NZ546273A - Alkoxy substituted imidazoquinolines - Google Patents

Info

Publication number

NZ546273A

NZ546273A NZ546273A NZ54627304A NZ546273A NZ 546273 A NZ546273 A NZ 546273A NZ 546273 A NZ546273 A NZ 546273A NZ 54627304 A NZ54627304 A NZ 54627304A NZ 546273 A NZ546273 A NZ 546273A

Authority

NZ

New Zealand

Prior art keywords

group

alkyl

compound

salt

alkylene

Prior art date

2003-10-03

Links

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• 125000003545 alkoxy group Chemical group 0.000 title claims description 58
• 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 abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 164
• 102000004127 Cytokines Human genes 0.000 claims abstract description 32
• 108090000695 Cytokines Proteins 0.000 claims abstract description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
• 201000010099 disease Diseases 0.000 claims abstract description 30
• 241001465754 Metazoa Species 0.000 claims abstract description 29
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 26
• 230000003612 virological effect Effects 0.000 claims abstract description 13
• 230000001613 neoplastic effect Effects 0.000 claims abstract description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 230000001939 inductive effect Effects 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 218
• 125000002947 alkylene group Chemical group 0.000 claims description 142
• -1 nitro, hydroxy, mercapto Chemical group 0.000 claims description 132
• 150000003839 salts Chemical class 0.000 claims description 119
• 125000003118 aryl group Chemical group 0.000 claims description 107
• 229910052739 hydrogen Inorganic materials 0.000 claims description 105
• 239000001257 hydrogen Substances 0.000 claims description 104
• 125000000623 heterocyclic group Chemical group 0.000 claims description 99
• 239000000203 mixture Substances 0.000 claims description 89
• 125000001072 heteroaryl group Chemical group 0.000 claims description 81
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 81
• 125000003342 alkenyl group Chemical group 0.000 claims description 69
• 229910052736 halogen Inorganic materials 0.000 claims description 63
• 150000002367 halogens Chemical group 0.000 claims description 63
• 125000004450 alkenylene group Chemical group 0.000 claims description 62
• 125000004419 alkynylene group Chemical group 0.000 claims description 62
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 50
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
• 125000000304 alkynyl group Chemical group 0.000 claims description 42
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 40
• 125000005549 heteroarylene group Chemical group 0.000 claims description 38
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 36
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 36
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 36
• 125000004104 aryloxy group Chemical group 0.000 claims description 35
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• 125000000732 arylene group Chemical group 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
• 125000001188 haloalkyl group Chemical group 0.000 claims description 28
• 125000003282 alkyl amino group Chemical group 0.000 claims description 26
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 26
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 26
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 20
• 125000004043 oxo group Chemical group O=* 0.000 claims description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 9
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
• 239000005977 Ethylene Substances 0.000 claims description 7
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000003725 azepanyl group Chemical group 0.000 claims description 4
• 125000004069 aziridinyl group Chemical group 0.000 claims description 4
• 125000005959 diazepanyl group Chemical group 0.000 claims description 4
• 125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000001419 dependent effect Effects 0.000 claims 4
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 4
• 101100484510 Caenorhabditis elegans vha-9 gene Proteins 0.000 claims 1
• 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 92
• 238000011282 treatment Methods 0.000 abstract description 14
• 239000000543 intermediate Substances 0.000 abstract description 11
• 230000002401 inhibitory effect Effects 0.000 abstract description 4
• 239000002955 immunomodulating agent Substances 0.000 abstract description 2
• 229940121354 immunomodulator Drugs 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 480
• 238000006243 chemical reaction Methods 0.000 description 231
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 216
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 201
• 239000007787 solid Substances 0.000 description 185
• 239000000243 solution Substances 0.000 description 179
• 230000002829 reductive effect Effects 0.000 description 164
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 129
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 125
• 229910001868 water Inorganic materials 0.000 description 125
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 120
• 238000005481 NMR spectroscopy Methods 0.000 description 111
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 76
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 71
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
• 238000001914 filtration Methods 0.000 description 67
• 239000002904 solvent Substances 0.000 description 63
• 239000000741 silica gel Substances 0.000 description 57
• 229910002027 silica gel Inorganic materials 0.000 description 57
• 239000011541 reaction mixture Substances 0.000 description 56
• 239000000047 product Substances 0.000 description 55
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• 239000012267 brine Substances 0.000 description 51
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 51
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 49
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• 239000002244 precipitate Substances 0.000 description 48
• 239000010410 layer Substances 0.000 description 44
• 239000000843 powder Substances 0.000 description 43
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 41
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 41
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 40
• 239000012043 crude product Substances 0.000 description 39
• 239000012044 organic layer Substances 0.000 description 39
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 36
• 235000019341 magnesium sulphate Nutrition 0.000 description 36
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
• 238000004440 column chromatography Methods 0.000 description 34
• 238000007796 conventional method Methods 0.000 description 34
• 229920006395 saturated elastomer Polymers 0.000 description 34
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 33
• 238000007429 general method Methods 0.000 description 32
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 31
• 230000004048 modification Effects 0.000 description 31
• 238000012986 modification Methods 0.000 description 31
• 239000000908 ammonium hydroxide Substances 0.000 description 30
• 239000013078 crystal Substances 0.000 description 30
• 239000000463 material Substances 0.000 description 30
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 29
• 239000000706 filtrate Substances 0.000 description 29
• 239000003921 oil Substances 0.000 description 28
• 235000019198 oils Nutrition 0.000 description 28
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
• 238000000746 purification Methods 0.000 description 24
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 23
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 23
• XCRPPAPDRUBKRJ-UHFFFAOYSA-N quinolin-7-ol Chemical compound C1=CC=NC2=CC(O)=CC=C21 XCRPPAPDRUBKRJ-UHFFFAOYSA-N 0.000 description 23
• 238000010992 reflux Methods 0.000 description 23
• 229910052717 sulfur Inorganic materials 0.000 description 23
• 238000010828 elution Methods 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• 238000001953 recrystallisation Methods 0.000 description 19
• 229910000029 sodium carbonate Inorganic materials 0.000 description 19
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
• 150000001412 amines Chemical class 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 229910052938 sodium sulfate Inorganic materials 0.000 description 18
• 235000011152 sodium sulphate Nutrition 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• 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 16
• 125000003277 amino group Chemical group 0.000 description 15
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 14
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 238000007792 addition Methods 0.000 description 13
• 239000012948 isocyanate Substances 0.000 description 13
• IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 13
• 239000012299 nitrogen atmosphere Substances 0.000 description 13
• 239000011780 sodium chloride Substances 0.000 description 13
• 239000000725 suspension Substances 0.000 description 13
• 239000002585 base Substances 0.000 description 12
• 239000003153 chemical reaction reagent Substances 0.000 description 12
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 12
• 150000002513 isocyanates Chemical class 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 11
• 102100040247 Tumor necrosis factor Human genes 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 238000004519 manufacturing process Methods 0.000 description 11
• 238000010189 synthetic method Methods 0.000 description 11
• KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 238000002953 preparative HPLC Methods 0.000 description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
• 229910000024 caesium carbonate Inorganic materials 0.000 description 9
• 238000010438 heat treatment Methods 0.000 description 9
• 230000028993 immune response Effects 0.000 description 9
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 9
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 9
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
• 235000017557 sodium bicarbonate Nutrition 0.000 description 9
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
• 125000003396 thiol group Chemical class [H]S* 0.000 description 9
• 239000003039 volatile agent Substances 0.000 description 9
• 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 8
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 8
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 150000001408 amides Chemical class 0.000 description 8
• 125000004432 carbon atom Chemical group C* 0.000 description 8
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
• IGPFOKFDBICQMC-UHFFFAOYSA-N 3-phenylmethoxyaniline Chemical compound NC1=CC=CC(OCC=2C=CC=CC=2)=C1 IGPFOKFDBICQMC-UHFFFAOYSA-N 0.000 description 7
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 238000004458 analytical method Methods 0.000 description 7
• 150000008064 anhydrides Chemical class 0.000 description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
• 238000000354 decomposition reaction Methods 0.000 description 7
• 239000000284 extract Substances 0.000 description 7
• 239000012065 filter cake Substances 0.000 description 7
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
• 238000010626 work up procedure Methods 0.000 description 7
• GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 6
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
• FIIDVVUUWRJXLF-UHFFFAOYSA-N 4-phenylmethoxyaniline Chemical compound C1=CC(N)=CC=C1OCC1=CC=CC=C1 FIIDVVUUWRJXLF-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 206010028980 Neoplasm Diseases 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 150000001805 chlorine compounds 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
• 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 230000002452 interceptive effect Effects 0.000 description 6
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
• 238000004809 thin layer chromatography Methods 0.000 description 6
• MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 5
• GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 5
• DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 5
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
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