Plural Ring Hetero Atoms In The Bicyclo Ring System, Or Ring Nitrogen Is Shared By The Two Cyclos Of The Bicyclo Ring System Patents (Class 548/453)
  • Patent number: 5789587
    Abstract: There are disclosed certain novel compounds identified as heterocyclic-fused lactams which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to increase the stature of those afflicted with a lack of a normal secretion of natural growth hormone. Growth promoting compositions containing such heterocyclic-fused lactams as the active ingredient thereof are also disclosed.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: August 4, 1998
    Assignee: Merck & Co., Inc.
    Inventors: Michael H. Fisher, Helmut Mrozik, William R. Schoen, Thomas L. Shih, Matthew J. Wyvratt
  • Patent number: 5786487
    Abstract: The present invention relates to pyrrolopyrrole derivatives of the formula (I) ##STR1## wherein A and B are identical or different aryl radicals, and DPP is a diaryldiketopyrrolopyrrole radical; which diketopyrrolopyrrole derivative is substituted by from 0 to 6 moles of --SO.sub.3 M per mole of the pyrrolopyrrole derivative; wherein M is hydrogen or a metal or ammonium cation. The pyrrolopyrrole derivatives of formula I are useful as rheology-improving agents for pigment dispersions.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: July 28, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventor: Shivakumar B. Hendi
  • Patent number: 5780495
    Abstract: This invention is directed to nitric esters of derivatives of propionic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid, 5-benzoyl-1,2-dihidro-3H-pyrrolo ?1,2-a!pyrrole-1-carboxylic acid, 6-methoxy-2-napthylacetic acid, characterized in that they have the following general formula: ##STR1## These nitric ester derivatives may be formulated into pharmaceutical compositions and administered for their anti-inflammatory and/or analgesic activity.
    Type: Grant
    Filed: July 29, 1997
    Date of Patent: July 14, 1998
    Assignee: Nicox S.A.
    Inventor: Piero Del Soldato
  • Patent number: 5780633
    Abstract: A new process for preparing a compound of the formula: ##STR1##
    Type: Grant
    Filed: May 6, 1996
    Date of Patent: July 14, 1998
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Satoshi Okada, Kozo Sawada, Akio Kuroda, Shinya Watanabe, Hirokazu Tanaka
  • Patent number: 5756746
    Abstract: The present invention relates to a solid solution consisting of 60-90 mol-% of an asymmetric 2,5-dihydro-1,4-diketopyrrolo?3,4-c!pyrrole of the formula (I) ##STR1## in which G.sub.1 and G.sub.2 independently of one another are different substituted or unsubstituted aromatic radicals or pyridyl, but the volume of all substituents on G.sub.1 and G.sub.2 is greater than that of two methyl groups;and 40-10 mol-% of a 2,5-dihydro-1,4-diketopyrrolo?3,4-c!pyrrole of the formula (IIa) ##STR2## in which G.sub.3 and G.sub.4 independently of one another are different substituted or unsubstituted aromatic radicals or pyridyl, but the volume of all substituents on G.sub.3 and G.sub.4 is less than that of two butoxy groups;or 40-10 mol-% of a quinacridone of the formula (IIb) ##STR3## in which R.sub.9 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;which is a single-phase solid solution having the crystal structure of the asymmetric 2,5-dihydro-1,4-diketopyrrolo?3,4-c!pyrrole of the formula (I).
