NZ548864A - New cyrstalline form V of agomelatine, a process for its preparation and pharmaceutical compositions containing it - Google Patents
New cyrstalline form V of agomelatine, a process for its preparation and pharmaceutical compositions containing itInfo
- Publication number
- NZ548864A NZ548864A NZ548864A NZ54886406A NZ548864A NZ 548864 A NZ548864 A NZ 548864A NZ 548864 A NZ548864 A NZ 548864A NZ 54886406 A NZ54886406 A NZ 54886406A NZ 548864 A NZ548864 A NZ 548864A
- Authority
- NZ
- New Zealand
- Prior art keywords
- agomelatine
- disorders
- crystalline form
- insomnia
- disease
- Prior art date
Links
- 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 32
- 229960002629 agomelatine Drugs 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 12
- 230000007170 pathology Effects 0.000 claims abstract description 11
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims abstract description 10
- 206010022437 insomnia Diseases 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 8
- 238000002425 crystallisation Methods 0.000 claims abstract description 7
- 208000027559 Appetite disease Diseases 0.000 claims abstract description 6
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims abstract description 6
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 6
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims abstract description 6
- 208000008589 Obesity Diseases 0.000 claims abstract description 6
- 230000002526 effect on cardiovascular system Effects 0.000 claims abstract description 6
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims abstract description 6
- 235000020824 obesity Nutrition 0.000 claims abstract description 6
- 208000019116 sleep disease Diseases 0.000 claims abstract description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052802 copper Inorganic materials 0.000 claims abstract description 5
- 239000010949 copper Substances 0.000 claims abstract description 5
- 238000010586 diagram Methods 0.000 claims abstract description 5
- 210000002249 digestive system Anatomy 0.000 claims abstract description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 5
- 208000012672 seasonal affective disease Diseases 0.000 claims abstract description 5
- 208000000044 Amnesia Diseases 0.000 claims abstract description 4
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 4
- 208000020401 Depressive disease Diseases 0.000 claims abstract description 4
- 208000026139 Memory disease Diseases 0.000 claims abstract description 4
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 4
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 4
- 206010033664 Panic attack Diseases 0.000 claims abstract description 4
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 4
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 4
- 206010039966 Senile dementia Diseases 0.000 claims abstract description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 4
- 230000032683 aging Effects 0.000 claims abstract description 4
- 230000036506 anxiety Effects 0.000 claims abstract description 4
- 230000002490 cerebral effect Effects 0.000 claims abstract description 4
- 230000004087 circulation Effects 0.000 claims abstract description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 4
- 206010015037 epilepsy Diseases 0.000 claims abstract description 4
- 238000000227 grinding Methods 0.000 claims abstract description 4
- 208000024714 major depressive disease Diseases 0.000 claims abstract description 4
- 201000003995 melancholia Diseases 0.000 claims abstract description 4
- 230000006984 memory degeneration Effects 0.000 claims abstract description 4
- 208000023060 memory loss Diseases 0.000 claims abstract description 4
- 206010027599 migraine Diseases 0.000 claims abstract description 4
- 208000019906 panic disease Diseases 0.000 claims abstract description 4
- 230000001575 pathological effect Effects 0.000 claims abstract description 4
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 4
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 4
- 230000035882 stress Effects 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- 239000003433 contraceptive agent Substances 0.000 claims abstract 3
- 239000002955 immunomodulating agent Substances 0.000 claims abstract 3
- 229940121354 immunomodulator Drugs 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 11
- 230000001193 melatoninergic effect Effects 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000000969 carrier Substances 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 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
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003826 tablet Substances 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
- 239000007787 solid Substances 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
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 239000008298 dragée Substances 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
- 230000002519 immonomodulatory effect Effects 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
- 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
- 230000001932 seasonal effect Effects 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
- 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
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- 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
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/20—Hypnotics; Sedatives
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- A61P3/00—Drugs for disorders of the metabolism
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P35/00—Antineoplastic agents
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- A61P37/00—Drugs for immunological or allergic disorders
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- 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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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
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- Neurology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Gynecology & Obstetrics (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Cardiology (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)
Abstract
Crystalline form V of agomelatine (N-[2-(7-methoxy-1-naphthyl)ethyl]acetamide) is disclosed, wherein the crystalline form V of agomelatine has powder X-ray diffraction diagram, measured using a diffractometer (copper anticathode) and expressed in terms of inter-planar distance d (8.979-3.239 A[deg]), Bragg's angle 2 theta (9.84-27.51 degrees), intensity and relative intensity (expressed as a percentage with respect to the most intense ray). A process for the preparation of the crystalline form V of agomelatine is disclosed, wherein agomelatine is subjected to high energy mechanical grinding. Another process for the preparation of the crystalline form V of agomelatine is also disclosed, wherein agomelatine is heated until completely melted, then immediately placed at room temperature and simultaneously a small quantity of crystalline form V of agomelatine freshly prepared is added, and the mixture is cooled until crystallisation is complete. A pharmaceutical composition comprising as active ingredient an effective amount of crystalline form V 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 548864
*10052303729*
4 8 8 6 A
INTELLECTUAL PROPERTY OFFICE OF N.Z.
