IL177173A - Crystalline form v of agomelatine, process for its preparation using high energy grinder and pharmaceutical compositions containing it - Google Patents

Crystalline form v of agomelatine, process for its preparation using high energy grinder and pharmaceutical compositions containing it

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Publication number
IL177173A
IL177173A IL177173A IL17717306A IL177173A IL 177173 A IL177173 A IL 177173A IL 177173 A IL177173 A IL 177173A IL 17717306 A IL17717306 A IL 17717306A IL 177173 A IL177173 A IL 177173A
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crystalline form
compound
disorders
agomelatine
formula
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IL177173A
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IL177173A0 (en
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Servier Lab
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    • 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
    • C07C231/24—Separation; Purification
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
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    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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    • A—HUMAN NECESSITIES
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    • 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
    • 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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  • Obesity (AREA)
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  • Gynecology & Obstetrics (AREA)
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  • Cardiology (AREA)
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  • Psychology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pregnancy & Childbirth (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Medicinal Preparation (AREA)

Description

177173/2 177173 i?'Ji I 453548 mx New crystalline form V of agomelatine, a process for its preparation using high energy grinder and pharmaceutical compositions containing it Les Laboratoires Servier C. 168538 177173/1 la N-[2-(7-Metheoxy-l-naphthyl)ethyl]-acetamide, a Potent Melatonin Analog, Acta Cryst. (1994) C50, P. 907-910 - describes crystallography data (unit cell) of crystalline agomelatine, based on which it is possible to obtain an XRD template using the appropriate software.
Antidepressant Treatment of Bipolar Disorder Melatonin Agonist/5-HT2C Antagonist, Dugs of the Future 2003, 28(1), P. 7-13 -describes use of agomelatine as an antidepressant.
Synthesis and Structure -Activity Relationship of Novel Naphthalenic and Bioisosteric Related Amidic Derivatives as Melatonin Receptor Ligands, J. Med. Chem. 1994, 37, P. 3231-3239 - describes a process for preparing agomelatine (see Example 7, Tables 1 and 2, page 3326, 4th paragraph on the left). The polymer obtained by the process is not described, however, its melting point in the range of 109-1 IOC is identical with the melting point of the polymorph described in page 3, line 7 of the present application; US7358395B describes crystalline form V of the compound of formula (I): characterised by its powder X-ray diffraction diagram. Medicinal products containing the same which are useful in the treatment of melatoninergic disorders. 01685387X51-01 - - The present invention relates to a new crystalline form V of agomelatine, or N-[2-(7-methoxy-l-naphthyl)ethyl]acetamide, of formula (I) : a process for its preparation and pharmaceutical compositions containing it.
Agomelatine, or N-[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 dissolution and 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. 177173/2 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 dissolution and formulation.
More specifically, the present invention relates to the crystalline form V 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) : The invention relates also to a process for the preparation of the crystalline form V of the compound of formula (I), which process is characterised in that agomelatine is subjected to a high energy mechanical grinder of the vario-planetary mill type.
In the crystallisation process according to the invention it is possible to use the compound of formula (I) obtained by any process. 177173/2 The invention relates also to another process for the preparation of the crystalline form V of the compound of formula (I), which process is characterised in that agomelatine is heated until complete melting, then immediately put at room temperature and simultaneously a small quantity of crystalline form V of compound of formula (I) obtained by the grinding as defined above is added and the mixture is cooled until crystallization is complete.
Preferably, in that second crystallisation process according to the invention, agomelatine will be melted at 110°C.
The amount of crystalline form V added in that second process according to the invention will be preferably contained between 1/100 and 1/50 of agomelatine weight.
In that second crystallisation process according to the invention, it is possible to use the compound of formula (I) obtained by any process.
An advantage of obtaining that crystalline form is that it allows the preparation of pharmaceutical formulations having a consistent and reproducible composition, which as a result exhibits valuable characteristics in terms of dissolution which is especially advantageous when the formulations are to be used for oral administration.
A pharmacological study of the form V 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 V of agomelatine is useful in the treatment of stress, sleep disorders, anxiety, severe depression, seasonal 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 another field of activity, it appears that the crystalline V form of agomelatine can be used in the treatment of sexual dysfunction, that it has ovulation-inl ibiting and immunomodulating properties and that it lends itself to use in the treatment of cancers.
The crystalline form V of agomelatine will preferably be used in the treatment of severe depression, seasonal affective disorders, sleep disorders, cardiovascular pathologies, insomnia and fatigue due to jetlag, appetite disorders and obesity.
The invention relates also to pharmaceutical compositions comprising as active ingredient the crystalline form V 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 (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 and weight of the patient. The dosage varies from 0.1 mg to 1 g per day in one or more administrations.
The Examples below illustrate the invention but do not limit it in any way.
Example 1 : Crystalline form V of N-[2-(7-Methoxy-l-naphthyl)ethyl]acetamide 100 g of N-[2-(7-Methoxy-l-naphthyl)ethyl]acetamide are put in a mechanical grinder of the vario-planetary mill type for about 6 hours and the solid 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) : Example 2 : Crystalline form V of N-[2-(7-Methoxy-l-naphthyI)ethyl]acetamide 4 g of N-[2-(7-Memoxy-l-naphmyl)ethyl]acetarnide are put in a ventilatedincubator at 110°C. After 1 hour at 110°C, the product is immediately placed at room temperature and seeded with 0.05 g of crystalline form V of N-[2-(7-Methoxy-l-naphthyl)ethyl]acetamide structurally pure obtained by mechanical grinding of high energy. After 5 minutes, the crystallisation is complete and the solid 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) : Example 3 : Pharmaceutical composition Formulation for the preparation of 1000 tablets each containing a dose of 25 mg : Compound of Example 1 or 2 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 4 : Pharmaceutical composition Formulation for the preparation of 1000 tablets each containing a dose of 25 mg : Compound of Example 1 or 2 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 (6)

8 177173/2 claims
1. A crystalline form V of the compound of formula (I): wherein the compound exhibits essentially the following powder X-ray diffraction diagram, measured using a diffractometer (copper anticathode) and expressed in terms of inter-planar distance d (expressed in A), Bragg's angle 2 theta (expressed in degrees), intensity and relative intensity (expressed as a percentage with respect to the most intense ray) : 01685387X21-01 9 177173/3
2. A process for the preparation of the crystalline form V of the compound of formula (I) of claim 1, wherein agomelatine is subjected to high energy mechanical grinder of the vario-planetary mill type.
3. A process for the preparation of the crystalline form V of the compound of formula (I) of claim 1, wherein agomelatine is heated until completely melted, then immediately placed at room temperature and simultaneously a small quantity of crystalline form V of compound of formula (I) according to claim 2 is added, and the mixture is cooled until crystallisation is complete.
4. A pharmaceutical composition comprising as active ingredient an effective amount of crystalline form V of the compound of claim 1, in combination with one or more pharmaceutically acceptable, inert, non-toxic carriers.
5. Use of crystalline form V of the compound of claim 1 in the manufacture of a medicament for treating a living animal body, including a human, afflicted with disorders of the melatoninergic system.
6. Use of crystalline form V of the compound of claim 1, in the manufacture of a medicament for treating a living animal body, including a human, afflicted with 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, migraine, memory loss, Alzheimer's disease, and cerebral circulation disorders. For the Applicants, 01685387X21-01
IL177173A 2005-08-03 2006-07-31 Crystalline form v of agomelatine, process for its preparation using high energy grinder and pharmaceutical compositions containing it IL177173A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0508278A FR2889523B1 (en) 2005-08-03 2005-08-03 NOVEL CRYSTALLINE FORM V OF AGOMELATIN, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME

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IL177173A0 IL177173A0 (en) 2006-12-10
IL177173A true IL177173A (en) 2011-10-31

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AU (1) AU2006203342B2 (en)
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CA (1) CA2555115C (en)
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HK (1) HK1098128A1 (en)
HR (1) HRP20120779T1 (en)
IL (1) IL177173A (en)
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SA (1) SA06270255B1 (en)
SG (1) SG130110A1 (en)
SI (1) SI1752443T1 (en)
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UA (1) UA83720C2 (en)
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FR2934856B1 (en) * 2008-08-05 2010-08-13 Servier Lab NEW PROCESS FOR OBTAINING THE V-CRYSTALLINE FORM OF AGOMELATIN
CN101481321B (en) * 2009-02-27 2012-04-18 上海医药工业研究院 Agomelatine halogen hydride complex and preparation thereof
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
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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
CN102000583B (en) * 2010-11-18 2012-08-15 烟台万华聚氨酯股份有限公司 Catalyst for preparing chlorine by oxidizing hydrogen chloride and preparation method thereof
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
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
CN106349138A (en) * 2011-06-02 2017-01-25 奇诺因私人有限公司 Process for the preparation of chemically stable novel crystalline form of bimatoprost
FR2978916B1 (en) 2011-08-10 2013-07-26 Servier Lab SOLID PHARMACEUTICAL COMPOSITION FOR BUCCAL ADMINISTRATION OF AGOMELATIN
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