CA2634017A1 - Imidazoquinoleines, imidazonaphtyridines et imidazopyridines substituees, compositions et procedes correspondants - Google Patents

Info

Publication number

CA2634017A1

CA2634017A1 CA002634017A CA2634017A CA2634017A1 CA 2634017 A1 CA2634017 A1 CA 2634017A1 CA 002634017 A CA002634017 A CA 002634017A CA 2634017 A CA2634017 A CA 2634017A CA 2634017 A1 CA2634017 A1 CA 2634017A1

Authority

CA

Canada

Prior art keywords

group

alkyl

pyran

tetrahydo

pharmaceutical composition

Prior art date

2005-12-16

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 57
• 239000000203 mixture Chemical class 0.000 title description 123
• 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 title description 2
• 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 description 2
• 150000005232 imidazopyridines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 264
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 83
• 102000004127 Cytokines Human genes 0.000 claims abstract description 43
• 108090000695 Cytokines Proteins 0.000 claims abstract description 43
• 241001465754 Metazoa Species 0.000 claims abstract description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
• 201000010099 disease Diseases 0.000 claims abstract description 28
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 17
• 230000003612 virological effect Effects 0.000 claims abstract description 13
• 230000001613 neoplastic effect Effects 0.000 claims abstract description 11
• 230000001939 inductive effect Effects 0.000 claims abstract description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 223
• 150000003839 salts Chemical class 0.000 claims description 120
• -1 tetrahydrofuran-3-yl Chemical group 0.000 claims description 94
• 229910052739 hydrogen Inorganic materials 0.000 claims description 76
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 239000001257 hydrogen Substances 0.000 claims description 75
• 125000003118 aryl group Chemical group 0.000 claims description 56
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 125000002947 alkylene group Chemical group 0.000 claims description 48
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 47
• 125000001072 heteroaryl group Chemical group 0.000 claims description 47
• 125000003545 alkoxy group Chemical group 0.000 claims description 37
• 125000005466 alkylenyl group Chemical group 0.000 claims description 36
• 150000002367 halogens Chemical group 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• 125000004450 alkenylene group Chemical group 0.000 claims description 26
• 125000000732 arylene group Chemical group 0.000 claims description 25
• 239000003937 drug carrier Substances 0.000 claims description 25
• 125000001188 haloalkyl group Chemical group 0.000 claims description 25
• 125000005549 heteroarylene group Chemical group 0.000 claims description 24
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
• 125000004419 alkynylene group Chemical group 0.000 claims description 22
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 21
• 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 17
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000003282 alkyl amino group Chemical group 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 13
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 10
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 9
• 125000005532 aryl alkyleneoxy group Chemical group 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 9
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 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 claims description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 2
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 10
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
• 230000001419 dependent effect Effects 0.000 claims 3
• 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 abstract description 13
• 238000011282 treatment Methods 0.000 abstract description 11
• 150000005239 1H-imidazo[4,5-c]pyridines Chemical group 0.000 abstract description 2
• FGGPIDNXZDDRSG-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c][1,5]naphthyridine Chemical group C1CCNC2=C1N=CC1=C2N=CN1 FGGPIDNXZDDRSG-UHFFFAOYSA-N 0.000 abstract description 2
• 239000002955 immunomodulating agent Substances 0.000 abstract description 2
• 229940121354 immunomodulator Drugs 0.000 abstract description 2
• CZTQJCYFLGFVLG-UHFFFAOYSA-N 6,7,8,9-tetrahydro-3h-imidazo[4,5-c]quinoline Chemical class C1CCCC2=C1N=CC1=C2NC=N1 CZTQJCYFLGFVLG-UHFFFAOYSA-N 0.000 abstract 1
• 150000005054 naphthyridines Chemical class 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 199
• 238000006243 chemical reaction Methods 0.000 description 176
• 239000007787 solid Substances 0.000 description 176
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 158
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 152
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 144
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 122
• 230000002829 reductive effect Effects 0.000 description 109
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 107
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 105
• 239000000243 solution Substances 0.000 description 102
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 97
• 239000011541 reaction mixture Substances 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
• 229910001868 water Inorganic materials 0.000 description 74
