TW202304921A - 製造雙環酮化合物之方法 - Google Patents

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Publication number

TW202304921A

TW202304921A TW111112842A TW111112842A TW202304921A TW 202304921 A TW202304921 A TW 202304921A TW 111112842 A TW111112842 A TW 111112842A TW 111112842 A TW111112842 A TW 111112842A TW 202304921 A TW202304921 A TW 202304921A

Authority

TW

Taiwan

Prior art keywords

compound

formula

stereoisomer

chiral

salt

Prior art date

2021-04-02

Links

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• -1 bicyclic ketone compounds Chemical class 0.000 title claims abstract description 277
• 238000000034 method Methods 0.000 title claims abstract description 187
• 230000008569 process Effects 0.000 title abstract description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 197
• 150000003839 salts Chemical class 0.000 claims abstract description 129
• 238000002360 preparation method Methods 0.000 claims abstract description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 137
• 239000002253 acid Substances 0.000 claims description 95
• 239000000203 mixture Substances 0.000 claims description 71
• 239000000654 additive Substances 0.000 claims description 60
• 238000006243 chemical reaction Methods 0.000 claims description 50
• 230000000996 additive effect Effects 0.000 claims description 49
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
• 101001110310 Lentilactobacillus kefiri NADP-dependent (R)-specific alcohol dehydrogenase Proteins 0.000 claims description 46
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
• 239000002904 solvent Substances 0.000 claims description 38
• 239000003960 organic solvent Substances 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
• 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 22
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 20
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 20
• 239000000543 intermediate Substances 0.000 claims description 20
• 239000005515 coenzyme Substances 0.000 claims description 18
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 235000019253 formic acid Nutrition 0.000 claims description 11
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 10
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 10
• 230000002140 halogenating effect Effects 0.000 claims description 10
• 150000003333 secondary alcohols Chemical class 0.000 claims description 10
• 125000006242 amine protecting group Chemical group 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 150000007530 organic bases Chemical class 0.000 claims description 9
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 9
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
• 108010050375 Glucose 1-Dehydrogenase Proteins 0.000 claims description 8
• 230000001476 alcoholic effect Effects 0.000 claims description 8
• 150000007524 organic acids Chemical class 0.000 claims description 8
• LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 claims description 7
• 230000000707 stereoselective effect Effects 0.000 claims description 7
• 239000002841 Lewis acid Substances 0.000 claims description 6
• 102100021669 Stromal cell-derived factor 1 Human genes 0.000 claims description 6
• 101710088580 Stromal cell-derived factor 1 Proteins 0.000 claims description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
• 150000007517 lewis acids Chemical class 0.000 claims description 6
• FCFXLXGZHDHJLB-UHFFFAOYSA-N pyridine-2-sulfonyl fluoride Chemical compound FS(=O)(=O)C1=CC=CC=N1 FCFXLXGZHDHJLB-UHFFFAOYSA-N 0.000 claims description 6
• QCICYPQPGJJZGW-UHFFFAOYSA-N 2-hydroxypropanehydrazide Chemical compound CC(O)C(=O)NN QCICYPQPGJJZGW-UHFFFAOYSA-N 0.000 claims description 5
• 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 5
• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 239000007822 coupling agent Substances 0.000 claims description 5
• 239000013078 crystal Substances 0.000 claims description 5
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical group F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
• 239000005456 alcohol based solvent Substances 0.000 claims description 3
• 150000001491 aromatic compounds Chemical class 0.000 claims description 3
• BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical group NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 claims description 2
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 2
• XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 claims 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical group Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
• 239000000243 solution Substances 0.000 description 62
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
• 238000005481 NMR spectroscopy Methods 0.000 description 29
• 239000003153 chemical reaction reagent Substances 0.000 description 29
• 125000004122 cyclic group Chemical group 0.000 description 29
• 239000000706 filtrate Substances 0.000 description 28
• 239000012065 filter cake Substances 0.000 description 27
• 239000007787 solid Substances 0.000 description 27
• 230000015572 biosynthetic process Effects 0.000 description 24
• 238000004128 high performance liquid chromatography Methods 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• 239000000460 chlorine Substances 0.000 description 23
• 239000011521 glass Substances 0.000 description 23
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
• 102000004190 Enzymes Human genes 0.000 description 18
• 108090000790 Enzymes Proteins 0.000 description 18
• 239000002585 base Substances 0.000 description 18
• HEWAMPODKFTBJZ-LLVKDONJSA-N ethyl (2r)-2-hydroxy-4-oxo-4-phenylbutanoate Chemical compound CCOC(=O)[C@H](O)CC(=O)C1=CC=CC=C1 HEWAMPODKFTBJZ-LLVKDONJSA-N 0.000 description 18
• 229910052757 nitrogen Inorganic materials 0.000 description 18
• 238000006722 reduction reaction Methods 0.000 description 18
• 102100022501 Receptor-interacting serine/threonine-protein kinase 1 Human genes 0.000 description 17
