The Tricyclo Ring System Consists Of A Benzene Ring Which Shares Ring Carbons With Two Nitrogen Containing Hetero Rings (e.g., Pyromellitic Diimide, Etc.) Patents (Class 548/433)
  • Patent number: 6534657
    Abstract: Ferrocene anchored chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. The new ligands are effective for asymmetric Pd-catalyzed allylic alkylation reactions and Ag-catalyzed [3+2] cyclization of azomethine ylides.
    Type: Grant
    Filed: February 9, 2001
    Date of Patent: March 18, 2003
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Patent number: 6268391
    Abstract: Compounds of general formula (I) wherein: R1 is H or optionally joined with R2 to form a fused ring selected from the group consisting of five to ten membered aryl, heteroaryl or heterocyclyl rings, R2 and R3 are independently H, HET, aryl, C1-12 aliphatic, CN, NO2, halogen, R10, —OR10, —SR10, —S(O)R10, —SO2R10, —NR10R11, —NR11R12, —NR12COR11, —NR12CO2R11, —NR12CONR11R12, —NO12SO2R11, —NR12C(NR 12)NHR11, —COR11, —CO2R11, —CONR12R11, —SO2NR12R11, —OCONR12R11, C(NR12)NR12R11, R6 and R7 are independently halogen, CN, NO2, —CONR10R11, —SO2NR10R11, —NR10R11, or —OR11, where R10 and R11 are as defined below; R8 is OH, NHSO2R12 or NHCOCF3; and their use in therapy, especially in the treatment of disorders mediated by cRaf1 kinase.
    Type: Grant
    Filed: April 7, 2000
    Date of Patent: July 31, 2001
    Assignee: Glaxo Wellcome Inc.
    Inventors: Scott Howard Dickerson, Philip Anthony Harris, Robert Neil Hunter, III, David Kendall Jung, Karen Elizabeth Lackey, Robert Walton McNutt, Jr., Michael Robert Peel, James Marvin Veal
  • Patent number: 6201129
    Abstract: A compound having the formula wherein R1 is COOR8 wherein R8 is alkyl having from 1 to 10 carbon atoms or aralkyl, the aralkyl having from one to four carbon atoms in the alkyl portion and a carbocyclic or heterocyclic group in the aryl portion; R2 is H, alkyl having from 1 to 10 carbon atoms, or COOR7 wherein R7 is alkyl having from 1 to 10 carbon atoms; R3 is H, alkyl having from 1 to 10 carbon atoms, or COOR8; R4 is H, alkyl having from 1 to 10 carbon atoms, or COOR8; R5 is H, alkyl having from 1 to 10 carbon atoms, aralkyl having from 1 to 4 carbon atoms in the alkyl portion, aryl having from 1 to 10 carbon atoms, acyl having from 1 to 10 carbon atoms, or COOCH3; and R6 is H or COOCH3; and thereof.
    Type: Grant
    Filed: August 1, 1997
    Date of Patent: March 13, 2001
    Assignee: Univ. College Cardiff Consultants
    Inventors: David Drysdale Miller, Patrick Vivian Richard Shannon, Laddawan Chuncharprasert
  • Patent number: 6162822
    Abstract: A compound of formula (I) ##STR1## in which: m, and n, which may be identical or different, represent 0 or 1,X and Y, which may be identical or different, represent hydrogen or halogen or alky, trihaloalkyl, alkoxy, hydroxyl, cyano, nitro, amino, alkylamino or dialkylamino,Z represent a linear or branched C.sub.4 to C.sub.12 alkylene chain in which one or more --CH.sub.2 -- are optionally replaced by any one of the following atoms or groups: --NR--, --O--, --S--, --SO--, --SO.sub.2 --, or --CONH--, or by a substituted or unsubstituted heterocylcic,A forms, with two adjacent carbon atoms of the phenyl ring, a phenyl, naphthyl or tetrahydronaphthyl ring or a heterocycle, ##STR2## and medicinal products containing the same are useful as anticancer agent.
    Type: Grant
    Filed: December 28, 1998
    Date of Patent: December 19, 2000
    Assignee: Adir et Compagnie
    Inventors: Gilbert Lavielle, Patrick Hautefaye, Ghanem Atassi, Alain Pierre, Laurence Kraus-Berthier, Stephane Leonce
  • Patent number: 6153764
    Abstract: This invention relates to a process for preparing perylene pigment compositions by reaction of(a) a perylene tetracarboxylic compound;(b) about 0.01 to about 20% by weight, relative to the perylene tetracarboxylic compound, of a non-pigmentary cyclic anhydride or imide of formula (I) ##STR1## wherein W is O or NR.sup.1 (where R.sup.1 is hydrogen, a metal, or optionally substituted alkyl, cycloalkyl, aralkyl, or aryl), R.sup.2, R.sup.3, and R.sup.4 are various combinations of substituents and/or fused-on rings, and the dotted line is an optional double bond representing R.sup.2 --C.dbd.C--R.sup.3 ;(c) ammonia or a primary alkyl, aralkyl, or aryl amine; optionally in the presence of(d) a solvent and/or(e) one or more dispersants.
