FI66379C - Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara 6-halogen-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1-substituerade 1,8-naftyridin-3-karboxylsyror och salter daerav - Google Patents
Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara 6-halogen-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1-substituerade 1,8-naftyridin-3-karboxylsyror och salter daerav Download PDFInfo
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- FI66379C FI66379C FI792645A FI792645A FI66379C FI 66379 C FI66379 C FI 66379C FI 792645 A FI792645 A FI 792645A FI 792645 A FI792645 A FI 792645A FI 66379 C FI66379 C FI 66379C
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- Finland
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- compound
- formula
- ethyl
- piperazinyl
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- -1 1-PIPERAZINYL Chemical class 0.000 title claims description 53
- 230000001225 therapeutic effect Effects 0.000 title description 14
- 238000004458 analytical method Methods 0.000 title description 2
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- 238000000034 method Methods 0.000 claims description 65
- 238000002360 preparation method Methods 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 21
- 239000007795 chemical reaction product Substances 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 14
- 231100000252 nontoxic Toxicity 0.000 claims description 11
- 230000003000 nontoxic effect Effects 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
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- 239000000284 extract Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- LKQWLZQAQJRLHC-UHFFFAOYSA-M [OH-].C(C)(=O)N1CCN(CC1)C([N+](C)(C)CC)N1C=C(C(C2=CC(=CN=C12)F)=O)C(=O)OCC Chemical compound [OH-].C(C)(=O)N1CCN(CC1)C([N+](C)(C)CC)N1C=C(C(C2=CC(=CN=C12)F)=O)C(=O)OCC LKQWLZQAQJRLHC-UHFFFAOYSA-M 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940107816 ammonium iodide Drugs 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- 230000001572 anti-trichomonad Effects 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 229960003328 benzoyl peroxide Drugs 0.000 description 1
- FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 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
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- IZCQTHXLOQWUTC-UHFFFAOYSA-N ethyl 1-ethenyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylate Chemical compound FC=1C=C2C(=O)C(C(=O)OCC)=CN(C=C)C2=NC=1N1CCNCC1 IZCQTHXLOQWUTC-UHFFFAOYSA-N 0.000 description 1
- NDESOPVYUOKSCO-UHFFFAOYSA-N ethyl 1-ethyl-7-ethylsulfonyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound CCS(=O)(=O)C1=C(F)C=C2C(=O)C(C(=O)OCC)=CN(CC)C2=N1 NDESOPVYUOKSCO-UHFFFAOYSA-N 0.000 description 1
- KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 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
- KOLLAFJZPNUYKT-UHFFFAOYSA-N ethyl 4-(6-amino-3-nitropyridin-2-yl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C1=NC(N)=CC=C1[N+]([O-])=O KOLLAFJZPNUYKT-UHFFFAOYSA-N 0.000 description 1
- ACSLBRULOFKMND-UHFFFAOYSA-N ethyl 6-amino-1-ethyl-4-oxo-7-[4-(2,2,2-trifluoroacetyl)piperazin-1-yl]-1,8-naphthyridine-3-carboxylate Chemical compound NC=1C=C2C(C(=CN(C2=NC1N1CCN(CC1)C(C(F)(F)F)=O)CC)C(=O)OCC)=O ACSLBRULOFKMND-UHFFFAOYSA-N 0.000 description 1
