RU2374246C2 - N-{2-[4-АМИНО-2-(ЭТОКСИМЕТИЛ)-1Н-ИМИДАЗО-[4,5-с]-ХИНОЛИН-1-ИЛ]-1,1-ДИМЕТИЛЭТИЛ}-МЕТАНСУЛЬФОНАМИД И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ЕГО ОСНОВЕ - Google Patents
N-{2-[4-АМИНО-2-(ЭТОКСИМЕТИЛ)-1Н-ИМИДАЗО-[4,5-с]-ХИНОЛИН-1-ИЛ]-1,1-ДИМЕТИЛЭТИЛ}-МЕТАНСУЛЬФОНАМИД И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ЕГО ОСНОВЕ Download PDFInfo
- Publication number
- RU2374246C2 RU2374246C2 RU2005138915/04A RU2005138915A RU2374246C2 RU 2374246 C2 RU2374246 C2 RU 2374246C2 RU 2005138915/04 A RU2005138915/04 A RU 2005138915/04A RU 2005138915 A RU2005138915 A RU 2005138915A RU 2374246 C2 RU2374246 C2 RU 2374246C2
- Authority
- RU
- Russia
- Prior art keywords
- imidazo
- quinolin
- amino
- butyl
- mmol
- Prior art date
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- 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 title claims description 5
- 150000001875 compounds Chemical class 0.000 title abstract description 46
- 239000000126 substance Substances 0.000 claims abstract description 66
- 102000004127 Cytokines Human genes 0.000 claims abstract description 26
- 108090000695 Cytokines Proteins 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 241001465754 Metazoa Species 0.000 claims abstract description 20
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000003612 virological effect Effects 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 230000001939 inductive effect Effects 0.000 claims abstract description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 9
- 229940124530 sulfonamide Drugs 0.000 abstract description 6
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 abstract description 5
- 150000003456 sulfonamides Chemical group 0.000 abstract description 5
- 230000000771 oncological effect Effects 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 86
- 229910052757 nitrogen Inorganic materials 0.000 description 81
- 229910052799 carbon Inorganic materials 0.000 description 80
- 238000006243 chemical reaction Methods 0.000 description 73
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- 239000007787 solid Substances 0.000 description 54
- 239000000243 solution Substances 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- 238000007429 general method Methods 0.000 description 42
- 238000004458 analytical method Methods 0.000 description 39
- 238000004364 calculation method Methods 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 33
- 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
- 239000000463 material Substances 0.000 description 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 18
- -1 quinolin-1-yl Chemical group 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 125000000623 heterocyclic group Chemical group 0.000 description 16
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 15
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 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
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 14
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000006698 induction Effects 0.000 description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-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
- 238000010561 standard procedure Methods 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 9
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 8
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000028993 immune response Effects 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
- 150000001204 N-oxides Chemical class 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 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 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 102000006992 Interferon-alpha Human genes 0.000 description 6
- 108010047761 Interferon-alpha Proteins 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
- 150000001412 amines Chemical class 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 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 5
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 5
- 108010050904 Interferons Proteins 0.000 description 5
