KR20060035637A - 술폰아미드 치환된 이미다조퀴놀린 - Google Patents
술폰아미드 치환된 이미다조퀴놀린 Download PDFInfo
- Publication number
- KR20060035637A KR20060035637A KR1020057024904A KR20057024904A KR20060035637A KR 20060035637 A KR20060035637 A KR 20060035637A KR 1020057024904 A KR1020057024904 A KR 1020057024904A KR 20057024904 A KR20057024904 A KR 20057024904A KR 20060035637 A KR20060035637 A KR 20060035637A
- Authority
- KR
- South Korea
- Prior art keywords
- imidazo
- quinolin
- amino
- butyl
- mmol
- 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.)
- Ceased
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 abstract description 5
- 125000000565 sulfonamide group Chemical group 0.000 title abstract description 3
- 229940124530 sulfonamide Drugs 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 102000004127 Cytokines Human genes 0.000 claims abstract description 25
- 108090000695 Cytokines Proteins 0.000 claims abstract description 25
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 16
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 13
- 230000003612 virological effect Effects 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims description 22
- 241001465754 Metazoa Species 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 230000001939 inductive effect Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- NVNWHRIYBUUBAJ-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 NVNWHRIYBUUBAJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 1
- 230000028993 immune response Effects 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 9
- GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 86
- 229910052757 nitrogen Inorganic materials 0.000 description 83
- 229910052799 carbon Inorganic materials 0.000 description 77
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000007787 solid Substances 0.000 description 55
- 238000002844 melting Methods 0.000 description 45
- 230000008018 melting Effects 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- 239000000243 solution Substances 0.000 description 43
- 238000007429 general method Methods 0.000 description 41
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- -1 imidazoquinoline compound Chemical class 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000463 material Substances 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 13
- 229940086542 triethylamine Drugs 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 11
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 11
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 11
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 230000006698 induction Effects 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000005576 amination reaction Methods 0.000 description 8
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 108010050904 Interferons Proteins 0.000 description 7
- 102000014150 Interferons Human genes 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 229940079322 interferon Drugs 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 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 6
- 0 C[n]1c2c(cccc3)c3nc(N)c2nc1* Chemical compound C[n]1c2c(cccc3)c3nc(N)c2nc1* 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004103 aminoalkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 102000006992 Interferon-alpha Human genes 0.000 description 5
- 108010047761 Interferon-alpha Proteins 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229940124669 imidazoquinoline Drugs 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000003456 sulfonamides Chemical group 0.000 description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 4
- KZWUQTRMSBGBBN-UHFFFAOYSA-N 1-(3-aminopropyl)-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCN)C3=C(N)N=C21 KZWUQTRMSBGBBN-UHFFFAOYSA-N 0.000 description 4
- ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- GHDRXJRPAIWZSQ-UHFFFAOYSA-N 1-(4-aminobutyl)-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCCN)C3=C(N)N=C21 GHDRXJRPAIWZSQ-UHFFFAOYSA-N 0.000 description 3
