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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| PCT/US2002/018284 WO2003050119A2 (en) | 2001-12-06 | 2002-06-07 | Urea substituted imidazopyridines |
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| JP2005511746A JP2005511746A (ja) | 2005-04-28 |
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| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| AU2004266658A1 (en) * | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| US7799800B2 (en) * | 2003-08-14 | 2010-09-21 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
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| BRPI0414856A (pt) | 2003-10-03 | 2006-11-21 | 3M Innovative Properties Co | imidazoquinolinas alcóxi-substituìdas |
| JP2007508305A (ja) | 2003-10-03 | 2007-04-05 | スリーエム イノベイティブ プロパティズ カンパニー | ピラゾロピリジンおよびその類似物 |
| US20070276009A1 (en) * | 2003-10-15 | 2007-11-29 | Zhi-Jie Ni | Compositions and Methods for Viral Inhibition |
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| CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| WO2005051324A2 (en) * | 2003-11-25 | 2005-06-09 | 3M Innovative Properties Company | Hydroxylamine and oxime substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
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| JP2007530450A (ja) * | 2003-12-29 | 2007-11-01 | スリーエム イノベイティブ プロパティズ カンパニー | ピペラジン、［１，４］ジアゼパン、［１，４］ジアゾカン、および［１，５］ジアゾカン縮合イミダゾ環化合物 |
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| US8158794B2 (en) | 2005-02-23 | 2012-04-17 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazoquinoline compounds and methods |
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| CN100344325C (zh) * | 2005-10-17 | 2007-10-24 | 华南师范大学 | 一种治疗宫颈癌的药物及其制备方法与应用 |
| KR20080083270A (ko) | 2005-11-04 | 2008-09-17 | 콜레이 파마시티컬 그룹, 인코포레이티드 | 하이드록시 및 알콕시 치환된 1에이치 이미다조퀴놀린 및방법 |
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| GB0625827D0 (en) * | 2006-12-22 | 2007-02-07 | Astex Therapeutics Ltd | New compounds |
| US20080149123A1 (en) | 2006-12-22 | 2008-06-26 | Mckay William D | Particulate material dispensing hairbrush with combination bristles |
| GB0720041D0 (en) | 2007-10-12 | 2007-11-21 | Astex Therapeutics Ltd | New Compounds |
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| CN101239978A (zh) * | 2008-03-05 | 2008-08-13 | 南方医科大学 | 一种咪唑并吡啶类化合物 |
| GB0810902D0 (en) | 2008-06-13 | 2008-07-23 | Astex Therapeutics Ltd | New compounds |
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| CN105693597A (zh) * | 2009-12-21 | 2016-06-22 | 国家健康与医学研究院（Inserm） | 新的亲环素抑制剂及其用途 |
| SI2606047T1 (sl) | 2010-08-17 | 2017-04-26 | 3M Innovative Properties Company | Lipidirani sestavki spojine, ki modificira imunski odgovor, formulacije in postopki |
| AU2011305525B2 (en) | 2010-09-22 | 2016-08-18 | Arena Pharmaceuticals, Inc. | Modulators of the GPR119 receptor and the treatment of disorders related thereto |
| EP2718292B1 (en) | 2011-06-03 | 2018-03-14 | 3M Innovative Properties Company | Hydrazino 1h-imidazoquinolin-4-amines and conjugates made therefrom |
| US9475804B2 (en) | 2011-06-03 | 2016-10-25 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| US10471139B2 (en) * | 2013-08-15 | 2019-11-12 | The University Of Kansas | Toll-like receptor agonists |
| CN116850181A (zh) | 2015-01-06 | 2023-10-10 | 艾尼纳制药公司 | 治疗与s1p1受体有关的病症的方法 |
| AU2016284162A1 (en) | 2015-06-22 | 2018-02-01 | 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 SIP1 receptor-associated disorders |
| WO2018107173A1 (en) * | 2016-12-09 | 2018-06-14 | Vanderbilt University | Glutamine transport inhibitors and methods for treating cancer |
| AU2018220521A1 (en) | 2017-02-16 | 2019-09-05 | 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE195735T1 (de) * | 1993-07-15 | 2000-09-15 | Minnesota Mining & Mfg | Imidazo (4,5-c)pyridin-4-amine |
| EP0938315B9 (en) * | 1996-10-25 | 2008-02-20 | Minnesota Mining And Manufacturing Company | Immune response modifier compounds for treatment of th2 mediated and related diseases |
