JP5670698B2 - イロペリドンの結晶を含有する注射用デポ製剤 - Google Patents
イロペリドンの結晶を含有する注射用デポ製剤 Download PDFInfo
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Description
本発明は、血漿への結晶成分の放出および吸収が結晶サイズに関連し得るイロペリドン(iloperidone)またはその代謝物の結晶を含む注射用デポ製剤に関する。
ポリ(d,l−ラクチド−コ−グリコリド)ミクロスフェアからの活性薬剤の制御された放出およびラクチド使用の一般的な現状は文献「L. M. Sanders et al., J. of Pharm. Sci., 73, No. 9, Sept. (1984); Controlled Release of a Luteininizing Hormone-Releasing Hormone Analogue from Poly(d,l-lactide-co-glycolide) Microspheres(黄体化ホルモン放出ホルモン誘導体のポリ(d,l−ラクチド−コ−グリコリド)ミクロスフェアからの制御された放出)」に記載されている。
本発明は平均粒子サイズ(X50値)が1〜200ミクロンである、イロペリドンまたはその代謝物またはその医薬上許容される塩、水和物、溶媒和物、多形体または立体異性体の結晶を含有する注射用デポ製剤を提供する。
イロペリドンは1−[4−[3−[4−(6−フルオロ−1,2−ベンズイソオキサゾール−3−イル)−1−ピペリジニル]プロポキシ]−3−メトシキフェニル]エタノンである。本明細書で使用する「イロペリドン」にはその塩、水和物、溶媒和物、無晶形物のような多形体および/または立体異性体も含まれる。イロペリドンの代謝物は1−[4−[3−[4−(6−フルオロ(d)イソオキサゾール−3−イル)ピペリジン−1−イル]プロポキシ]−3−メトシキフェニル]エタノールである。本明細書で使用する「イロペリドンの代謝物」には、その塩、水和物、溶媒和物、無晶形のような多形体および/または立体異性体のいずれも包含するものとする。
(R)エナンチオマーは構造式(III):
次式で示される1−[4−[3−[4−(6−フルオロ−1,2−ベンズイソオキサゾール−3−イル)−1−ピペリジニル]プロポキシ]−3−メトシキフェニル]エタノンの製造:
実施例1で製造した粒子サイズX50=32μmのイロペリドン結晶120mgをナトリウムカルボキシメチルセルロース、プルロニックス(Pluronics)F68およびマンニトールを含有する混合物1mL中で振盪して再構築し、均質な懸濁液を得た。この懸濁液をバイアルから注射器で吸い出し、ウサギに注射した。
実施例1で製造した粒子サイズX50=15μmのイロペリドン結晶850mgをナトリウムカルボキシメチルセルロース、プルロニックスF68およびマンニトールを含有する混合物2mL中で振盪または撹拌して再構築し、均質な懸濁液を得た。このペースト状懸濁液をバイアルから注射器で吸い出し、ウサギに注射した。
実施例1で製造した粒子サイズX50=51μmのイロペリドン結晶850mgカルボキシメチルセルロースナトリウム、プルロニックスF68およびマンニトールを含有する混合物2mL中で振盪して再構築し、均質な懸濁液を得た。この懸濁液をバイアルから注射器で吸い出し、ウサギに注射した。
図面に関して、図3はX50値16ミクロンおよび30ミクロンを持つイロペリドン結晶デポ製剤の雌性ウサギにおける平均血漿中濃度の所定時間にわたるグラフである。製剤は各ウサギkgあたりイロペリドン20mgになるように用量を標準化した。各製剤をウサギ6匹に注射した。図3はX50=16ミクロンを持つイロペリドン結晶を用いて調製したデポ製剤はウサギ血漿中に少なくとも16日間残存したことを示す。X50値=30ミクロンを持つイロペリドン結晶で調製したデポ製剤はウサギの血漿中に少なくとも25日間残存した。血漿中のイロペリドンの薬動力学的パラメータで標準化した平均用量を各結晶サイズについて表Iに要約する。
図面に関して、図4はX50値170ミクロンを持つイロペリドン結晶デポ製剤の雌性ウサギにおける平均血漿中濃度の所定時間にわたるグラフである。製剤は各ウサギの体重kgあたりイロペリドン20mgになるように用量を標準化した。各製剤をウサギ6匹に注射した。図4はX50=170ミクロンを持つイロペリドン結晶で調製したデポ製剤はウサギ血漿中に少なくとも30日間残留することを示す。血漿中のイロペリドンの薬動力学パラメータに標準化した平均用量を表IIに示す。
(i)この結晶の血漿中への放出を結晶サイズに相関させることができること;
(ii)この結晶の血漿中への吸収を結晶サイズに相関させることができること;
(iii)この結晶の粒子サイズを結晶化技術および/または粉砕で制御できること;および
(iv)この結晶は保存に対して安定であり、またガンマ線照射のような滅菌操作に対して安定である。
Claims (21)
- 1回注射により患者に投与するための注射用デポ製剤の製造方法であって、イロペリドンと酢酸ブチルの溶液にイロペリドン種晶を添加し、
得られたイロペリドン結晶を回収し、そして
100〜750mgのイロペリドンの結晶を水性媒体に懸濁させる
ことを含み、ここで、該結晶のX 50 値が16〜170ミクロンである、方法。 - 該製剤が、精神疾患の患者に対して皮下または筋肉内注射により投与後、2〜8週間にわたってイロペリドンの有効な処置量を提供する、請求項1に記載の方法。