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- XYYKPSXKBVBMHJ-UHFFFAOYSA-N 3-(2-butylimidazo[4,5-c]quinolin-1-yl)propan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCN)C3=CN=C21 XYYKPSXKBVBMHJ-UHFFFAOYSA-N 0.000 description 3
- BHBQPNUVSWIHOD-UHFFFAOYSA-N 4-(2-hexylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCN)C3=CN=C21 BHBQPNUVSWIHOD-UHFFFAOYSA-N 0.000 description 3
- YHQPYMQQMBVULM-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinolin-4-amine Chemical class C1CCCC2=C1N=C(N)C1=C2NC=N1 YHQPYMQQMBVULM-UHFFFAOYSA-N 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000002965 ELISA Methods 0.000 description 3
- 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 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 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000002955 immunomodulating agent Substances 0.000 description 3
- 229940121354 immunomodulator Drugs 0.000 description 3
- VQDBDUUBRYJICF-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]-4-methylbenzenesulfonamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCNS(=O)(=O)C1=CC=C(C)C=C1 VQDBDUUBRYJICF-UHFFFAOYSA-N 0.000 description 3
- XCXOKNJKBTXVOO-UHFFFAOYSA-N n-[2-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCNS(C)(=O)=O)C3=C(N)N=C21 XCXOKNJKBTXVOO-UHFFFAOYSA-N 0.000 description 3
- NAKYGPHKOSYEKG-UHFFFAOYSA-N n-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]-5-(dimethylamino)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCCC)=CC=CC2=C1N(C)C NAKYGPHKOSYEKG-UHFFFAOYSA-N 0.000 description 3
- YSRVRSNRDOIDKT-UHFFFAOYSA-N n-[3-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)propyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 YSRVRSNRDOIDKT-UHFFFAOYSA-N 0.000 description 3
- NPUKURXYLSVTBZ-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound C1CCCC2=C(N(C(CCOC)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 NPUKURXYLSVTBZ-UHFFFAOYSA-N 0.000 description 3
- PSBXFVDVSGBSCS-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CC(C)(C)CNS(C)(=O)=O)C3=C(N)N=C21 PSBXFVDVSGBSCS-UHFFFAOYSA-N 0.000 description 3
- XKWXZYMYHSFUJW-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]-4-methylbenzenesulfonamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=C(C)C=C1 XKWXZYMYHSFUJW-UHFFFAOYSA-N 0.000 description 3
- YODWHKFJJPXAQD-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]benzenesulfonamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=CC=C1 YODWHKFJJPXAQD-UHFFFAOYSA-N 0.000 description 3
- OCGIGXADEWZZPL-UHFFFAOYSA-N n-[3-[4-amino-2-(3-phenoxypropyl)imidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CCCNS(=O)(=O)C)C=1CCCOC1=CC=CC=C1 OCGIGXADEWZZPL-UHFFFAOYSA-N 0.000 description 3
- GUWKXTZVCYGDQL-UHFFFAOYSA-N n-[3-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 GUWKXTZVCYGDQL-UHFFFAOYSA-N 0.000 description 3
- BKSGGCIFTFXQAH-UHFFFAOYSA-N n-[4-(4-amino-2-ethylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 BKSGGCIFTFXQAH-UHFFFAOYSA-N 0.000 description 3
- HBPLVGFQUJGBPG-UHFFFAOYSA-N n-[4-(4-amino-2-methyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1CCCC2=C(N(C(C)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 HBPLVGFQUJGBPG-UHFFFAOYSA-N 0.000 description 3
- WMJJJJKGVPSSSN-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 WMJJJJKGVPSSSN-UHFFFAOYSA-N 0.000 description 3
- CCJISYWPWXKKRX-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]ethanesulfonamide Chemical compound C1=CC=CC2=C3N(CCCCNS(=O)(=O)CC)C(C)=NC3=C(N)N=C21 CCJISYWPWXKKRX-UHFFFAOYSA-N 0.000 description 3
- DOZGTYGEBVOOFZ-UHFFFAOYSA-N n-[4-(4-amino-2-methylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 DOZGTYGEBVOOFZ-UHFFFAOYSA-N 0.000 description 3
- ASKWICZHWUUNCD-UHFFFAOYSA-N n-[4-(4-amino-2-pentyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1CCCC2=C(N(C(CCCCC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 ASKWICZHWUUNCD-UHFFFAOYSA-N 0.000 description 3
- TWCMRMWDBFPHTQ-UHFFFAOYSA-N n-[4-(4-amino-2-pentylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 TWCMRMWDBFPHTQ-UHFFFAOYSA-N 0.000 description 3
- GYAGKIRWXLWSHY-UHFFFAOYSA-N n-[4-(4-amino-2-pentylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCCC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 GYAGKIRWXLWSHY-UHFFFAOYSA-N 0.000 description 3
