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
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 2
DSPMDOZVHYDTSO-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)-n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N(CCNC(=O)CN2C(C3=CC=CC=C3C2=O)=O)C=1C1=CC=CC=C1 DSPMDOZVHYDTSO-UHFFFAOYSA-N 0.000 description 2
XQPVZYJBLZAEEL-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1=CC(F)=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=CC=C3)C3=C2N1CCC1CCNCC1 XQPVZYJBLZAEEL-UHFFFAOYSA-N 0.000 description 2
BDHMYEXCAFRKAM-UHFFFAOYSA-N 2-(4-iodophenyl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=C(I)C=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 BDHMYEXCAFRKAM-UHFFFAOYSA-N 0.000 description 2
GROOAWILZDAAFL-UHFFFAOYSA-N 2-(methylamino)-n-[2-[2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)CNC)C=1C1=CC=CN1 GROOAWILZDAAFL-UHFFFAOYSA-N 0.000 description 2
CZRAWPFERYEPEN-UHFFFAOYSA-N 2-[7-chloro-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CCNCC1 CZRAWPFERYEPEN-UHFFFAOYSA-N 0.000 description 2
CYGQQBKPRJPUHE-UHFFFAOYSA-N 2-cyclohexyl-7-fluoro-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCN1CCNCC1 CYGQQBKPRJPUHE-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
OFRLFXPLCHUGSB-UHFFFAOYSA-N 3-nitro-2-(trifluoromethyl)-1h-quinolin-4-one Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C(C(F)(F)F)=NC2=C1 OFRLFXPLCHUGSB-UHFFFAOYSA-N 0.000 description 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical group C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 description 2
CPAHZFQOIPVJLO-UHFFFAOYSA-N 4-chloro-3-nitro-2-(trifluoromethyl)quinoline Chemical compound C1=CC=C2N=C(C(F)(F)F)C([N+](=O)[O-])=C(Cl)C2=C1 CPAHZFQOIPVJLO-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
XIQFBDIWOXNUGT-UHFFFAOYSA-N 7-chloro-1-(2-piperazin-1-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 XIQFBDIWOXNUGT-UHFFFAOYSA-N 0.000 description 2
PJIQKVJGLJDFRK-UHFFFAOYSA-N 7-chloro-2-(1H-imidazol-2-yl)-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 PJIQKVJGLJDFRK-UHFFFAOYSA-N 0.000 description 2
LYTWNXLYCIGUEB-UHFFFAOYSA-N 7-chloro-2-(furan-2-yl)-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 LYTWNXLYCIGUEB-UHFFFAOYSA-N 0.000 description 2
XQMHRRXXJKRIMB-UHFFFAOYSA-N 7-fluoro-1-(2-piperidin-4-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CCNCC1 XQMHRRXXJKRIMB-UHFFFAOYSA-N 0.000 description 2
OMBDFTFMVHXBHK-UHFFFAOYSA-N 7-fluoro-2-(furan-2-yl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CCNCC1 OMBDFTFMVHXBHK-UHFFFAOYSA-N 0.000 description 2
NZFMBEUDRFNJEH-UHFFFAOYSA-N 7-methyl-1-(2-piperidin-4-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 NZFMBEUDRFNJEH-UHFFFAOYSA-N 0.000 description 2
JFEIHHSWBHTDOG-UHFFFAOYSA-N 8-methoxy-2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN1C=2C3=CC(OC)=CC=C3N=C(C(F)(F)F)C=2N=C1C1=CC=CC=C1 JFEIHHSWBHTDOG-UHFFFAOYSA-N 0.000 description 2
LXDQAYVVBNBFNK-UHFFFAOYSA-N 8-methyl-2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN1C=2C3=CC(C)=CC=C3N=C(C(F)(F)F)C=2N=C1C1=CC=CC=C1 LXDQAYVVBNBFNK-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
208000023275 Autoimmune disease Diseases 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
241000282693 Cercopithecidae Species 0.000 description 2
206010008685 Chondritis Diseases 0.000 description 2
206010008909 Chronic Hepatitis Diseases 0.000 description 2
206010009900 Colitis ulcerative Diseases 0.000 description 2
208000011231 Crohn disease Diseases 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
206010012438 Dermatitis atopic Diseases 0.000 description 2
206010012442 Dermatitis contact Diseases 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
208000003556 Dry Eye Syndromes Diseases 0.000 description 2
206010013774 Dry eye Diseases 0.000 description 2
206010060742 Endocrine ophthalmopathy Diseases 0.000 description 2
208000032027 Essential Thrombocythemia Diseases 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
206010018691 Granuloma Diseases 0.000 description 2
208000015023 Graves' disease Diseases 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
208000009319 Keratoconjunctivitis Sicca Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
206010037083 Prurigo Diseases 0.000 description 2
208000003251 Pruritus Diseases 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
206010040047 Sepsis Diseases 0.000 description 2
206010040070 Septic Shock Diseases 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
201000006704 Ulcerative Colitis Diseases 0.000 description 2
208000024780 Urticaria Diseases 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
201000010105 allergic rhinitis Diseases 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000004103 aminoalkyl group Chemical group 0.000 description 2
208000007502 anemia Diseases 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000004391 aryl sulfonyl group Chemical group 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
201000008937 atopic dermatitis Diseases 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
208000037976 chronic inflammation Diseases 0.000 description 2
208000037893 chronic inflammatory disorder Diseases 0.000 description 2
235000015165 citric acid Nutrition 0.000 description 2
208000010247 contact dermatitis Diseases 0.000 description 2
239000012228 culture supernatant Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
239000003221 ear drop Substances 0.000 description 2
229940047652 ear drops Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000002158 endotoxin Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000003889 eye drop Substances 0.000 description 2
229940012356 eye drops Drugs 0.000 description 2
239000003885 eye ointment Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
208000007475 hemolytic anemia Diseases 0.000 description 2
208000006454 hepatitis Diseases 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
229960002751 imiquimod Drugs 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
208000028774 intestinal disease Diseases 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229920006008 lipopolysaccharide Polymers 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000005259 measurement Methods 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 2
201000006417 multiple sclerosis Diseases 0.000 description 2
206010028417 myasthenia gravis Diseases 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
201000009240 nasopharyngitis Diseases 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
