HRP20170575T1 - Miješani kristalni (oblik-viii) agomelatina, postupak njegove priprave i farmaceutski pripravak koji ga sadrži - Google Patents
Miješani kristalni (oblik-viii) agomelatina, postupak njegove priprave i farmaceutski pripravak koji ga sadrži Download PDFInfo
- Publication number
- HRP20170575T1 HRP20170575T1 HRP20170575TT HRP20170575T HRP20170575T1 HR P20170575 T1 HRP20170575 T1 HR P20170575T1 HR P20170575T T HRP20170575T T HR P20170575TT HR P20170575 T HRP20170575 T HR P20170575T HR P20170575 T1 HRP20170575 T1 HR P20170575T1
- Authority
- HR
- Croatia
- Prior art keywords
- preparation
- agomelatine
- mixed
- diseases
- pharmaceutical
- Prior art date
Links
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 title claims 10
- 238000002360 preparation method Methods 0.000 title claims 9
- 229960002629 agomelatine Drugs 0.000 title claims 8
- 239000013078 crystal Substances 0.000 title claims 5
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- 238000002425 crystallisation Methods 0.000 claims 4
- 230000008025 crystallization Effects 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 239000011541 reaction mixture Substances 0.000 claims 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 239000001632 sodium acetate Substances 0.000 claims 3
- 235000017281 sodium acetate Nutrition 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 2
- 206010034912 Phobia Diseases 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 210000002249 digestive system Anatomy 0.000 claims 2
- 206010022437 insomnia Diseases 0.000 claims 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000019899 phobic disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 230000035882 stress Effects 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000012672 seasonal affective disease Diseases 0.000 claims 1
- 230000001932 seasonal effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
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- 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
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/08—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
- 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
Claims (14)
1. Mješoviti kristalni oblik agomelatina, naznačen time, da njegov rendgenski difrakcijski dijagram ima slijedeće vrijednosti Braggovog kuta 2θ:
[image]
uključujući kristale čiji su vršni kutovi difrakcije unutar 2θ±0.2° od gore navedenih.
2. Mješoviti kristalni oblik agomelatina, naznačen time, da njegov rendgenski difrakcijski dijagram ima sljedeće vrijednosti interplanarnog razmaka kristala d, Braggovog kuta 2θ i relativnog intenziteta:
[image]
uključujući kristale čiji su vršni kutovi difrakcije unutar 2θ±0.2° od gore navedenih
3. Mješoviti kristalni oblik agomelatina u skladu s patentnim zahtjevom 1 ili 2, naznačen time, da je u njegovom DSC dijagramu promjene apsorpcije raspon pojava vrijednosti od 97 do 98°C, endotermno vršno područje nije manje od 90 % pri čemu je poželjni omjer od 95 % do 99 %.
4. Postupak pripreme za mješoviti kristalni oblik agomelatina u skladu s bilo kojim od patentnih zahtjeva 1-3, naznačen time, da se spojevi agomelatina formule (II) otope u octenoj kiselini, kojoj se potom doda natrij acetat, nakon čega slijedi dodavanje vode u kapljicama ovoj reakcijskoj smjesi, koja se zatim miješa na temperaturi od 7 do 13°C, da se potakne kristalizacija, a kristali se zatim odvoje od otopine.
[image]
5. Postupak za pripravu u skladu s patentnim zahtjevom 4, naznačen time, da je molarni omjer spojeva agomelatina formule (II) i natrijevog acetata reda veličine od 1:1 do 1.5, najpovoljnije od 1:1 do 1.1.
6. Postupak za pripravu u skladu s patentnim zahtjevom 4 ili 5, naznačen time, da je volumni omjer octene kiseline i vode 1:15-30.
7. Postupak pripreme u skladu s bilo kojim od patentnih zahtjeva 4 do 6, naznačen time, da kada se postigne temperatura dobivene reakcijske smjese 12 do 18°C, a posebice pri 15°C, u kapljicama se dodaje voda, kako bi došlo do kristalizacije.
8. Postupak za pripravu u skladu s bilo kojim od patentnih zahtjeva 4 do 7, naznačen time, da se u dobivenu reakcijsku smjesu u kapljicama dodaje voda, koja se zatim miješa na temperaturi od 10°C kako bi došlo do kristalizacije.
9. Postupak za pripravu u skladu s bilo kojim od patentnih zahtjeva 4 do 8, naznačen time, da se nakon dodavanja natrijevog acetata reakcijska smjesa zagrijava do 40 do 80°C; navedena otopina se ostavi da se sama od sebe ohladi , te se u kapljicama dodaje voda kako bi došlo do kristalizacije.
10. Farmaceutski pripravak, naznačen time, da uključuje miješani kristalni oblik agomelatina u skladu s bilo kojim od patentnih zahtjeva 1 do 3 i njihove farmaceutski prihvatljive pomoćne tvari ili ekscipijense.
