KR102713561B1 - 헤테로사이클릭 화합물 및 세균성 감염을 예방 또는 치료하는 이의 용도 - Google Patents

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Publication number

KR102713561B1

KR102713561B1 KR1020177031802A KR20177031802A KR102713561B1 KR 102713561 B1 KR102713561 B1 KR 102713561B1 KR 1020177031802 A KR1020177031802 A KR 1020177031802A KR 20177031802 A KR20177031802 A KR 20177031802A KR 102713561 B1 KR102713561 B1 KR 102713561B1

Authority

KR

South Korea

Prior art keywords

mmol

oxo

oct

diazabicyclo

alkyl

Prior art date

2015-05-07

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 208000035143 Bacterial infection Diseases 0.000 title claims abstract description 41
• 208000022362 bacterial infectious disease Diseases 0.000 title claims abstract description 41
• 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 210
• -1 beta-lactam compounds Chemical class 0.000 claims abstract description 39
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 230000002265 prevention Effects 0.000 claims abstract description 14
• 229910020008 S(O) Inorganic materials 0.000 claims description 116
• 239000000203 mixture Substances 0.000 claims description 101
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 87
• 125000005842 heteroatom Chemical group 0.000 claims description 72
• 241000894006 Bacteria Species 0.000 claims description 58
• 125000000623 heterocyclic group Chemical group 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 229910052717 sulfur Inorganic materials 0.000 claims description 38
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 37
• 229920006395 saturated elastomer Polymers 0.000 claims description 36
• 229910052760 oxygen Inorganic materials 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 24
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
• 102000006635 beta-lactamase Human genes 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 14
• 229960000484 ceftazidime Drugs 0.000 claims description 13
• 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 claims description 13
• 239000004599 antimicrobial Substances 0.000 claims description 12
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 150000003952 β-lactams Chemical class 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 108020004256 Beta-lactamase Proteins 0.000 claims description 5
• 230000000845 anti-microbial effect Effects 0.000 claims description 5
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000001302 tertiary amino group Chemical group 0.000 claims description 3
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
• 108010015899 Glycopeptides Proteins 0.000 claims description 2
• 102000002068 Glycopeptides Human genes 0.000 claims description 2
• 108010028921 Lipopeptides Proteins 0.000 claims description 2
• 108010040201 Polymyxins Proteins 0.000 claims description 2
• 108010034396 Streptogramins Proteins 0.000 claims description 2
• 239000004098 Tetracycline Substances 0.000 claims description 2
• 229940126575 aminoglycoside Drugs 0.000 claims description 2
• 230000000844 anti-bacterial effect Effects 0.000 claims description 2
• 229940124307 fluoroquinolone Drugs 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• 239000003835 ketolide antibiotic agent Substances 0.000 claims description 2
• 229940041028 lincosamides Drugs 0.000 claims description 2
• 239000003120 macrolide antibiotic agent Substances 0.000 claims description 2
• 229940041033 macrolides Drugs 0.000 claims description 2
• 229940041153 polymyxins Drugs 0.000 claims description 2
• 150000007660 quinolones Chemical class 0.000 claims description 2
• 229940041030 streptogramins Drugs 0.000 claims description 2
• 235000019364 tetracycline Nutrition 0.000 claims description 2
• 150000003522 tetracyclines Chemical class 0.000 claims description 2
• 229940040944 tetracyclines Drugs 0.000 claims description 2
• FPZLLRFZJZRHSY-HJYUBDRYSA-N tigecycline Chemical class C([C@H]1C2)C3=C(N(C)C)C=C(NC(=O)CNC(C)(C)C)C(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O FPZLLRFZJZRHSY-HJYUBDRYSA-N 0.000 claims description 2
• 229960004089 tigecycline Drugs 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 abstract description 211
• 238000000034 method Methods 0.000 abstract description 125
• 239000003242 anti bacterial agent Substances 0.000 abstract description 16
• 239000003781 beta lactamase inhibitor Substances 0.000 abstract description 7
• 229940126813 beta-lactamase inhibitor Drugs 0.000 abstract description 7
• 230000008569 process Effects 0.000 abstract description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 270
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 261
• 239000000543 intermediate Substances 0.000 description 229
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 128
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 128
• 239000000741 silica gel Substances 0.000 description 115
• 229910002027 silica gel Inorganic materials 0.000 description 115
• 238000005481 NMR spectroscopy Methods 0.000 description 110
