WO2010102554A1 - 阿戈美拉汀的新晶型ⅵ及其制备方法和应用 - Google Patents
阿戈美拉汀的新晶型ⅵ及其制备方法和应用 Download PDFInfo
- Publication number
- WO2010102554A1 WO2010102554A1 PCT/CN2010/070931 CN2010070931W WO2010102554A1 WO 2010102554 A1 WO2010102554 A1 WO 2010102554A1 CN 2010070931 W CN2010070931 W CN 2010070931W WO 2010102554 A1 WO2010102554 A1 WO 2010102554A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- agomelatine
- crystal form
- preparation
- diseases
- crystalline form
- Prior art date
Links
- 229960002629 agomelatine Drugs 0.000 title claims abstract description 31
- 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 31
- 238000002360 preparation method Methods 0.000 title abstract description 12
- 239000013078 crystal Substances 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 4
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 claims description 3
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 3
- 208000010643 digestive system disease Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 206010022437 insomnia Diseases 0.000 claims description 3
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims description 3
- 229960003987 melatonin Drugs 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 208000012672 seasonal affective disease Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010034912 Phobia Diseases 0.000 claims description 2
- 208000019899 phobic disease Diseases 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000024714 major depressive disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 abstract description 3
- 239000000843 powder Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010812 external standard method Methods 0.000 description 2
- 206010016256 fatigue Diseases 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 208000027559 Appetite disease Diseases 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 102000001419 Melatonin receptor Human genes 0.000 description 1
- 108050009605 Melatonin receptor Proteins 0.000 description 1
- 206010029216 Nervousness Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- UIIMQLOIIQMODF-UHFFFAOYSA-N [Ge].C(CCCCCCCCCCCCCCCCC)[Si] Chemical group [Ge].C(CCCCCCCCCCCCCCCCC)[Si] UIIMQLOIIQMODF-UHFFFAOYSA-N 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- 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
-
- 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
-
- 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
Definitions
- the crystalline form is obtained by recrystallization of ethanol and water.
- Method for the preparation of Form III Agomelatine is heated at 110 ° C until it is completely melted, and then slowly cooled until crystallization is obtained.
- Preparation of Form IV Agomelatine is heated at 110 ° C until it is completely melted, then rapidly cooled between 50 and 70 ° C, and maintained at 70 ° C for about 5 hours until crystallization is obtained.
- Preparation of crystal form V The so-called "high energy" mechanical grinding of agomelatine is obtained. Summary of invention
- Another object of the present invention is to provide a process for preparing agomelatine crystal form VI which is simple in operation and good in reproducibility.
- the crystal form of agomelatine, in the powder X-ray diffraction pattern, at the diffraction angle of 2 ⁇ is 11.13, 11.82, 17.49, 18.29, 19.48, 19.72, 20. 50 21. 76, 22.54, 22.97, 24.56, 25.36, 27.16, 31. There is a main peak at 93 degrees.
- the crystal form of agomelatine in the powder X-ray diffraction pattern, corresponds to the relative intensity (in hundredths) at the diffraction angle 2 ⁇ of the main peak as follows:
- a method for preparing agomelatine crystal form VI which first dissolves agomelatine in acetic acid, and then adds water at 0-25 ° C to crystallize.
- the preparation method of the above-mentioned agomelatine crystal form VI is preferably added slowly when added to water, and the specific operation can be carried out by dropping, and stirring is continued to facilitate crystallization.
- the agomelatine crystal form VI obtained by the present invention shows that it can be used for treating melatonin system diseases, sleep disorders, nervousness, anxiety, seasonal affective disorder or severe depression, heart Vascular disease, digestive system disease, insomnia or fatigue caused by jet lag, schizophrenia, phobia, depression, etc.
- the agomelatine crystalline form VI provided by the invention can be used together with various pharmaceutically acceptable excipients or excipients to prepare various pharmaceutical dosage forms for oral or injectable use.
- the invention obtains a new crystal form VI of agomelatine, which has good purity, stable crystal form and good reproducibility, and has advantages in preparation. In addition, it is better than the existing ones in stability and solubility. Crystal form.
