JPWO2019206798A5 - - Google Patents
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- Publication number
- JPWO2019206798A5 JPWO2019206798A5 JP2020556943A JP2020556943A JPWO2019206798A5 JP WO2019206798 A5 JPWO2019206798 A5 JP WO2019206798A5 JP 2020556943 A JP2020556943 A JP 2020556943A JP 2020556943 A JP2020556943 A JP 2020556943A JP WO2019206798 A5 JPWO2019206798 A5 JP WO2019206798A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- dihydro
- oxo
- cyclopropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- KNEXGVPHPGXAGF-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 KNEXGVPHPGXAGF-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- NMASXYCNDJMMFR-UHFFFAOYSA-N 1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 NMASXYCNDJMMFR-UHFFFAOYSA-N 0.000 claims description 2
- FKKUVCHFRDLBHN-UHFFFAOYSA-N 1-ethyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylic acid Chemical compound FC1=C(F)C(F)=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 FKKUVCHFRDLBHN-UHFFFAOYSA-N 0.000 claims description 2
- ZHFGWIOLVRSZNQ-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ZHFGWIOLVRSZNQ-UHFFFAOYSA-N 0.000 claims description 2
- CSQLANIHEKGKAU-UHFFFAOYSA-N 8-cyano-1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(C#N)C(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 CSQLANIHEKGKAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000006419 fluorocyclopropyl group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXTYIFUOEXJZEN-UHFFFAOYSA-N 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(C#N)C(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 PXTYIFUOEXJZEN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18169170 | 2018-04-25 | ||
| EP18169170.0 | 2018-04-25 | ||
| PCT/EP2019/060072 WO2019206798A1 (fr) | 2018-04-25 | 2019-04-18 | Procédé d'hydrolyse d'esters d'acides quinolone-carboxyliques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021521238A JP2021521238A (ja) | 2021-08-26 |
| JPWO2019206798A5 true JPWO2019206798A5 (fr) | 2023-11-06 |
| JP7410050B2 JP7410050B2 (ja) | 2024-01-09 |
Family
ID=62063375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020556943A Active JP7410050B2 (ja) | 2018-04-25 | 2019-04-18 | キノロンカルボン酸エステルの加水分解プロセス |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US11332444B2 (fr) |
| EP (1) | EP3784656B1 (fr) |
| JP (1) | JP7410050B2 (fr) |
| KR (1) | KR20210005079A (fr) |
| CN (1) | CN111989314B (fr) |
| AU (1) | AU2019260015B2 (fr) |
| BR (1) | BR112020021635A2 (fr) |
| CA (1) | CA3098060A1 (fr) |
| CL (1) | CL2020002735A1 (fr) |
| CO (1) | CO2020013343A2 (fr) |
| CR (1) | CR20200502A (fr) |
| DK (1) | DK3784656T3 (fr) |
| DO (1) | DOP2020000189A (fr) |
| ES (1) | ES2956316T3 (fr) |
| IL (1) | IL278175A (fr) |
| MX (1) | MX2020011280A (fr) |
| PE (1) | PE20201257A1 (fr) |
| PH (1) | PH12020551750A1 (fr) |
| PT (1) | PT3784656T (fr) |
| SG (1) | SG11202010544TA (fr) |
| TW (1) | TW202003470A (fr) |
| UY (1) | UY38201A (fr) |
| WO (1) | WO2019206798A1 (fr) |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3420798A1 (de) | 1984-06-04 | 1985-12-05 | Bayer Ag, 5090 Leverkusen | 7-(3-aryl-l-piperazinyl)- sowie 7-(3-cyclohexyl-l-piperazinyl)-3-chinoloncarbonsaeuren |
| DE3702393A1 (de) | 1987-01-28 | 1988-08-11 | Bayer Ag | 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo- 3-chinolincarbonsaeuren, verfahren zu ihrer herstellung und diese enthaltende antibakterielle mittel |
