NO322223B1 - Amidsubstituerte imidazokinoliner - Google Patents
Amidsubstituerte imidazokinoliner Download PDFInfo
- Publication number
- NO322223B1 NO322223B1 NO20015503A NO20015503A NO322223B1 NO 322223 B1 NO322223 B1 NO 322223B1 NO 20015503 A NO20015503 A NO 20015503A NO 20015503 A NO20015503 A NO 20015503A NO 322223 B1 NO322223 B1 NO 322223B1
- Authority
- NO
- Norway
- Prior art keywords
- imidazo
- amino
- quinolin
- butyl
- methoxyethyl
- Prior art date
Links
- 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 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 171
- 150000001875 compounds Chemical class 0.000 claims description 114
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 68
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 50
- -1 C1-ioalkyl Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 102000004127 Cytokines Human genes 0.000 claims description 26
- 108090000695 Cytokines Proteins 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 13
- 230000003612 virological effect Effects 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 11
- 235000005152 nicotinamide Nutrition 0.000 claims description 10
- 239000011570 nicotinamide Substances 0.000 claims description 10
- 229960003966 nicotinamide Drugs 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 230000001613 neoplastic effect Effects 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 3
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 2
- XZOWIJDBQIHMFC-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O.CCCC(N)=O XZOWIJDBQIHMFC-UHFFFAOYSA-N 0.000 claims 2
- OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 1
- 229960003497 diloxanide furoate Drugs 0.000 claims 1
- KKSZSACCVDIWIE-UHFFFAOYSA-N isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(=O)N)=CC2=C1 KKSZSACCVDIWIE-UHFFFAOYSA-N 0.000 claims 1
- YTWBMRXEDRJFTK-UHFFFAOYSA-N n-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]benzamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNC(=O)C1=CC=CC=C1 YTWBMRXEDRJFTK-UHFFFAOYSA-N 0.000 claims 1
- OABOYSITBOLTJD-UHFFFAOYSA-N n-[3-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)propyl]cyclohexanecarboxamide Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNC(=O)C1CCCCC1 OABOYSITBOLTJD-UHFFFAOYSA-N 0.000 claims 1
- URPPPXYGBMRVST-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropyl]benzamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)CNC(=O)C1=CC=CC=C1 URPPPXYGBMRVST-UHFFFAOYSA-N 0.000 claims 1
- AYIJWYQSZASHHL-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(=O)NCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCOC)=CC2=C1 AYIJWYQSZASHHL-UHFFFAOYSA-N 0.000 claims 1
- IHZTWOQHKGUNPL-UHFFFAOYSA-N n-[3-[4-amino-2-(3-phenoxypropyl)imidazo[4,5-c]quinolin-1-yl]propyl]-4-bromobenzamide Chemical compound C=1C=CC=CC=1OCCCC1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCNC(=O)C1=CC=C(Br)C=C1 IHZTWOQHKGUNPL-UHFFFAOYSA-N 0.000 claims 1
- YYWDGTFNDCEKAS-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]-2-methylpropanamide Chemical compound C1=CC=CC2=C3N(CCCCNC(=O)C(C)C)C(C)=NC3=C(N)N=C21 YYWDGTFNDCEKAS-UHFFFAOYSA-N 0.000 claims 1
- KXCIAFBBDRSVED-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]cyclohexanecarboxamide Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)C1CCCCC1 KXCIAFBBDRSVED-UHFFFAOYSA-N 0.000 claims 1
- JXUYXFFPUCFRSC-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-2-chloropyridine-3-carboxamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=CN=C1Cl JXUYXFFPUCFRSC-UHFFFAOYSA-N 0.000 claims 1
- KKFQMSFWNIFODM-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-2-phenylacetamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)CC1=CC=CC=C1 KKFQMSFWNIFODM-UHFFFAOYSA-N 0.000 claims 1
- QHVAVOCEIMSOND-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-3-cyanobenzamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=CC(C#N)=C1 QHVAVOCEIMSOND-UHFFFAOYSA-N 0.000 claims 1
