KR20010020465A - 벤즈이미다졸 유도체 - Google Patents
벤즈이미다졸 유도체 Download PDFInfo
- Publication number
- KR20010020465A KR20010020465A KR1019997011599A KR19997011599A KR20010020465A KR 20010020465 A KR20010020465 A KR 20010020465A KR 1019997011599 A KR1019997011599 A KR 1019997011599A KR 19997011599 A KR19997011599 A KR 19997011599A KR 20010020465 A KR20010020465 A KR 20010020465A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- benzimidazole
- hydrogen atom
- bromo
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title abstract description 7
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract 3
- 238000000034 method Methods 0.000 claims abstract description 56
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 208000036142 Viral infection Diseases 0.000 claims abstract description 22
- 230000009385 viral infection Effects 0.000 claims abstract description 22
- 230000002265 prevention Effects 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 242
- 125000000217 alkyl group Chemical group 0.000 claims description 182
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 108
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 105
- -1 hydroxy, amino Chemical group 0.000 claims description 70
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 208000024891 symptom Diseases 0.000 claims description 16
- 150000001336 alkenes Chemical class 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- OOAVDXDURLPULP-GWOFURMSSA-N (2r,3r,4r,5r)-2-(2-bromo-5,6-dichlorobenzimidazol-1-yl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1N1C2=CC(Cl)=C(Cl)C=C2N=C1Br OOAVDXDURLPULP-GWOFURMSSA-N 0.000 claims description 9
- 241001465754 Metazoa Species 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- WKTYQVXOAVBLIO-ZYHUDNBSSA-N (1r,2r)-2-(2-bromo-5,6-dichlorobenzimidazol-1-yl)cyclohexan-1-ol Chemical compound O[C@@H]1CCCC[C@H]1N1C2=CC(Cl)=C(Cl)C=C2N=C1Br WKTYQVXOAVBLIO-ZYHUDNBSSA-N 0.000 claims description 5
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims description 5
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 5
- ZHKNTGOJXGQPEL-DDHJBXDOSA-N (2r,3r,4r,5r)-2-(2-bromo-6-chloro-5-methylbenzimidazol-1-yl)oxane-3,4,5-triol Chemical compound C1=2C=C(Cl)C(C)=CC=2N=C(Br)N1[C@@H]1OC[C@@H](O)[C@@H](O)[C@H]1O ZHKNTGOJXGQPEL-DDHJBXDOSA-N 0.000 claims description 4
- IJESABNALPBLAO-QBPKDAKJSA-N [(3r,4r,5r,6r)-4,5-diacetyloxy-6-(2-bromo-5,6-dichlorobenzimidazol-1-yl)oxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@H](OC(=O)C)CO[C@H]1N1C2=CC(Cl)=C(Cl)C=C2N=C1Br IJESABNALPBLAO-QBPKDAKJSA-N 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- YEUHNIIKVBNHKQ-YFKTTZPYSA-N (2s,3r,4r,5s)-5-(2-bromo-5,6-dichlorobenzimidazol-1-yl)-2-(hydroxymethyl)oxane-3,4-diol Chemical compound O[C@H]1[C@@H](O)[C@H](CO)OC[C@@H]1N1C2=CC(Cl)=C(Cl)C=C2N=C1Br YEUHNIIKVBNHKQ-YFKTTZPYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- ASICPWKBTMIXNS-GMTAPVOTSA-N (2r,3r,4r)-2-(2-bromo-5,6-dichlorobenzimidazol-1-yl)oxane-3,4-diol Chemical compound O[C@@H]1[C@H](O)CCO[C@H]1N1C2=CC(Cl)=C(Cl)C=C2N=C1Br ASICPWKBTMIXNS-GMTAPVOTSA-N 0.000 claims description 2
- LOMBFOAWBUJDCF-VVFBATEQSA-N (2r,3r,4r,5r)-2-(2-bromo-5,6-dichloro-4-fluorobenzimidazol-1-yl)oxane-3,4,5-triol Chemical compound O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1N1C2=CC(Cl)=C(Cl)C(F)=C2N=C1Br LOMBFOAWBUJDCF-VVFBATEQSA-N 0.000 claims description 2
- WXZYRKDMQCTYPO-AAVRWANBSA-N (2r,3r,4r,5r)-2-[5,6-dichloro-2-(propan-2-ylamino)benzimidazol-1-yl]oxane-3,4,5-triol Chemical compound CC(C)NC1=NC2=CC(Cl)=C(Cl)C=C2N1[C@@H]1OC[C@@H](O)[C@@H](O)[C@H]1O WXZYRKDMQCTYPO-AAVRWANBSA-N 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 7
- 241001529453 unidentified herpesvirus Species 0.000 abstract description 5
- 238000012961 medicinal therapy Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 334
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 169
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
- 239000000243 solution Substances 0.000 description 144