- KCQWOAPKZGATTP-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 KCQWOAPKZGATTP-UHFFFAOYSA-N 0.000 description 3
- IOHFRCYGKLBIJH-UHFFFAOYSA-N n-[4-[4-amino-2-(3-phenoxypropyl)imidazo[4,5-c]quinolin-1-yl]butyl]methanesulfonamide Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CCCCNS(=O)(=O)C)C=1CCCOC1=CC=CC=C1 IOHFRCYGKLBIJH-UHFFFAOYSA-N 0.000 description 3
- RUKUTJCNUFLTPJ-UHFFFAOYSA-N n-[4-[4-amino-2-(cyclopropylmethyl)imidazo[4,5-c]quinolin-1-yl]butyl]methanesulfonamide Chemical compound N=1C2=C(N)N=C3C=CC=CC3=C2N(CCCCNS(=O)(=O)C)C=1CC1CC1 RUKUTJCNUFLTPJ-UHFFFAOYSA-N 0.000 description 3
- NIXWJLVPEUCHEH-UHFFFAOYSA-N n-[8-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)octyl]benzenesulfonamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCCCCCNS(=O)(=O)C1=CC=CC=C1 NIXWJLVPEUCHEH-UHFFFAOYSA-N 0.000 description 3
- ZMSMSQMXTFIFJO-UHFFFAOYSA-N n-[8-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)octyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCCCCCNS(C)(=O)=O)C3=C(N)N=C21 ZMSMSQMXTFIFJO-UHFFFAOYSA-N 0.000 description 3
- OEWIOBQTRKZSJO-UHFFFAOYSA-N n-[8-(4-aminoimidazo[4,5-c]quinolin-1-yl)octyl]methanesulfonamide Chemical compound C1=CC=CC2=C3N(CCCCCCCCNS(=O)(=O)C)C=NC3=C(N)N=C21 OEWIOBQTRKZSJO-UHFFFAOYSA-N 0.000 description 3
- DWLBGOWKIPBKHE-UHFFFAOYSA-N n-[8-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]octyl]benzenesulfonamide Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCCCCCNS(=O)(=O)C1=CC=CC=C1 DWLBGOWKIPBKHE-UHFFFAOYSA-N 0.000 description 3
- ZOCPCRFSEJMATG-UHFFFAOYSA-N n-[8-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]octyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCCCCCNS(C)(=O)=O)C3=C(N)N=C21 ZOCPCRFSEJMATG-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- SVBZCXQPNPURIX-UHFFFAOYSA-N 1-(2-amino-2-methylpropyl)-2-(ethoxymethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)N)C3=C(N)N=C21 SVBZCXQPNPURIX-UHFFFAOYSA-N 0.000 description 2
- YETCZFGQAKYIEX-UHFFFAOYSA-N 1-(2-aminoethyl)-2-butylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCN)C3=C(N)N=C21 YETCZFGQAKYIEX-UHFFFAOYSA-N 0.000 description 2
- KRQJNCKJBILJJJ-UHFFFAOYSA-N 1-(3-aminopropyl)-2-butylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCN)C3=C(N)N=C21 KRQJNCKJBILJJJ-UHFFFAOYSA-N 0.000 description 2
- OCBWXUGUCGMZBA-UHFFFAOYSA-N 1-(4-aminobutyl)-2-pentylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCCC)=N3)CCCCN)C3=C(N)N=C21 OCBWXUGUCGMZBA-UHFFFAOYSA-N 0.000 description 2
- JUWNVLFAZIWTMU-UHFFFAOYSA-N 1-(8-aminooctyl)-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCCCCCN)C3=C(N)N=C21 JUWNVLFAZIWTMU-UHFFFAOYSA-N 0.000 description 2
- ZMEHZFJSLRYXOO-UHFFFAOYSA-N 1-(8-aminooctyl)-2-butylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCCCCCCN)C3=C(N)N=C21 ZMEHZFJSLRYXOO-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- MJWNZUXIXLDUET-UHFFFAOYSA-N 2-methyl-1-n-(3-nitroquinolin-4-yl)propane-1,2-diamine Chemical compound C1=CC=C2C(NCC(C)(N)C)=C([N+]([O-])=O)C=NC2=C1 MJWNZUXIXLDUET-UHFFFAOYSA-N 0.000 description 2
- GPKDGVXBXQTHRY-UHFFFAOYSA-N 3-chloropropane-1-sulfonyl chloride Chemical compound ClCCCS(Cl)(=O)=O GPKDGVXBXQTHRY-UHFFFAOYSA-N 0.000 description 2
- LTPVCZQGBDHLMG-UHFFFAOYSA-N 4-(2-ethylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCN)C3=CN=C21 LTPVCZQGBDHLMG-UHFFFAOYSA-N 0.000 description 2
- HKHKLZGFYFCZFA-UHFFFAOYSA-N 4-(2-propylimidazo[4,5-c]quinolin-1-yl)butan-1-amine Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCN)C3=CN=C21 HKHKLZGFYFCZFA-UHFFFAOYSA-N 0.000 description 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 2
- 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 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- XPDXVDYUQZHFPV-UHFFFAOYSA-N Dansyl Chloride Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(Cl)(=O)=O XPDXVDYUQZHFPV-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 241000701806 Human papillomavirus Species 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 102000000589 Interleukin-1 Human genes 0.000 description 2
- 108010063738 Interleukins Proteins 0.000 description 2
