DD240016A5 - Verfahren zur herstellung von 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeuren - Google Patents
Verfahren zur herstellung von 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeuren Download PDFInfo
- Publication number
- DD240016A5 DD240016A5 DD85276974A DD27697485A DD240016A5 DD 240016 A5 DD240016 A5 DD 240016A5 DD 85276974 A DD85276974 A DD 85276974A DD 27697485 A DD27697485 A DD 27697485A DD 240016 A5 DD240016 A5 DD 240016A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxo
- cyclopropyl
- piperazinyl
- dihydro
- formula
- Prior art date
Links
- -1 1-PIPERAZINYL Chemical class 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 239000011737 fluorine Chemical group 0.000 claims abstract description 15
- 229910052731 fluorine Chemical group 0.000 claims abstract description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000005188 oxoalkyl group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 150000004677 hydrates Chemical class 0.000 claims abstract description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004885 piperazines Chemical class 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical class C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 14
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000013543 active substance Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 6
- XWCKIXLTBNGIHV-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoyl chloride Chemical compound FC1=CC(C(Cl)=O)=C(F)C(F)=C1F XWCKIXLTBNGIHV-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 5
- 229960001180 norfloxacin Drugs 0.000 description 5
- 244000052769 pathogen Species 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- RIMRLBGNCLMSNH-UHFFFAOYSA-N 2-phenylpiperazine Chemical compound C1NCCNC1C1=CC=CC=C1 RIMRLBGNCLMSNH-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 241000191940 Staphylococcus Species 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000588748 Klebsiella Species 0.000 description 3
- 241000588769 Proteus <enterobacteria> Species 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 230000001668 ameliorated effect Effects 0.000 description 3
- 235000012216 bentonite Nutrition 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- WFZMKGKYUACCTB-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-4-oxo-7-(3-phenylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C12=CC(N3CC(NCC3)C=3C=CC=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 WFZMKGKYUACCTB-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- TXALMWNWYDSWQO-UHFFFAOYSA-N 2,4,5-trifluorobenzoyl fluoride Chemical compound FC(=O)C1=CC(F)=C(F)C=C1F TXALMWNWYDSWQO-UHFFFAOYSA-N 0.000 description 2
- WWYFHDNQGVTJJJ-UHFFFAOYSA-N 2-cyclohexylpiperazine Chemical class C1CCCCC1C1NCCNC1 WWYFHDNQGVTJJJ-UHFFFAOYSA-N 0.000 description 2
- BFVCDPJJFUPNAQ-UHFFFAOYSA-N 2-thiophen-2-ylpiperazine Chemical compound C1NCCNC1C1=CC=CS1 BFVCDPJJFUPNAQ-UHFFFAOYSA-N 0.000 description 2
- VUHYROBFXQJOMM-UHFFFAOYSA-N 3-oxo-7-piperazin-1-yl-2h-quinoline-2-carboxylic acid Chemical compound C1=CC2=CC(=O)C(C(=O)O)N=C2C=C1N1CCNCC1 VUHYROBFXQJOMM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000588914 Enterobacter Species 0.000 description 2
- 241000588921 Enterobacteriaceae Species 0.000 description 2
- 241000192125 Firmicutes Species 0.000 description 2
- 241000206672 Gelidium Species 0.000 description 2
- 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 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000607720 Serratia Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 235000010215 titanium dioxide Nutrition 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- YBYFWABNVZMZGS-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-(3-phenylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(NCC3)C=3C=CC=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 YBYFWABNVZMZGS-UHFFFAOYSA-N 0.000 description 1
