CA2464068C - .alpha.-form or .beta.-form crystal of (r)-2-(2-aminothiazol-4yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl)acetanilide - Google Patents

.alpha.-form or .beta.-form crystal of (r)-2-(2-aminothiazol-4yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl)acetanilide Download PDF

Info

Publication number
CA2464068C
CA2464068C CA002464068A CA2464068A CA2464068C CA 2464068 C CA2464068 C CA 2464068C CA 002464068 A CA002464068 A CA 002464068A CA 2464068 A CA2464068 A CA 2464068A CA 2464068 C CA2464068 C CA 2464068C
Authority
CA
Canada
Prior art keywords
form crystal
ethyl
amino
crystal
acetanilide
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.)
Expired - Lifetime
Application number
CA002464068A
Other languages
English (en)
French (fr)
Other versions
CA2464068A1 (en
Inventor
Souichirou Kawazoe
Kenichirou Sakamoto
Yuji Awamura
Tatsuya Maruyama
Takayuki Suzuki
Kenichi Onda
Toshiyuki Takasu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Astellas Pharma Inc
Original Assignee
Astellas Pharma Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=19148268&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2464068(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Astellas Pharma Inc filed Critical Astellas Pharma Inc
Publication of CA2464068A1 publication Critical patent/CA2464068A1/en
Application granted granted Critical
Publication of CA2464068C publication Critical patent/CA2464068C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Diabetes (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
CA002464068A 2001-10-30 2002-10-29 .alpha.-form or .beta.-form crystal of (r)-2-(2-aminothiazol-4yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl)acetanilide Expired - Lifetime CA2464068C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2001332914 2001-10-30
JP2001-332914 2001-10-30
PCT/JP2002/011217 WO2003037881A1 (en) 2001-10-30 2002-10-29 α-FORM OR ß-FORM CRYSTAL OF ACETANILIDE DERIVATIVE

Publications (2)

Publication Number Publication Date
CA2464068A1 CA2464068A1 (en) 2003-05-08
CA2464068C true CA2464068C (en) 2007-10-16

Family

ID=19148268

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002464068A Expired - Lifetime CA2464068C (en) 2001-10-30 2002-10-29 .alpha.-form or .beta.-form crystal of (r)-2-(2-aminothiazol-4yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl)acetanilide

Country Status (17)

Country Link
US (2) US7342117B2 (enExample)
EP (3) EP1932838A3 (enExample)
JP (1) JP3800220B2 (enExample)
KR (1) KR100908796B1 (enExample)
CN (1) CN1243740C (enExample)
AU (1) AU2002344419C1 (enExample)
BR (1) BRPI0213570B8 (enExample)
CA (1) CA2464068C (enExample)
ES (1) ES2404071T3 (enExample)
HU (1) HU230481B1 (enExample)
MX (1) MXPA04003936A (enExample)
NO (1) NO326965B1 (enExample)
PL (1) PL218982B1 (enExample)
RU (1) RU2303033C2 (enExample)
TW (1) TW200300020A (enExample)
WO (1) WO2003037881A1 (enExample)
ZA (1) ZA200403044B (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016049749A1 (en) * 2014-10-01 2016-04-07 Apotex Inc. Solid forms of mirabegron

