AU2006203336B2 - New crystalline form III of agomelatine, a process for its preparation and pharmaceutical compositions containing it - Google Patents
New crystalline form III of agomelatine, a process for its preparation and pharmaceutical compositions containing it Download PDFInfo
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- AU2006203336B2 AU2006203336B2 AU2006203336A AU2006203336A AU2006203336B2 AU 2006203336 B2 AU2006203336 B2 AU 2006203336B2 AU 2006203336 A AU2006203336 A AU 2006203336A AU 2006203336 A AU2006203336 A AU 2006203336A AU 2006203336 B2 AU2006203336 B2 AU 2006203336B2
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- agomelatine
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- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229960002629 agomelatine Drugs 0.000 title claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 7
- 238000010586 diagram Methods 0.000 claims abstract description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 208000035475 disorder Diseases 0.000 claims description 19
- 230000007170 pathology Effects 0.000 claims description 15
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 14
- 206010022437 insomnia Diseases 0.000 claims description 14
- 208000024827 Alzheimer disease Diseases 0.000 claims description 12
- 208000027559 Appetite disease Diseases 0.000 claims description 8
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 8
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 8
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 8
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 8
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 208000019116 sleep disease Diseases 0.000 claims description 8
- 210000002249 digestive system Anatomy 0.000 claims description 7
- 208000012672 seasonal affective disease Diseases 0.000 claims description 7
- 208000000044 Amnesia Diseases 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000020401 Depressive disease Diseases 0.000 claims description 6
- 208000026139 Memory disease Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 206010033664 Panic attack Diseases 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 206010039966 Senile dementia Diseases 0.000 claims description 6
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 6
- 230000032683 aging Effects 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 230000002490 cerebral effect Effects 0.000 claims description 6
- 230000004087 circulation Effects 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 208000024714 major depressive disease Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 201000003995 melancholia Diseases 0.000 claims description 6
- 230000001193 melatoninergic effect Effects 0.000 claims description 6
- 230000006984 memory degeneration Effects 0.000 claims description 6
- 208000023060 memory loss Diseases 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 208000019906 panic disease Diseases 0.000 claims description 6
- 230000001575 pathological effect Effects 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 6
- 230000035882 stress Effects 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 230000002519 immonomodulatory effect Effects 0.000 claims description 5
- 231100000546 inhibition of ovulation Toxicity 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 230000001932 seasonal effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 229960001021 lactose monohydrate Drugs 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 1
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 description 1
- GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- 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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- 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
NEW CRYSTALLINE FORM III OF AGOMELATINE, A PROCESS FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT Crystalline form III 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 Ill 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 III of agomelatine, or N-[2-(7 methoxy-1-naphthyl)ethyl]acetamide, of formula (I) : NHCOMe MeO (D) 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-HT2c 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 III 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) Intensity exp. exp. (%) 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 The invention relates also to a process for the preparation of the crystalline form III of compound of formula (I), which process is characterised in that agomelatine is heated at 110 C until the melting be completed, and is then slowly cooled until crystallisation. An advantage of obtaining that crystalline form is that it allows the preparation of 5 pharmaceutical formulations having a consistent and reproducible composition, which is especially advantageous when the formulations are to be used for oral administration. A pharmacological study of the form III 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 III of agomelatine 10 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, 15 migraine, memory loss, Alzheimer's disease, and in cerebral circulation disorders. In another field of activity, it appears that the crystalline III 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 III of agomelatine will preferably be used in the treatment of severe 20 depression, seasonal affective disorders, sleep