- 102000015696 Interleukins Human genes 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 102100040247 Tumor necrosis factor Human genes 0.000 description 2
- 206010052428 Wound Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 210000003719 b-lymphocyte Anatomy 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 210000002443 helper t lymphocyte Anatomy 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 210000005260 human cell Anatomy 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NSHFLKZNBPJNPA-UHFFFAOYSA-N imidazo[4,5-c]quinolin-2-one Chemical class C1=CC=C2C3=NC(=O)N=C3C=NC2=C1 NSHFLKZNBPJNPA-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229940047122 interleukins Drugs 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- CFAXOSMOLWQBGF-UHFFFAOYSA-N n-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]-4-methylbenzenesulfonamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=C(C)C=C1 CFAXOSMOLWQBGF-UHFFFAOYSA-N 0.000 description 2
- ZGEPNYAAUQVVLM-UHFFFAOYSA-N n-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]benzenesulfonamide Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=CC=C1 ZGEPNYAAUQVVLM-UHFFFAOYSA-N 0.000 description 2
- MZXTVCBMZQDXTJ-UHFFFAOYSA-N n-[3-(4-amino-2-butylimidazo[4,5-c]quinolin-1-yl)propyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 MZXTVCBMZQDXTJ-UHFFFAOYSA-N 0.000 description 2
- FRXDVFQORNBEFL-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 FRXDVFQORNBEFL-UHFFFAOYSA-N 0.000 description 2
- FDURDVQGNXYXGG-UHFFFAOYSA-N n-[3-[4-amino-2-(ethoxymethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-1-yl]propyl]methanesulfonamide Chemical compound C1CCCC2=C(N(C(COCC)=N3)CCCNS(C)(=O)=O)C3=C(N)N=C21 FDURDVQGNXYXGG-UHFFFAOYSA-N 0.000 description 2
- MHKJUVWISSLCEC-UHFFFAOYSA-N n-[4-(2-hexylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCNS(C)(=O)=O)C3=CN=C21 MHKJUVWISSLCEC-UHFFFAOYSA-N 0.000 description 2
- GMDODJQAFXHURB-UHFFFAOYSA-N n-[4-(2-propylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCC1=NC2=CN=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 GMDODJQAFXHURB-UHFFFAOYSA-N 0.000 description 2
- YZOQZEXYFLXNKA-UHFFFAOYSA-N n-[4-(4-amino-2-ethylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 YZOQZEXYFLXNKA-UHFFFAOYSA-N 0.000 description 2
- TWEWOQRUFLEQNL-UHFFFAOYSA-N n-[4-(4-amino-2-hexylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 TWEWOQRUFLEQNL-UHFFFAOYSA-N 0.000 description 2
- ZUFWEBGOLJHBJM-UHFFFAOYSA-N n-[4-(4-amino-2-hexylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCCCC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 ZUFWEBGOLJHBJM-UHFFFAOYSA-N 0.000 description 2
- KSQUPKPKVHSLDC-UHFFFAOYSA-N n-[4-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 KSQUPKPKVHSLDC-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 210000001539 phagocyte Anatomy 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000013014 purified material Substances 0.000 description 2
- UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 201000010153 skin papilloma Diseases 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YJKZDGOMTKOYQK-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CCC1CCNCC1 YJKZDGOMTKOYQK-UHFFFAOYSA-N 0.000 description 1
- MTROHLWKMKQWOD-UHFFFAOYSA-N 1-(3-aminopropyl)-2-(2-methoxyethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(CCOC)=N3)CCCN)C3=C(N)N=C21 MTROHLWKMKQWOD-UHFFFAOYSA-N 0.000 description 1
- RYYIXBUGTMXUKX-UHFFFAOYSA-N 1-(3-aminopropyl)-2-(ethoxymethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(COCC)=N3)CCCN)C3=C(N)N=C21 RYYIXBUGTMXUKX-UHFFFAOYSA-N 0.000 description 1
- HVJUMTMMTHTXOF-UHFFFAOYSA-N 1-(3-aminopropyl)-2-(ethoxymethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CCCN)C3=C(N)N=C21 HVJUMTMMTHTXOF-UHFFFAOYSA-N 0.000 description 1
- KESMJWJYOFRFNM-UHFFFAOYSA-N 1-(3-aminopropyl)-2-methylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(C)=N3)CCCN)C3=C(N)N=C21 KESMJWJYOFRFNM-UHFFFAOYSA-N 0.000 description 1
- CDRXULFWJQDMKB-UHFFFAOYSA-N 1-(4-aminobutyl)-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CCOC)=N3)CCCCN)C3=C(N)N=C21 CDRXULFWJQDMKB-UHFFFAOYSA-N 0.000 description 1
