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Substituted 9,10-anthracenebishydrazones

Assignee: Wyeth Holdings LLC
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Filing: 1979-05-07
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Granted: 1981-03-24
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Expires: 1999-05-07
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Abstract

Abstract This disclosure describes anthracene-9,10-bis-carbonyl-hydrazones and derivatives thereof useful as antibacterial agents, for inhibiting the growth of transplanted mouse tumors, and for inducing the regression and/or palliation of leukemia and related cancers.

Inventors

  • 👤 Keith C. Murdock
  • 👤 Frederick E. Durr

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 13:34
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/12; C07D295/125; C07D295/13; C07C; C07C249/00; C07C249/16; A; A61; A61P; A61P35/00; C07C17/00; C07C17/26; C07C17/32; C07C251/00; C07C251/72; C07C251/86; C07C281/00; C07C281/16; C07C281/18; C07C47/00; C07C47/38; C07C47/453; C07C47/457; C07C47/47; C07C47/52; C07C47/55; C07C47/56; C07C47/57; C07C47/575; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/42; C07D213/60; C07D213/72; C07D213/76; C07D213/77; C07D233/00; C07D233/04; C07D233/28; C07D233/44; C07D233/52; C07D239/00; C07D239/02; C07D239/06; C07D239/08; C07D239/12; C07D239/18; C07D243/00; C07D243/04; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/52; C07D317/00; C07D317/08; C07D317/44; C07D317/70; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/20; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/22; C07C2603/24

