JP4891088B2 - 置換されたイミダゾ環系および方法 - Google Patents

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Publication number

JP4891088B2

JP4891088B2 JP2006541697A JP2006541697A JP4891088B2 JP 4891088 B2 JP4891088 B2 JP 4891088B2 JP 2006541697 A JP2006541697 A JP 2006541697A JP 2006541697 A JP2006541697 A JP 2006541697A JP 4891088 B2 JP4891088 B2 JP 4891088B2

Authority

JP

Japan

Prior art keywords

alkyl

group

aryl

alkylene

heteroaryl

Prior art date

2003-11-25

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.)

Expired - Fee Related

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• 238000000034 method Methods 0.000 title description 19
• 125000000217 alkyl group Chemical group 0.000 claims description 229
• 125000003118 aryl group Chemical group 0.000 claims description 122
• 150000001875 compounds Chemical class 0.000 claims description 111
• 125000001072 heteroaryl group Chemical group 0.000 claims description 109
• -1 nitro, hydroxy, mercapto Chemical class 0.000 claims description 102
• 229910052739 hydrogen Inorganic materials 0.000 claims description 86
• 239000001257 hydrogen Substances 0.000 claims description 86
• 125000005275 alkylenearyl group Chemical group 0.000 claims description 66
• 125000003545 alkoxy group Chemical group 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 64
• 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 62
• 125000001188 haloalkyl group Chemical group 0.000 claims description 59
• 150000002431 hydrogen Chemical class 0.000 claims description 59
• 229910052736 halogen Inorganic materials 0.000 claims description 57
• 150000002367 halogens Chemical class 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 54
• 125000002947 alkylene group Chemical group 0.000 claims description 46
• 125000003342 alkenyl group Chemical group 0.000 claims description 45
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 45
• 125000004414 alkyl thio group Chemical group 0.000 claims description 42
• 229920006395 saturated elastomer Polymers 0.000 claims description 41
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 39
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 125000000304 alkynyl group Chemical group 0.000 claims description 22
• 125000000732 arylene group Chemical group 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 14
• 125000004419 alkynylene group Chemical group 0.000 claims description 14
• 125000005549 heteroarylene group Chemical group 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 8
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 6
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 5
• 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 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 246
• 238000006243 chemical reaction Methods 0.000 description 217
• 239000000243 solution Substances 0.000 description 132
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 96
• 239000007787 solid Substances 0.000 description 74
• 238000007429 general method Methods 0.000 description 64
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 56
• 239000000203 mixture Substances 0.000 description 56
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
• 238000000746 purification Methods 0.000 description 42
• 239000011541 reaction mixture Substances 0.000 description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• 238000007796 conventional method Methods 0.000 description 32
• 239000003921 oil Substances 0.000 description 31
• 235000019198 oils Nutrition 0.000 description 31
• 238000004458 analytical method Methods 0.000 description 30
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 29
• 239000000908 ammonium hydroxide Substances 0.000 description 29
• 239000000047 product Substances 0.000 description 29
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 28
• 235000017557 sodium bicarbonate Nutrition 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 238000002844 melting Methods 0.000 description 27
• 230000008018 melting Effects 0.000 description 27
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
• 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 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 24
• 102000004127 Cytokines Human genes 0.000 description 23
• 108090000695 Cytokines Proteins 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• 238000001953 recrystallisation Methods 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000010410 layer Substances 0.000 description 20
• 125000004122 cyclic group Chemical group 0.000 description 19
• 238000010828 elution Methods 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 201000010099 disease Diseases 0.000 description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
• 229910000027 potassium carbonate Inorganic materials 0.000 description 17
• ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 16
• 241001465754 Metazoa Species 0.000 description 16
• 150000002576 ketones Chemical class 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
• 150000001204 N-oxides Chemical class 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 230000015572 biosynthetic process Effects 0.000 description 13
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 238000004587 chromatography analysis Methods 0.000 description 11
• 239000000463 material Substances 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 0.000 description 10
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical class C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 10
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
• 230000009467 reduction Effects 0.000 description 10
• 230000003612 virological effect Effects 0.000 description 10
• 239000012267 brine Substances 0.000 description 9
• 150000002148 esters Chemical class 0.000 description 9
• 229910052760 oxygen Inorganic materials 0.000 description 9
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
• UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 9
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
• 229910052717 sulfur Inorganic materials 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 239000013078 crystal Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 150000004795 grignard reagents Chemical class 0.000 description 8
• USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• 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
• 239000007818 Grignard reagent Substances 0.000 description 7
• 206010028980 Neoplasm Diseases 0.000 description 7
• 150000001241 acetals Chemical class 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 238000005984 hydrogenation reaction Methods 0.000 description 7
• 230000028993 immune response Effects 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
• 235000019341 magnesium sulphate Nutrition 0.000 description 7
• 230000001613 neoplastic effect Effects 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
• HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 150000001412 amines Chemical class 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 239000011777 magnesium Substances 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• 230000006698 induction Effects 0.000 description 5
• PGPJIZPZLAPJPU-UHFFFAOYSA-N n-methoxy-n-methyl-4-(2-propylimidazo[4,5-c]quinolin-1-yl)butanamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCC(=O)N(C)OC)C3=CN=C21 PGPJIZPZLAPJPU-UHFFFAOYSA-N 0.000 description 5
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• 0 Cc1nc(N)c2nc(*)[n](***)c2c1* Chemical compound Cc1nc(N)c2nc(*)[n](***)c2c1* 0.000 description 4
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• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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• 239000012141 concentrate Substances 0.000 description 4
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• MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 description 4
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• 150000004820 halides Chemical group 0.000 description 4
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• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 4
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• 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
• XUXVVQKJULMMKX-UHFFFAOYSA-N 1,1,1-trimethoxypentane Chemical compound CCCCC(OC)(OC)OC XUXVVQKJULMMKX-UHFFFAOYSA-N 0.000 description 3
• ABUFEAKDTQPJQZ-UHFFFAOYSA-N 2,2-diethylbutane-1,1,1-triol Chemical group CCC(CC)(CC)C(O)(O)O ABUFEAKDTQPJQZ-UHFFFAOYSA-N 0.000 description 3
• RTXYIHGMYDJHEU-UHFFFAOYSA-N 2,4-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=C(Cl)C=CN=C1Cl RTXYIHGMYDJHEU-UHFFFAOYSA-N 0.000 description 3
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 3
• IGBIYFMZLHXWJJ-UHFFFAOYSA-N 4-(2-butylimidazo[4,5-c]quinolin-1-yl)butanal Chemical compound C1=CC=CC2=C(N(C(CCCC)=N3)CCCC=O)C3=CN=C21 IGBIYFMZLHXWJJ-UHFFFAOYSA-N 0.000 description 3
• RPKKNEPABGBNIC-UHFFFAOYSA-N 5-(4-amino-2-propylimidazo[4,5-c]quinolin-1-yl)-n-methoxy-n-methylpentanamide Chemical compound C1=CC=CC2=C(N(C(CCC)=N3)CCCCC(=O)N(C)OC)C3=C(N)N=C21 RPKKNEPABGBNIC-UHFFFAOYSA-N 0.000 description 3
• DDRVABYGPQTODO-UHFFFAOYSA-N 5-(4-amino-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-1-yl)pentan-2-one Chemical compound N1=C(C)C(C)=C2N(CCCC(C)=O)C(CCC)=NC2=C1N DDRVABYGPQTODO-UHFFFAOYSA-N 0.000 description 3
• FJXGNKGKSKSQLA-UHFFFAOYSA-N 6-[(3-aminoquinolin-4-yl)amino]-1-phenylhexan-1-one Chemical compound NC1=CN=C2C=CC=CC2=C1NCCCCCC(=O)C1=CC=CC=C1 FJXGNKGKSKSQLA-UHFFFAOYSA-N 0.000 description 3
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