JP5237522B2 - 改善された安定性を有する酸性インスリン調製物 - Google Patents
改善された安定性を有する酸性インスリン調製物 Download PDFInfo
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- JP5237522B2 JP5237522B2 JP2004512789A JP2004512789A JP5237522B2 JP 5237522 B2 JP5237522 B2 JP 5237522B2 JP 2004512789 A JP2004512789 A JP 2004512789A JP 2004512789 A JP2004512789 A JP 2004512789A JP 5237522 B2 JP5237522 B2 JP 5237522B2
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- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- 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
- A61P3/06—Antihyperlipidemics
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- 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
-
- 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
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- 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
- 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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- Engineering & Computer Science (AREA)
- Diabetes (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
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- Obesity (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Description
の類似体であり、これらは、少なくとも1個の天然アミノ酸残基が他のアミノ酸で置換されていること、そして/またはその他の点では同一の相当する天然インスリンに、またはそれから、少なくとも1個のアミノ酸残基が付加または除去されていることによって異なる。また、この場合のアミノ酸は天然に存在しないものであってもよい。
0 375 437およびEP 0 678 522に記載されている。EP 0 124 826は、特にB27およびB28の置換に関する。EP 0 678 522は、B29位に種々のアミノ酸、好ましくはプロリンを有するが、グルタミン酸を有さないインスリン類似体を記載している。
)(Brangeら,J.Ph.Sci 86:517−525(1997))。
常は医薬組成物中に100〜250mMの濃度で、NaClは150mMまでの濃度で存在する。例えばリン酸塩、酢酸塩、クエン酸塩、アルギニン、グリシルグリシンまたはTRIS(すなわち、2−アミノ−2−ヒドロキシメチル−1,3−プロパンジオール)緩衝剤および相当する塩のような緩衝物質は、5〜250mM、好ましくは10〜100mMの濃度で存在する。他の添加剤、特に塩またはアルギニンが存在していてもよい。
インスリン類似体が、Gly(A21)−Arg(B31)−Arg(B32)−ヒトインスリン;Lys(B3)−Glu(B29)−ヒトインスリン;LysB28ProB29ヒトインスリン、B28Asp−ヒトインスリン、B28位のプロリンがAsp、Lys、Leu、ValまたはAlaで置換されており、かつB29位のLysがProで置換されていてもよいヒトインスリン;AlaB26−ヒトインスリン;des(B28−B30)−ヒトインスリン;des(B27)−ヒトインスリンまたはdes(B30)−ヒトインスリンからなる群から選択される;
インスリン誘導体が、B29−N−ミリストイル−des(B30)ヒトインスリン、B29−N−パルミトイル−des(B30)ヒトインスリン、B29−N−ミリストイルヒトインスリン、B29−N−パルミトイルヒトインスリン、B28−N−ミリストイル−LysB28ProB29ヒトインスリン、B28−N−パルミトイル−LysB28ProB29ヒトインスリン、B30−N−ミリストイル−ThrB29LysB30ヒトインスリン、B30−N−パルミトイル−ThrB29LysB30ヒトインスリン、B29−N−(N−パルミトイル−γ−グルタミル)−des(B39)ヒトインスリン、B29−N−(N−リトコリル−γ−グルタミル)−des(B30)ヒトインスリン、B29−N−(ω−カルボキシヘプタデカノイル)−des(B30)ヒトインスリンおよびB29−N−(ω−カルボキシヘプタデカノイル)ヒトインスリンからなる群から選択される。