- 得られたイロペリドン結晶が回収前に16〜170ミクロンのX50値に成長する、請求項1に記載の方法。
- 得られたイロペリドンを懸濁前に16〜170ミクロンのX50値とするためにさらに粉砕または製粉する、請求項1に記載の方法。
- 結晶が針状晶、三方晶、正方晶、平板な棒状晶、立方体晶、平行六面体晶および板状針状晶から構成される群から選択される形態である、請求項1〜8のいずれかに記載の方法。
- 結晶のX50値が16〜70ミクロンである、請求項1〜9のいずれかに記載の方法。
- 注射用デポ製剤にさらに追加的成分を添加することを含み、該追加的成分が界面活性剤、溶解剤、乳化剤、保存剤、等張剤、分散剤、湿潤剤、充填剤、溶媒、緩衝剤、安定化剤、滑沢剤、濃稠化剤およびこれらの組み合わせから構成される群から選択される、請求項1〜10のいずれかに記載の方法。
- 界面活性剤がソルビタンの脂肪酸エステル、ホスファチド、ポリオキシエチル化ソルビタンモノオレエート、プロピレングリコールのポリオキシアルキレン誘導体、ポリオキシエチル化脂肪、ポリオキシエチル化オレオトリグリセリド、リノル化オレオトリグリセリド、ポリエチレンオキシドと脂肪アルコールとの縮合物およびアルキルフェノールから構成される群から選択される、請求項11に記載の方法。
- 界面活性剤がプロピレングリコールのポリオキシアルキレン誘導体である、請求項12に記載の方法。
- 界面活性剤の濃度が0.5〜10mg/mLの範囲内にある、請求項11〜13のいずれかに記載の方法。
- 濃稠化剤がカルボキシメチルセルロースナトリウム、ヒドロキシプロピルセルロース、カルボキシメチルセルロースカルシウムおよび交差結合カルボキシメチルセルロースから構成される群から選択される、請求項11に記載の方法。
- 濃稠化剤がカルボキシメチルセルロースナトリウムである、請求項15に記載の方法。
- 濃稠化剤の濃度が2〜25mg/mLの範囲内である、請求項11、15または16のいずれかに記載の方法。
- 等張剤が塩類および糖類から構成される群から選択される、請求項11に記載の方法。
- 等張剤が塩類であり塩化ナトリウムであるかまたは糖でありデキストロース、マンニトールまたは乳糖である、請求項18に記載の方法。
- 等張剤がマンニトールである、請求項18に記載の方法。
- 水性媒体が水である、請求項1〜20のいずれかに記載の方法。
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GBGB0216416.8A GB0216416D0 (en) | 2002-07-15 | 2002-07-15 | Organic compounds |
GB0216416.8 | 2002-07-15 |
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JP2010236087A Expired - Lifetime JP5670698B2 (ja) | 2002-07-15 | 2010-10-21 | イロペリドンの結晶を含有する注射用デポ製剤 |
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US (5) | US20050250813A1 (ja) |
EP (1) | EP1523335B1 (ja) |
JP (2) | JP5392961B2 (ja) |
AT (1) | ATE348635T1 (ja) |
AU (1) | AU2003281154B2 (ja) |
CA (1) | CA2492467C (ja) |
CY (1) | CY1106305T1 (ja) |
DE (1) | DE60310564T2 (ja) |
DK (1) | DK1523335T3 (ja) |
ES (1) | ES2279153T3 (ja) |
GB (1) | GB0216416D0 (ja) |
HK (1) | HK1076029A1 (ja) |
NZ (1) | NZ537598A (ja) |
PT (1) | PT1523335E (ja) |
WO (1) | WO2004006886A2 (ja) |
ZA (1) | ZA200410323B (ja) |
Families Citing this family (44)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003037337A1 (en) | 2001-10-30 | 2003-05-08 | Novartis Ag | Depot formulations of iloperidone and a star polymer |
GB0216416D0 (en) * | 2002-07-15 | 2002-08-21 | Novartis Ag | Organic compounds |
JP4836797B2 (ja) | 2003-10-23 | 2011-12-14 | 大塚製薬株式会社 | 放出制御性無菌注射アリピプラゾール製剤および方法 |
CA3113166A1 (en) | 2004-09-30 | 2006-04-13 | Vanda Pharmaceuticals Inc. | Methods for the administration of iloperidone |
EP2029136A4 (en) | 2006-05-22 | 2010-01-06 | Vanda Pharmaceuticals Inc | TREATMENT FOR DEPRESSION DISEASES |
