Oxygen Bonded Directly At Alpha Position (i.e., 1-, 4-, 5-, Or 8-position) Patents (Class 552/262)
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Publication number: 20140056834Abstract: A novel use of chrysophanol for skin whitening is provided, in which chrysophanol is included in a cosmetic composition as an effective ingredient for skin whitening. The chrysophanol compound has excellent stability and can also effectively inhibit melanin production via mechanism of inhibiting expression and activity of tyrosinase.Type: ApplicationFiled: October 31, 2012Publication date: February 27, 2014Applicant: Pukyong National University Industry-University Cooperation FoundationInventors: Se-Kwon KIM, Wijesekara Liyanae Isuru WIJESEKARA
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Publication number: 20130288989Abstract: Use of chemical ingredients in Cynomorium as phytoestrogen is provided by the present invention. Particularly, use of Cynomorium, extracts of Cynomorium, or at least one ingredient chosen from chrysophanol, emodin, catechin, (?)-epicatechin-3-O-gallate, naringenin-4?-O-glucopyranoside, and phlorizin, in manufacturing medicaments for treating and/or preventing diseases related to insufficient of estrogen secretion in mammal (for example, human), or use in manufacturing medicaments used as phytoestrogens is provided by the present invention. The extracts of Cynomorium, compositions containing extracts of Cynomorium or active ingredients thereof, and methods of treating and/or preventing diseases related to insufficient of estrogen secretion are also provided by the present invention.Type: ApplicationFiled: October 14, 2010Publication date: October 31, 2013Applicant: TIANJIN UNIVERSITY OF TRADITIONAL CHINESE MEDICINEInventor: Xiumei Gao
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Patent number: 8324411Abstract: The invention concerns a new process for the preparation of high purity diacerein, by oxidization of the protected aloe-emodin in the presence of an oxidizing system and radical catalyst and subsequent substitution of the protector groups with acetyl groups.Type: GrantFiled: December 19, 2008Date of Patent: December 4, 2012Assignee: Laboratorio Chimico Internazionale S.p.A.Inventors: Annibale Salvi, Antonio Nardi, Stefano Maiorana, Mara Sada
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Patent number: 8273906Abstract: It is intended to provide a method for producing aglycone from a glycoside efficiently at low cost without using an acid catalyst or an organic solvent. The method for producing aglycone, characterized by bringing a glycoside into contact with high temperature high pressure water. The temperature of the high temperature high pressure water is generally from 100 to 374° C., preferably from 140 to 320° C., more preferably from 200 to 300° C. The pressure of the high temperature high pressure water may be not lower than the saturated water vapor pressure at the temperature, i.e., a pressure at which the liquid state is maintained.Type: GrantFiled: June 13, 2008Date of Patent: September 25, 2012Assignee: J-Oil Mills, Inc.Inventors: Yosuke Isobe, Shuichi Kamo, Toshiro Sato, Hiroyuki Yoshida
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Publication number: 20110015269Abstract: The invention concerns a new process for the preparation of high purity diacerein, by oxidisation of the protected aloe-emodin in the presence of an oxidising system and radical catalyst and subsequent substitution of the protector groups with acetyl groups.Type: ApplicationFiled: December 19, 2008Publication date: January 20, 2011Inventors: Annibale Salvi, Antonio Nardi, Stefano Maiorana, Mara Sada
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Publication number: 20090312437Abstract: Compositions derived from Rheum palmatum are provided. Also provided are methods of using said extracts to induce apoptosis in specific cells, especially in a human.Type: ApplicationFiled: June 5, 2009Publication date: December 17, 2009Inventor: Isaac Cohen
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Publication number: 20080168608Abstract: The subject of the present invention is the use, for dyeing in particular human keratin materials, of a specific direct anthraquinone dye by dry thermal transfer. Its subject is furthermore a method for dyeing keratin materials, in which at least one direct anthraquinone dye contained in a dry composition is applied to or close to the keratin materials, and a source of heat is applied, causing the thermal transfer of the direct dye(s) at the surface and/or inside the keratin materials. It relates furthermore to the dry composition and a method for preparing it.Type: ApplicationFiled: February 28, 2006Publication date: July 17, 2008Inventors: Gregory Plos, Luc Gourlaouen, Jean-Dominique Bazin De Bezons
