Patents Examined by Henry R. Jiles
  • Patent number: 4711901
    Abstract: The present invention describes 1,6-naphthyridine derivatives of the general formula: ##STR1## wherein R.sup.1 is an unsubstituted or substituted aromtic or heteroaromatic ring, R.sup.2 is a straight-chained or branched alkyl radical containing up to four carbon atoms or a benzyl radical, R.sup.3 is a hydrogen atom, a straight-chained or branched alkyl radical or an alkoxycarbonyl radical containing up to four carbon atoms, R.sup.4 is a straight-chained or branched alkyl radical containing up to four carbons and R.sup.5 is a carbonyl group or a straight-chained, branched or cyclic alkoxycarbonyl radical which contains up to 17 carbon atoms and optionally also contains an oxygen, sulphur or nitrogen atom; as well as the pharamacologically acceptable salts thereof, which are useful for treating diseases of the blood vessels.
    Type: Grant
    Filed: July 30, 1986
    Date of Patent: December 8, 1987
    Inventors: Gerhard Satzinger, Johannes Hartenstein, Karl Mannhardt, Jurgen Kleinschroth, Hartmut Osswald, Gunter Weinheimer, Edgar Fritschi
  • Patent number: 4711679
    Abstract: Hexakis (2-nitroxyethyl) melamine which is useful as an energetic plasticr.
    Type: Grant
    Filed: October 22, 1985
    Date of Patent: December 8, 1987
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Everett E. Gilbert
  • Patent number: 4710501
    Abstract: Novel compounds of the formula ##STR1## in which R.sup.2 is hydrogen or a substituent, andR.sup.1 is optionally substituted alkyl or alkenyl,exhibit positive inotropic activity on the cardiac muscle, intensifying the contraction power.
    Type: Grant
    Filed: May 13, 1986
    Date of Patent: December 1, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Franckowiak, Martin Bechem, Rainer Gross, Michael Kayser, Matthias Schramm, Gunter Thomas
  • Patent number: 4710510
    Abstract: The present invention provides new pyrrolobenzimidazoles of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl, alkenyl or cycloalkyl radical; R.sub.2 is a hydrogen atom, cyano group or alkyl or alkenyl radical or a carbonyl group substituted by hydroxyl, alkyl, alkoxy, amino, alkylamino, dialkylamino or hydrazino or together with R.sub.1 forms a cycloalkylene radical or R.sub.1 and R.sub.2 together form an alkylidene or cycloalkylidene radical; R.sub.3, R.sub.4 and R.sub.
    Type: Grant
    Filed: December 10, 1985
    Date of Patent: December 1, 1987
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Jens-Peter Holck, Wolfgang Kampe, Bernd Muller-Beckmann, Klaus Strein, Wolfgang Schaumann
  • Patent number: 4710506
    Abstract: Novel thienopyridones with antihypertensive activity have the formula I, ##STR1## wherein the ring A represents an optionally substituted thiophene ring; m is 0 or 1; n is 0, 1 or 2; R is lower alkyl and R.sub.1 is lower alkyl.The fused thieno-ring may carry one or two substituents.Formula I encompasses thieno[3,2-b]pyridones, thieno[3,4-b]pyridones and thieno[2,3-b]pyridones.Processes for preparing the novel thienopyridones and pharmaceutical compositions containing them are described. Pharmaceutically acceptable acid addition salts of the compounds of formula I are also described.The thienopyridones of formula I are antihypertensive agents and are also indicated for use in treating heart failure and ischaemic heart disease.
    Type: Grant
    Filed: June 13, 1986
    Date of Patent: December 1, 1987
    Assignee: The Boots Company PLC
    Inventors: Roy V. Davies, James Fraser
  • Patent number: 4710504
    Abstract: Substituted hexahydro arylquinolizines and pharmaceutically acceptable salts thereof are selective .alpha..sub.2 -adrenergic receptor antagonists and thereby useful as antidepressants, antihypertensives, ocular antihypertensives, antidiabetics, platelet aggregation inhibitors, antiobesity agents, and modifiers of gastrointestinal motility.
    Type: Grant
    Filed: April 4, 1986
    Date of Patent: December 1, 1987
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, Joel R. Huff, Joseph P. Vacca, Steven D. Young, Jane deSolms, James P. Guare, Jr.
