CA2686163A1 - Imidazoquinolines with immuno-modulating properties - Google Patents
Imidazoquinolines with immuno-modulating properties Download PDFInfo
- Publication number
- CA2686163A1 CA2686163A1 CA002686163A CA2686163A CA2686163A1 CA 2686163 A1 CA2686163 A1 CA 2686163A1 CA 002686163 A CA002686163 A CA 002686163A CA 2686163 A CA2686163 A CA 2686163A CA 2686163 A1 CA2686163 A1 CA 2686163A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- amino
- imidazo
- quinolin
- propyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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 4
- 230000002519 immonomodulatory effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 334
- 238000000034 method Methods 0.000 claims abstract description 84
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 10
- -1 cyano, hydroxyl Chemical group 0.000 claims description 94
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 37
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- OAFYFGINDSGHDR-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 OAFYFGINDSGHDR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 101000669402 Homo sapiens Toll-like receptor 7 Proteins 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 claims description 6
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 6
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 6
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 6
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 150000003573 thiols Chemical class 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 5
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- CARVEAKPQSZLKP-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(1-methylpiperidin-4-yl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C1CCN(C)CC1)CC1=CC=CC(CC(=O)OC)=C1 CARVEAKPQSZLKP-UHFFFAOYSA-N 0.000 claims description 4
- LZHLVRRBAUBVRX-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[3-(dimethylamino)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CCCN(C)C)CC1=CC=CC(CC(=O)OC)=C1 LZHLVRRBAUBVRX-UHFFFAOYSA-N 0.000 claims description 4
- LEISSPDNWSLBRZ-UHFFFAOYSA-N methyl 2-[3-[[3-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=CC(CC(=O)OC)=C1 LEISSPDNWSLBRZ-UHFFFAOYSA-N 0.000 claims description 4
- DMIPROXJBJIXPM-UHFFFAOYSA-N methyl 2-[3-[[4-[[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]methyl]piperidin-1-yl]methyl]phenyl]acetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(CC1)CCN1CC1=CC=CC(CC(=O)OC)=C1 DMIPROXJBJIXPM-UHFFFAOYSA-N 0.000 claims description 4
- XIQQEASYCSFTBJ-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propylamino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNCC1=CC=C(CC(=O)OC)C=C1 XIQQEASYCSFTBJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 208000005176 Hepatitis C Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
- 230000000172 allergic effect Effects 0.000 claims description 3
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 208000002672 hepatitis B Diseases 0.000 claims description 3
- UIVIPXGEVSLKEY-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(2-morpholin-4-ylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCOCC1)CC1=CC=CC(CC(=O)OC)=C1 UIVIPXGEVSLKEY-UHFFFAOYSA-N 0.000 claims description 3
- HCCJVWXUQYDTCH-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(2-piperidin-1-ylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCCCC1)CC1=CC=CC(CC(=O)OC)=C1 HCCJVWXUQYDTCH-UHFFFAOYSA-N 0.000 claims description 3
- CQWGSSPDVHWUFF-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(2-pyrrolidin-1-ylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCCC1)CC1=CC=CC(CC(=O)OC)=C1 CQWGSSPDVHWUFF-UHFFFAOYSA-N 0.000 claims description 3
- JXRWVFKUUVEFAW-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(3-morpholin-4-ylpropyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1CCOCC1 JXRWVFKUUVEFAW-UHFFFAOYSA-N 0.000 claims description 3
- XDCGQPFRLPMZKQ-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(1,4-oxazepan-4-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCOCCC1)CC1=CC=CC(CC(=O)OC)=C1 XDCGQPFRLPMZKQ-UHFFFAOYSA-N 0.000 claims description 3
- VIUKMRIXTOCAIL-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(3-hydroxyazetidin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CC(O)C1)CC1=CC=CC(CC(=O)OC)=C1 VIUKMRIXTOCAIL-UHFFFAOYSA-N 0.000 claims description 3
- YWFAPMNKHRMMFS-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(3-hydroxypyrrolidin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CC(O)CC1)CC1=CC=CC(CC(=O)OC)=C1 YWFAPMNKHRMMFS-UHFFFAOYSA-N 0.000 claims description 3
