EP2595976A1 - Verfahren zur herstellung von aminobenzoylbenzofuranderivaten - Google Patents
Verfahren zur herstellung von aminobenzoylbenzofuranderivatenInfo
- Publication number
- EP2595976A1 EP2595976A1 EP11754698.6A EP11754698A EP2595976A1 EP 2595976 A1 EP2595976 A1 EP 2595976A1 EP 11754698 A EP11754698 A EP 11754698A EP 2595976 A1 EP2595976 A1 EP 2595976A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- butyl
- linear
- branched
- benzofuran
- ether
- 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.)
- Withdrawn
Links
Classifications
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
Definitions
- the present invention relates generally to the preparation of amino benzoyl benzofuran derivatives.
- the invention relates to a process for the preparation of 5-amino-benzoylbenzofuran derivatives of general formula:
- R 1 is hydrogen or alkyl and R 2 is hydrogen, alkyl, alkoxy or dialkylaminoalkoxy.
- R 1 represents, in particular, a linear or branched C 1 -C 8 alkyl group, in particular a linear or branched C 1 -C 4 alkyl group such as methyl, ethyl, n-propyl, isopropyl or n-butyl, and butyl or tert-butyl,
- R 2 represents in particular a linear or branched C 1 -C 8 alkyl group, especially a group C 1 -C 4 linear or branched alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl; a linear or branched C 1 -C 6 alkoxy group, in particular a linear or branched C 1 -C 4 alkoxy group such as methoxy, ethoxy, n-propoxy, iso-hydroxy, n-butoxy, sec-butoxy or tert-butoxy; still a dialkylaminoalkoxy group in which each linear or branched alkyl group is C 1 -C 5 and the linear or branched alkoxy group is C 1 -C 5 in which each linear or branched alkyl group is C 1 -C 4 such as methyl, ethyl, n-propyl, isopropyl
- R 1 is n-butyl and R 2 is 3- (di-n-butylamino) propoxy.
- this method requires the isolation of Compound A from its formation medium, the isolation of this compound, usually in the form of its oxalate, thus constituting an additional step in the preparation of dronedarone.
- aminoalkoxybenzoyl-benzofuran derivatives of EP 0 471 609 in particular dronedarone, may be synthesized, therefore, in the very medium for forming the appropriate compound of formula I.
- the 5-amino-benzofuran derivatives of formula I can be prepared by reducing a 5-nitro-benzofuran derivative of general formula:
- R 1 and R 2 have the same meaning as above, by means of a hydrogen transfer agent, in the presence of palladium-carbon as catalyst and in an ether or a mixture of ethers as solvent, which forms the compounds desired.
- R 1 is preferably n-butyl and R 2 is preferably 3- (di-n-butylamino) propoxy.
- the invention relates to a process for the preparation of sulphonamido-benzofuran derivatives of general formula:
- R 1 and R 2 have the same meaning as above and R 3 represents an alkyl group, the process according to which:
- a 5-nitro-benzofuran derivative of formula II is reduced by means of a hydrogen transfer agent, in the presence of palladium-carbon as a catalyst and in an ether or a mixture of ethers as solvent, to form a reaction medium containing a 5-amino-benzoyl-benzofuran derivative of formula I, above, in free base form, b) treating the reaction medium containing the 5-amino-benzoyl-benzofuran derivative of formula I in the form of of free base obtained above, with a halide of general formula:
- the pharmaceutically acceptable salt of the compound of formula III can be recovered from its forming medium, for example by crystallization.
- R 3 represents in particular a linear or branched C 1 -C 6 alkyl group, in particular a C 1 -C 4 linear or branched alkyl group such as methyl, ethyl, n-propyl or isopropyl, n-butyl or tert-butyl.
- R 1 is n-butyl
- R 2 is 3- (di-n-butylamino) propoxy
- R 3 is methyl in formula III above.
- the reduction by hydrogen transfer according to the invention is usually carried out in an ether or a mixture of ethers as a solvent, unlike the state of the art where this type of reaction is generally carried out in an alcohol.
