AT402501B - Verfahren zur herstellung von 8-chlorochinolonderivaten - Google Patents
Verfahren zur herstellung von 8-chlorochinolonderivaten Download PDFInfo
- Publication number
- AT402501B AT402501B AT0206691A AT206691A AT402501B AT 402501 B AT402501 B AT 402501B AT 0206691 A AT0206691 A AT 0206691A AT 206691 A AT206691 A AT 206691A AT 402501 B AT402501 B AT 402501B
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- Austria
- Prior art keywords
- sep
- group
- carbon atoms
- compound
- atom
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- JNXUGJMCFLONJN-UHFFFAOYSA-N 8-chloroquinolin-2(1H)-one Chemical class C1=CC(=O)NC2=C1C=CC=C2Cl JNXUGJMCFLONJN-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000012320 chlorinating reagent Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- DTYLXDLAOLOTKT-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=C1 DTYLXDLAOLOTKT-UHFFFAOYSA-N 0.000 claims 1
- 239000005708 Sodium hypochlorite Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 33
- 125000003277 amino group Chemical group 0.000 abstract description 26
- 125000000217 alkyl group Chemical group 0.000 abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 14
- 125000001424 substituent group Chemical group 0.000 abstract description 10
- 125000005843 halogen group Chemical group 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 238000005660 chlorination reaction Methods 0.000 abstract description 7
- 229910052799 carbon Inorganic materials 0.000 abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 6
- 125000002947 alkylene group Chemical group 0.000 abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 5
- 125000003003 spiro group Chemical group 0.000 abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- -1 8-chloro-7-substituted-1- (2-fluorocyclopropyl) -4-quinolone Chemical class 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 3
- KBESHLYCSZINAJ-UHFFFAOYSA-N 3-chloro-2,4,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(Cl)=C1F KBESHLYCSZINAJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YJMPDZLZEKRKFR-ZJIMSODOSA-N (7s)-5-azaspiro[2.4]heptan-7-amine;dihydrochloride Chemical compound Cl.Cl.N[C@@H]1CNCC11CC1 YJMPDZLZEKRKFR-ZJIMSODOSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- ONUWJJIRDXEMLU-UHFFFAOYSA-N 2-methylpropyl hypochlorite Chemical compound CC(C)COCl ONUWJJIRDXEMLU-UHFFFAOYSA-N 0.000 description 1
- UXKKFPGAZIINBX-UHFFFAOYSA-N 3-chloro-1h-quinolin-2-one Chemical class C1=CC=C2NC(=O)C(Cl)=CC2=C1 UXKKFPGAZIINBX-UHFFFAOYSA-N 0.000 description 1
- DVCFPCHNBNBXPN-VEVZXVCZSA-N 7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid hydrochloride Chemical compound Cl.N[C@@H]1CN(CC12CC2)C2=C(C=C1C(C(=CN(C1=C2)[C@H]2[C@H](C2)F)C(=O)O)=O)F DVCFPCHNBNBXPN-VEVZXVCZSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WWBKUNAAULHLNW-UHFFFAOYSA-N 8-chloro-2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC(Cl)=C2NC(=O)C(C(=O)O)=CC2=C1 WWBKUNAAULHLNW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- GGUKKWVQUROSDV-UHFFFAOYSA-N butan-2-yl hypochlorite Chemical compound CCC(C)OCl GGUKKWVQUROSDV-UHFFFAOYSA-N 0.000 description 1
