UA123668C2 - Конденсовані біциклічні гетероарильні похідні з активністю інгібіторів пролілгідроксилази - Google Patents

Info

Publication number

UA123668C2

UA123668C2 UAA201708877A UAA201708877A UA123668C2 UA 123668 C2 UA123668 C2 UA 123668C2 UA A201708877 A UAA201708877 A UA A201708877A UA A201708877 A UAA201708877 A UA A201708877A UA 123668 C2 UA123668 C2 UA 123668C2

Authority

UA

Ukraine

Prior art keywords

pyridin

griazolo

benzonitrile

cyano

ipyridin

Prior art date

2015-03-18

Links

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• Global Dossier
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• 230000000694 effects Effects 0.000 title description 8
• 229940078467 Prolyl hydroxylase inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 224
• 150000003839 salts Chemical class 0.000 claims abstract description 39
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 8
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 917
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 189
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 156
• 125000001424 substituent group Chemical group 0.000 claims description 114
• -1 ME ?B"E Chemical group 0.000 claims description 106
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 94
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 88
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 84
• 125000000623 heterocyclic group Chemical group 0.000 claims description 83
• 229910052757 nitrogen Inorganic materials 0.000 claims description 83
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 82
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 66
• 229910052736 halogen Inorganic materials 0.000 claims description 56
• 150000002367 halogens Chemical class 0.000 claims description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 239000001257 hydrogen Substances 0.000 claims description 50
• 150000003857 carboxamides Chemical class 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
• 229910052731 fluorine Inorganic materials 0.000 claims description 38
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 37
• 125000004043 oxo group Chemical group O=* 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 239000011737 fluorine Substances 0.000 claims description 34
• 125000001072 heteroaryl group Chemical group 0.000 claims description 34
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 28
• 229910052801 chlorine Inorganic materials 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 239000000460 chlorine Substances 0.000 claims description 25
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
• 150000002431 hydrogen Chemical class 0.000 claims description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
• 229910052760 oxygen Chemical group 0.000 claims description 22
• 239000001301 oxygen Chemical group 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 19
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 239000000126 substance Substances 0.000 claims description 16
• 238000011282 treatment Methods 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
• AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 229940124530 sulfonamide Drugs 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 11
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 206010019280 Heart failures Diseases 0.000 claims description 10
• 208000010125 myocardial infarction Diseases 0.000 claims description 10
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
• 102000004079 Prolyl Hydroxylases Human genes 0.000 claims description 9
• 108010043005 Prolyl Hydroxylases Proteins 0.000 claims description 9
• 125000005475 oxolanyl group Chemical group 0.000 claims description 9
• 208000009304 Acute Kidney Injury Diseases 0.000 claims description 8
• 206010007556 Cardiac failure acute Diseases 0.000 claims description 8
• 208000033626 Renal failure acute Diseases 0.000 claims description 8
• 201000011040 acute kidney failure Diseases 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 125000003566 oxetanyl group Chemical group 0.000 claims description 8
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
• 208000012998 acute renal failure Diseases 0.000 claims description 7
• 208000020832 chronic kidney disease Diseases 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 7
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 239000003112 inhibitor Substances 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 5
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 5
• GDHXJNRAJRCGMX-UHFFFAOYSA-N 2-fluorobenzonitrile Chemical compound FC1=CC=CC=C1C#N GDHXJNRAJRCGMX-UHFFFAOYSA-N 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• DJDBLBBSUAQYAA-UHFFFAOYSA-N piperazine-1-carbonitrile Chemical compound N#CN1CCNCC1 DJDBLBBSUAQYAA-UHFFFAOYSA-N 0.000 claims description 4
• IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims description 3
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 3
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• VQKCYXWRTWMTBP-UHFFFAOYSA-N 2-pyridin-3-ylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1=CC=CN=C1 VQKCYXWRTWMTBP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
• GXHAENUAJYZNOA-UHFFFAOYSA-N oxolane-2-carboxamide Chemical compound NC(=O)C1CCCO1 GXHAENUAJYZNOA-UHFFFAOYSA-N 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 49
• 238000002360 preparation method Methods 0.000 abstract description 10
• 230000008569 process Effects 0.000 abstract description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 347
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 195
• 238000006243 chemical reaction Methods 0.000 description 188
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 170
• 239000012071 phase Substances 0.000 description 130
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 125
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 120
• 239000000243 solution Substances 0.000 description 115
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 92
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 76
• 239000000047 product Substances 0.000 description 69
• 239000011541 reaction mixture Substances 0.000 description 67
• 235000019439 ethyl acetate Nutrition 0.000 description 62
• 238000003818 flash chromatography Methods 0.000 description 60
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 59
