NO20023750L - 1H-imidazopyridinderivater - Google Patents

1H-imidazopyridinderivater Download PDF

Info

Publication number: NO20023750L
Authority: NO; Norway
Prior art keywords: group; substituted; ethyl; imidazo; trifluoromethyl
Prior art date: 2000-02-09

Application number

NO20023750A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023750D0 (no

Inventor

Hideo Kato

Jun Sakaguchi

Tomoyuki Izumi

Ken-Ichi Kato

Original Assignee

Hokuriku Pharmaceutical

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.)

2000-02-09

Filing date

2002-08-08

Publication date

2002-10-07

2002-08-08 Application filed by Hokuriku Pharmaceutical filed Critical Hokuriku Pharmaceutical

2002-08-08 Publication of NO20023750D0 publication Critical patent/NO20023750D0/no

2002-10-07 Publication of NO20023750L publication Critical patent/NO20023750L/no

Links

GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims description 11
-1 thiocarbamoyl group Chemical group 0.000 claims description 182
150000001875 compounds Chemical class 0.000 claims description 113
150000003839 salts Chemical class 0.000 claims description 29
125000000623 heterocyclic group Chemical group 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 19
238000004519 manufacturing process Methods 0.000 claims description 18
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 17
102000004127 Cytokines Human genes 0.000 claims description 16
108090000695 Cytokines Proteins 0.000 claims description 16
108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 16
125000003277 amino group Chemical group 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 15
229920006395 saturated elastomer Polymers 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 14
102000000589 Interleukin-1 Human genes 0.000 claims description 13
108010002352 Interleukin-1 Proteins 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
229940079593 drug Drugs 0.000 claims description 11
125000002252 acyl group Chemical group 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
238000011282 treatment Methods 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
230000001225 therapeutic effect Effects 0.000 claims description 7
230000000069 prophylactic effect Effects 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
239000003112 inhibitor Substances 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 3
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
102000003390 tumor necrosis factor Human genes 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
239000002904 solvent Substances 0.000 description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
239000013078 crystal Substances 0.000 description 55
229910052799 carbon Inorganic materials 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 35
239000000243 solution Substances 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
238000000921 elemental analysis Methods 0.000 description 24
238000001953 recrystallisation Methods 0.000 description 24
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 19
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 14
238000010992 reflux Methods 0.000 description 14
125000001424 substituent group Chemical group 0.000 description 14
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
229910000027 potassium carbonate Inorganic materials 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007788 liquid Substances 0.000 description 11
239000002253 acid Substances 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
KRNSYSYRLQDHDK-UHFFFAOYSA-N 2,3-Cyclopentenopyridine Natural products C1=CN=C2CCCC2=C1 KRNSYSYRLQDHDK-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
DLKYQYMXPSONJP-UHFFFAOYSA-N cyclopenta[b]pyridine Chemical compound C1=C[N]C2=CC=CC2=C1 DLKYQYMXPSONJP-UHFFFAOYSA-N 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
238000001914 filtration Methods 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
125000000524 functional group Chemical group 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
238000001308 synthesis method Methods 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
ABZGJBAMTLQZAW-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 ABZGJBAMTLQZAW-UHFFFAOYSA-N 0.000 description 5
108010001336 Horseradish Peroxidase Proteins 0.000 description 5
108090000193 Interleukin-1 beta Proteins 0.000 description 5
102000003777 Interleukin-1 beta Human genes 0.000 description 5
230000001363 autoimmune Effects 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000012046 mixed solvent Substances 0.000 description 5
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
238000012360 testing method Methods 0.000 description 5
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
PSBNTDYPNNVSIJ-UHFFFAOYSA-N 8-chloro-2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=C(Cl)C=C3C=2N1CCC1CCNCC1 PSBNTDYPNNVSIJ-UHFFFAOYSA-N 0.000 description 4
206010006895 Cachexia Diseases 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
101001033249 Homo sapiens Interleukin-1 beta Proteins 0.000 description 4
