FI71144C - Foerfarande foer framstaellning av terapeutiskt aktiv 1-etyl-6-fluor-1,4-dihydro-4-oxo-(1-piperazinyl)-1,8-naftyridin-3-karboxylsyraseskvihydrat - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiv 1-etyl-6-fluor-1,4-dihydro-4-oxo-(1-piperazinyl)-1,8-naftyridin-3-karboxylsyraseskvihydrat Download PDFInfo
- Publication number
- FI71144C FI71144C FI820466A FI820466A FI71144C FI 71144 C FI71144 C FI 71144C FI 820466 A FI820466 A FI 820466A FI 820466 A FI820466 A FI 820466A FI 71144 C FI71144 C FI 71144C
- Authority
- FI
- Finland
- Prior art keywords
- piperazinyl
- fluoro
- dihydro
- oxo
- naphthyridine
- Prior art date
Links
- -1 1-PIPERAZINYL Chemical class 0.000 title claims description 22
- 230000001225 therapeutic effect Effects 0.000 title claims 2
- 230000003213 activating effect Effects 0.000 title 1
- IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 claims description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
- 150000004684 trihydrates Chemical class 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 13
- 239000000725 suspension Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- DGNFGMQSESJJPM-UHFFFAOYSA-N CCN(C=C(C(OC(C(C(C1=C2)=O)=CN(CC)C1=NC(N1CCNCC1)=C2F)=O)=O)C(C1=C2)=O)C1=NC(N1CCNCC1)=C2F Chemical compound CCN(C=C(C(OC(C(C(C1=C2)=O)=CN(CC)C1=NC(N1CCNCC1)=C2F)=O)=O)C(C1=C2)=O)C1=NC(N1CCNCC1)=C2F DGNFGMQSESJJPM-UHFFFAOYSA-N 0.000 claims 8
- GNMIQQQKZXTFOL-UHFFFAOYSA-N 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid;trihydrate Chemical compound O.O.O.N1=C2N(CC)C=C(C([O-])=O)C(=O)C2=CC(F)=C1N1CC[NH2+]CC1 GNMIQQQKZXTFOL-UHFFFAOYSA-N 0.000 claims 2
- 210000000653 nervous system Anatomy 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 description 18
- 239000013078 crystal Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000002076 thermal analysis method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000000634 powder X-ray diffraction Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000004455 differential thermal analysis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- DKNNITGJCMPHKE-UHFFFAOYSA-N 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid;trihydrate Chemical compound O.O.O.N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1.N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 DKNNITGJCMPHKE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- SHCWQWRTKPNTEM-UHFFFAOYSA-N 2,6-dichloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1Cl SHCWQWRTKPNTEM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- APOUXKRSGOMQBC-UHFFFAOYSA-N CCN(C=CC(C1=C2)=O)C1=NC(N(CC1)CCN1C(OCC)=O)=C2F Chemical compound CCN(C=CC(C1=C2)=O)C1=NC(N(CC1)CCN1C(OCC)=O)=C2F APOUXKRSGOMQBC-UHFFFAOYSA-N 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
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 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
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000002835 absorbance Methods 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
- 238000007605 air drying Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 229940021013 electrolyte solution Drugs 0.000 description 1
- UDVGWVUGMCOVOI-UHFFFAOYSA-N ethyl 4-(6-acetamido-3-aminopyridin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=NC(NC(C)=O)=CC=C1N UDVGWVUGMCOVOI-UHFFFAOYSA-N 0.000 description 1
- PUSNQEMOWJWZQT-UHFFFAOYSA-N ethyl 4-(6-acetamido-3-fluoropyridin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=NC(NC(C)=O)=CC=C1F PUSNQEMOWJWZQT-UHFFFAOYSA-N 0.000 description 1