-1 AUG 2006 RECEIVED
NEW ZEALAND PATENTS ACT, 1953
No:
Date:
COMPLETE SPECIFICATION
NEW CRYSTALLINE FORM V 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)
- 1 a-
The present invention relates to a new crystalline form V of agomelatine, or jV-[2-(7-methoxy-l-naphthyl)ethyl]acetamide, of formula (I):
NHCOMe
MeO-^
(I)
a process for its preparation and pharmaceutical compositions containing it.
Agomelatine, or iV-[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.
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 5 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.
(%)
9.84
8.979
17
12.40
7.134
13.31
6.646
19
.14
.848
18
.98
.543
18
16.62
.329
19
17.95
4.939
100
18.88
4.697
65
.49
4.332
24
.99
4.228
34
23.07
3.852
39
23.44
3.792
36
24.28
3.663
58
.10
3.545
19
26.02
3.422
26.82
3.322
19
27.51
3.239
16
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 mechanical grinding which is said to be "of high energy".
In the crystallisation process according to the invention it is possible to use the compound of formula (I) obtained by any process.
INTELLECTUAL PROPERTY OFFICE OF N.Z.
G S JUL 2007
p F d EIV E D
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) freshly 5 prepared is added, and the mixture is cooled until crystallisation 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 15 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 20 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 25 activity, it appears that the crystalline V 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 V of agomelatine will preferably be used in the treatment of severe depression, seasonal affective disorders, sleep disorders, cardiovascular pathologies, 30 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 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 V of A42-(7-Methoxy-l-naphthyI)ethyl]acetamide
100 g of jV-[2-(7-Methoxy-1 -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 dififractometer (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):
INTELLECTUAL PROPERTY OFFICE OF N.Z.
06 JUL 2007
received
2-Theta (°)
d(A)
Intensity exp.
exp.
(%)
9.84
8.979
17
12.40
7.134
13.31
6.646
19
.14
.848
18
.98
.543
18
16.62
.329
19
17.95
4.939
100
18.88
4.697
65
.49
4.332
24
.99
4.228
34
23.07
3.852
39
23.44
3.792
36
24.28
3.663
58
.10
3.545
19
26.02
3.422
26.82
3.322
19
27.51
3.239
16
Example 2 : Crystalline form V of iV-[2-(7-Methoxy-l-naphthyl)ethylIacetamide
4 g of iV-[2-(7-Methoxy-1 -naphthyl)ethyl]acetamide are put in a ventilated incubator at 110°C. After 1 hour at 110°C, the product is immediately placed at room temperature and seeded with 5 0.05 g of crystalline form V of iV-[2-(7-Methoxy-1 -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 10 (expressed as a percentage of the most intense ray):
2-Theta (°)
d(A)
Intensity exp.
exp.
(%)
9.84
8.979
17
12.40
7.134
13.31
6.646
19
.14
.848
18
.98
.543
18
16.62
.329
19
17.95
4.939
100
18.88
4.697
65
.49
4.332
24
.99
4.228
34
23.07
3.852
39
23.44
3.792
36
24.28
3.663
58
.10
3.545
19
26.02
3.422
26.82
3.322
19
27.51
3.239
16
Exampie 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 (12)
1, Crystalline form V of agomelatine of formula (I): MeO NHCOMe 0) characterised by the following powder X-ray diffraction diagram, measured using a dififractometer (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. (%) 9.84 8.979 17 12.40 7.134 15 13.31 6.646 19 15.14 5.848 18 15.98 5.543 18 16.62 5.329 19 17.95 4.939 100 18.88 4.697 65 20.49 4.332 24 20.99 4.228 34 23.07 3.852 39 23.44 3.792 36 24.28 3.663 58 25.10 3.545 19 26.02 3.422 15 26.82 3.322 19 27.51 3.239 16 INTELLECTUAL PROPERTY OFFICE OF N.Z. OS JUL 2007 R E CEIVED -9-
2. Process for the preparation of the crystalline form V of the compound of formula (I) according to claim 1, characterised in that agomelatine is subjected to a mechanical grinding which is said to be "of high energy".
3. Process for the preparation of the crystalline form V of the compound of formula (I) 5 according to claim 1, 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) freshly prepared is added, and the mixture is cooled until crystallisation is complete.
4. Pharmaceutical compositions comprising as active ingredient crystalline form V of 10 agomelatine according to claim 1, in combination with one or more pharmaceutically acceptable, inert, non-toxic carriers.
5. Pharmaceutical compositions according to claim 4 for use in the manufacture of a medicament for the treatment of melatoninergic disorders.