• 239000011734 sodium Substances 0.000 description 110
• 238000003818 flash chromatography Methods 0.000 description 96
• 239000007787 solid Substances 0.000 description 93
• 239000000243 solution Substances 0.000 description 91
• 230000015572 biosynthetic process Effects 0.000 description 83
• 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 80
• 229910052708 sodium Inorganic materials 0.000 description 73
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 72
• 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 72
• 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 62
• 238000006243 chemical reaction Methods 0.000 description 59
• 238000000746 purification Methods 0.000 description 55
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 52
• 239000011541 reaction mixture Substances 0.000 description 50
• 230000002829 reductive effect Effects 0.000 description 50
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 49
• 238000003786 synthesis reaction Methods 0.000 description 48
• 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 46
• 238000004587 chromatography analysis Methods 0.000 description 38
• 238000004108 freeze drying Methods 0.000 description 38
• 229910052786 argon Inorganic materials 0.000 description 36
• 238000005342 ion exchange Methods 0.000 description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• 239000012044 organic layer Substances 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
• 239000012298 atmosphere Substances 0.000 description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
• WMKYKQWKLILFBM-UHFFFAOYSA-N 2h-pyridine-1-carboxylic acid Chemical compound OC(=O)N1CC=CC=C1 WMKYKQWKLILFBM-UHFFFAOYSA-N 0.000 description 28
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 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
• 239000000725 suspension Substances 0.000 description 23
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 23
• 239000003054 catalyst Substances 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 22
• 238000005160 1H NMR spectroscopy Methods 0.000 description 21
• 239000012071 phase Substances 0.000 description 21
• 239000013058 crude material Substances 0.000 description 20
• 238000003756 stirring Methods 0.000 description 20
• 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 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 239000003921 oil Substances 0.000 description 18
• 235000019198 oils Nutrition 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
• 239000007864 aqueous solution Substances 0.000 description 17
• 230000002441 reversible effect Effects 0.000 description 17
• 239000012267 brine Substances 0.000 description 16
• 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 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
• 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 15
• 229910001873 dinitrogen Inorganic materials 0.000 description 14
• 208000015181 infectious disease Diseases 0.000 description 14
• 238000004519 manufacturing process Methods 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 13
• 239000012043 crude product Substances 0.000 description 12
• 238000012746 preparative thin layer chromatography Methods 0.000 description 12
• 239000007858 starting material Substances 0.000 description 12
• 229910001868 water Inorganic materials 0.000 description 12
• 108090000204 Dipeptidase 1 Proteins 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 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 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
• 239000003814 drug Substances 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• 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 10
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
• 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 9
• 230000007935 neutral effect Effects 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• 102000004190 Enzymes Human genes 0.000 description 8
• 108090000790 Enzymes Proteins 0.000 description 8
• 230000014509 gene expression 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
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 7
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 7
• 241000192125 Firmicutes Species 0.000 description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 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 7
• 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 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
• 239000004810 polytetrafluoroethylene Substances 0.000 description 7
• 229920001343 polytetrafluoroethylene Polymers 0.000 description 7
• 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 7
• 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 7
• 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 7
• 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 7
• 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 6
• 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
• JKKJNVBCEPRDPH-UHFFFAOYSA-M (7-oxo-4-pyrimidin-5-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=C2c2cncnc2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 JKKJNVBCEPRDPH-UHFFFAOYSA-M 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
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• OJCLJYUHBRHVBJ-UHFFFAOYSA-N 1-benzyl-5-oxo-2,6-dihydropyridine-3-carbonitrile Chemical compound O=C1CN(CC2=CC=CC=C2)CC(=C1)C#N OJCLJYUHBRHVBJ-UHFFFAOYSA-N 0.000 description 6
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• CQJBCYRZBYMDFT-UHFFFAOYSA-M [4-(1,2-oxazol-4-yl)-7-oxo-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=C2c2cnoc2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 CQJBCYRZBYMDFT-UHFFFAOYSA-M 0.000 description 6
• VFEZHPNKSPGYNM-UHFFFAOYSA-M [4-(1,3-oxazol-2-yl)-7-oxo-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=C2c2ncco2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 VFEZHPNKSPGYNM-UHFFFAOYSA-M 0.000 description 6
• YLYYDXURXWMRFN-UHFFFAOYSA-M [4-(1,3-oxazol-5-yl)-7-oxo-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=C2c2cnco2)C1=O.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 YLYYDXURXWMRFN-UHFFFAOYSA-M 0.000 description 6
• BEZWPEQYUXLNGZ-UHFFFAOYSA-M [4-(1-methyl-2-oxopyrimidin-5-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1cc(cnc1=O)C1=CCN2CC1N(OS([O-])(=O)=O)C2=O BEZWPEQYUXLNGZ-UHFFFAOYSA-M 0.000 description 6
• HNXAVJIEGXBVPT-UHFFFAOYSA-M [4-(1-methyl-6-oxopyridazin-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1nc(ccc1=O)C1=CCN2CC1N(OS([O-])(=O)=O)C2=O HNXAVJIEGXBVPT-UHFFFAOYSA-M 0.000 description 6
• KHBWTZKVAWSXJH-UHFFFAOYSA-M [4-(1-methyl-6-oxopyridazin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1ncc(cc1=O)C1=CCN2CC1N(OS([O-])(=O)=O)C2=O KHBWTZKVAWSXJH-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
• YSKMSGOFMKNPIX-UHFFFAOYSA-M [4-(4-methyl-5-oxopyrazin-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1cc(ncc1=O)C1=CCN2CC1N(OS([O-])(=O)=O)C2=O YSKMSGOFMKNPIX-UHFFFAOYSA-M 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 6
• 125000005336 allyloxy group Chemical group 0.000 description 6
• 230000001580 bacterial effect Effects 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
• 230000005587 bubbling Effects 0.000 description 6
• 150000007942 carboxylates Chemical class 0.000 description 6
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• 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 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
• 125000003226 pyrazolyl group Chemical group 0.000 description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
• 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 6
• 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 6
• 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 6
• 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 6
• 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 6
• 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 6
• 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 6
• 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 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
• 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 6
• UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 6
• 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 6
• 125000003831 tetrazolyl group Chemical group 0.000 description 6
• CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Substances C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• 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 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• 206010035664 Pneumonia Diseases 0.000 description 5
• 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 5
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• KVXLTTDVOBCPCN-UHFFFAOYSA-M [4-(1-methyl-2-oxopyridin-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1cccc(C2=CCN3CC2N(OS([O-])(=O)=O)C3=O)c1=O KVXLTTDVOBCPCN-UHFFFAOYSA-M 0.000 description 5
• QOVJGYFIQWHYLP-UHFFFAOYSA-M [4-(1-methyl-2-oxopyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1ccc(cc1=O)C1=CCN2CC1N(OS([O-])(=O)=O)C2=O QOVJGYFIQWHYLP-UHFFFAOYSA-M 0.000 description 5
• ZRKVQQAYGMJULB-UHFFFAOYSA-M [4-(1-methyl-6-oxopyridin-2-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1c(cccc1=O)C1=CCN2CC1N(OS([O-])(=O)=O)C2=O ZRKVQQAYGMJULB-UHFFFAOYSA-M 0.000 description 5
• RQFPYYJMDRMEFK-UHFFFAOYSA-M [4-(1-methyl-6-oxopyridin-3-yl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.Cn1cc(ccc1=O)C1=CCN2CC1N(OS([O-])(=O)=O)C2=O RQFPYYJMDRMEFK-UHFFFAOYSA-M 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 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 5
• 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 5
• SHXSZTVURYQJHE-UHFFFAOYSA-N benzyl 3-bromo-5-oxo-2,6-dihydropyridine-1-carboxylate Chemical compound BrC1=CC(=O)CN(C1)C(=O)OCC1=CC=CC=C1 SHXSZTVURYQJHE-UHFFFAOYSA-N 0.000 description 5
• GNJQKTROVZLPMX-UHFFFAOYSA-N benzyl 3-hydroxy-5-(1,2-oxazol-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylate Chemical compound OC1CN(CC(=C1)C=1C=NOC=1)C(=O)OCC1=CC=CC=C1 GNJQKTROVZLPMX-UHFFFAOYSA-N 0.000 description 5
