CA2771190C - Heat shock protein binding compounds, compositions, and methods for making and using same - Google Patents
Heat shock protein binding compounds, compositions, and methods for making and using same Download PDFInfo
- Publication number
- CA2771190C CA2771190C CA2771190A CA2771190A CA2771190C CA 2771190 C CA2771190 C CA 2771190C CA 2771190 A CA2771190 A CA 2771190A CA 2771190 A CA2771190 A CA 2771190A CA 2771190 C CA2771190 C CA 2771190C
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- Prior art keywords
- alkyl
- pyrimidin
- alkoxy
- ylthio
- amino
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 246
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000027455 binding Effects 0.000 title claims description 85
- 238000009739 binding Methods 0.000 title claims description 85
- 239000000203 mixture Substances 0.000 title claims description 11
- 102000002812 Heat-Shock Proteins Human genes 0.000 title description 6
- 108010004889 Heat-Shock Proteins Proteins 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 121
- 101100507655 Canis lupus familiaris HSPA1 gene Proteins 0.000 claims abstract description 120
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 40
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 35
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 35
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
- 108010036652 HSC70 Heat-Shock Proteins Proteins 0.000 claims abstract description 16
- 102000012215 HSC70 Heat-Shock Proteins Human genes 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 238000012544 monitoring process Methods 0.000 claims abstract 7
- -1 alkylamido Chemical group 0.000 claims description 217
- 230000000694 effects Effects 0.000 claims description 91
- 238000011282 treatment Methods 0.000 claims description 37
- 210000004027 cell Anatomy 0.000 claims description 35
- 235000018102 proteins Nutrition 0.000 claims description 34
- 201000011510 cancer Diseases 0.000 claims description 26
- 230000002401 inhibitory effect Effects 0.000 claims description 21
- 230000006907 apoptotic process Effects 0.000 claims description 13
- 230000001939 inductive effect Effects 0.000 claims description 8
- 239000002773 nucleotide Substances 0.000 claims description 8
- 125000003729 nucleotide group Chemical group 0.000 claims description 8
- 230000009286 beneficial effect Effects 0.000 claims description 7
- 210000004881 tumor cell Anatomy 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims 485
- 125000004093 cyano group Chemical group *C#N 0.000 claims 351
- 125000003342 alkenyl group Chemical group 0.000 claims 284
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 283
- 125000000304 alkynyl group Chemical group 0.000 claims 282
- 125000001769 aryl amino group Chemical group 0.000 claims 282
- 125000004986 diarylamino group Chemical group 0.000 claims 281
- 125000004663 dialkyl amino group Chemical group 0.000 claims 280
- 125000000623 heterocyclic group Chemical group 0.000 claims 269
- 125000000217 alkyl group Chemical group 0.000 claims 257
- 125000004104 aryloxy group Chemical group 0.000 claims 242
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 242
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 242
- 229920006395 saturated elastomer Polymers 0.000 claims 242
- 125000003368 amide group Chemical group 0.000 claims 241
- 125000003302 alkenyloxy group Chemical group 0.000 claims 240
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 239
- 125000004442 acylamino group Chemical group 0.000 claims 238
- 125000003118 aryl group Chemical group 0.000 claims 238
- 125000000753 cycloalkyl group Chemical group 0.000 claims 217
