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)
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Patent number: 6534657Abstract: 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: GrantFiled: February 9, 2001Date of Patent: March 18, 2003Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Patent number: 6268391Abstract: 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: GrantFiled: April 7, 2000Date of Patent: July 31, 2001Assignee: 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
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Patent number: 6201129Abstract: 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: GrantFiled: August 1, 1997Date of Patent: March 13, 2001Assignee: Univ. College Cardiff ConsultantsInventors: David Drysdale Miller, Patrick Vivian Richard Shannon, Laddawan Chuncharprasert
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Patent number: 6162822Abstract: 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: GrantFiled: December 28, 1998Date of Patent: December 19, 2000Assignee: Adir et CompagnieInventors: Gilbert Lavielle, Patrick Hautefaye, Ghanem Atassi, Alain Pierre, Laurence Kraus-Berthier, Stephane Leonce
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Patent number: 6153764Abstract: 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: GrantFiled: January 25, 2000Date of Patent: November 28, 2000Assignee: Bayer CorporationInventors: Gregory R. Schulz, Michael J. Greene
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Patent number: 6130237Abstract: 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: GrantFiled: March 12, 1999Date of Patent: October 10, 2000Assignee: Cancer Research Campaign Technology LimitedInventors: William A. Denny, Moana Tercel, Graham J. Atwell
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Patent number: 6114419Abstract: 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: GrantFiled: April 7, 1998Date of Patent: September 5, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Theodor Arthur Liss, Kimberly Gheysen Raiford, Edward James Greenwood
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Patent number: 6080859Abstract: 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: GrantFiled: July 19, 1999Date of Patent: June 27, 2000Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Yasumichi Fukuda, Rumiko Shimazawa, Yasuo Oomori, Shiro Terashima
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Patent number: 6066742Abstract: 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: GrantFiled: March 9, 1999Date of Patent: May 23, 2000Assignees: Kyorin Pharmaceutical Co., Ltd., Sagami Chemical Research CenterInventors: Yasumichi Fukuda, Shiro Terashima
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Patent number: 6018055Abstract: 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: GrantFiled: July 15, 1997Date of Patent: January 25, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Kil-Yeong Choi, Dong-Hack Suh, Young-Taik Hong, Eun-Young Chung
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Patent number: 5917053Abstract: 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: GrantFiled: May 20, 1997Date of Patent: June 29, 1999Assignee: Neurosearch A/SInventors: Peter Moldt, Frank Watjen
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Patent number: 5843937Abstract: 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: GrantFiled: May 23, 1996Date of Patent: December 1, 1998Assignee: Panorama Research, Inc.Inventors: Yuqiang Wang, Susan C. Wright, James W. Larrick
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Patent number: 5801174Abstract: 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: GrantFiled: May 20, 1997Date of Patent: September 1, 1998Assignee: Neurosearch A/SInventors: Peter Moldt, Frank Watjen
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Patent number: 5789491Abstract: 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: GrantFiled: June 19, 1997Date of Patent: August 4, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Theodor Arthur Liss, Kimberly Gheysen Raiford, Edward James Greenwood
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Patent number: 5786486Abstract: 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: GrantFiled: May 13, 1997Date of Patent: July 28, 1998Assignees: Kyorin Pharmaceutical Co., Ltd., Sagami Chemical Research CenterInventors: Yasumichi Fukuda, Shigeki Seto, Yasuo Oomori, Hiroyuki Ebisu, Shiro Terashima
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Patent number: 5786377Abstract: 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: GrantFiled: January 29, 1997Date of Patent: July 28, 1998Assignee: Universidad de Santiago de CompostelaInventors: Jose Delamano Garcia, Gabriel Tojo Suarez, Carmen Lopez Goti, Jesus Fernandez Almeida, Dolores Garcia Gravalos, Glynn Thomas Faircloth
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Patent number: 5780493Abstract: 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: GrantFiled: October 16, 1997Date of Patent: July 14, 1998Assignee: NeuroSearch A/SInventors: Frank Watjen, Jorgen Drejer