  • Patent number: 4708732
    Abstract: Herbicidal compounds having the formula ##STR1## wherein R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.3 and R.sup.4 together are oxo;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen or C.sub.1 -C.sub.4 alkyl; andR.sup.7 and R.sup.8 independently are (1) hydrogen; (2) halogen; (3) C.sub.1 -C.sub.4 alkyl; (4) C.sub.1 -C.sub.4 alkoxy; (5) trifluoromethoxy; (6) cyano; (7) nitro; (8) C.sub.1 -C.sub.4 haloalkyl; (9) R.sup.b SO.sub.n -- wherein n is the integer 0, 1 or 2; and R.sup.b is (a) C.sub.1 -C.sub.4 alkyl; (b) C.sub.1 -C.sub.4 alkyl substituted with halogen or cyano; (c) phenyl; or (d) benzyl; (10) --NR.sup.c R.sup.d wherein R.sup.c and R.sup.
    Type: Grant
    Filed: October 24, 1986
    Date of Patent: November 24, 1987
    Assignee: Stauffer Chemical Company
    Inventor: Charles G. Carter
  • Patent number: 4708733
    Abstract: The invention relates to new 4-chloro-aryloxy-acetyl- or 4-chloro-aryloxy-propionyl-malonates of the general Formula I, ##STR1## a process for the preparation thereof and herbicidal compositions comprising the same.In the general Formula IR.sup.1 stands for chlorine or methyl;R.sup.2 represents hydrogen or chlorine;R.sup.3 stands for hydrogen or methyl;R.sup.4 represents C.sub.1-4 alkyl and the two R.sup.4 groups may be identical or different; andX is --N.dbd. or --CH.dbd..The compounds of the general Formula I may be prepared by reacting a compound of the general Formula II ##STR2## with a metal derivative of a malonate of the general Formula III; ##STR3## or in the presence of an metal compound with a malonate of the general Formula III; or by reacting a compound of the general Formula IV ##STR4## with a compound of the general Formula V ##STR5## (in which Formulae R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X are as stated above; Z stands for halogen and Y represents halogen, cyano or alkylcarbonyloxy).
    Type: Grant
    Filed: September 23, 1986
    Date of Patent: November 24, 1987
    Assignees: Budapesti Vegyimuvek, MTA Kozponti Kemiai I Kutato Intezet
    Inventors: Tamas Komives, Ferenc Dutka, Istvan Barta, Istvan Jablonkai, Agnes Hulesch, Ferenc Bihari, Gyula Eifert, Peter Bohus, Mihaly Nagy, Gyorgy Bacskai, Istvan Kuronya
  • Patent number: 4709043
    Abstract: Novel imidazolonecarbonylarylimidazoles are described having cardiovascular properties, especially as cardiotonic agents in the treatment of congestive heart failure. Pharmaceutical formulations containing such compounds are also provided. Further, a novel process for the preparation of the compounds and intermediates useful thereto of this invention is disclosed.
    Type: Grant
    Filed: November 26, 1985
    Date of Patent: November 24, 1987
    Assignee: Schering A.G.
    Inventors: Paul W. Erhardt, Alfred A. Hagedorn, III, William C. Lumma, Jr., Ronald A. Wohl
  • Patent number: 4709045
    Abstract: A 1,2-substituted imidazoline compound having the formula (I): ##STR1## in which R2 is an alkyl or alkenyl group having 8 to 22 carbon atoms and n is 2 or 3, is produced by (1) feeding in a reactor a dialkylenetriamine (II) with a higher fatty acid of R2COOH or an ester thereof (III) at a molar ratio of the compound (III) to the compound (II) in the range of 1.5:1 to 1.8:1, (2) effecting the reaction at an internal temperature of 100.degree. to 250.degree. C. at a reduced pressure, (3) adding to the reaction mixture so that the above defined molar ratio in total may reach at least 2.0:1 and (4) continuing the reaction at an internal temperature of 100.degree. to 250.degree. C. at a reduced pressure. The reaction proceeds with a high yield of the product (I), without by-production to primary and second amines.
    Type: Grant
    Filed: June 6, 1986
    Date of Patent: November 24, 1987
    Assignee: Kao Corporation
    Inventors: Makoto Kubo, Koshiro Sotoya, Kazuhiko Okabe
  • Patent number: 4707494
    Abstract: 7-Oxabicyclo(2.2.1)heptane analogs are disclosed having the general formula ##STR1## wherein R.sub.1 is lower alkyl, alkenyl, substituted alkenyl or alkynyl; R.sub.2 is lower alkyl, alkenyl or alkynyl; A is --CH.sub.2 --CH.dbd.CH-- or a single bond; X is --CH.sub.2, --CH(CH.sub.3) or --C(CH.sub.3).sub.2 ; n is an integer from 0 to 9, with the proviso that when A is a single bond, n is an integer from 1 to 9; including all stereoisomers.These new compounds have been found to be inhibitors of arachidonic acid cyclooxygenase and are therefore useful as antiinflammatory antipyretic and analgesic agents.
