ZA200305270B - Heterocyclic ether substituted imidazoquinolines. - Google Patents
Heterocyclic ether substituted imidazoquinolines. Download PDFInfo
- Publication number
- ZA200305270B ZA200305270B ZA200305270A ZA200305270A ZA200305270B ZA 200305270 B ZA200305270 B ZA 200305270B ZA 200305270 A ZA200305270 A ZA 200305270A ZA 200305270 A ZA200305270 A ZA 200305270A ZA 200305270 B ZA200305270 B ZA 200305270B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- heteroaryl
- compound
- alkenyl
- imidazo
- Prior art date
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 23
- 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 6
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 58
- 241001465754 Metazoa Species 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- -1 2-thiazolyl Chemical group 0.000 claims description 18
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 claims description 17
- 102000004127 Cytokines Human genes 0.000 claims description 16
- 108090000695 Cytokines Proteins 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 230000001939 inductive effect Effects 0.000 claims description 8
- 230000001613 neoplastic effect Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000003612 virological effect Effects 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- YWQATZQXFPGFMH-UHFFFAOYSA-N 1-(1-pyridin-2-yloxybutan-2-yl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC2=C(N)N=C3C=CC=CC3=C2N1C(CC)COC1=CC=CC=N1 YWQATZQXFPGFMH-UHFFFAOYSA-N 0.000 claims 1
- AMFDYQBMFBQOOS-UHFFFAOYSA-N 1-(3-methyl-1-pyridin-2-yloxybutan-2-yl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC2=C(N)N=C3C=CC=CC3=C2N1C(C(C)C)COC1=CC=CC=N1 AMFDYQBMFBQOOS-UHFFFAOYSA-N 0.000 claims 1
- NHLFFJAEEKRXTG-UHFFFAOYSA-N 1-[2-(1-benzofuran-2-ylmethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=C2OC(COCCN3C=4C5=CC=CC=C5N=C(C=4N=C3)N)=CC2=C1 NHLFFJAEEKRXTG-UHFFFAOYSA-N 0.000 claims 1
- LJBCZFPGPQDFBK-UHFFFAOYSA-N 1-[2-(3-pyridin-2-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCCCC1=CC=CC=N1 LJBCZFPGPQDFBK-UHFFFAOYSA-N 0.000 claims 1
- KCVMNBOTCYCHDQ-UHFFFAOYSA-N 1-[2-(3-pyridin-4-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCCCC1=CC=NC=C1 KCVMNBOTCYCHDQ-UHFFFAOYSA-N 0.000 claims 1
- OJHPYVFQANZJPK-UHFFFAOYSA-N 1-[2-(3-pyrimidin-5-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCCCC1=CN=CN=C1 OJHPYVFQANZJPK-UHFFFAOYSA-N 0.000 claims 1
- BJYQPYYJASXSNS-UHFFFAOYSA-N 1-[2-(3-thiophen-2-ylprop-2-ynoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC#CC1=CC=CS1 BJYQPYYJASXSNS-UHFFFAOYSA-N 0.000 claims 1
- JWCCGPJCZRUYLU-UHFFFAOYSA-N 1-[2-(3-thiophen-2-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCCCC1=CC=CS1 JWCCGPJCZRUYLU-UHFFFAOYSA-N 0.000 claims 1
- ORWATXHBSJOMRW-UHFFFAOYSA-N 1-[2-(pyridin-3-ylmethoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC1=CC=CN=C1 ORWATXHBSJOMRW-UHFFFAOYSA-N 0.000 claims 1
- XYYHSYYIABWPSZ-UHFFFAOYSA-N 1-[2-[(1-benzyltriazol-4-yl)methoxy]ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC(N=N1)=CN1CC1=CC=CC=C1 XYYHSYYIABWPSZ-UHFFFAOYSA-N 0.000 claims 1
- NIFLEXCTXLZLJM-UHFFFAOYSA-N 1-[2-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CC1=NOC(C)=C1COCCN1C2=C3C=CC=CC3=NC(N)=C2N=C1 NIFLEXCTXLZLJM-UHFFFAOYSA-N 0.000 claims 1
- MTUOLEBHBRNJDR-UHFFFAOYSA-N 1-[2-[3-(1h-pyrazol-4-yl)propoxy]ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCCCC=1C=NNC=1 MTUOLEBHBRNJDR-UHFFFAOYSA-N 0.000 claims 1
- FSSQKWZGRNLBOV-UHFFFAOYSA-N 1-[2-[[1-(phenylsulfanylmethyl)triazol-4-yl]methoxy]ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC(N=N1)=CN1CSC1=CC=CC=C1 FSSQKWZGRNLBOV-UHFFFAOYSA-N 0.000 claims 1
- JCXUOMGWTBFBGP-UHFFFAOYSA-N 1-[2-[[3-(phenylsulfanylmethyl)triazol-4-yl]methoxy]ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC1=CN=NN1CSC1=CC=CC=C1 JCXUOMGWTBFBGP-UHFFFAOYSA-N 0.000 claims 1
- IRERCXFJSVRCLT-UHFFFAOYSA-N 1-[3-methyl-1-(3-nitropyridin-2-yl)oxybutan-2-yl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC2=C(N)N=C3C=CC=CC3=C2N1C(C(C)C)COC1=NC=CC=C1[N+]([O-])=O IRERCXFJSVRCLT-UHFFFAOYSA-N 0.000 claims 1
- MLJGHBGWWYRYJD-UHFFFAOYSA-N 2-butyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCC1=CC=CN=C1 MLJGHBGWWYRYJD-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- DBESIXFNTXKNRT-UHFFFAOYSA-N 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound CC1=NC2=C(N)N=C3CCCCC3=C2N1CCOCCCC1=CC=CN=C1 DBESIXFNTXKNRT-UHFFFAOYSA-N 0.000 claims 1
- YFGKUOLOYSLLSF-UHFFFAOYSA-N 2-methyl-1-[2-(3-pyridin-3-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCC1=CC=CN=C1 YFGKUOLOYSLLSF-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 150000004820 halides Chemical class 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 9
- 150000004703 alkoxides Chemical class 0.000 description 7
- 230000028993 immune response Effects 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 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 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- SHKUAAUCZDOPDI-UHFFFAOYSA-N 4-chloro-3h-imidazo[4,5-c]quinoline Chemical compound ClC1=NC2=CC=CC=C2C2=C1N=CN2 SHKUAAUCZDOPDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000012455 biphasic mixture Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- YJKZDGOMTKOYQK-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CCC1CCNCC1 YJKZDGOMTKOYQK-UHFFFAOYSA-N 0.000 description 1
- QUJSHZMLFMCARS-UHFFFAOYSA-N 1-hydroxyimidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(O)C=NC3=CN=C21 QUJSHZMLFMCARS-UHFFFAOYSA-N 0.000 description 1
- VCNWVTNERDDKEA-UHFFFAOYSA-N 1-imidazo[4,5-c]quinolin-1-yloxyimidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1ON1C2=C3C=CC=CC3=NC=C2N=C1 VCNWVTNERDDKEA-UHFFFAOYSA-N 0.000 description 1
- UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical class NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 1
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 1
- HLFGXPKPTDQYBN-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1N=C2C=CC=CC2=C2C1NCN2 HLFGXPKPTDQYBN-UHFFFAOYSA-N 0.000 description 1
- SSDYFZUPEUFHOR-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-c]quinoline Chemical class C1N=C2C=CC=CC2=C2C1NCN2 SSDYFZUPEUFHOR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- KGEGVJJFFQXJTG-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,8]naphthyridin-4-amine Chemical class NC1=NC2=NC=CC=C2C2=C1N=CN2 KGEGVJJFFQXJTG-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- JTKVJIJQXNQAAI-UHFFFAOYSA-N 4-phenoxy-1-(4-phenoxyimidazo[4,5-c]quinolin-1-yl)oxyimidazo[4,5-c]quinoline Chemical compound N=1C2=CC=CC=C2C=2N(ON3C4=C5C=CC=CC5=NC(OC=5C=CC=CC=5)=C4N=C3)C=NC=2C=1OC1=CC=CC=C1 JTKVJIJQXNQAAI-UHFFFAOYSA-N 0.000 description 1
- OYTRPNUFEBDWKQ-UHFFFAOYSA-N 4-phenoxy-3h-imidazo[4,5-c]quinoline Chemical compound N=1C2=CC=CC=C2C=2NC=NC=2C=1OC1=CC=CC=C1 OYTRPNUFEBDWKQ-UHFFFAOYSA-N 0.000 description 1