    Type: Grant
    Filed: January 25, 2000
    Date of Patent: November 28, 2000
    Assignee: Bayer Corporation
    Inventors: Gregory R. Schulz, Michael J. Greene
  • Patent number: 6130237
    Abstract: The invention provides compounds of general formula (I), wherein: X is halogen or OSO.sub.2 R, where R represents H or is unsubstituted or hydroxy-or amino-substituted lower alkyl; Y is a nitro or amine group or a substituted derivative thereof; W is selected from the structures of formulae (Ia, Ib or Ic), where E is --N.dbd. or --CH.dbd., G is O, S, or NH, and Q is either up to three of R, OR, NRR, NO.sub.2, CONHR, NHCOR or NHCONHR, or is an additional group of formulae (Ia, Ib or Ic) and HET represents a 5- or 6-membered carbocycle or heterocycle; and A and B collectively represent a fused benzene or 2-CO.sub.2 R pyrrole ring. In one embodiment, the group Y is an amine derivative substituted by a group which is a substrate for a nitroreductase or carboxypeptidase enzyme such that one of said enzymes is able to bring about removal of that group.
    Type: Grant
    Filed: March 12, 1999
    Date of Patent: October 10, 2000
    Assignee: Cancer Research Campaign Technology Limited
    Inventors: William A. Denny, Moana Tercel, Graham J. Atwell
  • Patent number: 6114419
    Abstract: Fluorinated imides useful for imparting repellency of low surface tension fluids to thermoplastic polymers of formulae ##STR1## wherein R.sub.1 is F(CF.sub.2).sub.x --(CH.sub.2).sub.m, or F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5) (CH.sub.2)p wherein x is from about 4 to about 20, m is from about 2 to about 6, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.2 is a linear, branched or cyclic alkylene or poly(oxyalkylene) hydrocarbon group having from about 2 to about 15 carbons;R.sub.3 is selected from the group consisting of F(CF.sub.2).sub.x --(CH.sub.2).sub.m, F(CF.sub.2).sub.x --(CH.sub.2).sub.m --OC(O)--(CH.sub.2).sub.n, and F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5)(CH.sub.2).sub.p OC(O)(CH.sub.2).sub.n wherein x is from about 4 to about 20, m is from about 2 to about 6, n is about 2 to about 12, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.4 is an alkyl or alkenyl group of from about 4 to about 20 carbons, andR.sub.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: September 5, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Theodor Arthur Liss, Kimberly Gheysen Raiford, Edward James Greenwood
  • Patent number: 6080859
    Abstract: Pyrroloindole derivatives having antimicrobial and antitumor activities and having a carbamoyloxy group represented by the following general formula (1), optical isomers thereof, and pharmacologically acceptable salts thereof; and intermediates for production thereof: ##STR1## where R.sup.1 is OH, or a pyrrolidinyl group; n is 1 or 2; R.sup.2 is a lower alkyl group of C.sub.1 -C.sub.4 ; X--Y or Y--X is CH.sub.2, CHOH, CH.sub.2 -CH.sub.2, O--CH.sub.2, or NMe--CH.sub.2 ; Z.sup.1 is Cl or Br; and Ar.sup.1 is ##STR2## wherein Z.sup.2 and Z.sup.3 are O or NH; m is 0 or an integer of 1 to 4; and Ar.sup.2 is any of the above groups a, b, c, and d.
    Type: Grant
    Filed: July 19, 1999
    Date of Patent: June 27, 2000
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Yasumichi Fukuda, Rumiko Shimazawa, Yasuo Oomori, Shiro Terashima
  • Patent number: 6066742
    Abstract: Indole derivatives shown by the formulae (1), (2a) and (2b) ##STR1## (wherein R.sup.1 is a protecting group for amino group; R.sup.2 is a protecting group for hydroxyl group; R.sup.3 is a protecting group for hydroxyl group; R.sup.4 is a C.sub.1 -C.sub.6 linear or branched lower alkyl group, or benzyl group), and pyrroloindole derivatives shown by formula (3) ##STR2## (wherein R.sup.1 is a protecting group for amino group; R.sup.2 is a protecting group for hydroxyl group; R.sup.3 is a protecting group for hydroxyl group; R.sup.4 is a C.sub.1 -C.sub.6 linear or branched lower alkyl group, or benzyl group), both of which are intermediates for duocarmycin SA, which is expected to be used as an anticancer agent, and derivatives thereof; and a method for producing the same.
    Type: Grant
    Filed: March 9, 1999
    Date of Patent: May 23, 2000
    Assignees: Kyorin Pharmaceutical Co., Ltd., Sagami Chemical Research Center
    Inventors: Yasumichi Fukuda, Shiro Terashima
  • Patent number: 6018055
    Abstract: A polyarylether of the formula (VIII) ##STR1## wherein wherein Z' is 1-3 optionally substituted rings selected from the group consisting of an aromatic ring, a hetero aromatic ring or an aliphatic ring.A is --R.sub.1 --Z--Y in which R.sub.1 is H, C.sub.1 -C.sub.30 -alkyl or -aralkyl or phenyl, Z is a direct bond or CH.sub.2, S, O or NH, Y is CH.sub.3, OR.sub.3, SR.sub.3, NHR.sub.3, N(R.sub.3).sub.2, COOR.sub.3, COOM, SO.sub.3 R.sub.3 or SO.sub.3 M in which R.sub.3 is C.sub.1 -C.sub.30 alkyl and M is alkali metal,produced from 3,6-dihalogen- or -dintro-1,2,4,5-diimide having an N,N-substituent and which is suitable for use as a monomer for high temperature structural and functional polymers, and a process for producing the same are disclosed.
