RU2741496C2 - Гетероциклические соединения и их применение в лечении или предотвращении бактериальных инфекций - Google Patents

Info

Publication number

RU2741496C2

RU2741496C2 RU2017135321A RU2017135321A RU2741496C2 RU 2741496 C2 RU2741496 C2 RU 2741496C2 RU 2017135321 A RU2017135321 A RU 2017135321A RU 2017135321 A RU2017135321 A RU 2017135321A RU 2741496 C2 RU2741496 C2 RU 2741496C2

Authority

RU

Russia

Prior art keywords

mmol

oxo

oct

diazabicyclo

alkyl

Prior art date

2015-05-07

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• 208000035143 Bacterial infection Diseases 0.000 title claims abstract description 32
• 208000022362 bacterial infectious disease Diseases 0.000 title claims abstract description 32
• 150000002391 heterocyclic compounds Chemical class 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 189
• 239000000203 mixture Substances 0.000 claims abstract description 105
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 90
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 74
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 71
• 241000894006 Bacteria Species 0.000 claims abstract description 59
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 58
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 49
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 48
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 44
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 125000003118 aryl group Chemical group 0.000 claims abstract description 19
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 19
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 14
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
• 239000003814 drug Substances 0.000 claims abstract description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
• 125000001424 substituent group Chemical group 0.000 claims description 67
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 28
• 239000003242 anti bacterial agent Substances 0.000 claims description 26
• 102000006635 beta-lactamase Human genes 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 229960000484 ceftazidime Drugs 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 10
• 239000003781 beta lactamase inhibitor Substances 0.000 claims description 6
• 229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000006239 protecting group Chemical group 0.000 claims description 3
• 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 3
• 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 108020004256 Beta-lactamase Proteins 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 2
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 claims 2
• 230000000694 effects Effects 0.000 abstract description 5
• 239000000126 substance Substances 0.000 abstract description 5
• 229910006069 SO3H Inorganic materials 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 289
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 276
• 239000000543 intermediate Substances 0.000 description 229
• 238000002360 preparation method Methods 0.000 description 200
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 156
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 133
• 238000005481 NMR spectroscopy Methods 0.000 description 126
• 238000000034 method Methods 0.000 description 125
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 123
• 239000000243 solution Substances 0.000 description 120
• 239000000741 silica gel Substances 0.000 description 114
• 229910002027 silica gel Inorganic materials 0.000 description 114
• 238000003818 flash chromatography Methods 0.000 description 98