- BWWLDQWFSQRTHC-UHFFFAOYSA-N ethyl 6-chloro-7-(4-ethoxycarbonylpiperazin-1-yl)-4-oxo-1H-1,8-naphthyridine-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C(=C1)Cl)=NC2=C1C(=O)C(C(=O)OCC)=CN2 BWWLDQWFSQRTHC-UHFFFAOYSA-N 0.000 description 1
- QQSWUPHTEYPMCA-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-7-[4-(2,2,2-trifluoroacetyl)piperazin-1-yl]-1h-1,8-naphthyridine-3-carboxylate Chemical compound FC=1C=C2C(=O)C(C(=O)OCC)=CNC2=NC=1N1CCN(C(=O)C(F)(F)F)CC1 QQSWUPHTEYPMCA-UHFFFAOYSA-N 0.000 description 1
- FIYQQMBWWGACMN-UHFFFAOYSA-N ethyl 7-(4-acetylpiperazin-1-yl)-1-ethenyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C(C)(=O)N1CCN(CC1)C1=C(C=C2C(C(=CN(C2=N1)C=C)C(=O)OCC)=O)F FIYQQMBWWGACMN-UHFFFAOYSA-N 0.000 description 1
- GNQIMTPFLPCWDY-UHFFFAOYSA-N ethyl 7-(4-acetylpiperazin-1-yl)-1-ethyl-6-nitro-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C(C)(=O)N1CCN(CC1)C1=C(C=C2C(C(=CN(C2=N1)CC)C(=O)OCC)=O)[N+](=O)[O-] GNQIMTPFLPCWDY-UHFFFAOYSA-N 0.000 description 1
- SDFDMCIQVYEQBE-UHFFFAOYSA-N ethyl 7-(4-acetylpiperazin-1-yl)-6-amino-1-ethyl-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C(C)(=O)N1CCN(CC1)C1=C(C=C2C(C(=CN(C2=N1)CC)C(=O)OCC)=O)N SDFDMCIQVYEQBE-UHFFFAOYSA-N 0.000 description 1
- JSEMSFSGERZMRY-UHFFFAOYSA-N ethyl 7-(4-acetylpiperazin-1-yl)-6-chloro-1-(2-chloroethyl)-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound ClC=1C=C2C(=O)C(C(=O)OCC)=CN(CCCl)C2=NC=1N1CCN(C(C)=O)CC1 JSEMSFSGERZMRY-UHFFFAOYSA-N 0.000 description 1
- WWAVBQJXMSCEKX-UHFFFAOYSA-N ethyl 7-(4-ethoxycarbonylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(C(=C1)F)=NC2=C1C(=O)C(C(=O)OCC)=CN2CC WWAVBQJXMSCEKX-UHFFFAOYSA-N 0.000 description 1
- ANNNGOUEZBONHD-UHFFFAOYSA-N ethyl phenylmethanesulfonate Chemical compound CCOS(=O)(=O)CC1=CC=CC=C1 ANNNGOUEZBONHD-UHFFFAOYSA-N 0.000 description 1
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960001732 pipemidic acid Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZCZNNPCUZCIWFT-UHFFFAOYSA-M potassium;7-(4-acetylpiperazin-1-yl)-6-chloro-1-ethenyl-4-oxo-1,8-naphthyridine-3-carboxylate Chemical compound [K+].C1CN(C(=O)C)CCN1C(C(=C1)Cl)=NC2=C1C(=O)C(C([O-])=O)=CN2C=C ZCZNNPCUZCIWFT-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 238000006886 vinylation reaction Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C07D213/74—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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10423578 | 1978-08-25 | ||
| JP10423578A JPS5531042A (en) | 1978-08-25 | 1978-08-25 | 1,8-naphthylidine derivative and its salt |
| JP15793978A JPS5583785A (en) | 1978-12-20 | 1978-12-20 | 6-fluoro-1,8-naphthyridine derivative and its salt |
| JP15793978 | 1978-12-20 | ||
| JP16209578 | 1978-12-29 | ||
| JP16209578A JPS5592385A (en) | 1978-12-29 | 1978-12-29 | 1-vinyl-1,8-naphthylidine derivative and its salt |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI792645A7 FI792645A7 (fi) | 1980-02-26 |
| FI66379B FI66379B (fi) | 1984-06-29 |
| FI66379C true FI66379C (fi) | 1984-10-10 |
Family
ID=27310175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI792645A FI66379C (fi) | 1978-08-25 | 1979-08-24 | Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara 6-halogen-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1-substituerade 1,8-naftyridin-3-karboxylsyror och salter daerav |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4359578A (cs) |