    Type: Grant
    Filed: July 15, 1997
    Date of Patent: January 25, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Kil-Yeong Choi, Dong-Hack Suh, Young-Taik Hong, Eun-Young Chung
  • Patent number: 5917053
    Abstract: The present patent application discloses compounds having the formula ##STR1## or a pharmaceutically acceptable salt thereof wherein R.sup.1, X and R.sup.5 have the meanings set further in the specification.A is a ring of five to seven atoms fused with the benzo ring at the positions marked a and b.The compounds are useful in the treatment of cerebrovascular disorders for example.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: June 29, 1999
    Assignee: Neurosearch A/S
    Inventors: Peter Moldt, Frank Watjen
  • Patent number: 5843937
    Abstract: The present invention relates to novel DNA alkylating agents and the prodrugs of these agents which are useful as antitumor agents and DNA labelling agents. The compounds are hydroxy dihydrobenzindole oligopeptides and prodrugs thereof wherein the monomeric constituents are derived from monocyclic or bicyclic heterocyclic aromatic residues.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: December 1, 1998
    Assignee: Panorama Research, Inc.
    Inventors: Yuqiang Wang, Susan C. Wright, James W. Larrick
  • Patent number: 5801174
    Abstract: The present patent application discloses compounds having the formula ##STR1## or a pharmaceutically acceptable salt thereof whereinR.sup.1 is hydrogen, alkyl or benzyl;X is O or NOR.sup.2, wherein R.sup.2 is hydrogen, alkyl or benzyl;Y is N--R.sup.4 wherein R.sup.4 is hydrogen, OH or alkyl;n is 0 or 1;R.sup.6 is phenyl which is substituted one or more times with substituents selected from the group consisting of SO.sub.2 NR'R", CONR'R", and COR'"wherein R' and R" each independently are hydrogen, alkyl, or --(CH.sub.2).sub.p --W, wherein p is 0, 1, 2, 3, 4, 5, or 6, and W is hydroxy, amino, alkoxycarbonyl, or phenyl which may be substituted one or more times with substituents selected from the group consisting of halogen, CF.sub.3, NO.sub.2, amino, alkyl, alkoxy or methylenedioxy; or wherein R' and R" together is (CH.sub.2).sub.r Z(CH.sub.2).sub.s wherein r and s each independently are 0, 1, 2, 3, 4, 5, or 6 and Z is O, S, CH.sub.2 or NR"" wherein R"" is hydrogen, alkyl, or --(CH.sub.2).sub.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: September 1, 1998
    Assignee: Neurosearch A/S
    Inventors: Peter Moldt, Frank Watjen
  • Patent number: 5789491
    Abstract: Fluorinated imides useful for imparting repellency of low surface tension fluids to thermoplastic polymers of formulae ##STR1## wherein R.sub.1 is F(CF.sub.2).sub.x --(CH.sub.2).sub.m, or F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5)(CH.sub.2)p wherein x is from about 4 to about 20, m is from about 2 to about 6, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.2 is a linear, branched or cyclic alkylene or poly(oxyalkylene) hydrocarbon group having from about 2 to about 15 carbons;R.sub.3 is selected from the group consisting of F(CF.sub.2).sub.x --(CH.sub.2).sub.m, F(CF.sub.2).sub.x --(CH.sub.2).sub.m --OC(O)--(CH.sub.2).sub.n, and F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5)(CH.sub.2).sub.p OC(O)(CH.sub.2).sub.nwherein x is from about 4 to about 20, m is from about 2 to about 6, n is about 2 to about 12, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.4 is an alkyl or alkenyl group of from about 4 to about 20 carbons, andR.sub.
    Type: Grant
    Filed: June 19, 1997
    Date of Patent: August 4, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Theodor Arthur Liss, Kimberly Gheysen Raiford, Edward James Greenwood
  • Patent number: 5786486
    Abstract: Acrylamide derivatives represented by General Formula (1) below: ##STR1## (One specific example of General Formula (1) is methyl (S,S)-3,3'-?3,3'-(1,4-phenylenediacryloyl)!-bis?1-chloromethyl-5-hydroxy-7 -triflouromethyl-1, 2,3,6-tetrahydropyrrolo?3,2-e!indole-8-carboxylate.)The acrylamide derivatives represented by General Formula (1) is highly selective to cancer cells, less toxic, and highly active also against solid tumor.