- GUGRBFQNXVKOGR-UHFFFAOYSA-N butyl hypochlorite Chemical compound CCCCOCl GUGRBFQNXVKOGR-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical class ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BIZGMTWBKDPTLH-UHFFFAOYSA-N propan-2-yl hypochlorite Chemical compound CC(C)OCl BIZGMTWBKDPTLH-UHFFFAOYSA-N 0.000 description 1
- PMYRRVREJIBUQU-UHFFFAOYSA-N propyl hypochlorite Chemical compound CCCOCl PMYRRVREJIBUQU-UHFFFAOYSA-N 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27977890 | 1990-10-18 | ||
| JP22815391 | 1991-05-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA206691A ATA206691A (de) | 1996-10-15 |
| AT402501B true AT402501B (de) | 1997-06-25 |
Family
ID=26528079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0206691A AT402501B (de) | 1990-10-18 | 1991-10-17 | Verfahren zur herstellung von 8-chlorochinolonderivaten |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR100253047B1 (et) |
| CN (1) | CN1038509C (et) |
| AR (1) | AR247884A1 (et) |
| AT (1) | AT402501B (et) |
| EE (1) | EE03027B1 (et) |
| ES (1) | ES2039300B1 (et) |
| FI (1) | FI100531B (et) |
| GR (1) | GR1000997B (et) |
| HU (1) | HU221195B1 (et) |
| MX (1) | MX9101668A (et) |
| MY (1) | MY109714A (et) |
| NO (1) | NO179517C (et) |
| PL (1) | PL168831B1 (et) |
| PT (1) | PT99268B (et) |
| RU (1) | RU2049778C1 (et) |
| YU (1) | YU48819B (et) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2100351C1 (ru) * | 1991-05-28 | 1997-12-27 | Дайити Фармасьютикал Ко., Лтд. | Производные пиридонкарбоновой кислоты и композиция на их основе |
| ZA946853B (en) * | 1993-09-10 | 1995-04-24 | Daiichi Seiyaku Co | Crystals of antimicrobial compound. |
| CN1184221C (zh) * | 2001-08-08 | 2005-01-12 | 中国医学科学院医药生物技术研究所 | 有7－(7－氨甲基－5－氮杂螺[2,4]庚烷)取代基的新喹啉羧酸衍生物及其制备方法 |
| CN103483315B (zh) * | 2013-09-18 | 2015-07-01 | 浙江司太立制药股份有限公司 | 7-(3-氨甲基-4-烷氧亚胺基-1-吡咯烷基)-1-[(1r,2s)-2-氟环丙基]喹诺酮羧酸类化合物及其制备方法 |
| CN103709100A (zh) * | 2013-12-31 | 2014-04-09 | 南京工业大学 | 一种8-氯代喹诺酮衍生物的制备方法 |
| CN104892600B (zh) * | 2015-06-04 | 2017-02-01 | 浙江司太立制药股份有限公司 | 7‑（3‑氨甲基‑4‑取代苄氧亚胺基‑1‑吡咯烷基）萘啶酮羧酸类化合物 |
| CN105061395A (zh) * | 2015-08-10 | 2015-11-18 | 江苏吴中医药集团有限公司 | 一种西他沙星水合物的制备方法 |
| CN105669646B (zh) * | 2016-02-26 | 2018-03-09 | 济川药业集团有限公司 | 一种西他沙星的合成方法 |
| CN113527200B (zh) * | 2021-05-27 | 2022-12-02 | 北京斯利安药业有限公司 | 一种氯喹那多的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0191185A1 (en) * | 1984-12-14 | 1986-08-20 | Daiichi Seiyaku Co., Ltd. | Quinoline-carboxylic acid derivatives |
| EP0341493A2 (en) * | 1988-04-27 | 1989-11-15 | Daiichi Pharmaceutical Co., Ltd. | Optically active pyridonecarboxylic acid derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840437A1 (de) * | 1978-09-16 | 1980-04-03 | Hoechst Ag | 8-chlor-5,6,7,8-tetrahydro-2-chinolon und 8-brom-5,6,7,8-tetrahydro-2-chinolon, deren hydrochlorid bzw. hydrobromid und verfahren zu deren herstellung |
| JPH0635457B2 (ja) * | 1985-06-28 | 1994-05-11 | 杏林製薬株式会社 | ピリドンカルボン酸誘導体およびその製造方法 |
