Nitrogen Attached Directly To The Piperazine Ring By Nonionic Bonding Patents (Class 544/382)
  • Patent number: 5366997
    Abstract: There are disclosed cardiovascularly active compounds possessing antihypertensive properties, and pharmaceutical compositions containing these agents and a method of treating cardiovascular disorders with the compounds. The active components of the pharmaceutical compositions are compounds of formula I ##STR1## wherein R.sub.1 and R.sub.2 are independently chosen from straight chain and branched chain alkyl and olefinic groups, which may be unsubstituted or substituted; or R.sub.1 and R.sub.2 together with the nitrogen atom they are bonded to form a heterocyclic group; and R.sub.3 is a pharmaceutically acceptable organic group selected from alkyl and olefinic groups which may be unsubstituted or substituted, acyl, a sulfonyl, sulfinyl, sulfenyl, carbonate, or carbamate derivative; or R.sub.3 is a group of the formula--(CH.sub.2).sub.n ONN(O)NR.sub.1 R.sub.2, wherein n is 2-8, and R.sub.1 and R.sub.2 are as described above. Novel compounds are disclosed wherein at least one of R.sub.1, R.sub.2 and R.sub.
    Type: Grant
    Filed: September 23, 1992
    Date of Patent: November 22, 1994
    Assignee: The United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Larry K. Keefer, Tambra M. Dunams, Joseph E. Saavedra
  • Patent number: 5326762
    Abstract: Amides of the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently heteroaryl, X-substituted heteroaryl, X-substituted phenyl, N-substituted triazinyl or N-substituted imidazolyl;and in addition, one of R.sub.1 and R.sub.2 can be as defined above and the other can be phenyl;R.sub.3 is an alkyl chain of 2 to 25 carbon atoms, saturated or unsaturated; an alkyl chain as defined substituted by one or more substituents selected from the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl; an alkyl chain as defined interrupted by one or more groups independently selected from the group consisting of --O--, --S--, --SO--, --SO.sub.2 --, --NH--, --N(lower alkyl)--, --C(O)--, phenylene, X-substituted phenylene, heteroarylene and X-substituted heteroarylene; or an interrupted alkyl chain as defined substituted by one or more substituents selected form the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl;R.sub.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: July 5, 1994
    Assignee: Schering Corporation
    Inventors: John Clader, Sundeep Dugar, Timothy Kogan, Bradley Tait, Wayne Vaccaro
  • 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: 5250550
    Abstract: There are disclosed novel complexes of nitric oxide and polyamines which are useful in treating cardiovascular disorders, including hypertension. The disclosed compounds release nitric oxide (endothelium-derived relaxing factor) under physiological conditions in a sustained and controllable fashion, and possess long mechanisms of action.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: October 5, 1993
    Assignee: The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Larry K. Keefer, Joseph A. Hrabie
  • Patent number: 5250528
    Abstract: This invention relates to new aminopiperazine derivatives having the potentiation of the cholinergic activity and represented by the general formula [I]: ##STR1## wherein R.sup.1 is lower alkyl, aryl, ar(lower)alkoxy or a heterocyclic group, each of which may be substituted with halogen,R.sup.2 is hydrogen or lower alkyl,R.sup.3 is cyclo(lower)alkyl, aryl or ar(lower)-alkyl, each of which may be substituted with halogen,A is ##STR2## or lower alkylene, and Y is ##STR3## and pharmaceutically acceptable salts thereof, to processes for the preparation thereof and to a pharmaceutical composition comprising the same.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: October 5, 1993
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Teruo Oku, Eishiro Todo, Yoshihiro Yokota, Hiroshi Kayakiri, Masashi Hashimoto
  • Patent number: 5200494
    Abstract: A one-pack type epoxide composition which has excellent storage stability and which can be rapidly cured at relatively low temperature is provided. It comprises as effective components (A) at least one epoxide having more than one, preferably more than 1.5 epoxy groups per a molecule, and (B) a curing agent prepared by heating and reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (c) at least one diisocyanate, or (C) a curing agent prepared by heating and reacting (a) at least one N,N-dialkylaminoalkylamine, (b) at least one amine having one or two nitrogen atoms with active hydrogen and having a ring structure in its molecule, (d) at least one epoxide having one or more epoxy groups in a molecule, and (c) at least on diisocyanate.