- 125000003282 alkyl amino group Chemical group 0.000 claims 206
- 229910052736 halogen Inorganic materials 0.000 claims 197
- 150000002367 halogens Chemical class 0.000 claims 197
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 193
- 229910052739 hydrogen Inorganic materials 0.000 claims 183
- 239000001257 hydrogen Substances 0.000 claims 183
- 150000002431 hydrogen Chemical class 0.000 claims 183
- 125000004001 thioalkyl group Chemical group 0.000 claims 176
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 174
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 166
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 159
- 229910052799 carbon Inorganic materials 0.000 claims 78
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 49
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 34
- 230000002062 proliferating effect Effects 0.000 claims 30
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 26
- 102100023038 WD and tetratricopeptide repeats protein 1 Human genes 0.000 claims 18
- 125000000539 amino acid group Chemical group 0.000 claims 18
- 239000012472 biological sample Substances 0.000 claims 18
- 239000003814 drug Substances 0.000 claims 18
- 238000004519 manufacturing process Methods 0.000 claims 18
- 230000008856 allosteric binding Effects 0.000 claims 12
- 235000001014 amino acid Nutrition 0.000 claims 12
- 150000001413 amino acids Chemical class 0.000 claims 12
- 108020001756 ligand binding domains Proteins 0.000 claims 12
- 230000017066 negative regulation of growth Effects 0.000 claims 12
- 241001465754 Metazoa Species 0.000 claims 8
- 125000002837 carbocyclic group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- ZYAVZIQPWICPQI-UHFFFAOYSA-N n-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]prop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC(N)=CC(NC(=O)C=C)=N1 ZYAVZIQPWICPQI-UHFFFAOYSA-N 0.000 claims 7
- 206010006187 Breast cancer Diseases 0.000 claims 6
- 208000026310 Breast neoplasm Diseases 0.000 claims 6
- 210000004204 blood vessel Anatomy 0.000 claims 6
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- VPXOPMWNCDOOHY-UHFFFAOYSA-N 2-amino-n-[3-[4-[(4-chlorophenyl)methoxy]-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CC(Cl)=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 VPXOPMWNCDOOHY-UHFFFAOYSA-N 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- WFGSXUGRJBWBKO-UHFFFAOYSA-N n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]pyrrolidine-2-carboxamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(=O)C2NCCC2)=C1 WFGSXUGRJBWBKO-UHFFFAOYSA-N 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims 3
- NEQAQYRTBUUDRM-AATRIKPKSA-N (E)-N-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound n1c(OC)c(Sc2nc(NC(=O)\C=C\C)ccn2)c(OC)nc1N1CCN(C)CC1 NEQAQYRTBUUDRM-AATRIKPKSA-N 0.000 claims 2
- BRMOSVCLPVVKIZ-VOTSOKGWSA-N (e)-n-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-3-(furan-2-yl)prop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC(N=1)=NC(N)=CC=1NC(=O)\C=C\C1=CC=CO1 BRMOSVCLPVVKIZ-VOTSOKGWSA-N 0.000 claims 2
- FUOCSRXYVJZEQY-UHFFFAOYSA-N 2-amino-3-methyl-n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]butanamide Chemical compound CC(C)C(N)C(=O)NC1=CC=CC(SC=2C(=NC(=NC=2)N2CCN(C)CC2)OCC=2C=CC=CC=2)=C1 FUOCSRXYVJZEQY-UHFFFAOYSA-N 0.000 claims 2
- DIBDGXQADBJDRK-UHFFFAOYSA-N 2-amino-n-[3-[2-(4-methylpiperazin-1-yl)-4-(pyridin-3-ylmethoxy)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=NC=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 DIBDGXQADBJDRK-UHFFFAOYSA-N 0.000 claims 2