201000008482 osteoarthritis Diseases 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
NOOLISFMXDJSKH-UHFFFAOYSA-N p-menthan-3-ol Chemical compound CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
208000005069 pulmonary fibrosis Diseases 0.000 description 2
125000003373 pyrazinyl group Chemical group 0.000 description 2
206010039073 rheumatoid arthritis Diseases 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
201000000306 sarcoidosis Diseases 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000036303 septic shock Effects 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000012453 solvate Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
CKZFJESKIMEODW-UHFFFAOYSA-N tert-butyl 4-[2-(4-cyano-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(C#N)=C2N=C1C1=CC=CC=C1 CKZFJESKIMEODW-UHFFFAOYSA-N 0.000 description 2
BOEDFAOCQPHVGX-UHFFFAOYSA-N tert-butyl 4-[2-[[3-amino-2-(trifluoromethyl)quinolin-4-yl]amino]ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CCNC1=C(N)C(C(F)(F)F)=NC2=CC=CC=C12 BOEDFAOCQPHVGX-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
SXTPLJVONLKSRV-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-(dimethylamino)-n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound OC(=O)\C=C\C(O)=O.N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)CN(C)C)C=1C1=CC=CC=C1 SXTPLJVONLKSRV-WLHGVMLRSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 description 1
125000001506 1,2,3-triazol-5-yl group Chemical group [H]N1N=NC([H])=C1[*] 0.000 description 1
125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 description 1
GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical group C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
XEQDMNMCRPHFDQ-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCN1CCNCC1 XEQDMNMCRPHFDQ-UHFFFAOYSA-N 0.000 description 1
RLKSHTSGQVALNC-UHFFFAOYSA-N 1-(2-piperidin-1-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1CCN1CCCCC1 RLKSHTSGQVALNC-UHFFFAOYSA-N 0.000 description 1
JBFLOMASXXXGND-UHFFFAOYSA-N 1-(2-piperidin-3-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCCNC1 JBFLOMASXXXGND-UHFFFAOYSA-N 0.000 description 1
FYSYVVFOPRAZJC-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)-2,4-bis(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound FC(F)(F)C1=NC2=C(C(F)(F)F)N=C3C=CC=CC3=C2N1CCC1CCNCC1 FYSYVVFOPRAZJC-UHFFFAOYSA-N 0.000 description 1
RUADREGHSFBZSO-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 RUADREGHSFBZSO-UHFFFAOYSA-N 0.000 description 1
QIVPJDYQEZTUFL-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 QIVPJDYQEZTUFL-UHFFFAOYSA-N 0.000 description 1
IGLVBJRUTLNNPY-UHFFFAOYSA-N 1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]imidazo[4,5-c]quinoline Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=CC=C3)C3=C2N1CCC1CCNCC1 IGLVBJRUTLNNPY-UHFFFAOYSA-N 0.000 description 1
USBXXAJHGZKTAZ-UHFFFAOYSA-N 1-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound FC(F)(F)N1C=NC=2C=NC=3C=CC=CC=3C=21 USBXXAJHGZKTAZ-UHFFFAOYSA-N 0.000 description 1
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
GUQZNJYTURCFHV-UHFFFAOYSA-N 1-[2-(1-benzylpiperidin-4-yl)ethyl]-2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC(CC1)CCN1CC1=CC=CC=C1 GUQZNJYTURCFHV-UHFFFAOYSA-N 0.000 description 1
VEXBETARPAVNJN-UHFFFAOYSA-N 1-[2-(8-azabicyclo[3.2.1]octan-3-yl)ethyl]-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N(CCC2CC3CCC(N3)C2)C=1C1=CC=CN1 VEXBETARPAVNJN-UHFFFAOYSA-N 0.000 description 1
YADXZDAPVFSCIT-UHFFFAOYSA-N 1-[2-(8-azabicyclo[3.2.1]octan-3-yl)ethyl]-2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N(CCC2CC3CCC(N3)C2)C=1C1=CC=CC=C1 YADXZDAPVFSCIT-UHFFFAOYSA-N 0.000 description 1
GKPIBWZMXGMQEB-UHFFFAOYSA-N 1-[2-(azetidin-3-yl)ethyl]-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CNC1 GKPIBWZMXGMQEB-UHFFFAOYSA-N 0.000 description 1
OFXOYSMMEXAMTO-UHFFFAOYSA-N 1-[4-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1CCN1C2=C3C=CC=CC3=NC(C(F)(F)F)=C2N=C1C1=CC=CC=C1 OFXOYSMMEXAMTO-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
MBOWNLKRDDXYDL-UHFFFAOYSA-N 2,4-diphenyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN(C1=C2C=CC=CC2=N2)C(C=3C=CC=CC=3)=NC1=C2C1=CC=CC=C1 MBOWNLKRDDXYDL-UHFFFAOYSA-N 0.000 description 1
XYDFQLSXQOETDO-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 XYDFQLSXQOETDO-UHFFFAOYSA-N 0.000 description 1
IKEOSIYXFOWULO-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-6-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCN1CCNCC1 IKEOSIYXFOWULO-UHFFFAOYSA-N 0.000 description 1
CQEKBEMLOAYAOI-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-6-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 CQEKBEMLOAYAOI-UHFFFAOYSA-N 0.000 description 1
QXAFURRIIHACHY-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-7-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 QXAFURRIIHACHY-UHFFFAOYSA-N 0.000 description 1
DIGXTESBJGPZHD-UHFFFAOYSA-N 2-(1H-imidazol-2-yl)-7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 DIGXTESBJGPZHD-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
ZXYRXIDOXSHBRB-UHFFFAOYSA-N 2-(2-methoxyphenyl)-7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound COC1=CC=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=C(C)C=C3)C3=C2N1CCC1CCNCC1 ZXYRXIDOXSHBRB-UHFFFAOYSA-N 0.000 description 1
KDSVIEFROPSPJX-UHFFFAOYSA-N 2-(3-methoxyphenyl)-7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound COC1=CC=CC(C=2N(C3=C4C=CC(C)=CC4=NC(=C3N=2)C(F)(F)F)CCC2CCNCC2)=C1 KDSVIEFROPSPJX-UHFFFAOYSA-N 0.000 description 1
YCCQCVYTGPGTDX-UHFFFAOYSA-N 2-(3-methylthiophen-2-yl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1=CSC(C=2N(C3=C4C=CC=CC4=NC(=C3N=2)C(F)(F)F)CCC2CCNCC2)=C1C YCCQCVYTGPGTDX-UHFFFAOYSA-N 0.000 description 1
BHTRQHIJQUSMDL-UHFFFAOYSA-N 2-(4-methoxyphenyl)-7-methyl-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=C(C)C=C3)C3=C2N1CCC1CCNCC1 BHTRQHIJQUSMDL-UHFFFAOYSA-N 0.000 description 1
FGCMYSBCRMBPJV-UHFFFAOYSA-N 2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)-n-tritylethanamine Chemical compound C=1C=CC=CC=1C1=NC=2C(C)=NC3=CC=CC=C3C=2N1CCNC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FGCMYSBCRMBPJV-UHFFFAOYSA-N 0.000 description 1
NJKYKKSVCHRUOO-UHFFFAOYSA-N 2-(4-methylphenyl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1=CC(C)=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=CC=C3)C3=C2N1CCC1CCNCC1 NJKYKKSVCHRUOO-UHFFFAOYSA-N 0.000 description 1