- Figure 1 is an X-ray diffraction pattern of a crystalline form VI obtained in Example 1 of the present invention. Using Bruker D8
- the measurement conditions are as follows: CuKa 40Kv 40 mA is the light source, step size is 0. 02 °, scanning speed: 8 ° / min, scanning range: 3 ° ⁇ 80 °, room temperature.
- the lg agomelatine was stirred and dissolved in 4 ml of acetic acid, slowly added dropwise to 80 ml of water, and stirred at 5 ° C for 3 hours, filtered, and the solid was washed with water 8 ml * 2 and dried under vacuum at 55 ° C to a constant weight.
- White solid 0. 90g. Purity: 99.6%, melting point: 97-98 °C o
- agomelatine 2 g was stirred and dissolved in 8 ml of acetic acid, slowly added dropwise to 160 ml of water, and stirred at 20 ° C for 3 hours, filtered, and the solid was washed with water 16 ml * 2 and dried under vacuum at 55 ° C to a constant weight.
- White solid 1.76 g. Purity: 99.6%, melting point: 97-98 °C.
- the crystal form of agomelatine obtained in Example 2 in the measured X-ray diffraction pattern of the dried powdery product, the interplanar spacing d, the Bragg 2 angle and the relative intensity values are: 2 ⁇ ° d (A) relative strength
- Forms II, III, IV, and VI were placed in an incubator at 40 ° C for 20 days, and the stability of these crystal forms was investigated by high performance liquid chromatography.
- Chromatographic conditions using octadecyl silicon germanium bonded silica as a filler; a mixed solution of 10 mM / L phosphate buffer salt (pH adjusted to 7.0 with sodium hydroxide) and acetonitrile volume ratio of 2: 7 as mobile phase ;
- the column temperature was 40 ° C; the detection wavelength was 220 nm.
- the purity was determined by an internal standard method.
- the crystal forms II, III, IV, and VI were each placed in a lmg/mL solution using a mobile phase, and each was injected into a liquid chromatograph to record a chromatogram.
- the measurement method refers to the method for determining the purity of the sample, and the measurement is performed by an external standard method.
- the results are shown in Table 1:
- the novel gemetastatin VI of the present invention is more advantageous in stability and solubility than several existing crystal forms. Moreover, in the preparation method, it has more industrial application value than the existing crystal forms III, IV and V.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Battery Electrode And Active Subsutance (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
Claims
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SG2011058559A SG173692A1 (en) | 2009-03-10 | 2010-03-09 | New crystalline form vi of agomelatine, preparation method and application thereof |
MX2011009339A MX2011009339A (es) | 2009-03-10 | 2010-03-09 | Nueva forma cristalina iv de la agomelatina, preparacion y uso de la misma. |
AU2010223720A AU2010223720B2 (en) | 2009-03-10 | 2010-03-09 | New crystalline form VI of Agomelatine, preparation method and application thereof |
US13/138,615 US8614251B2 (en) | 2009-03-10 | 2010-03-09 | Crystalline form VI of agomelatine, preparation method and application thereof |
CA2754276A CA2754276A1 (en) | 2009-03-10 | 2010-03-09 | New crystalline form vi of agomelatine, preparation method and application thereof |