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: April 6, 1993
    Assignee: Fuji Kasei Kogyo Co., Ltd.
    Inventors: Masao Kubota, Ritaro Nagabuchi, Yasuo Chiba
  • Patent number: 5196583
    Abstract: The invention provides a novel class of propargyl compounds represented by the formula: ##STR1## wherein R is an C.sub.1 -C.sub.20 alkyl group, C.sub.1 -C.sub.20 alkylene group, C.sub.1 -C.sub.20 alkylene group interrupted by --NH-- group(s), C.sub.6 -C.sub.7 alicyclic group and an aromatic group; R.sub.1 comprises 1-100% --CH.sub.2 --C.tbd.CH group and 99-0% hydrogen atom and n is an integer of 1 to 4, and preparation thereof.These compounds are useful as coating material or sealer or rim-injection molding material.
    Type: Grant
    Filed: December 4, 1990
    Date of Patent: March 23, 1993
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Mitsuo Yamada, Kei Aoki
  • Patent number: 5182284
    Abstract: Disclosed are a piperazine compound of the formula below or a pharmaceutically acceptable salt thereof, medical uses thereof, and processes for preparing the same: ##STR1## wherein each of R and R' is --OH, a lower alkoxy, a halo, H, a di(lower alkyl) hydrogenphosphate residue or a group --OR" (R" is an aralkyl group, etc.), etc., Y is --CH.dbd.CH-- or --(CH.sub.2).sub.m -- (m is 0, 1 or 2), and Y.sub.1 is a group of the formula ##STR2## (wherein A is --NH-- or --O--, A.sub.1 is a methylene or a carbonyl, n is 6-20, X is --OH, H or a lower alkoxycarbonyl, and X.sub.1 is an optionally halo-substituted phenyl or H) or a group of the formula ##STR3## (wherein X and n are as defined above), provided that when Y.sub.1 is the group of the formula (3), each of R and R' is an --OH group.
    Type: Grant
    Filed: September 25, 1991
    Date of Patent: January 26, 1993
    Assignee: Taiho Pharmaceutical Co., Ltd.
    Inventors: Masahiro Suzuki, Kenji Nozaki, Makoto Kajitani, Mitsugi Yasumoto, Naohiko Ono, Takashi Shindo
  • Patent number: 5155137
    Abstract: There are disclosed novel complexes of nitric oxide and polyamines which are useful in treating cardiovascular disorders, including hypertension. The disclosed compounds release nitric oxide (endothelium-derived relaxing factor) under physiological conditions in a sustained and controllable fashion, and possess long mechanisms of action.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: October 13, 1992
    Assignee: The United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Larry K. Keefer, Joseph A. Hrabie
  • Patent number: 5149872
    Abstract: A new process for preparing oxalyl- and oxamyl-hydrazides which comprises contacting oxamide or diacetyloxamide with the corresponding hydrazine derivative of formulaR.sub.1 R.sub.2 N--NHR.sub.3wherein R.sub.1 represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl, or aryl-alkyl group, R.sub.2 is a hydrogen atom or an optionally substituted alkyl group, or R.sub.1 and R.sub.2 taken together with the adjacent nitrogen atom represent a saturated heterocyclic ring, and R.sub.3 is a hydrogen atom or an optionally substituted alkyl group.
    Type: Grant
    Filed: February 14, 1991
    Date of Patent: September 22, 1992
    Assignee: Enichem Anic S.p.A.
    Inventors: Giuseppe Messina, Loreno Lorenzoni, Paolo Calaresu, Giovanni M. Sechi
  • Patent number: 5075337
    Abstract: Deuterated 2-alkylaminoacetamide compounds are described having the alpha carbon of the alkyl side chain of the compounds substituted by one or two deuterium atoms. These compounds have pharmacokinetic properties which enable treatment of CNS diseases with lower toxic effects. These compounds are also useful in evaluating the metabolic fate of non-deuterated counterpart compounds. Of particular interest are compounds of Formula I: ##STR1## wherein X is deutero or hydrido; wherein R.sup.1 is selected from alkyl and aralkenyl; wherein each of R.sup.2 and R.sup.3 is independently selected from hydrido and alkyl; wherein each of R.sup.1, R.sup.2 and R.sup.3 having a substitutable position may be substituted with one or more halo radicals; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: July 26, 1989
    Date of Patent: December 24, 1991
    Assignee: G. D. Searle & Co.
