PROCESS FOR OBTAINING NEW ANTHRACENE-9,10-BIS-CARBONYL-HYDRAZONE

There are disclosed anthracene-9, 10- bis- carbonyllydrazones and derivatives thereof useful for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers. The compounds can be represented by the formula: wherein Z is a triv...

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DURR F.E
description There are disclosed anthracene-9, 10- bis- carbonyllydrazones and derivatives thereof useful for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers. The compounds can be represented by the formula: wherein Z is a trivalent moiety selected from the group consisting of those of the formulae: -(CH2)n-@= and -@H-CH= wherein n is 0, 1, 2 or 3 and R is hydrogen, lower alkyl, cycloalkyl, phenyl or benzyl; R1 is of hydrogen or lower alkyl; R2 is selected from the group consisting of monovalent moieties of the formulae: wherein p is 1, 2 or 3, q is 0, 1 or 2, R min is hydrogen or lower alkyl, R sec is lower alkyl R7 is a moiety of the formula: wherein m is 2, 3, 4 or 5, R1, R min and R sec are as hereinbefore defined and the moiety -NR min R sec may be pyrrolidino, piperidino, morpholino or N-methylpiperazino, X is oxo (O =), thioxo (S =) or imino (R min -N =) wherein R min is as hereinbefore defined), and R3, R4, R5 and R6 are each individually selected from the group consisting of hydrogen, halogen, hydroxy, nitro, amino, sulfonamido, lower alkyl; and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof. These compunds can be prepared by reaction of 9,10-anthracenedialdehyde with a hydrazine. The dialdehyde is obtained from the reaction of anthracene with paraformaldehyde and hydrochloric acid, giving the 9,10-bis-(chloromethyl)anthracene derivative, which then is treated with sodium in ethanol. Or anthracene can be reacted with vinylene carbonate, to give a cyclic carbonate which is hydrolised to the diol, which in turn is treated with lead tetraacetate in acetic acid to give the 9,10-anthracenedicarboxaldehyde. Or 9,10-anthracenediacetonitrile, a substituted hydrazine hyrochloride, sodium acetate and Raney nickel is reduced with hydrogen to give the anthracene bis-hydrazone.
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The compounds can be represented by the formula: wherein Z is a trivalent moiety selected from the group consisting of those of the formulae: -(CH2)n-@= and -@H-CH= wherein n is 0, 1, 2 or 3 and R is hydrogen, lower alkyl, cycloalkyl, phenyl or benzyl; R1 is of hydrogen or lower alkyl; R2 is selected from the group consisting of monovalent moieties of the formulae: wherein p is 1, 2 or 3, q is 0, 1 or 2, R min is hydrogen or lower alkyl, R sec is lower alkyl R7 is a moiety of the formula: wherein m is 2, 3, 4 or 5, R1, R min and R sec are as hereinbefore defined and the moiety -NR min R sec may be pyrrolidino, piperidino, morpholino or N-methylpiperazino, X is oxo (O =), thioxo (S =) or imino (R min -N =) wherein R min is as hereinbefore defined), and R3, R4, R5 and R6 are each individually selected from the group consisting of hydrogen, halogen, hydroxy, nitro, amino, sulfonamido, lower alkyl; and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof. These compunds can be prepared by reaction of 9,10-anthracenedialdehyde with a hydrazine. The dialdehyde is obtained from the reaction of anthracene with paraformaldehyde and hydrochloric acid, giving the 9,10-bis-(chloromethyl)anthracene derivative, which then is treated with sodium in ethanol. Or anthracene can be reacted with vinylene carbonate, to give a cyclic carbonate which is hydrolised to the diol, which in turn is treated with lead tetraacetate in acetic acid to give the 9,10-anthracenedicarboxaldehyde. Or 9,10-anthracenediacetonitrile, a substituted hydrazine hyrochloride, sodium acetate and Raney nickel is reduced with hydrogen to give the anthracene bis-hydrazone.</description><edition>3</edition><language>eng</language><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS ; CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; HUMAN NECESSITIES ; HYGIENE ; MEDICAL OR VETERINARY SCIENCE ; METALLURGY ; ORGANIC CHEMISTRY ; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES ; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</subject><creationdate>1983</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=19830930&amp;DB=EPODOC&amp;CC=YU&amp;NR=111980A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25563,76318</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&amp;date=19830930&amp;DB=EPODOC&amp;CC=YU&amp;NR=111980A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>MURDOCK K.C</creatorcontrib><creatorcontrib>DURR F.E</creatorcontrib><title>PROCESS FOR OBTAINING NEW ANTHRACENE-9,10-BIS-CARBONYL-HYDRAZONE</title><description>There are disclosed anthracene-9, 10- bis- carbonyllydrazones and derivatives thereof useful for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers. The compounds can be represented by the formula: wherein Z is a trivalent moiety selected from the group consisting of those of the formulae: -(CH2)n-@= and -@H-CH= wherein n is 0, 1, 2 or 3 and R is hydrogen, lower alkyl, cycloalkyl, phenyl or benzyl; R1 is of hydrogen or lower alkyl; R2 is selected from the group consisting