ZA200204296B - Benzo(a) phenazin-11-carboxamide derivatives and their use as joint inhibitors of topomerase I and II. - Google Patents

Info

Publication number

ZA200204296B

ZA200204296B ZA200204296A ZA200204296A ZA200204296B ZA 200204296 B ZA200204296 B ZA 200204296B ZA 200204296 A ZA200204296 A ZA 200204296A ZA 200204296 A ZA200204296 A ZA 200204296A ZA 200204296 B ZA200204296 B ZA 200204296B

Authority

ZA

South Africa

Prior art keywords

benzo

phenazine

carboxylic acid

amide

dimethylamino

Prior art date

1999-12-02

Links

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• 239000003112 inhibitor Substances 0.000 title claims description 18
• QDGSQQMUZONPER-UHFFFAOYSA-N benzo[a]phenazine-11-carboxamide Chemical class C1=CC=CC2=C(N=C3C(C(=O)N)=CC=CC3=N3)C3=CC=C21 QDGSQQMUZONPER-UHFFFAOYSA-N 0.000 title claims description 15
• 150000001875 compounds Chemical class 0.000 claims description 138
• -1 2-Methoxy-benzo[a]phenazine- 11-carboxylic acid (2-dimethylamino-ethyl)-amide 2-Hydroxy-benzo[a]phenazine-11-carboxylic acid (2-dimethylamino-ethyl)-amide 4-Nitro-benzo[a]phenazine-11-carboxylic acid Chemical compound 0.000 claims description 42
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
• 206010028980 Neoplasm Diseases 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• GMAMQZVLSLMBFK-UHFFFAOYSA-N 4-methoxybenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC2=NC3=CC=CC(C(O)=O)=C3N=C2C2=C1C(OC)=CC=C2 GMAMQZVLSLMBFK-UHFFFAOYSA-N 0.000 claims description 18
• 102000003915 DNA Topoisomerases Human genes 0.000 claims description 18
• 108090000323 DNA Topoisomerases Proteins 0.000 claims description 18
• 102000007537 Type II DNA Topoisomerases Human genes 0.000 claims description 18
• 108010046308 Type II DNA Topoisomerases Proteins 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 230000008569 process Effects 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 9
• 239000003960 organic solvent Substances 0.000 claims description 9
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000004480 active ingredient Substances 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 claims description 5
• 229940105324 1,2-naphthoquinone Drugs 0.000 claims description 5
• 235000010233 benzoic acid Nutrition 0.000 claims description 5
• 238000007385 chemical modification Methods 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• JGCSKOVQDXEQHI-UHFFFAOYSA-N phenazinecarboxylic acid Natural products C1=CC=C2N=C3C(C(=O)O)=CC=CC3=NC2=C1 JGCSKOVQDXEQHI-UHFFFAOYSA-N 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 claims description 4
• 239000005711 Benzoic acid Substances 0.000 claims description 4