    Inventors: Alex A. Cordi, Philippe Janssens de Varebeke, Hugo Gorissen
  • Patent number: 5073635
    Abstract: A process of preparing linearly-extended polyalkylenepolyamines, such as linear and branched polyethylenepolyamines, comprising contacting a difunctional aliphatic alcohol, such as monoethanolamine, with a reactant aliphatic amine, such as ethylenediamine, in the presence of a metal silicate catalyst wherein the metal is selected from Groups IIIB, IVB, VB and the lanthanide rare earth metals. Reactions of piperazines with alkanolamines to yield alcohol-extended and/or amine-extended piperazines are included in the process of this invention.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: December 17, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5047425
    Abstract: Compounds of the formula ##STR1## wherein Ar, R, R.sub.1, R.sub.2, R.sub.3, R.sub.4, X and n have the meanings mentioned in the description, processes and intermediates for their preparation, pharmaceutical compositions which contain them and their use in therapy in the treatment of cardiovascular diseases.
    Type: Grant
    Filed: November 30, 1988
    Date of Patent: September 10, 1991
    Assignee: Simes Societa Italiana Medicinali & Sintetici SpA
    Inventors: Cesare Casagrande, Francesco Santangelo, Luisa Calabi
  • Patent number: 5017721
    Abstract: A new process for preparing oxalyl- and oxamyl-hydrazides which comprises contacting oxamide or diacetyloxamide with the corresponding hydrazine derivative of formulaR.sub.1 R.sub.2 N--NHR.sub.3wherein R.sub.1 represents a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl, or aryl-alkyl group, R.sub.2 is a hydrogen atom or an optionally substituted alkyl group, or R.sub.1 and R.sub.2 taken together with the adjacent nitrogen atom represent a saturated heterocyclic ring, and R.sub.3 is a hydrogen atom or an optionally substituted alkyl group.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: May 21, 1991
    Assignee: Enichim ANIC S.p.A.
    Inventors: Giuseppe Messina, Loreno Lorenzoni, Paolo Calaresu, Giovanni M. Sechi
  • Patent number: 4997836
    Abstract: Novel trisubstituted piperazine compounds of the formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.
    Type: Grant
    Filed: November 9, 1989
    Date of Patent: March 5, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hirosada Sugihara, Kohei Nishikawa
  • Patent number: 4981963
    Abstract: A new process is described for the preparation of oxalic acid esters and amides of general formula (I) ##STR1## wherein Z designates an --OR or --NR.sup.1 R.sup.2 group, wherein R represents substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, or aryl-alkyl, R.sup.1 is hydrogen or substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, or aryl-alkyl, R.sup.2 represents substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, or aryl-alkyl, or R.sup.1 and R.sup.2 taken together with the adjacent nitrogen atom represent a saturated 5-, 6-, 7-, or 8-membered heterocyclic ring, which may contain an additional heteroatom selected from --O--, --S--, and --N(H, Alkyl)--, and optionally bear one or more alkyl or alkenyl substituents, andZ.sup.1 designates an --OR or --NR.sup.1 R.sup.2 group, wherein R, R.sup.1, and R.sup.2 are as defined before, or a group --NHCOCH.sub.3, which comprises the base-catalysed reaction of diacetyloxamide with an alcohol ROH or/and an amine HNR.sup.1 R.sup.2.
    Type: Grant
    Filed: April 21, 1989
    Date of Patent: January 1, 1991
    Assignee: Enichem Anic S.p.A.
    Inventors: Giuseppe Messina, Giovanni M. Sechi, Loreno Lorenzoni, Giovanni Chessa
  • Patent number: 4940727
    Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors are useful as anti-hypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1##
    Type: Grant
    Filed: October 6, 1988
    Date of Patent: July 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Edward S. Inamine, Otto D. Hensens, David R. Houck, Ta J. Lee, Robert L. Smith, Wasyl Halczenko, George D. Hartman, Gerald E. Stokker
  • Patent number: 4940793
    Abstract: New piperazino derivatives of formula ##STR1## in which R is a phenyl radical substituted with at least one sulphonamido group or a substituted nitrogenated heterocyclic ring, and A is CO, CH.sub.2, SO.sub.2, possessing inhibiting activity towards carbonic anhydrase.The new products are prepared from compounds of formula R-A-X in which X is OH, SH, halogen, OR"" or SR"" in which R"" is methyl, ethyl, phenyl, carbomethoxy, carboethoxy, and from a piperazino derivative of formula ##STR2## The R' group can also be introduced on termination of the reaction, by removing and substituting a protective group present at the nitrogen.