- JTLISYWXNAOUAB-UHFFFAOYSA-N 2-amino-n-[3-[2-(4-methylpiperazin-1-yl)-4-(pyridin-4-ylmethoxy)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CN=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 JTLISYWXNAOUAB-UHFFFAOYSA-N 0.000 claims 2
- LBJCUDZMNPAWPX-UHFFFAOYSA-N 2-amino-n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 LBJCUDZMNPAWPX-UHFFFAOYSA-N 0.000 claims 2
- POHPIHISICFSPX-UHFFFAOYSA-N 2-amino-n-[3-[4-[(3-aminophenyl)methoxy]-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=C(N)C=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 POHPIHISICFSPX-UHFFFAOYSA-N 0.000 claims 2
- BWUSQVQDYKPTOB-UHFFFAOYSA-N 2-amino-n-[3-[4-methoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 BWUSQVQDYKPTOB-UHFFFAOYSA-N 0.000 claims 2
- NQOSOTSVNLLLOU-UHFFFAOYSA-N N-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]furan-2-carboxamide Chemical compound COc1nc(nc(OC)c1Sc1nccc(NC(=O)c2ccco2)n1)N1CCN(C)CC1 NQOSOTSVNLLLOU-UHFFFAOYSA-N 0.000 claims 2
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- OSGZIPATAUFTOB-UHFFFAOYSA-N n-[2-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylpyrimidin-4-yl]prop-2-enamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CC=CC=2)=NC=C1SC1=NC=CC(NC(=O)C=C)=N1 OSGZIPATAUFTOB-UHFFFAOYSA-N 0.000 claims 2
- PDASYYUDODOITL-UHFFFAOYSA-N n-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-2-methylprop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC=CC(NC(=O)C(C)=C)=N1 PDASYYUDODOITL-UHFFFAOYSA-N 0.000 claims 2
- SDOIRFGGAJEHHN-UHFFFAOYSA-N n-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]propanamide Chemical compound CCC(=O)NC1=CC=NC(SC=2C(=NC(=NC=2OC)N2CCN(C)CC2)OC)=N1 SDOIRFGGAJEHHN-UHFFFAOYSA-N 0.000 claims 2
- SXCYNWXZUZUHKI-UHFFFAOYSA-N n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(C)=O)=C1 SXCYNWXZUZUHKI-UHFFFAOYSA-N 0.000 claims 2
- DNCACTLFFFYPLO-UHFFFAOYSA-N n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]benzamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(=O)C=2C=CC=CC=2)=C1 DNCACTLFFFYPLO-UHFFFAOYSA-N 0.000 claims 2
- NVOGKZHADXJLOK-UHFFFAOYSA-N n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]prop-2-enamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(=O)C=C)=C1 NVOGKZHADXJLOK-UHFFFAOYSA-N 0.000 claims 2
- INYVTQNZEYWIPX-UHFFFAOYSA-N n-[3-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]prop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=CC=CC(NC(=O)C=C)=C1 INYVTQNZEYWIPX-UHFFFAOYSA-N 0.000 claims 2
- SKNSZDZQCZNECV-UHFFFAOYSA-N n-[3-[4,6-dimethyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(SC=2C(=NC(=NC=2C)N2CCN(C)CC2)C)=C1 SKNSZDZQCZNECV-UHFFFAOYSA-N 0.000 claims 2
- YBBRZWICSZOVDL-UHFFFAOYSA-N n-[6-amino-2-[4,6-diethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]prop-2-enamide Chemical compound CCOC1=NC(N2CCN(C)CC2)=NC(OCC)=C1SC1=NC(N)=CC(NC(=O)C=C)=N1 YBBRZWICSZOVDL-UHFFFAOYSA-N 0.000 claims 2
- FGJQLMDWCCXABP-UHFFFAOYSA-N n-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]prop-2-ynamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC(N)=CC(NC(=O)C#C)=N1 FGJQLMDWCCXABP-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- SEQFBBKYBYAZHS-XBXARRHUSA-N (E)-N-[2-(4,6-dimethoxy-2-piperidin-1-ylpyrimidin-5-yl)sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound n1c(OC)c(Sc2nc(NC(=O)\C=C\C)ccn2)c(OC)nc1N1CCCCC1 SEQFBBKYBYAZHS-XBXARRHUSA-N 0.000 claims 1
- GMPYYBGTWDCJDM-QPJJXVBHSA-N (E)-N-[2-(4,6-dimethoxy-2-pyrrolidin-1-ylpyrimidin-5-yl)sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound n1c(OC)c(Sc2nc(NC(=O)\C=C\C)ccn2)c(OC)nc1N1CCCC1 GMPYYBGTWDCJDM-QPJJXVBHSA-N 0.000 claims 1
