group and a 2-heterocyclyl alkylamino group. The alkyl group of 2-position substituents is preferably interrupted by sulfur or oxygen. The compounds of the invention are preferably dihydropyrroles or tetrahydropyrridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.
    Type: Grant
    Filed: December 2, 1981
    Date of Patent: September 20, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Michael L. Roantree, Rodney C. Young
  • Patent number: 4389236
    Abstract: The invention relates to 3-phenoxymethylene-anilines of the formula ##STR1## wherein R is a ##STR2## radical or C.sub.1 -C.sub.4 alkoxy, R is halogen or C.sub.1 -C.sub.2 haloalkyl,R.sub.2, R.sub.3 and R.sub.4, each independently of the other, are hydrogen or halogenR.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkylR.sub.6 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, andR.sub.7 is hydrogen or C.sub.1 -C.sub.4 alkyl, while R.sub.5 and R.sub.6, or R.sub.6 and R.sub.7, together with the nitrogen atom to which they are attached, can form a heterocyclic ring system which may be interrupted by further hetero-atoms.Where R is a --NR.sub.6 R.sub.7 radical, the salts with acids also fall within the scope of formula I. These compounds have excellent selective herbicidal properties.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: June 21, 1983
    Assignee: Ciba-Geigy Corporation
    Inventor: Dieter Durr
  • Patent number: 4335124
    Abstract: The compounds are 4-phenyl-4-lower alkyl-substituted-3-buten-2-ones, and -2-halo-1,3-butadienes, e.g., 2-(p-biphenylyl)-2-penten-4-one, and are useful as pharmaceuticals.
    Type: Grant
    Filed: October 14, 1980
    Date of Patent: June 15, 1982
    Assignee: Sandoz, Inc.
    Inventor: Eugene E. Galantay