- DJILPZGMLMGVDD-UHFFFAOYSA-N 1-(4-aminobutyl)-2-ethylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCN)C3=C(N)N=C21 DJILPZGMLMGVDD-UHFFFAOYSA-N 0.000 description 1
- QDRPAMSKNPUKMS-UHFFFAOYSA-N 1-(4-aminobutyl)-2-methyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(C)=N3)CCCCN)C3=C(N)N=C21 QDRPAMSKNPUKMS-UHFFFAOYSA-N 0.000 description 1
- HLCXAADJSWAECI-UHFFFAOYSA-N 1-(4-aminobutyl)-2-pentyl-6,7,8,9-tetrahydroimidazo[4,5-c]quinolin-4-amine Chemical compound C1CCCC2=C(N(C(CCCCC)=N3)CCCCN)C3=C(N)N=C21 HLCXAADJSWAECI-UHFFFAOYSA-N 0.000 description 1
- HDDNSPWJCZZICL-UHFFFAOYSA-N 1-(6-methoxyquinolin-8-yl)-2-methylimidazo[4,5-c]quinoline Chemical compound N1=CC=CC2=CC(OC)=CC(N3C4=C5C=CC=CC5=NC=C4N=C3C)=C21 HDDNSPWJCZZICL-UHFFFAOYSA-N 0.000 description 1
- GQFYPRWOJHWGIV-UHFFFAOYSA-N 1-(8-aminooctyl)imidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C3N(CCCCCCCCN)C=NC3=C(N)N=C21 GQFYPRWOJHWGIV-UHFFFAOYSA-N 0.000 description 1
- URMAKSLECABUCE-UHFFFAOYSA-N 1-(sulfamoylamino)imidazo[4,5-c]quinoline Chemical compound C1=CC=CC2=C3N(NS(=O)(=O)N)C=NC3=CN=C21 URMAKSLECABUCE-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 1
- HLFGXPKPTDQYBN-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1N=C2C=CC=CC2=C2C1NCN2 HLFGXPKPTDQYBN-UHFFFAOYSA-N 0.000 description 1
- ZPJBFQVJSMEECU-UHFFFAOYSA-N 2-butyl-1-[4-(1,1-dioxo-1,2-thiazolidin-2-yl)butyl]imidazo[4,5-c]quinolin-4-amine Chemical compound CCCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCN1CCCS1(=O)=O ZPJBFQVJSMEECU-UHFFFAOYSA-N 0.000 description 1
- ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 1
- PDJXJKGLLBUYFS-UHFFFAOYSA-N 3-(2-butylimidazo[4,5-c]quinolin-1-yl)propan-1-amine;hydrochloride Chemical compound Cl.C1=CC=CC2=C(N(C(CCCC)=N3)CCCN)C3=CN=C21 PDJXJKGLLBUYFS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 206010059313 Anogenital warts Diseases 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 208000012657 Atopic disease Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000013165 Bowen disease Diseases 0.000 description 1
- 208000019337 Bowen disease of the skin Diseases 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- 208000000907 Condylomata Acuminata Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- 206010014950 Eosinophilia Diseases 0.000 description 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 description 1
- 208000005176 Hepatitis C Diseases 0.000 description 1
- 201000002563 Histoplasmosis Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- 108090000176 Interleukin-13 Proteins 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 108010002616 Interleukin-5 Proteins 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 206010024229 Leprosy Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 206010033733 Papule Diseases 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QTENRWWVYAAPBI-YZTFXSNBSA-N Streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@H]1[C@H](N=C(N)N)[C@@H](O)[C@H](N=C(N)N)[C@@H](O)[C@@H]1O QTENRWWVYAAPBI-YZTFXSNBSA-N 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 description 1
- 201000005485 Toxoplasmosis Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000033289 adaptive immune response Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005090 alkenylcarbonyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 description 1
- 201000004201 anogenital venereal wart Diseases 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229940125692 cardiovascular agent Drugs 0.000 description 1
- 239000002327 cardiovascular agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012228 culture supernatant Substances 0.000 description 1
- 201000007241 cutaneous T cell lymphoma Diseases 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 238000000432 density-gradient centrifugation Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 210000003495 flagella Anatomy 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- AYMLKIRJIAFRKA-UHFFFAOYSA-N imidazo[4,5-c]quinoline-1-sulfonamide Chemical compound C1=CC=CC2=C3N(S(=O)(=O)N)C=NC3=CN=C21 AYMLKIRJIAFRKA-UHFFFAOYSA-N 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 229960002751 imiquimod Drugs 0.000 description 1
