BG61947B1 - Еднофазов метод за получаване на производни на 3-хинолонкарбонова киселина - Google Patents
Еднофазов метод за получаване на производни на 3-хинолонкарбонова киселина Download PDFInfo
- Publication number
- BG61947B1 BG61947B1 BG99248A BG9924894A BG61947B1 BG 61947 B1 BG61947 B1 BG 61947B1 BG 99248 A BG99248 A BG 99248A BG 9924894 A BG9924894 A BG 9924894A BG 61947 B1 BG61947 B1 BG 61947B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- formula
- ester
- compounds
- halogen
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000002253 acid Substances 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- -1 dimethylaminoacrylic acid ester Chemical class 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 12
- 150000004820 halides Chemical class 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- UBIKHJZIEKPIBU-UHFFFAOYSA-N 3-oxo-2h-quinoline-2-carboxylic acid Chemical class C1=CC=CC2=CC(=O)C(C(=O)O)N=C21 UBIKHJZIEKPIBU-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 239000000543 intermediate Chemical group 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 238000007127 saponification reaction Methods 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims 2
- 125000006519 CCH3 Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 6
- 239000013543 active substance Substances 0.000 abstract description 5
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 abstract description 5
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 abstract description 2
- 229960003405 ciprofloxacin Drugs 0.000 abstract description 2
- 229960000740 enrofloxacin Drugs 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
- QGPKADBNRMWEQR-UHFFFAOYSA-N clinafloxacin Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1Cl QGPKADBNRMWEQR-UHFFFAOYSA-N 0.000 description 7
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
- STBGCAUUOPNJBH-UHFFFAOYSA-N 2,4,5-trifluorobenzoyl chloride Chemical compound FC1=CC(F)=C(C(Cl)=O)C=C1F STBGCAUUOPNJBH-UHFFFAOYSA-N 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229960003237 betaine Drugs 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 2
- BCLPBTWFAXCEPU-UHFFFAOYSA-N 2-(cyclopropylamino)prop-2-enoic acid Chemical compound OC(=O)C(=C)NC1CC1 BCLPBTWFAXCEPU-UHFFFAOYSA-N 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- JODDVGWNUWGSMG-UHFFFAOYSA-N ethyl 2-(dimethylamino)prop-2-enoate Chemical compound CCOC(=O)C(=C)N(C)C JODDVGWNUWGSMG-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007040 multi-step synthesis reaction Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- UDWYGWMSVGVBCG-UHFFFAOYSA-N 2-(dimethylamino)prop-2-enoic acid Chemical compound CN(C)C(=C)C(O)=O UDWYGWMSVGVBCG-UHFFFAOYSA-N 0.000 description 1
- WVGSPMZLNNRZRH-UHFFFAOYSA-N 2-chloro-4,5-difluorobenzoyl chloride Chemical compound FC1=CC(Cl)=C(C(Cl)=O)C=C1F WVGSPMZLNNRZRH-UHFFFAOYSA-N 0.000 description 1
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- HDCCJUCOIKLZNM-UHFFFAOYSA-N n-pyrrolidin-3-ylacetamide Chemical compound CC(=O)NC1CCNC1 HDCCJUCOIKLZNM-UHFFFAOYSA-N 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005188 oxoalkyl group Chemical group 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Inorganic materials [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
-
- 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
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4342186A DE4342186A1 (de) | 1993-12-10 | 1993-12-10 | Eintopfverfahren zur Herstellung von 3-Chinoloncarbonsäurederivaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG99248A BG99248A (en) | 1995-09-29 |
| BG61947B1 true BG61947B1 (bg) | 1998-10-30 |
Family
ID=6504693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG99248A BG61947B1 (bg) | 1993-12-10 | 1994-12-08 | Еднофазов метод за получаване на производни на 3-хинолонкарбонова киселина |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US5639886A (sk) |