- SVFXDRXNTFGFAD-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-hydroxypiperidin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC(O)CC1)CC1=CC=CC(CC(=O)OC)=C1 SVFXDRXNTFGFAD-UHFFFAOYSA-N 0.000 claims description 3
- LYPNDXHMUCFPAF-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-methoxypiperidin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC(CC1)OC)CC1=CC=CC(CC(=O)OC)=C1 LYPNDXHMUCFPAF-UHFFFAOYSA-N 0.000 claims description 3
- KYPGMBKNBVAKPS-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-methylsulfonyl-1,4-diazepan-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCC1)S(C)(=O)=O)CC1=CC=CC(CC(=O)OC)=C1 KYPGMBKNBVAKPS-UHFFFAOYSA-N 0.000 claims description 3
- CSCIBDSZYKIPNE-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-methylsulfonylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CC1)S(C)(=O)=O)CC1=CC=CC(CC(=O)OC)=C1 CSCIBDSZYKIPNE-UHFFFAOYSA-N 0.000 claims description 3
- ASIRWIVQGZUAHB-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(azepan-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCCCCC1)CC1=CC=CC(CC(=O)OC)=C1 ASIRWIVQGZUAHB-UHFFFAOYSA-N 0.000 claims description 3
- WJZDYZUKXBCLFY-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(azetidin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC1)CC1=CC=CC(CC(=O)OC)=C1 WJZDYZUKXBCLFY-UHFFFAOYSA-N 0.000 claims description 3
- XJRQEYKDFZPUDL-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=CC(CC(=O)OC)=C1 XJRQEYKDFZPUDL-UHFFFAOYSA-N 0.000 claims description 3
- REYOPNVVVPNASZ-PLQXJYEYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[(2r,6s)-2,6-dimethylmorpholin-4-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1C[C@@H](C)O[C@@H](C)C1)CC1=CC=CC(CC(=O)OC)=C1 REYOPNVVVPNASZ-PLQXJYEYSA-N 0.000 claims description 3
- IWDSQAIXLBTIEE-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[2-methoxyethyl(methyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)CCOC)CC1=CC=CC(CC(=O)OC)=C1 IWDSQAIXLBTIEE-UHFFFAOYSA-N 0.000 claims description 3
- CNNGXIJZBNMYPP-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[4-(2-hydroxyethyl)piperazin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCO)CC1)CC1=CC=CC(CC(=O)OC)=C1 CNNGXIJZBNMYPP-UHFFFAOYSA-N 0.000 claims description 3
- JXQDWYKXXBRDST-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[4-(2-methoxyethyl)piperazin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCOC)CC1)CC1=CC=CC(CC(=O)OC)=C1 JXQDWYKXXBRDST-UHFFFAOYSA-N 0.000 claims description 3
- ZAFKGINZBRIOFW-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[4-(dimethylcarbamoyl)piperidin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC(CC1)C(=O)N(C)C)CC1=CC=CC(CC(=O)OC)=C1 ZAFKGINZBRIOFW-UHFFFAOYSA-N 0.000 claims description 3
- AJXWMDOGABJQCB-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[4-(ethylcarbamoyl)-1,4-diazepan-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCC1)C(=O)NCC)CC1=CC=CC(CC(=O)OC)=C1 AJXWMDOGABJQCB-UHFFFAOYSA-N 0.000 claims description 3
- ICEKWPYJHOUFIF-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[bis(2-hydroxyethyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(CCO)CCO)CC1=CC=CC(CC(=O)OC)=C1 ICEKWPYJHOUFIF-UHFFFAOYSA-N 0.000 claims description 3
- KPQFVWZPJIIRQQ-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[butyl(methyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)CCCC)CC1=CC=CC(CC(=O)OC)=C1 KPQFVWZPJIIRQQ-UHFFFAOYSA-N 0.000 claims description 3
- KZPHNBDDMMHSPN-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[methyl(oxan-4-yl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C1CCOCC1)CC1=CC=CC(CC(=O)OC)=C1 KZPHNBDDMMHSPN-UHFFFAOYSA-N 0.000 claims description 3
- VEDCUJSSWBHNNY-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[3-(4-methylpiperazin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1CCN(C)CC1 VEDCUJSSWBHNNY-UHFFFAOYSA-N 0.000 claims description 3
- DPFWTVXXNGIJTB-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[3-[ethyl(methyl)amino]propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CCCN(C)CC)CC1=CC=CC(CC(=O)OC)=C1 DPFWTVXXNGIJTB-UHFFFAOYSA-N 0.000 claims description 3
- LKRPXKGFSKFBQC-UHFFFAOYSA-N methyl 2-[3-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(C)CC1)CC1=CC=CC(CC(=O)OC)=C1 LKRPXKGFSKFBQC-UHFFFAOYSA-N 0.000 claims description 3
- ROHZFOMXMXPLTC-UHFFFAOYSA-N methyl 2-[3-[[[2-(4-acetylpiperazin-1-yl)acetyl]-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CC1)C(C)=O)CC1=CC=CC(CC(=O)OC)=C1 ROHZFOMXMXPLTC-UHFFFAOYSA-N 0.000 claims description 3
- GOXIVZHBIPWDCC-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(1-methylpiperidin-4-yl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C1CCN(C)CC1)CC1=CC=C(CC(=O)OC)C=C1 GOXIVZHBIPWDCC-UHFFFAOYSA-N 0.000 claims description 3
