BR112017016428B1 - Composto ou sal farmaceuticamente aceitável, composição farmacêutica, e, uso de um composto ou sal farmaceuticamente aceitável - Google Patents

Info

Publication number

BR112017016428B1

BR112017016428B1 BR112017016428-0A BR112017016428A BR112017016428B1 BR 112017016428 B1 BR112017016428 B1 BR 112017016428B1 BR 112017016428 A BR112017016428 A BR 112017016428A BR 112017016428 B1 BR112017016428 B1 BR 112017016428B1

Authority

BR

Brazil

Prior art keywords

pyridin

amino

imidazo

chloro

phenoxy

Prior art date

2015-02-02

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 244
• 150000003839 salts Chemical class 0.000 title claims abstract description 54
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
• 208000035475 disorder Diseases 0.000 claims abstract description 26
• 230000002503 metabolic effect Effects 0.000 claims abstract description 16
• 208000008589 Obesity Diseases 0.000 claims abstract description 14
• 235000020824 obesity Nutrition 0.000 claims abstract description 14
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 12
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 12
• 230000003211 malignant effect Effects 0.000 claims abstract description 12
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 193
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 139
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 134
• 125000004122 cyclic group Chemical group 0.000 claims description 116
• 125000000623 heterocyclic group Chemical group 0.000 claims description 86
• 229910052736 halogen Inorganic materials 0.000 claims description 64
• 150000002367 halogens Chemical class 0.000 claims description 63
• 229910052760 oxygen Inorganic materials 0.000 claims description 54
• 125000004429 atom Chemical group 0.000 claims description 51
• 229910052717 sulfur Inorganic materials 0.000 claims description 48
• 125000005842 heteroatom Chemical group 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 43
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• -1 1-benzylpiperidin-4-yl Chemical group 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 7
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 230000001363 autoimmune Effects 0.000 claims description 3
• KQEJRGVONMKKJF-UHFFFAOYSA-N 2-[4-[6-bromo-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC KQEJRGVONMKKJF-UHFFFAOYSA-N 0.000 claims description 2
• DEBIFPJQQVOTQW-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)-methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(diethylamino)ethyl]acetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NCCN(CC)CC)C=C1)C DEBIFPJQQVOTQW-UHFFFAOYSA-N 0.000 claims description 2
• HGPUZPOMFGHTBJ-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[1-(dimethylamino)-2-methylpropan-2-yl]acetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC(CN(C)C)(C)C)C=C1 HGPUZPOMFGHTBJ-UHFFFAOYSA-N 0.000 claims description 2
• PUBCULABZDVDDO-UHFFFAOYSA-N 3-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-[2-(dimethylamino)ethyl]propanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NCCN(C)C)NC1CCN(CC1)CC1=CC=C(C=C1)OC PUBCULABZDVDDO-UHFFFAOYSA-N 0.000 claims description 2
• JSIPSIFOVVZDLF-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]-2-methylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(C(C)C)=O)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC JSIPSIFOVVZDLF-UHFFFAOYSA-N 0.000 claims description 2
• YFJXJNUDHRRVRS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrazin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CN=C2)C=C1)NC1CCN(CC1)C YFJXJNUDHRRVRS-UHFFFAOYSA-N 0.000 claims 2
• PFGREAAARAPYCI-UHFFFAOYSA-N 2-[3-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C=1C=C(OCC(=O)NC)C=CC=1)NC1CCN(CC1)C PFGREAAARAPYCI-UHFFFAOYSA-N 0.000 claims 1
• PJANUZARGOKUEM-IBGZPJMESA-N 2-[3-[6-chloro-7-[[(3S)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C=1C=C(OCC(=O)NC)C=CC=1)N[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC PJANUZARGOKUEM-IBGZPJMESA-N 0.000 claims 1
• QUUHBPJTHLVUIK-UHFFFAOYSA-N 2-[3-[6-chloro-7-[[1-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C=1C=C(OCC(=O)NC)C=CC=1)NC1CCN(CC1)CC=1C=CC2=C(CCO2)C=1 QUUHBPJTHLVUIK-UHFFFAOYSA-N 0.000 claims 1
• YICFECJDOFPZPI-UHFFFAOYSA-N 2-[3-[6-chloro-7-[[1-(2-phenoxyethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC(=CC=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CCOC2=CC=CC=C2)CC1 YICFECJDOFPZPI-UHFFFAOYSA-N 0.000 claims 1
• BJFMYXMEASIHNJ-UHFFFAOYSA-N 2-[3-[6-chloro-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC(=CC=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=CS2)CC1 BJFMYXMEASIHNJ-UHFFFAOYSA-N 0.000 claims 1
• CYYZNOBYKFLABJ-UHFFFAOYSA-N 2-[3-[6-chloro-7-[[1-(thiophen-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC(=CC=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CSC=C2)CC1 CYYZNOBYKFLABJ-UHFFFAOYSA-N 0.000 claims 1
• RSPUDPSRWQPMHW-UHFFFAOYSA-N 2-[3-[6-chloro-7-[[1-[(3-hydroxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC(=CC=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(O)=CC=C2)CC1 RSPUDPSRWQPMHW-UHFFFAOYSA-N 0.000 claims 1
• QUDAHHCYWDLDQR-UHFFFAOYSA-N 2-[3-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC(=CC=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(OC)C=C2)CC1 QUDAHHCYWDLDQR-UHFFFAOYSA-N 0.000 claims 1
• YWCJHZOMCPVYBP-UHFFFAOYSA-N 2-[3-[6-chloro-7-[[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C=1C=C(OCC(=O)NC)C=CC=1)NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 YWCJHZOMCPVYBP-UHFFFAOYSA-N 0.000 claims 1
• AEGNCPXEHFKKRV-IBGZPJMESA-N 2-[3-[7-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C=1C=C(OCC(=O)NC)C=CC=1 AEGNCPXEHFKKRV-IBGZPJMESA-N 0.000 claims 1
• CLZBSPYTAZGEQB-UHFFFAOYSA-N 2-[3-[7-[[1-(1,3-benzodioxol-5-ylmethyl)piperidin-4-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC(=CC=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC3=C(OCO3)C=C2)CC1 CLZBSPYTAZGEQB-UHFFFAOYSA-N 0.000 claims 1
• WHYHJALYFQADLC-UHFFFAOYSA-N 2-[4-[5-chloro-4-[(1-methylpiperidin-4-yl)amino]-1H-pyrrolo[2,3-b]pyridin-2-yl]phenoxy]-N-(5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=C2)C1=CC=C(OCC(=O)NC2=NOC(=C2)C)C=C1)NC1CCN(CC1)C WHYHJALYFQADLC-UHFFFAOYSA-N 0.000 claims 1
• PPQPAUMPYJCXEY-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)F)NC1CCN(CC1)CC PPQPAUMPYJCXEY-UHFFFAOYSA-N 0.000 claims 1
• AYULLZAEYBJCLL-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC AYULLZAEYBJCLL-UHFFFAOYSA-N 0.000 claims 1
• SEHPIBDETXXZDD-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC SEHPIBDETXXZDD-UHFFFAOYSA-N 0.000 claims 1
• IMIINPYCPZUMJA-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,2-dimethylpropanamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OC(C(=O)NC)(C)C)C=C1)NC1CCN(CC1)CC IMIINPYCPZUMJA-UHFFFAOYSA-N 0.000 claims 1
• GEZCXYIYASMCCK-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC GEZCXYIYASMCCK-UHFFFAOYSA-N 0.000 claims 1
• BGZHBZIXQAOBGE-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,5-dimethylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1C)C)NC1CCN(CC1)C BGZHBZIXQAOBGE-UHFFFAOYSA-N 0.000 claims 1
• GPYGHFMJDJITKV-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C(=C1)C)C)NC1CCN(CC1)C GPYGHFMJDJITKV-UHFFFAOYSA-N 0.000 claims 1
• WKLKCQBXEDMLAP-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)F)NC1CCN(CC1)C WKLKCQBXEDMLAP-UHFFFAOYSA-N 0.000 claims 1
• JMVPOEXLLBHZRI-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methoxyphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)OC)NC1CCN(CC1)C JMVPOEXLLBHZRI-UHFFFAOYSA-N 0.000 claims 1
• APRUNWQSIBAXCL-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)C APRUNWQSIBAXCL-UHFFFAOYSA-N 0.000 claims 1
• NEGGKSLODBFGJM-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)C NEGGKSLODBFGJM-UHFFFAOYSA-N 0.000 claims 1
• INPJEWPYUVKQIP-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]anilino]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)NCC(=O)NC)NC1CCN(CC1)C INPJEWPYUVKQIP-UHFFFAOYSA-N 0.000 claims 1
• HRAURCVYVPHICM-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,2-dimethylpropanamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OC(C(=O)NC)(C)C)C=C1)NC1CCN(CC1)C HRAURCVYVPHICM-UHFFFAOYSA-N 0.000 claims 1
• OXWQDDUURXATEM-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,2-oxazol-3-yl)acetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1)NC1CCN(CC1)C OXWQDDUURXATEM-UHFFFAOYSA-N 0.000 claims 1
• DCNZELRSBDBYQE-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1-methoxybutan-2-yl)acetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(CC)COC)C=C1)NC1CCN(CC1)C DCNZELRSBDBYQE-UHFFFAOYSA-N 0.000 claims 1
• UAIBIQIASCOJKC-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-methylbutan-2-yl)acetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(CC)(C)C)C=C1)NC1CCN(CC1)C UAIBIQIASCOJKC-UHFFFAOYSA-N 0.000 claims 1
• IWBIUGUUTIIISD-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-methylpropyl)acetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC(C)C)C=C1)NC1CCN(CC1)C IWBIUGUUTIIISD-UHFFFAOYSA-N 0.000 claims 1
• YSIIBXAERPEBMD-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclohexylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCCC2)C=C1)NC1CCN(CC1)C YSIIBXAERPEBMD-UHFFFAOYSA-N 0.000 claims 1
• NIARDDQTWCLNFS-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclopentylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCC2)C=C1)NC1CCN(CC1)C NIARDDQTWCLNFS-UHFFFAOYSA-N 0.000 claims 1
• MDOXJKROLCOMHT-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-ethylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC)C=C1)NC1CCN(CC1)C MDOXJKROLCOMHT-UHFFFAOYSA-N 0.000 claims 1
• AUGINJYMWNKSOR-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)C AUGINJYMWNKSOR-UHFFFAOYSA-N 0.000 claims 1
• PWLJCIUQSCXZRL-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-propan-2-ylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(C)C)C=C1)NC1CCN(CC1)C PWLJCIUQSCXZRL-UHFFFAOYSA-N 0.000 claims 1
• CWJWHVJPRZSWMV-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-propylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCC)C=C1)NC1CCN(CC1)C CWJWHVJPRZSWMV-UHFFFAOYSA-N 0.000 claims 1
• KNAMRXVXXPIUDC-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrazin-2-ylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CN=C2)C=C1)NC1CCN(CC1)C KNAMRXVXXPIUDC-UHFFFAOYSA-N 0.000 claims 1
• OOKBYSWLKOFUKD-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyridin-4-ylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=CC=NC=C2)C=C1)NC1CCN(CC1)C OOKBYSWLKOFUKD-UHFFFAOYSA-N 0.000 claims 1
• BAIJRMXYDVOHRU-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-tert-butylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(C)(C)C)C=C1)NC1CCN(CC1)C BAIJRMXYDVOHRU-UHFFFAOYSA-N 0.000 claims 1
• FFAYIPCBERMWAO-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CC(=O)NC)NC1CCN(CC1)C FFAYIPCBERMWAO-UHFFFAOYSA-N 0.000 claims 1
• PVVMLFKAIIIZHX-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C(=C1)C)C)NC1CCN(CC1)C(C)C PVVMLFKAIIIZHX-UHFFFAOYSA-N 0.000 claims 1
• QRGDQMGNAMGYEK-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Br)=C2NC1CCN(CC1)C(C)C QRGDQMGNAMGYEK-UHFFFAOYSA-N 0.000 claims 1
• SNMGMRZFEKOUPL-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound CNC(=O)CC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Br)=C2NC1CCN(CC1)C(C)C SNMGMRZFEKOUPL-UHFFFAOYSA-N 0.000 claims 1
• ASMLYJBUASNRGZ-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methoxyphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)OC)NC1CCN(CC1)CCC ASMLYJBUASNRGZ-UHFFFAOYSA-N 0.000 claims 1
• XHRGWSHILVEEGO-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CCC XHRGWSHILVEEGO-UHFFFAOYSA-N 0.000 claims 1
• IZBLKGLVKBVRQH-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CCC IZBLKGLVKBVRQH-UHFFFAOYSA-N 0.000 claims 1
• SIOSVPOYEIOSAT-UHFFFAOYSA-N 2-[4-[6-bromo-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CC(=O)NC)NC1CCN(CC1)CCC SIOSVPOYEIOSAT-UHFFFAOYSA-N 0.000 claims 1
• MPDLHDOMYYJZDG-IBGZPJMESA-N 2-[4-[6-bromo-7-[[(3S)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC MPDLHDOMYYJZDG-IBGZPJMESA-N 0.000 claims 1
• SJYNDJXGSLEYOW-ZDUSSCGKSA-N 2-[4-[6-bromo-7-[[(3S)-1-methylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)C SJYNDJXGSLEYOW-ZDUSSCGKSA-N 0.000 claims 1
• SQMKFZMKLBJRFS-UHFFFAOYSA-N 2-[4-[6-bromo-7-[[1-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Br)=C2NC1CCN(CC2=CC3=C(OCC3)C=C2)CC1 SQMKFZMKLBJRFS-UHFFFAOYSA-N 0.000 claims 1
• QCGIKNWFHNRCQH-UHFFFAOYSA-N 2-[4-[6-bromo-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C(=C1)C)C)NC1CCN(CC1)CC=1SC=CC=1 QCGIKNWFHNRCQH-UHFFFAOYSA-N 0.000 claims 1
• NBJUABGPHSJVBU-UHFFFAOYSA-N 2-[4-[6-bromo-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1SC=CC=1 NBJUABGPHSJVBU-UHFFFAOYSA-N 0.000 claims 1
• DYMBPRHEFUKZAC-UHFFFAOYSA-N 2-[4-[6-bromo-7-[[1-[(1,3,5-trimethylpyrazol-4-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1C(=NN(C=1C)C)C DYMBPRHEFUKZAC-UHFFFAOYSA-N 0.000 claims 1
• SAWSKIHAIXJLTN-UHFFFAOYSA-N 2-[4-[6-bromo-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC1=CC=C(C=C1)OC SAWSKIHAIXJLTN-UHFFFAOYSA-N 0.000 claims 1
• QVUKQALSGUVITM-UHFFFAOYSA-N 2-[4-[6-bromo-7-[[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 QVUKQALSGUVITM-UHFFFAOYSA-N 0.000 claims 1
• QXNPHBVAMYBWKR-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CC(N(C(C1)(C)C)C)(C)C QXNPHBVAMYBWKR-UHFFFAOYSA-N 0.000 claims 1
• YOOJXSDKWJRHNQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-cyclohexylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)C1CCCCC1 YOOJXSDKWJRHNQ-UHFFFAOYSA-N 0.000 claims 1
• GENAJBNMPQOTAY-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,5-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1C)C)NC1CCN(CC1)CC GENAJBNMPQOTAY-UHFFFAOYSA-N 0.000 claims 1
• CXWSDZJBBDMMBL-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C(=C1)C)C)NC1CCN(CC1)CC CXWSDZJBBDMMBL-UHFFFAOYSA-N 0.000 claims 1
• UKNVGMSVOHQINX-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)F)NC1CCN(CC1)CC UKNVGMSVOHQINX-UHFFFAOYSA-N 0.000 claims 1
• YILJFNXPRGRXOQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-propan-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC(C)C)C=C1)F)NC1CCN(CC1)CC YILJFNXPRGRXOQ-UHFFFAOYSA-N 0.000 claims 1
• YUAXXUFGSSWCDB-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methoxyphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)OC)NC1CCN(CC1)CC YUAXXUFGSSWCDB-UHFFFAOYSA-N 0.000 claims 1
• DXTSFQBCRWKNGA-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC DXTSFQBCRWKNGA-UHFFFAOYSA-N 0.000 claims 1
• ODOCDCBEGYTDLF-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC ODOCDCBEGYTDLF-UHFFFAOYSA-N 0.000 claims 1
• KWNJSWZYKBLCGA-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]anilino]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)NCC(=O)NC)NC1CCN(CC1)CC KWNJSWZYKBLCGA-UHFFFAOYSA-N 0.000 claims 1
• BSJAIJISOFKGCH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,2-dimethylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OC(C(=O)NC)(C)C)C=C1)NC1CCN(CC1)CC BSJAIJISOFKGCH-UHFFFAOYSA-N 0.000 claims 1
• YXZZWWDGCKXECU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC YXZZWWDGCKXECU-UHFFFAOYSA-N 0.000 claims 1
• FONBOAUQIVWDPG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CC(=O)NC)NC1CCN(CC1)CC FONBOAUQIVWDPG-UHFFFAOYSA-N 0.000 claims 1
• MUERKUAHJXHJKS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,5-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1C)C)NC1CCN(CC1)C MUERKUAHJXHJKS-UHFFFAOYSA-N 0.000 claims 1
• SDFRJLKBYBKJGF-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C(=C1)C)C)NC1CCN(CC1)C SDFRJLKBYBKJGF-UHFFFAOYSA-N 0.000 claims 1
• COCYYQAONCLISW-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)F)NC1CCN(CC1)C COCYYQAONCLISW-UHFFFAOYSA-N 0.000 claims 1
• DVLUPNWOMMHWAH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-propan-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC(C)C)C=C1)F)NC1CCN(CC1)C DVLUPNWOMMHWAH-UHFFFAOYSA-N 0.000 claims 1
• FYDFQLPERAEMPQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methoxyphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)OC)NC1CCN(CC1)C FYDFQLPERAEMPQ-UHFFFAOYSA-N 0.000 claims 1
• YPVONIDRLRDEJN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)C YPVONIDRLRDEJN-UHFFFAOYSA-N 0.000 claims 1
• QTUREFWMYFTBKY-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)C QTUREFWMYFTBKY-UHFFFAOYSA-N 0.000 claims 1
• VTCSVALJFXQBED-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-N-methylanilino]-N-pyridin-3-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)N(CC(=O)NC=1C=NC=CC=1)C)NC1CCN(CC1)C VTCSVALJFXQBED-UHFFFAOYSA-N 0.000 claims 1
• TTXGASQUHPTMPP-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]anilino]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)NCC(=O)NC)NC1CCN(CC1)C TTXGASQUHPTMPP-UHFFFAOYSA-N 0.000 claims 1
• ARMHGQVTFQNPRE-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,2-dimethylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OC(C(=O)NC)(C)C)C=C1)NC1CCN(CC1)C ARMHGQVTFQNPRE-UHFFFAOYSA-N 0.000 claims 1
• MYULWYQSMUFNIQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,2-oxazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1)NC1CCN(CC1)C MYULWYQSMUFNIQ-UHFFFAOYSA-N 0.000 claims 1
• WLLSKPANLFELPL-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,3,4-thiadiazol-2-yl)acetamide Chemical compound CN1CCC(CC1)NC1=C(Cl)C=NC2=C1N=C(N2)C1=CC=C(OCC(=O)NC2=NN=CS2)C=C1 WLLSKPANLFELPL-UHFFFAOYSA-N 0.000 claims 1
• WOHNWVOXPGFMEK-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,3-thiazol-2-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC=2SC=CN=2)C=C1)NC1CCN(CC1)C WOHNWVOXPGFMEK-UHFFFAOYSA-N 0.000 claims 1
• QAQPRGNWCGDNLH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1-methoxybutan-2-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(CC)COC)C=C1)NC1CCN(CC1)C QAQPRGNWCGDNLH-UHFFFAOYSA-N 0.000 claims 1
• SNHJXHIXTDVFFA-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1-methoxypropan-2-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(COC)C)C=C1)NC1CCN(CC1)C SNHJXHIXTDVFFA-UHFFFAOYSA-N 0.000 claims 1
• DJKCTBOXDPRHNG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1-phenylethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(C)C2=CC=CC=C2)C=C1)NC1CCN(CC1)C DJKCTBOXDPRHNG-UHFFFAOYSA-N 0.000 claims 1
• OPKLHFQZNVRIMT-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1H-1,2,4-triazol-5-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NNC=N2)C=C1)NC1CCN(CC1)C OPKLHFQZNVRIMT-UHFFFAOYSA-N 0.000 claims 1
• KWMBRWMLXOFQRB-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2,2,2-trifluoroethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC(F)(F)F)C=C1)NC1CCN(CC1)C KWMBRWMLXOFQRB-UHFFFAOYSA-N 0.000 claims 1
• VIMUHMVCBXLNMV-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-cyclohexylethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCC2CCCCC2)C=C1)NC1CCN(CC1)C VIMUHMVCBXLNMV-UHFFFAOYSA-N 0.000 claims 1
• HGOOWKSOHBUHQV-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-methoxyethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCOC)C=C1)NC1CCN(CC1)C HGOOWKSOHBUHQV-UHFFFAOYSA-N 0.000 claims 1
• TWEKJTGTTPIJSI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-methylbutan-2-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(CC)(C)C)C=C1)NC1CCN(CC1)C TWEKJTGTTPIJSI-UHFFFAOYSA-N 0.000 claims 1
• JWAITHOXSULBTL-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-methylpropyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC(C)C)C=C1)NC1CCN(CC1)C JWAITHOXSULBTL-UHFFFAOYSA-N 0.000 claims 1
• GZFRINKMDGQSCZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-methylpyrazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=CC=NN2C)C=C1)NC1CCN(CC1)C GZFRINKMDGQSCZ-UHFFFAOYSA-N 0.000 claims 1
• JPARYCWWCUCJQN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-morpholin-4-ylethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN2CCOCC2)C=C1)NC1CCN(CC1)C JPARYCWWCUCJQN-UHFFFAOYSA-N 0.000 claims 1
• BFXDOAKPTJTTJQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-piperidin-4-ylethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCC2CCNCC2)C=C1)NC1CCN(CC1)C BFXDOAKPTJTTJQ-UHFFFAOYSA-N 0.000 claims 1
• UGUGCWONLXENQE-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-propan-2-yloxyethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCOC(C)C)C=C1)NC1CCN(CC1)C UGUGCWONLXENQE-UHFFFAOYSA-N 0.000 claims 1
