NO322458B1 - Benzimidazoler og imidazopyridiner, deres fremstilling og sammensetninger omfattende dem, samt deres anvendelse - Google Patents

Benzimidazoler og imidazopyridiner, deres fremstilling og sammensetninger omfattende dem, samt deres anvendelse Download PDF

Info

Publication number: NO322458B1
Authority: NO; Norway
Prior art keywords: formula; methyl; amine; pyridinyl; piperidinyl
Prior art date: 1999-06-28

Application number

NO20016369A

Other languages

English (en)

Norwegian (no)

Other versions

NO20016369D0 (no

NO20016369L (no

Inventor

Koenraad Jozef Lodewij Andries

Kathleen Petrus Meersman

Frans Eduard Janssens

Francois Maria Sommen

Original Assignee

Janssen Pharmaceutica Nv

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.)

1999-06-28

Filing date

2001-12-27

Publication date

2006-10-09

2001-12-27 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2001-12-27 Publication of NO20016369D0 publication Critical patent/NO20016369D0/no

2002-02-20 Publication of NO20016369L publication Critical patent/NO20016369L/no

2006-10-09 Publication of NO322458B1 publication Critical patent/NO322458B1/no

Links

239000000203 mixture Substances 0.000 title claims description 75
238000002360 preparation method Methods 0.000 title description 18
150000001556 benzimidazoles Chemical class 0.000 title description 2
150000005232 imidazopyridines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 120
239000002904 solvent Substances 0.000 claims description 75
238000006243 chemical reaction Methods 0.000 claims description 38
-1 d-alkyl Chemical group 0.000 claims description 38
239000012442 inert solvent Substances 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 31
239000002585 base Substances 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 17
150000001412 amines Chemical group 0.000 claims description 16
150000002431 hydrogen Chemical group 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
239000003638 chemical reducing agent Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
238000005576 amination reaction Methods 0.000 claims description 3
ITHFMXUNCGKKML-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-1-[2-(6-bromopyridin-2-yl)ethoxymethyl]benzimidazol-2-amine Chemical compound C1CN(CC(N)C(C)C)CCC1NC1=NC2=CC=CC=C2N1COCCC1=CC=CC(Br)=N1 ITHFMXUNCGKKML-UHFFFAOYSA-N 0.000 claims description 3
WKAYRRDIBGZUEO-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-1-[2-ethoxyethoxy-(6-phenylpyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CC(N)C(C)C)CCC1NC1=NC2=CC=CC=C2N1C(OCCOCC)C(N=1)=CC=CC=1C1=CC=CC=C1 WKAYRRDIBGZUEO-UHFFFAOYSA-N 0.000 claims description 3
LGHANUAZYINPCD-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-3-[2-methoxyethoxy-(6-methylpyridin-2-yl)methyl]-7-methylimidazo[4,5-b]pyridin-2-amine Chemical compound C1CN(CC(N)C(C)C)CCC1NC1=NC2=C(C)C=CN=C2N1C(OCCOC)C1=CC=CC(C)=N1 LGHANUAZYINPCD-UHFFFAOYSA-N 0.000 claims description 3
XBFLEAOBNOWGRN-UHFFFAOYSA-N n-[1-(2-aminopropyl)piperidin-4-yl]-1-[ethoxy-(6-methylpyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CC(C)N)CCC1NC1=NC2=CC=CC=C2N1C(OCC)C1=CC=CC(C)=N1 XBFLEAOBNOWGRN-UHFFFAOYSA-N 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 2
MLJSFVJKUOQFMW-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-1-[ethoxy-(6-methylpyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CC(N)C(C)C)CCC1NC1=NC2=CC=CC=C2N1C(OCC)C1=CC=CC(C)=N1 MLJSFVJKUOQFMW-UHFFFAOYSA-N 0.000 claims description 2
KEWOBSMGDOVGLX-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-6-chloro-1-[2-methoxyethoxy-(6-methylpyridin-2-yl)methyl]-4-methylbenzimidazol-2-amine;trihydrate;trihydrochloride Chemical compound O.O.O.Cl.Cl.Cl.C1CN(CC(N)C(C)C)CCC1NC1=NC2=C(C)C=C(Cl)C=C2N1C(OCCOC)C1=CC=CC(C)=N1 KEWOBSMGDOVGLX-UHFFFAOYSA-N 0.000 claims description 2
GMHWLJJKLAMEJF-UHFFFAOYSA-N n-[1-(2-aminoethyl)piperidin-4-yl]-1-[2-methoxyethoxy-(6-methylpyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CCN)CCC1NC1=NC2=CC=CC=C2N1C(OCCOC)C1=CC=CC(C)=N1 GMHWLJJKLAMEJF-UHFFFAOYSA-N 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
UOZHEKIEYHSSGM-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-1-[2-(6-bromopyridin-2-yl)ethoxymethyl]-4-methylbenzimidazol-2-amine;hydrate Chemical compound O.C1CN(CC(N)C(C)C)CCC1NC1=NC2=C(C)C=CC=C2N1COCCC1=CC=CC(Br)=N1 UOZHEKIEYHSSGM-UHFFFAOYSA-N 0.000 claims 1
AJCOXCKQNFSSLE-UHFFFAOYSA-N n-[1-(2-aminoethyl)piperidin-4-yl]-1-[2-ethoxyethoxy-(6-methylpyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CCN)CCC1NC1=NC2=CC=CC=C2N1C(OCCOCC)C1=CC=CC(C)=N1 AJCOXCKQNFSSLE-UHFFFAOYSA-N 0.000 claims 1