- JLZYNSUWKGHCOQ-UHFFFAOYSA-N ethyl 4-(6-acetamido-3-nitropyridin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=NC(NC(C)=O)=CC=C1[N+]([O-])=O JLZYNSUWKGHCOQ-UHFFFAOYSA-N 0.000 description 1
- LVIWVLLZMXHNRD-UHFFFAOYSA-N ethyl 4-(6-amino-3-fluoropyridin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=NC(N)=CC=C1F LVIWVLLZMXHNRD-UHFFFAOYSA-N 0.000 description 1
- AKMFLNXSGUYKJX-UHFFFAOYSA-N ethyl 4-(6-chloro-3-nitropyridin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=NC(Cl)=CC=C1[N+]([O-])=O AKMFLNXSGUYKJX-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56020749A JPS57134482A (en) | 1981-02-13 | 1981-02-13 | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation |
| JP2074981 | 1981-02-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI820466L FI820466L (fi) | 1982-08-14 |
| FI71144B FI71144B (fi) | 1986-08-14 |
| FI71144C true FI71144C (fi) | 1986-11-24 |
Family
ID=12035831
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI820466A FI71144C (fi) | 1981-02-13 | 1982-02-12 | Foerfarande foer framstaellning av terapeutiskt aktiv 1-etyl-6-fluor-1,4-dihydro-4-oxo-(1-piperazinyl)-1,8-naftyridin-3-karboxylsyraseskvihydrat |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4442101A (cs) |
| EP (1) | EP0058614B1 (cs) |
| JP (1) | JPS57134482A (cs) |
| KR (1) | KR870000322B1 (cs) |
| AU (1) | AU547082B2 (cs) |
| CA (1) | CA1216292A (cs) |
| CS (1) | CS254958B2 (cs) |
| DD (1) | DD202573A5 (cs) |
| DE (1) | DE3266261D1 (cs) |
| DK (1) | DK160046C (cs) |
| ES (1) | ES509538A0 (cs) |
| FI (1) | FI71144C (cs) |
| HU (1) | HU186473B (cs) |
| MX (1) | MX158194A (cs) |
| NO (1) | NO156721C (cs) |
| PH (1) | PH18177A (cs) |
| PL (1) | PL137259B1 (cs) |
| YU (1) | YU43785B (cs) |
| ZA (1) | ZA82740B (cs) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2758259A (en) * | 1953-06-23 | 1956-08-07 | Mallory & Co Inc P R | Electrolytic capacitor device |
| US2856570A (en) * | 1954-06-02 | 1958-10-14 | Mallory & Co Inc P R | Electrolytic capacitor |
| JPS57134482A (en) * | 1981-02-13 | 1982-08-19 | Dainippon Pharmaceut Co Ltd | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation |
| DE3308908A1 (de) * | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel |
| US4639458A (en) * | 1985-01-22 | 1987-01-27 | Merck & Co., Inc. | Tablet and formulation |
| HUT40429A (en) * | 1985-04-29 | 1986-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for production of salts of derivatives of kynolin carbonic acid |
| US5422350A (en) * | 1992-09-10 | 1995-06-06 | Warner-Lambert Company | Nitrogen substituted acridine and cytochrome P450 inhibitors and methods of use |
| US5466696A (en) * | 1992-09-10 | 1995-11-14 | Warner Lambert Company | Tacrine and cytochrome P450 oxidase inhibitors and methods of use |
| JP3449658B2 (ja) * | 1994-12-21 | 2003-09-22 | 杏林製薬株式会社 | 安定性に優れた８−アルコキシキノロンカルボン酸水和物並びにその製造方法 |
| GB9820405D0 (en) * | 1998-09-18 | 1998-11-11 | Smithkline Beecham Plc | Process |
| GB9920917D0 (en) | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel process |
| GB9920919D0 (en) | 1999-09-03 | 1999-11-10 | Sb Pharmco Inc | Novel compound |
| KR100517638B1 (ko) | 2002-04-08 | 2005-09-28 | 주식회사 엘지생명과학 | 게미플록사신 산염의 새로운 제조방법 |
| US7842791B2 (en) * | 2002-12-19 | 2010-11-30 | Nancy Jean Britten | Dispersible pharmaceutical compositions |
| US8629178B2 (en) * | 2009-11-03 | 2014-01-14 | Li Liu | Sodium tanshinone IIA sulfonate hydrate and preparation method and use thereof |
| EP2964652A4 (en) * | 2013-03-08 | 2016-10-12 | Melinta Therapeutics Inc | CRYSTALLINE FORMS OF D-GLUCITOL, 1-DEOXY-1- (METHYLAMINO) -, 1- (6-AMINO-3, 5-DIFLUORPYRIDIN-2-YL) -8-CHLORO-6-FLUORO-1, 4-DIHYDRO- 7- (3-hydroxyazetidine-1-yl) -4-oxo-3-QUINOLINECARBOXYLAT |