OJSMSJRBEKURRE-UHFFFAOYSA-N 2-(5-methylthiophen-2-yl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound S1C(C)=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=CC=C3)C3=C2N1CCC1CCNCC1 OJSMSJRBEKURRE-UHFFFAOYSA-N 0.000 description 1
WFVAUHOPUOMJJF-UHFFFAOYSA-N 2-(dimethylamino)-n-[2-[2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)CN(C)C)C=1C1=CC=CN1 WFVAUHOPUOMJJF-UHFFFAOYSA-N 0.000 description 1
RPKCZPBFYPVCHU-UHFFFAOYSA-N 2-(dimethylamino)-n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)CN(C)C)C=1C1=CC=CC=C1 RPKCZPBFYPVCHU-UHFFFAOYSA-N 0.000 description 1
PCZWTLNSLXXUEQ-UHFFFAOYSA-N 2-(furan-2-yl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 PCZWTLNSLXXUEQ-UHFFFAOYSA-N 0.000 description 1
VFHVCJYNRXXYQA-UHFFFAOYSA-N 2-(furan-2-yl)-6-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCN1CCNCC1 VFHVCJYNRXXYQA-UHFFFAOYSA-N 0.000 description 1
PUFYKHFOEYIQHP-UHFFFAOYSA-N 2-(furan-2-yl)-6-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 PUFYKHFOEYIQHP-UHFFFAOYSA-N 0.000 description 1
NYOVRDLXXOBGDA-UHFFFAOYSA-N 2-(furan-2-yl)-7-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 NYOVRDLXXOBGDA-UHFFFAOYSA-N 0.000 description 1
ZKWBHPAIWCUUQJ-UHFFFAOYSA-N 2-(furan-2-yl)-7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 ZKWBHPAIWCUUQJ-UHFFFAOYSA-N 0.000 description 1
IWSKDWRNDDSWKX-UHFFFAOYSA-N 2-(methylamino)-n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)CNC)C=1C1=CC=CC=C1 IWSKDWRNDDSWKX-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
UEZHCIRDHODSBF-UHFFFAOYSA-N 2-[1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 UEZHCIRDHODSBF-UHFFFAOYSA-N 0.000 description 1
OZUHXTHIQSUXKW-UHFFFAOYSA-N 2-[2-(1h-pyrrol-2-yl)-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=CN1 OZUHXTHIQSUXKW-UHFFFAOYSA-N 0.000 description 1
QAHXLMHJBMIASO-UHFFFAOYSA-N 2-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]guanidine Chemical compound N=1C=2C(C)=NC3=CC=CC=C3C=2N(CCNC(N)=N)C=1C1=CC=CC=C1 QAHXLMHJBMIASO-UHFFFAOYSA-N 0.000 description 1
GURLFOGUNZCKDW-UHFFFAOYSA-N 2-[2-[2-(1H-imidazol-2-yl)-6-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CNC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 GURLFOGUNZCKDW-UHFFFAOYSA-N 0.000 description 1
IBLIBFYWPVKFRG-UHFFFAOYSA-N 2-[2-[2-(1H-imidazol-2-yl)-7-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CNCCO1 IBLIBFYWPVKFRG-UHFFFAOYSA-N 0.000 description 1
YZSFOTNXAWPPAU-UHFFFAOYSA-N 2-[2-[2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CNCCO1 YZSFOTNXAWPPAU-UHFFFAOYSA-N 0.000 description 1
PKNWLJJAVYSGEW-UHFFFAOYSA-N 2-[2-[2-(ethoxymethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]thiomorpholine Chemical compound CCOCC1=NC2=C(C(F)(F)F)N=C3C=CC=CC3=C2N1CCC1CNCCS1 PKNWLJJAVYSGEW-UHFFFAOYSA-N 0.000 description 1
QHFYRFCJAOHHMQ-UHFFFAOYSA-N 2-[2-[2-(furan-2-yl)-6-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=COC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 QHFYRFCJAOHHMQ-UHFFFAOYSA-N 0.000 description 1
DSRVFDYQONGNIU-UHFFFAOYSA-N 2-[2-[2-(furan-2-yl)-7-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CNCCO1 DSRVFDYQONGNIU-UHFFFAOYSA-N 0.000 description 1
UJEIWMIKPRBZQY-UHFFFAOYSA-N 2-[2-[2-cyclohexyl-6-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCCC1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 UJEIWMIKPRBZQY-UHFFFAOYSA-N 0.000 description 1
LBSBEUJIJHDTOX-UHFFFAOYSA-N 2-[2-[2-cyclohexyl-7-fluoro-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 LBSBEUJIJHDTOX-UHFFFAOYSA-N 0.000 description 1
NMQPNNWJEOFXNN-UHFFFAOYSA-N 2-[2-[2-cyclohexyl-7-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CNCCO1 NMQPNNWJEOFXNN-UHFFFAOYSA-N 0.000 description 1
QWPIUPYCNOEMCD-UHFFFAOYSA-N 2-[2-[2-cyclopentyl-6-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCC1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 QWPIUPYCNOEMCD-UHFFFAOYSA-N 0.000 description 1
ZFSJVVPFFCHUIU-UHFFFAOYSA-N 2-[2-[2-cyclopentyl-7-fluoro-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 ZFSJVVPFFCHUIU-UHFFFAOYSA-N 0.000 description 1
IXTVDCVQIBHQRU-UHFFFAOYSA-N 2-[2-[2-cyclopentyl-7-methyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CNCCO1 IXTVDCVQIBHQRU-UHFFFAOYSA-N 0.000 description 1
CWSYVAWKXNQXJZ-UHFFFAOYSA-N 2-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CNCCO1 CWSYVAWKXNQXJZ-UHFFFAOYSA-N 0.000 description 1
HPQGEROXOZLMOA-UHFFFAOYSA-N 2-[2-[6-methyl-2-(1,3-thiazol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CSC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 HPQGEROXOZLMOA-UHFFFAOYSA-N 0.000 description 1
HVHLBRKTYIXXJS-UHFFFAOYSA-N 2-[2-[6-methyl-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CNC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 HVHLBRKTYIXXJS-UHFFFAOYSA-N 0.000 description 1
HDICJRDOKGGYNL-UHFFFAOYSA-N 2-[2-[6-methyl-2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CC=CC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 HDICJRDOKGGYNL-UHFFFAOYSA-N 0.000 description 1
KDAZKGSDYXKUIL-UHFFFAOYSA-N 2-[2-[6-methyl-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CSC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CNCCO1 KDAZKGSDYXKUIL-UHFFFAOYSA-N 0.000 description 1
AEKGULIILRXMHN-UHFFFAOYSA-N 2-[2-[7-chloro-2-(1,3-thiazol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CNCCO1 AEKGULIILRXMHN-UHFFFAOYSA-N 0.000 description 1
DHNUYLMGTCAZQP-UHFFFAOYSA-N 2-[2-[7-chloro-2-(1H-imidazol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CNCCO1 DHNUYLMGTCAZQP-UHFFFAOYSA-N 0.000 description 1
BQUIMVDQJYSDAM-UHFFFAOYSA-N 2-[2-[7-chloro-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CNCCO1 BQUIMVDQJYSDAM-UHFFFAOYSA-N 0.000 description 1
QJEFULMNSJQLDL-UHFFFAOYSA-N 2-[2-[7-chloro-2-cyclohexyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CNCCO1 QJEFULMNSJQLDL-UHFFFAOYSA-N 0.000 description 1
BFGPYFKFFSCHHS-UHFFFAOYSA-N 2-[2-[7-chloro-2-cyclopentyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CNCCO1 BFGPYFKFFSCHHS-UHFFFAOYSA-N 0.000 description 1
QZMIBASKFHCOJD-UHFFFAOYSA-N 2-[2-[7-chloro-2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CNCCO1 QZMIBASKFHCOJD-UHFFFAOYSA-N 0.000 description 1
CEXWAHBAVQYVCG-UHFFFAOYSA-N 2-[2-[7-chloro-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CNCCO1 CEXWAHBAVQYVCG-UHFFFAOYSA-N 0.000 description 1
HQFLBWBMCFMPII-UHFFFAOYSA-N 2-[2-[7-fluoro-2-(1,3-thiazol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 HQFLBWBMCFMPII-UHFFFAOYSA-N 0.000 description 1
MLAZUYXUKFTAQS-UHFFFAOYSA-N 2-[2-[7-fluoro-2-(1H-imidazol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 MLAZUYXUKFTAQS-UHFFFAOYSA-N 0.000 description 1
