ZA200305274B - Thioether substituted imidazoquinolines. - Google Patents
Thioether substituted imidazoquinolines. Download PDFInfo
- Publication number
- ZA200305274B ZA200305274B ZA200305274A ZA200305274A ZA200305274B ZA 200305274 B ZA200305274 B ZA 200305274B ZA 200305274 A ZA200305274 A ZA 200305274A ZA 200305274 A ZA200305274 A ZA 200305274A ZA 200305274 B ZA200305274 B ZA 200305274B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- imidazo
- animal
- alkyl
- composition
- Prior art date
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- 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 description 136
- 238000000034 method Methods 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 54
- 241001465754 Metazoa Species 0.000 claims description 50
- 108090000695 Cytokines Proteins 0.000 claims description 41
- 102000004127 Cytokines Human genes 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 239000000126 substance Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 230000015572 biosynthetic process Effects 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 19
- -1 5-(methylsulfonyl)pentyl Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 230000001939 inductive effect Effects 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 230000003612 virological effect Effects 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 230000001613 neoplastic effect Effects 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 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
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- 108090001069 Chymopapain Proteins 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 2
- 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 2
- XXAXVMUWHZHZMJ-UHFFFAOYSA-N Chymopapain Chemical compound OC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O XXAXVMUWHZHZMJ-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 100
- 239000000243 solution Substances 0.000 description 71
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000007787 solid Substances 0.000 description 67
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 49
- 238000003756 stirring Methods 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 45
- 239000000463 material Substances 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- 238000000746 purification Methods 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 239000010410 layer Substances 0.000 description 31
- 238000007429 general method Methods 0.000 description 28
- 229920006395 saturated elastomer Polymers 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000012267 brine Substances 0.000 description 21
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
- 235000017557 sodium bicarbonate Nutrition 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 13
- 239000012456 homogeneous solution Substances 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 230000028993 immune response Effects 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 239000003039 volatile agent Substances 0.000 description 11
- 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
- 238000007796 conventional method Methods 0.000 description 10
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 10
- UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
- 150000003568 thioethers Chemical group 0.000 description 9
- 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 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 235000019270 ammonium chloride Nutrition 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
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 230000000694 effects Effects 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 239000003607 modifier Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 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
- 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
- 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
- 150000001204 N-oxides Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical group CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 2
- AKIJIZNXVMIBLK-UHFFFAOYSA-N 1-(2-chloroethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2CCCl AKIJIZNXVMIBLK-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 description 2