    Type: Grant
    Filed: July 18, 1985
    Date of Patent: July 10, 1990
    Assignee: Ravizza S.p.a.
    Inventors: Francesco Botre, Roberto Signorini
  • Patent number: 4889953
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 is a higher alkyl group which may be substituted; R.sup.2 is a hydrogen, a lower alkyl group which may be substituted, a lower alkanoyl group which may be substituted or a lower alkylthiocarbamoyl group; R.sup.3 is a primary to tertiary amino group or a quaternary ammonium group; and n is 2 or 3, and salts thereof, have antitumor activity and platelet activating factor inhibitory activity.
    Type: Grant
    Filed: July 22, 1987
    Date of Patent: December 26, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keizo Inoue, Hiroaki Nomura, Tetsuya Okutani
  • Patent number: 4857644
    Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each, independently, hydrogen, lower alkyl or phenyl; or R.sup.1 and R.sup.2 taken together represent --(CH.sub.2).sub.4 --or ##STR2## where the dotted line represents an optional double bond; R.sup.3 is hydrogen, lower alkyl, lower alkoxy or halo;R.sup.4 is pyridinyl, pyrimidinyl, pyrazinyl, benzyl, phenyl or phenyl substituted by lower alkyl, lower alkoxy, or halo;Z is --SO.sub.2 --or ##STR3## where R.sup.5 is hydrogen or lower alkyl; m is 0-4;n is 0-2; andthe pharmaceutically acceptable salts thereof, and their use as anti-inflammatory agents.
    Type: Grant
    Filed: June 9, 1988
    Date of Patent: August 15, 1989
    Assignee: American Home Products Corporation
    Inventor: Magid A. Abou-Gharbia
  • Patent number: 4839358
    Abstract: Novel .alpha.-mercaptomethyl-benzene propanamides of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and ##STR2## R.sub.1 ' is selected from the group consisting of alkyl of 1 to 5 carbon atoms and aryl optionally substituted with at least one member of the group consisting of --OH, --NO.sub.2, halogen and alkyl and alkoxy of 1 to 5 carbon atoms, X and X' are individually selected from the group consisting of hydrogen, alkyl and alkoxy of 1 to 5 carbon atoms, --OH, halogen and --CF.sub.3, R.sub.2 is selected from the group consisting of pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl, tetrahydrothiazinyl and hexahydroazepinyl, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, --OH, --NO.sub.2, --CF.sub.
    Type: Grant
    Filed: February 23, 1988
    Date of Patent: June 13, 1989
    Assignee: Roussel Uclaf
    Inventors: Jean-Paul Vevert, Francoise Delevallee, Jean-Claude Gasc, Francis Petit
  • Patent number: 4803277
    Abstract: Novel insecticidally active heterocyclic compounds of the formula ##STR1## wherein W represents a substituted pyridyl group, or a 5- or 6-membered optionally substituted heterocyclic group containing at least two hetero atoms selected from oxygen, sulfur and nitrogen atoms,R represents a hydrogen atom or an alkyl group,Y represents .dbd.N--or ##STR2## R' represents a hydrogen atom, an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group or a cyano group,Z represents a nitro group or a cyano group, andT represents 3 or 4 optionally substituted ring members of a 5- or 6-membered unsaturated heterocyclic ring which it forms together with the adjoining carbon atom and nitrogen atom, said 5- or 6-membered unsaturated heterocyclic ring containing 1 to 3 hetero atoms which are selected from oxygen, sulfur and nitrogen atoms and at least one of which is a nitrogen atom.