| KR102214067B1 (ko) | 2014-02-27 | 2021-02-09 | 엘지전자 주식회사 | 산 질화물 형광체, 그 제조 방법 및 이를 이용한 발광 소자 패키지 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3149104A (en) * | 1961-01-03 | 1964-09-15 | Sterling Drug Inc | 4-hydroxy-7-styryl-1, 8-naphthyridine-3-carboxylic acids and esters |
| US3590036A (en) * | 1968-11-18 | 1971-06-29 | George Y Lesher | Naphthyridine-3-carboxylic acids,their derivatives and preparation thereof |
| NL7101049A (cs) * | 1970-01-28 | 1971-07-30 | ||
| US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
| JPS53141286A (en) * | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
| AR223983A1 (es) * | 1978-08-25 | 1981-10-15 | Dainippon Pharmaceutical Co | Un procedimiento para-preparar derivados de acido 6-halogeno-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-carboxilico |
| JPS5845426B2 (ja) * | 1978-09-29 | 1983-10-08 | 杏林製薬株式会社 | 置換キノリンカルボン酸誘導体 |
| JPS57134482A (en) * | 1981-02-13 | 1982-08-19 | Dainippon Pharmaceut Co Ltd | 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8- naphthyridine-3-carboxylic acid-3/2 hydrate and its preparation |
-
1981
- 1981-02-13 JP JP56020749A patent/JPS57134482A/ja active Granted
-
1982
- 1982-02-03 AU AU80173/82A patent/AU547082B2/en not_active Expired
- 1982-02-04 US US06/345,916 patent/US4442101A/en not_active Expired - Lifetime
- 1982-02-05 ZA ZA82740A patent/ZA82740B/xx unknown
- 1982-02-08 YU YU265/82A patent/YU43785B/xx unknown
- 1982-02-11 EP EP82400247A patent/EP0058614B1/en not_active Expired
- 1982-02-11 DE DE8282400247T patent/DE3266261D1/de not_active Expired
- 1982-02-11 DD DD82237353A patent/DD202573A5/de not_active IP Right Cessation
- 1982-02-12 CA CA000396209A patent/CA1216292A/en not_active Expired
- 1982-02-12 PH PH26864A patent/PH18177A/en unknown
- 1982-02-12 HU HU82439A patent/HU186473B/hu unknown
- 1982-02-12 DK DK063482A patent/DK160046C/da not_active IP Right Cessation
- 1982-02-12 NO NO820430A patent/NO156721C/no not_active IP Right Cessation
- 1982-02-12 ES ES509538A patent/ES509538A0/es active Granted
- 1982-02-12 MX MX191383A patent/MX158194A/es unknown
- 1982-02-12 PL PL1982235049A patent/PL137259B1/pl unknown
- 1982-02-12 CS CS82998A patent/CS254958B2/cs unknown
- 1982-02-12 FI FI820466A patent/FI71144C/fi not_active IP Right Cessation
- 1982-02-13 KR KR8200633A patent/KR870000322B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK160046C (da) | 1991-06-10 |
| US4442101A (en) | 1984-04-10 |
| ES8307793A1 (es) | 1983-08-01 |
| NO156721C (no) | 1987-11-11 |
| YU43785B (en) | 1989-12-31 |
| DK63482A (da) | 1982-08-14 |
| FI71144B (fi) | 1986-08-14 |
| DK160046B (da) | 1991-01-21 |
| CS254958B2 (en) | 1988-02-15 |
| PL137259B1 (en) | 1986-05-31 |
| AU547082B2 (en) | 1985-10-03 |
| AU8017382A (en) | 1982-08-19 |
| CS99882A2 (en) | 1987-07-16 |
| NO156721B (no) | 1987-08-03 |
| DE3266261D1 (en) | 1985-10-24 |
| PL235049A1 (cs) | 1982-09-27 |
| DD202573A5 (de) | 1983-09-21 |
| EP0058614B1 (en) | 1985-09-18 |
| FI820466L (fi) | 1982-08-14 |
| CA1216292A (en) | 1987-01-06 |
| JPS57134482A (en) | 1982-08-19 |
| NO820430L (no) | 1982-08-16 |
| PH18177A (en) | 1985-04-12 |
| EP0058614A1 (en) | 1982-08-25 |
| MX158194A (es) | 1989-01-16 |
| YU26582A (en) | 1986-04-30 |
| JPH0243753B2 (cs) | 1990-10-01 |
| HU186473B (en) | 1985-08-28 |
| KR830009096A (ko) | 1983-12-17 |
| KR870000322B1 (ko) | 1987-02-27 |
| ZA82740B (en) | 1982-12-29 |
| ES509538A0 (es) | 1983-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: DAINIPPON PHARMACEUTICAL CO.,_LTD. |