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 210000003292 kidney cell Anatomy 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- GVVGTUISEJMHQM-UHFFFAOYSA-N n-[3-(2-butyl-5-oxidoimidazo[4,5-c]quinolin-5-ium-1-yl)propyl]benzenesulfonamide Chemical compound CCCCC1=NC2=C[N+]([O-])=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=CC=C1 GVVGTUISEJMHQM-UHFFFAOYSA-N 0.000 description 1
- MYSLFHVYCIHDQS-UHFFFAOYSA-N n-[3-(2-butylimidazo[4,5-c]quinolin-1-yl)propyl]benzenesulfonamide Chemical compound CCCCC1=NC2=CN=C3C=CC=CC3=C2N1CCCNS(=O)(=O)C1=CC=CC=C1 MYSLFHVYCIHDQS-UHFFFAOYSA-N 0.000 description 1
- OMRJMEKCCRXQBD-UHFFFAOYSA-N n-[3-(2-butylimidazo[4,5-c]quinolin-1-yl)propyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCNS(C)(=O)=O)C3=CN=C21 OMRJMEKCCRXQBD-UHFFFAOYSA-N 0.000 description 1
- RNOGFRHXFPQSIM-UHFFFAOYSA-N n-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]propyl]-5-(dimethylamino)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCCN3C4=C5C=CC=CC5=NC(N)=C4N=C3CCOC)=CC=CC2=C1N(C)C RNOGFRHXFPQSIM-UHFFFAOYSA-N 0.000 description 1
- CREBTFZCRHJEQE-UHFFFAOYSA-N n-[4-(2-ethylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CC)=N3)CCCCNS(C)(=O)=O)C3=CN=C21 CREBTFZCRHJEQE-UHFFFAOYSA-N 0.000 description 1
- XHFIIYXNIHVLAV-UHFFFAOYSA-N n-[4-(2-hexylimidazo[4,5-c]quinolin-1-yl)butyl]benzenesulfonamide Chemical compound CCCCCCC1=NC2=CN=C3C=CC=CC3=C2N1CCCCNS(=O)(=O)C1=CC=CC=C1 XHFIIYXNIHVLAV-UHFFFAOYSA-N 0.000 description 1
- LQDZOYWVFOTSOD-UHFFFAOYSA-N n-[4-(2-propylimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCNS(C)(=O)=O)C3=CN=C21 LQDZOYWVFOTSOD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- GRBNWOQDLWHDOX-UHFFFAOYSA-N tert-butyl n-[1-[2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]carbamate Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)NC(=O)OC(C)(C)C)C3=CN=C21 GRBNWOQDLWHDOX-UHFFFAOYSA-N 0.000 description 1
- PPHLYKFEQMEWND-UHFFFAOYSA-N tert-butyl n-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]carbamate Chemical compound C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)NC(=O)OC(C)(C)C)C3=C(N)N=C21 PPHLYKFEQMEWND-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 230000029069 type 2 immune response Effects 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 239000012646 vaccine adjuvant Substances 0.000 description 1
- 229940124931 vaccine adjuvant Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48320003P | 2003-06-27 | 2003-06-27 | |
| US60/483,200 | 2003-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060035637A true KR20060035637A (ko) | 2006-04-26 |
Family
ID=33563911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057024904A Ceased KR20060035637A (ko) | 2003-06-27 | 2004-06-25 | 술폰아미드 치환된 이미다조퀴놀린 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1638566A4 (https=) |
| JP (1) | JP2007521280A (https=) |
| KR (1) | KR20060035637A (https=) |
| CN (1) | CN1812789B (https=) |
| AR (2) | AR044923A1 (https=) |
| AU (1) | AU2004253929A1 (https=) |
| BR (1) | BRPI0411916A (https=) |
| CA (1) | CA2529322A1 (https=) |
| IL (1) | IL172427A0 (https=) |
| MX (1) | MXPA06000144A (https=) |
| MY (1) | MY157827A (https=) |
| NZ (1) | NZ544330A (https=) |
| RU (1) | RU2374246C2 (https=) |
| TW (2) | TW200514784A (https=) |
| WO (2) | WO2005003065A2 (https=) |
| ZA (1) | ZA200600769B (https=) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| BRPI0413558A (pt) | 2003-08-12 | 2006-10-17 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por hidroxilamina |
| AU2004268625B2 (en) | 2003-08-27 | 2011-03-31 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| AU2004270201A1 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| KR20060120069A (ko) | 2003-10-03 | 2006-11-24 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 피라졸로피리딘 및 그의 유사체 |
