Acyclic Nitrogen Double Or Triple Bonded To Carbon Which Is Attached Directly Or Indirectly To The Isoquinoline Ring System By Nonionic Bonding Patents (Class 546/145)
  • Patent number: 5559140
    Abstract: This invention relates to novel difluoro statone analogs, to the processes and intermediates useful for their preparation and to their use as anti-viral agents.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: September 24, 1996
    Assignee: Merrell Pharmaceuticals Inc.
    Inventors: Daniel Schirlin, Viviane Van Dorsselaer, Celine Tarnus
  • Patent number: 5532243
    Abstract: There are provided nitrogen-containing bicyclic compounds, pharmaceutical compositions containing these compounds and methods of using these compounds to treat physiological or drug-induced psychosis or diskinesia in a mammal.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: July 2, 1996
    Assignee: The DuPont Merck Pharmaceutical Company
    Inventor: Paul J. Gilligan
  • Patent number: 5529978
    Abstract: Certain N-acetonyl-substituted-amides of the formula: ##STR1## wherein A is a heterocycle, a phenylalkyl, a phenylalkoxy, naphthyl, cycloalkyl, alkoxyalkyl, alkyl, haloalkyl or alkenyl group; X, Y and Z are selected from the group consisting of hydrogen, halo, cyano, thiocyano, isothiocyano, methylsulfonyloxy, thio(C.sub.1 -C.sub.2)alkyl, (C.sub.1 -C.sub.2)alkoxy, carbamoyl, dithiocarbamoyl, hydroxy, azide, trifluoromethylcarboxy, (C.sub.1 -C.sub.4)alkylcarbonyloxy, phenylcarbonyloxy, phenoxy, thiophenyl, imidazolyl or triazolyl group as described herein; R.sup.1 and R.sup.2 are each independently a hydrogen atom or a (C.sub.1 -C.sub.6)alkyl group; and compositions containing these amides are fungicidally active, particularly against phytopathogenic fungi.
    Type: Grant
    Filed: May 3, 1994
    Date of Patent: June 25, 1996
    Assignee: Rohm and Haas Company
    Inventor: Ashok K. Sharma
  • Patent number: 5518735
    Abstract: D,L-, L- and D-phenyl alanine derivatives of formula (I) defined in claim 1 in which R.sub.1 is an amidino-, guanidino-, oxamidino-, aminomethyl- or amino group have been discovered which effectively prevent blood coagulation or thrombosis. The antithrombotically active compounds have low toxicity and may be administered by mouth, subcutaneously or intravenously.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: May 21, 1996
    Assignee: Pentapharm AG
    Inventors: Jorg Sturzebecher, Helmut Vieweg, Peter Wikstroem
  • Patent number: 5519036
    Abstract: The invention relates to cyclic derivatives of general formula ##STR1## wherein R.sub.a, R.sub.b, X and Y are as defined in claim 1, the tautomers, the stereoisomers including the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with organic or inorganic acids or bases, which have valuable pharmacological properties, preferably aggregation-inhibiting effects, pharmaceutical compositions containing the compounds and processes for preparing them.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: May 21, 1996
    Assignee: Karl Thomae GmbH
    Inventors: F. Himmelsbach, Helmut Pieper, Volkhard Austel, Gunter Linz, Brian Guth, Thomas Muller, Johannes Weisenberger
  • Patent number: 5519034
    Abstract: Tetrahydroisoquinoline compounds of formula I ##STR1## and pharmaceutically acceptable salts and lipophilic ester thereof have utility as analgesics and in the treatment of psychoses, Parinson's disease, Lesch-Nyan syndrome, attention deficit disorder or cognitive impairment or in the relief of drug dependence or tardive dyskinesia.
    Type: Grant
    Filed: August 18, 1994
    Date of Patent: May 21, 1996
    Assignee: The Boots Company PLC
    Inventors: Antonin Kozlik, Bruce J. Sargent, Patricia L. Needham
  • Patent number: 5516913
    Abstract: Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)--, --N(acyl)-- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: May 14, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
  • Patent number: 5514801
    Abstract: The present invention relates to cyclic sulfone moiety-containing hydroxyethylamine protease inhibitor compounds and pharmaceutical or method of use therefor, particularly as an inhibitor of HIV protease.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: May 7, 1996
    Assignee: Monsanto Company
    Inventors: Deborah E. Bertenshaw, Daniel Getman, Robert M. Heintz, John J. Talley, Kathryn L. Reed
  • Patent number: 5489603
    Abstract: An insecticidal composition containing a guanidine derivative of the formula: ##STR1## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic group, n is 0 or 1, R.sup.2 is a hydrogen atom or an optionally substituted hydrocarbon group, R.sup.3 is a primary, secondary or tertiary amino group, X is an electron attractive group such as nitro or trifluoroacetyl group, provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group or a salt thereof.