WO2008128166A1 (en) * | 2007-04-13 | 2008-10-23 | Concert Pharmaceuticals Inc. | Deuterated derivatives of 4-(6-fluoro-1, 2-benzisoxazol-3-yl) piperidine compounds |
DK2170279T3 (en) | 2007-07-31 | 2018-03-12 | Otsuka Pharma Co Ltd | PROCEDURES FOR PREPARING AN ARIPIPRAZOL SUSPENSION AND A FREEZER DRIED FORMULATION |
CA2698534C (en) | 2007-09-10 | 2018-10-09 | Vanda Pharmaceuticals, Inc. | Prediction of qt prolongation based on snp genotype |
SI2222300T1 (sl) | 2007-12-13 | 2014-11-28 | Vanda Pharmaceuticals Inc. | Postopek in sestavek za zdravljenje stanja, posredovanega z receptorjem serotonina |
JP5729808B2 (ja) | 2007-12-13 | 2015-06-03 | ヴァンダ ファーマシューティカルズ インコーポレイテッド | αアドレナリン受容体介在状態を治療する方法及び組成物 |
WO2010031497A1 (en) * | 2008-09-19 | 2010-03-25 | Miklos Vertessy | New process for the preparation of iloperidone |
CN101822673B (zh) * | 2009-03-04 | 2013-09-18 | 北京德众万全药物技术开发有限公司 | 一种含有伊潘立酮的固体药物组合物 |
WO2011009102A1 (en) | 2009-07-16 | 2011-01-20 | Vanda Pharmaceuticals Inc. | Use of a melatonin agonist for the treatment of sleep disorders including primary insomnia |
EP2479176B1 (en) * | 2009-09-19 | 2014-09-17 | Zhejiang Huahai Pharmaceutical Co., Ltd. | Method for preparation of iloperidone and crystallization method thereof |
CN102030744B (zh) * | 2009-09-30 | 2013-04-17 | 天津药物研究院 | 伊潘立酮晶体、其制备方法及药物组合物 |
WO2011055188A1 (en) * | 2009-11-05 | 2011-05-12 | Orchid Chemicals And Pharmaceuticals Limited | An improved process for the preparation of iloperidone |
MX2012007365A (es) * | 2009-12-23 | 2012-08-15 | Lupin Ltd | Composiciones farmaceuticas de liberacion lenta de iloperidona. |
CN102108081A (zh) * | 2009-12-25 | 2011-06-29 | 重庆医药工业研究院有限责任公司 | 伊潘立酮的新晶型及其制备方法 |
SG10201502588UA (en) | 2010-01-11 | 2015-05-28 | Inotek Pharmaceuticals Corp | Combination, kit and method of reducing intraocular pressure |
JP2013523739A (ja) | 2010-03-26 | 2013-06-17 | イノテック ファーマシューティカルズ コーポレイション | N6−シクロペンチルアデノシン(cpa)、cpa誘導体またはそれらのプロドラッグを用いてヒトにおける眼内圧を低下させる方法 |
CN101822674B (zh) * | 2010-05-27 | 2015-03-11 | 北京德众万全医药科技有限公司 | 一种伊潘立酮药物组合物及其制备方法 |
CN107595771A (zh) * | 2010-10-18 | 2018-01-19 | 大日本住友制药株式会社 | 注射用缓释制剂 |
WO2012063269A2 (en) | 2010-11-12 | 2012-05-18 | Cadila Healthcare Limited | Process for preparing iloperidone |
WO2012090138A1 (en) | 2010-12-27 | 2012-07-05 | Ranbaxy Laboratories Limited | Processes for the preparation of iloperidone |