• IKJKZWCBJFSYGP-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(3-methyl-1,2-oxazol-5-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=CC(=NO2)C)C=C1)NC1CCN(CC1)C IKJKZWCBJFSYGP-UHFFFAOYSA-N 0.000 claims 1
• UXIZJEPOTSDSHG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(3-morpholin-4-ylpropyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCCN2CCOCC2)C=C1)NC1CCN(CC1)C UXIZJEPOTSDSHG-UHFFFAOYSA-N 0.000 claims 1
• DZMKMDJOXDQLTN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(4-methylcyclohexyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCC(CC2)C)C=C1)NC1CCN(CC1)C DZMKMDJOXDQLTN-UHFFFAOYSA-N 0.000 claims 1
• ZGVYGPJONOBMJR-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(5-chloropyridin-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC=2C=NC=C(C=2)Cl)C=C1)NC1CCN(CC1)C ZGVYGPJONOBMJR-UHFFFAOYSA-N 0.000 claims 1
• SODRXQNBKMYMMN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(cyclohexylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2CCCCC2)C=C1)NC1CCN(CC1)C SODRXQNBKMYMMN-UHFFFAOYSA-N 0.000 claims 1
• ROOUGFOWFMYDSG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(furan-2-ylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC=2OC=CC=2)C=C1)NC1CCN(CC1)C ROOUGFOWFMYDSG-UHFFFAOYSA-N 0.000 claims 1
• KMGQLVABTWOAEA-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(oxan-4-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCOCC2)C=C1)NC1CCN(CC1)C KMGQLVABTWOAEA-UHFFFAOYSA-N 0.000 claims 1
• IOXXHUAXTWIGDT-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(oxan-4-ylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2CCOCC2)C=C1)NC1CCN(CC1)C IOXXHUAXTWIGDT-UHFFFAOYSA-N 0.000 claims 1
• XGSLEIUSWYSSCS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(oxolan-2-ylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2OCCC2)C=C1)NC1CCN(CC1)C XGSLEIUSWYSSCS-UHFFFAOYSA-N 0.000 claims 1
• RUBITKTUQNVKRN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(piperidin-4-ylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2CCNCC2)C=C1)NC1CCN(CC1)C RUBITKTUQNVKRN-UHFFFAOYSA-N 0.000 claims 1
• XPJHHCVZOISMFG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(pyridin-4-ylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2=CC=NC=C2)C=C1)NC1CCN(CC1)C XPJHHCVZOISMFG-UHFFFAOYSA-N 0.000 claims 1
• QHLLZSJBBGVBBB-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(thian-4-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCSCC2)C=C1)NC1CCN(CC1)C QHLLZSJBBGVBBB-UHFFFAOYSA-N 0.000 claims 1
• JJZQZJMEVISNGT-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(thiophen-2-ylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC=2SC=CC=2)C=C1)NC1CCN(CC1)C JJZQZJMEVISNGT-UHFFFAOYSA-N 0.000 claims 1
• LWLLOCIMERAKOH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[(1-methylpiperidin-4-yl)methyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2CCN(CC2)C)C=C1)NC1CCN(CC1)C LWLLOCIMERAKOH-UHFFFAOYSA-N 0.000 claims 1
• WUQYEYAAEQNEKK-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[(4-methoxyphenyl)methyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2=CC=C(C=C2)OC)C=C1)NC1CCN(CC1)C WUQYEYAAEQNEKK-UHFFFAOYSA-N 0.000 claims 1
• IWJYOTJVWGOXFS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(1-methylpiperidin-4-yl)ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCC2CCN(CC2)C)C=C1)NC1CCN(CC1)C IWJYOTJVWGOXFS-UHFFFAOYSA-N 0.000 claims 1
• XUXOYNYOYKUHEV-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1)NC1CCN(CC1)C XUXOYNYOYKUHEV-UHFFFAOYSA-N 0.000 claims 1
• FQJLXWISRCKMGV-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(oxan-4-yl)ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCC2CCOCC2)C=C1)NC1CCN(CC1)C FQJLXWISRCKMGV-UHFFFAOYSA-N 0.000 claims 1
• FFTSPNUOOXOFTC-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cycloheptylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCCCC2)C=C1)NC1CCN(CC1)C FFTSPNUOOXOFTC-UHFFFAOYSA-N 0.000 claims 1
• DQKQZRYFOADALD-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclohexylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCCC2)C=C1)NC1CCN(CC1)C DQKQZRYFOADALD-UHFFFAOYSA-N 0.000 claims 1
• CHFTUZOTVIIQOO-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclopentylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCC2)C=C1)NC1CCN(CC1)C CHFTUZOTVIIQOO-UHFFFAOYSA-N 0.000 claims 1
• BPMOJEBROGTPGQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-ethylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC)C=C1)NC1CCN(CC1)C BPMOJEBROGTPGQ-UHFFFAOYSA-N 0.000 claims 1
• ZEPYYZGGZJVHPP-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methoxyacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NOC)C=C1)NC1CCN(CC1)C ZEPYYZGGZJVHPP-UHFFFAOYSA-N 0.000 claims 1
• KEXBBGUQXLBEDM-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)C KEXBBGUQXLBEDM-UHFFFAOYSA-N 0.000 claims 1
• MKGDHDRUDFAOLO-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-propan-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(C)C)C=C1)NC1CCN(CC1)C MKGDHDRUDFAOLO-UHFFFAOYSA-N 0.000 claims 1
• UQYOVALMMNMDQU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-propylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCC)C=C1)NC1CCN(CC1)C UQYOVALMMNMDQU-UHFFFAOYSA-N 0.000 claims 1
• LZZZVHPBLZFJRI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyridin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CC=C2)C=C1)NC1CCN(CC1)C LZZZVHPBLZFJRI-UHFFFAOYSA-N 0.000 claims 1
• JWNSQZHDFJFDIO-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyridin-3-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC=2C=NC=CC=2)C=C1)NC1CCN(CC1)C JWNSQZHDFJFDIO-UHFFFAOYSA-N 0.000 claims 1
• GWNJLDUZELLVJM-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyridin-4-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=CC=NC=C2)C=C1)NC1CCN(CC1)C GWNJLDUZELLVJM-UHFFFAOYSA-N 0.000 claims 1
• WIAYKAWNLBIUOD-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrimidin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CC=N2)C=C1)NC1CCN(CC1)C WIAYKAWNLBIUOD-UHFFFAOYSA-N 0.000 claims 1
• HUXOPWZPBQCBCF-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrimidin-5-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC=2C=NC=NC=2)C=C1)NC1CCN(CC1)C HUXOPWZPBQCBCF-UHFFFAOYSA-N 0.000 claims 1
• WLXLMVUBXDSBKU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CC(=O)NC)NC1CCN(CC1)C WLXLMVUBXDSBKU-UHFFFAOYSA-N 0.000 claims 1
• LBXLSUJHANNZDV-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)F)NC1CCN(CC1)C(C)C LBXLSUJHANNZDV-UHFFFAOYSA-N 0.000 claims 1
• DHKOKFSZLXJLNE-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-propan-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC(C)C)C=C1)F)NC1CCN(CC1)C(C)C DHKOKFSZLXJLNE-UHFFFAOYSA-N 0.000 claims 1
• RLWDFPZKZOXWEI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methoxyphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)OC)NC1CCN(CC1)C(C)C RLWDFPZKZOXWEI-UHFFFAOYSA-N 0.000 claims 1
• NDCWMBFOKLWJMS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]anilino]-N-methylacetamide Chemical compound CNC(=O)CNC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC1)C(C)C NDCWMBFOKLWJMS-UHFFFAOYSA-N 0.000 claims 1
• LJUZQGCAZDWJNH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,2-dimethylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OC(C(=O)NC)(C)C)C=C1)NC1CCN(CC1)C(C)C LJUZQGCAZDWJNH-UHFFFAOYSA-N 0.000 claims 1
• JWLKLXHCANBEDZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,2-oxazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1)NC1CCN(CC1)C(C)C JWLKLXHCANBEDZ-UHFFFAOYSA-N 0.000 claims 1
• BYZLDRKRYLPRHJ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclohexylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCCC2)C=C1)NC1CCN(CC1)C(C)C BYZLDRKRYLPRHJ-UHFFFAOYSA-N 0.000 claims 1
• HZNWBPZZAQKGCU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)C(C)C HZNWBPZZAQKGCU-UHFFFAOYSA-N 0.000 claims 1
• BUWBPMOEIOXTGL-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrazin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CN=C2)C=C1)NC1CCN(CC1)C(C)C BUWBPMOEIOXTGL-UHFFFAOYSA-N 0.000 claims 1
• ZOVIHFYMCKRKBQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CC(=O)NC)NC1CCN(CC1)C(C)C ZOVIHFYMCKRKBQ-UHFFFAOYSA-N 0.000 claims 1
• OYQLVVPFOMLERY-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,5-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1C)C)NC1CCN(CC1)CCC OYQLVVPFOMLERY-UHFFFAOYSA-N 0.000 claims 1
• WPYCRDZXNYWZAK-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CCC WPYCRDZXNYWZAK-UHFFFAOYSA-N 0.000 claims 1
• KCYJAFZOPFODMJ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,2-oxazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1)NC1CCN(CC1)CCC KCYJAFZOPFODMJ-UHFFFAOYSA-N 0.000 claims 1
• GQIUKPCPCDLNON-UHFFFAOYSA-N 2-[4-[6-chloro-7-[(1-propylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CC(=O)NC)NC1CCN(CC1)CCC GQIUKPCPCDLNON-UHFFFAOYSA-N 0.000 claims 1
• XZVSFBYVQOPRCO-LJQANCHMSA-N 2-[4-[6-chloro-7-[[(3R)-1-[(4-fluorophenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@H]1CN(CC1)CC1=CC=C(C=C1)F XZVSFBYVQOPRCO-LJQANCHMSA-N 0.000 claims 1
• IRZXRVDMGDGJCO-HNNXBMFYSA-N 2-[4-[6-chloro-7-[[(3S)-1-(1,3-thiazol-2-ylmethyl)pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC=1SC=CN=1 IRZXRVDMGDGJCO-HNNXBMFYSA-N 0.000 claims 1
• ZCZDCVZBPKRLPE-FQEVSTJZSA-N 2-[4-[6-chloro-7-[[(3S)-1-(2-phenylethyl)pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CCC1=CC=CC=C1 ZCZDCVZBPKRLPE-FQEVSTJZSA-N 0.000 claims 1
• DNJBHCHLNRNEDU-INIZCTEOSA-N 2-[4-[6-chloro-7-[[(3S)-1-(thiophen-2-ylmethyl)pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC=1SC=CC=1 DNJBHCHLNRNEDU-INIZCTEOSA-N 0.000 claims 1
• OUJYXWGEQJBPSS-KRWDZBQOSA-N 2-[4-[6-chloro-7-[[(3S)-1-(thiophen-3-ylmethyl)pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CSC=C1 OUJYXWGEQJBPSS-KRWDZBQOSA-N 0.000 claims 1
• FLTLJMIMFBVQTN-FQEVSTJZSA-N 2-[4-[6-chloro-7-[[(3S)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)N[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC FLTLJMIMFBVQTN-FQEVSTJZSA-N 0.000 claims 1
• HCZPHUFESHNHPL-IBGZPJMESA-N 2-[4-[6-chloro-7-[[(3S)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC HCZPHUFESHNHPL-IBGZPJMESA-N 0.000 claims 1
• FSCSNVSPZSKXHI-FQEVSTJZSA-N 2-[4-[6-chloro-7-[[(3S)-1-[(2-methylphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=C(C=CC=C1)C FSCSNVSPZSKXHI-FQEVSTJZSA-N 0.000 claims 1
• OLBSLAAWHWODCT-FQEVSTJZSA-N 2-[4-[6-chloro-7-[[(3S)-1-[(3,4-difluorophenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1)N[C@@H]1CN(CC1)CC1=CC(=C(C=C1)F)F OLBSLAAWHWODCT-FQEVSTJZSA-N 0.000 claims 1
• WQPPHOPWWJGZQO-KRWDZBQOSA-N 2-[4-[6-chloro-7-[[(3S)-1-[(3,4-difluorophenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CC(=C(C=C1)F)F WQPPHOPWWJGZQO-KRWDZBQOSA-N 0.000 claims 1
• YTLWYONIEQZQEP-IBGZPJMESA-N 2-[4-[6-chloro-7-[[(3S)-1-[(3-methoxyphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CC(=CC=C1)OC YTLWYONIEQZQEP-IBGZPJMESA-N 0.000 claims 1
• JPAIMTGOJLRIRY-FQEVSTJZSA-N 2-[4-[6-chloro-7-[[(3S)-1-[(3-methylphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CC(=CC=C1)C JPAIMTGOJLRIRY-FQEVSTJZSA-N 0.000 claims 1
• ZKGRULKWHSTHQJ-KRWDZBQOSA-N 2-[4-[6-chloro-7-[[(3S)-1-[(3-methylthiophen-2-yl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC=1SC=CC=1C ZKGRULKWHSTHQJ-KRWDZBQOSA-N 0.000 claims 1
• XZVSFBYVQOPRCO-IBGZPJMESA-N 2-[4-[6-chloro-7-[[(3S)-1-[(4-fluorophenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CC=C(C=C1)F XZVSFBYVQOPRCO-IBGZPJMESA-N 0.000 claims 1
• VPISJSAGKAVSGY-IBGZPJMESA-N 2-[4-[6-chloro-7-[[(3S)-1-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CC=C(C=C1)OC VPISJSAGKAVSGY-IBGZPJMESA-N 0.000 claims 1
• GPABALKJOWFHMN-FQEVSTJZSA-N 2-[4-[6-chloro-7-[[(3S)-1-[(4-methylphenyl)methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CC=C(C=C1)C GPABALKJOWFHMN-FQEVSTJZSA-N 0.000 claims 1
• ANHTVGWIFLYNHR-IBGZPJMESA-N 2-[4-[6-chloro-7-[[(3S)-1-[[4-(trifluoromethyl)phenyl]methyl]pyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC1=CC=C(C=C1)C(F)(F)F ANHTVGWIFLYNHR-IBGZPJMESA-N 0.000 claims 1
• GRADFYHLCMDQLA-INIZCTEOSA-N 2-[4-[6-chloro-7-[[(3S)-1-ethylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C(=C1)C)C)N[C@@H]1CN(CC1)CC GRADFYHLCMDQLA-INIZCTEOSA-N 0.000 claims 1
• PCXQHTJHRRCFNN-ZDUSSCGKSA-N 2-[4-[6-chloro-7-[[(3S)-1-ethylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)F)N[C@@H]1CN(CC1)CC PCXQHTJHRRCFNN-ZDUSSCGKSA-N 0.000 claims 1
• YBHNYUPWCLMRSX-AWEZNQCLSA-N 2-[4-[6-chloro-7-[[(3S)-1-ethylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CC YBHNYUPWCLMRSX-AWEZNQCLSA-N 0.000 claims 1
• FVHSFXZLUXJCQY-ZDUSSCGKSA-N 2-[4-[6-chloro-7-[[(3S)-1-methylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)C FVHSFXZLUXJCQY-ZDUSSCGKSA-N 0.000 claims 1
• UHXXXQOMWBGTAD-KRWDZBQOSA-N 2-[4-[6-chloro-7-[[(3S)-1-propan-2-ylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C(=C1)C)C)N[C@@H]1CN(CC1)C(C)C UHXXXQOMWBGTAD-KRWDZBQOSA-N 0.000 claims 1
• YQRONCVLBUVQKR-HNNXBMFYSA-N 2-[4-[6-chloro-7-[[(3S)-1-propan-2-ylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methoxyphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)OC)N[C@@H]1CN(CC1)C(C)C YQRONCVLBUVQKR-HNNXBMFYSA-N 0.000 claims 1
• LOQGLRXCVSMQQT-INIZCTEOSA-N 2-[4-[6-chloro-7-[[(3S)-1-propan-2-ylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)N[C@@H]1CN(CC1)C(C)C LOQGLRXCVSMQQT-INIZCTEOSA-N 0.000 claims 1
• CTKUWKLLDRGGBK-INIZCTEOSA-N 2-[4-[6-chloro-7-[[(3S)-1-propan-2-ylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,2-dimethylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OC(C(=O)NC)(C)C)C=C1)N[C@@H]1CN(CC1)C(C)C CTKUWKLLDRGGBK-INIZCTEOSA-N 0.000 claims 1
• YODQQJHLHIOEMJ-HNNXBMFYSA-N 2-[4-[6-chloro-7-[[(3S)-1-propan-2-ylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)C(C)C YODQQJHLHIOEMJ-HNNXBMFYSA-N 0.000 claims 1
• UEWITTUKMREGDO-HNNXBMFYSA-N 2-[4-[6-chloro-7-[[(3S)-1-propylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)N[C@@H]1CN(CC1)CCC UEWITTUKMREGDO-HNNXBMFYSA-N 0.000 claims 1
• RCFIITPDOWSMDG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(1,3-thiazol-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=NC=CS2)CC1 RCFIITPDOWSMDG-UHFFFAOYSA-N 0.000 claims 1
• JDKSWQICNYOPSJ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(1,3-thiazol-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=NC=CS2)CC1 JDKSWQICNYOPSJ-UHFFFAOYSA-N 0.000 claims 1
• YEJHVBMQPKBRKQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2,2-dimethylpropyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC(C)(C)C)CC1 YEJHVBMQPKBRKQ-UHFFFAOYSA-N 0.000 claims 1
• BGAUFEGBVUFYRZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC2=C(OCCO2)C=C1 BGAUFEGBVUFYRZ-UHFFFAOYSA-N 0.000 claims 1
• NHZJKLCGYBLUNI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC=1C=CC2=C(CCO2)C=1 NHZJKLCGYBLUNI-UHFFFAOYSA-N 0.000 claims 1
• VMFWCDJJPOBQKH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1C=CC2=C(CCO2)C=1 VMFWCDJJPOBQKH-UHFFFAOYSA-N 0.000 claims 1
• JXVLUHIEXCRYKR-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrazin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CN=C2)C=C1)NC1CCN(CC1)CC=1C=CC2=C(CCO2)C=1 JXVLUHIEXCRYKR-UHFFFAOYSA-N 0.000 claims 1
• WYPZDIMGOOWUMU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2-methoxyethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CCOC WYPZDIMGOOWUMU-UHFFFAOYSA-N 0.000 claims 1
• DMKDQVCCLVNHST-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2-methoxyethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CCOC DMKDQVCCLVNHST-UHFFFAOYSA-N 0.000 claims 1
• GYFOLHLDMHKWDW-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2-phenoxyethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CCOC2=CC=CC=C2)CC1 GYFOLHLDMHKWDW-UHFFFAOYSA-N 0.000 claims 1
• FEXRVDFQTQGZRP-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2-phenylethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CCC2=CC=CC=C2)CC1 FEXRVDFQTQGZRP-UHFFFAOYSA-N 0.000 claims 1
• TXBRNQNSLVYASK-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(2-phenylethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CCC2=CC=CC=C2)CC1 TXBRNQNSLVYASK-UHFFFAOYSA-N 0.000 claims 1
• SCZITHHOHCJVDH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(cyclohexylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1CCCCC1 SCZITHHOHCJVDH-UHFFFAOYSA-N 0.000 claims 1
• IZUFTSRFBHFAHF-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(furan-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=COC=C1 IZUFTSRFBHFAHF-UHFFFAOYSA-N 0.000 claims 1
• BUQKKQOPCQWXNL-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(pyridin-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=CN=C2)CC1 BUQKKQOPCQWXNL-UHFFFAOYSA-N 0.000 claims 1
• SXIZPHCOQADNAW-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(pyridin-4-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=NC=C2)CC1 SXIZPHCOQADNAW-UHFFFAOYSA-N 0.000 claims 1
• LJUYCQNOXLPDOX-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclohexylacetamide Chemical compound ClC1=C(NC2CCN(CC3=CC=CS3)CC2)C2=C(NC(=N2)C2=CC=C(OCC(=O)NC3CCCCC3)C=C2)N=C1 LJUYCQNOXLPDOX-UHFFFAOYSA-N 0.000 claims 1
• HSFARCJLQGFZEN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclopentylacetamide Chemical compound ClC1=C(NC2CCN(CC3=CC=CS3)CC2)C2=C(NC(=N2)C2=CC=C(OCC(=O)NC3CCCC3)C=C2)N=C1 HSFARCJLQGFZEN-UHFFFAOYSA-N 0.000 claims 1
• SCBSRBLZRWLNSN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1SC=CC=1 SCBSRBLZRWLNSN-UHFFFAOYSA-N 0.000 claims 1
• PYVSZGRDGVEEQZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrimidin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CC=N2)C=C1)NC1CCN(CC1)CC=1SC=CC=1 PYVSZGRDGVEEQZ-UHFFFAOYSA-N 0.000 claims 1
• XAEXHIFDMODZLH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC1=CSC=C1 XAEXHIFDMODZLH-UHFFFAOYSA-N 0.000 claims 1
• VGFPZGDLEOSCND-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC1=CSC=C1 VGFPZGDLEOSCND-UHFFFAOYSA-N 0.000 claims 1
• PROZVPLHJRMZOU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,2-oxazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1)NC1CCN(CC1)CC1=CSC=C1 PROZVPLHJRMZOU-UHFFFAOYSA-N 0.000 claims 1
• UBXDPXOKKGFKQU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1)NC1CCN(CC1)CC1=CSC=C1 UBXDPXOKKGFKQU-UHFFFAOYSA-N 0.000 claims 1
• LOHRPIYOFCXVBS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CSC=C2)CC1 LOHRPIYOFCXVBS-UHFFFAOYSA-N 0.000 claims 1
• XNOUTUZKCOKCJX-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-(thiophen-3-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrazin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CN=C2)C=C1)NC1CCN(CC1)CC1=CSC=C1 XNOUTUZKCOKCJX-UHFFFAOYSA-N 0.000 claims 1
• UELRGDOJUAOQDD-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(1,3,5-trimethylpyrazol-4-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1C(=NN(C=1C)C)C UELRGDOJUAOQDD-UHFFFAOYSA-N 0.000 claims 1
• YEQIOXSDJRHTLT-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(1-methylpyrrol-2-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1N(C=CC=1)C YEQIOXSDJRHTLT-UHFFFAOYSA-N 0.000 claims 1
• JCNCDMFLWUPRBL-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(2,4-dimethoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=C(C=C(C=C1)OC)OC JCNCDMFLWUPRBL-UHFFFAOYSA-N 0.000 claims 1
• GCGNIKSZZXIPDP-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(2-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=C(C=CC=C1)OC GCGNIKSZZXIPDP-UHFFFAOYSA-N 0.000 claims 1
• MXXPDYBEHZQTKI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(F)=C(F)C=C2)CC1 MXXPDYBEHZQTKI-UHFFFAOYSA-N 0.000 claims 1
• YEFQWYAJAXKPMQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3,4-dimethoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(OC)=C(OC)C=C2)CC1 YEFQWYAJAXKPMQ-UHFFFAOYSA-N 0.000 claims 1
• DSIWJKVDLJSMIJ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-cyanophenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(=CC=C2)C#N)CC1 DSIWJKVDLJSMIJ-UHFFFAOYSA-N 0.000 claims 1
• LCDFMBICSYCTSA-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-hydroxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(O)=CC=C2)CC1 LCDFMBICSYCTSA-UHFFFAOYSA-N 0.000 claims 1
• VIRKWTJYQKUJAI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC(=CC=C1)OC VIRKWTJYQKUJAI-UHFFFAOYSA-N 0.000 claims 1
• ULEGWFNFPUWMIM-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-methylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)-2-methylpropyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC(C)(C)N(C)C)C=C1)NC1CCN(CC1)CC1=CC(=CC=C1)C ULEGWFNFPUWMIM-UHFFFAOYSA-N 0.000 claims 1