    Type: Grant
    Filed: July 15, 1993
    Date of Patent: February 6, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideki Uneme, Koichi Iwanaga, Noriko Higuchi, Isao Minamida, Tetsuo Okauchi
  • Patent number: 5488057
    Abstract: The present invention provides novel aryl- and heteroarylethenylene derivatives which are useful as tyrosine kinase activity inhibitors.
    Type: Grant
    Filed: August 23, 1994
    Date of Patent: January 30, 1996
    Assignee: Farmitalia Carlo Erba S.r.l.
    Inventors: Franco Buzzetti, Antonio Longo, Maristella Colombo
  • Patent number: 5455348
    Abstract: The invention relates to cyclic imino derivatives of general formulaB--X.sub.5 --X.sub.4 --X.sub.3 --X.sub.2 --X.sub.1 --A--Y--E(I)whereinA, B, E, X.sub.2 to X.sub.5 and Y are defined as in claim 1, the stereoisomers, tautomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable pharmacological properties, preferably aggregation-inhibiting effects, pharmaceutical compositions which contain these compounds and processes for preparing them.
    Type: Grant
    Filed: December 23, 1993
    Date of Patent: October 3, 1995
    Assignee: Karl Thomae
    Inventors: Volkhard Austel, Wolfgang Eisert, Frank Himmelsbach, Guenter Linz, Thomas Mueller, Helmut Pieper, Johannes Weisenberger
  • Patent number: 5451678
    Abstract: Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)-, --N(acyl)- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.
    Type: Grant
    Filed: September 29, 1993
    Date of Patent: September 19, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
  • Patent number: 5439888
    Abstract: This invention relates to L-Arginine aldehyde derivatives, pharmaceutical formulations containing those compound and methods of their use as thrombin inhibitors.
    Type: Grant
    Filed: March 4, 1994
    Date of Patent: August 8, 1995
    Assignee: Eli Lilly and Company
    Inventors: Robert T. Shuman, Gerald F. Smith
  • Patent number: 5434162
    Abstract: Compounds characterized as quinolinyl- or isoquinolinyl-terminated alkylamino ethynyl alanine amino diol derivatives are useful as renin inhibitors for the treatment of hypertension and are of Formula I ##STR1## wherein A is selected from CO and SO.sub.2 ; X is selected from oxygen atom and methylene; G is a quinolinyl or isoquinolinyl group; R.sub.1 is selected from hydrido, methyl, ethyl, isopropyl and n-propyl; R.sub.2 is phenylmethyl; each of R.sub.3 and R.sub.5 is hydrido; R.sub.4 is--(CH.sub.2).sub.q --C--V;V is selected from hydrido and methyl; R.sub.6 is cyclohexylmethyl; R.sub.7 is selected from isobutyl, cyclopropyl and cyclopropylmethyl; q is a number selected from zero through three, inclusive; and n is a number selected from zero through three, inclusive; or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: September 13, 1993
    Date of Patent: July 18, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Gunnar J. Hanson, Robert E. Manning
  • Patent number: 5434163
    Abstract: A method of treatment of Cryptococcus neoformans infection by administering to a patient in need thereof an effective amount of a benzimidazile compound.
    Type: Grant
    Filed: May 14, 1993
    Date of Patent: July 18, 1995
    Assignee: The Medical College of Pennsylvania
    Inventors: Thomas D. Edlind, Maria C. Cruz
  • Patent number: 5401751
    Abstract: The invention concerns a heterocycle of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents orAr is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, cyano-(1-4C)alkyl or (2-4C)alkanoyl, or optionally substituted benzoyl;and R.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.
    Type: Grant
    Filed: May 24, 1993
    Date of Patent: March 28, 1995
    Assignees: Zeneca Limited, Zeneca Pharma
    Inventors: Graham C. Crawley, Philip N. Edwards, Jean-Marc M. M. Girodeau
  • Patent number: 5391705
    Abstract: This invention relates to novel polyfluorinated alkyl derivatives of certain tripeptides, to the methods for their preparation, the intermediates therefore, to their use in inhibiting thrombin and lung tryptase and in their end-use application as anti-coagulants useful in treating thrombophlebitis and coronary thrombosis and in the treatment of asthma.
    Type: Grant
    Filed: February 18, 1994
    Date of Patent: February 21, 1995
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Bernhard Neises, Axel Ganzhorn, Celine Tarnus, Robert J. Broersma, Jr.
  • Patent number: 5389649
    Abstract: Oxathiane derivatives of formula ##STR1## in which R represents alkyl and A represents optionally substituted phenyl or a heteroaromatic group containing 1 or 2 nitrogen atoms optionally substituted by alkyl, alkoxy or halogen, and salts thereof possess pharmacological activity and are also useful in inhibiting head hair loss.
    Type: Grant
    Filed: July 20, 1992
    Date of Patent: February 14, 1995
    Assignee: Rhone-Poulenc Rorer Limited
    Inventors: Iain M. McLay, Roger J. A. Walsh
  • Patent number: 5338851
    Abstract: This invention provides a process for the synthesis of cis-decahydroisoquinoline-3-carboxylic acids and provides intermediates in the synthesis thereof.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: August 16, 1994
    Assignee: Eli Lilly and Company
    Inventors: Bret E. Huff, Vien V. Khau, Michael J. Martinelli, Barry C. Peterson
  • Patent number: 5328906
    Abstract: Hydroximic acid derivatives of the formula ##STR1## These compounds are useful for treating diabetes angiopathy.
    Type: Grant
    Filed: June 7, 1993
    Date of Patent: July 12, 1994
    Assignee: Biorex Kutato-Fejleszto KFT
    Inventors: Peter L. Nagy, Bela Balazs, Maria Boross, Jeno Szilbereky, Gizella Zsila, Lajos Abraham, Gyorgy Blasko, Bela Gachalyi, Attila Almasi, Gabor Nemet
  • Patent number: 5314889
    Abstract: A 2-Acylaminothiazole of formula: ##STR1## in which R.sub.1 is H, an alkyl or a substituted alkyl; R.sub.IV is a cycloalkyl, an aromatic group such as phenyl or a heterocyclic group which are unsubstituted or substituted; R.sub.V is a substituted alkyl, a substituted carboxy such as an ester or an amide; or R.sub.IV and R.sub.V together represent a phenoxyalkylene group which may be substituted on the phenyl; and Z is a heterocyclic e.g. indolyl group; or a salt of compound (I).
    Type: Grant
    Filed: May 29, 1992
    Date of Patent: May 24, 1994
    Assignee: Elf Sanofi
    Inventors: Robert Boigegrain, Roger Brodin, Danielle Gully, Jean-Charles Molimard, Dominique Olliero
  • Patent number: 5296483
    Abstract: The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are compounds of the formula ##STR1## and the non-toxic pharmaceutically acceptable salts thereof, wherein D is the residue of a centrally acting primary, secondary or tertiary amine and ##STR2## is an unsubstituted or substituted dihydropyridyl, dihydroquinolyl or dihydroisoquinolyl radical. The corresponding ionic pyridinium, quinolinium and isoquinolinium salts ##STR3## wherein X.sup.- is the anion of a non-toxic pharmaceutically acceptable acid, are also disclosed.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: March 22, 1994
    Assignee: University of Florida
    Inventor: Nicholas S. Bodor
  • Patent number: 5266702
    Abstract: Disclosed are reactive anionic initiators of the general formula [ArCHR.sub.1 R.sub.2 N(R.sub.3 R.sub.4 R.sub.5 R.sub.6 ] wherein Ar=phenyl, substituted phenyl, or a heterocyclic compound, R.sub.1 =R.sub.2 =H, ester, cyano, alkyl, aryl, 1,3-oxazoline, N,N-dimethyl amide and other similar alpha activating groups, or combination of them, or one of R.sub.1 or R.sub.2 together with Ar, where Ar is a phenyl or substituted phenyl, is a nitrogen atom containing heterocyclic compound and the other being a nitrile group, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 may be same or different and represent substituted alkyl, cycloalkyl, arylalkyl or aryl or to of the R.sub.3, R.sub.4, R.sub.5 and R.sub.6 together with nitrogen atom form a heterocycle with the condition that the sum of all carbon atoms of all R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is from 12 to 50 and no more than one of the R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is an aryl derivative.