Families Citing this family (77)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7342117B2 (en) * 2001-10-30 2008-03-11 Astellas Pharma Inc. α-form or β-form crystal of acetanilide derivative
CA2503570C (en) 2002-11-07 2011-04-19 Yamanouchi Pharmaceutical Co., Ltd. Remedy for overactive bladder comprising acetic acid anilide derivative as the active ingredient
US7772188B2 (en) 2003-01-28 2010-08-10 Ironwood Pharmaceuticals, Inc. Methods and compositions for the treatment of gastrointestinal disorders
US20080125403A1 (en) 2004-04-02 2008-05-29 Merck & Co., Inc. Method of Treating Men with Metabolic and Anthropometric Disorders
WO2008151257A2 (en) 2007-06-04 2008-12-11 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
SI2216021T1 (sl) 2007-11-02 2013-01-31 Astellas Pharma Inc. Farmacevtski sestavek za zdravljenje prekomerno aktivnega sečnega mehurja
ES2627848T3 (es) 2008-06-04 2017-07-31 Synergy Pharmaceuticals Inc. Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos
ES2624828T3 (es) 2008-07-16 2017-07-17 Synergy Pharmaceuticals Inc. Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros
TWI478712B (zh) * 2008-09-30 2015-04-01 Astellas Pharma Inc 釋控性醫藥組成物
US8410284B2 (en) 2008-10-22 2013-04-02 Merck Sharp & Dohme Corp Cyclic benzimidazole derivatives useful as anti-diabetic agents
WO2010051206A1 (en) 2008-10-31 2010-05-06 Merck Sharp & Dohme Corp. Novel cyclic benzimidazole derivatives useful anti-diabetic agents
WO2010147830A2 (en) * 2009-06-15 2010-12-23 Auspex Pharmaceuticals, Inc. Aminothiazole modulators of beta-3-adrenoreceptor
JP2013520502A (ja) 2010-02-25 2013-06-06 メルク・シャープ・エンド・ドーム・コーポレイション 有用な抗糖尿病薬である新規な環状ベンズイミダゾール誘導体
ES2665467T3 (es) * 2010-03-29 2018-04-25 Astellas Pharma Inc. Composición farmacéutica de liberación modificada
CN103068816B (zh) * 2010-06-16 2015-01-07 武田药品工业株式会社 酰胺化合物的结晶
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
CA2826649C (en) 2011-02-25 2016-07-26 Merck Sharp & Dohme Corp. Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents
IN2013CN09704A (enExample) * 2011-05-18 2015-07-03 Reddys Lab Ltd Dr
US9655885B2 (en) 2011-05-18 2017-05-23 Dr. Reddy's Laboratories Ltd. Amorphous mirabegron and processes for crystal forms of mirabegron
JP6217938B2 (ja) 2011-10-28 2017-10-25 ルメナ ファーマシューティカルズ エルエルシー 小児の胆汁うっ滞性肝疾患の処置のための胆汁酸再循環阻害剤
EP2832730A4 (en) 2012-03-30 2015-09-09 Astellas Pharma Inc MIRABEGRAPHIC PHARMACEUTICAL COMPOSITION
CN103387500A (zh) * 2012-05-11 2013-11-13 上海医药工业研究院 一种米拉贝隆及其中间体的制备方法
US20140045746A1 (en) 2012-08-02 2014-02-13 Merck Sharp & Dohme Corp. Antidiabetic tricyclic compounds
TW201424772A (zh) 2012-08-31 2014-07-01 Astellas Pharma Inc 經口投與用醫藥組成物
JP2016516004A (ja) 2013-02-22 2016-06-02 メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． 抗糖尿病二環式化合物
WO2014132270A2 (en) * 2013-02-27 2014-09-04 Msn Laboratories Limited Process for the preparation of 2-(2-aminothiazol-4-yl)-n-[4-(2-{[(2r)-2-hydroxy-2-phenyl ethyl]amino}ethyl)phenyl]acetamide monohydrochloride, its intermediates and polymorph thereof
WO2014139388A1 (en) 2013-03-14 2014-09-18 Merck Sharp & Dohme Corp. Novel indole derivatives useful as anti-diabetic agents
EP2968439A2 (en) 2013-03-15 2016-01-20 Synergy Pharmaceuticals Inc. Compositions useful for the treatment of gastrointestinal disorders
US9708367B2 (en) 2013-03-15 2017-07-18 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase and their uses
CN103193730A (zh) * 2013-04-17 2013-07-10 苏州永健生物医药有限公司 一种米拉贝隆的合成方法
CN103232368B (zh) * 2013-04-18 2015-08-12 苏州永健生物医药有限公司 一种(r)-4-硝基苯乙基-(2-羟基-2-苯乙基)-氨基甲酸叔丁酯的合成方法
CN103232352B (zh) * 2013-05-11 2015-12-23 苏州永健生物医药有限公司 (r)-4-(2-(2-羟基-2-苯乙胺基)乙基)苯胺基甲酸叔丁基酯
PL3004138T3 (pl) 2013-06-05 2024-07-29 Bausch Health Ireland Limited Ultra-oczyszczeni agoniści peptydowi cyklazy guanylanowej C, sposób ich uzyskiwania i ich zastosowanie
WO2015040605A1 (en) 2013-09-23 2015-03-26 Ranbaxy Laboratories Limited Crystalline form of mirabegron
WO2015040573A1 (en) 2013-09-23 2015-03-26 Ranbaxy Laboratories Limited Mirabegron dimethyl sulphoxide solvate and its use for the treatment of overactive bladder