• 239000011541 reaction mixture Substances 0.000 description 94
• 239000007787 solid Substances 0.000 description 92
• -1 beta-lactam compounds Chemical class 0.000 description 84
• 238000000746 purification Methods 0.000 description 84
• 239000011734 sodium Substances 0.000 description 84
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
• KYVUXHPBYKHSFQ-UHFFFAOYSA-N [3-[5-(aminomethyl)-1,3-thiazol-2-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] hydrogen sulfate Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1SC(=CN=1)CN)O KYVUXHPBYKHSFQ-UHFFFAOYSA-N 0.000 description 82
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
• 235000019439 ethyl acetate Nutrition 0.000 description 63
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 60
• 230000015572 biosynthetic process Effects 0.000 description 53
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 52
• 230000002829 reductive effect Effects 0.000 description 51
• 238000003786 synthesis reaction Methods 0.000 description 51
• 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 50
• GTDZRCHHWHXSRA-UHFFFAOYSA-N triphenyl(prop-1-enyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=CC)C1=CC=CC=C1 GTDZRCHHWHXSRA-UHFFFAOYSA-N 0.000 description 50
• 229910052708 sodium Inorganic materials 0.000 description 44
• 238000004108 freeze drying Methods 0.000 description 40
• 239000012043 crude product Substances 0.000 description 37
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
• 238000004255 ion exchange chromatography Methods 0.000 description 34
• 239000012044 organic layer Substances 0.000 description 32
• 229910052786 argon Inorganic materials 0.000 description 30
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• 239000000725 suspension Substances 0.000 description 26
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 239000012298 atmosphere Substances 0.000 description 25
• 238000004587 chromatography analysis Methods 0.000 description 24
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 24
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 239000003054 catalyst Substances 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 22
• 238000003756 stirring Methods 0.000 description 21
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 20
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• 239000012071 phase Substances 0.000 description 18
• 239000011780 sodium chloride Substances 0.000 description 18
• YDVVUNFRVPSJND-UHFFFAOYSA-N (1-benzyl-5-oxo-2,6-dihydropyridin-3-yl) trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC(=O)CN(CC2=CC=CC=C2)C1 YDVVUNFRVPSJND-UHFFFAOYSA-N 0.000 description 17
• BLYYWRLMNVVLBI-UHFFFAOYSA-M sodium (7-oxo-4-pyridin-3-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NC=CC=1)[O-].[Na+] BLYYWRLMNVVLBI-UHFFFAOYSA-M 0.000 description 17
• DTUARSVTGOUEGE-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1OC=CN=1)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1OC=CN=1)[O-].[Na+] DTUARSVTGOUEGE-UHFFFAOYSA-M 0.000 description 16
• 239000000047 product Substances 0.000 description 15
• 230000002441 reversible effect Effects 0.000 description 15
• 108090000204 Dipeptidase 1 Proteins 0.000 description 14
• HKCHJEBECHNSKM-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)N1C=NC=C1)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)N1C=NC=C1)[O-].[Na+] HKCHJEBECHNSKM-UHFFFAOYSA-M 0.000 description 14
• 239000012299 nitrogen atmosphere Substances 0.000 description 14
• 125000003709 fluoroalkyl group Chemical group 0.000 description 13
