JP2005538057A - エーテル置換イミダゾピリジン - Google Patents

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Publication number

JP2005538057A

JP2005538057A JP2004510705A JP2004510705A JP2005538057A JP 2005538057 A JP2005538057 A JP 2005538057A JP 2004510705 A JP2004510705 A JP 2004510705A JP 2004510705 A JP2004510705 A JP 2004510705A JP 2005538057 A JP2005538057 A JP 2005538057A

Authority

JP

Japan

Prior art keywords

alkyl

imidazo

alkylene

pyridin

amine

Prior art date

2002-06-07

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.)

Pending

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• 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 329
• -1 imidazopyridine compound Chemical class 0.000 claims abstract description 100
• 238000000034 method Methods 0.000 claims abstract description 63
• 102000004127 Cytokines Human genes 0.000 claims abstract description 33
• 108090000695 Cytokines Proteins 0.000 claims abstract description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
• 201000010099 disease Diseases 0.000 claims abstract description 28
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 26
• 230000003612 virological effect Effects 0.000 claims abstract description 14
• 230000001613 neoplastic effect Effects 0.000 claims abstract description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 193
• 125000000217 alkyl group Chemical group 0.000 claims description 174
• 239000001257 hydrogen Substances 0.000 claims description 157
• 150000003839 salts Chemical class 0.000 claims description 128
• 150000002431 hydrogen Chemical class 0.000 claims description 97
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 66
• 229910052736 halogen Inorganic materials 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 65
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
• 125000002947 alkylene group Chemical group 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 59
• 125000003342 alkenyl group Chemical group 0.000 claims description 55
• 125000003118 aryl group Chemical group 0.000 claims description 55
• 241001465754 Metazoa Species 0.000 claims description 54
• 229910052799 carbon Inorganic materials 0.000 claims description 54
• 125000004450 alkenylene group Chemical group 0.000 claims description 53
• 125000004419 alkynylene group Chemical group 0.000 claims description 53
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 48
• 125000000304 alkynyl group Chemical group 0.000 claims description 45
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
• 125000001424 substituent group Chemical group 0.000 claims description 43
• 150000002367 halogens Chemical class 0.000 claims description 39
• 125000004414 alkyl thio group Chemical group 0.000 claims description 34
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• 125000003282 alkyl amino group Chemical group 0.000 claims description 33
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 33
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• 230000001939 inductive effect Effects 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 238000007363 ring formation reaction Methods 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 230000002452 interceptive effect Effects 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
• 150000002828 nitro derivatives Chemical class 0.000 claims 6
• 239000000203 mixture Substances 0.000 abstract description 51
• 239000000543 intermediate Substances 0.000 abstract description 31
• 230000028993 immune response Effects 0.000 abstract description 7
• 239000003607 modifier Substances 0.000 abstract description 5
• 125000001033 ether group Chemical group 0.000 abstract description 4
• 238000002360 preparation method Methods 0.000 abstract description 2
• 238000006243 chemical reaction Methods 0.000 description 333
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 231
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 223
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 158
• 239000000243 solution Substances 0.000 description 139
• 239000000047 product Substances 0.000 description 131
• 239000011541 reaction mixture Substances 0.000 description 128
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 116
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 108
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 103
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 100
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 99
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 95
• 239000002904 solvent Substances 0.000 description 91
• 239000007787 solid Substances 0.000 description 90
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 77
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 72
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
• 238000007796 conventional method Methods 0.000 description 67
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 60
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 58
• 235000019341 magnesium sulphate Nutrition 0.000 description 58
• 229910052757 nitrogen Inorganic materials 0.000 description 55
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
• 239000003921 oil Substances 0.000 description 53
• 235000019198 oils Nutrition 0.000 description 53
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 42
• 238000005481 NMR spectroscopy Methods 0.000 description 40
• 239000012267 brine Substances 0.000 description 37
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 37
• 238000004458 analytical method Methods 0.000 description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 35
• 239000003054 catalyst Substances 0.000 description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 30
• 239000012044 organic layer Substances 0.000 description 29
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 29
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 238000010992 reflux Methods 0.000 description 26
• 238000004128 high performance liquid chromatography Methods 0.000 description 25