• PGNGWDIGSDBYNF-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-methylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(C)=CC=C2)CC1 PGNGWDIGSDBYNF-UHFFFAOYSA-N 0.000 claims 1
• OQTPGROQFGBSKY-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-methylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(C)=CC=C2)CC1 OQTPGROQFGBSKY-UHFFFAOYSA-N 0.000 claims 1
• GGHODAZPIXFDRU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-methylthiophen-2-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[1-(dimethylamino)-2-methylpropan-2-yl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(CN(C)C)(C)C)C=C1)NC1CCN(CC1)CC=1SC=CC=1C GGHODAZPIXFDRU-UHFFFAOYSA-N 0.000 claims 1
• ZJKIXCAZGHTAQI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(3-methylthiophen-2-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1SC=CC=1C ZJKIXCAZGHTAQI-UHFFFAOYSA-N 0.000 claims 1
• QGYTYFINTYIVDE-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(Cl)C=C2)CC1 QGYTYFINTYIVDE-UHFFFAOYSA-N 0.000 claims 1
• JDNCSRCHQKJRNE-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-chlorophenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(Cl)C=C2)CC1 JDNCSRCHQKJRNE-UHFFFAOYSA-N 0.000 claims 1
• MOSAINGJDXZOGM-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-cyanophenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(C=C2)C#N)CC1 MOSAINGJDXZOGM-UHFFFAOYSA-N 0.000 claims 1
• IAOVGNUQMKDIMX-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-ethoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OCC IAOVGNUQMKDIMX-UHFFFAOYSA-N 0.000 claims 1
• FLGQXUPZLOJSPS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[1-(dimethylamino)-2-methylpropan-2-yl]acetamide Chemical compound CN(C)CC(C)(C)NC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(F)C=C2)CC1 FLGQXUPZLOJSPS-UHFFFAOYSA-N 0.000 claims 1
• MBYDJDMZTVBDLO-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(F)C=C2)CC1 MBYDJDMZTVBDLO-UHFFFAOYSA-N 0.000 claims 1
• OJVRLAFQZOEKMD-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-hydroxy-3-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC(=C(C=C1)O)OC OJVRLAFQZOEKMD-UHFFFAOYSA-N 0.000 claims 1
• OUZXRNLTKLVQOH-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-hydroxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(O)C=C2)CC1 OUZXRNLTKLVQOH-UHFFFAOYSA-N 0.000 claims 1
• QMUWCDCNLFVTBC-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxy-3,5-dimethylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(C)=C(OC)C(C)=C2)CC1 QMUWCDCNLFVTBC-UHFFFAOYSA-N 0.000 claims 1
• DTZZIBWWAQRUAY-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxy-3-methylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC(C)=C(OC)C=C2)CC1 DTZZIBWWAQRUAY-UHFFFAOYSA-N 0.000 claims 1
• APHLNDUQTXASCC-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,5-dimethylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1C)C)NC1CCN(CC1)CC1=CC=C(C=C1)OC APHLNDUQTXASCC-UHFFFAOYSA-N 0.000 claims 1
• YYCLMJLRGUAAEI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2,6-dimethylphenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=C(C)C=C(C=C1C)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(OC)C=C2)CC1 YYCLMJLRGUAAEI-UHFFFAOYSA-N 0.000 claims 1
• BPOQTFQATHYTRO-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-fluorophenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=C(F)C=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(OC)C=C2)CC1 BPOQTFQATHYTRO-UHFFFAOYSA-N 0.000 claims 1
• VFMJOOYHKSRSNI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methoxyphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)OC)NC1CCN(CC1)CC1=CC=C(C=C1)OC VFMJOOYHKSRSNI-UHFFFAOYSA-N 0.000 claims 1
• NITHTRLXJHLKJN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-2-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC(=C(OCC(=O)NC)C=C1)C)NC1CCN(CC1)CC1=CC=C(C=C1)OC NITHTRLXJHLKJN-UHFFFAOYSA-N 0.000 claims 1
• FJUIMDZJXWNNAG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]-3-methylphenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC(C)=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(OC)C=C2)CC1 FJUIMDZJXWNNAG-UHFFFAOYSA-N 0.000 claims 1
• RGSXNLNMNMEUSI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]anilino]-N-methylacetamide Chemical compound CNC(=O)CNC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(OC)C=C2)CC1 RGSXNLNMNMEUSI-UHFFFAOYSA-N 0.000 claims 1
• WZDOEFUKBRHJIG-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,2-dimethylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OC(C(=O)NC)(C)C)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC WZDOEFUKBRHJIG-UHFFFAOYSA-N 0.000 claims 1
• DVICUXCQFMDHMZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1,2-oxazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC DVICUXCQFMDHMZ-UHFFFAOYSA-N 0.000 claims 1
• NPCNKLCHUBKENC-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(1H-1,2,4-triazol-5-yl)acetamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCC(=O)NC3=NNC=N3)C=C2)C=C1 NPCNKLCHUBKENC-UHFFFAOYSA-N 0.000 claims 1
• FXBMKRGSJLUYPW-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-hydroxyethyl)acetamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCC(=O)NCCO)C=C2)C=C1 FXBMKRGSJLUYPW-UHFFFAOYSA-N 0.000 claims 1
• LWETUOLATKTMIX-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-methylpyrazol-3-yl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=CC=NN2C)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC LWETUOLATKTMIX-UHFFFAOYSA-N 0.000 claims 1
• VEBWABUYYOQSMM-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(2-propan-2-yloxyethyl)acetamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCC(=O)NCCOC(C)C)C=C2)C=C1 VEBWABUYYOQSMM-UHFFFAOYSA-N 0.000 claims 1
• YZJSFGGKQZUTQZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(cyclohexylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2CCCCC2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC YZJSFGGKQZUTQZ-UHFFFAOYSA-N 0.000 claims 1
• LJEAYXRUXVWPCI-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-(pyridin-4-ylmethyl)acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC2=CC=NC=C2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC LJEAYXRUXVWPCI-UHFFFAOYSA-N 0.000 claims 1
• DXLHWYFEOBRFBD-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)-2-methylpropyl]acetamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCC(=O)NCC(C)(C)N(C)C)C=C2)C=C1 DXLHWYFEOBRFBD-UHFFFAOYSA-N 0.000 claims 1
• AODZQYGCLKCMDZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCC(=O)NCCN(C)C)C=C2)C=C1 AODZQYGCLKCMDZ-UHFFFAOYSA-N 0.000 claims 1
• NJAVEAITUWZDBX-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(oxan-4-yl)ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCC2CCOCC2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC NJAVEAITUWZDBX-UHFFFAOYSA-N 0.000 claims 1
• WJKACBLBNVDJPY-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cycloheptylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCCCC2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC WJKACBLBNVDJPY-UHFFFAOYSA-N 0.000 claims 1
• MECZIPQSXBDCIV-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-cyclopentylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2CCCC2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC MECZIPQSXBDCIV-UHFFFAOYSA-N 0.000 claims 1
• LFUCNRCEJOAJLX-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC LFUCNRCEJOAJLX-UHFFFAOYSA-N 0.000 claims 1
• VVXGGYGSBOZUBK-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-propan-2-ylacetamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCC(=O)NC(C)C)C=C2)C=C1 VVXGGYGSBOZUBK-UHFFFAOYSA-N 0.000 claims 1
• JMSWKCVXTXEHRC-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrazin-2-ylacetamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCC(=O)NC3=CN=CC=N3)C=C2)C=C1 JMSWKCVXTXEHRC-UHFFFAOYSA-N 0.000 claims 1
• IQKPMQAIFKMOKR-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyridin-3-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC=2C=NC=CC=2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC IQKPMQAIFKMOKR-UHFFFAOYSA-N 0.000 claims 1
• XUAOMXBPEZTTFZ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-pyrimidin-2-ylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC2=NC=CC=N2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC XUAOMXBPEZTTFZ-UHFFFAOYSA-N 0.000 claims 1
• RBNIIPIWHJKCSR-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CC(=O)NC)NC1CCN(CC1)CC1=CC=C(C=C1)OC RBNIIPIWHJKCSR-UHFFFAOYSA-N 0.000 claims 1
• VFRBBLNRYUIUBS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)-2-methylpropyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC(C)(C)N(C)C)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)C VFRBBLNRYUIUBS-UHFFFAOYSA-N 0.000 claims 1
• CMALSMIIPAOYSU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(C)C=C2)CC1 CMALSMIIPAOYSU-UHFFFAOYSA-N 0.000 claims 1
• QHMUFSHOVRUKMD-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)C QHMUFSHOVRUKMD-UHFFFAOYSA-N 0.000 claims 1
• BXOKPRGKMKCVEK-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methylsulfanylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)SC BXOKPRGKMKCVEK-UHFFFAOYSA-N 0.000 claims 1
• FJYHMLKDHQYLIQ-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-methylsulfonylphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)S(=O)(=O)C FJYHMLKDHQYLIQ-UHFFFAOYSA-N 0.000 claims 1
• COMURPDMSOYNSN-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(4-propan-2-yloxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(OC(C)C)C=C2)CC1 COMURPDMSOYNSN-UHFFFAOYSA-N 0.000 claims 1
• NSHRRGROPSLIDD-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(5-methylfuran-2-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(C)O2)CC1 NSHRRGROPSLIDD-UHFFFAOYSA-N 0.000 claims 1
• PQXGZSHSRGOHNK-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(5-methylfuran-2-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC=1OC(=CC=1)C PQXGZSHSRGOHNK-UHFFFAOYSA-N 0.000 claims 1
• WPNQTUYZSVCSBE-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[(6-methylpyridin-2-yl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=NC(=CC=C1)C WPNQTUYZSVCSBE-UHFFFAOYSA-N 0.000 claims 1
• YUKMROGJBOGWSA-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CCC1=CC=C(C=C1)OC YUKMROGJBOGWSA-UHFFFAOYSA-N 0.000 claims 1
• CNBBEFUEHAWGQS-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 CNBBEFUEHAWGQS-UHFFFAOYSA-N 0.000 claims 1
• RWSNGUAMDJDBDU-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[[4-(difluoromethoxy)phenyl]methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC(F)F RWSNGUAMDJDBDU-UHFFFAOYSA-N 0.000 claims 1
• DCMQZIWRZHAFIC-UHFFFAOYSA-N 2-[4-[6-chloro-7-[[1-[[4-(dimethylamino)phenyl]methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)N(C)C DCMQZIWRZHAFIC-UHFFFAOYSA-N 0.000 claims 1
• KCEZFUALQCIMKU-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-3-yl)amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[1-(dimethylamino)-2-methylpropan-2-yl]acetamide Chemical compound C(C1=CC=CC=C1)N1CC(CCC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC(CN(C)C)(C)C)C=C1 KCEZFUALQCIMKU-UHFFFAOYSA-N 0.000 claims 1
• WZIYWZKNLNNATK-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)-methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)-2-methylpropyl]acetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NCC(C)(C)N(C)C)C=C1)C WZIYWZKNLNNATK-UHFFFAOYSA-N 0.000 claims 1
• MFMOXNNUKBAPJY-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)-methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1)C MFMOXNNUKBAPJY-UHFFFAOYSA-N 0.000 claims 1
• MGOMDXXEJGOXAQ-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)-methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)C MGOMDXXEJGOXAQ-UHFFFAOYSA-N 0.000 claims 1
• JACVPRFVQFYZOJ-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,N-dimethylacetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)N(C)C)C=C1 JACVPRFVQFYZOJ-UHFFFAOYSA-N 0.000 claims 1
• SRRMQSGOZMNPKS-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)-2-methylpropyl]acetamide Chemical compound CN(C)C(C)(C)CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=CC=C2)CC1 SRRMQSGOZMNPKS-UHFFFAOYSA-N 0.000 claims 1
• PMQYAHWUUKCQDK-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1 PMQYAHWUUKCQDK-UHFFFAOYSA-N 0.000 claims 1
• PEKZKKQCWMIWAC-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1 PEKZKKQCWMIWAC-UHFFFAOYSA-N 0.000 claims 1
• IQAGCNCQGCTOKB-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)-2-methylpropyl]acetamide Chemical compound CN(C)C(C)(C)CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NCC1CCN(CC2=CC=CC=C2)CC1 IQAGCNCQGCTOKB-UHFFFAOYSA-N 0.000 claims 1
• UYRIAGXHMPBHQK-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)CNC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1 UYRIAGXHMPBHQK-UHFFFAOYSA-N 0.000 claims 1
• WORYZWCDXXENJQ-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)CNC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1 WORYZWCDXXENJQ-UHFFFAOYSA-N 0.000 claims 1
• UVKUXAOBPQKBSI-LJQANCHMSA-N 2-[4-[7-[[(3R)-1-benzylpyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound C(C1=CC=CC=C1)N1C[C@@H](CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1 UVKUXAOBPQKBSI-LJQANCHMSA-N 0.000 claims 1
• ZFEAWWJCNOBVDF-SFHVURJKSA-N 2-[4-[7-[[(3S)-1-(1,3-benzodioxol-5-ylmethyl)pyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound O1COC2=C1C=CC(=C2)CN1C[C@H](CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1 ZFEAWWJCNOBVDF-SFHVURJKSA-N 0.000 claims 1
• QYTWNENPAAGNFM-FQEVSTJZSA-N 2-[4-[7-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N,N-dimethylacetamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)N(C)C)C=C1 QYTWNENPAAGNFM-FQEVSTJZSA-N 0.000 claims 1
• QCINSNQMUHCMNB-QHCPKHFHSA-N 2-[4-[7-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[1-(dimethylamino)-2-methylpropan-2-yl]acetamide Chemical compound CN(C)CC(C)(C)NC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@H]1CCN(CC2=CC=CC=C2)C1 QCINSNQMUHCMNB-QHCPKHFHSA-N 0.000 claims 1
• UAKZHZZMRIYAGT-QHCPKHFHSA-N 2-[4-[7-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)-2-methylpropyl]acetamide Chemical compound CN(C)C(C)(C)CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@H]1CCN(CC2=CC=CC=C2)C1 UAKZHZZMRIYAGT-QHCPKHFHSA-N 0.000 claims 1
• NNCBIXGEOYOMCB-QFIPXVFZSA-N 2-[4-[7-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@H]1CCN(CC2=CC=CC=C2)C1 NNCBIXGEOYOMCB-QFIPXVFZSA-N 0.000 claims 1
• UVKUXAOBPQKBSI-IBGZPJMESA-N 2-[4-[7-[[(3S)-1-benzylpyrrolidin-3-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound C(C1=CC=CC=C1)N1C[C@H](CC1)NC1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1 UVKUXAOBPQKBSI-IBGZPJMESA-N 0.000 claims 1
• KZRBZKSJEKDYCX-UHFFFAOYSA-N 2-[4-[7-[[1-(1,3-benzodioxol-5-ylmethyl)piperidin-4-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-[2-(dimethylamino)ethyl]acetamide Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC3=C(OCO3)C=C2)CC1 KZRBZKSJEKDYCX-UHFFFAOYSA-N 0.000 claims 1
• WDFZVOYGFHLPLM-UHFFFAOYSA-N 2-[4-[7-[[1-(1,3-benzodioxol-5-ylmethyl)piperidin-4-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC3=C(OCO3)C=C2)CC1 WDFZVOYGFHLPLM-UHFFFAOYSA-N 0.000 claims 1
• NUMMXHBUCSQXDY-UHFFFAOYSA-N 2-[4-[7-[[1-[(4-acetamidophenyl)methyl]piperidin-4-yl]amino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]-N-methylacetamide Chemical compound C(C)(=O)NC1=CC=C(CN2CCC(CC2)NC2=C3C(=NC=C2Cl)NC(=N3)C2=CC=C(OCC(=O)NC)C=C2)C=C1 NUMMXHBUCSQXDY-UHFFFAOYSA-N 0.000 claims 1
• ROSFTKYWGVIARV-UHFFFAOYSA-N 3-[4-[6-bromo-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NC)NC1CCN(CC1)CC ROSFTKYWGVIARV-UHFFFAOYSA-N 0.000 claims 1
• AIQSAFFUZJDFMB-UHFFFAOYSA-N 3-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NC)NC1CCN(CC1)C AIQSAFFUZJDFMB-UHFFFAOYSA-N 0.000 claims 1
• WTFQRUGMTLWANO-UHFFFAOYSA-N 3-[4-[6-bromo-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NC)NC1CCN(CC1)C(C)C WTFQRUGMTLWANO-UHFFFAOYSA-N 0.000 claims 1
• DCDFTXPYXDITAW-UHFFFAOYSA-N 3-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NC)NC1CCN(CC1)CC DCDFTXPYXDITAW-UHFFFAOYSA-N 0.000 claims 1
• CNSKPEVXMOSLON-UHFFFAOYSA-N 3-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NC)NC1CCN(CC1)C CNSKPEVXMOSLON-UHFFFAOYSA-N 0.000 claims 1
• NNTOLLXTZFQKHZ-UHFFFAOYSA-N 3-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NC)NC1CCN(CC1)C(C)C NNTOLLXTZFQKHZ-UHFFFAOYSA-N 0.000 claims 1
• RWDFIKLCRIWPGZ-INIZCTEOSA-N 3-[4-[6-chloro-7-[[(3S)-1-ethylpyrrolidin-3-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NC)N[C@@H]1CN(CC1)CC RWDFIKLCRIWPGZ-INIZCTEOSA-N 0.000 claims 1
• OMHLWSFDTYXFHY-UHFFFAOYSA-N 3-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methoxypropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)NOC)NC1CCN(CC1)CC1=CC=C(C=C1)OC OMHLWSFDTYXFHY-UHFFFAOYSA-N 0.000 claims 1
• YDLICFQTESNRGW-UHFFFAOYSA-N 3-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenyl]-N-methylpropanamide Chemical compound CNC(=O)CCC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2NC1CCN(CC2=CC=C(OC)C=C2)CC1 YDLICFQTESNRGW-UHFFFAOYSA-N 0.000 claims 1
• UAKZHZZMRIYAGT-HSZRJFAPSA-N CN(C)C(C)(C)CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@@H]1CCN(CC2=CC=CC=C2)C1 Chemical compound CN(C)C(C)(C)CNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@@H]1CCN(CC2=CC=CC=C2)C1 UAKZHZZMRIYAGT-HSZRJFAPSA-N 0.000 claims 1
• CRQKAFQZIPIVLT-JOCHJYFZSA-N CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@@H]1CCN(CC2=CC=C(F)C=C2)C1 Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@@H]1CCN(CC2=CC=C(F)C=C2)C1 CRQKAFQZIPIVLT-JOCHJYFZSA-N 0.000 claims 1
• NNCBIXGEOYOMCB-JOCHJYFZSA-N CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@@H]1CCN(CC2=CC=CC=C2)C1 Chemical compound CN(C)CCNC(=O)COC1=CC=C(C=C1)C1=NC2=C(N1)N=CC(Cl)=C2N[C@@H]1CCN(CC2=CC=CC=C2)C1 NNCBIXGEOYOMCB-JOCHJYFZSA-N 0.000 claims 1
• GRSCURFRTNYWJT-UHFFFAOYSA-N N-(5-tert-butyl-1,2-oxazol-3-yl)-2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]acetamide Chemical compound CN1CCC(CC1)NC1=C(Cl)C=NC2=C1N=C(N2)C1=CC=C(OCC(=O)NC2=NOC(=C2)C(C)(C)C)C=C1 GRSCURFRTNYWJT-UHFFFAOYSA-N 0.000 claims 1
• UIFUTMSAABAQHG-UHFFFAOYSA-N N-[2-[4-[6-bromo-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound CN1CCC(CC1)NC1=C(Br)C=NC2=C1N=C(N2)C1=CC=C(OCCNC(C)=O)C=C1 UIFUTMSAABAQHG-UHFFFAOYSA-N 0.000 claims 1
• HFTCGKWGZCPTGA-UHFFFAOYSA-N N-[2-[4-[6-bromo-7-[[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound BrC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(C)=O)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 HFTCGKWGZCPTGA-UHFFFAOYSA-N 0.000 claims 1
• PJWOVITUIRESEA-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-ethylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound CCN1CCC(CC1)NC1=C(Cl)C=NC2=C1N=C(N2)C1=CC=C(OCCNC(C)=O)C=C1 PJWOVITUIRESEA-UHFFFAOYSA-N 0.000 claims 1
• OJYHXPBRMHWGOA-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]-2,2-dimethylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(C(C)(C)C)=O)C=C1)NC1CCN(CC1)C OJYHXPBRMHWGOA-UHFFFAOYSA-N 0.000 claims 1
• MYLWAJDQUVYHDH-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]-2-methoxyacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(COC)=O)C=C1)NC1CCN(CC1)C MYLWAJDQUVYHDH-UHFFFAOYSA-N 0.000 claims 1
• AYOYKWFODBVRIF-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]-2-methylpropanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(C(C)C)=O)C=C1)NC1CCN(CC1)C AYOYKWFODBVRIF-UHFFFAOYSA-N 0.000 claims 1
• GNECURWMSKBIMQ-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound C(C)(=O)NCCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C=2NC2CCN(CC2)C)Cl)N1 GNECURWMSKBIMQ-UHFFFAOYSA-N 0.000 claims 1
• VGIBYLDQGXHMGB-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]cyclohexanecarboxamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(=O)C2CCCCC2)C=C1)NC1CCN(CC1)C VGIBYLDQGXHMGB-UHFFFAOYSA-N 0.000 claims 1
• XUSBOMBKZBCOFZ-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]cyclopentanecarboxamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(=O)C2CCCC2)C=C1)NC1CCN(CC1)C XUSBOMBKZBCOFZ-UHFFFAOYSA-N 0.000 claims 1
• UMMZQCCJWXJXPQ-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]cyclopropanecarboxamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(=O)C2CC2)C=C1)NC1CCN(CC1)C UMMZQCCJWXJXPQ-UHFFFAOYSA-N 0.000 claims 1