• 238000012746 preparative thin layer chromatography Methods 0.000 description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• QWLZCOFQOVSKKH-UHFFFAOYSA-M sodium [4-(2-methylpyrazol-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1N(N=CC=1)C)[O-].[Na+] QWLZCOFQOVSKKH-UHFFFAOYSA-M 0.000 description 13
• 238000009472 formulation Methods 0.000 description 12
• 239000010410 layer Substances 0.000 description 12
• WHYQCQRHPQBZHM-UHFFFAOYSA-N pyrazole-1-carboxylic acid Chemical compound OC(=O)N1C=CC=N1 WHYQCQRHPQBZHM-UHFFFAOYSA-N 0.000 description 12
• 208000015181 infectious disease Diseases 0.000 description 11
• XRIVVNPFRJZLGS-UHFFFAOYSA-M sodium (7-oxo-4-pyrimidin-5-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NC=NC=1)[O-].[Na+] XRIVVNPFRJZLGS-UHFFFAOYSA-M 0.000 description 11
• 150000003952 β-lactams Chemical class 0.000 description 11
• 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 10
• 241000588724 Escherichia coli Species 0.000 description 10
• ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 238000010438 heat treatment Methods 0.000 description 10
• 229920005989 resin Polymers 0.000 description 10
• 239000011347 resin Substances 0.000 description 10
• 239000007858 starting material Substances 0.000 description 10
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 10
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
• 241000192125 Firmicutes Species 0.000 description 9
• 125000000217 alkyl group Chemical group 0.000 description 9
• 238000001704 evaporation Methods 0.000 description 9
• 230000007935 neutral effect Effects 0.000 description 9
• GQVYDGQITFZZQS-UHFFFAOYSA-M sodium [3-(1,2-oxazol-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1C=NOC=1)[O-].[Na+] GQVYDGQITFZZQS-UHFFFAOYSA-M 0.000 description 9
• 102000004190 Enzymes Human genes 0.000 description 8
• 108090000790 Enzymes Proteins 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• PBOXFSPISITSHJ-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=CC=NC=C1)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=CC=NC=C1)[O-].[Na+] PBOXFSPISITSHJ-UHFFFAOYSA-M 0.000 description 8
• YVEOKEJYCVKKIT-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=CN=C(S1)OC)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=CN=C(S1)OC)[O-].[Na+] YVEOKEJYCVKKIT-UHFFFAOYSA-M 0.000 description 8
• AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 8
• 239000002552 dosage form Substances 0.000 description 8
• 230000008020 evaporation Effects 0.000 description 8
• 239000003208 petroleum Substances 0.000 description 8
• VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 8
• GAIXVZWHKRWSLD-UHFFFAOYSA-M sodium (7-oxo-4-pyrazin-2-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=NC=CN=C1)[O-].[Na+] GAIXVZWHKRWSLD-UHFFFAOYSA-M 0.000 description 8
• DUZLYNLJRMDCNX-UHFFFAOYSA-M sodium (7-oxo-4-pyridin-2-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=NC=CC=C1)[O-].[Na+] DUZLYNLJRMDCNX-UHFFFAOYSA-M 0.000 description 8
• DTUARSVTGOUEGE-OGFXRTJISA-M sodium [(5R)-3-(1,3-oxazol-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1[C@@H]2C=C(CN(C1=O)C2)C=1OC=CN=1)[O-].[Na+] DTUARSVTGOUEGE-OGFXRTJISA-M 0.000 description 8
• UQJJPDFNDHGEOR-UHFFFAOYSA-M sodium [4-(1,3-oxazol-5-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=CN=CO1)[O-].[Na+] UQJJPDFNDHGEOR-UHFFFAOYSA-M 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• KWXXTMXRZVICGM-UHFFFAOYSA-M S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C2=CC=NS2)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C2=CC=NS2)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 KWXXTMXRZVICGM-UHFFFAOYSA-M 0.000 description 7
• FMBYVTRWAANVEV-UHFFFAOYSA-M S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C(N(C(N(C=1)C)=O)C)=O)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C(N(C(N(C=1)C)=O)C)=O)[O-].[Na+] FMBYVTRWAANVEV-UHFFFAOYSA-M 0.000 description 7