CWBQUSPLFIAWRK-UHFFFAOYSA-N 2-[2-[7-fluoro-2-(furan-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 CWBQUSPLFIAWRK-UHFFFAOYSA-N 0.000 description 1
KDWZTVCIPCGDIP-UHFFFAOYSA-N 2-[2-[7-fluoro-2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 KDWZTVCIPCGDIP-UHFFFAOYSA-N 0.000 description 1
BEQYJCXRZALRJN-UHFFFAOYSA-N 2-[2-[7-fluoro-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CNCCO1 BEQYJCXRZALRJN-UHFFFAOYSA-N 0.000 description 1
JQTXDLIGNCHBAX-UHFFFAOYSA-N 2-[2-[7-methyl-2-(1,3-thiazol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CNCCO1 JQTXDLIGNCHBAX-UHFFFAOYSA-N 0.000 description 1
QAZCHEFJUXGFPS-UHFFFAOYSA-N 2-[2-[7-methyl-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CNCCO1 QAZCHEFJUXGFPS-UHFFFAOYSA-N 0.000 description 1
BKXNUUBJSLKKOF-UHFFFAOYSA-N 2-[2-[7-methyl-2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]morpholine Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CNCCO1 BKXNUUBJSLKKOF-UHFFFAOYSA-N 0.000 description 1
VXWYQEYFYNAZOD-UHFFFAOYSA-N 2-[3-[(4,4-difluoropiperidin-1-yl)methyl]-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC1(F)CCN(CC2=NN(CC(=O)N3CCC4=C(C3)N=NN4)C=C2C2=CN=C(NC3CC4=C(C3)C=CC=C4)N=C2)CC1 VXWYQEYFYNAZOD-UHFFFAOYSA-N 0.000 description 1
ZMRVPESYGNMNQL-UHFFFAOYSA-N 2-[6-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCN1CCNCC1 ZMRVPESYGNMNQL-UHFFFAOYSA-N 0.000 description 1
AIYSIRNEJXECJO-UHFFFAOYSA-N 2-[6-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 AIYSIRNEJXECJO-UHFFFAOYSA-N 0.000 description 1
QFPQNOYBXXBJDH-UHFFFAOYSA-N 2-[7-chloro-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 QFPQNOYBXXBJDH-UHFFFAOYSA-N 0.000 description 1
RCKRZORGFPWSPJ-UHFFFAOYSA-N 2-[7-chloro-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]phenol Chemical compound OC1=CC=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=C(Cl)C=C3)C3=C2N1CCC1CCNCC1 RCKRZORGFPWSPJ-UHFFFAOYSA-N 0.000 description 1
MZXXNTDQZISEJN-UHFFFAOYSA-N 2-[7-fluoro-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCN1CCNCC1 MZXXNTDQZISEJN-UHFFFAOYSA-N 0.000 description 1
VZFVSCJFGQGIHA-UHFFFAOYSA-N 2-[7-fluoro-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CCNCC1 VZFVSCJFGQGIHA-UHFFFAOYSA-N 0.000 description 1
CIBBBQQLNSWRBZ-UHFFFAOYSA-N 2-[7-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 CIBBBQQLNSWRBZ-UHFFFAOYSA-N 0.000 description 1
TYKPPRLOHWAFSB-UHFFFAOYSA-N 2-[7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]-1,3-thiazole Chemical compound N=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 TYKPPRLOHWAFSB-UHFFFAOYSA-N 0.000 description 1
CHRNHOJPAYXEKX-UHFFFAOYSA-N 2-[7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]phenol Chemical compound C=1C=CC=C(O)C=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 CHRNHOJPAYXEKX-UHFFFAOYSA-N 0.000 description 1
IAIBZVBNHOQEEA-UHFFFAOYSA-N 2-amino-n-[2-[2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)CN)C=1C1=CC=CN1 IAIBZVBNHOQEEA-UHFFFAOYSA-N 0.000 description 1
OORNVXUZSCYSEF-UHFFFAOYSA-N 2-amino-n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)CN)C=1C1=CC=CC=C1 OORNVXUZSCYSEF-UHFFFAOYSA-N 0.000 description 1
AFDPYTMVDPUIMP-UHFFFAOYSA-N 2-chloro-n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N(CCNC(=O)CCl)C=1C1=CC=CC=C1 AFDPYTMVDPUIMP-UHFFFAOYSA-N 0.000 description 1
FTZWNHXSZYXEJO-UHFFFAOYSA-N 2-cyclohexyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 FTZWNHXSZYXEJO-UHFFFAOYSA-N 0.000 description 1
FGJNXQOKZPFORZ-UHFFFAOYSA-N 2-cyclohexyl-6-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCN1CCNCC1 FGJNXQOKZPFORZ-UHFFFAOYSA-N 0.000 description 1
RMQBGOSUWINVIM-UHFFFAOYSA-N 2-cyclohexyl-6-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 RMQBGOSUWINVIM-UHFFFAOYSA-N 0.000 description 1
NSTMXOGPCOTBFR-UHFFFAOYSA-N 2-cyclohexyl-7-fluoro-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CCNCC1 NSTMXOGPCOTBFR-UHFFFAOYSA-N 0.000 description 1
SAQBOYBHFAXLKS-UHFFFAOYSA-N 2-cyclohexyl-7-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 SAQBOYBHFAXLKS-UHFFFAOYSA-N 0.000 description 1
YQJJBKBEOIXHCU-UHFFFAOYSA-N 2-cyclohexyl-7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 YQJJBKBEOIXHCU-UHFFFAOYSA-N 0.000 description 1
AARNGHURTCDFGO-UHFFFAOYSA-N 2-cyclopentyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 AARNGHURTCDFGO-UHFFFAOYSA-N 0.000 description 1
NXJGWWGJOUNVCO-UHFFFAOYSA-N 2-cyclopentyl-6-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCC1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 NXJGWWGJOUNVCO-UHFFFAOYSA-N 0.000 description 1
SJYFHSLFEPBVAS-UHFFFAOYSA-N 2-cyclopentyl-7-fluoro-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCN1CCNCC1 SJYFHSLFEPBVAS-UHFFFAOYSA-N 0.000 description 1
MVWPDWCMKTYQSR-UHFFFAOYSA-N 2-cyclopentyl-7-fluoro-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CCNCC1 MVWPDWCMKTYQSR-UHFFFAOYSA-N 0.000 description 1
RKCHKGFDLHFASV-UHFFFAOYSA-N 2-cyclopentyl-7-methyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 RKCHKGFDLHFASV-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
WMHBFRJMZLTUIC-UHFFFAOYSA-N 2-phenyl-1-(2-piperazin-1-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=2N1CCN1CCNCC1 WMHBFRJMZLTUIC-UHFFFAOYSA-N 0.000 description 1
DKGXHNGQBLEYOE-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-3-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=2N1CCC1CCCNC1 DKGXHNGQBLEYOE-UHFFFAOYSA-N 0.000 description 1
XJWCEZGGADRRAE-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)-4,7-bis(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C(F)(F)F)=CC=C3C=2N1CCC1CCNCC1 XJWCEZGGADRRAE-UHFFFAOYSA-N 0.000 description 1
PEDPGYSQQAQCFA-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)-6,7,8,9-tetrahydroimidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC=3CCCCC=3C=2N1CCC1CCNCC1 PEDPGYSQQAQCFA-UHFFFAOYSA-N 0.000 description 1
ZTLDCRQVEASPGL-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c][1,5]naphthyridine Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CN=C3C=2N1CCC1CCNCC1 ZTLDCRQVEASPGL-UHFFFAOYSA-N 0.000 description 1
VPZBCTCLTVOBGN-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)-4-thiophen-2-ylimidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN(C1=C2C=CC=CC2=N2)C(C=3C=CC=CC=3)=NC1=C2C1=CC=CS1 VPZBCTCLTVOBGN-UHFFFAOYSA-N 0.000 description 1
KEURHLUDVIUFBY-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)-5h-imidazo[4,5-c]quinoline-4-thione Chemical compound C=1C=CC=CC=1C1=NC=2C(=S)NC3=CC=CC=C3C=2N1CCC1CCNCC1 KEURHLUDVIUFBY-UHFFFAOYSA-N 0.000 description 1