• 241001465754 Metazoa Species 0.000 claims description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• YWKFCDIYCCGIDC-UHFFFAOYSA-N 3-nitrobenzo[a]phenazine-11-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=CC2=C(N=C3C(C(=O)O)=CC=CC3=N3)C3=CC=C21 YWKFCDIYCCGIDC-UHFFFAOYSA-N 0.000 claims description 3
• LKHUWHQEMJTELV-UHFFFAOYSA-N 4-fluorobenzo[a]phenazine-11-carboxylic acid Chemical compound FC1=CC=CC2=C(N=C3C(C(=O)O)=CC=CC3=N3)C3=CC=C21 LKHUWHQEMJTELV-UHFFFAOYSA-N 0.000 claims description 3
• YCJGYBFINMOPQD-UHFFFAOYSA-N 4-nitrobenzo[a]phenazine-11-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=CC2=C(N=C3C(C(=O)O)=CC=CC3=N3)C3=CC=C21 YCJGYBFINMOPQD-UHFFFAOYSA-N 0.000 claims description 3
• 108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 230000000844 anti-bacterial effect Effects 0.000 claims description 3
• 229940121375 antifungal agent Drugs 0.000 claims description 3
• 239000003443 antiviral agent Substances 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
• 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
• 239000011707 mineral Substances 0.000 claims description 3
• TXYHMWWZBDEXFS-UHFFFAOYSA-N 2-nitrobenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC([N+]([O-])=O)=CC2=C(N=C3C(C(=O)O)=CC=CC3=N3)C3=CC=C21 TXYHMWWZBDEXFS-UHFFFAOYSA-N 0.000 claims description 2
• GJINSKDYCZDTNC-UHFFFAOYSA-N 3-aminobenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2N=C3C4=CC=C(N)C=C4C=CC3=NC2=C1 GJINSKDYCZDTNC-UHFFFAOYSA-N 0.000 claims description 2
• FYYPVCVHISPYJR-UHFFFAOYSA-N 4,10-dimethoxybenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC=C2C3=NC4=C(C(O)=O)C(OC)=CC=C4N=C3C=CC2=C1OC FYYPVCVHISPYJR-UHFFFAOYSA-N 0.000 claims description 2
• KPPIVWLVGCNHBK-UHFFFAOYSA-N 4-(2-methoxyethoxy)benzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC2=NC3=CC=CC(C(O)=O)=C3N=C2C2=C1C(OCCOC)=CC=C2 KPPIVWLVGCNHBK-UHFFFAOYSA-N 0.000 claims description 2
• QUQUQZHBQSXVDN-UHFFFAOYSA-N 4-aminobenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC2=NC3=CC=CC(C(O)=O)=C3N=C2C2=C1C(N)=CC=C2 QUQUQZHBQSXVDN-UHFFFAOYSA-N 0.000 claims description 2
• SOFSGGQTMQBVNT-UHFFFAOYSA-N 4-azidobenzo[a]phenazine-11-carboxylic acid Chemical compound [N-]=[N+]=NC1=CC=CC2=C(N=C3C(C(=O)O)=CC=CC3=N3)C3=CC=C21 SOFSGGQTMQBVNT-UHFFFAOYSA-N 0.000 claims description 2
• JFEUGWJSZOECHU-UHFFFAOYSA-N 4-cyanobenzo[a]phenazine-11-carboxylic acid Chemical compound N#CC1=CC=CC2=C(N=C3C(C(=O)O)=CC=CC3=N3)C3=CC=C21 JFEUGWJSZOECHU-UHFFFAOYSA-N 0.000 claims description 2
• UFNMPAVHVUBBSY-UHFFFAOYSA-N 4-methoxy-8-methylbenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC2=NC3=C(C)C=CC(C(O)=O)=C3N=C2C2=C1C(OC)=CC=C2 UFNMPAVHVUBBSY-UHFFFAOYSA-N 0.000 claims description 2
• KFTKDMSJDGPIQK-UHFFFAOYSA-N 4-methylbenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC2=NC3=CC=CC(C(O)=O)=C3N=C2C2=C1C(C)=CC=C2 KFTKDMSJDGPIQK-UHFFFAOYSA-N 0.000 claims description 2