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 394 words
A compound selected from the group consisting of those of the formula: ##STR14## wherein Z is a trivalent moiety selected from the group consisting of those of the formulae: ##STR15## wherein n is 0, 1, 2 or 3 and R is hydrogen, alkyl having up to 4 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, phenyl or benzyl; R 1 is selected from the group consisting of hydrogen and alkyl having up to 4 carbon atoms; R 2 is selected from the group consisting of hydrogen, alkyl having up to 4 carbon atoms, phenyl and monovalent moieties of the formulae: ##STR16## wherein m is 2, 3, 4 or 5, p is 1, 2 or 3, q is 0, 1 or 2, R' is hydrogen or alkyl having up to 4 carbon atoms, R" is hydrogen or alkyl having up to 4 carbon atoms, R 7 is alkyl having up to 4 carbon atoms, amino, anilino, hydrazino, monohydroxyalkylamino having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear an hydroxy group, alkylamino having up to 4 carbon atoms, dialkylamino wherein each alkyl group has up to 4 carbon atoms, cycloalkylamino having from 3 to 6 carbon atoms, benzylamino, α-phenethylamino, β-phenethylamino, 2-furfurylamino, 3-furfurylamino, α-thenylamino, β-thenylamino, α-pyridylmethylamino, β-pyridylmethylamino, γ-pyridylmethylamino, indanylamino, pyrrolidino, piperidino, morpholino, thiomorpholino, N-methylpiperazino, alkoxy having up to 4 carbon atoms, alkylthio having up to 4 carbon atoms or a moiety of the formula: ##STR17## wherein m, R 1 , R' and R" are as hereinbefore defined and the moiety --NR'R" may be pyrrolidino, piperidino, morpholino or N-methylpiperazino, X is oxo (O═), thioxo (S═) or imino (R'--N═ wherein R' is as hereinbefore defined) and Y is oxy (--O--), thio (--S--), methylene (--CH 2 --) or a divalent group of the formula: ##STR18## wherein R 8 is alkyl having up to 4 carbon atoms or monohydroxyalkyl having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear an hydroxy group; and R 3 , R 4 , R 5 and R 6 are each individually selected from the group consisting of hydrogen, halogen (F, Cl, Br, I), hydroxy, nitro, amino, sulfonamido, alkyl having up to 3 carbon atoms and alkoxy having up to 3 carbon atoms; and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof.
Claim 2
Dependent Claim 394 words
A compound selected from the group consisting of those of the formula: ##STR14## wherein Z is a trivalent moiety selected from the group consisting of those of the formulae: ##STR15## wherein n is 0, 1, 2 or 3 and R is hydrogen, alkyl having up to 4 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, phenyl or benzyl; R 1 is selected from the group consisting of hydrogen and alkyl having up to 4 carbon atoms; R 2 is selected from the group consisting of hydrogen, alkyl having up to 4 carbon atoms, phenyl and monovalent moieties of the formulae: ##STR16## wherein m is 2, 3, 4 or 5, p is 1, 2 or 3, q is 0, 1 or 2, R' is hydrogen or alkyl having up to 4 carbon atoms, R" is hydrogen or alkyl having up to 4 carbon atoms, R 7 is alkyl having up to 4 carbon atoms, amino, anilino, hydrazino, monohydroxyalkylamino having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear an hydroxy group, alkylamino having up to 4 carbon atoms, dialkylamino wherein each alkyl group has up to 4 carbon atoms, cycloalkylamino having from 3 to 6 carbon atoms, benzylamino, α-phenethylamino, β-phenethylamino, 2-furfurylamino, 3-furfurylamino, α-thenylamino, β-thenylamino, α-pyridylmethylamino, β-pyridylmethylamino, γ-pyridylmethylamino, indanylamino, pyrrolidino, piperidino, morpholino, thiomorpholino, N-methylpiperazino, alkoxy having up to 4 carbon atoms, alkylthio having up to 4 carbon atoms or a moiety of the formula: ##STR17## wherein m, R 1 , R' and R" are as hereinbefore defined and the moiety --NR'R" may be pyrrolidino, piperidino, morpholino or N-methylpiperazino, X is oxo (O═), thioxo (S═) or imino (R'--N═ wherein R' is as hereinbefore defined) and Y is oxy (--O--), thio (--S--), methylene (--CH 2 --) or a divalent group of the formula: ##STR18## wherein R 8 is alkyl having up to 4 carbon atoms or monohydroxyalkyl having from 2 to 4 carbon atoms and wherein the carbon atom alpha to the nitrogen atom may not bear an hydroxy group; and R 3 , R 4 , R 5 and R 6 are each individually selected from the group consisting of hydrogen, halogen (F, Cl, Br, I), hydroxy, nitro, amino, sulfonamido, alkyl having up to 3 carbon atoms and alkoxy having up to 3 carbon atoms; and the pharmacologically acceptable acid-addition and quaternary ammonium salts thereof.
Claim 3
Dependent Claim 35 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR19## bis(2-imidazolin-2-yl)hydrazone of 9,10-anthracenedicarboxaldehyde dihydrochloride.
