JP2014522388A5 - - Google Patents
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- Publication number
- JP2014522388A5 JP2014522388A5 JP2014506792A JP2014506792A JP2014522388A5 JP 2014522388 A5 JP2014522388 A5 JP 2014522388A5 JP 2014506792 A JP2014506792 A JP 2014506792A JP 2014506792 A JP2014506792 A JP 2014506792A JP 2014522388 A5 JP2014522388 A5 JP 2014522388A5
- Authority
- JP
- Japan
- Prior art keywords
- crystal
- acetamide
- naphthyl
- methoxy
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- YJYPHIXNFHFHND-UHFFFAOYSA-N Agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 claims 3
- -1 7-methoxy-1-naphthyl Chemical group 0.000 claims 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 2
- 238000001069 Raman spectroscopy Methods 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 229960002629 agomelatine Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
Claims (5)
- アゴメラチンとして知られるＮ‐［２‐（７‐メトキシ‐１‐ナフチル）エチル］アセトアミドと、クエン酸及びベンゼンスルホン酸からなる群から選択される共結晶形成剤との共結晶。
- 以下の特性：
ｉ）５．２；１２．２；１７．０；１９．３；２０．６；２２．７及び２７．３±０．２°の２θ値で、主要なピークを有するＸ線粉末回折（ＸＲＰＤ）パターン、
ｉｉ）１２３〜１２７℃の範囲での融点、及び
ｉｉｉ）波数２９６３、１７４９、１６８１、９４４、７８３ｃｍ-1でのラマン散乱ピーク
の１つ以上によって特徴付けられる、請求項１に記載のＮ‐［２‐（７‐メトキシ‐１‐ナフチル）エチル］アセトアミドとクエン酸との共結晶。 - 以下の特性：
ｉ）１１．５；１５．７；１７．４；１９．０；２４．５及び２６．４±０．２°の２θ値で、主要なピークを有するＸ線粉末回折（ＸＲＰＤ）パターン、
ｉｉ）１２８〜１３２℃の範囲での融点、及び
ｉｉｉ）波数３０７３、１５８５、１１６３、９９７、７２７ｃｍ-1でのラマン散乱ピーク
の１つ以上によって特徴付けられる、請求項１に記載のＮ‐［２‐（７‐メトキシ‐１‐ナフチル）エチル］アセトアミドとベンゼンスルホン酸との共結晶。 - 以下のステップ：
Ｎ‐［２‐（７‐メトキシ‐１‐ナフチル）エチル］アセトアミドを、適切な溶媒又は溶媒の混合物中に、共結晶形成剤と共に溶解し、そして
前記溶液を冷却することによって、又は前記溶液を蒸発させることによって２元系共結晶を結晶化する
ことを含む、請求項１〜３のいずれか１項に記載の共結晶を調製するための方法。 - ある量の共結晶が、前記溶液に種晶として添加されることを特徴とする、請求項４に記載の方法。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11075073.4A EP2517700B1 (en) | 2011-04-28 | 2011-04-28 | Pharmaceutically acceptable cocrystals of N-[2-(7-methoxy-1-naphthyl]acetamide and methods of their preparation |
| EP11075073.4 | 2011-04-28 | ||
| PCT/EP2012/001761 WO2012146371A1 (en) | 2011-04-28 | 2012-04-25 | Pharmaceutically acceptable cocrystals of n-[2-(7-methoxy-1-naphtyl)ethyl]acetamide and methods of their preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014522388A JP2014522388A (ja) | 2014-09-04 |
| JP2014522388A5 true JP2014522388A5 (ja) | 2015-05-28 |
| JP5770928B2 JP5770928B2 (ja) | 2015-08-26 |
Family
ID=44519907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014506792A Expired - Fee Related JP5770928B2 (ja) | 2011-04-28 | 2012-04-25 | Ｎ‐［２‐（７‐メトキシ‐１‐ナフチル）エチル］アセトアミドの医薬的に許容される共結晶及びそれらの調製方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8927771B2 (ja) |
| EP (1) | EP2517700B1 (ja) |
| JP (1) | JP5770928B2 (ja) |
| KR (1) | KR20140008370A (ja) |
| CN (1) | CN103501777B (ja) |
| BR (1) | BR112013023471A2 (ja) |
| EA (1) | EA024422B1 (ja) |
| ES (1) | ES2429348T3 (ja) |
| IL (1) | IL228916A (ja) |
| MX (1) | MX342807B (ja) |
| PL (1) | PL2517700T3 (ja) |
| PT (1) | PT2517700E (ja) |
| RS (1) | RS52982B (ja) |
| UA (1) | UA111844C2 (ja) |
| WO (1) | WO2012146371A1 (ja) |
| ZA (1) | ZA201307688B (ja) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12012000132A1 (en) | 2011-06-09 | 2014-10-20 | Servier Lab | New co-crystals of agomelatine, a process for their preparation and pharmaceutical compositions containing them |
| EP2551257A1 (en) * | 2011-07-28 | 2013-01-30 | Laboratorios Del. Dr. Esteve, S.A. | Co-crystals of agomelatine with co-crystal-formers |
| US9409857B2 (en) | 2012-05-14 | 2016-08-09 | Shanghai Righthand Pharmtech, Co., Ltd. | Agomelatine sulfuric acid complex, and preparation method and application thereof |
| US10098859B2 (en) | 2012-09-05 | 2018-10-16 | Amri Ssci, Llc | Cocrystals of p-coumaric acid |
| EP2743255B1 (en) | 2012-12-17 | 2016-06-22 | Dr. Reddy's Laboratories Ltd. | Cocrystal of agomelatine with phosphoric acid |
| 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 |