- YHQPYMQQMBVULM-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C1N=C(N)C1=C2NC=N1 YHQPYMQQMBVULM-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- FHRRJZZGSJXPRQ-UHFFFAOYSA-N benzyl phenylmethoxycarbonyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OC(=O)OCC1=CC=CC=C1 FHRRJZZGSJXPRQ-UHFFFAOYSA-N 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- WUUCVVFSWNXYRD-UHFFFAOYSA-N chembl19191 Chemical compound C1=CC=C2C3=NC=NC3=C(N)NC2=C1 WUUCVVFSWNXYRD-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- WZDWLAXDMLUYBD-UHFFFAOYSA-N n-(3h-imidazo[4,5-c]quinolin-4-yl)acetamide Chemical compound CC(=O)NC1=NC2=CC=CC=C2C2=C1NC=N2 WZDWLAXDMLUYBD-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
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ZA2003/05272A ZA200305272B (en) | 2000-12-08 | 2003-07-08 | Urea substituted imidazoquinoline ethers |
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ZA200305273A ZA200305273B (en) | 2000-12-08 | 2003-07-08 | Sulfonamido ether substituted imidazoquinolines. |
ZA200305275A ZA200305275B (en) | 2000-12-08 | 2003-07-08 | Aryl ether substituted imidazoquinolines. |
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RU (6) | RU2003116123A (sk) |
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UA (2) | UA74852C2 (sk) |
WO (6) | WO2002046192A2 (sk) |
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Families Citing this family (206)
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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 |
US6541485B1 (en) | 1999-06-10 | 2003-04-01 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
US6573273B1 (en) | 1999-06-10 | 2003-06-03 | 3M Innovative Properties Company | Urea substituted imidazoquinolines |
US6756382B2 (en) | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
US6916925B1 (en) | 1999-11-05 | 2005-07-12 | 3M Innovative Properties Co. | Dye labeled imidazoquinoline compounds |
JP3436512B2 (ja) * | 1999-12-28 | 2003-08-11 | 株式会社デンソー | アクセル装置 |
US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
US6660735B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Urea substituted imidazoquinoline ethers |
US6545016B1 (en) | 2000-12-08 | 2003-04-08 | 3M Innovative Properties Company | Amide substituted imidazopyridines |
US6664264B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
US6660747B2 (en) * | 2000-12-08 | 2003-12-09 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
UA74852C2 (en) | 2000-12-08 | 2006-02-15 | 3M Innovative Properties Co | Urea-substituted imidazoquinoline ethers |
US6664265B2 (en) | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Amido ether substituted imidazoquinolines |
US6667312B2 (en) | 2000-12-08 | 2003-12-23 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
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US6525064B1 (en) | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
US7226928B2 (en) * | 2001-06-15 | 2007-06-05 | 3M Innovative Properties Company | Methods for the treatment of periodontal disease |
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AU2003281340B2 (en) | 2002-07-02 | 2009-04-09 | Southern Research Institute | Inhibitors of FtsZ and uses thereof |
CN1671412B (zh) | 2002-08-15 | 2010-05-26 | 3M创新有限公司 | 免疫刺激组合物及刺激免疫反应的方法 |
WO2004028539A2 (en) | 2002-09-26 | 2004-04-08 | 3M Innovative Properties Company | 1h-imidazo dimers |
NZ540826A (en) * | 2002-12-20 | 2008-07-31 | 3M Innovative Properties Co | Aryl / hetaryl substituted imidazoquinolines |
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2004
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2005
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2007
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