    Type: Grant
    Filed: May 13, 1997
    Date of Patent: July 28, 1998
    Assignees: Kyorin Pharmaceutical Co., Ltd., Sagami Chemical Research Center
    Inventors: Yasumichi Fukuda, Shigeki Seto, Yasuo Oomori, Hiroyuki Ebisu, Shiro Terashima
  • Patent number: 5786377
    Abstract: The pyrrolo?3,2-e! derivatives of the present invention have the formulae (I), (Ia) and (II) wherein R is substituted or unsubstituted aryl or heteroaryl, R' is substituted or unsubstituted alkanoyl, alkenoyl, alkynoyl, arenocarbonyl or heteroarenocarbonyl and X is chloro, bromo, iodo or alkylsulfonyl or arylsulfonyl. The compounds find utility as agents having antitumor activity, and are thus useful agents in the treatment of cancer.
    Type: Grant
    Filed: January 29, 1997
    Date of Patent: July 28, 1998
    Assignee: Universidad de Santiago de Compostela
    Inventors: Jose Delamano Garcia, Gabriel Tojo Suarez, Carmen Lopez Goti, Jesus Fernandez Almeida, Dolores Garcia Gravalos, Glynn Thomas Faircloth
  • Patent number: 5780493
    Abstract: The present patent application discloses compounds having formula (I) or a pharmaceutically acceptable salt thereof wherein R.sup.1 is hydrogen, alkyl or benzyl; X is O or NOR.sup.2, wherein R.sup.2 is hydrogen, alkyl or benzyl; Y is N--R.sup.4 wherein R.sup.4 is hydrogen, OH or alkyl; n is 0 or 1; R.sup.6 is phenyl, naphthyl, thienyl, pyridyl, all of which may be substituted one or more times with substituents selected from the group consisting of halogen; CF.sub.3, NO.sub.2, amino, alkyl, alkoxy and phenyl; A is a ring of five to seven atoms fused with the benzo ring at the positions marked a and b. The compounds are useful in the treatment of cerebrovascular disorders for example.
    Type: Grant
    Filed: October 16, 1997
    Date of Patent: July 14, 1998
    Assignee: NeuroSearch A/S
    Inventors: Frank Watjen, Jorgen Drejer
  • Patent number: 5760165
    Abstract: Monoallyloxyimides, diallyloxyimides and polyallyloxyimides of general Formula I. ##STR1## wherein: X is an integer from 1 to 4 inclusive;R.sup.1, R.sup.2, and R.sup.3 are independently selected from the group comprising hydrogen, alkyl, arylalkyl or halogen; andA is all or part of an aromatic, alicyclic or mixed aromatic/alicyclic ring system optionally substituted with one or more alkyl, alkoxy, alkylthio, aryl, heteroaryl, aryloxy, carboxy, alkylamino, dialkylamino, amino, nitro, cyano, halo or haloalkyl groups.This new class of reactive monomer can be used as co-reactants in themosetting matrix resins. The reactive monomers, either alone or with other comonomers, can give rise to cured resin matrix materials with high thermal stability. Mixed with suitable bismaleimide monomers, they can be cured into useful composites having substantially improved thermal stabilities.
    Type: Grant
    Filed: May 6, 1997
    Date of Patent: June 2, 1998
    Assignee: Commonwealth Scientific and Industrial Research Organization (CSIRO)
    Inventors: Buu Dao, Trevor Morton
  • Patent number: 5755875
    Abstract: Compounds selected from the series consisting of the perylenecarboximide, quinacridone, isoindoline, indigoid, azo, benzodipyrrolone, benzodifuranone, furanofuran, pyrrolo?2,5-b!pyrrole and bianthraquinone chromophores containing at least one grouping of formula ##STR1## wherein each A may be N--CN or O, with the proviso that at least one A must be N--CN, X is --N(R)--, --O-- or --S--, R is hydrogen, C.sub.1 -C.sub.18 alkyl, unsubstituted or halogen- or C.sub.1 -C.sub.4 alkyl-substituted phenyl, benzyl or phenethyl, and m and n are each independently of the other 0 or 1.Depending on the nature of their substituents, these compounds can be used as polymer-soluble dyes or as pigments for coloring high molecular weight organic material. They are distinguished by a surprisingly high solid-state fluorescence.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: May 26, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: John S. Zambounis, Zhimin Hao, Abul Iqbal
  • Patent number: 5739350
    Abstract: This invention provides some new synthetically obtained compounds of formula I and II ##STR1## which are useful as chemical intermediates. Representative formula I or II compounds have also been shown to possess useful ranges of antitumor activity in standard laboratory animal tests.In addition, the compounds of formula I or II can be linked to monoclonal antibodies, either directly or via known linking group, as a means of selectively delivering the CC-1065 analogs (Compounds of Formula I and II) to those target cells expressing the target antigen and thus selectively eliminating those diseased cells from the animal or human. Further, the compounds of formula I and II can be linked to soluble human CD4 or a soluble human CD4 protein fragment capable of binding to the gp120 envelope protein of the human immuno-virus and thus eliminate virally infected cells.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 14, 1998
    Assignee: Pharmacia & Upjohn Company
    Inventors: Robert C. Kelly, Mark A. Mitchell, Paul A. Aristoff
  • Patent number: 5710281
    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: January 20, 1998
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
  • Patent number: 5709947
