PE20201257A1 - Proceso para la hidrolisis de esteres carboxilicos de quinolona - Google Patents
Proceso para la hidrolisis de esteres carboxilicos de quinolonaInfo
- Publication number
- PE20201257A1 PE20201257A1 PE2020001673A PE2020001673A PE20201257A1 PE 20201257 A1 PE20201257 A1 PE 20201257A1 PE 2020001673 A PE2020001673 A PE 2020001673A PE 2020001673 A PE2020001673 A PE 2020001673A PE 20201257 A1 PE20201257 A1 PE 20201257A1
- Authority
- PE
- Peru
- Prior art keywords
- equal
- formula
- acid
- alkyl
- less
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- 230000007062 hydrolysis Effects 0.000 title abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 title abstract 3
- -1 QUINOLONE CARBOXYL ESTERS Chemical class 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 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 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 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 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- LZLXHGFNOWILIY-APPDUMDISA-N pradofloxacin Chemical compound C12=C(C#N)C(N3C[C@H]4NCCC[C@H]4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 LZLXHGFNOWILIY-APPDUMDISA-N 0.000 abstract 1
- 229960001248 pradofloxacin Drugs 0.000 abstract 1
- 150000007660 quinolones Chemical class 0.000 abstract 1
- JATLJHBAMQKRDH-UHFFFAOYSA-N vebufloxacin Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)CCC3=C1N1CCN(C)CC1 JATLJHBAMQKRDH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002699 waste material Substances 0.000 abstract 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
- C07D215/48—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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Health & Medical Sciences (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
La presente invencion se refiere a un procedimiento para la hidrolisis de los esteres del acido carboxilicos de quinolona de formula (II) para obtener acidos quinoloncarboxilicos de la formula general (I), donde en la formula (II) R1 es alquilo C1-C4 y en las formulas (I) y (II) concordantemente: R2 es hidrogeno, alquilo C1-C4, entre otros; R3 y R4 son halogeno; R5 es hidrogeno, alquilo C1-C4, halogeno o nitro e Y es alquilo C1-C6, ciclopropilo o fenilo, donde R2 e Y juntos tambien pueden ser un puente -CH2-CH2-O- o -CH(CH3)-CH2-O unido al atomo de nitrogeno con un atono de C. Dicho procedimiento comprende la etapa: A) reaccion de compuestos de formula (II) con una mezcla que contiene acido acetico, acido sulfurico y agua, caracterizado porque en la etapa A) se utilizan por mol de compuestos de la formula (II): mayor o igual a 30 a menor o igual a 40 mol de acido acetico, mayor o igual a 0.3 a menor o igual a 1 mol de acido sulfurico y mayor o igual a 0.9 a menor o igual a 2.5 mol de agua, adicionalmente, la temperatura de reaccion de la etapa A) es de mayor o igual a 90 a menor o igual a 99 °C. Son compuestos especificos de formula (I): acido 1-ciclopropil-6,7,8-trifluoro-1,4-dihidro-4-oxo-3-quinolincarboxilico, acido 1-ciclopropil-6,7-difluoro-1,4-dihidro-4-oxo-3-quinolincarboxilico, entre otros. Es un procedimiento especifico cuando las formulas (II) y (I) tiene el significado segun las formulas (II-1) o (I-1). Dicho procedimiento mejora la hidrolisis de esteres del acido quinoloncarboxilico, en el que se producen la menor cantidad de desechos posibles y en el que el acido quinoloncarboxilico obtenido tiene la mayor pureza posible, siendo particularmente adecuado para la sintesis del intermedio (I) en la sintesis de compuestos antibioticos farmaceuticamente activos conocidos de la clase de las quinolonas, tales como pradofloxacina, benofloxacina, entre otros.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18169170 | 2018-04-25 | ||