238000000844 transformation Methods 0.000 claims 1
239000000543 intermediate Substances 0.000 description 172
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 42
235000019441 ethanol Nutrition 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000460 chlorine Substances 0.000 description 34
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
239000003480 eluent Substances 0.000 description 24
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
239000003054 catalyst Substances 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000004440 column chromatography Methods 0.000 description 18
239000002244 precipitate Substances 0.000 description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
125000005843 halogen group Chemical group 0.000 description 15
150000003254 radicals Chemical class 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
230000000840 anti-viral effect Effects 0.000 description 14
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
239000012074 organic phase Substances 0.000 description 13
241000725643 Respiratory syncytial virus Species 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 10
229910000104 sodium hydride Inorganic materials 0.000 description 10
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
235000011114 ammonium hydroxide Nutrition 0.000 description 9
239000003245 coal Substances 0.000 description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
150000001721 carbon Chemical group 0.000 description 8
229940079593 drug Drugs 0.000 description 8
235000015320 potassium carbonate Nutrition 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
206010061603 Respiratory syncytial virus infection Diseases 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
231100000135 cytotoxicity Toxicity 0.000 description 7
230000003013 cytotoxicity Effects 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
229930195734 saturated hydrocarbon Natural products 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
229910000033 sodium borohydride Inorganic materials 0.000 description 7
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
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125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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125000006545 (C1-C9) alkyl group Chemical group 0.000 description 3
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
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 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 3
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239000012280 lithium aluminium hydride Substances 0.000 description 2
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GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
IMLIPHSGYFXWAA-UHFFFAOYSA-N ethyl 4-(1h-benzimidazol-2-ylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC2=CC=CC=C2N1 IMLIPHSGYFXWAA-UHFFFAOYSA-N 0.000 description 1
GHBNSPBYQRCCIG-UHFFFAOYSA-N ethyl 4-(1h-imidazo[4,5-b]pyridin-2-ylmethyl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1CC1=NC2=NC=CC=C2N1 GHBNSPBYQRCCIG-UHFFFAOYSA-N 0.000 description 1
OMEPSRDWESOKOP-UHFFFAOYSA-N ethyl 4-(2-ethoxy-2-iminoethyl)piperidine-1-carboxylate;hydrochloride Chemical compound Cl.CCOC(=N)CC1CCN(C(=O)OCC)CC1 OMEPSRDWESOKOP-UHFFFAOYSA-N 0.000 description 1
HFVILTJYZQVFQQ-UHFFFAOYSA-N ethyl 4-[(1-phenacylimidazo[4,5-b]pyridin-2-yl)methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1CC1=NC2=NC=CC=C2N1CC(=O)C1=CC=CC=C1 HFVILTJYZQVFQQ-UHFFFAOYSA-N 0.000 description 1
GPBVJNRTFUUWER-UHFFFAOYSA-N ethyl 4-[[1-(2-hydroxy-2-phenylethyl)imidazo[4,5-b]pyridin-2-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC2=NC=CC=C2N1CC(O)C1=CC=CC=C1 GPBVJNRTFUUWER-UHFFFAOYSA-N 0.000 description 1
LKKAWMNEPUOSKW-UHFFFAOYSA-N ethyl 4-isothiocyanatopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N=C=S)CC1 LKKAWMNEPUOSKW-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000013100 final test Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
229960001438 immunostimulant agent Drugs 0.000 description 1
239000003022 immunostimulating agent Substances 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229940031551 inactivated vaccine Drugs 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229960001388 interferon-beta Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
231100000516 lung damage Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