- FZGNZZSFHWQJNV-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-(3-thiophen-2-ylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(NCC3)C=3SC=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 FZGNZZSFHWQJNV-UHFFFAOYSA-N 0.000 description 1
- BMAKQOOEAMDNGD-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-(4-formyl-3-thiophen-2-ylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(N(C=O)CC3)C=3SC=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 BMAKQOOEAMDNGD-UHFFFAOYSA-N 0.000 description 1
- VKQFFKFLBVCBLL-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-4-oxo-7-[3-(3,4,5-trimethoxyphenyl)piperazin-1-yl]quinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C2NCCN(C2)C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)=C1 VKQFFKFLBVCBLL-UHFFFAOYSA-N 0.000 description 1
- KMGTUXQAENRADC-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-(4-methyl-3-phenylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound CN1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1C1=CC=CC=C1 KMGTUXQAENRADC-UHFFFAOYSA-N 0.000 description 1
- TWCZVQCYGNEACG-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-[4-(2-hydroxyethyl)-3-phenylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound OCCN1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1C1=CC=CC=C1 TWCZVQCYGNEACG-UHFFFAOYSA-N 0.000 description 1
- LJEFAPGPJISENB-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethyl-3-phenylpiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound CCN1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1C1=CC=CC=C1 LJEFAPGPJISENB-UHFFFAOYSA-N 0.000 description 1
- SZESLTPCOVTJOL-UHFFFAOYSA-N 1-cyclopropyl-7-fluoro-4-oxoquinoline-3-carboxylic acid Chemical class C12=CC(F)=CC=C2C(=O)C(C(=O)O)=CN1C1CC1 SZESLTPCOVTJOL-UHFFFAOYSA-N 0.000 description 1
- SFKRXQKJTIYUAG-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(F)=C1F SFKRXQKJTIYUAG-UHFFFAOYSA-N 0.000 description 1
- ZYEWNAMVVRPNJX-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoyl fluoride Chemical compound FC(=O)C1=CC(F)=C(F)C(F)=C1F ZYEWNAMVVRPNJX-UHFFFAOYSA-N 0.000 description 1
- AKAMNXFLKYKFOJ-UHFFFAOYSA-N 2,4,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C=C1F AKAMNXFLKYKFOJ-UHFFFAOYSA-N 0.000 description 1
- IFBLQYWVJXGZPY-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)piperazine Chemical compound C1=C2OCOC2=CC=C1C1CNCCN1 IFBLQYWVJXGZPY-UHFFFAOYSA-N 0.000 description 1
- SZZIGSBHEDAVBX-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)piperazine Chemical compound COC1=C(OC)C(OC)=CC(C2NCCNC2)=C1 SZZIGSBHEDAVBX-UHFFFAOYSA-N 0.000 description 1
- XMTDOVQYBQWJAL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)piperazine Chemical compound C1=C(OC)C(OC)=CC=C1C1NCCNC1 XMTDOVQYBQWJAL-UHFFFAOYSA-N 0.000 description 1
- VGANTLKDSNLDDD-UHFFFAOYSA-N 2-(3-nitrophenyl)piperazine Chemical compound [O-][N+](=O)C1=CC=CC(C2NCCNC2)=C1 VGANTLKDSNLDDD-UHFFFAOYSA-N 0.000 description 1
- ZXWFFOCOSVMOPB-UHFFFAOYSA-N 2-(4-bromophenyl)piperazine Chemical compound C1=CC(Br)=CC=C1C1NCCNC1 ZXWFFOCOSVMOPB-UHFFFAOYSA-N 0.000 description 1
- OTOVNNDSINVUBR-UHFFFAOYSA-N 2-(4-chlorophenyl)piperazine Chemical compound C1=CC(Cl)=CC=C1C1NCCNC1 OTOVNNDSINVUBR-UHFFFAOYSA-N 0.000 description 1
- NZAKSEMIIIZYEM-UHFFFAOYSA-N 2-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1C1NCCNC1 NZAKSEMIIIZYEM-UHFFFAOYSA-N 0.000 description 1
- INKLSJITWMAFRT-UHFFFAOYSA-N 2-(4-methoxyphenyl)piperazine Chemical compound C1=CC(OC)=CC=C1C1NCCNC1 INKLSJITWMAFRT-UHFFFAOYSA-N 0.000 description 1
- FCNXNUWTNOYQME-UHFFFAOYSA-N 2-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1C1NCCNC1 FCNXNUWTNOYQME-UHFFFAOYSA-N 0.000 description 1