of monovalent moieties of the formulae: wherein p is 1, 2 or 3, q is 0, 1 or 2, R min is hydrogen or lower alkyl, R sec is lower alkyl R7 is a moiety of the formula: wherein m is 2, 3, 4 or 5, R1, R min and R sec are as hereinbefore defined and the moiety -NR min R sec may be pyrrolidino, piperidino, morpholino or N-methylpiperazino, X is oxo (O =), thioxo (S =) or imino (R min -N =) wherein R min is as hereinbefore defined), and R3, R4, R5 and R6 are each individually selected from the group consisting of hydrogen, halogen, hydroxy, nitro, amino, sulfonamido, lower alkyl; and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof. These compunds can be prepared by reaction of 9,10-anthracenedialdehyde with a hydrazine. The dialdehyde is obtained from the reaction of anthracene with paraformaldehyde and hydrochloric acid, giving the 9,10-bis-(chloromethyl)anthracene derivative, which then is treated with sodium in ethanol. Or anthracene can be reacted with vinylene carbonate, to give a cyclic carbonate which is hydrolised to the diol, which in turn is treated with lead tetraacetate in acetic acid to give the 9,10-anthracenedicarboxaldehyde. Or 9,10-anthracenediacetonitrile, a substituted hydrazine hyrochloride, sodium acetate and Raney nickel is reduced with hydrogen to give the anthracene bis-hydrazone.</description><subject>ACYCLIC OR CARBOCYCLIC COMPOUNDS</subject><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>HUMAN NECESSITIES</subject><subject>HYGIENE</subject><subject>MEDICAL OR VETERINARY SCIENCE</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><subject>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</subject><subject>SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1983</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZHAICPJ3dg0OVnDzD1Lwdwpx9PTz9HNX8HMNV3D0C_EIcnR29XPVtdQxNNB18gzWdXYMcvL3i_TR9Yh0CXKM8vdz5WFgTUvMKU7lhdLcDHJuriHOHrqpBfnxqcUFicmpeakl8ZGhhoaGlhYGjsYEFQAApA4pbQ</recordid><startdate>19830930</startdate><enddate>19830930</enddate><creator>MURDOCK K.C</creator><creator>DURR F.E</creator><scope>EVB</scope></search><sort><creationdate>19830930</creationdate><title>PROCESS FOR OBTAINING NEW ANTHRACENE-9,10-BIS-CARBONYL-HYDRAZONE</title><author>MURDOCK K.C ; DURR F.E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_YU111980A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>1983</creationdate><topic>ACYCLIC OR CARBOCYCLIC COMPOUNDS</topic><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>HUMAN NECESSITIES</topic><topic>HYGIENE</topic><topic>MEDICAL OR VETERINARY SCIENCE</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><topic>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</topic><topic>SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</topic><toplevel>online_resources</toplevel><creatorcontrib>MURDOCK K.C</creatorcontrib><creatorcontrib>DURR F.E</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>MURDOCK K.C</au><au>DURR F.E</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>PROCESS FOR OBTAINING NEW ANTHRACENE-9,10-BIS-CARBONYL-HYDRAZONE</title><date>1983-09-30</date><risdate>1983</risdate><abstract>There are disclosed anthracene-9, 10- bis- carbonyllydrazones and derivatives thereof useful for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers. The compounds can be represented by the formula: wherein Z is a trivalent moiety selected from the group consisting of those of the formulae: -(CH2)n-@= and -@H-CH= wherein n is 0, 1, 2 or 3 and R is hydrogen, lower alkyl, cycloalkyl, phenyl or benzyl; R1 is of hydrogen or lower alkyl; R2 is selected from the group consisting of monovalent moieties of the formulae: wherein p is 1, 2 or 3, q is 0, 1 or 2, R min is hydrogen or lower alkyl, R sec is lower alkyl R7 is a moiety of the formula: wherein m is 2, 3, 4 or 5, R1, R min and R sec are as hereinbefore defined and the moiety -NR min R sec may be pyrrolidino, piperidino, morpholino or N-methylpiperazino, X is oxo (O =), thioxo (S =) or imino (R min -N =) wherein R min is as hereinbefore defined), and R3, R4, R5 and R6 are each individually selected from the group consisting of hydrogen, halogen, hydroxy, nitro, amino, sulfonamido, lower alkyl; and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof. These compunds can be prepared by reaction of 9,10-anthracenedialdehyde with a hydrazine. The dialdehyde is obtained from the reaction of anthracene with paraformaldehyde and hydrochloric acid, giving the 9,10-bis-(chloromethyl)anthracene derivative, which then is treated with sodium in ethanol. Or anthracene can be reacted with vinylene carbonate, to give a cyclic carbonate which is hydrolised to the diol, which in turn is treated with lead tetraacetate in acetic acid to give the 9,10-anthracenedicarboxaldehyde. Or 9,10-anthracenediacetonitrile, a substituted hydrazine hyrochloride, sodium acetate and Raney nickel is reduced with hydrogen to give the anthracene bis-hydrazone.</abstract><edition>3</edition><oa>free_for_read</oa></addata></record>
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subjects ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
title PROCESS FOR OBTAINING NEW ANTHRACENE-9,10-BIS-CARBONYL-HYDRAZONE
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