CA2552101A1

CA2552101A1 - Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds

Piperazine, [1,4]diazepane, [1,4]diazocane, and [1,5]diazocane fused imidazo ring compounds Download PDF

Info

Publication number: CA2552101A1
Authority: CA; Canada
Prior art keywords: group; alkyl; aryl; alkenyl; heterocyclyl
Prior art date: 2003-12-29
Legal status : Abandoned

Application number

CA002552101A

Other languages

English (en)

French (fr)

Inventor

Tushar A. Kshirsagar

George W. Griesgraber

Azim A. Celebi

Philip D. Heppner

Current Assignee

3M Innovative Properties Co

Original Assignee

Individual

Priority date

2003-12-29

Filing date

2004-12-22

Publication date

2005-07-21

2004-12-22 Application filed by Individual filed Critical Individual

2005-07-21 Publication of CA2552101A1 publication Critical patent/CA2552101A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 210
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract description 6
CXPUAWQOXQINEX-UHFFFAOYSA-N 1,4-diazocane Chemical compound C1CCNCCNC1 CXPUAWQOXQINEX-UHFFFAOYSA-N 0.000 title abstract description 3
HTSQWLLKIZBMEO-UHFFFAOYSA-N 1,5-diazocane Chemical compound C1CNCCCNC1 HTSQWLLKIZBMEO-UHFFFAOYSA-N 0.000 title abstract description 3
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 title abstract 2
238000000034 method Methods 0.000 claims abstract description 70
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 32
230000015572 biosynthetic process Effects 0.000 claims abstract description 31
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
201000010099 disease Diseases 0.000 claims abstract description 28
230000003612 virological effect Effects 0.000 claims abstract description 11
230000001613 neoplastic effect Effects 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
230000001939 inductive effect Effects 0.000 claims abstract description 6
-1 nitro, hydroxy, mercapto Chemical group 0.000 claims description 212
125000000217 alkyl group Chemical group 0.000 claims description 193
125000003118 aryl group Chemical group 0.000 claims description 125
125000003342 alkenyl group Chemical group 0.000 claims description 116
125000000623 heterocyclic group Chemical group 0.000 claims description 116
150000003839 salts Chemical class 0.000 claims description 115
125000001072 heteroaryl group Chemical group 0.000 claims description 103
229910052739 hydrogen Inorganic materials 0.000 claims description 99
239000001257 hydrogen Substances 0.000 claims description 99
125000000304 alkynyl group Chemical group 0.000 claims description 84
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 75
125000002947 alkylene group Chemical group 0.000 claims description 73
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
125000004432 carbon atom Chemical group C* 0.000 claims description 69
229910052736 halogen Inorganic materials 0.000 claims description 68
150000002367 halogens Chemical class 0.000 claims description 63
125000003545 alkoxy group Chemical group 0.000 claims description 57
229910052757 nitrogen Inorganic materials 0.000 claims description 56
125000004663 dialkyl amino group Chemical group 0.000 claims description 54
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
125000001424 substituent group Chemical group 0.000 claims description 45
125000004414 alkyl thio group Chemical group 0.000 claims description 43
125000001188 haloalkyl group Chemical group 0.000 claims description 41
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
229910052799 carbon Inorganic materials 0.000 claims description 39
125000005466 alkylenyl group Chemical group 0.000 claims description 35
125000005843 halogen group Chemical group 0.000 claims description 32
229910052717 sulfur Inorganic materials 0.000 claims description 29
125000003282 alkyl amino group Chemical group 0.000 claims description 27
125000005529 alkyleneoxy group Chemical group 0.000 claims description 27
125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 27
125000004093 cyano group Chemical group *C#N 0.000 claims description 27
125000004438 haloalkoxy group Chemical group 0.000 claims description 27
125000005553 heteroaryloxy group Chemical group 0.000 claims description 27
125000004104 aryloxy group Chemical group 0.000 claims description 26
125000004043 oxo group Chemical group O=* 0.000 claims description 26
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
125000004450 alkenylene group Chemical group 0.000 claims description 24
125000000732 arylene group Chemical group 0.000 claims description 24
125000005549 heteroarylene group Chemical group 0.000 claims description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 20
125000004419 alkynylene group Chemical group 0.000 claims description 19
125000001589 carboacyl group Chemical group 0.000 claims description 18
125000004423 acyloxy group Chemical group 0.000 claims description 17
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
125000005110 aryl thio group Chemical group 0.000 claims description 17
229920006395 saturated elastomer Polymers 0.000 claims description 14
230000002452 interceptive effect Effects 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
UVDTYBZFXURMNE-UHFFFAOYSA-N 9-(methylsulfonyl)-9,10,11,12-tetrahydro-8h-[1,4]diazepino[1',2':1,2]imidazo[4,5-c]quinolin-6-amine Chemical compound C1N(S(=O)(=O)C)CCCN2C3=C4C=CC=CC4=NC(N)=C3N=C12 UVDTYBZFXURMNE-UHFFFAOYSA-N 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
230000001419 dependent effect Effects 0.000 claims 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 12
RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 abstract description 8
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 abstract description 6
239000000543 intermediate Substances 0.000 abstract description 6
239000002955 immunomodulating agent Substances 0.000 abstract description 4
229940121354 immunomodulator Drugs 0.000 abstract description 4
230000002401 inhibitory effect Effects 0.000 abstract description 3
150000005232 imidazopyridines Chemical class 0.000 abstract description 2
ZZXQWFQBPSUCAF-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-b][1,8]naphthyridine Chemical class N1C2=NC=CC=C2C=C2C1NCN2 ZZXQWFQBPSUCAF-UHFFFAOYSA-N 0.000 abstract 1
GCGNWZMOENODOJ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-h]quinoline Chemical class C1C=C2C=CC=NC2=C2C1NCN2 GCGNWZMOENODOJ-UHFFFAOYSA-N 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 258
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 235
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 216
239000000243 solution Substances 0.000 description 148
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 128
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 117
230000002829 reductive effect Effects 0.000 description 109
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 105
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 96