- 239000000203 mixture Substances 0.000 description 139
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 122
- 229940093499 ethyl acetate Drugs 0.000 description 111
- 235000019439 ethyl acetate Nutrition 0.000 description 111
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
- 238000006243 chemical reaction Methods 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 75
- 239000000460 chlorine Substances 0.000 description 73
- 239000002904 solvent Substances 0.000 description 68
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- 239000000047 product Substances 0.000 description 55
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 53
- 238000009472 formulation Methods 0.000 description 52
- 230000008570 general process Effects 0.000 description 49
- 239000007787 solid Substances 0.000 description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 46
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 45
- 239000004480 active ingredient Substances 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 41
- 235000019441 ethanol Nutrition 0.000 description 40
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 37
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
- 235000019341 magnesium sulphate Nutrition 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 34
- 239000000741 silica gel Substances 0.000 description 33
- 229910002027 silica gel Inorganic materials 0.000 description 33
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 31
- 238000010992 reflux Methods 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Substances [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 208000015181 infectious disease Diseases 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 21
- 235000017557 sodium bicarbonate Nutrition 0.000 description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 18
- 229910000029 sodium carbonate Inorganic materials 0.000 description 18
- 239000011734 sodium Substances 0.000 description 17
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 16
- 229960000583 acetic acid Drugs 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 235000011054 acetic acid Nutrition 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 239000006260 foam Substances 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 238000004809 thin layer chromatography Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229910014265 BrCl Inorganic materials 0.000 description 12
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 12
- 239000002775 capsule Substances 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 238000010828 elution Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- 239000003826 tablet Substances 0.000 description 11
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000004587 chromatography analysis Methods 0.000 description 10
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 10
- 239000003039 volatile agent Substances 0.000 description 10
- 241000701022 Cytomegalovirus Species 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- KEZMBKQTCPNSOF-UHFFFAOYSA-N 2-bromo-5,6-dichloro-1h-benzimidazole Chemical compound C1=C(Cl)C(Cl)=CC2=C1NC(Br)=N2 KEZMBKQTCPNSOF-UHFFFAOYSA-N 0.000 description 8
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 8
- 241000700721 Hepatitis B virus Species 0.000 description 8
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 8
- 150000001556 benzimidazoles Chemical class 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 238000010511 deprotection reaction Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 8
- 239000008101 lactose Substances 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 8
- 229940069328 povidone Drugs 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- 241000701085 Human alphaherpesvirus 3 Species 0.000 description 7
- 241000700605 Viruses Species 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000000306 component Substances 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000002777 nucleoside Substances 0.000 description 7