- YCKIVURWWNHFNE-SNAWJCMRSA-N (E)-N-[2-(4,6-dimethyl-2-piperazin-1-ylpyrimidin-5-yl)sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound n1c(NC(=O)/C=C/C)ccnc1Sc1c(C)nc(N2CCNCC2)nc1C YCKIVURWWNHFNE-SNAWJCMRSA-N 0.000 claims 1
- OOXXIGVMZLNCBT-FNORWQNLSA-N (E)-N-[3-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]but-2-enamide Chemical compound COC1=NC(=NC(=C1SC=1C=C(C=CC=1)NC(\C=C\C)=O)OC)N1CCN(CC1)C OOXXIGVMZLNCBT-FNORWQNLSA-N 0.000 claims 1
- VTWWZMKUNWANBO-ONNFQVAWSA-N (E)-N-[6-amino-2-(4,6-diethoxy-2-piperidin-1-ylpyrimidin-5-yl)sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound n1c(OCC)c(Sc2nc(NC(=O)\C=C\C)cc(N)n2)c(OCC)nc1N1CCCCC1 VTWWZMKUNWANBO-ONNFQVAWSA-N 0.000 claims 1
- ASIRZMWSLHJTRC-VMPITWQZSA-N (E)-N-[6-amino-2-[4,6-diethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound NC1=CC(=NC(=N1)SC=1C(=NC(=NC=1OCC)N1CCN(CC1)C)OCC)NC(\C=C\C)=O ASIRZMWSLHJTRC-VMPITWQZSA-N 0.000 claims 1
- XYDDQKZAXGDWGB-VOTSOKGWSA-N (E)-N-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-4-(dimethylamino)but-2-enamide Chemical compound n1c(OC)c(Sc2nc(NC(=O)\C=C\CN(C)C)cc(N)n2)c(OC)nc1N1CCN(C)CC1 XYDDQKZAXGDWGB-VOTSOKGWSA-N 0.000 claims 1
- NEQAQYRTBUUDRM-WAYWQWQTSA-N (Z)-N-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound n1c(OC)c(Sc2nc(NC(=O)\C=C/C)ccn2)c(OC)nc1N1CCN(C)CC1 NEQAQYRTBUUDRM-WAYWQWQTSA-N 0.000 claims 1
- IWPBUIJRURIDEE-SNAWJCMRSA-N (e)-n-[2-(4,6-dimethoxy-2-morpholin-4-ylpyrimidin-5-yl)sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound COC1=NC(N2CCOCC2)=NC(OC)=C1SC1=NC=CC(NC(=O)\C=C\C)=N1 IWPBUIJRURIDEE-SNAWJCMRSA-N 0.000 claims 1
- QQWKFHIECZTSCU-SNAWJCMRSA-N (e)-n-[2-(4,6-dimethyl-2-morpholin-4-ylpyrimidin-5-yl)sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound C\C=C\C(=O)NC1=CC=NC(SC=2C(=NC(=NC=2C)N2CCOCC2)C)=N1 QQWKFHIECZTSCU-SNAWJCMRSA-N 0.000 claims 1
- UNDHHPTYENIFJF-VOTSOKGWSA-N (e)-n-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-3-pyridin-3-ylprop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC(N=1)=NC=CC=1NC(=O)\C=C\C1=CC=CN=C1 UNDHHPTYENIFJF-VOTSOKGWSA-N 0.000 claims 1
- VDUBEIAEAGPINY-VOTSOKGWSA-N (e)-n-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-3-thiophen-2-ylprop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC(N=1)=NC=CC=1NC(=O)\C=C\C1=CC=CS1 VDUBEIAEAGPINY-VOTSOKGWSA-N 0.000 claims 1
- SPUQKNOJJYDUGN-VOTSOKGWSA-N (e)-n-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-4-(dimethylamino)but-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC=CC(NC(=O)\C=C\CN(C)C)=N1 SPUQKNOJJYDUGN-VOTSOKGWSA-N 0.000 claims 1
- UDPXWYWUGCNNBS-AATRIKPKSA-N (e)-n-[2-[4,6-dimethyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound C\C=C\C(=O)NC1=CC=NC(SC=2C(=NC(=NC=2C)N2CCN(C)CC2)C)=N1 UDPXWYWUGCNNBS-AATRIKPKSA-N 0.000 claims 1
- DOJOESBANUMVMS-FNORWQNLSA-N (e)-n-[3-[4,6-dimethyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]but-2-enamide Chemical compound C\C=C\C(=O)NC1=CC=CC(SC=2C(=NC(=NC=2C)N2CCN(C)CC2)C)=C1 DOJOESBANUMVMS-FNORWQNLSA-N 0.000 claims 1
- ZNFKBMLHEVKVGD-QPJJXVBHSA-N (e)-n-[6-amino-2-(4,6-diethoxy-2-morpholin-4-ylpyrimidin-5-yl)sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound CCOC1=NC(N2CCOCC2)=NC(OCC)=C1SC1=NC(N)=CC(NC(=O)\C=C\C)=N1 ZNFKBMLHEVKVGD-QPJJXVBHSA-N 0.000 claims 1
- MRZYZOJFPPVTNM-VOTSOKGWSA-N (e)-n-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-3-pyridin-3-ylprop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC(N=1)=NC(N)=CC=1NC(=O)\C=C\C1=CC=CN=C1 MRZYZOJFPPVTNM-VOTSOKGWSA-N 0.000 claims 1
- QGCUKVMRFDETPP-VOTSOKGWSA-N (e)-n-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]-3-thiophen-2-ylprop-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC(N=1)=NC(N)=CC=1NC(=O)\C=C\C1=CC=CS1 QGCUKVMRFDETPP-VOTSOKGWSA-N 0.000 claims 1
