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 PDF

Info

Publication number: RU2374246C2
Authority: RU; Russia
Prior art keywords: imidazo; quinolin; amino; butyl; mmol
Prior art date: 2003-06-27

Application number

RU2005138915/04A

Other languages

English (en)

Russian (ru)

Other versions

RU2005138915A (ru

Inventor

Джордж В. ГРИЕСГРАБЕР (US)

Джордж В. ГРИЕСГРАБЕР

Original Assignee

3М Инновейтив Пропертиз Компани

Priority date (The priority date 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 date listed.)

2003-06-27

Filing date

2004-06-25

Publication date

2009-11-27

2004-06-25 Application filed by 3М Инновейтив Пропертиз Компани filed Critical 3М Инновейтив Пропертиз Компани

2006-06-27 Publication of RU2005138915A publication Critical patent/RU2005138915A/ru

2009-11-27 Application granted granted Critical

2009-11-27 Publication of RU2374246C2 publication Critical patent/RU2374246C2/ru

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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
239000012044 organic layer Substances 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 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
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
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
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
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
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
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
239000012299 nitrogen atmosphere Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
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
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
229910004298 SiO 2 Inorganic materials 0.000 description 3
241000700605 Viruses Species 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000006260 foam Substances 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000002955 immunomodulating agent Substances 0.000 description 3
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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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)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (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)
Oncology (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

RU2005138915/04A 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 RU2374246C2 (ru)

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)

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RU2005138915A RU2005138915A (ru)	2006-06-27
RU2374246C2 true RU2374246C2 (ru)	2009-11-27

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EP (1)	EP1638566A4 (fr)
JP (1)	JP2007521280A (fr)
KR (1)	KR20060035637A (fr)
CN (1)	CN1812789B (fr)
AR (2)	AR044923A1 (fr)
AU (1)	AU2004253929A1 (fr)
BR (1)	BRPI0411916A (fr)
CA (1)	CA2529322A1 (fr)
IL (1)	IL172427A0 (fr)
MX (1)	MXPA06000144A (fr)
MY (1)	MY157827A (fr)
NZ (1)	NZ544330A (fr)
RU (1)	RU2374246C2 (fr)
TW (2)	TW200514784A (fr)
WO (2)	WO2005003064A2 (fr)
ZA (1)	ZA200600769B (fr)

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PT2606047T (pt)	2010-08-17	2017-04-07	3M Innovative Properties Co	Composições, formulações e métodos de um composto lipidado modificador da resposta imunitária
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ES2663622T3 (es)	2013-12-17	2018-04-16	Pfizer Inc.	Novedosas 1H-pirrolo[2,3-b]piridinas 3,4-disustituidas y 7H-pirrolo[2,3-c]piridacinas 4,5-disustituidas como inhibidores de LRRK2
MX377305B (es)	2015-09-14	2025-03-07	Pfizer	DERIVADOS DE IMIDAZO[4,5-c]QUINOLINA E IMIDAZO[4,5-c][1,5]NAFTIRIDINA NOVEDOSOS COMO INHIBIDORES DE LRRK2.
ES2990113T3 (es)	2016-07-07	2024-11-28	The Board Of Trustees Of The Leland Stanfordjunior Univ	Conjugados de adyuvantes de anticuerpos
BR112019018688A2 (pt)	2017-03-10	2020-04-07	Pfizer	derivados de imidazo[4,5-c] quinolina como inibidores de lrrk2
WO2019123178A1 (fr)	2017-12-20	2019-06-27	3M Innovative Properties Company	Composés imidazo [4,5-c]quinoléine à substitution amide ayant un groupe de liaison à chaîne ramifiée destinés à être utilisés en tant que modificateur de la réponse immunitaire
WO2020190725A1 (fr)	2019-03-15	2020-09-24	Bolt Biotherapeutics, Inc.	Immunoconjugués ciblant le her2
KR20220119085A (ko) *	2019-12-20	2022-08-26	남미 테라퓨틱스, 인크.	암의 치료에 유용한 톨-유사 수용체 (“tlr”) 효능제 전구약물을 함유하는 제제화된 및/또는 공동-제제화된 리포솜 조성물 및 그의 방법

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- 2004-06-25 WO PCT/US2004/020606 patent/WO2005003064A2/fr not_active Ceased
- 2004-06-25 EP EP04756208A patent/EP1638566A4/fr not_active Withdrawn
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- 2004-06-25 WO PCT/US2004/020607 patent/WO2005003065A2/fr not_active Ceased
- 2004-06-25 RU RU2005138915/04A patent/RU2374246C2/ru not_active IP Right Cessation
- 2004-06-25 KR KR1020057024904A patent/KR20060035637A/ko not_active Ceased
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2005
- 2005-12-07 IL IL172427A patent/IL172427A0/en unknown
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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
WO2005003065A2 (fr)	2005-01-13
TW200511992A (en)	2005-04-01
WO2005003064A2 (fr)	2005-01-13
MY157827A (en)	2016-07-29
JP2007521280A (ja)	2007-08-02
IL172427A0 (en)	2006-04-10
CN1812789B (zh)	2010-07-14
CN1812789A (zh)	2006-08-02
WO2005003064A3 (fr)	2005-03-31
MXPA06000144A (es)	2006-04-07
EP1638566A4 (fr)	2009-03-25
NZ544330A (en)	2009-06-26
KR20060035637A (ko)	2006-04-26
AR044923A1 (es)	2005-10-12
ZA200600769B (en)	2007-05-30
RU2005138915A (ru)	2006-06-27
BRPI0411916A (pt)	2006-08-15
WO2005003065A3 (fr)	2005-03-10
AU2004253929A1 (en)	2005-01-13
TW200514784A (en)	2005-05-01
CA2529322A1 (fr)	2005-01-13
AR044922A1 (es)	2005-10-12
EP1638566A2 (fr)	2006-03-29

Publication	Publication Date	Title
RU2374246C2 (ru)	2009-11-27	N-{2-[4-АМИНО-2-(ЭТОКСИМЕТИЛ)-1Н-ИМИДАЗО-[4,5-с]-ХИНОЛИН-1-ИЛ]-1,1-ДИМЕТИЛЭТИЛ}-МЕТАНСУЛЬФОНАМИД И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ЕГО ОСНОВЕ
US6677349B1 (en)	2004-01-13	Sulfonamide and sulfamide substituted imidazoquinolines
KR100781428B1 (ko)	2007-12-03	술폰아미드 및 술파미드 치환된 이미다조퀴놀린
US7214675B2 (en)	2007-05-08	Urea substituted imidazoquinoline ethers
US6656938B2 (en)	2003-12-02	Urea substituted imidazoquinoline ethers
US20020107262A1 (en)	2002-08-08	Substituted imidazopyridines
AU2002232497A1 (en)	2002-08-22	Urea substituted imidazoquinoline ethers
EP1642580B1 (fr)	2009-08-19	Sulfonamides d' imidazoquinoline
HK1088836A (en)	2006-11-17	Sulfonamide substituted imidazoquinolines
HK1086762B (en)	2010-04-30	Sulfonamide substituted imidazoquinolines

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2012-04-20	MM4A	The patent is invalid due to non-payment of fees	Effective date: 20110626