- 102000014150 Interferons Human genes 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 125000004103 aminoalkyl group Chemical group 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 5
- 229940124669 imidazoquinoline Drugs 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 229940079322 interferon Drugs 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 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
- 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
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- 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
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- 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 4
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- 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 4
- 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 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
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- 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 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
- 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 3
- CRHYJWBCRXKHRN-UHFFFAOYSA-N 1-[4-(1,1-dioxo-1,2-thiazolidin-2-yl)butyl]-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-4-amine Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CCCCN1CCCS1(=O)=O CRHYJWBCRXKHRN-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- 241000700605 Viruses Species 0.000 description 3
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
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- 239000000706 filtrate Substances 0.000 description 3
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 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
- 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
- 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 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
- 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 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
- 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
- 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
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (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)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (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 (2)
| Publication Number | Publication Date |
|---|---|
| RU2005138915A RU2005138915A (ru) | 2006-06-27 |
| RU2374246C2 true RU2374246C2 (ru) | 2009-11-27 |
Family
ID=33563911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005138915/04A RU2374246C2 (ru) | 2003-06-27 | 2004-06-25 | N-{2-[4-АМИНО-2-(ЭТОКСИМЕТИЛ)-1Н-ИМИДАЗО-[4,5-с]-ХИНОЛИН-1-ИЛ]-1,1-ДИМЕТИЛЭТИЛ}-МЕТАНСУЛЬФОНАМИД И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ЕГО ОСНОВЕ |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1638566A4 (enExample) |
| JP (1) | JP2007521280A (enExample) |
| KR (1) | KR20060035637A (enExample) |
| CN (1) | CN1812789B (enExample) |
| AR (2) | AR044923A1 (enExample) |
| AU (1) | AU2004253929A1 (enExample) |
| BR (1) | BRPI0411916A (enExample) |
| CA (1) | CA2529322A1 (enExample) |
| IL (1) | IL172427A0 (enExample) |
| MX (1) | MXPA06000144A (enExample) |
| MY (1) | MY157827A (enExample) |
| NZ (1) | NZ544330A (enExample) |
| RU (1) | RU2374246C2 (enExample) |
| TW (2) | TW200514784A (enExample) |
| WO (2) | WO2005003064A2 (enExample) |
| ZA (1) | ZA200600769B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11279684B2 (en) | 2017-09-06 | 2022-03-22 | Bointech SE | Substituted imidazoquinolines as agonists of TLR7 |
| RU2773516C2 (ru) * | 2017-03-10 | 2022-06-06 | Пфайзер Инк. | Новые производные имидазо[4,5-с]хинолина в качестве ингибиторов LRRK2 |
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| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| WO2005018556A2 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| PH12006500401A1 (en) | 2003-08-27 | 2005-03-10 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| EP1660026A4 (en) | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | TREATMENT FOR CD5 + B CELL LYMPHOMA |
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| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| WO2005048945A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo ring compounds |