101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 4
102000014150 Interferons Human genes 0.000 description 4
108010050904 Interferons Proteins 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000001514 detection method Methods 0.000 description 4
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 4
102000057041 human TNF Human genes 0.000 description 4
229940079322 interferon Drugs 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
238000010189 synthetic method Methods 0.000 description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 3
MEOYIJFTDKUQMA-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 MEOYIJFTDKUQMA-UHFFFAOYSA-N 0.000 description 3
LEQHEYNRMJITKW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1=CC(OC)=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=CC=C3)C3=C2N1CCC1CCNCC1 LEQHEYNRMJITKW-UHFFFAOYSA-N 0.000 description 3
HKXLCKHMOVSPFA-UHFFFAOYSA-N 2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethanamine Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCN)C=1C1=CC=CC=C1 HKXLCKHMOVSPFA-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000011088 calibration curve Methods 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000005457 ice water Substances 0.000 description 3
DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 3
125000005936 piperidyl group Chemical group 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
IOJJYEFEMXFEGB-UHFFFAOYSA-N 2,2,2-trifluoro-n-[2-(2-nitroacetyl)phenyl]acetamide Chemical compound [O-][N+](=O)CC(=O)C1=CC=CC=C1NC(=O)C(F)(F)F IOJJYEFEMXFEGB-UHFFFAOYSA-N 0.000 description 2
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
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239000011664 nicotinic acid Substances 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
239000003002 pH adjusting agent Substances 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
108040007629 peroxidase activity proteins Proteins 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UCQFSGCWHRTMGG-UHFFFAOYSA-N pyrazole-1-carboximidamide Chemical compound NC(=N)N1C=CC=N1 UCQFSGCWHRTMGG-UHFFFAOYSA-N 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical compound OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Substances [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LBQDLHPFISVBRU-UHFFFAOYSA-N tert-butyl 4-(2-aminoethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CCN)CC1 LBQDLHPFISVBRU-UHFFFAOYSA-N 0.000 description 1
MNQQQCKGOPEKNY-UHFFFAOYSA-N tert-butyl 4-[2-(2-phenyl-4-sulfanylidene-5h-imidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC(S)=C2N=C1C1=CC=CC=C1 MNQQQCKGOPEKNY-UHFFFAOYSA-N 0.000 description 1
FSROTDSLIAOVEJ-UHFFFAOYSA-N tert-butyl 4-[2-(2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC=C2N=C1C1=CC=CC=C1 FSROTDSLIAOVEJ-UHFFFAOYSA-N 0.000 description 1
KXZVDQAMYGQXBP-UHFFFAOYSA-N tert-butyl 4-[2-(4-chloro-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC(Cl)=C2N=C1C1=CC=CC=C1 KXZVDQAMYGQXBP-UHFFFAOYSA-N 0.000 description 1
OAOYTKFLHIOBAU-UHFFFAOYSA-N tert-butyl 4-[2-[2-(4-iodophenyl)-8-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C=2C3=CC(C)=CC=C3N=C(C(F)(F)F)C=2N=C1C1=CC=C(I)C=C1 OAOYTKFLHIOBAU-UHFFFAOYSA-N 0.000 description 1
PFUNHNGQUCDGDX-UHFFFAOYSA-N tert-butyl 4-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCN1C2=C3C=CC=CC3=NC(C(F)(F)F)=C2N=C1C1=CC=CC=C1 PFUNHNGQUCDGDX-UHFFFAOYSA-N 0.000 description 1
LCLPKKKLIPFUGL-UHFFFAOYSA-N tert-butyl 4-[2-[[3-amino-6-methyl-2-(trifluoromethyl)quinolin-4-yl]amino]ethyl]piperidine-1-carboxylate Chemical compound C12=CC(C)=CC=C2N=C(C(F)(F)F)C(N)=C1NCCC1CCN(C(=O)OC(C)(C)C)CC1 LCLPKKKLIPFUGL-UHFFFAOYSA-N 0.000 description 1
VTVAUYPEELMWPX-UHFFFAOYSA-N tert-butyl 4-[2-[[3-nitro-2-(trifluoromethyl)quinolin-4-yl]amino]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCNC1=C([N+]([O-])=O)C(C(F)(F)F)=NC2=CC=CC=C12 VTVAUYPEELMWPX-UHFFFAOYSA-N 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
239000001069 triethyl citrate Substances 0.000 description 1
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
235000013769 triethyl citrate Nutrition 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
229910021642 ultra pure water Inorganic materials 0.000 description 1
239000012498 ultrapure water Substances 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- 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
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Neurology (AREA)
Communicable Diseases (AREA)
Hematology (AREA)
Obesity (AREA)
Biomedical Technology (AREA)
Emergency Medicine (AREA)
Neurosurgery (AREA)
Endocrinology (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Transplantation (AREA)
Dermatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO20023750A 2000-02-09 2002-08-08 1H-imidazopyridinderivater NO20023750L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2000031270		2000-02-09
JP2000277507		2000-09-13
PCT/JP2001/000816 WO2001058900A1 (fr)	2000-02-09	2001-02-06	Derives de 1h-imidazopyridine

