SK7152003A3 - Heterocyclic ether substituted imidazoquinolines - Google Patents

Heterocyclic ether substituted imidazoquinolines Download PDF

Info

Publication number: SK7152003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; imidazo; heteroaryl; quinolin; amine
Prior art date: 2000-12-08

Application number

SK715-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Leslie J Charles

Joseph F Dellaria

George W Griesgraber

Philip D Heppner

Karl J Manske

John W Mickelson

Michael J Rice

Original Assignee

3M Innovative Properties Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-12-08

Filing date

2001-12-06

Publication date

2003-09-11

2001-12-06 Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co

2003-09-11 Publication of SK7152003A3 publication Critical patent/SK7152003A3/sk

Links

RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 83
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 abstract description 165
125000003118 aryl group Chemical group 0.000 claims abstract description 41
125000003342 alkenyl group Chemical group 0.000 claims abstract description 39
102000004127 Cytokines Human genes 0.000 claims abstract description 33
108090000695 Cytokines Proteins 0.000 claims abstract description 33
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
201000010099 disease Diseases 0.000 claims abstract description 27
230000015572 biosynthetic process Effects 0.000 claims abstract description 18
230000003612 virological effect Effects 0.000 claims abstract description 13
230000001613 neoplastic effect Effects 0.000 claims abstract description 11
-1 2-thiazolyl Chemical group 0.000 claims description 100
229910052739 hydrogen Inorganic materials 0.000 claims description 92
125000000217 alkyl group Chemical group 0.000 claims description 89
229910052799 carbon Inorganic materials 0.000 claims description 87
238000000034 method Methods 0.000 claims description 70
150000003839 salts Chemical class 0.000 claims description 69
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 57
241001465754 Metazoa Species 0.000 claims description 43
229910052736 halogen Inorganic materials 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 35
125000001072 heteroaryl group Chemical group 0.000 claims description 29
FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 28
150000002367 halogens Chemical class 0.000 claims description 21
125000000623 heterocyclic group Chemical group 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 16
102000006992 Interferon-alpha Human genes 0.000 claims description 10
108010047761 Interferon-alpha Proteins 0.000 claims description 10
230000001939 inductive effect Effects 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical group CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
OFNOWGYRUZBPSQ-UHFFFAOYSA-N 1-[2-(3-pyrimidin-2-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCCCC1=NC=CC=N1 OFNOWGYRUZBPSQ-UHFFFAOYSA-N 0.000 claims description 3
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 description 3
KEAQWVLBTNUKFC-UHFFFAOYSA-N 1-[2-[3-(1,3-thiazol-2-yl)prop-2-ynoxy]ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC#CC1=NC=CS1 KEAQWVLBTNUKFC-UHFFFAOYSA-N 0.000 claims description 3
PDNKPIOOOXBYJU-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-[2-(3-pyridin-3-ylpropoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCOCCCC1=CC=CN=C1 PDNKPIOOOXBYJU-UHFFFAOYSA-N 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
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 description 2
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 description 2
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 description 2
PSJRWOALAMLXHG-UHFFFAOYSA-N 1-[2-(3-pyridin-4-ylprop-2-ynoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC#CC1=CC=NC=C1 PSJRWOALAMLXHG-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 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
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
PEKHKJNRALDRTL-UHFFFAOYSA-N 1-[1-[(5-chloro-1-benzothiophen-3-yl)methoxy]-3-methylbutan-2-yl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC2=C(N)N=C3C=CC=CC3=C2N1C(C(C)C)COCC1=CSC2=CC=C(Cl)C=C12 PEKHKJNRALDRTL-UHFFFAOYSA-N 0.000 claims 1
VPCGRCPMOPURLJ-UHFFFAOYSA-N 1-[2-(3-nitropyridin-2-yl)oxypropyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)OC1=NC=CC=C1[N+]([O-])=O VPCGRCPMOPURLJ-UHFFFAOYSA-N 0.000 claims 1
OASXBJBPTCHLEH-UHFFFAOYSA-N 1-[2-(3-pyrimidin-2-ylprop-2-ynoxy)ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCC#CC1=NC=CC=N1 OASXBJBPTCHLEH-UHFFFAOYSA-N 0.000 claims 1
PPBYDAYPQWSJQG-UHFFFAOYSA-N 1-[2-(9h-carbazol-3-yloxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=C2C3=CC(OC(CN4C5=C6C=CC=CC6=NC(N)=C5N=C4)C)=CC=C3NC2=C1 PPBYDAYPQWSJQG-UHFFFAOYSA-N 0.000 claims 1
KQTLTIZVAIZLSN-UHFFFAOYSA-N 1-[2-(oxolan-2-ylmethoxy)propyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)OCC1CCCO1 KQTLTIZVAIZLSN-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
XWPBSYQXQJJSRI-UHFFFAOYSA-N 1-[2-[3-(1,3-thiazol-2-yl)propoxy]ethyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCOCCCC1=NC=CS1 XWPBSYQXQJJSRI-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
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
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 59
230000028993 immune response Effects 0.000 abstract description 12
238000011282 treatment Methods 0.000 abstract description 11
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 6
239000003607 modifier Substances 0.000 abstract description 4
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 1
229940124669 imidazoquinoline Drugs 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 243
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
238000006243 chemical reaction Methods 0.000 description 157
239000007787 solid Substances 0.000 description 101
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
229910052757 nitrogen Inorganic materials 0.000 description 83
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 80
239000000243 solution Substances 0.000 description 72
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
239000011541 reaction mixture Substances 0.000 description 57
238000005481 NMR spectroscopy Methods 0.000 description 56
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
239000002904 solvent Substances 0.000 description 35
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
239000000047 product Substances 0.000 description 31
238000004458 analytical method Methods 0.000 description 30
239000000463 material Substances 0.000 description 28
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
238000001914 filtration Methods 0.000 description 26
239000003921 oil Substances 0.000 description 25
235000019198 oils Nutrition 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
238000003756 stirring Methods 0.000 description 24
239000012299 nitrogen atmosphere Substances 0.000 description 23
238000004809 thin layer chromatography Methods 0.000 description 23
239000003054 catalyst Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000012267 brine Substances 0.000 description 21
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
238000010898 silica gel chromatography Methods 0.000 description 20
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
150000004820 halides Chemical class 0.000 description 19
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
239000002244 precipitate Substances 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
239000010410 layer Substances 0.000 description 15
238000010992 reflux Methods 0.000 description 15
238000010561 standard procedure Methods 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
229910021595 Copper(I) iodide Inorganic materials 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 14
108060008682 Tumor Necrosis Factor Proteins 0.000 description 13
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 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
238000011894 semi-preparative HPLC Methods 0.000 description 12
239000012312 sodium hydride Substances 0.000 description 12
229910000104 sodium hydride Inorganic materials 0.000 description 12
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 description 11
239000012043 crude product Substances 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
239000000543 intermediate Substances 0.000 description 11
239000012071 phase Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
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239000012223 aqueous fraction Substances 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
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RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
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206010028980 Neoplasm Diseases 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
150000004703 alkoxides Chemical class 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical group C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 9
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 9
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
102000003390 tumor necrosis factor Human genes 0.000 description 9
239000003039 volatile agent Substances 0.000 description 9
KDRFSAWHTAWZAC-UHFFFAOYSA-N 1-(2-prop-2-ynoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2CCOCC#C KDRFSAWHTAWZAC-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
230000006698 induction Effects 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 8
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000010189 synthetic method Methods 0.000 description 8
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239000005695 Ammonium acetate Substances 0.000 description 7
235000019257 ammonium acetate Nutrition 0.000 description 7
229940043376 ammonium acetate Drugs 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
108010050904 Interferons Proteins 0.000 description 6
102000014150 Interferons Human genes 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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Classifications

