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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- C07D—HETEROCYCLIC COMPOUNDS
- 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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- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
- Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
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- AIDS & HIV (AREA)
- Biotechnology (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91658607P | 2007-05-08 | 2007-05-08 | |
| 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)
| Publication Number | Publication Date |
|---|---|
| CA2686163A1 true CA2686163A1 (en) | 2008-11-13 |
Family
ID=39596464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002686163A Abandoned CA2686163A1 (en) | 2007-05-08 | 2008-05-06 | Imidazoquinolines with immuno-modulating properties |
Country Status (27)
| Country | Link |
|---|---|
| US (2) | US8436178B2 (OSRAM) |
| EP (1) | EP2155743B1 (OSRAM) |
| JP (1) | JP5400763B2 (OSRAM) |
| KR (1) | KR20100016289A (OSRAM) |
| CN (1) | CN101687867B (OSRAM) |
| AR (1) | AR066492A1 (OSRAM) |
| AU (1) | AU2008247165B2 (OSRAM) |
| BR (1) | BRPI0811125A2 (OSRAM) |
| CA (1) | CA2686163A1 (OSRAM) |
| CL (1) | CL2008001357A1 (OSRAM) |
| CO (1) | CO6251247A2 (OSRAM) |
| CY (1) | CY1113339T1 (OSRAM) |
| DK (1) | DK2155743T3 (OSRAM) |
| EC (1) | ECSP099750A (OSRAM) |
| ES (1) | ES2393037T3 (OSRAM) |
| HR (1) | HRP20120895T1 (OSRAM) |
| IL (1) | IL201572A0 (OSRAM) |
| MX (1) | MX2009011802A (OSRAM) |
| MY (1) | MY150519A (OSRAM) |
| PE (1) | PE20090276A1 (OSRAM) |
| PL (1) | PL2155743T3 (OSRAM) |
| PT (1) | PT2155743E (OSRAM) |
| RU (1) | RU2475487C2 (OSRAM) |
| TW (1) | TW200902529A (OSRAM) |
| UY (1) | UY31069A1 (OSRAM) |
| WO (1) | WO2008135791A1 (OSRAM) |
| ZA (1) | ZA200907547B (OSRAM) |
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| ES2563952T3 (es) | 2004-03-26 | 2016-03-16 | Sumitomo Dainippon Pharma Co., Ltd. | Compuesto de 8-oxoadenina 9-sustituido |
| US8138172B2 (en) * | 2006-07-05 | 2012-03-20 | 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 |
| JPWO2008114819A1 (ja) | 2007-03-20 | 2010-07-08 | 大日本住友製薬株式会社 | 新規アデニン化合物 |
| 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 |
| CA2691444C (en) * | 2007-06-29 | 2016-06-14 | Gilead Sciences, Inc. | Purine derivatives and their use as modulators of toll-like receptor 7 |
| PE20091236A1 (es) | 2007-11-22 | 2009-09-16 | Astrazeneca Ab | Derivados de pirimidina como immunomoduladores de tlr7 |
| 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 |
| 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 |
| JP5577099B2 (ja) | 2008-01-17 | 2014-08-20 | 大日本住友製薬株式会社 | アデニン化合物の製造方法 |
| PL2268618T3 (pl) * | 2008-03-03 | 2015-11-30 | Novartis Ag | Związki i kompozycje jako modulatory aktywności receptorów TLR |
| CN103396415B (zh) * | 2008-03-24 | 2016-08-10 | 4Sc股份有限公司 | 新的取代的咪唑并喹啉化合物 |
| NZ593110A (en) | 2008-12-09 | 2013-06-28 | Gilead Sciences Inc | pteridinone derivatives as MODULATORS OF TOLL-LIKE RECEPTORS |
| GB0908772D0 (en) * | 2009-05-21 | 2009-07-01 | Astrazeneca Ab | New salts 756 |
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