- WWRUGVIJFUXWFW-UHFFFAOYSA-N 2-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1NCCNC1 WWRUGVIJFUXWFW-UHFFFAOYSA-N 0.000 description 1
- MUECOXPJCJWOTK-UHFFFAOYSA-N 2-(4-phenylmethoxyphenyl)piperazine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1C1CNCCN1 MUECOXPJCJWOTK-UHFFFAOYSA-N 0.000 description 1
- QUINYTMXFWCKTN-UHFFFAOYSA-N 2-(4-phenylphenyl)piperazine Chemical compound C1NCCNC1C1=CC=C(C=2C=CC=CC=2)C=C1 QUINYTMXFWCKTN-UHFFFAOYSA-N 0.000 description 1
- HIEDNYNFVIKPKN-UHFFFAOYSA-N 2-(4-piperidin-1-ylphenyl)piperazine Chemical compound C1CCCCN1C1=CC=C(C2NCCNC2)C=C1 HIEDNYNFVIKPKN-UHFFFAOYSA-N 0.000 description 1
- LOKVZWIGUJYFLY-UHFFFAOYSA-N 2-(furan-2-yl)piperazine Chemical compound C1NCCNC1C1=CC=CO1 LOKVZWIGUJYFLY-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- OCGGVAKKHYAFJW-UHFFFAOYSA-N 2-piperazin-2-ylphenol Chemical compound OC1=CC=CC=C1C1NCCNC1 OCGGVAKKHYAFJW-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-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
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- QFOVQRZDLIWFLD-UHFFFAOYSA-N 3-oxo-3-(2,4,5-trifluorophenyl)propanoic acid Chemical compound OC(=O)CC(=O)C1=CC(F)=C(F)C=C1F QFOVQRZDLIWFLD-UHFFFAOYSA-N 0.000 description 1
- DCIVTGUMDABITM-UHFFFAOYSA-N 3-piperazin-2-ylphenol Chemical compound OC1=CC=CC(C2NCCNC2)=C1 DCIVTGUMDABITM-UHFFFAOYSA-N 0.000 description 1
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- OVPROXCERHBLGN-UHFFFAOYSA-N 4-piperazin-2-ylaniline Chemical compound C1=CC(N)=CC=C1C1NCCNC1 OVPROXCERHBLGN-UHFFFAOYSA-N 0.000 description 1
- XIBWDDFMRMJKHQ-UHFFFAOYSA-N 4-piperazin-2-ylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1NCCNC1 XIBWDDFMRMJKHQ-UHFFFAOYSA-N 0.000 description 1
- SASIFHOHGBPKMK-UHFFFAOYSA-N 4-piperazin-2-ylphenol Chemical compound C1=CC(O)=CC=C1C1NCCNC1 SASIFHOHGBPKMK-UHFFFAOYSA-N 0.000 description 1
- DBWZVKBBIHZJDP-UHFFFAOYSA-N 7-(4-acetyl-3-phenylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound CC(=O)N1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1C1=CC=CC=C1 DBWZVKBBIHZJDP-UHFFFAOYSA-N 0.000 description 1
- FDGPRVDELSLIQF-UHFFFAOYSA-N 7-(4-butyl-3-phenylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound CCCCN1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1C1=CC=CC=C1 FDGPRVDELSLIQF-UHFFFAOYSA-N 0.000 description 1
- NMYSKEULMDDBJM-UHFFFAOYSA-N 7-[3-(4-cyanophenyl)piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CC(NCC3)C=3C=CC(=CC=3)C#N)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 NMYSKEULMDDBJM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241000606126 Bacteroidaceae Species 0.000 description 1
- 241000606125 Bacteroides Species 0.000 description 1
- 241001261624 Brevundimonas bacteroides Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000192017 Micrococcaceae Species 0.000 description 1
- 241000219470 Mirabilis Species 0.000 description 1
- 241001430197 Mollicutes Species 0.000 description 1
- 241000186362 Mycobacterium leprae Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 208000001572 Mycoplasma Pneumonia Diseases 0.000 description 1
- 201000008235 Mycoplasma pneumoniae pneumonia Diseases 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 241000588768 Providencia Species 0.000 description 1
- 241000947836 Pseudomonadaceae Species 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 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 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HPMLGNIUXVXALD-UHFFFAOYSA-N benzoyl fluoride Chemical compound FC(=O)C1=CC=CC=C1 HPMLGNIUXVXALD-UHFFFAOYSA-N 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- WNSKAEJGWQCOQH-UHFFFAOYSA-N diethyl 2-(2,3,4,5-tetrafluorobenzoyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C1=CC(F)=C(F)C(F)=C1F WNSKAEJGWQCOQH-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 206010014665 endocarditis Diseases 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- UCKBRIDVNDEKNN-VURMDHGXSA-N ethyl (z)-3-ethoxy-2-(2,3,4,5-tetrafluorobenzoyl)prop-2-enoate Chemical compound CCO\C=C(/C(=O)OCC)C(=O)C1=CC(F)=C(F)C(F)=C1F UCKBRIDVNDEKNN-VURMDHGXSA-N 0.000 description 1