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 23
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 22
• 230000009467 reduction Effects 0.000 description 22
• UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical compound NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 19
• 239000005695 Ammonium acetate Substances 0.000 description 19
• 235000019257 ammonium acetate Nutrition 0.000 description 19
• 229940043376 ammonium acetate Drugs 0.000 description 19
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• 239000012299 nitrogen atmosphere Substances 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 239000012312 sodium hydride Substances 0.000 description 18
• 229910000104 sodium hydride Inorganic materials 0.000 description 18
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 17
• 238000004809 thin layer chromatography Methods 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• 150000001408 amides Chemical group 0.000 description 16
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 16
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
• 150000001266 acyl halides Chemical class 0.000 description 15
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 14
• 229960004979 fampridine Drugs 0.000 description 14
• HPYDPDYKFJEKPK-UHFFFAOYSA-N 4-phenoxy-1h-imidazo[4,5-c]pyridine Chemical compound N=1C=CC=2NC=NC=2C=1OC1=CC=CC=C1 HPYDPDYKFJEKPK-UHFFFAOYSA-N 0.000 description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• 238000004440 column chromatography Methods 0.000 description 13
• 150000004985 diamines Chemical class 0.000 description 13
• 239000003480 eluent Substances 0.000 description 13
• 238000010438 heat treatment Methods 0.000 description 13
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 13
• UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 12
• 239000003638 chemical reducing agent Substances 0.000 description 12
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 11
• 239000000377 silicon dioxide Substances 0.000 description 11
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
• 239000000284 extract Substances 0.000 description 10
• 238000004519 manufacturing process Methods 0.000 description 10
• MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 9
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 150000001721 carbon Chemical group 0.000 description 9
• 238000011065 in-situ storage Methods 0.000 description 9
• ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• JPEPQJIRNGWRCA-UHFFFAOYSA-N 1-[2-(2-aminoethoxy)ethyl]-2,6,7-trimethylimidazo[4,5-c]pyridin-4-amine Chemical group N1=C(C)C(C)=C2N(CCOCCN)C(C)=NC2=C1N JPEPQJIRNGWRCA-UHFFFAOYSA-N 0.000 description 8
• KSQNRBBVJBZZTG-UHFFFAOYSA-N 2-phenoxypyridine-3,4-diamine Chemical compound NC1=CC=NC(OC=2C=CC=CC=2)=C1N KSQNRBBVJBZZTG-UHFFFAOYSA-N 0.000 description 8
• SUUZDNBBAQOFQR-UHFFFAOYSA-N 3-nitro-2-phenoxypyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1OC1=CC=CC=C1 SUUZDNBBAQOFQR-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• 206010028980 Neoplasm Diseases 0.000 description 8
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
• 239000002638 heterogeneous catalyst Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000002244 precipitate Substances 0.000 description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 8
• 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 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 238000005984 hydrogenation reaction Methods 0.000 description 7
• 239000012442 inert solvent Substances 0.000 description 7
• 239000012948 isocyanate Substances 0.000 description 7
• 150000002513 isocyanates Chemical class 0.000 description 7
• 239000012279 sodium borohydride Substances 0.000 description 7
• 229910000033 sodium borohydride Inorganic materials 0.000 description 7
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 7
• XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 6
• AFQMWBUNDONXED-UHFFFAOYSA-N 2-phenylmethoxyethanamine;hydrochloride Chemical compound Cl.NCCOCC1=CC=CC=C1 AFQMWBUNDONXED-UHFFFAOYSA-N 0.000 description 6
• UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical compound C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 229910052783 alkali metal Inorganic materials 0.000 description 6
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 6
• 239000006227 byproduct Substances 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• 230000007062 hydrolysis Effects 0.000 description 6
• 238000006460 hydrolysis reaction Methods 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 239000002480 mineral oil Substances 0.000 description 6
• 235000010446 mineral oil Nutrition 0.000 description 6
• 150000002905 orthoesters Chemical class 0.000 description 6
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 6
• 229910003446 platinum oxide Inorganic materials 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 6
• 229910052717 sulfur Inorganic materials 0.000 description 6
• 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 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 6
• CEGLXJGCOGYSFS-UHFFFAOYSA-N 2,4-dichloro-5,6-dimethyl-3-nitropyridine Chemical compound CC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=C1C CEGLXJGCOGYSFS-UHFFFAOYSA-N 0.000 description 5
• 125000006516 2-(benzyloxy)ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
• 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 5
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 5
• 102000006992 Interferon-alpha Human genes 0.000 description 5
• 108010047761 Interferon-alpha Proteins 0.000 description 5
• 235000013877 carbamide Nutrition 0.000 description 5
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 239000011521 glass Substances 0.000 description 5
• 239000012535 impurity Substances 0.000 description 5
• 230000006698 induction Effects 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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