SFMOHUCOGMWKCG-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline-4-carbonitrile Chemical compound C=1C=CC=CC=1C1=NC=2C(C#N)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 SFMOHUCOGMWKCG-UHFFFAOYSA-N 0.000 description 1
ZCUQZLFCSBPBOX-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline-4-carboxamide Chemical compound C=1C=CC=CC=1C1=NC=2C(C(=O)N)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 ZCUQZLFCSBPBOX-UHFFFAOYSA-N 0.000 description 1
YBDYBYWHQZFBGQ-UHFFFAOYSA-N 2-phenyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline-4-carboxylic acid Chemical compound C=1C=CC=CC=1C1=NC=2C(C(=O)O)=NC3=CC=CC=C3C=2N1CCC1CCNCC1 YBDYBYWHQZFBGQ-UHFFFAOYSA-N 0.000 description 1
JCSXTTWNDFRCAX-UHFFFAOYSA-N 2-phenyl-1-(2-pyrrolidin-3-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=2N1CCC1CCNC1 JCSXTTWNDFRCAX-UHFFFAOYSA-N 0.000 description 1
UWOOHJVMEGYYGO-UHFFFAOYSA-N 2-phenyl-1-(3-piperidin-4-ylpropyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1CCCC1CCNCC1 UWOOHJVMEGYYGO-UHFFFAOYSA-N 0.000 description 1
AWGGHVHGYQVIDE-UHFFFAOYSA-N 2-phenyl-1-piperidin-4-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC=CC=C3C=2N1C1CCNCC1 AWGGHVHGYQVIDE-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
IMLJFDZUGNFYDT-UHFFFAOYSA-N 2-tert-butyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound CC(C)(C)C1=NC2=C(C(F)(F)F)N=C3C=CC=CC3=C2N1CCC1CCNCC1 IMLJFDZUGNFYDT-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
LWIOKLPTUYZVIR-UHFFFAOYSA-N 3-[7-chloro-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N(C3=C4C=CC(Cl)=CC4=NC(=C3N=2)C(F)(F)F)CCC2CCNCC2)=C1 LWIOKLPTUYZVIR-UHFFFAOYSA-N 0.000 description 1
DDXBAIOTZFARPQ-UHFFFAOYSA-N 3-[7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]phenol Chemical compound C=1C=CC(O)=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 DDXBAIOTZFARPQ-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
YUWOLBZMQDGRFV-UHFFFAOYSA-N 3-nitro-1h-pyridin-4-one Chemical class [O-][N+](=O)C1=CNC=CC1=O YUWOLBZMQDGRFV-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
BLZCNPVKPAKANK-UHFFFAOYSA-N 4-(furan-2-yl)-2-phenyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN(C1=C2C=CC=CC2=N2)C(C=3C=CC=CC=3)=NC1=C2C1=CC=CO1 BLZCNPVKPAKANK-UHFFFAOYSA-N 0.000 description 1
YRNWIFYIFSBPAU-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CC=C(N(C)C)C=C1 YRNWIFYIFSBPAU-UHFFFAOYSA-N 0.000 description 1
NGOHINMVXCIVEK-UHFFFAOYSA-N 4-[7-chloro-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=C(Cl)C=C3)C3=C2N1CCC1CCNCC1 NGOHINMVXCIVEK-UHFFFAOYSA-N 0.000 description 1
RIXHCYVBRUVQSQ-UHFFFAOYSA-N 4-[7-methyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinolin-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 RIXHCYVBRUVQSQ-UHFFFAOYSA-N 0.000 description 1
FQLXFNAAYUMCKN-UHFFFAOYSA-N 4-cyclopropyl-1-(2-piperidin-4-ylethyl)-2-(1h-pyrrol-2-yl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN(C1=C2C=CC=CC2=N2)C(C=3NC=CC=3)=NC1=C2C1CC1 FQLXFNAAYUMCKN-UHFFFAOYSA-N 0.000 description 1
FYAHFUPEJYTQRA-UHFFFAOYSA-N 4-cyclopropyl-2-phenyl-1-(2-piperidin-4-ylethyl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN(C1=C2C=CC=CC2=N2)C(C=3C=CC=CC=3)=NC1=C2C1CC1 FYAHFUPEJYTQRA-UHFFFAOYSA-N 0.000 description 1
BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 1
NJAKCIUOTIPYED-UHFFFAOYSA-N 4-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(I)C=C1 NJAKCIUOTIPYED-UHFFFAOYSA-N 0.000 description 1
NJKNCULGFZRPSB-UHFFFAOYSA-N 4-methyl-n-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NCCN1C2=C3C=CC=CC3=NC(C)=C2N=C1C1=CC=CC=C1 NJKNCULGFZRPSB-UHFFFAOYSA-N 0.000 description 1
FJKMQDNQNGINII-UHFFFAOYSA-N 4-phenyl-1-(2-piperidin-4-ylethyl)-2-(1h-pyrrol-2-yl)imidazo[4,5-c]quinoline Chemical compound C1CNCCC1CCN(C1=C2C=CC=CC2=N2)C(C=3NC=CC=3)=NC1=C2C1=CC=CC=C1 FJKMQDNQNGINII-UHFFFAOYSA-N 0.000 description 1
LUUOVFLCLFQIKG-UHFFFAOYSA-N 4-phenyl-3-(2-piperidin-4-ylethyl)-7-(trifluoromethyl)-12-thia-3,5,8-triazatricyclo[7.3.0.02,6]dodeca-1(9),2(6),4,7,10-pentaene Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC=3C=CSC=3C=2N1CCC1CCNCC1 LUUOVFLCLFQIKG-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
CKIAJLXAICDJJF-UHFFFAOYSA-N 6-methyl-1-(2-piperazin-1-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCN1CCNCC1 CKIAJLXAICDJJF-UHFFFAOYSA-N 0.000 description 1
XICDCYTZZAHEON-UHFFFAOYSA-N 6-methyl-1-(2-piperazin-1-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCN1CCNCC1 XICDCYTZZAHEON-UHFFFAOYSA-N 0.000 description 1
HGGOJJJCECSMTL-UHFFFAOYSA-N 6-methyl-1-(2-piperidin-4-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 HGGOJJJCECSMTL-UHFFFAOYSA-N 0.000 description 1
YQUDWEVVAMIDDR-UHFFFAOYSA-N 6-methyl-1-(2-piperidin-4-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 YQUDWEVVAMIDDR-UHFFFAOYSA-N 0.000 description 1
TXXQESFMYPASNO-UHFFFAOYSA-N 6-methyl-2-phenyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCN1CCNCC1 TXXQESFMYPASNO-UHFFFAOYSA-N 0.000 description 1
YANNAKSSBBZZCH-UHFFFAOYSA-N 6-methyl-2-phenyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC2=C(C(F)(F)F)N=C3C(C)=CC=CC3=C2N1CCC1CCNCC1 YANNAKSSBBZZCH-UHFFFAOYSA-N 0.000 description 1
IDNAQEOGXSULBP-UHFFFAOYSA-N 7-chloro-1-(2-piperazin-1-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 IDNAQEOGXSULBP-UHFFFAOYSA-N 0.000 description 1
KNTTZFDNOWFCTI-UHFFFAOYSA-N 7-chloro-1-(2-piperidin-4-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CCNCC1 KNTTZFDNOWFCTI-UHFFFAOYSA-N 0.000 description 1
RFZSOFAXEAMYBL-UHFFFAOYSA-N 7-chloro-2-(1H-imidazol-2-yl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CCNCC1 RFZSOFAXEAMYBL-UHFFFAOYSA-N 0.000 description 1
QECCOLYGLTWMAU-UHFFFAOYSA-N 7-chloro-2-(2-methoxyphenyl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound COC1=CC=CC=C1C1=NC2=C(C(F)(F)F)N=C(C=C(Cl)C=C3)C3=C2N1CCC1CCNCC1 QECCOLYGLTWMAU-UHFFFAOYSA-N 0.000 description 1
UGCPKHXHMWMCKN-UHFFFAOYSA-N 7-chloro-2-(3-methoxyphenyl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound COC1=CC=CC(C=2N(C3=C4C=CC(Cl)=CC4=NC(=C3N=2)C(F)(F)F)CCC2CCNCC2)=C1 UGCPKHXHMWMCKN-UHFFFAOYSA-N 0.000 description 1
MQYNPTPLJWDXNG-UHFFFAOYSA-N 7-chloro-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=C(Cl)C=C3)C3=C2N1CCC1CCNCC1 MQYNPTPLJWDXNG-UHFFFAOYSA-N 0.000 description 1
RQZCDGNXSPJQIJ-UHFFFAOYSA-N 7-chloro-2-(furan-2-yl)-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CCNCC1 RQZCDGNXSPJQIJ-UHFFFAOYSA-N 0.000 description 1
FDPITXCTDSIJQS-UHFFFAOYSA-N 7-chloro-2-cyclohexyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 FDPITXCTDSIJQS-UHFFFAOYSA-N 0.000 description 1
