CA2797694A1 - Activators of human pyruvate kinase - Google Patents
Activators of human pyruvate kinase Download PDFInfo
- Publication number
- CA2797694A1 CA2797694A1 CA2797694A CA2797694A CA2797694A1 CA 2797694 A1 CA2797694 A1 CA 2797694A1 CA 2797694 A CA2797694 A CA 2797694A CA 2797694 A CA2797694 A CA 2797694A CA 2797694 A1 CA2797694 A1 CA 2797694A1
- Authority
- CA
- Canada
- Prior art keywords
- cancer
- oxo
- sulfonamide
- alkyl
- tetrahydroquinoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 102000013009 Pyruvate Kinase Human genes 0.000 title abstract 2
- 108020005115 Pyruvate Kinase Proteins 0.000 title abstract 2
- 239000012190 activator Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 206010028980 Neoplasm Diseases 0.000 claims abstract 25
- 201000011510 cancer Diseases 0.000 claims abstract 25
- 230000004913 activation Effects 0.000 claims abstract 5
- 201000010099 disease Diseases 0.000 claims abstract 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 5
- -1 (C1-C4)alkyl-CO- Chemical group 0.000 claims 73
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 28
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 150000002367 halogens Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical group O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 claims 5
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 4
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- 208000009956 adenocarcinoma Diseases 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 229910052794 bromium Inorganic materials 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 201000010982 kidney cancer Diseases 0.000 claims 4
- 201000007270 liver cancer Diseases 0.000 claims 4
- 208000014018 liver neoplasm Diseases 0.000 claims 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
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- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
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- 206010014967 Ependymoma Diseases 0.000 claims 2
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 claims 2
- 208000036566 Erythroleukaemia Diseases 0.000 claims 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims 2
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- 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims 2
- 208000007641 Pinealoma Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
- 201000000582 Retinoblastoma Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
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- 208000024770 Thyroid neoplasm Diseases 0.000 claims 2
- 208000023915 Ureteral Neoplasms Diseases 0.000 claims 2
- 206010046392 Ureteric cancer Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 2
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 2
- 208000014070 Vestibular schwannoma Diseases 0.000 claims 2
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims 2
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 claims 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
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- 208000017733 acquired polycythemia vera Diseases 0.000 claims 2
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- 125000005157 alkyl carboxy group Chemical group 0.000 claims 2
- 206010065867 alveolar rhabdomyosarcoma Diseases 0.000 claims 2
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims 2
- 210000002255 anal canal Anatomy 0.000 claims 2
- 201000007180 bile duct carcinoma Diseases 0.000 claims 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 2
- 208000003362 bronchogenic carcinoma Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
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- XESJSVKSJFRHPE-UHFFFAOYSA-N 1-acetyl-n-(3,4-dimethylphenyl)-2,3-dihydroindole-5-sulfonamide Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1S(=O)(=O)NC1=CC=C(C)C(C)=C1 XESJSVKSJFRHPE-UHFFFAOYSA-N 0.000 claims 1