- JESLMFCDDXPVAC-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(2-methylsulfonylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CS(C)(=O)=O)CC1=CC=C(CC(=O)OC)C=C1 JESLMFCDDXPVAC-UHFFFAOYSA-N 0.000 claims description 3
- QZTUTIRJBODVLE-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(2-morpholin-4-ylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCOCC1)CC1=CC=C(CC(=O)OC)C=C1 QZTUTIRJBODVLE-UHFFFAOYSA-N 0.000 claims description 3
- DWFOPGQSOBAJKR-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-(2-piperidin-1-ylacetyl)amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCCCC1)CC1=CC=C(CC(=O)OC)C=C1 DWFOPGQSOBAJKR-UHFFFAOYSA-N 0.000 claims description 3
- MMFRJKPGXIZWQR-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-ethylsulfonylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CC1)S(=O)(=O)CC)CC1=CC=C(CC(=O)OC)C=C1 MMFRJKPGXIZWQR-UHFFFAOYSA-N 0.000 claims description 3
- BJHUVAVJIWESCC-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(C)CC1)CC1=CC=C(CC(=O)OC)C=C1 BJHUVAVJIWESCC-UHFFFAOYSA-N 0.000 claims description 3
- HJIFSDUTJZSBIF-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-methylsulfonyl-1,4-diazepan-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCC1)S(C)(=O)=O)CC1=CC=C(CC(=O)OC)C=C1 HJIFSDUTJZSBIF-UHFFFAOYSA-N 0.000 claims description 3
- JUEZMCCALJINEA-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-pyrimidin-2-ylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CC1)C=1N=CC=CN=1)CC1=CC=C(CC(=O)OC)C=C1 JUEZMCCALJINEA-UHFFFAOYSA-N 0.000 claims description 3
- XHNJWZRQHYJISF-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)ethyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CCN(C)C)CC1=CC=C(CC(=O)OC)C=C1 XHNJWZRQHYJISF-UHFFFAOYSA-N 0.000 claims description 3
- WPISGLOWKAPJDW-RUZDIDTESA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[(3r)-3-hydroxypyrrolidin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1C[C@H](O)CC1)CC1=CC=C(CC(=O)OC)C=C1 WPISGLOWKAPJDW-RUZDIDTESA-N 0.000 claims description 3
- XXMCSDCNXCWIMX-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[2-methoxyethyl(methyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)CCOC)CC1=CC=C(CC(=O)OC)C=C1 XXMCSDCNXCWIMX-UHFFFAOYSA-N 0.000 claims description 3
- RDGRORCYIFMENB-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[4-(2-methoxyethyl)piperazin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCOC)CC1)CC1=CC=C(CC(=O)OC)C=C1 RDGRORCYIFMENB-UHFFFAOYSA-N 0.000 claims description 3
- IFMMVHLTGHKTQC-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC(CC1)NC(=O)OC(C)(C)C)CC1=CC=C(CC(=O)OC)C=C1 IFMMVHLTGHKTQC-UHFFFAOYSA-N 0.000 claims description 3
- KCBBBQYACGRFSU-UHFFFAOYSA-N methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]piperidin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC(CC1)N(C)C(=O)OC(C)(C)C)CC1=CC=C(CC(=O)OC)C=C1 KCBBBQYACGRFSU-UHFFFAOYSA-N 0.000 claims description 3
- VXXSVMYETJWPJF-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-(2-piperidin-1-ylacetyl)amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCCCC1)CC1=CC=C(CC(=O)OC)C=C1 VXXSVMYETJWPJF-UHFFFAOYSA-N 0.000 claims description 3
- WCZWCGDYHVIAEI-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-(3-morpholin-4-ylpropyl)amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(CC=1C=CC(CC(=O)OC)=CC=1)CCCN1CCOCC1 WCZWCGDYHVIAEI-UHFFFAOYSA-N 0.000 claims description 3
- QSNHNVFMEXXRHY-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-(3-piperidin-1-ylpropanoyl)amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CCN1CCCCC1)CC1=CC=C(CC(=O)OC)C=C1 QSNHNVFMEXXRHY-UHFFFAOYSA-N 0.000 claims description 3
- JAFVJOPWLXIGNO-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(C)CC1)CC1=CC=C(CC(=O)OC)C=C1 JAFVJOPWLXIGNO-UHFFFAOYSA-N 0.000 claims description 3
- RRDDJWNSVSLZSN-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 RRDDJWNSVSLZSN-UHFFFAOYSA-N 0.000 claims description 3
- LTFLHHBTALZTMI-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-[2-methoxyethyl(methyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)CCOC)CC1=CC=C(CC(=O)OC)C=C1 LTFLHHBTALZTMI-UHFFFAOYSA-N 0.000 claims description 3
- PVLZGSGXJDZIPR-UHFFFAOYSA-N methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-[4-(2-methoxyethyl)piperazin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound C1CN(CCOC)CCN1CC(=O)N(CC=1C=CC(CC(=O)OC)=CC=1)CCCN1C2=C3C=CC=CC3=NC(N)=C2N=C1CCOC PVLZGSGXJDZIPR-UHFFFAOYSA-N 0.000 claims description 3
- WQCJXYOLFCQCPI-UHFFFAOYSA-N methyl 2-[4-[[[2-(4-acetyl-1,4-diazepan-1-yl)acetyl]-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCC1)C(C)=O)CC1=CC=C(CC(=O)OC)C=C1 WQCJXYOLFCQCPI-UHFFFAOYSA-N 0.000 claims description 3