| EP1685129A4 (en) | 2003-11-14 | 2008-10-22 | 3M Innovative Properties Co | OXIMSUBSTITUTED IMIDAZORING CONNECTIONS |
| 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 |
| WO2005055932A2 (en) * | 2003-12-02 | 2005-06-23 | 3M Innovative Properties Company | Therapeutic combinations and methods including irm compounds |
| US8802853B2 (en) | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| WO2005066169A2 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| AU2005228150A1 (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 |
| WO2006065280A2 (en) | 2004-06-18 | 2006-06-22 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods |
| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| 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 |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| JP5313502B2 (ja) | 2004-12-30 | 2013-10-09 | スリーエム イノベイティブ プロパティズ カンパニー | 置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| ZA200706251B (en) * | 2004-12-30 | 2008-11-26 | Coley Pharm Group Inc | Immune response modifier formulations and methods |
| CA2597092A1 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| WO2006086449A2 (en) | 2005-02-09 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| CA2597587A1 (en) | 2005-02-11 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| EP1863814A1 (en) | 2005-04-01 | 2007-12-12 | 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 |
| AU2006287270A1 (en) | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of N-{2-[4-amino-2- (ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| 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 |
| WO2007035935A1 (en) * | 2005-09-23 | 2007-03-29 | Coley Pharmaceutical Group, Inc. | METHOD FOR 1H-IMIDAZO[4,5-c]PYRIDINES AND ANALOGS THEREOF |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2008008432A2 (en) | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
| HRP20131139T1 (hr) * | 2008-03-24 | 2014-01-03 | 4Sc Discovery Gmbh | Novi supstituirani imidazokinolini |
| EP3222621B1 (en) | 2010-08-17 | 2023-03-08 | 3M Innovative Properties Company | Lipidated immune response modifier compound and its medical use |
| WO2012167088A1 (en) | 2011-06-03 | 2012-12-06 | 3M Innovative Properties Company | Heterobifunctional linkers with polyethylene glycol segments and immune response modifier conjugates made therefrom |
| EP3366311B1 (en) | 2011-06-03 | 2020-02-26 | 3M Innovative Properties Co. | Hydrazino-1h-imidazoquinolin-4-amines and conjugates made therefrom |
| US9695171B2 (en) | 2013-12-17 | 2017-07-04 | Pfizer Inc. | 3,4-disubstituted-1 H-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7H-pyrrolo[2,3-c]pyridazines as LRRK2 inhibitors |
| JP6873980B2 (ja) | 2015-09-14 | 2021-05-19 | ファイザー・インク | ＬＲＲＫ２阻害薬としての新規のイミダゾ［４，５−ｃ］キノリンおよびイミダゾ［４，５−ｃ］［１，５］ナフチリジン誘導体 |
| EP3484518B1 (en) | 2016-07-07 | 2024-08-14 | The Board of Trustees of the Leland Stanford Junior University | Antibody adjuvant conjugates |
| SG11201908322WA (en) | 2017-03-10 | 2019-10-30 | Pfizer | Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors |
| CA3086439A1 (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 |
| JP2022525594A (ja) | 2019-03-15 | 2022-05-18 | ボルト バイオセラピューティクス、インコーポレーテッド | Ｈｅｒ２を標的とする免疫結合体 |
| CA3161668A1 (en) * | 2019-12-20 | 2021-06-24 | Nammi Therapeutics, Inc. | Formulated and/or co-formulated liposome compositions containing toll-like receptor ("tlr") agonist prodrugs useful in the treatment of cancer and methods thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998030562A1 (en) * | 1997-01-09 | 1998-07-16 | Terumo Kabushiki Kaisha | Novel amide derivatives and intermediates for the synthesis thereof |
| RU2127273C1 (ru) * | 1991-10-30 | 1999-03-10 | Жансен Фармасетика Н.В. | Производное 1,3-дигидро-2h-имидазо/4,5-b/хинолин-2-она в качестве ингибитора фосфодиэстеразы, способ его получения, промежуточные для него, фармацевтическая композиция и способ ее получения |
| WO2000009506A1 (en) * | 1998-08-12 | 2000-02-24 | Hokuriku Seiyaku Co., Ltd. | 1h-imidazopyridine derivatives |