    Type: Grant
    Filed: August 26, 1986
    Date of Patent: November 17, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Ravi K. Varma, Carl P. Ciosek, Eric M. Gordon
  • Patent number: 4707554
    Abstract: A new method has been disclosed for obtaining derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi.,5.dbd.-dihydroxy-3,3a.beta.,4,5,6,6a.beta.- hexahydro-2H-cyclopenta [b] furane useful in the synthesis of prostaglandins or their analogs, and a method for obtaining new sulphonyl initial compounds of the general formula 4, in which Z denotes a hydrogen atom or a protective group, Y denotes a group of the formula .dbd.CHOZ.sup.1, in which Z.sup.1 has the meaning stated for Z, whereby protective groups Z and Z.sup.1 may be the same or different, and Ar denotes optionally a substituted aryl group.In the method according to the invention the new sulphonyl derivative of the general formula 4 is alkylated with an electrophilic agent comprising: carbonyl derivatives, oxiranes and halohydrins or their derivatives; the alkylation product is transformed into derivatives of 4.beta.-/1'-alken-1'-yl/-2.xi.,5.alpha.-dihydroxy-3,3a.beta.,4,5,6,6a.beta .
    Type: Grant
    Filed: November 27, 1985
    Date of Patent: November 17, 1987
    Assignee: Polska Akademia Nauk-Instytut Chemii Organicznej
    Inventors: Barbara Achmatowicz, Andrzej R. Daniewski, Stanislaw Marczak, Jacek Pankowski, Jerzy Wicha
  • Patent number: 4705794
    Abstract: Pyridinecarboxylic acid esters of the formula ##STR1## in which R is an optionally substituted aryl or heterocyclic radical,R.sup.1 and R.sup.2 are hydrogen, alkyl, aryl, aralkyl, acyloxyalkyl or hydroxyalkyl, or R.sup.1 with X forms a carbonyl-containing heterocyclic ring,X is --CN, --CO--R.sup.4, --COOR.sup.5 or --SO.sub.2 R.sup.6,R.sup.4, R.sup.5 and R.sup.6 are various optionally substituted radicals, andR.sup.3 is different from R.sup.5 and is a substituted or interrupted hydrocarbon radical,or pharmaceutically acceptable salts thereof control the otherwise negative effects of ischaemia and/or hypoxia.
    Type: Grant
    Filed: February 28, 1983
    Date of Patent: November 10, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Egbert Wehinger, Horst Meyer, Ulrich Benz
  • Patent number: 4705856
    Abstract: .beta.-carbolines of formula I ##STR1## can be prepared by reacting an indole of formula II: ##STR2## with an azabutadiene of formula III ##STR3## in the presence of an acid at 50.degree.-200.degree. C.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: November 10, 1987
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Biere
  • Patent number: 4705786
    Abstract: A compound of the formula ##STR1## wherein T.sub.1 is lower alkylene, lower alkenylene or a single bond; X is ##STR2## T.sub.2 is carbonyl, lower alkylene or a single bond; R.sub.2 is phenyl, phenoxy, pyridyl, pyrimidinyl, furyl, thienyl, lower cycloalkyl or adamantyl;R.sub.2 and R.sub.6, when taken together with the nitrogen to which they are attached form pyrrolidinyl, piperidinyl or azacyclooctanyl;R.sub.14 is COOR.sub.8 or --R.sub.3 R.sub.9 wherein T.sub.3 is lower alkylene and R.sub.9 is lower alkoxy, lower cycloalkyl, cyano, polyfluoro-lower alkyl or pyridyl; andR.sub.1 and R.sub.5 are each lower alkyl or lower alkenyl, useful in the treatment of cardiovascular diseases.