ULXNFZOHIHQLTH-UHFFFAOYSA-N 7-chloro-2-cyclohexyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CCNCC1 ULXNFZOHIHQLTH-UHFFFAOYSA-N 0.000 description 1
HEXUAQVVWKNZLY-UHFFFAOYSA-N 7-chloro-2-cyclopentyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 HEXUAQVVWKNZLY-UHFFFAOYSA-N 0.000 description 1
LEMHBOKSUDKUBO-UHFFFAOYSA-N 7-chloro-2-cyclopentyl-1-(2-piperidin-4-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C1CCCC1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCC1CCNCC1 LEMHBOKSUDKUBO-UHFFFAOYSA-N 0.000 description 1
OSEJHYQSAVJDHE-UHFFFAOYSA-N 7-chloro-2-phenyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(Cl)=CC=C3C=2N1CCN1CCNCC1 OSEJHYQSAVJDHE-UHFFFAOYSA-N 0.000 description 1
TWVCROGHTVPVIA-UHFFFAOYSA-N 7-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(Cl)=CC=C3C=2N1CCC1CCNCC1 TWVCROGHTVPVIA-UHFFFAOYSA-N 0.000 description 1
PZWLWKDWUOHFII-UHFFFAOYSA-N 7-fluoro-1-(2-piperazin-1-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCN1CCNCC1 PZWLWKDWUOHFII-UHFFFAOYSA-N 0.000 description 1
NSQSHAWTVUVVAZ-UHFFFAOYSA-N 7-fluoro-1-(2-piperidin-4-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCC1CCNCC1 NSQSHAWTVUVVAZ-UHFFFAOYSA-N 0.000 description 1
LMWBAQAQLYXIQF-UHFFFAOYSA-N 7-fluoro-2-(1H-imidazol-2-yl)-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound N=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCN1CCNCC1 LMWBAQAQLYXIQF-UHFFFAOYSA-N 0.000 description 1
IXNUHOZMCRSDPD-UHFFFAOYSA-N 7-fluoro-2-(furan-2-yl)-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=COC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCN1CCNCC1 IXNUHOZMCRSDPD-UHFFFAOYSA-N 0.000 description 1
PSSUABLPQIPJLP-UHFFFAOYSA-N 7-fluoro-2-phenyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(F)=CC=C3C=2N1CCN1CCNCC1 PSSUABLPQIPJLP-UHFFFAOYSA-N 0.000 description 1
KYVILQHUDWMQHF-UHFFFAOYSA-N 7-fluoro-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(F)=CC=C3C=2N1CCC1CCNCC1 KYVILQHUDWMQHF-UHFFFAOYSA-N 0.000 description 1
WAHFNDGANPOBJS-UHFFFAOYSA-N 7-methoxy-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(OC)=CC=C3C=2N1CCC1CCNCC1 WAHFNDGANPOBJS-UHFFFAOYSA-N 0.000 description 1
NFGPQMINJONFEA-UHFFFAOYSA-N 7-methyl-1-(2-piperazin-1-ylethyl)-2-(1h-pyrrol-2-yl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CNC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 NFGPQMINJONFEA-UHFFFAOYSA-N 0.000 description 1
JNZFQTVAPZUUFW-UHFFFAOYSA-N 7-methyl-1-(2-piperazin-1-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 JNZFQTVAPZUUFW-UHFFFAOYSA-N 0.000 description 1
DPFZJGTXWWEXJR-UHFFFAOYSA-N 7-methyl-1-(2-piperidin-4-ylethyl)-2-thiophen-2-yl-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CSC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCC1CCNCC1 DPFZJGTXWWEXJR-UHFFFAOYSA-N 0.000 description 1
NMTMKDBQAXZUJE-UHFFFAOYSA-N 7-methyl-2-phenyl-1-(2-piperazin-1-ylethyl)-4-(trifluoromethyl)imidazo[4,5-c]quinoline Chemical compound C=1C=CC=CC=1C1=NC=2C(C(F)(F)F)=NC3=CC(C)=CC=C3C=2N1CCN1CCNCC1 NMTMKDBQAXZUJE-UHFFFAOYSA-N 0.000 description 1
CFICYMKRRWTOLS-UHFFFAOYSA-N 7-methyl-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)=CC=C3C=2N1CCC1CCNCC1 CFICYMKRRWTOLS-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000023328 Basedow disease Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
238000002965 ELISA Methods 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
208000003807 Graves Disease Diseases 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
229930182816 L-glutamine Natural products 0.000 description 1
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 1
239000005639 Lauric acid Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
241001494479 Pecora Species 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
102000003992 Peroxidases Human genes 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
239000012980 RPMI-1640 medium Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
NZHXEWZGTQSYJM-UHFFFAOYSA-N [bromo(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Br)C1=CC=CC=C1 NZHXEWZGTQSYJM-UHFFFAOYSA-N 0.000 description 1
ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000007825 activation reagent Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000676 alkoxyimino group Chemical group 0.000 description 1
125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000003092 anti-cytokine Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000002785 azepinyl group Chemical group 0.000 description 1
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
HTTLBYITFHMYFK-UHFFFAOYSA-N bentranil Chemical compound N=1C2=CC=CC=C2C(=O)OC=1C1=CC=CC=C1 HTTLBYITFHMYFK-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
NPSUPLVNCUARLF-UHFFFAOYSA-N benzyl n-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]carbamate Chemical compound C=1C=CC=CC=1C1=NC=2C(C)=NC3=CC=CC=C3C=2N1CCNC(=O)OCC1=CC=CC=C1 NPSUPLVNCUARLF-UHFFFAOYSA-N 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000008436 biogenesis Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000000601 blood cell Anatomy 0.000 description 1
OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
239000004203 carnauba wax Substances 0.000 description 1
235000013869 carnauba wax Nutrition 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
229960000913 crospovidone Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000006317 cyclopropyl amino group Chemical group 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000016396 cytokine production Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229940116364 hard fat Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
208000014951 hematologic disease Diseases 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
150000005232 imidazopyridines Chemical class 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
KYBACXVGKUQXIA-UHFFFAOYSA-N n,n-diethyl-2-imidazo[4,5-c]quinolin-1-ylethanamine Chemical compound C1=CC=CC2=C3N(CCN(CC)CC)C=NC3=CN=C21 KYBACXVGKUQXIA-UHFFFAOYSA-N 0.000 description 1
KADFKGHAUOOYCT-UHFFFAOYSA-N n,n-dimethyl-2-[2-(1h-pyrrol-2-yl)-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)C)C=1C1=CC=CN1 KADFKGHAUOOYCT-UHFFFAOYSA-N 0.000 description 1
SWSWZLCYLHJUPT-UHFFFAOYSA-N n,n-dimethyl-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)C)C=1C1=CC=CC=C1 SWSWZLCYLHJUPT-UHFFFAOYSA-N 0.000 description 1
XGESBBVBKVRDTR-UHFFFAOYSA-N n-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]acetamide Chemical compound N=1C2=C(C)N=C3C=CC=CC3=C2N(CCNC(=O)C)C=1C1=CC=CC=C1 XGESBBVBKVRDTR-UHFFFAOYSA-N 0.000 description 1
