JP2009519955A - 置換されたイミダゾキノリン、イミダゾナフチリジンおよびイミダゾピリジン、組成物ならびに方法 - Google Patents

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Publication number

JP2009519955A

JP2009519955A JP2008545861A JP2008545861A JP2009519955A JP 2009519955 A JP2009519955 A JP 2009519955A JP 2008545861 A JP2008545861 A JP 2008545861A JP 2008545861 A JP2008545861 A JP 2008545861A JP 2009519955 A JP2009519955 A JP 2009519955A

Authority

JP

Japan

Prior art keywords

group

alkyl

tetrahydro

pyran

alkylenyl

Prior art date

2005-12-16

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

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• 238000000034 method Methods 0.000 title claims abstract description 75
• 239000000203 mixture Chemical class 0.000 title description 114
• VFTLXHXYGQSOEN-UHFFFAOYSA-N 1h-imidazo[4,5-b][1,8]naphthyridine Chemical class C1=CN=C2NC3=NC=NC3=CC2=C1 VFTLXHXYGQSOEN-UHFFFAOYSA-N 0.000 title description 2
• RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 2
• 150000005232 imidazopyridines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 266
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 83
• 102000004127 Cytokines Human genes 0.000 claims abstract description 41
• 108090000695 Cytokines Proteins 0.000 claims abstract description 41
• 241001465754 Metazoa Species 0.000 claims abstract description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 201000010099 disease Diseases 0.000 claims abstract description 26
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 18
• 230000003612 virological effect Effects 0.000 claims abstract description 14
• 230000001613 neoplastic effect Effects 0.000 claims abstract description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 281
• -1 tetrahydrofuran-3-yl Chemical group 0.000 claims description 188
• 150000003839 salts Chemical class 0.000 claims description 117
• 125000000623 heterocyclic group Chemical group 0.000 claims description 77
• 239000001257 hydrogen Substances 0.000 claims description 75
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 59
• 229910052736 halogen Inorganic materials 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 50
• 125000002947 alkylene group Chemical group 0.000 claims description 49
• 150000002367 halogens Chemical class 0.000 claims description 48
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
• 125000001072 heteroaryl group Chemical group 0.000 claims description 47
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 45
• 125000001424 substituent group Chemical group 0.000 claims description 44
• 125000005466 alkylenyl group Chemical group 0.000 claims description 42
• 125000003342 alkenyl group Chemical group 0.000 claims description 30
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 125000004450 alkenylene group Chemical group 0.000 claims description 25
• 125000000732 arylene group Chemical group 0.000 claims description 25
• 125000001188 haloalkyl group Chemical group 0.000 claims description 25
• 125000005549 heteroarylene group Chemical group 0.000 claims description 24
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 23
• 125000004419 alkynylene group Chemical group 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
• 239000003937 drug carrier Substances 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 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 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 16
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 15
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 8
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 7
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 8
• 230000001419 dependent effect Effects 0.000 claims 2
• ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical group C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 abstract description 17
• IDUUCDZKSKUCOP-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridine Chemical class C1=CC=NC2=C(NC=N3)C3=CN=C21 IDUUCDZKSKUCOP-UHFFFAOYSA-N 0.000 abstract description 12
• 230000001939 inductive effect Effects 0.000 abstract description 7
• 150000005239 1H-imidazo[4,5-c]pyridines Chemical class 0.000 abstract description 2
• FGGPIDNXZDDRSG-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c][1,5]naphthyridine Chemical class C1CCNC2=C1N=CC1=C2N=CN1 FGGPIDNXZDDRSG-UHFFFAOYSA-N 0.000 abstract description 2
• CZTQJCYFLGFVLG-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinoline Chemical class C1CCCC2=C1N=CC1=C2NC=N1 CZTQJCYFLGFVLG-UHFFFAOYSA-N 0.000 abstract description 2
• 239000002955 immunomodulating agent Substances 0.000 abstract 1
• 229940121354 immunomodulator Drugs 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 204
• 239000007787 solid Substances 0.000 description 175
• 238000006243 chemical reaction Methods 0.000 description 160
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 148
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 147
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 131
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 105
