HRP20010889A2 - Urea substituted imidazoquinolines - Google Patents
Urea substituted imidazoquinolines Download PDFInfo
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- HRP20010889A2 HRP20010889A2 HR20010889A HRP20010889A HRP20010889A2 HR P20010889 A2 HRP20010889 A2 HR P20010889A2 HR 20010889 A HR20010889 A HR 20010889A HR P20010889 A HRP20010889 A HR P20010889A HR P20010889 A2 HRP20010889 A2 HR P20010889A2
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- Prior art keywords
- alkyl
- substituted
- amino
- compound
- butyl
- Prior art date
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 239000004202 carbamide Substances 0.000 title claims abstract description 13
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 102000004127 Cytokines Human genes 0.000 claims abstract description 30
- 108090000695 Cytokines Proteins 0.000 claims abstract description 30
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 241001465754 Metazoa Species 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- -1 N-[4-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-N'-(2-methoxybenzyl)urea Chemical compound 0.000 claims description 20
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 208000036142 Viral infection Diseases 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 230000009385 viral infection Effects 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 230000001939 inductive effect Effects 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- 150000003235 pyrrolidines Chemical class 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- BPLHTXPSAXJAFU-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-propylurea Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCNC(=O)NCCC)C3=C(N)N=C21 BPLHTXPSAXJAFU-UHFFFAOYSA-N 0.000 claims 2
- SRFTUXVTTTWQNV-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-naphthalen-1-ylthiourea Chemical compound C1=CC=C2C(NC(=S)NCCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCOC)=CC=CC2=C1 SRFTUXVTTTWQNV-UHFFFAOYSA-N 0.000 claims 2
- HOSCYTXZFKKPPR-UHFFFAOYSA-N 1-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]-3-(4-methylphenyl)sulfonylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 HOSCYTXZFKKPPR-UHFFFAOYSA-N 0.000 claims 1
- OWQMXPKYEJAJQQ-UHFFFAOYSA-N 1-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]-3-(4-phenoxyphenyl)urea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 OWQMXPKYEJAJQQ-UHFFFAOYSA-N 0.000 claims 1
- HSFXSDZZAZVAGZ-UHFFFAOYSA-N 1-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]-3-benzylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNC(=O)NCC1=CC=CC=C1 HSFXSDZZAZVAGZ-UHFFFAOYSA-N 0.000 claims 1
- JMTKPGBQTLEPJZ-UHFFFAOYSA-N 1-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]-3-phenylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNC(=O)NC1=CC=CC=C1 JMTKPGBQTLEPJZ-UHFFFAOYSA-N 0.000 claims 1
- TZQBUVWAAPKQHB-UHFFFAOYSA-N 1-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]-3-propylurea Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCNC(=O)NCCC)C3=C(N)N=C21 TZQBUVWAAPKQHB-UHFFFAOYSA-N 0.000 claims 1
- RPOVWKUOUVVSNE-UHFFFAOYSA-N 1-[2-[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]ethyl]-3-cyclohexylurea Chemical compound CCOCC1=NC2=C(N)N=C3CCCCC3=C2N1CCNC(=O)NC1CCCCC1 RPOVWKUOUVVSNE-UHFFFAOYSA-N 0.000 claims 1
- UCJAQFKRULMLAG-UHFFFAOYSA-N 1-[2-[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]ethyl]-3-phenylurea Chemical compound CCOCC1=NC2=C(N)N=C3CCCCC3=C2N1CCNC(=O)NC1=CC=CC=C1 UCJAQFKRULMLAG-UHFFFAOYSA-N 0.000 claims 1