• QFSDLDHPWZFDOK-UHFFFAOYSA-M S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NC(=NC=1)OC)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NC(=NC=1)OC)[O-].[Na+] QFSDLDHPWZFDOK-UHFFFAOYSA-M 0.000 description 7
• ZKFPBWMMRCNGGF-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=CN=CO1)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=CN=CO1)[O-].[Na+] ZKFPBWMMRCNGGF-UHFFFAOYSA-M 0.000 description 7
• CPUOMMXVKNHVCZ-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=NC=CC=C1)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=NC=CC=C1)[O-].[Na+] CPUOMMXVKNHVCZ-UHFFFAOYSA-M 0.000 description 7
• HWDAWCJNMCDPBT-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=NOC=N1)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=NOC=N1)[O-].[Na+] HWDAWCJNMCDPBT-UHFFFAOYSA-M 0.000 description 7
• WEBXEKUOAQXNJW-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1C=NC=CC=1)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1C=NC=CC=1)[O-].[Na+] WEBXEKUOAQXNJW-UHFFFAOYSA-M 0.000 description 7
• XWWFYPJREMUAOG-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)N1C(CCC1)=O)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)N1C(CCC1)=O)[O-].[Na+] XWWFYPJREMUAOG-UHFFFAOYSA-M 0.000 description 7
• 229960000583 acetic acid Drugs 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 7
• 125000000753 cycloalkyl group Chemical group 0.000 description 7
• OMDIZACDPTXGIX-UHFFFAOYSA-M lithium 2,2-difluoro-2-[[4-(1,2-oxazol-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl]oxy]acetate Chemical compound FC(C(=O)[O-])(ON1C2C(=CCN(C1=O)C2)C=1C=NOC=1)F.[Li+] OMDIZACDPTXGIX-UHFFFAOYSA-M 0.000 description 7
• NBFKNCBRFJKDDR-UHFFFAOYSA-N oct-5-en-2-one Chemical compound CCC=CCCC(C)=O NBFKNCBRFJKDDR-UHFFFAOYSA-N 0.000 description 7
• 239000004810 polytetrafluoroethylene Substances 0.000 description 7
• 229920001343 polytetrafluoroethylene Polymers 0.000 description 7
• 239000011148 porous material Substances 0.000 description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
• DCKPSLSYIJYXAS-UHFFFAOYSA-M sodium (7-oxo-4-pyridin-4-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=CC=NC=C1)[O-].[Na+] DCKPSLSYIJYXAS-UHFFFAOYSA-M 0.000 description 7
• ZURFSZRSDIKKDF-UHFFFAOYSA-M sodium [3-(1,3-benzothiazol-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1SC2=C(N=1)C=CC=C2)[O-].[Na+] ZURFSZRSDIKKDF-UHFFFAOYSA-M 0.000 description 7
• BRNNASYTKCVOTM-UHFFFAOYSA-M sodium [3-(1-methyl-6-oxopyridin-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C1=CN(C(C=C1)=O)C)[O-].[Na+] BRNNASYTKCVOTM-UHFFFAOYSA-M 0.000 description 7
• VZSABGDLMFHTMJ-UHFFFAOYSA-M sodium [4-(1,2-oxazol-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NOC=1)[O-].[Na+] VZSABGDLMFHTMJ-UHFFFAOYSA-M 0.000 description 7
• IEXKRQABTTVXKK-UHFFFAOYSA-M sodium [4-(1,3-oxazol-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1OC=CN=1)[O-].[Na+] IEXKRQABTTVXKK-UHFFFAOYSA-M 0.000 description 7
• MKODBASFEOTOGG-UHFFFAOYSA-M sodium [4-(1-methyl-2-oxopyridin-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C(N(C=CC=1)C)=O)[O-] MKODBASFEOTOGG-UHFFFAOYSA-M 0.000 description 7
• UWQNIZGQAQDGEG-UHFFFAOYSA-M sodium [4-(1-methyl-2-oxopyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=CC(N(C=C1)C)=O)[O-] UWQNIZGQAQDGEG-UHFFFAOYSA-M 0.000 description 7
• KRYGEUWUCCBJOJ-UHFFFAOYSA-M sodium [4-(1-methyl-2-oxopyrimidin-5-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NC(N(C=1)C)=O)[O-] KRYGEUWUCCBJOJ-UHFFFAOYSA-M 0.000 description 7
