AU2006203340B2 - 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 Download PDF

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AU2006203340B2
AU2006203340B2 AU2006203340A AU2006203340A AU2006203340B2 AU 2006203340 B2 AU2006203340 B2 AU 2006203340B2 AU 2006203340 A AU2006203340 A AU 2006203340A AU 2006203340 A AU2006203340 A AU 2006203340A AU 2006203340 B2 AU2006203340 B2 AU 2006203340B2
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disorders
crystalline form
agomelatine
treatment
insomnia
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Gerard Coquerel
Julie Linol
Jean-Claude Souvie
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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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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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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

Abstract

NEW CRYSTALLINE FORM IV OF AGOMELATINE, A PROCESS FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT Crystalline form IV of the compound of formula (I) : NHCOMe MeO (I) characterised by its powder X-ray diffraction diagram. Medicaments.

Description

Pool Section 29 Regulation 3.2(2) AUSTRALIA Patents Act 1990 COMPLETE SPECIFICATION STANDARD PATENT Application Number: Lodged: Invention Title: New crystalline form IV of agomelatine, a process for its preparation and pharmaceutical compositions containing it The following statement is a full description of this invention, including the best method of performing it known to us: - 1 The present invention relates to a new crystalline form IV of agomelatine, or N-[2-(7 methoxy-1-naphthyl)ethyl]acetamide, of formula (I) : NHCOMe MeO GI) a process for its preparation and pharmaceutical compositions containing it. 5 Agomelatine, or N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide, has valuable pharmaco logical 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-HT 2 c receptor. Those properties confer activity in the central nervous system and, more especially, in the 10 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. 15 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. 20 Patent Specification EP 0 447 285 describes the preparation of agomelatine in eight steps, starting from 7-methoxy-1-tetralone. However, that document does not specify the -2 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 5 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 10 a percentage of the most intense ray): 2-Theta (*) d (A) Intensit6 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 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 3 I 10 C until the melting be completed, and is then rapidly cooled between 50*C and 70*C, and maintained for about 5 hours at 70C 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. Accordingly, in one embodiment the invention relates to a method for the treatment of melatoninergic disorders comprising administering to a patient requiring such treatment 20 an effective amount of crystalline form IV of agomelatine or a pharmaceutical composition thereof. In another embodiment the invention relates to a method for the treatment of sleep disorders, stress, anxiety, seasonal affective disorders, severe depression, cardiovascular pathologies, pathologies of the digestive system, insomnia or fatigue due to jetlag, 25 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, sexual dysfunction, or cancers, or for ovulation-inhibition, or immunomodulation, the method comprising administering to a 30 patient requiring such treatment an effective amount of crystalline form IV of agomelatine or a pharmaceutical composition thereof.
3a In a further embodiment the invention relates to the use of crystalline form IV of agomelatine or a pharmaceutical composition thereof in the manufacture of a medicament for the treatment of melatoninergic disorders. In another embodiment the invention relates to the use of crystalline form IV of 5 agomelatine or a pharmaceutical composition thereof in the manufacture of a medicament for the treatment of sleep disorders, stress, anxiety, seasonal affective disorders, severe depression, cardiovascular pathologies, pathologies of the digestive system, insomnia or fatigue due to jetlag, schizophrenia, panic attacks, melancholia, appetite disorders, obesity, insomnia, psychotic disorders, epilepsy, diabetes, Parkinson's 10 disease, senile dementia, various disorders associated with normal or pathological ageing, migraine, memory loss, Alzheimer's disease, cerebral circulation disorders, sexual dysfunction, or cancers, or for ovulation-inhibition, or immunomodulation. The crystalline form IV of agomelatine will preferably be used in the treatment of severe depression, seasonal affective disorders, sleep disorders, cardiovascular pathologies, 15 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, non-toxic excipients. Among the pharmaceutical compositions according to the invention there may be mentioned, more especially, those which are suitable for oral, 20 parenteral (intravenous or subcutaneous) or nasal administration, tablets or drag6es, granules, sublingual tablets, gelatin capsules, lozenges, suppositories, creams, ointments, dermal gels, injectable preparations, drinkable suspensions and disintegrable pastes.
-4 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. 5 Example 1 : Crystalline form IV of N-[2-(7-methoxy-1-naphthyl)ethyllacetamide 100 g of N-[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 10 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) Intensit6 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 5 Example 2: Pharmaceutical composition Formulation for the preparation of 1000 tables each containing a dose of 25 mg: Compound of Example 1 25 g Lactose monohydrate 62 g 5 Magnesium stearate 1.3 g Maize starch 26 g Maltodextrins 9 g Silica, colloidal anhydrous 0.3 g Sodium starch glycolate type A 4 g 10 Stearic acid 2.6 g Example 3: Pharmaceutical composition Formulation for the preparation of 1000 tables each containing a dose of 25 mg: Compound of Example 1 25 g 15 Lactose monohydrate 62 g Magnesium stearate 1.3 g Povidone 9 g Silica, colloidal anhydrous 0.3 g Sodium cellulose glycolate 30g 20 Stearic acid 2.6 g Comprises/comprising and grammatical variations thereof when used in this specification are to be taken to specify the presence of stated features, integers, steps or components or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, components or groups thereof. 25 Any discussion of documents, acts, materials, devices, articles or the like which has been included in the present specification is solely for the purpose of providing a context for the present invention. It is not to be taken as an admission that any or all of these - matters form part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date of each claim of this 30 specification.

Claims (14)

1. Crystalline form IV of agomelatine of formula (I): NHCOMe MeO (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 (0) d (A) Intensit6 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 -7 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 70C, and maintained for about 5 hours at 70C until crystallisation. 5 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. 10 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, 15 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. 8 6. A crystalline form IV of agomelatine of formula I as described herein with reference to Example 1. 7. A pharmaceutical composition comprising as active ingredient crystalline form IV of agomelatine as hereinbefore described with reference to Example 2 or 3. 5 8. A method for the treatment of melatoninergic disorders comprising administering to a patient requiring such treatment an effective amount of the crystalline form IV of agomelatine according to claim I or 6, or a pharmaceutical composition according to claim 3 or 7. 9. A method for the treatment of sleep disorders, stress, anxiety, seasonal affective 10 disorders, severe depression, cardiovascular pathologies, pathologies of the digestive system, insomnia or 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, 15 cerebral circulation disorders, sexual dysfunction, or cancers, or for ovulation inhibition, or immunomodulation, the method comprising administering to a patient requiring such treatment an effective amount of the crystalline form IV of agomelatine according to claim I or 6, or a pharmaceutical composition according to claim 3 or 7. 20 10. Use of crystalline form IV of agomelatine according to claim 1 or 6, or a pharmaceutical composition according to claim 3 or 7 in the manufacture of a medicament for the treatment of melatoninergic disorders. 11. Use of crystalline form IV of agomelatine according to claim I or 6, or a pharmaceutical composition according to claim 3 or 7 in the manufacture of a 25 medicament for the treatment of sleep disorders, stress, anxiety, seasonal affective disorders, severe depression, cardiovascular pathologies, pathologies of the digestive system, insomnia or 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 30 normal or pathological ageing, migraine, memory loss, Alzheimer's disease, cerebral circulation disorders, sexual dysfunction, or cancers, or for ovulation inhibition, or immunomodulation.
AU2006203340A 2005-08-03 2006-08-03 New crystalline form IV of agomelatine, a process for its preparation and pharmaceutical compositions containing it Ceased AU2006203340B2 (en)

Applications Claiming Priority (2)

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FR05/08277 2005-08-03
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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CA (1) CA2555119A1 (en)
CO (1) CO5780132A1 (en)
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US9029420B2 (en) 2009-12-23 2015-05-12 Tianjin Taipu Pharmaceutical Science & Technology Development Co., Ltd. Agomelatine and pharmaceutical compositions thereof

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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
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
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