RS55499B1 - Novi kristalni oblik iii agomelatina, postupak njegove proizvodnje i farmaceutske kompozicije koje ga sadrže - Google Patents
Novi kristalni oblik iii agomelatina, postupak njegove proizvodnje i farmaceutske kompozicije koje ga sadržeInfo
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- RS55499B1 RS55499B1 RS20161179A RSP20161179A RS55499B1 RS 55499 B1 RS55499 B1 RS 55499B1 RS 20161179 A RS20161179 A RS 20161179A RS P20161179 A RSP20161179 A RS P20161179A RS 55499 B1 RS55499 B1 RS 55499B1
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- C—CHEMISTRY; METALLURGY
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- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
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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
- C07C233/16—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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Child & Adolescent Psychology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Ovaj pronalazak se odnosi na novi kristalni III oblik agomelatina ili<y>V-[2-(7-metoksi-l-naftil)etil]acetamid formule (I):
postupak njegove proizvodnje, kao i na farmaceutske kompozicije koje ga sadrže.
Agomelatin ili Af-[2-(7-metoksi-l-naftil)etiI]acetamid ima korisna farmakološka svojstva.
Ispoljava dejstvo dvostruke osobenosti, da je sa jedne strane agonist na receptorima melatoninergičnog sistema, a sa druge strane je antagonist receptora 5-HT2C- Ova svojstva mu daju aktivnost u centralnom nervnom sistemu i, preciznije, u lečenju depresije major, sezonskih depresija, poremećaja spavanja, kardiovaskularnih patologija, patologija digestivnog sistema, nesanica i umora kao posledica vremenske razlike, poremećaja apetita i gojaznosti.
Agomelatin, njegova proizvodnja i njegova upotreba u terapeutske svrhe, opisani su u evropskom patentu EP 0 447 285.
Uzimajući u obzir farmaceutsku korist od ovog jedinjenja, prioritet će biti dobijanje istog u stanju odlične čistoće i, pre svega, u obliku koji ima perfektnu reproducibilnost, koji ima povoljna svojstva koja olakšavaju formulisanje koje omogućava njegovo čuvanje u dužem vremenskom periodu bez posebnih uslova u pogledu temperature, svetla, vlažnosti ili sadržaja kiseonika.
Patent EP 0 447 285 opisuje dobijanje agomelatina u osam koraka polazeći od 7-metoksi-l-tetralona. Međutim, ovaj dokument ne precizira uslove dobijanja agomelatina u obliku koji ima ove karakteristike na reproducibilan način.
Podnosilac zahteva sada ističe postupak dobijanja agomelatina u kristalnom obliku koji je dobro definisan, savršeno reproduktibilan i ispoljava povoljne osobine u pogledu jednostavnog formulisanja.
Preciznije, ovaj pronalazak se odnosi na kristalan oblik III jedinjenja formule (I), koji je naznačen sledećim dijagramom difrakcije X zraka na prašku, koji je izmeren na difraktometru Siemens D5005 (bakarna antikatoda) i izražen pomoću međuravanske udaljenosti d, Bragg 2 teta ugla i relativnog intenziteta (izražen kao procenat u odnosu na traku najvećeg intenziteta) :
Pronalazak se, takođe, odnosi na postupak izrade kristalnog oblika III jedinjenja formule (I), koji je naznačen time što se agomelatin greje na 110°C do potpunog topljenja, zatim se polako ohladi sve dok ne rekristališe.
Dobijanje ovog kristalnog oblika ima za prednost omogućavanje proizvodnje farmaceutskih formulacija koje će imati konstantan sastav i biti reproducibilne, što je od posebne prednosti s obzirom na to da su ove formulacije namenjene za oralnu primenu.
Tako, dobijeni rezultati farmakološkog istraživanja oblika III, pokazuju njegovu veoma važnu aktivnost u centralnom nervnom sistemu, kao i dejstvo na mikrocirkulaciju što mu omogućava primenu u lečenju stresa, poremećaja spavanja, anksioznosti, depresije major, sezonskih depresija, kardiovaskularnih patologija, patologija sistema za varenje, nesanica i umora kao posledica vremenske razlike. Šizofrenije, napada panike, melanholije, poremećaja apetita, gojaznosti, nesanice, bola, psihotičnih poremećaja, epilepsije, dijabetesa, Parkinsonove bolesti, senilne demencije, različitih poremećaja povezanih sa normalnim ili patološkim starenjem, migrene, gubitka pamćenja, Alzheimerove bolesti, kao i poremećaja moždane cirkulacije. U drugom domenu aktivnosti, jasno je da se u lečenju, oblik III agomelatina može koristiti kod seksualnih disfunkcija, poseduje svojstva inhibitora ovulacije, imunomodulatora i može da se koristi u lečenju kancera.
Kristalni oblik III agomelatina se poželjno može koristiti za lečenje depresije major, sezonskih depresija, poremećaja spavanja, kardiovaskularnih patologija, patologija digestivnog sistema, nesanice i umora kao posledica vremenske razlike, poremećaja apetita i gojaznosti.
