UA125644C2 - ЗАМІЩЕНІ 5,6,7,8-ТЕТРАГІДРО[1,2,4]ТРИАЗОЛО[4,3-а]ПІРИДИН-3(2Н)-ОНИ ТА 2,5,6,7-ТЕТРАГІДРО-3Н-ПІРОЛО[2,1-с][1,2,4]ТРИАЗОЛ-3-ОНИ ТА ЇХ ЗАСТОСУВАННЯ - Google Patents

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Publication number

UA125644C2

UA125644C2 UAA201811797A UAA201811797A UA125644C2 UA 125644 C2 UA125644 C2 UA 125644C2 UA A201811797 A UAA201811797 A UA A201811797A UA A201811797 A UAA201811797 A UA A201811797A UA 125644 C2 UA125644 C2 UA 125644C2

Authority

UA

Ukraine

Prior art keywords

fluorine

substituted

methyl

hydrogen

unsubstituted

Prior art date

2016-05-09

Links

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• Global Dossier
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• VNJXPEWQUVGHKM-UHFFFAOYSA-N 5,6,7,8-tetrahydro-2h-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical class C1CCCN2C(=O)NN=C21 VNJXPEWQUVGHKM-UHFFFAOYSA-N 0.000 title abstract 2
• 238000000034 method Methods 0.000 claims abstract description 86
• 238000011282 treatment Methods 0.000 claims abstract description 49
• 230000002265 prevention Effects 0.000 claims abstract description 26
• 230000002757 inflammatory effect Effects 0.000 claims abstract description 23
• 238000002360 preparation method Methods 0.000 claims abstract description 19
• 208000019693 Lung disease Diseases 0.000 claims abstract description 12
• 238000004519 manufacturing process Methods 0.000 claims abstract description 6
• 150000001875 compounds Chemical class 0.000 claims description 283
• -1 5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl ring Chemical group 0.000 claims description 253
• 239000011737 fluorine Substances 0.000 claims description 217
• 229910052731 fluorine Inorganic materials 0.000 claims description 217
• 229910052739 hydrogen Inorganic materials 0.000 claims description 208
• 239000001257 hydrogen Substances 0.000 claims description 208
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 151
• 150000002431 hydrogen Chemical class 0.000 claims description 143
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 143
• 229910052799 carbon Inorganic materials 0.000 claims description 100
• 150000003839 salts Chemical class 0.000 claims description 92
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 91
• 125000001153 fluoro group Chemical group F* 0.000 claims description 78
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 73
• 125000004432 carbon atom Chemical group C* 0.000 claims description 71
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 64
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 62
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 58
• 239000002904 solvent Substances 0.000 claims description 57
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 49
• 239000000460 chlorine Chemical group 0.000 claims description 44
• 229910052801 chlorine Inorganic materials 0.000 claims description 44
• 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 44
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims description 39
• 239000003112 inhibitor Substances 0.000 claims description 39
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 38
• 230000009466 transformation Effects 0.000 claims description 38
• 125000004076 pyridyl group Chemical group 0.000 claims description 35
• 239000012442 inert solvent Substances 0.000 claims description 34
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 26
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 23
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 239000011593 sulfur Substances 0.000 claims description 21
• 208000011580 syndromic disease Diseases 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 17
• 239000005557 antagonist Substances 0.000 claims description 16
• 208000006673 asthma Diseases 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical group 0.000 claims description 16
• VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 15
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
• 125000002883 imidazolyl group Chemical group 0.000 claims description 14
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 14
• 125000002971 oxazolyl group Chemical group 0.000 claims description 14
• 125000000335 thiazolyl group Chemical group 0.000 claims description 14
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 201000009267 bronchiectasis Diseases 0.000 claims description 13
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 13
• 229910052763 palladium Inorganic materials 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
• 206010006451 bronchitis Diseases 0.000 claims description 12
• 229940126601 medicinal product Drugs 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 150000007513 acids Chemical class 0.000 claims description 11
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 11
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 11
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 11
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 10
• 239000013543 active substance Substances 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• 208000007451 chronic bronchitis Diseases 0.000 claims description 10
• 208000027866 inflammatory disease Diseases 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
• 206010014561 Emphysema Diseases 0.000 claims description 9
• 208000009525 Myocarditis Diseases 0.000 claims description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 210000001508 eye Anatomy 0.000 claims description 9
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 9
• 230000009798 acute exacerbation Effects 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 7
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