| US6331559B1 (en) * | 1998-10-26 | 2001-12-18 | The Research Foundation Of State University Of New York At Stony Brook | Lipoic acid derivatives and their use in treatment of disease |
| RU2204560C2 (ru) * | 1997-06-26 | 2003-05-20 | Акцо Нобель Н.В. | Производные тетрагидроимидазо [2,1-а]изохинолина и фармацевтический препарат на их основе |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| EP1719511B1 (en) * | 2001-11-16 | 2008-12-10 | 3M Innovative Properties Company | N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide, a pharmaceutical composition comprising the same and use thereof |
| 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 RU RU2005138915/04A patent/RU2374246C2/ru not_active IP Right Cessation
- 2004-06-25 BR BRPI0411916-9A patent/BRPI0411916A/pt not_active IP Right Cessation
- 2004-06-25 AU AU2004253929A patent/AU2004253929A1/en not_active Abandoned
- 2004-06-25 AR ARP040102248A patent/AR044923A1/es unknown
- 2004-06-25 MX MXPA06000144A patent/MXPA06000144A/es unknown
- 2004-06-25 TW TW093118635A patent/TW200514784A/zh unknown
- 2004-06-25 CN CN2004800181459A patent/CN1812789B/zh not_active Expired - Fee Related
- 2004-06-25 WO PCT/US2004/020606 patent/WO2005003064A2/en not_active Ceased
- 2004-06-25 EP EP04756208A patent/EP1638566A4/en not_active Withdrawn
- 2004-06-25 KR KR1020057024904A patent/KR20060035637A/ko not_active Ceased
- 2004-06-25 JP JP2006517711A patent/JP2007521280A/ja active Pending
- 2004-06-25 TW TW093118636A patent/TW200511992A/zh unknown
- 2004-06-25 AR ARP040102247A patent/AR044922A1/es unknown
- 2004-06-25 WO PCT/US2004/020607 patent/WO2005003065A2/en not_active Ceased
- 2004-06-25 CA CA002529322A patent/CA2529322A1/en not_active Abandoned
- 2004-06-25 NZ NZ544330A patent/NZ544330A/en unknown
-
2005
- 2005-12-07 IL IL172427A patent/IL172427A0/en unknown
-
2006
- 2006-01-26 ZA ZA200600769A patent/ZA200600769B/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2127273C1 (ru) * | 1991-10-30 | 1999-03-10 | Жансен Фармасетика Н.В. | Производное 1,3-дигидро-2h-имидазо/4,5-b/хинолин-2-она в качестве ингибитора фосфодиэстеразы, способ его получения, промежуточные для него, фармацевтическая композиция и способ ее получения |
| WO1998030562A1 (en) * | 1997-01-09 | 1998-07-16 | Terumo Kabushiki Kaisha | Novel amide derivatives and intermediates for the synthesis thereof |
| RU2204560C2 (ru) * | 1997-06-26 | 2003-05-20 | Акцо Нобель Н.В. | Производные тетрагидроимидазо [2,1-а]изохинолина и фармацевтический препарат на их основе |
| WO2000009506A1 (en) * | 1998-08-12 | 2000-02-24 | Hokuriku Seiyaku Co., Ltd. | 1h-imidazopyridine derivatives |
| US6331559B1 (en) * | 1998-10-26 | 2001-12-18 | The Research Foundation Of State University Of New York At Stony Brook | Lipoic acid derivatives and their use in treatment of disease |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2773516C2 (ru) * | 2017-03-10 | 2022-06-06 | Пфайзер Инк. | Новые производные имидазо[4,5-с]хинолина в качестве ингибиторов LRRK2 |
| US11279684B2 (en) | 2017-09-06 | 2022-03-22 | Bointech SE | Substituted imidazoquinolines as agonists of TLR7 |
| RU2776748C2 (ru) * | 2017-09-06 | 2022-07-26 | Бионтех Се | Замещенные имидазохинолины в качестве агонистов tlr7 |
| US11987569B2 (en) | 2017-09-06 | 2024-05-21 | BioNTech SE | Substituted imidazoquinolines as agonists of TLR7 |
Also Published As
| Publication number | Publication date |
|---|---|
| IL172427A0 (en) | 2006-04-10 |
| AR044923A1 (es) | 2005-10-12 |
| WO2005003065A3 (en) | 2005-03-10 |
| CA2529322A1 (en) | 2005-01-13 |
| RU2005138915A (ru) | 2006-06-27 |
| TW200511992A (en) | 2005-04-01 |
| AU2004253929A1 (en) | 2005-01-13 |
| WO2005003064A2 (en) | 2005-01-13 |
| NZ544330A (en) | 2009-06-26 |
| TW200514784A (en) | 2005-05-01 |
| MXPA06000144A (es) | 2006-04-07 |
| KR20060035637A (ko) | 2006-04-26 |
| JP2007521280A (ja) | 2007-08-02 |
| EP1638566A2 (en) | 2006-03-29 |
| AR044922A1 (es) | 2005-10-12 |
| WO2005003065A2 (en) | 2005-01-13 |
| EP1638566A4 (en) | 2009-03-25 |
| CN1812789A (zh) | 2006-08-02 |
| CN1812789B (zh) | 2010-07-14 |
| WO2005003064A3 (en) | 2005-03-31 |
| MY157827A (en) | 2016-07-29 |
| BRPI0411916A (pt) | 2006-08-15 |
| ZA200600769B (en) | 2007-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110626 |