Pronalazak se, takođe, odnosi na farmaceutske kompozicije, koje kao aktivan princip sadrže kristalni oblik III jedinjenja formule (I) zajedno sa jednom ili više inertnih podloga, koje nisu toksične i koje su odgovarajuće. Od farmaceutskih kompozicija prema pronalasku, mogu se navesti preciznije one, koje su prikladne za oralno, parenteralno (intravensko ili subkutano), nazalno primenjivanje, jednostavne pilule ili dražeje. granule, sublingvalne tablete, želatinske kapsule, tablete, supozitorije, kremovi, masti, gelovi za kožu, injektabilni preparati, oralne suspenzije i paste za žvakanje.
Doziranje, koje će se primeniti, prilagodljivo je s obzirom na prirodu i težinu bolesti, način primenjivanja, kao i starost i težinu pacijenta. Ovo doziranje varira od 0.1 mg do 1 g dnevno, u jednoj ili više doza.
Primeri u nastavku ilustruju pronalazak.
Primer 1:Kristalni oblik III iV-(l-(7-metoksi-l-naftil)etiI]acetamida
100 g 7^-[2-(7-metoksi-l-naftil)etil]acetamida se greje na 110°C u sušnici dok se ne istopi, zatim se polako ohladi da bi došlo do rekristalizacije. Dobijeni oblik III je opisan sledećim dijagramom difrakcije X zraka na prašku, koji je izmeren na difraktometru Siemens D5005 (bakarna antikatoda) i izražen pomoću međuravanske udaljenosti d, Bragg 2 teta ugla i relativnog intenziteta (izražen kao procenat u odnosu na traku najvećeg intenziteta):
Primer 2 :Farmaceutska kompozicija
Formula za proizvodnju 1000 tableta doze 25 mg :
Primer 3: Farmaceutska kompozicija
Formula za proizvodnju 1000 tableta doze 25 mg:
Claims (5)
1. Kristalni oblik III agomelatina formule (I) :
naznačensledećim dijagramom difrakcije X zraka na prašku, koji je izmeren na difraktometru Siemens D5005 (bakama antikatoda) i izražen pomoću međuravanske udaljenosti d, Bragg 2 teta ugla i relativnog intenziteta (izražen kao procenat u odnosu na traku najvećeg intenziteta) :
2. Postupak proizvodnje kristalnog oblikaIIIjedinjenja formule (I) prema zahtevu 1,naznačen timeŠto se agomelatin greje na 110°C sve dok se potpuno ne istopi, a zatim se polako hladi dok se ne postigne rekristalizacija.
3. Farmaceutske kompozicije koje kao aktivan princip sadrže kristalni oblik III agomelatina prema zahtevu 1, u kombinaciji sa jednim ili više inertnih, netoksičnih i farmaceutski prihvatljivih nosača.
4. Farmaceutske kompozicije prema zahtevu 3 za upotrebu u proizvodnji lekova za lečenje poremećaja melatoninergičnog suistema.
5. Farmaceutske kompozicije prema zahtevu 3 za upotrebu u proizvodnji lekova za lečenje poremećaja spavanja, stresa, anksioznosti, sezonskih depresija ili depresije major, kardiovaskularnih patologija, patologija digestivnog sistema, nesanice i umora kao posledice vremenske razlike, šizofrenije, napada panike, melanholije, poremećaja apetita, gojaznosti, nesanice, psihotičnih poremećaja, epilepsije, dijabetesa, Parkinsonove bolesti, senilne demencije, različitih poremećaja koji su u vezi sa normalnim ili patološkim starenjem, migrene, gubitka pamćenja, Alzheimerove bolesti, poremećaja moždane cirkulacije, kao i u seksualnim disfunkcijama, kao inhibitori ovulacije i imunomodulatori i u lečenju kancera.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0508276A FR2889521B1 (fr) | 2005-08-03 | 2005-08-03 | Nouvelle forme cristalline iii de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| EP10003436.2A EP2210872B1 (fr) | 2005-08-03 | 2006-08-02 | Nouvelle forme cristalline iii de l'agomélatine, son procédé de préparation et les compositions pharmaceutiques qui la contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RS55499B1 true RS55499B1 (sr) | 2017-05-31 |
Family
ID=36587257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RS20161179A RS55499B1 (sr) | 2005-08-03 | 2006-08-02 | Novi kristalni oblik iii agomelatina, postupak njegove proizvodnje i farmaceutske kompozicije koje ga sadrže |
Country Status (35)
| Country | Link |
|---|---|
| EP (3) | EP1752445A1 (sr) |
| JP (1) | JP4580370B2 (sr) |
| CN (1) | CN100450995C (sr) |