• YUILNHYZSVKJSL-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]pyridine-3-carboxamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(=O)C=2C=NC=CC=2)C=C1)NC1CCN(CC1)C YUILNHYZSVKJSL-UHFFFAOYSA-N 0.000 claims 1
• WTFBSIAAEDPXIQ-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]pyridine-4-carboxamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(=O)C2=CC=NC=C2)C=C1)NC1CCN(CC1)C WTFBSIAAEDPXIQ-UHFFFAOYSA-N 0.000 claims 1
• QESAJMJBYCEQSJ-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[(1-propan-2-ylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound CC(C)N1CCC(CC1)NC1=C(Cl)C=NC2=C1N=C(N2)C1=CC=C(OCCNC(C)=O)C=C1 QESAJMJBYCEQSJ-UHFFFAOYSA-N 0.000 claims 1
• USFWPFIIVZLLNM-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[[1-(thiophen-2-ylmethyl)piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(C)=O)C=C1)NC1CCN(CC1)CC=1SC=CC=1 USFWPFIIVZLLNM-UHFFFAOYSA-N 0.000 claims 1
• KGUXYYPHWNIYAC-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(C)=O)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC KGUXYYPHWNIYAC-UHFFFAOYSA-N 0.000 claims 1
• JWNFLUMKBKZIAT-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]cyclopentanecarboxamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(=O)C2CCCC2)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC JWNFLUMKBKZIAT-UHFFFAOYSA-N 0.000 claims 1
• ZXVLBUSHAIKCOU-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]propanamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(CC)=O)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)OC ZXVLBUSHAIKCOU-UHFFFAOYSA-N 0.000 claims 1
• CPRLUJBGTNORQJ-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]pyridine-4-carboxamide Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(Cl)C=NC3=C2N=C(N3)C2=CC=C(OCCNC(=O)C3=CC=NC=C3)C=C2)C=C1 CPRLUJBGTNORQJ-UHFFFAOYSA-N 0.000 claims 1
• GOKLKTIZTYUYJS-UHFFFAOYSA-N N-[2-[4-[6-chloro-7-[[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]piperidin-4-yl]amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]ethyl]acetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCCNC(C)=O)C=C1)NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 GOKLKTIZTYUYJS-UHFFFAOYSA-N 0.000 claims 1
• DUJONUNUPQJMPC-UHFFFAOYSA-N N-benzyl-2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]acetamide Chemical compound C(C1=CC=CC=C1)NC(COC1=CC=C(C=C1)C1=NC=2C(=NC=C(C=2NC2CCN(CC2)C)Cl)N1)=O DUJONUNUPQJMPC-UHFFFAOYSA-N 0.000 claims 1
• BUGKYCKPOHXMCV-UHFFFAOYSA-N N-tert-butyl-2-[4-[6-chloro-7-[(1-methylpiperidin-4-yl)amino]-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]acetamide Chemical compound C(C)(C)(C)NC(COC1=CC=C(C=C1)C1=NC=2C(=NC=C(C=2NC2CCN(CC2)C)Cl)N1)=O BUGKYCKPOHXMCV-UHFFFAOYSA-N 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 166
• 230000000694 effects Effects 0.000 abstract description 16
• 108010006700 Receptor Tyrosine Kinase-like Orphan Receptors Proteins 0.000 abstract description 6
• 102000005435 Receptor Tyrosine Kinase-like Orphan Receptors Human genes 0.000 abstract description 6
• 239000003112 inhibitor Substances 0.000 abstract description 5
• 108091000080 Phosphotransferase Proteins 0.000 abstract description 4
• 102000020233 phosphotransferase Human genes 0.000 abstract description 4
• 239000000543 intermediate Substances 0.000 description 384
• 239000000047 product Substances 0.000 description 190
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 184
• 201000006417 multiple sclerosis Diseases 0.000 description 175
• 238000005160 1H NMR spectroscopy Methods 0.000 description 161
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 96
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
• 239000000203 mixture Substances 0.000 description 72
• 239000007787 solid Substances 0.000 description 60
• OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 54
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 46
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
• 101001103039 Homo sapiens Inactive tyrosine-protein kinase transmembrane receptor ROR1 Proteins 0.000 description 40
• 102100039615 Inactive tyrosine-protein kinase transmembrane receptor ROR1 Human genes 0.000 description 37
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 34
• 101001103036 Homo sapiens Nuclear receptor ROR-alpha Proteins 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• 239000000460 chlorine Substances 0.000 description 31
• 239000012074 organic phase Substances 0.000 description 31
• 210000004027 cell Anatomy 0.000 description 30
• 239000002904 solvent Substances 0.000 description 29
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 26
• DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 25
• OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 24
• 239000012267 brine Substances 0.000 description 24
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 24
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
• 206010028980 Neoplasm Diseases 0.000 description 22
• 229910052801 chlorine Inorganic materials 0.000 description 22
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
• 235000019439 ethyl acetate Nutrition 0.000 description 22
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 21
• 239000000243 solution Substances 0.000 description 21
• 238000006243 chemical reaction Methods 0.000 description 20
• 241000282414 Homo sapiens Species 0.000 description 19
• 125000003118 aryl group Chemical group 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
• KYVDKOZOAOAFDC-UHFFFAOYSA-N 4,5-dichloro-3-nitropyridin-2-amine Chemical compound NC1=NC=C(Cl)C(Cl)=C1[N+]([O-])=O KYVDKOZOAOAFDC-UHFFFAOYSA-N 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
• 239000002253 acid Substances 0.000 description 16
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 239000007832 Na2SO4 Substances 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 229910052794 bromium Inorganic materials 0.000 description 15
• 201000010099 disease Diseases 0.000 description 15
• 239000012071 phase Substances 0.000 description 15
• 229910052938 sodium sulfate Inorganic materials 0.000 description 15
• 235000011152 sodium sulphate Nutrition 0.000 description 15
• WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 14
• 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000008346 aqueous phase Substances 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• JDACBLXRPFJSHT-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1CN1CCC(N)CC1 JDACBLXRPFJSHT-UHFFFAOYSA-N 0.000 description 13
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
• 235000019341 magnesium sulphate Nutrition 0.000 description 13
• BLGCPXIDEMLKMS-UHFFFAOYSA-N 5-bromo-4-chloro-3-nitropyridin-2-amine Chemical compound NC1=NC=C(Br)C(Cl)=C1[N+]([O-])=O BLGCPXIDEMLKMS-UHFFFAOYSA-N 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 239000000463 material Substances 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• 201000011510 cancer Diseases 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 239000006228 supernatant Substances 0.000 description 10
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 9
• 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 9
• 108090000623 proteins and genes Proteins 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 230000006907 apoptotic process Effects 0.000 description 8
• IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 8
• 230000000155 isotopic effect Effects 0.000 description 8
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
• 238000003786 synthesis reaction Methods 0.000 description 8
• 208000031261 Acute myeloid leukaemia Diseases 0.000 description 7
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 7
• 230000009286 beneficial effect Effects 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 238000004128 high performance liquid chromatography Methods 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 239000002002 slurry Substances 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• GOVJRSTWOQZULF-UHFFFAOYSA-N 4,5-dichloropyridine-2,3-diamine Chemical compound NC1=NC=C(Cl)C(Cl)=C1N GOVJRSTWOQZULF-UHFFFAOYSA-N 0.000 description 6
• RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
• 125000006163 5-membered heteroaryl group Chemical group 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
• 241000124008 Mammalia Species 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 239000013058 crude material Substances 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 229910052731 fluorine Inorganic materials 0.000 description 6
• 230000014509 gene expression Effects 0.000 description 6
• 230000004968 inflammatory condition Effects 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 235000011149 sulphuric acid Nutrition 0.000 description 6
• 210000001519 tissue Anatomy 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• SEPGYEWOCAOBRW-UHFFFAOYSA-N 5-chloro-4-N-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]-3-nitropyridine-2,4-diamine Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(C(N)=NC=C2Cl)[N+]([O-])=O)C=C1 SEPGYEWOCAOBRW-UHFFFAOYSA-N 0.000 description 5
• 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 5
• 208000026310 Breast neoplasm Diseases 0.000 description 5
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 5
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 5
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 230000004913 activation Effects 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 238000001802 infusion Methods 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• 201000001441 melanoma Diseases 0.000 description 5
• 210000000056 organ Anatomy 0.000 description 5
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
• 238000004007 reversed phase HPLC Methods 0.000 description 5
• 210000000130 stem cell Anatomy 0.000 description 5
• PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 4
• IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
• WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 4
• SYBOEAMERMZLDN-UHFFFAOYSA-N 5-chloro-4-N-(1-methylpiperidin-4-yl)-3-nitropyridine-2,4-diamine Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)C SYBOEAMERMZLDN-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 206010006187 Breast cancer Diseases 0.000 description 4
• 102000005636 Cyclic AMP Response Element-Binding Protein Human genes 0.000 description 4
• 108010045171 Cyclic AMP Response Element-Binding Protein Proteins 0.000 description 4
• 206010018338 Glioma Diseases 0.000 description 4
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 4
• 241001465754 Metazoa Species 0.000 description 4
• 102000038030 PI3Ks Human genes 0.000 description 4
• 108091007960 PI3Ks Proteins 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 108020004459 Small interfering RNA Proteins 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 210000003719 b-lymphocyte Anatomy 0.000 description 4
• 210000004369 blood Anatomy 0.000 description 4
• 239000008280 blood Substances 0.000 description 4
• 210000003169 central nervous system Anatomy 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 239000003085 diluting agent Substances 0.000 description 4
• 239000002270 dispersing agent Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 208000036971 interstitial lung disease 2 Diseases 0.000 description 4
• LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
• ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
• SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
• 238000001556 precipitation Methods 0.000 description 4
• 239000003755 preservative agent Substances 0.000 description 4
• QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
• 102000004169 proteins and genes Human genes 0.000 description 4
• ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• 239000011701 zinc Substances 0.000 description 4
• UNHOPMIDKWXFMF-YFKPBYRVSA-N (3s)-1-methylpyrrolidin-3-amine Chemical compound CN1CC[C@H](N)C1 UNHOPMIDKWXFMF-YFKPBYRVSA-N 0.000 description 3
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
• NQQVCDIEQDMPOD-UHFFFAOYSA-N 1-(thiophen-2-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CS1 NQQVCDIEQDMPOD-UHFFFAOYSA-N 0.000 description 3
• IYYXLZOFUOPDAM-UHFFFAOYSA-N 1-[(1,3,5-trimethylpyrazol-4-yl)methyl]piperidin-4-amine Chemical compound CC1=NN(C)C(C)=C1CN1CCC(N)CC1 IYYXLZOFUOPDAM-UHFFFAOYSA-N 0.000 description 3
• AVLVOGLURNXDQE-UHFFFAOYSA-N 1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]piperidin-4-amine Chemical compound NC1CCN(CC2=CC=C(C=C2)N2C=NC=N2)CC1 AVLVOGLURNXDQE-UHFFFAOYSA-N 0.000 description 3
• ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 description 3
• OMBQRGCYHSVMHE-UHFFFAOYSA-N 2-(4-formylphenoxy)-n-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=O)C=C1 OMBQRGCYHSVMHE-UHFFFAOYSA-N 0.000 description 3
• CRRAQLWJVYODCL-UHFFFAOYSA-N 4,5-dichloropyridin-2-amine Chemical compound NC1=CC(Cl)=C(Cl)C=N1 CRRAQLWJVYODCL-UHFFFAOYSA-N 0.000 description 3
• UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 3
• 208000031212 Autoimmune polyendocrinopathy Diseases 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• 208000011231 Crohn disease Diseases 0.000 description 3
• 201000004624 Dermatitis Diseases 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 208000007465 Giant cell arteritis Diseases 0.000 description 3
• 208000032612 Glial tumor Diseases 0.000 description 3
• 239000004471 Glycine Substances 0.000 description 3
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 description 3
• 206010025323 Lymphomas Diseases 0.000 description 3
• DLGAQEYVNNYFQF-UHFFFAOYSA-N N-(4,5-dichloropyridin-2-yl)nitramide Chemical compound ClC1=CC(=NC=C1Cl)N[N+](=O)[O-] DLGAQEYVNNYFQF-UHFFFAOYSA-N 0.000 description 3
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
• MNPVNGIRGVJBIM-UHFFFAOYSA-N N-[2-(dimethylamino)ethyl]-2-(4-formylphenoxy)acetamide Chemical compound CN(CCNC(COC1=CC=C(C=C1)C=O)=O)C MNPVNGIRGVJBIM-UHFFFAOYSA-N 0.000 description 3
• 206010033128 Ovarian cancer Diseases 0.000 description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 description 3
• 206010034277 Pemphigoid Diseases 0.000 description 3
• 206010035664 Pneumonia Diseases 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 208000006011 Stroke Diseases 0.000 description 3
• 206010047115 Vasculitis Diseases 0.000 description 3
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
• 239000012346 acetyl chloride Substances 0.000 description 3
• 230000001154 acute effect Effects 0.000 description 3
• 125000002947 alkylene group Chemical group 0.000 description 3
• 239000007864 aqueous solution Substances 0.000 description 3
• 239000007900 aqueous suspension Substances 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 230000003197 catalytic effect Effects 0.000 description 3
• 230000007541 cellular toxicity Effects 0.000 description 3
• 238000005119 centrifugation Methods 0.000 description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
• 230000003247 decreasing effect Effects 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 206010014599 encephalitis Diseases 0.000 description 3
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
• 239000000796 flavoring agent Substances 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 239000012458 free base Substances 0.000 description 3
• 239000000499 gel Substances 0.000 description 3
• 230000030279 gene silencing Effects 0.000 description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
• 239000005457 ice water Substances 0.000 description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 210000000265 leukocyte Anatomy 0.000 description 3
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
• 210000004072 lung Anatomy 0.000 description 3
• 201000005202 lung cancer Diseases 0.000 description 3
• 208000020816 lung neoplasm Diseases 0.000 description 3
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical class O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 3
• 201000005962 mycosis fungoides Diseases 0.000 description 3
• 230000007935 neutral effect Effects 0.000 description 3
• 231100000252 nontoxic Toxicity 0.000 description 3
• 230000003000 nontoxic effect Effects 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• 239000012044 organic layer Substances 0.000 description 3
• 230000002611 ovarian Effects 0.000 description 3
• 201000002528 pancreatic cancer Diseases 0.000 description 3
• 238000007911 parenteral administration Methods 0.000 description 3
• 235000018102 proteins Nutrition 0.000 description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
• 150000003254 radicals Chemical class 0.000 description 3
• 230000004044 response Effects 0.000 description 3
• 239000000377 silicon dioxide Substances 0.000 description 3
• 235000017550 sodium carbonate Nutrition 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
• 239000003381 stabilizer Substances 0.000 description 3
• 239000011550 stock solution Substances 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 230000004083 survival effect Effects 0.000 description 3
• 239000000375 suspending agent Substances 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• CNHQURYHQWUQLL-UHFFFAOYSA-N tert-butyl n-[2-(4-formylphenoxy)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCOC1=CC=C(C=O)C=C1 CNHQURYHQWUQLL-UHFFFAOYSA-N 0.000 description 3
• 208000008732 thymoma Diseases 0.000 description 3
• QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 2
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• MBAGLGVPJNVVJH-NSHDSACASA-N (3s)-1-[(2-methoxyphenyl)methyl]pyrrolidin-3-amine Chemical compound COC1=CC=CC=C1CN1C[C@@H](N)CC1 MBAGLGVPJNVVJH-NSHDSACASA-N 0.000 description 2
• GOLVGZOPWLLUSF-LURJTMIESA-N (3s)-1-ethylpyrrolidin-3-amine Chemical compound CCN1CC[C@H](N)C1 GOLVGZOPWLLUSF-LURJTMIESA-N 0.000 description 2
• SYMMPPWYYXRLJX-ZETCQYMHSA-N (3s)-1-propan-2-ylpyrrolidin-3-amine Chemical compound CC(C)N1CC[C@H](N)C1 SYMMPPWYYXRLJX-ZETCQYMHSA-N 0.000 description 2
• QQBSLNKWDXZLKL-ZETCQYMHSA-N (3s)-1-propylpyrrolidin-3-amine Chemical compound CCCN1CC[C@H](N)C1 QQBSLNKWDXZLKL-ZETCQYMHSA-N 0.000 description 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
• ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 2
• TZXBALTUSCDXLU-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(OCC2)C2=C1 TZXBALTUSCDXLU-UHFFFAOYSA-N 0.000 description 2
• ZXVWFOMYPHVUGO-UHFFFAOYSA-N 1-(2-methylpropyl)piperidin-4-amine Chemical compound CC(C)CN1CCC(N)CC1 ZXVWFOMYPHVUGO-UHFFFAOYSA-N 0.000 description 2
• UFETTXCVHFVMPU-UHFFFAOYSA-N 1-ethylpiperidin-4-amine Chemical compound CCN1CCC(N)CC1 UFETTXCVHFVMPU-UHFFFAOYSA-N 0.000 description 2
• IRNAEDHJBNPCEZ-UHFFFAOYSA-N 1-n,1-n,2-trimethylpropane-1,2-diamine Chemical compound CN(C)CC(C)(C)N IRNAEDHJBNPCEZ-UHFFFAOYSA-N 0.000 description 2
• ZCYVGFQRDRGDJM-UHFFFAOYSA-N 1-propylpiperidin-4-amine Chemical compound CCCN1CCC(N)CC1 ZCYVGFQRDRGDJM-UHFFFAOYSA-N 0.000 description 2
• FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
• LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
• CPUAYRUYCAEGCU-UHFFFAOYSA-N 2-(3-formylphenoxy)-n-methylacetamide Chemical compound CNC(=O)COC1=CC=CC(C=O)=C1 CPUAYRUYCAEGCU-UHFFFAOYSA-N 0.000 description 2
• IBZDPHIZLREMLS-UHFFFAOYSA-N 2-(4-formyl-3-methylphenoxy)-N-methylacetamide Chemical compound C(=O)C1=C(C=C(OCC(=O)NC)C=C1)C IBZDPHIZLREMLS-UHFFFAOYSA-N 0.000 description 2
• GNMSZDCHTBBZAV-UHFFFAOYSA-N 2-(4-formyl-n-methylanilino)acetic acid Chemical compound OC(=O)CN(C)C1=CC=C(C=O)C=C1 GNMSZDCHTBBZAV-UHFFFAOYSA-N 0.000 description 2
• ZPTCUHGUXYTJJK-UHFFFAOYSA-N 2-(4-formylanilino)acetic acid Chemical compound OC(=O)CNC1=CC=C(C=O)C=C1 ZPTCUHGUXYTJJK-UHFFFAOYSA-N 0.000 description 2
• YLJFPXRGJPDBOB-UHFFFAOYSA-N 2-(4-formylphenoxy)-n,n-dimethylacetamide Chemical compound CN(C)C(=O)COC1=CC=C(C=O)C=C1 YLJFPXRGJPDBOB-UHFFFAOYSA-N 0.000 description 2
• RIDGSEGTBIWFTK-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropanenitrile Chemical compound CN(C)C(C)(C)C#N RIDGSEGTBIWFTK-UHFFFAOYSA-N 0.000 description 2
• BDYDMRYPUIYCOY-UHFFFAOYSA-N 2-[4-(hydroxymethyl)phenyl]-n-methylacetamide Chemical compound CNC(=O)CC1=CC=C(CO)C=C1 BDYDMRYPUIYCOY-UHFFFAOYSA-N 0.000 description 2
• ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 2
• WXZYJVGQZNZIRC-UHFFFAOYSA-N 2-n,2-n,2-trimethylpropane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.CN(C)C(C)(C)CN WXZYJVGQZNZIRC-UHFFFAOYSA-N 0.000 description 2
• DYKJXWALYRGLPF-UHFFFAOYSA-N 2-phenyl-1h-imidazo[4,5-b]pyridine Chemical class C1=CC=CC=C1C1=NC2=NC=CC=C2N1 DYKJXWALYRGLPF-UHFFFAOYSA-N 0.000 description 2