    Type: Grant
    Filed: August 24, 1987
    Date of Patent: February 7, 1989
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shoko Sasaki, Koichi Moriya, Yumi Hattori, Katsuhiko Shibuya
  • Patent number: 4780495
    Abstract: N-(substituted)-1-(piperazinealkyl)-.alpha.-(3,5-dialkyl-4-hydroxyphenyl)-. alpha.,.alpha.-disubstited acetamides, are novel compounds prepared by a novel modification of the ketoform process. The compounds are useful as stabilizers for organic materials subject to degradation in an environment in which the materials are exposed to heat, oxidation and light, particularly ultraviolet light. The compounds are especially useful in combination with known secondary stabilizers.
    Type: Grant
    Filed: January 25, 1988
    Date of Patent: October 25, 1988
    Assignee: The B. F. Goodrich Company
    Inventors: John T. Lai, Pyong N. Son
  • Patent number: 4766116
    Abstract: A diaryl butyric acid derivative having the general formula: ##STR1## wherein R.sup.1 represents a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or an acyl group having 2 to 4 carbon atoms; R.sup.2 represents an alkyl group having 1 to 3 carbon atoms; andX represents a variety of substituents.This diaryl butyric acid derivative or the pharmaceutically acceptable salt thereof can be prepared by reacting a benzoxepin derivative having the general formula: ##STR2## wherein R.sup.2 is the same as defined above with an amine or alcohol derivative having the general formula;X--Hwherein X is the same as defined above in the presence of an acid catalyst at room temperature or at an elevated temperature and, optionally, further reading the reaction product with an alkylation agent having 1 to 3 carbon atoms or an acylation agent having 2 to 4 carbon atoms.
    Type: Grant
    Filed: December 19, 1985
    Date of Patent: August 23, 1988
    Assignee: Suntory Limited
    Inventors: Toshio Tatsuoka, Kenji Suzuki, Kayoko Imao, Kunihiro Sumoto
  • Patent number: 4739083
    Abstract: A new process for preparing a pyrone-3-carboxamide compound of the formula (IV): ##STR1## wherein R.sub.1 is aryl or heterocyclic group optionally substituted, R.sub.2 is alkyl, aralkyl or like group, comprising reacting a compound of the formula (I) or (I'): ##STR2## wherein R.sub.3 is dialkylamino group and n is 0 to 6, and R.sub.1 and R.sub.2 are as above,with a compound of the formula (II): ##STR3## wherein R.sub.4 and R.sub.5 are hydrogen atom, alkyl or like group, or reacting a compound of the formula (III): ##STR4## wherein R.sub.6 is alkyl, aryl or like group, and R.sub.1 and R.sub.2 are as above,with a compound of the formula (II) or diketene in the presence of a tertiary organic base.
    Type: Grant
    Filed: January 2, 1986
    Date of Patent: April 19, 1988
    Assignee: Daicel Chemical Industries Ltd.
    Inventors: Yoichiro Ueda, Yukihisa Goto, Kazuhisa Masamoto
  • Patent number: 4701447
    Abstract: This invention relates to organic acid-substituted guanidine compounds. Also disclosed are methods for preparing the compounds, compositions containing them, and methods for their use as anthelmintics.
    Type: Grant
    Filed: September 23, 1983
    Date of Patent: October 20, 1987
    Assignee: Schering Corporation
    Inventors: Dhiru B. Vashi, Jeffrey N. Clark, Neil A. Lindo
  • Patent number: 4650871
    Abstract: This invention relates to sulfamoylbenzoic acid derivatives which possess diuretic and uricosuric activities, and which are of the formula (I) ##STR1## wherein R.sub.1 is a chlorine atom or phenoxy group, R.sub.2 is a hydrogen atom, halogen atom, lower alkyl group, lower alkoxy group or methylenedioxy group.
    Type: Grant
    Filed: December 3, 1985
    Date of Patent: March 17, 1987
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Irikura, Kyuya Okamura, Hideo Okubo, Hidemichi Mizuguchi, Shigeru Yamanaka
  • Patent number: 4564677
    Abstract: Disclosed is a method of preparing N-amino compounds from corresponding secondary amines by reacting a secondary amine with nitrous acid and zinc in a neutral pH reaction media to form the corresponding N-amine.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: January 14, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventor: Martin L. Kantor
  • Patent number: 4539405
    Abstract: The novel explosive compound, 1,4-dinitrofurazano[3,4-b]piperazine, is prred by the reaction of 2,3-dioximinopiperazine with a base, followed by the nitration of the intermediate furazano[3,4-b]piperazine. The nitrated compound has a density, detonation pressure, detonation velocity and Isp similar to RDX while being highly insensitive.