界面活性剤が、5〜200μg/ml、好ましくは5〜120μg/ml、特に好ましくは20〜75μg/mlの濃度で存在する、上記のような医薬製剤である。
1. 使用中の試験: 容器を折り返し蓋付き箱に入れ、28日の調査期間中+25℃および制御した室内湿度で遮光して貯蔵する。患者による投薬を模倣するために、普通のインスリンシリンジを用いて毎日1回、5IUの溶液を抜き取って捨てる。週末の投薬を模倣するために、この操作を実験週間の初めと終わりに2回行う。それぞれ抜き取る前に、容器中の溶液の肉眼評価を濁りおよび/または粒子形成について行う。
2. 振盪試験: インキュベーターおよびサーモスタットを有する実験室用振盪装置に載せた折り返し蓋付き箱に容器を入れ、25℃で水平運動に対して平行に90運動/分で10日の期間振盪する。所定の時間の後、サンプルの濁度を実験室用濁り光度計(比濁計)によりホルマールダジン比濁計単位(formaldazine nephelometric unit=FNU)で測定する。濁度は、サンプル中の懸濁粒子への入射光の散乱輻射の強度に相当する。
a)溶液を、0.2μmおよび0.1μmフィルターの組み合わせに通して滅菌濾過する。次いで、それを10ml注射バイアルに注ぎ、差込み密閉ディスクを有するクリンプキャップを用いて密封する。
b)比較溶液を同様に製造するが、最初に適量の界面活性剤(10〜30ppmのポリソルベート20)を注射用水に懸濁させる。
サンプルを+5℃、25℃および37℃で所定の時間貯蔵する。次いで、それぞれの場合に10個のサンプルを、使用中の試験に供する。結果を下記の表に示す。
a)溶液を、0.2μmおよび0.1μmフィルターの組み合わせに通して滅菌濾過する。次いで、それを10ml注射バイアルに注ぎ、差込み密閉ディスクを有するクリンプキャップを用いて密封する。
b)比較溶液を同様に製造するが、最初に適量の界面活性剤(0.010〜0.030mg/mlのポリソルベート20)を注射用水に懸濁させる。
サンプルを+5℃、25℃および37℃で所定の時間貯蔵する。次いで、それぞれの場合に5個のサンプルを振盪試験に供する。結果を下記の表に示す。限界15FNUは、日光で認識できる濁りに相当する。
それぞれの場合に10本のバイアルを開封して、5mlのインスリングラルギンの注射溶液とし、
a)0.001mg/mlのポリソルベート20を添加し、
b)0.01mg/mlのポリソルベート20を添加し、
c)0.001mg/mlのポリソルベート80を添加し、
d)0.01mg/mlのポリソルベート80を添加する。
次いで、サンプルを使用中の試験に供する。
結果を下記の表に示す
Claims (18)
- 240〜6000nmol/mlのGly(A21),Arg(B31),Arg(B32)−ヒトインスリン;
5〜75μg/mlの少なくとも1種の界面活性剤;
少なくとも1種の保存剤;および
水
を含む、医薬製剤であって、前記少なくとも1種の界面活性剤はポリソルベート20およびポリソルベート80からなる群から選択され、pH1〜4.5の酸性範囲のpHを有する医薬製剤。 - pH3.5〜4.5の酸性範囲のpHを有する、請求項1記載の医薬製剤。
- 少なくとも1種の界面活性剤が、ポリソルベート20である請求項1または2記載の医薬製剤。
- 少なくとも1種の保存剤が、フェノール、クレゾール、クロロクレゾール、ベンジルアルコールおよびパラベンからなる群から選択される請求項1〜3のいずれか1項に記載の医薬製剤。
- 少なくとも1種の保存剤がクレゾールである請求項4記載の医薬製剤。
- さらに少なくとも1種の等張化剤を含む請求項1〜5のいずれか1項に記載の医薬製剤。
- 少なくとも1種の等張化剤が、マンニトール、ソルビトール、ラクトース、デキストロース、トレハロース、塩化ナトリウムおよびグリセロールからなる群から選択される請求項6記載の医薬製剤。
- さらに緩衝剤を含む請求項1〜7のいずれか1項に記載の医薬製剤。
- 緩衝剤が、TRIS、リン酸塩、クエン酸塩、酢酸塩およびグリシルグリシンからなる群から選択される請求項8記載の医薬製剤。
- さらに酸、アルカリおよび塩からなる群から選択される1種またはそれより多くの添加剤を含む請求項1〜9のいずれか1項に記載の医薬製剤。
- Gly(A21),Arg(B31),Arg(B32)−ヒトインスリンが、240〜3000nmol/mlの濃度で存在する請求項1〜10のいずれか1項に記載の医薬製剤。
- 少なくとも1種の界面活性剤が、20〜75μg/mlの濃度で存在する請求項1〜11のいずれか1項に記載の医薬製剤。
- 少なくとも1種の等張化剤がグリセロールおよびマンニトールからなる群から選択され、前記少なくとも1種の等張化剤が100〜250mMの濃度で存在する請求項7記載の医薬製剤。
- 塩化ナトリウムが150mMまでの濃度で存在する請求項7記載の医薬製剤。
- 緩衝剤が、5〜250mMの濃度で存在する請求項8記載の医薬製剤。
- 少なくとも1種の界面活性剤がポリソルベート20であり、少なくとも1種の保存剤がクレゾールであり、そしてpH3.5〜4.5の酸性範囲のpHを有する、請求項1〜15のいずれか1項に記載の医薬製剤。
- 240〜6000nmol/mlのGly(A21),Arg(B31),Arg(B32)−ヒトインスリン;
5〜75μg/mlの少なくとも1種の界面活性剤;
少なくとも1種の保存剤;および
水
