TW319766B - - Google Patents
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- TW319766B TW319766B TW084106729A TW84106729A TW319766B TW 319766 B TW319766 B TW 319766B TW 084106729 A TW084106729 A TW 084106729A TW 84106729 A TW84106729 A TW 84106729A TW 319766 B TW319766 B TW 319766B
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- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 9
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 238000011049 filling Methods 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 239000002253 acid Chemical group 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000002516 radical scavenger Substances 0.000 claims description 2
- 229910052705 radium Inorganic materials 0.000 claims description 2
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical group [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 235000012054 meals Nutrition 0.000 claims 1
- -1 benzoxazine compounds Chemical class 0.000 abstract description 27
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 6
- 150000002431 hydrogen Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000123 paper Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- CKOIBBUUNORFJQ-UHFFFAOYSA-N non-4-ene Chemical compound [CH2]CCC=CCCCC CKOIBBUUNORFJQ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002357 guanidines Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UOTAVRHXGRHIAL-UHFFFAOYSA-N 2,3,3a,4,5,7a-hexahydro-1h-isoindole Chemical compound C1=CCCC2CNCC21 UOTAVRHXGRHIAL-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DXMKFMBLOIOTLF-UHFFFAOYSA-N N=1COC=C2C=1C=CC(=C2)C(=O)O Chemical compound N=1COC=C2C=1C=CC(=C2)C(=O)O DXMKFMBLOIOTLF-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 229940032049 enterococcus faecalis Drugs 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229910052743 krypton Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- CVSWUEXZWSBDMC-UHFFFAOYSA-N non-2-ene Chemical compound CCCCCC[CH]C=C CVSWUEXZWSBDMC-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- LGKANOVVJSORFA-ONEGZZNKSA-N (3e)-5-bromopenta-1,3-diene Chemical compound BrC\C=C\C=C LGKANOVVJSORFA-ONEGZZNKSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- RVDHGRQELZPGCO-UHFFFAOYSA-N 1-benzofuran-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=COC2=C1 RVDHGRQELZPGCO-UHFFFAOYSA-N 0.000 description 1
- ZQVRACDRCQNBGK-UHFFFAOYSA-N 2,3,3a,4,5,7a-hexahydro-1h-indene Chemical compound C1CC=CC2CCCC21 ZQVRACDRCQNBGK-UHFFFAOYSA-N 0.000 description 1
- NWINMFPKWXLODD-UHFFFAOYSA-N 2,3,3a,4,5,7a-hexahydro-1h-isoindol-4-ylmethanol Chemical compound OCC1CC=CC2CNCC12 NWINMFPKWXLODD-UHFFFAOYSA-N 0.000 description 1
- KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 1
- GTYZDORKFFSTLS-UHFFFAOYSA-N 2h-3,1-benzoxazine Chemical class C1=CC=CC2=NCOC=C21 GTYZDORKFFSTLS-UHFFFAOYSA-N 0.000 description 1
- AOEYFVKFGKTMAG-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine-3-carboxylic acid Chemical compound N1=CC=CC2=C(ONC(C(=O)O)=C3)C3=CC=C21 AOEYFVKFGKTMAG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- HTNUCKDQVIZWMJ-UHFFFAOYSA-N 7(alpha)-Hydroxy-1,3-dioxo-friedelan Natural products C1CC(=O)C(C)(C)C2C31CC13CCC3(C)C(C(CCC(=C)C(C)C(O)=O)C)CCC3(C)C1CC2 HTNUCKDQVIZWMJ-UHFFFAOYSA-N 0.000 description 1
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- 241000335053 Beta vulgaris Species 0.000 description 1
- OCDPIBHMYYOVIC-UHFFFAOYSA-N C1(CC1)NC1C2CNCC2C=CC1.C(C)NC1C2CNCC2C=CC1.CNC1C2CNCC2C=CC1 Chemical compound C1(CC1)NC1C2CNCC2C=CC1.C(C)NC1C2CNCC2C=CC1.CNC1C2CNCC2C=CC1 OCDPIBHMYYOVIC-UHFFFAOYSA-N 0.000 description 1
- PWHYOHFBTKEQFY-UHFFFAOYSA-N C=CC.C(C)(=O)N Chemical compound C=CC.C(C)(=O)N PWHYOHFBTKEQFY-UHFFFAOYSA-N 0.000 description 1
- HTNUCKDQVIZWMJ-AMIGDOOGSA-N C[C@H](CCC(=C)[C@@H](C)C(O)=O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C Chemical compound C[C@H](CCC(=C)[C@@H](C)C(O)=O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CCC(=O)C4(C)C HTNUCKDQVIZWMJ-AMIGDOOGSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 238000006290 Diels-Alder intramolecular cycloaddition reaction Methods 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