• 206010029888 Obliterative bronchiolitis Diseases 0.000 claims description 7
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
• 201000003848 bronchiolitis obliterans Diseases 0.000 claims description 7
• 208000023367 bronchiolitis obliterans with obstructive pulmonary disease Diseases 0.000 claims description 7
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
• 229910052700 potassium Inorganic materials 0.000 claims description 7
• SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 claims description 6
• 201000004624 Dermatitis Diseases 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• 229910052790 beryllium Inorganic materials 0.000 claims description 6
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 6
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 6
• 210000001835 viscera Anatomy 0.000 claims description 6
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
• 230000008878 coupling Effects 0.000 claims description 5
• 238000010168 coupling process Methods 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• 231100000252 nontoxic Toxicity 0.000 claims description 5
• 230000003000 nontoxic effect Effects 0.000 claims description 5
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• 208000030533 eye disease Diseases 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• 230000019491 signal transduction Effects 0.000 claims description 4
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 3
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 239000012190 activator Substances 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
• 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims description 3
• 229960003073 pirfenidone Drugs 0.000 claims description 3
• ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims description 3
• 150000003815 prostacyclins Chemical class 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 102000002045 Endothelin Human genes 0.000 claims description 2
• 108050009340 Endothelin Proteins 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims description 2
• 125000004185 ester group Chemical group 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
• 229940044601 receptor agonist Drugs 0.000 claims description 2
• 239000000018 receptor agonist Substances 0.000 claims description 2
• 229910052720 vanadium Inorganic materials 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 24
• 229940122210 Prolyl endopeptidase inhibitor Drugs 0.000 claims 3
• ORZXYSPOAVJYRU-UHFFFAOYSA-N benzyl 2-(2-formylpyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate Chemical compound O=CC1CCCN1C(=O)C1N(C(=O)OCC=2C=CC=CC=2)CCC1 ORZXYSPOAVJYRU-UHFFFAOYSA-N 0.000 claims 3
• 239000003649 prolyl endopeptidase inhibitor Substances 0.000 claims 3
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 3
• AJZAPEZJWWQJHC-UWNKZCSISA-N (2r,3r,4r,5r)-3,4-dihydroxy-n,n'-bis[(2s)-3-methyl-1-(methylamino)-1-oxobutan-2-yl]-2,5-bis[(4-thiophen-3-ylphenyl)methoxy]hexanediamide Chemical compound O([C@@H](C(=O)N[C@H](C(=O)NC)C(C)C)[C@H](O)[C@@H](O)[C@@H](OCC=1C=CC(=CC=1)C1=CSC=C1)C(=O)N[C@@H](C(C)C)C(=O)NC)CC(C=C1)=CC=C1C=1C=CSC=1 AJZAPEZJWWQJHC-UWNKZCSISA-N 0.000 claims 2
• DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 claims 2
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• 239000011022 opal Substances 0.000 claims 1
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• 230000006806 disease prevention Effects 0.000 abstract description 14
• 239000003814 drug Substances 0.000 abstract description 7
• 229940079593 drug Drugs 0.000 abstract description 6
• WTMDBOJIFXBWBL-UHFFFAOYSA-N 2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-3-one Chemical class C1CCN2C(=O)NN=C21 WTMDBOJIFXBWBL-UHFFFAOYSA-N 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
• 239000012453 solvate Substances 0.000 description 71
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 150000001721 carbon Chemical group 0.000 description 61
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 55
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
• 201000010099 disease Diseases 0.000 description 45
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
• 239000003480 eluent Substances 0.000 description 42
• AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 34
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 239000000203 mixture Substances 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• 229910052805 deuterium Inorganic materials 0.000 description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 25
• 239000002585 base Substances 0.000 description 25
• 238000006243 chemical reaction Methods 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 22
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 18
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• 239000013067 intermediate product Substances 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 18
• 230000015572 biosynthetic process Effects 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
• 235000019253 formic acid Nutrition 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 15
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• 235000019439 ethyl acetate Nutrition 0.000 description 15
• 210000004072 lung Anatomy 0.000 description 15
• 239000000243 solution Substances 0.000 description 15
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
• 239000011575 calcium Substances 0.000 description 14
• 230000000694 effects Effects 0.000 description 14
• 235000015424 sodium Nutrition 0.000 description 14
• 238000005160 1H NMR spectroscopy Methods 0.000 description 13
• 230000006378 damage Effects 0.000 description 13
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