- BPZZWUMXCXBSHE-UHFFFAOYSA-N methyl 2-[4-[[[2-(4-acetylpiperazin-1-yl)acetyl]-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CC1)C(C)=O)CC1=CC=C(CC(=O)OC)C=C1 BPZZWUMXCXBSHE-UHFFFAOYSA-N 0.000 claims description 3
- UTDBMWAVSHBXLP-UHFFFAOYSA-N methyl 2-[4-[[[2-[(1-acetylpiperidin-4-yl)-methylamino]acetyl]-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C1CCN(CC1)C(C)=O)CC1=CC=C(CC(=O)OC)C=C1 UTDBMWAVSHBXLP-UHFFFAOYSA-N 0.000 claims description 3
- NIOHPZFOZHREKH-UHFFFAOYSA-N methyl 2-[4-[[acetyl-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(C)=O)CC1=CC=C(CC(=O)OC)C=C1 NIOHPZFOZHREKH-UHFFFAOYSA-N 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 230000003612 virological effect Effects 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- WMGXYISEDFFZJJ-UHFFFAOYSA-N 1,1-dioxo-1,2-benzothiazol-3-one;methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-(2-pyrrolidin-1-ylacetyl)amino]methyl]phenyl]acetate Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1.COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCCC1)CC1=CC=C(CC(=O)OC)C=C1 WMGXYISEDFFZJJ-UHFFFAOYSA-N 0.000 claims description 2
- GOPXPFFHGOMCHI-FBHGDYMESA-N 1,1-dioxo-1,2-benzothiazol-3-one;methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1.COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1[C@H](CCC1)COC)CC1=CC=C(CC(=O)OC)C=C1 GOPXPFFHGOMCHI-FBHGDYMESA-N 0.000 claims description 2
- XELMNKRTPKTECU-UHFFFAOYSA-N 1,1-dioxo-1,2-benzothiazol-3-one;methyl 2-[4-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-[2-hydroxyethyl(methyl)amino]acetyl]amino]methyl]phenyl]acetate Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1.COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)CCO)CC1=CC=C(CC(=O)OC)C=C1 XELMNKRTPKTECU-UHFFFAOYSA-N 0.000 claims description 2
- GOPXPFFHGOMCHI-ROPHLPQBSA-N C1=CC=C2C(=O)NS(=O)(=O)C2=C1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1.COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1[C@@H](CCC1)COC)CC1=CC=C(CC(=O)OC)C=C1 Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1.COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1[C@@H](CCC1)COC)CC1=CC=C(CC(=O)OC)C=C1 GOPXPFFHGOMCHI-ROPHLPQBSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 206010048768 Dermatosis Diseases 0.000 claims description 2
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- GHHLGTJMHFABRG-UHFFFAOYSA-N ethyl 2-[1-[2-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[[4-(2-methoxy-2-oxoethyl)phenyl]methyl]amino]-2-oxoethyl]piperidin-4-yl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC(CC(=O)OCC)CC1)CC1=CC=C(CC(=O)OC)C=C1 GHHLGTJMHFABRG-UHFFFAOYSA-N 0.000 claims description 2
- QULMLROHZCOFFO-UHFFFAOYSA-N ethyl 4-[2-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[[4-(2-methoxy-2-oxoethyl)phenyl]methyl]amino]-2-oxoethyl]piperazine-1-carboxylate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CC1)C(=O)OCC)CC1=CC=C(CC(=O)OC)C=C1 QULMLROHZCOFFO-UHFFFAOYSA-N 0.000 claims description 2
- GBWWJSVWFPTHKO-UHFFFAOYSA-N methyl 1-[2-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[[4-(2-methoxy-2-oxoethyl)phenyl]methyl]amino]-2-oxoethyl]piperidine-4-carboxylate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCC(CC1)C(=O)OC)CC1=CC=C(CC(=O)OC)C=C1 GBWWJSVWFPTHKO-UHFFFAOYSA-N 0.000 claims description 2
- ZJCGWXDMMYLJHZ-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-methyl-1,4-diazepan-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(C)CCC1)CC1=CC=CC(CC(=O)OC)=C1 ZJCGWXDMMYLJHZ-UHFFFAOYSA-N 0.000 claims description 2
- XLYSJIJBMCZOFD-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(4-methylpiperazin-1-yl)acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(C)CC1)CC1=CC=CC(CC(=O)OC)=C1 XLYSJIJBMCZOFD-UHFFFAOYSA-N 0.000 claims description 2
- YWFAPMNKHRMMFS-RUZDIDTESA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-[(3r)-3-hydroxypyrrolidin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1C[C@H](O)CC1)CC1=CC=CC(CC(=O)OC)=C1 YWFAPMNKHRMMFS-RUZDIDTESA-N 0.000 claims description 2
- VIMMXFYSJXUVJE-UHFFFAOYSA-N methyl 2-[3-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propylamino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNCC1=CC=CC(CC(=O)OC)=C1 VIMMXFYSJXUVJE-UHFFFAOYSA-N 0.000 claims description 2
- PDZQKBRQBIPYRX-UHFFFAOYSA-N methyl 2-[3-[[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl-[2-[4-(2-methoxyethyl)piperazin-1-yl]acetyl]amino]methyl]phenyl]acetate Chemical compound C1CN(CCOC)CCN1CC(=O)N(CC=1C=C(CC(=O)OC)C=CC=1)CCCN1C2=C3C=CC=CC3=NC(N)=C2N=C1CCOC PDZQKBRQBIPYRX-UHFFFAOYSA-N 0.000 claims description 2