| AR (1) | AR057713A1 (sr) |
| AU (1) | AU2006203336B2 (sr) |
| BR (1) | BRPI0603074A (sr) |
| CA (1) | CA2555117A1 (sr) |
| CY (1) | CY1118637T1 (sr) |
| DK (1) | DK2210872T3 (sr) |
| EA (1) | EA011031B1 (sr) |
| ES (1) | ES2614934T3 (sr) |
| FR (1) | FR2889521B1 (sr) |
| GE (1) | GEP20094576B (sr) |
| GT (1) | GT200600347A (sr) |
| HR (1) | HRP20170095T1 (sr) |
| HU (1) | HUE030506T2 (sr) |
| JO (1) | JO3360B1 (sr) |
| LT (1) | LT2210872T (sr) |
| MA (1) | MA28449B1 (sr) |
| ME (1) | ME02689B (sr) |
| MX (1) | MXPA06008790A (sr) |
| MY (1) | MY142856A (sr) |
| NO (1) | NO337010B1 (sr) |
| NZ (1) | NZ548862A (sr) |
| PE (1) | PE20070213A1 (sr) |
| PL (1) | PL2210872T3 (sr) |
| PT (1) | PT2210872T (sr) |
| RS (1) | RS55499B1 (sr) |
| SA (1) | SA06270253B1 (sr) |
| SG (1) | SG130112A1 (sr) |
| SI (1) | SI2210872T1 (sr) |
| TW (1) | TWI389873B (sr) |
| UA (1) | UA83719C2 (sr) |
| WO (1) | WO2007015003A2 (sr) |
| ZA (1) | ZA200606454B (sr) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2934856B1 (fr) * | 2008-08-05 | 2010-08-13 | Servier Lab | Nouveau procede d'obtention de la forme cristalline v de l'agomelatine |
| 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 |
| CN102001959B (zh) * | 2009-09-01 | 2014-07-02 | 北京本草天源药物研究院 | 一种药物晶体及其制备方法和用途 |
| CN102050755B (zh) * | 2009-10-29 | 2014-11-05 | 重庆医药工业研究院有限责任公司 | 阿戈美拉汀的晶型及其制备方法 |
| CN101709036B (zh) * | 2009-12-17 | 2012-07-04 | 天津药物研究院 | 阿戈美拉汀中间体2-(7-甲氧基-1-萘基)乙胺的制备 |
| 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 |
| CN101774937B (zh) * | 2010-02-05 | 2014-01-08 | 天津市汉康医药生物技术有限公司 | N-[2-(7-甲氧基-1-萘基)乙基]乙酰胺及其组合物 |
| EP2580183B1 (en) | 2010-06-10 | 2014-07-23 | Gador S.A. | New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide |
| CZ303787B6 (cs) * | 2011-01-21 | 2013-05-02 | Zentiva, K.S. | Metastabilní krystalové formy agomelatinu a jejich farmaceutické kompozice |
| CN102690210A (zh) * | 2011-03-23 | 2012-09-26 | 上海医药工业研究院 | 阿戈美拉汀的新晶型ⅶ、其制备方法、应用和包含其的药物组合物 |
| CN102690209A (zh) * | 2011-03-23 | 2012-09-26 | 上海医药工业研究院 | 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 |
| FR2978916B1 (fr) | 2011-08-10 | 2013-07-26 | Servier Lab | Composition pharmaceutique solide pour administration buccale d'agomelatine |
| EP2771312B1 (en) | 2011-11-30 | 2017-05-31 | ratiopharm GmbH | Agomelatine-urea complex and crystalline forms thereof |
| CZ2012108A3 (en) | 2012-02-15 | 2013-02-27 | Zentiva Ks | A method for the manufacture of a polymorphously stable pharmaceutical composition containing agomelatine |
| EP2934502A1 (en) | 2012-12-21 | 2015-10-28 | Laboratorios Lesvi S.L. | Process for prepararing n-(2-(7-methoxy-1-naphthalenyl)ethyl) acetamide and solid forms thereof |
| FR3001894A1 (fr) | 2013-02-08 | 2014-08-15 | Servier Lab | Composition pharmaceutique solide pour administration buccale d'agomelatine |
| ES2645223T3 (es) | 2013-06-06 | 2017-12-04 | Zentiva, K.S. | Formulaciones de agomelatina que comprenden agomelatina en forma de co-cristales |
| EP2810647A1 (en) | 2013-06-06 | 2014-12-10 | Zentiva, a.s. | Pharmaceutical formulations comprising agomelatine in the form of agomelatine co-crystal with an organic acid |
| CZ2013621A3 (cs) | 2013-08-13 | 2015-02-25 | Zentiva, K.S. | Termodynamicky stabilní tuhý roztok agomelatinu pro použití ve farmaceutické formulaci |
| WO2015124496A1 (en) | 2014-02-19 | 2015-08-27 | Synthon B.V. | Pharmaceutical composition comprising amorphous agomelatine |
| EP3075724B1 (en) | 2015-03-31 | 2023-07-12 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Solid form of agomelatine |
Family Cites Families (3)
| 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. |
| FR2866336B1 (fr) * | 2004-02-13 | 2006-03-24 | Servier Lab | Nouveau procede de synthese du (7-methoxy-3,4-dihydro-1-naphtalenyl) acetonitrile et application a la synthese de l'agomelatine |
| FR2866335B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
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2005
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