JPS58966A - 抗菌性ナフチリジンおよびキノリン化合物の塩 - Google Patents
抗菌性ナフチリジンおよびキノリン化合物の塩Info
- Publication number
- JPS58966A JPS58966A JP57098576A JP9857682A JPS58966A JP S58966 A JPS58966 A JP S58966A JP 57098576 A JP57098576 A JP 57098576A JP 9857682 A JP9857682 A JP 9857682A JP S58966 A JPS58966 A JP S58966A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- compound
- ethyl
- oxo
- gluconate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 title claims description 37
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 11
- -1 quinoline compound Chemical class 0.000 title description 8
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 title 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 111
- 239000002253 acid Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 41
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 38
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 36
- 229940050410 gluconate Drugs 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 24
- 235000012208 gluconic acid Nutrition 0.000 claims description 24
- 239000000174 gluconic acid Substances 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 13
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 10
- 235000003704 aspartic acid Nutrition 0.000 claims description 8
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
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- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 229940009098 aspartate Drugs 0.000 claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 claims 3
- 150000002736 metal compounds Chemical class 0.000 claims 2
- 229930182830 galactose Natural products 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 229950006191 gluconic acid Drugs 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000006201 parenteral dosage form Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 10
- 239000002775 capsule Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
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- 238000000354 decomposition reaction Methods 0.000 description 8
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- 150000007513 acids Chemical class 0.000 description 7
- 229960005261 aspartic acid Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 239000006186 oral dosage form Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- 239000003153 chemical reaction reagent Substances 0.000 description 5
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- 238000001990 intravenous administration Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000036765 blood level Effects 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 125000000422 delta-lactone group Chemical group 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 4
- 229940049906 glutamate Drugs 0.000 description 4
- 229930195712 glutamate Natural products 0.000 description 4
- 229960002989 glutamic acid Drugs 0.000 description 4
- 239000004220 glutamic acid Substances 0.000 description 4
- 235000013922 glutamic acid Nutrition 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 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 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 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 2
- 239000005973 Carvone Substances 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
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- 235000011187 glycerol Nutrition 0.000 description 2
- 229960000443 hydrochloric acid Drugs 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 229960000448 lactic acid Drugs 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003182 parenteral nutrition solution Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- HOZBSSWDEKVXNO-BXRBKJIMSA-N (2s)-2-azanylbutanedioic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O.OC(=O)[C@@H](N)CC(O)=O HOZBSSWDEKVXNO-BXRBKJIMSA-N 0.000 description 1
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
- GXTSEMWAXIHJOM-UHFFFAOYSA-N 7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C1=CC2=CC(C(=O)O)=CN=C2C=C1N1CCNCC1 GXTSEMWAXIHJOM-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- RGHNJXZEOKUKBD-MGCNEYSASA-N D-galactonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-MGCNEYSASA-N 0.000 description 1
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-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
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- 241001465754 Metazoa Species 0.000 description 1
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- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
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- 241000194017 Streptococcus Species 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
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- 208000003443 Unconsciousness Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- GAMPNQJDUFQVQO-UHFFFAOYSA-N acetic acid;phthalic acid Chemical compound CC(O)=O.OC(=O)C1=CC=CC=C1C(O)=O GAMPNQJDUFQVQO-UHFFFAOYSA-N 0.000 description 1
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000003242 anti bacterial agent Substances 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
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- 239000000969 carrier Substances 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
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- 239000008103 glucose Substances 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
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- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- UJKDYMOBUGTJLZ-RUCXOUQFSA-N ksc605q1h Chemical compound OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CCC(O)=O UJKDYMOBUGTJLZ-RUCXOUQFSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
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- 235000019446 polyethylene glycol 8000 Nutrition 0.000 description 1
- 229940085678 polyethylene glycol 8000 Drugs 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Landscapes
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27260181A | 1981-06-11 | 1981-06-11 | |
| US272601 | 1981-06-11 | ||
| US334182 | 1981-12-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58966A true JPS58966A (ja) | 1983-01-06 |
| JPH0315632B2 JPH0315632B2 (en, 2012) | 1991-03-01 |
Family
ID=23040486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57098576A Granted JPS58966A (ja) | 1981-06-11 | 1982-06-10 | 抗菌性ナフチリジンおよびキノリン化合物の塩 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS58966A (en, 2012) |
| ZA (1) | ZA824096B (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500200A (en) * | 1984-12-06 | 1996-03-19 | Hyperion Catalysis International, Inc. | Fibrils |
| JP2010523649A (ja) * | 2007-04-13 | 2010-07-15 | ドン ファ ファーマシューティカル カンパニー リミテッド | １−シクロプロピル−６−フルオロ−７−（８−メトキシイミノ−２，６−ジアザ−スピロ［３．４］オクト−６−イル）−４−オキソ−１，４−ジヒドロ−［１，８］ナフチリジン−３−カルボン酸のアスパラギンサン酸塩、その製造方法、およびそれを含む抗菌用薬学組成物 |
| JP2013500251A (ja) * | 2009-07-27 | 2013-01-07 | アリメド インコーポレーテッド | Ｒ−７−（３−アミノメチル−４−メトキシイミノ−３−メチル−ピロリジン−１−イル）−１−シクロプロピル−６−フルオロ−４−オキソ−１，４−ジヒドロ−［１，８］ナフチリジン−３−カルボキシル酸ｌ−アスパラギン酸塩、その製造方法及びこれを含む抗菌用薬学的組成物 |
-
1982
- 1982-06-10 JP JP57098576A patent/JPS58966A/ja active Granted
- 1982-06-10 ZA ZA824096A patent/ZA824096B/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500200A (en) * | 1984-12-06 | 1996-03-19 | Hyperion Catalysis International, Inc. | Fibrils |
| US6375917B1 (en) | 1984-12-06 | 2002-04-23 | Hyperion Catalysis International, Inc. | Apparatus for the production of carbon fibrils by catalysis and methods thereof |
| JP2010523649A (ja) * | 2007-04-13 | 2010-07-15 | ドン ファ ファーマシューティカル カンパニー リミテッド | １−シクロプロピル−６−フルオロ−７−（８−メトキシイミノ−２，６−ジアザ−スピロ［３．４］オクト−６−イル）−４−オキソ−１，４−ジヒドロ−［１，８］ナフチリジン−３−カルボン酸のアスパラギンサン酸塩、その製造方法、およびそれを含む抗菌用薬学組成物 |
| JP2013500251A (ja) * | 2009-07-27 | 2013-01-07 | アリメド インコーポレーテッド | Ｒ−７−（３−アミノメチル−４−メトキシイミノ−３−メチル−ピロリジン−１−イル）−１−シクロプロピル−６−フルオロ−４−オキソ−１，４−ジヒドロ−［１，８］ナフチリジン−３−カルボキシル酸ｌ−アスパラギン酸塩、その製造方法及びこれを含む抗菌用薬学的組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA824096B (en) | 1983-04-27 |
| JPH0315632B2 (en, 2012) | 1991-03-01 |
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