CN102680636A (zh) * | 2011-03-11 | 2012-09-19 | 天津药物研究院 | 一种伊潘立酮原料药及其中间体的质量控制方法 |
SG11201403979TA (en) | 2012-01-26 | 2014-08-28 | Inotek Pharmaceuticals Corp | Anhydrous polymorphs of (2r,3s,4r,5r)-5-(6-(cyclopentylamino)-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl) } methyl nitrate and processes of preparation thereof |
CA2861111C (en) | 2012-01-26 | 2021-11-23 | Vanda Pharmaceuticals Inc. | Treatment of circadian rhythm disorders |
US11918557B2 (en) | 2012-01-26 | 2024-03-05 | Vanda Pharmaceuticals Inc. | Treatment of circadian rhythm disorders |
CN102633786B (zh) * | 2012-04-18 | 2013-11-27 | 吉林三善恩科技开发有限公司 | 一种伊潘立酮药物共晶及其制备方法 |
CN102659771B (zh) * | 2012-04-18 | 2013-11-27 | 吉林三善恩科技开发有限公司 | 一种伊潘立酮药物共晶及其制备方法 |
CA2872324C (en) | 2012-05-18 | 2017-06-06 | Vanda Pharmaceuticals Inc. | Metabolites of (1r-trans)-n-[[2-(2,3-dihydro-4-benzofuranyl)cyclopropyl]methyl]propanamide |
ES2805376T3 (es) | 2012-12-18 | 2021-02-11 | Vanda Pharmaceuticals Inc | Tasimelteón para el tratamiento de trastornos del ritmo circadiano |
EP2968389A4 (en) | 2013-03-15 | 2016-08-24 | Inotek Pharmaceuticals Corp | OPHTHALMIC FORMULATIONS |
US11090285B2 (en) | 2013-11-12 | 2021-08-17 | Vanda Pharmaceuticals Inc | Treatment of circadian rhythm disorders |
US10376487B2 (en) | 2013-11-12 | 2019-08-13 | Vanda Pharmaceuticals Inc. | Method of treatment |
CN103599074A (zh) * | 2013-11-26 | 2014-02-26 | 重庆医药工业研究院有限责任公司 | 一种伊潘立酮缓释微球及其制备方法 |
KR20170118830A (ko) | 2015-02-17 | 2017-10-25 | 반다 파마슈티칼즈, 인코퍼레이티드. | 조현병의 치료를 위한 일로페리돈 |
US11071728B2 (en) | 2015-12-11 | 2021-07-27 | Vanda Pharmaceuticals Inc. | Treatment of schizophrenia |
CN106831741B (zh) * | 2016-12-28 | 2019-08-23 | 北京医药集团有限责任公司 | 一种伊潘立酮超细粉体的制备方法 |
US10935106B2 (en) * | 2018-06-14 | 2021-03-02 | Serapid, Inc. | Block chain with monolithic links |
US20200171018A1 (en) * | 2018-12-04 | 2020-06-04 | Vanda Pharmaceuticals Inc. | Depot administration of iloperidone |
JP2022510454A (ja) * | 2018-12-04 | 2022-01-26 | バンダ・ファーマシューティカルズ・インコーポレイテッド | イロペリドンの持効性投与 |
US11607408B2 (en) | 2019-10-15 | 2023-03-21 | Vanda Pharmaceuticals Inc. | Method of treatment of schizophrenia |
WO2024137439A1 (en) | 2022-12-19 | 2024-06-27 | Vanda Pharmaceuticals Inc. | Dosage regime of iloperidone for treating bipolar i disorder and schizophrenia |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB216416A (en) | 1923-09-06 | 1924-05-29 | James Baker And Sons Ltd | Improvements in boots and shoes |
