ES2614934T3 - Nueva forma cristalina III de agomelatina, su procedimiento de preparación y composiciones farmacéuticas que la contienen - Google Patents

Nueva forma cristalina III de agomelatina, su procedimiento de preparación y composiciones farmacéuticas que la contienen Download PDF

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ES2614934T3
ES2614934T3 ES10003436.2T ES10003436T ES2614934T3 ES 2614934 T3 ES2614934 T3 ES 2614934T3 ES 10003436 T ES10003436 T ES 10003436T ES 2614934 T3 ES2614934 T3 ES 2614934T3
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agomelatine
crystalline form
form iii
expressed
pharmaceutical compositions
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Gérard Coquerel
Julie Linol
Jean-Claude Souvie
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Les Laboratoires Servier SAS
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    • 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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Abstract

Forma cristalina III de agomelatina, de fórmula (I):**Fórmula** caracterizada por el siguiente diagrama de difracción de rayos X sobre polvo, medido con un difractómetro Siemens D5005 (anticátodo de cobre) y expresado en términos de distancia interreticular d, ángulo de Bragg 2 theta e intensidad relativa (expresada en porcentaje con respecto a la línea más intensa):**Fórmula**

Description

imagen1
condiciones de obtención de agomelatina en una forma que presente estas características de modo reproducible.
La solicitante ha puesto a punto ahora un procedimiento de obtención de agomelatina en una forma cristalina bien definida, perfectamente reproducible, y 5 que, por ello, presenta características interesantes de facilidad de formulación.
Más específicamente, la presente invención se refiere a la forma cristalina III del compuesto de fórmula (I), caracterizada por el siguiente diagrama de difracción de rayos X sobre polvo, medido con un difractómetro Siemens D5005 (anticátodo de cobre) y expresado en términos de distancia interreticular d, ángulo de Bragg 2
10 theta e intensidad relativa (expresada en porcentaje con respecto a la línea más intensa):
2 theta (º) exp.
d (Å) exp. Intensidad (%)
10,52
8,405 100
12,92
6,848 40
16,15
5,482 53
17,38
5,097 69
17,84
4,968 96
18,55
4,779 22
19,20
4,619 97
19,89
4,460 30
20,32
4,366 24
21,15
4,197 26
22,08
4,022 16
22,96
3,870 23
23,33
3,810 95
23,84
3,730 33
24,52
3,628 25
24,88
3,576 59
25,07
3,550 90
26,27
3,390 61
26,86
3,316 22
27,97
3,187 20
29,51
3,024 43
-3
imagen2
La posología útil se puede adaptar en función de la naturaleza y la gravedad de la afección, la vía de administración y la edad y el peso del paciente. Esta posología varía de 0,1 mg a 1 g al día, en una o varias tomas.
Los siguientes ejemplos ilustran la invención.
5 Ejemplo 1: Forma cristalina III de N-[2-(7-metoxi-1-naftil)etil]acetamida
100 g de N-[2-(7-metoxi-1-naftil)etil]acetamida se calientan a 110ºC en una estufa con ventilación hasta fusión completa y después se enfrían lentamente hasta recristalización. La forma III obtenida se caracteriza por el siguiente diagrama de difracción de rayos X sobre polvo, medido con un difractómetro Siemens D5005
10 (anticátodo de cobre) y expresado en términos de distancia interreticular d, ángulo de Bragg 2 theta e intensidad relativa (expresada en porcentaje con respecto a la línea más intensa):
2 theta (º) exp.
d (Å) exp. Intensidad (%)
10,52
8,405 100
12,92
6,848 40
16,15
5,482 53
17,38
5,097 69
17,84
4,968 96
18,55
4,779 22
19,20
4,619 97
19,89
4,460 30
20,32
4,366 24
21,15
4,197 26
22,08
4,022 16
22,96
3,870 23
23,33
3,810 95
23,84
3,730 33
24,52
3,628 25
24,88
3,576 59
25,07
3,550 90
26,27
3,390 61
26,86
3,316 22
27,97
3,187 20
29,51
3,024 43
-5
imagen3

Claims (1)

  1. Reivindicaciones
    1. Forma cristalina III de agomelatina, de fórmula (I):
    imagen1
    caracterizada por el siguiente diagrama de difracción de rayos X sobre polvo,
    5 medido con un difractómetro Siemens D5005 (anticátodo de cobre) y expresado en términos de distancia interreticular d, ángulo de Bragg 2 theta e intensidad relativa (expresada en porcentaje con respecto a la línea más intensa):
    2 theta (º) exp.
    d (Å) exp. Intensidad (%)
    10,52
    8,405 100
    12,92
    6,848 40
    16,15
    5,482 53
    17,38
    5,097 69
    17,84
    4,968 96
    18,55
    4,779 22
    19,20
    4,619 97
    19,89
    4,460 30
    20,32
    4,366 24
    21,15
    4,197 26
    22,08
    4,022 16
    22,96
    3,870 23
    23,33
    3,810 95
    23,84
    3,730 33
    24,52
    3,628 25
    24,88
    3,576 59
    25,07
    3,550 90
    26,27
    3,390 61
    26,86
    3,316 22
    27,97
    3,187 20
    29,51
    3,024 43
    -7
    imagen2
ES10003436.2T 2005-08-03 2006-08-02 Nueva forma cristalina III de agomelatina, su procedimiento de preparación y composiciones farmacéuticas que la contienen Active ES2614934T3 (es)

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FR0508276 2005-08-03
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

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ES2614934T3 true ES2614934T3 (es) 2017-06-02

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EP (3) EP2210872B1 (es)
JP (1) JP4580370B2 (es)
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AR (1) AR057713A1 (es)
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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
WO2011154140A2 (en) 2010-06-10 2011-12-15 Gador S.A. New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide and new crystalline form
CZ303787B6 (cs) * 2011-01-21 2013-05-02 Zentiva, K.S. Metastabilní krystalové formy agomelatinu a jejich farmaceutické kompozice
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
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
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
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
ES2645223T3 (es) 2013-06-06 2017-12-04 Zentiva, K.S. Formulaciones de agomelatina que comprenden agomelatina en forma de co-cristales
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
PL3075724T3 (pl) 2015-03-31 2023-12-27 F.I.S.- Fabbrica Italiana Sintetici S.P.A. Stała postać agomelatyny

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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
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

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MY142856A (en) 2011-01-14
MA28449B1 (fr) 2007-03-01
TWI389873B (zh) 2013-03-21
PY0622197A (es) 2012-09-03
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JP2007051140A (ja) 2007-03-01
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SG130112A1 (en) 2007-03-20
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FR2889521A1 (fr) 2007-02-09
EP2210872A1 (fr) 2010-07-28
JO3360B1 (ar) 2019-03-13
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CA2555117A1 (fr) 2007-02-03
SA06270253B1 (ar) 2011-05-14
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