ZA200405336B - Urea substituted imidazopyridines - Google Patents
Urea substituted imidazopyridines Download PDFInfo
- Publication number
- ZA200405336B ZA200405336B ZA200405336A ZA200405336A ZA200405336B ZA 200405336 B ZA200405336 B ZA 200405336B ZA 200405336 A ZA200405336 A ZA 200405336A ZA 200405336 A ZA200405336 A ZA 200405336A ZA 200405336 B ZA200405336 B ZA 200405336B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino
- imidazo
- pyridin
- ethoxymethyl
- alkyl
- Prior art date
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 50
- 239000004202 carbamide Substances 0.000 title claims description 20
- 150000005232 imidazopyridines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 115
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 102000004127 Cytokines Human genes 0.000 claims description 25
- 108090000695 Cytokines Proteins 0.000 claims description 25
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- -1 morpholin-4-ylcarbonyl Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 230000003612 virological effect Effects 0.000 claims description 8
- 230000001613 neoplastic effect Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 230000001939 inductive effect Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 2
- XTDRDLKEBWEOFY-UHFFFAOYSA-N 1-[1-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-yl]-3-phenylurea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CC(C)(C)NC(=O)NC1=CC=CC=C1 XTDRDLKEBWEOFY-UHFFFAOYSA-N 0.000 claims 1
- DAZXWUZWVFKBNW-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(2-chlorophenyl)sulfonylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)NS(=O)(=O)C1=CC=CC=C1Cl DAZXWUZWVFKBNW-UHFFFAOYSA-N 0.000 claims 1
- LPNMGSLZAQRGHK-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(3-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC(NC(=O)NCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 LPNMGSLZAQRGHK-UHFFFAOYSA-N 0.000 claims 1
- STTHSDUJRJMGFC-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(4-methoxyphenyl)thiourea Chemical compound C1=CC(OC)=CC=C1NC(=S)NCCN1C2=C(C)C(C)=NC(N)=C2N=C1C STTHSDUJRJMGFC-UHFFFAOYSA-N 0.000 claims 1
- NQSWLKBDUSQGCB-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(4-phenoxyphenyl)urea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 NQSWLKBDUSQGCB-UHFFFAOYSA-N 0.000 claims 1
- NUQUKWYFSVCYBE-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NCCN1C2=C(C)C(C)=NC(N)=C2N=C1C NUQUKWYFSVCYBE-UHFFFAOYSA-N 0.000 claims 1
- UJWOOTSVRNTNTN-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyclohexylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)NC1CCCCC1 UJWOOTSVRNTNTN-UHFFFAOYSA-N 0.000 claims 1
- JURACIZLUDJDCG-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-phenylthiourea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=S)NC1=CC=CC=C1 JURACIZLUDJDCG-UHFFFAOYSA-N 0.000 claims 1
- DWWSAFMTBSYOEZ-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-phenylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)NC1=CC=CC=C1 DWWSAFMTBSYOEZ-UHFFFAOYSA-N 0.000 claims 1
- QMTUXOJSINPYPW-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-cyclohexylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NC1CCCCC1 QMTUXOJSINPYPW-UHFFFAOYSA-N 0.000 claims 1
- WPWOWRAVOUKORB-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-phenylthiourea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=S)NC1=CC=CC=C1 WPWOWRAVOUKORB-UHFFFAOYSA-N 0.000 claims 1
- KJVKTKMVWSAADG-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-(3-cyanophenyl)urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NC1=CC=CC(C#N)=C1 KJVKTKMVWSAADG-UHFFFAOYSA-N 0.000 claims 1
- VRFRELHOUJZTNI-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-[3-(diethylamino)propyl]thiourea Chemical compound N1=C(C)C(C)=C2N(CCCNC(=S)NCCCN(CC)CC)C(COCC)=NC2=C1N VRFRELHOUJZTNI-UHFFFAOYSA-N 0.000 claims 1
- GYPABZOHUHATSZ-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NC1=CC=C(C(F)(F)F)C=C1 GYPABZOHUHATSZ-UHFFFAOYSA-N 0.000 claims 1
