PT2739605E - Processo para a preparação da forma cristalina i da agomelatina - Google Patents
Processo para a preparação da forma cristalina i da agomelatina Download PDFInfo
- Publication number
- PT2739605E PT2739605E PT117705079T PT11770507T PT2739605E PT 2739605 E PT2739605 E PT 2739605E PT 117705079 T PT117705079 T PT 117705079T PT 11770507 T PT11770507 T PT 11770507T PT 2739605 E PT2739605 E PT 2739605E
- Authority
- PT
- Portugal
- Prior art keywords
- solvent
- solution
- crystalline form
- agomeltin
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 11
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 title description 4
- 229960002629 agomelatine Drugs 0.000 title description 3
- 239000002904 solvent Substances 0.000 claims description 29
- 239000003960 organic solvent Substances 0.000 claims description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 9
- 239000000556 agonist Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000005092 sublimation method Methods 0.000 description 2
- -1 2- (7-methoxy-naphth-1-yl) -ethyl ether Chemical compound 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 244000118350 Andrographis paniculata Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Battery Electrode And Active Subsutance (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IB2011/001805 WO2013017903A1 (en) | 2011-08-03 | 2011-08-03 | Process for the preparation of crystalline form i of agomelatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT2739605E true PT2739605E (pt) | 2016-06-20 |
Family
ID=44802320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT117705079T PT2739605E (pt) | 2011-08-03 | 2011-08-03 | Processo para a preparação da forma cristalina i da agomelatina |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20150291508A1 (enExample) |
| EP (1) | EP2739605B1 (enExample) |
| CN (1) | CN103827078B (enExample) |
| BR (1) | BR112014002523A2 (enExample) |
| CA (1) | CA2843827A1 (enExample) |
| CY (1) | CY1117823T1 (enExample) |
| DK (1) | DK2739605T3 (enExample) |
| EA (1) | EA024650B1 (enExample) |
| ES (1) | ES2577177T3 (enExample) |
| HR (1) | HRP20160767T1 (enExample) |
| HU (1) | HUE030282T2 (enExample) |
| IN (1) | IN2014CN00348A (enExample) |
| PL (1) | PL2739605T3 (enExample) |
| PT (1) | PT2739605E (enExample) |
| SI (1) | SI2739605T1 (enExample) |
| WO (1) | WO2013017903A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104876830A (zh) * | 2015-06-09 | 2015-09-02 | 江苏中邦制药有限公司 | 一种阿戈美拉汀i晶型晶体的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2658818B1 (fr) | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2866335B1 (fr) | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| EP2319827A1 (en) * | 2009-11-09 | 2011-05-11 | Ratiopharm GmbH | Process for the production of polymorph form I of agomelatine |
| CN101704763B (zh) | 2009-11-25 | 2012-03-28 | 天津泰普药品科技发展有限公司 | 阿戈美拉汀i型晶体的制备方法 |
| CN101921205B (zh) * | 2010-08-30 | 2013-11-20 | 江苏恩华药业股份有限公司 | 阿戈美拉汀ⅰ晶型的制备方法 |
-
2011
- 2011-08-03 CN CN201180072630.4A patent/CN103827078B/zh not_active Expired - Fee Related
- 2011-08-03 HR HRP20160767TT patent/HRP20160767T1/hr unknown
- 2011-08-03 PL PL11770507.9T patent/PL2739605T3/pl unknown
- 2011-08-03 BR BR112014002523A patent/BR112014002523A2/pt not_active Application Discontinuation
- 2011-08-03 IN IN348CHN2014 patent/IN2014CN00348A/en unknown
- 2011-08-03 WO PCT/IB2011/001805 patent/WO2013017903A1/en not_active Ceased
- 2011-08-03 CA CA2843827A patent/CA2843827A1/en not_active Abandoned
- 2011-08-03 PT PT117705079T patent/PT2739605E/pt unknown
- 2011-08-03 EP EP11770507.9A patent/EP2739605B1/en not_active Not-in-force
- 2011-08-03 SI SI201130880A patent/SI2739605T1/sl unknown
- 2011-08-03 HU HUE11770507A patent/HUE030282T2/en unknown
- 2011-08-03 EA EA201400188A patent/EA024650B1/ru not_active IP Right Cessation
- 2011-08-03 DK DK11770507.9T patent/DK2739605T3/en active
- 2011-08-03 ES ES11770507.9T patent/ES2577177T3/es active Active
- 2011-08-03 US US14/236,772 patent/US20150291508A1/en not_active Abandoned
-
2016
- 2016-07-20 CY CY20161100712T patent/CY1117823T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014002523A2 (pt) | 2017-03-14 |
| EP2739605A1 (en) | 2014-06-11 |
| WO2013017903A1 (en) | 2013-02-07 |
| CN103827078B (zh) | 2015-08-05 |
| DK2739605T3 (en) | 2016-07-25 |
| EA024650B1 (ru) | 2016-10-31 |
| EP2739605B1 (en) | 2016-04-27 |
| ES2577177T3 (es) | 2016-07-13 |
| HRP20160767T1 (hr) | 2016-08-12 |
| PL2739605T3 (pl) | 2016-11-30 |
| IN2014CN00348A (enExample) | 2015-04-03 |
| CY1117823T1 (el) | 2017-05-17 |
| HUE030282T2 (en) | 2017-05-29 |
| SI2739605T1 (sl) | 2016-08-31 |
| CN103827078A (zh) | 2014-05-28 |
| EA201400188A1 (ru) | 2014-07-30 |
| US20150291508A1 (en) | 2015-10-15 |
| CA2843827A1 (en) | 2013-02-07 |
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