を含む、医薬製剤であって、前記少なくとも1種の界面活性剤はポリソルベートであり、pH1〜4.5の酸性範囲のpHを有する医薬製剤。 - 少なくとも1種の保存剤がクレゾールであり、そしてpH3.5〜4.5の酸性範囲のpHを有する、請求項17記載の医薬製剤。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10227232.8 | 2002-06-18 | ||
DE10227232A DE10227232A1 (de) | 2002-06-18 | 2002-06-18 | Saure Insulinzubereitungen mit verbesserter Stabilität |
PCT/EP2003/005887 WO2003105888A1 (de) | 2002-06-18 | 2003-06-05 | Saure insulinzubereitungen mit verbesserter stabilität |
Related Child Applications (1)
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JP2010232142A Division JP2011006492A (ja) | 2002-06-18 | 2010-10-15 | 改善された安定性を有する酸性インスリン調製物 |
Publications (2)
Publication Number | Publication Date |
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JP2005532365A JP2005532365A (ja) | 2005-10-27 |
JP5237522B2 true JP5237522B2 (ja) | 2013-07-17 |
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JP2004512789A Expired - Lifetime JP5237522B2 (ja) | 2002-06-18 | 2003-06-05 | 改善された安定性を有する酸性インスリン調製物 |
JP2010232142A Pending JP2011006492A (ja) | 2002-06-18 | 2010-10-15 | 改善された安定性を有する酸性インスリン調製物 |
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JP2010232142A Pending JP2011006492A (ja) | 2002-06-18 | 2010-10-15 | 改善された安定性を有する酸性インスリン調製物 |
Country Status (38)
Country | Link |
---|---|
US (4) | US20040048783A1 (ja) |
EP (2) | EP2305288B1 (ja) |
JP (2) | JP5237522B2 (ja) |
KR (1) | KR101040029B1 (ja) |
CN (2) | CN1662252A (ja) |
AR (1) | AR039688A1 (ja) |
AU (1) | AU2003238471B2 (ja) |
BR (1) | BRPI0311877B8 (ja) |
CA (1) | CA2490116C (ja) |
CR (1) | CR7614A (ja) |
CY (1) | CY1113537T1 (ja) |
DE (1) | DE10227232A1 (ja) |
DK (1) | DK1517697T3 (ja) |
EC (1) | ECSP045496A (ja) |
ES (2) | ES2397158T3 (ja) |
HN (1) | HN2003000184A (ja) |
HR (1) | HRP20041200B1 (ja) |
IL (1) | IL165788A (ja) |
MA (1) | MA27205A1 (ja) |
ME (1) | ME00180B (ja) |
MX (1) | MXPA04012233A (ja) |
MY (1) | MY142354A (ja) |
NO (1) | NO328567B1 (ja) |
NZ (1) | NZ537211A (ja) |
OA (1) | OA12870A (ja) |
PA (1) | PA8575701A1 (ja) |
PE (1) | PE20040560A1 (ja) |
PL (1) | PL208773B1 (ja) |
PT (2) | PT2305288T (ja) |
RS (1) | RS52388B (ja) |
RU (1) | RU2313362C2 (ja) |
SV (1) | SV2004001556A (ja) |
TN (1) | TNSN04249A1 (ja) |
TW (1) | TWI315201B (ja) |
UA (1) | UA79477C2 (ja) |
UY (1) | UY27854A1 (ja) |
WO (1) | WO2003105888A1 (ja) |
ZA (1) | ZA200409273B (ja) |