PPAKZWZXDSHBFO-UHFFFAOYSA-N n-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]butan-1-amine Chemical compound N=1C2=C(C)N=C3C=CC=CC3=C2N(CCNCCCC)C=1C1=CC=CC=C1 PPAKZWZXDSHBFO-UHFFFAOYSA-N 0.000 description 1
UKAFFMLOESTQKB-UHFFFAOYSA-N n-[2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide Chemical compound N=1C=2C(C)=NC3=CC=CC=C3C=2N(CCNS(C)(=O)=O)C=1C1=CC=CC=C1 UKAFFMLOESTQKB-UHFFFAOYSA-N 0.000 description 1
KRIGCHTYSRHJNQ-UHFFFAOYSA-N n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]acetamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNC(=O)C)C=1C1=CC=CC=C1 KRIGCHTYSRHJNQ-UHFFFAOYSA-N 0.000 description 1
LJHWDTJTJRGFGS-UHFFFAOYSA-N n-[2-[2-phenyl-4-(trifluoromethyl)imidazo[4,5-c]quinolin-1-yl]ethyl]methanesulfonamide Chemical compound N=1C2=C(C(F)(F)F)N=C3C=CC=CC3=C2N(CCNS(=O)(=O)C)C=1C1=CC=CC=C1 LJHWDTJTJRGFGS-UHFFFAOYSA-N 0.000 description 1
FGXZCUYEVITYCY-UHFFFAOYSA-N n-benzyl-2-(4-methyl-2-phenylimidazo[4,5-c]quinolin-1-yl)ethanamine Chemical compound C=1C=CC=CC=1C1=NC=2C(C)=NC3=CC=CC=C3C=2N1CCNCC1=CC=CC=C1 FGXZCUYEVITYCY-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
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)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pulmonology (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Neurology (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Neurosurgery (AREA)
Obesity (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Dermatology (AREA)
Transplantation (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 (en)	2000-02-09	2001-02-06	1h-imidazopyridine derivatives

Publications (2)

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

Family

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

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1474425T3 (da)	2002-01-07	2006-09-25	Eisai Co Ltd	Deazapuriner og anvendelser deraf
GB0211649D0 (en) *	2002-05-21	2002-07-03	Novartis Ag	Organic compounds
PT1539752E (pt)	2002-07-26	2007-05-31	Teva Gyogyszergyar Zartkoeruen	Preparação de 1h-imidazo [4,5-c] quinolina-4-aminas via novos intermediários imidazo [4,5-c] quinolina-4-ciano e 1h-imidazo [4,5-c] quinolina-4-carboxamida
MXPA05007485A (es)	2003-01-14	2006-01-30	Arena Pharm Inc	Derivados de arilo y heteroarilo 1,2,3-trisubstituidos como moduladores del metabolismo y la profilaxis y tratamiento de trastornos relacionados con ello tales como diabetes e hiperglicemia.
BRPI0407519A (pt)	2003-03-07	2006-02-14	Kowa Co	derivados de benzofurano
JP2006519877A (ja) *	2003-03-07	2006-08-31	スリーエムイノベイティブプロパティズカンパニー	１−アミノ１ｈ−イミダゾキノリン
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
BRPI0413558A (pt)	2003-08-12	2006-10-17	3M Innovative Properties Co	compostos contendo imidazo substituìdo por hidroxilamina
AU2004268625B2 (en)	2003-08-27	2011-03-31	3M Innovative Properties Company	Aryloxy and arylalkyleneoxy substituted imidazoquinolines
AU2004270201A1 (en)	2003-09-05	2005-03-17	3M Innovative Properties Company	Treatment for CD5+ B cell lymphoma
AR046046A1 (es)	2003-10-03	2005-11-23	3M Innovative Properties Co	Imidazoquinolinas alcoxi sustituidas. composiciones farmaceuticas.
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
EP1685129A4 (en)	2003-11-14	2008-10-22	3M Innovative Properties Co	OXIMSUBSTITUTED IMIDAZORING CONNECTIONS
CA2545825A1 (en)	2003-11-14	2005-06-02	3M Innovative Properties Company	Hydroxylamine substituted imidazo ring compounds
PT1687305E (pt) *	2003-11-21	2008-10-17	Novartis Ag	Derivados de 1h-imidazoquinolina como inibidores de proteína quinase
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
CA2547020C (en)	2003-11-25	2014-03-25	3M Innovative Properties Company	1h-imidazo[4,5-c]pyridine-4-amine derivatives as immune response modifier
JP2007517035A (ja)	2003-12-29	2007-06-28	スリーエムイノベイティブプロパティズカンパニー	アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン
EP1699788A2 (en)	2003-12-30	2006-09-13	3M Innovative Properties Company	Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides
WO2005094531A2 (en)	2004-03-24	2005-10-13	3M Innovative Properties Company	Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
US20080154210A1 (en)	2004-05-28	2008-06-26	Oryxe	Mixture for Transdermal Delivery of Low and High Molecular Weight Compounds
US8017779B2 (en)	2004-06-15	2011-09-13	3M Innovative Properties Company	Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
WO2006065280A2 (en)	2004-06-18	2006-06-22	3M Innovative Properties Company	Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and methods
US8026366B2 (en)	2004-06-18	2011-09-27	3M Innovative Properties Company	Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
WO2006038923A2 (en)	2004-06-18	2006-04-13	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
JP5543068B2 (ja)	2004-12-30	2014-07-09	スリーエムイノベイティブプロパティズカンパニー	キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物
EP1831221B1 (en)	2004-12-30	2012-08-08	3M Innovative Properties Company	Substituted chiral fused 1,2 imidazo 4,5-c ring compounds
AU2006210392A1 (en)	2005-02-04	2006-08-10	Coley Pharmaceutical Group, Inc.	Aqueous gel formulations containing immune response modifiers
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
AU2006213746A1 (en)	2005-02-11	2006-08-17	Coley Pharmaceutical Group, Inc.	Oxime and hydroxylamine substituted imidazo(4,5-c) ring compounds and methods
AU2006232375A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
EP1869043A2 (en)	2005-04-01	2007-12-26	Coley Pharmaceutical Group, Inc.	Pyrazolopyridine-1,4-diamines and analogs thereof
JP2008535831A (ja) *	2005-04-01	2008-09-04	コーリーファーマシューティカルグループ，インコーポレーテッド	環閉鎖および関連する方法および中間体
AU2006292119A1 (en) *	2005-09-23	2007-03-29	3M Innovative Properties Company	Method for 1H-imidazo[4,5-c]pyridines and analogs thereof
US7906506B2 (en)	2006-07-12	2011-03-15	3M Innovative Properties Company	Substituted chiral fused [1,2] imidazo [4,5-c] ring compounds and methods
EP3323818A1 (en)	2010-09-22	2018-05-23	Arena Pharmaceuticals, Inc.	Modulators of the gpr119 receptor and the treatment of disorders related thereto
PL3242666T3 (pl)	2015-01-06	2025-02-17	Arena Pharmaceuticals, Inc.	Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1
BR112017027656B1 (pt)	2015-06-22	2023-12-05	Arena Pharmaceuticals, Inc.	Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo
US11260018B2 (en)	2015-09-17	2022-03-01	Jrx Biotechnology, Inc.	Approaches for improving skin hydration and moisturization
MX2019009841A (es)	2017-02-16	2020-01-30	Arena Pharm Inc	Compuestos y metodos para el tratamiento de la colangitis biliar primaria.