| PCT/EP2019/060072 WO2019206798A1 (de) | 2018-04-25 | 2019-04-18 | Verfahren zur hydrolyse von chinoloncarbonsäureestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20201257A1 true PE20201257A1 (es) | 2020-11-16 |
Family
ID=62063375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2020001673A PE20201257A1 (es) | 2018-04-25 | 2019-04-18 | Proceso para la hidrolisis de esteres carboxilicos de quinolona |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US11332444B2 (es) |
| EP (1) | EP3784656B1 (es) |
| JP (1) | JP7410050B2 (es) |
| KR (1) | KR102727204B1 (es) |
| CN (1) | CN111989314B (es) |
| AU (1) | AU2019260015C1 (es) |
| CA (1) | CA3098060A1 (es) |
| CL (1) | CL2020002735A1 (es) |
| CO (1) | CO2020013343A2 (es) |
| CR (1) | CR20200502A (es) |
| DK (1) | DK3784656T3 (es) |
| DO (1) | DOP2020000189A (es) |
| ES (1) | ES2956316T3 (es) |
| IL (1) | IL278175A (es) |
| MX (1) | MX2020011280A (es) |
| MY (1) | MY204213A (es) |
| PE (1) | PE20201257A1 (es) |
| PH (1) | PH12020551750A1 (es) |
| PT (1) | PT3784656T (es) |
| SG (1) | SG11202010544TA (es) |
| TW (1) | TW202003470A (es) |
| UY (1) | UY38201A (es) |
| WO (1) | WO2019206798A1 (es) |
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 |
| HU228036B1 (en) | 1996-02-23 | 2012-08-28 | Bayer Animal Health Gmbh | Optionally substituted 8-cyano-1-cyclopropyl-7-(2,8-diazabicyclo-[4,3,0]-nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolin carboxylic acids and their derivatives, process producing them and medicaments thereof |
| 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 AU AU2019260015A patent/AU2019260015C1/en active Active
- 2019-04-18 DK DK19720502.4T patent/DK3784656T3/da active
- 2019-04-18 CN CN201980026978.6A patent/CN111989314B/zh active Active
- 2019-04-18 SG SG11202010544TA patent/SG11202010544TA/en unknown
- 2019-04-18 PT PT197205024T patent/PT3784656T/pt unknown
- 2019-04-18 MX MX2020011280A patent/MX2020011280A/es unknown
- 2019-04-18 EP EP19720502.4A patent/EP3784656B1/de active Active
- 2019-04-18 WO PCT/EP2019/060072 patent/WO2019206798A1/de not_active Ceased
- 2019-04-18 US US17/049,925 patent/US11332444B2/en active Active
- 2019-04-18 CA CA3098060A patent/CA3098060A1/en active Pending
- 2019-04-18 KR KR1020207033003A patent/KR102727204B1/ko active Active
- 2019-04-18 ES ES19720502T patent/ES2956316T3/es active Active
- 2019-04-18 JP JP2020556943A patent/JP7410050B2/ja active Active
- 2019-04-18 CR CR20200502A patent/CR20200502A/es unknown
- 2019-04-18 MY MYPI2020005538A patent/MY204213A/en unknown
- 2019-04-18 PE PE2020001673A patent/PE20201257A1/es unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| AU2019260015B2 (en) | 2024-07-11 |
| MX2020011280A (es) | 2020-11-13 |
| CL2020002735A1 (es) | 2021-02-26 |
| CN111989314A (zh) | 2020-11-24 |
| JP7410050B2 (ja) | 2024-01-09 |
| US11332444B2 (en) | 2022-05-17 |
| JP2021521238A (ja) | 2021-08-26 |
| MY204213A (en) | 2024-08-16 |
| AU2019260015C1 (en) | 2024-11-21 |
| WO2019206798A1 (de) | 2019-10-31 |
| EP3784656A1 (de) | 2021-03-03 |
| CR20200502A (es) | 2020-12-22 |
| TW202003470A (zh) | 2020-01-16 |
| UY38201A (es) | 2019-11-29 |
| DOP2020000189A (es) | 2020-11-30 |
| DK3784656T3 (da) | 2023-09-18 |
| CO2020013343A2 (es) | 2020-10-30 |
| BR112020021635A2 (pt) | 2021-01-26 |
| IL278175A (en) | 2020-11-30 |
| KR20210005079A (ko) | 2021-01-13 |
| KR102727204B1 (ko) | 2024-11-06 |
| CN111989314B (zh) | 2024-04-30 |
| PH12020551750A1 (en) | 2021-07-26 |
| CA3098060A1 (en) | 2019-10-31 |
| AU2019260015A1 (en) | 2020-12-17 |
| SG11202010544TA (en) | 2020-11-27 |
| EP3784656B1 (de) | 2023-06-28 |
| PT3784656T (pt) | 2023-09-22 |
| ES2956316T3 (es) | 2023-12-19 |
| US20210078950A1 (en) | 2021-03-18 |
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