CA2578975A1

CA2578975A1 - 2-amino 1h imidazo ring systems and methods

2-amino 1h imidazo ring systems and methods Download PDF

Info

Publication number: CA2578975A1
Authority: CA; Canada
Prior art keywords: group; alkyl; alkylenyl; heterocyclyl; hydrogen
Prior art date: 2004-09-02
Legal status : Abandoned

Application number

CA002578975A

Other languages

English (en)

French (fr)

Inventor

Tushar A. Kshirsagar

Scott E. Langer

Shri Niwas

Philip D. Heppner

David T. Amos

Current Assignee

3M Innovative Properties Co

Original Assignee

Individual

Priority date

2004-09-02

Filing date

2005-09-01

Publication date

2006-03-16

2005-09-01 Application filed by Individual filed Critical Individual

2006-03-16 Publication of CA2578975A1 publication Critical patent/CA2578975A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 76
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 335
102000004127 Cytokines Human genes 0.000 claims abstract description 49
108090000695 Cytokines Proteins 0.000 claims abstract description 49
241001465754 Metazoa Species 0.000 claims abstract description 38
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
201000010099 disease Diseases 0.000 claims abstract description 31
230000015572 biosynthetic process Effects 0.000 claims abstract description 27
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 10
125000000217 alkyl group Chemical group 0.000 claims description 314
125000005466 alkylenyl group Chemical group 0.000 claims description 264
-1 C1-4 alkylarylenyl Chemical group 0.000 claims description 258
229910052739 hydrogen Inorganic materials 0.000 claims description 179
239000001257 hydrogen Substances 0.000 claims description 179
125000000623 heterocyclic group Chemical group 0.000 claims description 174
125000002947 alkylene group Chemical group 0.000 claims description 137
150000003839 salts Chemical class 0.000 claims description 135
125000003118 aryl group Chemical group 0.000 claims description 131
125000001072 heteroaryl group Chemical group 0.000 claims description 130
150000002431 hydrogen Chemical group 0.000 claims description 98
125000003342 alkenyl group Chemical group 0.000 claims description 95
125000003545 alkoxy group Chemical group 0.000 claims description 90
229910052736 halogen Inorganic materials 0.000 claims description 83
150000002367 halogens Chemical class 0.000 claims description 83
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 74
125000000304 alkynyl group Chemical group 0.000 claims description 69
125000001424 substituent group Chemical group 0.000 claims description 68
125000004450 alkenylene group Chemical group 0.000 claims description 60
125000001188 haloalkyl group Chemical group 0.000 claims description 54
239000000203 mixture Substances 0.000 claims description 54
125000000732 arylene group Chemical group 0.000 claims description 50
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
125000005549 heteroarylene group Chemical group 0.000 claims description 49
125000004663 dialkyl amino group Chemical group 0.000 claims description 48
125000004043 oxo group Chemical group O=* 0.000 claims description 44
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
125000004419 alkynylene group Chemical group 0.000 claims description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 38
125000003282 alkyl amino group Chemical group 0.000 claims description 36
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 35
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
229920006395 saturated elastomer Polymers 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
125000004093 cyano group Chemical group *C#N 0.000 claims description 30
125000004438 haloalkoxy group Chemical group 0.000 claims description 30
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 29
125000004414 alkyl thio group Chemical group 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 24
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
125000005529 alkyleneoxy group Chemical group 0.000 claims description 18
125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 18
125000004104 aryloxy group Chemical group 0.000 claims description 18
125000005553 heteroaryloxy group Chemical group 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 14
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000004990 dihydroxyalkyl group Chemical group 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
230000002452 interceptive effect Effects 0.000 claims description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
150000008575 L-amino acids Chemical class 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
230000001939 inductive effect Effects 0.000 claims description 5
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[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
150000001413 amino acids Chemical class 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
238000011282 treatment Methods 0.000 abstract description 13
239000000543 intermediate Substances 0.000 abstract description 12
125000004122 cyclic group Chemical group 0.000 abstract description 11
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 5
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 3
239000002955 immunomodulating agent Substances 0.000 abstract description 2
229940121354 immunomodulator Drugs 0.000 abstract description 2
JDQVYSWJFCKKPX-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-h]quinoline Chemical class C1CCNC2=C1C=CC1=C2N=CN1 JDQVYSWJFCKKPX-UHFFFAOYSA-N 0.000 abstract 1
150000005232 imidazopyridines Chemical class 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 285
238000006243 chemical reaction Methods 0.000 description 213
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 183
239000000243 solution Substances 0.000 description 135
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 96
230000002829 reductive effect Effects 0.000 description 94
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 88
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
239000007787 solid Substances 0.000 description 71
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
239000002904 solvent Substances 0.000 description 59
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 58
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
229910001868 water Inorganic materials 0.000 description 41
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 40
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 34
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
102100040247 Tumor necrosis factor Human genes 0.000 description 34
108060008682 Tumor Necrosis Factor Proteins 0.000 description 33
229940086542 triethylamine Drugs 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