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: May 26, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, Abul Iqbal
  • Patent number: 5750702
    Abstract: The present invention encompasses structures of the formula: ##STR1## or the pharmaceutically acceptable non-toxic salts thereof wherein: ##STR2## wherein: W represents substituted or unsubstituted phenyl;X is hydrogen, hydroxy or lower alkyl;T is hydrogen, halogen, hydroxy, nitro, amino or alkyl;R.sub.3 is hydrogen or an organic group;R.sub.4 is hydrogen or substituted or unsubstituted organic substituent;R.sub.5 and R.sub.6 represent organic, and inorganic substituents; andn is 1, 2, 3, or 4,which compounds are highly selective agonists, antagonists or inverse agonists for GABAa brain receptors or prodrugs of agonists, antagonists or inverse agonists for GABAa brain receptors. These compounds are useful in the diagnosis and treatment of anxiety, sleep and seizure disorders, overdose with benzodiazepine drugs and for enhancement of memory.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: May 12, 1998
    Assignee: Neurogen Corporation
    Inventors: Pamela Albaugh, Alan Hutchison
  • Patent number: 5750723
    Abstract: 1,4-diketopyrrolopyrroles of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are hydrogen, C.sub.12 -C.sub.24 alkyl, C.sub.6 -C.sub.24 alkyl which is interrupted one or more times by O or S, or are a group of the formula ##STR2## in which R.sub.5 is C.sub.4 -C.sub.18 alkyl or C.sub.5 -C.sub.10 cycloalkyl,R.sub.3 is a polymerizable reactive group,R.sub.4, if R.sub.1 and R.sub.2 are hydrogen, is C.sub.6 -C.sub.24 alkyl which is attached directly or by way of O or S to the benzene ring and is uninterrupted or is interrupted one or more times by O or S, andR.sub.4, if R.sub.1 and/or R.sub.2 are C.sub.12 -C.sub.24 alkyl, is C.sub.6 -C.sub.24 alkyl which is interrupted one or more times by O or S or is a group ##STR3## hydrogen, halogen, methyl, methoxy, CN or phenyl, or is the same as R.sub.3.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: May 12, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Sameer Hosam Eldin, Abul Iqbal, Zhimin Hao, Bernd Lamatsch
  • Patent number: 5739340
    Abstract: The invention relates to indolizine derivatives of general formula: ##STR1## in which: X denotes an --S or --SO.sub.2 -- group,each of R.sub.1 and R.sub.2, which are identical or different, denotes hydrogen, the methyl or ethyl radical or a halogen atom,R.sub.3 denotes hydrogen or a C.sub.1 -C.sub.4 alkyl radical,R.sub.4 denotes a precursor radical of a carboxyl group,R denotes a C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or phenyl radical, and their use as intermediates for the preparation of pharmaceutically active aminoalkoxybenzenesulphonylindolizine derivatives.
    Type: Grant
    Filed: April 2, 1997
    Date of Patent: April 14, 1998
    Assignee: Elf Sanofi
    Inventors: Jean Gubin, Michel Renard
  • Patent number: 5738719
    Abstract: A pigment composition, comprisinga) 80-99.8 mol % of a diketopyrrolopyrrole of formula ##STR1## wherein A and B are each independently of the other a ##STR2## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, chloro, bromo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.2 -C.sub.19 alkoxycarbonyl, C.sub.2 -C.sub.19 alkylcarbamoyl, C.sub.1 -C.sub.18 alkylmercapto, C.sub.1 -C.sub.18 alkylamino, C.sub.5 -C.sub.6 cycloalkyl, G is a direct bond or --O--, --S--, --SO--, --SO.sub.2 -- or --NR.sub.5 --, R.sub.3 and R.sub.4 are each independently of the other hydrogen, chloro, bromo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.18 alkoxy or C.sub.1 -C.sub.18 alkylamino, and R.sub.5 is hydrogen or C.sub.1 -C.sub.6 alkyl, andb) 20-0.2 mol % of a diketopyrrolopyrrole of formula ##STR3## wherein one of R.sub.6 or R.sub.7 is hydrogen and the other is --CN. Such pigment compositions are distinguished by excellent resistance to recrystallisation and heat.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: April 14, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Olof Wallquist, Ingo Schloder, Gary Wooden
  • Patent number: 5733648
    Abstract: Organic compounds having at least one ethylenically-unsaturated group are described, the organic compounds being suitable for use in coatable compositions as reactive diluents; compounds of the invention preferably have a divalent organic linking moiety devoid of reactive groups other than optional ethylenically-unsaturated groups, and a polar organic moiety and are particularly adept in solubilizing aminoplast resins having radiation-curable pendant groups.
    Type: Grant
    Filed: February 23, 1996
    Date of Patent: March 31, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
  • Patent number: 5726159
    Abstract: This invention relates to thrombin inhibiting compounds having the Formula IX--Y--NH--(CH.sub.2).sub.r --G Iwhere X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.
    Type: Grant
    Filed: September 1, 1995
    Date of Patent: March 10, 1998
    Assignee: Eli Lilly and Company
    Inventors: Aaron L. Schacht, Robert T. Shuman, Gerald F. Smith, Michael R. Wiley
  • Patent number: 5719104
    Abstract: Bicyclic imides of formulae (I) and (II) and their agriculturally-suitable salts, are disclosed which are useful for controlling undesirable vegatation, wherein G is O or S; n and m are each independently 0; 1; 2; or 3; provided that m+n is 2 or 3; q is 1 or 2; X is CH.sub.2 ; CH(halogen); CF.sub.2 ; CHOCH.sub.2 F; CHOCF.sub.3 ; CHOCH.sub.2 CF.sub.3 ; O; S(O).sub.0-2 ; NH; N(C.sub.1 -C.sub.4 alkyl); or N(C.sub.1 -C.sub.4 haloalkyl); and R.sup.1. R.sup.2, and Q are as defined in the disclosure. Also disclosed are compositions containing the bicyclic imides of formulae (I) and (II) and a method for controlling growth of undesired vegetation comprising applying to the locus to be protected an effective amount, of the bicyclic imides formulae (I) and (II).
