KR20130136544A - 아고멜라틴의 신규한 결정성 형태 vii, 및 이의 제조 방법 및 용도 및 이를 함유하는 약학적 조성물 - Google Patents
아고멜라틴의 신규한 결정성 형태 vii, 및 이의 제조 방법 및 용도 및 이를 함유하는 약학적 조성물 Download PDFInfo
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- KR20130136544A KR20130136544A KR1020137027637A KR20137027637A KR20130136544A KR 20130136544 A KR20130136544 A KR 20130136544A KR 1020137027637 A KR1020137027637 A KR 1020137027637A KR 20137027637 A KR20137027637 A KR 20137027637A KR 20130136544 A KR20130136544 A KR 20130136544A
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- agomelatine
- crystalline form
- acetate
- water
- temperature
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- 229960002629 agomelatine Drugs 0.000 title claims abstract description 44
- 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 39
- 239000013078 crystal Substances 0.000 title claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 14
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 238000002425 crystallisation Methods 0.000 claims description 10
- 230000008025 crystallization Effects 0.000 claims description 10
- -1 agomelatine compound Chemical class 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical group [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 238000002441 X-ray diffraction Methods 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 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 4
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 4
- 208000010643 digestive system disease Diseases 0.000 claims description 4
- 206010016256 fatigue Diseases 0.000 claims description 4
- 206010022437 insomnia Diseases 0.000 claims description 4
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 claims description 4
- 229960003987 melatonin Drugs 0.000 claims description 4
- 208000012672 seasonal affective disease Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005695 Ammonium acetate Substances 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 235000019257 ammonium acetate Nutrition 0.000 claims description 3
- 229940043376 ammonium acetate Drugs 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 238000010586 diagram Methods 0.000 claims description 3
- 208000019899 phobic disease Diseases 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000035882 stress Effects 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 206010034912 Phobia Diseases 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- 238000001757 thermogravimetry curve Methods 0.000 description 4
- 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
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010812 external standard method Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 238000001159 Fisher's combined probability test Methods 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
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- 235000014632 disordered eating Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
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- 238000000227 grinding Methods 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000005426 pharmaceutical component Substances 0.000 description 1
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- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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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
- C07C233/22—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 an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
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- A—HUMAN NECESSITIES
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
Description
Claims (14)
- 제 3항에 있어서, 화학식 (II) 또는 (III)의 아고멜라틴 화합물 및 아세테이트의 몰 비가 약 1:1-1.5, 가장 적합하게는 1:1-1.1인 제조 방법.
- 제 3항 또는 제 4항에 있어서, 아세트산 대 물의 부피 비가 1:10-30인 제조 방법.
- 제 3항 내지 제 5항 중 어느 한 항에 있어서, 상기 아세테이트가 포타슘 아세테이트 또는 암모늄 아세테이트인 제조 방법.
- 제 3항 내지 제 6항 중 어느 한 항에 있어서, 생성된 반응 혼합물의 온도가 19-25℃, 특히 약 22℃ 또는 23℃에 도달하는 경우, 물을 적가하여 결정화를 발생시키는 제조 방법.
- 제 3항 내지 제 7항 중 어느 한 항에 있어서, 생성된 반응 혼합물에 물을 적가한 후, 20℃의 온도에서 교반하여 결정화를 발생시키는 제조 방법.
- 제 3항 내지 제 8항 중 어느 한 항에 있어서, 아세테이트의 첨가 후, 반응 혼합물을 30-50℃로 가열하여 투명한 용액을 생성시킨 후; 상기 용액을 자체적으로 냉각되도록 방치시키고, 물을 적가하여 결정화를 발생시키는 제조 방법.
- 제 1항 또는 제 2항에 따른 아고멜라틴의 결정체 형태 및 약학적으로 허용되는 애쥬번트 또는 부형제를 포함하는 약학적 조성물.
- 제 10항에 있어서, 멜라토닌계의 질병을 치료하기 위해 사용되는 약제의 제조에 사용되는 약학적 조성물.