- KUMQIRFCKBSETE-UHFFFAOYSA-N 1-acetyl-n-(3,4-dimethylphenyl)-2-methyl-2,3-dihydroindole-5-sulfonamide Chemical compound C=1C=C2N(C(C)=O)C(C)CC2=CC=1S(=O)(=O)NC1=CC=C(C)C(C)=C1 KUMQIRFCKBSETE-UHFFFAOYSA-N 0.000 claims 1
- WVMOGAPSTDCYRO-UHFFFAOYSA-N 2-oxo-n-(3-phenylphenyl)-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 WVMOGAPSTDCYRO-UHFFFAOYSA-N 0.000 claims 1
- WQRPZEZBGHLTAC-UHFFFAOYSA-N 2-oxo-n-[3-(trifluoromethyl)phenyl]-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound FC(F)(F)C1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 WQRPZEZBGHLTAC-UHFFFAOYSA-N 0.000 claims 1
- DWLBYLGNERHAIR-UHFFFAOYSA-N 2-oxo-n-pyridin-3-yl-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)NC1=CC=CN=C1 DWLBYLGNERHAIR-UHFFFAOYSA-N 0.000 claims 1
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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- FVLSXGNSQKPXJN-UHFFFAOYSA-N N-(3-methylphenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound CC1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 FVLSXGNSQKPXJN-UHFFFAOYSA-N 0.000 claims 1
- GTFOCOKDGPLBEK-UHFFFAOYSA-N N-(4-chloro-3-methylphenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(C)=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 GTFOCOKDGPLBEK-UHFFFAOYSA-N 0.000 claims 1
- BANOCBYMYBHZCK-UHFFFAOYSA-N N-(4-fluorophenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound C1=CC(F)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 BANOCBYMYBHZCK-UHFFFAOYSA-N 0.000 claims 1
- YIKOTMZSQQKCNN-UHFFFAOYSA-N N-(4-methylphenyl)-2-oxo-3,4-dihydro-1H-quinoline-6-sulfonamide Chemical compound C1=CC(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 YIKOTMZSQQKCNN-UHFFFAOYSA-N 0.000 claims 1
- AIEOBFOLWRLWFY-UHFFFAOYSA-N [3-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)sulfonylamino]phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 AIEOBFOLWRLWFY-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- FXULHVBWXADQIT-UHFFFAOYSA-N n-(2-fluorophenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound FC1=CC=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 FXULHVBWXADQIT-UHFFFAOYSA-N 0.000 claims 1
- HPTNHSMTBSTARS-UHFFFAOYSA-N n-(2-methoxyphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound COC1=CC=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 HPTNHSMTBSTARS-UHFFFAOYSA-N 0.000 claims 1
- WDMSYXZEYIVUAV-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 WDMSYXZEYIVUAV-UHFFFAOYSA-N 0.000 claims 1
- TVEWYQNBFLBJON-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound FC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 TVEWYQNBFLBJON-UHFFFAOYSA-N 0.000 claims 1
- OZCHLLBJIJDZSV-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-1,3-dimethyl-2-oxobenzimidazole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(N(C)C(=O)N2C)C2=C1 OZCHLLBJIJDZSV-UHFFFAOYSA-N 0.000 claims 1
- PQRJAXXCZAABJD-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-1-methylindole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(N(C)C=C2)C2=C1 PQRJAXXCZAABJD-UHFFFAOYSA-N 0.000 claims 1
- CKACPEDULOKSHJ-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-1,3,4,5-tetrahydro-1-benzazepine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CCC2)C2=C1 CKACPEDULOKSHJ-UHFFFAOYSA-N 0.000 claims 1
- BSEGVWNGGVEPQX-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-1,3-dihydrobenzimidazole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)N2)C2=C1 BSEGVWNGGVEPQX-UHFFFAOYSA-N 0.000 claims 1
- XMTTXQUJUKTALG-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)C2)C2=C1 XMTTXQUJUKTALG-UHFFFAOYSA-N 0.000 claims 1
- ABPIVUMUUZSCTQ-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=C(NC(=O)CC2)C2=C1 ABPIVUMUUZSCTQ-UHFFFAOYSA-N 0.000 claims 1