239000000047 product Substances 0.000 description 68
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
239000007787 solid Substances 0.000 description 62
239000002904 solvent Substances 0.000 description 60
239000000203 mixture Substances 0.000 description 58
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
239000000463 material Substances 0.000 description 43
239000011541 reaction mixture Substances 0.000 description 43
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
238000007796 conventional method Methods 0.000 description 39
238000001914 filtration Methods 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
229910001868 water Inorganic materials 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 35
238000012360 testing method Methods 0.000 description 35
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
239000003153 chemical reaction reagent Substances 0.000 description 29
239000000706 filtrate Substances 0.000 description 29
239000012948 isocyanate Substances 0.000 description 29
238000002953 preparative HPLC Methods 0.000 description 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
239000002253 acid Substances 0.000 description 28
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 27
150000002513 isocyanates Chemical class 0.000 description 27
239000002244 precipitate Substances 0.000 description 25
239000000741 silica gel Substances 0.000 description 25
229910002027 silica gel Inorganic materials 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 24
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 23
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
YHEPBWTXCZVUHG-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-6-amine Chemical compound N1=C2C(N)=CC=CC2=C2NC=NC2=C1 YHEPBWTXCZVUHG-UHFFFAOYSA-N 0.000 description 21
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 21
239000000908 ammonium hydroxide Substances 0.000 description 21
238000004440 column chromatography Methods 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
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 19
239000012359 Methanesulfonyl chloride Substances 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000010410 layer Substances 0.000 description 18
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 18
229910021529 ammonia Inorganic materials 0.000 description 17
239000000725 suspension Substances 0.000 description 17
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
239000000843 powder Substances 0.000 description 16
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
238000005160 1H NMR spectroscopy Methods 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
125000001181 organosilyl group Chemical group [SiH3]* 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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
239000012267 brine Substances 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
235000019341 magnesium sulphate Nutrition 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 13
229910052700 potassium Inorganic materials 0.000 description 13
239000011591 potassium Substances 0.000 description 13
150000001408 amides Chemical class 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 12
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 12
150000001299 aldehydes Chemical class 0.000 description 11
238000005119 centrifugation Methods 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
238000005984 hydrogenation reaction Methods 0.000 description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
230000004048 modification Effects 0.000 description 11
238000012986 modification Methods 0.000 description 11
229960005235 piperonyl butoxide Drugs 0.000 description 11
229910000029 sodium carbonate Inorganic materials 0.000 description 11
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 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000002585 base Substances 0.000 description 10
239000013078 crystal Substances 0.000 description 10
150000004820 halides Chemical class 0.000 description 10
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
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 9
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 9
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 9
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000013877 carbamide Nutrition 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000012299 nitrogen atmosphere Substances 0.000 description 9
238000000746 purification Methods 0.000 description 9
230000009467 reduction Effects 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
239000004202 carbamide Substances 0.000 description 8
239000002158 endotoxin Substances 0.000 description 8
230000028993 immune response Effects 0.000 description 8
230000006698 induction Effects 0.000 description 8
229920006008 lipopolysaccharide Polymers 0.000 description 8
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
229940124530 sulfonamide Drugs 0.000 description 8
150000003456 sulfonamides Chemical class 0.000 description 8
102000003390 tumor necrosis factor Human genes 0.000 description 8
239000003643 water by type Substances 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 7
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 7
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 7
239000002168 alkylating agent Substances 0.000 description 7
229940100198 alkylating agent Drugs 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
150000002576 ketones Chemical class 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
238000003756 stirring Methods 0.000 description 7
238000010189 synthetic method Methods 0.000 description 7
150000003512 tertiary amines Chemical class 0.000 description 7
WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 6
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
238000002965 ELISA Methods 0.000 description 6
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
102000014150 Interferons Human genes 0.000 description 6
108010050904 Interferons Proteins 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
125000001246 bromo group Chemical group Br* 0.000 description 6
WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 6
238000006073 displacement reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
BGWMHFKCAUBYJJ-UHFFFAOYSA-N ethyl 2-chloroethanimidate;hydrochloride Chemical compound Cl.CCOC(=N)CCl BGWMHFKCAUBYJJ-UHFFFAOYSA-N 0.000 description 6
239000012065 filter cake Substances 0.000 description 6
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
238000007429 general method Methods 0.000 description 6
238000011534 incubation Methods 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
229940079322 interferon Drugs 0.000 description 6
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 6
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
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