WO2015044965A1 (en) 2013-09-30 2015-04-02 Megafine Pharma (P) Ltd. A process for preparation of mirabegron and alpha crystalline form thereof
ITMI20131653A1 (it) * 2013-10-07 2015-04-08 Dipharma Francis Srl Forme cristalline di un agonista adrenergico
WO2015051496A1 (en) 2013-10-08 2015-04-16 Merck Sharp & Dohme Corp. Antidiabetic tricyclic compounds
CN103641792B (zh) * 2013-12-27 2015-07-22 国药集团国瑞药业有限公司 一种米拉贝隆有关物质或其盐、其制备方法和用途
CN104876889B (zh) * 2014-02-27 2017-02-22 人福医药集团股份公司 化合物的合成方法
WO2015155664A1 (en) * 2014-04-08 2015-10-15 Suven Life Sciences Limited An improved process for the preparation of 2-(2-aminothiazol-4-yl)-n-[4-(2-[[(2r)-2-hydroxy-2- phenylethyl]amino]-ethyl)phenyl]acetamide
CN103896872A (zh) * 2014-04-29 2014-07-02 黑龙江大学 米拉贝隆的合成方法
CN104016943A (zh) * 2014-05-23 2014-09-03 苏州凯瑞医药科技有限公司 一种米拉贝隆的合成方法
CN104016877B (zh) * 2014-06-13 2017-02-15 南京海融制药有限公司 一种苯基乙酰胺类化合物及在制备米拉贝隆中的应用
WO2016020440A1 (en) * 2014-08-06 2016-02-11 Interquim, S.A. Method for the synthesis of mirabegron and its derivatives
WO2016024284A2 (en) 2014-08-07 2016-02-18 Wanbury Ltd. A process for the preparation of mirabegron and its intermediates
CN105481705A (zh) * 2014-08-23 2016-04-13 南京海纳医药科技有限公司 (r)-2-[[2-(4-氨基苯基)乙基]氨基]-1-苯乙醇的制备及应用
CN104230840A (zh) * 2014-09-05 2014-12-24 安徽联创药物化学有限公司 米拉贝隆的合成方法
US10149837B2 (en) 2014-09-26 2018-12-11 Universita' Degli Studi Di Bari Selective agonists of beta-adrenergic type 3 receptors (BAR3) and use thereof
JP2018508497A (ja) * 2015-02-02 2018-03-29 ルピン・リミテッド ミラベグロンの多形型の調製方法
JP2018090490A (ja) 2015-03-31 2018-06-14 アステラス製薬株式会社 ミラベグロン含有医薬組成物
FR3043555B1 (fr) * 2015-11-17 2019-10-25 Centre National De La Recherche Scientifique (Cnrs) Mirabegron pour le traitement de maladies retiniennes
EP3184516A1 (en) 2015-12-23 2017-06-28 Enantia, S.L. Crystalline inclusion complexes of mirabegron with beta-cyclodextrin
CN105801438A (zh) * 2016-04-12 2016-07-27 济南大学 一种米拉贝隆中间体的合成方法
CN107963976A (zh) * 2016-10-20 2018-04-27 中国动物疫病预防控制中心 一种苯乙醇胺类化合物中间体的制备方法
WO2018106518A1 (en) 2016-12-06 2018-06-14 Merck Sharp & Dohme Corp. Antidiabetic heterocyclic compounds
WO2018118670A1 (en) 2016-12-20 2018-06-28 Merck Sharp & Dohme Corp. Antidiabetic spirochroman compounds
EP3360866B1 (en) 2017-02-14 2019-01-02 Alfred E. Tiefenbacher (GmbH & Co. KG) Mirabegron prodrugs
KR101868438B1 (ko) 2017-04-13 2018-06-20 (주) 성운파마코피아 아미드 유도체의 제조방법
KR20250099259A (ko) 2017-06-06 2025-07-01 유로반트 사이언시즈 게엠베하 과민성 방광의 치료를 위한 비베그론의 용도
KR102398639B1 (ko) 2017-06-20 2022-05-17 (주) 성운파마코피아 아미드 유도체의 염 및 그 제조방법
CN108658797A (zh) * 2018-06-19 2018-10-16 安徽德信佳生物医药有限公司 一种米拉贝隆中间体(r)-2-(4-硝基苯乙基氨基)-1-苯基乙醇盐酸盐的合成
CN108947853A (zh) * 2018-06-29 2018-12-07 黑龙江鑫创生物科技开发有限公司 一种微通道反应器合成米拉贝隆中间体的方法
KR101928987B1 (ko) * 2018-08-28 2018-12-13 (주) 성운파마코피아 신규한 고순도 미라베그론의 결정질 일수화물, 이의 제조방법 또는 용도
TW202038963A (zh) 2018-12-05 2020-11-01 瑞士商優洛凡特科學公司 維貝隆（ｖｉｂｅｇｒｏｎ）於治療患有良性前列腺增生之男性中膀胱過動症症狀之用途
KR20200117091A (ko) 2019-04-02 2020-10-14 제이투에이치바이오텍 (주) 미라베그론 전구체 약물 화합물 및 이의 과민성 방광 질환의 치료 또는 개선을 위한 의약 용도
CN110590699B (zh) * 2019-09-29 2022-11-15 广东先强药业有限公司 一种米拉贝隆的精制方法
EP3722285B1 (en) 2020-04-08 2022-03-30 Alfred E. Tiefenbacher (GmbH & Co. KG) Process for preparing mirabegron enacarbil
CN113816864B (zh) * 2020-06-18 2024-03-29 南京正大天晴制药有限公司 一种(r)-2-羟基-n-[2-(4-氨基苯基)乙基]-2-苯乙胺的制备方法
CN114539084B (zh) * 2020-11-24 2024-04-02 威智医药股份有限公司 米拉贝隆及其中间体的制备方法
CN114539182B (zh) * 2020-11-24 2024-08-09 威智医药股份有限公司 转晶溶剂及其应用和米拉贝隆α晶型的制备方法
KR20220081033A (ko) 2020-12-08 2022-06-15 주식회사 한서켐 미라베그론 α형 결정의 제조방법
CN112574137A (zh) * 2021-01-19 2021-03-30 南京美瑞制药有限公司 一种α晶型米拉贝隆的制备方法
KR20240116208A (ko) 2023-01-20 2024-07-29 이니스트에스티 주식회사 결정형의 미라베그론 신규염, 이의 제조방법 및 이를 포함하는 약학적 조성물
US12097189B1 (en) 2024-02-09 2024-09-24 Astellas Pharma Inc. Pharmaceutical composition for modified release
WO2026064392A1 (en) 2024-09-17 2026-03-26 Flavostar Llc Fixed dose combination of flavoxate and beta-3 adrenergic receptor agonists, and formulations and manufacturing processes thereof

