UA120764C2 - Конденсовані пентациклічні похідні імідазолу - Google Patents

Info

Publication number

UA120764C2

UA120764C2 UAA201702002A UAA201702002A UA120764C2 UA 120764 C2 UA120764 C2 UA 120764C2 UA A201702002 A UAA201702002 A UA A201702002A UA A201702002 A UAA201702002 A UA A201702002A UA 120764 C2 UA120764 C2 UA 120764C2

Authority

UA

Ukraine

Prior art keywords

alkyl

formula

difluoromethoxy

hydrogen

hydroxy

Prior art date

2014-10-03

Links

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• Global Dossier
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• 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 208000035475 disorder Diseases 0.000 claims abstract description 19
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 17
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 13
• 230000002265 prevention Effects 0.000 claims abstract description 13
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 12
• 208000030159 metabolic disease Diseases 0.000 claims abstract description 12
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 12
• 208000029257 vision disease Diseases 0.000 claims abstract description 12
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 11
• 208000002193 Pain Diseases 0.000 claims abstract description 11
• 230000000926 neurological effect Effects 0.000 claims abstract description 11
• 230000003040 nociceptive effect Effects 0.000 claims abstract description 11
• 201000011510 cancer Diseases 0.000 claims abstract description 10
• -1 (C3-7)ucycloalkyl Chemical group 0.000 claims description 546
• 150000001875 compounds Chemical class 0.000 claims description 546
• 238000000034 method Methods 0.000 claims description 204
• 229910052739 hydrogen Inorganic materials 0.000 claims description 202
• 239000001257 hydrogen Substances 0.000 claims description 198
• 125000000217 alkyl group Chemical group 0.000 claims description 184
• 125000001424 substituent group Chemical group 0.000 claims description 104
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 101
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 95
• 229910052736 halogen Inorganic materials 0.000 claims description 95
• 150000002367 halogens Chemical class 0.000 claims description 89
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 78
• 125000001072 heteroaryl group Chemical group 0.000 claims description 70
• 150000003839 salts Chemical class 0.000 claims description 52
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 50
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 125000003282 alkyl amino group Chemical group 0.000 claims description 26
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 26
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 23
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 19
• 239000011737 fluorine Substances 0.000 claims description 19
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 18
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
• 229910019142 PO4 Inorganic materials 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 239000010452 phosphate Substances 0.000 claims description 16
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
• 125000004043 oxo group Chemical group O=* 0.000 claims description 11
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 10
• 150000001768 cations Chemical class 0.000 claims description 9
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 7
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 7
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
• 229910052790 beryllium Inorganic materials 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 5
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• 206010047571 Visual impairment Diseases 0.000 claims description 4
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 4
• 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
• 230000004393 visual impairment Effects 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
• 238000011161 development Methods 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 5
• 125000001475 halogen functional group Chemical group 0.000 claims 2
• 241001424341 Tara spinosa Species 0.000 claims 1
• 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 9
• 230000000694 effects Effects 0.000 abstract description 9
• 241000282414 Homo sapiens Species 0.000 abstract description 7
• 208000025966 Neurological disease Diseases 0.000 abstract description 5
• 150000002460 imidazoles Chemical class 0.000 abstract description 5
• 241000282412 Homo Species 0.000 abstract description 2
• 208000013521 Visual disease Diseases 0.000 abstract description 2
• 230000003389 potentiating effect Effects 0.000 abstract description 2
• RYFZCJDZUMKKFN-UHFFFAOYSA-N 2,9,12-triazapentacyclo[9.8.1.02,10.03,8.014,19]icosa-3,5,7,9,14,16,18-heptaen-13-one Chemical class C1=CC=CC=2C(NC3C=4N(C(C=21)C3)C1=C(N=4)C=CC=C1)=O RYFZCJDZUMKKFN-UHFFFAOYSA-N 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 description 378
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 151
• 239000011541 reaction mixture Substances 0.000 description 135
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 134
• 239000002904 solvent Substances 0.000 description 127
• 239000000203 mixture Substances 0.000 description 105
• 238000006243 chemical reaction Methods 0.000 description 100
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 93
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
• 239000007787 solid Substances 0.000 description 66
• 239000000243 solution Substances 0.000 description 65
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 61
• 235000019439 ethyl acetate Nutrition 0.000 description 60
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 56
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 52
• 238000005160 1H NMR spectroscopy Methods 0.000 description 48
• 239000002585 base Substances 0.000 description 47
• 239000012044 organic layer Substances 0.000 description 46
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 42
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
• 239000002253 acid Substances 0.000 description 33