- CAPFLYHFMYQPBI-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-7-(propan-2-ylamino)-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CC(C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 CAPFLYHFMYQPBI-UHFFFAOYSA-N 0.000 claims 1
- PFQAFZFSUCEPGW-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-7-piperidin-1-yl-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)N2CCCCC2)=CC2=C1NC(=O)CC2 PFQAFZFSUCEPGW-UHFFFAOYSA-N 0.000 claims 1
- ZMERFADMZRTONY-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-oxo-7-pyrrolidin-1-yl-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)N2CCCC2)=CC2=C1NC(=O)CC2 ZMERFADMZRTONY-UHFFFAOYSA-N 0.000 claims 1
- FLRPVXLMOJGRDV-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-3-oxo-4h-1,4-benzoxazine-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(OCC(=O)N2)C2=C1 FLRPVXLMOJGRDV-UHFFFAOYSA-N 0.000 claims 1
- LFKHSAHGVHJEPF-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-3-oxo-6-phenyl-4h-1,4-benzoxazine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)C=2C=CC=CC=2)=CC2=C1NC(=O)CO2 LFKHSAHGVHJEPF-UHFFFAOYSA-N 0.000 claims 1
- CRZDZXNDKULTHH-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-4-methyl-3-oxo-1,4-benzoxazine-6-sulfonamide Chemical compound C1=C2N(C)C(=O)COC2=CC=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 CRZDZXNDKULTHH-UHFFFAOYSA-N 0.000 claims 1
- OHQSSKLYMQFLQN-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-6-methyl-3-oxo-4h-1,4-benzoxazine-7-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)C)=CC2=C1NC(=O)CO2 OHQSSKLYMQFLQN-UHFFFAOYSA-N 0.000 claims 1
- FTLNYBCPHCLODH-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-(1-hydroxypropan-2-ylamino)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OCC(C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 FTLNYBCPHCLODH-UHFFFAOYSA-N 0.000 claims 1
- WQEYRSZNQWSCKO-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-(2-hydroxyethylamino)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)NCCO)=CC2=C1NC(=O)CC2 WQEYRSZNQWSCKO-UHFFFAOYSA-N 0.000 claims 1
- RDJVVXIZIXTZEL-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-(methylamino)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CNC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 RDJVVXIZIXTZEL-UHFFFAOYSA-N 0.000 claims 1
- IAJXECZPLGLEKB-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-[(2-hydroxy-2-methylpropyl)amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)NCC(C)(C)O)=CC2=C1NC(=O)CC2 IAJXECZPLGLEKB-UHFFFAOYSA-N 0.000 claims 1
- FTLNYBCPHCLODH-CQSZACIVSA-N n-(3,4-dimethylphenyl)-7-[[(2r)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 FTLNYBCPHCLODH-CQSZACIVSA-N 0.000 claims 1
- FTLNYBCPHCLODH-AWEZNQCLSA-N n-(3,4-dimethylphenyl)-7-[[(2s)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(C)=C1 FTLNYBCPHCLODH-AWEZNQCLSA-N 0.000 claims 1
- MSHCFYZEHSRAPG-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1NC(=O)CC2 MSHCFYZEHSRAPG-UHFFFAOYSA-N 0.000 claims 1
- QITDSYIYIPIMLL-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-n-methyl-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)N(C)C1=CC=C(C)C(C)=C1 QITDSYIYIPIMLL-UHFFFAOYSA-N 0.000 claims 1
- HOPSYFZHYRZZBT-UHFFFAOYSA-N n-(3-chloro-2-methylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CC1=C(Cl)C=CC=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1NC(=O)CC2 HOPSYFZHYRZZBT-UHFFFAOYSA-N 0.000 claims 1
- CUZDABRLLGGXKI-JTQLQIEISA-N n-(3-chloro-4-fluorophenyl)-7-[[(2s)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(F)C(Cl)=C1 CUZDABRLLGGXKI-JTQLQIEISA-N 0.000 claims 1
- NRHQXXODPRXAER-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 NRHQXXODPRXAER-UHFFFAOYSA-N 0.000 claims 1
- VLRYVDZPCCVRIS-LBPRGKRZSA-N n-(3-chloro-4-methylphenyl)-7-[[(2s)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(C)C(Cl)=C1 VLRYVDZPCCVRIS-LBPRGKRZSA-N 0.000 claims 1
- HYOLJEHGMOJMNR-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(C)=CC=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1NC(=O)CC2 HYOLJEHGMOJMNR-UHFFFAOYSA-N 0.000 claims 1