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 239000000741 silica gel Substances 0.000 description 62
• 229910002027 silica gel Inorganic materials 0.000 description 62
• 238000001914 filtration Methods 0.000 description 59
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 58
• 239000003921 oil Substances 0.000 description 57
• 235000019198 oils Nutrition 0.000 description 57
• 238000002953 preparative HPLC Methods 0.000 description 57
• 239000000463 material Substances 0.000 description 54
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
• 229910052757 nitrogen Inorganic materials 0.000 description 44
• 238000005481 NMR spectroscopy Methods 0.000 description 43
• 239000012043 crude product Substances 0.000 description 41
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 40
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 39
• 238000007429 general method Methods 0.000 description 39
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
• 239000002253 acid Substances 0.000 description 37
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 37
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
• 239000002904 solvent Substances 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• 239000010410 layer Substances 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
• 239000000706 filtrate Substances 0.000 description 29
• 238000010992 reflux Methods 0.000 description 27
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
• 239000003153 chemical reaction reagent Substances 0.000 description 26
• 239000012299 nitrogen atmosphere Substances 0.000 description 25
• 238000012360 testing method Methods 0.000 description 23
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 21
• 238000004458 analytical method Methods 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
• 238000002474 experimental method Methods 0.000 description 19
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• 229910000029 sodium carbonate Inorganic materials 0.000 description 18
• ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 2-ethoxyacetyl chloride Chemical compound CCOCC(Cl)=O ZPMWWAIBJJFPPQ-UHFFFAOYSA-N 0.000 description 17
• JSMDUOFOPDSKIQ-UHFFFAOYSA-N 3-methoxypropanoyl chloride Chemical compound COCCC(Cl)=O JSMDUOFOPDSKIQ-UHFFFAOYSA-N 0.000 description 17
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 17
• 239000013078 crystal Substances 0.000 description 17
• 125000005843 halogen group Chemical group 0.000 description 17
• 239000000047 product Substances 0.000 description 17
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• IDUUCDZKSKUCOP-UHFFFAOYSA-N 3h-imidazo[4,5-c][1,5]naphthyridine Chemical compound C1=CC=NC2=C(NC=N3)C3=CN=C21 IDUUCDZKSKUCOP-UHFFFAOYSA-N 0.000 description 15
• 238000009835 boiling Methods 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 238000010189 synthetic method Methods 0.000 description 15
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
• 102100040247 Tumor necrosis factor Human genes 0.000 description 14
• 150000001408 amides Chemical class 0.000 description 14
• 229910052938 sodium sulfate Inorganic materials 0.000 description 14
• 235000011152 sodium sulphate Nutrition 0.000 description 14
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• 210000004027 cell Anatomy 0.000 description 12
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 12
• UTOMICFLROGMAE-UHFFFAOYSA-N quinoline-3,4-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CN=C21 UTOMICFLROGMAE-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 238000001953 recrystallisation Methods 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• MIDQVYLLSDOPIL-UHFFFAOYSA-N 1,5-naphthyridine-3,4-diamine Chemical compound C1=CC=NC2=C(N)C(N)=CN=C21 MIDQVYLLSDOPIL-UHFFFAOYSA-N 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000003814 drug Substances 0.000 description 10
• 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 10
• 239000005457 ice water Substances 0.000 description 10
• 230000006698 induction Effects 0.000 description 10
• 238000004519 manufacturing process Methods 0.000 description 10
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
• 125000004122 cyclic group Chemical group 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 239000012065 filter cake Substances 0.000 description 9
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
• 235000019341 magnesium sulphate Nutrition 0.000 description 9
• 239000010502 orange oil Substances 0.000 description 9
• 238000002360 preparation method Methods 0.000 description 9
• 239000000651 prodrug Substances 0.000 description 9
• 229940002612 prodrug Drugs 0.000 description 9
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 9
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• GIROJVFYHQUUFX-UHFFFAOYSA-N 8-bromo-2-(2-methoxyethyl)-1-(oxan-4-ylmethyl)imidazo[4,5-c]quinoline Chemical compound COCCC1=NC2=CN=C3C=CC(Br)=CC3=C2N1CC1CCOCC1 GIROJVFYHQUUFX-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
• 210000004369 blood Anatomy 0.000 description 8
• 239000008280 blood Substances 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
• 230000028993 immune response Effects 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
• YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 8
• 230000009467 reduction Effects 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
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