    Type: Grant
    Filed: April 16, 1984
    Date of Patent: September 3, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Rodney L. Willer
  • Patent number: 4523013
    Abstract: 2-Acyl-1,3,4,6,7,11b-hexahydro-2H-pyrazino-[2,1-a]-4-isoquinoleinones having anthelmintic activity of the formula ##STR1## are prepared from 4-acyl-2,6-dioxopierazines by reaction with a phenethyl halide, selective reduction of one of the oxo groups and cyclization, by the novel intermediates of formula ##STR2## in which Y represents O or H, OH.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: June 11, 1985
    Assignee: Sanofi, S.A.
    Inventors: Daniel Frehel, Jean-Pierre Maffrand
  • Patent number: 4421754
    Abstract: A 3-[4-(benzoylalkyl)piperazin-1-yl]sydnonimine compound represented by the following formula ##STR1## wherein R represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and n represents zero or an integer of 1 to 10,and its acid addition salt. The above sydnonimine compounds are useful for the treatment of troubles of the circulatory system and can be produced by contacting a 4-(benzoylalkyl)-1-(N-nitrosocyanomethylamino)piperazine represented by the following formula ##STR2## wherein R and n are as defined, with an acid.
    Type: Grant
    Filed: July 29, 1982
    Date of Patent: December 20, 1983
    Assignee: Hiroyoshi Hidaka
    Inventors: Hiroyoshi Hidaka, Ikuo Matsumoto, Junji Yoshizawa, Shigenori Kotani
  • Patent number: 4419363
    Abstract: Novel 1-aryloxy-3-amidoamidoalkylamino-2-propanol derivatives, processes for their manufacture, pharmaceutical compositions containing them and methods of using them in the treatment of heart diseases. Representative of the compounds disclosed is 1-(o-cyanophenoxy)-3-.beta.-(2-thenamidoacetamido)ethylaminopropan-2-ol.
    Type: Grant
    Filed: June 4, 1982
    Date of Patent: December 6, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Leslie H. Smith
  • Patent number: 4375470
    Abstract: 2-(1-Piperazinyl)-cycloheptimidazole derivatives are disclosed. The foregoing compounds are useful antihypertensive agents.
    Type: Grant
    Filed: October 17, 1980
    Date of Patent: March 1, 1983
    Assignee: American Home Products Corporation
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4362886
    Abstract: A process for selectively preparing predominantly non-cyclic polyalkylene polyamine compounds is disclosed wherein an alkylene polyamine compound is contacted with a hydroxy compound in the presence of a catalytically effective amount of a substance of arsenic, antimony or bismuth at a temperature of from 250.degree. to 300.degree. C. under a pressure sufficient to maintain the reaction mixture essentially in liquid phase. The polyalkylene polyamine thus formed is recovered from the reaction mixture.
    Type: Grant
    Filed: January 5, 1981
    Date of Patent: December 7, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Thomas A. Johnson
  • Patent number: 4348406
    Abstract: Compounds of the formula: ##STR1## and their pharmaceutically acceptable acid addition salts, useful as anthelmintics are disclosed.
    Type: Grant
    Filed: October 20, 1980
    Date of Patent: September 7, 1982
    Assignee: Schering Corporation
    Inventor: M. Mehdi Nafissi-Varchei
  • Patent number: 4304937
    Abstract: A process of preparing a carboxylic acid amide which comprises reacting (a) an aldehyde with (b) at least one compound selected from the group consisting of ammonia, a primary amine and a secondary amine in the presence of a molecular oxygen-containing gas and palladium metal or platinum metal as the catalyst.
    Type: Grant
    Filed: November 13, 1979
    Date of Patent: December 8, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Nishikido Joji, Tamura Nobuhiro, Fukuoka Yohei
  • Patent number: 4274837
    Abstract: Fuel compositions for internal combustion engines are provided containing deposit control additives which maintain cleanliness of intake systems without contributing to combustion chamber deposits. The additives are hydrocarbylpoly(oxyalkylene) aminocarbamates comprising a hydrocarbyl-terminated poly(oxyalkylene) moiety composed of 2-5 carbon oxyalkylene units and one or more 9-30 carbon oxyalkylene groups. Certain additives also find use as dispersants in lubricating oils.