    Abstract: A method for the preparation of a diaminobisimide compound of the formula (I) substantially free of oligomers: ##STR1## wherein Ar.sup.1 is an optionally substituted aromatic residue which provides for good conjugation between the nitrogen containing groups; andAr is an optionally substituted aromatic residue characterized in that at least two molar proportions of an aromatic diamine of the formula (II)H.sub.2 N--Ar.sup.1 --NH.sub.2 (II)wherein Ar.sup.1 is as defined above,are heated with one molar proportion of an aromatic tetracarboxylic acid of the formula (III) or the corresponding dianhydride,(HOOC).sub.2 Ar(COOH).sub.2 (III)wherein Ar is as defined above,optionally in the presence of a polar solvent and optionally including 0.1 to 2 molar proportions of a tertiary amine.The compounds of formula (I) are useful curing agents in epoxy resin formulations.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: January 20, 1998
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Jonathan Howard Hodgkin, Mervyn Benjamin Jackson, John West Loder
  • Patent number: 5693822
    Abstract: A method for the preparation of diaminobisimide compounds of the formula (I) which are substantially free of oligomers and are useful as curing agents in epoxy resin formulations: ##STR1## wherein Ar.sup.1 is an optionally substituted aromatic residue which provides for good conjugation between the nitrogen containing groups; and Ar is an optionally substituted aromatic residue, comprising heating an aromatic diamine of the formula H.sub.2 N--Ar.sup.1 --NH.sub.2, with an aromatic tetracarboxylic acid of the formula (HOOC).sub.2 (COOH).sub.2 or the corresponding dianhydride.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: December 2, 1997
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Jonathan Howard Hodgkin, Mervyn Benjamin Jackson, John West Loder
  • Patent number: 5693741
    Abstract: Low molecular weight resins that usually are aliphatic and that include crosslinking thermal functional groups are useful as liquid molding compounds for reaction injection molding or resin transfer molding. The compounds eliminate the need to handle solvents when preparing thermoset composites.
    Type: Grant
    Filed: March 15, 1988
    Date of Patent: December 2, 1997
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5681963
    Abstract: Fluorinated imides useful for imparting repellency of low surface tension fluids to thermoplastic polymers of formulae ##STR1## wherein R.sub.1 is F(CF.sub.2).sub.x --(CH.sub.2).sub.m, or F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5) (CH.sub.2) .sub.p wherein x is from about 4 to about 20, m is from about 2 to about 6, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.2 is a linear, branched or cyclic alkylene or poly(oxyalkylene) hydrocarbon group having from about 2 to about 15 carbons;R.sub.3 is selected from the group consisting of F(CF.sub.2).sub.x --(CH.sub.2).sub.m, F(CF.sub.2).sub.x --(CH.sub.2).sub.m --OC(O)--(CH.sub.2).sub.n, and F(CF.sub.2).sub.x SO.sub.2 N(R.sub.5)(CH.sub.2).sub.p OC(O)(CH.sub.2).sub.n wherein x is from about 4 to about 20, m is from about 2 to about 6, n is about 2 to about 12, p is from 1 to about 12, and R.sub.5 is an alkyl radical of from 1 to about 4 carbons;R.sub.4 is an alkyl or alkenyl group of from about 4 to about 20 carbons, andR.sub.
    Type: Grant
    Filed: December 21, 1995
    Date of Patent: October 28, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Theodor Arthur Liss
  • Patent number: 5670492
    Abstract: Provided are DC-89 derivatives represented by the formula: ##STR1## wherein X represents Cl or Br, R represents hydrogen or COR.sup.1, and W represents ##STR2## and pharmaceutically acceptable salts thereof. The compounds of the present invention have excellent anti-tumor activity and are useful as anti-tumor agents.
    Type: Grant
    Filed: November 28, 1995
    Date of Patent: September 23, 1997
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Nobuyoshi Amishiro, Satoru Nagamura, Hiromitsu Saito, Eiji Kobayashi, Akihiko Okamoto, Katsushige Gomi
  • Patent number: 5646298
    Abstract: The present invention describes cyclopropylindole cytotoxic prodrugs of formulas (I), (II) and (III) as shown in the specification. The present invention is also directed to a method for the site-specific treatment of neoplastic diseases in a mammal which method includes the following steps: (i) administering to an afflicted mammal an effective amount of a targeting agent- enzyme donor peptide conjugate wherein the targeting agent is selected from the group of antibodies, monoclonal antibodies, adhesion molecules and tumor cell surface binding ligands; (ii) administering to the afflicted mammal an effective amount of an enzyme acceptor dimer thereby forming active enzymatic sites at a tumor cell surface; and (iii) administering to the afflicted mammal a therapeutically effective amount of an enzyme-activateable, cytotoxic pro-drug thereby releasing the cytotoxic drug at the tumor site.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 8, 1997
    Assignee: ProCoron, Inc.
    Inventor: Michael J. Powell
  • Patent number: 5641780
    Abstract: DC-89 derivatives represented by the formula ##STR1## wherein X represents CL or Br; R represents substituted or unsubstituted alkyl, substituted or unsubstituted aralkyl, COR.sup.1 or S.sub.2 OR.sup.7 ; and Y represents ##STR2## and pharmaceutically acceptable salts thereof. The compounds of the present invention exhibit excellent anti-tumor activity and are useful as anti-tumor agents.