- CELXNFCKFARNTI-AATRIKPKSA-N (e)-n-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC(N)=CC(NC(=O)\C=C\C)=N1 CELXNFCKFARNTI-AATRIKPKSA-N 0.000 claims 1
- CELXNFCKFARNTI-WAYWQWQTSA-N (z)-n-[6-amino-2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]but-2-enamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC(N)=CC(NC(=O)\C=C/C)=N1 CELXNFCKFARNTI-WAYWQWQTSA-N 0.000 claims 1
- FJBBXASQIJDFGA-UHFFFAOYSA-N 1-[2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]but-3-en-2-one Chemical compound COc1nc(nc(OC)c1Sc1nccc(CC(=O)C=C)n1)N1CCN(C)CC1 FJBBXASQIJDFGA-UHFFFAOYSA-N 0.000 claims 1
- FWJBAKXPTKFPDA-UHFFFAOYSA-N 2-(4,6-diethoxy-2-piperidin-1-ylpyrimidin-5-yl)sulfanylpyrimidine-4,6-diamine Chemical compound CCOC1=NC(N2CCCCC2)=NC(OCC)=C1SC1=NC(N)=CC(N)=N1 FWJBAKXPTKFPDA-UHFFFAOYSA-N 0.000 claims 1
- XARXCCXKSAFQQH-UHFFFAOYSA-N 2-(4,6-dimethoxy-2-morpholin-4-ylpyrimidin-5-yl)sulfanyl-6-(trifluoromethyl)-1h-pyrimidin-4-one Chemical compound COC1=NC(N2CCOCC2)=NC(OC)=C1SC1=NC(=O)C=C(C(F)(F)F)N1 XARXCCXKSAFQQH-UHFFFAOYSA-N 0.000 claims 1
- PXQMHOFHXOOGKJ-UHFFFAOYSA-N 2-(4,6-dimethoxy-2-morpholin-4-ylpyrimidin-5-yl)sulfanylpyrimidin-4-amine Chemical compound COC1=NC(=NC(=C1SC1=NC=CC(=N1)N)OC)N1CCOCC1 PXQMHOFHXOOGKJ-UHFFFAOYSA-N 0.000 claims 1
- KBLNGNHDCCAZMK-UHFFFAOYSA-N 2-(4,6-dimethoxy-2-morpholin-4-ylpyrimidin-5-yl)sulfanylpyrimidine-4,6-diamine Chemical compound COC1=NC(=NC(=C1SC1=NC(=CC(=N1)N)N)OC)N1CCOCC1 KBLNGNHDCCAZMK-UHFFFAOYSA-N 0.000 claims 1
- DRHZYVWYLJATQL-UHFFFAOYSA-N 2-(4,6-dimethoxy-2-piperidin-1-ylpyrimidin-5-yl)sulfanylpyrimidin-4-amine Chemical compound COC1=NC(=NC(=C1SC1=NC=CC(=N1)N)OC)N1CCCCC1 DRHZYVWYLJATQL-UHFFFAOYSA-N 0.000 claims 1
- NVWSBTSWDRPQBG-UHFFFAOYSA-N 2-(4,6-dimethoxy-2-piperidin-1-ylpyrimidin-5-yl)sulfanylpyrimidine-4,6-diamine Chemical compound COC1=NC(=NC(=C1SC1=NC(=CC(=N1)N)N)OC)N1CCCCC1 NVWSBTSWDRPQBG-UHFFFAOYSA-N 0.000 claims 1
- ZFAQHSKBUWHWNW-UHFFFAOYSA-N 2-(4,6-dimethoxy-2-pyrrolidin-1-ylpyrimidin-5-yl)sulfanylpyrimidin-4-amine Chemical compound COC1=NC(=NC(=C1SC1=NC=CC(=N1)N)OC)N1CCCC1 ZFAQHSKBUWHWNW-UHFFFAOYSA-N 0.000 claims 1
- QHFJQLSZQTUOAP-UHFFFAOYSA-N 2-(4,6-dimethyl-2-piperazin-1-ylpyrimidin-5-yl)sulfanylpyrimidin-4-amine Chemical compound CC1=NC(N2CCNCC2)=NC(C)=C1SC1=NC=CC(N)=N1 QHFJQLSZQTUOAP-UHFFFAOYSA-N 0.000 claims 1
- BSVVWTAODSTIRY-UHFFFAOYSA-N 2-[2-(4-butylpiperazin-1-yl)-4,6-dimethoxypyrimidin-5-yl]sulfanylpyrimidine-4,6-diamine Chemical compound C(CCC)N1CCN(CC1)C1=NC(=C(C(=N1)OC)SC1=NC(=CC(=N1)N)N)OC BSVVWTAODSTIRY-UHFFFAOYSA-N 0.000 claims 1
- SIWBVILNPKZRSU-UHFFFAOYSA-N 2-[2-[2-[2-[4-[4,6-dimethoxy-5-[3-(propanoylamino)phenyl]sulfanylpyrimidin-2-yl]piperazin-1-yl]ethoxy]ethoxy]ethoxy]ethyl 5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoate Chemical compound CCC(=O)NC1=CC=CC(SC=2C(=NC(=NC=2OC)N2CCN(CCOCCOCCOCCOC(=O)CCCCC3C4NC(=O)NC4CS3)CC2)OC)=C1 SIWBVILNPKZRSU-UHFFFAOYSA-N 0.000 claims 1
- FCZYOHJJOKZLPV-UHFFFAOYSA-N 2-[2-[2-[2-[4-[5-[4-(furan-2-carbonylamino)pyrimidin-2-yl]sulfanyl-4,6-dimethylpyrimidin-2-yl]piperazin-1-yl]ethoxy]ethoxy]ethoxy]ethyl 5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoate Chemical compound Cc1nc(nc(C)c1Sc1nccc(NC(=O)c2ccco2)n1)N1CCN(CCOCCOCCOCCOC(=O)CCCCC2SCC3NC(=O)NC23)CC1 FCZYOHJJOKZLPV-UHFFFAOYSA-N 0.000 claims 1
- IUFORQJMSLNIRD-UHFFFAOYSA-N 2-[2-[2-[2-[4-[5-[4-amino-6-(prop-2-enoylamino)pyrimidin-2-yl]sulfanyl-4,6-dimethoxypyrimidin-2-yl]piperazin-1-yl]ethoxy]ethoxy]ethoxy]ethyl 5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoate Chemical compound O=C1NC2C(N1)CSC2CCCCC(=O)OCCOCCOCCOCCN1CCN(CC1)C1=NC(=C(C(=N1)OC)SC1=NC(=CC(=N1)NC(C=C)=O)N)OC IUFORQJMSLNIRD-UHFFFAOYSA-N 0.000 claims 1