- SEUTWMMPCIBAPW-UHFFFAOYSA-N 1-[2-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]-3-cyclohexylthiourea Chemical compound CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNC(=S)NC1CCCCC1 SEUTWMMPCIBAPW-UHFFFAOYSA-N 0.000 claims 1
- SXBPCLFGOCWHSG-UHFFFAOYSA-N 1-[2-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]-3-cyclohexylurea Chemical compound CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNC(=O)NC1CCCCC1 SXBPCLFGOCWHSG-UHFFFAOYSA-N 0.000 claims 1
- WETRTSFKYRYJTL-UHFFFAOYSA-N 1-[2-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]-3-phenylurea Chemical compound CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNC(=O)NC1=CC=CC=C1 WETRTSFKYRYJTL-UHFFFAOYSA-N 0.000 claims 1
- AYLFRRUGIWQQMF-UHFFFAOYSA-N 1-[2-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]-3-propylurea Chemical compound C1=CC=CC2=C3N(CCNC(=O)NCCC)C(COCC)=NC3=C(N)N=C21 AYLFRRUGIWQQMF-UHFFFAOYSA-N 0.000 claims 1
- RTKDLGBCPLRAGE-UHFFFAOYSA-N 1-[4-(4-amino-2-butyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl)butyl]-3-(benzenesulfonyl)urea Chemical compound CCCCC1=NC2=C(N)N=C3CCCCC3=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 RTKDLGBCPLRAGE-UHFFFAOYSA-N 0.000 claims 1
- VPBUUTYNKJMWSG-UHFFFAOYSA-N 1-[4-(4-amino-2-butyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl)butyl]-3-benzylurea Chemical compound CCCCC1=NC2=C(N)N=C3CCCCC3=C2N1CCCCNC(=O)NCC1=CC=CC=C1 VPBUUTYNKJMWSG-UHFFFAOYSA-N 0.000 claims 1
- UBWGTRAAHCDRMQ-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-(2-methoxyphenyl)urea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NC1=CC=CC=C1OC UBWGTRAAHCDRMQ-UHFFFAOYSA-N 0.000 claims 1
- WDPFVVXLBXEWSV-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-(4-chlorophenyl)sulfonylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 WDPFVVXLBXEWSV-UHFFFAOYSA-N 0.000 claims 1
- UWDVETLRQZEDJW-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-(4-ethylphenyl)sulfonylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=C(CC)C=C1 UWDVETLRQZEDJW-UHFFFAOYSA-N 0.000 claims 1
- SEOGCPUBWIHCBE-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-(4-fluorophenyl)sulfonylurea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=C(F)C=C1 SEOGCPUBWIHCBE-UHFFFAOYSA-N 0.000 claims 1
- PTTYRTVPNPWXRG-UHFFFAOYSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-(benzenesulfonyl)urea Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 PTTYRTVPNPWXRG-UHFFFAOYSA-N 0.000 claims 1
- WGOGYKSWZJXMRD-LJQANCHMSA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-[(1r)-1-phenylethyl]urea Chemical compound C1([C@@H](C)NC(=O)NCCCCN2C3=C4C=CC=CC4=NC(N)=C3N=C2CCCC)=CC=CC=C1 WGOGYKSWZJXMRD-LJQANCHMSA-N 0.000 claims 1
- WGOGYKSWZJXMRD-IBGZPJMESA-N 1-[4-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)butyl]-3-[(1s)-1-phenylethyl]urea Chemical compound C1([C@H](C)NC(=O)NCCCCN2C3=C4C=CC=CC4=NC(N)=C3N=C2CCCC)=CC=CC=C1 WGOGYKSWZJXMRD-IBGZPJMESA-N 0.000 claims 1
- GGRKOPMXBXDKKB-UHFFFAOYSA-N 1-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NCCCCN1C2=C3C=CC=CC3=NC(N)=C2N=C1 GGRKOPMXBXDKKB-UHFFFAOYSA-N 0.000 claims 1
- IBVSEJCWAUPECO-UHFFFAOYSA-N 1-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-3-benzylurea Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)NCC1=CC=CC=C1 IBVSEJCWAUPECO-UHFFFAOYSA-N 0.000 claims 1