- This reduction in an ether or a mixture of ethers allows a significant chemo-selectivity of the nitro function to the detriment of the ketone function also present and which is also likely to reduce alcohol.
- This selective reduction of the nitro function therefore avoids the isolation of the compound of formula I in any way, in particular by transformation. of this compound, obtained in basic form, into a salt easily separable from its formation medium.
- the ether used as a solvent is usually a dialkyl ether such as methyl tert-butyl ether or a cyclic ether, for example tetrahydrofuran, while the mixture of ethers generally corresponds to a mixture of dialkyl ether and cyclic ether, for example a mixture methyl tert-butyl ether and tetrahydrofuran.
- Methyl tert-butyl ether represents a particularly preferred solvent in the context of the present invention, in particular for the preparation of Compound A and subsequently of dronedarone.
- the hydrogen transfer agent is a formate, preferably ammonium formate or phosphinate, especially sodium phosphinate.
- This hydrogen transfer agent is used in excess of the compound of formula II, this excess being up to 3 to 5 equivalents of hydrogen transfer agent per equivalent of compound of formula II or more.
- 5 or approximately 5 equivalents of hydrogen transfer agent per equivalent of compound of formula II for example 5 or approximately 5 equivalents of dissolved hydrogen transfer agent, for example in a volume of water, are used.
- 5 equivalents of dissolved ammonium formate are used, for example, in one volume of water.
- the reduction can take place at room temperature. However, this is generally undertaken by heating the reaction medium to a temperature ranging from up to, for example, 50 ° C to 60 ° C, preferably at a temperature of the order of 40 ° C, in particular at 40 ° C.
- the invention also relates to a process for the preparation of 2-n-butyl-3- ⁇ 4- [3- (di-n-butylamino) -propoxy] -benzoyl ⁇ - 5-amino-benzofuran, in which 2-n-butyl-3- ⁇ 4- [3- (di-n-butylamino) -propoxy] -benzoyl ⁇ -5-nitro-benzofuran is reduced by means of formate d ammonium or sodium phosphinate as a hydrogen transfer agent, in the presence of palladium on carbon as catalyst and in methyl tert-butyl ether or a mixture of methyl tert-butyl ether and tetrahydrofuran as solvent, to form a reaction medium containing 2-n-butyl-3- ⁇ 4- [3- (di-n-butylamino) -propoxy] -benzoyl ⁇ -5-amino-benz
- the invention relates to a process for the preparation of 2-n-butyl-3- ⁇ 4- [3- (di-n-butylamino) -propoxy] -benzoyl 5-methanesulfonamido-benzofuran or dronedarone and its pharmaceutically acceptable salts, the process according to which:
- the pharmaceutically acceptable salt of dronedarone can be recovered from its formation medium, for example by crystallization.
- the complex formed by a 5-nitro-benzofuran derivative of formula II, a hydrogen transfer agent, palladium on carbon and an ether or a mixture of ethers as a solvent is particularly interesting as a reaction medium for the preparation of various compounds including the compounds of formula I and those of formula III above.
- Another object of the invention relates to a reaction medium, characterized in that it is formed:
- an ether such as methyl tert-butyl ether or a mixture of ethers such as a mixture of methyl tert-butyl ether and tetrahydrofuran, as solvent.
- the mixture is cooled to 23 ° C. (+/- 2 ° C.) and the palladium-based carbon is then filtered, which is then washed with methyl tert-butyl ether and water. Then decanted, at room temperature, the organic phase is washed with some water. These settling and washing operations are then repeated once more. The mixture is again decanted and the solution is concentrated at 40 ° C. under vacuum. The concentrate is then diluted with tetrahydrofuran to provide 3.47 kg of a solution of the desired compound in a mixture of methyl tert-butyl ether and tetrahydrofuran.
- the nitro function of the compound of formula II can be reduced in a standard reactor, which avoids the need to operate with hydrogen under pressure in a hydrogenation apparatus.