- YMPAHNUADICOHE-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-4-(morpholin-4-ylmethyl)benzamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C(C=C1)=CC=C1CN1CCOCC1 YMPAHNUADICOHE-UHFFFAOYSA-N 0.000 claims 1
- LZFBIQUFNGHARE-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-4-(trifluoromethyl)benzamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=C(C(F)(F)F)C=C1 LZFBIQUFNGHARE-UHFFFAOYSA-N 0.000 claims 1
- CKGIXSMWSJNGQU-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-5-nitrofuran-2-carboxamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=C([N+]([O-])=O)O1 CKGIXSMWSJNGQU-UHFFFAOYSA-N 0.000 claims 1
- INKBMAFTIQZMHQ-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=C(OCC(F)(F)F)N=C1 INKBMAFTIQZMHQ-UHFFFAOYSA-N 0.000 claims 1
- BJZIOAYOIIJXPJ-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-6-chloropyridine-3-carboxamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=C(Cl)N=C1 BJZIOAYOIIJXPJ-UHFFFAOYSA-N 0.000 claims 1
- WPYNHVGHFLQECU-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]-6-cyanopyridine-3-carboxamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=C(C#N)N=C1 WPYNHVGHFLQECU-UHFFFAOYSA-N 0.000 claims 1
- KTEKNBTXLMTZSE-UHFFFAOYSA-N n-[4-(4-aminoimidazo[4,5-c]quinolin-1-yl)butyl]furan-2-carboxamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCNC(=O)C1=CC=CO1 KTEKNBTXLMTZSE-UHFFFAOYSA-N 0.000 claims 1
- BHYXSCSFHMCKLU-UHFFFAOYSA-N n-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]-6-pyrrol-1-ylpyridine-3-carboxamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNC(=O)C(C=N1)=CC=C1N1C=CC=C1 BHYXSCSFHMCKLU-UHFFFAOYSA-N 0.000 claims 1
- RLHXDLCPDBJQJA-UHFFFAOYSA-N n-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(=O)NCCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCOC)=CC2=C1 RLHXDLCPDBJQJA-UHFFFAOYSA-N 0.000 claims 1
- PTOGBYCOOSGDMP-UHFFFAOYSA-N n-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)NCCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCOC)=CC=C21 PTOGBYCOOSGDMP-UHFFFAOYSA-N 0.000 claims 1
- QULPNWVRKDTPRY-UHFFFAOYSA-N n-[4-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]butyl]quinoxaline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)NCCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCOC)=CN=C21 QULPNWVRKDTPRY-UHFFFAOYSA-N 0.000 claims 1
- JYXQYBFBBANTTN-UHFFFAOYSA-N n-[4-[4-amino-2-[(4-methoxyphenyl)methyl]imidazo[4,5-c]quinolin-1-yl]butyl]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CC1=NC2=C(N)N=C(C=CC=C3)C3=C2N1CCCCNC(=O)C1=CC=CC=N1 JYXQYBFBBANTTN-UHFFFAOYSA-N 0.000 claims 1
- UFWPDWHFBZURKW-UHFFFAOYSA-N n-[4-[4-amino-2-[(4-methoxyphenyl)methyl]imidazo[4,5-c]quinolin-1-yl]butyl]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CC1=NC2=C(N)N=C(C=CC=C3)C3=C2N1CCCCNC(=O)C1=CC=CN=C1 UFWPDWHFBZURKW-UHFFFAOYSA-N 0.000 claims 1
- RORPEWLHZVPJEP-UHFFFAOYSA-N n-[4-[4-amino-2-[(4-methoxyphenyl)methyl]imidazo[4,5-c]quinolin-1-yl]butyl]quinoline-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CC1=NC2=C(N)N=C(C=CC=C3)C3=C2N1CCCCNC(=O)C1=CC=C(C=CC=C2)C2=N1 RORPEWLHZVPJEP-UHFFFAOYSA-N 0.000 claims 1
- WPKMNZSKGOHTEB-UHFFFAOYSA-N n-[5-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)pentyl]benzamide Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCCNC(=O)C1=CC=CC=C1 WPKMNZSKGOHTEB-UHFFFAOYSA-N 0.000 claims 1
- TYHPNYNPFIHIBB-UHFFFAOYSA-N n-[8-(4-aminoimidazo[4,5-c]quinolin-1-yl)octyl]benzamide Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCCCCCNC(=O)C1=CC=CC=C1 TYHPNYNPFIHIBB-UHFFFAOYSA-N 0.000 claims 1
- NUECKCRKNOMMDO-UHFFFAOYSA-N n-[8-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]octyl]benzamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCCCCCNC(=O)C1=CC=CC=C1 NUECKCRKNOMMDO-UHFFFAOYSA-N 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 104
- 238000006243 chemical reaction Methods 0.000 description 70