| EP (1) | EP0009425B1 (cs) |
| AR (3) | AR223983A1 (cs) |
| AU (1) | AU530052B2 (cs) |
| CA (1) | CA1168241A (cs) |
| CS (1) | CS235502B2 (cs) |
| DD (1) | DD145753A5 (cs) |
| DE (1) | DE2961979D1 (cs) |
| DK (1) | DK153552C (cs) |
| ES (1) | ES483629A1 (cs) |
| FI (1) | FI66379C (cs) |
| HU (1) | HU179927B (cs) |
| NO (1) | NO153136C (cs) |
| PH (1) | PH14287A (cs) |
| PL (1) | PL120114B1 (cs) |
| YU (4) | YU42193B (cs) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS5649382A (en) * | 1979-09-28 | 1981-05-02 | Dainippon Pharmaceut Co Ltd | 6-fluoro-7-cyclic amino-1,8-naphthylidine derivative and its salt |
| US4670444B1 (en) * | 1980-09-03 | 1999-02-09 | Bayer Ag | and-naphthyridine-3-carboxylic acids and antibacte7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-rial agents containing these compounds |
| US4620007A (en) * | 1980-09-03 | 1986-10-28 | Bayer Aktiengesellschaft | 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid |
| JPS57106681A (en) * | 1980-12-24 | 1982-07-02 | Dainippon Pharmaceut Co Ltd | 1,8-naphthyridine derivative and its salt |
| 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 |
| ES8304117A1 (es) * | 1981-06-11 | 1983-02-16 | Warner Lambert Co | "un procedimiento para preparar sales de compuestos de naftiridina y quinoleina". |
| JPS5925391A (ja) * | 1982-07-30 | 1984-02-09 | Dainippon Pharmaceut Co Ltd | ピリジルナフチリジン誘導体およびその塩 |
| DE3308908A1 (de) * | 1983-03-12 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Bakterizide mittel |
| FR2559484B2 (fr) * | 1983-07-06 | 1986-09-26 | Provesan Sa | Nouveau derive 7-(pyrrol-1-yl) de l'acide 1-ethyl-1,4-dihydro-4-oxo-(1,8-naphtyridin)-3-carboxylique, sa preparation et son application en tant que medicament |
| FR2548664B1 (fr) * | 1983-07-06 | 1986-03-21 | Provesan Sa | Derives 7-(pyrrol-l-yl) des acides l-ethyl-1,4-dihydro-4-oxoquinoleine-3-carboxyliques et l-ethyl-1,4-dihydro-4-oxo-(1,8-naphtyridine)-3-carboxyliques substitues, leur preparation et leur application en tant que medicaments |
| US4730000A (en) * | 1984-04-09 | 1988-03-08 | Abbott Laboratories | Quinoline antibacterial compounds |
| CS274601B2 (en) * | 1983-07-27 | 1991-09-15 | Dainippon Pharmaceutical Co | Method of 1,8-naphthyridine derivative production |
| DE3333719A1 (de) * | 1983-09-17 | 1985-04-04 | Bayer Ag | Loesungen milchsaurer salze von piperazinylchinolon- und piperazinyl-azachinoloncarbonsaeuren |
| US4551456A (en) * | 1983-11-14 | 1985-11-05 | Merck & Co., Inc. | Ophthalmic use of norfloxacin and related antibiotics |
| US4774246A (en) * | 1984-01-26 | 1988-09-27 | Abbott Laboratories | Quinoline antibacterial compounds |
| NZ210847A (en) * | 1984-01-26 | 1988-02-29 | Abbott Lab | Naphthyridine and pyridopyrimidine derivatives and pharmaceutical compositions |
| IL74244A (en) * | 1984-02-17 | 1988-06-30 | Warner Lambert Co | Quinoline derivatives,their preparation and pharmaceutical compositions containing them |
| DE3409922A1 (de) * | 1984-03-17 | 1985-09-26 | Bayer Ag, 5090 Leverkusen | 1,7-diamino-1,4-dihydro-4-oxo-3-(aza)chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie ihre verwendung bei der bekaempfung bakterieller erkrankungen |
| US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
| JPS60228479A (ja) * | 1984-04-26 | 1985-11-13 | Toyama Chem Co Ltd | 1,4−ジヒドロ−4−オキソナフチリジン誘導体およびその塩 |