| EP (1) | EP0657448B1 (sk) |
| JP (1) | JP3963490B2 (sk) |
| KR (1) | KR950018008A (sk) |
| CN (1) | CN1109877A (sk) |
| AT (1) | ATE163645T1 (sk) |
| AU (1) | AU693818B2 (sk) |
| BG (1) | BG61947B1 (sk) |
| CA (1) | CA2137523C (sk) |
| CO (1) | CO4180607A1 (sk) |
| CZ (1) | CZ288078B6 (sk) |
| DE (2) | DE4342186A1 (sk) |
| DK (1) | DK0657448T3 (sk) |
| EE (1) | EE03215B1 (sk) |
| ES (1) | ES2113040T3 (sk) |
| FI (1) | FI945776A (sk) |
| GR (1) | GR3026383T3 (sk) |
| HR (1) | HRP940950B1 (sk) |
| HU (1) | HU220597B1 (sk) |
| IL (1) | IL111921A (sk) |
| LV (1) | LV11470B (sk) |
| MY (1) | MY113302A (sk) |
| NO (1) | NO307180B1 (sk) |
| NZ (1) | NZ270086A (sk) |
| PE (1) | PE33795A1 (sk) |
| PL (1) | PL180022B1 (sk) |
| RO (1) | RO113345B1 (sk) |
| RU (1) | RU2138483C1 (sk) |
| SI (1) | SI0657448T1 (sk) |
| SK (1) | SK279950B6 (sk) |
| SV (1) | SV1994000071A (sk) |
| TW (1) | TW401412B (sk) |
| UA (1) | UA41323C2 (sk) |
| YU (1) | YU48865B (sk) |
| ZA (1) | ZA949830B (sk) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19826050A1 (de) * | 1998-06-12 | 1999-12-16 | Bayer Ag | Verfahren zur Herstellung von Chinolon- und Naphthyridoncarbonsäuren und deren Ester |
| IL151451A0 (en) * | 2000-02-25 | 2003-04-10 | Daiichi Seiyaku Co | Process for producing quinolonecarboxylic acids and intermediates thereof |
| US6608078B2 (en) | 2000-05-08 | 2003-08-19 | Wockhardt Limited | Antibacterial chiral 8-(substituted piperidino)-benzo [i,j] quinolizines, processes, compositions and methods of treatment |
| DE10026903A1 (de) * | 2000-06-03 | 2002-01-10 | Cpc Cellular Process Chemistry | Verfahren zur Herstellung von Chinolon-3-carbonsäuren |
| US7098219B2 (en) | 2000-08-01 | 2006-08-29 | Wockhart Limited | Inhibitors of cellular efflux pumps of microbes |
| US6964966B2 (en) | 2001-04-25 | 2005-11-15 | Wockhardt Limited | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| US6878713B2 (en) * | 2001-04-25 | 2005-04-12 | Wockhardt Limited | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| US6664267B1 (en) | 2002-05-28 | 2003-12-16 | Wockhardt Limited | Crystalline fluoroquinolone arginine salt form |
| KR100519158B1 (ko) * | 2002-12-21 | 2005-10-06 | 주식회사유한양행 | 퀴놀론 카르복실레이트 유도체의 제조방법 |
| JP5255183B2 (ja) | 2003-09-04 | 2013-08-07 | ウォックハート リミテッド | ベンゾキノリジン−２−カルボン酸アルギニン塩四水和物 |
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| CN100412075C (zh) * | 2004-06-22 | 2008-08-20 | 浙江医药股份有限公司新昌制药厂 | 左旋氧氟沙星和氧氟沙星的制备方法 |
| KR20150048920A (ko) | 2006-11-13 | 2015-05-07 | 씨아이피엘에이 엘티디. | 목시플록사신 염산염의 합성방법 |
| EP1992626A1 (en) * | 2007-05-10 | 2008-11-19 | Sandoz AG | Process for the preparation of moxifloxacin hydrochloride |
| FR2916446B1 (fr) * | 2007-05-24 | 2009-08-21 | Biocodex Sa | Nouveau procede de synthese de fluoroquinolones |
| EP2083010A1 (en) | 2008-01-08 | 2009-07-29 | Chemo Ibérica, S.A. | Polymorphic Forms of Moxifloxacin hydrochloride and processes for preparation thereof |
| CN101781299B (zh) * | 2010-01-13 | 2012-06-27 | 杭州师范大学 | 一种喹诺酮类药物关键中间体的一锅法合成方法 |
| IT1398952B1 (it) | 2010-03-19 | 2013-03-28 | F S I Fabbrica Italiana Sint | Processo di preparazione della moxifloxacina e suoi sali |
| CN102675306A (zh) * | 2011-03-17 | 2012-09-19 | 苏州中科天马肽工程中心有限公司 | 一种莫西沙星或其盐的制备方法 |
| CN102267994B (zh) * | 2011-06-17 | 2013-01-30 | 江苏正大丰海制药有限公司 | 一种盐酸莫西沙星已知杂质的制备方法 |
| WO2013157018A1 (en) | 2012-04-18 | 2013-10-24 | Indian Institute Of Technology Madras | A process for the preparation of the core structure in quinolone and napthyridone class of antibiotics |
| WO2014087292A1 (en) | 2012-12-04 | 2014-06-12 | Mankind Research Centre | An improved process for the preparation of moxifloxacin hydrochloride |
| UA106556C2 (uk) | 2013-05-13 | 2014-09-10 | Наталья Николаевна Деркач | СПОСІБ ОДЕРЖАННЯ (1-ЦИКЛОПРОПІЛ-6-ФТОР-1,4-ДИГІДРО-8-МЕТОКСІ-7-[(4aS,7aS)-ОКТАГІДРО-6Н-ПІРОЛО[3,4-b]-4-ОКСО-3-ХІНОЛІНКАРБОНОВОЇ КИСЛОТИ |