• JKUBOZLNPSTRAZ-UHFFFAOYSA-N 4-methylsulfanylbenzo[a]phenazine-11-carboxylic acid Chemical compound C1=CC2=NC3=CC=CC(C(O)=O)=C3N=C2C2=C1C(SC)=CC=C2 JKUBOZLNPSTRAZ-UHFFFAOYSA-N 0.000 claims description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
• 239000003242 anti bacterial agent Substances 0.000 claims description 2
• 230000000840 anti-viral effect Effects 0.000 claims description 2
• 239000003429 antifungal agent Substances 0.000 claims description 2
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 2
• 150000002825 nitriles Chemical class 0.000 claims description 2
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 21
• HDMBEBSSLSPIRB-UHFFFAOYSA-N 10-hydroxy-4-methoxybenzo[a]phenazine-11-carboxylic acid Chemical compound COc1cccc2c1ccc1nc3ccc(O)c(C(O)=O)c3nc21 HDMBEBSSLSPIRB-UHFFFAOYSA-N 0.000 claims 2
• 230000001404 mediated effect Effects 0.000 claims 2
• UQMQCALFRXNWFZ-UHFFFAOYSA-N 2-[11-[2-(dimethylamino)ethylcarbamoyl]benzo[a]phenazin-4-yl]oxyacetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)COC1=CC=CC2=C(N=C3C(C(=O)NCCN(C)C)=CC=CC3=N3)C3=CC=C21 UQMQCALFRXNWFZ-UHFFFAOYSA-N 0.000 claims 1
• DSFGJZOVQQZIKE-UHFFFAOYSA-N 3-acetamido-n-[2-(dimethylamino)ethyl]benzo[a]phenazine-11-carboxamide Chemical compound C1=C(NC(C)=O)C=CC2=C(N=C3C(C(=O)NCCN(C)C)=CC=CC3=N3)C3=CC=C21 DSFGJZOVQQZIKE-UHFFFAOYSA-N 0.000 claims 1
• WVAIBSCPDIUYOG-UHFFFAOYSA-N 4-(cyanomethylamino)-n-[2-(dimethylamino)ethyl]benzo[a]phenazine-11-carboxamide Chemical compound N#CCNC1=CC=CC2=C(N=C3C(C(=O)NCCN(C)C)=CC=CC3=N3)C3=CC=C21 WVAIBSCPDIUYOG-UHFFFAOYSA-N 0.000 claims 1
• DOARFNKQLWLGLK-UHFFFAOYSA-N 4-(dimethylamino)-n-[2-(dimethylamino)ethyl]benzo[a]phenazine-11-carboxamide Chemical compound CN(C)C1=CC=CC2=C(N=C3C(C(=O)NCCN(C)C)=CC=CC3=N3)C3=CC=C21 DOARFNKQLWLGLK-UHFFFAOYSA-N 0.000 claims 1
• SGVZTTYHLNLLJR-UHFFFAOYSA-N 4-[(4-chlorophenyl)methoxy]-n-[2-(dimethylamino)ethyl]benzo[a]phenazine-11-carboxamide Chemical compound C=1C=CC2=C3N=C4C(C(=O)NCCN(C)C)=CC=CC4=NC3=CC=C2C=1OCC1=CC=C(Cl)C=C1 SGVZTTYHLNLLJR-UHFFFAOYSA-N 0.000 claims 1
• UGUKOIDCJQGTHA-UHFFFAOYSA-N 4-chlorobenzo[a]phenazine-11-carboxylic acid Chemical compound ClC1=CC=CC2=C(N=C3C(C(=O)O)=CC=CC3=N3)C3=CC=C21 UGUKOIDCJQGTHA-UHFFFAOYSA-N 0.000 claims 1
• YJGCRSHWTREEPU-UHFFFAOYSA-N CN(CCNC(=O)C1=CC=CC2=NC3=CC=C4C(=C3N=C12)C=CC(=C4)S(N)(=O)=O)C.CN(CCNC(=O)C4=C(C=CC1=NC2=CC=C3C(=C2N=C41)C(=CC=C3OC)Cl)OC)C Chemical compound CN(CCNC(=O)C1=CC=CC2=NC3=CC=C4C(=C3N=C12)C=CC(=C4)S(N)(=O)=O)C.CN(CCNC(=O)C4=C(C=CC1=NC2=CC=C3C(=C2N=C41)C(=CC=C3OC)Cl)OC)C YJGCRSHWTREEPU-UHFFFAOYSA-N 0.000 claims 1