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Patent number: 7132403Abstract: Anthraquinones are described which are antihelminthic and in particular, are useful in compositions for inhibiting Schistosoma sp. in vitro or in vivo. The preferred anthraquinones have the formula: wherein R1, R2, R3, and R4 are each hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, or combination thereof, R is a group containing 1 to 12 carbons such as methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, or combination thereof, and the halogen is I, F, Br, or Cl.Type: GrantFiled: January 20, 2004Date of Patent: November 7, 2006Assignees: Board of Trustees of Michigan State University, Regents of the University of CaliforniaInventors: Robert H. Cichewicz, Muraleedharan G. Nair, James H. McKerrow
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Patent number: 6903076Abstract: Anthraquinones are described which are antihelminthic and in particular, are useful in compositions for inhibiting Schistosoma sp. in vitro or in vivo. The preferred anthraquinones have the formula: wherein R1, R2, R3, and R4 are each hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, or combination thereof, R is a group containing 1 to 12 carbons such as methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, or combination thereof, and the halogen is I, F, Br, or Cl.Type: GrantFiled: November 26, 2003Date of Patent: June 7, 2005Assignees: Board of Trustees of Michigan State University, The Regents of the University of CaliforniaInventors: Robert H. Cichewicz, Muraleedharan G. Nair, James H. McKerrow
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Patent number: 6875746Abstract: Anthraquinones are described which have anticancer or antitumor activity and which are useful for inhibiting cancer cells and cells comprising tumors in vitro or in vivo. Preferably, the anthraquinones have the chemical formula: wherein R1 is selected from the group consisting of hydrogen, alkyl, and substituted alkyl; R2 is a group containing 1-12 carbons selected from the group consisting of alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate and combinations thereof; and R3 is a group containing 1 to 12 carbons selected from the group consisting of methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, and combinations thereof.Type: GrantFiled: January 31, 2003Date of Patent: April 5, 2005Assignee: Board of Trustees of Michigan State UniversityInventors: Muraleedharan G. Nair, Robert H. Cichewicz, Navindra P. Seeram, Yanjun Zhang
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Patent number: 6838443Abstract: Anthraquinones are described which are antihelminthic and in particular, are useful in compositions for inhibiting Schistosoma sp. in vitro or in vivo. The preferred anthraquinones have the formula: wherein R1, R2, R3, and R4 are each hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, or combination thereof, R is a group containing 1 to 12 carbons such as methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, or combination thereof, and the halogen is I, F, Br, or Cl.Type: GrantFiled: November 26, 2003Date of Patent: January 4, 2005Assignees: Board of Trustees of Michigan State University, The Regents of the University of California, The United States of America as represented by the Department of Veterans AffairsInventors: Robert H. Cichewicz, Muraleedharan G. Nair, James H. McKerrow
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Patent number: 6800615Abstract: Anthraquinones are described which are antihelminthic and in particular, are useful in compositions for inhibiting Schistosoma sp. in vitro or in vivo. The preferred anthraquinones have the formula: wherein R1, R2, R3, and R4 are each hydrogen, hydroxy, halogen, alkyl, substituted alkyl, alkene, substituted alkene, alkyne, aryl, substituted aryl, cyclic, substituted cyclic, acid group, carbohydrate, or combination thereof, R is a group containing 1 to 12 carbons such as methyl, alkyl, substituted alkyl, aldehyde, hydroxy, hydroxymethyl, acid group, carbohydrate, or combination thereof, and the halogen is I, F, Br, or Cl.Type: GrantFiled: December 12, 2002Date of Patent: October 5, 2004Assignees: Board of Trustees of Michigan State University, The Regent of the University of California, The United States of America as represented by the Department of Veterans AffairsInventors: Robert H. Cichewicz, Muraleedharan G. Nair, James H. McKerrow