| CZ291251B6 (cs) | 1996-02-23 | 2003-01-15 | Bayer Aktiengesellschaft | Popřípadě substituované 8-kyan-1-cyklopropyl-7-(2,8-diazabicyklo-[4,3,0]-nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolinkarboxylové kyseliny a jejich deriváty, způsob jejich výroby, léčiva tyto látka obsahující a jejich pouľití |
| DE19652239A1 (de) | 1996-12-16 | 1998-06-18 | Bayer Ag | Verwendung von 7-(2-Oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-chinolon- und -naphthyridoncarbonsäure-Derivaten zur Therapie von Helicobacter-pylori-Infektionen und den damit assoziierten gastroduodenalen Erkrankungen |
| CN1338455A (zh) * | 2000-08-16 | 2002-03-06 | 大连绿源实业有限公司 | 新的喹诺酮羧酸的制备方法 |
| DE10108750A1 (de) * | 2001-02-23 | 2002-09-05 | Bayer Ag | Verbessertes Verfahren zur Herstellung von Fluorchinoloncarbonsäuren |
| DE10134719A1 (de) | 2001-07-17 | 2003-02-06 | Bayer Ag | Pharmazeutische Zubereitungen enthaltend wirkstoffbeladene Ionentauscherharze |
| DE10224086A1 (de) | 2002-05-31 | 2003-12-11 | Bayer Ag | Pharmazeutische Zubereitungen zur oralen Anwendung enthaltend wirkstoffbeladene Ionentauscherharze sowie strukturviskose Gelbildner als Verdicker |
| US6900224B2 (en) * | 2002-07-31 | 2005-05-31 | The Procter & Gamble Company | Antimicrobial quinolones, their compositions and uses |
| DE10312346A1 (de) | 2003-03-20 | 2004-09-30 | Bayer Healthcare Ag | Kontrolliertes Freisetzungssystem |
| DE10337191A1 (de) | 2003-08-13 | 2005-03-17 | Bayer Healthcare Ag | Neue Verwendung von Chinolon-Antibiotika |
| DE10351448A1 (de) | 2003-11-04 | 2005-06-09 | Bayer Healthcare Ag | Geschmackstoffhaltige Arzneimittelformulierungen mit verbesserten pharmazeutischen Eigenschaften |
| DE102005055385A1 (de) | 2004-12-09 | 2006-06-14 | Bayer Healthcare Ag | Arzneimittel zur hygienischen Applikation im Ohr |
| CN105622632B (zh) * | 2014-10-29 | 2018-06-29 | 浙江海森药业股份有限公司 | 一种喹诺酮类化合物及其制备方法 |
-
2019
- 2019-04-18 CN CN201980026978.6A patent/CN111989314B/zh active Active
- 2019-04-18 ES ES19720502T patent/ES2956316T3/es active Active
- 2019-04-18 WO PCT/EP2019/060072 patent/WO2019206798A1/fr unknown
- 2019-04-18 MX MX2020011280A patent/MX2020011280A/es unknown
- 2019-04-18 CA CA3098060A patent/CA3098060A1/fr active Pending
- 2019-04-18 DK DK19720502.4T patent/DK3784656T3/da active
- 2019-04-18 PT PT197205024T patent/PT3784656T/pt unknown
- 2019-04-18 AU AU2019260015A patent/AU2019260015B2/en active Active
- 2019-04-18 KR KR1020207033003A patent/KR20210005079A/ko active IP Right Grant
- 2019-04-18 US US17/049,925 patent/US11332444B2/en active Active
- 2019-04-18 CR CR20200502A patent/CR20200502A/es unknown
- 2019-04-18 PE PE2020001673A patent/PE20201257A1/es unknown
- 2019-04-18 EP EP19720502.4A patent/EP3784656B1/fr active Active
- 2019-04-18 JP JP2020556943A patent/JP7410050B2/ja active Active
- 2019-04-18 SG SG11202010544TA patent/SG11202010544TA/en unknown
- 2019-04-18 BR BR112020021635-6A patent/BR112020021635A2/pt active Search and Examination
- 2019-04-23 TW TW108114080A patent/TW202003470A/zh unknown
- 2019-04-25 UY UY0001038201A patent/UY38201A/es not_active Application Discontinuation
-
2020
- 2020-10-20 IL IL278175A patent/IL278175A/en unknown
- 2020-10-21 PH PH12020551750A patent/PH12020551750A1/en unknown
- 2020-10-21 DO DO2020000189A patent/DOP2020000189A/es unknown
- 2020-10-22 CL CL2020002735A patent/CL2020002735A1/es unknown
- 2020-10-23 CO CONC2020/0013343A patent/CO2020013343A2/es unknown
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