| AR046046A1 (es) | 2003-10-03 | 2005-11-23 | 3M Innovative Properties Co | Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas. |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| EP1685129A4 (en) | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| CA2545825A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| CA2547020C (en) | 2003-11-25 | 2014-03-25 | 3M Innovative Properties Company | 1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier |
| US8940755B2 (en) * | 2003-12-02 | 2015-01-27 | 3M Innovative Properties Company | Therapeutic combinations and methods including IRM compounds |
| JP2007517035A (ja) | 2003-12-29 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン |
| EP1699788A2 (en) | 2003-12-30 | 2006-09-13 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides |
| WO2005094531A2 (en) | 2004-03-24 | 2005-10-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| WO2006038923A2 (en) | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| EP1831221B1 (en) | 2004-12-30 | 2012-08-08 | 3M Innovative Properties Company | Substituted chiral fused 1,2 imidazo 4,5-c ring compounds |
| JP5543068B2 (ja) | 2004-12-30 | 2014-07-09 | スリーエム イノベイティブ プロパティズ カンパニー | キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| JP2008526752A (ja) * | 2004-12-30 | 2008-07-24 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答調節剤化合物の多経路投与 |
| AU2006210392A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune response modifiers |
| AU2006212765B2 (en) | 2005-02-09 | 2012-02-02 | 3M Innovative Properties Company | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| AU2006213746A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| EP1869043A2 (en) | 2005-04-01 | 2007-12-26 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| EA200800782A1 (ru) | 2005-09-09 | 2008-08-29 | Коли Фармасьютикал Груп, Инк. | ПРОИЗВОДНЫЕ АМИДА И КАРБАМАТА N-{2-[4-АМИНО-2-(ЭТОКСИМЕТИЛ)-1Н-ИМИДАЗОЛО[4,5-c]ХИНОЛИН-1-IL]-1,1-ДИМЕТИЛЭТИЛ}МЕТАНСУЛЬФОНАМИДА И СПОСОБЫ |
| AU2006292119A1 (en) * | 2005-09-23 | 2007-03-29 | 3M Innovative Properties Company | Method for 1H-imidazo[4,5-c]pyridines and analogs thereof |
| EP1988896A4 (en) | 2006-02-22 | 2011-07-27 | 3M Innovative Properties Co | CONJUGATES TO MODIFY IMMUNE REACTIONS |
| US7906506B2 (en) | 2006-07-12 | 2011-03-15 | 3M Innovative Properties Company | Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods |
| DK2276486T3 (da) * | 2008-03-24 | 2013-11-25 | 4Sc Discovery Gmbh | Nye substituerede imidazo-quinoliner |
| US9242980B2 (en) | 2010-08-17 | 2016-01-26 | 3M Innovative Properties Company | Lipidated immune response modifier compound compositions, formulations, and methods |
| BR112013031039B1 (pt) | 2011-06-03 | 2020-04-28 | 3M Innovative Properties Co | compostos de hidrazino 1h-imidazoquinolina-4-aminas, conjugados feitos destes compostos, composição e composição farmacêutica compreendendo ditos compostos e conjugados, usos dos mesmos e método de fabricação do conjugado |
| JP6460789B2 (ja) | 2011-06-03 | 2019-01-30 | スリーエム イノベイティブ プロパティズ カンパニー | ポリエチレングリコールセグメントを有するヘテロ２官能性リンカー及び該リンカーから調製された免疫反応調節複合体 |
| EP3083618B1 (en) | 2013-12-17 | 2018-02-21 | Pfizer Inc | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| RU2722149C1 (ru) * | 2015-09-14 | 2020-05-27 | Пфайзер Инк. | Новые производные имидазо[4,5-c] хинолинов и имидазо[4,5-c][1,5] нафтиридинов в качестве ингибиторов LRRK2 |
| CN109843327B (zh) | 2016-07-07 | 2022-05-13 | 小利兰·斯坦福大学托管委员会 | 抗体佐剂缀合物 |
| AU2018230236B2 (en) | 2017-03-10 | 2022-05-19 | Pfizer Inc. | Novel imidazo[4,5-c]quinoline derivatives as LRRK2 inhibitors |
| BR112020004505A2 (pt) | 2017-09-06 | 2020-09-15 | BioNTech SE | imidazoquinolinas substituídas como agonistas de tlr7 |
| WO2019123178A1 (en) | 2017-12-20 | 2019-06-27 | 3M Innovative Properties Company | Amide substitued imidazo[4,5-c]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| WO2020190725A1 (en) | 2019-03-15 | 2020-09-24 | Bolt Biotherapeutics, Inc. | Immunoconjugates targeting her2 |
| JP7829485B2 (ja) * | 2019-12-20 | 2026-03-13 | ナミ セラピューティクス， インコーポレイテッド | がんの処置において有用なＴｏｌｌ様受容体（「ＴＬＲ」）アゴニストプロドラッグを含有する製剤化および／または共製剤化リポソーム組成物ならびにその方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH31245A (en) * | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| US6069149A (en) * | 1997-01-09 | 2000-05-30 | Terumo Kabushiki Kaisha | Amide derivatives and intermediates for the synthesis thereof |