    Type: Grant
    Filed: September 19, 1990
    Date of Patent: November 30, 1993
    Assignee: Council of Scientific & Industrial Research
    Inventors: Durairaj Bhaskaran, Pradeep K. Dhal, Sanjay P. Kashikar, Ratnaprabha S. Khisti, Babanrao M. Shinde, Swaminathan Sivaram
  • Patent number: 5252566
    Abstract: Thrombin inhibitors represented by the formula ##STR1## as provided wherein A is e.g. phenylglycyl, and phenylalanyl, .alpha.-methylphenylalanine and .alpha.-methylphenylglycine wherein the amino group is preferably substituted with lower alkyl alkanoyl or lower alkoxycarbonyl, or a bicyclo group e.g. 1,2,3,4-tetrahydroisoquinolin-1-yl. Also provided are a method for inhibiting clot formation in man and animals, pharmaceutical formulations useful in the method and intermediates for the inhibitors.
    Type: Grant
    Filed: October 16, 1992
    Date of Patent: October 12, 1993
    Assignee: Eli Lilly and Company
    Inventor: Robert T. Shuman
  • Patent number: 5242939
    Abstract: This invention relates to anilide derivatives of Formula I ##STR1## which antagonize the binding of angiotensin II to its receptors. The compounds are useful in the treatment of hypertension, heart failure, glaucoma, and hyperaldosteronism. Methods of making the compounds, novel intermediates useful in the preparation of the compounds, compositions containing the compounds and methods of using them are also covered.
    Type: Grant
    Filed: September 13, 1991
    Date of Patent: September 7, 1993
    Assignee: Warner-Lambert Company
    Inventor: Ila Sircar
  • Patent number: 5238935
    Abstract: N-acyltetrahydroisoquinolines including novel compounds of the formula ##STR1## wherein R.sup.1 is a C10-C25 alkyl chain; a substituted C10-C25 alkyl chain; an interrupted C10-C25 alkyl chain; a substituted interrupted C10-C25 alkyl chain; diphenylamino; di-(R.sup.2 -substituted phenyl)amino; di-(heteroaryl)amino; di-(R.sup.2 -substituted heteroaryl)amino; diphenylmethyl; or di-(R.sup.2 -substituted phenyl)methyl;R.sup.2 is hydroxy, lower alkyl, lower alkoxy, halogeno, amino, lower alkylamino or di-(lower alkyl)amino;R.sup.3, R.sup.4 and R.sup.5 are independently H or --(CH.sub.2).sub.n --Ar;Ar is phenyl, R.sup.2 -substituted phenyl, heteroaryl or R.sup.2 - substituted heteroaryl;n=0,1 or 2;m=0,1 or 2;or a pharmaceutically acceptable salt thereof, useful in the treatment of atherosclerosis are disclosed.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: August 24, 1993
    Assignee: Schering Corporation
    Inventors: Sundeep Dugar, Timothy Kogan
  • Patent number: 5231109
    Abstract: Novel fungicides of the formula ##STR1## in which R.sup.1 represents optionally substituted hydroxyalkyl, optionally substituted hydroxyalkoxyalkyl, optionally substituted heteroarylalkyl or optionally substituted heteroaryl, andR.sup.2 represents optionally substituted alkyl, optionally substituted alkenyl, or alkinyl.Intermediates therefor, wherein R.sup.2 is hydrogen or an alkali metal cation, are also new.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: July 27, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Klaus Jellch, Winfried Lunkenhelmer, Wilhelm Brandes, Gerd Hanssler
  • Patent number: 5221677
    Abstract: The invention concerns a heterocyclic derivative of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;X.sup.1 is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl or (3-6C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.2 --X.sup.2 --A.sup.3 -- which, together with the carbon atom to which A.sup.2 and A.sup.3 are attached, defines a ring having 4 to 7 ring atoms, wherein A.sup.2 and A.sup.3, which may be the same or different, each is (1-4C)alkylene and X.sup.2 is oxy, thio, sulphinyl, sulphonyl or imino;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: September 21, 1990
    Date of Patent: June 22, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Philip N. Edwards
  • Patent number: 5218117
    Abstract: The invention relates to novel compounds of the general formula (I), ##STR1## The compounds of the invention antagonize the effects of constrictive mediators, e.g. histamine, acetylcholine or serotonin; they show an antiallergic action and possess an antiinflammatory effect. Thus, these compounds can therapeutically be used as bronchodilators as well as antiallergic or antiinflammatory drugs, particularly in the treatment of bronchial asthma.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: June 8, 1993
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Kalman Takacs, Iloma Kiss nee Ajzert, Istvan Hermecz, Janos Ori, Maria H. Pap, Zsolt Bencze, Peter Szekely Kormoczy, Maria Szabo, Judit Szeredy, Csaba Vertesi, Lorand Debreczeni, Jozsef Gaal, Zoltan Kapui
  • Patent number: 5204348
    Abstract: Novel heterocyclic compounds, which are represented by the following general formula, useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.