BXLWWQRYRLBKRP-UHFFFAOYSA-N n-(1-benzylpiperidin-4-yl)-1-[ethoxy(pyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CC=2C=CC=CC=2)CCC1NC1=NC2=CC=CC=C2N1C(OCC)C1=CC=CC=N1 BXLWWQRYRLBKRP-UHFFFAOYSA-N 0.000 description 1
VYMQMKTUYSTHEX-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-1-[2-ethoxyethoxy-(6-methylpyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CC(N)C(C)C)CCC1NC1=NC2=CC=CC=C2N1C(OCCOCC)C1=CC=CC(C)=N1 VYMQMKTUYSTHEX-UHFFFAOYSA-N 0.000 description 1
MLFNCCYNYSLFKS-UHFFFAOYSA-N n-[1-(2-amino-3-methylbutyl)piperidin-4-yl]-1-[2-methoxyethoxy-(6-methylpyridin-2-yl)methyl]benzimidazol-2-amine Chemical compound C1CN(CC(N)C(C)C)CCC1NC1=NC2=CC=CC=C2N1C(OCCOC)C1=CC=CC(C)=N1 MLFNCCYNYSLFKS-UHFFFAOYSA-N 0.000 description 1
FLWJOGQIGWFRKH-UHFFFAOYSA-N n-[1-(2-aminoethyl)piperidin-4-yl]-1-[(6-methylpyridin-2-yl)-(2-phenylmethoxyethoxy)methyl]benzimidazol-2-amine Chemical compound CC1=CC=CC(C(OCCOCC=2C=CC=CC=2)N2C3=CC=CC=C3N=C2NC2CCN(CCN)CC2)=N1 FLWJOGQIGWFRKH-UHFFFAOYSA-N 0.000 description 1
SBHOLOODOKZVDC-UHFFFAOYSA-N n-[1-(2-aminoethyl)piperidin-4-yl]-1-[2-(6-bromopyridin-2-yl)ethoxymethyl]benzimidazol-2-amine Chemical compound C1CN(CCN)CCC1NC1=NC2=CC=CC=C2N1COCCC1=CC=CC(Br)=N1 SBHOLOODOKZVDC-UHFFFAOYSA-N 0.000 description 1
CWCPQDOTWZGFSH-UHFFFAOYSA-N n-[1-(2-aminopropyl)piperidin-4-yl]-1-[ethoxy-(6-methylpyridin-2-yl)methyl]benzimidazol-2-amine;hydrate Chemical compound O.C1CN(CC(C)N)CCC1NC1=NC2=CC=CC=C2N1C(OCC)C1=CC=CC(C)=N1 CWCPQDOTWZGFSH-UHFFFAOYSA-N 0.000 description 1
YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
HLDKASZRJPWADR-UHFFFAOYSA-N n-piperidin-4-yl-1h-benzimidazol-2-amine;dihydrobromide Chemical compound Br.Br.C1CNCCC1NC1=NC2=CC=CC=C2N1 HLDKASZRJPWADR-UHFFFAOYSA-N 0.000 description 1
201000009240 nasopharyngitis Diseases 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229960000402 palivizumab Drugs 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229960000329 ribavirin Drugs 0.000 description 1
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229960005137 succinic acid Drugs 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
231100000211 teratogenicity Toxicity 0.000 description 1
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 1
OSDUDPQWLGJWGL-UHFFFAOYSA-N tert-butyl 4-(1h-benzimidazol-2-ylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1 OSDUDPQWLGJWGL-UHFFFAOYSA-N 0.000 description 1
XFPMCSZSEOSWCI-UHFFFAOYSA-N tert-butyl 4-[(1-phenacylbenzimidazol-2-yl)amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1CC(=O)C1=CC=CC=C1 XFPMCSZSEOSWCI-UHFFFAOYSA-N 0.000 description 1
NBWWFMNRBCTCNZ-UHFFFAOYSA-N tert-butyl 4-[[1-(2-methoxy-2-phenylethyl)benzimidazol-2-yl]amino]piperidine-1-carboxylate Chemical compound C=1C=CC=CC=1C(OC)CN(C1=CC=CC=C1N=1)C=1NC1CCN(C(=O)OC(C)(C)C)CC1 NBWWFMNRBCTCNZ-UHFFFAOYSA-N 0.000 description 1
LZHSVIWHGROZQX-UHFFFAOYSA-N tert-butyl 4-[[1-[2-(6-bromopyridin-2-yl)ethoxymethyl]benzimidazol-2-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1COCCC1=CC=CC(Br)=N1 LZHSVIWHGROZQX-UHFFFAOYSA-N 0.000 description 1
FCRRSXONVUDSGW-UHFFFAOYSA-N tert-butyl 4-[[1-[2-hydroxy-2-(6-methylpyridin-2-yl)ethyl]benzimidazol-2-yl]amino]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C(O)CN2C3=CC=CC=C3N=C2NC2CCN(CC2)C(=O)OC(C)(C)C)=N1 FCRRSXONVUDSGW-UHFFFAOYSA-N 0.000 description 1
OOQRRYDVICNJGC-UHFFFAOYSA-N tert-butyl n-(1-hydroxy-3-methylbutan-2-yl)carbamate Chemical compound CC(C)C(CO)NC(=O)OC(C)(C)C OOQRRYDVICNJGC-UHFFFAOYSA-N 0.000 description 1
RQGAABUMZBIDNX-UHFFFAOYSA-N tert-butyl n-[2-[4-[[1-[2-(6-bromopyridin-2-yl)ethoxymethyl]benzimidazol-2-yl]amino]piperidin-1-yl]ethyl]carbamate Chemical compound C1CN(CCNC(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1COCCC1=CC=CC(Br)=N1 RQGAABUMZBIDNX-UHFFFAOYSA-N 0.000 description 1
JDVLZSZDSGIGQW-UHFFFAOYSA-N tert-butyl n-[2-[4-[[1-[ethoxy-(6-methyl-3-phenylmethoxypyridin-2-yl)methyl]benzimidazol-2-yl]amino]piperidin-1-yl]ethyl]carbamate Chemical compound C1CN(CCNC(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1C(OCC)C1=NC(C)=CC=C1OCC1=CC=CC=C1 JDVLZSZDSGIGQW-UHFFFAOYSA-N 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- A61P31/14—Antivirals for RNA viruses
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Virology (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO20016369A 1999-06-28 2001-12-27 Benzimidazoler og imidazopyridiner, deres fremstilling og sammensetninger omfattende dem, samt deres anvendelse NO322458B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99202088		1999-06-28
PCT/EP2000/005675 WO2001000612A2 (fr)	1999-06-28	2000-06-20	Inhibiteurs de replication du virus respiratoire syncytial