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Patent number: 6624192Abstract: The present invention provides a process for obtaining diacetylrhein, wherein diacetylrhein containing aloe-emodin components is subjected to a liquid—liquid partitioning between a polar organic solvent which is only partly miscible with water and an aqueous phase of pH 6.5 to 7.5 and the diacetylrhein is recovered and optionally recrystallized. The present invention is also concerned with diacetylrhein obtainable by this process and with pharmaceutical compositions containing it.Type: GrantFiled: November 2, 1994Date of Patent: September 23, 2003Assignee: Madaus AGInventors: Alfons Carcasona, Wolf Grimminger, Pentti Hêitala, Klaus Witthohn, Helga Zaeske
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Patent number: 6596764Abstract: The present invention provides a process for treating arthritis utilizing substantially pure diacetylrhein having an aloe-emodin content of less than 20 ppm.Type: GrantFiled: November 10, 1994Date of Patent: July 22, 2003Assignee: Laboratoire Medidom S.A.Inventors: Alfons Carcasona, Wolf Grimminger, Pentti Hietala, Helga Zaeske, Klaus Witthohn
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Patent number: 6057461Abstract: The invention relates to a process for the preparation of substituted anthraquinones represented by the general formula (I): ##STR1## by Diels-Alder reaction between a 1,4-naphthoquinone of general formula (II): ##STR2## and an acyclic diene of formula (III):CH.sub.2 .dbd.CR--CH.dbd.CH--OR.sub.3 (III)followed by an oxidizing deprotection reaction by means of the Jones reagent, in order to obtain the substituted anthraquinone of general formula (I).Application to the preparation of rheins of use in pharmaceuticals.Type: GrantFiled: October 2, 1998Date of Patent: May 2, 2000Assignee: GirexInventors: Cyril Estanove, Fran.cedilla.ois Pruvost
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Patent number: 5948924Abstract: A process for the preparation of substituted anthraquinones is provided. The anthraquinones can be used to prepare pharmaceutically useful rheins.Type: GrantFiled: July 1, 1997Date of Patent: September 7, 1999Assignee: Girex (Societe Anonyme)Inventors: Cyril Estanove, Fran.cedilla.ois Pruvost
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Patent number: 5756782Abstract: The present invention discloses a method for preparing purified diacetylrhein to be used in the preparation of drugs which includes the steps of:(a) suspending a diacetylrhein containing various impurities and, in particular, relatively high amounts of aloe-emodin derivatives, in a mixture of organic solvent/water;(b) adding a tertiary amine;(c) adding to the solution obtained a salt of an acid and of an alkali metal or of an alkaline-earth metal;(d) carrying out a hydrolysis in a weakly acidic medium;(e) collecting the purified diacetylrhein, by filtration.Type: GrantFiled: March 18, 1997Date of Patent: May 26, 1998Assignee: Steba Beheer B.V.Inventor: Avraham Cohen
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Patent number: 5670695Abstract: The present invention relates to a process for the preparation of 1,8-diacetoxy-3-carboxyanthraquinone, also known as diacerein, via aloin acetylation, oxidation of the acetylated product, and purification of the raw diacerein obtained by means of crystallization from 2-methoxyethanol or N,N-dimethylacetamide and optionally by dissolution of the corresponding salt with triethylamine in methylene chloride, followed by removal of the insoluble residue.Type: GrantFiled: January 23, 1995Date of Patent: September 23, 1997Assignee: Laboratoire Medidom S.A.Inventor: Guido Di Napoli
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Patent number: 5668172Abstract: A pharmaceutical compound of the formula ##STR1## in which R is hydrogen, halo or F.sub.2 HCO--; or a salt, amide or ester thereof, useful in the treatment of skeletal diseases.Type: GrantFiled: August 23, 1995Date of Patent: September 16, 1997Assignee: Lilly Industries LimitedInventors: Peter Thaddeus Gallagher, William Martin Owton, Andrew Caerwyn Williams