- GERCYVFOWLKCQI-UHFFFAOYSA-N 1-[4-(benzenesulfonyl)butyl]-n,n-dibenzylimidazo[4,5-c]quinolin-4-amine Chemical compound C=1C=CC=CC=1S(=O)(=O)CCCCN(C1=C2C=CC=CC2=N2)C=NC1=C2N(CC=1C=CC=CC=1)CC1=CC=CC=C1 GERCYVFOWLKCQI-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- ZUIKRGWWTXWONA-UHFFFAOYSA-N 2-(2-methoxyethyl)-1-(5-methylsulfanylpentyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCCSC)C3=CN=C21 ZUIKRGWWTXWONA-UHFFFAOYSA-N 0.000 description 2
- GKUMQOXCEWXRNG-UHFFFAOYSA-N 2-butyl-1-(2-phenylsulfanylethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine;hydrochloride Chemical compound Cl.CCCCC1=NC2=C(N)N=C3CCCCC3=C2N1CCSC1=CC=CC=C1 GKUMQOXCEWXRNG-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- UNIZYILOSNKXJS-UHFFFAOYSA-N 2-butyl-1-(5-methylsulfanylpentyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCCSC)C3=CN=C21 UNIZYILOSNKXJS-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- WHVBPOJIJMSCAH-UHFFFAOYSA-N 2-ethyl-1-(5-methylsulfanylpentyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCCSC)C3=CN=C21 WHVBPOJIJMSCAH-UHFFFAOYSA-N 0.000 description 2
- QSAQUNLLOBJDJG-UHFFFAOYSA-N 2-hexyl-1-(5-methylsulfanylpentyl)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCCSC)C3=CN=C21 QSAQUNLLOBJDJG-UHFFFAOYSA-N 0.000 description 2
- WDIZFBONYOHZQR-UHFFFAOYSA-N 4-[(3-nitroquinolin-4-yl)amino]butan-1-ol Chemical compound C1=CC=C2C(NCCCCO)=C([N+]([O-])=O)C=NC2=C1 WDIZFBONYOHZQR-UHFFFAOYSA-N 0.000 description 2
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25421800P | 2000-12-08 | 2000-12-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305274B true ZA200305274B (en) | 2004-10-18 |
Family
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Family Applications (6)
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| ZA200305274A ZA200305274B (en) | 2000-12-08 | 2003-07-08 | Thioether substituted imidazoquinolines. |
| ZA200305273A ZA200305273B (en) | 2000-12-08 | 2003-07-08 | Sulfonamido ether substituted imidazoquinolines. |
| ZA2003/05272A ZA200305272B (en) | 2000-12-08 | 2003-07-08 | Urea substituted imidazoquinoline ethers |
| ZA200305271A ZA200305271B (en) | 2000-12-08 | 2003-07-08 | Amido ether substituted imidazoquinolines. |
| ZA200305270A ZA200305270B (en) | 2000-12-08 | 2003-07-08 | Heterocyclic ether substituted imidazoquinolines. |
| ZA200305275A ZA200305275B (en) | 2000-12-08 | 2003-07-08 | Aryl ether substituted imidazoquinolines. |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305273A ZA200305273B (en) | 2000-12-08 | 2003-07-08 | Sulfonamido ether substituted imidazoquinolines. |
| ZA2003/05272A ZA200305272B (en) | 2000-12-08 | 2003-07-08 | Urea substituted imidazoquinoline ethers |
| ZA200305271A ZA200305271B (en) | 2000-12-08 | 2003-07-08 | Amido ether substituted imidazoquinolines. |
| ZA200305270A ZA200305270B (en) | 2000-12-08 | 2003-07-08 | Heterocyclic ether substituted imidazoquinolines. |
| ZA200305275A ZA200305275B (en) | 2000-12-08 | 2003-07-08 | Aryl ether substituted imidazoquinolines. |
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| EP (6) | EP1341791B1 (xx) |
| JP (7) | JP2004521092A (xx) |
| KR (6) | KR20030070049A (xx) |
| CN (6) | CN1479739A (xx) |
| AR (6) | AR035669A1 (xx) |
| AT (3) | ATE296301T1 (xx) |
| AU (12) | AU3951602A (xx) |
| BR (6) | BR0116026A (xx) |
| CA (6) | CA2436983A1 (xx) |
| CY (2) | CY1105586T1 (xx) |
| CZ (6) | CZ20031561A3 (xx) |
| DE (3) | DE60117859T2 (xx) |
| DK (3) | DK1343784T3 (xx) |
| EE (6) | EE200300270A (xx) |
| ES (3) | ES2242782T3 (xx) |
| HK (3) | HK1064383A1 (xx) |
| HR (6) | HRP20030463A2 (xx) |
| HU (6) | HUP0600600A2 (xx) |
| IL (6) | IL155950A0 (xx) |
| MX (6) | MXPA03004975A (xx) |
| NO (6) | NO20032451L (xx) |
| NZ (6) | NZ526089A (xx) |
| PL (7) | PL361948A1 (xx) |
| PT (2) | PT1341791E (xx) |
| RU (6) | RU2003116063A (xx) |
| SI (1) | SI1341790T1 (xx) |
| SK (6) | SK7122003A3 (xx) |
| TW (3) | TWI222972B (xx) |
| UA (2) | UA74852C2 (xx) |
| WO (6) | WO2002046189A2 (xx) |
| ZA (6) | ZA200305274B (xx) |
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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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