- CIVXWYSFRLYIBQ-UHFFFAOYSA-N 1-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-3-butylurea Chemical compound C1=CC=CC2=C3N(CCCCNC(=O)NCCCC)C=NC3=C(N)N=C21 CIVXWYSFRLYIBQ-UHFFFAOYSA-N 0.000 claims 1
- QVUYBNCPLXLSOM-UHFFFAOYSA-N 1-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-3-cyclohexylurea Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)NC1CCCCC1 QVUYBNCPLXLSOM-UHFFFAOYSA-N 0.000 claims 1
- VLDXADUEBXLIKK-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]butyl]-1-phenylurea Chemical compound COCCC1=NC2=C(N)N=C3CCCCC3=C2N1CCCCN(C(N)=O)C1=CC=CC=C1 VLDXADUEBXLIKK-UHFFFAOYSA-N 0.000 claims 1
- FGDCEHUKYFFYSG-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]butyl]-3-phenylthiourea Chemical compound COCCC1=NC2=C(N)N=C3CCCCC3=C2N1CCCCNC(=S)NC1=CC=CC=C1 FGDCEHUKYFFYSG-UHFFFAOYSA-N 0.000 claims 1
- XVGXGNCPJYXEFD-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]butyl]-3-tert-butylthiourea Chemical compound C1CCCC2=C(N(C(CCOC)=N3)CCCCNC(=S)NC(C)(C)C)C3=C(N)N=C21 XVGXGNCPJYXEFD-UHFFFAOYSA-N 0.000 claims 1
- SCWHOPDQWUYJNI-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-(3-fluorophenyl)urea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NC1=CC=CC(F)=C1 SCWHOPDQWUYJNI-UHFFFAOYSA-N 0.000 claims 1
- FMLKLQPJEWBNJU-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-(3-methylphenyl)urea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NC1=CC=CC(C)=C1 FMLKLQPJEWBNJU-UHFFFAOYSA-N 0.000 claims 1
- NWYYVKKGSXWJPM-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-(4-methylphenyl)sulfonylurea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 NWYYVKKGSXWJPM-UHFFFAOYSA-N 0.000 claims 1
- JMVRMPNRQGKIDG-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-(benzenesulfonyl)urea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 JMVRMPNRQGKIDG-UHFFFAOYSA-N 0.000 claims 1
- NFHIDOZMKRSPNR-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-[4-(dimethylamino)naphthalen-1-yl]thiourea Chemical compound C1=CC=C2C(NC(=S)NCCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCOC)=CC=C(N(C)C)C2=C1 NFHIDOZMKRSPNR-UHFFFAOYSA-N 0.000 claims 1
- MHCWPXSFTKWKAB-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-cyclohexylurea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NC1CCCCC1 MHCWPXSFTKWKAB-UHFFFAOYSA-N 0.000 claims 1
- MNYAFLXNTWMTJK-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-phenylthiourea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=S)NC1=CC=CC=C1 MNYAFLXNTWMTJK-UHFFFAOYSA-N 0.000 claims 1
- WCECXWCZICKLSW-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-phenylurea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)NC1=CC=CC=C1 WCECXWCZICKLSW-UHFFFAOYSA-N 0.000 claims 1
- FAVHQMCYQHQJSJ-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-propylthiourea Chemical compound C1=CC=CC2=C3N(CCCCNC(=S)NCCC)C(CCOC)=NC3=C(N)N=C21 FAVHQMCYQHQJSJ-UHFFFAOYSA-N 0.000 claims 1
- LUWQUDYZESLXFJ-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-propylurea Chemical compound C1=CC=CC2=C3N(CCCCNC(=O)NCCC)C(CCOC)=NC3=C(N)N=C21 LUWQUDYZESLXFJ-UHFFFAOYSA-N 0.000 claims 1
- NPXMDLDRTNPBGV-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-pyridin-3-ylthiourea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=S)NC1=CC=CN=C1 NPXMDLDRTNPBGV-UHFFFAOYSA-N 0.000 claims 1
- DORQDPPEOIHDNH-UHFFFAOYSA-N 1-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-3-tert-butylthiourea Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCNC(=S)NC(C)(C)C)C3=C(N)N=C21 DORQDPPEOIHDNH-UHFFFAOYSA-N 0.000 claims 1