| DE3635218A1 (de) * | 1986-10-16 | 1988-04-21 | Bayer Ag | 7-amino-1-cyclopropyl-8-chlor-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| JPS6490183A (en) * | 1987-09-30 | 1989-04-06 | Kyorin Seiyaku Kk | Production of quinolonecarboxylic acid derivative |
| JPH0196786A (ja) * | 1987-10-09 | 1989-04-14 | Toshiba Corp | 改札装置のデータ集計処理方式 |
| CA1336090C (en) * | 1988-08-31 | 1995-06-27 | Isao Hayakawa | Spiro-substituted cyclic amines of quinolone derivatives |
-
1991
- 1991-10-12 MY MYPI91001865A patent/MY109714A/en unknown
- 1991-10-14 YU YU165791A patent/YU48819B/sh unknown
- 1991-10-16 FI FI914875A patent/FI100531B/fi active
- 1991-10-16 NO NO914053A patent/NO179517C/no unknown
- 1991-10-17 RU SU915010041A patent/RU2049778C1/ru not_active IP Right Cessation
- 1991-10-17 GR GR910100427A patent/GR1000997B/el not_active IP Right Cessation
- 1991-10-17 AT AT0206691A patent/AT402501B/de not_active IP Right Cessation
- 1991-10-17 PL PL91292087A patent/PL168831B1/pl not_active IP Right Cessation
- 1991-10-17 HU HU280/91A patent/HU221195B1/hu not_active IP Right Cessation
- 1991-10-17 PT PT99268A patent/PT99268B/pt not_active IP Right Cessation
- 1991-10-17 ES ES09102304A patent/ES2039300B1/es not_active Expired - Fee Related
- 1991-10-17 AR AR91320942A patent/AR247884A1/es active
- 1991-10-18 CN CN91110833A patent/CN1038509C/zh not_active Expired - Lifetime
- 1991-10-18 MX MX9101668A patent/MX9101668A/es unknown
- 1991-10-18 KR KR1019910018376A patent/KR100253047B1/ko not_active Expired - Lifetime
-
1994
- 1994-11-22 EE EE9400253A patent/EE03027B1/et not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0191185A1 (en) * | 1984-12-14 | 1986-08-20 | Daiichi Seiyaku Co., Ltd. | Quinoline-carboxylic acid derivatives |
| EP0341493A2 (en) * | 1988-04-27 | 1989-11-15 | Daiichi Pharmaceutical Co., Ltd. | Optically active pyridonecarboxylic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FI100531B (fi) | 1997-12-31 |
| NO914053D0 (no) | 1991-10-16 |
| GR1000997B (el) | 1993-03-31 |
| YU48819B (sh) | 2001-12-26 |
| YU165791A (sh) | 1994-05-10 |
| ES2039300B1 (es) | 1994-05-16 |
| PL168831B1 (pl) | 1996-04-30 |
| HU913280D0 (en) | 1992-01-28 |
| NO179517C (no) | 1996-10-23 |
| ES2039300A1 (es) | 1993-09-16 |
| FI914875A7 (fi) | 1992-04-19 |
| PL292087A1 (en) | 1992-11-16 |
| GR910100427A (en) | 1992-09-25 |
| HUT59388A (en) | 1992-05-28 |
| NO179517B (no) | 1996-07-15 |
| CN1062906A (zh) | 1992-07-22 |
| NO914053L (no) | 1992-04-21 |
| ATA206691A (de) | 1996-10-15 |
| PT99268B (pt) | 1999-04-30 |
| RU2049778C1 (ru) | 1995-12-10 |
| MX9101668A (es) | 1992-06-05 |
| KR920008007A (ko) | 1992-05-27 |
| CN1038509C (zh) | 1998-05-27 |
| AR247884A1 (es) | 1995-04-28 |
| MY109714A (en) | 1997-04-30 |
| PT99268A (pt) | 1992-08-31 |
| HU221195B1 (en) | 2002-08-28 |
| EE03027B1 (et) | 1997-08-15 |
| KR100253047B1 (ko) | 2000-05-01 |
| FI914875A0 (fi) | 1991-10-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties | ||
| ELJ | Ceased due to non-payment of the annual fee |