| ES2645223T3 (es) | 2013-06-06 | 2017-12-04 | Zentiva, K.S. | Formulaciones de agomelatina que comprenden agomelatina en forma de co-cristales |
| WO2015013865A1 (en) * | 2013-07-29 | 2015-02-05 | Les Laboratoires Servier | Agomelatine sulfonic acids complexes and preparation thereof |
| FR3012142B1 (fr) * | 2013-10-17 | 2016-07-15 | Servier Lab | Nouveaux complexes d'agomelatine et d'acides sulfoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PL3027588T3 (pl) * | 2013-07-29 | 2020-11-02 | Les Laboratoires Servier | Kompleksy agomelatyny i kwasów sulfonowych, sposób ich wytwarzania i kompozycje farmaceutyczne je zawierające |
| CN105473551B (zh) * | 2013-07-31 | 2019-01-11 | 法国施维雅药厂 | 阿戈美拉汀和对甲苯磺酸的共晶的新形式、其制备方法和包含其的药物组合物 |
| US9663451B2 (en) * | 2013-07-31 | 2017-05-30 | Les Laboratoires Servier | Forms of co-crystals of agomelatine and p toluenesulphonic acid, a process for their preparation and pharmaceutical compositions containing them |
| WO2015013903A1 (en) * | 2013-07-31 | 2015-02-05 | Les Laboratoires Servier | NEW AGOMELATINE p-TOLUENESULFONIC ACID CO-CRYSTAL FORMS AND PREPARATION THEREOF |
| KR101404836B1 (ko) | 2014-03-21 | 2014-06-09 | 순천향대학교 산학협력단 | 아고멜라틴의 공결정 및 그의 제조방법 |
| KR101470794B1 (ko) * | 2014-06-30 | 2014-12-08 | 순천향대학교 산학협력단 | 아고멜라틴 공결정의 제조 방법 및 이를 포함하는 조성물 |
| EP3075724B1 (en) | 2015-03-31 | 2023-07-12 | F.I.S.- Fabbrica Italiana Sintetici S.p.A. | Solid form of agomelatine |
| WO2017115284A1 (en) * | 2015-12-28 | 2017-07-06 | Leiutis Pharmaceuticals Pvt, Ltd. | Novel co-crystal forms of agomelatine |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007524596A (ja) * | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| AR047553A1 (es) * | 2003-07-04 | 2006-01-25 | Lundbeck & Co As H | La combinacion de un inhibidor de reabsorcion de serotonina y agomelatina |
| WO2008035177A2 (en) * | 2006-09-18 | 2008-03-27 | Copharm | Combination of mt1 and mt2 melatonin receptor agonists and a norepinephrine/dopamine reuptake inhibitor |
| CN101481321B (zh) * | 2009-02-27 | 2012-04-18 | 上海医药工业研究院 | 阿戈美拉汀卤化氢复合物及其制备方法 |
| CN102106806B (zh) * | 2009-12-29 | 2013-04-17 | 上海中西制药有限公司 | 一种固体制剂的制备方法及所得固体制剂 |
| WO2012046253A2 (en) * | 2010-10-08 | 2012-04-12 | Msn Laboratories Limited | Process for the preparation of n-[2- (7-methoxy-l-naphthyl) ethyl] acetamide and its novel crystalline forms |
| PH12012000132A1 (en) * | 2011-06-09 | 2014-10-20 | Servier Lab | New co-crystals of agomelatine, a process for their preparation and pharmaceutical compositions containing them |
-
2011
- 2011-04-28 PL PL11075073T patent/PL2517700T3/pl unknown
- 2011-04-28 RS RS20130436A patent/RS52982B/en unknown
- 2011-04-28 ES ES11075073T patent/ES2429348T3/es active Active
- 2011-04-28 EP EP11075073.4A patent/EP2517700B1/en not_active Not-in-force
- 2011-04-28 PT PT110750734T patent/PT2517700E/pt unknown
-
2012
- 2012-04-25 US US14/114,211 patent/US8927771B2/en not_active Expired - Fee Related
- 2012-04-25 EA EA201391574A patent/EA024422B1/ru not_active IP Right Cessation
- 2012-04-25 BR BR112013023471A patent/BR112013023471A2/pt not_active Application Discontinuation
- 2012-04-25 MX MX2013012103A patent/MX342807B/es active IP Right Grant
- 2012-04-25 WO PCT/EP2012/001761 patent/WO2012146371A1/en active Application Filing
- 2012-04-25 KR KR1020137024023A patent/KR20140008370A/ko not_active Application Discontinuation
- 2012-04-25 CN CN201280020790.9A patent/CN103501777B/zh not_active Expired - Fee Related
- 2012-04-25 UA UAA201313793A patent/UA111844C2/uk unknown
- 2012-04-25 JP JP2014506792A patent/JP5770928B2/ja not_active Expired - Fee Related
-
2013
- 2013-10-16 IL IL228916A patent/IL228916A/en active IP Right Grant
- 2013-10-16 ZA ZA2013/07688A patent/ZA201307688B/en unknown
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