11. Farmaceutski pripravak u skladu s patentnim zahtjevom 10 koji se koristi u pripravi lijeka, naznačen time, da se ovaj lijek koristi za liječenje bolesti melatonergičkog sustava.
12. Farmaceutski pripravak u skladu s patentnim zahtjevom 10 koji se koristi u pripravi lijeka, naznačen time, da se ovaj lijek koristi za liječenje poremećaja spavanja, stresa, anksioznosti, sezonskog afektivnog poremećaja, teške depresije, kardiovaskularnih bolesti, bolesti probavnog sustava, nesanice i umora izazvanog promjenom vremenskih zona (jet lag), shizofrenije, fobije, ili depresije.
13. Farmaceutska primjena miješanog oblika agomelatina u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačena time, da se navedena farmaceutska primjena odnosi na liječenje bolesti melatonergičkog sustava.
14. Farmaceutska primjena miješanog oblika agomelatina u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačena time, da se navedena farmaceutska primjena odnosi na liječenje poremećaja spavanja, stresa, anksioznosti, sezonskih poremećaj teške depresije, kardiovaskularnih bolesti, bolesti probavnog sustava, nesanice i umora izazvanog promjenom vremenskih zona (jet lag), shizofrenije, fobije, ili depresije.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100706340A CN102690209A (zh) | 2011-03-23 | 2011-03-23 | 阿戈美拉汀的混晶(形式-ⅷ)、其制备方法、应用和包含其的药物组合物 |
| PCT/CN2012/072818 WO2012126386A1 (zh) | 2011-03-23 | 2012-03-22 | 阿戈美拉汀的混晶(形式-ⅷ)、其制备方法、应用和包含其的药物组合物 |
| EP12761142.4A EP2690088B1 (en) | 2011-03-23 | 2012-03-22 | Mixed crystal agomelatine (form-viii), preparation method and use thereof and pharmaceutical composition containing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170575T1 true HRP20170575T1 (hr) | 2017-06-30 |
Family
ID=46855965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170575TT HRP20170575T1 (hr) | 2011-03-23 | 2017-04-11 | Miješani kristalni (oblik-viii) agomelatina, postupak njegove priprave i farmaceutski pripravak koji ga sadrži |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US20140088197A1 (hr) |
| EP (1) | EP2690088B1 (hr) |
| JP (1) | JP6203171B2 (hr) |
| KR (1) | KR20130136546A (hr) |
| CN (2) | CN102690209A (hr) |
| AR (1) | AR085915A1 (hr) |
| AU (1) | AU2012231548B2 (hr) |
| BR (1) | BR112013024022A2 (hr) |
| CA (1) | CA2829690C (hr) |
| CY (1) | CY1118751T1 (hr) |
| DK (1) | DK2690088T3 (hr) |
| EA (1) | EA023278B1 (hr) |
| ES (1) | ES2626030T3 (hr) |
| GE (1) | GEP201606567B (hr) |
| HK (1) | HK1193086A1 (hr) |
| HR (1) | HRP20170575T1 (hr) |
| HU (1) | HUE034329T2 (hr) |
| LT (1) | LT2690088T (hr) |
| MA (1) | MA34959B1 (hr) |
| MD (1) | MD4484C1 (hr) |
| ME (1) | ME02731B (hr) |
| MX (1) | MX355551B (hr) |
| MY (1) | MY166444A (hr) |
| PL (1) | PL2690088T3 (hr) |
| PT (1) | PT2690088T (hr) |
| RS (1) | RS55918B1 (hr) |
| SG (1) | SG193305A1 (hr) |
| SI (1) | SI2690088T1 (hr) |
| WO (1) | WO2012126386A1 (hr) |
| ZA (1) | ZA201306761B (hr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12012000132A1 (en) * | 2011-06-09 | 2014-10-20 | Servier Lab | New co-crystals of agomelatine, a process for their preparation and pharmaceutical compositions containing them |
| JP6595990B2 (ja) * | 2013-07-29 | 2019-10-23 | レ ラボラトワール セルヴィエ | アゴメラチンとスルホン酸との新規な複合体、これらの製造方法及びこれらを含有する医薬組成物 |
| CN104529804A (zh) * | 2014-12-11 | 2015-04-22 | 连云港金康医药科技有限公司 | 阿戈美拉汀的新晶型 |
| EP3075724B1 (en) | 2015-03-31 | 2023-07-12 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Solid form of agomelatine |
| EP3466923A1 (en) * | 2017-10-09 | 2019-04-10 | KRKA, d.d., Novo mesto | Process for the preparation of agomelatine in crystalline form |
Family Cites Families (17)
| 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 |
| US7498466B2 (en) * | 2004-02-13 | 2009-03-03 | Les Laboratoires Servier | Process for the synthesis and crystalline form of agomelatine |