• JPHKMYXKNKLNDF-UHFFFAOYSA-N 3,4-difluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1F JPHKMYXKNKLNDF-UHFFFAOYSA-N 0.000 description 2
• NRCCSDVEUWXOMG-UHFFFAOYSA-N 3-(4-formylphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(C=O)C=C1 NRCCSDVEUWXOMG-UHFFFAOYSA-N 0.000 description 2
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
• QSBHJTCAPWOIIE-UHFFFAOYSA-N 3-fluoro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1F QSBHJTCAPWOIIE-UHFFFAOYSA-N 0.000 description 2
• RBIGKSZIQCTIJF-UHFFFAOYSA-N 3-formylthiophene Chemical compound O=CC=1C=CSC=1 RBIGKSZIQCTIJF-UHFFFAOYSA-N 0.000 description 2
• BSQKBHXYEKVKMN-UHFFFAOYSA-N 3-methylthiophene-2-carbaldehyde Chemical compound CC=1C=CSC=1C=O BSQKBHXYEKVKMN-UHFFFAOYSA-N 0.000 description 2
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
• UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 description 2
• JSQPJYCQODOBRW-UHFFFAOYSA-N 5-bromo-4-N-(1-methylpiperidin-4-yl)-3-nitropyridine-2,4-diamine Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)C JSQPJYCQODOBRW-UHFFFAOYSA-N 0.000 description 2
• LVUIVVSOVBLPTN-UHFFFAOYSA-N 5-chloro-3-nitro-4-N-(1-propan-2-ylpiperidin-4-yl)pyridine-2,4-diamine Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)C(C)C LVUIVVSOVBLPTN-UHFFFAOYSA-N 0.000 description 2
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 2
• 208000008190 Agammaglobulinemia Diseases 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• 206010060971 Astrocytoma malignant Diseases 0.000 description 2
• 206010003827 Autoimmune hepatitis Diseases 0.000 description 2
• 208000027496 Behcet disease Diseases 0.000 description 2
• 208000009299 Benign Mucous Membrane Pemphigoid Diseases 0.000 description 2
• 206010004593 Bile duct cancer Diseases 0.000 description 2
• CGXAUQQVPUGHEB-UHFFFAOYSA-N BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CCC Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CCC CGXAUQQVPUGHEB-UHFFFAOYSA-N 0.000 description 2
• IZTZXGBLWVCANU-UHFFFAOYSA-N C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C(C(=NC=C1Cl)N)[N+](=O)[O-])C Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C(C(=NC=C1Cl)N)[N+](=O)[O-])C IZTZXGBLWVCANU-UHFFFAOYSA-N 0.000 description 2
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
• 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 description 2
• UOOPOMDCFNSQFW-UHFFFAOYSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1SC=CC=1 Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1SC=CC=1 UOOPOMDCFNSQFW-UHFFFAOYSA-N 0.000 description 2
• AWESDCPXDVRXHJ-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(CN(C)C)(C)C)C=C1)Cl Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC(CN(C)C)(C)C)C=C1)Cl AWESDCPXDVRXHJ-UHFFFAOYSA-N 0.000 description 2
• 206010009900 Colitis ulcerative Diseases 0.000 description 2
• 206010009944 Colon cancer Diseases 0.000 description 2
• RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
• 206010012438 Dermatitis atopic Diseases 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 208000021309 Germ cell tumor Diseases 0.000 description 2
• 206010018364 Glomerulonephritis Diseases 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• 208000035895 Guillain-Barré syndrome Diseases 0.000 description 2
• 208000002250 Hematologic Neoplasms Diseases 0.000 description 2
• 102100031573 Hematopoietic progenitor cell antigen CD34 Human genes 0.000 description 2
• 101000777663 Homo sapiens Hematopoietic progenitor cell antigen CD34 Proteins 0.000 description 2
• 206010020751 Hypersensitivity Diseases 0.000 description 2
• 206010020983 Hypogammaglobulinaemia Diseases 0.000 description 2
• 208000010159 IgA glomerulonephritis Diseases 0.000 description 2
• 206010021263 IgA nephropathy Diseases 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 208000003456 Juvenile Arthritis Diseases 0.000 description 2
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 2
• 208000032514 Leukocytoclastic vasculitis Diseases 0.000 description 2
• 208000025205 Mantle-Cell Lymphoma Diseases 0.000 description 2
• 208000001145 Metabolic Syndrome Diseases 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• 206010049567 Miller Fisher syndrome Diseases 0.000 description 2
• 208000003250 Mixed connective tissue disease Diseases 0.000 description 2
• 241000699670 Mus sp. Species 0.000 description 2
• YYFSTSWXSALKLC-UHFFFAOYSA-N N-[1-(dimethylamino)-2-methylpropan-2-yl]-2-(4-formylphenoxy)acetamide Chemical compound CN(CC(C)(C)NC(COC1=CC=C(C=C1)C=O)=O)C YYFSTSWXSALKLC-UHFFFAOYSA-N 0.000 description 2
• NYKNXEUHOUCKSL-UHFFFAOYSA-N N-[2-(dimethylamino)-2-methylpropyl]-2-(4-formylphenoxy)acetamide Chemical compound CN(C(CNC(COC1=CC=C(C=C1)C=O)=O)(C)C)C NYKNXEUHOUCKSL-UHFFFAOYSA-N 0.000 description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 2
• 229910004878 Na2S2O4 Inorganic materials 0.000 description 2
• 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 description 2
• 206010029260 Neuroblastoma Diseases 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• 108700020796 Oncogene Proteins 0.000 description 2
• 102000016978 Orphan receptors Human genes 0.000 description 2
• 108070000031 Orphan receptors Proteins 0.000 description 2
• 208000000733 Paroxysmal Hemoglobinuria Diseases 0.000 description 2
• 208000008223 Pemphigoid Gestationis Diseases 0.000 description 2
• 102100036050 Phosphatidylinositol N-acetylglucosaminyltransferase subunit A Human genes 0.000 description 2
• 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
• 201000004681 Psoriasis Diseases 0.000 description 2
• PLXBWHJQWKZRKG-UHFFFAOYSA-N Resazurin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3[N+]([O-])=C21 PLXBWHJQWKZRKG-UHFFFAOYSA-N 0.000 description 2
• 229910006124 SOCl2 Inorganic materials 0.000 description 2
• 206010040047 Sepsis Diseases 0.000 description 2
• 208000021386 Sjogren Syndrome Diseases 0.000 description 2
• 208000000453 Skin Neoplasms Diseases 0.000 description 2
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
• 208000006045 Spondylarthropathies Diseases 0.000 description 2
• 206010042276 Subacute endocarditis Diseases 0.000 description 2
• 201000009594 Systemic Scleroderma Diseases 0.000 description 2
• 206010042953 Systemic sclerosis Diseases 0.000 description 2
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 2
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 2
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 2
• 201000006704 Ulcerative Colitis Diseases 0.000 description 2
• 206010046851 Uveitis Diseases 0.000 description 2
• 208000004354 Vulvar Neoplasms Diseases 0.000 description 2
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 2
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
• 239000004480 active ingredient Substances 0.000 description 2
• 208000002552 acute disseminated encephalomyelitis Diseases 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 150000001408 amides Chemical group 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 150000001413 amino acids Chemical group 0.000 description 2
• 235000012538 ammonium bicarbonate Nutrition 0.000 description 2
• 201000008937 atopic dermatitis Diseases 0.000 description 2
• 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 2
• 229960000686 benzalkonium chloride Drugs 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 235000019445 benzyl alcohol Nutrition 0.000 description 2
• CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
• UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 230000008827 biological function Effects 0.000 description 2
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
• 239000001768 carboxy methyl cellulose Substances 0.000 description 2
• 230000024245 cell differentiation Effects 0.000 description 2
• 201000007335 cerebellar astrocytoma Diseases 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 239000003086 colorant Substances 0.000 description 2
• 239000012230 colorless oil Substances 0.000 description 2
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 201000001981 dermatomyositis Diseases 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
• 230000003828 downregulation Effects 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 239000003937 drug carrier Substances 0.000 description 2
• 238000000132 electrospray ionisation Methods 0.000 description 2
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 2
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 2
• 208000024519 eye neoplasm Diseases 0.000 description 2
• 230000001605 fetal effect Effects 0.000 description 2
• CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
• 230000002496 gastric effect Effects 0.000 description 2
• 238000011223 gene expression profiling Methods 0.000 description 2
• 201000007116 gestational trophoblastic neoplasm Diseases 0.000 description 2
• 125000005456 glyceride group Chemical group 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• 230000036541 health Effects 0.000 description 2
• 201000005787 hematologic cancer Diseases 0.000 description 2
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
• 230000006872 improvement Effects 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 230000002757 inflammatory effect Effects 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
• 201000002215 juvenile rheumatoid arthritis Diseases 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 230000000670 limiting effect Effects 0.000 description 2
• 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 2
• 239000006210 lotion Substances 0.000 description 2
• 239000000314 lubricant Substances 0.000 description 2
• 208000037841 lung tumor Diseases 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• 238000002844 melting Methods 0.000 description 2
• 230000008018 melting Effects 0.000 description 2
• SEGLMAZHEMCYEC-UHFFFAOYSA-N methyl 2-(2-fluoro-4-formylphenoxy)acetate Chemical compound FC1=C(OCC(=O)OC)C=CC(=C1)C=O SEGLMAZHEMCYEC-UHFFFAOYSA-N 0.000 description 2
• AYMQCLGUHSIDFY-UHFFFAOYSA-N methyl 2-(3-formylphenoxy)acetate Chemical compound COC(=O)COC1=CC=CC(C=O)=C1 AYMQCLGUHSIDFY-UHFFFAOYSA-N 0.000 description 2
• INMBNUKPYFMOOV-UHFFFAOYSA-N methyl 2-(4-formylanilino)acetate Chemical compound COC(=O)CNC1=CC=C(C=O)C=C1 INMBNUKPYFMOOV-UHFFFAOYSA-N 0.000 description 2
• LLDQUDYCTIKKFV-UHFFFAOYSA-N methyl 2-[4-(hydroxymethyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=C(CO)C=C1 LLDQUDYCTIKKFV-UHFFFAOYSA-N 0.000 description 2
• PQUSVJVVRXWKDG-UHFFFAOYSA-N methyl 2-bromo-2-methylpropanoate Chemical compound COC(=O)C(C)(C)Br PQUSVJVVRXWKDG-UHFFFAOYSA-N 0.000 description 2
• YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
• 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 235000010981 methylcellulose Nutrition 0.000 description 2
• 229960002216 methylparaben Drugs 0.000 description 2
• 239000002480 mineral oil Substances 0.000 description 2
• 235000010446 mineral oil Nutrition 0.000 description 2
• TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical compound OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 2
• PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
• 208000008795 neuromyelitis optica Diseases 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
• 239000000346 nonvolatile oil Substances 0.000 description 2
• BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
• 201000008106 ocular cancer Diseases 0.000 description 2
• 125000004430 oxygen atom Chemical group O* 0.000 description 2
• FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 description 2
• 201000003045 paroxysmal nocturnal hemoglobinuria Diseases 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 235000011007 phosphoric acid Nutrition 0.000 description 2
• 230000026731 phosphorylation Effects 0.000 description 2
• 238000006366 phosphorylation reaction Methods 0.000 description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
• 229940081310 piperonal Drugs 0.000 description 2
• 208000005987 polymyositis Diseases 0.000 description 2
• 235000015320 potassium carbonate Nutrition 0.000 description 2
• 238000004393 prognosis Methods 0.000 description 2
• 230000000750 progressive effect Effects 0.000 description 2
• 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 2
• 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
• 229960003415 propylparaben Drugs 0.000 description 2
• 108091008598 receptor tyrosine kinases Proteins 0.000 description 2
• 102000027426 receptor tyrosine kinases Human genes 0.000 description 2
• 230000010410 reperfusion Effects 0.000 description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 201000000306 sarcoidosis Diseases 0.000 description 2
• FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
• 230000019491 signal transduction Effects 0.000 description 2
• 201000000849 skin cancer Diseases 0.000 description 2
• 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
• 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
• 239000011343 solid material Substances 0.000 description 2
• 241000894007 species Species 0.000 description 2
• 201000005671 spondyloarthropathy Diseases 0.000 description 2
• 206010041823 squamous cell carcinoma Diseases 0.000 description 2
• 239000012258 stirred mixture Substances 0.000 description 2
• 208000008467 subacute bacterial endocarditis Diseases 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 208000011580 syndromic disease Diseases 0.000 description 2
• 230000008685 targeting Effects 0.000 description 2
• 206010043207 temporal arteritis Diseases 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• TZRQZPMQUXEZMC-UHFFFAOYSA-N tert-butyl n-(2-bromoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCBr TZRQZPMQUXEZMC-UHFFFAOYSA-N 0.000 description 2
• 238000012360 testing method Methods 0.000 description 2
• 239000002562 thickening agent Substances 0.000 description 2
• 230000000699 topical effect Effects 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• 238000001291 vacuum drying Methods 0.000 description 2
• MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
• WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
• 201000005102 vulva cancer Diseases 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
• UKQMAHIMUWQIPL-ZETCQYMHSA-N (3S)-1-(1,3-thiazol-2-ylmethyl)pyrrolidin-3-amine Chemical compound [C@H]1(N)CCN(C1)CC=1SC=CN=1 UKQMAHIMUWQIPL-ZETCQYMHSA-N 0.000 description 1
• HOMXVWQSBMJCBB-VIFPVBQESA-N (3S)-1-(thiophen-3-ylmethyl)pyrrolidin-3-amine Chemical compound S1C=C(C=C1)CN1C[C@H](CC1)N HOMXVWQSBMJCBB-VIFPVBQESA-N 0.000 description 1
• PBMGBUITGIKFMH-VIFPVBQESA-N (3S)-1-[(3-methylthiophen-2-yl)methyl]pyrrolidin-3-amine Chemical compound CC1=C(SC=C1)CN1C[C@H](CC1)N PBMGBUITGIKFMH-VIFPVBQESA-N 0.000 description 1
• ISIRAXCAUITZIH-JTQLQIEISA-N (3s)-1-(1,3-benzodioxol-5-ylmethyl)pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1CC1=CC=C(OCO2)C2=C1 ISIRAXCAUITZIH-JTQLQIEISA-N 0.000 description 1
• YRKRLJLVSPPREA-LBPRGKRZSA-N (3s)-1-(2-phenylethyl)pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1CCC1=CC=CC=C1 YRKRLJLVSPPREA-LBPRGKRZSA-N 0.000 description 1
• GMXRYOASLQUMPP-QMMMGPOBSA-N (3s)-1-(thiophen-2-ylmethyl)pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1CC1=CC=CS1 GMXRYOASLQUMPP-QMMMGPOBSA-N 0.000 description 1
• KBQWAGIDBNRGMT-LBPRGKRZSA-N (3s)-1-[(2-methylphenyl)methyl]pyrrolidin-3-amine Chemical compound CC1=CC=CC=C1CN1C[C@@H](N)CC1 KBQWAGIDBNRGMT-LBPRGKRZSA-N 0.000 description 1
• VKVICYGZWPAIHB-VIFPVBQESA-N (3s)-1-[(3,4-difluorophenyl)methyl]pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1CC1=CC=C(F)C(F)=C1 VKVICYGZWPAIHB-VIFPVBQESA-N 0.000 description 1
• YFXLADVUIYRKLL-NSHDSACASA-N (3s)-1-[(3-methoxyphenyl)methyl]pyrrolidin-3-amine Chemical compound COC1=CC=CC(CN2C[C@@H](N)CC2)=C1 YFXLADVUIYRKLL-NSHDSACASA-N 0.000 description 1
• BEHYEDRAAKQLCM-LBPRGKRZSA-N (3s)-1-[(3-methylphenyl)methyl]pyrrolidin-3-amine Chemical compound CC1=CC=CC(CN2C[C@@H](N)CC2)=C1 BEHYEDRAAKQLCM-LBPRGKRZSA-N 0.000 description 1
• XQBNUZCWBALDMP-NSHDSACASA-N (3s)-1-[(4-fluorophenyl)methyl]pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1CC1=CC=C(F)C=C1 XQBNUZCWBALDMP-NSHDSACASA-N 0.000 description 1
• XCAHYEUISIUALY-NSHDSACASA-N (3s)-1-[(4-methoxyphenyl)methyl]pyrrolidin-3-amine Chemical compound C1=CC(OC)=CC=C1CN1C[C@@H](N)CC1 XCAHYEUISIUALY-NSHDSACASA-N 0.000 description 1
• INUIZQJUGAJHBH-LBPRGKRZSA-N (3s)-1-[(4-methylphenyl)methyl]pyrrolidin-3-amine Chemical compound C1=CC(C)=CC=C1CN1C[C@@H](N)CC1 INUIZQJUGAJHBH-LBPRGKRZSA-N 0.000 description 1
• QPMFCOOSBGLJNO-NSHDSACASA-N (3s)-1-[[4-(trifluoromethyl)phenyl]methyl]pyrrolidin-3-amine Chemical compound C1[C@@H](N)CCN1CC1=CC=C(C(F)(F)F)C=C1 QPMFCOOSBGLJNO-NSHDSACASA-N 0.000 description 1
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 description 1
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
• RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 description 1
• QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 1
• HMTUBXVXHHITGO-UHFFFAOYSA-N 1,3,5-trimethylpyrazole-4-carbaldehyde Chemical compound CC1=NN(C)C(C)=C1C=O HMTUBXVXHHITGO-UHFFFAOYSA-N 0.000 description 1
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
• CHPNPFRWYMETGD-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(OCO2)C2=C1 CHPNPFRWYMETGD-UHFFFAOYSA-N 0.000 description 1
• NEEREDNBUVBCOK-UHFFFAOYSA-N 1-(1,3-thiazol-2-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=NC=CS1 NEEREDNBUVBCOK-UHFFFAOYSA-N 0.000 description 1
• BJOFVKOYOSXKPD-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)piperidin-4-amine Chemical compound CC(C)(C)CN1CCC(N)CC1 BJOFVKOYOSXKPD-UHFFFAOYSA-N 0.000 description 1
• PCNBAXKQILQDMV-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(OCCO2)C2=C1 PCNBAXKQILQDMV-UHFFFAOYSA-N 0.000 description 1
• OXHPTABOQVHKLN-UHFFFAOYSA-N 1-(2-bromoethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCBr)C=C1 OXHPTABOQVHKLN-UHFFFAOYSA-N 0.000 description 1
• ILMDRDDKNWKCNX-UHFFFAOYSA-N 1-(2-methoxyethyl)piperidin-4-amine Chemical compound COCCN1CCC(N)CC1 ILMDRDDKNWKCNX-UHFFFAOYSA-N 0.000 description 1
• FIXAVWUOHALGPB-UHFFFAOYSA-N 1-(2-phenoxyethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CCOC1=CC=CC=C1 FIXAVWUOHALGPB-UHFFFAOYSA-N 0.000 description 1
• BCEKLYJIVXGPLQ-UHFFFAOYSA-N 1-(2-phenylethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CCC1=CC=CC=C1 BCEKLYJIVXGPLQ-UHFFFAOYSA-N 0.000 description 1
• WYDUUQNGNSXLRC-UHFFFAOYSA-N 1-(cyclohexylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1CCCCC1 WYDUUQNGNSXLRC-UHFFFAOYSA-N 0.000 description 1
• MMHWXHGXQNBQIR-UHFFFAOYSA-N 1-(furan-3-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=COC=C1 MMHWXHGXQNBQIR-UHFFFAOYSA-N 0.000 description 1
• MSXJQLZTWITCEC-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CN=C1 MSXJQLZTWITCEC-UHFFFAOYSA-N 0.000 description 1
• XFBCPLXWYFVCTB-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=NC=C1 XFBCPLXWYFVCTB-UHFFFAOYSA-N 0.000 description 1
• NTNFMOPKOCZICX-UHFFFAOYSA-N 1-(thiophen-3-ylmethyl)piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CSC=C1 NTNFMOPKOCZICX-UHFFFAOYSA-N 0.000 description 1
• OUKQTRFCDKSEPL-UHFFFAOYSA-N 1-Methyl-2-pyrrolecarboxaldehyde Chemical compound CN1C=CC=C1C=O OUKQTRFCDKSEPL-UHFFFAOYSA-N 0.000 description 1
• VMRLENHVJMEDMH-UHFFFAOYSA-N 1-[(1-methylpyrrol-2-yl)methyl]piperidin-4-amine Chemical compound CN1C=CC=C1CN1CCC(N)CC1 VMRLENHVJMEDMH-UHFFFAOYSA-N 0.000 description 1
• APFLDIWBHKFGQN-UHFFFAOYSA-N 1-[(2,4-dimethoxyphenyl)methyl]piperidin-4-amine Chemical compound COC1=CC(OC)=CC=C1CN1CCC(N)CC1 APFLDIWBHKFGQN-UHFFFAOYSA-N 0.000 description 1
• DVBRJIYUDLSVGV-UHFFFAOYSA-N 1-[(2-methoxyphenyl)methyl]piperidin-4-amine Chemical compound COC1=CC=CC=C1CN1CCC(N)CC1 DVBRJIYUDLSVGV-UHFFFAOYSA-N 0.000 description 1
• WNQXIWMYWRHSNU-UHFFFAOYSA-N 1-[(3,4-difluorophenyl)methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(F)C(F)=C1 WNQXIWMYWRHSNU-UHFFFAOYSA-N 0.000 description 1
• SFGKHXRAIWBGPR-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]piperidin-4-amine Chemical compound C1=C(OC)C(OC)=CC=C1CN1CCC(N)CC1 SFGKHXRAIWBGPR-UHFFFAOYSA-N 0.000 description 1
• ZSNTXKRANYMRKW-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]piperidin-4-amine Chemical compound COC1=CC=CC(CN2CCC(N)CC2)=C1 ZSNTXKRANYMRKW-UHFFFAOYSA-N 0.000 description 1
