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)
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Patent number: 5789587Abstract: 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: GrantFiled: November 6, 1996Date of Patent: August 4, 1998Assignee: Merck & Co., Inc.Inventors: Michael H. Fisher, Helmut Mrozik, William R. Schoen, Thomas L. Shih, Matthew J. Wyvratt
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Patent number: 5786487Abstract: 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: GrantFiled: September 26, 1997Date of Patent: July 28, 1998Assignee: Ciba Specialty Chemicals CorporationInventor: Shivakumar B. Hendi
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Patent number: 5780495Abstract: 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: GrantFiled: July 29, 1997Date of Patent: July 14, 1998Assignee: Nicox S.A.Inventor: Piero Del Soldato
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Patent number: 5780633Abstract: A new process for preparing a compound of the formula: ##STR1##Type: GrantFiled: May 6, 1996Date of Patent: July 14, 1998Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Satoshi Okada, Kozo Sawada, Akio Kuroda, Shinya Watanabe, Hirokazu Tanaka
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Patent number: 5756746Abstract: 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: GrantFiled: September 23, 1996Date of Patent: May 26, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Zhimin Hao, Abul Iqbal
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Patent number: 5750702Abstract: 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: GrantFiled: July 16, 1996Date of Patent: May 12, 1998Assignee: Neurogen CorporationInventors: Pamela Albaugh, Alan Hutchison
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Patent number: 5750723Abstract: 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: GrantFiled: January 29, 1997Date of Patent: May 12, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Sameer Hosam Eldin, Abul Iqbal, Zhimin Hao, Bernd Lamatsch
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Patent number: 5739340Abstract: 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: GrantFiled: April 2, 1997Date of Patent: April 14, 1998Assignee: Elf SanofiInventors: Jean Gubin, Michel Renard
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Patent number: 5738719Abstract: 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: GrantFiled: February 14, 1997Date of Patent: April 14, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Olof Wallquist, Ingo Schloder, Gary Wooden
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Patent number: 5733648Abstract: 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: GrantFiled: February 23, 1996Date of Patent: March 31, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
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Patent number: 5726159Abstract: 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: GrantFiled: September 1, 1995Date of Patent: March 10, 1998Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Robert T. Shuman, Gerald F. Smith, Michael R. Wiley
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Patent number: 5719104Abstract: 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: GrantFiled: October 3, 1996Date of Patent: February 17, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: John J. Kilama, Karlheinz Drauz, Wonpyo Hong, Matthias Schafer
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Patent number: 5710130Abstract: 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: GrantFiled: September 1, 1995Date of Patent: January 20, 1998Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
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Patent number: 5707966Abstract: 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: GrantFiled: September 1, 1995Date of Patent: January 13, 1998Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
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Patent number: 5708169Abstract: 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: GrantFiled: September 5, 1996Date of Patent: January 13, 1998Assignee: Pharmacia & Upjohn CompanyInventors: Jackson B. Hester, Jr., Steven Joseph Brickner, Michael Robert Barbachyn, Douglas K. Hutchinson, Dana Scott Toops
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Patent number: 5708188Abstract: 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: GrantFiled: September 28, 1995Date of Patent: January 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Zhimin Hao, Abul Iqbal, Bernhard Medinger, Olof Wallquist
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Patent number: 5705487Abstract: 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: GrantFiled: September 1, 1995Date of Patent: January 6, 1998Assignee: Eli Lilly and CompanyInventors: Aaron L. Schacht, Gerald F. Smith, Michael R. Wiley
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Patent number: 5703091Abstract: 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: GrantFiled: June 6, 1996Date of Patent: December 30, 1997Assignee: BASF AktiengesellschaftInventors: Gerd Steiner, Rainer Munschauer, Liliane Unger, Hans-Jurgen Teschendorf, Thomas Hoger
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Patent number: 5693824Abstract: 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: GrantFiled: September 12, 1996Date of Patent: December 2, 1997Assignee: Ciba Specialty Chemicals CorporationInventors: Jin Mizuguchi, Zhimin Hao, Olof Wallquist, Abul Iqbal
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Patent number: 5688790Abstract: 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: GrantFiled: September 28, 1995Date of Patent: November 18, 1997Assignee: SmithKline Beecham PlcInventors: Michael Stewart Hadley, Christopher Norbert Johnson, Geoffrey Stemp
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Patent number: 5686459Abstract: 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: GrantFiled: February 26, 1996Date of Patent: November 11, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Francois Diederich, Ulrike Obst, Sabine Wallbaum, Lutz Weber
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Patent number: 5683965Abstract: 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: GrantFiled: May 13, 1996Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventors: Jurgen Bachmann, Thomas Bretschneider, Reiner Fischer, Bernd-Wieland Kruger, Hans-Joachim Santel, Markus Dollinger, Christoph Erdelen, Ulrike Wachendorff-Neumann
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Patent number: 5679693Abstract: 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: GrantFiled: July 24, 1996Date of Patent: October 21, 1997Assignee: SanofiInventors: Xavier Emonds-Alt, Patrick Gueule, Vincenzo Proietto, Didier Van Broeck
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Patent number: 5674877Abstract: 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: GrantFiled: April 24, 1996Date of Patent: October 7, 1997Assignee: Allelix Biopharmaceuticals Inc.Inventors: Ashok Tehim, Sumanas Rakhit
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Patent number: 5672716Abstract: 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: GrantFiled: October 31, 1995Date of Patent: September 30, 1997Assignee: Ciba-Geigy CorporationInventors: Bernd Lamatsch, Olof Wallquist, Ingo Schloder