    Type: Grant
    Filed: July 2, 1979
    Date of Patent: June 23, 1981
    Assignee: Chevron Research Company
    Inventor: Jennifer E. Lilburn
  • Patent number: 4267175
    Abstract: A compound of the formula (I), and pharmaceutically acceptable salts thereof: ##STR1## wherein: R.sub.1 is a C.sub.1-6 alkoxy group;R.sub.2 and R.sub.3 are the same or different and are hydrogen, halogen, CF.sub.3, hydroxy, C.sub.1-6 alkoxy, C.sub.2-7 acyl, amino, amino substituted by one or two C.sub.1-6 alkyl groups, C.sub.2-10 acyl amino, aminosulphone, aminosulphone substituted by one or two C.sub.1-6 alkyl groups, C.sub.1-6 alkyl sulphone or nitro groups; andA is a C.sub.2-4 alkylene group;R.sub.5 and R.sub.6 are joined so that they form with the --N--A--N-- group to which they are attached, a 6, 7 or 8 membered heterocyclic ring;R.sub.7 is a C.sub.1-6 alkyl group, or an aryl --C.sub.1-6 akyl group in which the alkyl moiety is optionally substituted by a C.sub.1-6 alkyl or aryl group; have useful pharmacological activity, such as the ability to regulate the gastrointestinal function and to treat emesis.
    Type: Grant
    Filed: March 8, 1979
    Date of Patent: May 12, 1981
    Assignee: Beecham Group Limited
    Inventor: Eric A. Watts
  • Patent number: 4258188
    Abstract: 2-(1-Piperazinyl)-cycloheptimidazole derivatives are disclosed. The foregoing compounds are useful antihypertensive agents.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: March 24, 1981
    Assignee: American Home Products Corporation
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4256800
    Abstract: The antistatic composition for application to flat fibrous articles such as textiles, carpets, fabrics and the like which comprises a salt of a polymeric acid with an amine of the general formula ##STR1## wherein A=H, --OR.sub.2, ##STR2## R.sub.1 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.2 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.3 =H, a lower alkyl radical, a hydroxyalkyl, aminoalkyl, polyalkylene imine or polyalkylene glycol ether radical;R.sub.
    Type: Grant
    Filed: January 18, 1978
    Date of Patent: March 17, 1981
    Assignee: Chemische Fabrik Stockhausen & Cie
    Inventors: Dolf Stockhausen, Reinmar Peppmoller
  • Patent number: 4252804
    Abstract: Compounds of the formula I ##STR1## wherein m and n are 0, 1 or 2, X represents oxygen, imino, benzylimino, or morpholinoethylimino, Y represents CO, CONH, COO or SO.sub.2, and NR.sub.1 R.sub.2 represents a dimethylamino, diethylamino, dipropylamino, dibutylamino, allylamino, isobutenylamino, cyclopentylamino, cyclohexylamino, cycloheptylamino, cyclooctylamino, N-methyl N-cyclopentylamino, N-methyl N-cyclohexylamino, N-allyl N-cyclohexylamino, adamantylamino, diethoxyethylamino, dimethylaminoethylamino, dimethylaminopropylamino, N-methyl N-dimethylaminopropyl-amino, benzylamino, 3,4,5-trimethoxybenzylamino, phenethylamino, p-chlorophenethylamino, tetrahydrofurfurylamino, tetrahydropyranylmethylamino, pyrrolidino, isoxazolidinyl, piperidino, 4-hydroxypiperidino, 4-m-chlorophenyl-4-hydroxypiperidino, homopiperidino, 1,2,3,6-tetrahydropyridyl, morpholino, 2-methylmorpholino, 2,6-dimethylmorpholino, 2-morpholinoethylamino, thiamorpholino, piperazino, 4-methylpiperazino, 4-(.alpha.
    Type: Grant
    Filed: January 13, 1978
    Date of Patent: February 24, 1981
    Assignee: Metabio-Joullie
    Inventors: Maurice Joullie, Gabriel Maillard, Lucien Lakah, Christian J. M. Warolin
  • Patent number: 4242344
    Abstract: Piperazinyl-imidazo[1,2-a]pyrazines, derived from reactions between halo-imidazo[1,2-a]pyrazines with piperazine derivatives, are found to be active anorexic, antidepressant, antihypertensive, analgesic, antiarrhythmic, and/or anti-smoking agents.