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- 241000192125 Firmicutes Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
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- 241000191938 Micrococcus luteus Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ZHAYRPSYUGLFIQ-UHFFFAOYSA-N NC1C2CNC(C2C=CC1)C.NC1C2CNCC2(C=CC1)C Chemical compound NC1C2CNC(C2C=CC1)C.NC1C2CNCC2(C=CC1)C ZHAYRPSYUGLFIQ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 241000282320 Panthera leo Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 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 1
- 241000589516 Pseudomonas Species 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 101100340774 Xenopus laevis ilf3-a gene Proteins 0.000 description 1
- DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical compound [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
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- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
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- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000003972 cyclic carboxylic anhydrides Chemical class 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
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- 210000004268 dentin Anatomy 0.000 description 1
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- LJWKFGGDMBPPAZ-UHFFFAOYSA-N ethoxyethane;toluene Chemical compound CCOCC.CC1=CC=CC=C1 LJWKFGGDMBPPAZ-UHFFFAOYSA-N 0.000 description 1
- SFFNNTIOVURBBE-UHFFFAOYSA-N ethyl n-(2,3,3a,4,5,7a-hexahydro-1h-isoindol-4-yl)carbamate Chemical compound CCOC(=O)NC1CC=CC2CNCC12 SFFNNTIOVURBBE-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 101150040667 ilf3 gene Proteins 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052704 radon Inorganic materials 0.000 description 1
- SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Paper (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Seasonings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4424369A DE4424369A1 (de) | 1994-07-11 | 1994-07-11 | Pyrido[3,2,1.i,j][3,1]benzoxazinderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW319766B true TW319766B (en, 2012) | 1997-11-11 |
Family
ID=6522819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW084106729A TW319766B (en, 2012) | 1994-07-11 | 1995-06-30 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5854241A (en, 2012) |
| EP (1) | EP0770083B1 (en, 2012) |
| JP (1) | JPH10502377A (en, 2012) |
| KR (1) | KR100372978B1 (en, 2012) |
| CN (1) | CN1086706C (en, 2012) |
| AT (1) | ATE195941T1 (en, 2012) |
| AU (1) | AU684651B2 (en, 2012) |
| BR (1) | BR9508384A (en, 2012) |
| CA (1) | CA2194694A1 (en, 2012) |
| CZ (1) | CZ5697A3 (en, 2012) |
| DE (2) | DE4424369A1 (en, 2012) |
| DK (1) | DK0770083T3 (en, 2012) |
| ES (1) | ES2150576T3 (en, 2012) |
| FI (1) | FI970092A0 (en, 2012) |
| HU (1) | HUT77138A (en, 2012) |
| IL (1) | IL114499A0 (en, 2012) |
| MX (1) | MX9700306A (en, 2012) |
| NO (1) | NO970079L (en, 2012) |
| NZ (1) | NZ289419A (en, 2012) |
| PL (1) | PL318097A1 (en, 2012) |
| SK (1) | SK2797A3 (en, 2012) |
| TW (1) | TW319766B (en, 2012) |
| WO (1) | WO1996001829A1 (en, 2012) |
| ZA (1) | ZA955707B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6509327B1 (en) | 1998-09-30 | 2003-01-21 | Alcon Manufacturing, Ltd. | Compositions and methods for treating otic, ophthalmic and nasal infections |
| US6716830B2 (en) | 1998-09-30 | 2004-04-06 | Alcon, Inc. | Ophthalmic antibiotic compositions containing moxifloxacin |
| AR020661A1 (es) * | 1998-09-30 | 2002-05-22 | Alcon Lab Inc | Una composicion farmaceutica topica oftalmica, otica o nasal y el uso de la misma para la manufactura de un medicamento |
| US6395746B1 (en) | 1998-09-30 | 2002-05-28 | Alcon Manufacturing, Ltd. | Methods of treating ophthalmic, otic and nasal infections and attendant inflammation |