6. Pharmaceutical compositions according to claim 4 for use in the manufacture of a 15 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 20 pathological ageing, migraine, memory loss, Alzheimer's disease, cerebral circulation disorders, and also in sexual dysfunction, as ovulation inhibitors, immunomodulators and cancers.
7. A use of a crystalline form V of agomelatine as defined in claim 1 in the manufacture of a medicament for treating melatoninergic disorders. intellectual property office of n.2. 66 JUL 2007 RECEIVED -10-
8. A use of a crystalline form V 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.
9. A crystalline form V of agomelatine according to claim 1 substantially as herein described with reference to any example thereof.
10. A process according to claim 2 or claim 3 substantially as herein described with reference to any example thereof.
11. A pharmaceutical composition according to claim 4 substantially as herein described with reference to any example thereof.
12. A use according to claim 7 or claim 8 substantially as herein described with reference to any example thereof. 974123-1 INTELLECTUAL PROPERTY OFFICE OF N.Z. OS JUL 2007 RECEIVED
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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| Publication Number | Publication Date |
|---|---|
| NZ548864A true NZ548864A (en) | 2008-03-28 |
Family
ID=36581629
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ548864A NZ548864A (en) | 2005-08-03 | 2006-08-01 | New cyrstalline form V of agomelatine, a process for its preparation and pharmaceutical compositions containing it |
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| Country | Link |
|---|---|
| EP (2) | EP1752443B1 (en) |
| JP (1) | JP4575337B2 (en) |
| CN (1) | CN100448843C (en) |
| AP (1) | AP2486A (en) |
| AR (1) | AR057715A1 (en) |
| AU (1) | AU2006203342B2 (en) |
| BR (1) | BRPI0603059A (en) |
| CA (1) | CA2555115C (en) |
| CR (1) | CR8529A (en) |
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| CY (1) | CY1113011T1 (en) |
| DK (1) | DK1752443T3 (en) |
| EA (1) | EA011030B1 (en) |
| EC (1) | ECSP066715A (en) |
| ES (1) | ES2391406T3 (en) |
| FR (1) | FR2889523B1 (en) |
| GT (1) | GT200600346A (en) |
| HK (1) | HK1098128A1 (en) |
| HR (1) | HRP20120779T1 (en) |
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| MA (1) | MA28451B1 (en) |
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| SA (1) | SA06270255B1 (en) |
| SG (1) | SG130110A1 (en) |
| SI (1) | SI1752443T1 (en) |
| TW (1) | TWI359128B (en) |
| UA (1) | UA83720C2 (en) |
| WO (1) | WO2007015004A2 (en) |
| ZA (1) | ZA200606453B (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 hydrogen halide compound and preparation method 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 |
| 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 |
| 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 |
| 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 |
| WO2012164324A1 (en) * | 2011-06-02 | 2012-12-06 | CHINOIN Zrt. | Novel processes for the preparation of prostaglandin amides |
| FR2978916B1 (en) | 2011-08-10 | 2013-07-26 | Servier Lab | SOLID PHARMACEUTICAL COMPOSITION FOR BUCCAL ADMINISTRATION OF AGOMELATIN |
| WO2013082302A1 (en) | 2011-11-30 | 2013-06-06 | 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 |
| CN103360275B (en) * | 2012-03-30 | 2015-04-22 | 上海创诺制药有限公司 | Method for preparing agomelatine I-type crystal |
| 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 |
| 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 |
| PT2810656T (en) | 2013-06-06 | 2017-11-13 | Zentiva As | Agomelatine formulations comprising agomelatine in the form of co-crystals |
| 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 |
| FR3033131B1 (en) | 2015-02-26 | 2017-11-17 | Servitronique | SLIDE FOR ITS SLIDING ADJUSTMENT SYSTEMS AND ASSEMBLY METHOD |
| PL3075724T3 (en) | 2015-03-31 | 2023-12-27 | F.I.S.- Fabbrica Italiana Sintetici S.P.A. | Solid form of agomelatine |
| EP3466923A1 (en) | 2017-10-09 | 2019-04-10 | KRKA, d.d., Novo mesto | Process for the preparation of agomelatine in crystalline form |
| EP3466413A1 (en) | 2017-10-09 | 2019-04-10 | KRKA, d.d., Novo mesto | Pharmaceutical composition containing agomelatine and process for the preparation thereof |
| CN113952323A (en) * | 2021-12-10 | 2022-01-21 | 李甜 | Application of agomelatine in inhibition of Ube2c protein expression |
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| FR2658818B1 (en) * | 1990-02-27 | 1993-12-31 | Adir Cie | NOVEL DERIVATIVES WITH NAPHTHALENIC STRUCTURE, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| FR2866335B1 (en) * | 2004-02-13 | 2006-05-26 | Servier Lab | NEW PROCESS FOR THE SYNTHESIS OF AGOMELATIN |
| 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 |
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