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Patent number: 5480873Abstract: Pharmaceutical compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are each hydrogen, hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl-C.sub.1-4 alkoxy;R.sup.3 istetrazolyl, orand R.sup.4 and R.sup.5 are each hydrogen, hydroxy, acyloxy, nitro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, halo, optionally substituted phenyl, --SO.sub.3 H or --NR'R" where R' and R" are each hydrogen or C.sub.1-4 alkyl;provided that when R.sup.3 is --CR'R".CHR'"CO.sub.2 H or tetrazolyl, R.sup.1 and R.sup.2 are each hydroxyl, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acyloxy, --O-glucoside, optionally substituted phenyl or optionally substituted phenyl C.sub.1-4 alkoxy; andor a pharmaceutically acceptable salt or ester thereof.Type: GrantFiled: February 25, 1993Date of Patent: January 2, 1996Assignee: Lilly Industries LimitedInventors: Michael Brunavs, Colin P. Dell, David R. Dobson, Peter T. Gallagher, Terence A. Hicks, William M. Owton, Colin W. Smith
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Patent number: 5451606Abstract: The present invention concerns a compound of formula (I) ##STR1## wherein: X is selected from H and OH;R is a residue which, linked to the ##STR2## group, forms an amino acid; the enantiomers and racemic mixtures thereof; and the pharmaceutically acceptable salts thereof.The invention further concerns a pharmaceutical composition which comprises the above compound or salts thereof and the use of the compound for treating an articular pathology.Type: GrantFiled: October 6, 1993Date of Patent: September 19, 1995Assignee: Istituto Gentili S.p.A.Inventors: Sergio Rosini, Maurizio Mian
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Patent number: 5430067Abstract: Pharmaceutical compounds as follows:9,10-dihydro-9,10-dioxo-4,5,8-trimethoxyanthracene-2-carboxylic acid,4,5-diethoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid,9,10-dihydro-9,10-dioxo-4,5-dipropoxyanthracene-2-carboxylic acid,4,5-dibutoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid,9,10-dihydro-5,8-dimethoxy-9,10-dioxoanthracene-2-carboxylic acid,7-acetoxy-9,10-dihydro-9,10-dioxoanthracene-2-carboxylic acid;and salts and esters thereof.Type: GrantFiled: August 11, 1994Date of Patent: July 4, 1995Assignee: Eli Lilly and CompanyInventors: Peter T. Gallagher, Terence A. Hicks, William M. Owton
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Patent number: 5424421Abstract: The invention relates to the synthesis of 6-deoxykermesates, 6-deoxykermesic acid, and carminic acid, based on a reaction of a 2-halogenonapthazarin with a bis-trimethylsilyl-diene.Type: GrantFiled: March 17, 1993Date of Patent: June 13, 1995Assignee: European Colour PLCInventors: John H. P. Tyman, Alberto Fiecchi, deceased
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Patent number: 5412123Abstract: Derivatives of anthraquinone and anthracene are synthesized and formulated into pharmaceutical formulations. When the formulations are administered the derivatives act as ligands binding to an interrupting the biological chain of events associated with selectin receptors in the human body.Type: GrantFiled: February 8, 1993Date of Patent: May 2, 1995Assignee: Glycomed IncorporatedInventors: Narasinga Rao, Peng C. Tang, John H. Musser
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Patent number: 5393898Abstract: Diacetylrhein which is substantially free of aloe-emodin components, is prepared by a process whereina) rhein-9-anthrone-8-glusoside containing aloe-emodin components is subjected to a liquid-liquid partitioning of the compounds obtained is carried out between a polar organic solvent which is only partly miscible with water and an aqueous phase,b) the rhein-9-anthrone-8-glucoside contained after the partitioning in the aqueous phase is oxidized to rhein-8-glucoside,c) the glucose residue in the 8-position of the rhein-8-glucoside is split off in an acidic medium and,d) the rhein obtained is acetylated and the diacetylrhein recovered.Type: GrantFiled: April 28, 1994Date of Patent: February 28, 1995Assignee: Madaus AGInventors: Alfons Carcasona, Wolf Grimminger, Pentti Hietala, Helga Zaeske, Klaus Witthohn
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Patent number: 5391775Abstract: The present invention provides a process for obtaining diacetylrhein, wherein diacetylrhein containing aloe-emodin components is subjected to a liquid-liquid partitioning between a polar organic solvent which is only partly miscible with water and an aqueous phase of pH 6.5. to 7.5 and the diacetylrhein is recovered and optionally recrystallised.The present invention is also concerned with diacetylrhein obtainable by this process and with pharmaceutical compositions containing it.Type: GrantFiled: April 29, 1994Date of Patent: February 21, 1995Assignee: Madaus AGInventors: Alfons Carcasona, Wolf Grimminger, Pentti Heitala, Klaus Witthohn, Helga Zaeske