- DPLPFGMTBVGJAY-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-butylurea Chemical compound N1=C(C)C(C)=C2N(CCCNC(=O)NCCCC)C(COCC)=NC2=C1N DPLPFGMTBVGJAY-UHFFFAOYSA-N 0.000 claims 1
- NEXBVIAZKYNOSA-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-phenylurea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NC1=CC=CC=C1 NEXBVIAZKYNOSA-UHFFFAOYSA-N 0.000 claims 1
- FSYBTNHKANYYBR-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(2,4-dimethoxyphenyl)urea Chemical compound COC1=CC(OC)=CC=C1NC(=O)NCCCCN1C2=C(C)C(C)=NC(N)=C2N=C1 FSYBTNHKANYYBR-UHFFFAOYSA-N 0.000 claims 1
- NCVYTRDWNZYQPT-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NCCCCN2C3=C(C)C(C)=NC(N)=C3N=C2)=C1 NCVYTRDWNZYQPT-UHFFFAOYSA-N 0.000 claims 1
- HCPGRVFZNMHPLB-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-chlorophenyl)sulfonylurea Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 HCPGRVFZNMHPLB-UHFFFAOYSA-N 0.000 claims 1
- ULCFYOAGZIQUSF-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-methoxyphenyl)thiourea Chemical compound C1=CC(OC)=CC=C1NC(=S)NCCCCN1C2=C(C)C(C)=NC(N)=C2N=C1 ULCFYOAGZIQUSF-UHFFFAOYSA-N 0.000 claims 1
- WVRFBYZNAPIVHB-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(benzenesulfonyl)urea Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 WVRFBYZNAPIVHB-UHFFFAOYSA-N 0.000 claims 1
- OIMXOCFWCQVUNX-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NCCCCN1C2=C(C)C(C)=NC(N)=C2N=C1 OIMXOCFWCQVUNX-UHFFFAOYSA-N 0.000 claims 1
- WYJGREACYUBCKC-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-butylurea Chemical compound N1=C(C)C(C)=C2N(CCCCNC(=O)NCCCC)C=NC2=C1N WYJGREACYUBCKC-UHFFFAOYSA-N 0.000 claims 1
- DJTYGBUIOPSIOQ-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-cyclohexylurea Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=O)NC1CCCCC1 DJTYGBUIOPSIOQ-UHFFFAOYSA-N 0.000 claims 1
- GFZAYUKBEODNLS-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-methylthiourea Chemical compound N1=C(C)C(C)=C2N(CCCCNC(=S)NC)C=NC2=C1N GFZAYUKBEODNLS-UHFFFAOYSA-N 0.000 claims 1
- LSJYGAHSDXNKKO-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylthiourea Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=S)NC1=CC=CC=C1 LSJYGAHSDXNKKO-UHFFFAOYSA-N 0.000 claims 1
- JCFCNDCTFCVNIW-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylurea Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=O)NC1=CC=CC=C1 JCFCNDCTFCVNIW-UHFFFAOYSA-N 0.000 claims 1
- ODGWEVORNGGBHT-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-tert-butylurea Chemical compound CC1=NC(N)=C2N=CN(CCCCNC(=O)NC(C)(C)C)C2=C1C ODGWEVORNGGBHT-UHFFFAOYSA-N 0.000 claims 1
- HRZNYYZOSXFSAZ-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(2-phenylethyl)thiourea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=S)NCCC1=CC=CC=C1 HRZNYYZOSXFSAZ-UHFFFAOYSA-N 0.000 claims 1
- XEISZTVBJLUWGV-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(4-methoxyphenyl)thiourea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=S)NC1=CC=C(OC)C=C1 XEISZTVBJLUWGV-UHFFFAOYSA-N 0.000 claims 1
- STIKECIRPOBICX-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(benzenesulfonyl)urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 STIKECIRPOBICX-UHFFFAOYSA-N 0.000 claims 1
- ATUCPNHULWGLGZ-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)NC1=CC=C(N(C)C)C=C1 ATUCPNHULWGLGZ-UHFFFAOYSA-N 0.000 claims 1
- GUPFMYFQEOABMH-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-butylurea Chemical compound N1=C(C)C=C2N(CCCCNC(=O)NCCCC)C(COCC)=NC2=C1N GUPFMYFQEOABMH-UHFFFAOYSA-N 0.000 claims 1
- SBBWGIULXKHNBR-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-phenylurea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)NC1=CC=CC=C1 SBBWGIULXKHNBR-UHFFFAOYSA-N 0.000 claims 1
- RKQVPOWJPYQUKK-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(2-chlorophenyl)sulfonylurea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1Cl RKQVPOWJPYQUKK-UHFFFAOYSA-N 0.000 claims 1