    Type: Grant
    Filed: September 27, 1985
    Date of Patent: November 10, 1987
    Assignee: Sumitomo Pharmaceuticals Company, Limited
    Inventors: Michihiro Yamamoto, Yukinori Ozato, Nobuhiko Tamura, Akira Miyagishi, Youichi Hara
  • Patent number: 4705797
    Abstract: Novel antihypertensive and coronary dilating asymmetric diesters of 1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylic acid (or the stereoisomers or pharmaceutically acceptable acid addition salts thereof) have the general formula (I): ##STR1## wherein Ph is phenyl, Ar is 2-nitrophenyl, 3-nitrophenyl, 2,3-dichlorophenyl or benzofurazan-4-yl, A is a straight or branched chain alkylene radical having from 2 to 6 carbon atoms, R is a straight or branched chain alkyl radical having from 1 to 6 carbon atoms, optionally mono-substituted by an alkoxy substituent having from 1 to 6 carbon atoms, R.sub.1 is hydrogen, hydroxy or an alkyl radical having from 1 to 4 carbon atoms, and R.sub.2 is hydrogen or methyl. The subject diesters are facilely prepared from the aldehydes ArCHO and esters of acetoacetic and 3-aminocrotonic acids.
    Type: Grant
    Filed: February 14, 1985
    Date of Patent: November 10, 1987
    Assignee: Recordati S.A., Chemical and Pharmaceutical Company
    Inventors: Dante Nardi, Amedeo Leonardi, Gabriele Graziani, Giorgio Bianchi
  • Patent number: 4705859
    Abstract: Polychloropyridines containing chlorine substituents in the 2, 3, and 6 positions and, optionally, in the 4 and 5 positions, are prepared from polychloro-2,3-lutidines containing at least one chlorine substituent in each methyl group and, optionally, a chlorine substituent in the 6 position by liquid phase chlorination. Lewis acid metal halide catalysts are, optionally, employed. 2,3,5,6-Tetrachloropyridine is, accordingly, prepared by chlorination at about 200.degree. to about 260.degree. C. in the presence of ferric chloride catalyst of a mixture of polychloro-2,3-lutidines obtained by the vapor phase chlorination of 2,3-lutidine.
    Type: Grant
    Filed: July 22, 1986
    Date of Patent: November 10, 1987
    Assignee: The Dow Chemical Company
    Inventors: Jon A. Orvik, Thomas J. Dietsche
  • Patent number: 4705857
    Abstract: Indole derivatives of formula I ##STR1## R is hydrogen, one or two halogen atoms or one or two organic radicals in the 4-, 5-, 6- or 7-position(s),R.sup.1 and R.sup.4 are the same or different and each is hydrogen, alkyl of 1 to 3 carbon atoms or alkoxyalkyl of 1 to 3 carbon atoms in each of the alkoxy and alkyl portions,R.sup.3 is phenyl, --COOalkyl, --PO.sub.3 (alkyl).sub.2, --SO.sub.2 aryl, --SO.sub.2 alkyl, ##STR2## each of 1 to 3 carbon atoms in each alkyl group, and A and B each independently is alkyl of 1 to 3 carbon atoms or together with the connecting N-atom form a pyrrolidono, piperidino, morpholino or piperazino group,are valuable intermediates for preparing valuable tryptophans and .beta.-carbolines.
    Type: Grant
    Filed: October 28, 1983
    Date of Patent: November 10, 1987
    Assignee: Schering Aktiengesellschaft
    Inventor: Helmut Biere
  • Patent number: 4705867
    Abstract: 1,2-Dithiolane-3-pentanoic acid (D,L-thioctic acid) of the formula ##STR1## is prepared by a process comprising (a) reacting a 2-(3-alkylthiopropionyl)-cyclopentanone-1 of the formula ##STR2## where R is a C.sub.1 -C.sub.4 alkyl, phenyl or benzyl in aqueous alkaline solution at a temperature of about 20.degree. C. to about 90.degree. C. to form the corresponding carboxylic acid of formula VI ##STR3## (b) reacting the compound of formula VI with an alkyl mercaptan at a temperature between -20.degree. C. and 0.degree. C. to form the corresponding thioketal of formula VII ##STR4## (c) reacting the compound of formula VII with sodium in liquid ammonia at a temperature between -60.degree. C. and -10.degree. C.
    Type: Grant
    Filed: April 4, 1986
    Date of Patent: November 10, 1987
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenes Giray, Klaus Huthmacher, Axel Kleemann, Thomas Lied
  • Patent number: 4705888
    Abstract: This disclosure relates to novel peroxy esters carrying a t-alkenyl, e.g. 2-methyl-3-butene-2-yl, peroxy group. These peroxy esters have shorter half-life periods of decomposition and are more reactive polymerization initiators and unsaturated polyester resin curing agents than the corresponding prior art peroxy esters carrying a t-alkyl, e.g. t-amyl, peroxy group.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: November 10, 1987
    Assignee: Akzo NV
    Inventors: John Meijer, Hans Westmijze, Eltjo Boelema