• DFJQENRMQNZDNL-UHFFFAOYSA-N 1-[(3-methylphenyl)methyl]piperidin-4-amine Chemical compound CC1=CC=CC(CN2CCC(N)CC2)=C1 DFJQENRMQNZDNL-UHFFFAOYSA-N 0.000 description 1
• QPAFCHITAPDUDC-UHFFFAOYSA-N 1-[(3-methylthiophen-2-yl)methyl]piperidin-4-amine Chemical compound C1=CSC(CN2CCC(N)CC2)=C1C QPAFCHITAPDUDC-UHFFFAOYSA-N 0.000 description 1
• BIMZLZOTBSPLRM-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(Cl)C=C1 BIMZLZOTBSPLRM-UHFFFAOYSA-N 0.000 description 1
• VYAFGMJUYVSISF-UHFFFAOYSA-N 1-[(4-ethoxyphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(OCC)=CC=C1CN1CCC(N)CC1 VYAFGMJUYVSISF-UHFFFAOYSA-N 0.000 description 1
• KRIHULMCWJRKQE-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(F)C=C1 KRIHULMCWJRKQE-UHFFFAOYSA-N 0.000 description 1
• MKXDXJLEIXOVOD-UHFFFAOYSA-N 1-[(4-methoxy-3,5-dimethylphenyl)methyl]piperidin-4-amine Chemical compound C1=C(C)C(OC)=C(C)C=C1CN1CCC(N)CC1 MKXDXJLEIXOVOD-UHFFFAOYSA-N 0.000 description 1
• WKSLXYCTQDBDDR-UHFFFAOYSA-N 1-[(4-methoxy-3-methylphenyl)methyl]piperidin-4-amine Chemical compound C1=C(C)C(OC)=CC=C1CN1CCC(N)CC1 WKSLXYCTQDBDDR-UHFFFAOYSA-N 0.000 description 1
• BRUKSTGIAUDJQX-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(C)=CC=C1CN1CCC(N)CC1 BRUKSTGIAUDJQX-UHFFFAOYSA-N 0.000 description 1
• ORKBVCSMWCIDAJ-UHFFFAOYSA-N 1-[(4-methylsulfonylphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CN1CCC(N)CC1 ORKBVCSMWCIDAJ-UHFFFAOYSA-N 0.000 description 1
• RDADMNIYJZRZCQ-UHFFFAOYSA-N 1-[(4-propan-2-yloxyphenyl)methyl]piperidin-4-amine Chemical compound C1=CC(OC(C)C)=CC=C1CN1CCC(N)CC1 RDADMNIYJZRZCQ-UHFFFAOYSA-N 0.000 description 1
• SKYURCFJFSFYMB-UHFFFAOYSA-N 1-[(5-methylfuran-2-yl)methyl]piperidin-4-amine Chemical compound O1C(C)=CC=C1CN1CCC(N)CC1 SKYURCFJFSFYMB-UHFFFAOYSA-N 0.000 description 1
• CPRWTWWKEVYCTA-UHFFFAOYSA-N 1-[(6-methylpyridin-2-yl)methyl]piperidin-4-amine Chemical compound CC1=CC=CC(CN2CCC(N)CC2)=N1 CPRWTWWKEVYCTA-UHFFFAOYSA-N 0.000 description 1
• HTGMIBQQTLUEKV-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]piperidin-4-amine Chemical compound C1=CC(OC)=CC=C1CCN1CCC(N)CC1 HTGMIBQQTLUEKV-UHFFFAOYSA-N 0.000 description 1
• QIXTXHJKQMEABL-UHFFFAOYSA-N 1-[[4-(difluoromethoxy)phenyl]methyl]piperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=C(OC(F)F)C=C1 QIXTXHJKQMEABL-UHFFFAOYSA-N 0.000 description 1
• CZEBDZMBUKUETA-UHFFFAOYSA-N 1-[[4-(dimethylamino)phenyl]methyl]piperidin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1CN1CCC(N)CC1 CZEBDZMBUKUETA-UHFFFAOYSA-N 0.000 description 1
• RGEQSTMITLEXKD-UHFFFAOYSA-N 1-benzyl-n-methylpiperidin-4-amine Chemical compound C1CC(NC)CCN1CC1=CC=CC=C1 RGEQSTMITLEXKD-UHFFFAOYSA-N 0.000 description 1
• YUBDLZGUSSWQSS-UHFFFAOYSA-N 1-benzylpiperidin-4-amine Chemical compound C1CC(N)CCN1CC1=CC=CC=C1 YUBDLZGUSSWQSS-UHFFFAOYSA-N 0.000 description 1
• FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
• MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
• MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-UHFFFAOYSA-N 0.000 description 1
• GZWFMQMAEUUNCC-UHFFFAOYSA-N 1-cyclohexylpiperidin-4-amine Chemical compound C1CC(N)CCN1C1CCCCC1 GZWFMQMAEUUNCC-UHFFFAOYSA-N 0.000 description 1
• ZRKJGYYOBCLVPV-UHFFFAOYSA-N 1-hexylpiperidin-4-amine Chemical compound CCCCCCN1CCC(N)CC1 ZRKJGYYOBCLVPV-UHFFFAOYSA-N 0.000 description 1
• ALOCUZOKRULSAA-UHFFFAOYSA-N 1-methylpiperidin-4-amine Chemical compound CN1CCC(N)CC1 ALOCUZOKRULSAA-UHFFFAOYSA-N 0.000 description 1
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• CWKXDPPQCVWXAG-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde Chemical compound O1CCOC2=CC(C=O)=CC=C21 CWKXDPPQCVWXAG-UHFFFAOYSA-N 0.000 description 1
• WEBVDBDZSOJGPB-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-carbaldehyde Chemical compound O=CC1=CC=C2OCCC2=C1 WEBVDBDZSOJGPB-UHFFFAOYSA-N 0.000 description 1
• PSOZMUMWCXLRKX-UHFFFAOYSA-N 2,4-dinitro-6-pentan-2-ylphenol Chemical compound CCCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O PSOZMUMWCXLRKX-UHFFFAOYSA-N 0.000 description 1
• IMXGRGYVMVVAOG-UHFFFAOYSA-N 2-(2-fluoro-4-formylphenoxy)-N-methylacetamide Chemical compound FC1=C(OCC(=O)NC)C=CC(=C1)C=O IMXGRGYVMVVAOG-UHFFFAOYSA-N 0.000 description 1
• MEZDQWHYVCFJSS-UHFFFAOYSA-N 2-(2-fluoro-4-formylphenoxy)-N-propan-2-ylacetamide Chemical compound FC1=C(OCC(=O)NC(C)C)C=CC(=C1)C=O MEZDQWHYVCFJSS-UHFFFAOYSA-N 0.000 description 1
• DXMYUKICWKDCHW-UHFFFAOYSA-N 2-(4-formyl-2,6-dimethylphenoxy)-n-methylacetamide Chemical compound CNC(=O)COC1=C(C)C=C(C=O)C=C1C DXMYUKICWKDCHW-UHFFFAOYSA-N 0.000 description 1
• DYSUWBZLDDHWMV-UHFFFAOYSA-N 2-(4-formyl-2-methoxyphenoxy)-n-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C=O)C=C1OC DYSUWBZLDDHWMV-UHFFFAOYSA-N 0.000 description 1
• LCUSIECADLMWEU-UHFFFAOYSA-N 2-(4-formylphenoxy)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(C=O)C=C1 LCUSIECADLMWEU-UHFFFAOYSA-N 0.000 description 1
• LVTYODRZCXHXBR-UHFFFAOYSA-N 2-(4-formylphenoxy)-N-(1,3,4-thiadiazol-2-yl)acetamide Chemical compound O=CC1=CC=C(OCC(=O)NC2=NN=CS2)C=C1 LVTYODRZCXHXBR-UHFFFAOYSA-N 0.000 description 1
• PPZNQBNAOOCWSX-UHFFFAOYSA-N 2-(4-formylphenoxy)-N-(3-methyl-1,2-oxazol-5-yl)acetamide Chemical compound C(=O)C1=CC=C(OCC(=O)NC2=CC(=NO2)C)C=C1 PPZNQBNAOOCWSX-UHFFFAOYSA-N 0.000 description 1
• HDLPREPUZUZXBF-UHFFFAOYSA-N 2-(4-formylphenoxy)-N-pyrimidin-2-ylacetamide Chemical compound C(=O)C1=CC=C(OCC(=O)NC2=NC=CC=N2)C=C1 HDLPREPUZUZXBF-UHFFFAOYSA-N 0.000 description 1
• WCQUPWCZRBFFIJ-UHFFFAOYSA-N 2-(4-formylphenoxy)-N-pyrimidin-5-ylacetamide Chemical compound C(=O)C1=CC=C(OCC(=O)NC=2C=NC=NC=2)C=C1 WCQUPWCZRBFFIJ-UHFFFAOYSA-N 0.000 description 1
• MXGHVNKPNQEZPM-UHFFFAOYSA-N 2-(4-formylphenoxy)-n-(1,3-thiazol-2-yl)acetamide Chemical compound C1=CC(C=O)=CC=C1OCC(=O)NC1=NC=CS1 MXGHVNKPNQEZPM-UHFFFAOYSA-N 0.000 description 1
• MQWNZEVYMRFPAY-UHFFFAOYSA-N 2-(4-formylphenoxy)-n-(5-methyl-1,2-oxazol-3-yl)acetamide Chemical compound O1C(C)=CC(NC(=O)COC=2C=CC(C=O)=CC=2)=N1 MQWNZEVYMRFPAY-UHFFFAOYSA-N 0.000 description 1
• YESRHUCGAHWTSL-UHFFFAOYSA-N 2-(4-formylphenyl)-n-methylacetamide Chemical compound CNC(=O)CC1=CC=C(C=O)C=C1 YESRHUCGAHWTSL-UHFFFAOYSA-N 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
• IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
• IAJHDJTXMUHGNM-UHFFFAOYSA-N 2-[4-(6,7-dichloro-1H-imidazo[4,5-b]pyridin-2-yl)-3-methylphenoxy]-N-methylacetamide Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=C(C=C(OCC(=O)NC)C=C1)C)Cl IAJHDJTXMUHGNM-UHFFFAOYSA-N 0.000 description 1
• FWZBPBKAANKOJQ-UHFFFAOYSA-N 2-[4-(hydroxymethyl)phenyl]acetic acid Chemical compound OCC1=CC=C(CC(O)=O)C=C1 FWZBPBKAANKOJQ-UHFFFAOYSA-N 0.000 description 1
• XESOREUKSDZNOO-UHFFFAOYSA-N 2-[4-[7-[(1-benzylpiperidin-4-yl)-methylamino]-6-chloro-1H-imidazo[4,5-b]pyridin-2-yl]phenoxy]acetic acid Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)N(C1=C2C(=NC=C1Cl)NC(=N2)C1=CC=C(OCC(=O)O)C=C1)C XESOREUKSDZNOO-UHFFFAOYSA-N 0.000 description 1
• JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
• NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
• UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
• 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
• DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
• JESRNIJXVIFVOV-UHFFFAOYSA-N 2-methylpyrazol-3-amine Chemical compound CN1N=CC=C1N JESRNIJXVIFVOV-UHFFFAOYSA-N 0.000 description 1
• FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
• LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• LXXDAJSGINOLSW-UHFFFAOYSA-N 3-[(4-aminopiperidin-1-yl)methyl]benzonitrile Chemical compound C1CC(N)CCN1CC1=CC=CC(C#N)=C1 LXXDAJSGINOLSW-UHFFFAOYSA-N 0.000 description 1
• WAURZPJBMDKXCF-UHFFFAOYSA-N 3-[(4-aminopiperidin-1-yl)methyl]phenol Chemical compound C1CC(N)CCN1CC1=CC=CC(O)=C1 WAURZPJBMDKXCF-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• HGZJJKZPPMFIBU-UHFFFAOYSA-N 3-formylbenzonitrile Chemical compound O=CC1=CC=CC(C#N)=C1 HGZJJKZPPMFIBU-UHFFFAOYSA-N 0.000 description 1
• AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 1
• FNXYWHTZDAVRTB-UHFFFAOYSA-N 3-methyl-1,2-oxazol-5-amine Chemical compound CC=1C=C(N)ON=1 FNXYWHTZDAVRTB-UHFFFAOYSA-N 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• TVEJNWMWDIXPAX-UHFFFAOYSA-N 4-(1,2,4-triazol-1-yl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1N=CN=C1 TVEJNWMWDIXPAX-UHFFFAOYSA-N 0.000 description 1
• ZWCXOJYJJINQGU-UHFFFAOYSA-N 4-(difluoromethoxy)benzaldehyde Chemical compound FC(F)OC1=CC=C(C=O)C=C1 ZWCXOJYJJINQGU-UHFFFAOYSA-N 0.000 description 1
• BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
• BEOBZEOPTQQELP-UHFFFAOYSA-N 4-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=C(C=O)C=C1 BEOBZEOPTQQELP-UHFFFAOYSA-N 0.000 description 1
• SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
• BAKYASSDAXQKKY-UHFFFAOYSA-N 4-Hydroxy-3-methylbenzaldehyde Chemical compound CC1=CC(C=O)=CC=C1O BAKYASSDAXQKKY-UHFFFAOYSA-N 0.000 description 1
• DTAODPWLQDLNCE-UHFFFAOYSA-N 4-[(4-aminopiperidin-1-yl)methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(CN2CCC(N)CC2)=C1 DTAODPWLQDLNCE-UHFFFAOYSA-N 0.000 description 1
• NPRFHMPSSNCLDY-UHFFFAOYSA-N 4-[(4-aminopiperidin-1-yl)methyl]benzonitrile Chemical compound C1CC(N)CCN1CC1=CC=C(C#N)C=C1 NPRFHMPSSNCLDY-UHFFFAOYSA-N 0.000 description 1
• AMGFIJVPWRHZFG-UHFFFAOYSA-N 4-[(4-aminopiperidin-1-yl)methyl]phenol Chemical compound C1CC(N)CCN1CC1=CC=C(O)C=C1 AMGFIJVPWRHZFG-UHFFFAOYSA-N 0.000 description 1
• DIRINUVNYFAWQF-UHFFFAOYSA-N 4-chloro-3-nitropyridin-2-amine Chemical compound NC1=NC=CC(Cl)=C1[N+]([O-])=O DIRINUVNYFAWQF-UHFFFAOYSA-N 0.000 description 1
• AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
• RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 description 1
• WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
• JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 description 1
• XLIMLVMYIYSMIQ-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=C(C)C=C1O XLIMLVMYIYSMIQ-UHFFFAOYSA-N 0.000 description 1
• JDWWIEFMFPWBST-UHFFFAOYSA-N 4-hydroxy-2-methylbenzaldehyde Chemical compound CC1=CC(O)=CC=C1C=O JDWWIEFMFPWBST-UHFFFAOYSA-N 0.000 description 1
• SNIGEINPLSDHBQ-UHFFFAOYSA-N 4-methoxy-3,5-dimethylbenzaldehyde Chemical compound COC1=C(C)C=C(C=O)C=C1C SNIGEINPLSDHBQ-UHFFFAOYSA-N 0.000 description 1
• MYLBIQHZWFWSMH-UHFFFAOYSA-N 4-methoxy-3-methylbenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1C MYLBIQHZWFWSMH-UHFFFAOYSA-N 0.000 description 1
• QRVYABWJVXXOTN-UHFFFAOYSA-N 4-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(C=O)C=C1 QRVYABWJVXXOTN-UHFFFAOYSA-N 0.000 description 1
• PSVPUHBSBYJSMQ-UHFFFAOYSA-N 4-methylsulfonylbenzaldehyde Chemical compound CS(=O)(=O)C1=CC=C(C=O)C=C1 PSVPUHBSBYJSMQ-UHFFFAOYSA-N 0.000 description 1
• WDANSDASCKBVKH-UHFFFAOYSA-N 4-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=C(C=O)C=C1 WDANSDASCKBVKH-UHFFFAOYSA-N 0.000 description 1
• LBGXGCBGOLGUHV-UHFFFAOYSA-N 5-bromo-3-nitro-4-N-[1-[(1,3,5-trimethylpyrazol-4-yl)methyl]piperidin-4-yl]pyridine-2,4-diamine Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1C(=NN(C=1C)C)C LBGXGCBGOLGUHV-UHFFFAOYSA-N 0.000 description 1
• OKHNANPSEBYVDZ-UHFFFAOYSA-N 5-bromo-4-N-(1-ethylpiperidin-4-yl)-3-nitropyridine-2,4-diamine Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC OKHNANPSEBYVDZ-UHFFFAOYSA-N 0.000 description 1
• ZIFOKHJJPSZBCL-UHFFFAOYSA-N 5-bromo-4-N-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]-3-nitropyridine-2,4-diamine Chemical compound COC1=CC=C(CN2CCC(CC2)NC2=C(C(N)=NC=C2Br)[N+]([O-])=O)C=C1 ZIFOKHJJPSZBCL-UHFFFAOYSA-N 0.000 description 1
• DDOFUMWLNSICHU-UHFFFAOYSA-N 5-bromo-4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=C(Br)C=N1 DDOFUMWLNSICHU-UHFFFAOYSA-N 0.000 description 1
• ZHMASVAJFJFFLS-UHFFFAOYSA-N 5-chloropyridin-3-amine Chemical compound NC1=CN=CC(Cl)=C1 ZHMASVAJFJFFLS-UHFFFAOYSA-N 0.000 description 1
• FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 description 1
• OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 description 1
• GGXGVZJHUKEJHO-UHFFFAOYSA-N 5-tert-butyl-1,2-oxazol-3-amine Chemical compound CC(C)(C)C1=CC(N)=NO1 GGXGVZJHUKEJHO-UHFFFAOYSA-N 0.000 description 1
• AHISYUZBWDSPQL-UHFFFAOYSA-N 6-methylpyridine-2-carbaldehyde Chemical compound CC1=CC=CC(C=O)=N1 AHISYUZBWDSPQL-UHFFFAOYSA-N 0.000 description 1
• FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical compound C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 208000030507 AIDS Diseases 0.000 description 1
• 208000002008 AIDS-Related Lymphoma Diseases 0.000 description 1
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
• 206010056508 Acquired epidermolysis bullosa Diseases 0.000 description 1
• 206010000748 Acute febrile neutrophilic dermatosis Diseases 0.000 description 1
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
• 208000026872 Addison Disease Diseases 0.000 description 1
• 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 1
• 208000003200 Adenoma Diseases 0.000 description 1
• 208000002485 Adiposis dolorosa Diseases 0.000 description 1
• 244000003363 Allium ursinum Species 0.000 description 1
• 206010001889 Alveolitis Diseases 0.000 description 1
• 206010001935 American trypanosomiasis Diseases 0.000 description 1
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 1
• 206010061424 Anal cancer Diseases 0.000 description 1
• 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
• 208000003343 Antiphospholipid Syndrome Diseases 0.000 description 1
• 208000001839 Antisynthetase syndrome Diseases 0.000 description 1
• 208000007860 Anus Neoplasms Diseases 0.000 description 1
• 206010073360 Appendix cancer Diseases 0.000 description 1
• 206010003497 Asphyxia Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 206010003571 Astrocytoma Diseases 0.000 description 1
• 206010003645 Atopy Diseases 0.000 description 1
• 206010071576 Autoimmune aplastic anaemia Diseases 0.000 description 1
• 208000000659 Autoimmune lymphoproliferative syndrome Diseases 0.000 description 1
• 206010069002 Autoimmune pancreatitis Diseases 0.000 description 1
• 208000022106 Autoimmune polyendocrinopathy type 2 Diseases 0.000 description 1
• 108091008875 B cell receptors Proteins 0.000 description 1
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 1
• 201000001178 Bacterial Pneumonia Diseases 0.000 description 1
• 206010004146 Basal cell carcinoma Diseases 0.000 description 1
• 208000023328 Basedow disease Diseases 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
• 208000033222 Biliary cirrhosis primary Diseases 0.000 description 1
• 208000009766 Blau syndrome Diseases 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• JPUREEYSXHCOOQ-UHFFFAOYSA-N BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 JPUREEYSXHCOOQ-UHFFFAOYSA-N 0.000 description 1
• FSHIBAFJMRRFKL-UHFFFAOYSA-N BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1C=CC2=C(CCO2)C=1 Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1C=CC2=C(CCO2)C=1 FSHIBAFJMRRFKL-UHFFFAOYSA-N 0.000 description 1
• ZHWVVTCRSONIRP-UHFFFAOYSA-N BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1SC=CC=1 Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1SC=CC=1 ZHWVVTCRSONIRP-UHFFFAOYSA-N 0.000 description 1
• ZXZZRVXTLNJYOH-LURJTMIESA-N BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)C Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)C ZXZZRVXTLNJYOH-LURJTMIESA-N 0.000 description 1
• IMBNNIJXHKKALJ-LBPRGKRZSA-N BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC Chemical compound BrC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)CC1=C(C=CC=C1)OC IMBNNIJXHKKALJ-LBPRGKRZSA-N 0.000 description 1
• 201000006390 Brachial Plexus Neuritis Diseases 0.000 description 1
• 208000003174 Brain Neoplasms Diseases 0.000 description 1
• 206010048962 Brain oedema Diseases 0.000 description 1
• 206010006143 Brain stem glioma Diseases 0.000 description 1
• 206010006458 Bronchitis chronic Diseases 0.000 description 1
• BLXXPCWOXZHBCU-UHFFFAOYSA-N C(=O)C1=C(C=C(OCC(=O)OC)C=C1)C Chemical compound C(=O)C1=C(C=C(OCC(=O)OC)C=C1)C BLXXPCWOXZHBCU-UHFFFAOYSA-N 0.000 description 1
• BKUVASDNWACFAM-UHFFFAOYSA-N C(=O)C1=CC(=C(OCC(=O)NC)C=C1)C Chemical compound C(=O)C1=CC(=C(OCC(=O)NC)C=C1)C BKUVASDNWACFAM-UHFFFAOYSA-N 0.000 description 1
• PSSUGRJXRLQSJQ-UHFFFAOYSA-N C(=O)C1=CC(=C(OCC(=O)NC)C=C1C)C Chemical compound C(=O)C1=CC(=C(OCC(=O)NC)C=C1C)C PSSUGRJXRLQSJQ-UHFFFAOYSA-N 0.000 description 1
• VJMBNRXBAAYGLD-UHFFFAOYSA-N C(=O)C1=CC=C(C=C1)CCC(=O)NC Chemical compound C(=O)C1=CC=C(C=C1)CCC(=O)NC VJMBNRXBAAYGLD-UHFFFAOYSA-N 0.000 description 1
• SPBHUESJCZZGGX-UHFFFAOYSA-N C(=O)C1=CC=C(C=C1)N(CC(=O)NC=1C=NC=CC=1)C Chemical compound C(=O)C1=CC=C(C=C1)N(CC(=O)NC=1C=NC=CC=1)C SPBHUESJCZZGGX-UHFFFAOYSA-N 0.000 description 1
• XQWDAAOVXWTECS-UHFFFAOYSA-N C(=O)C1=CC=C(C=C1)NCCC(=O)NC Chemical compound C(=O)C1=CC=C(C=C1)NCCC(=O)NC XQWDAAOVXWTECS-UHFFFAOYSA-N 0.000 description 1
• GGGYFBQEWRZEGM-UHFFFAOYSA-N C(=O)C1=CC=C(OC(C(=O)NC)(C)C)C=C1 Chemical compound C(=O)C1=CC=C(OC(C(=O)NC)(C)C)C=C1 GGGYFBQEWRZEGM-UHFFFAOYSA-N 0.000 description 1
• PHBZFZWEVVUVLR-UHFFFAOYSA-N C(=O)C1=CC=C(OCC(=O)NC2=CC=NN2C)C=C1 Chemical compound C(=O)C1=CC=C(OCC(=O)NC2=CC=NN2C)C=C1 PHBZFZWEVVUVLR-UHFFFAOYSA-N 0.000 description 1
• GPDRTNQIAZQZDH-UHFFFAOYSA-N C(=O)C1=CC=C(OCC(=O)NC2=NC=CN=C2)C=C1 Chemical compound C(=O)C1=CC=C(OCC(=O)NC2=NC=CN=C2)C=C1 GPDRTNQIAZQZDH-UHFFFAOYSA-N 0.000 description 1
• VXSSTHWFPXTEAC-UHFFFAOYSA-N C(=O)C1=CC=C(OCC(=O)NC2=NNC=N2)C=C1 Chemical compound C(=O)C1=CC=C(OCC(=O)NC2=NNC=N2)C=C1 VXSSTHWFPXTEAC-UHFFFAOYSA-N 0.000 description 1
• FDKJALWSIDUHQS-UHFFFAOYSA-N C(=O)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1 Chemical compound C(=O)C1=CC=C(OCC(=O)NC2=NOC=C2)C=C1 FDKJALWSIDUHQS-UHFFFAOYSA-N 0.000 description 1
• MLBHWUWDBKOAQN-UHFFFAOYSA-N CNC(=O)CNC1=CC=C(C=O)C=C1 Chemical compound CNC(=O)CNC1=CC=C(C=O)C=C1 MLBHWUWDBKOAQN-UHFFFAOYSA-N 0.000 description 1
• 201000002829 CREST Syndrome Diseases 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 206010007279 Carcinoid tumour of the gastrointestinal tract Diseases 0.000 description 1
• 208000005024 Castleman disease Diseases 0.000 description 1
• 108010001857 Cell Surface Receptors Proteins 0.000 description 1
• 102000000844 Cell Surface Receptors Human genes 0.000 description 1
• 206010007953 Central nervous system lymphoma Diseases 0.000 description 1
• 241000282693 Cercopithecidae Species 0.000 description 1
• 206010008342 Cervix carcinoma Diseases 0.000 description 1
• 208000024699 Chagas disease Diseases 0.000 description 1
• 206010008609 Cholangitis sclerosing Diseases 0.000 description 1
• 208000031404 Chromosome Aberrations Diseases 0.000 description 1
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
• 201000000724 Chronic recurrent multifocal osteomyelitis Diseases 0.000 description 1
• DOQGFZVVRBRZSI-UHFFFAOYSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC(C)C Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC(C)C DOQGFZVVRBRZSI-UHFFFAOYSA-N 0.000 description 1
• MWJLJKKNPIPJBI-UHFFFAOYSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC1=CC=C(C=C1)N1N=CN=C1 MWJLJKKNPIPJBI-UHFFFAOYSA-N 0.000 description 1
• LYWNYZSURYYZRD-UHFFFAOYSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1C(=NN(C=1C)C)C Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCN(CC1)CC=1C(=NN(C=1C)C)C LYWNYZSURYYZRD-UHFFFAOYSA-N 0.000 description 1
• CJZFGNFUYODJCI-UHFFFAOYSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCNCC1 Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])NC1CCNCC1 CJZFGNFUYODJCI-UHFFFAOYSA-N 0.000 description 1
• WJZUEEYDJNGEGN-LURJTMIESA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)C Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)C WJZUEEYDJNGEGN-LURJTMIESA-N 0.000 description 1
• WJIVOGATDZSQLC-QMMMGPOBSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)C(C)C Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)C(C)C WJIVOGATDZSQLC-QMMMGPOBSA-N 0.000 description 1
• XYLGBXMQMNGMST-ZETCQYMHSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)CC Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)CC XYLGBXMQMNGMST-ZETCQYMHSA-N 0.000 description 1
• AKWQQDIAXNDYFY-QMMMGPOBSA-N ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)CCC Chemical compound ClC=1C(=C(C(=NC=1)N)[N+](=O)[O-])N[C@@H]1CN(CC1)CCC AKWQQDIAXNDYFY-QMMMGPOBSA-N 0.000 description 1