- QCJJOIMEELVKHK-UHFFFAOYSA-N 2-[2-[4-(4-aminobutyl)piperazin-1-yl]-4,6-dimethoxypyrimidin-5-yl]sulfanylpyrimidin-4-amine Chemical compound COC1=NC(N2CCN(CCCCN)CC2)=NC(OC)=C1SC1=NC=CC(N)=N1 QCJJOIMEELVKHK-UHFFFAOYSA-N 0.000 claims 1
- DRHRXTUIIDYQJD-UHFFFAOYSA-N 2-[2-[4-(4-aminobutyl)piperazin-1-yl]-4,6-dimethoxypyrimidin-5-yl]sulfanylpyrimidine-4,6-diamine Chemical compound COC1=NC(N2CCN(CCCCN)CC2)=NC(OC)=C1SC1=NC(N)=CC(N)=N1 DRHRXTUIIDYQJD-UHFFFAOYSA-N 0.000 claims 1
- LJRISXBDNWFJDH-UHFFFAOYSA-N 2-[3-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]-1,2-dihydropyrrol-5-one Chemical compound COc1nc(nc(OC)c1Sc1cccc(c1)C1NC(=O)C=C1)N1CCN(C)CC1 LJRISXBDNWFJDH-UHFFFAOYSA-N 0.000 claims 1
- NMWZZCJECIOJEJ-UHFFFAOYSA-N 2-[4,6-diethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidine-4,6-diamine Chemical compound CCOC1=NC(N2CCN(C)CC2)=NC(OCC)=C1SC1=NC(N)=CC(N)=N1 NMWZZCJECIOJEJ-UHFFFAOYSA-N 0.000 claims 1
- JTDZPNOTJVCRSK-UHFFFAOYSA-N 2-[4,6-dimethoxy-2-(4-methyl-4-oxidopiperazin-4-ium-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-amine Chemical compound NC1=NC(=NC=C1)SC=1C(=NC(=NC1OC)N1CC[N+](CC1)(C)[O-])OC JTDZPNOTJVCRSK-UHFFFAOYSA-N 0.000 claims 1
- YMRCYFCTHMBEIM-UHFFFAOYSA-N 2-[4,6-dimethoxy-2-(4-methyl-4-oxidopiperazin-4-ium-1-yl)pyrimidin-5-yl]sulfinylpyrimidin-4-amine Chemical compound NC1=NC(=NC=C1)S(=O)C=1C(=NC(=NC1OC)N1CC[N+](CC1)(C)[O-])OC YMRCYFCTHMBEIM-UHFFFAOYSA-N 0.000 claims 1
- RVVJCGDWMRLSCY-UHFFFAOYSA-N 2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanyl-4-n-prop-2-ynylpyrimidine-4,6-diamine Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC(N)=CC(NCC#C)=N1 RVVJCGDWMRLSCY-UHFFFAOYSA-N 0.000 claims 1
- SCYDPJWGHRGLDE-UHFFFAOYSA-N 2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanyl-n-prop-2-ynylpyrimidin-4-amine Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC=CC(NCC#C)=N1 SCYDPJWGHRGLDE-UHFFFAOYSA-N 0.000 claims 1
- GXKUNEURMIPZNE-UHFFFAOYSA-N 2-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidine-4,6-diamine Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=NC(N)=CC(N)=N1 GXKUNEURMIPZNE-UHFFFAOYSA-N 0.000 claims 1
- RFYIHQRIUSDBJM-UHFFFAOYSA-N 2-[4,6-dimethyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-amine Chemical compound C1CN(C)CCN1C(N=C1C)=NC(C)=C1SC1=NC=CC(N)=N1 RFYIHQRIUSDBJM-UHFFFAOYSA-N 0.000 claims 1
- HEAJNVKLDCVNJK-UHFFFAOYSA-N 2-[4-[5-(4,6-diaminopyrimidin-2-yl)sulfanyl-4,6-dimethoxypyrimidin-2-yl]piperazin-1-yl]ethanol Chemical compound COC1=NC(N2CCN(CCO)CC2)=NC(OC)=C1SC1=NC(N)=CC(N)=N1 HEAJNVKLDCVNJK-UHFFFAOYSA-N 0.000 claims 1
- UJRSGBDTEAAXIQ-UHFFFAOYSA-N 2-amino-3-(1H-imidazol-5-yl)-N-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]propanamide Chemical compound CN1CCN(CC1)c1ncc(Sc2cccc(NC(=O)C(N)Cc3c[nH]cn3)c2)c(OCc2ccccc2)n1 UJRSGBDTEAAXIQ-UHFFFAOYSA-N 0.000 claims 1
- DUYPUTNYDZJOSY-UHFFFAOYSA-N 2-amino-3-methyl-n-[3-[2-(4-methylpiperazin-1-yl)-4-(pyridin-3-ylmethoxy)pyrimidin-5-yl]sulfonylphenyl]pentanamide Chemical compound CCC(C)C(N)C(=O)NC1=CC=CC(S(=O)(=O)C=2C(=NC(=NC=2)N2CCN(C)CC2)OCC=2C=NC=CC=2)=C1 DUYPUTNYDZJOSY-UHFFFAOYSA-N 0.000 claims 1
- JIDGQLCWPXMSMN-UHFFFAOYSA-N 2-amino-N-[3-(furan-3-ylamino)-5-[2-(4-methylpiperazin-1-yl)-4-(pyrimidin-2-ylmethoxy)pyrimidin-5-yl]sulfinylphenyl]-4-methylpentanamide Chemical compound NC(C(=O)NC1=CC(=CC(=C1)S(=O)C=1C(=NC(=NC=1)N1CCN(CC1)C)OCC1=NC=CC=N1)NC1=COC=C1)CC(C)C JIDGQLCWPXMSMN-UHFFFAOYSA-N 0.000 claims 1
- MLIYXZPJIBOWDH-UHFFFAOYSA-N 2-amino-N-[3-[2-(4-methylpiperazin-1-yl)-4-(1H-pyrrol-3-yl)pyrimidin-5-yl]sulfanylphenyl]propanamide Chemical compound NC(C(=O)NC1=CC(=CC=C1)SC=1C(=NC(=NC=1)N1CCN(CC1)C)C1=CNC=C1)C MLIYXZPJIBOWDH-UHFFFAOYSA-N 0.000 claims 1
