CN101220028A - 亚磺酰氨基取代的咪唑并吡啶 - Google Patents
亚磺酰氨基取代的咪唑并吡啶 Download PDFInfo
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- CN101220028A CN101220028A CNA2008100030374A CN200810003037A CN101220028A CN 101220028 A CN101220028 A CN 101220028A CN A2008100030374 A CNA2008100030374 A CN A2008100030374A CN 200810003037 A CN200810003037 A CN 200810003037A CN 101220028 A CN101220028 A CN 101220028A
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- Prior art keywords
- alkyl
- compound
- aryl
- amino
- pyridine
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- 239000004202 carbamide Substances 0.000 title description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 2
- 150000005232 imidazopyridines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 201000010099 disease Diseases 0.000 claims abstract description 28
- 102000004127 Cytokines Human genes 0.000 claims abstract description 25
- 108090000695 Cytokines Proteins 0.000 claims abstract description 25
- -1 heterocyclic radical Chemical class 0.000 claims description 154
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 72
- 229910052799 carbon Inorganic materials 0.000 claims description 67
- 150000003839 salts Chemical class 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 15
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 230000001225 therapeutic effect Effects 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001118 alkylidene group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000003368 amide group Chemical group 0.000 claims description 9
- RCFKEIREOSXLET-UHFFFAOYSA-N disulfamide Chemical compound CC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O RCFKEIREOSXLET-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 230000001851 biosynthetic effect Effects 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000003851 azoles Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 230000001988 toxicity Effects 0.000 claims 3
- 231100000419 toxicity Toxicity 0.000 claims 3
- 206010048282 zoonosis Diseases 0.000 claims 3
- GNXMSXQEEFMDPJ-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-methylsulfonylpiperidin-4-yl)ethyl]imidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC1CCN(S(C)(=O)=O)CC1 GNXMSXQEEFMDPJ-UHFFFAOYSA-N 0.000 claims 1
- KAKVXKNFAGWHQV-UHFFFAOYSA-N n-[4-(4-amino-2-butyl-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]-4-fluorobenzenesulfonamide Chemical compound CCCCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCCNS(=O)(=O)C1=CC=C(F)C=C1 KAKVXKNFAGWHQV-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 60
- 230000028993 immune response Effects 0.000 abstract description 9
- 230000001613 neoplastic effect Effects 0.000 abstract description 6
- 239000003607 modifier Substances 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 125000000565 sulfonamide group Chemical group 0.000 abstract description 2
- 230000003612 virological effect Effects 0.000 abstract description 2
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 176
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 115
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 101
- 238000006243 chemical reaction Methods 0.000 description 100
- 239000000243 solution Substances 0.000 description 100
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
- 239000011541 reaction mixture Substances 0.000 description 90
- 239000000047 product Substances 0.000 description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- 239000007787 solid Substances 0.000 description 65
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 238000005406 washing Methods 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 38
- 239000010410 layer Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 239000003921 oil Substances 0.000 description 29
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 238000004458 analytical method Methods 0.000 description 27
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 25
- 238000001914 filtration Methods 0.000 description 25
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 25
- 238000012360 testing method Methods 0.000 description 25
- 239000012044 organic layer Substances 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 21
- 229910002027 silica gel Inorganic materials 0.000 description 21
- 229960001866 silicon dioxide Drugs 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 239000000284 extract Substances 0.000 description 18
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- 238000000605 extraction Methods 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 230000006837 decompression Effects 0.000 description 15
- 229960004756 ethanol Drugs 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 238000000926 separation method Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- 229940124530 sulfonamide Drugs 0.000 description 13
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 13
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 12
- 239000005695 Ammonium acetate Substances 0.000 description 12
- 239000003513 alkali Substances 0.000 description 12
- 235000019257 ammonium acetate Nutrition 0.000 description 12
- 229940043376 ammonium acetate Drugs 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 235000008504 concentrate Nutrition 0.000 description 12
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 12
- 230000001939 inductive effect Effects 0.000 description 12
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
- 235000017550 sodium carbonate Nutrition 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 239000012046 mixed solvent Substances 0.000 description 11
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical group NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 241000700605 Viruses Species 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 8
- 102100040247 Tumor necrosis factor Human genes 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
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- 108010050904 Interferons Proteins 0.000 description 7
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
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- ISTGQSQWSKCNFJ-UHFFFAOYSA-N tert-butyl n-ethylcarbamate Chemical compound CCNC(=O)OC(C)(C)C ISTGQSQWSKCNFJ-UHFFFAOYSA-N 0.000 description 7
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Classifications
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Landscapes
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Applications Claiming Priority (2)
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| US10/016,073 | 2001-12-06 | ||
| US10/016,073 US20020107262A1 (en) | 2000-12-08 | 2001-12-06 | Substituted imidazopyridines |
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| CNB028242858A Expired - Fee Related CN100402528C (zh) | 2001-12-06 | 2002-06-07 | 脲取代的咪唑并吡啶 |
| CNB028242874A Expired - Fee Related CN100387597C (zh) | 2001-12-06 | 2002-06-07 | 酰胺基取代的咪唑并吡啶 |
| CNB028242866A Expired - Fee Related CN100372846C (zh) | 2001-12-06 | 2002-06-07 | 亚磺酰氨基取代的咪唑并吡啶 |
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| CNB028242858A Expired - Fee Related CN100402528C (zh) | 2001-12-06 | 2002-06-07 | 脲取代的咪唑并吡啶 |
| CNB028242874A Expired - Fee Related CN100387597C (zh) | 2001-12-06 | 2002-06-07 | 酰胺基取代的咪唑并吡啶 |
| CNB028242866A Expired - Fee Related CN100372846C (zh) | 2001-12-06 | 2002-06-07 | 亚磺酰氨基取代的咪唑并吡啶 |
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| CA (3) | CA2468164A1 (enExample) |
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| AU2003237386A1 (en) | 2002-06-07 | 2003-12-22 | 3M Innovative Properties Company | Ether substituted imidazopyridines |
| DE602004009295T2 (de) | 2003-01-14 | 2008-07-03 | Arena Pharmaceuticals, Inc., San Diego | 1,2,3-trisubstituierte aryl- und heteroarylderivate als modulatoren des metabolismus zur vorbeugung und behandlung von metabolismus-bedingten krankheiten wie diabetes oder hyperglykämie |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| WO2004091500A2 (en) * | 2003-04-10 | 2004-10-28 | 3M Innovative Properties Company | Delivery of immune response modifier compounds |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| WO2005018556A2 (en) * | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| WO2005018555A2 (en) * | 2003-08-14 | 2005-03-03 | 3M Innovative Properties Company | Lipid-modified immune response modifiers |
| 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 |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| EP1673087B1 (en) | 2003-10-03 | 2015-05-13 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
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| EP0708772B1 (en) * | 1993-07-15 | 2000-08-23 | Minnesota Mining And Manufacturing Company | IMIDAZO [4,5-c]PYRIDIN-4-AMINES |
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