- MZDPKSLQWLUMTD-UHFFFAOYSA-N methyl 2-[3-[[[2-(4-acetyl-1,4-diazepan-1-yl)acetyl]-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]amino]methyl]phenyl]acetate Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN1CCN(CCC1)C(C)=O)CC1=CC=CC(CC(=O)OC)=C1 MZDPKSLQWLUMTD-UHFFFAOYSA-N 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- KBCNCIRXZHHXRQ-WLHGVMLRSA-N (E)-but-2-enedioic acid methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound OC(=O)\C=C\C(O)=O.CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 KBCNCIRXZHHXRQ-WLHGVMLRSA-N 0.000 claims 1
- LRKSXFWMHRNXTM-UHFFFAOYSA-N 1,1-dioxo-1,2-benzothiazol-3-one;methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1.CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 LRKSXFWMHRNXTM-UHFFFAOYSA-N 0.000 claims 1
- IZVKDZDCGUZAME-UHFFFAOYSA-N C1=CC=C2C(=O)NS(=O)(=O)C2=C1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1.CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1.CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 IZVKDZDCGUZAME-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims 1
- 208000022361 Human papillomavirus infectious disease Diseases 0.000 claims 1
- 229910005948 SO2Cl Inorganic materials 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- OHCKSNOGTYWQHJ-UHFFFAOYSA-N benzenesulfonic acid;methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound OS(=O)(=O)C1=CC=CC=C1.OS(=O)(=O)C1=CC=CC=C1.CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 OHCKSNOGTYWQHJ-UHFFFAOYSA-N 0.000 claims 1
- ZSQVBVDZMSNMTB-UHFFFAOYSA-N methanesulfonic acid;methyl 2-[4-[[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl-[2-(dimethylamino)acetyl]amino]methyl]phenyl]acetate Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCN(C(=O)CN(C)C)CC1=CC=C(CC(=O)OC)C=C1 ZSQVBVDZMSNMTB-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract description 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 113
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 112
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- 238000005481 NMR spectroscopy Methods 0.000 description 67
- 239000007787 solid Substances 0.000 description 64
- 239000000203 mixture Substances 0.000 description 59
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
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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
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (5)
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|---|---|---|---|
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| US60/916,586 | 2007-05-08 | ||
| US2495708P | 2008-01-31 | 2008-01-31 | |
| US61/024,957 | 2008-01-31 | ||
| PCT/GB2008/050328 WO2008135791A1 (en) | 2007-05-08 | 2008-05-06 | Imidazoquinolines with immuno-modulating properties |
Publications (1)
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|---|---|
| CA2686163A1 true CA2686163A1 (en) | 2008-11-13 |
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| CA002686163A Abandoned CA2686163A1 (en) | 2007-05-08 | 2008-05-06 | Imidazoquinolines with immuno-modulating properties |
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| US (2) | US8436178B2 (enExample) |
| EP (1) | EP2155743B1 (enExample) |
| JP (1) | JP5400763B2 (enExample) |
| KR (1) | KR20100016289A (enExample) |
| CN (1) | CN101687867B (enExample) |
| AR (1) | AR066492A1 (enExample) |
| AU (1) | AU2008247165B2 (enExample) |
| BR (1) | BRPI0811125A2 (enExample) |
| CA (1) | CA2686163A1 (enExample) |
| CL (1) | CL2008001357A1 (enExample) |
| CO (1) | CO6251247A2 (enExample) |
| CY (1) | CY1113339T1 (enExample) |
| DK (1) | DK2155743T3 (enExample) |
| EC (1) | ECSP099750A (enExample) |
| ES (1) | ES2393037T3 (enExample) |
| HR (1) | HRP20120895T1 (enExample) |
| IL (1) | IL201572A0 (enExample) |
| MX (1) | MX2009011802A (enExample) |
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| TWI392678B (zh) | 2004-03-26 | 2013-04-11 | Dainippon Sumitomo Pharma Co | ９-取代-８-氧基腺嘌呤化合物 |
| WO2008004948A1 (en) * | 2006-07-05 | 2008-01-10 | Astrazeneca Ab | 8-oxoadenine derivatives acting as modulators of tlr7 |
| TW200831105A (en) | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| EP2139894B1 (en) * | 2007-03-19 | 2011-10-26 | AstraZeneca AB | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7) modulators |
| WO2008114008A1 (en) | 2007-03-19 | 2008-09-25 | Astrazeneca Ab | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7 ) modulators |
| AR065784A1 (es) * | 2007-03-20 | 2009-07-01 | Dainippon Sumitomo Pharma Co | Derivados de 8-oxo adenina,medicamentos que los contienen y usos como agentes terapeuticos para enfermedades alergicas, antivirales o antibacterianas. |
| EP2138497A4 (en) | 2007-03-20 | 2012-01-04 | Dainippon Sumitomo Pharma Co | NEW ADENINE CONNECTION |
| JP5400763B2 (ja) * | 2007-05-08 | 2014-01-29 | アストラゼネカ・アクチエボラーグ | 免疫調節特性を有するイミダゾキノリン類 |