Publications (2)

Publication Number	Publication Date
NO20023750D0 NO20023750D0 (no)	2002-08-08
NO20023750L true NO20023750L (no)	2002-10-07

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ID=26585077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20023750A NO20023750L (no)	2000-02-09	2002-08-08	1H-imidazopyridinderivater

Country Status (16)

Country	Link
US (1)	US20040054182A1 (fr)
EP (1)	EP1256582A1 (fr)
KR (1)	KR20020073211A (fr)
CN (1)	CN1422269A (fr)
AU (1)	AU2001230584A1 (fr)
BG (1)	BG107067A (fr)
BR (1)	BR0108303A (fr)
CA (1)	CA2399136A1 (fr)
CZ (1)	CZ20022626A3 (fr)
HU (1)	HUP0204474A3 (fr)
IL (1)	IL150841A0 (fr)
MX (1)	MXPA02007525A (fr)
NO (1)	NO20023750L (fr)
PL (1)	PL355866A1 (fr)
SK (1)	SK11202002A3 (fr)
WO (1)	WO2001058900A1 (fr)

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CN102558155A (zh)	2003-01-14	2012-07-11	阿伦纳药品公司	作为代谢调节剂的芳基和杂芳基衍生物及其所涉及的疾病如糖尿病和高血糖症的预防和治疗
US7314877B2 (en)	2003-03-07	2008-01-01	Kowa Co., Ltd.	Benzofuran derivative
AU2004220534A1 (en) *	2003-03-07	2004-09-23	3M Innovative Properties Company	1-amino 1H-imidazoquinolines
US7163947B2 (en)	2003-03-07	2007-01-16	3M Innovative Properties Company	1-Amino 1H-imidazoquinolines
AR045047A1 (es)	2003-07-11	2005-10-12	Arena Pharm Inc	Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
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EP1658076B1 (fr)	2003-08-27	2013-03-06	3M Innovative Properties Company	Imidazoquinolines substituees par aryloxy et arylalkyleneoxy
EP1660026A4 (fr)	2003-09-05	2008-07-16	3M Innovative Properties Co	Traitement pour le lymphome a cellules b cd5+
NZ546273A (en)	2003-10-03	2009-05-31	Coley Pharm Group Inc	Alkoxy substituted imidazoquinolines
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
CA2545825A1 (fr)	2003-11-14	2005-06-02	3M Innovative Properties Company	Composes d'un anneau d'imidazo substitue par hydroxylamine
AU2004291101A1 (en)	2003-11-14	2005-06-02	3M Innovative Properties Company	Oxime substituted imidazo ring compounds
RU2006121646A (ru) *	2003-11-21	2008-01-10	Новартис АГ (CH)	Производные 1h-имидазохинолина в качестве ингибиторов протеинкиназы
AR046845A1 (es) *	2003-11-21	2005-12-28	Novartis Ag	Derivados de 1h-imidazo[4,5-c]quinolina para tratamiento de enfermedades dependientes de las proteino-quinasas
AR046781A1 (es)	2003-11-25	2005-12-21	3M Innovative Properties Co	Derivados de imidazoquinolinas. composiciones farmaceuticas.
EP1701955A1 (fr)	2003-12-29	2006-09-20	3M Innovative Properties Company	Imidazoquinolines a substitution arylalcenyle et arylalkynyle
WO2005066169A2 (fr)	2003-12-30	2005-07-21	3M Innovative Properties Company	Sulfonamides d'imidazoquinolinyle, d'imidazopyridinyle et d'imidazonaphtyridinyle
EP1730143A2 (fr)	2004-03-24	2006-12-13	3M Innovative Properties Company	Imidazopyridines, imidazoquinolines, et imidazonaphthyridines a substitution amide
DK1765310T3 (en)	2004-05-28	2016-01-11	Oryxe	MIXING for transdermal delivery of LAV AND HØJMOLEKYLVÆGTFORBINDELSER