• QFJROTQTMGIHLN-ZOWNYOTGSA-N CN(C[C@@H](CO)NC(=O)C1=C(C=CC2=NC3=CC=C4C(=C3N=C12)C=CC=C4OC)O)C.CNCCNC(=O)C4=CC=CC1=NC2=CC=C3C(=C2N=C41)C=CC=C3OC Chemical compound CN(C[C@@H](CO)NC(=O)C1=C(C=CC2=NC3=CC=C4C(=C3N=C12)C=CC=C4OC)O)C.CNCCNC(=O)C4=CC=CC1=NC2=CC=C3C(=C2N=C41)C=CC=C3OC QFJROTQTMGIHLN-ZOWNYOTGSA-N 0.000 claims 1
• PGIOVAFRAORHSC-PFEQFJNWSA-N COC1=CC=CC=2C1=CC=C1N=C3C=CC=C(C3=NC21)C(=O)O.CN2C[C@@H](CC2)NC(=O)C2=CC=CC1=NC3=CC=C4C(=C3N=C21)C=CC=C4OC Chemical compound COC1=CC=CC=2C1=CC=C1N=C3C=CC=C(C3=NC21)C(=O)O.CN2C[C@@H](CC2)NC(=O)C2=CC=CC1=NC3=CC=C4C(=C3N=C21)C=CC=C4OC PGIOVAFRAORHSC-PFEQFJNWSA-N 0.000 claims 1
• KQRJQPPMHIMOGH-UHFFFAOYSA-N N-[2-(dimethylamino)ethyl]-3-(methylsulfamoyl)benzo[a]phenazine-11-carboxamide 2,2,2-trifluoroacetic acid Chemical compound CN(CCNC(=O)C1=CC=CC2=NC3=CC=C4C(=C3N=C12)C=CC(=C4)S(NC)(=O)=O)C.FC(C(=O)O)(F)F KQRJQPPMHIMOGH-UHFFFAOYSA-N 0.000 claims 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
• HUGNQLRMXGSIFH-UHFFFAOYSA-N [11-[2-(dimethylamino)ethylcarbamoyl]benzo[a]phenazin-4-yl] n-ethylcarbamate Chemical compound C1=CC2=NC3=CC=CC(C(=O)NCCN(C)C)=C3N=C2C2=C1C(OC(=O)NCC)=CC=C2 HUGNQLRMXGSIFH-UHFFFAOYSA-N 0.000 claims 1
• HYLVKTVGIFHDMG-UHFFFAOYSA-N benzo[a]phenazine-4,11-dicarboxylic acid Chemical compound C1=CC2=NC3=CC=CC(C(O)=O)=C3N=C2C2=C1C(C(=O)O)=CC=C2 HYLVKTVGIFHDMG-UHFFFAOYSA-N 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
• OCJYFEUOQDYVDJ-UHFFFAOYSA-N ethyl 2-[11-[2-(dimethylamino)ethylcarbamoyl]benzo[a]phenazin-4-yl]oxyacetate Chemical compound C1=CC2=NC3=CC=CC(C(=O)NCCN(C)C)=C3N=C2C2=C1C(OCC(=O)OCC)=CC=C2 OCJYFEUOQDYVDJ-UHFFFAOYSA-N 0.000 claims 1
• IBMHXIHITBJPCY-UHFFFAOYSA-N methyl 3-(dimethylamino)-2-[(4-methoxybenzo[a]phenazine-11-carbonyl)amino]propanoate Chemical compound COC1=CC=CC2=C(N=C3C(C(=O)NC(CN(C)C)C(=O)OC)=CC=CC3=N3)C3=CC=C21 IBMHXIHITBJPCY-UHFFFAOYSA-N 0.000 claims 1
• PFVICZIZAJIINM-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-10-hydroxy-4-oxo-7h-benzo[a]phenazine-11-carboxamide Chemical compound C12=NC=3C(C(=O)NCCN(C)C)=C(O)C=CC=3NC2=CC=C2C1=CC=CC2=O PFVICZIZAJIINM-UHFFFAOYSA-N 0.000 claims 1
• GICSPTVTMVUSFH-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-3-methoxybenzo[a]phenazine-11-carboxamide Chemical compound C1=CC(C(=O)NCCN(C)C)=C2N=C3C4=CC=C(OC)C=C4C=CC3=NC2=C1 GICSPTVTMVUSFH-UHFFFAOYSA-N 0.000 claims 1
• PDGLDIMONSIRHT-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(hydroxymethyl)benzo[a]phenazine-11-carboxamide Chemical compound OCC1=CC=CC2=C(N=C3C(C(=O)NCCN(C)C)=CC=CC3=N3)C3=CC=C21 PDGLDIMONSIRHT-UHFFFAOYSA-N 0.000 claims 1
• OYPDBVPVJYEKLP-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-methoxy-10-(methylamino)benzo[a]phenazine-11-carboxamide Chemical compound C1=CC=C2C3=NC4=C(C(=O)NCCN(C)C)C(NC)=CC=C4N=C3C=CC2=C1OC OYPDBVPVJYEKLP-UHFFFAOYSA-N 0.000 claims 1
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