    Type: Grant
    Filed: September 7, 1979
    Date of Patent: December 30, 1980
    Assignee: Merck & Co., Inc.
    Inventor: William C. Lumma
  • Patent number: 4217439
    Abstract: Crosslinked acrylate-acetoacetamide polymers are disclosed. These polymers are prepared by the reaction of at least one polyfunctional acrylate with at least one diacetoacetamide in the presence of a catalyst capable of promoting the reaction between the polyfunctional acrylate and the diacetoacetamide. In a preferred embodiment, the polymers are employed to produce wear layer compositions for surface coverings.
    Type: Grant
    Filed: June 19, 1978
    Date of Patent: August 12, 1980
    Assignee: Armstrong Cork Company
    Inventor: John S. Heckles
  • Patent number: 4182762
    Abstract: New dioxo-piperazine derivatives suitable for use as medicaments and .beta.-lactam antibiotic intermediates of the formula ##STR1## in which Z is ##STR2## and, R.sup.1 and R.sup.2 each independently is hydrogen or various optionally substituted aliphatic, aromatic or heterocyclic radicals or together form an optionally substituted ring,are formed by reacting(a) 1-amino-2,3-dioxo-piperazine of the formula ##STR3## with a compound of the formula ##STR4## or a hydrate, acetal, ketal, sulphite, hydrogen halide or hydrocyanic acid addition product thereof or, ##STR5## with an oxalic acid ester in the presence of a diluent, thereby to effect cyclization. The new derivatives are anti-virally active and can also be chlorocarbonated with phosgene to form a reactive derivative which can be condensed with the amino group of .alpha.-amino penicillins to form antibiotics.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: January 8, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventor: Michael Preiss
  • Patent number: 4172945
    Abstract: Compounds are provided having the structure ##STR1## wherein n is 1, 2 or 3, m is 0, 1 or 2, R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 may be the same or different and can be hydrogen, lower alkyl, halo-lower alkyl, acyl, lower alkoxy-carbonyl ##STR2## amido ##STR3## or lower alkoxyalkylene, X is a straight or branched bivalent aliphatic radical and Y is ##STR4## These compounds are useful in the treatment of hypertension.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: October 30, 1979
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Joseph E. Sundeen, Joyce Reid
  • Patent number: 4161591
    Abstract: Substituted 2-(carbamoyl)oxyimino-3-imino-butyramides and 2-(carbamoyl)oxyimino-3-iminobutyrates of the formula ##STR1## where Q is --OR.sub.4 or --NR.sub.5 R.sub.6, and A, R, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are as hereinafter defined are useful as aphicides. The compounds are made by reacting an amine with a substituted 2-hydroxyiminoacetoacetamide (or 2-hydroxyiminopropionylacetamide) or an alkyl 2-hydroxyiminoacetoacetate (or 2-hydroxyiminopropionylacetate), then carbamylating the resulting substituted 2-hydroxyimino-3-iminobutyramide (or 2-hydroxyimino-3-iminovaleramide) or 2-hydroxyimino-3-iminobutyrate (or 2-hydroxyimino-3-iminovalerate).
    Type: Grant
    Filed: October 25, 1977
    Date of Patent: July 17, 1979
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Russell F. Bellina
  • Patent number: 4160648
    Abstract: Fuel compositions for internal combustion engines are provided which contain deposit control additives which maintain cleanliness of intake systems without contributing to combustion chamber deposits. The additives are polyloxyalkylene carbamates comprising a hydroxy- or hydrocarbyloxy-terminated polyloxyalkylene chain of 2-5 carbon oxyalkylene units bonded through an oxycarbonyl group to a nitrogen atom of a polyamine having from 2 to 10 amine nitrogens and from 2 to 40 carbons with a carbon:nitrogen ratio between about 1:1 and 10:1.
    Type: Grant
    Filed: May 27, 1977
    Date of Patent: July 10, 1979
    Assignee: Chevron Research Company
    Inventors: Robert A. Lewis, Lewis R. Honnen