Claim 4
Dependent Claim 42 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR20## wherein X is imino and R 7 is methylamino; 1,1-[9,10-anthrylenebis(methylidynenitrilo)]bis-3-methylguanidine dihydroiodide.
Claim 5
Dependent Claim 41 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR21## wherein X is methylimino and R 7 is methylamino; 1,1'-[9,10-anthrylene-bis(methylidynenitrilo)]bis-(2,3-dimethylguanidine)dihydroiodide.
Claim 6
Dependent Claim 41 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR22## wherein X is imino and R 7 is dimethylamino; 1,1'-[9,10-anthrylenebis(methylidynenitrilo)]bis-(3,3-dimethylguanidine)dihydroiodide.
Claim 7
Dependent Claim 41 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR23## wherein X is imino and R 7 is hydroxyethylamino; 1,1'-[9,10-anthrylenebis(methylidynenitrilo)]bis-[3-(2-hydroxyethyl)guanidine]dihydroiodide.
Claim 8
Dependent Claim 42 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR24## wherein X is imino and R 7 is amino; 1,1'-[9,10-anthrylenebis(methylidynenitrilo)]diguanidine dihydrochloride.
Claim 9
Dependent Claim 35 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR25## bis(1,4,5,6-tetrahydro-2-pyrimidin-2-ylhydrazone) of 9,10-anthracenedicarboxaldehyde dihydrochloride.
Claim 10
Dependent Claim 35 words
The compound according to claim 1 wherein Z is methylidyne, R 1 is methyl, R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 ##STR26## bis(2-imidazolin-2-ylmethylhydrazone) of 9,10-anthracenedicarboxaldehyde dihydroiodide.
Claim 11
Dependent Claim 41 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR27## wherein X is imino and R 7 is benzylamino; 1,1'-[9,10-anthrylenebis)methylidynenitrilo)]bis(3-benzylguanidine)dihydroiodide.
Claim 12
Dependent Claim 38 words
The compound according to claim 1 wherein Z=methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR28## wherein X is imino and R 7 is 2-furfurylamino:1,1'[9,10-anthrylenebis(methylidynenitrilo)]bis[3-(2-furfuryl)guanidine]dihydrochloride.
Claim 13
Dependent Claim 41 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR29## wherein X is imino and R 7 is cyclohexylamino; 1,1'-[9,10-anthrylenebis(methylidynenitrilo)]bis(3-cyclohexylguanidine)dihydroiodide.
Claim 14
Dependent Claim 38 words
The compound according to claim 1 wherein Z=methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR30## wherein X is imino and R 7 is 2-thenylamino:1,1'-[9,10-anthrylenebis(methylidynenitrilo)]bis[3-(2-thenyl)guanidine]dihydrochloride.
Claim 15
Dependent Claim 38 words
The compound according to claim 1 wherein Z=methylidyne, R 1 , R 3 , R 4 , R 5 and R 6 are hydrogen and R 2 is ##STR31## wherein X is imino and R 7 is 4-pyridylmethylamino:1,1'-[9,10-Anthrylenebis(methylidynenitrilo)]bis[3-(4-pyridylmethyl)guanidine]tetrahydroiodide.
Claim 16
Dependent Claim 36 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 and R 6 are hydrogen, R 5 is 2-chloro and R 2 is ##STR32## bis(2-imidazolin-2-ylhydrazone) of 2-chloro-9,10-anthracenedicarboxaldehyde dihydrochloride.
Claim 17
Dependent Claim 36 words
The compound according to claim 1 wherein Z is methylidyne, R 1 , R 3 , R 4 and R 6 are hydrogen, R 5 is 2-methyl and R 2 is ##STR33## bis(2-imidazolin-2-ylhydrazone) of 2-methyl-9,10-anthracenedicarboxaldehyde dihydrochloride.
Claim 18
Dependent Claim 35 words
The compound according to claim 1 wherein Z=methylidyne, R 5 is 1-hydroxy, R 6 is 4-hydroxy, R 1 , R 3 and R 4 are hydrogen and R 2 is ##STR34## bis(2-imidazolin-2-ylhydrazone) of 1,4-dihydroxy-9,10-anthracenedicarboxaldehyde dihydrochloride.
Claim 19
Dependent Claim 33 words
The compound according to claim 1 wherein Z=methylidyne, R 1 , R 4 and R 6 are hydrogen, R 3 and R 5 are fluorine, and R 2 is ##STR35## bis(2-imidazolin-2-ylhydrazone) of 2,6-difluoro-9,10-anthracenedicarboxaldehyde.
Claim 20
Dependent Claim 10 words
The compound according to claim 2 as the diacetate salt.
Claim 21
Dependent Claim 13 words
An acid-addition salt according to claim 1 wherein the acid is acetic acid.
Claim 22
Dependent Claim 13 words
An acid-addition salt according to claim 1 wherein the acid is hydrochloric acid.
Claim 23
Dependent Claim 13 words
An acid-addition salt according to claim 1 wherein the acid is maleic acid.
Claim 24
Dependent Claim 13 words
An acid-addition salt according to claim 1 wherein the acid is gluconic acid.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-03-23 1984-09-22 1985-03-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-03-23 1988-09-22 1989-03-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-03-23 1992-09-22 1993-03-24 $7700.00 Window Closed / Lapsed

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