WO2018163030A1 (en) *	2017-03-10	2018-09-13	Pfizer Inc.	Cyclic substituted imidazo[4,5-c]quinoline derivatives
CA3102136A1 (en)	2018-06-06	2019-12-12	Arena Pharmaceuticals, Inc.	Methods of treating conditions related to the s1p1 receptor

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT998979B (it) *	1973-10-26	1976-02-20	Snam Progetti	Processo per la preparazione di chelati di uranio iv
US4293547A (en) *	1980-08-25	1981-10-06	The Upjohn Company	Method of treating malaria
US6001355A (en) *	1982-12-14	1999-12-14	Dowdle; Eugene Bernard Davey	Pro-tPA for the treatment of thrombosis, embolism and related conditions
DE3665609D1 (en) *	1985-05-28	1989-10-19	Sumitomo Chemical Co	Recovery of metals adsorbed on chelating agents
GB8601421D0 (en) *	1986-01-21	1986-02-26	Welding Inst	Charged particle beam generator
US4988815A (en) *	1989-10-26	1991-01-29	Riker Laboratories, Inc.	3-Amino or 3-nitro quinoline compounds which are intermediates in preparing 1H-imidazo[4,5-c]quinolines
US5175296A (en) *	1991-03-01	1992-12-29	Minnesota Mining And Manufacturing Company	Imidazo[4,5-c]quinolin-4-amines and processes for their preparation
US5243041A (en) *	1991-08-22	1993-09-07	Fernandez Pol Jose A	DNA vector with isolated CDNA gene encoding metallopanstimulin
US6140466A (en) *	1994-01-18	2000-10-31	The Scripps Research Institute	Zinc finger protein derivatives and methods therefor
US5780455A (en) *	1994-08-24	1998-07-14	Merck & Co., Inc.	Intravenous alendronate formulations
US5854215A (en) *	1995-03-14	1998-12-29	Praecis Pharmaceuticals Incorporated	Modulators of β-amyloid peptide aggregation
US6127393A (en) *	1995-12-29	2000-10-03	Novactyl, Inc.	Antiproliferative, antiinfective, antiinflammatory, autologous immunization agent and method
US5668016A (en) *	1995-12-29	1997-09-16	Fernandez-Pol; Jose Alberto	Method of preparing and activating samples for radioimmunoassay and other test
US5955287A (en) *	1995-12-29	1999-09-21	Fernandez-Pol; Jose Alberto	Method of determining level of biological substances elevated in the presence of cancer and other neoplasms
US5767135A (en) *	1995-12-29	1998-06-16	Fernandez-Pol; Jose Alberto	Antiviral agent
CZ295118B6 (cs) *	1996-08-13	2005-05-18	P. N. Gerolymatos S. A.	Farmaceutický prostředek
JP2000119271A (ja) *	1998-08-12	2000-04-25	Hokuriku Seiyaku Co Ltd	１ｈ―イミダゾピリジン誘導体

2001
- 2001-02-06 CA CA002399136A patent/CA2399136A1/en not_active Abandoned
- 2001-02-06 CZ CZ20022626A patent/CZ20022626A3/cs unknown
- 2001-02-06 EP EP01902774A patent/EP1256582A1/en not_active Withdrawn
- 2001-02-06 HU HU0204474A patent/HUP0204474A3/hu unknown
- 2001-02-06 CN CN01807727A patent/CN1422269A/zh active Pending
- 2001-02-06 KR KR1020027010326A patent/KR20020073211A/ko not_active Withdrawn
- 2001-02-06 WO PCT/JP2001/000816 patent/WO2001058900A1/ja not_active Ceased
- 2001-02-06 MX MXPA02007525A patent/MXPA02007525A/es not_active Application Discontinuation
- 2001-02-06 PL PL01355866A patent/PL355866A1/xx unknown
- 2001-02-06 US US10/181,407 patent/US20040054182A1/en not_active Abandoned
- 2001-02-06 SK SK1120-2002A patent/SK11202002A3/sk unknown
- 2001-02-06 BR BR0108303-1A patent/BR0108303A/pt not_active Application Discontinuation
- 2001-02-06 AU AU2001230584A patent/AU2001230584A1/en not_active Abandoned
- 2001-02-06 IL IL15084101A patent/IL150841A0/xx unknown
2002
- 2002-08-08 NO NO20023750A patent/NO20023750L/no not_active Application Discontinuation
- 2002-09-05 BG BG107067A patent/BG107067A/bg unknown

Also Published As

Publication number	Publication date
US20040054182A1 (en)	2004-03-18
HUP0204474A2 (hu)	2003-04-28
CN1422269A (zh)	2003-06-04
BG107067A (bg)	2003-09-30
CZ20022626A3 (cs)	2003-02-12
PL355866A1 (en)	2004-05-31
HUP0204474A3 (en)	2004-07-28
KR20020073211A (ko)	2002-09-19
WO2001058900A1 (en)	2001-08-16
EP1256582A1 (en)	2002-11-13
SK11202002A3 (sk)	2003-03-04
IL150841A0 (en)	2003-02-12
MXPA02007525A (es)	2002-12-13
BR0108303A (pt)	2003-03-05
NO20023750D0 (no)	2002-08-08
AU2001230584A1 (en)	2001-08-20
CA2399136A1 (en)	2001-08-16

Legal Events

Date	Code	Title	Description
2003-12-22	FC2A	Withdrawal, rejection or dismissal of laid open patent application

Publication	Publication Date	Title
NO20023750L (no)	2002-10-07	1H-imidazopyridinderivater
AU744388B2 (en)	2002-02-21	1H-imidazopyridine derivatives
AU2006295645B2 (en)	2011-09-29	2-heteroaryl-substituted indole derivative
EP2730564B1 (en)	2018-04-18	Heterocycle amines and uses thereof
EP1221443B1 (en)	2004-09-01	Substituted imidazolidinone derivatives
US7164024B2 (en)	2007-01-16	Benzimidazolone derivatives
US20160289230A1 (en)	2016-10-06	Novel azaindole derivatives as selective histone deacetylase (hdac) inhibitors and pharmaceutical compositions comprising the same
JP2019530739A (ja)	2019-10-24	Ｎ−（ピリジン−２−イル）ピリジン−スルホンアミド誘導体および疾患の処置におけるそれらの使用
JP2023524821A (ja)	2023-06-13	Ｅｎｐｐ１のイミノスルファノン阻害剤
WO2019205983A1 (zh)	2019-10-31	氧杂螺环类化合物及其制备方法和用途
WO2021060453A1 (ja)	2021-04-01	架橋型光学活性２級アミン誘導体
WO2002016370A1 (en)	2002-02-28	1h-imidazopyridine derivatives
KR101004156B1 (ko)	2010-12-27	키나제 억제제
AU2004222341A1 (en)	2004-09-30	Tetrahydropyranyl cyclopentyl heterocylic amide modulators of chemokine receptor activity
KR20240168922A (ko)	2024-12-02	방향족 헤테로사이클릭 화합물, 그의 제조 방법 및 그의 용도
CN107849047B (zh)	2021-01-15	一种联苯衍生物及其制备方法和在医药上的用途
JP2022532145A (ja)	2022-07-13	置換ベンズイミダゾロン化合物
US7405210B2 (en)	2008-07-29	Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase
WO2023185073A1 (zh)	2023-10-05	Parp7抑制剂及其用途
US11992494B2 (en)	2024-05-28	Cyclopentathiophene carboxamide derivatives as platelet activating factor receptor antagonists
JP2002161095A (ja)	2002-06-04	１ｈ−イミダゾピリジン誘導体
JP2003002890A (ja)	2003-01-08	１ｈ−イミダゾピリジン誘導体
MXPA01001378A (es)	2002-07-25	Derivados de 1h-imidazopiridina
HK40083035B (zh)	2024-11-29	Parp7抑制剂及其用途
KR20110006171A (ko)	2011-01-20	테트라히드로이미다조피리딘기가 치환된 퀴놀리논 화합물