IT1093097B (it) * | 1976-10-28 | 1985-07-19 | Hoechst France | Acidi n-carbetossi(alfa-amminofenilacetici)otticamente attivi relativo procedimento di produzione e loro impiego per la produzione di acidi alfa-ammino-fenilacetici otticamente attivi corrispondenti |
CH656884A5 (de) | 1983-08-26 | 1986-07-31 | Sandoz Ag | Polyolester, deren herstellung und verwendung. |
DE3345355A1 (de) * | 1983-12-15 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | Verfahren zur racematspaltung bicyclischer imino-(alpha)-carbonsaeureester |
DE3511587A1 (de) * | 1985-03-27 | 1986-10-02 | Schering AG, Berlin und Bergkamen, 1000 Berlin | Glykoester des estradiols und estriols |
US4886370A (en) | 1987-08-25 | 1989-12-12 | Nkk Corporation | Method for detecting a state of substance existing in pipe |
US5776963A (en) | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
US5364866A (en) | 1989-05-19 | 1994-11-15 | Hoechst-Roussel Pharmaceuticals, Inc. | Heteroarylpiperidines, pyrrolidines and piperazines and their use as antipsychotics and analetics |
ES2076253T3 (es) * | 1989-05-19 | 1995-11-01 | Hoechst Roussel Pharma | N-(ariloxialquil)-heteroarilpiperidinas y -heteroarilpiperazinas, un procedimiento para su preparacion y su uso como medicamentos. |
US5538739A (en) | 1989-07-07 | 1996-07-23 | Sandoz Ltd. | Sustained release formulations of water soluble peptides |
MX9203319A (es) * | 1990-06-04 | 1992-07-31 | Schering Corp | Metodo para la preparacion de cristales de alfa-2 interferona. |
CA2095499A1 (en) * | 1992-05-08 | 1993-11-09 | Petrus J. M. Van Den Oetelaar | Depot preparation |
DK0669128T3 (da) * | 1992-11-17 | 2000-06-19 | Yoshitomi Pharmaceutical | Sustained-release mikrosfære indeholdende antipsykotikum og fremgangsmåde til at fremstille samme |
SK282231B6 (sk) | 1993-11-19 | 2001-12-03 | Janssen Pharmaceutica N. V. | Farmaceutický prostriedok na liečenie psychotických porúch |
US5902882A (en) * | 1996-04-17 | 1999-05-11 | Hoffmann-La Roche Inc. | Assymetric synthesis of azepines |
TW487572B (en) * | 1996-05-20 | 2002-05-21 | Janssen Pharmaceutica Nv | Aqueous suspensions of 9-hydroxyrisperidone fatty acid esters |
HUP0002106A3 (en) * | 1997-05-26 | 2001-11-28 | Akzo Nobel Nv | Aromatic sulfonates of trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz-[2,3:6,7]oxepino[4,5-c]pyrrole and pharmaceutical compositions containing it |