    Type: Grant
    Filed: October 3, 1996
    Date of Patent: February 17, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: John J. Kilama, Karlheinz Drauz, Wonpyo Hong, Matthias Schafer
  • Patent number: 5710130
    Abstract: This invention relates to thrombin inhibiting compounds having the Formula IX--Y--NH--(CH.sub.2).sub.r --G Iwhere X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.
    Type: Grant
    Filed: September 1, 1995
    Date of Patent: January 20, 1998
    Assignee: Eli Lilly and Company
    Inventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
  • Patent number: 5707966
    Abstract: This invention relates to thrombin inhibiting compounds having the Formula IX--Y--NH--(CH.sub.2).sub.r --G Iwhere X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.
    Type: Grant
    Filed: September 1, 1995
    Date of Patent: January 13, 1998
    Assignee: Eli Lilly and Company
    Inventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
  • Patent number: 5708169
    Abstract: The present invention provides for new 5-amidomethyl, .alpha.,.beta.-saturated and--unsaturated butyrolactone antibacterial agents of formula I ##STR1## characterized by 3-aryl substituents that include, for example, indolinyl and phenyl substituted with zero (0) to two(2) halogen atoms and substituted in the para position with, e.g., piperazinyl, thiomorpholinyl (and corresponding sulfoxide and sulfone), thiazolidinyl (and sulfoxide and sulfone), morpholinyl, azetidinyl, pyrrolidinyl, piperidinyl, pyrrolyl, azepinyl, troponyl, 3,7-diazabicyclo?3.3.0!octan-3-yl, bridged thiazinyl or bridged oxazinyl moieties. In those cases where a ring nitrogen is present, then this is substituted to form an amide, formamide, sulfonamide, urethane, or alkylated with a wide variety of moieties.
    Type: Grant
    Filed: September 5, 1996
    Date of Patent: January 13, 1998
    Assignee: Pharmacia & Upjohn Company
    Inventors: Jackson B. Hester, Jr., Steven Joseph Brickner, Michael Robert Barbachyn, Douglas K. Hutchinson, Dana Scott Toops
  • Patent number: 5708188
    Abstract: The invention relates to mixed crystals of 1,4-diketopyrrolo?3,4-c!pyrroles, consisting of 1 mol each of two different compounds of formulae ##STR1## as well as single-phase solid solutions of two different compounds of formulae I and II, wherein the diketopyrrolopyrrole having the smaller geometrical constitution is present in an amount of 53 to 70 mol %. A and B are as defined in claim 1. The novel mixed crystals as well as the novel solid solutions are admirably suited for pigmenting organic material of high molecular weight.
    Type: Grant
    Filed: September 28, 1995
    Date of Patent: January 13, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Zhimin Hao, Abul Iqbal, Bernhard Medinger, Olof Wallquist
  • Patent number: 5705487
    Abstract: This invention relates to thrombin inhibiting compounds having the Formula IX--Y--NH--(CH.sub.2).sub.r --G Iwhere X, Y, r and G have the values defined in the description, as well as pharmaceutical formulations containing those compounds and methods of their use as thrombin inhibitors, coagulation inhibitors, and thromboembolic disorder agents.
    Type: Grant
    Filed: September 1, 1995
    Date of Patent: January 6, 1998
    Assignee: Eli Lilly and Company
    Inventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
  • Patent number: 5703091
    Abstract: Compounds of the formula I ##STR1## where B, R.sup.1, R.sup.2, n and A have the meanings given in the description, and their preparation are described. The novel compounds are suitable for the control of diseases.