238000001914 filtration Methods 0.000 description 30
238000003818 flash chromatography Methods 0.000 description 30
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 29
229910021529 ammonia Inorganic materials 0.000 description 29
239000000908 ammonium hydroxide Substances 0.000 description 29
238000004458 analytical method Methods 0.000 description 29
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 29
239000010410 layer Substances 0.000 description 28
239000003795 chemical substances by application Substances 0.000 description 27
229910052943 magnesium sulfate Inorganic materials 0.000 description 27
235000019341 magnesium sulphate Nutrition 0.000 description 27
238000012360 testing method Methods 0.000 description 26
239000000377 silicon dioxide Substances 0.000 description 23
150000001412 amines Chemical class 0.000 description 22
239000000047 product Substances 0.000 description 22
210000004027 cell Anatomy 0.000 description 21
239000003921 oil Substances 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
239000000463 material Substances 0.000 description 20
239000007858 starting material Substances 0.000 description 20
239000002585 base Substances 0.000 description 19
238000002474 experimental method Methods 0.000 description 19
239000002244 precipitate Substances 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 17
238000010992 reflux Methods 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
125000004356 hydroxy functional group Chemical group O* 0.000 description 16
239000012267 brine Substances 0.000 description 15
239000003153 chemical reaction reagent Substances 0.000 description 15
238000007796 conventional method Methods 0.000 description 15
239000000706 filtrate Substances 0.000 description 15
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 15
238000000746 purification Methods 0.000 description 15
CUVUDLDZZGOOKF-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinoline-2,4-diamine Chemical compound C1=CC=CC2=C(NC(N)=N3)C3=C(N)N=C21 CUVUDLDZZGOOKF-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 14
239000000651 prodrug Substances 0.000 description 14
229940002612 prodrug Drugs 0.000 description 14
125000004432 carbon atom Chemical group C* 0.000 description 13
238000010438 heat treatment Methods 0.000 description 13
239000000725 suspension Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
150000002540 isothiocyanates Chemical class 0.000 description 12
238000002360 preparation method Methods 0.000 description 12
NKXSJFUIFJMXED-UHFFFAOYSA-N quinoline-2,4-diamine Chemical compound C1=CC=CC2=NC(N)=CC(N)=C21 NKXSJFUIFJMXED-UHFFFAOYSA-N 0.000 description 12
230000028993 immune response Effects 0.000 description 11
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 11
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 11
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 10
239000012043 crude product Substances 0.000 description 10
HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 10
239000012948 isocyanate Substances 0.000 description 10
150000002513 isocyanates Chemical class 0.000 description 10
239000000843 powder Substances 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
RSFJVCHKGRUCIC-UHFFFAOYSA-N 2,4-dichloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=C(Cl)N=C21 RSFJVCHKGRUCIC-UHFFFAOYSA-N 0.000 description 9
230000006698 induction Effects 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
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
229910052770 Uranium Inorganic materials 0.000 description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 8
210000004369 blood Anatomy 0.000 description 8
239000008280 blood Substances 0.000 description 8
239000002158 endotoxin Substances 0.000 description 8
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 8
239000012065 filter cake Substances 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 8
238000011534 incubation Methods 0.000 description 8
229920006008 lipopolysaccharide Polymers 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
230000009467 reduction Effects 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
229910052727 yttrium Inorganic materials 0.000 description 8
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
125000005842 heteroatom Chemical group 0.000 description 7
238000002953 preparative HPLC Methods 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
238000010189 synthetic method Methods 0.000 description 7
108091003079 Bovine Serum Albumin Proteins 0.000 description 6
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 6
101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
206010028980 Neoplasm Diseases 0.000 description 6
238000003556 assay Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
125000000524 functional group Chemical group 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
210000000265 leukocyte Anatomy 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
230000004044 response Effects 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
BGTSRZGPEKKEAT-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridine-2,4-diamine Chemical class C1=CC=NC2=C(NC(N)=N3)C3=C(N)N=C21 BGTSRZGPEKKEAT-UHFFFAOYSA-N 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
LUTSRLYCMSCGCS-BWOMAWGNSA-N [(3s,8r,9s,10r,13s)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,16-decahydrocyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(=O)CC=C3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 LUTSRLYCMSCGCS-BWOMAWGNSA-N 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
210000000601 blood cell Anatomy 0.000 description 5
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000005119 centrifugation Methods 0.000 description 5
238000011097 chromatography purification Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000012091 fetal bovine serum Substances 0.000 description 5
239000002609 medium Substances 0.000 description 5
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
239000003607 modifier Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
230000001225 therapeutic effect Effects 0.000 description 5
239000003643 water by type Substances 0.000 description 5
JWPNEOAPCXBCDC-UHFFFAOYSA-N 1-[(3-amino-2-chloroquinolin-4-yl)amino]-2-methylpropan-2-ol Chemical compound C1=CC=C2C(NCC(C)(O)C)=C(N)C(Cl)=NC2=C1 JWPNEOAPCXBCDC-UHFFFAOYSA-N 0.000 description 4
FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 4
SHZUGBYEPDMAPC-UHFFFAOYSA-N 4-hydroxy-3-nitro-1h-quinolin-2-one Chemical compound C1=CC=C2C(=O)C([N+]([O-])=O)=C(O)NC2=C1 SHZUGBYEPDMAPC-UHFFFAOYSA-N 0.000 description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
239000012591 Dulbecco’s Phosphate Buffered Saline Substances 0.000 description 4
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