JP2005511746A5 - - Google Patents
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- JP2005511746A5 JP2005511746A5 JP2003551143A JP2003551143A JP2005511746A5 JP 2005511746 A5 JP2005511746 A5 JP 2005511746A5 JP 2003551143 A JP2003551143 A JP 2003551143A JP 2003551143 A JP2003551143 A JP 2003551143A JP 2005511746 A5 JP2005511746 A5 JP 2005511746A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- imidazo
- pyridin
- ethoxymethyl
- butyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 43
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 39
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 31
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 239000004202 carbamide Substances 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 11
- -1 4-Amino-6,7-dimethyl-1H-imidazo [4,5-c] pyridin-1-yl Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- LWFUYHSPLINKEW-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NCCCCN2C3=C(C)C(C)=NC(N)=C3N=C2)=C1 LWFUYHSPLINKEW-UHFFFAOYSA-N 0.000 claims 1
- OIYDESYQTFUREL-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)NC1=CC=CC(C(C)=O)=C1 OIYDESYQTFUREL-UHFFFAOYSA-N 0.000 claims 1
- 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
- YKIZADDLEXDYCK-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-(2-chlorophenyl)sulfonylurea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NS(=O)(=O)C1=CC=CC=C1Cl YKIZADDLEXDYCK-UHFFFAOYSA-N 0.000 claims 1
- KDDPNEFXKKXBOV-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 KDDPNEFXKKXBOV-UHFFFAOYSA-N 0.000 claims 1
- OYPQWXPXNXBMQD-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-(benzenesulfonyl)urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 OYPQWXPXNXBMQD-UHFFFAOYSA-N 0.000 claims 1
- SHYKDGMRSBMXPB-UHFFFAOYSA-N 1-[4-(4-amino-2-butyl-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylthiourea Chemical compound CCCCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCCNC(=S)NC1=CC=CC=C1 SHYKDGMRSBMXPB-UHFFFAOYSA-N 0.000 claims 1
- VKVHSWCHAYCXHZ-UHFFFAOYSA-N 1-[4-(4-amino-2-butyl-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-phenylurea Chemical compound CCCCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCCNC(=O)NC1=CC=CC=C1 VKVHSWCHAYCXHZ-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
- UVAGDABZFICNIO-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(2-phenylethyl)thiourea Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=S)NCCC1=CC=CC=C1 UVAGDABZFICNIO-UHFFFAOYSA-N 0.000 claims 1
- FNPAYWMRJXYKET-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(3-cyanophenyl)urea Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=O)NC1=CC=CC(C#N)=C1 FNPAYWMRJXYKET-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
- URQBAHJFRLITDX-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(3-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC(NC(=O)NCCCCN2C3=C(C)C(C)=NC(N)=C3N=C2)=C1 URQBAHJFRLITDX-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
- UQVASIPCJGTITM-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCCCCN1C2=C(C)C(C)=NC(N)=C2N=C1 UQVASIPCJGTITM-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
- BLELKOLLVDDNCI-UHFFFAOYSA-N 1-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-3-propan-2-ylurea Chemical compound N1=C(C)C(C)=C2N(CCCCNC(=O)NC(C)C)C=NC2=C1N BLELKOLLVDDNCI-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
- GPJNTROCFYIHNS-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(2,4-dimethoxyphenyl)urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)NC1=CC=C(OC)C=C1OC GPJNTROCFYIHNS-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
- LCXGLJKNXKWZKV-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(3-cyanophenyl)urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)NC1=CC=CC(C#N)=C1 LCXGLJKNXKWZKV-UHFFFAOYSA-N 0.000 claims 1
- DZNVVQQMELNSKX-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(3-methylsulfanylphenyl)urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)NC1=CC=CC(SC)=C1 DZNVVQQMELNSKX-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
- 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
- PCFHUTWERMEFJD-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-methylthiourea Chemical compound N1=C(C)C=C2N(CCCCNC(=S)NC)C(COCC)=NC2=C1N PCFHUTWERMEFJD-UHFFFAOYSA-N 0.000 claims 1
- QXTDNCAESIZUGN-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-phenylthiourea Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=S)NC1=CC=CC=C1 QXTDNCAESIZUGN-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
- PORNKGRBHUGIRO-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-propan-2-ylurea Chemical compound N1=C(C)C=C2N(CCCCNC(=O)NC(C)C)C(COCC)=NC2=C1N PORNKGRBHUGIRO-UHFFFAOYSA-N 0.000 claims 1
- RVTBCYWYANZOGQ-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-tert-butylurea Chemical compound N1=C(C)C=C2N(CCCCNC(=O)NC(C)(C)C)C(COCC)=NC2=C1N RVTBCYWYANZOGQ-UHFFFAOYSA-N 0.000 claims 1
- VUSJZIYCHDZUQE-UHFFFAOYSA-N 1-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 VUSJZIYCHDZUQE-UHFFFAOYSA-N 0.000 claims 1
