HRP20040506A2 - Urea substituted imidazopyridines - Google Patents
Urea substituted imidazopyridinesInfo
- Publication number
- HRP20040506A2 HRP20040506A2 HRP20040506A HRP20040506A2 HR P20040506 A2 HRP20040506 A2 HR P20040506A2 HR P20040506 A HRP20040506 A HR P20040506A HR P20040506 A2 HRP20040506 A2 HR P20040506A2
- Authority
- HR
- Croatia
- Prior art keywords
- amino
- imidazo
- pyridin
- ethoxymethyl
- butyl
- Prior art date
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims description 34
- 239000004202 carbamide Substances 0.000 title claims description 16
- 150000005232 imidazopyridines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 130
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 150000003839 salts Chemical class 0.000 claims description 28
- -1 -alkyl-Y-alkenyl Chemical class 0.000 claims description 27
- 102000004127 Cytokines Human genes 0.000 claims description 26
- 108090000695 Cytokines Proteins 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 241001465754 Metazoa Species 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 13
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
- 230000006698 induction Effects 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 9
- 230000003612 virological effect Effects 0.000 claims description 9
- 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
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 230000001613 neoplastic effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 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 description 4
- 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 description 4
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 3
- 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 description 3
- 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 description 2
- 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 description 2
- 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 description 2
- QQSAADHASCBHOH-UHFFFAOYSA-N 3-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-1-methyl-1-phenylurea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)N(C)C1=CC=CC=C1 QQSAADHASCBHOH-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 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 description 2
- IJBGRJLFMPCNRK-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propylcarbamothioyl]furan-2-carboxamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=S)NC(=O)C1=CC=CO1 IJBGRJLFMPCNRK-UHFFFAOYSA-N 0.000 claims description 2
- RQUKVAVDVPZVSL-UHFFFAOYSA-N n-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propylcarbamothioyl]furan-2-carboxamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=S)NC(=O)C1=CC=CO1 RQUKVAVDVPZVSL-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- DSQVSJRWWPGLPJ-UHFFFAOYSA-N 1-(1-adamantyl)-3-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]thiourea Chemical compound C1C(C2)CC(C3)CC2CC13NC(=S)NCCN1C2=C(C)C(C)=NC(N)=C2N=C1C DSQVSJRWWPGLPJ-UHFFFAOYSA-N 0.000 claims 1
- IYIJVBGVSJLXJY-UHFFFAOYSA-N 1-(1-adamantyl)-3-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]urea Chemical compound C12(CC3CC(CC(C1)C3)C2)NC(=O)NCCN2C(=NC=3C(=NC(=C(C32)C)C)N)C IYIJVBGVSJLXJY-UHFFFAOYSA-N 0.000 claims 1
- ZFHUMWMUCGVVGO-UHFFFAOYSA-N 1-(1-adamantyl)-3-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]urea Chemical compound C1C(C2)CC(C3)CC2CC13NC(=O)NCCCCN1C2=C(C)C=NC(N)=C2N=C1COCC ZFHUMWMUCGVVGO-UHFFFAOYSA-N 0.000 claims 1
- QKNRJRNYWAZVSM-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 QKNRJRNYWAZVSM-UHFFFAOYSA-N 0.000 claims 1
- TXZFVYMUJLFQPU-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NCCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 TXZFVYMUJLFQPU-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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
- SQGPEMMUKPXDIJ-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(2-morpholin-4-ylethyl)thiourea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=S)NCCN1CCOCC1 SQGPEMMUKPXDIJ-UHFFFAOYSA-N 0.000 claims 1
- YVZYWRWPQRSIOX-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(3-cyanophenyl)urea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)NC1=CC=CC(C#N)=C1 YVZYWRWPQRSIOX-UHFFFAOYSA-N 0.000 claims 1
- RGFUOVWNJRLMIW-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 RGFUOVWNJRLMIW-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
- AQOUWHJCFDPESV-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-(benzenesulfonyl)urea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AQOUWHJCFDPESV-UHFFFAOYSA-N 0.000 claims 1
- VOOBZWQZJQOOAU-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-[3-(diethylamino)propyl]thiourea Chemical compound N1=C(C)C(C)=C2N(CCNC(=S)NCCCN(CC)CC)C(C)=NC2=C1N VOOBZWQZJQOOAU-UHFFFAOYSA-N 0.000 claims 1