EP10750350A EP2431355A4 (en) | 2009-03-10 | 2010-03-09 | NOVEL VI-CRYSTALLINE FORM OF AGOMÉLATINE ITS PREPARATION METHOD AND APPLICATION |
MA34144A MA33100B1 (fr) | 2009-03-10 | 2010-03-09 | Nouvelle forme cristalline vi de l'agomelatine son procede de preparation et son application |
JP2011553265A JP2012519715A (ja) | 2009-03-10 | 2010-03-09 | アゴメラチンの新規結晶形態vi、製造方法及びその応用 |
AP2011005914A AP3049A (en) | 2009-03-10 | 2010-03-09 | New crystalline form VI of agomelatine, preparation method and application thereof |
BRPI1013249A BRPI1013249A2 (pt) | 2009-03-10 | 2010-03-09 | "forma cristalina vi da agomelatina, preparação e uso da mesma." |
EA201101304A EA019127B1 (ru) | 2009-03-10 | 2010-03-09 | Новая кристаллическая форма vi агомелатина, ее получение и применение |
IL214683A IL214683A0 (en) | 2009-03-10 | 2011-08-16 | New crystalline form vi of agomelatine, preparation method and application thereof |
TN2011000426A TN2011000426A1 (en) | 2009-03-10 | 2011-08-17 | New crystalline form vi of agomelatine, preparation method and application thereof |
ZA2011/06049A ZA201106049B (en) | 2009-03-10 | 2011-08-17 | New crystalline form vi of agomelatine, preparation method and application thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200910047329.2A CN101585779B (zh) | 2009-03-10 | 2009-03-10 | 阿戈美拉汀的晶型vi及其制备方法和应用 |
CN200910047329.2 | 2009-03-10 |
Publications (1)
Publication Number | Publication Date |
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WO2010102554A1 true WO2010102554A1 (zh) | 2010-09-16 |
Family
ID=41370233
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2010/070931 WO2010102554A1 (zh) | 2009-03-10 | 2010-03-09 | 阿戈美拉汀的新晶型ⅵ及其制备方法和应用 |
Country Status (27)
Country | Link |
---|---|
US (1) | US8614251B2 (zh) |
EP (1) | EP2431355A4 (zh) |
JP (1) | JP2012519715A (zh) |
KR (1) | KR20110123266A (zh) |
CN (1) | CN101585779B (zh) |
AP (1) | AP3049A (zh) |
AU (1) | AU2010223720B2 (zh) |
BR (1) | BRPI1013249A2 (zh) |
CA (1) | CA2754276A1 (zh) |
CL (1) | CL2011002231A1 (zh) |
CO (1) | CO6410293A2 (zh) |
CR (1) | CR20110457A (zh) |
CU (1) | CU20110162A7 (zh) |
EA (1) | EA019127B1 (zh) |
EC (1) | ECSP11011309A (zh) |
GE (1) | GEP20146114B (zh) |
HN (1) | HN2011002408A (zh) |
IL (1) | IL214683A0 (zh) |
MA (1) | MA33100B1 (zh) |
MX (1) | MX2011009339A (zh) |
NI (1) | NI201100167A (zh) |
PE (1) | PE20120653A1 (zh) |
SG (2) | SG173692A1 (zh) |
TN (1) | TN2011000426A1 (zh) |
UA (1) | UA100476C2 (zh) |
WO (1) | WO2010102554A1 (zh) |
ZA (1) | ZA201106049B (zh) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2556824A1 (fr) | 2011-08-10 | 2013-02-13 | Les Laboratoires Servier | Composition pharmaceutique solide pour administration buccale d'agomelatine |
US20140088197A1 (en) * | 2011-03-23 | 2014-03-27 | Les Laboratories Servier | Mixed crystal agomelatine (form viii), preparation method and use thereof and pharmaceutical composition containing same |
WO2014122405A1 (fr) | 2013-02-08 | 2014-08-14 | Les Laboratoires Servier | Composition pharmaceutique solide pour l'administration buccale d'agomélatine |
EP2705023A4 (en) * | 2011-01-04 | 2014-11-19 | Symed Labs Ltd | PROCESSES FOR THE PREPARATION OF N- [2- (7-METHOXY-1-NAPHTHYLLELYHYL) ACETAMIDE |
