SK6842003A3 - Aryl ether substituted imidazoquinolines - Google Patents

Aryl ether substituted imidazoquinolines Download PDF

Info

Publication number: SK6842003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; aryl; imidazo; alkenyl; compound
Prior art date: 2000-12-08

Application number

SK684-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Leslie J Charles

Joseph F Dellaria

Philip D Heppner

Bryon A Merrill

John W Mickelson

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

2003-12-02

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

2003-12-02 Publication of SK6842003A3 publication Critical patent/SK6842003A3/sk

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 5
125000005013 aryl ether group Chemical group 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 170
125000003118 aryl group Chemical group 0.000 claims abstract description 75
125000003342 alkenyl group Chemical group 0.000 claims abstract description 48
102000004127 Cytokines Human genes 0.000 claims abstract description 37
108090000695 Cytokines Proteins 0.000 claims abstract description 37
230000015572 biosynthetic process Effects 0.000 claims abstract description 27
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
201000010099 disease Diseases 0.000 claims abstract description 20
230000003612 virological effect Effects 0.000 claims abstract description 11
230000001613 neoplastic effect Effects 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 130
229910052799 carbon Inorganic materials 0.000 claims description 117
125000000217 alkyl group Chemical group 0.000 claims description 102
238000000034 method Methods 0.000 claims description 93
150000003839 salts Chemical class 0.000 claims description 68
229910052736 halogen Inorganic materials 0.000 claims description 41
125000001424 substituent group Chemical group 0.000 claims description 32
241001465754 Metazoa Species 0.000 claims description 31
150000002367 halogens Chemical class 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
102000006992 Interferon-alpha Human genes 0.000 claims description 9
108010047761 Interferon-alpha Proteins 0.000 claims description 9
230000001939 inductive effect Effects 0.000 claims description 8
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 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 71
239000000203 mixture Substances 0.000 abstract description 55
230000028993 immune response Effects 0.000 abstract description 12
238000011282 treatment Methods 0.000 abstract description 12
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 408
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 354
238000006243 chemical reaction Methods 0.000 description 227
239000007787 solid Substances 0.000 description 150
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 137
229910052757 nitrogen Inorganic materials 0.000 description 112
-1 4-amino-1H-imidazo [4,5-c] quinolin-1-yl Chemical group 0.000 description 104
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 93
239000000243 solution Substances 0.000 description 93
239000011541 reaction mixture Substances 0.000 description 81
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 76
238000004458 analytical method Methods 0.000 description 73
238000007429 general method Methods 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
239000003921 oil Substances 0.000 description 62
235000019198 oils Nutrition 0.000 description 62
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 61
239000000047 product Substances 0.000 description 56
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 55
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 53
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000000463 material Substances 0.000 description 50
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
SORQIYFSJAWBNQ-UHFFFAOYSA-N 1-iodo-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1I SORQIYFSJAWBNQ-UHFFFAOYSA-N 0.000 description 47
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
239000002904 solvent Substances 0.000 description 38
239000012458 free base Substances 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 31
HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 30
229910052943 magnesium sulfate Inorganic materials 0.000 description 30
235000019341 magnesium sulphate Nutrition 0.000 description 30
238000000746 purification Methods 0.000 description 30
238000005259 measurement Methods 0.000 description 27
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 26
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 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
238000001914 filtration Methods 0.000 description 24
239000002244 precipitate Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
238000001953 recrystallisation Methods 0.000 description 22
239000000741 silica gel Substances 0.000 description 22
229910002027 silica gel Inorganic materials 0.000 description 22
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 21
239000012267 brine Substances 0.000 description 21
239000003054 catalyst Substances 0.000 description 21
150000004820 halides Chemical class 0.000 description 21
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
239000000706 filtrate Substances 0.000 description 20
238000003818 flash chromatography Methods 0.000 description 20
238000003756 stirring Methods 0.000 description 20
238000004809 thin layer chromatography Methods 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
239000012299 nitrogen atmosphere Substances 0.000 description 18
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 18