    Type: Grant
    Filed: December 3, 1991
    Date of Patent: April 20, 1993
    Assignee: Mitsui Toatsu Chemicals Inc.
    Inventors: Nobuyuki Fukazawa, Makoto Odate, Tsuneji Suzuki, Kengo Otsuka, Takashi Tsuruo, Wakao Sato
  • Patent number: 5202326
    Abstract: The invention concerns a heterocyclic ether of the formula I ##STR1## wherein Q is an optionally substituted 6-membered monocyclic or 10-membered bicyclic heterocyclic moiety containing one or two nitrogen atoms;A is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene;X is oxy, thio, sulphinyl, sulphonyl or imino;Ar is phenylene which may optionally bear one or two substituents or Ar is an optionally substituted 6-membered heterocyclene moiety containing up to three nitrogen atoms;R.sup.1 is (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl or (2-4 C)alkanoyl, or optionally substituted benzoyl;R.sup.2 is (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl; andR.sup.3 is substituted (1-4C)alkyl;or a pharmaceutically-acceptable salt thereof.The compounds of the invention are inhibitors of the enzyme 5-lipoxygenase.
    Type: Grant
    Filed: November 25, 1991
    Date of Patent: April 13, 1993
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Graham C. Crawley, Jean-Marc M. M. Girodeau
  • Patent number: 5185335
    Abstract: Piperidine derivatives of formula ##STR1## wherein A is a radical of formula ##STR2## wherein one or two hydrogen atoms in said radicals (a-1) to (a-3) may be replaced by a C.sub.1-6 alkyl radical;R.sup.1 is hydrogen or halo; R.sup.2 is hydrogen, amino, mono or di(C.sub.1-6 alkyl)amino or C.sub.1-6 alkylcarbonylamino; R.sup.3 is hydrogen or C.sub.1-6 alkyl; L is C.sub.3-6 cycloalkyl, C.sub.5-6 cycloalkanone, C.sub.3-6 alkenyl optionally substituted with aryl, or L is a radical of formula ##STR3## the N-oxide forms, addition salts and stereochemically isomeric forms thereof, said compounds having gastrointestinal motility stimulating properties. Pharmaceutical compositions containing these compounds as active ingredient, and a method of preparing said compounds and pharmaceutical compositions.
    Type: Grant
    Filed: February 4, 1991
    Date of Patent: February 9, 1993
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Jean-Paul R. M. A. Bosmans, Michel A. J. De Cleyn
  • Patent number: 5179089
    Abstract: The invention relates to novel compounds of the general formula (I), ##STR1## wherein R means hydrogen or a straight or branched chain C.sub.1-6 alkoxy group;R.sup.1 stands for hydrogen or a straight or branched chain C.sub.1-6 alkyl group;R.sup.2 represents hydrogen or a straight or branched chain C.sub.1-6 alkyl group;R.sup.3 means hydrogen, a straight or branched chain C.sub.1-6 alkyl group optionally substituted by one or two hydroxyl and/or one or two straight or branched chain C.sub.1-4 alkoxy group(s); or a C.sub.4-7 cycloalkyl group;R.sup.4 stands for hydrogen or a straight or branched chain C.sub.1-6 alkyl group optionally substituted by one or two hydroxyl and/or one or two straight or branched chain C.sub.1-4 alkoxy group(s); or a C.sub.4-7 cycloalkyl group; orR.sup.3 and R.sup.4 together with the nitrogen atom, to which they are attached form a 4 to 8-membered cyclic group of formula ##STR2## optionally substituted by one or two straight or branched chain C.sub.
    Type: Grant
    Filed: November 14, 1991
    Date of Patent: January 12, 1993
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Kalman Takacs, Iloma Kiss neAjzert, Istvan Hermecz, Janos Ori, Maria H. Pap, Zsolt Bencze, Peter S. Kormoczy, Maria Szabo, Judit Szeredy nee Varga, Csaba Vertesi, Lorand Debreczeni, Jozsef Gaal, Zoltan Kapui
  • Patent number: 5169948
    Abstract: This invention relates to a process for producing spiro-isoquinolinepyrrolidines. The compounds have pharmaceutical properties which render them beneficial for the prevention or treatment of diabetes mellitus associated complications.