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SK715-2003A 2000-12-08 2001-12-06 Heterocyclic ether substituted imidazoquinolines SK7152003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US25421800P	2000-12-08	2000-12-08
PCT/US2001/046704 WO2002046193A2 (en)	2000-12-08	2001-12-06	Heterocyclic ether substituted imidazoquinolines

Publications (1)

Publication Number	Publication Date
SK7152003A3 true SK7152003A3 (en)	2003-09-11

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ID=22963391

Family Applications (6)

Application Number	Title	Priority Date	Filing Date
SK712-2003A SK7122003A3 (en)	2000-12-08	2001-12-06	Urea substituted imidazoquinoline ethers
SK713-2003A SK287732B6 (en)	2000-12-08	2001-12-06	Amido ether substituted imidazoquinolines, pharmaceutical composition and use thereof
SK715-2003A SK7152003A3 (en)	2000-12-08	2001-12-06	Heterocyclic ether substituted imidazoquinolines
SK710-2003A SK287264B6 (sk)	2000-12-08	2001-12-06	Deriváty imidazochinolínu a tetrahydroimidazochinolínu, farmaceutické kompozície s ich obsahom a ich použitie
SK684-2003A SK6842003A3 (en)	2000-12-08	2001-12-06	Aryl ether substituted imidazoquinolines
SK711-2003A SK7112003A3 (en)	2000-12-08	2001-12-06	Sulfonamido ether substituted imidazoquinolines

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
SK712-2003A SK7122003A3 (en)	2000-12-08	2001-12-06	Urea substituted imidazoquinoline ethers
SK713-2003A SK287732B6 (en)	2000-12-08	2001-12-06	Amido ether substituted imidazoquinolines, pharmaceutical composition and use thereof

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
SK710-2003A SK287264B6 (sk)	2000-12-08	2001-12-06	Deriváty imidazochinolínu a tetrahydroimidazochinolínu, farmaceutické kompozície s ich obsahom a ich použitie
SK684-2003A SK6842003A3 (en)	2000-12-08	2001-12-06	Aryl ether substituted imidazoquinolines
SK711-2003A SK7112003A3 (en)	2000-12-08	2001-12-06	Sulfonamido ether substituted imidazoquinolines