- JMEHSOLNHBTJLF-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-(2,3,4,5-tetrafluorobenzoyl)prop-2-enoate Chemical compound C=1C(F)=C(F)C(F)=C(F)C=1C(=O)C(C(=O)OCC)=CNC1CC1 JMEHSOLNHBTJLF-UHFFFAOYSA-N 0.000 description 1
- KWDVJYLIAJHEOW-UHFFFAOYSA-N ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propanoate Chemical compound CCOC(=O)CC(=O)C1=CC(F)=C(F)C(F)=C1F KWDVJYLIAJHEOW-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 229940044949 eucalyptus oil Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- 229940074076 glycerol formal Drugs 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 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
- 239000003906 humectant Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- XDKQUSKHRIUJEO-UHFFFAOYSA-N magnesium;ethanolate Chemical compound [Mg+2].CC[O-].CC[O-] XDKQUSKHRIUJEO-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- TZBAVQKIEKDGFH-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-1-benzothiophene-2-carboxamide;hydrochloride Chemical compound [Cl-].C1=CC=C2SC(C(=O)NCC[NH+](CC)CC)=CC2=C1 TZBAVQKIEKDGFH-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- MJEQGDCEXYIIQX-UHFFFAOYSA-N quinoline-2-carboxylic acid hydrobromide Chemical compound Br.N1=C(C=CC2=CC=CC=C12)C(=O)O MJEQGDCEXYIIQX-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 229940076156 streptococcus pyogenes Drugs 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843420798 DE3420798A1 (de) | 1984-06-04 | 1984-06-04 | 7-(3-aryl-l-piperazinyl)- sowie 7-(3-cyclohexyl-l-piperazinyl)-3-chinoloncarbonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD240016A5 true DD240016A5 (de) | 1986-10-15 |
Family
ID=6237597
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85276974A DD240016A5 (de) | 1984-06-04 | 1985-06-03 | Verfahren zur herstellung von 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-chinolincarbonsaeuren |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4599334A (enExample) |
| EP (1) | EP0169993B1 (enExample) |
| JP (2) | JPS611683A (enExample) |
| KR (1) | KR920000759B1 (enExample) |
| AT (1) | ATE39488T1 (enExample) |
| AU (1) | AU571333B2 (enExample) |
| CA (1) | CA1248954A (enExample) |
| DD (1) | DD240016A5 (enExample) |
| DE (2) | DE3420798A1 (enExample) |
| DK (1) | DK162527C (enExample) |
| ES (3) | ES8607294A1 (enExample) |
| FI (1) | FI82041C (enExample) |
| GR (1) | GR851314B (enExample) |
| HU (1) | HU194866B (enExample) |
| IE (1) | IE57814B1 (enExample) |
| IL (1) | IL75370A (enExample) |
| NO (1) | NO165105C (enExample) |
| NZ (1) | NZ212271A (enExample) |
| PH (1) | PH22492A (enExample) |
| PT (1) | PT80580B (enExample) |
| ZA (1) | ZA854168B (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3420743A1 (de) * | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| US5468861A (en) * | 1984-06-04 | 1995-11-21 | Bayer Aktiengesellschaft | 8-chloro-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and alkyl esters thereof |
| JPS6259263A (ja) * | 1985-09-10 | 1987-03-14 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
| JPH0637489B2 (ja) * | 1985-09-21 | 1994-05-18 | 杏林製薬株式会社 | キノロンカルボン酸誘導体およびその製造方法 |
| DE3683922D1 (de) * | 1985-09-24 | 1992-03-26 | Hoffmann La Roche | Chinolinderivate. |
| AU594983B2 (en) * | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