| IL124914A (en) * | 1997-06-26 | 2000-10-31 | Akzo Nobel Nv | Pharmaceutical compositions containing 6-aryl-2,3,5,6-tetrahydroimidazo¬2,1-a¾isoquinoline derivatives and some new such compounds |
| JP2000119271A (ja) * | 1998-08-12 | 2000-04-25 | Hokuriku Seiyaku Co Ltd | １ｈ―イミダゾピリジン誘導体 |
| DE69920497T2 (de) * | 1998-10-26 | 2006-02-09 | The Research Foundation Of State University Of New York | Liponsaürederivate und deren verwendung bei der behandlung von krankheiten |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| EP1455700A4 (en) * | 2001-11-16 | 2007-02-14 | 3M Innovative Properties Co | METHODS AND COMPOSITIONS RELATED TO MRI COMPOUNDS AND TO TOLL-TYPE RECEPTOR (TLR) PATHWAYS |
| US6677349B1 (en) * | 2001-12-21 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
-
2004
- 2004-06-24 MY MYPI20042461A patent/MY157827A/en unknown
- 2004-06-25 AR ARP040102248A patent/AR044923A1/es unknown
- 2004-06-25 NZ NZ544330A patent/NZ544330A/en unknown
- 2004-06-25 WO PCT/US2004/020607 patent/WO2005003065A2/en not_active Ceased
- 2004-06-25 TW TW093118635A patent/TW200514784A/zh unknown
- 2004-06-25 RU RU2005138915/04A patent/RU2374246C2/ru not_active IP Right Cessation
- 2004-06-25 TW TW093118636A patent/TW200511992A/zh unknown
- 2004-06-25 AR ARP040102247A patent/AR044922A1/es unknown
- 2004-06-25 CN CN2004800181459A patent/CN1812789B/zh not_active Expired - Fee Related
- 2004-06-25 KR KR1020057024904A patent/KR20060035637A/ko not_active Ceased
- 2004-06-25 JP JP2006517711A patent/JP2007521280A/ja active Pending
- 2004-06-25 CA CA002529322A patent/CA2529322A1/en not_active Abandoned
- 2004-06-25 EP EP04756208A patent/EP1638566A4/en not_active Withdrawn
- 2004-06-25 AU AU2004253929A patent/AU2004253929A1/en not_active Abandoned
- 2004-06-25 MX MXPA06000144A patent/MXPA06000144A/es unknown
- 2004-06-25 BR BRPI0411916-9A patent/BRPI0411916A/pt not_active IP Right Cessation
- 2004-06-25 WO PCT/US2004/020606 patent/WO2005003064A2/en not_active Ceased
-
2005
- 2005-12-07 IL IL172427A patent/IL172427A0/en unknown
-
2006
- 2006-01-26 ZA ZA200600769A patent/ZA200600769B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY157827A (en) | 2016-07-29 |
| TW200511992A (en) | 2005-04-01 |
| EP1638566A4 (en) | 2009-03-25 |
| AR044922A1 (es) | 2005-10-12 |
| CN1812789B (zh) | 2010-07-14 |
| CN1812789A (zh) | 2006-08-02 |
| WO2005003065A2 (en) | 2005-01-13 |
| WO2005003064A3 (en) | 2005-03-31 |
| MXPA06000144A (es) | 2006-04-07 |
| RU2374246C2 (ru) | 2009-11-27 |
| AR044923A1 (es) | 2005-10-12 |
| TW200514784A (en) | 2005-05-01 |
| CA2529322A1 (en) | 2005-01-13 |
| AU2004253929A1 (en) | 2005-01-13 |
| NZ544330A (en) | 2009-06-26 |
| RU2005138915A (ru) | 2006-06-27 |
| JP2007521280A (ja) | 2007-08-02 |
| ZA200600769B (en) | 2007-05-30 |
| IL172427A0 (en) | 2006-04-10 |
| BRPI0411916A (pt) | 2006-08-15 |
| EP1638566A2 (en) | 2006-03-29 |
| WO2005003064A2 (en) | 2005-01-13 |
| WO2005003065A3 (en) | 2005-03-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20060035637A (ko) | 술폰아미드 치환된 이미다조퀴놀린 | |
| US6677349B1 (en) | Sulfonamide and sulfamide substituted imidazoquinolines | |
| KR100781428B1 (ko) | 술폰아미드 및 술파미드 치환된 이미다조퀴놀린 | |
| US7132429B2 (en) | Sulfonamido ether substituted imidazoquinolines | |
| US6573273B1 (en) | Urea substituted imidazoquinolines | |
| US20020107262A1 (en) | Substituted imidazopyridines | |
| WO2000076518A1 (en) | Urea substituted imidazoquinolines | |
| AU2002232497A1 (en) | Urea substituted imidazoquinoline ethers | |
| EP1642580B1 (en) | Sulfonamide substituted imidazoquinolines | |
| HK1088836A (en) | Sulfonamide substituted imidazoquinolines | |
| HK1086762B (en) | Sulfonamide substituted imidazoquinolines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20051226 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20090624 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20110517 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20111121 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20110517 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |