NZ548863A - New crystalline form IV of agomelatine, a process for its preparation and pharmaceutical compositions containing it - Google Patents

New crystalline form IV of agomelatine, a process for its preparation and pharmaceutical compositions containing it

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Publication number
NZ548863A
NZ548863A NZ548863A NZ54886306A NZ548863A NZ 548863 A NZ548863 A NZ 548863A NZ 548863 A NZ548863 A NZ 548863A NZ 54886306 A NZ54886306 A NZ 54886306A NZ 548863 A NZ548863 A NZ 548863A
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NZ
New Zealand
Prior art keywords
disorders
agomelatine
crystalline form
insomnia
disease
Prior art date
Application number
NZ548863A
Inventor
Gerard Coquerel
Julie Linol
Jean-Claude Souvie
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Servier Lab
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Publication of NZ548863A publication Critical patent/NZ548863A/en

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    • 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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    • A—HUMAN NECESSITIES
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    • 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

Crystalline form IV of agomelatine (N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide) is disclosed, wherein the crystalline form IV of agomelatine has powder X-ray diffraction diagram, measured using a diffractometer (copper anticathode) and expressed in terms of inter-planar distance d (17.524-3.190 A[deg]), Bragg's angle 2 theta (5.04-27.95 degree), intensity and relative intensity (expressed as a percentage with respect to the most intense ray). A process for the preparation of the crystalline form IV of agomelatine is disclosed, wherein agomelatine is heated at 110[deg.] C. until completely melted, is then rapidly cooled between 50 and 70[deg.] C, and is maintained for about 5 hours at 70[deg.] C until crystallisation occurs. A pharmaceutical composition comprising as active ingredient an effective amount of crystalline form IV of agomelatine is suitable for treating sleep disorders, stress, anxiety, seasonal affective disorders or severe depression, cardiovascular pathologies, pathologies of the digestive system, insomnia and fatigue due to jetlag, schizophrenia, panic attacks, melancholia, appetite disorders, obesity, insomnia, psychotic disorders, epilepsy, diabetes, Parkinson's disease, senile dementia, various disorders associated with normal or pathological ageing, migraine, memory loss, Alzheimer's disease, cerebral circulation disorders, and also in sexual dysfunction, as ovulation inhibitors, immunomodulators and cancers.

Description

New Zealand Paient Spedficaiion for Paient Number 548863 *10052303718* 548863 NEW ZEALAND PATENTS ACT, 1953 No: Date: COMPLETE SPECIFICATION NEW CRYSTALLINE FORM IV OF AGOMELATINE, A PROCESS FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT We, LES LABORATOIRES SERVIER, a French body corporate of 12, place de La Defense, 92415 Courbevoie Cedex, France, do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: (followed by page la) The present invention relates to a new crystalline form IV of agomelatine, or AL[2-(7-methoxy-l-naphthyl)ethyl]acetamide, of formula (I): MeO NHCOMe (I) a process for its preparation and pharmaceutical compositions containing it.
Agomelatine, or Ar-[2-(7-methoxy-l-naphthyl)ethyl]acetamide, has valuable pharmacological properties.
Indeed it has the double feature of being, on the one hand, an agonist of melatoninergic system receptors and, on the other hand, an antagonist of the 5-HT2C receptor. Those properties confer activity in the central nervous system and, more especially, in the treatment of severe depression, seasonal affective disorders, sleep disorders, cardiovascular pathologies, pathologies of the digestive system, insomnia and fatigue resulting from jetlag, appetite disorders and obesity.
Agomelatine, its preparation and its therapeutic use have been described in European Patent Specification EP 0 447 285.
In view of the pharmaceutical value of this compound, it has been important to be able to obtain it with excellent purity, with well defined crystalline form, perfectly reproducible, which as a result exhibits valuable characteristics in terms of formulation and sufficiently stable to allow its storage for long periods without particular requirements for temperature, light, humidity or oxygen level.
Patent Specification EP 0 447 285 describes the preparation of agomelatine in eight steps, starting from 7-methoxy-l-tetralone. However, that document does not specify the conditions for obtaining agomelatine in a form that exhibits those characteristics in a reproducible manner.
The Applicant has now developed a new synthesis process that allows agomelatine to be obtained in a well defined, perfectly reproducible crystalline form that especially exhibits valuable characteristics for formulation.
More specifically, the present invention relates to the crystalline form IV of the compound of formula (I), characterised by the following powder X-ray diffraction diagram, measured using a Siemens D5005 diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage of the most intense ray): 2-Theta (°) d(A) Intensity exp. exp. (%) .04 17.524 8 .16 8.703 68 .51 8.409 9 .22 .818 28 16.75 .288 39 17.41 .089 60 18.03 4.915 100 18.81 4.714 71 .48 4.333 37 21.61 4.110 16 23.27 3.819 11 24.04 3.699 26 24.27 3.665 42 24.77 3.591 24 .57 3.481 13 27.06 3.292 6 27.95 3.190 11 The invention relates also to a process for the preparation of the crystalline form IV of the compound of formula (I), which process is characterised in that agomelatine is heated at intellectual property office of n.z. 06 JUL 2007 RECEIVED 110°C until the melting be completed, and is then rapidly cooled between 50 and 70°C, and maintained for about 5 hours at 70°C until crystallisation.
An advantage of obtaining that crystalline form is that it allows the preparation of pharmaceutical formulations having a consistent and reproducible composition, which is 5 especially advantageous when the formulations are to be used for oral administration.
A pharmacological study of the form IV so obtained has demonstrated that it has substantial activity in respect of the central nervous system and in respect of microcirculation, enabling it to be established that the crystalline form IV of agomelatine is useful in the treatment of stress, sleep disorders, anxiety, severe depression, seasonal 10 affective disorders, cardiovascular pathologies, pathologies of the digestive system, insomnia and fatigue due to jetlag, schizophrenia, panic attacks, melancholia, appetite disorders, obesity, insomnia, pain, psychotic disorders, epilepsy, diabetes, Parkinson's disease, senile dementia, various disorders associated with normal or pathological ageing, migraine, memory loss, Alzheimer's disease, and in cerebral circulation disorders. In 15 another field of activity, it appears that the crystalline IV form of agomelatine can be used in the treatment of sexual dysfunction, that it has ovulation-inhibiting and immunomodulating properties and that it lends itself to use in the treatment of cancers.
The crystalline form IV of agomelatine will preferably be used in the treatment of severe depression, seasonal affective disorders, sleep disorders, cardiovascular pathologies, 20 insomnia and fatigue due to jetlag, appetite disorders and obesity.
The invention relates also to pharmaceutical compositions comprising as active ingredient the crystalline form IV of agomelatine together with one or more appropriate inert, nontoxic excipients. Among the pharmaceutical compositions according to the invention there may be mentioned, more especially, those which are suitable for oral, parenteral 25 (intravenous or subcutaneous) or nasal administration, tablets or dragees, granules, sublingual tablets, gelatin capsules, lozenges, suppositories, creams, ointments, dermal gels, injectable preparations, drinkable suspensions and disintegrable pastes.
The useful dosage can be adapted according to the nature and the severity of the disorder, the administration route and the age aid weight of the patient. The dosage varies from 0.1 mg to 1 g per day in one or more administrations.
The term "comprising" as used in this specification means "consisting at least in part of'. When interpreting each statement in this specification that includes the term "comprising", features other than that or those prefaced by the term may also be present. Related terms such as "comprise" and "comprises" are to be interpreted in the same manner.
The Examples below illustrate the invention but do not limit it in any way.
Example 1 : Crystalline form IV of iV-[2-(7-methoxy-l-naphthyI)ethyl]acetamide 100 g of 7V-[2-(7-methoxy-1 -naphthyl)ethyl]acetamide are heated at 110°C until the melting be completed, and is then rapidly cooled between 50 and 70°C, and maintained for 5 hours at 70°C until crystallisation. The crystalline form IV obtained is characterised by the following powder X-ray diffraction diagram, measured using a Siemens D5005 diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage of the most intense ray) : 2-Theta (°) exp. d(A) Intensity exp. (%) .04 .16 .51 .22 16.75 17.41 18.03 18.81 20.48 21.61 23.27 24.04 24.27 24.77 25.57 27.06 27.95 17.524 8.703 8.409 .818 5.288 5.089 4.915 4.714 4.333 4.110 3.819 3.699 3.665 3.591 3.481 3.292 3.190 8 68 9 28 39 60 100 71 37 16 11 26 42 24 13 6 11 intellectual property office of n Z.
O S JUL 2007 RECEIVED Example 2 : Pharmaceutical composition Formulation for the preparation of 1000 tablets each containing a dose of 25 mg : Compound of Example 1 25 g Lactose monohydrate 62 g Magnesium stearate 1.3 g Maize starch 26 g Maltodextrines 9 g Silica, colloidal anhydrous 0.3 g Sodium starch glycolate type A 4 g Stearic acid 2.6 g Example 3 : Pharmaceutical composition Formulation for the preparation of 1000 tablets each containing a dose of 25 mg: Compound of Example 1 25 g Lactose monohydrate 62 g Magnesium stearate 1.3 g Povidone 9 g Silica, colloidal anhydrous 0.3 g Sodium cellulose glycolate 30 g Stearic acid 2.6 g

Claims (11)

WHAT WE CLAIM IS:
1. Crystalline form IV of agomelatine of formula (I): characterised by the following powder X-ray diffraction diagram, measured using a 5 diffractometer (copper anticathode) and expressed in terms of inter-planar distance d, Bragg's angle 2 theta, intensity and relative intensity (expressed as a percentage with respect to the most intense ray) : 2-Theta (°) d(A) Intensity exp. exp. (%) 5.04 17.524 8 10.16 8.703 68 10.51 8.409 9 15.22 5.818 28 16.75 5.288 39 17.41 5.089 60 18.03 4.915 100 18.81 4.714 71 20.48 4.333 37 21.61 4.110 16 23.27 3.819 11 24.04 3.699 26 24.27 3.665 42 24.77 3.591 24 25.57 3.481 13 27.06 3.292 6 27.95 3.190 11 intellectual property office of n.z. O S JUL 2007 RECEIVED
2. Process for the preparation of the crystalline form IV of the compound of formula (I) according to claim 1, characterised in that agomelatine is heated at 110°C until the melting be completed, and is then rapidly cooled between 50 and 70°C, and maintained for about 5 hours at 70°C until crystallisation.
3. Pharmaceutical compositions comprising as active ingredient crystalline form IV of agomelatine according to claim 1, in combination with one or more pharmaceutically acceptable, inert, non-toxic carriers.
4. Pharmaceutical compositions according to claim 3 for use in the manufacture of a medicament for the treatment of melatoninergic disorders.
5. Pharmaceutical compositions according to claim 3 for use in the manufacture of a medicament for the treatment of sleep disorders, stress, anxiety, seasonal affective disorders or severe depression, cardiovascular pathologies, pathologies of the digestive system, insomnia and fatigue due to jetlag, schizophrenia, panic attacks, melancholia, appetite disorders, obesity, insomnia, psychotic disorders, epilepsy, diabetes, Parkinson's disease, senile dementia, various disorders associated with normal or pathological ageing, migraine, memory loss, Alzheimer's disease, cerebral circulation disorders, and also in sexual dysfunction, as ovulation inhibitors, immunomodulators and cancers. \
6. A use of a crystalline form IV of agomelatine as defined in claim 1 in the manufacture of a medicament for treating melatoninergic disorders.
7. A use of a crystalline form IV of agomelatine as defined in claim 1 in the manufacture of a medicament for treating sleep disorders, stress, anxiety, seasonal affective disorders or severe depression, cardiovascular pathologies, pathologies of the digestive system, insomnia and fatigue due to jetlag, schizophrenia, panic attacks, melancholia, appetite disorders, obesity, insomnia, psychotic disorders, epilepsy, diabetes, Parkinson's disease, senile dementia, various disorders associated with normal or pathological ageing, migraine, memory loss, Alzheimer's disease, cerebral circulation disorders, and also in sexual dysfunction, as ovulation inhibitors, immunomodulators and cancers. ___ intellectual property office of n.z. 0 6 JUL 2007
8. A crystalline form IV of agomelatine according to claim 1 substantially as herein described with reference to any example thereof.
9. A process according to claim 2 substantially as herein described with reference to any example thereof.
10. A pharmaceutical composition according to claim 3 substantially as herein described with reference to any example thereof.
11. A use according to claim 6 or claim 7 substantially as herein described with reference to any example thereof. 973880-1 intellectual propehiti office of n.z. | 06 JUL 2007 1
NZ548863A 2005-08-03 2006-08-01 New crystalline form IV of agomelatine, a process for its preparation and pharmaceutical compositions containing it NZ548863A (en)

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FR0508277A FR2889522B1 (en) 2005-08-03 2005-08-03 NOVEL IV CRYSTALLINE FORM OF AGOMELATIN, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME

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EP (2) EP1752444A1 (en)
JP (1) JP4580371B2 (en)
CN (1) CN100445264C (en)
AR (1) AR057714A1 (en)
AU (1) AU2006203340B2 (en)
BR (1) BRPI0603043A (en)
CA (1) CA2555119A1 (en)
CO (1) CO5780132A1 (en)
EA (1) EA010867B1 (en)
FR (1) FR2889522B1 (en)
GE (1) GEP20094577B (en)
GT (1) GT200600345A (en)
HK (1) HK1098129A1 (en)
MA (1) MA28450B1 (en)
MX (1) MXPA06008693A (en)
MY (1) MY141306A (en)
NO (1) NO20063518L (en)
NZ (1) NZ548863A (en)
PE (1) PE20070242A1 (en)
SA (1) SA06270254B1 (en)
SG (1) SG130111A1 (en)
TW (1) TWI327564B (en)
UA (1) UA83718C2 (en)
WO (1) WO2007015002A2 (en)
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FR2923482B1 (en) * 2007-11-09 2010-01-29 Servier Lab NOVEL VI CRYSTALLINE FORM OF AGOMELATIN, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
FR2934856B1 (en) * 2008-08-05 2010-08-13 Servier Lab NEW PROCESS FOR OBTAINING THE V-CRYSTALLINE FORM OF AGOMELATIN
CN101585779B (en) * 2009-03-10 2014-04-02 上海医药工业研究院 New crystal form of Agomelatine, preparation method and use thereof
WO2011006387A1 (en) * 2009-07-11 2011-01-20 浙江华海药业股份有限公司 Process for preparing agomelatine, crystals of agomelatine and preparing process thereof
CN102001959B (en) * 2009-09-01 2014-07-02 北京本草天源药物研究院 Medicinal crystal as well as preparation method and application thereof
CN102050755B (en) * 2009-10-29 2014-11-05 重庆医药工业研究院有限责任公司 Novel agomelatine crystal forms and preparation methods of agomelatine crystal forms
CN101781226B (en) * 2009-12-23 2012-03-28 天津泰普药品科技发展有限公司 Agomelatine and medicine composition thereof
CN101870662B (en) * 2010-05-21 2013-03-20 中山大学 Crystalline Agomelatine solvate and preparation method thereof
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
CN102690210A (en) 2011-03-23 2012-09-26 上海医药工业研究院 Novel crystal form VII of agomelatine, preparation method and application thereof and pharmaceutical composition containing the same
CN102690209A (en) * 2011-03-23 2012-09-26 上海医药工业研究院 Mixed crystal of agomelatine (form-VIII), preparation method and application thereof and pharmaceutical composition containing the same
FR2978916B1 (en) 2011-08-10 2013-07-26 Servier Lab SOLID PHARMACEUTICAL COMPOSITION FOR BUCCAL ADMINISTRATION OF AGOMELATIN
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