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US (8)	US6670372B2 (de)
EP (6)	EP1341791B1 (de)
JP (7)	JP2004523498A (de)
KR (6)	KR20030070050A (de)
CN (6)	CN1247575C (de)
AR (6)	AR035667A1 (de)
AT (3)	ATE296301T1 (de)
AU (12)	AU3061802A (de)
BR (6)	BR0116047A (de)
CA (6)	CA2431151A1 (de)
CY (2)	CY1105586T1 (de)
CZ (6)	CZ295848B6 (de)
DE (3)	DE60126645T2 (de)
DK (3)	DK1341790T3 (de)
EE (6)	EE200300274A (de)
ES (3)	ES2260323T3 (de)
HR (6)	HRP20030467B1 (de)
HU (6)	HUP0600605A2 (de)
IL (6)	IL155950A0 (de)
MX (6)	MXPA03004973A (de)
NO (6)	NO20032449D0 (de)
NZ (6)	NZ526086A (de)
PL (7)	PL361948A1 (de)
PT (2)	PT1341791E (de)
RU (6)	RU2315049C2 (de)
SI (1)	SI1341790T1 (de)
SK (6)	SK7122003A3 (de)
TW (3)	TW584633B (de)
UA (2)	UA75622C2 (de)
WO (6)	WO2002046192A2 (de)
ZA (6)	ZA200305272B (de)

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2001
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2003
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- 2003-07-08 ZA ZA200305275A patent/ZA200305275B/en unknown
- 2003-07-08 ZA ZA200305274A patent/ZA200305274B/en unknown
- 2003-10-07 US US10/680,989 patent/US7049439B2/en not_active Expired - Fee Related
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- 2003-10-29 US US10/696,476 patent/US20040092545A1/en not_active Abandoned
2005
- 2005-02-28 US US11/069,033 patent/US7132429B2/en not_active Expired - Fee Related
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2007
- 2007-05-09 CY CY20071100621T patent/CY1106569T1/el unknown
2009
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Also Published As

Publication number	Publication date
PL365883A1 (en)	2005-01-10
PL392462A1 (pl)	2010-11-22
US6670372B2 (en)	2003-12-30
HRP20030464A2 (en)	2004-06-30
EE200300272A (et)	2003-10-15
EE200300271A (et)	2003-10-15
CZ20031591A3 (cs)	2003-11-12
CN1487939A (zh)	2004-04-07
EE200300274A (et)	2003-10-15
IL156044A0 (en)	2003-12-23
MXPA03005011A (es)	2003-09-05
HUP0600605A2 (en)	2006-11-28
WO2002046193A2 (en)	2002-06-13
EP1341790A2 (de)	2003-09-10
AR035669A1 (es)	2004-06-23
WO2002046192A2 (en)	2002-06-13
RU2003116059A (ru)	2005-02-10
SK7102003A3 (en)	2003-10-07
CN1479738A (zh)	2004-03-03
EE200300270A (et)	2003-10-15
WO2002046192A3 (en)	2003-02-13
BR0116470A (pt)	2005-08-16
KR20040028690A (ko)	2004-04-03
RU2351598C2 (ru)	2009-04-10
US7132429B2 (en)	2006-11-07
IL155884A0 (en)	2003-12-23
ATE319711T1 (de)	2006-03-15
US20040077678A1 (en)	2004-04-22
BR0116052A (pt)	2006-02-21
AR035668A1 (es)	2004-06-23
NO20032473L (no)	2003-05-30
HUP0600600A2 (en)	2006-11-28
JP2004515501A (ja)	2004-05-27
HUP0600338A2 (en)	2006-08-28
NO20032451D0 (no)	2003-05-28
BR0116464A (pt)	2006-02-21
RU2003116649A (ru)	2005-02-10
JP2004532810A (ja)	2004-10-28
JP2004515500A (ja)	2004-05-27
ZA200305270B (en)	2004-08-26
PT1341791E (pt)	2005-09-30
CZ20031592A3 (cs)	2004-01-14
EP1341790B1 (de)	2007-02-14
PT1341790E (pt)	2007-05-31
ZA200305271B (en)	2004-10-08
US20030212091A1 (en)	2003-11-13
KR20030070049A (ko)	2003-08-27
US20030158192A1 (en)	2003-08-21
WO2002046190A2 (en)	2002-06-13
AU2002239516B2 (en)	2006-11-09
NO20032449L (no)	2003-05-28
AU2002239517B2 (en)	2006-11-02
HUP0400710A2 (hu)	2004-06-28
TWI222972B (en)	2004-11-01
US6953804B2 (en)	2005-10-11
DK1341791T3 (da)	2005-09-19
DK1343784T3 (da)	2006-07-10
WO2002046191A2 (en)	2002-06-13
NZ526089A (en)	2004-11-26
ES2281456T3 (es)	2007-10-01
NO20032473D0 (no)	2003-05-30
ZA200305272B (en)	2005-01-26
UA74852C2 (en)	2006-02-15
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Publication	Publication Date	Title
SK7152003A3 (en)	2003-09-11	Heterocyclic ether substituted imidazoquinolines
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JP2007502293A (ja)	2007-02-08	ヒドロキシルアミン置換イミダゾ含有化合物
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