238000004440 column chromatography Methods 0.000 description 17
238000007796 conventional method Methods 0.000 description 17
239000000843 powder Substances 0.000 description 17
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
108060008682 Tumor Necrosis Factor Proteins 0.000 description 16
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 16
150000004703 alkoxides Chemical class 0.000 description 16
238000011894 semi-preparative HPLC Methods 0.000 description 16
239000012312 sodium hydride Substances 0.000 description 16
229910000104 sodium hydride Inorganic materials 0.000 description 16
238000010438 heat treatment Methods 0.000 description 15
GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 14
125000005977 3-phenylpropyloxy group Chemical group 0.000 description 14
FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 14
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
239000012223 aqueous fraction Substances 0.000 description 14
OVPPDFOKBBTFHT-UHFFFAOYSA-N 4-n-(2-phenoxyethyl)quinoline-3,4-diamine Chemical compound NC1=CN=C2C=CC=CC2=C1NCCOC1=CC=CC=C1 OVPPDFOKBBTFHT-UHFFFAOYSA-N 0.000 description 13
150000001412 amines Chemical class 0.000 description 13
230000006698 induction Effects 0.000 description 13
239000010410 layer Substances 0.000 description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
239000003039 volatile agent Substances 0.000 description 13
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 11
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 11
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
229910021595 Copper(I) iodide Inorganic materials 0.000 description 11
108010050904 Interferons Proteins 0.000 description 11
102000014150 Interferons Human genes 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
239000000908 ammonium hydroxide Substances 0.000 description 11
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 11
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 11
229940079322 interferon Drugs 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 10
239000012071 phase Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
238000010189 synthetic method Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
206010028980 Neoplasm Diseases 0.000 description 9
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 9
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000002480 mineral oil Substances 0.000 description 9
235000010446 mineral oil Nutrition 0.000 description 9
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 9
125000000714 pyrimidinyl group Chemical group 0.000 description 9
238000010898 silica gel chromatography Methods 0.000 description 9
125000006516 2-(benzyloxy)ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 8
239000012043 crude product Substances 0.000 description 8
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 8
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 8
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 7
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 7
150000001204 N-oxides Chemical class 0.000 description 7
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 7
239000012467 final product Substances 0.000 description 7
125000001072 heteroaryl group Chemical group 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
210000005260 human cell Anatomy 0.000 description 7
239000012948 isocyanate Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 7
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 6
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 6
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
239000005711 Benzoic acid Substances 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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 6
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 6
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 6
150000002513 isocyanates Chemical class 0.000 description 6
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000001665 trituration Methods 0.000 description 6
238000003828 vacuum filtration Methods 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
238000002604 ultrasonography Methods 0.000 description 5
SKOBGLOJJGVOSV-SNVBAGLBSA-N (2r)-2-imidazo[4,5-c]quinolin-1-ylbutan-1-ol Chemical compound C1=CC=CC2=C3N([C@@H](CO)CC)C=NC3=CN=C21 SKOBGLOJJGVOSV-SNVBAGLBSA-N 0.000 description 4
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 4
DMQAXDOKKRWQEE-UHFFFAOYSA-N 1-(2H-quinolin-1-yloxy)-2H-quinoline Chemical compound N1(CC=CC2=CC=CC=C12)ON1CC=CC2=CC=CC=C12 DMQAXDOKKRWQEE-UHFFFAOYSA-N 0.000 description 4
JWRNUPCIPGBNGE-UHFFFAOYSA-N 2-[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]ethanol Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCO)C3=CN=C21 JWRNUPCIPGBNGE-UHFFFAOYSA-N 0.000 description 4
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Classifications

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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
- 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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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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SK684-2003A 2000-12-08 2001-12-06 Aryl ether substituted imidazoquinolines SK6842003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US25421800P	2000-12-08	2000-12-08
PCT/US2001/046581 WO2002046189A2 (en)	2000-12-08	2001-12-06	Aryl ether substituted imidazoquinolines

Publications (1)

Publication Number	Publication Date
SK6842003A3 true SK6842003A3 (en)	2003-12-02

Family

ID=22963391

Family Applications (6)