UA72189C2 (uk) * | 1997-11-17 | 2005-02-15 | Янссен Фармацевтика Н.В. | Фармацевтична композиція, що містить водну суспензію субмікронних ефірів 9-гідроксирисперидон жирних кислот |
US5955459A (en) * | 1997-11-26 | 1999-09-21 | Neuromedica, Inc. | Fatty acid-antipsychotic compositions and uses thereof |
US6541606B2 (en) * | 1997-12-31 | 2003-04-01 | Altus Biologics Inc. | Stabilized protein crystals formulations containing them and methods of making them |
DE19816070A1 (de) | 1998-04-09 | 1999-10-14 | Aventis Res & Tech Gmbh & Co | Retardtablette hergestellt aus linearen wasserunlöslichen Polysacchariden |
CA2345767A1 (en) | 1998-10-16 | 2000-04-27 | Paul Leonce Irma De Nijs | Therapy for improving cognition |
US6509310B1 (en) | 2000-06-01 | 2003-01-21 | Huish Detergents, Inc. | Compositions containing α-sulfofatty acid esters and method of making the same |
AU2001263775A1 (en) | 2000-06-02 | 2001-12-11 | Novo-Nordisk A/S | Glucose dependent release of insulin from glucose sensing insulin derivatives |
DK2305656T3 (da) * | 2001-08-31 | 2013-02-11 | Novartis Ag | Optiske isomerer of en iloperidonmetabolit |
WO2003037337A1 (en) * | 2001-10-30 | 2003-05-08 | Novartis Ag | Depot formulations of iloperidone and a star polymer |
GB0216416D0 (en) | 2002-07-15 | 2002-08-21 | Novartis Ag | Organic compounds |
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CY1106305T1 (el) | 2011-10-12 |
HK1076029A1 (en) | 2006-01-06 |
US20050250813A1 (en) | 2005-11-10 |
DE60310564T2 (de) | 2007-10-04 |
JP2011016849A (ja) | 2011-01-27 |
WO2004006886A3 (en) | 2004-02-19 |
US8227488B2 (en) | 2012-07-24 |
CA2492467C (en) | 2010-03-16 |
DK1523335T3 (da) | 2007-01-29 |
GB0216416D0 (en) | 2002-08-21 |
EP1523335A2 (en) | 2005-04-20 |
US20090099232A1 (en) | 2009-04-16 |
US20120156264A1 (en) | 2012-06-21 |
ZA200410323B (en) | 2006-06-28 |
DE60310564D1 (de) | 2007-02-01 |
JP5392961B2 (ja) | 2014-01-22 |
PT1523335E (pt) | 2007-02-28 |
US8614232B2 (en) | 2013-12-24 |
US8293765B2 (en) | 2012-10-23 |
WO2004006886A2 (en) | 2004-01-22 |
AU2003281154B2 (en) | 2006-10-12 |
ATE348635T1 (de) | 2007-01-15 |
EP1523335B1 (en) | 2006-12-20 |
AU2003281154A1 (en) | 2004-02-02 |
US20130012542A1 (en) | 2013-01-10 |
JP2005533093A (ja) | 2005-11-04 |
US20110212141A1 (en) | 2011-09-01 |
ES2279153T3 (es) | 2007-08-16 |
NZ537598A (en) | 2006-07-28 |
CA2492467A1 (en) | 2004-01-22 |
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