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Patent number: 5760165Abstract: 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: GrantFiled: May 6, 1997Date of Patent: June 2, 1998Assignee: Commonwealth Scientific and Industrial Research Organization (CSIRO)Inventors: Buu Dao, Trevor Morton
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Patent number: 5755875Abstract: 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: GrantFiled: March 22, 1996Date of Patent: May 26, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: John S. Zambounis, Zhimin Hao, Abul Iqbal
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Patent number: 5739350Abstract: 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: GrantFiled: June 7, 1995Date of Patent: April 14, 1998Assignee: Pharmacia & Upjohn CompanyInventors: Robert C. Kelly, Mark A. Mitchell, Paul A. Aristoff
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Patent number: 5710281Abstract: 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: January 20, 1998Assignee: Minnesota Mining and Manufacturing CompanyInventors: Ernest L. Thurber, Eric G. Larson, Alan R. Kirk, Gregg D. Dahlke
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Patent number: 5709947Abstract: 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: GrantFiled: June 2, 1995Date of Patent: January 20, 1998Assignee: Commonwealth Scientific and Industrial Research OrganisationInventors: Jonathan Howard Hodgkin, Mervyn Benjamin Jackson, John West Loder
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Patent number: 5693822Abstract: 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: GrantFiled: January 11, 1996Date of Patent: December 2, 1997Assignee: Commonwealth Scientific and Industrial Research OrganisationInventors: Jonathan Howard Hodgkin, Mervyn Benjamin Jackson, John West Loder
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Patent number: 5693741Abstract: 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: GrantFiled: March 15, 1988Date of Patent: December 2, 1997Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5681963Abstract: 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: GrantFiled: December 21, 1995Date of Patent: October 28, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventor: Theodor Arthur Liss
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Patent number: 5670492Abstract: 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: GrantFiled: November 28, 1995Date of Patent: September 23, 1997Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Nobuyoshi Amishiro, Satoru Nagamura, Hiromitsu Saito, Eiji Kobayashi, Akihiko Okamoto, Katsushige Gomi
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Patent number: 5646298Abstract: 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: GrantFiled: June 7, 1995Date of Patent: July 8, 1997Assignee: ProCoron, Inc.Inventor: Michael J. Powell
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Patent number: 5641780Abstract: 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: GrantFiled: December 15, 1995Date of Patent: June 24, 1997Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Nobuyoshi Amishiro, Satoru Nagamura, Hiromitsu Saito, Eiji Kobayashi, Akihiko Okamoto, Katsushige Gomi
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Patent number: 5631384Abstract: The compounds (I) are useful as intermediates in the synthesis of hexahydroareno(e)cyclopropa(c)indol-4-ones with antitumoral activity.Type: GrantFiled: July 3, 1996Date of Patent: May 20, 1997Assignee: Pharma-Mar, S.A.-PharmarInventors: Koen Alexander, Jose Delamano Garcia, Benedikt Sas, Gabriel Tojo Suarez, Dolores Garcia Gravalos
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Patent number: 5629430Abstract: 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: GrantFiled: June 14, 1995Date of Patent: May 13, 1997Assignees: Kyorin Pharmaceutical Co., Ltd., Sagami Chemical Research CenterInventors: Shiro Terashima, Yasumichi Fukuda, Yasuo Oomori
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Patent number: 5585499Abstract: 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: GrantFiled: July 6, 1995Date of Patent: December 17, 1996Assignee: Immunogen Inc.Inventors: Ravi V. J. Chari, Viktor S. Goldmakher, Walter A. Blattler
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Patent number: 5571927Abstract: 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: GrantFiled: May 19, 1994Date of Patent: November 5, 1996Assignee: Pharma-Mar, S.A.- PharmarInventors: Koen Alexander, Jose Delamano Garcia, Benedikt Sas, Gabriel Tojo Suarez, Dolores Garcia Gravalos
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Patent number: 5563273Abstract: 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: GrantFiled: February 9, 1994Date of Patent: October 8, 1996Assignee: International Business Machines CorporationInventors: Stephen L. Buchwalter, Martin J. Goldberg, Revathi Iyengar, Terrence R. O'Toole, Alfred Viehbeck
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Patent number: 5541339Abstract: 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: GrantFiled: March 8, 1991Date of Patent: July 30, 1996Assignee: The Upjohn CompanyInventors: Robert C. Kelly, Paul A. Aristoff
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Patent number: 5475092Abstract: 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: GrantFiled: March 21, 1994Date of Patent: December 12, 1995Assignee: Immunogen Inc.Inventors: Ravi V. J. Chari, Viktor S. Goldmakher, Walter A. Blattler
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Patent number: 5414013Abstract: 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: GrantFiled: March 26, 1993Date of Patent: May 9, 1995Assignee: E. R. Squibb & Sons, Inc.Inventors: Norma G. Delaney, George C. Rovnyak, Melanie J. Loots
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Patent number: 5332837Abstract: 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: GrantFiled: January 22, 1993Date of Patent: July 26, 1994Assignee: The Upjohn CompanyInventors: Robert C. Kelly, David G. Martin, Paul A. Aristoff
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Patent number: 5292765Abstract: 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: GrantFiled: November 27, 1991Date of Patent: March 8, 1994Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Dennis W. Choi, Dean M. Hartley
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Patent number: 5258383Abstract: 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: GrantFiled: June 25, 1992Date of Patent: November 2, 1993Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Satoru Nagamura, Hiromitsu Saito, Eiji Kobayashi, Katsushige Gomi
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Patent number: 5252560Abstract: 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: GrantFiled: June 29, 1992Date of Patent: October 12, 1993Assignee: Glaxo Inc.Inventors: Peter L. Myers, Andrew B. McElroy, Michael Gregson, Peter J. Brown, Howard G. Davies, David H. Drewry, Michael A. Foley
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Patent number: 5242551Abstract: 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: GrantFiled: October 3, 1991Date of Patent: September 7, 1993Assignee: International Business Machines CorporationInventors: Ernest R. Frank, Terrence R. O'Toole, Alfred Viehbeck
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Patent number: 5216173Abstract: 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: GrantFiled: July 23, 1990Date of Patent: June 1, 1993Assignee: Henkel Research CorporationInventors: Randall Stephens, Linda A. Domeier
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Patent number: 5210213Abstract: 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: GrantFiled: January 5, 1987Date of Patent: May 11, 1993Assignee: The Boeing CompanyInventors: Clyde H. Sheppard, Hyman R. Lubowitz
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Patent number: 5138059Abstract: 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: GrantFiled: July 17, 1989Date of Patent: August 11, 1992Assignee: 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
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Patent number: 5132396Abstract: 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: GrantFiled: April 30, 1990Date of Patent: July 21, 1992Assignee: The United States of America as represented by the Secretary of the NavyInventor: Teddy M. Keller
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Patent number: 5108485Abstract: 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: GrantFiled: August 31, 1990Date of Patent: April 28, 1992Assignee: American Cyanamid CompanyInventor: Robert F. Doehner, Jr.
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Patent number: 5089517Abstract: 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: GrantFiled: August 3, 1990Date of Patent: February 18, 1992Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Dennis W. Choi, Dean M. Hartley
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Patent number: 5084468Abstract: 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: GrantFiled: August 10, 1989Date of Patent: January 28, 1992Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Hiromitsu Saito, Masaji Kasai, Makoto Morimoto, Eiji Kobayashi, Yoichi Uosaki, Yutaka Kanda, Hiroshi Sano
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Patent number: 5070092Abstract: 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: GrantFiled: June 29, 1990Date of Patent: December 3, 1991Assignee: Kyowa Hakko Kogyo Co., Ltd.Inventors: Yutaka Kanda, Youichi Uosaki, Hiromitsu Saito, Hiroshi Sano, Eiji Kobayashi, Makoto Morimoto, Satoru Nagamura
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Patent number: 5037993Abstract: 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: GrantFiled: May 8, 1990Date of Patent: August 6, 1991Assignee: Meiji Seika Kaisha Ltd.Inventors: Kazunori Ohba, Masaji Sezaki, Shinichi Kondo, Masao Koyama, Tadashi Nakazawa, Haruo Yamamoto