- 239000008363 phosphate buffer Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000004364 calculation method Methods 0.000 description 6
- 150000001720 carbohydrates Chemical class 0.000 description 6
- 235000014633 carbohydrates Nutrition 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 6
- PHPYXVIHDRDPDI-UHFFFAOYSA-N 2-bromo-1h-benzimidazole Chemical compound C1=CC=C2NC(Br)=NC2=C1 PHPYXVIHDRDPDI-UHFFFAOYSA-N 0.000 description 5
- IPRDZAMUYMOJTA-UHFFFAOYSA-N 5,6-dichloro-1h-benzimidazole Chemical compound C1=C(Cl)C(Cl)=CC2=C1NC=N2 IPRDZAMUYMOJTA-UHFFFAOYSA-N 0.000 description 5
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- LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical compound SC[C@@H](N)C(=O)N[C@H](CO)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@H](CO)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(O)=O)C(O)=O LCJVIYPJPCBWKS-NXPQJCNCSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- LGSAOJLQTXCYHF-UHFFFAOYSA-N tri(propan-2-yl)-tri(propan-2-yl)silyloxysilane Chemical compound CC(C)[Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)C(C)C LGSAOJLQTXCYHF-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical class OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229940093257 valacyclovir Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9711982.0A GB9711982D0 (en) | 1997-06-10 | 1997-06-10 | Benzimidazole derivatives |
| GB9711982.0 | 1997-06-10 | ||
| GB9714552.8 | 1997-07-11 | ||
| GBGB9714552.8A GB9714552D0 (en) | 1997-07-11 | 1997-07-11 | Benzimidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20010020465A true KR20010020465A (ko) | 2001-03-15 |
Family
ID=26311687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019997011599A Ceased KR20010020465A (ko) | 1997-06-10 | 1998-06-08 | 벤즈이미다졸 유도체 |
Country Status (34)
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19990081940A (ko) | 1996-01-23 | 1999-11-15 | 그레이엄 브레레톤, 레슬리 에드워즈 | 항바이러스제로서 변형된 벤즈이미다졸 누클레오시드 |
| CA2297076A1 (en) | 1997-07-30 | 1999-02-11 | The Regents Of The University Of Michigan | Lyxofuranosyl benzimidazoles as antiviral agents |
| DE19741715A1 (de) * | 1997-09-22 | 1999-03-25 | Hoechst Ag | Pentopyranosyl-Nucleosid, seine Herstellung und Verwendung |
| GB0008939D0 (en) | 2000-04-11 | 2000-05-31 | Glaxo Group Ltd | Process for preparing substituted benzimidazole compounds |
| PT1368028E (pt) | 2001-03-12 | 2007-11-26 | Avanir Pharmaceuticals | Compostos de benzimidazole para modulação de ige e inibição da proliferação celular |
| AU2003270426A1 (en) | 2002-09-12 | 2004-04-30 | Avanir Pharmaceuticals | PHENYL-INDOLE COMPOUNDS FOR MODULATING IgE AND INHIBITING CELLULAR PROLIFERATION |
| TWI276631B (en) | 2002-09-12 | 2007-03-21 | Avanir Pharmaceuticals | Phenyl-aza-benzimidazole compounds for modulating IgE and inhibiting cellular proliferation |
| AU2004261663A1 (en) * | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted benzimidazole-, benztriazole-, and benzimidazolone-O-glucosides |
| US20110070192A1 (en) * | 2003-11-14 | 2011-03-24 | Bruno Tse | Method of preparation of novel nucleoside analogs and uses |
| WO2006091646A2 (en) * | 2005-02-22 | 2006-08-31 | The Regents Of The University Of Michigan | Small molecule inhibitors of mdm2 and uses thereof |
| DE102005019549A1 (de) * | 2005-04-25 | 2006-12-14 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an Diaminobenzimidazol |
| WO2007070947A1 (en) * | 2005-12-22 | 2007-06-28 | Alchemia Ltd | Antibacterial agents |
| US8927528B2 (en) | 2006-01-19 | 2015-01-06 | The Regents Of The University Of Michigan | Composition for treating hearing loss |
| US8338397B2 (en) | 2006-01-19 | 2012-12-25 | The Regents Of The University Of Michigan | Composition and method of treating side effects from antibiotic treatment |
| US7951845B2 (en) | 2006-01-19 | 2011-05-31 | The Regents Of The University Of Michigan | Composition and method of treating hearing loss |
| US9889156B2 (en) | 2006-01-19 | 2018-02-13 | The Regents Of The University Of Michigan | Method for treating noise-induced hearing loss (NIHL) |