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 32
• 239000012267 brine Substances 0.000 description 32
• 239000010410 layer Substances 0.000 description 32
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
• 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
• 238000004587 chromatography analysis Methods 0.000 description 28
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 27
• 229910052794 bromium Inorganic materials 0.000 description 27
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• 235000019253 formic acid Nutrition 0.000 description 26
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 26
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 25
• 239000003921 oil Substances 0.000 description 25
• 235000019198 oils Nutrition 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 23
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
• 239000000460 chlorine Substances 0.000 description 22
• 229910052801 chlorine Inorganic materials 0.000 description 22
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• 239000003480 eluent Substances 0.000 description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• 239000007864 aqueous solution Substances 0.000 description 20
• 238000004440 column chromatography Methods 0.000 description 20
• 229920006395 saturated elastomer Polymers 0.000 description 20
• 229910052938 sodium sulfate Inorganic materials 0.000 description 20
• 235000011152 sodium sulphate Nutrition 0.000 description 20
• 239000000725 suspension Substances 0.000 description 20
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 19
• 239000012043 crude product Substances 0.000 description 19
• 238000000746 purification Methods 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 239000003054 catalyst Substances 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
• 239000000706 filtrate Substances 0.000 description 17
• 229910000027 potassium carbonate Inorganic materials 0.000 description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• 125000000714 pyrimidinyl group Chemical group 0.000 description 16
• 229910052723 transition metal Inorganic materials 0.000 description 16
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
• 239000013058 crude material Substances 0.000 description 15
• 239000012071 phase Substances 0.000 description 15
• 235000011181 potassium carbonates Nutrition 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• 150000003624 transition metals Chemical class 0.000 description 15
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 238000002347 injection Methods 0.000 description 14
• 239000007924 injection Substances 0.000 description 14
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 14
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
• 229910052770 Uranium Inorganic materials 0.000 description 13
• 238000010828 elution Methods 0.000 description 13
• 239000012634 fragment Substances 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• 238000004458 analytical method Methods 0.000 description 12
• 229910052799 carbon Inorganic materials 0.000 description 12
• 229910052740 iodine Inorganic materials 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 12
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• 239000000741 silica gel Substances 0.000 description 11
• 229910002027 silica gel Inorganic materials 0.000 description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 10
• 229910000024 caesium carbonate Inorganic materials 0.000 description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
• 238000001514 detection method Methods 0.000 description 10
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 230000002829 reductive effect Effects 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• 239000012298 atmosphere Substances 0.000 description 9
• 125000005843 halogen group Chemical group 0.000 description 9
• 229910052763 palladium Inorganic materials 0.000 description 9
• 239000012312 sodium hydride Substances 0.000 description 9
• 229910000104 sodium hydride Inorganic materials 0.000 description 9
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 229910052700 potassium Inorganic materials 0.000 description 8
• 238000000926 separation method Methods 0.000 description 8
• 239000000377 silicon dioxide Substances 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• 125000003107 substituted aryl group Chemical group 0.000 description 8
• 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 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 7
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 7
• 229910021529 ammonia Inorganic materials 0.000 description 7
• 239000008346 aqueous phase Substances 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 150000002148 esters Chemical group 0.000 description 7
• 238000003818 flash chromatography Methods 0.000 description 7
• 230000006870 function Effects 0.000 description 7
• 239000011521 glass Substances 0.000 description 7
• 239000012299 nitrogen atmosphere Substances 0.000 description 7
• 125000004076 pyridyl group Chemical group 0.000 description 7
• 230000009467 reduction Effects 0.000 description 7
• 239000011347 resin Substances 0.000 description 7
• 229920005989 resin Polymers 0.000 description 7
• 229910000029 sodium carbonate Inorganic materials 0.000 description 7
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 238000011247 total mesorectal excision Methods 0.000 description 7
• 208000037956 transmissible mink encephalopathy Diseases 0.000 description 7
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 7
• 229910052725 zinc Inorganic materials 0.000 description 7
• 239000011701 zinc Substances 0.000 description 7
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 229910052783 alkali metal Inorganic materials 0.000 description 6
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
• 230000001363 autoimmune Effects 0.000 description 6
• 239000003638 chemical reducing agent Substances 0.000 description 6
• 238000005516 engineering process Methods 0.000 description 6
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