    Type: Grant
    Filed: June 6, 1996
    Date of Patent: December 30, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Steiner, Rainer Munschauer, Liliane Unger, Hans-Jurgen Teschendorf, Thomas Hoger
  • Patent number: 5693824
    Abstract: A process for the preparation of mixed crystals of 1,4-diketopyrrolo?3,4-c!pyrroles, consisting of 1 mol each of two different compounds of formula ##STR1## by heating a corresponding mixture in solid form to the temperature range from 220.degree. to 380.degree. C.A and B are, for example, each a group of formula ##STR2## wherein R.sub.1 and R.sub.2 are each independently hydrogen, chloro, bromo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylamino, phenyl or --CN, G is --O--, --NR.sub.7 --, --N.dbd.N-- or --SO.sub.2 --, R.sub.3 and R.sub.4 are hydrogen, and R.sub.7 is hydrogen, methyl or ethyl.The mixed crystals and solid solutions obtained are excellently suited for pigmenting high molecular weight material.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: December 2, 1997
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Jin Mizuguchi, Zhimin Hao, Olof Wallquist, Abul Iqbal
  • Patent number: 5688790
    Abstract: This invention relates to compounds of formula (I): ##STR1## wherein R.sup.1 represents C.sub.1-4 alkyl; andR.sup.2, R.sup.3, R.sup.4 and R.sup.5 each independently represent hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxyC.sub.1-4 alkyl, C.sub.1-4 alkylsulphonyl, trifluoromethylsulphonyl; optionally substituted arylsulphonyl, optionally substituted heteroarylsulphonyl, optionally substituted aralkylsulphonyl, optionally substituted heteroaralkylsulphonyl, nitro, cyano, amino, mono- or di-alkylamino, trifluoromethyl, trifluoromethoxy, hydroxyl, hydroxyC.sub.1-4 alkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkanoyl, C.sub.1-4 alkoxycarbonyl, aminosulphonyl, or mono- or diC.sub.1-4 alkylaminosulphonyl; orR.sup.1 and R.sup.2 together form a linking chain --(CH.sub.2).sub.m Op; (wherein m is 2 to 4 and p is zero or 1) which chain may be optionally substituted by one or two C.sub.1-4 alkyl groups;and Y represents a group of formula (.alpha.
    Type: Grant
    Filed: September 28, 1995
    Date of Patent: November 18, 1997
    Assignee: SmithKline Beecham Plc
    Inventors: Michael Stewart Hadley, Christopher Norbert Johnson, Geoffrey Stemp
  • Patent number: 5686459
    Abstract: Novel dioxopyrrolo-pyrrole derivatives of the formula ##STR1## as well as hydrates or solvates thereof, which inhibit thrombin-induced or Factor Xa-induced platelet aggregation and fibrinogen clotting in blood plasma. The derivatives can be manufactured from the corresponding maleimides which are N-substituted by .alpha.-amino carboxylic acids of the formula HN(R.sup.2)CH(R.sup.4)COOH, or functional derivatives thereof; and ketones or aldehydes of the formula R.sup.5 C(O)R.sup.6.
    Type: Grant
    Filed: February 26, 1996
    Date of Patent: November 11, 1997
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Francois Diederich, Ulrike Obst, Sabine Wallbaum, Lutz Weber
  • Patent number: 5683965
    Abstract: The aryl-keto-enolic heterocycles according to the invention have the formula (I), in which Het stands for a heterocyclic group from the series (a), (b) or (c), and X, Y, Z, n, A, B, E, L and M have the meanings given in the description. The compounds having the formula (I) are pesticides, in particular acaricides, insecticides, fungicides and herbicides. Also disclosed is their preparation.
    Type: Grant
    Filed: May 13, 1996
    Date of Patent: November 4, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Bachmann, Thomas Bretschneider, Reiner Fischer, Bernd-Wieland Kruger, Hans-Joachim Santel, Markus Dollinger, Christoph Erdelen, Ulrike Wachendorff-Neumann
  • Patent number: 5679693
    Abstract: The invention relates to quaternary basic amides of the formula ##STR1## in which Ar is an optionally substituted mono-, di- or tricyclic aromatic or heteroaromatic group;T is a direct bond, a hydroxymethylene group, an alkoxymethylene group in which the alkoxy group is C.sub.1 -C.sub.4, or a C.sub.1 -C.sub.5 -alkylene group;Ar' is an unsubstituted or mono- or poly-substituted phenyl, a thienyl, a benzothienyl, a naphthyl or an indolyl;R is hydrogen or a C.sub.1 -C.sub.4 -alkyl, or a C.sub.1 -C.sub.4 -.omega.-alkoxy(C.sub.2 -C.sub.4)alkyl, or a C.sub.2 -C.sub.4 -.omega.-alkanoyloxy (C.sub.1 -C.sub.4)alkyl;.Q is hydrogen;or else Q and R together form a 1,2-ethylene, 1,3-propylene or 1,4-butylene group;Am.sup..sym. is the radical ##STR2## in which X.sub.1, X.sub.2 and X.sub.3, together with the nitrogen atom to which they are bonded, form a 1-AZONIABICYCLO?2.2.1!HEPTANE optionally substituted by a phenyl or benzyl group; andA.sup..crclbar. is a pharmaceutically acceptable anion.