    Type: Grant
    Filed: December 15, 1995
    Date of Patent: June 24, 1997
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Nobuyoshi Amishiro, Satoru Nagamura, Hiromitsu Saito, Eiji Kobayashi, Akihiko Okamoto, Katsushige Gomi
  • Patent number: 5631384
    Abstract: The compounds (I) are useful as intermediates in the synthesis of hexahydroareno(e)cyclopropa(c)indol-4-ones with antitumoral activity.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: May 20, 1997
    Assignee: Pharma-Mar, S.A.-Pharmar
    Inventors: Koen Alexander, Jose Delamano Garcia, Benedikt Sas, Gabriel Tojo Suarez, Dolores Garcia Gravalos
  • Patent number: 5629430
    Abstract: Trifluoromethylpyrroloindolecarboxylic acid ester derivatives, and optical isomers and pharmaceutically acceptable salts thereof are provided which are represented by the general formula (1): ##STR1## or the general formula (2): ##STR2## The compounds are antineoplastic agents which are selective to cancer cells, effective also to solid cancer, and less toxic.
    Type: Grant
    Filed: June 14, 1995
    Date of Patent: May 13, 1997
    Assignees: Kyorin Pharmaceutical Co., Ltd., Sagami Chemical Research Center
    Inventors: Shiro Terashima, Yasumichi Fukuda, Yasuo Oomori
  • Patent number: 5585499
    Abstract: Novel cytotoxic agents comprising a cell binding agent chemically linked to one or more analogue or derivative of CC-1065 are described. The therapeutic use of the cytotoxic agents is also described. These cytotoxic agents have therapeutic use because they deliver the cytotoxic drugs to a specific cell population in a targeted fashion.
    Type: Grant
    Filed: July 6, 1995
    Date of Patent: December 17, 1996
    Assignee: Immunogen Inc.
    Inventors: Ravi V. J. Chari, Viktor S. Goldmakher, Walter A. Blattler
  • Patent number: 5571927
    Abstract: The areno[e]indols have the formula (I). The methods comprises: (a) reacting (VI) with an aldehyde Ar"--CHO to obtain (VII); (b) oxidizing (VII) to yield the cetone (VIII); (c) reating (VIII) with a strong base and thereafter with an acycle chloride ClCOR, to produce (IX); (d) subjecting to a photochemical cyclization (IX) to produce (I). In said formulas Ar is phenyl or substituted phenyl; Ar' is radical (i) or (ii); R is an acyle group, Ar" is a phenyl, pyrolyl, furanyl or thiophenyl group substituted up to three times by any of the radials R, R.sup.1, R.sup.2, or R.sup.3. The compounds (I) are useful as intermediates in the synthesis of hexahydroareno(e)cyclopropa(c)indol-4-ones with antitumoral activity.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: November 5, 1996
    Assignee: Pharma-Mar, S.A.- Pharmar
    Inventors: Koen Alexander, Jose Delamano Garcia, Benedikt Sas, Gabriel Tojo Suarez, Dolores Garcia Gravalos
  • Patent number: 5563273
    Abstract: An electrochemical color change cell incorporating as a color changing agent intramolecular charge transfer salt or an intermolecular charge transfer salt. The intermolecular charge transfer salts and the intramolecular charge transfer salts have a plurality of oxidation states and a wide variation in color change. The intermolecular and intramolecular charge transfer salts preferably contain a violene moiety and a moiety having a carbonyl group conjugated to an aromatic moiety. The intramolecular charge transfer salts have a stable covalent radical-anion/radical-cation configuration. The intermolecular charge transfer salts have a stable ionic radical-anion/radical-cation configuration.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: October 8, 1996
    Assignee: International Business Machines Corporation
    Inventors: Stephen L. Buchwalter, Martin J. Goldberg, Revathi Iyengar, Terrence R. O'Toole, Alfred Viehbeck
  • Patent number: 5541339
    Abstract: This invention concerns chemical compounds of general Formula ICPI.sub.1 -R.sub.5 -T-R'.sub.5 -CPI.sub.2 IThe compounds of Formula I are useful as uv light absorbers, antibacterial agents, and are particularly useful as antitumor agents. Representative compounds of Formula I have been shown to possess useful ranges of antitumor activity in standard laboratory animal tests.
    Type: Grant
    Filed: March 8, 1991
    Date of Patent: July 30, 1996
    Assignee: The Upjohn Company
    Inventors: Robert C. Kelly, Paul A. Aristoff
  • Patent number: 5475092
    Abstract: Novel cytotoxic agents comprising a cell binding agent chemically linked to one or more analogue or derivative of CC-1065 are described. The therapeutic use of the cytotoxic agents is also described. These cytotoxic agents have therapeutic use because they deliver the cytotoxic drugs to a specific cell population in a targeted fashion.
    Type: Grant
    Filed: March 21, 1994
    Date of Patent: December 12, 1995
    Assignee: Immunogen Inc.