Publications (3)

Publication Number	Publication Date
NO20016369D0 NO20016369D0 (no)	2001-12-27
NO20016369L NO20016369L (no)	2002-02-20
NO322458B1 true NO322458B1 (no)	2006-10-09

Family

ID=8240373

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20016369A NO322458B1 (no)	1999-06-28	2001-12-27	Benzimidazoler og imidazopyridiner, deres fremstilling og sammensetninger omfattende dem, samt deres anvendelse

Country Status (33)

Country	Link
US (3)	US6747028B1 (fr)
EP (1)	EP1196409B1 (fr)
JP (1)	JP2003503402A (fr)
KR (1)	KR100731271B1 (fr)
CN (1)	CN1210275C (fr)
AR (1)	AR035991A1 (fr)
AT (1)	ATE258928T1 (fr)
AU (1)	AU778218B2 (fr)
BG (1)	BG65328B1 (fr)
BR (1)	BR0012047A (fr)
CA (1)	CA2376676C (fr)
DE (1)	DE60008112T2 (fr)
DK (1)	DK1196409T3 (fr)
EA (1)	EA005027B1 (fr)
EE (1)	EE04591B1 (fr)
ES (1)	ES2215683T3 (fr)
HK (1)	HK1045997A1 (fr)
HR (1)	HRP20010935A2 (fr)
HU (1)	HUP0201869A3 (fr)
IL (2)	IL147327A0 (fr)
MX (1)	MXPA02000120A (fr)
MY (1)	MY127687A (fr)
NO (1)	NO322458B1 (fr)
NZ (1)	NZ515664A (fr)
PL (1)	PL200674B1 (fr)
PT (1)	PT1196409E (fr)
SI (1)	SI1196409T1 (fr)
SK (1)	SK19122001A3 (fr)
TR (1)	TR200103806T2 (fr)
TW (1)	TWI278454B (fr)
UA (1)	UA74787C2 (fr)
WO (1)	WO2001000612A2 (fr)
ZA (1)	ZA200110479B (fr)