| ES2541434T3 (es) * | 2007-06-29 | 2015-07-20 | Gilead Sciences, Inc. | Derivados de purina y su uso como moduladores del receptor de tipo Toll 7 |
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| PE20091156A1 (es) | 2007-12-17 | 2009-09-03 | Astrazeneca Ab | Sales de (3-{[[3-(6-amino-2-butoxi-8-oxo-7,8-dihidro-9h-purin-9-il)propil](3-morfolin-4-ilpropil)amino]metil}fenil)acetato de metilo |
| CN102143964A (zh) | 2008-01-17 | 2011-08-03 | 大日本住友制药株式会社 | 制备腺嘌呤化合物的方法 |
| JPWO2009091031A1 (ja) * | 2008-01-17 | 2011-05-26 | 大日本住友製薬株式会社 | アデニン化合物の製造方法 |
| SI2268618T1 (sl) * | 2008-03-03 | 2015-09-30 | Novartis Ag | Spojine in sestavki kot modulatorji aktivnosti TLR |
| US9073913B2 (en) * | 2008-03-24 | 2015-07-07 | 4Sc Ag | Substituted imidazoquinolines |
| EA026557B1 (ru) | 2008-12-09 | 2017-04-28 | Джилид Сайэнс, Инк. | Промежуточные соединения для получения модуляторов толл-подобных рецепторов |
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| MX2012002723A (es) | 2009-09-02 | 2012-04-11 | Novartis Ag | Composiciones inmunogenicas que incluyen moduladores de la actividad de receptores tipo toll. |
| CA2772253C (en) * | 2009-09-14 | 2018-02-27 | Gilead Sciences, Inc. | Modulators of toll-like receptors |
| US8507507B2 (en) | 2009-10-22 | 2013-08-13 | Gilead Sciences, Inc. | Modulators of toll-like receptors |
| EP2507237A1 (en) * | 2009-12-03 | 2012-10-10 | Dainippon Sumitomo Pharma Co., Ltd. | Imidazoquinolines which act via toll - like receptors (tlr) |
| WO2011084725A1 (en) * | 2009-12-21 | 2011-07-14 | 3M Innovative Properties Company | 4-AMINO-2-(ETHOXYMETHYL)-1-(2-HYDROXY-2-METHYLPROPYL)-1H-IMIDAZO[4,5-c]QUINOLIN-5-IUM 1-HYDROXYNAPHTHALENE-2-CARBOXYLATE COMPOSITIONS AND METHODS |
| US20110150836A1 (en) * | 2009-12-22 | 2011-06-23 | Gilead Sciences, Inc. | Methods of treating hbv and hcv infection |
| CN105999275A (zh) | 2010-09-01 | 2016-10-12 | 诺华有限公司 | 免疫增强剂吸附不溶性金属离子 |
| WO2012080728A1 (en) | 2010-12-16 | 2012-06-21 | Astrazeneca Ab | Imidazo [4, 5 -c] quinolin- 1 -yl derivative useful in therapy |
| US8895570B2 (en) | 2010-12-17 | 2014-11-25 | Astrazeneca Ab | Purine derivatives |
| ES2681698T3 (es) | 2011-03-02 | 2018-09-14 | Glaxosmithkline Biologicals Sa | Vacunas de combinación con menores dosis de antígeno y/o adyuvante |
| US20140363461A1 (en) | 2011-09-01 | 2014-12-11 | Fabio Bagnoli | Adjuvanted formulations of staphylococcus aureus antigens |
| CN104519910B (zh) | 2012-03-07 | 2017-05-03 | 诺华股份有限公司 | 肺炎链球菌抗原的含佐剂制剂 |
| CN104582726A (zh) | 2012-03-07 | 2015-04-29 | 诺华股份有限公司 | 狂犬病病毒免疫原的含佐剂制剂 |
| AU2013229432A1 (en) | 2012-03-08 | 2014-10-16 | Novartis Ag | Adjuvanted formulations of booster vaccines |
| JP6184423B2 (ja) | 2012-05-18 | 2017-08-23 | 大日本住友製薬株式会社 | カルボン酸化合物 |
| US9526776B2 (en) | 2012-09-06 | 2016-12-27 | Glaxosmithkline Biologicals Sa | Combination vaccines with serogroup B meningococcus and D/T/P |
| CN105899537A (zh) | 2014-01-10 | 2016-08-24 | 博笛生物科技（北京）有限公司 | 靶向表达egfr的肿瘤的化合物和组合物 |
| EP4001311B1 (en) | 2014-07-09 | 2025-11-05 | Birdie Biopharmaceuticals Inc. | Anti-pd-l1/pd-1 combinations for treating tumors |
| PT3166607T (pt) | 2014-07-11 | 2022-12-07 | Gilead Sciences Inc | Moduladores de receptores de tipo toll para o tratamento do vih |
| AU2015318061B2 (en) | 2014-09-16 | 2018-05-17 | Gilead Sciences, Inc. | Solid forms of a toll-like receptor modulator |
| CN106943597A (zh) | 2016-01-07 | 2017-07-14 | 博笛生物科技（北京）有限公司 | 用于治疗肿瘤的抗-egfr组合 |
| CN106943596A (zh) | 2016-01-07 | 2017-07-14 | 博笛生物科技（北京）有限公司 | 用于治疗肿瘤的抗-cd20组合 |
| EP3565819B1 (en) * | 2017-01-06 | 2025-11-19 | F. Hoffmann-La Roche AG | Solid forms of [(1s)-1-[(2s,4r,5r)-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl] acetate |
| TWI674261B (zh) | 2017-02-17 | 2019-10-11 | 美商英能腫瘤免疫股份有限公司 | Nlrp3 調節劑 |
| FI3603619T3 (fi) | 2017-03-29 | 2025-09-25 | Sumitomo Pharma Co Ltd | Rokoteadjuvanttiformulaatio |
| CN108794467A (zh) | 2017-04-27 | 2018-11-13 | 博笛生物科技有限公司 | 2-氨基-喹啉衍生物 |
| CA3067268A1 (en) | 2017-06-23 | 2018-12-27 | Birdie Biopharmaceuticals, Inc. | Crystalline resiquimod monosulfate anhydrate and its preparation and uses |
| US12012421B2 (en) | 2017-07-07 | 2024-06-18 | Hoffmann-La Roche Inc. | Solid forms of [(1S)-1-[(2S,4R,5R)-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl] acetate |
| WO2019048036A1 (en) | 2017-09-06 | 2019-03-14 | Biontech Ag | SUBSTITUTED IMIDAZOQUINOLINES |
| US12012420B2 (en) | 2017-11-21 | 2024-06-18 | Hoffmann-La Roche, Inc. | Solid forms of [(1S)-1-[(2S,4R,5R)-5-(5-amino-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydrofuran-2-yl]propyl] acetate |
| JP7197244B2 (ja) | 2017-12-20 | 2022-12-27 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤として使用するための分岐鎖連結基を有するアミド置換イミダゾ［４，５－ｃ］キノリン化合物 |
| US12226480B2 (en) | 2017-12-21 | 2025-02-18 | Sumitomo Pharma Co., Ltd. | Combination drug including TLR7 agonist |
| PH12021550175A1 (en) | 2018-07-23 | 2022-07-11 | Japan As Represented By Director General Of Nat Institute Of Infectious Diseases | Composition containing influenza vaccine |
| US20220144822A1 (en) * | 2019-03-07 | 2022-05-12 | BioNTech SE | Process for the preparation of a substituted imidazoquinoline |
| US11339159B2 (en) | 2019-07-17 | 2022-05-24 | Pfizer Inc. | Toll-like receptor agonists |
| EP4069693B1 (en) * | 2019-12-03 | 2024-03-20 | F. Hoffmann-La Roche AG | Hydropyrido[1,2-alpha]pyrazine compounds for the treatment of autoimmune diseases |
| AU2021305193A1 (en) * | 2020-07-08 | 2023-02-09 | Purdue Research Foundation | Compounds, compositions, and methods for the treatment of fibrotic diseases and cancer |
| KR20230141754A (ko) | 2020-10-30 | 2023-10-10 | 아박타 라이프 사이언시스 리미티드 | Fap-활성화 혈청 반감기 연장된 치료 접합체 |
| WO2024138157A1 (en) * | 2022-12-22 | 2024-06-27 | Synovo Gmbh | Novel imidazoquinolines with immunostimulatory effects |
Family Cites Families (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8404768L (sv) | 1983-09-27 | 1985-03-28 | Ceskoslovenska Akademie Ved | 9-(aminoalkyl)-8-hydroxiadeniner och sett for deras framstellning |
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| ZA848968B (en) * | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| IL78643A0 (en) * | 1985-05-02 | 1986-08-31 | Wellcome Found | Purine derivatives,their preparation and pharmaceutical compositions containing them |
| GB8918267D0 (en) * | 1989-08-10 | 1990-04-25 | British Aerospace | Weapon systems |
| WO1992015582A1 (en) * | 1991-03-01 | 1992-09-17 | Minnesota Mining And Manufacturing Company | 1-SUBSTITUTED, 2-SUBSTITUTED 1H-IMIDAZO[4,5-c]QUINOLIN-4-AMINES |
| JPH08165292A (ja) | 1993-10-07 | 1996-06-25 | Techno Res Kk | アデニン誘導体、その製造法及び用途 |
| US6110923A (en) * | 1994-06-22 | 2000-08-29 | Biochem Pharma Inc. | Method for treating cancer using novel substituted purinyl derivatives with immunomodulating activity |
| PL319485A1 (en) * | 1994-10-05 | 1997-08-04 | Chiroscience Ltd | Purinic and guanic compounds as pnp inhibitors |
| ATE283855T1 (de) | 1996-07-03 | 2004-12-15 | Sumitomo Pharma | Neue purinderivate |
| CA2311742C (en) * | 1997-11-28 | 2009-06-16 | Sumitomo Pharmaceuticals Co., Ltd. | 6-amino-9-benzyl-8-hydroxypurine derivatives |
| JPH11180981A (ja) | 1997-12-19 | 1999-07-06 | Sumitomo Pharmaceut Co Ltd | 複素環誘導体 |
| TW572758B (en) * | 1997-12-22 | 2004-01-21 | Sumitomo Pharma | Type 2 helper T cell-selective immune response inhibitors comprising purine derivatives |
| JP4160645B2 (ja) | 1997-12-24 | 2008-10-01 | 大日本住友製薬株式会社 | 新規アデニン誘導体及びその医薬用途 |
| JP4189048B2 (ja) | 1997-12-26 | 2008-12-03 | 大日本住友製薬株式会社 | 複素環化合物 |
| DE69917469T2 (de) * | 1998-08-27 | 2005-05-12 | Sumitomo Pharmaceuticals Co., Ltd. | Pyrimidin derivate |
| JP2000159767A (ja) | 1998-11-26 | 2000-06-13 | Sumitomo Pharmaceut Co Ltd | ８−ヒドロキシアデニン誘導体の新規製造法 |
| CZ27399A3 (cs) | 1999-01-26 | 2000-08-16 | Ústav Experimentální Botaniky Av Čr | Substituované dusíkaté heterocyklické deriváty, způsob jejich přípravy, tyto deriváty pro použití jako léčiva, farmaceutická kompozice a kombinovaný farmaceutický přípravek tyto deriváty obsahující a použití těchto derivátů pro výrobu léčiv |
| 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 |
| US6451810B1 (en) * | 1999-06-10 | 2002-09-17 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| GB9924361D0 (en) * | 1999-10-14 | 1999-12-15 | Pfizer Ltd | Purine derivatives |
| US20020040032A1 (en) * | 2000-07-07 | 2002-04-04 | Glasky Michelle S. | Methods for stimulation of synthesis of synaptophysin in the central nervous system |
| US20020128264A1 (en) * | 2000-07-07 | 2002-09-12 | Taylor Eve M. | Methods for treatment of conditions affected by activity of multidrug transporters |
| DK1790344T3 (da) * | 2000-07-07 | 2011-05-02 | Spectrum Pharmaceuticals Inc | Fremgangsmåder til behandling af sygdomsfremkaldt perifer neuropati og beslægtede tilstande |
| WO2002040481A2 (en) * | 2000-11-20 | 2002-05-23 | Millennium Pharmaceuticals, Inc. | Adenine based inhibitors of adenylyl cyclase, pharmaceutical compositions and method of use thereof |
| US6677348B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Aryl ether substituted imidazoquinolines |
| EP1541572A1 (en) | 2000-12-08 | 2005-06-15 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| DE60228229D1 (de) * | 2001-04-17 | 2008-09-25 | Dainippon Sumitomo Pharma Co | Neue adeninderivate |