• 101710138589 Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 description 17
• 125000001072 heteroaryl group Chemical group 0.000 description 17
• 239000008346 aqueous phase Substances 0.000 description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
• 230000009467 reduction Effects 0.000 description 16
• 238000003786 synthesis reaction Methods 0.000 description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
• 239000012074 organic phase Substances 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 14
• 230000002829 reductive effect Effects 0.000 description 14
• XVZCIIVQCIBTGQ-DTWKUNHWSA-N NN([C@@H](C[C@H]1O)C2=CC=CC=C2)C1=O Chemical compound NN([C@@H](C[C@H]1O)C2=CC=CC=C2)C1=O XVZCIIVQCIBTGQ-DTWKUNHWSA-N 0.000 description 13
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
• 125000004429 atom Chemical group 0.000 description 13
• 201000010099 disease Diseases 0.000 description 13
• 229940002612 prodrug Drugs 0.000 description 13
• 239000000651 prodrug Substances 0.000 description 13
• 125000006239 protecting group Chemical group 0.000 description 13
• XJLXINKUBYWONI-NNYOXOHSSA-O NADP(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-O 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• ROLJNUSAWXADTD-UHFFFAOYSA-N ethyl 2-ethoxy-2-iminoacetate;hydrochloride Chemical compound Cl.CCOC(=N)C(=O)OCC ROLJNUSAWXADTD-UHFFFAOYSA-N 0.000 description 12
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 12
• 239000011734 sodium Substances 0.000 description 12
• DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 12
• 235000011054 acetic acid Nutrition 0.000 description 11
• 238000013019 agitation Methods 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
• 238000006073 displacement reaction Methods 0.000 description 10
• 150000002576 ketones Chemical class 0.000 description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
• 239000002002 slurry Substances 0.000 description 10
• JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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• 125000004430 oxygen atom Chemical group O* 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 239000011541 reaction mixture Substances 0.000 description 9
• 238000012546 transfer Methods 0.000 description 9
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
• 230000001580 bacterial effect Effects 0.000 description 8
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical group CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
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• 239000000758 substrate Substances 0.000 description 8
• 238000011282 treatment Methods 0.000 description 8
• LKNPNZKIOSOWES-UHFFFAOYSA-N triethyl 1,3,5-triazine-2,4,6-tricarboxylate Chemical compound CCOC(=O)C1=NC(C(=O)OCC)=NC(C(=O)OCC)=N1 LKNPNZKIOSOWES-UHFFFAOYSA-N 0.000 description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
• UARJMNREPJSYHA-LLVKDONJSA-N (2r)-2-acetyloxy-4-oxo-4-phenylbutanoic acid Chemical compound CC(=O)O[C@@H](C(O)=O)CC(=O)C1=CC=CC=C1 UARJMNREPJSYHA-LLVKDONJSA-N 0.000 description 7
• IWJCFZFZUVJTHQ-QWRGUYRKSA-N CON(C)C(=O)c1nc2[C@@H](F)C[C@@H](c3ccccc3)n2n1 Chemical group CON(C)C(=O)c1nc2[C@@H](F)C[C@@H](c3ccccc3)n2n1 IWJCFZFZUVJTHQ-QWRGUYRKSA-N 0.000 description 7
• LMXPZWQVDDSYHH-RYUDHWBXSA-N F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 Chemical group F[C@H]1C[C@H](N2N=C(N=C12)C(=O)C1CC1)C1=CC=CC=C1 LMXPZWQVDDSYHH-RYUDHWBXSA-N 0.000 description 7
• SSWJHSASZZAIAU-BYPYZUCNSA-N [(3s)-2,5-dioxooxolan-3-yl] acetate Chemical compound CC(=O)O[C@H]1CC(=O)OC1=O SSWJHSASZZAIAU-BYPYZUCNSA-N 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• MSMGXWFHBSCQFB-UHFFFAOYSA-N ethyl cyanoformate Chemical compound CCOC(=O)C#N MSMGXWFHBSCQFB-UHFFFAOYSA-N 0.000 description 7
• 125000005842 heteroatom Chemical group 0.000 description 7
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• 239000011780 sodium chloride Substances 0.000 description 7
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 125000000217 alkyl group Chemical group 0.000 description 6
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• 230000002255 enzymatic effect Effects 0.000 description 6
• UVJQQYMWMAISMQ-UHFFFAOYSA-N ethyl 2,4-dioxo-4-phenylbutanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CC=C1 UVJQQYMWMAISMQ-UHFFFAOYSA-N 0.000 description 6
• 125000000524 functional group Chemical group 0.000 description 6
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• 229940043355 kinase inhibitor Drugs 0.000 description 6
• SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 6
• 230000017074 necrotic cell death Effects 0.000 description 6
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• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
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• 239000000523 sample Substances 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000011593 sulfur Chemical group 0.000 description 6
• XYIXSPVKODNXKZ-IUCAKERBSA-N (5S,7S)-7-fluoro-5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole-2-carboxylic acid Chemical compound OC(=O)C1=NN2[C@@H](C[C@H](F)C2=N1)C1=CC=CC=C1 XYIXSPVKODNXKZ-IUCAKERBSA-N 0.000 description 5
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• 125000003545 alkoxy group Chemical group 0.000 description 5
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• MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical group CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
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• 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 4
• TXUWMXQFNYDOEZ-UHFFFAOYSA-N 5-(1H-indol-3-ylmethyl)-3-methyl-2-sulfanylidene-4-imidazolidinone Chemical compound O=C1N(C)C(=S)NC1CC1=CNC2=CC=CC=C12 TXUWMXQFNYDOEZ-UHFFFAOYSA-N 0.000 description 4
• 102000007698 Alcohol dehydrogenase Human genes 0.000 description 4
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