    Inventors: Ravi V. J. Chari, Viktor S. Goldmakher, Walter A. Blattler
  • Patent number: 5414013
    Abstract: Compounds of the formula ##STR1## wherein Z is ##STR2## proline, pipecolic acid, an indolecarboxylic acid or an isoquinolinecarboxylic acid. These compounds are useful as cardiovascular agents.
    Type: Grant
    Filed: March 26, 1993
    Date of Patent: May 9, 1995
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Norma G. Delaney, George C. Rovnyak, Melanie J. Loots
  • Patent number: 5332837
    Abstract: This invention concerns 2-acyl-4,5,8,8a-tetrahydro-4-oxycyclopropan[c]pyrrol(3,2-e) indole derivatives of Formula I': ##STR1## the compounds of Formula I' are useful as uv light absorber substances, as chemical intermediates and as prodrugs of known spirocyclopropylpyrroloindole CC-1065 analogs. Representative Formula I' compounds have been shown to possess useful ranges of antitumor activity in standard laboratory animal tests.
    Type: Grant
    Filed: January 22, 1993
    Date of Patent: July 26, 1994
    Assignee: The Upjohn Company
    Inventors: Robert C. Kelly, David G. Martin, Paul A. Aristoff
  • Patent number: 5292765
    Abstract: A method for reducing adverse effects of neurotoxic injury, which comprises administering to a patient susceptible to neurotoxic injury an effective amount, sufficient to reduce the injury, of a compound having an indolactam V ring system. Particularly preferred are compounds having ring stereochemistry as indicated in the following formula: ##STR1## The indicated substituents show preferred locations of substituents; preferred substituents are defined in the specification.
    Type: Grant
    Filed: November 27, 1991
    Date of Patent: March 8, 1994
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Dennis W. Choi, Dean M. Hartley
  • Patent number: 5258383
    Abstract: DC-89 derivatives represented by the formula: ##STR1## wherein X represents hydrogen or CO.sub.2 CH.sub.3 ; and ##STR2## wherein Z represents Cl or Br; R represents hydrogen, CONR.sup.1 R.sup.2 (in which R.sup.1 and R.sup.2 independently represent hydrogen, a straight-chain or branched alkyl group having 1 to 4 carbon atoms or phenyl) or ##STR3## (in which n represents an integer of 0 to 4; R.sup.3 represents CH.sub.2, ##STR4## oxygen, N--CH.sub.3, or N--CH.sub.2 CONR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 have the same significances as defined above); and W represents hydrogen or ##STR5## (in which W.sup.1 and W.sup.2 independently represent hydrogen or OR.sup.2 in which R.sup.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: November 2, 1993
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Satoru Nagamura, Hiromitsu Saito, Eiji Kobayashi, Katsushige Gomi
  • Patent number: 5252560
    Abstract: Compounds are described of the formula ##STR1## wherein: R.sup.1 is C.sub.3-6 alkyl or C.sub.1-3 alkylthioC.sub.1-3 alkyl;R.sup.2 is an optionally substituted C.sub.1-6 alkyl or C.sub.1-6 alkoxy group, aryl, heteroaryl, arylC.sub.1-4 alkyl, heteroarylC.sub.1-4 alkyl or a side-chain of a natural .alpha.-amino acid;R.sup.3 is hydrogen, C.sub.1-6 alkyl, CHR.sup.4 COR.sup.5 (where R.sup.4 is a side-chain of a natural .alpha.-amino acid and R.sup.5 is hydroxyl, C.sub.1-6 alkoxy or NHR.sup.6 where R.sup.6 represents a hydrogen atom or a C.sub.1-6 alkyl group) or a group (CH.sub.2).sub.n X (where n is 1 to 6 and X is hydroxyl, C.sub.1-4 alkoxy, heteroaryl or a group NR.sup.7 R.sup.8 where R.sup.7 and R.sup.8 are each hydrogen or C.sub.1-6 alkyl or the group NR.sup.7 R.sup.
    Type: Grant
    Filed: June 29, 1992
    Date of Patent: October 12, 1993
    Assignee: Glaxo Inc.
    Inventors: Peter L. Myers, Andrew B. McElroy, Michael Gregson, Peter J. Brown, Howard G. Davies, David H. Drewry, Michael A. Foley
  • Patent number: 5242551
    Abstract: A method of isomerizing an isoimide to an n-imide is described wherein an electron is supplied to the isoimide which induces the isomerization and wherein the isomerization is catalytic to the electron which remains available to initiate further isomerization. A polyimide is deposited onto a conductive substrate by providing a composition containing a polyisoimide and an electrolyte providing the substrate and a counter electrode in the composition, and providing a bias between the substrate and counter electrode to thereby supply an electron to the polyisoimide which isomerizes to deposit the insoluble polyimide on the substrate.