| DE3542002A1 (de) * | 1985-11-28 | 1987-06-04 | Bayer Ag | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| EP0230053A3 (en) * | 1986-01-17 | 1988-03-30 | American Cyanamid Company | 7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
| HU204512B (en) * | 1986-01-20 | 1992-01-28 | Kyorin Seiyaku Kk | New process for producing quinoline-carboxylic acid derivatives |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| US4689423A (en) * | 1986-04-01 | 1987-08-25 | Warner-Lambert Company | Process for the preparation of 2,3,4,5-tetrafluorobenzoyl acetates |
| HU196987B (en) * | 1986-10-15 | 1989-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| DE3639465A1 (de) * | 1986-11-18 | 1988-05-19 | Hoechst Ag | Optisch aktive gyrasehemmer, ihre herstellung und verwendung als antibiotika |
| NZ229605A (en) * | 1988-07-15 | 1990-07-26 | Abbott Lab | Preparation of 1,4-dihydro-6-fluoro-7-(piperazin-1-yl)-4-oxo-3-quinoline (or naphthyridine) carboxylic acid derivatives |
| FR2664595B1 (fr) * | 1990-07-10 | 1992-09-18 | Bellon Labor Sa Roger | Nouveaux derives de benzonaphtyridine-1,8, leur preparation et les compositions qui les contiennent. |
| FR2653663A1 (en) * | 1989-10-30 | 1991-05-03 | Bellon Labor Sa Roger | Novel benzo[1,8]naphthyridine derivatives, their preparation and compositions containing them |
| RO108347B1 (ro) * | 1989-10-30 | 1994-04-28 | Bellon Labor Sa Roger | DERIVATI DE BENZO-(b)-NAFTIRIDIN-1,8 SI PROCEDEU DE PREPARARE A ACESTORA |
| EP0449445A3 (en) * | 1990-03-27 | 1993-08-25 | Pfizer Inc. | Preparation of beta-ketoesters useful in preparing quinolone antibiotics |
| JPH05506033A (ja) | 1990-04-18 | 1993-09-02 | ノーウィッチ、イートン、ファーマスーティカルズ、インコーポレーテッド | 抗微生物性キノロニルラクタム類 |
| DE10108750A1 (de) * | 2001-02-23 | 2002-09-05 | Bayer Ag | Verbessertes Verfahren zur Herstellung von Fluorchinoloncarbonsäuren |
| KR100519158B1 (ko) * | 2002-12-21 | 2005-10-06 | 주식회사유한양행 | 퀴놀론 카르복실레이트 유도체의 제조방법 |
| DK2001862T3 (da) * | 2006-03-28 | 2011-08-08 | Warner Chilcott Co Llc | Malatsalte og polymorfe af (3S,5S)-7-[3-amino-5-methyl-piperidinyl]-1-cyklopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolincarboxylsyre |
| BRPI0709220A2 (pt) * | 2006-03-28 | 2011-07-12 | Procter & Gamble | processo de acoplamento para preparo de intermediários de quinolona |
| PE20201257A1 (es) | 2018-04-25 | 2020-11-16 | Bayer Animal Health Gmbh | Proceso para la hidrolisis de esteres carboxilicos de quinolona |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3142854A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-piperazino-chinolin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| SE440354B (sv) * | 1981-02-19 | 1985-07-29 | Kyorin Seiyaku Kk | Kinolinkarboxylsyraderivat |
| DE3142856A1 (de) * | 1981-10-29 | 1983-05-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 2,4-dichlor-5-fluor-benzoylchlorid |
| JPS5910580A (ja) * | 1982-07-09 | 1984-01-20 | Hokuriku Seiyaku Co Ltd | ７−フエニル置換ピペラジノ−４−オキソ−１，４−ジヒドロキノリン−３−カルボン酸誘導体 |
| JPS5929685A (ja) * | 1982-08-11 | 1984-02-16 | Hokuriku Seiyaku Co Ltd | ７−置換フエニルピペラジノ−４−オキソ−１，４−ジヒドロキノリン−３−カルボン酸誘導体 |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| DE3248506A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7(alkyl-1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3248507A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | Mikrobizide mittel auf chinoloncarbonsaeure basis |
| DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3318145A1 (de) * | 1983-05-18 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
-
1984
- 1984-06-04 DE DE19843420798 patent/DE3420798A1/de not_active Withdrawn
-
1985
- 1985-05-17 US US06/735,493 patent/US4599334A/en not_active Expired - Fee Related
- 1985-05-22 EP EP85106252A patent/EP0169993B1/de not_active Expired
- 1985-05-22 DE DE8585106252T patent/DE3567021D1/de not_active Expired