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Patent number: 5362750Abstract: 4,5-Dihydroxy- and 4,5,8-trihydroxy-9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid dicarbonates and urethanes having therapeutic activities, a process for the preparation thereof and pharmaceutical compositions containing them.Type: GrantFiled: June 7, 1993Date of Patent: November 8, 1994Assignee: Istituto Gentili S.p.A.Inventors: Sergio Rosini, Maurizio Mian
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Patent number: 5330981Abstract: This application describes 3-arylalkyl esters of 4,5-dihydro-9,10-dioxo-2-anthracenecarboxylic acid and a process for making them. Also described is a method of using the compounds in the treatment of arthritis.Type: GrantFiled: December 30, 1992Date of Patent: July 19, 1994Assignee: Istituto Gentili S.p.A.Inventors: Sergio Rosini, Maurizio Mian
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Patent number: 5322946Abstract: An industrially useful process for the production of an aromatic hydroxy compound which comprises reacting an aromatic sulfonic acid alkali metal salt and/or an aromatic sulfonic acid with an alkali metal hydroxide in the presence of a surface active agent, wherein the reaction is effected by uniformly dispersing these-materials in a reaction medium selected from aliphatic, alicyclic and aromatic hydrocarbons. By employing this process, the product can be obtained with high purity, high yield and high selectivity using a minimum amount of the alkali metal hydroxide.Type: GrantFiled: January 8, 1993Date of Patent: June 21, 1994Assignee: Kawasaki Steel CorporationInventors: Masato Takagi, Yoshihiro Naruse, Akinori Matsuura, Kyohko Kobayashi
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Patent number: 5294701Abstract: This invention provides novel anti-tumour compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen or together form an alkyl-, alkoxy- or OH-substituted aromatic group, which optionally contains an N atom as a hetero-atom; R is --COCH.sub.3 or --C.tbd.C--R.sub.4 and R.sub.4 is H or trimethylsilyl; and R.sub.3 is H or --COCF.sub.3 ; and acid addition salts thereof; as well as compositions containing these compounds.Type: GrantFiled: May 6, 1992Date of Patent: March 15, 1994Assignee: Pharmachemie B.V.Inventors: Johan W. Scheeren, Joannes F. M. de Bie, Dirk de Vos
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Patent number: 5166319Abstract: This invention provides a method of preparing conjugates of bioactive compounds and site-specific compounds in which covalent bonding between the compounds is effected by interfacial condensation while protecting the active binding sites from the condensation reaction. This provides very high yields of the bioactive, site-specific conjugate, the products are homogeneous and it provides novel conjugate products. It is of particular advantage for monoclonal antibodies conjugated with cytotoxic agents.Type: GrantFiled: October 10, 1989Date of Patent: November 24, 1992Assignee: Brunswick CorporationInventor: Wolfgang J. Wrasidlo
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Patent number: 5081270Abstract: 1-Hydroxyanthraquinones are prepared in an improved process by reacting phthalic anhydride or derivatives thereof with phenol derivatives in the presence of a Lewis acid as catalyst and in the presence or absence of a diluent, wherein the improvement comprises conducting the reaction in a self-cleaning apparatus having a mixing effect, at a temperature of from 120.degree. C. to 300.degree. C. for from 5 to 1,000 seconds, the self-cleaning apparatus having a mixing effect subjecting the reactants to a shear gradient of from 50 to 20,000 sec.sup.-1 with an energy input of from 0.01 to 0.2 kwh/kg of reactants.Type: GrantFiled: October 19, 1990Date of Patent: January 14, 1992Assignee: BASF AktiengesellschaftInventors: Juergen Pfister, Michael Schiessl, Rainer Nachtrab
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Patent number: 4966918Abstract: The present invention concerns compounds of the formula: ##STR1## wherein R.sup.1 hydrogen, a hydroxyl group or a methoxy group;R.sup.2 is hydrogen or a methyl group;R.sup.3 is hydrogen or a methyl group;Y is a halogen, a secondary amino group or a tertiary amino group; andZ is hydrogen or a halogen.The invention further concerns pharmaceutical compositions which comprises the above-identified compound or the acid salts thereof, and the use of the compound or compositions for treating a malignancy in a subject.Type: GrantFiled: January 27, 1989Date of Patent: October 30, 1990Assignee: Sloan-Kettering Institute for Cancer ResearchInventors: Kyoichi A. Watanabe, Masao Koyama