CA2436846C - Thioether substituted imidazoquinolines - Google Patents
Thioether substituted imidazoquinolines Download PDFInfo
- Publication number
- CA2436846C CA2436846C CA2436846A CA2436846A CA2436846C CA 2436846 C CA2436846 C CA 2436846C CA 2436846 A CA2436846 A CA 2436846A CA 2436846 A CA2436846 A CA 2436846A CA 2436846 C CA2436846 C CA 2436846C
- Authority
- CA
- Canada
- Prior art keywords
- imidazo
- butyl
- quinolin
- amine
- alkyl
- 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.)
- Expired - Fee Related
Links
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 5
- 125000000101 thioether group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 102000004127 Cytokines Human genes 0.000 claims abstract description 36
- 108090000695 Cytokines Proteins 0.000 claims abstract description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 230000003612 virological effect Effects 0.000 claims abstract description 12
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 241001465754 Metazoa Species 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000001939 inductive effect Effects 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
- GGQPBQDBBOPNRE-UHFFFAOYSA-N 2-butyl-1-(4-methylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCSC)C3=C(N)N=C21 GGQPBQDBBOPNRE-UHFFFAOYSA-N 0.000 claims description 5
- IYYQHIKYOLNSII-UHFFFAOYSA-N 2-butyl-1-(5-methylsulfanylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCCSC)C3=C(N)N=C21 IYYQHIKYOLNSII-UHFFFAOYSA-N 0.000 claims description 5
- GOLWPSYGOUZWJW-UHFFFAOYSA-N 2-butyl-1-(5-methylsulfonylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCCS(C)(=O)=O)C3=C(N)N=C21 GOLWPSYGOUZWJW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- YGHNDRUQXWKZTE-UHFFFAOYSA-N 1-(2-phenylsulfanylethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCSC1=CC=CC=C1 YGHNDRUQXWKZTE-UHFFFAOYSA-N 0.000 claims description 4
- MGPQKILVFQBILK-UHFFFAOYSA-N 1-(4-methylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCSC)C=NC3=C(N)N=C21 MGPQKILVFQBILK-UHFFFAOYSA-N 0.000 claims description 4
- HQIIWMIWSDDYEN-UHFFFAOYSA-N 1-(5-methylsulfonylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCCS(=O)(=O)C)C=NC3=C(N)N=C21 HQIIWMIWSDDYEN-UHFFFAOYSA-N 0.000 claims description 4
- PQFXURFRUXOEAP-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)propyl]-2-butylimidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCS(=O)(=O)C1=CC=CC=C1 PQFXURFRUXOEAP-UHFFFAOYSA-N 0.000 claims description 4
- SQWJZYADOGELTF-UHFFFAOYSA-N 1-[4-(benzenesulfonyl)butyl]-2-butylimidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCS(=O)(=O)C1=CC=CC=C1 SQWJZYADOGELTF-UHFFFAOYSA-N 0.000 claims description 4
- RFZSZPJGVHUALX-UHFFFAOYSA-N 2-butyl-1-(3-methylsulfonylpropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCS(C)(=O)=O)C3=C(N)N=C21 RFZSZPJGVHUALX-UHFFFAOYSA-N 0.000 claims description 4
- MJHQZBHZDWKOFC-UHFFFAOYSA-N 2-butyl-1-(4-methylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCS(C)(=O)=O)C3=C(N)N=C21 MJHQZBHZDWKOFC-UHFFFAOYSA-N 0.000 claims description 4
- JRJNASADLBHSEQ-UHFFFAOYSA-N 2-butyl-1-(4-phenylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCSC1=CC=CC=C1 JRJNASADLBHSEQ-UHFFFAOYSA-N 0.000 claims description 4
- AESUFKUCZZMYMP-UHFFFAOYSA-N 2-ethyl-1-(5-methylsulfonylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCCS(C)(=O)=O)C3=C(N)N=C21 AESUFKUCZZMYMP-UHFFFAOYSA-N 0.000 claims description 4
- BUTWVWNILGEQEP-UHFFFAOYSA-N 2-hexyl-1-(5-methylsulfonylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCCS(C)(=O)=O)C3=C(N)N=C21 BUTWVWNILGEQEP-UHFFFAOYSA-N 0.000 claims description 4
- WDLQXBIQXNCFEJ-UHFFFAOYSA-N 2-methyl-1-(5-methylsulfonylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCCCS(C)(=O)=O)C3=C(N)N=C21 WDLQXBIQXNCFEJ-UHFFFAOYSA-N 0.000 claims description 4