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Patent number: 5650520Abstract: 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: GrantFiled: June 22, 1995Date of Patent: July 22, 1997Assignee: Ciba-Geigy CorporationInventors: Zhimin Hao, Ingo Schloder, Abul Iqbal
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Patent number: 5648501Abstract: 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: GrantFiled: July 22, 1996Date of Patent: July 15, 1997Assignee: Merck & Co., Inc.Inventor: Karel M. J. Brands
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Patent number: 5646295Abstract: 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: GrantFiled: January 31, 1996Date of Patent: July 8, 1997Assignee: Boehringer Mannheim GmbHInventors: Rudolf Gompper, Manfred Kubbies, Axel Schmidt, Bernhard Virnekas
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Patent number: 5646299Abstract: 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: GrantFiled: June 22, 1995Date of Patent: July 8, 1997Assignee: Ciba-Geigy CorporationInventors: Zhimin Hao, Abul Iqbal, Fritz Herren
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Patent number: 5621115Abstract: 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: GrantFiled: February 21, 1996Date of Patent: April 15, 1997Assignee: Ohmeda Pharmaceutical Products Division Inc.Inventors: Ralph A. Lessor, Linas V. Kudzma, Keith Ramig
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Patent number: 5616725Abstract: 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: GrantFiled: October 11, 1995Date of Patent: April 1, 1997Assignee: Ciba-Geigy CorporationInventors: John S. Zambounis, Zhimin Hao, Abul Iqbal
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Patent number: 5612366Abstract: 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: GrantFiled: April 28, 1994Date of Patent: March 18, 1997Assignee: G. D. Searle & Co.Inventors: Daniel P. Becker, Daniel L. Flynn, Alan E. Moorman, Roger Nosal, Clara I. Villamil
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Patent number: 5604252Abstract: 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: GrantFiled: December 14, 1993Date of Patent: February 18, 1997Assignee: Pfizer Inc.Inventor: Brian T. O'Neill
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Patent number: 5591865Abstract: 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: GrantFiled: June 22, 1995Date of Patent: January 7, 1997Assignee: Ciba-Geigy CorporationInventors: Zhimin Hao, Abul Iqbal, Fritz Herren
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Patent number: 5580999Abstract: 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: GrantFiled: May 12, 1995Date of Patent: December 3, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
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Patent number: 5571920Abstract: 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: GrantFiled: January 26, 1996Date of Patent: November 5, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
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Patent number: 5565578Abstract: 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: GrantFiled: January 16, 1996Date of Patent: October 15, 1996Assignee: Ciba-Geigy CorporationInventor: Fridolin B abler
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Patent number: 5554763Abstract: 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: GrantFiled: June 6, 1995Date of Patent: September 10, 1996Assignee: SanofiInventors: Xavier Emonds-Alt, Patrick Gueule, Vincenzo Proietto, Didier Van Broeck
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Patent number: 5541194Abstract: 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: GrantFiled: January 6, 1995Date of Patent: July 30, 1996Assignee: Beecham Group p.l.c.Inventors: Barry S. Orlek, Paul A. Wyman, Harry J. Wadsworth
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Patent number: 5539125Abstract: 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: GrantFiled: June 13, 1995Date of Patent: July 23, 1996Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.Inventors: Yutaka Baba, Toshinao Usui, Takuji Kakigami, Yoshiro Ozeki, Katsura Tsukamoto, Nobuyuki Itoh
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Patent number: 5532266Abstract: 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: GrantFiled: May 30, 1995Date of Patent: July 2, 1996Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Gottschlich, Karl-August Ackermann, Helmut Prucher, Christoph Seyfried, Hartmut Greiner, Gerd Bartoszyk, Frank Mauler, Manfred Stohrer, Andrew Barber
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Patent number: 5532381Abstract: 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: GrantFiled: November 30, 1994Date of Patent: July 2, 1996Assignee: Dong Kook Pharmaceutical Co., Ltd.Inventors: Yong H. Kim, Hee S. Park, Dong H. Lee
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Patent number: 5529623Abstract: 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: GrantFiled: September 28, 1994Date of Patent: June 25, 1996Assignee: Ciba-Geigy CorporationInventors: Shivakumar B. Hendi, James B. Ganci, Edward E. Jaffe
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Patent number: 5530138Abstract: 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: GrantFiled: September 27, 1994Date of Patent: June 25, 1996Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.Inventors: Yutaka Baba, Tomoo Suzuki, Tsunemasa Suzuki, Kiyotaka Hirooka, Masayasu Kurono, Kiichi Sawai
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Patent number: 5527922Abstract: 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: GrantFiled: March 21, 1995Date of Patent: June 18, 1996Assignee: Ciba-Geigy CorporationInventors: John S. Zambounis, Zhimin Hao, Abul Iqbal
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Patent number: 5525735Abstract: 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: GrantFiled: December 12, 1994Date of Patent: June 11, 1996Assignee: AFFYMAX Technologies NVInventors: Mark A. Gallop, Martin A. Murphy
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Patent number: 5525734Abstract: 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: GrantFiled: June 22, 1994Date of Patent: June 11, 1996Assignee: Affymax Technologies N.V.Inventors: Mark A. Gallop, Martin A. Murphy
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Patent number: 5521213Abstract: 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: GrantFiled: August 29, 1994Date of Patent: May 28, 1996Assignee: Merck Frosst Canada, Inc.Inventors: Petpiboon Prasit, Daniel Guay, Zhaoyin Wang, Serge Leger, Michel Therien
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Patent number: 5516913Abstract: 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: GrantFiled: May 12, 1995Date of Patent: May 14, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
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Patent number: RE35593Abstract: 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: GrantFiled: January 11, 1996Date of Patent: August 19, 1997Assignee: Beecham Group p.l.c.Inventors: Barry S. Orlek, Steven M. Bromidge, Steven Dabbs