    Type: Grant
    Filed: October 3, 1991
    Date of Patent: September 7, 1993
    Assignee: International Business Machines Corporation
    Inventors: Ernest R. Frank, Terrence R. O'Toole, Alfred Viehbeck
  • Patent number: 5216173
    Abstract: Polyfunctional N-cyanoimides and their precursors and derivatives are disclosed along with methods for their preparation and interconversion. Also disclosed are curable compositions comprising the N-cyanoimides or poly(amide-cyanoamides) and reactive diluents as well as novel dianhydrides, polyimides, and poly(amide-cyanoamides) and methods for making them.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: June 1, 1993
    Assignee: Henkel Research Corporation
    Inventors: Randall Stephens, Linda A. Domeier
  • Patent number: 5210213
    Abstract: Multidimensional oligomers of the present invention are surprisingly useful for advanced composites because each generally has a use temperature greatly in excess of its curing temperature. The oligomers have essentially no arms, and comprise crosslinking phenylimide end caps condensed directly onto an aromatic hub (preferably, phenyl) through "commodity" polymeric linkages, such as amide, diimide, ether, or ester. For example, p-nadicimidobenzoylchloride can be condensed with triaminobenzene to yield a multidimensional, crosslinking amide oligomer. Short chains of ether/carbonyl aromatic chains can be included, if desired. Methods for making these high-performance oligomers with ether/carbonyl aromatic chains use an Ullmann ether synthesis followed by a Friedel Craft reaction.
    Type: Grant
    Filed: January 5, 1987
    Date of Patent: May 11, 1993
    Assignee: The Boeing Company
    Inventors: Clyde H. Sheppard, Hyman R. Lubowitz
  • Patent number: 5138059
    Abstract: Novel DC-89 compounds represented by the general formula: ##STR1## wherein X represents a single bond or --CH.sub.2 --; and when X represents a single bond, Y represents --CH.sub.2 Br or --CH.sub.2 Cl and when X represents --CH.sub.2 --, Y represents Br, are obtained by the present invention. The compounds have antibacterial and anti-tumor activity.
    Type: Grant
    Filed: July 17, 1989
    Date of Patent: August 11, 1992
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Keiichi Takahashi, Michio Ichimura, Shigeo Katsumata, Tatsuhiro Ogawa, Makoto Morimoto, Tadashi Ashizawa, Masaji Kasai, Kenichi Muroi, Hiromitsu Saito, Hiroshi Sano, Toru Yasuzawa
  • Patent number: 5132396
    Abstract: Highly aromatic oligomeric imide-containing phthalonitriles are prepared by reacting an aromatic dianhydride with an aromatic or aliphatic diamine and endcapping the resulting reaction product with 4-aminophthalonitrile. The prepolymers are highly stable to storage. When heated above their melting or softening points, they polymerize to a thermosetting polymeric material useful as an advanced matrix material. In the case where the oligomeric monomers are produced by reacting dianhydrides with aromatic diamines, they polymerize to form high-temperature adhesives.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: July 21, 1992
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventor: Teddy M. Keller
  • Patent number: 5108485
    Abstract: There are provided o-carboxy-(5-oxo-2-imidazolin-2-yl)benzoheterocyclic compounds wherein the fused heterocyclic ring system is a 5-membered ring containing one, two or three nitrogen atoms, derivatives of said benzoheterocyclic compounds and a method for the use therewith to control monocotyledonous and dicotyledonous plant species.
    Type: Grant
    Filed: August 31, 1990
    Date of Patent: April 28, 1992
    Assignee: American Cyanamid Company
    Inventor: Robert F. Doehner, Jr.
  • Patent number: 5089517
    Abstract: A method for reducing adverse effects of neurotoxic injury, which comprises administering to a patient susceptible to neurotoxic injury an effective amount, sufficient to reduce the injury, of a compound having an indolactam V ring system. Particularly preferred are compounds having ring stereochemistry as indicated in the following formula: ##STR1## The indicated substituents show preferred locations of substituents; preferred substituents are defined in the specification.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: February 18, 1992
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Dennis W. Choi, Dean M. Hartley
  • Patent number: 5084468
    Abstract: A novel DC-88A derivative represented by general formula: ##STR1## wherein ##STR2## represents ##STR3## has an excellent antitumor activity and is useful as an antitumor agent.
    Type: Grant
    Filed: August 10, 1989
    Date of Patent: January 28, 1992
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Hiromitsu Saito, Masaji Kasai, Makoto Morimoto, Eiji Kobayashi, Yoichi Uosaki, Yutaka Kanda, Hiroshi Sano
  • Patent number: 5070092
    Abstract: DC-88A derivatives represented by the general formula: ##STR1## wherein X represents hydrogen or CO.sub.2 R.sup.1 (in which R.sup.1 represents hydrogen, a straight-chain or branched alkyl having 1 to 4 carbon atoms, allyl, or benzyl); and ##STR2## have an excellent anti-tumor activity and are useful as anti-tumor agents.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: December 3, 1991
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Yutaka Kanda, Youichi Uosaki, Hiromitsu Saito, Hiroshi Sano, Eiji Kobayashi, Makoto Morimoto, Satoru Nagamura
  • Patent number: 5037993
    Abstract: Novel substances exhibiting antimicrobial activity and antitumor activity, a process for producing them by cultivating a microorganism belonging to the genus Streptomyces and capable of producing them and derivatives of such substances.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: August 6, 1991
    Assignee: Meiji Seika Kaisha Ltd.
    Inventors: Kazunori Ohba, Masaji Sezaki, Shinichi Kondo, Masao Koyama, Tadashi Nakazawa, Haruo Yamamoto