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 55
• 239000003208 petroleum Substances 0.000 description 54
• 150000002825 nitriles Chemical class 0.000 description 53
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 52
• 238000002953 preparative HPLC Methods 0.000 description 51
• 239000000725 suspension Substances 0.000 description 49
• 239000000203 mixture Substances 0.000 description 48
• 229910021529 ammonia Inorganic materials 0.000 description 46
• 239000000741 silica gel Substances 0.000 description 44
• 229910002027 silica gel Inorganic materials 0.000 description 44
• 239000012074 organic phase Substances 0.000 description 42
• 239000002253 acid Substances 0.000 description 41
• 239000012043 crude product Substances 0.000 description 36
• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 33
• 235000002639 sodium chloride Nutrition 0.000 description 33
• 230000015572 biosynthetic process Effects 0.000 description 31
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 28
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 28
• 239000003708 ampul Substances 0.000 description 23
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
• 239000007858 starting material Substances 0.000 description 21
• CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 19
• 239000012267 brine Substances 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• 239000003153 chemical reaction reagent Substances 0.000 description 17
• 208000035475 disorder Diseases 0.000 description 17
• 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 16
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• 235000019253 formic acid Nutrition 0.000 description 16
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
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• 206010021143 Hypoxia Diseases 0.000 description 15
• 238000004128 high performance liquid chromatography Methods 0.000 description 15
• 239000013067 intermediate product Substances 0.000 description 15
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
• 150000001412 amines Chemical class 0.000 description 14
• 229910052799 carbon Inorganic materials 0.000 description 14
• 239000005416 organic matter Substances 0.000 description 14
• 208000008589 Obesity Diseases 0.000 description 13
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 13
• 235000020824 obesity Nutrition 0.000 description 13
• 238000000746 purification Methods 0.000 description 13
• 239000002904 solvent Substances 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• 108010000684 Matrix Metalloproteinases Proteins 0.000 description 12
• 206010028980 Neoplasm Diseases 0.000 description 12
• 239000000706 filtrate Substances 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 11
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 11
• 239000008346 aqueous phase Substances 0.000 description 11
• 201000010099 disease Diseases 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 11
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
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• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 229920003189 Nylon 4,6 Polymers 0.000 description 9
• 239000012299 nitrogen atmosphere Substances 0.000 description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 9
• HFAUMAIVCYTVQR-UHFFFAOYSA-N (4-cyano-2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1F HFAUMAIVCYTVQR-UHFFFAOYSA-N 0.000 description 8
• AVBKISZUVMWQIA-UHFFFAOYSA-N 4-bromo-2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC(C#N)=C(F)C=C1Br AVBKISZUVMWQIA-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 229910052786 argon Inorganic materials 0.000 description 8
• 125000002393 azetidinyl group Chemical group 0.000 description 8
• 239000004305 biphenyl Substances 0.000 description 8
• 206010012601 diabetes mellitus Diseases 0.000 description 8
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• 230000007954 hypoxia Effects 0.000 description 8
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• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
• 230000003595 spectral effect Effects 0.000 description 8
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 7
• 101100237844 Mus musculus Mmp19 gene Proteins 0.000 description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
• 150000001502 aryl halides Chemical class 0.000 description 7
• IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 7
• XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 7
• 229910052717 sulfur Chemical group 0.000 description 7
• 239000011593 sulfur Chemical group 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
• DECWLXUOZUMPBF-UHFFFAOYSA-N (4-cyano-3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C(F)=C1 DECWLXUOZUMPBF-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
• 229910021595 Copper(I) iodide Inorganic materials 0.000 description 6
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
• 235000010290 biphenyl Nutrition 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
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• 230000001684 chronic effect Effects 0.000 description 6
• LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 6
• 230000006378 damage Effects 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 125000002950 monocyclic group Chemical group 0.000 description 6
• 125000003386 piperidinyl group Chemical group 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 208000024891 symptom Diseases 0.000 description 6
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• 208000029523 Interstitial Lung disease Diseases 0.000 description 5
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• 208000011775 arteriosclerosis disease Diseases 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 201000011510 cancer Diseases 0.000 description 5
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• 238000009833 condensation Methods 0.000 description 5
• 230000005494 condensation Effects 0.000 description 5
• WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 description 5
• 239000012634 fragment Substances 0.000 description 5
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• 238000004172 nitrogen cycle Methods 0.000 description 5
• 239000002798 polar solvent Substances 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
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