- RUJRPGRCDWWGBJ-UHFFFAOYSA-N 1-(4-methylsulfonylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCS(=O)(=O)C)C=NC3=C(N)N=C21 RUJRPGRCDWWGBJ-UHFFFAOYSA-N 0.000 claims description 3
- WPIAYGIYAOYXOR-UHFFFAOYSA-N 1-(4-phenylsulfanylbutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCSC1=CC=CC=C1 WPIAYGIYAOYXOR-UHFFFAOYSA-N 0.000 claims description 3
- YYSCCZQXBYPCOK-UHFFFAOYSA-N 1-[4-(benzenesulfonyl)butyl]imidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1CCCCS(=O)(=O)C1=CC=CC=C1 YYSCCZQXBYPCOK-UHFFFAOYSA-N 0.000 claims description 3
- AWLYMRYTWLQFEZ-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-(5-methylsulfonylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCCS(C)(=O)=O)C3=C(N)N=C21 AWLYMRYTWLQFEZ-UHFFFAOYSA-N 0.000 claims description 3
- CAQCTXINZFFYPZ-UHFFFAOYSA-N 2-butyl-1-(5-methylsulfinylpentyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCCS(C)=O)C3=C(N)N=C21 CAQCTXINZFFYPZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- VGGJZPGKFGNYRQ-UHFFFAOYSA-N 2-butyl-1-(2-phenylsulfanylethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3CCCCC3=C2N1CCSC1=CC=CC=C1 VGGJZPGKFGNYRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 22
- 230000028993 immune response Effects 0.000 abstract description 12
- 150000003568 thioethers Chemical group 0.000 abstract description 10
- 238000011282 treatment Methods 0.000 abstract description 10
- 239000003607 modifier Substances 0.000 abstract description 5
- GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 abstract description 2
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 abstract 1
- 229940124669 imidazoquinoline Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 103
- 239000007787 solid Substances 0.000 description 94
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 80
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 50
- 238000003756 stirring Methods 0.000 description 50
- 229910052799 carbon Inorganic materials 0.000 description 49
- 229910052757 nitrogen Inorganic materials 0.000 description 47
- 239000000463 material Substances 0.000 description 44
- 238000000746 purification Methods 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 238000007429 general method Methods 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000010410 layer Substances 0.000 description 34
- 229920006395 saturated elastomer Polymers 0.000 description 33
- 239000012044 organic layer Substances 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 239000012267 brine Substances 0.000 description 25
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
- 229910001868 water Inorganic materials 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 24
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
- 235000017557 sodium bicarbonate Nutrition 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000001914 filtration Methods 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
- -1 Compounds Compounds Chemical class 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 18
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 16
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 239000012456 homogeneous solution Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 13
- 102100040247 Tumor necrosis factor Human genes 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000003039 volatile agent Substances 0.000 description 12
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 11
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 11
- UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 11
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000007796 conventional method Methods 0.000 description 10
- 230000006698 induction Effects 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 8