WO2005123080A2 (fr)	2004-06-15	2005-12-29	3M Innovative Properties Company	Imidazoquinolines et imidazonaphthyridines substituees par un heterocyclyle contenant un azote
WO2006009826A1 (fr)	2004-06-18	2006-01-26	3M Innovative Properties Company	Thiazoloquinolines et thiazolonaphtyridines substitues par aryloxy et arylalkyleneoxy
US7897609B2 (en)	2004-06-18	2011-03-01	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
US7915281B2 (en)	2004-06-18	2011-03-29	3M Innovative Properties Company	Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method
US8034938B2 (en)	2004-12-30	2011-10-11	3M Innovative Properties Company	Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds
CA2592904C (fr)	2004-12-30	2015-04-07	3M Innovative Properties Company	Composes chiraux a cycle [1,2]imidazo[4,5] fusionne
US7683171B2 (en)	2005-02-04	2010-03-23	Bristol-Myers Squibb Company	1H-imidazo[4,5-d]thieno[3,2-b]pyridine based tricyclic compounds and pharmaceutical compositions comprising same
AU2006210392A1 (en)	2005-02-04	2006-08-10	Coley Pharmaceutical Group, Inc.	Aqueous gel formulations containing immune response modifiers
CA2597587A1 (fr)	2005-02-11	2006-08-17	Coley Pharmaceutical Group, Inc.	Composes cycliques imidazo[4,5-c] substitues par oxime et hydroxylamine et procedes associes
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2001
- 2001-02-06 US US10/181,407 patent/US20040054182A1/en not_active Abandoned
- 2001-02-06 CN CN01807727A patent/CN1422269A/zh active Pending
- 2001-02-06 BR BR0108303-1A patent/BR0108303A/pt not_active Application Discontinuation
- 2001-02-06 EP EP01902774A patent/EP1256582A1/fr not_active Withdrawn
- 2001-02-06 CA CA002399136A patent/CA2399136A1/fr not_active Abandoned
- 2001-02-06 KR KR1020027010326A patent/KR20020073211A/ko not_active Withdrawn
- 2001-02-06 CZ CZ20022626A patent/CZ20022626A3/cs unknown
- 2001-02-06 SK SK1120-2002A patent/SK11202002A3/sk unknown
- 2001-02-06 AU AU2001230584A patent/AU2001230584A1/en not_active Abandoned
- 2001-02-06 PL PL01355866A patent/PL355866A1/xx unknown
- 2001-02-06 HU HU0204474A patent/HUP0204474A3/hu unknown
- 2001-02-06 MX MXPA02007525A patent/MXPA02007525A/es not_active Application Discontinuation
- 2001-02-06 IL IL15084101A patent/IL150841A0/xx unknown
- 2001-02-06 WO PCT/JP2001/000816 patent/WO2001058900A1/fr not_active Ceased
2002
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Publication number	Publication date
BG107067A (bg)	2003-09-30
WO2001058900A1 (fr)	2001-08-16
CA2399136A1 (fr)	2001-08-16
EP1256582A1 (fr)	2002-11-13
US20040054182A1 (en)	2004-03-18
SK11202002A3 (sk)	2003-03-04
CN1422269A (zh)	2003-06-04
PL355866A1 (en)	2004-05-31
CZ20022626A3 (cs)	2003-02-12
MXPA02007525A (es)	2002-12-13
KR20020073211A (ko)	2002-09-19
AU2001230584A1 (en)	2001-08-20
HUP0204474A2 (hu)	2003-04-28
NO20023750D0 (no)	2002-08-08
IL150841A0 (en)	2003-02-12
BR0108303A (pt)	2003-03-05
HUP0204474A3 (en)	2004-07-28

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