    Type: Grant
    Filed: July 24, 1996
    Date of Patent: October 21, 1997
    Assignee: Sanofi
    Inventors: Xavier Emonds-Alt, Patrick Gueule, Vincenzo Proietto, Didier Van Broeck
  • Patent number: 5674877
    Abstract: Described herein are D4 receptor-selective compounds of the general formula I: ##STR1## wherein: A and B are independently selected, optionally substituted, saturated or unsaturated 5- or 6-membered, homo- or heterocyclic rings;X.sub.1 is selected from CH.sub.2, O, NH, S, C.dbd.O, CH--OH, CH--NEt.sub.2, C.dbd.CHCl, C.dbd.CHCN, N--C.sub.1-4 alkyl, N-acetyl, So.sub.2 and SO;X.sub.2 - - - is selected from N.dbd., CH.sub.2 --, CH.dbd., C(O)--, O--, and S--;n is 1 or 2; andZ is selected from C.sub.1-6 alkyl optionally substituted with a substituent selected from OH, halo, C.sub.1-4 alkyl and C.sub.1-4 alkoxy;and acid addition salts, solvates and hydrates thereof. Their use as ligands for dopamine receptor identification and in a drug screening program, and as pharmaceuticals to treat indications in which the M1/M2 receptor is implicated, such as schizophrenia, is also described.
    Type: Grant
    Filed: April 24, 1996
    Date of Patent: October 7, 1997
    Assignee: Allelix Biopharmaceuticals Inc.
    Inventors: Ashok Tehim, Sumanas Rakhit
  • Patent number: 5672716
    Abstract: The invention relates to diketopyrrolo?3,4-c!pyrroles of formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently of the other hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, cyano or a --OR.sub.3, --COOR.sub.3, --CON(R.sub.3)(R.sub.4), --COR.sub.3 or --N(R.sub.3)(R.sub.4) group, and R.sub.3 and R.sub.4 are each independently of the other hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.6 alkyl.Said diketopyrrolo?3,4-c!pyrroles are pigments colored in a strong yellow shade having good fastness properties.
    Type: Grant
    Filed: October 31, 1995
    Date of Patent: September 30, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Bernd Lamatsch, Olof Wallquist, Ingo Schloder
  • Patent number: 5650520
    Abstract: Diketopyrrolopyrrole of the formula ##STR1## in its .beta.-modification. The new .beta.-modification is likewise suitable as a pigment for coloring high-molecular weight organic material and, in comparison to the a-modification, shows a shift in shade towards yellowish-red.
    Type: Grant
    Filed: June 22, 1995
    Date of Patent: July 22, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Zhimin Hao, Ingo Schloder, Abul Iqbal
  • Patent number: 5648501
    Abstract: A process of synthesizing a compound of the formula I: ##STR1## is described. A compound of the formula II: ##STR2## is reacted with diphenylphosphinic chloride to activate the carboxylic acid group, and then reacted with methanesulfonyl chloride to produce a compound of formula IV: ##STR3## Compound IV is then reacted with Na.sub.2 S in water to produce a compound of formula I.
    Type: Grant
    Filed: July 22, 1996
    Date of Patent: July 15, 1997
    Assignee: Merck & Co., Inc.
    Inventor: Karel M. J. Brands
  • Patent number: 5646295
    Abstract: The invention concerns diazapentalene derivatives of formula I ##STR1## in which X and Y represent leaving groups which are less nucleophilic than thiol compounds, as thiol-specific fluorochromes for the detection of compounds containing thiol groups, in particular in cells.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: July 8, 1997
    Assignee: Boehringer Mannheim GmbH
    Inventors: Rudolf Gompper, Manfred Kubbies, Axel Schmidt, Bernhard Virnekas
  • Patent number: 5646299
    Abstract: Diketopyrrolopyrrole of the formula ##STR1## in its .beta.-modification and in its .gamma.-modification. Both the .beta.-modification and the .gamma.-modification are suitable as pigments for coloring high-molecular weight organic material. In comparison to the .alpha.-modification, the .beta.-modification shows a shift in shade towards yellowish-red. The .gamma.-modification gives brilliant orange colorations.