• CIDUSXRLICQBBQ-UHFFFAOYSA-M sodium [4-(1-methyl-6-oxopyridazin-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=NN(C(C=C1)=O)C)[O-].[Na+] CIDUSXRLICQBBQ-UHFFFAOYSA-M 0.000 description 7
• GWLHOFSTJMKJJX-UHFFFAOYSA-M sodium [4-(1-methyl-6-oxopyridazin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NN(C(C=1)=O)C)[O-].[Na+] GWLHOFSTJMKJJX-UHFFFAOYSA-M 0.000 description 7
• AUWGRJHCXUOISV-UHFFFAOYSA-M sodium [4-(1-methyl-6-oxopyridin-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1N(C(C=CC=1)=O)C)[O-] AUWGRJHCXUOISV-UHFFFAOYSA-M 0.000 description 7
• NJIMLUGPWUUFRP-UHFFFAOYSA-M sodium [4-(1-methyl-6-oxopyridin-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=CN(C(C=C1)=O)C)[O-] NJIMLUGPWUUFRP-UHFFFAOYSA-M 0.000 description 7
• NDSFOZWJOAGTHG-UHFFFAOYSA-M sodium [4-(1-methyl-6-oxopyrimidin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1N=CN(C(C=1)=O)C)[O-] NDSFOZWJOAGTHG-UHFFFAOYSA-M 0.000 description 7
• RKDICIOIHNXYNG-UHFFFAOYSA-M sodium [4-(4-methyl-5-oxopyrazin-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1N=CC(N(C=1)C)=O)[O-].[Na+] RKDICIOIHNXYNG-UHFFFAOYSA-M 0.000 description 7
• FEXJVLPFEUBARK-UHFFFAOYSA-M sodium [4-methyl-7-oxo-3-(1,3-thiazol-2-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=C(CN(C1=O)C2)C=1SC=CN=1)C)[O-].[Na+] FEXJVLPFEUBARK-UHFFFAOYSA-M 0.000 description 7
• NWJBYGRSKRHLNI-UHFFFAOYSA-M sodium [7-oxo-3-(1H-pyrazol-4-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1C=NNC=1)[O-].[Na+] NWJBYGRSKRHLNI-UHFFFAOYSA-M 0.000 description 7
• IGORADVIVCYPCY-UHFFFAOYSA-M sodium [7-oxo-3-([1,3]thiazolo[5,4-b]pyridin-2-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1SC2=NC=CC=C2N=1)[O-].[Na+] IGORADVIVCYPCY-UHFFFAOYSA-M 0.000 description 7
• YWJKCUDVKDRVRQ-UHFFFAOYSA-M sodium [7-oxo-4-(1,2-thiazol-5-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=CC=NS1)[O-].[Na+] YWJKCUDVKDRVRQ-UHFFFAOYSA-M 0.000 description 7
• DJNYAAIGMXOXCU-UHFFFAOYSA-N tert-butyl 4-bromo-3-hydroxy-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC=C(Br)C(O)C1 DJNYAAIGMXOXCU-UHFFFAOYSA-N 0.000 description 7
• NQUYSHIVQWPEHV-UHFFFAOYSA-N tert-butyl 4-methyl-3-oxo-5-tributylstannyl-2,6-dihydropyridine-1-carboxylate Chemical compound CCCC[Sn](CCCC)(CCCC)C1=C(C)C(=O)CN(C(=O)OC(C)(C)C)C1 NQUYSHIVQWPEHV-UHFFFAOYSA-N 0.000 description 7
• OERUWJQPWPUJND-UHFFFAOYSA-M (7-oxo-4-pyridin-2-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound [O-]S(=O)(=O)ON1C2CN(CC=C2c2ccccn2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 OERUWJQPWPUJND-UHFFFAOYSA-M 0.000 description 6
• OJJBJOWEOJBUON-UHFFFAOYSA-M (7-oxo-4-pyridin-3-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound [O-]S(=O)(=O)ON1C2CN(CC=C2c2cccnc2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 OJJBJOWEOJBUON-UHFFFAOYSA-M 0.000 description 6
• FWPKKWDKYJKLTE-UHFFFAOYSA-M (7-oxo-4-pyridin-4-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound [O-]S(=O)(=O)ON1C2CN(CC=C2c2ccncc2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 FWPKKWDKYJKLTE-UHFFFAOYSA-M 0.000 description 6
• RHMUXOYWBXMBKP-UHFFFAOYSA-N 1-benzyl-3-hydroxy-3,6-dihydro-2H-pyridine-5-carbonitrile Chemical compound C(C1=CC=CC=C1)N1CC(C=C(C1)C#N)O RHMUXOYWBXMBKP-UHFFFAOYSA-N 0.000 description 6
• XBLBBTDGGKEQQA-UHFFFAOYSA-N 1-benzyl-5-(1,2-oxazol-4-yl)-2,6-dihydropyridin-3-one Chemical compound O=C1CN(CC2=CC=CC=C2)CC(=C1)C1=CON=C1 XBLBBTDGGKEQQA-UHFFFAOYSA-N 0.000 description 6
• IETPRUOPLKCJPP-UHFFFAOYSA-N 1-benzyl-5-(1,3-oxazol-2-yl)-2,6-dihydropyridin-3-one Chemical compound O=C1CN(CC2=CC=CC=C2)CC(=C1)C1=NC=CO1 IETPRUOPLKCJPP-UHFFFAOYSA-N 0.000 description 6
• XMZAJMNIMWYZKD-UHFFFAOYSA-N 1-benzyl-5-bromo-2,6-dihydropyridin-3-one Chemical compound BrC1=CC(=O)CN(CC2=CC=CC=C2)C1 XMZAJMNIMWYZKD-UHFFFAOYSA-N 0.000 description 6