- 제 10항에 있어서, 수면 장애(sleep disorder), 스트레스, 불안(anxiety), 계절성 정동 장애(seasonal affective disorder), 중증 우울증(severe depression), 심장혈관 질병(cardiovascular disease), 소화계통 질병(digestive system disease), 비행 시차에 의해 발생하는 불면증 및 피로(insomnia and fatigue brought on by jet lag), 정신분열병(schizophrenia), 공포증(phobia), 또는 우울증(depression)을 치료하기 위해 사용되는 약제의 제조에서 사용되는 약학적 조성물.
- 멜라토닌계의 질병의 치료와 관련된, 제 1항 또는 제 2항에 따른 아고멜라틴의 결정체 형태의 약학적 적용.
- 수면 장애, 스트레스, 불안, 계절성 정동 장애, 중증 우울증, 심장혈관 질병, 소화계통 질병, 비행 시차에 의해 발생하는 불면증 및 피로, 정신분열병, 공포증, 또는 우울증의 치료와 관련된, 제 1항 또는 제 2항에 따른 아고멜라틴의 결정체 형태의 약학적 적용.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CN201110070828.0 | 2011-03-23 | ||
CN2011100708280A CN102690210A (zh) | 2011-03-23 | 2011-03-23 | 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 |
PCT/CN2012/072816 WO2012126385A1 (zh) | 2011-03-23 | 2012-03-22 | 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 |
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US (1) | US9527803B2 (ko) |
EP (1) | EP2690087B1 (ko) |
JP (1) | JP6203170B2 (ko) |
KR (1) | KR20130136544A (ko) |
CN (2) | CN102690210A (ko) |
AR (1) | AR085543A1 (ko) |
AU (1) | AU2012231547B2 (ko) |
BR (1) | BR112013024219A2 (ko) |
CA (1) | CA2829687C (ko) |
CY (1) | CY1119625T1 (ko) |
DK (1) | DK2690087T3 (ko) |
EA (1) | EA023297B1 (ko) |
ES (1) | ES2650604T3 (ko) |
GE (1) | GEP20156386B (ko) |
HK (1) | HK1193087A1 (ko) |
HR (1) | HRP20171831T1 (ko) |
HU (1) | HUE037264T2 (ko) |
LT (1) | LT2690087T (ko) |
MA (1) | MA34958B1 (ko) |
MD (1) | MD4391C1 (ko) |
ME (1) | ME02921B (ko) |
MX (1) | MX355552B (ko) |
MY (1) | MY185235A (ko) |
NO (1) | NO2690087T3 (ko) |
PL (1) | PL2690087T3 (ko) |
PT (1) | PT2690087T (ko) |
RS (1) | RS56444B1 (ko) |
SG (1) | SG193300A1 (ko) |
SI (1) | SI2690087T1 (ko) |
UA (1) | UA113058C2 (ko) |
WO (1) | WO2012126385A1 (ko) |
ZA (1) | ZA201306760B (ko) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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PH12012000132B1 (en) * | 2011-06-09 | 2014-10-20 | Servier Lab | New co-crystals of agomelatine, a process for their preparation and pharmaceutical compositions containing them |
HUE049928T2 (hu) * | 2013-07-29 | 2020-11-30 | Servier Lab | Agomelatin és szulfonsavak komplexei, eljárás elõállításukra, és ezeket tartalmazó gyógyszerészeti készítmények |
KR101470794B1 (ko) * | 2014-06-30 | 2014-12-08 | 순천향대학교 산학협력단 | 아고멜라틴 공결정의 제조 방법 및 이를 포함하는 조성물 |
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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 |
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FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
US7498466B2 (en) * | 2004-02-13 | 2009-03-03 | Les Laboratoires Servier | Process for the synthesis and crystalline form of agomelatine |
FR2866335B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
FR2889522B1 (fr) | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iv de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
US7358395B2 (en) * | 2005-08-03 | 2008-04-15 | Les Laboratories Servier | Crystalline form V of agomelatine, a process for its preparation and pharmaceutical compositions containing it |
FR2889523B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline v de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
FR2889521B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iii de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
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EP2319827A1 (en) | 2009-11-09 | 2011-05-11 | Ratiopharm GmbH | Process for the production of polymorph form I of agomelatine |
CN101704763B (zh) * | 2009-11-25 | 2012-03-28 | 天津泰普药品科技发展有限公司 | 阿戈美拉汀i型晶体的制备方法 |
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