- PAXRMHXVJCJMBS-UHFFFAOYSA-N 4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]-n-(4-chlorophenyl)sulfonylpiperidine-1-carboxamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 PAXRMHXVJCJMBS-UHFFFAOYSA-N 0.000 claims 1
- ZMNRLJDQVSNWMM-UHFFFAOYSA-N 4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]-n-(benzenesulfonyl)piperidine-1-carboxamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)NS(=O)(=O)C1=CC=CC=C1 ZMNRLJDQVSNWMM-UHFFFAOYSA-N 0.000 claims 1
- CLFGNQWYGNAMTP-UHFFFAOYSA-N 4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]-n-phenylpiperidine-1-carbothioamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=S)NC1=CC=CC=C1 CLFGNQWYGNAMTP-UHFFFAOYSA-N 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- UKZKLHXMLICIGB-UHFFFAOYSA-N [4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1C(=O)N1CCOCC1 UKZKLHXMLICIGB-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- NLFLYNPLOQAXSQ-UHFFFAOYSA-N ethyl 2-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butylcarbamoylamino]acetate Chemical compound N1=C(C)C=C2N(CCCCNC(=O)NCC(=O)OCC)C(COCC)=NC2=C1N NLFLYNPLOQAXSQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- JUVUAQGQQRBWHC-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)piperidine-1-carboxamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)N1CCCCC1 JUVUAQGQQRBWHC-UHFFFAOYSA-N 0.000 claims 1
- WIJUADBJWJMUGE-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-yl]morpholine-4-carboxamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CC(C)(C)NC(=O)N1CCOCC1 WIJUADBJWJMUGE-UHFFFAOYSA-N 0.000 claims 1
- JWQQGPWOGBNCRC-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]morpholine-4-carboxamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)N1CCOCC1 JWQQGPWOGBNCRC-UHFFFAOYSA-N 0.000 claims 1
- GQFVTOGAKQNFEC-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]morpholine-4-carboxamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)N1CCOCC1 GQFVTOGAKQNFEC-UHFFFAOYSA-N 0.000 claims 1
- FVCPBXWXGNEPMA-UHFFFAOYSA-N n-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]morpholine-4-carboxamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)N1CCOCC1 FVCPBXWXGNEPMA-UHFFFAOYSA-N 0.000 claims 1
- GGCNXOWEVVGGCX-UHFFFAOYSA-N n-[4-(4-amino-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]morpholine-4-carboxamide Chemical compound C12=C(C)C(C)=NC(N)=C2N=CN1CCCCNC(=O)N1CCOCC1 GGCNXOWEVVGGCX-UHFFFAOYSA-N 0.000 claims 1
- CSOCSDKWCKYIQQ-UHFFFAOYSA-N n-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]morpholine-4-carboxamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=O)N1CCOCC1 CSOCSDKWCKYIQQ-UHFFFAOYSA-N 0.000 claims 1
- RPKDMZAJCYLRTR-UHFFFAOYSA-N n-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butylcarbamothioyl]furan-2-carboxamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNC(=S)NC(=O)C1=CC=CO1 RPKDMZAJCYLRTR-UHFFFAOYSA-N 0.000 claims 1
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
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| JP5947724B2 (ja) * | 2009-12-21 | 2016-07-06 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | シクロフィリンの新しいインヒビター及びその使用 |
| DK2606047T3 (en) | 2010-08-17 | 2017-03-27 | 3M Innovative Properties Co | COMPOSITIONS AND FORMULATIONS WITH LIPIDIZED IMMUNE RESPONSE-MODIFIING COMPOUND AND PROCEDURES THEREOF |
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| US10471139B2 (en) * | 2013-08-15 | 2019-11-12 | The University Of Kansas | Toll-like receptor agonists |
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| CA3086439A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| JP7397011B2 (ja) | 2018-06-06 | 2023-12-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | Ｓ１ｐ１受容体に関連する状態を治療する方法 |
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| DK0708772T3 (da) * | 1993-07-15 | 2000-09-18 | Minnesota Mining & Mfg | Imidazo[4,5,-c]pyridin-4-aminer |
| JP4391592B2 (ja) * | 1996-10-25 | 2009-12-24 | スリーエム カンパニー | Ｔｈ２介在性および関連疾患治療のための免疫応答修飾化合物 |
| 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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- 2002-06-07 EP EP02739783A patent/EP1453829A1/en not_active Withdrawn
- 2002-06-07 WO PCT/US2002/018282 patent/WO2003050118A1/en not_active Ceased
- 2002-06-07 CN CNB028242866A patent/CN100372846C/zh not_active Expired - Fee Related
- 2002-06-07 JP JP2003551143A patent/JP2005511746A/ja active Pending
- 2002-06-07 KR KR10-2004-7008686A patent/KR20040105696A/ko not_active Ceased
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- 2002-06-07 MX MXPA04005412A patent/MXPA04005412A/es not_active Application Discontinuation
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- 2002-06-07 HR HRP20040506 patent/HRP20040506A2/hr not_active Application Discontinuation
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- 2004-06-24 NO NO20042661A patent/NO20042661L/no not_active Application Discontinuation
- 2004-06-29 NO NO20042755A patent/NO20042755L/no not_active Application Discontinuation
- 2004-07-05 ZA ZA200405336A patent/ZA200405336B/en unknown
- 2004-07-05 ZA ZA200405337A patent/ZA200405337B/en unknown
- 2004-07-05 ZA ZA200405334A patent/ZA200405334B/en unknown