- OOAKVMRLGCVMBV-UHFFFAOYSA-N 1-[4-[4-amino-2-[(4-methoxyphenyl)methyl]imidazo[4,5-c]quinolin-1-yl]butyl]-3-phenylurea Chemical compound C1=CC(OC)=CC=C1CC1=NC2=C(N)N=C(C=CC=C3)C3=C2N1CCCCNC(=O)NC1=CC=CC=C1 OOAKVMRLGCVMBV-UHFFFAOYSA-N 0.000 claims 1
- WTGGOZCMQCQGBB-UHFFFAOYSA-N 1-[4-[4-amino-2-[(4-methoxyphenyl)methyl]imidazo[4,5-c]quinolin-1-yl]butyl]-3-propylurea Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CCCCNC(=O)NCCC)C=1CC1=CC=C(OC)C=C1 WTGGOZCMQCQGBB-UHFFFAOYSA-N 0.000 claims 1
- JLEFQGODJSNJQR-UHFFFAOYSA-N 1-[4-[4-amino-2-[(4-methoxyphenyl)methyl]imidazo[4,5-c]quinolin-1-yl]butyl]-3-pyridin-3-ylurea Chemical compound C1=CC(OC)=CC=C1CC1=NC2=C(N)N=C(C=CC=C3)C3=C2N1CCCCNC(=O)NC1=CC=CN=C1 JLEFQGODJSNJQR-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- CISMPAKZXSMGHX-UHFFFAOYSA-N 3-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-1-methyl-1-phenylurea Chemical compound C1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)N(C)C1=CC=CC=C1 CISMPAKZXSMGHX-UHFFFAOYSA-N 0.000 claims 1
- GOCMKRVOVGTUMM-UHFFFAOYSA-N n-[4-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]butyl]morpholine-4-carboxamide Chemical compound COCCC1=NC2=C(N)N=C3CCCCC3=C2N1CCCCNC(=O)N1CCOCC1 GOCMKRVOVGTUMM-UHFFFAOYSA-N 0.000 claims 1
- DBDMYVZPCMVHFE-UHFFFAOYSA-N n-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]morpholine-4-carboxamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)N1CCOCC1 DBDMYVZPCMVHFE-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 23
- 238000011282 treatment Methods 0.000 abstract description 15
- 230000028993 immune response Effects 0.000 abstract description 9
- 230000003612 virological effect Effects 0.000 abstract description 9
- GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 abstract description 5
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003607 modifier Substances 0.000 abstract description 3
- 150000007945 N-acyl ureas Chemical class 0.000 abstract description 2
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 abstract description 2
- 229940124669 imidazoquinoline Drugs 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13836599P | 1999-06-10 | 1999-06-10 | |
| US09/589,236 US6541485B1 (en) | 1999-06-10 | 2000-06-07 | Urea substituted imidazoquinolines |
| PCT/US2000/015656 WO2000076518A1 (en) | 1999-06-10 | 2000-06-08 | Urea substituted imidazoquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20010889A2 true HRP20010889A2 (en) | 2003-08-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20010889A HRP20010889A2 (en) | 1999-06-10 | 2001-11-29 | Urea substituted imidazoquinolines |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6541485B1 (de) |
| EP (1) | EP1198232B1 (de) |
| JP (1) | JP2003501473A (de) |
| KR (1) | KR20020008223A (de) |
| CN (1) | CN1181070C (de) |
| AT (1) | ATE337007T1 (de) |
| AU (1) | AU766565B2 (de) |
| BR (1) | BR0014214A (de) |
| CA (1) | CA2376296A1 (de) |
| DE (1) | DE60030293T2 (de) |
| DK (1) | DK1198232T3 (de) |
| EE (1) | EE05065B1 (de) |
| ES (1) | ES2270839T3 (de) |
| HK (1) | HK1047224A1 (de) |
| HR (1) | HRP20010889A2 (de) |
| HU (1) | HUP0201664A2 (de) |
| IL (1) | IL146572A0 (de) |
| MX (1) | MXPA01012598A (de) |
| NO (1) | NO320853B1 (de) |
| NZ (1) | NZ515968A (de) |
| PL (1) | PL352257A1 (de) |
| PT (1) | PT1198232E (de) |
| RU (1) | RU2265020C2 (de) |
| SK (1) | SK17972001A3 (de) |
| TR (1) | TR200103576T2 (de) |
| WO (1) | WO2000076518A1 (de) |
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