| CN1332962C (zh) * | 2005-07-12 | 2007-08-22 | 武汉人福药业有限责任公司 | 一种合成甲磺酸帕珠沙星中间体的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3055894A (en) * | 1960-03-09 | 1962-09-25 | Pfizer & Co C | New heterocyclic amides |
| US3551565A (en) * | 1968-04-26 | 1970-12-29 | Geigy Chem Corp | Pharmaceutical compositions and uses of oxazinoisoquinoline derivatives |
| US3966743A (en) * | 1968-07-23 | 1976-06-29 | Boehringer Mannheim G.M.B.H. | Ortho fused cycloalkano-4-quinolone-3-carboxylic acid derivatives |
| US3984548A (en) * | 1974-02-11 | 1976-10-05 | Riker Laboratories, Inc. | Substituted pyrido[1,2,3,-de]-1,4-benzoxazines as bactericides |
| US3883522A (en) * | 1974-02-11 | 1975-05-13 | Riker Laboratories Inc | Substituted pyrido(1,2,3-de)-1,4-benzoxazines |
| JPS5746986A (en) * | 1980-09-02 | 1982-03-17 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazine derivative |
| FR2593810B1 (fr) * | 1986-01-24 | 1988-04-22 | Sanofi Sa | Derives de la quinoleine, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant |
| JPH02157282A (ja) * | 1988-12-12 | 1990-06-18 | Wakunaga Pharmaceut Co Ltd | 新規ピリドベンゾオキサジン誘導体 |
| GB2236751B (en) * | 1989-10-14 | 1993-04-28 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| TW222276B (en, 2012) * | 1992-01-27 | 1994-04-11 | Fujisawa Pharmaceutical Co |
-
1994
- 1994-07-11 DE DE4424369A patent/DE4424369A1/de not_active Withdrawn
-
1995
- 1995-06-28 AU AU29256/95A patent/AU684651B2/en not_active Ceased
- 1995-06-28 EP EP95924949A patent/EP0770083B1/de not_active Expired - Lifetime
- 1995-06-28 HU HU9700075A patent/HUT77138A/hu unknown
- 1995-06-28 NZ NZ289419A patent/NZ289419A/en unknown
- 1995-06-28 CA CA002194694A patent/CA2194694A1/en not_active Abandoned
- 1995-06-28 AT AT95924949T patent/ATE195941T1/de not_active IP Right Cessation
- 1995-06-28 US US08/765,212 patent/US5854241A/en not_active Expired - Fee Related
- 1995-06-28 DK DK95924949T patent/DK0770083T3/da active
- 1995-06-28 JP JP8504083A patent/JPH10502377A/ja active Pending
- 1995-06-28 PL PL95318097A patent/PL318097A1/xx unknown
- 1995-06-28 DE DE59508689T patent/DE59508689D1/de not_active Expired - Fee Related
- 1995-06-28 BR BR9508384A patent/BR9508384A/pt not_active IP Right Cessation
- 1995-06-28 KR KR1019970700058A patent/KR100372978B1/ko not_active Expired - Fee Related
- 1995-06-28 CN CN95194072A patent/CN1086706C/zh not_active Expired - Fee Related
- 1995-06-28 CZ CZ9756A patent/CZ5697A3/cs unknown
- 1995-06-28 ES ES95924949T patent/ES2150576T3/es not_active Expired - Lifetime
- 1995-06-28 WO PCT/EP1995/002510 patent/WO1996001829A1/de active IP Right Grant
- 1995-06-28 MX MX9700306A patent/MX9700306A/es unknown
- 1995-06-28 SK SK27-97A patent/SK2797A3/sk unknown
- 1995-06-30 TW TW084106729A patent/TW319766B/zh active
- 1995-07-07 IL IL11449995A patent/IL114499A0/xx unknown
- 1995-07-10 ZA ZA955707A patent/ZA955707B/xx unknown
-
1997
- 1997-01-09 FI FI970092A patent/FI970092A0/fi unknown
- 1997-01-09 NO NO970079A patent/NO970079L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE59508689D1 (de) | 2000-10-05 |
| HU9700075D0 (en) | 1997-02-28 |
| EP0770083B1 (de) | 2000-08-30 |
| NZ289419A (en) | 1998-09-24 |
| HUT77138A (hu) | 1998-03-02 |
| ATE195941T1 (de) | 2000-09-15 |
| ZA955707B (en) | 1996-02-21 |
| BR9508384A (pt) | 1997-12-23 |
| CZ5697A3 (en) | 1997-05-14 |
| MX9700306A (es) | 1997-05-31 |
| WO1996001829A1 (de) | 1996-01-25 |
| DE4424369A1 (de) | 1996-01-18 |
| FI970092A7 (fi) | 1997-01-09 |
| NO970079D0 (no) | 1997-01-09 |
| CA2194694A1 (en) | 1996-01-25 |
| ES2150576T3 (es) | 2000-12-01 |
| JPH10502377A (ja) | 1998-03-03 |
| FI970092A0 (fi) | 1997-01-09 |
| CN1152921A (zh) | 1997-06-25 |
| SK2797A3 (en) | 1997-07-09 |
| AU2925695A (en) | 1996-02-09 |
| KR100372978B1 (ko) | 2003-06-12 |
| DK0770083T3 (da) | 2000-10-16 |
| NO970079L (no) | 1997-01-09 |
| US5854241A (en) | 1998-12-29 |
| IL114499A0 (en) | 1995-11-27 |
| PL318097A1 (en) | 1997-05-12 |
| CN1086706C (zh) | 2002-06-26 |
| AU684651B2 (en) | 1997-12-18 |
| EP0770083A1 (de) | 1997-05-02 |
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