WO2015124496A1 (en) | 2014-02-19 | 2015-08-27 | Synthon B.V. | Pharmaceutical composition comprising amorphous agomelatine |
EP3075724A1 (en) | 2015-03-31 | 2016-10-05 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Solid form of agomelatine |
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CN101585779B (zh) * | 2009-03-10 | 2014-04-02 | 上海医药工业研究院 | 阿戈美拉汀的晶型vi及其制备方法和应用 |
WO2011006387A1 (zh) * | 2009-07-11 | 2011-01-20 | 浙江华海药业股份有限公司 | 阿戈美拉汀的制备方法、阿戈美拉汀晶形及其制备方法 |
CN101955440B (zh) * | 2009-07-17 | 2014-04-09 | 江苏万特制药有限公司 | 一种阿戈美拉汀新晶型及其制备方法 |
CN102050756A (zh) * | 2009-11-09 | 2011-05-11 | 北京利乐生制药科技有限公司 | 阿戈美拉汀新晶型及其制备方法 |
CN102190595A (zh) | 2010-03-17 | 2011-09-21 | 上海医药工业研究院 | 阿戈美拉汀溴化氢水合物及其制备方法 |
CN102557979B (zh) * | 2010-12-16 | 2014-11-26 | 北大方正集团有限公司 | 一种阿戈美拉汀的晶型、其制备方法、用途及药物组合物 |
CN102690210A (zh) * | 2011-03-23 | 2012-09-26 | 上海医药工业研究院 | 阿戈美拉汀的新晶型ⅶ、其制备方法、应用和包含其的药物组合物 |
ES2634243T3 (es) | 2011-11-30 | 2017-09-27 | Ratiopharm Gmbh | Complejo de agomelatina-urea y formas cristalinas del mismo |
CN103690499B (zh) * | 2013-12-23 | 2015-05-06 | 天津泰普药品科技发展有限公司 | 一种稳定的晶i型阿戈美拉汀片剂及其制备方法 |
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EP0447285A1 (fr) | 1990-02-27 | 1991-09-18 | Adir Et Compagnie | Nouveaux dérivés à structure naphtalénique, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
CN1907958A (zh) * | 2005-08-03 | 2007-02-07 | 瑟维尔实验室 | 阿戈美拉汀的新晶形ⅴ、它的制备方法和包含它的药物组合物 |
CN100445264C (zh) * | 2005-08-03 | 2008-12-24 | 瑟维尔实验室 | 阿戈美拉汀的新晶形ⅳ、它的制备方法和包含它的药物组合物 |
CN101429134A (zh) * | 2007-11-09 | 2009-05-13 | 瑟维尔实验室 | 阿戈美拉汀的新晶形vi、它的制备方法和包含它的药物组合物 |
CN101585779A (zh) * | 2009-03-10 | 2009-11-25 | 上海医药工业研究院 | 阿戈美拉汀的新晶型ⅵ及其制备方法和应用 |
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2009
- 2009-03-10 CN CN200910047329.2A patent/CN101585779B/zh not_active Expired - Fee Related
-
2010
- 2010-03-09 EP EP10750350A patent/EP2431355A4/en not_active Withdrawn
- 2010-03-09 SG SG2011058559A patent/SG173692A1/en unknown
- 2010-03-09 WO PCT/CN2010/070931 patent/WO2010102554A1/zh active Application Filing
- 2010-03-09 JP JP2011553265A patent/JP2012519715A/ja active Pending
- 2010-03-09 AU AU2010223720A patent/AU2010223720B2/en not_active Ceased
- 2010-03-09 US US13/138,615 patent/US8614251B2/en not_active Expired - Fee Related
- 2010-03-09 MX MX2011009339A patent/MX2011009339A/es not_active Application Discontinuation
- 2010-03-09 SG SG2011088564A patent/SG177886A1/en unknown
- 2010-03-09 AP AP2011005914A patent/AP3049A/xx active
- 2010-03-09 PE PE2011001513A patent/PE20120653A1/es not_active Application Discontinuation
- 2010-03-09 BR BRPI1013249A patent/BRPI1013249A2/pt not_active Application Discontinuation
- 2010-03-09 UA UAA201111757A patent/UA100476C2/ru unknown
- 2010-03-09 KR KR1020117021813A patent/KR20110123266A/ko not_active Application Discontinuation
- 2010-03-09 GE GEAP201012406A patent/GEP20146114B/en unknown
- 2010-03-09 CA CA2754276A patent/CA2754276A1/en not_active Abandoned
- 2010-03-09 EA EA201101304A patent/EA019127B1/ru not_active IP Right Cessation
- 2010-03-09 MA MA34144A patent/MA33100B1/fr unknown
-
2011
- 2011-08-16 IL IL214683A patent/IL214683A0/en unknown