    Type: Grant
    Filed: June 22, 1995
    Date of Patent: July 8, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Zhimin Hao, Abul Iqbal, Fritz Herren
  • Patent number: 5621115
    Abstract: This invention pertains to methods for preparing 5-aroyl-1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1-carboxylic acids represented by formula (I): ##STR1## In a first embodiment, the method comprises the sequential steps of cyclizing, via a free radical ring closure reaction, and hydrolyzing a compound represented by formula (IV): ##STR2## wherein R.sub.1 is lower alkyl.
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: April 15, 1997
    Assignee: Ohmeda Pharmaceutical Products Division Inc.
    Inventors: Ralph A. Lessor, Linas V. Kudzma, Keith Ramig
  • Patent number: 5616725
    Abstract: Pyrrolo[3,4-c]pyrroles of formula ##STR1## wherein D and E are each independently of the other a group of formula ##STR2## The symbols Q, R.sub.8, R.sub.9, R.sub.10, R.sub.11, X, Y, Z, m and n are as defined in claim 1.These pyrrolo[3,4-c]pyrroles are distinguished by outstanding solid state fluorescence in the UV range as well as by the ease with which they can be converted to pyrrolopyrrole pigments even in the substrate in which they are incorporated.
    Type: Grant
    Filed: October 11, 1995
    Date of Patent: April 1, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: John S. Zambounis, Zhimin Hao, Abul Iqbal
  • Patent number: 5612366
    Abstract: The meso-azacyclic aromatic acid amides and esters of the present invention are useful in the treatment of the central nervous system and gastrointestinal motility disorders such as gastroesophageal reflux, non-ulcer dyspepsia, delayed gastric emptying, ileus, irritable bowel syndrome, and the like. Additionally, the compounds of the present invention find utility as antagonists of serotonin 5-HT.sub.3 receptors. As such they are useful for the treatment of humans and animals wherein antagonism of 5-HT.sub.3 receptors is beneficial. Therapy is indicated for, but not limited to, the treatment of anxiety, psychoses, depression (especially depression accompanied by anxiety), cognitive disorders, substance abuse dependence and/or withdrawal, irritable bowel syndrome, emesis caused by chemotherapeutic agents, and visceral pain. Additionally, the compounds of the present invention may find utility as enhancers of nasal absorption of bioactive compounds.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: March 18, 1997
    Assignee: G. D. Searle & Co.
    Inventors: Daniel P. Becker, Daniel L. Flynn, Alan E. Moorman, Roger Nosal, Clara I. Villamil
  • Patent number: 5604252
    Abstract: The present invention relates to novel azanorbornane derivatives having the formula ##STR1## wherein R.sup.1 through R.sup.12 are defined as below, and to novel intermediates used in their synthesis. The compounds having formula I are useful in the treatment of inflammatory and central nervous system disorders, as well as other disorders.
    Type: Grant
    Filed: December 14, 1993
    Date of Patent: February 18, 1997
    Assignee: Pfizer Inc.
    Inventor: Brian T. O'Neill
  • Patent number: 5591865
    Abstract: Diketopyrrolopyrrole of the formula ##STR1## in its .beta.-modification. The new .beta.-modification is suitable as a pigment for coloring high-molecular weight organic material and shows, in comparison to the .alpha.-modification, a shift in shade towards yellowish-red.
    Type: Grant
    Filed: June 22, 1995
    Date of Patent: January 7, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Zhimin Hao, Abul Iqbal, Fritz Herren
  • Patent number: 5580999
    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: December 3, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
  • Patent number: 5571920
    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: January 26, 1996
    Date of Patent: November 5, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
  • Patent number: 5565578
    Abstract: A process for conditioning diaryldiketopyrrolo[3,4-c]pyrrole pigments (DPP) and for preparing solid solutions having a DPP component are disclosed. The inventive processes involve dissolving the DPP in aqueous, basic DMSO, alone, or in mixture with additional components in the case of a solid solution, and then precipitating the conditioned pigment or pigment solid solution by methods known in the art.