    Type: Grant
    Filed: January 2, 1992
    Date of Patent: December 8, 1992
    Assignee: American Home Products Corporation
    Inventor: Michael S. Malamas
  • Patent number: 5132311
    Abstract: Cyanoguanidines which have activity as Class III antiarrhythmic agents, acting by prolonging cardiac action potential repolarization. The invention further provides for compositions incorporating the compounds and methods of their use, as well as providing for pharmaceutically acceptable salts of the compounds.
    Type: Grant
    Filed: July 30, 1991
    Date of Patent: July 21, 1992
    Assignee: G. D. Searle & Co.
    Inventor: Chi-Dean Liang
  • Patent number: 5120745
    Abstract: This invention relates to 1-dimethylcarbamoyl-3-substituted-5-substituted-1H-1,2,4-triazoles of the formula ##STR1## wherein the substituents are as defined herein, compositions containing those compounds and methods of use.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: June 9, 1992
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventors: Richard M. Jacobson, Luong T. Nguyen, Muthuvelu Thirugnanam
  • Patent number: 5116985
    Abstract: The invention provides novel compounds and salts thereof, have the structure ##STR1## wherein R.sub.1 is a guianidinobenzoyloxy group and R.sub.2 is a hydrogen atom, a hydroxy, cyano, --COR.sub.3 (wherein R.sub.3 is an amino or lower alkyl group) or --COOR.sub.4 group [wherein R.sub.4 is a hydrogen atom, lower alkyl, phenyl, benzyl or --CH.sub.2 CONR.sub.5 R.sub.6 group (wherein R.sub.5 and R.sub.6 are the same or different and selected from a hydrogen atom and lower alkyl groups)], and wherein R.sub.1 is a hydroxy group and wherein R.sub.2 is a --COR.sub.3 (wherein R.sub.3 is an amino or lower alkyl group) or --COOR.sub.4 group [wherein R.sub.4 is a (C.sub.1, C.sub.3 or C.sub.4) alkyl, phenyl, benzyl or --CH.sub.2 CONR.sub.5 R.sub.6 group (wherein R.sub.5 and R.sub.6 are the same or different and selected from a hydrogen atom and lower alkyl groups)]. The compounds, wherein R.sub.1 is a guanidinobenzoyloxy group, are useful protease inhibitors as anti-trypsin agents.
    Type: Grant
    Filed: December 19, 1990
    Date of Patent: May 26, 1992
    Assignee: Snow Brand Milk Products Co., Ltd.
    Inventors: Yasuyoshi Takeshita, Hiroshi Nakamura, Susumu Ishiguro, Noboru Kwaguchi, Shin'ichi Shimada, Tadayoshi Koyama, Motohide Seya, Noriko Abe, Shin Nomoto
  • Patent number: 5104872
    Abstract: Compound of the general formula (I), which is useful as an agricultural and horticultural fungicide, an agricultural and horticultural fungicidal composition containing said compound, use of said composition for controlling plant disease, and process for the production of said compound: ##STR1## wherein ##STR2## shows a case in which R.sup.3 and R.sup.4 together form a cyclic substituent, and R.sup.1 and R.sup.4 are substituents disclosed in the specification.
    Type: Grant
    Filed: August 15, 1990
    Date of Patent: April 14, 1992
    Assignee: Nihon Hohyaku Co., Ltd.
    Inventors: Kenji Tsubata, Nobuyuki Niino, Katsutoshi Endo, Yoshinobu Yamamoto, Hideo Kanno
  • Patent number: 5082853
    Abstract: The subject compounds, which are adapted for the site-specific/sustained delivery of centrally acting drug species to the brain, are compounds of the formula ##STR1## and the non-toxic pharmaceutically acceptable salts thereof, wherein D is the residue of a centrally acting primary, secondary or tertiary amine and ##STR2## is an unsubstituted or substituted dihydropyridyl, dihydroquinolyl or dihydroisoquinolyl radical. The corresponding ionic pyridinium, quinolinium and isoquinolinium salts ##STR3## wherein X.sup.- is the anion of a non-toxic pharmaceutically acceptable acid, are also disclosed.
    Type: Grant
    Filed: April 4, 1990
    Date of Patent: January 21, 1992
    Inventor: Nicholas S. Bodor
  • Patent number: 5071860
    Abstract: Insecticidally active substituted heteroaryl phenyl ethers of the formula ##STR1## in which Het represents an optionally substituted heteroaromatic radical,X represents O, S, --CH.sub.2 --, --O--CH.sub.2 --, --S--CH.sub.2 --, --CH.sub.2 --O--, ##STR2## Y represents O, --O--CH.sub.2 -- or S, Z represents an optionally substituted aromatic or heteroaromatic radical;m represents integers from 1-4n represents 0, 1, 2, 3, 4O represents 0, 1, 2, 3, 4, provided than n and o do not simultaneously represent 0p represents integers from 1-4,R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently of one another represent hydrogen, C.sub.1 -C.sub.6 -alkyl which is optionally substituted; two radicals adjacent to one another can also, together with the C atoms to which they are bonded, form a saturated carbocyclic 5- or 6-ring,R.sup.1 represents identical or different radicals hydrogen, halogen, CN, C.sub.1-4 -alkyl, 1-5-halogeno-C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy, C.sub.1-4 -alkylthio, 1-5-halogeno-C.sub.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Alig, Wilhelm Stendel, Michael Londershausen
  • Patent number: 5043443
    Abstract: Novel aminomethyloxooxazolidinyl arylbenzene derivatives, wherein the aryl includes the phenyl, substituted phenyl, pyridyl, and substituted pyridyl groups, such as (l)-N-{3-[4- (4'-pyridyl)phenyl]-2-oxooxazolidin-5-ylmethyl}acetamide, possess useful antibacterial activity.
    Type: Grant
    Filed: July 24, 1990
    Date of Patent: August 27, 1991
    Assignee: Du Pont Merck Pharmaceutical Company
    Inventors: Randall K. Carlson, Chung-Ho Park, Walter A. Gregory
  • Patent number: 5032590
    Abstract: Substituted hydroxylamines of the formula ##STR1## in which R.sup.1 stands for an aromatic or heterocyclic radical,are especially useful in the treatment of hyperlipoproteinaemia, lipoproteinaemia and atherosclerosis.
    Type: Grant
    Filed: March 8, 1990
    Date of Patent: July 16, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
  • Patent number: 4975431
    Abstract: The invention concerns compounds of formula I ##STR1## or a salt thereof, wherein R.sup.1 and R.sup.2 each independently represent hydrogen, lower alkyl, lower alkoxy, carboxyloweralkyl, carboxy, hydroxyloweralkyl, halogen, haloloweralkyl, lower alkoxycarbonyl, optionally substituted aryl or optionally substituted aralkyl, n represents an integer from 3 to 6; R.sup.3 represents hydrogen or single or multiple substitution on one or more of the aliphatic carbons by one or more substituents selected from lower alkyl, optionally substituted aryl and optionally substituted aralkyl; A represents a group of formula (i) or (ii) below:--CR.sup.4 R.sup.5 --(CR.sup.6 R.sup.7).sub.m -- (i)--CX--(CR.sup.6 R.sup.7).sub.m -- (ii)in which R.sup.4, R.sup.6 and R.sup.7 each independently represent hydrogen or lower alkyl (providing that when R.sup.5 is NH.sub.2, R.sup.4 is hydrogen); m is O or 1; R.sup.5 represents hydrogen, NH.sub.2, OH or loweralkoxy, and X is .dbd.O, .dbd.NH or .dbd.
    Type: Grant
    Filed: June 16, 1989
    Date of Patent: December 4, 1990
    Assignee: John Wyeth & Brother Limited
    Inventors: Roger Crossley, Albert Opalko
  • Patent number: 4968698
    Abstract: Compounds of the formula (III): ##STR1## or salts or acyl derivatives thereof, for use as antifungal and antiprotozoal agents are disclosed. Compositions containing the compounds are also disclosed as are method for the preparation of the compounds and intermediates in their preparation.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: November 6, 1990
    Assignee: Burroughs Wellcome Co.
    Inventor: Karl W. Franzmann
  • Patent number: 4968681
    Abstract: Substituted hydroxylamines of the formula ##STR1## in which R.sup.1 stands for an aromatic or heterocyclic radical, are especially useful in the treatment of hyperlipoproteinaemia, lipoproteinaemia and atherosclerosis.
    Type: Grant
    Filed: November 15, 1988
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Walter Hubsch, Rolf Angerbauer, Peter Fey, Hilmar Bischoff, Dieter Petzinna, Delf Schmidt
  • Patent number: 4965360
    Abstract: Novel 4-amino-6,7-dimethoxy-2-(6,7-disubstituted-1,2,3,4-tetrahydroisoquinol-2-y l)quinoline compounds have been prepared, including their pharmaceutically acceptable salts and various novel key intermediates therefor. These compounds are useful in therapy as anti-arrhythmic agents and therefore, are of value in the treatment of various cardiac arrhythmias. Preferred compounds include 4-amino-6,7-dimethoxy-2-(6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinol-2 -yl)quinoline and 4-amino-6,7-dimethoxy-2-(7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinol-2 -yl)-quinoline. Methods for preparing these compounds from known starting materials are provided.
    Type: Grant
    Filed: August 23, 1989
    Date of Patent: October 23, 1990
    Assignee: Pfizer Inc.
    Inventor: Nigel J. Cussans
  • Patent number: 4960890
    Abstract: Methine dyes (I) which conform in one of their tautomeric forms to the general formula ##STR1## where Y.sup.1 is in both or either case an electron-attracting group and the other Y.sup.1 is hydrogen,Y.sup.2 is in each case, independently of the others, hydrogen, --CN, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, pyridyl or together with a further Y.sup.2 a five- or six-membered ring which may have a fused-on benzene ring,R is hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.7 -C.sub.10 -aralkyl or .beta.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Ewald Daltrozzo, Werner Sulger
  • Patent number: 4954509
    Abstract: A compound, or a solvate or salt thereof, of formula (I): ##STR1## in which: RCO is an acyl group in which the group R contains a substituted or unsubstituted carbocyclic aromatic or heterocyclic aromatic ring and R.sub.1 R.sub.2 are independently hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.3-6 cycloalkyl or C.sub.4 -12 cycloalkylalkyl groups or together form a C.sub.2-8 branched or linear polymethylene or C.sub.2-6 alkenylene group optionally substituted with a hetero-atom;R.sub.3 is hydrogen, C.sub.1-6 alkyl, or phenyl, or R.sub.3 together with R.sub.1 forms a --(CH.sub.2).sub.3 -- or --(CH.sub.2).sub.4 --, group; R.sub.4 and R.sub.5, which may be the same or different and may be attached to the same or different carbon atoms of the isoquinoline nucleus, are each hydrogen, halogen, hydroxy, C.sub.1-6 alkyl, aryl, or R.sub.4 together with R.sub.5 form a --(CH.sub.2).sub.p -- group, where p is an integer of from 1 to 5 and one or more of the --(CH.sub.2)-- moieties is optionally substituted by a C.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: September 4, 1990
    Assignee: Dr. Lo. Zambeletti S.p.A.
    Inventors: Vittorio Vecchietti, Giuseppe Giardina
  • Patent number: 4945096
    Abstract: A compound of formula (I) ##STR1## in which R is (a) a hydrogen atom;(b) a linear or branched (C.sub.1 -C.sub.6) alkyl group; an allyl group; a cycloalkylmethyl group in which the cycloalkyl moiety has from 3 to 6 carbon atoms; a phenylmethyl group unsubstituted or substituted with one to three substituents chosen from halogen atoms and trifluoromethyl, nitro, amino, dimethylamino, cyano, aminocarbonyl, linear or branched (C.sub.1 -C.sub.3) alkyl, liner or branched (C.sub.1 -C.sub.3) alkoxy and linear or branched (C.sub.1 -C.sub.3) alkylthio groups; a 2-phenylethyl group; a 3-phenylpropyl group; a 3-phenyl-2-propenyl group; a phenylcarbonylmethyl group; a naphthylmethyl group; a pyridylmethyl group; a furylmethyl group; or a thienylmethyl group; or(c) a linear or branched (C.sub.2 -C.sub.
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: July 31, 1990
    Assignee: Synthelabo
    Inventors: Pascal George, Mireille Sevrin
  • Patent number: 4945098
    Abstract: A derivative of 2-methylenepropane-1,3-diol of the general formula I ##STR1## where O--A.sup.1 and O--A.sup.2, which can be the same or different, each represents O, O--C(O), O--C(O)NH, O--C(S)NH or O--C(O)O, R.sup.1 represents an alkyl or alkenyl group of 10-22 carbon atoms, n is an integer from 1 to 11, B.sup.+ represents a quaternary ammonium group, either N.sup.+ R.sup.4 R.sup.5 R.sup.6, or N.sup.+ (Het), where R.sup.4, R.sup.5 and R.sup.6 are similar or different alkyl groups of 1-4 carbon atoms, or two or all of R.sup.4, R.sup.5 and R.sup.6 may be incorporated into a cyclic or bicyclic structure, which may contain additional hetero atoms; X.sup.- means the anion of a pharmceutically acceptable inorganic or organic acid; and R.sup.2 and R.sup.3 are the same or different, and represent hydrogen or alkl groups of 1-4 carbon atoms.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: July 31, 1990
    Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)
    Inventors: Gunnar Grue-Sorensen, Christian K. Nielsen