- RZADMBULTJQWJB-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNC(=O)NC1=CC=C(C(F)(F)F)C=C1 RZADMBULTJQWJB-UHFFFAOYSA-N 0.000 claims 1
- MQTJPRKBBQDBSD-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-butylurea Chemical compound N1=C(C)C(C)=C2N(CCNC(=O)NCCCC)C(C)=NC2=C1N MQTJPRKBBQDBSD-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
- MSUVHKAGWOBJSA-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-diethoxyphosphorylurea Chemical class N1=C(C)C(C)=C2N(CCNC(=O)NP(=O)(OCC)OCC)C(C)=NC2=C1N MSUVHKAGWOBJSA-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
- IAIREPXWSGIKAF-UHFFFAOYSA-N 1-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-tert-butylurea Chemical compound N1=C(C)C(C)=C2N(CCNC(=O)NC(C)(C)C)C(C)=NC2=C1N IAIREPXWSGIKAF-UHFFFAOYSA-N 0.000 claims 1
- MSGKPCCYEFJVOH-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(2,4-dimethoxyphenyl)urea Chemical compound COC1=CC(OC)=CC=C1NC(=O)NCCCN1C2=C(C)C(C)=NC(N)=C2N=C1C MSGKPCCYEFJVOH-UHFFFAOYSA-N 0.000 claims 1
- QUEXRCBCNVEDJI-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(2-chlorophenyl)sulfonylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NS(=O)(=O)C1=CC=CC=C1Cl QUEXRCBCNVEDJI-UHFFFAOYSA-N 0.000 claims 1
- PILZBQVUCWDKBT-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(2-phenylethyl)thiourea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=S)NCCC1=CC=CC=C1 PILZBQVUCWDKBT-UHFFFAOYSA-N 0.000 claims 1
- PADPEXGUVOBCLO-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(3-cyanophenyl)urea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NC1=CC=CC(C#N)=C1 PADPEXGUVOBCLO-UHFFFAOYSA-N 0.000 claims 1
- UWZIFQWVIJBGCG-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NCCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 UWZIFQWVIJBGCG-UHFFFAOYSA-N 0.000 claims 1
- GLKVOOUOCBFZTG-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(3-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC(NC(=O)NCCCN2C3=C(C)C(C)=NC(N)=C3N=C2C)=C1 GLKVOOUOCBFZTG-UHFFFAOYSA-N 0.000 claims 1
- LWYULGPXWBTZKG-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(4-methoxyphenyl)thiourea Chemical compound C1=CC(OC)=CC=C1NC(=S)NCCCN1C2=C(C)C(C)=NC(N)=C2N=C1C LWYULGPXWBTZKG-UHFFFAOYSA-N 0.000 claims 1
- KWZHYZMOEOSTJM-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 KWZHYZMOEOSTJM-UHFFFAOYSA-N 0.000 claims 1
- IQTYSGPLFOJBRQ-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)NCCCN1C2=C(C)C(C)=NC(N)=C2N=C1C IQTYSGPLFOJBRQ-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
- REAMDQUYTQQEBD-UHFFFAOYSA-N 1-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-propan-2-ylurea Chemical compound N1=C(C)C(C)=C2N(CCCNC(=O)NC(C)C)C(C)=NC2=C1N REAMDQUYTQQEBD-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
- GQUQENLJUVPYRG-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-(2-morpholin-4-ylethyl)thiourea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=S)NCCN1CCOCC1 GQUQENLJUVPYRG-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
- DVFOGSDDEPWLSA-UHFFFAOYSA-N 1-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-3-(3-methoxyphenyl)urea Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNC(=O)NC1=CC=CC(OC)=C1 DVFOGSDDEPWLSA-UHFFFAOYSA-N 0.000 claims 1
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- JMJJXMFMLJSYGW-UHFFFAOYSA-N tert-butyl n-[4-[[2-chloro-6-(dibenzylamino)-3-methyl-5-nitropyridin-4-yl]amino]butyl]carbamate Chemical compound [O-][N+](=O)C1=C(NCCCCNC(=O)OC(C)(C)C)C(C)=C(Cl)N=C1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 JMJJXMFMLJSYGW-UHFFFAOYSA-N 0.000 description 1
- KCHHMWLEMRAUPC-UHFFFAOYSA-N tert-butyl n-[4-[[3-[(2-ethoxyacetyl)amino]-6-methyl-2-phenoxypyridin-4-yl]amino]butyl]carbamate Chemical compound CCOCC(=O)NC1=C(NCCCCNC(=O)OC(C)(C)C)C=C(C)N=C1OC1=CC=CC=C1 KCHHMWLEMRAUPC-UHFFFAOYSA-N 0.000 description 1
- MFIPZIUOGXJJHK-UHFFFAOYSA-N tert-butyl n-[4-[[3-amino-2-(dibenzylamino)-5,6-dimethylpyridin-4-yl]amino]butyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCCNC1=C(C)C(C)=NC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1N MFIPZIUOGXJJHK-UHFFFAOYSA-N 0.000 description 1
- MWHQFJOTIJDBDY-UHFFFAOYSA-N tert-butyl n-[4-[[5-[(2-ethoxyacetyl)amino]-2,3-dimethyl-6-phenoxypyridin-4-yl]amino]butyl]carbamate Chemical compound N1=C(C)C(C)=C(NCCCCNC(=O)OC(C)(C)C)C(NC(=O)COCC)=C1OC1=CC=CC=C1 MWHQFJOTIJDBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000029069 type 2 immune response Effects 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
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- Communicable Diseases (AREA)
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- Tropical Medicine & Parasitology (AREA)
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- Neurosurgery (AREA)