| 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 |
| DE3517709A1 (de) * | 1985-01-05 | 1986-07-10 | Bayer Ag | Basische zubereitungen von chinoloncarbonsaeuren |
| DE3508816A1 (de) * | 1985-01-10 | 1986-07-10 | Bayer Ag, 5090 Leverkusen | 6,7-disubstituierte 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphtyridin-3-carbonsaeuren |
| US4851535A (en) * | 1985-01-23 | 1989-07-25 | Toyama Chemical Co., Ltd. | Nicotinic acid derivatives |
| AT392789B (de) * | 1985-01-23 | 1991-06-10 | Toyama Chemical Co Ltd | Verfahren zur herstellung von 1-substituierten aryl-1,4-dihydro-4-oxonaphthyridinderivaten |
| AT392791B (de) * | 1985-01-23 | 1991-06-10 | Toyama Chemical Co Ltd | Verfahren zur herstellung von 1-substituierten aryl-1,4-dihydro-4-oxonaphthyridinderivaten |
| DE3525108A1 (de) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | Antibakteriell wirksame chinoloncarbonsaeureester |
| DE3608745A1 (de) * | 1985-07-24 | 1987-01-29 | Bayer Ag | Bakterizide zubereitungen zur anwendung auf dem gebiet der veterinaermedizin |
| 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 |
| US4689325A (en) * | 1985-12-23 | 1987-08-25 | Abbott Laboratories | Isoxazolo-pyrido-phenoxazine and isothiazolo-pyrido-phenoxazine derivatives |
| US4687770A (en) * | 1985-12-23 | 1987-08-18 | Abbott Laboratories | Isoxazolo-pyrido-benzoxazine and isothiazolo-pyrido-benzoxazine derivatives |
| US4940710A (en) * | 1986-01-17 | 1990-07-10 | American Cyanamid Company | 7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
| US5210193A (en) * | 1986-01-17 | 1993-05-11 | American Cyanamid Company | Piperazine derivatives |
| HU196987B (en) * | 1986-10-15 | 1989-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing quinoline-carboxylic acid derivatives |
| IL80459A (en) * | 1986-10-30 | 1991-04-15 | Abic Ltd | Water-soluble adduct of norfloxacin and nicotinic acid |
| IE873504L (en) * | 1987-01-28 | 1988-07-28 | Harvard College | Stabilized ophthalmic compositions |
| IL90635A0 (en) * | 1988-07-15 | 1990-01-18 | Abbott Lab | Process for the preparation of quinoline antibacterial compounds |
| US5262417A (en) * | 1988-12-06 | 1993-11-16 | The Upjohn Company | Antibacterial quinolone compounds |
| NZ232091A (en) * | 1989-01-16 | 1990-12-21 | Bellon Labor Sa Roger | 7-fluoro-8-(piperazin-1-yl)-4-oxo-1,4-dihydro-benzo(b)(1,8)naphthyridine-3-carboxylic acid derivatives, preparation and pharmaceutical compositions thereof |
| FR2641783B1 (fr) * | 1989-01-16 | 1991-04-05 | Bellon Labor Sa Roger | Nouveaux derives de benzonaphtyridine-1,8, leur preparation et les compositions qui les contiennent |
| US5466696A (en) * | 1992-09-10 | 1995-11-14 | Warner Lambert Company | Tacrine and cytochrome P450 oxidase inhibitors and methods of use |
| US5422350A (en) * | 1992-09-10 | 1995-06-06 | Warner-Lambert Company | Nitrogen substituted acridine and cytochrome P450 inhibitors and methods of use |
| US5290794A (en) * | 1992-10-27 | 1994-03-01 | Warner Lambert Co. | Soluble calcium lactate antibacterial complexes as non-irritating parenteral forms |
| AU4272793A (en) * | 1993-04-24 | 1994-11-21 | Korea Research Institute Of Chemical Technology | Novel quinolone carboxylic acid derivatives and process for preparing the same |
| KR950018003A (ko) * | 1993-12-09 | 1995-07-22 | 스미스클라인 비참 피엘씨 | 신규한 퀴놀론 유도체 및 그의 제조 방법 |