- 1985-05-22 AT AT85106252T patent/ATE39488T1/de active
- 1985-05-23 NO NO852063A patent/NO165105C/no unknown
- 1985-05-27 PH PH32319A patent/PH22492A/en unknown
- 1985-05-29 GR GR851314A patent/GR851314B/el unknown
- 1985-05-31 NZ NZ212271A patent/NZ212271A/xx unknown
- 1985-05-31 FI FI852205A patent/FI82041C/fi not_active IP Right Cessation
- 1985-05-31 IE IE1364/85A patent/IE57814B1/en not_active IP Right Cessation
- 1985-05-31 AU AU43206/85A patent/AU571333B2/en not_active Ceased
- 1985-05-31 CA CA000482912A patent/CA1248954A/en not_active Expired
- 1985-05-31 IL IL75370A patent/IL75370A/xx unknown
- 1985-05-31 JP JP60116836A patent/JPS611683A/ja active Pending
- 1985-06-03 DK DK249685A patent/DK162527C/da not_active IP Right Cessation
- 1985-06-03 ES ES543839A patent/ES8607294A1/es not_active Expired
- 1985-06-03 ZA ZA854168A patent/ZA854168B/xx unknown
- 1985-06-03 PT PT80580A patent/PT80580B/pt not_active IP Right Cessation
- 1985-06-03 HU HU852145A patent/HU194866B/hu not_active IP Right Cessation
- 1985-06-03 DD DD85276974A patent/DD240016A5/de not_active IP Right Cessation
- 1985-06-03 KR KR1019850003855A patent/KR920000759B1/ko not_active Expired
-
1986
- 1986-02-28 ES ES552573A patent/ES8800195A1/es not_active Expired
- 1986-02-28 ES ES552574A patent/ES8800196A1/es not_active Expired
-
1993
- 1993-12-15 JP JP5342256A patent/JPH06279411A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0126355B1 (de) | 7-Amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| EP0169993B1 (de) | 7-(3-Aryl-1-piperazinyl)-sowie 7-(3-Cyclohexyl-1-piperazinyl)-3-chinoloncarbonsäuren | |
| EP0167763B1 (de) | 7-Amino-1-cyclopropyl-6,8-dihalogen-1,4-dihydro-4-oxo-3-chinolincarbonsäuren, Verfahren zur ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| EP0198192B1 (de) | 7-Amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| EP0113093B1 (de) | 1-Cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(alkyl-1-piperazinyl)-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| EP0164619B1 (de) | 2,4,5-Trihalogen- bzw. 2,3,4,5-Tetrahalogenbenzolderivate und Verfahren zu ihrer Herstellung | |
| EP0155587B1 (de) | 1,7-Diamino-1,4-dihydro-4-oxo-3-(aza) chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie ihre Verwendung bei der Bekämpfung bakterieller Erkrankungen | |
| EP0276700A1 (de) | 8-Cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung und diese enthaltende antibakterielle Mittel | |
| DE3522406A1 (de) | Verfahren zur herstellung von 1,8-verbrueckten 4-chinolon-3-carbonsaeuren | |
| EP0187376B1 (de) | 6,7-Disubstituierte 1-Cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridin-3-carbonsäuren | |
| EP0113092B1 (de) | 1-Cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(4-(oxoalkyl)-1-piperazinyl)-3-chinolincarbonsäuren und ihre Derivate, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| EP0205029A2 (de) | Antibakteriell wirksame Chinoloncarbonsäureester | |
| EP0201829A1 (de) | 1-Aryl-4-chinolon-3-carbonsäuren | |
| EP0166939B1 (de) | 1-Cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(3-oxo-1-piperazinyl)-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| EP0191390B1 (de) | 1-Cyclopropyl-1,4-dihydro-4-oxo-7-[4-(2-oxo-1,3-dioxol-4-yl-methyl)-1-piperazinyl]-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel | |
| DE3542002A1 (de) | 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel | |
| DE3543513A1 (de) | Enantiomerenreine 1,8-verbrueckte 4-chinolon-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel und ihre verwendung zur herstellung von arzneimitteln | |
| DD241258A5 (de) | Verfahren zur herstellung 6,7-disubstituierter 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphthyridin-3-carbonsaeuren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |