TW201247661A - Monobactams - Google Patents

Info

Publication number

TW201247661A

TW201247661A TW100143172A TW100143172A TW201247661A TW 201247661 A TW201247661 A TW 201247661A TW 100143172 A TW100143172 A TW 100143172A TW 100143172 A TW100143172 A TW 100143172A TW 201247661 A TW201247661 A TW 201247661A

Authority

TW

Taiwan

Prior art keywords

mmol

formula

compound

etoac

preparation

Prior art date

2010-11-29

Links

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• 229940041009 monobactams Drugs 0.000 title 1
• 208000035143 Bacterial infection Diseases 0.000 claims abstract description 11
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims description 227
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 96
• 229910052739 hydrogen Inorganic materials 0.000 claims description 93
• 239000001257 hydrogen Substances 0.000 claims description 91
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 75
• -1 substituted Chemical class 0.000 claims description 72
• 150000003839 salts Chemical class 0.000 claims description 61
• 125000000217 alkyl group Chemical group 0.000 claims description 49
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
• 229910052799 carbon Inorganic materials 0.000 claims description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 239000003814 drug Substances 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 18
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
• 239000000126 substance Substances 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 11
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 150000003852 triazoles Chemical class 0.000 claims description 6
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
• WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical class O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 680
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 317
• 235000019439 ethyl acetate Nutrition 0.000 description 291
• 239000000203 mixture Substances 0.000 description 244
• 238000002360 preparation method Methods 0.000 description 230
• 239000000243 solution Substances 0.000 description 211
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 196
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 174
• 239000007787 solid Substances 0.000 description 165
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
• 238000005481 NMR spectroscopy Methods 0.000 description 153
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 142
• 239000011541 reaction mixture Substances 0.000 description 138
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 115
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 112
• 238000000034 method Methods 0.000 description 97
• 238000006243 chemical reaction Methods 0.000 description 89
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 87
• 239000002904 solvent Substances 0.000 description 84
• 239000012044 organic layer Substances 0.000 description 82
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 81
• 208000015181 infectious disease Diseases 0.000 description 79
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 63
• 238000004587 chromatography analysis Methods 0.000 description 62
• 239000010410 layer Substances 0.000 description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 56
• 239000000725 suspension Substances 0.000 description 54
• 206010057190 Respiratory tract infections Diseases 0.000 description 52
• 239000013058 crude material Substances 0.000 description 52
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 50
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 48
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
• 229910052757 nitrogen Inorganic materials 0.000 description 44
• 235000019441 ethanol Nutrition 0.000 description 40
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
• 238000001914 filtration Methods 0.000 description 34
• 229910052938 sodium sulfate Inorganic materials 0.000 description 34
• 235000011152 sodium sulphate Nutrition 0.000 description 34
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 239000000706 filtrate Substances 0.000 description 33
• 150000001721 carbon Chemical group 0.000 description 32
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
• 238000003756 stirring Methods 0.000 description 31
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 29
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 28
• 235000019253 formic acid Nutrition 0.000 description 28
• 239000000047 product Substances 0.000 description 28
• 239000012267 brine Substances 0.000 description 27
• 239000012065 filter cake Substances 0.000 description 27
• 239000002002 slurry Substances 0.000 description 27
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 25
• 101150041968 CDC13 gene Proteins 0.000 description 24
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 24
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 24
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 24
• 235000019341 magnesium sulphate Nutrition 0.000 description 24
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 24
• 235000017557 sodium bicarbonate Nutrition 0.000 description 24
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
• 239000012043 crude product Substances 0.000 description 22
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 22
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
• 150000001412 amines Chemical class 0.000 description 15
• 239000003242 anti bacterial agent Substances 0.000 description 15
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 15
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 14
• 230000015572 biosynthetic process Effects 0.000 description 14
• 125000006239 protecting group Chemical group 0.000 description 14
• 239000002253 acid Substances 0.000 description 13
• 239000000460 chlorine Substances 0.000 description 13
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 13
• 238000010828 elution Methods 0.000 description 13
• 208000027096 gram-negative bacterial infections Diseases 0.000 description 13
• 238000004128 high performance liquid chromatography Methods 0.000 description 13
• 239000002244 precipitate Substances 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 229940079593 drug Drugs 0.000 description 12
• 238000003786 synthesis reaction Methods 0.000 description 12
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
• 239000012467 final product Substances 0.000 description 11
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
• 239000003607 modifier Substances 0.000 description 11
• 229910000027 potassium carbonate Inorganic materials 0.000 description 11
• 238000005160 1H NMR spectroscopy Methods 0.000 description 10
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
• 239000000010 aprotic solvent Substances 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000000543 intermediate Substances 0.000 description 10
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 10
• 125000002950 monocyclic group Chemical group 0.000 description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• 210000003491 skin Anatomy 0.000 description 10
• 241000588724 Escherichia coli Species 0.000 description 9
• 241000588747 Klebsiella pneumoniae Species 0.000 description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• 125000001424 substituent group Chemical group 0.000 description 9
• 208000031729 Bacteremia Diseases 0.000 description 8
• 241000894006 Bacteria Species 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• 208000014912 Central Nervous System Infections Diseases 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 206010011409 Cross infection Diseases 0.000 description 8
• 208000036209 Intraabdominal Infections Diseases 0.000 description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• 206010031252 Osteomyelitis Diseases 0.000 description 8
• 206010040047 Sepsis Diseases 0.000 description 8
• 206010062255 Soft tissue infection Diseases 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• 238000001514 detection method Methods 0.000 description 8
• 206010014665 endocarditis Diseases 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 239000006260 foam Substances 0.000 description 8
• 239000011521 glass Substances 0.000 description 8
• 230000002685 pulmonary effect Effects 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• 229910052717 sulfur Inorganic materials 0.000 description 8
• AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
• 230000009885 systemic effect Effects 0.000 description 8
• 208000019206 urinary tract infection Diseases 0.000 description 8
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 7
• JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 241000588626 Acinetobacter baumannii Species 0.000 description 7
• 206010060803 Diabetic foot infection Diseases 0.000 description 7
• 208000001860 Eye Infections Diseases 0.000 description 7
• 208000005141 Otitis Diseases 0.000 description 7
• 206010035664 Pneumonia Diseases 0.000 description 7
• 208000005718 Stomach Neoplasms Diseases 0.000 description 7
• 125000004093 cyano group Chemical group *C#N 0.000 description 7
• 208000019258 ear infection Diseases 0.000 description 7
• 206010017758 gastric cancer Diseases 0.000 description 7
• 229910052736 halogen Inorganic materials 0.000 description 7
• 150000002367 halogens Chemical group 0.000 description 7
• 208000014674 injury Diseases 0.000 description 7
• 125000000842 isoxazolyl group Chemical group 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
• 125000004430 oxygen atom Chemical group O* 0.000 description 7
• 201000011549 stomach cancer Diseases 0.000 description 7
• 230000008733 trauma Effects 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• 201000003883 Cystic fibrosis Diseases 0.000 description 6
• 206010029803 Nosocomial infection Diseases 0.000 description 6
• 229910019142 PO4 Inorganic materials 0.000 description 6
• 208000008469 Peptic Ulcer Diseases 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 241000589517 Pseudomonas aeruginosa Species 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 125000003545 alkoxy group Chemical group 0.000 description 6
• 238000010511 deprotection reaction Methods 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 230000002496 gastric effect Effects 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• 238000002347 injection Methods 0.000 description 6
• 239000007924 injection Substances 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
• 239000010452 phosphate Substances 0.000 description 6
• 239000011698 potassium fluoride Substances 0.000 description 6
• 239000000376 reactant Substances 0.000 description 6
• 206010040872 skin infection Diseases 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 125000004434 sulfur atom Chemical group 0.000 description 6
• 125000001425 triazolyl group Chemical group 0.000 description 6
• 238000003828 vacuum filtration Methods 0.000 description 6
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 5
• 229930186147 Cephalosporin Natural products 0.000 description 5
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 5
• 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 5
• 230000002378 acidificating effect Effects 0.000 description 5
• 239000004202 carbamide Substances 0.000 description 5
• 235000013877 carbamide Nutrition 0.000 description 5
• 208000025222 central nervous system infectious disease Diseases 0.000 description 5
• 229940124587 cephalosporin Drugs 0.000 description 5
• 150000001780 cephalosporins Chemical class 0.000 description 5
• 238000001816 cooling Methods 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
• 208000011323 eye infectious disease Diseases 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 5
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
• 239000000651 prodrug Substances 0.000 description 5
• 229940002612 prodrug Drugs 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 230000000699 topical effect Effects 0.000 description 5
• FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 5
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
• 241000589291 Acinetobacter Species 0.000 description 4
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
• 239000005695 Ammonium acetate Substances 0.000 description 4
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 4
• 241000590002 Helicobacter pylori Species 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
• 229930182555 Penicillin Natural products 0.000 description 4
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
• 241000589516 Pseudomonas Species 0.000 description 4
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