    Type: Grant
    Filed: January 16, 1996
    Date of Patent: October 15, 1996
    Assignee: Ciba-Geigy Corporation
    Inventor: Fridolin B abler
  • Patent number: 5554763
    Abstract: The invention relates to quaternary basic amides of the formula ##STR1## in which Ar is an optionally substituted mono-, di- or tri-cyclic aromatic or heteroaromatic group;T is a direct bond, a hydroxymethylene group, an alkoxymethylene group in which the alkoxy group is C.sub.1 -C.sub.4, or a C.sub.1 -C.sub.5 -alkylene group;Ar' is an unsubstituted or mono- or poly-substituted phenyl, a thienyl, a benzothienyl, a naphthyl or an indolyl;R is hydrogen or a C.sub.1 -C.sub.4 -alkyl, or a .omega.-C.sub.1 -C.sub.4 -alkoxy(C.sub.2 -C.sub.4)alkyl, or a .omega.-C.sub.2 -C.sub.4 -alkanoyloxy (C.sub.1 -C.sub.4)alkyl;.Q is hydrogen;or else Q and R together form a 1,2-ethylene, 1,3-propylene or 1,4-butylene group;Am.sup..sym. is the radical ##STR2## in which X.sub.1, X.sub.2 and X.sub.3, together with the nitrogen atom to which they are bonded, form an azabicyclic or azatricyclic system optionally substituted by a phenyl or benzyl group; andA.sup..crclbar. is a pharmaceutically acceptable anion.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: September 10, 1996
    Assignee: Sanofi
    Inventors: Xavier Emonds-Alt, Patrick Gueule, Vincenzo Proietto, Didier Van Broeck
  • Patent number: 5541194
    Abstract: Novel compounds of formula (I), processes for their preparation, and their use as pharmaceutical agents are described: ##STR1## in which p represents an integer of 2 to 4; r represents an integer of 1 or 2; s represents 0 or 1; and X represents a group ##STR2## in which A.sub.1 is oxygen or sulphur, one of A.sub.2 and A.sub.3 is CR.sub.1 and the other is nitrogen or CR.sub.2, or A.sub.2 is oxygen or sulphur, A.sub.1 is CH and A.sub.3 is CR.sub.1, where R.sub.1 and R.sub.2 are independently selected from hydrogen and C.sub.1-2 alkyl, with the proviso that when r is 2, R.sub.1 and R.sub.2 are hydrogen or methyl. The novel compounds of this invention may be used to treat or to prevent dementia in mammals.
    Type: Grant
    Filed: January 6, 1995
    Date of Patent: July 30, 1996
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Paul A. Wyman, Harry J. Wadsworth
  • Patent number: 5539125
    Abstract: There are disclosed a 1-azabicyclo[3.3.0]octan derivative of the formula ##STR1## wherein n is an integer of 1-5; and Ar is an aromatic residue. a pharmacologically acceptable salt of the compound, a process for the preparation of the compound and salt as well as use thereof as hypermotility agents.
    Type: Grant
    Filed: June 13, 1995
    Date of Patent: July 23, 1996
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Yutaka Baba, Toshinao Usui, Takuji Kakigami, Yoshiro Ozeki, Katsura Tsukamoto, Nobuyuki Itoh
  • Patent number: 5532266
    Abstract: Novel arylacetamides of the formula I ##STR1## in which Q is R.sup.4 --CH(CH.sub.2 Z)--NA--, ##STR2## R.sup.1 is Ar, cycloalkyl with 3-7 C atoms or C.sub.4 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.7 -alkyl,R.sup.2 is Ar,R.sup.3 is H, OH, OA or A,R.sup.4 is A or phenyl which can optionally be substituted once or twice by F, Cl, Br, I, OH, OA, CF.sub.3, NO.sub.2, NH.sub.2, NHA, NHCOA, NHSO.sub.2 A or NA.sub.2,R.sup.5 and R.sup.6 are each, independently of one another, H, F, Cl, Br, I, OH, OA, CF.sub.3, NH.sub.2, NHA, NA.sub.2, NHCOA, NHCONH.sub.2, NO.sub.2 or taken together are methylenedioxy,A is alkyl with 1-7 C atoms, and physiologically acceptable salts thereof.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: July 2, 1996
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Gottschlich, Karl-August Ackermann, Helmut Prucher, Christoph Seyfried, Hartmut Greiner, Gerd Bartoszyk, Frank Mauler, Manfred Stohrer, Andrew Barber
  • Patent number: 5532381
    Abstract: This invention relates to novel processes for preparing substituted pyrrolizine compounds. More particularly, it relates to novel processes for preparing 5-aroyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate of the following formula (I) from pyrrole.
    Type: Grant
    Filed: November 30, 1994
    Date of Patent: July 2, 1996
    Assignee: Dong Kook Pharmaceutical Co., Ltd.
