JP5128815B2 - アリールオキシ置換およびアリールアルキレンオキシ置換イミダゾキノリン - Google Patents

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Publication number

JP5128815B2

JP5128815B2 JP2006524906A JP2006524906A JP5128815B2 JP 5128815 B2 JP5128815 B2 JP 5128815B2 JP 2006524906 A JP2006524906 A JP 2006524906A JP 2006524906 A JP2006524906 A JP 2006524906A JP 5128815 B2 JP5128815 B2 JP 5128815B2

Authority

JP

Japan

Prior art keywords

group

alkyl

imidazo

independently

benzyloxy

Prior art date

2003-08-27

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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• 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 1
• 229910052739 hydrogen Inorganic materials 0.000 claims description 274
• -1 methylenedioxy Chemical group 0.000 claims description 186
• 125000000217 alkyl group Chemical group 0.000 claims description 152
• 150000001875 compounds Chemical class 0.000 claims description 136
• 125000002947 alkylene group Chemical group 0.000 claims description 97
• 125000001072 heteroaryl group Chemical group 0.000 claims description 89
• 125000003118 aryl group Chemical group 0.000 claims description 77
• 125000000623 heterocyclic group Chemical group 0.000 claims description 76
• 239000001257 hydrogen Substances 0.000 claims description 76
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 61
• 150000003839 salts Chemical class 0.000 claims description 59
• 125000003342 alkenyl group Chemical group 0.000 claims description 57
• 229910052736 halogen Inorganic materials 0.000 claims description 52
• 150000002367 halogens Chemical class 0.000 claims description 52
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 50
• 125000003545 alkoxy group Chemical group 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 125000000304 alkynyl group Chemical group 0.000 claims description 45
• 125000004450 alkenylene group Chemical group 0.000 claims description 44
• 125000004419 alkynylene group Chemical group 0.000 claims description 44
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 125000000732 arylene group Chemical group 0.000 claims description 36
• 125000005549 heteroarylene group Chemical group 0.000 claims description 35
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 34
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 33
• 125000003282 alkyl amino group Chemical group 0.000 claims description 31
• 150000002431 hydrogen Chemical class 0.000 claims description 31
• 125000001188 haloalkyl group Chemical group 0.000 claims description 28
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 28
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 22
• 125000004104 aryloxy group Chemical group 0.000 claims description 22
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 11
• 125000005466 alkylenyl 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
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001041 indolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• VBPCJXULFWAEQR-UHFFFAOYSA-N 1-(4-aminobutyl)-2-butyl-8-phenylmethoxyimidazo[4,5-c]quinolin-4-amine Chemical compound C=1C2=C3N(CCCCN)C(CCCC)=NC3=C(N)N=C2C=CC=1OCC1=CC=CC=C1 VBPCJXULFWAEQR-UHFFFAOYSA-N 0.000 claims description 3
• 241001024304 Mino Species 0.000 claims description 3
• DMUIEMKJAAPBFE-UHFFFAOYSA-N N-[1-[4-amino-2-(ethoxymethyl)-7-hydroxyimidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical compound C1=C(O)C=CC2=C(N(C(COCC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 DMUIEMKJAAPBFE-UHFFFAOYSA-N 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• FAYJSGIWQXGWPI-UHFFFAOYSA-N N-[4-(4-amino-2-ethyl-7-hydroxyimidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide Chemical compound C1=C(O)C=CC2=C(N(C(CC)=N3)CCCCNS(C)(=O)=O)C3=C(N)N=C21 FAYJSGIWQXGWPI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 3
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
• LFJLJCHGXYWQKP-UHFFFAOYSA-N 7-(4-aminophenoxy)-1-(2-methylpropyl)-2-propylimidazo[4,5-c]quinolin-4-amine Chemical compound C1=CC2=C3N(CC(C)C)C(CCC)=NC3=C(N)N=C2C=C1OC1=CC=C(N)C=C1 LFJLJCHGXYWQKP-UHFFFAOYSA-N 0.000 claims 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 393
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 378
• 238000006243 chemical reaction Methods 0.000 description 306
• 239000000243 solution Substances 0.000 description 303
• 229910052757 nitrogen Inorganic materials 0.000 description 201
• 229910052799 carbon Inorganic materials 0.000 description 199
• 239000007787 solid Substances 0.000 description 174
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 146
• 230000002829 reductive effect Effects 0.000 description 136
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 128
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 126
• 238000005160 1H NMR spectroscopy Methods 0.000 description 115
• 238000004458 analytical method Methods 0.000 description 113
• 238000001914 filtration Methods 0.000 description 112
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 105
• 239000007795 chemical reaction product Substances 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
• 238000005481 NMR spectroscopy Methods 0.000 description 77
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
• 239000002244 precipitate Substances 0.000 description 67
• 238000000034 method Methods 0.000 description 62
• 239000000203 mixture Substances 0.000 description 60
• 239000002904 solvent Substances 0.000 description 60
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
• 239000000843 powder Substances 0.000 description 54
• 239000012043 crude product Substances 0.000 description 51
• 239000000741 silica gel Substances 0.000 description 47
• 229910002027 silica gel Inorganic materials 0.000 description 47
• 239000013078 crystal Substances 0.000 description 46
• 239000003480 eluent Substances 0.000 description 44
• 238000007429 general method Methods 0.000 description 44
• 239000011541 reaction mixture Substances 0.000 description 43
• 238000004440 column chromatography Methods 0.000 description 42
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 37
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
• 238000010992 reflux Methods 0.000 description 36
• 239000010410 layer Substances 0.000 description 33
• 241001465754 Metazoa Species 0.000 description 32
• 239000000706 filtrate Substances 0.000 description 32
• 238000000746 purification Methods 0.000 description 28
• 102000004127 Cytokines Human genes 0.000 description 27
• 108090000695 Cytokines Proteins 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 238000007796 conventional method Methods 0.000 description 27
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 25
• 230000004048 modification Effects 0.000 description 24
• 238000012986 modification Methods 0.000 description 24
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 23
• 239000000908 ammonium hydroxide Substances 0.000 description 23
• 201000010099 disease Diseases 0.000 description 23
• 239000007858 starting material Substances 0.000 description 23
• 239000012299 nitrogen atmosphere Substances 0.000 description 22
• 239000003921 oil Substances 0.000 description 22
• 235000019198 oils Nutrition 0.000 description 22
• 239000012267 brine Substances 0.000 description 21
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
• 238000011282 treatment Methods 0.000 description 21
• 230000015572 biosynthetic process Effects 0.000 description 20
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
• 238000004809 thin layer chromatography Methods 0.000 description 19
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
• 235000019341 magnesium sulphate Nutrition 0.000 description 18
• 238000003756 stirring Methods 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 150000001412 amines Chemical class 0.000 description 17
• 239000000460 chlorine Substances 0.000 description 17
• 229910052717 sulfur Inorganic materials 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• 239000012065 filter cake Substances 0.000 description 16
• 239000000463 material Substances 0.000 description 16
• 229910052938 sodium sulfate Inorganic materials 0.000 description 16
• 235000011152 sodium sulphate Nutrition 0.000 description 16
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 15
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 239000003054 catalyst Substances 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 14
• XVVHIWSUAUILLM-UHFFFAOYSA-N 1-phenylmethoxyimidazo[4,5-c]quinolin-4-amine Chemical compound C1=NC=2C(N)=NC3=CC=CC=C3C=2N1OCC1=CC=CC=C1 XVVHIWSUAUILLM-UHFFFAOYSA-N 0.000 description 13
• ITIRVXDSMXFTPW-UHFFFAOYSA-N 1H-imidazo[4,5-c]quinoline Chemical class C1=CC=CC2=C(NC=N3)C3=CN=C21 ITIRVXDSMXFTPW-UHFFFAOYSA-N 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 230000003612 virological effect Effects 0.000 description 13
• GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 12
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 12
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 12
• 229910000024 caesium carbonate Inorganic materials 0.000 description 12
• 239000008367 deionised water Substances 0.000 description 12
• 229910021641 deionized water Inorganic materials 0.000 description 12
• 238000010438 heat treatment Methods 0.000 description 12
• QVXHUWFRLYPSCY-UHFFFAOYSA-N 3-nitro-2-phenylmethoxyquinolin-4-amine Chemical compound N=1C2=CC=CC=C2C(N)=C([N+]([O-])=O)C=1OCC1=CC=CC=C1 QVXHUWFRLYPSCY-UHFFFAOYSA-N 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 10
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 10
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 10
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 10
• 230000001613 neoplastic effect Effects 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• 238000010189 synthetic method Methods 0.000 description 10
• 125000003396 thiol group Chemical class [H]S* 0.000 description 10
• 239000003039 volatile agent Substances 0.000 description 10
• XTAVMVXAGPRMKN-UHFFFAOYSA-N 1-phenylmethoxyimidazo[4,5-c]quinoline Chemical compound C1=NC2=CN=C3C=CC=CC3=C2N1OCC1=CC=CC=C1 XTAVMVXAGPRMKN-UHFFFAOYSA-N 0.000 description 9
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 9
• XIIMGQMTEDEDNC-UHFFFAOYSA-N 4-chloro-3-nitro-7-phenylmethoxyquinoline Chemical compound C1=CC2=C(Cl)C([N+](=O)[O-])=CN=C2C=C1OCC1=CC=CC=C1 XIIMGQMTEDEDNC-UHFFFAOYSA-N 0.000 description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
• 238000004587 chromatography analysis Methods 0.000 description 9
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 9
• 229910000029 sodium carbonate Inorganic materials 0.000 description 9
• 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 8
• IQYPSFAWXDKDBA-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-c]quinolin-2-one Chemical compound C1=CC=CC2=C(NC(=O)N3)C3=CN=C21 IQYPSFAWXDKDBA-UHFFFAOYSA-N 0.000 description 8
• HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical compound NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 230000028993 immune response Effects 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• 238000012916 structural analysis Methods 0.000 description 8
• 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 description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
• 150000001204 N-oxides Chemical class 0.000 description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 7
• 238000000921 elemental analysis Methods 0.000 description 7
• 238000005984 hydrogenation reaction Methods 0.000 description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 206010028980 Neoplasm Diseases 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 241000700605 Viruses Species 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
• 150000004820 halides Chemical class 0.000 description 6
• 230000002452 interceptive effect Effects 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 238000002953 preparative HPLC Methods 0.000 description 6
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
• 235000017557 sodium bicarbonate Nutrition 0.000 description 6
• GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 6
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