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1921577B2 (de) * 1969-04-28 1972-04-06 Nixdorf Computer Ag, 4790 Paderborn Trommelartige vorrichtung zn buchungs- und schreibautomaten mit greifeinrichtung zum erfassen und einziehen von kontokarten o dgl
JPH02279685A (ja) 1989-04-18 1990-11-15 Yoshitomi Pharmaceut Ind Ltd 新規な結晶構造を有するチアジアジン化合物およびその製造法
KR100519870B1 (ko) * 1997-01-23 2005-10-12 아스텔라스세이야쿠 가부시키가이샤 신규한 아미드 유도체 및 이를 함유하는 약제학적 조성물
KR100506568B1 (ko) * 1997-10-17 2006-04-21 아스텔라스세이야쿠 가부시키가이샤 아미드유도체및이의염,및이를포함하는약제학적제제
JP3901832B2 (ja) 1998-03-13 2007-04-04 大日本インキ化学工業株式会社 キノリノン誘導体製剤、及びその製造法
JP2000212168A (ja) 1999-01-22 2000-08-02 Yamanouchi Pharmaceut Co Ltd ヘキサヒドロ―１，４―ジアゼピン誘導体塩水和物の新規結晶
KR100602617B1 (ko) * 1999-09-10 2006-07-20 다이니혼 잉키 가가쿠 고교 가부시키가이샤 퀴놀리논 유도체 제제 및 그것의 제조 방법
US6706733B2 (en) * 2001-05-08 2004-03-16 Dainippon Ink And Chemicals, Inc. Quinolinone derivative formulation and its production method
US7342117B2 (en) * 2001-10-30 2008-03-11 Astellas Pharma Inc. α-form or β-form crystal of acetanilide derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016049749A1 (en) * 2014-10-01 2016-04-07 Apotex Inc. Solid forms of mirabegron

Also Published As

Publication number Publication date
HU230481B1 (hu) 2016-07-28
HUP0401665A3 (en) 2008-05-28
JPWO2003037881A1 (ja) 2005-02-17
PL369874A1 (en) 2005-05-02
KR100908796B1 (ko) 2009-07-22
ZA200403044B (en) 2005-06-29
CA2464068A1 (en) 2003-05-08
US20080214633A1 (en) 2008-09-04
BR0213570A (pt) 2004-10-26
HUP0401665A1 (hu) 2004-11-29
TW200300020A (en) 2003-05-01
ES2404071T3 (es) 2013-05-23
US7342117B2 (en) 2008-03-11
US20050004190A1 (en) 2005-01-06
NO326965B1 (no) 2009-03-23
BRPI0213570B1 (pt) 2018-02-27
PL218982B1 (pl) 2015-02-27
MXPA04003936A (es) 2004-06-18
RU2303033C2 (ru) 2007-07-20
KR100908796B9 (ko) 2024-07-17
AU2002344419B2 (en) 2007-12-13
JP3800220B2 (ja) 2006-07-26
CN1243740C (zh) 2006-03-01
BRPI0213570B8 (pt) 2021-05-25
US7982049B2 (en) 2011-07-19
EP1932838A3 (en) 2008-07-30
TWI322805B (enExample) 2010-04-01
EP2298752B1 (en) 2013-03-27
RU2004116313A (ru) 2005-03-27
EP1440969A1 (en) 2004-07-28
WO2003037881A1 (en) 2003-05-08
EP1440969A4 (en) 2005-01-19
NO20042227L (no) 2004-05-28
AU2002344419C1 (en) 2024-02-01
EP2298752A1 (en) 2011-03-23
CN1575287A (zh) 2005-02-02
KR20050040837A (ko) 2005-05-03
EP1932838A2 (en) 2008-06-18

Similar Documents

Publication Publication Date Title
US7982049B2 (en) α-form or β-form crystal of acetanilide derivative
JP5870220B2 (ja) ５−（｛［２−アミノ−３−（４−カルバモイル−２，６−ジメチル−フェニル）−プロピオニル］−［１−（４−フェニル−１ｈ−イミダゾール−２−イル）−エチル］−アミノ｝−メチル）−２−メトキシ−安息香酸の新規な結晶及び製造方法
EP2547649B1 (en) Agomelatine hydrochloride hydrate and preparation thereof
JP2008509953A (ja) ４−［［（７ｒ）−８−シクロペンチル−７−エチル−５，６，７，８−テトラヒドロ−５−メチル−４−６−オキソ−２−ピペリジニル］アミノ］−３−メトキシ−ｎ−（１−メチル−４−ピペリジニル）ベンズアミドの水和物及び多形、その製造方法、並びにその薬物としての使用
EP3322704B1 (en) Crystalline form of n-[(3-amino-3-oxetanyl)methyl]-2-(2,3-dihydro-1,1-dioxido-1,4-benzothiazepin-4(5h)-yl)-6-methyl-4-quinazolinamine for the treatment of respiratory syncytial virus (rsv) infections
US7141595B2 (en) Amino benzothiazole compounds with NOS inhibitory activity
TW202333739A (zh) 二肽基肽酶1抑制劑多晶型物及其製備方法和用途
JP4567889B2 (ja) （（アミノイミノメチル）アミノ）アルカンカルボキシアミドおよび治療におけるその適用
CN113683534A (zh) 甲磺酸卡莫司他及其溶剂化物的晶型和它们的制备方法和用途
CN109438388B (zh) 具有降糖作用化合物的晶型及制备方法和含其的组合物
US5041462A (en) Novel substituted acetamide compounds and use as anti-allergic agents
JPH01216980A (ja) アルキル―ピペラジニル―５，６―アルキレンピリミジン類
JP2010180169A (ja) アミド化合物の結晶
CN102321082A (zh) 萘啶酮羧酸类化合物及其制备方法

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20221031