- SKPRPEJLFKCOAB-UHFFFAOYSA-N 3-nitroquinolin-4-amine Chemical compound C1=CC=C2C(N)=C([N+]([O-])=O)C=NC2=C1 SKPRPEJLFKCOAB-UHFFFAOYSA-N 0.000 description 7
- 102000014150 Interferons Human genes 0.000 description 7
- 108010050904 Interferons Proteins 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 229940079322 interferon Drugs 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 6
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- SWNVKLSIDCAMHR-UHFFFAOYSA-N 2-butyl-1-(4-chlorobutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCCl)C3=C(N)N=C21 SWNVKLSIDCAMHR-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical group CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- KDMZAUSUQUNVKZ-UHFFFAOYSA-N 1-(4-chlorobutyl)imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2CCCCCl KDMZAUSUQUNVKZ-UHFFFAOYSA-N 0.000 description 3
- CVLYGNCKTLGOLP-UHFFFAOYSA-N 2-butyl-1-(3-chloropropyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCl)C3=C(N)N=C21 CVLYGNCKTLGOLP-UHFFFAOYSA-N 0.000 description 3
- ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 3
- IFBOAZTZKKYYGI-UHFFFAOYSA-N 4-n-(5-methylsulfanylpentyl)quinoline-3,4-diamine Chemical compound C1=CC=C2C(NCCCCCSC)=C(N)C=NC2=C1 IFBOAZTZKKYYGI-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 210000005260 human cell Anatomy 0.000 description 3
- 239000002955 immunomodulating agent Substances 0.000 description 3
- 229940121354 immunomodulator Drugs 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US25421800P | 2000-12-08 | 2000-12-08 | |
| US60/254,218 | 2000-12-08 | ||
| PCT/US2001/046697 WO2002046192A2 (en) | 2000-12-08 | 2001-12-06 | Thioether substituted imidazoquinolines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2436846A1 CA2436846A1 (en) | 2002-06-13 |
| CA2436846C true CA2436846C (en) | 2010-11-16 |
Family
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| CA002431151A Withdrawn CA2431151A1 (en) | 2000-12-08 | 2001-12-06 | Heterocyclic ether substituted imidazoquinolines |
| CA002436984A Abandoned CA2436984A1 (en) | 2000-12-08 | 2001-12-06 | Urea substituted imidazoquinoline ethers |
| CA002430844A Withdrawn CA2430844A1 (en) | 2000-12-08 | 2001-12-06 | Aryl ether substituted imidazoquinolines |
| CA002436983A Abandoned CA2436983A1 (en) | 2000-12-08 | 2001-12-06 | Sulfonamido ether substituted imidazoquinolines |
| CA2436846A Expired - Fee Related CA2436846C (en) | 2000-12-08 | 2001-12-06 | Thioether substituted imidazoquinolines |
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| CA2436980A Expired - Fee Related CA2436980C (en) | 2000-12-08 | 2001-12-06 | Amido ether substituted imidazoquinolines |
| CA002431151A Withdrawn CA2431151A1 (en) | 2000-12-08 | 2001-12-06 | Heterocyclic ether substituted imidazoquinolines |
| CA002436984A Abandoned CA2436984A1 (en) | 2000-12-08 | 2001-12-06 | Urea substituted imidazoquinoline ethers |
| CA002430844A Withdrawn CA2430844A1 (en) | 2000-12-08 | 2001-12-06 | Aryl ether substituted imidazoquinolines |
| CA002436983A Abandoned CA2436983A1 (en) | 2000-12-08 | 2001-12-06 | Sulfonamido ether substituted imidazoquinolines |
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| US5741908A (en) | 1996-06-21 | 1998-04-21 | Minnesota Mining And Manufacturing Company | Process for reparing imidazoquinolinamines |
| UA67760C2 (uk) * | 1997-12-11 | 2004-07-15 | Міннесота Майнінг Енд Мануфакчурінг Компані | Імідазонафтиридин та тетрагідроімідазонафтиридин, фармацевтична композиція, спосіб індукування біосинтезу цитокінів та спосіб лікування вірусної інфекції, проміжні сполуки |
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| SI1478327T1 (sl) | 2002-02-22 | 2015-08-31 | Meda Ab | Metoda za zmanjšanje in zdravljenje imunosupresije, inducirane z UV-B |
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