- the quality of the compound of formula I in base form is significantly improved since there is a formation of different impurities in fewer numbers and lower contents. This advantage makes it possible to avoid the preparation and isolation of the oxalate of the compound of formula I, an operation which poses numerous problems on an industrial scale.
- non-isolated compounds of formula I in a process for the preparation of the derivatives pharmacologically active aminoalkoxybenzoyl-benzofuran of patent EP 0 471 609 and in particular in a process for the preparation of the compounds of formula III above, makes it possible to very significantly improve the yield of this process.
- the overall yield of its synthesis, from its corresponding 5-nitro-benzofuran derivative amounts to 60% according to the state of the art to 95% by implementation of the chemo process. -selective of the invention. This improvement is related in particular to the absence of isolation of the oxalate of the compound of formula I and the associated losses.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1055824A FR2962731B1 (fr) | 2010-07-19 | 2010-07-19 | Procede de preparation de derives d'amino-benzoyl-benzofurane |
PCT/FR2011/051710 WO2012010788A1 (fr) | 2010-07-19 | 2011-07-18 | Procede de preparation de derives d'amino-benzoyl-benzofurane |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2595976A1 true EP2595976A1 (de) | 2013-05-29 |
Family
ID=42797382
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP11754698.6A Withdrawn EP2595976A1 (de) | 2010-07-19 | 2011-07-18 | Verfahren zur herstellung von aminobenzoylbenzofuranderivaten |
Country Status (13)
Country | Link |
---|---|
US (1) | US8884033B2 (de) |
EP (1) | EP2595976A1 (de) |
JP (1) | JP2013531054A (de) |
KR (1) | KR20130129180A (de) |
CN (1) | CN103108869A (de) |
AU (1) | AU2011281421A1 (de) |
BR (1) | BR112013001335A2 (de) |
CA (1) | CA2805815A1 (de) |
FR (1) | FR2962731B1 (de) |
MX (1) | MX2013000773A (de) |
RU (1) | RU2013107023A (de) |
SG (1) | SG187140A1 (de) |
WO (1) | WO2012010788A1 (de) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUP0900759A2 (en) | 2009-12-08 | 2011-11-28 | Sanofi Aventis | Novel process for producing dronedarone |
HUP1000010A2 (en) | 2010-01-08 | 2011-11-28 | Sanofi Sa | Process for producing dronedarone |
FR2958290B1 (fr) | 2010-03-30 | 2012-10-19 | Sanofi Aventis | Procede de preparation de derives de sulfonamido-benzofurane |
HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
FR2963006B1 (fr) | 2010-07-21 | 2013-03-15 | Sanofi Aventis | Procede de preparation de derives de nitro-benzofurane |
HUP1100167A2 (en) | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
FR2983198B1 (fr) | 2011-11-29 | 2013-11-15 | Sanofi Sa | Procede de preparation de derives de 5-amino-benzoyl-benzofurane |
EP2617718A1 (de) | 2012-01-20 | 2013-07-24 | Sanofi | Verfahren zur Herstellung von Dronedaron unter Verwendung von Dibutylaminopropanolreagenz |
WO2013121235A2 (en) | 2012-02-13 | 2013-08-22 | Sanofi | Process for preparation of dronedarone by removal of hydroxyl group |
WO2013121234A1 (en) | 2012-02-14 | 2013-08-22 | Sanofi | Process for the preparation of dronedarone by oxidation of a sulphenyl group |
US9382223B2 (en) | 2012-02-22 | 2016-07-05 | Sanofi | Process for preparation of dronedarone by oxidation of a hydroxyl group |
CN102690250A (zh) * | 2012-05-08 | 2012-09-26 | 郑州明泽医药科技有限公司 | 决奈达隆中间体及其制备方法 |
WO2013178337A1 (en) | 2012-05-31 | 2013-12-05 | Sanofi | Process for preparation of dronedarone by grignard reaction |