• VSRLLRQTVJMQPH-UHFFFAOYSA-N 1-benzyl-5-iodo-2,6-dihydropyridin-3-one Chemical compound IC1=CC(=O)CN(CC2=CC=CC=C2)C1 VSRLLRQTVJMQPH-UHFFFAOYSA-N 0.000 description 6
• CEWUFXYIWJLKRT-UHFFFAOYSA-N 1-benzyl-5-iodo-3,6-dihydro-2H-pyridin-3-ol Chemical compound C(C1=CC=CC=C1)N1CC(C=C(C1)I)O CEWUFXYIWJLKRT-UHFFFAOYSA-N 0.000 description 6
• VDEPEZFGUJAFPJ-UHFFFAOYSA-N 2-pyridin-2-yl-1,6-diazabicyclo[3.2.1]oct-3-en-7-one Chemical compound N1=C(C=CC=C1)C1N2C(NC(C=C1)C2)=O VDEPEZFGUJAFPJ-UHFFFAOYSA-N 0.000 description 6
• DLDHUFARLCARAN-UHFFFAOYSA-N 5-(1,3-benzothiazol-2-yl)-1-benzyl-2,6-dihydropyridin-3-one Chemical compound O=C1CN(CC2=CC=CC=C2)CC(=C1)C1=NC2=CC=CC=C2S1 DLDHUFARLCARAN-UHFFFAOYSA-N 0.000 description 6
• RBJVOXQDMPFOHD-UHFFFAOYSA-N 5-(1-benzyl-5-oxo-2,6-dihydropyridin-3-yl)-1-methylpyridin-2-one Chemical compound C(C1=CC=CC=C1)N1CC(C=C(C1)C1=CN(C(C=C1)=O)C)=O RBJVOXQDMPFOHD-UHFFFAOYSA-N 0.000 description 6
• QHXUGIILWFRDII-UHFFFAOYSA-N CC1=C(CN(CC1O)C(=O)OC(C)(C)C)[Sn](CCCC)(CCCC)CCCC Chemical compound CC1=C(CN(CC1O)C(=O)OC(C)(C)C)[Sn](CCCC)(CCCC)CCCC QHXUGIILWFRDII-UHFFFAOYSA-N 0.000 description 6
• SJHCRUZGZBGWBZ-UHFFFAOYSA-N CN1N=CC(=CC1=O)[Sn](C)(C)C Chemical compound CN1N=CC(=CC1=O)[Sn](C)(C)C SJHCRUZGZBGWBZ-UHFFFAOYSA-N 0.000 description 6
• 241000588697 Enterobacter cloacae Species 0.000 description 6
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 6
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 6
• ILHJUALHTBVBBW-UHFFFAOYSA-M S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C2=CN=C(S2)CNC(=O)OC(C)(C)C)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C2=CN=C(S2)CNC(=O)OC(C)(C)C)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 ILHJUALHTBVBBW-UHFFFAOYSA-M 0.000 description 6
• FFSWMEPDYFEQMU-UHFFFAOYSA-M S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=2C(N(C(N(C2)C)=O)C)=O)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=2C(N(C(N(C2)C)=O)C)=O)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 FFSWMEPDYFEQMU-UHFFFAOYSA-M 0.000 description 6
• VOPBOIOTYFKAEP-UHFFFAOYSA-M S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=2C=NC(=NC2)OC)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=2C=NC(=NC2)OC)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 VOPBOIOTYFKAEP-UHFFFAOYSA-M 0.000 description 6
• ZUJLSEGUJYHSOQ-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C2=NC=CC=C2)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C2=NC=CC=C2)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 ZUJLSEGUJYHSOQ-UHFFFAOYSA-M 0.000 description 6
• BUVDGGYLWLEDII-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1C=NC=CC=1)[O-].C1(=CC=CC=C1)[P+](C=CC)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=1C=NC=CC=1)[O-].C1(=CC=CC=C1)[P+](C=CC)(C1=CC=CC=C1)C1=CC=CC=C1 BUVDGGYLWLEDII-UHFFFAOYSA-M 0.000 description 6
• YGNRVZJFYOAAEB-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=2SC1=C(N2)C=CC=C1)[O-].C1(=CC=CC=C1)[P+](C=CC)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)C=2SC1=C(N2)C=CC=C1)[O-].C1(=CC=CC=C1)[P+](C=CC)(C1=CC=CC=C1)C1=CC=CC=C1 YGNRVZJFYOAAEB-UHFFFAOYSA-M 0.000 description 6
• ZVSJPVAUBPKVIY-UHFFFAOYSA-M [4-(2-methylpyrazol-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound Cn1nccc1C1=CCN2CC1N(OS([O-])(=O)=O)C2=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 ZVSJPVAUBPKVIY-UHFFFAOYSA-M 0.000 description 6
• MOXAEDDHSMGUCK-UHFFFAOYSA-N [4-[2-(aminomethyl)-1,3-thiazol-5-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] hydrogen sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=CN=C(S1)CN)O MOXAEDDHSMGUCK-UHFFFAOYSA-N 0.000 description 6