| ITRM20010465A1 (it) * | 2001-07-31 | 2003-01-31 | Sigma Tau Ind Farmaceuti | Derivati della triazolil-imidazopiridina e delle triazolilpurine utili come ligandi del recettore a2a dell'adenosina e loro uso come medicam |
| EP1719511B1 (en) * | 2001-11-16 | 2008-12-10 | 3M Innovative Properties Company | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide, a pharmaceutical composition comprising the same and use thereof |
| US20060252774A1 (en) * | 2002-05-02 | 2006-11-09 | Vatner Stephen F | Regulation of type 5 adenylyl cyclase for treatment of neurodegenerative and cardiac diseases |
| ATE488246T1 (de) * | 2002-08-15 | 2010-12-15 | 3M Innovative Properties Co | Immunstimulatorische zusammensetzungen und verfahren zur stimulierung einer immunantwort |
| NZ539064A (en) | 2002-09-27 | 2007-09-28 | Dainippon Sumitomo Pharma Co | Novel adenine compound and use thereof |
| JP2004137157A (ja) | 2002-10-16 | 2004-05-13 | Sumitomo Pharmaceut Co Ltd | 新規アデニン誘導体を有効成分として含有する医薬 |
| EA200600069A1 (ru) * | 2003-06-20 | 2006-08-25 | Коли Фармасьютикал Гмбх | Низкомолекулярные антагонисты toll-подобных рецепторов (tlr) |
| WO2005025583A2 (en) * | 2003-09-05 | 2005-03-24 | Anadys Pharmaceuticals, Inc. | Tlr7 ligands for the treatment of hepatitis c |
| JP2005089334A (ja) | 2003-09-12 | 2005-04-07 | Sumitomo Pharmaceut Co Ltd | ８−ヒドロキシアデニン化合物 |
| TWI392678B (zh) | 2004-03-26 | 2013-04-11 | Dainippon Sumitomo Pharma Co | ９-取代-８-氧基腺嘌呤化合物 |
| EP1728792A4 (en) * | 2004-03-26 | 2010-12-15 | Dainippon Sumitomo Pharma Co | 8-OXOADENINE COMPOUND |
| BRPI0611435A2 (pt) * | 2005-05-04 | 2010-09-08 | Pfizer Ltd | derivados de 2-amido-6-amino-8-oxopurina, composições farmacêuticas, uso e processo de preparo dos mesmos |
| EP1908480A4 (en) | 2005-06-03 | 2009-07-01 | Riken | INTERFERON-ALPHA-REGULATOR |
| ES2577514T3 (es) * | 2005-08-22 | 2016-07-15 | The Regents Of The University Of California | Antagonistas de TLR |
| TW200801003A (en) * | 2005-09-16 | 2008-01-01 | Astrazeneca Ab | Novel compounds |
| WO2007034917A1 (ja) * | 2005-09-22 | 2007-03-29 | Dainippon Sumitomo Pharma Co., Ltd. | 新規なアデニン化合物 |
| JPWO2007034882A1 (ja) * | 2005-09-22 | 2009-03-26 | 大日本住友製薬株式会社 | 新規アデニン化合物 |
| JPWO2007034817A1 (ja) * | 2005-09-22 | 2009-03-26 | 大日本住友製薬株式会社 | 新規アデニン化合物 |
| EP1939198A4 (en) * | 2005-09-22 | 2012-02-15 | Dainippon Sumitomo Pharma Co | NEW ADENINE CONNECTION |
| US20090099216A1 (en) * | 2005-09-22 | 2009-04-16 | Astrazeneca Aktiebolag A Corporation Of Sweden | Novel adenine compound |
| TW200745114A (en) * | 2005-09-22 | 2007-12-16 | Astrazeneca Ab | Novel compounds |
| US20090281075A1 (en) * | 2006-02-17 | 2009-11-12 | Pharmacopeia, Inc. | Isomeric purinones and 1h-imidazopyridinones as pkc-theta inhibitors |
| WO2008004948A1 (en) * | 2006-07-05 | 2008-01-10 | Astrazeneca Ab | 8-oxoadenine derivatives acting as modulators of tlr7 |
| AU2007269557B2 (en) * | 2006-07-07 | 2013-11-07 | Gilead Sciences, Inc. | Modulators of toll-like receptor 7 |
| TW200831105A (en) * | 2006-12-14 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| PT2125792E (pt) * | 2007-02-19 | 2011-03-01 | Glaxosmithkline Llc | Derivados de purina como imunomoduladores |
| WO2008114008A1 (en) * | 2007-03-19 | 2008-09-25 | Astrazeneca Ab | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7 ) modulators |
| EP2139894B1 (en) * | 2007-03-19 | 2011-10-26 | AstraZeneca AB | 9-substituted-8-oxo-adenine compounds as toll-like receptor (tlr7) modulators |
| EP2138497A4 (en) | 2007-03-20 | 2012-01-04 | Dainippon Sumitomo Pharma Co | NEW ADENINE CONNECTION |
| AR065784A1 (es) | 2007-03-20 | 2009-07-01 | Dainippon Sumitomo Pharma Co | Derivados de 8-oxo adenina,medicamentos que los contienen y usos como agentes terapeuticos para enfermedades alergicas, antivirales o antibacterianas. |
| JP5400763B2 (ja) * | 2007-05-08 | 2014-01-29 | アストラゼネカ・アクチエボラーグ | 免疫調節特性を有するイミダゾキノリン類 |
| ES2541434T3 (es) * | 2007-06-29 | 2015-07-20 | Gilead Sciences, Inc. | Derivados de purina y su uso como moduladores del receptor de tipo Toll 7 |
| PE20091236A1 (es) * | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| CN102143964A (zh) * | 2008-01-17 | 2011-08-03 | 大日本住友制药株式会社 | 制备腺嘌呤化合物的方法 |
| JPWO2009091031A1 (ja) * | 2008-01-17 | 2011-05-26 | 大日本住友製薬株式会社 | アデニン化合物の製造方法 |
| CN101239980B (zh) | 2008-02-18 | 2011-06-22 | 靳广毅 | 免疫受体调节剂偶联体前体和偶联体及其应用 |
| WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
| UA103195C2 (uk) * | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| GB0908772D0 (en) * | 2009-05-21 | 2009-07-01 | Astrazeneca Ab | New salts 756 |
| EP2507237A1 (en) * | 2009-12-03 | 2012-10-10 | Dainippon Sumitomo Pharma Co., Ltd. | Imidazoquinolines which act via toll - like receptors (tlr) |
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