disorders, cardiovascular pathologies, insomnia and fatigue due to jetlag, appetite disorders and obesity. Accordingly, in one embodiment the invention relates to a method for the treatment of melatoninergic disorders comprising administering to a patient requiring such treatment an effective amount of crystalline form III of agomelatine or a pharmaceutical 25 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, schizophrenia, panic attacks, melancholia, appetite disorders, obesity, insomnia, 30 psychotic disorders, epilepsy, diabetes, Parkinson's disease, senile dementia, various 3a 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 patient requiring such treatment an effective amount of crystalline form III of 5 agomelatine or a pharmaceutical composition thereof. In a further embodiment the invention relates to the use of crystalline form III 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 III of 10 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 15 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 invention relates also to pharmaceutical compositions comprising as active ingredient the crystalline form III of agomelatine together with one or more appropriate 20 inert, non-toxic 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 dragdes, 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 III of N-[2-(7-methoxy-1-naphthyl)ethyllacetamide 100 g of N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide are heated at 1 10 C in a ventilated incubator until the melting be completed, and are then slowly cooled until crystallisation. The crystalline form III obtained is characterised by the following powder X-ray diffraction diagram, measured using a Siemens D5005 diffractometer (copper anticathode) 10 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. (%) 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 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 (17)
1. Crystalline form III 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) Intensity exp. exp. (%)
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 2. Process for the preparation of the crystalline form III 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 slowly cooled until crystallisation. 3. Pharmaceutical compositions comprising as active ingredient crystalline form III of 5 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 10 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 15 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 III of agomelatine of formula I as described herein with reference to Example 1. 7. A pharmaceutical composition comprising as active ingredient crystalline form III 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 III 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 III of agomelatine according to claim 1 or 6, or a pharmaceutical composition according to claim 3 or 7. 20 10. Use of crystalline form III of agomelatine according to claim I 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 III of agomelatine according to claim 1 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.
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| FR0508276A FR2889521B1 (en) | 2005-08-03 | 2005-08-03 | NOVEL CRYSTALLINE FORM III OF AGOMELATIN, PROCESS FOR PREPARING THE SAME AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
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| 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 |
| CN101709036B (en) * | 2009-12-17 | 2012-07-04 | 天津药物研究院 | Preparation of agomelatine midbody, 2-(7-anisyl-1-naphthyl) ethylamine |
| 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 |
| CN101774937B (en) * | 2010-02-05 | 2014-01-08 | 天津市汉康医药生物技术有限公司 | N-[2-(7-methoxyl-1-naphthyl)ethyl]acetamide and compound thereof |
| 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 (en) * | 2011-01-21 | 2013-05-02 | Zentiva, K.S. | Agomelatine metastable crystal forms and pharmaceutical composition thereof |
| 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 |
| ES2634243T3 (en) | 2011-11-30 | 2017-09-27 | 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 |
| WO2014096373A1 (en) | 2012-12-21 | 2014-06-26 | Laboratorios Lesvi, S. L. | Process for prepararing n-(2-(7-methoxy-1-naphthalenyl)ethyl) acetamide and solid forms thereof |
| FR3001894A1 (en) | 2013-02-08 | 2014-08-15 | Servier Lab | SOLID PHARMACEUTICAL COMPOSITION FOR BUCCAL ADMINISTRATION OF AGOMELATIN |
| PT2810656T (en) | 2013-06-06 | 2017-11-13 | Zentiva As | Agomelatine formulations comprising agomelatine in the form of co-crystals |
| 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 (en) | 2013-08-13 | 2015-02-25 | Zentiva, K.S. | Agomelatine thermodynamically stable congealed solution for use in pharmaceutical formulation |
| WO2015124496A1 (en) | 2014-02-19 | 2015-08-27 | Synthon B.V. | Pharmaceutical composition comprising amorphous agomelatine |
| ES2959460T3 (en) | 2015-03-31 | 2024-02-26 | Fis Fabbrica Italiana Sintetici Spa | solid form of agomelatine |
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| FR2866336B1 (en) * | 2004-02-13 | 2006-03-24 | Servier Lab | NOVEL PROCESS FOR THE SYNTHESIS OF (7-METHOXY-3,4-DIHYDRO-1-NAPHTHALENYL) ACETONITRILE AND APPLICATION TO THE SYNTHESIS OF AGOMELATIN |
| FR2866335B1 (en) * | 2004-02-13 | 2006-05-26 | Servier Lab | NEW PROCESS FOR THE SYNTHESIS OF AGOMELATIN |
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