• 125000005336 allyloxy group Chemical group 0.000 description 6
• HGFFKBHQNWRMIT-UHFFFAOYSA-N benzyl 3-(1,2-oxazol-4-yl)-5-oxo-2,6-dihydropyridine-1-carboxylate Chemical compound O=C(OCC1=CC=CC=C1)N1CC(=O)C=C(C1)C1=CON=C1 HGFFKBHQNWRMIT-UHFFFAOYSA-N 0.000 description 6
• XFQGRQXCDWSNQZ-UHFFFAOYSA-N benzyl 3-(1,3-benzothiazol-2-yl)-5-oxo-2,6-dihydropyridine-1-carboxylate Chemical compound O=C(OCC1=CC=CC=C1)N1CC(=O)C=C(C1)C1=NC2=CC=CC=C2S1 XFQGRQXCDWSNQZ-UHFFFAOYSA-N 0.000 description 6
• FHTOIALSTDZMCK-UHFFFAOYSA-N benzyl 3-(1,3-oxazol-2-yl)-5-oxo-2,6-dihydropyridine-1-carboxylate Chemical compound O=C(OCC1=CC=CC=C1)N1CC(=O)C=C(C1)C1=NC=CO1 FHTOIALSTDZMCK-UHFFFAOYSA-N 0.000 description 6
• GFWXNQAEDMVCAO-UHFFFAOYSA-N benzyl 3-(1-methyl-6-oxopyridin-3-yl)-5-oxo-2,6-dihydropyridine-1-carboxylate Chemical compound CN1C=C(C=CC1=O)C1=CC(=O)CN(C1)C(=O)OCC1=CC=CC=C1 GFWXNQAEDMVCAO-UHFFFAOYSA-N 0.000 description 6
• BZWVILQSBHDYAW-UHFFFAOYSA-N benzyl 3-hydroxy-5-(1,3-oxazol-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound OC1CN(CC(=C1)C1=NC=CO1)C(=O)OCC1=CC=CC=C1 BZWVILQSBHDYAW-UHFFFAOYSA-N 0.000 description 6
• LNIBXCAGGGQOMJ-UHFFFAOYSA-N benzyl 3-hydroxy-5-(1-methyl-6-oxopyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound OC1CN(CC(=C1)C1=CN(C(C=C1)=O)C)C(=O)OCC1=CC=CC=C1 LNIBXCAGGGQOMJ-UHFFFAOYSA-N 0.000 description 6
• COWXRPZPCAIUAD-UHFFFAOYSA-N benzyl 5-(1,3-benzothiazol-2-yl)-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound S1C(=NC2=C1C=CC=C2)C1=CC(CN(C1)C(=O)OCC1=CC=CC=C1)O COWXRPZPCAIUAD-UHFFFAOYSA-N 0.000 description 6
• OTKIVFGCFDGPAI-UHFFFAOYSA-N benzyl 5-bromo-3-hydroxy-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound BrC1=CC(CN(C1)C(=O)OCC1=CC=CC=C1)O OTKIVFGCFDGPAI-UHFFFAOYSA-N 0.000 description 6
• 230000005587 bubbling Effects 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 6
• 230000008034 disappearance Effects 0.000 description 6
• 125000005348 fluorocycloalkyl group Chemical group 0.000 description 6
• 239000012362 glacial acetic acid Substances 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
• 238000010898 silica gel chromatography Methods 0.000 description 6
• CXKIFIHIKWDVMQ-UHFFFAOYSA-M sodium (7-oxo-3-pyrazol-1-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)N1N=CC=C1)[O-].[Na+] CXKIFIHIKWDVMQ-UHFFFAOYSA-M 0.000 description 6
• GXYLNHNNBZBOJI-UHFFFAOYSA-M sodium [4-[2-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-1,3-thiazol-5-yl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C1=CN=C(S1)CNC(=O)OC(C)(C)C)[O-].[Na+] GXYLNHNNBZBOJI-UHFFFAOYSA-M 0.000 description 6
• UCSRWFPRWBCRCA-UHFFFAOYSA-M sodium [7-oxo-4-(1,2-thiazol-4-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1C=NSC=1)[O-].[Na+] UCSRWFPRWBCRCA-UHFFFAOYSA-M 0.000 description 6
• ZEVBVAJMMFOKFP-UHFFFAOYSA-M sodium [7-oxo-4-(1,3-thiazol-4-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate Chemical compound S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=1N=CSC=1)[O-].[Na+] ZEVBVAJMMFOKFP-UHFFFAOYSA-M 0.000 description 6
• MQITUTWQBRZMCK-UHFFFAOYSA-N tert-butyl 3-bromo-5-(1,3-oxazol-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound BrC1CN(CC(=C1)C=1OC=CN=1)C(=O)OC(C)(C)C MQITUTWQBRZMCK-UHFFFAOYSA-N 0.000 description 6
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• IIGPIAFRXCAHAP-UHFFFAOYSA-M (7-oxo-4-pyrazin-2-yl-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl) sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound [O-]S(=O)(=O)ON1C2CN(CC=C2c2cnccn2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 IIGPIAFRXCAHAP-UHFFFAOYSA-M 0.000 description 5
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