| US9919008B2 (en) | 2006-01-19 | 2018-03-20 | The Regents Of The University Of Michigan | Method for treating age-related hearing loss (ARHL) |
| US9770433B2 (en) | 2006-01-19 | 2017-09-26 | The Regents Of The University Of Michigan | Composition and method for treating tinnitus |
| US10238599B2 (en) | 2006-01-19 | 2019-03-26 | The Regents Of The University Of Michigan | Composition and method for treating congenital cytomegalovirus induced hearing loss |
| USRE46372E1 (en) | 2006-01-19 | 2017-04-25 | The Regents Of The Univerity Of Michigan | Method for treating hearing loss |
| CN101821277B (zh) | 2007-08-15 | 2014-05-07 | Isis制药公司 | 四氢吡喃核酸类似物 |
| WO2009100045A1 (en) * | 2008-02-04 | 2009-08-13 | Translational Genomics Research Institute | Compounds, pharmaceutical compositions and methods of use of hydroxamic acid derivatives |
| EP2265627A2 (en) | 2008-02-07 | 2010-12-29 | Isis Pharmaceuticals, Inc. | Bicyclic cyclohexitol nucleic acid analogs |
| AU2009296820B2 (en) | 2008-09-26 | 2014-03-20 | Merck Sharp & Dohme Llc | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| US8410284B2 (en) | 2008-10-22 | 2013-04-02 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US8563746B2 (en) | 2008-10-29 | 2013-10-22 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US8329914B2 (en) | 2008-10-31 | 2012-12-11 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| WO2010091308A2 (en) | 2009-02-06 | 2010-08-12 | Isis Pharmaceuticals, Inc. | Oligomeric compounds and methods |
| US8536320B2 (en) | 2009-02-06 | 2013-09-17 | Isis Pharmaceuticals, Inc. | Tetrahydropyran nucleic acid analogs |
| JP2013520502A (ja) | 2010-02-25 | 2013-06-06 | メルク・シャープ・エンド・ドーム・コーポレイション | 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体 |
| JP6005628B2 (ja) | 2010-04-28 | 2016-10-12 | アイオーニス ファーマシューティカルズ， インコーポレーテッドＩｏｎｉｓ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ，Ｉｎｃ． | 修飾ヌクレオシド、その類似体、およびこれらから調製されるオリゴマー化合物 |
| US8546344B2 (en) | 2010-10-28 | 2013-10-01 | Viropharma Incorporated | Crystalline phases of 5,6-dichloro-2-(isopropylamino)-1-β-L-ribofuranosyl)-1H-benzimidazole |
| WO2014134493A1 (en) * | 2013-03-01 | 2014-09-04 | Los Alamos National Security, Llc | Broad spectrum antibiotic compounds and use thereof |
| US9926556B2 (en) | 2014-04-28 | 2018-03-27 | Ionis Pharmaceuticals, Inc. | Linkage modified oligomeric compounds |
| WO2016089845A1 (en) * | 2014-12-01 | 2016-06-09 | Virginia Commonwealth University | A convergent approach to the total synthesis of telmisartan via a suzuki cross-coupling reaction |
| RU2629670C2 (ru) * | 2016-08-04 | 2017-08-31 | Федеральное государственное бюджетное учреждение науки институт биоорганической химии им. академиков М.М. Шемякина и Ю.А. Овчинникова Российской академии наук (ИБХ РАН) | 2-Амино-5,6-дифтор-1-(бета-D-рибофуранозил)-бензимидазол, способ получения и противовирусная активность его в отношении вируса герпеса простого 1-го типа |
| KR102583547B1 (ko) | 2020-03-30 | 2023-10-06 | (주)바이오메트릭스 테크놀로지 | 신규한 벤지미다졸 유도체, 이의 제조방법 및 이의 항암제 용도 |
| EP3907230B1 (en) * | 2020-03-30 | 2024-08-28 | Biometrix Technology Inc. | Novel benzimidazole derivatives, preparation method thereof and use thereof as anti-cancer agent comprising the same |
| CN114096549A (zh) * | 2020-06-23 | 2022-02-25 | 博美利克斯技术公司 | 新型苯并咪唑衍生物、其制备方法及其作为抗癌剂或者抗病毒剂的用途 |
| KR102449266B1 (ko) | 2020-06-23 | 2022-09-30 | (주)바이오메트릭스 테크놀로지 | 항암 활성 그리고 항바이러스 활성을 갖는 신규한 벤지미다졸-탄수화물 결합체 화합물(Benzimidazole carbohydrate conjugate compound) 및 이의 제조 방법 |
| KR102342313B1 (ko) | 2021-08-27 | 2021-12-24 | (주)바이오메트릭스 테크놀로지 | 벤지미다졸-탄수화물 결합체 화합물을 포함하는 미셀, 이의 제조방법, 이의 항암제 또는 항바이러스제로서의 용도 |
| CN119119151A (zh) * | 2024-09-04 | 2024-12-13 | 斯坦德药典标准物质研发(湖北)有限公司 | 一种马立巴韦的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1491244A (fr) | 1966-03-09 | 1967-08-11 | Nouveaux benzimidazoles solubles | |
| FR1476350A (fr) | 1966-04-18 | 1967-04-07 | Yale & Towne G M B H | Ferme-porte automatique à frein |