• KQDBZYPTLABFTR-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)O)NC1CCN(CC1)CC1=CC=C(C=C1)OC Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(C=C1)CCC(=O)O)NC1CCN(CC1)CC1=CC=C(C=C1)OC KQDBZYPTLABFTR-UHFFFAOYSA-N 0.000 description 1
• POWSJHGCEZKCJP-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)N(C)C)C=C1)Cl Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)N(C)C)C=C1)Cl POWSJHGCEZKCJP-UHFFFAOYSA-N 0.000 description 1
• SPQMRRWADNFKQJ-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)Cl Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NC)C=C1)Cl SPQMRRWADNFKQJ-UHFFFAOYSA-N 0.000 description 1
• BXWCEBCYHIEWDN-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC(C)(C)N(C)C)C=C1)Cl Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCC(C)(C)N(C)C)C=C1)Cl BXWCEBCYHIEWDN-UHFFFAOYSA-N 0.000 description 1
• GHWCYZTWAMXYLU-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1)Cl Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1)Cl GHWCYZTWAMXYLU-UHFFFAOYSA-N 0.000 description 1
• DHHCPZFVBCQAJE-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)O)C=C1)NC1CCN(CC1)C Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)O)C=C1)NC1CCN(CC1)C DHHCPZFVBCQAJE-UHFFFAOYSA-N 0.000 description 1
• OOOIYVYFLKKLOC-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1)NC(=N2)C=1C=C(OCC(=O)NC)C=CC=1)Cl Chemical compound ClC=1C(=C2C(=NC=1)NC(=N2)C=1C=C(OCC(=O)NC)C=CC=1)Cl OOOIYVYFLKKLOC-UHFFFAOYSA-N 0.000 description 1
• LEIKCVDQRRLTQB-UHFFFAOYSA-N ClC=1C=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1 Chemical compound ClC=1C=C2C(=NC=1)NC(=N2)C1=CC=C(OCC(=O)NCCN(C)C)C=C1 LEIKCVDQRRLTQB-UHFFFAOYSA-N 0.000 description 1
• 108091026890 Coding region Proteins 0.000 description 1
• 208000015943 Coeliac disease Diseases 0.000 description 1
• 208000010007 Cogan syndrome Diseases 0.000 description 1
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
• 206010010252 Concentric sclerosis Diseases 0.000 description 1
• 208000019707 Cryoglobulinemic vasculitis Diseases 0.000 description 1
• 208000014311 Cushing syndrome Diseases 0.000 description 1
• 201000003883 Cystic fibrosis Diseases 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
• 208000016192 Demyelinating disease Diseases 0.000 description 1
• 206010012442 Dermatitis contact Diseases 0.000 description 1
• 206010012468 Dermatitis herpetiformis Diseases 0.000 description 1
• 239000004375 Dextrin Substances 0.000 description 1
• 229920001353 Dextrin Polymers 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 206010051392 Diapedesis Diseases 0.000 description 1
• 201000003066 Diffuse Scleroderma Diseases 0.000 description 1
• 208000024134 Diffuse cutaneous systemic sclerosis Diseases 0.000 description 1
• 208000006926 Discoid Lupus Erythematosus Diseases 0.000 description 1
• 206010061818 Disease progression Diseases 0.000 description 1
• 208000021866 Dressler syndrome Diseases 0.000 description 1
• 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
• 208000032928 Dyslipidaemia Diseases 0.000 description 1
• 206010014733 Endometrial cancer Diseases 0.000 description 1
• 206010014759 Endometrial neoplasm Diseases 0.000 description 1
• 201000009273 Endometriosis Diseases 0.000 description 1
• 241000792859 Enema Species 0.000 description 1
• 208000004232 Enteritis Diseases 0.000 description 1
• 102000004190 Enzymes Human genes 0.000 description 1
• 108090000790 Enzymes Proteins 0.000 description 1
• 206010014954 Eosinophilic fasciitis Diseases 0.000 description 1
• 206010014967 Ependymoma Diseases 0.000 description 1
• 241000283086 Equidae Species 0.000 description 1
• 206010015226 Erythema nodosum Diseases 0.000 description 1
• 206010015251 Erythroblastosis foetalis Diseases 0.000 description 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 description 1
• 208000004332 Evans syndrome Diseases 0.000 description 1
• 208000006168 Ewing Sarcoma Diseases 0.000 description 1
• 108700024394 Exon Proteins 0.000 description 1
• 208000017259 Extragonadal germ cell tumor Diseases 0.000 description 1
• 208000004930 Fatty Liver Diseases 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 208000007882 Gastritis Diseases 0.000 description 1
• 201000003741 Gastrointestinal carcinoma Diseases 0.000 description 1
• 206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 208000024869 Goodpasture syndrome Diseases 0.000 description 1
• 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 1
• 208000015023 Graves' disease Diseases 0.000 description 1
• 208000016905 Hashimoto encephalopathy Diseases 0.000 description 1
• 208000030836 Hashimoto thyroiditis Diseases 0.000 description 1
• 206010019196 Head injury Diseases 0.000 description 1
• 208000010496 Heart Arrest Diseases 0.000 description 1
• 201000004331 Henoch-Schoenlein purpura Diseases 0.000 description 1
• 206010019617 Henoch-Schonlein purpura Diseases 0.000 description 1
• 206010019708 Hepatic steatosis Diseases 0.000 description 1
• 206010019728 Hepatitis alcoholic Diseases 0.000 description 1
• 206010019939 Herpes gestationis Diseases 0.000 description 1
• 208000017604 Hodgkin disease Diseases 0.000 description 1
• 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
• 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
• 241000282412 Homo Species 0.000 description 1
• 101100038117 Homo sapiens ROR1 gene Proteins 0.000 description 1
• 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 1
• 208000029470 Hughes-Stovin syndrome Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 206010021042 Hypopharyngeal cancer Diseases 0.000 description 1
• 206010056305 Hypopharyngeal neoplasm Diseases 0.000 description 1
• 206010021138 Hypovolaemic shock Diseases 0.000 description 1
• 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
• 208000031814 IgA Vasculitis Diseases 0.000 description 1
• 208000014919 IgG4-related retroperitoneal fibrosis Diseases 0.000 description 1
• 108060003951 Immunoglobulin Proteins 0.000 description 1
• 206010061218 Inflammation Diseases 0.000 description 1
• 208000005615 Interstitial Cystitis Diseases 0.000 description 1
• 208000000209 Isaacs syndrome Diseases 0.000 description 1
• 208000007766 Kaposi sarcoma Diseases 0.000 description 1
• 208000011200 Kawasaki disease Diseases 0.000 description 1
• 208000008839 Kidney Neoplasms Diseases 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 201000010743 Lambert-Eaton myasthenic syndrome Diseases 0.000 description 1
• 206010023825 Laryngeal cancer Diseases 0.000 description 1
• 240000007472 Leucaena leucocephala Species 0.000 description 1
• 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
• 208000034624 Leukocytoclastic Cutaneous Vasculitis Diseases 0.000 description 1
• 229910010084 LiAlH4 Inorganic materials 0.000 description 1
• 206010024434 Lichen sclerosus Diseases 0.000 description 1
• 208000012309 Linear IgA disease Diseases 0.000 description 1
• 208000017170 Lipid metabolism disease Diseases 0.000 description 1
• 208000000185 Localized scleroderma Diseases 0.000 description 1
• 208000005777 Lupus Nephritis Diseases 0.000 description 1
• 206010025312 Lymphoma AIDS related Diseases 0.000 description 1
• 208000009777 Majeed syndrome Diseases 0.000 description 1
• 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
• 206010025537 Malignant anorectal neoplasms Diseases 0.000 description 1
• 206010064281 Malignant atrophic papulosis Diseases 0.000 description 1
• 208000032271 Malignant tumor of penis Diseases 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 208000000172 Medulloblastoma Diseases 0.000 description 1
• 201000009906 Meningitis Diseases 0.000 description 1
• 208000002030 Merkel cell carcinoma Diseases 0.000 description 1
• 206010027982 Morphoea Diseases 0.000 description 1
• 208000003445 Mouth Neoplasms Diseases 0.000 description 1
• TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Natural products OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
• 208000012192 Mucous membrane pemphigoid Diseases 0.000 description 1
• 208000034578 Multiple myelomas Diseases 0.000 description 1
• 241000699666 Mus <mouse, genus> Species 0.000 description 1
• 206010028424 Myasthenic syndrome Diseases 0.000 description 1
• 201000003793 Myelodysplastic syndrome Diseases 0.000 description 1
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
• 201000007224 Myeloproliferative neoplasm Diseases 0.000 description 1
• 201000002481 Myositis Diseases 0.000 description 1
• ZGMCGBHMQXTFHU-UHFFFAOYSA-N N-(5-bromo-4-chloropyridin-2-yl)nitramide Chemical compound BrC=1C(=CC(=NC=1)N[N+](=O)[O-])Cl ZGMCGBHMQXTFHU-UHFFFAOYSA-N 0.000 description 1
• WEXZMESYOJFOCT-UHFFFAOYSA-N N-(5-chloropyridin-3-yl)-2-(4-formylphenoxy)acetamide Chemical compound ClC=1C=C(C=NC=1)NC(COC1=CC=C(C=C1)C=O)=O WEXZMESYOJFOCT-UHFFFAOYSA-N 0.000 description 1
• NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Substances BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
• ZGCSOPKYGULVGH-UHFFFAOYSA-N N-methyl-2-[4-(methyliminomethyl)anilino]acetamide Chemical compound CNC(CNC1=CC=C(C=C1)C=NC)=O ZGCSOPKYGULVGH-UHFFFAOYSA-N 0.000 description 1
• DJYWDBDTQQQDDB-UHFFFAOYSA-N NCCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C=2NC2CCN(CC2)C)Cl)N1 Chemical compound NCCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C=2NC2CCN(CC2)C)Cl)N1 DJYWDBDTQQQDDB-UHFFFAOYSA-N 0.000 description 1
• RLARWPVNQGGDJB-UHFFFAOYSA-N NCCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C=2NC2CCN(CC2)CC2=CC=C(C=C2)OC)Cl)N1 Chemical compound NCCOC1=CC=C(C=C1)C1=NC=2C(=NC=C(C=2NC2CCN(CC2)CC2=CC=C(C=C2)OC)Cl)N1 RLARWPVNQGGDJB-UHFFFAOYSA-N 0.000 description 1
• 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 description 1
• 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
• 108010025020 Nerve Growth Factor Proteins 0.000 description 1
• 102000007072 Nerve Growth Factors Human genes 0.000 description 1
• 206010029229 Neuralgic amyotrophy Diseases 0.000 description 1
• 206010029266 Neuroendocrine carcinoma of the skin Diseases 0.000 description 1
• 206010072359 Neuromyotonia Diseases 0.000 description 1
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
• 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 208000005225 Opsoclonus-Myoclonus Syndrome Diseases 0.000 description 1
• 206010031096 Oropharyngeal cancer Diseases 0.000 description 1
• 206010057444 Oropharyngeal neoplasm Diseases 0.000 description 1
• 241000283973 Oryctolagus cuniculus Species 0.000 description 1
• 208000007571 Ovarian Epithelial Carcinoma Diseases 0.000 description 1
• 206010053869 POEMS syndrome Diseases 0.000 description 1
• 206010048705 Paraneoplastic cerebellar degeneration Diseases 0.000 description 1
• 208000000821 Parathyroid Neoplasms Diseases 0.000 description 1
• 208000004788 Pars Planitis Diseases 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 201000011152 Pemphigus Diseases 0.000 description 1
• 208000002471 Penile Neoplasms Diseases 0.000 description 1
• 206010034299 Penile cancer Diseases 0.000 description 1
• 208000031845 Pernicious anaemia Diseases 0.000 description 1
• 239000004264 Petrolatum Substances 0.000 description 1
• 206010050487 Pinealoblastoma Diseases 0.000 description 1
• 208000007641 Pinealoma Diseases 0.000 description 1
• 208000007913 Pituitary Neoplasms Diseases 0.000 description 1
• 241000101040 Pityriasis Species 0.000 description 1
• 208000000766 Pityriasis Lichenoides Diseases 0.000 description 1
• 206010048895 Pityriasis lichenoides et varioliformis acuta Diseases 0.000 description 1
• 206010035226 Plasma cell myeloma Diseases 0.000 description 1
• 201000008199 Pleuropulmonary blastoma Diseases 0.000 description 1
• 206010035742 Pneumonitis Diseases 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 206010065159 Polychondritis Diseases 0.000 description 1
• 208000007048 Polymyalgia Rheumatica Diseases 0.000 description 1
• 229920001214 Polysorbate 60 Polymers 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 208000012654 Primary biliary cholangitis Diseases 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 208000037534 Progressive hemifacial atrophy Diseases 0.000 description 1
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
• 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
• 208000003670 Pure Red-Cell Aplasia Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 108091008554 ROR receptors Proteins 0.000 description 1
• 101150001095 ROR1 gene Proteins 0.000 description 1
• 206010071141 Rasmussen encephalitis Diseases 0.000 description 1
• 208000004160 Rasmussen subacute encephalitis Diseases 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 208000012322 Raynaud phenomenon Diseases 0.000 description 1
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
• 102100029986 Receptor tyrosine-protein kinase erbB-3 Human genes 0.000 description 1
• 101710100969 Receptor tyrosine-protein kinase erbB-3 Proteins 0.000 description 1
• 206010070308 Refractory cancer Diseases 0.000 description 1
• 208000033464 Reiter syndrome Diseases 0.000 description 1
• 206010038389 Renal cancer Diseases 0.000 description 1
• 206010063837 Reperfusion injury Diseases 0.000 description 1
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
• 208000005793 Restless legs syndrome Diseases 0.000 description 1
• 201000000582 Retinoblastoma Diseases 0.000 description 1
• 206010038979 Retroperitoneal fibrosis Diseases 0.000 description 1
• 208000004337 Salivary Gland Neoplasms Diseases 0.000 description 1
• 206010061934 Salivary gland cancer Diseases 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 108010077895 Sarcosine Proteins 0.000 description 1
• 201000010848 Schnitzler Syndrome Diseases 0.000 description 1
• 206010039705 Scleritis Diseases 0.000 description 1
• 206010039710 Scleroderma Diseases 0.000 description 1
• 208000032384 Severe immune-mediated enteropathy Diseases 0.000 description 1
• 208000009359 Sezary Syndrome Diseases 0.000 description 1
• 208000021388 Sezary disease Diseases 0.000 description 1
• 206010041067 Small cell lung cancer Diseases 0.000 description 1
• 108091027967 Small hairpin RNA Proteins 0.000 description 1
• BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
• 208000021712 Soft tissue sarcoma Diseases 0.000 description 1
• HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 241000194017 Streptococcus Species 0.000 description 1
• 241000272534 Struthio camelus Species 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• 208000002286 Susac Syndrome Diseases 0.000 description 1
• 208000010265 Sweet syndrome Diseases 0.000 description 1
• 206010042742 Sympathetic ophthalmia Diseases 0.000 description 1
• 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
• 239000012317 TBTU Substances 0.000 description 1
• 208000001106 Takayasu Arteritis Diseases 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 208000024313 Testicular Neoplasms Diseases 0.000 description 1
• 206010057644 Testis cancer Diseases 0.000 description 1
• 206010043515 Throat cancer Diseases 0.000 description 1
• 201000009365 Thymic carcinoma Diseases 0.000 description 1
• 208000024770 Thyroid neoplasm Diseases 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 206010051526 Tolosa-Hunt syndrome Diseases 0.000 description 1
• 206010062129 Tongue neoplasm Diseases 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 206010044407 Transitional cell cancer of the renal pelvis and ureter Diseases 0.000 description 1
• OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
• 208000025851 Undifferentiated connective tissue disease Diseases 0.000 description 1
• 208000017379 Undifferentiated connective tissue syndrome Diseases 0.000 description 1
• 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
• 206010046431 Urethral cancer Diseases 0.000 description 1
• 206010046458 Urethral neoplasms Diseases 0.000 description 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
• 208000002495 Uterine Neoplasms Diseases 0.000 description 1
• 206010047642 Vitiligo Diseases 0.000 description 1
• 206010047741 Vulval cancer Diseases 0.000 description 1
• 208000033559 Waldenström macroglobulinemia Diseases 0.000 description 1
• 102000013814 Wnt Human genes 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 1
• 208000002223 abdominal aortic aneurysm Diseases 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 206010069351 acute lung injury Diseases 0.000 description 1
• 210000000577 adipose tissue Anatomy 0.000 description 1
• 230000011759 adipose tissue development Effects 0.000 description 1
• 208000020990 adrenal cortex carcinoma Diseases 0.000 description 1
• 208000007128 adrenocortical carcinoma Diseases 0.000 description 1
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
• 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 208000002353 alcoholic hepatitis Diseases 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• 208000004631 alopecia areata Diseases 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 235000001014 amino acid Nutrition 0.000 description 1
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
• 208000007502 anemia Diseases 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 201000011165 anus cancer Diseases 0.000 description 1
• 230000005756 apoptotic signaling Effects 0.000 description 1
• 208000021780 appendiceal neoplasm Diseases 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 238000010936 aqueous wash Methods 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 239000008122 artificial sweetener Substances 0.000 description 1
• 235000021311 artificial sweeteners Nutrition 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• 229960005070 ascorbic acid Drugs 0.000 description 1
• 230000000923 atherogenic effect Effects 0.000 description 1
• 208000010668 atopic eczema Diseases 0.000 description 1
• 201000004984 autoimmune cardiomyopathy Diseases 0.000 description 1
• 208000001974 autoimmune enteropathy Diseases 0.000 description 1
• 208000027625 autoimmune inner ear disease Diseases 0.000 description 1
• 201000004339 autoimmune neuropathy Diseases 0.000 description 1
• 201000005011 autoimmune peripheral neuropathy Diseases 0.000 description 1
• 201000011385 autoimmune polyendocrine syndrome Diseases 0.000 description 1
• 201000009780 autoimmune polyendocrine syndrome type 2 Diseases 0.000 description 1
• 206010071572 autoimmune progesterone dermatitis Diseases 0.000 description 1
• 208000029407 autoimmune urticaria Diseases 0.000 description 1
• 201000004982 autoimmune uveitis Diseases 0.000 description 1
• 230000005784 autoimmunity Effects 0.000 description 1
• 239000002585 base Substances 0.000 description 1
• OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 229940000635 beta-alanine Drugs 0.000 description 1
• 230000037396 body weight Effects 0.000 description 1
• 210000000988 bone and bone Anatomy 0.000 description 1
• 208000012172 borderline epithelial tumor of ovary Diseases 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 208000006752 brain edema Diseases 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 210000000069 breast epithelial cell Anatomy 0.000 description 1
• UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
• 201000009267 bronchiectasis Diseases 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 229940045348 brown mixture Drugs 0.000 description 1
• 230000005587 bubbling Effects 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 208000000594 bullous pemphigoid Diseases 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 208000002458 carcinoid tumor Diseases 0.000 description 1
• 238000007675 cardiac surgery Methods 0.000 description 1
• 239000004359 castor oil Substances 0.000 description 1
• 235000019438 castor oil Nutrition 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 230000032823 cell division Effects 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 238000003570 cell viability assay Methods 0.000 description 1
• 230000001413 cellular effect Effects 0.000 description 1
• 230000019522 cellular metabolic process Effects 0.000 description 1
• 201000007455 central nervous system cancer Diseases 0.000 description 1
• 208000030239 cerebral astrocytoma Diseases 0.000 description 1
• 201000010881 cervical cancer Diseases 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 208000011654 childhood malignant neoplasm Diseases 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 201000001883 cholelithiasis Diseases 0.000 description 1
• 238000013375 chromatographic separation Methods 0.000 description 1