- PPFOAADECGIUFW-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(2-morpholin-4-ylethyl)thiourea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=S)NCCN1CCOCC1 PPFOAADECGIUFW-UHFFFAOYSA-N 0.000 claims 1
- MWBWMTIQKRMAEB-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(3-cyanophenyl)urea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=O)NC1=CC=CC(C#N)=C1 MWBWMTIQKRMAEB-UHFFFAOYSA-N 0.000 claims 1
- PNDDLKWTIBLMRR-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(4-phenoxyphenyl)urea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 PNDDLKWTIBLMRR-UHFFFAOYSA-N 0.000 claims 1
- ONWJIPBLSPHRIF-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(4-sulfamoylphenyl)thiourea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=S)NC1=CC=C(S(N)(=O)=O)C=C1 ONWJIPBLSPHRIF-UHFFFAOYSA-N 0.000 claims 1
- GABVZTFMZTVBKD-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-[3-(diethylamino)propyl]thiourea Chemical compound N1=CC(C)=C2N(CCCCNC(=S)NCCCN(CC)CC)C(COCC)=NC2=C1N GABVZTFMZTVBKD-UHFFFAOYSA-N 0.000 claims 1
- GNSZATRROJNJSW-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=O)NC1=CC=C(C(F)(F)F)C=C1 GNSZATRROJNJSW-UHFFFAOYSA-N 0.000 claims 1
- YCGAYROXPWGLFC-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-butylurea Chemical compound N1=CC(C)=C2N(CCCCNC(=O)NCCCC)C(COCC)=NC2=C1N YCGAYROXPWGLFC-UHFFFAOYSA-N 0.000 claims 1
- GGWCBEAZIFWDGK-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-cyclohexylurea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=O)NC1CCCCC1 GGWCBEAZIFWDGK-UHFFFAOYSA-N 0.000 claims 1
- ZQFPPHWXZCHWEI-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-phenylthiourea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=S)NC1=CC=CC=C1 ZQFPPHWXZCHWEI-UHFFFAOYSA-N 0.000 claims 1
- ZNXIOLZFEUJCCN-UHFFFAOYSA-N 3-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-1,1-dimethylurea Chemical compound N1=C(C)C(C)=C2N(CCNC(=O)N(C)C)C(C)=NC2=C1N ZNXIOLZFEUJCCN-UHFFFAOYSA-N 0.000 claims 1
- AUDBRICLKHFZQE-UHFFFAOYSA-N 3-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-1-methyl-1-phenylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)N(C)C1=CC=CC=C1 AUDBRICLKHFZQE-UHFFFAOYSA-N 0.000 claims 1
- HRTDOVYORQKCNG-UHFFFAOYSA-N 3-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-1-methyl-1-phenylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)N(C)C1=CC=CC=C1 HRTDOVYORQKCNG-UHFFFAOYSA-N 0.000 claims 1
- GITZREMUFKRMNP-UHFFFAOYSA-N 3-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-1-methyl-1-phenylurea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=O)N(C)C1=CC=CC=C1 GITZREMUFKRMNP-UHFFFAOYSA-N 0.000 claims 1
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| WO2015023958A1 (en) * | 2013-08-15 | 2015-02-19 | The University Of Kansas | Toll-like receptor agonists |
| EP4445956A2 (en) | 2015-01-06 | 2024-10-16 | Arena Pharmaceuticals, Inc. | Compound for use in treating conditions related to the s1p1 receptor |
| WO2016209809A1 (en) | 2015-06-22 | 2016-12-29 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid(compound1) for use in sipi receptor-associated disorders |
| WO2018107173A1 (en) * | 2016-12-09 | 2018-06-14 | Vanderbilt University | Glutamine transport inhibitors and methods for treating cancer |
| WO2018151873A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| CN111511740B (zh) | 2017-12-20 | 2023-05-16 | 3M创新有限公司 | 用作免疫应答调节剂的带有支链连接基团的酰胺取代的咪唑并[4,5-c]喹啉化合物 |
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| EP0708772B1 (en) * | 1993-07-15 | 2000-08-23 | Minnesota Mining And Manufacturing Company | IMIDAZO [4,5-c]PYRIDIN-4-AMINES |
| KR100518903B1 (ko) * | 1996-10-25 | 2005-10-06 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | Ｔｈ2 매개 질병 및 관련 질병의 치료용 면역 반응 조절 화합물 |
| US6541485B1 (en) * | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6376669B1 (en) * | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| UA74593C2 (en) * | 2000-12-08 | 2006-01-16 | 3M Innovative Properties Co | Substituted imidazopyridines |
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2001
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