• 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 5
• 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 5
• 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 5
• 239000002775 capsule Substances 0.000 description 5
• 239000012230 colorless oil Substances 0.000 description 5
• 238000010586 diagram Methods 0.000 description 5
• ASDBEQDGWNZIHR-UHFFFAOYSA-N ethyl 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)OCC)(ON1C2C(=CCN(C1=O)C2)C=1C=NOC=1)F ASDBEQDGWNZIHR-UHFFFAOYSA-N 0.000 description 5
• 239000012362 glacial acetic acid Substances 0.000 description 5
• 239000012528 membrane Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 229920005989 resin Polymers 0.000 description 5
• 239000011347 resin Substances 0.000 description 5
• 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 5
• JYZXHFCNWURNST-UHFFFAOYSA-M sodium [3-(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=C(CN(C1=O)C2)C=1C=NN(C(C=1)=O)C)[O-].[Na+] JYZXHFCNWURNST-UHFFFAOYSA-M 0.000 description 5
• 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 5
• 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 5
• 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 5
• 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 5
• GGSJIBGLPBAJFO-UHFFFAOYSA-M sodium [7-oxo-3-[1-(2-trimethylsilylethoxymethyl)imidazol-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=1N(C=CN=1)COCC[Si](C)(C)C)[O-].[Na+] GGSJIBGLPBAJFO-UHFFFAOYSA-M 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
• 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 4
• 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 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• DWOZNANUEDYIOF-UHFFFAOYSA-L 4-ditert-butylphosphanyl-n,n-dimethylaniline;dichloropalladium Chemical compound Cl[Pd]Cl.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 DWOZNANUEDYIOF-UHFFFAOYSA-L 0.000 description 4
• UVRDIFOZBJEFGI-UHFFFAOYSA-N 6-methylsulfanyl-1h-1,3,5-triazine-2,4-dithione Chemical compound CSC1=NC(=S)NC(=S)N1 UVRDIFOZBJEFGI-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• QYSFCJHKZGUJNA-UHFFFAOYSA-M S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)N1C(CC1)=O)[O-].[Na+] Chemical compound S(=O)(=O)(ON1C2C=C(CN(C1=O)C2)N1C(CC1)=O)[O-].[Na+] QYSFCJHKZGUJNA-UHFFFAOYSA-M 0.000 description 4
• 229920002472 Starch Polymers 0.000 description 4
• 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 4
• PJOPXOVQDDHDEI-UHFFFAOYSA-L [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=2N=CSC2)[O-].[Na+].S2C=NC(=C2)C2=CCN1C(N(C2C1)OS(=O)(=O)[O-])=O Chemical compound [Na+].S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=2N=CSC2)[O-].[Na+].S2C=NC(=C2)C2=CCN1C(N(C2C1)OS(=O)(=O)[O-])=O PJOPXOVQDDHDEI-UHFFFAOYSA-L 0.000 description 4
• 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 4
• 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 4
• 239000011230 binding agent Substances 0.000 description 4
• 239000000872 buffer Substances 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 239000000499 gel Substances 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
• 229910052744 lithium Inorganic materials 0.000 description 4
• 244000005700 microbiome Species 0.000 description 4
• 125000002950 monocyclic group Chemical group 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 239000008107 starch Substances 0.000 description 4
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• 208000024891 symptom Diseases 0.000 description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 4
• 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 4
• VAELWSLNTRVXQS-UHFFFAOYSA-N 1,3-oxazole-4-carboxamide Chemical compound NC(=O)C1=COC=N1 VAELWSLNTRVXQS-UHFFFAOYSA-N 0.000 description 3
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 description 3
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 3
• CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 3
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• PINNDCVGOMAKPQ-UHFFFAOYSA-M S(=O)(=O)(ON1C2C(=CCN(C1=O)C2)C=2N=CSC2)[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=2N=CSC2)[O-].C2(=CC=CC=C2)[P+](C=CC)(C2=CC=CC=C2)C2=CC=CC=C2 PINNDCVGOMAKPQ-UHFFFAOYSA-M 0.000 description 3
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
• 229930006000 Sucrose Natural products 0.000 description 3
• MSGMCVWJMUOKAU-UHFFFAOYSA-M [4-methyl-7-oxo-3-(1,3-thiazol-2-yl)-1,6-diazabicyclo[3.2.1]oct-3-en-6-yl] sulfate triphenyl(prop-1-enyl)phosphanium Chemical compound CC1=C(CN2CC1N(OS([O-])(=O)=O)C2=O)c1nccs1.CC=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 MSGMCVWJMUOKAU-UHFFFAOYSA-M 0.000 description 3
• WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 description 3
• 230000002378 acidificating effect Effects 0.000 description 3
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• 125000002393 azetidinyl group Chemical group 0.000 description 3
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
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