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2000
- 2000-06-20 AT AT00943840T patent/ATE258928T1/de not_active IP Right Cessation
- 2000-06-20 AU AU58166/00A patent/AU778218B2/en not_active Ceased
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- 2000-06-20 DK DK00943840T patent/DK1196409T3/da active
- 2000-06-20 CN CNB008095442A patent/CN1210275C/zh not_active Expired - Fee Related
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- 2000-06-20 WO PCT/EP2000/005675 patent/WO2001000612A2/fr not_active Ceased
- 2000-06-20 US US10/019,380 patent/US6747028B1/en not_active Expired - Fee Related
- 2000-06-20 ES ES00943840T patent/ES2215683T3/es not_active Expired - Lifetime
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- 2000-06-20 EA EA200200088A patent/EA005027B1/ru not_active IP Right Cessation
- 2000-06-20 EP EP00943840A patent/EP1196409B1/fr not_active Expired - Lifetime
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- 2000-06-20 HK HK02107622.9A patent/HK1045997A1/zh unknown
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- 2000-06-20 KR KR1020017015295A patent/KR100731271B1/ko not_active Expired - Fee Related
- 2000-06-20 HR HR20010935A patent/HRP20010935A2/hr not_active Application Discontinuation
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- 2000-06-20 BR BR0012047-2A patent/BR0012047A/pt not_active Application Discontinuation
- 2000-06-26 TW TW089112478A patent/TWI278454B/zh not_active IP Right Cessation
- 2000-06-27 MY MYPI20002907A patent/MY127687A/en unknown
- 2000-06-27 AR ARP000103221A patent/AR035991A1/es not_active Application Discontinuation
2001
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- 2001-12-27 NO NO20016369A patent/NO322458B1/no unknown
2002
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Also Published As

Publication number	Publication date
CA2376676A1 (fr)	2001-01-04
BG65328B1 (bg)	2008-02-29
EA200200088A1 (ru)	2002-06-27
MY127687A (en)	2006-12-29
DE60008112D1 (en)	2004-03-11
DE60008112T2 (de)	2004-09-16
UA74787C2 (en)	2006-02-15
PT1196409E (pt)	2004-06-30
US20070015747A1 (en)	2007-01-18
PL352378A1 (en)	2003-08-25
SI1196409T1 (en)	2004-06-30
CA2376676C (fr)	2009-01-20
CN1358181A (zh)	2002-07-10
EP1196409A2 (fr)	2002-04-17
US20070135404A1 (en)	2007-06-14
ES2215683T3 (es)	2004-10-16
EE200100688A (et)	2003-04-15
US7528149B2 (en)	2009-05-05
HK1045997A1 (zh)	2002-12-20
US6747028B1 (en)	2004-06-08
US7179811B2 (en)	2007-02-20
JP2003503402A (ja)	2003-01-28
BG106286A (en)	2002-10-31
NZ515664A (en)	2004-01-30
CN1210275C (zh)	2005-07-13
AU5816600A (en)	2001-01-31
TWI278454B (en)	2007-04-11
BR0012047A (pt)	2002-03-12
MXPA02000120A (es)	2002-07-02
NO20016369D0 (no)	2001-12-27
NO20016369L (no)	2002-02-20
WO2001000612A3 (fr)	2001-03-29
KR100731271B1 (ko)	2007-06-21
EP1196409B1 (fr)	2004-02-04
ZA200110479B (en)	2003-03-20
HUP0201869A3 (en)	2003-12-29
EA005027B1 (ru)	2004-10-28
AU778218B2 (en)	2004-11-25
TR200103806T2 (tr)	2002-06-21
WO2001000612A2 (fr)	2001-01-04
IL147327A (en)	2007-06-03
HRP20010935A2 (en)	2003-06-30
AR035991A1 (es)	2004-08-04
ATE258928T1 (de)	2004-02-15
DK1196409T3 (da)	2004-06-07
HUP0201869A2 (hu)	2002-11-28
SK19122001A3 (sk)	2003-01-09
EE04591B1 (et)	2006-02-15
KR20020003884A (ko)	2002-01-15
PL200674B1 (pl)	2009-01-30
IL147327A0 (en)	2002-08-14

Publication	Publication Date	Title
US6747028B1 (en)	2004-06-08	Respiratory syncytial virus replication inhibitors
EP1196410B1 (fr)	2004-02-18	Inhibiteurs de replication de virus syncytiaux respiratoires
KR100731276B1 (ko)	2007-06-21	호흡기 신시티움 바이러스 복제 억제제
KR101074333B1 (ko)	2011-10-17	호흡기 세포융합 바이러스 복제 저해제로서의아미노-벤즈이미다졸 유도체
RU2434000C2 (ru)	2011-11-20	1-(2-амино-3-(замещенный алкил)-3н-бензимидазоилметил)-3-замещенные-1,3-дигидробензоимидазол-2-оны с активностью в отношении респираторно-синцитиального вируса