- VJJYIEZJOAQEOR-UHFFFAOYSA-N 2-amino-N-[3-[2-(4-methylpiperazin-1-yl)-4-(3-nitrophenyl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound CN1CCN(CC1)c1ncc(Sc2cccc(NC(=O)CN)c2)c(n1)-c1cccc(c1)[N+]([O-])=O VJJYIEZJOAQEOR-UHFFFAOYSA-N 0.000 claims 1
- PUGJXPZABYPEAD-UHFFFAOYSA-N 2-amino-N-[3-[2-(4-methylpiperazin-1-yl)-4-(3-sulfamoylphenyl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound NCC(=O)NC1=CC(=CC=C1)SC=1C(=NC(=NC=1)N1CCN(CC1)C)C1=CC(=CC=C1)S(N)(=O)=O PUGJXPZABYPEAD-UHFFFAOYSA-N 0.000 claims 1
- GIRFJZWOTXJJGY-UHFFFAOYSA-N 2-amino-N-[3-[2-(4-methylpiperazin-1-yl)-4-(pyrrolidin-2-ylmethoxy)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound NCC(=O)NC1=CC(=CC=C1)SC=1C(=NC(=NC=1)N1CCN(CC1)C)OCC1NCCC1 GIRFJZWOTXJJGY-UHFFFAOYSA-N 0.000 claims 1
- BTFGLWLPXHOAFA-UHFFFAOYSA-N 2-amino-N-[3-[2-(4-methylpiperazin-1-yl)-4-piperidin-4-yloxypyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound NCC(=O)NC1=CC(=CC=C1)SC=1C(=NC(=NC=1)N1CCN(CC1)C)OC1CCNCC1 BTFGLWLPXHOAFA-UHFFFAOYSA-N 0.000 claims 1
- UESJBRIBEVWVFV-UHFFFAOYSA-N 2-amino-N-[3-[4-(2-methoxyethyl)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]propanamide Chemical compound NC(C(=O)NC1=CC(=CC=C1)SC=1C(=NC(=NC1)N1CCN(CC1)C)CCOC)C UESJBRIBEVWVFV-UHFFFAOYSA-N 0.000 claims 1
- USDUCXSIOHVGHL-UHFFFAOYSA-N 2-amino-N-[3-[4-(3-cyanophenyl)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound NCC(=O)NC1=CC(=CC=C1)SC=1C(=NC(=NC=1)N1CCN(CC1)C)C1=CC(=CC=C1)C#N USDUCXSIOHVGHL-UHFFFAOYSA-N 0.000 claims 1
- AVOBOKQPKYYDDG-UHFFFAOYSA-N 2-amino-N-[3-[4-(furan-2-yl)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound NCC(=O)NC1=CC(=CC=C1)SC=1C(=NC(=NC=1)N1CCN(CC1)C)C=1OC=CC=1 AVOBOKQPKYYDDG-UHFFFAOYSA-N 0.000 claims 1
- QYENWZBSBLGLLS-UHFFFAOYSA-N 2-amino-N-[3-[4-benzyl-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound CN1CCN(CC1)c1ncc(Sc2cccc(NC(=O)CN)c2)c(Cc2ccccc2)n1 QYENWZBSBLGLLS-UHFFFAOYSA-N 0.000 claims 1
- BVJOIKIQJPDQKQ-UHFFFAOYSA-N 2-amino-N-[3-amino-5-[2-(4-methylpiperazin-1-yl)-4-(1H-pyrrol-2-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound CN1CCN(CC1)c1ncc(Sc2cc(N)cc(NC(=O)CN)c2)c(n1)-c1ccc[nH]1 BVJOIKIQJPDQKQ-UHFFFAOYSA-N 0.000 claims 1
- WXHIWCARTVJRKB-UHFFFAOYSA-N 2-amino-N-[3-amino-5-[4-[2-(dimethylamino)ethoxy]-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound CN(C)CCOc1nc(ncc1Sc1cc(N)cc(NC(=O)CN)c1)N1CCN(C)CC1 WXHIWCARTVJRKB-UHFFFAOYSA-N 0.000 claims 1
- YAUKIPWEEHSJRZ-UHFFFAOYSA-N 2-amino-N-[3-methoxy-5-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxy-6-(trifluoromethyl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound COc1cc(NC(=O)CN)cc(Sc2c(OCc3ccccc3)nc(nc2C(F)(F)F)N2CCN(C)CC2)c1 YAUKIPWEEHSJRZ-UHFFFAOYSA-N 0.000 claims 1
- TZGXYFXZWKJNIU-UHFFFAOYSA-N 2-amino-N-[5-[4-(3-aminophenoxy)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyridin-3-yl]acetamide Chemical compound CN1CCN(CC1)c1ncc(Sc2cncc(NC(=O)CN)c2)c(Oc2cccc(N)c2)n1 TZGXYFXZWKJNIU-UHFFFAOYSA-N 0.000 claims 1
- WBKYIVMRMRGAND-UHFFFAOYSA-N 2-amino-n-[2-[2-(4-methylpiperazin-1-yl)-4-pyridin-2-yloxypyrimidin-5-yl]sulfonylpyridin-4-yl]propanamide Chemical compound CC(N)C(=O)NC1=CC=NC(S(=O)(=O)C=2C(=NC(=NC=2)N2CCN(C)CC2)OC=2N=CC=CC=2)=C1 WBKYIVMRMRGAND-UHFFFAOYSA-N 0.000 claims 1
- ZPULTNBTXYNTGD-UHFFFAOYSA-N 2-amino-n-[2-[4-(3-carbamimidoylphenoxy)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylpyrimidin-4-yl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OC=2C=C(C=CC=2)C(N)=N)=NC=C1SC1=NC=CC(NC(=O)CN)=N1 ZPULTNBTXYNTGD-UHFFFAOYSA-N 0.000 claims 1