CN104892553B (zh) * | 2015-04-27 | 2017-06-20 | 惠州信立泰药业有限公司 | 一种盐酸决奈达隆的晶体及其制备方法和含有该晶体的药物组合物 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2665444B1 (fr) * | 1990-08-06 | 1992-11-27 | Sanofi Sa | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. |
FR2817865B1 (fr) | 2000-12-11 | 2005-02-18 | Sanofi Synthelabo | Derive aminoalkoxybenzoyle sous forme de sel, son procede de preparation et son utilisation comme intermediaire de synthese |
FR2817864B1 (fr) | 2000-12-11 | 2003-02-21 | Sanofi Synthelabo | Derive de methanesulfonamido-benzofurane, son procede de preparation et son utilisation comme intermediaire de synthese |
WO2007087684A1 (en) * | 2006-02-03 | 2007-08-09 | Bionomics Limited | Substituted benzofurans, benzothiophenes, benzoselenophenes and indoles and their use as tubulin polymerisation inhibitors |
GB0719180D0 (en) * | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
TW201107303A (en) | 2009-05-27 | 2011-03-01 | Sanofi Aventis | Process for the production of benzofurans |
TW201111354A (en) | 2009-05-27 | 2011-04-01 | Sanofi Aventis | Process for the production of Dronedarone intermediates |
HUP0900759A2 (en) | 2009-12-08 | 2011-11-28 | Sanofi Aventis | Novel process for producing dronedarone |
HUP1000010A2 (en) | 2010-01-08 | 2011-11-28 | Sanofi Sa | Process for producing dronedarone |
FR2957079B1 (fr) | 2010-03-02 | 2012-07-27 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
FR2963006B1 (fr) | 2010-07-21 | 2013-03-15 | Sanofi Aventis | Procede de preparation de derives de nitro-benzofurane |
FR2973027A1 (fr) | 2011-03-24 | 2012-09-28 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
HUP1100166A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Reductive amination process for preparation of dronedarone using amine intermediary compound |
HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
HUP1100167A2 (en) | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
-
2010
- 2010-07-19 FR FR1055824A patent/FR2962731B1/fr not_active Expired - Fee Related
-
2011
- 2011-07-18 AU AU2011281421A patent/AU2011281421A1/en not_active Abandoned
- 2011-07-18 EP EP11754698.6A patent/EP2595976A1/de not_active Withdrawn
- 2011-07-18 SG SG2013004296A patent/SG187140A1/en unknown
- 2011-07-18 BR BR112013001335A patent/BR112013001335A2/pt not_active Application Discontinuation
- 2011-07-18 JP JP2013520184A patent/JP2013531054A/ja active Pending
- 2011-07-18 MX MX2013000773A patent/MX2013000773A/es not_active Application Discontinuation
- 2011-07-18 CA CA2805815A patent/CA2805815A1/fr not_active Abandoned
- 2011-07-18 RU RU2013107023/04A patent/RU2013107023A/ru not_active Application Discontinuation
- 2011-07-18 CN CN2011800449848A patent/CN103108869A/zh active Pending
- 2011-07-18 WO PCT/FR2011/051710 patent/WO2012010788A1/fr active Application Filing
- 2011-07-18 KR KR1020137003998A patent/KR20130129180A/ko not_active Application Discontinuation
-
2013
- 2013-01-16 US US13/742,816 patent/US8884033B2/en active Active
Non-Patent Citations (1)
Title |
---|
See references of WO2012010788A1 * |
Also Published As
Publication number | Publication date |
---|---|
CN103108869A (zh) | 2013-05-15 |
MX2013000773A (es) | 2013-07-05 |
SG187140A1 (en) | 2013-02-28 |
KR20130129180A (ko) | 2013-11-27 |
CA2805815A1 (fr) | 2012-01-26 |
JP2013531054A (ja) | 2013-08-01 |
US8884033B2 (en) | 2014-11-11 |
AU2011281421A1 (en) | 2013-02-21 |
BR112013001335A2 (pt) | 2016-05-17 |
RU2013107023A (ru) | 2014-08-27 |
FR2962731B1 (fr) | 2012-08-17 |
US20130165675A1 (en) | 2013-06-27 |
WO2012010788A1 (fr) | 2012-01-26 |
FR2962731A1 (fr) | 2012-01-20 |
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