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- Biotechnology (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Gastroenterology & Hepatology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/016,073 US20020107262A1 (en) | 2000-12-08 | 2001-12-06 | Substituted imidazopyridines |
PCT/US2002/018284 WO2003050119A2 (en) | 2001-12-06 | 2002-06-07 | Urea substituted imidazopyridines |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20040506A2 true HRP20040506A2 (en) | 2004-12-31 |
Family
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Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20040503 HRP20040503A2 (en) | 2001-12-06 | 2004-06-04 | Amide supstituted imidazopyridines |
HRP20040506 HRP20040506A2 (en) | 2001-12-06 | 2004-06-04 | Urea substituted imidazopyridines |
HRP20040504 HRP20040504A2 (en) | 2001-12-06 | 2004-06-04 | Sulfonamido substituted imidazopyridines |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20040503 HRP20040503A2 (en) | 2001-12-06 | 2004-06-04 | Amide supstituted imidazopyridines |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HRP20040504 HRP20040504A2 (en) | 2001-12-06 | 2004-06-04 | Sulfonamido substituted imidazopyridines |
Country Status (18)
Country | Link |
---|---|
US (1) | US20020107262A1 (xx) |
EP (3) | EP1451186A2 (xx) |
JP (3) | JP2005511745A (xx) |
KR (3) | KR20040105695A (xx) |
CN (4) | CN100402528C (xx) |
AU (3) | AU2002312414B2 (xx) |
BR (3) | BR0214999A (xx) |
CA (3) | CA2468659A1 (xx) |
HR (3) | HRP20040503A2 (xx) |
IL (3) | IL161787A0 (xx) |
MX (3) | MXPA04005412A (xx) |
NO (3) | NO20042621L (xx) |
NZ (3) | NZ532926A (xx) |
PL (3) | PL374260A1 (xx) |
RU (3) | RU2004117159A (xx) |
UA (3) | UA77709C2 (xx) |
WO (3) | WO2003050117A1 (xx) |
ZA (3) | ZA200405336B (xx) |
Families Citing this family (78)
Publication number | Priority date | Publication date | Assignee | Title |
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AU2003237386A1 (en) | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
ATE374766T1 (de) | 2003-01-14 | 2007-10-15 | Arena Pharm Inc | 1,2,3-trisubstituierte aryl- und heteroarylderivate als modulatoren des metabolismus zur vorbeugung und behandlung von metabolismus-bedingten krankheiten wie diabetes oder hyperglykämie |
JP2006522823A (ja) * | 2003-04-10 | 2006-10-05 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫反応調節物質化合物の送達 |
US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
EP1653914A4 (en) * | 2003-08-12 | 2008-10-29 | 3M Innovative Properties Co | COMPOUNDS CONTAINING OXIME SUBSTITUTED IMIDAZO STRUCTURE |
CA2535338C (en) * | 2003-08-14 | 2013-05-28 | 3M Innovative Properties Company | Substituted 1h-imidazo[4,5-c]pyridin-4-amines,1h-imidazo[4,5-c]quinolin -4-amines and 1h-imidazo[4,5-c]naphthyridin-4-amines as immune response modifiers |
NZ545412A (en) | 2003-08-27 | 2008-12-24 | Coley Pharm Group Inc | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
CA2537763A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
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US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
BRPI0414867A (pt) | 2003-10-03 | 2006-11-21 | 3M Innovative Properties Co | pirazolopiridinas e seus análogos |
EP1678137A1 (en) * | 2003-10-15 | 2006-07-12 | Chiron Corporation | Compositions and methods for viral inhibition |
CN1906193A (zh) * | 2003-11-14 | 2007-01-31 | 3M创新有限公司 | 肟取代的咪唑环化合物 |
CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
MXPA06005910A (es) | 2003-11-25 | 2006-08-23 | 3M Innovative Properties Co | Sistemas de anillo imidazo sustituido y metodos. |
EP1686992A4 (en) * | 2003-11-25 | 2009-11-04 | 3M Innovative Properties Co | HYDROXYLAMINE, AND IMIDAZOQUINOLEINS, AND IMIDAZOPYRIDINES AND IMIDAZONAPHTYRIDINE SUBSTITUTED WITH OXIME |
AR048289A1 (es) * | 2003-12-04 | 2006-04-19 | 3M Innovative Properties Co | Eteres de anillos imidazo sulfona sustituidos. |
AU2004312510A1 (en) * | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds |
WO2005066170A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
JP2007517044A (ja) | 2003-12-30 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | イミダゾキノリニル、イミダゾピリジニル、およびイミダゾナフチリジニルスルホンアミド |
AU2005228150A1 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
WO2005123079A2 (en) * | 2004-06-14 | 2005-12-29 | 3M Innovative Properties Company | Urea substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
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WO2006028962A2 (en) * | 2004-09-02 | 2006-03-16 | 3M Innovative Properties Company | 1-alkoxy 1h-imidazo ring systems and methods |
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JP5313502B2 (ja) | 2004-12-30 | 2013-10-09 | スリーエム イノベイティブ プロパティズ カンパニー | 置換キラル縮合[1,2]イミダゾ[4,5−c]環状化合物 |
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WO1995002597A1 (en) * | 1993-07-15 | 1995-01-26 | Minnesota Mining And Manufacturing Company | IMIDAZO[4,5-c]PYRIDIN-4-AMINES |
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