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 95
• 239000000243 solution Substances 0.000 description 93
• 239000011541 reaction mixture Substances 0.000 description 91
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 80
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• 238000000921 elemental analysis Methods 0.000 description 66
• 239000003921 oil Substances 0.000 description 62
• 235000019198 oils Nutrition 0.000 description 62
• 239000000741 silica gel Substances 0.000 description 61
• 229910002027 silica gel Inorganic materials 0.000 description 61
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
• 238000001914 filtration Methods 0.000 description 58
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• 238000002953 preparative HPLC Methods 0.000 description 57
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 56
• 238000002844 melting Methods 0.000 description 56
• 230000008018 melting Effects 0.000 description 56
• 239000000463 material Substances 0.000 description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
• 239000012043 crude product Substances 0.000 description 41
• 229910052757 nitrogen Inorganic materials 0.000 description 41
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 40
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
• 239000002904 solvent Substances 0.000 description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
• 239000010410 layer Substances 0.000 description 34
• 238000005259 measurement Methods 0.000 description 34
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 239000000706 filtrate Substances 0.000 description 29
• 108010047761 Interferon-alpha Proteins 0.000 description 27
• 102000006992 Interferon-alpha Human genes 0.000 description 27
• 238000010992 reflux Methods 0.000 description 27
• 238000007429 general method Methods 0.000 description 26
• 239000012299 nitrogen atmosphere Substances 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 25
• OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 23
• 238000012360 testing method Methods 0.000 description 23
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 20
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 238000004458 analytical method Methods 0.000 description 19
• 239000000047 product Substances 0.000 description 19
• 239000013078 crystal Substances 0.000 description 18
• 238000002474 experimental method Methods 0.000 description 18
• 229910000029 sodium carbonate Inorganic materials 0.000 description 18
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 16
• JSMDUOFOPDSKIQ-UHFFFAOYSA-N 3-methoxypropanoyl chloride Chemical compound COCCC(Cl)=O JSMDUOFOPDSKIQ-UHFFFAOYSA-N 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• 239000003153 chemical reaction reagent Substances 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• 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 15
• 238000009835 boiling Methods 0.000 description 15
• 238000004811 liquid chromatography Methods 0.000 description 15
• GIROJVFYHQUUFX-UHFFFAOYSA-N 8-bromo-2-(2-methoxyethyl)-1-(oxan-4-ylmethyl)imidazo[4,5-c]quinoline Chemical compound COCCC1=NC2=CN=C3C=CC(Br)=CC3=C2N1CC1CCOCC1 GIROJVFYHQUUFX-UHFFFAOYSA-N 0.000 description 14
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• 238000010189 synthetic method Methods 0.000 description 14
• 238000011282 treatment Methods 0.000 description 14
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
• 125000000266 alpha-aminoacyl group Chemical group 0.000 description 13
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 12
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
• 239000004480 active ingredient Substances 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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• 241000700605 Viruses Species 0.000 description 9
• SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 9
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• 125000004122 cyclic group Chemical group 0.000 description 9
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• 239000000651 prodrug Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• 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 8
• JUGWZJLDVMJLIH-UHFFFAOYSA-N 2-(oxan-4-ylmethyl)quinoline-3,4-diamine Chemical compound N1=C2C=CC=CC2=C(N)C(N)=C1CC1CCOCC1 JUGWZJLDVMJLIH-UHFFFAOYSA-N 0.000 description 8
• ULTNKTPQGCEAHF-UHFFFAOYSA-N 8-bromo-2-(ethoxymethyl)-1-(oxan-4-ylmethyl)imidazo[4,5-c]quinoline Chemical compound CCOCC1=NC2=CN=C3C=CC(Br)=CC3=C2N1CC1CCOCC1 ULTNKTPQGCEAHF-UHFFFAOYSA-N 0.000 description 8
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
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• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• IJJRUJSOEDJQET-UHFFFAOYSA-N 4-n-(oxan-4-ylmethyl)quinoline-3,4-diamine Chemical compound NC1=CN=C2C=CC=CC2=C1NCC1CCOCC1 IJJRUJSOEDJQET-UHFFFAOYSA-N 0.000 description 7
• 0 C*1=*CCCC1 Chemical compound C*1=*CCCC1 0.000 description 7
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