Application Number	Title	Priority Date	Filing Date
SK684-2003A SK6842003A3 (en)	2000-12-08	2001-12-06	Aryl ether substituted imidazoquinolines
SK712-2003A SK7122003A3 (en)	2000-12-08	2001-12-06	Urea substituted imidazoquinoline ethers
SK715-2003A SK7152003A3 (en)	2000-12-08	2001-12-06	Heterocyclic ether substituted imidazoquinolines
SK713-2003A SK287732B6 (en)	2000-12-08	2001-12-06	Amido ether substituted imidazoquinolines, pharmaceutical composition and use thereof
SK711-2003A SK7112003A3 (en)	2000-12-08	2001-12-06	Sulfonamido 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

Family Applications After (5)

Application Number	Title	Priority Date	Filing Date
SK712-2003A SK7122003A3 (en)	2000-12-08	2001-12-06	Urea substituted imidazoquinoline ethers
SK715-2003A SK7152003A3 (en)	2000-12-08	2001-12-06	Heterocyclic ether substituted imidazoquinolines
SK713-2003A SK287732B6 (en)	2000-12-08	2001-12-06	Amido ether substituted imidazoquinolines, pharmaceutical composition and use thereof
SK711-2003A SK7112003A3 (en)	2000-12-08	2001-12-06	Sulfonamido 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

Country Status (31)

Country	Link
US (8)	US6656938B2 (pt)
EP (6)	EP1341791B1 (pt)
JP (7)	JP2004515500A (pt)
KR (6)	KR20040023576A (pt)
CN (6)	CN1247575C (pt)
AR (6)	AR035664A1 (pt)
AT (3)	ATE296301T1 (pt)
AU (12)	AU3248202A (pt)
BR (6)	BR0116052A (pt)
CA (6)	CA2430844A1 (pt)
CY (2)	CY1105586T1 (pt)
CZ (6)	CZ20031563A3 (pt)
DE (3)	DE60126645T2 (pt)
DK (3)	DK1341791T3 (pt)
EE (6)	EE200300270A (pt)
ES (3)	ES2281456T3 (pt)
HR (6)	HRP20030462A2 (pt)
HU (6)	HUP0700062A2 (pt)
IL (6)	IL156044A0 (pt)
MX (6)	MXPA03005011A (pt)
NO (6)	NO20032449L (pt)
NZ (6)	NZ526088A (pt)
PL (7)	PL365995A1 (pt)
PT (2)	PT1341791E (pt)
RU (6)	RU2302418C2 (pt)
SI (1)	SI1341790T1 (pt)
SK (6)	SK6842003A3 (pt)
TW (3)	TWI293300B (pt)
UA (2)	UA74852C2 (pt)
WO (6)	WO2002046191A2 (pt)
ZA (6)	ZA200305270B (pt)

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JP2006519877A (ja) *	2003-03-07	2006-08-31	スリーエムイノベイティブプロパティズカンパニー	１−アミノ１ｈ−イミダゾキノリン
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EP1663222A4 (en) *	2003-09-02	2008-05-21	3M Innovative Properties Co	METHODS RELATING TO THE TREATMENT OF GIANCES
AU2004270201A1 (en) *	2003-09-05	2005-03-17	3M Innovative Properties Company	Treatment for CD5+ B cell lymphoma
EP1664342A4 (en) *	2003-09-17	2007-12-26	3M Innovative Properties Co	SELECTIVE MODULATION OF TLR GENE EXPRESSION
AR046046A1 (es)	2003-10-03	2005-11-23	3M Innovative Properties Co	Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas.
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KR20060120069A (ko)	2003-10-03	2006-11-24	쓰리엠 이노베이티브 프로퍼티즈 컴파니	피라졸로피리딘 및 그의 유사체
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JP2007509987A (ja) *	2003-10-31	2007-04-19	スリーエムイノベイティブプロパティズカンパニー	免疫応答調節剤化合物による好中球活性化
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EP1685129A4 (en) *	2003-11-14	2008-10-22	3M Innovative Properties Co	OXIMSUBSTITUTED IMIDAZORING CONNECTIONS
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2001
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- 2001-12-06 RU RU2003116061/04A patent/RU2315049C2/ru not_active IP Right Cessation
- 2001-12-06 CA CA002431151A patent/CA2431151A1/en not_active Withdrawn
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- 2001-12-06 DE DE60117859T patent/DE60117859T2/de not_active Expired - Fee Related
- 2001-12-06 CZ CZ20031562A patent/CZ20031562A3/cs unknown
- 2001-12-06 HU HU0400710A patent/HUP0400710A2/hu unknown
- 2001-12-06 PL PL01366115A patent/PL366115A1/xx not_active Application Discontinuation
- 2001-12-06 SK SK710-2003A patent/SK287264B6/sk not_active IP Right Cessation
- 2001-12-06 CZ CZ20031591A patent/CZ20031591A3/cs unknown
- 2001-12-06 HU HU0600600A patent/HUP0600600A2/hu unknown
- 2001-12-06 AU AU2002230618A patent/AU2002230618B2/en not_active Ceased
- 2001-12-06 JP JP2002547925A patent/JP4437189B2/ja not_active Expired - Fee Related
- 2001-12-06 DE DE60111076T patent/DE60111076T2/de not_active Expired - Lifetime
- 2001-12-06 EP EP01992005A patent/EP1341792A2/en not_active Withdrawn
- 2001-12-06 AU AU3061802A patent/AU3061802A/xx active Pending
- 2001-12-06 RU RU2003116123/04A patent/RU2003116123A/ru not_active Application Discontinuation
- 2001-12-06 JP JP2002547930A patent/JP2004515501A/ja active Pending
- 2001-12-06 HR HR20030461A patent/HRP20030461A2/hr not_active Application Discontinuation
- 2001-12-06 EE EEP200300271A patent/EE200300271A/xx unknown
- 2001-12-07 TW TW090130404A patent/TWI293300B/zh active
- 2001-12-07 TW TW090130401A patent/TW584633B/zh not_active IP Right Cessation
- 2001-12-07 TW TW090130402A patent/TWI222972B/zh active
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2003
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- 2003-10-07 US US10/680,989 patent/US7049439B2/en not_active Expired - Fee Related
- 2003-10-29 US US10/696,476 patent/US20040092545A1/en not_active Abandoned
- 2003-10-29 US US10/696,753 patent/US6953804B2/en not_active Expired - Fee Related
2005
- 2005-02-28 US US11/069,033 patent/US7132429B2/en not_active Expired - Fee Related
- 2005-05-19 US US11/132,900 patent/US7612083B2/en not_active Expired - Fee Related
- 2005-08-24 CY CY20051101024T patent/CY1105586T1/el unknown
2007
- 2007-05-09 CY CY20071100621T patent/CY1106569T1/el unknown
2009
- 2009-11-06 JP JP2009255040A patent/JP2010031040A/ja not_active Ceased

Also Published As

Publication number	Publication date
NZ526087A (en)	2004-11-26
WO2002046193A2 (en)	2002-06-13
UA75622C2 (en)	2006-05-15
WO2002046193A3 (en)	2003-02-27
CZ20031592A3 (cs)	2004-01-14
JP2004532810A (ja)	2004-10-28
DE60126645D1 (de)	2007-03-29
MXPA03004974A (es)	2003-09-05
BR0116470A (pt)	2005-08-16
CN1479739A (zh)	2004-03-03
WO2002046191A3 (en)	2003-03-13
KR20040047733A (ko)	2004-06-05
CA2436846A1 (en)	2002-06-13
US7049439B2 (en)	2006-05-23
CZ303462B6 (cs)	2012-09-26
EE200300272A (et)	2003-10-15
CA2436984A1 (en)	2002-06-13
SI1341790T1 (sl)	2007-06-30
CN1537111A (zh)	2004-10-13
WO2002046192A3 (en)	2003-02-13
US7612083B2 (en)	2009-11-03
ZA200305274B (en)	2004-10-18
CN1252070C (zh)	2006-04-19
WO2002046189A3 (en)	2003-03-20
US6656938B2 (en)	2003-12-02
PL392462A1 (pl)	2010-11-22
AR035667A1 (es)	2004-06-23
CZ20031563A3 (cs)	2004-02-18
AU2002230618B2 (en)	2006-11-02
IL156043A0 (en)	2003-12-23
RU2003116059A (ru)	2005-02-10
NO20032451L (no)	2003-07-16
EP1341791B1 (en)	2005-05-25
HRP20030462A2 (en)	2004-04-30
EE200300275A (et)	2003-10-15
PL366330A1 (en)	2005-01-24
TWI293300B (en)	2008-02-11
DE60111076D1 (en)	2005-06-30
UA74852C2 (en)	2006-02-15
US20040092545A1 (en)	2004-05-13
PL366115A1 (en)	2005-01-24
JP2004529078A (ja)	2004-09-24
CN1253452C (zh)	2006-04-26
MXPA03004973A (es)	2004-01-29
NZ526089A (en)	2004-11-26
NO20032473L (no)	2003-05-30
HUP0600605A2 (en)	2006-11-28
RU2003116123A (ru)	2004-11-20
JP4437189B2 (ja)	2010-03-24
DE60117859T2 (de)	2006-11-23
EP1341789A2 (en)	2003-09-10
PL361948A1 (en)	2004-10-18
AR035668A1 (es)	2004-06-23
AU3061802A (en)	2002-06-18
IL156044A0 (en)	2003-12-23
AU2002239517B2 (en)	2006-11-02
DK1343784T3 (da)	2006-07-10
BR0116464A (pt)	2006-02-21
HRP20030467A2 (en)	2004-04-30
NO20032451D0 (no)	2003-05-28
AR035666A1 (es)	2004-06-23
PL365883A1 (en)	2005-01-10
NO20032596D0 (no)	2003-06-06
WO2002046192A2 (en)	2002-06-13
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AU2002232497B2 (en)	2006-11-02
CN1511155A (zh)	2004-07-07
CA2430844A1 (en)	2002-06-13
RU2315049C2 (ru)	2008-01-20
CA2436980A1 (en)	2002-06-13
MXPA03004972A (es)	2004-01-29
NO326159B1 (no)	2008-10-13
US6683088B2 (en)	2004-01-27
EP1341791A2 (en)	2003-09-10
WO2002046191A2 (en)	2002-06-13
MXPA03005011A (es)	2003-09-05
CN1247575C (zh)	2006-03-29
PL365995A1 (en)	2005-01-24
CY1106569T1 (el)	2012-01-25
NZ526088A (en)	2004-12-24
PL365907A1 (en)	2005-01-10
AU3953002A (en)	2002-06-18
US20020193396A1 (en)	2002-12-19
HK1069166A1 (en)	2005-05-13
BR0116047A (pt)	2003-09-30
ZA200305275B (en)	2004-10-08
HUP0600600A2 (en)	2006-11-28
KR20040023576A (ko)	2004-03-18
ES2281456T3 (es)	2007-10-01
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CA2431151A1 (en)	2002-06-13
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AU3249702A (en)	2002-06-18
ES2260323T3 (es)	2006-11-01
CZ20031591A3 (cs)	2003-11-12
WO2002046190A2 (en)	2002-06-13
NZ526105A (en)	2004-11-26
AU2002239530B2 (en)	2006-09-28
HK1066005A1 (en)	2005-03-11
NO20032449D0 (no)	2003-05-28
NZ526106A (en)	2004-11-26
MXPA03004975A (es)	2003-09-05
JP2004523498A (ja)	2004-08-05
EE200300274A (et)	2003-10-15
MXPA03005012A (es)	2003-09-05
ZA200305273B (en)	2004-10-08
EE200300270A (et)	2003-10-15
CZ20031561A3 (cs)	2004-04-14
NZ526086A (en)	2005-11-25
SK7132003A3 (en)	2003-10-07
ATE353895T1 (de)	2007-03-15
SK7102003A3 (en)	2003-10-07
SK287264B6 (sk)	2010-04-07
WO2002046188A3 (en)	2003-03-13
SK287732B6 (en)	2011-07-06
EP1343784B1 (en)	2006-03-08
JP2004515501A (ja)	2004-05-27
US20030158192A1 (en)	2003-08-21
CA2436846C (en)	2010-11-16
AU3951602A (en)	2002-06-18
IL155884A0 (en)	2003-12-23
IL155950A0 (en)	2003-12-23
TWI222972B (en)	2004-11-01
KR20030070050A (ko)	2003-08-27
SK7112003A3 (en)	2003-12-02
DK1341790T3 (da)	2007-06-04
EP1339715A2 (en)	2003-09-03
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US20050148619A1 (en)	2005-07-07
HUP0700062A2 (en)	2007-05-02
HRP20030461A2 (en)	2004-06-30
PT1341790E (pt)	2007-05-31
ZA200305271B (en)	2004-10-08
KR20040028691A (ko)	2004-04-03
AU3248202A (en)	2002-06-18
EE200300271A (et)	2003-10-15
ES2242782T3 (es)	2005-11-16
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US20040077678A1 (en)	2004-04-22
RU2003116649A (ru)	2005-02-10
RU2302418C2 (ru)	2007-07-10
ATE319711T1 (de)	2006-03-15
IL155904A0 (en)	2003-12-23
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EP1343784A2 (en)	2003-09-17
PT1341791E (pt)	2005-09-30
ZA200305272B (en)	2005-01-26
HRP20030466A2 (en)	2004-06-30
HUP0400710A2 (hu)	2004-06-28
HRP20030467B1 (hr)	2009-04-30
AU2002239516B2 (en)	2006-11-09
RU2003116063A (ru)	2004-12-10
US20050234088A1 (en)	2005-10-20
HUP0400704A2 (hu)	2004-06-28
NO20032452L (no)	2003-07-16
IL155903A0 (en)	2003-12-23
US20040106640A1 (en)	2004-06-03
SK7152003A3 (en)	2003-09-11
TW584633B (en)	2004-04-21
CN1894244A (zh)	2007-01-10
NO20032452D0 (no)	2003-05-28
AU2002232482B2 (en)	2006-10-19
NO20032449L (no)	2003-05-28
WO2002046188A2 (en)	2002-06-13
US20030212091A1 (en)	2003-11-13
BR0116052A (pt)	2006-02-21
PL207340B1 (pl)	2010-12-31
AR035664A1 (es)	2004-06-23
AU3951702A (en)	2002-06-18
CY1105586T1 (el)	2010-07-28
HK1064383A1 (en)	2005-01-28
HRP20030464A2 (en)	2004-06-30
US7132429B2 (en)	2006-11-07
HUP0600338A2 (en)	2006-08-28
CN1479738A (zh)	2004-03-03
NO20032596L (no)	2003-06-06
NO20032473D0 (no)	2003-05-30
CN1297554C (zh)	2007-01-31
JP2004521092A (ja)	2004-07-15
DE60117859D1 (de)	2006-05-04
CA2436980C (en)	2011-03-29
ZA200305270B (en)	2004-08-26
KR20030070049A (ko)	2003-08-27
SK7122003A3 (en)	2003-11-04
BR0116026A (pt)	2004-12-21
EP1341790B1 (en)	2007-02-14
DE60126645T2 (de)	2007-11-22
JP2010031040A (ja)	2010-02-12
JP2004515500A (ja)	2004-05-27
DE60111076T2 (de)	2006-05-04
EP1341792A2 (en)	2003-09-10
NO20032595D0 (no)	2003-06-06
ATE296301T1 (de)	2005-06-15
CZ20031560A3 (en)	2004-05-12
US6953804B2 (en)	2005-10-11
KR20040028690A (ko)	2004-04-03
RU2351598C2 (ru)	2009-04-10
AR035669A1 (es)	2004-06-23
BR0116032A (pt)	2006-02-21
AR035665A1 (es)	2004-06-23
CN1487939A (zh)	2004-04-07
RU2308456C2 (ru)	2007-10-20

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2011-07-06	FC9A	Refused patent application