    Inventors: Yong H. Kim, Hee S. Park, Dong H. Lee
  • Patent number: 5529623
    Abstract: Binary and ternary pigmentary solid solutions are disclosed. The binary solid solutions are binary solid compounds consisting of 35-45 weight-percent unsubstituted DPP and 55-65 weight-percent dichloro DPP. The ternary solid solutions are guest-host solid solutions wherein the binary solid compound is the host and up to 30 weight-percent of a disubstituted quinacridone pigment is the guest. The binary and ternary solid solutions are useful as pigments for coloring high-molecular-weight organic materials; especially as replacements for perylene pigments in automotive finishes.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: June 25, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Shivakumar B. Hendi, James B. Ganci, Edward E. Jaffe
  • Patent number: 5530138
    Abstract: There is disclosed a compound shown by a formula of ##STR1## wherein R.sub.1 is a hydrogen atom alkyl group having 1-4 carbon atoms or acyl group having 1-4 carbon atoms: R.sub.2 and R.sub.3 are a hydrogen atom, alkyl group having 1-4 carbon atoms, phenyl radical, halogen atom, cyano radical, acyl group having 1-4 carbon atoms, nitro radical, alkoxy group having 1 or 2 carbon atoms, or substituted or non-substituted amino group, respectively; n is an integer of 1-3; and dotted line means a possible ring, and a salt thereof. The compound and salt bind with muscarinic receptor in brain to develop a powerful actuation thereof and thus those can be used as an effective ingredient for preventing and curing senile dementias, and more particularly Alzheimer's disease.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: June 25, 1996
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Yutaka Baba, Tomoo Suzuki, Tsunemasa Suzuki, Kiyotaka Hirooka, Masayasu Kurono, Kiichi Sawai
  • Patent number: 5527922
    Abstract: The invention relates to pyrrolo[3,4-c]pyrroles of formula ##STR1## wherein D and E are each independently of the other hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.7 -C.sub.10 aralkyl, unsubstituted phenyl or phenyl which is substituted by chloro, bromo, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl or nitro, or --COO--C.sub.1 -C.sub.5 alkyl or a group --COOR.sub.8,wherein R.sub.8 is benzyl, piperidyl or a group ##STR2## and X and Y are N--CN or O, with the proviso that at least one of X or Y N--CN must be N--CN.These pyrrolo[3,4-c]pyrroles are preeminently suitable for use as colorants, i.e. as pigments or as polymer-soluble dyes, for colouring high molecular weight organic material. They are distinguished by unexpectedly high solid-state fluorescence.The substituents A and B are as defined in claim 1.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: June 18, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: John S. Zambounis, Zhimin Hao, Abul Iqbal
  • Patent number: 5525735
    Abstract: Disclosed are methods for synthesizing very large collections of diverse pyrrolidine compounds and derivatives thereof on solid supports and synthetic compound libraries comprising pyrrolidine groups and derivatives thereof prepared by such methods.
    Type: Grant
    Filed: December 12, 1994
    Date of Patent: June 11, 1996
    Assignee: AFFYMAX Technologies NV
    Inventors: Mark A. Gallop, Martin A. Murphy
  • Patent number: 5525734
    Abstract: Disclosed are methods for synthesizing very large collections of diverse pyrrolidine compounds on solid supports and synthetic compound libraries comprising pyrrolidine groups prepared by such methods.
    Type: Grant
    Filed: June 22, 1994
    Date of Patent: June 11, 1996
    Assignee: Affymax Technologies N.V.
    Inventors: Mark A. Gallop, Martin A. Murphy
  • Patent number: 5521213
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: May 28, 1996
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Petpiboon Prasit, Daniel Guay, Zhaoyin Wang, Serge Leger, Michel Therien
  • 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: RE35593
    Abstract: A compound of formula (I) or a pharmaceutically acceptable salt thereof: ##STR1## wherein R.sup.1 represents ##STR2## in which each of p and q independently represents an integer of 2 to 4, r represents an integer of 2 to 4, s represents 1 or 2 and t represents 0 or 1;R.sub.2 is a group OR.sub.4, where R.sub.4 is C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, a group OCOR.sub.5 where R.sub.5 is hydrogen or R.sub.4, or a group NHR.sub.6 or NR.sub.7 R.sub.8 where R.sub.6, R.sub.7 and R.sub.8 are independently C.sub.1-2 alkyl; andR.sub.3 is chloro, fluoro, bromo, cyclopropyl, C.sub.1-3 alkyl substituted by one, two or three halogen atoms, or R.sub.3 is a group (CH.sub.2).sub.n R.sub.9 where R.sub.9 is --CN, --OH, --OCH.sub.3, --SH, --SCH.sub.3, --C.tbd.CH or --CH.dbd.CH.sub.2 and n is O or 1, with the proviso that when n is 0, R.sub.9 is not --OH or --SH.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: August 19, 1997
    Assignee: Beecham Group p.l.c.
    Inventors: Barry S. Orlek, Steven M. Bromidge, Steven Dabbs