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| CN115385856A (zh) * | 2022-09-05 | 2022-11-25 | 常州大学 | 一锅法合成诺氟沙星中间体的方法 |
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| 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 |
| 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 |
| JPS62215572A (ja) * | 1986-03-17 | 1987-09-22 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体 |
| JPS63179856A (ja) | 1987-01-21 | 1988-07-23 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体の製造方法並びにその中間体 |
| DE3724466A1 (de) | 1987-07-24 | 1989-02-02 | Bayer Ag | Verfahren zur herstellung von chinoloncarbonsaeuren |
| US4780468A (en) * | 1987-08-07 | 1988-10-25 | Warner-Lambert Company | 8-trifluoromethyl quinolones as antibacterial agents |
| WO1989005643A1 (en) * | 1987-12-18 | 1989-06-29 | Pfizer Inc. | Heterocyclic-substituted quinoline-carboxylic acids |
| DE3906365A1 (de) | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
| DE4208792A1 (de) | 1992-03-19 | 1993-09-23 | Bayer Ag | Enantiomerenreine chinolincarbonsaeure-derivate |
| TW209865B (sk) * | 1992-01-10 | 1993-07-21 | Bayer Ag | |
| DE4208789A1 (de) | 1992-03-19 | 1993-09-23 | Bayer Ag | Enantiomerenreine chinolincarbonsaeure-derivate |
| 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 |
| CA2168764C (en) * | 1993-08-13 | 2000-01-18 | Sung June Yoon | Novel quinolone carboxylic acid derivatives |
-
1993
- 1993-12-10 DE DE4342186A patent/DE4342186A1/de not_active Withdrawn
-
1994
- 1994-11-18 EE EE9400332A patent/EE03215B1/xx not_active IP Right Cessation
- 1994-11-21 TW TW083110792A patent/TW401412B/zh not_active IP Right Cessation
- 1994-11-23 HR HRP4342186.5A patent/HRP940950B1/xx not_active IP Right Cessation
- 1994-11-28 CO CO94054149A patent/CO4180607A1/es unknown
- 1994-11-28 AT AT94118676T patent/ATE163645T1/de not_active IP Right Cessation
- 1994-11-28 DK DK94118676T patent/DK0657448T3/da active
- 1994-11-28 SI SI9430120T patent/SI0657448T1/xx unknown
- 1994-11-28 EP EP94118676A patent/EP0657448B1/de not_active Expired - Lifetime
- 1994-11-28 DE DE59405376T patent/DE59405376D1/de not_active Expired - Lifetime
- 1994-11-28 ES ES94118676T patent/ES2113040T3/es not_active Expired - Lifetime
- 1994-12-02 US US08/348,400 patent/US5639886A/en not_active Expired - Lifetime
- 1994-12-05 JP JP32920694A patent/JP3963490B2/ja not_active Expired - Lifetime
- 1994-12-06 AU AU80244/94A patent/AU693818B2/en not_active Ceased
- 1994-12-06 RO RO94-01949A patent/RO113345B1/ro unknown
- 1994-12-07 NZ NZ270086A patent/NZ270086A/en unknown
- 1994-12-07 SK SK1514-94A patent/SK279950B6/sk unknown
- 1994-12-07 IL IL11192194A patent/IL111921A/xx not_active IP Right Cessation
- 1994-12-07 CA CA002137523A patent/CA2137523C/en not_active Expired - Lifetime
- 1994-12-07 PE PE1994256625A patent/PE33795A1/es not_active Application Discontinuation
- 1994-12-08 FI FI945776A patent/FI945776A/fi unknown
- 1994-12-08 SV SV1994000071A patent/SV1994000071A/es not_active Application Discontinuation
- 1994-12-08 YU YU71694A patent/YU48865B/sh unknown
- 1994-12-08 BG BG99248A patent/BG61947B1/bg unknown
- 1994-12-09 LV LVP-94-241A patent/LV11470B/lv unknown
- 1994-12-09 RU RU94043645A patent/RU2138483C1/ru active
- 1994-12-09 KR KR1019940033433A patent/KR950018008A/ko not_active Application Discontinuation
- 1994-12-09 PL PL94306198A patent/PL180022B1/pl unknown
- 1994-12-09 HU HU9403553A patent/HU220597B1/hu not_active IP Right Cessation
- 1994-12-09 ZA ZA949830A patent/ZA949830B/xx unknown
- 1994-12-09 UA UA94129157A patent/UA41323C2/uk unknown
- 1994-12-09 NO NO944786A patent/NO307180B1/no not_active IP Right Cessation
- 1994-12-09 CN CN94112890A patent/CN1109877A/zh active Pending
- 1994-12-09 MY MYPI94003290A patent/MY113302A/en unknown
- 1994-12-09 CZ CZ19943105A patent/CZ288078B6/cs not_active IP Right Cessation
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1998
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