- 239000007787 solid Substances 0.000 description 69
- 239000000243 solution Substances 0.000 description 62
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 53
- 239000011541 reaction mixture Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000843 powder Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 239000000908 ammonium hydroxide Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
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- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
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- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- HNUSZIQSLZBZTO-UHFFFAOYSA-N quinoline-3-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CN=C21 HNUSZIQSLZBZTO-UHFFFAOYSA-N 0.000 description 1
- OTENSAQNLUSKHN-UHFFFAOYSA-N quinoline-4-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=NC2=C1 OTENSAQNLUSKHN-UHFFFAOYSA-N 0.000 description 1
- VXGYRCVTBHVXMZ-UHFFFAOYSA-N quinoline-6-carboxylic acid Chemical compound N1=CC=CC2=CC(C(=O)O)=CC=C21 VXGYRCVTBHVXMZ-UHFFFAOYSA-N 0.000 description 1
- JLZCPFISUMNHDT-UHFFFAOYSA-N quinoline-8-carbonyl chloride Chemical compound C1=CN=C2C(C(=O)Cl)=CC=CC2=C1 JLZCPFISUMNHDT-UHFFFAOYSA-N 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
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- 239000012898 sample dilution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
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- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
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- Neurology (AREA)
- Gastroenterology & Hepatology (AREA)
- Diabetes (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US13836599P | 1999-06-10 | 1999-06-10 | |
US09/589,580 US6451810B1 (en) | 1999-06-10 | 2000-06-07 | Amide substituted imidazoquinolines |
PCT/US2000/015702 WO2000076505A1 (en) | 1999-06-10 | 2000-06-08 | Amide substituted imidazoquinolines |
Publications (3)
Publication Number | Publication Date |
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NO20015503D0 NO20015503D0 (no) | 2001-11-09 |
NO20015503L NO20015503L (no) | 2002-02-08 |
NO322223B1 true NO322223B1 (no) | 2006-08-28 |
Family
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Application Number | Title | Priority Date | Filing Date |
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NO20015503A NO322223B1 (no) | 1999-06-10 | 2001-11-09 | Amidsubstituerte imidazokinoliner |
Country Status (28)
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US (1) | US6451810B1 (xx) |
EP (1) | EP1187613B9 (xx) |
JP (1) | JP2003501466A (xx) |
KR (1) | KR20020008222A (xx) |
CN (1) | CN1353609B (xx) |
AT (1) | ATE335479T1 (xx) |
AU (1) | AU773113B2 (xx) |
BR (1) | BR0011448A (xx) |
CA (1) | CA2376304C (xx) |
CY (1) | CY1108537T1 (xx) |
CZ (1) | CZ20014364A3 (xx) |
DE (1) | DE60029956T2 (xx) |
DK (1) | DK1187613T3 (xx) |
EE (1) | EE05089B1 (xx) |
ES (1) | ES2269164T3 (xx) |
HK (1) | HK1044488B (xx) |
HR (1) | HRP20010888A2 (xx) |
HU (1) | HUP0202254A3 (xx) |
IL (1) | IL146468A0 (xx) |
MX (1) | MXPA01012508A (xx) |
NO (1) | NO322223B1 (xx) |
NZ (1) | NZ515639A (xx) |
PL (1) | PL364249A1 (xx) |
PT (1) | PT1187613E (xx) |
RU (1) | RU2295343C2 (xx) |
SK (1) | SK17932001A3 (xx) |
TR (1) | TR200103574T2 (xx) |
WO (1) | WO2000076505A1 (xx) |
Families Citing this family (196)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
UA67760C2 (uk) | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
US6518280B2 (en) | 1998-12-11 | 2003-02-11 | 3M Innovative Properties Company | Imidazonaphthyridines |
US20020058674A1 (en) | 1999-01-08 | 2002-05-16 | Hedenstrom John C. | Systems and methods for treating a mucosal surface |
US6558951B1 (en) * | 1999-02-11 | 2003-05-06 | 3M Innovative Properties Company | Maturation of dendritic cells with immune response modifying compounds |
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