- SQSOAGNWLUZBQX-UHFFFAOYSA-N 2-amino-n-[3-(dimethylamino)-5-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound CN(C)C1=CC(NC(=O)CN)=CC(SC=2C(=NC(=NC=2)N2CCN(C)CC2)OCC=2C=CC=CC=2)=C1 SQSOAGNWLUZBQX-UHFFFAOYSA-N 0.000 claims 1
- IDEJWXAHLUIUFI-UHFFFAOYSA-N 2-amino-n-[3-[2-(4-methylpiperazin-1-yl)-4-(2-phenylethoxy)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCCC=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 IDEJWXAHLUIUFI-UHFFFAOYSA-N 0.000 claims 1
- NPWCUCNZGXDXLI-UHFFFAOYSA-N 2-amino-n-[3-[2-(4-methylpiperazin-1-yl)-4-phenoxypyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OC=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 NPWCUCNZGXDXLI-UHFFFAOYSA-N 0.000 claims 1
- HGVSBOBCHXUIDR-UHFFFAOYSA-N 2-amino-n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylmethoxypyrimidin-5-yl]sulfanylphenyl]propanamide Chemical compound CC(N)C(=O)NC1=CC=CC(SC=2C(=NC(=NC=2)N2CCN(C)CC2)OCC=2C=CC=CC=2)=C1 HGVSBOBCHXUIDR-UHFFFAOYSA-N 0.000 claims 1
- PRPJPXKHEXEWMD-UHFFFAOYSA-N 2-amino-n-[3-[2-(4-methylpiperazin-1-yl)-4-phenylpyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1C=2C=CC=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 PRPJPXKHEXEWMD-UHFFFAOYSA-N 0.000 claims 1
- MJUDNBMVFJCLNC-UHFFFAOYSA-N 2-amino-n-[3-[4,6-dimethoxy-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound COC1=NC(N2CCN(C)CC2)=NC(OC)=C1SC1=CC=CC(NC(=O)CN)=C1 MJUDNBMVFJCLNC-UHFFFAOYSA-N 0.000 claims 1
- OZVFORACOQABEZ-UHFFFAOYSA-N 2-amino-n-[3-[4-(2-cyclopentylethoxy)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCCC2CCCC2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 OZVFORACOQABEZ-UHFFFAOYSA-N 0.000 claims 1
- QSRYIMHCQSXOCQ-UHFFFAOYSA-N 2-amino-n-[3-[4-(cyclopentylmethoxy)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC2CCCC2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 QSRYIMHCQSXOCQ-UHFFFAOYSA-N 0.000 claims 1
- PWWSSBPMFQTSDQ-UHFFFAOYSA-N 2-amino-n-[3-[4-(furan-2-ylmethoxy)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2OC=CC=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 PWWSSBPMFQTSDQ-UHFFFAOYSA-N 0.000 claims 1
- BZDUTPGUENURCZ-UHFFFAOYSA-N 2-amino-n-[3-[4-(furan-3-ylmethoxy)-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC2=COC=C2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 BZDUTPGUENURCZ-UHFFFAOYSA-N 0.000 claims 1
- RCQAEBYGVAKXIV-UHFFFAOYSA-N 2-amino-n-[3-[4-[(2-aminophenyl)methoxy]-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C(=CC=CC=2)N)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 RCQAEBYGVAKXIV-UHFFFAOYSA-N 0.000 claims 1
- XPLNHOQLTBFIEV-UHFFFAOYSA-N 2-amino-n-[3-[4-[(3,5-difluorophenyl)methoxy]-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1CN(C)CCN1C(N=C1OCC=2C=C(F)C=C(F)C=2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 XPLNHOQLTBFIEV-UHFFFAOYSA-N 0.000 claims 1
- DLRYALOYUNFCPD-UHFFFAOYSA-N 2-amino-n-[3-[4-[(3-bromo-2-methoxyphenyl)methoxy]-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanyl-5-methoxyphenyl]acetamide Chemical compound COC1=CC(NC(=O)CN)=CC(SC=2C(=NC(=NC=2)N2CCN(C)CC2)OCC=2C(=C(Br)C=CC=2)OC)=C1 DLRYALOYUNFCPD-UHFFFAOYSA-N 0.000 claims 1
- QPRWHKWKQCPJTQ-UHFFFAOYSA-N 2-amino-n-[3-[4-[(4-methoxyphenyl)methoxy]-2-(4-methylpiperazin-1-yl)pyrimidin-5-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(OC)=CC=C1COC1=NC(N2CCN(C)CC2)=NC=C1SC1=CC=CC(NC(=O)CN)=C1 QPRWHKWKQCPJTQ-UHFFFAOYSA-N 0.000 claims 1
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A—HUMAN NECESSITIES
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- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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