| FR2889521B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iii de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2889523B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline v de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2889522B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iv de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2923482B1 (fr) * | 2007-11-09 | 2010-01-29 | Servier Lab | Nouvelle forme cristalline vi de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| CN101585779B (zh) * | 2009-03-10 | 2014-04-02 | 上海医药工业研究院 | 阿戈美拉汀的晶型vi及其制备方法和应用 |
| WO2011006387A1 (zh) * | 2009-07-11 | 2011-01-20 | 浙江华海药业股份有限公司 | 阿戈美拉汀的制备方法、阿戈美拉汀晶形及其制备方法 |
| CN101723844A (zh) * | 2009-11-21 | 2010-06-09 | 浙江华海药业股份有限公司 | 一种阿戈美拉汀晶形b、它的制备方法和包含它的药物组合物 |
| CN101955440B (zh) * | 2009-07-17 | 2014-04-09 | 江苏万特制药有限公司 | 一种阿戈美拉汀新晶型及其制备方法 |
| EP2319827A1 (en) * | 2009-11-09 | 2011-05-11 | Ratiopharm GmbH | Process for the production of polymorph form I of agomelatine |
| CN101781226B (zh) * | 2009-12-23 | 2012-03-28 | 天津泰普药品科技发展有限公司 | 阿戈美拉汀及其药物组合物 |
| CN101792400B (zh) * | 2010-03-16 | 2013-01-30 | 华东师范大学 | 一种阿戈美拉汀的合成方法 |
| CL2011001405A1 (es) * | 2010-06-10 | 2012-03-30 | Gador S A Conicet | Procedimiento para la preparacion de n-[2-(7-metoxi-1-naftil)etil]acetamida, agometalina. |
| WO2012046253A2 (en) * | 2010-10-08 | 2012-04-12 | Msn Laboratories Limited | Process for the preparation of n-[2- (7-methoxy-l-naphthyl) ethyl] acetamide and its novel crystalline forms |
| CN102452952A (zh) * | 2010-11-03 | 2012-05-16 | 天津药物研究院 | 一种高纯度的i型阿戈美拉汀晶体制备方法 |
-
2011
- 2011-03-23 CN CN2011100706340A patent/CN102690209A/zh active Pending
-
2012
- 2012-03-22 MA MA36226A patent/MA34959B1/fr unknown
- 2012-03-22 PT PT127611424T patent/PT2690088T/pt unknown
- 2012-03-22 WO PCT/CN2012/072818 patent/WO2012126386A1/zh active Application Filing
- 2012-03-22 AU AU2012231548A patent/AU2012231548B2/en not_active Ceased
- 2012-03-22 PL PL12761142T patent/PL2690088T3/pl unknown
- 2012-03-22 SI SI201230949A patent/SI2690088T1/sl unknown
- 2012-03-22 EP EP12761142.4A patent/EP2690088B1/en active Active
- 2012-03-22 HU HUE12761142A patent/HUE034329T2/en unknown
- 2012-03-22 CN CN201280013429.3A patent/CN103476743B/zh active Active
- 2012-03-22 DK DK12761142.4T patent/DK2690088T3/en active
- 2012-03-22 EA EA201301065A patent/EA023278B1/ru not_active IP Right Cessation
- 2012-03-22 KR KR1020137027641A patent/KR20130136546A/ko not_active Application Discontinuation
- 2012-03-22 US US14/006,484 patent/US20140088197A1/en not_active Abandoned
- 2012-03-22 LT LTEP12761142.4T patent/LT2690088T/lt unknown
- 2012-03-22 JP JP2014500244A patent/JP6203171B2/ja not_active Expired - Fee Related
- 2012-03-22 SG SG2013066600A patent/SG193305A1/en unknown
- 2012-03-22 MD MDA20130074A patent/MD4484C1/ro not_active IP Right Cessation
- 2012-03-22 CA CA2829690A patent/CA2829690C/en not_active Expired - Fee Related
- 2012-03-22 RS RS20170307A patent/RS55918B1/sr unknown
- 2012-03-22 ES ES12761142.4T patent/ES2626030T3/es active Active
- 2012-03-22 MX MX2013010634A patent/MX355551B/es active IP Right Grant
- 2012-03-22 MY MYPI2013701574A patent/MY166444A/en unknown
- 2012-03-22 GE GEAP201213264A patent/GEP201606567B/en unknown
- 2012-03-22 BR BR112013024022A patent/BR112013024022A2/pt not_active Application Discontinuation
- 2012-03-23 AR ARP120100969A patent/AR085915A1/es unknown
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2013
- 2013-09-09 ZA ZA2013/06761A patent/ZA201306761B/en unknown
-
2014
- 2014-06-24 HK HK14106352.3A patent/HK1193086A1/xx not_active IP Right Cessation
-
2017
- 2017-03-20 CY CY20171100351T patent/CY1118751T1/el unknown
- 2017-04-11 HR HRP20170575TT patent/HRP20170575T1/hr unknown
- 2017-06-12 ME MEP-2017-109A patent/ME02731B/me unknown
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