| 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 |
| US6541485B1 (en) * | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea 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
- 2001-12-06 US US10/016,073 patent/US20020107262A1/en not_active Abandoned
-
2002
- 2002-06-07 CA CA002468174A patent/CA2468174A1/en not_active Abandoned
- 2002-06-07 EP EP02739783A patent/EP1453829A1/en not_active Withdrawn
- 2002-06-07 JP JP2003551143A patent/JP2005511746A/ja active Pending
- 2002-06-07 BR BR0214999-0A patent/BR0214999A/pt not_active IP Right Cessation
- 2002-06-07 HR HRP20040504 patent/HRP20040504A2/hr not_active Application Discontinuation
- 2002-06-07 JP JP2003551141A patent/JP2005513052A/ja active Pending
- 2002-06-07 RU RU2004117156/04A patent/RU2004117156A/ru not_active Application Discontinuation
- 2002-06-07 CA CA002468164A patent/CA2468164A1/en not_active Abandoned
- 2002-06-07 AU AU2002312414A patent/AU2002312414B2/en not_active Expired - Fee Related
- 2002-06-07 AU AU2002315006A patent/AU2002315006B2/en not_active Expired - Fee Related
- 2002-06-07 PL PL02370702A patent/PL370702A1/xx not_active Application Discontinuation
- 2002-06-07 WO PCT/US2002/018220 patent/WO2003050117A1/en not_active Ceased
- 2002-06-07 BR BR0214752-1A patent/BR0214752A/pt not_active IP Right Cessation
- 2002-06-07 HR HRP20040503 patent/HRP20040503A2/hr not_active Application Discontinuation
- 2002-06-07 EP EP02741939A patent/EP1451186A2/en not_active Withdrawn
- 2002-06-07 AU AU2002345615A patent/AU2002345615B2/en not_active Expired - Fee Related
- 2002-06-07 EP EP02744260A patent/EP1451187A1/en not_active Withdrawn
- 2002-06-07 HR HRP20040506 patent/HRP20040506A2/hr not_active Application Discontinuation
- 2002-06-07 WO PCT/US2002/018282 patent/WO2003050118A1/en not_active Ceased
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- 2002-06-07 CN CNA2008100030374A patent/CN101220028A/zh active Pending
- 2002-06-07 NZ NZ532927A patent/NZ532927A/en unknown
- 2002-06-07 KR KR10-2004-7008644A patent/KR20040105694A/ko not_active Ceased
- 2002-06-07 RU RU2004117161/04A patent/RU2004117161A/ru not_active Application Discontinuation
- 2002-06-07 CN CNB028242858A patent/CN100402528C/zh not_active Expired - Fee Related
- 2002-06-07 RU RU2004117159/04A patent/RU2004117159A/ru not_active Application Discontinuation
- 2002-06-07 MX MXPA04005363A patent/MXPA04005363A/es unknown
- 2002-06-07 MX MXPA04005331A patent/MXPA04005331A/es unknown
- 2002-06-07 WO PCT/US2002/018284 patent/WO2003050119A2/en not_active Ceased
- 2002-06-07 JP JP2003551142A patent/JP2005511745A/ja active Pending
- 2002-06-07 CA CA002468659A patent/CA2468659A1/en not_active Abandoned
- 2002-06-07 NZ NZ532770A patent/NZ532770A/en unknown
- 2002-06-07 CN CNB028242874A patent/CN100387597C/zh not_active Expired - Fee Related
- 2002-06-07 IL IL16194602A patent/IL161946A0/xx unknown
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- 2002-06-07 BR BR0214749-1A patent/BR0214749A/pt not_active IP Right Cessation
- 2002-06-07 KR KR10-2004-7008676A patent/KR20040105695A/ko not_active Ceased
- 2002-06-07 PL PL02370738A patent/PL370738A1/xx not_active Application Discontinuation
- 2002-06-07 PL PL02374260A patent/PL374260A1/xx not_active Application Discontinuation
- 2002-06-07 MX MXPA04005412A patent/MXPA04005412A/es not_active Application Discontinuation
- 2002-06-07 IL IL16178702A patent/IL161787A0/xx unknown
- 2002-06-07 KR KR10-2004-7008686A patent/KR20040105696A/ko not_active Ceased
- 2002-07-06 UA UA20040604342A patent/UA77710C2/uk unknown
- 2002-07-06 UA UA20040604339A patent/UA77709C2/uk unknown
- 2002-07-06 UA UA20040604343A patent/UA77711C2/uk unknown
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2004
- 2004-06-22 NO NO20042621A patent/NO20042621L/no not_active Application Discontinuation
- 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 ZA200405334A patent/ZA200405334B/en unknown
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