• 230000002759 chromosomal effect Effects 0.000 description 1
• 231100000005 chromosome aberration Toxicity 0.000 description 1
• 208000007451 chronic bronchitis Diseases 0.000 description 1
• 208000019069 chronic childhood arthritis Diseases 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
• 208000024376 chronic urticaria Diseases 0.000 description 1
• 201000010002 cicatricial pemphigoid Diseases 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• 230000005757 colony formation Effects 0.000 description 1
• 238000004040 coloring Methods 0.000 description 1
• 238000004891 communication Methods 0.000 description 1
• 201000003056 complement component 2 deficiency Diseases 0.000 description 1
• 230000000295 complement effect Effects 0.000 description 1
• 239000000306 component Substances 0.000 description 1
• 238000004590 computer program Methods 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 208000010247 contact dermatitis Diseases 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 238000007887 coronary angioplasty Methods 0.000 description 1
• 208000029078 coronary artery disease Diseases 0.000 description 1
• 239000007822 coupling agent Substances 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• 201000003278 cryoglobulinemia Diseases 0.000 description 1
• 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
• 208000018261 cutaneous leukocytoclastic angiitis Diseases 0.000 description 1
• 208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
• 208000017763 cutaneous neuroendocrine carcinoma Diseases 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
• 235000018417 cysteine Nutrition 0.000 description 1
• 231100000433 cytotoxic Toxicity 0.000 description 1
• 230000001472 cytotoxic effect Effects 0.000 description 1
• 230000003013 cytotoxicity Effects 0.000 description 1
• 231100000135 cytotoxicity Toxicity 0.000 description 1
• DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 235000019425 dextrin Nutrition 0.000 description 1
• VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 206010062952 diffuse panbronchiolitis Diseases 0.000 description 1
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• 230000005750 disease progression Effects 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
• 231100000673 dose–response relationship Toxicity 0.000 description 1
• 238000009509 drug development Methods 0.000 description 1
• 239000013583 drug formulation Substances 0.000 description 1
• 201000004997 drug-induced lupus erythematosus Diseases 0.000 description 1
• 229940121647 egfr inhibitor Drugs 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000008387 emulsifying waxe Substances 0.000 description 1
• 201000002491 encephalomyelitis Diseases 0.000 description 1
• 239000007920 enema Substances 0.000 description 1
• 229940095399 enema Drugs 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 201000001564 eosinophilic gastroenteritis Diseases 0.000 description 1
• 201000011114 epidermolysis bullosa acquisita Diseases 0.000 description 1
• 201000004101 esophageal cancer Diseases 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 201000008819 extrahepatic bile duct carcinoma Diseases 0.000 description 1
• 201000001155 extrinsic allergic alveolitis Diseases 0.000 description 1
• 208000002980 facial hemiatrophy Diseases 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 208000010706 fatty liver disease Diseases 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 208000001031 fetal erythroblastosis Diseases 0.000 description 1
• 239000012065 filter cake Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 238000001640 fractional crystallisation Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 210000000232 gallbladder Anatomy 0.000 description 1
• 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 1
• 210000001035 gastrointestinal tract Anatomy 0.000 description 1
• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 1
• 229960002584 gefitinib Drugs 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 239000000174 gluconic acid Substances 0.000 description 1
• 235000012208 gluconic acid Nutrition 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 230000014101 glucose homeostasis Effects 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 229940093915 gynecological organic acid Drugs 0.000 description 1
• 201000009277 hairy cell leukemia Diseases 0.000 description 1
• 238000003306 harvesting Methods 0.000 description 1
• 201000010536 head and neck cancer Diseases 0.000 description 1
• 208000014829 head and neck neoplasm Diseases 0.000 description 1
• 210000002216 heart Anatomy 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 230000002949 hemolytic effect Effects 0.000 description 1
• 208000006454 hepatitis Diseases 0.000 description 1
• 231100000283 hepatitis Toxicity 0.000 description 1
• 239000008241 heterogeneous mixture Substances 0.000 description 1
• 208000002557 hidradenitis Diseases 0.000 description 1
• 201000007162 hidradenitis suppurativa Diseases 0.000 description 1
• 208000029824 high grade glioma Diseases 0.000 description 1
• 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 102000049583 human ROR1 Human genes 0.000 description 1
• DXMYKAREPXBRHQ-UHFFFAOYSA-N hydron;1-methylpiperidin-4-amine;chloride Chemical compound Cl.CN1CCC(N)CC1 DXMYKAREPXBRHQ-UHFFFAOYSA-N 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 208000022098 hypersensitivity pneumonitis Diseases 0.000 description 1
• 201000006362 hypersensitivity vasculitis Diseases 0.000 description 1
• 201000006866 hypopharynx cancer Diseases 0.000 description 1
• 230000002267 hypothalamic effect Effects 0.000 description 1
• 210000002865 immune cell Anatomy 0.000 description 1
• 230000028993 immune response Effects 0.000 description 1
• 102000018358 immunoglobulin Human genes 0.000 description 1
• 208000015446 immunoglobulin a vasculitis Diseases 0.000 description 1
• 230000002134 immunopathologic effect Effects 0.000 description 1
• 238000000099 in vitro assay Methods 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 201000008319 inclusion body myositis Diseases 0.000 description 1
• 230000008595 infiltration Effects 0.000 description 1
• 238000001764 infiltration Methods 0.000 description 1
• 230000004054 inflammatory process Effects 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 239000003999 initiator Substances 0.000 description 1
• 208000014674 injury Diseases 0.000 description 1
• 229940030980 inova Drugs 0.000 description 1
• 230000008611 intercellular interaction Effects 0.000 description 1
• UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
• 201000002313 intestinal cancer Diseases 0.000 description 1
• 238000001361 intraarterial administration Methods 0.000 description 1
• 238000000185 intracerebroventricular administration Methods 0.000 description 1
• 238000007917 intracranial administration Methods 0.000 description 1
• 210000003228 intrahepatic bile duct Anatomy 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007919 intrasynovial administration Methods 0.000 description 1
• 238000007913 intrathecal administration Methods 0.000 description 1
• 230000002601 intratumoral effect Effects 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• SYJRVVFAAIUVDH-UHFFFAOYSA-N ipa isopropanol Chemical compound CC(C)O.CC(C)O SYJRVVFAAIUVDH-UHFFFAOYSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 208000028867 ischemia Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 210000004153 islets of langerhan Anatomy 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 229960004592 isopropanol Drugs 0.000 description 1
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
• FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
• 210000003734 kidney Anatomy 0.000 description 1
• 201000010982 kidney cancer Diseases 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 206010023841 laryngeal neoplasm Diseases 0.000 description 1
• 239000010410 layer Substances 0.000 description 1
• 238000002386 leaching Methods 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 208000032839 leukemia Diseases 0.000 description 1
• 201000011486 lichen planus Diseases 0.000 description 1
• 150000002632 lipids Chemical class 0.000 description 1
• 239000012280 lithium aluminium hydride Substances 0.000 description 1
• 210000004185 liver Anatomy 0.000 description 1
• 239000007937 lozenge Substances 0.000 description 1
• 201000005249 lung adenocarcinoma Diseases 0.000 description 1
• 206010025135 lupus erythematosus Diseases 0.000 description 1
• 210000004324 lymphatic system Anatomy 0.000 description 1
• 208000019420 lymphoid neoplasm Diseases 0.000 description 1
• ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
• 239000001095 magnesium carbonate Substances 0.000 description 1
• 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 230000036210 malignancy Effects 0.000 description 1
• 208000030883 malignant astrocytoma Diseases 0.000 description 1
• 201000011614 malignant glioma Diseases 0.000 description 1
• 208000006178 malignant mesothelioma Diseases 0.000 description 1
• 208000026045 malignant tumor of parathyroid gland Diseases 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 230000035800 maturation Effects 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
• 108020004999 messenger RNA Proteins 0.000 description 1
• 230000001394 metastastic effect Effects 0.000 description 1
• 206010061289 metastatic neoplasm Diseases 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• MSJWOCJILYIXQQ-UHFFFAOYSA-N methyl 2-(4-formyl-2,6-dimethylphenoxy)acetate Chemical compound COC(=O)COC1=C(C)C=C(C=O)C=C1C MSJWOCJILYIXQQ-UHFFFAOYSA-N 0.000 description 1
• XBLWXYZXSFHFGR-UHFFFAOYSA-N methyl 2-(4-formyl-2-methoxyphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(C=O)C=C1OC XBLWXYZXSFHFGR-UHFFFAOYSA-N 0.000 description 1
• QXXIHGHDXQSZJG-UHFFFAOYSA-N methyl 2-(4-formyl-2-methylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(C=O)C=C1C QXXIHGHDXQSZJG-UHFFFAOYSA-N 0.000 description 1
• VURFUQZLYWBUIX-UHFFFAOYSA-N methyl 2-(4-formylphenoxy)-2-methylpropanoate Chemical compound COC(=O)C(C)(C)OC1=CC=C(C=O)C=C1 VURFUQZLYWBUIX-UHFFFAOYSA-N 0.000 description 1
• 206010063344 microscopic polyangiitis Diseases 0.000 description 1
• 229940042472 mineral oil Drugs 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 238000012544 monitoring process Methods 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 description 1
• 210000004400 mucous membrane Anatomy 0.000 description 1
• 206010051747 multiple endocrine neoplasia Diseases 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 206010028417 myasthenia gravis Diseases 0.000 description 1
• 208000017869 myelodysplastic/myeloproliferative disease Diseases 0.000 description 1
• 230000002107 myocardial effect Effects 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
• NAOOJIDHHYTBND-UHFFFAOYSA-N n,n,2-trimethyl-2-nitropropan-1-amine Chemical compound CN(C)CC(C)(C)[N+]([O-])=O NAOOJIDHHYTBND-UHFFFAOYSA-N 0.000 description 1
• LPGDHUSSRKJWQN-UHFFFAOYSA-N n-[2-(4-formylphenoxy)ethyl]acetamide Chemical compound CC(=O)NCCOC1=CC=C(C=O)C=C1 LPGDHUSSRKJWQN-UHFFFAOYSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• AXRLGJOCQBMUAP-UHFFFAOYSA-N n-[4-[(4-aminopiperidin-1-yl)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1CCC(N)CC1 AXRLGJOCQBMUAP-UHFFFAOYSA-N 0.000 description 1
• WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
• 201000003631 narcolepsy Diseases 0.000 description 1
• 208000018795 nasal cavity and paranasal sinus carcinoma Diseases 0.000 description 1
• 235000021096 natural sweeteners Nutrition 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 210000000653 nervous system Anatomy 0.000 description 1
• 201000011682 nervous system cancer Diseases 0.000 description 1
• 210000001020 neural plate Anatomy 0.000 description 1
• 210000002569 neuron Anatomy 0.000 description 1
• 201000001119 neuropathy Diseases 0.000 description 1
• 230000007823 neuropathy Effects 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
• 230000000269 nucleophilic effect Effects 0.000 description 1
• 208000015200 ocular cicatricial pemphigoid Diseases 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 239000004006 olive oil Substances 0.000 description 1
• 235000008390 olive oil Nutrition 0.000 description 1
• 201000005443 oral cavity cancer Diseases 0.000 description 1
• 230000008816 organ damage Effects 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 201000006958 oropharynx cancer Diseases 0.000 description 1
• 201000008482 osteoarthritis Diseases 0.000 description 1
• 201000008968 osteosarcoma Diseases 0.000 description 1
• 208000021284 ovarian germ cell tumor Diseases 0.000 description 1
• 230000002018 overexpression Effects 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 201000005580 palindromic rheumatism Diseases 0.000 description 1
• 210000000496 pancreas Anatomy 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 239000003182 parenteral nutrition solution Substances 0.000 description 1
• 230000036961 partial effect Effects 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 239000001814 pectin Substances 0.000 description 1
• 235000010987 pectin Nutrition 0.000 description 1
• 229920001277 pectin Polymers 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 201000001976 pemphigus vulgaris Diseases 0.000 description 1
• 208000033808 peripheral neuropathy Diseases 0.000 description 1
• 229940066842 petrolatum Drugs 0.000 description 1
• 235000019271 petrolatum Nutrition 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 229940124531 pharmaceutical excipient Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 208000028591 pheochromocytoma Diseases 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 201000003113 pineoblastoma Diseases 0.000 description 1
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• 208000010916 pituitary tumor Diseases 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
• 210000002826 placenta Anatomy 0.000 description 1
• 208000010626 plasma cell neoplasm Diseases 0.000 description 1
• 208000008423 pleurisy Diseases 0.000 description 1
• 201000006292 polyarteritis nodosa Diseases 0.000 description 1
• 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
• 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
• 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
• 229920001451 polypropylene glycol Polymers 0.000 description 1
• 229940113124 polysorbate 60 Drugs 0.000 description 1
• 229920000053 polysorbate 80 Polymers 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 238000002953 preparative HPLC Methods 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 208000016800 primary central nervous system lymphoma Diseases 0.000 description 1
• 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
• 201000000742 primary sclerosing cholangitis Diseases 0.000 description 1
• 210000001948 pro-b lymphocyte Anatomy 0.000 description 1
• 230000001686 pro-survival effect Effects 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• 230000002062 proliferating effect Effects 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
• NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
• 230000003331 prothrombotic effect Effects 0.000 description 1
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
• 208000005069 pulmonary fibrosis Diseases 0.000 description 1
• 208000009954 pyoderma gangrenosum Diseases 0.000 description 1
• XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
• 239000005297 pyrex Substances 0.000 description 1
• QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
• BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
• FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 208000002574 reactive arthritis Diseases 0.000 description 1
• 229940100618 rectal suppository Drugs 0.000 description 1
• 239000006215 rectal suppository Substances 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 230000002829 reductive effect Effects 0.000 description 1
• 208000016691 refractory malignant neoplasm Diseases 0.000 description 1
• 230000025053 regulation of cell proliferation Effects 0.000 description 1
• 208000009169 relapsing polychondritis Diseases 0.000 description 1
• 208000030859 renal pelvis/ureter urothelial carcinoma Diseases 0.000 description 1
• 239000011347 resin Substances 0.000 description 1
• 229920005989 resin Polymers 0.000 description 1
• HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 0.000 description 1
• 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
• 201000003068 rheumatic fever Diseases 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 201000000980 schizophrenia Diseases 0.000 description 1
• 208000010157 sclerosing cholangitis Diseases 0.000 description 1
• 208000013223 septicemia Diseases 0.000 description 1
• 206010040400 serum sickness Diseases 0.000 description 1
• 206010040560 shock Diseases 0.000 description 1
• 239000000741 silica gel Substances 0.000 description 1
• 229910002027 silica gel Inorganic materials 0.000 description 1
• 210000002027 skeletal muscle Anatomy 0.000 description 1
• 210000003491 skin Anatomy 0.000 description 1
• 239000004055 small Interfering RNA Substances 0.000 description 1
• 208000000587 small cell lung carcinoma Diseases 0.000 description 1
• WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
• 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
• 239000011780 sodium chloride Substances 0.000 description 1
• 235000010265 sodium sulphite Nutrition 0.000 description 1
• 230000003381 solubilizing effect Effects 0.000 description 1
• 239000001587 sorbitan monostearate Substances 0.000 description 1
• 235000011076 sorbitan monostearate Nutrition 0.000 description 1
• 229940035048 sorbitan monostearate Drugs 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 208000017572 squamous cell neoplasm Diseases 0.000 description 1
• 230000000087 stabilizing effect Effects 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• 231100000240 steatosis hepatitis Toxicity 0.000 description 1
• 239000008174 sterile solution Substances 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• 201000008205 supratentorial primitive neuroectodermal tumor Diseases 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 238000007910 systemic administration Methods 0.000 description 1
• 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• LZRDHSFPLUWYAX-UHFFFAOYSA-N tert-butyl 4-aminopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(N)CC1 LZRDHSFPLUWYAX-UHFFFAOYSA-N 0.000 description 1
• NMIBGWMOADPZHX-UHFFFAOYSA-N tert-butyl n-[1-[(3-methylphenyl)methyl]piperidin-4-yl]carbamate Chemical compound CC1=CC=CC(CN2CCC(CC2)NC(=O)OC(C)(C)C)=C1 NMIBGWMOADPZHX-UHFFFAOYSA-N 0.000 description 1
• 201000003120 testicular cancer Diseases 0.000 description 1
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
• UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 206010043554 thrombocytopenia Diseases 0.000 description 1
• 201000002510 thyroid cancer Diseases 0.000 description 1
• 206010043778 thyroiditis Diseases 0.000 description 1
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
• 229940098465 tincture Drugs 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
• 238000001890 transfection Methods 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 238000002054 transplantation Methods 0.000 description 1
• 208000009174 transverse myelitis Diseases 0.000 description 1
• 230000008733 trauma Effects 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
• 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
• 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
• 201000005112 urinary bladder cancer Diseases 0.000 description 1
• 230000002485 urinary effect Effects 0.000 description 1
• 206010046766 uterine cancer Diseases 0.000 description 1
• 208000037965 uterine sarcoma Diseases 0.000 description 1
• 206010046885 vaginal cancer Diseases 0.000 description 1
• 208000013139 vaginal neoplasm Diseases 0.000 description 1
• 235000012141 vanillin Nutrition 0.000 description 1
• FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
• 239000003981 vehicle Substances 0.000 description 1
• 239000011345 viscous material Substances 0.000 description 1
• 230000000007 visual effect Effects 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1