| US3655901A (en) | 1970-07-30 | 1972-04-11 | Merck & Co Inc | Method of inhibiting the formation of phenylethanalamine-n-methyl transferase with 2-aminobenzimidazoles |
| DE2130030A1 (de) | 1971-06-18 | 1972-12-21 | Bayer Ag | Fungizide und bakterizide Mittel |
| ES8101067A1 (es) | 1978-08-25 | 1980-12-01 | Thomae Gmbh Dr K | Procedimiento para la preparacion de nuevos bencimidazoles sustituidos en posicion 5 o 6 con un anillo de piridazinona |
| EP0304624A3 (de) | 1987-07-29 | 1989-03-22 | F. Hoffmann-La Roche Ag | Benzimidazol-2-yl-pyridiniumverbindungen |
| IT1226100B (it) | 1988-07-07 | 1990-12-10 | Dompe Farmaceutici Spa | Derivati benzimidazolici farmacologicamente attivi. |
| US5248672A (en) | 1990-11-01 | 1993-09-28 | The Regents Of The University Of Michigan | Polysubstituted benzimidazole nucleosides as antiviral agents |
| ZA923641B (en) | 1991-05-21 | 1993-02-24 | Iaf Biochem Int | Processes for the diastereoselective synthesis of nucleosides |
| EP0521463A3 (en) | 1991-07-04 | 1993-04-14 | Hoechst Aktiengesellschaft | Substituted cyclic cycloalkyltriols, process, intermediates for their preparation and their use as antiviral and antiparasitic agents |
| GB9205071D0 (en) | 1992-03-09 | 1992-04-22 | Wellcome Found | Therapeutic nucleosides |
| AU5447094A (en) | 1992-10-21 | 1994-05-09 | Regents Of The University Of Michigan, The | Polysubstituted benzimidazoles as antiviral agents |
| US5399580A (en) | 1993-03-08 | 1995-03-21 | Burroughs Wellcome Co. | Therapeutic nucleosides-uses |
| GB9413724D0 (en) * | 1994-07-07 | 1994-08-24 | Wellcome Found | Therapeutic nucleosides |
-
1998
- 1998-06-08 DK DK98936306T patent/DK0994890T3/da active
- 1998-06-08 HU HU0002224A patent/HUP0002224A3/hu unknown
- 1998-06-08 CN CN98807910A patent/CN1265665A/zh active Pending
- 1998-06-08 NZ NZ501415A patent/NZ501415A/en unknown
- 1998-06-08 AP APAP/P/1999/001707A patent/AP1262A/en active
- 1998-06-08 TR TR1999/03053T patent/TR199903053T2/xx unknown
- 1998-06-08 PT PT98936306T patent/PT994890E/pt unknown
- 1998-06-08 CA CA002293470A patent/CA2293470C/en not_active Expired - Lifetime
- 1998-06-08 KR KR1019997011599A patent/KR20010020465A/ko not_active Ceased
- 1998-06-08 AU AU85360/98A patent/AU740792C/en not_active Ceased
- 1998-06-08 ID IDW20000038A patent/ID24054A/id unknown
- 1998-06-08 MA MA25102A patent/MA26504A1/fr unknown
- 1998-06-08 EP EP98936306A patent/EP0994890B1/en not_active Expired - Lifetime
- 1998-06-08 PL PL98337773A patent/PL337773A1/xx unknown
- 1998-06-08 IL IL13328598A patent/IL133285A0/xx unknown
- 1998-06-08 SK SK1714-99A patent/SK171499A3/sk unknown
- 1998-06-08 EE EEP199900564A patent/EE9900564A/xx unknown
- 1998-06-08 JP JP50153899A patent/JP4548866B2/ja not_active Expired - Lifetime
- 1998-06-08 EA EA199901031A patent/EA002305B1/ru not_active IP Right Cessation
- 1998-06-08 US US09/424,934 patent/US6455507B1/en not_active Expired - Lifetime
- 1998-06-08 ES ES98936306T patent/ES2205527T3/es not_active Expired - Lifetime
- 1998-06-08 BR BR9810745-3A patent/BR9810745A/pt not_active IP Right Cessation
- 1998-06-08 WO PCT/EP1998/003380 patent/WO1998056761A2/en not_active Ceased
- 1998-06-08 DE DE69816992T patent/DE69816992T2/de not_active Expired - Lifetime
- 1998-06-08 AT AT98936306T patent/ATE246700T1/de not_active IP Right Cessation
- 1998-06-09 MY MYPI98002560A patent/MY132872A/en unknown
- 1998-06-09 TW TW087109162A patent/TW565566B/zh not_active IP Right Cessation
- 1998-06-09 HR HR980303A patent/HRP980303B1/xx not_active IP Right Cessation
- 1998-06-09 PE PE1998000488A patent/PE84099A1/es not_active Application Discontinuation
- 1998-06-09 CO CO98032828A patent/CO4970737A1/es unknown
- 1998-06-10 AR ARP980102756A patent/AR012964A1/es not_active Application Discontinuation
-
1999
- 1999-12-06 IS IS5285A patent/IS5285A/is unknown
- 1999-12-09 NO NO19996086A patent/NO314847B1/no not_active IP Right Cessation
- 1999-12-09 OA OA9900275A patent/OA11230A/en unknown
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