- 2011-08-17 TN TN2011000426A patent/TN2011000426A1/fr unknown
- 2011-08-17 ZA ZA2011/06049A patent/ZA201106049B/en unknown
- 2011-08-23 CU CU20110162A patent/CU20110162A7/es unknown
- 2011-08-24 CR CR20110457A patent/CR20110457A/es unknown
- 2011-08-26 CO CO11109271A patent/CO6410293A2/es not_active Application Discontinuation
- 2011-09-07 EC EC2011011309A patent/ECSP11011309A/es unknown
- 2011-09-08 NI NI201100167A patent/NI201100167A/es unknown
- 2011-09-09 CL CL2011002231A patent/CL2011002231A1/es unknown
- 2011-09-09 HN HN2011002408A patent/HN2011002408A/es unknown
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Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2705023A4 (en) * | 2011-01-04 | 2014-11-19 | Symed Labs Ltd | PROCESSES FOR THE PREPARATION OF N- [2- (7-METHOXY-1-NAPHTHYLLELYHYL) ACETAMIDE |
US20140088197A1 (en) * | 2011-03-23 | 2014-03-27 | Les Laboratories Servier | Mixed crystal agomelatine (form viii), preparation method and use thereof and pharmaceutical composition containing same |
JP2014516921A (ja) * | 2011-03-23 | 2014-07-17 | 上海医薬工業研究院 | 混晶アゴメラチン(viii型)、その調製方法及び使用、並びにこれを含有する医薬組成物 |
AU2012231548B2 (en) * | 2011-03-23 | 2015-11-19 | Les Laboratoires Servier | Mixed crystal agomelatine (Form-VIII), preparation method and use thereof and pharmaceutical composition containing same |
EP2556824A1 (fr) | 2011-08-10 | 2013-02-13 | Les Laboratoires Servier | Composition pharmaceutique solide pour administration buccale d'agomelatine |
WO2013021139A1 (fr) | 2011-08-10 | 2013-02-14 | Les Laboratoires Servier | Composition pharmaceutique solide pour administration buccale d'agomelatine |
WO2014122405A1 (fr) | 2013-02-08 | 2014-08-14 | Les Laboratoires Servier | Composition pharmaceutique solide pour l'administration buccale d'agomélatine |
WO2015124496A1 (en) | 2014-02-19 | 2015-08-27 | Synthon B.V. | Pharmaceutical composition comprising amorphous agomelatine |
EP3075724A1 (en) | 2015-03-31 | 2016-10-05 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Solid form of agomelatine |
Also Published As
Publication number | Publication date |
---|---|
EP2431355A1 (en) | 2012-03-21 |
NI201100167A (es) | 2012-01-11 |
CL2011002231A1 (es) | 2012-02-03 |
SG177886A1 (en) | 2012-02-28 |
GEP20146114B (en) | 2014-07-10 |
JP2012519715A (ja) | 2012-08-30 |
AU2010223720A1 (en) | 2011-09-08 |
EP2431355A4 (en) | 2012-08-08 |
AP2011005914A0 (en) | 2011-10-31 |
HN2011002408A (es) | 2014-06-23 |
MA33100B1 (fr) | 2012-03-01 |
CR20110457A (es) | 2011-09-21 |
ECSP11011309A (es) | 2011-10-31 |
AP3049A (en) | 2014-11-30 |
CN101585779B (zh) | 2014-04-02 |
CN101585779A (zh) | 2009-11-25 |
CO6410293A2 (es) | 2012-03-30 |
UA100476C2 (en) | 2012-12-25 |
IL214683A0 (en) | 2011-11-30 |
CU20110162A7 (es) | 2012-02-15 |
US8614251B2 (en) | 2013-12-24 |
SG173692A1 (en) | 2011-09-29 |
BRPI1013249A2 (pt) | 2016-04-05 |
CA2754276A1 (en) | 2010-09-16 |
KR20110123266A (ko) | 2011-11-14 |
TN2011000426A1 (en) | 2013-03-27 |
US20120004313A1 (en) | 2012-01-05 |
MX2011009339A (es) | 2011-09-27 |
ZA201106049B (en) | 2012-10-31 |
AU2010223720B2 (en) | 2012-05-03 |
EA201101304A1 (ru) | 2012-04-30 |
PE20120653A1 (es) | 2012-06-14 |
EA019127B1 (ru) | 2014-01-30 |
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