- NQPXVAUSZJKKDP-UHFFFAOYSA-N n-(3-cyanophenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)NC1=CC=CC(C#N)=C1 NQPXVAUSZJKKDP-UHFFFAOYSA-N 0.000 claims 1
- YBQWWIYDCVJQAW-UHFFFAOYSA-N n-(3-fluoro-4-methylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(F)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 YBQWWIYDCVJQAW-UHFFFAOYSA-N 0.000 claims 1
- CBBKJQADPAHXLO-UHFFFAOYSA-N n-(3-fluorophenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 CBBKJQADPAHXLO-UHFFFAOYSA-N 0.000 claims 1
- IZMRNRGXIQXSKA-UHFFFAOYSA-N n-(3-methoxyphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound COC1=CC=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 IZMRNRGXIQXSKA-UHFFFAOYSA-N 0.000 claims 1
- FGSXPFIJRVGTDM-UHFFFAOYSA-N n-(4-chloro-3-methylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(Cl)C(C)=CC(NS(=O)(=O)C=2C(=CC=3NC(=O)CCC=3C=2)F)=C1 FGSXPFIJRVGTDM-UHFFFAOYSA-N 0.000 claims 1
- AISVTQYDRIQDKU-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=CC(Cl)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 AISVTQYDRIQDKU-UHFFFAOYSA-N 0.000 claims 1
- LPVLUUBCUWKBJT-UHFFFAOYSA-N n-(4-fluoro-3-methylphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=C(F)C(C)=CC(NS(=O)(=O)C=2C=C3CCC(=O)NC3=CC=2)=C1 LPVLUUBCUWKBJT-UHFFFAOYSA-N 0.000 claims 1
- SLPTYIRATHEPAX-LBPRGKRZSA-N n-(4-fluoro-3-methylphenyl)-7-[[(2s)-1-hydroxypropan-2-yl]amino]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound OC[C@H](C)NC1=CC=2NC(=O)CCC=2C=C1S(=O)(=O)NC1=CC=C(F)C(C)=C1 SLPTYIRATHEPAX-LBPRGKRZSA-N 0.000 claims 1
- AEYRWLQXGYDIOE-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)CC2)C2=C1 AEYRWLQXGYDIOE-UHFFFAOYSA-N 0.000 claims 1
- RZCXGKSKBPHLSG-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)-7-fluoro-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound CC1=CC=C(Cl)C=C1NS(=O)(=O)C(C(=C1)F)=CC2=C1NC(=O)CC2 RZCXGKSKBPHLSG-UHFFFAOYSA-N 0.000 claims 1
- OCVBNKSYCFRIMO-UHFFFAOYSA-N n-benzyl-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)NCC1=CC=CC=C1 OCVBNKSYCFRIMO-UHFFFAOYSA-N 0.000 claims 1
- OZKITVZVEHPSNT-UHFFFAOYSA-N n-naphthalen-1-yl-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=CC=C2C(NS(=O)(=O)C=3C=C4CCC(NC4=CC=3)=O)=CC=CC2=C1 OZKITVZVEHPSNT-UHFFFAOYSA-N 0.000 claims 1
- DVUSSGILUNAHHB-UHFFFAOYSA-N n-naphthalen-2-yl-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=CC=CC2=CC(NS(=O)(=O)C=3C=C4CCC(NC4=CC=3)=O)=CC=C21 DVUSSGILUNAHHB-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 101001091538 Homo sapiens Pyruvate kinase PKM Proteins 0.000 abstract 1
- 102100034911 Pyruvate kinase PKM Human genes 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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| US61/329,158 | 2010-04-29 | ||
| PCT/US2011/033852 WO2011137089A1 (en) | 2010-04-29 | 2011-04-26 | Activators of human pyruvate kinase |
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| CA2797694A1 true CA2797694A1 (en) | 2011-11-03 |
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| JP (1) | JP2013525438A (OSRAM) |
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| CA (1) | CA2797694A1 (OSRAM) |
| WO (1) | WO2011137089A1 (OSRAM) |
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| TWI549947B (zh) | 2010-12-29 | 2016-09-21 | 阿吉歐斯製藥公司 | 治療化合物及組成物 |
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| CN108451955B (zh) | 2011-05-03 | 2022-02-01 | 安吉奥斯医药品有限公司 | 用于治疗的丙酮酸激酶活化剂 |
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| AU2011245441A1 (en) | 2012-11-15 |
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| US20130109672A1 (en) | 2013-05-02 |
| US9708267B2 (en) | 2017-07-18 |
| JP2013525438A (ja) | 2013-06-20 |
| EP2563761A1 (en) | 2013-03-06 |
| AU2011245441B2 (en) | 2014-12-18 |
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