| MA24500A1 (fr) | 1997-03-21 | 1998-10-01 | Lg Life Sciences Ltd | Derive du sel d'acide carboxylique de naphthyridine . |
Family Cites Families (6)
| 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 |
| DE2103805C3 (de) * | 1970-01-28 | 1980-03-20 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Verfahren zur Herstellung von N-substituierten 6,7-Methylendioxy-4chinolonen |
| US4017622A (en) * | 1972-12-18 | 1977-04-12 | Dainippon Pharmaceutical Co., Ltd. | Piperazine derivatives |
| JPS5936637B2 (ja) * | 1976-01-01 | 1984-09-05 | 第一製薬株式会社 | 6−ニトロ−1,8−ナフチリジン誘導体 |
| JPS53141286A (en) * | 1977-05-16 | 1978-12-08 | Kyorin Seiyaku Kk | Novel substituted quinolinecarboxylic acid |
| 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 |
-
1979
- 1979-08-09 AR AR277659A patent/AR223983A1/es active
- 1979-08-17 AU AU50049/79A patent/AU530052B2/en not_active Expired
- 1979-08-20 YU YU2032/79A patent/YU42193B/xx unknown
- 1979-08-22 DD DD79215122A patent/DD145753A5/de not_active IP Right Cessation
- 1979-08-23 HU HU79BE1361A patent/HU179927B/hu unknown
- 1979-08-23 US US06/068,966 patent/US4359578A/en not_active Expired - Lifetime
- 1979-08-24 CA CA000334439A patent/CA1168241A/en not_active Expired
- 1979-08-24 DE DE7979400587T patent/DE2961979D1/de not_active Expired
- 1979-08-24 CS CS795770A patent/CS235502B2/cs unknown
- 1979-08-24 ES ES483629A patent/ES483629A1/es not_active Expired
- 1979-08-24 EP EP79400587A patent/EP0009425B1/en not_active Expired
- 1979-08-24 FI FI792645A patent/FI66379C/fi not_active IP Right Cessation
- 1979-08-24 NO NO792760A patent/NO153136C/no unknown
- 1979-08-24 DK DK355679A patent/DK153552C/da not_active IP Right Cessation
- 1979-08-24 PL PL1979217926A patent/PL120114B1/pl unknown
- 1979-08-27 PH PH22967A patent/PH14287A/en unknown
-
1980
- 1980-10-28 AR AR283027A patent/AR227529A1/es active
- 1980-10-28 AR AR283026A patent/AR225195A1/es active
-
1981
- 1981-05-18 US US06/264,824 patent/US4352803A/en not_active Expired - Lifetime
-
1985
- 1985-02-28 YU YU318/85A patent/YU42614B/xx unknown
- 1985-02-28 YU YU319/85A patent/YU42615B/xx unknown
- 1985-02-28 YU YU317/85A patent/YU42637B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR225195A1 (es) | 1982-02-26 |
| DE2961979D1 (en) | 1982-03-11 |
| PL217926A1 (cs) | 1980-06-16 |
| YU203279A (en) | 1985-10-31 |
| PH14287A (en) | 1981-05-04 |
| DK355679A (da) | 1980-02-26 |
| DK153552C (da) | 1988-12-05 |
| AU530052B2 (en) | 1983-06-30 |
| YU31785A (en) | 1985-10-31 |
| YU42193B (en) | 1988-06-30 |
| ES483629A1 (es) | 1980-09-01 |
| US4352803A (en) | 1982-10-05 |
| EP0009425A1 (en) | 1980-04-02 |
| YU42637B (en) | 1988-10-31 |
| NO153136C (no) | 1986-01-22 |
| YU42614B (en) | 1988-10-31 |
| PL120114B1 (en) | 1982-02-27 |
| AU5004979A (en) | 1980-02-28 |
| CA1168241A (en) | 1984-05-29 |
| HU179927B (en) | 1983-01-28 |
| YU31885A (en) | 1985-10-31 |
| CS235502B2 (en) | 1985-05-15 |
| NO153136B (no) | 1985-10-14 |
| YU31985A (en) | 1985-10-31 |
| NO792760L (no) | 1980-02-26 |
| YU42615B (en) | 1988-10-31 |
| FI792645A7 (fi) | 1980-02-26 |
| US4359578A (en) | 1982-11-16 |
| EP0009425B1 (en) | 1982-01-27 |
| DK153552B (da) | 1988-07-25 |
| FI66379B (fi) | 1984-06-29 |
| AR227529A1 (es) | 1982-11-15 |
| DD145753A5 (de) | 1981-01-07 |
| AR223983A1 (es) | 1981-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: DAINIPPON PHARMACEUTICAL CO.,_LTD. |