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DE10227232A1 (de) * | 2002-06-18 | 2004-01-15 | Aventis Pharma Deutschland Gmbh | Saure Insulinzubereitungen mit verbesserter Stabilität |
PT1740154E (pt) * | 2004-03-12 | 2009-09-11 | Biodel Inc | Composições de insulina com absorção melhorada |
US20080108787A1 (en) * | 2004-05-24 | 2008-05-08 | Maharaj K Sahib | Purification of Insulin-Like Material by Reverse Phase Chromatography |
UA75030C2 (en) * | 2005-11-30 | 2006-03-15 | Viktor Oleksandrovych Bykov | Method for obtaining stable aqueous solutions of drugs |
WO2007135117A2 (en) * | 2006-05-24 | 2007-11-29 | Novo Nordisk A/S | Soluble, stable insulin-containing formulations |
DE102006031955A1 (de) | 2006-07-11 | 2008-01-17 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von Insulinanaloga mit dibasischem B-Kettenende |
DE102006031962A1 (de) * | 2006-07-11 | 2008-01-17 | Sanofi-Aventis Deutschland Gmbh | Amidiertes Insulin Glargin |
WO2008132229A2 (en) * | 2007-04-30 | 2008-11-06 | Novo Nordisk A/S | Highly concentrated insulin solutions and compositions |
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CA2711749A1 (en) | 2008-01-09 | 2009-07-16 | Sanofi-Aventis Deutschland Gmbh | Novel insulin derivatives having an extremely delayed time-action profile |
NZ586589A (en) | 2008-01-09 | 2012-04-27 | Sanofi Aventis Deutschland | Novel insulin analogues having an extremely delayed time-action profile |
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WO2010028055A1 (en) * | 2008-09-02 | 2010-03-11 | Biodel, Inc. | Insulin with a basal release profile |
LT2349324T (lt) | 2008-10-17 | 2017-12-27 | Sanofi-Aventis Deutschland Gmbh | Insulino ir glp-1 agonisto derinys |
US9060927B2 (en) * | 2009-03-03 | 2015-06-23 | Biodel Inc. | Insulin formulations for rapid uptake |
MA33442B1 (fr) * | 2009-07-06 | 2012-07-03 | Sanofi Aventis Deutschland | Préparations d'insuline contenant de la méthionine |
PL2498801T3 (pl) | 2009-11-13 | 2018-08-31 | Sanofi Aventis Deutschland | Kompozycja farmaceutyczna zawierająca desPro<sup>36</sup>eksendyno-4(1-39)-Lys6-NH2 i metioninę |
ES2534191T3 (es) | 2009-11-13 | 2015-04-20 | Sanofi-Aventis Deutschland Gmbh | Composición farmacéutica que comprende un agonista de GLP-1, una insulina y metionina |
TW201138808A (en) | 2010-05-03 | 2011-11-16 | Bristol Myers Squibb Co | Serum albumin binding molecules |
US8637458B2 (en) | 2010-05-12 | 2014-01-28 | Biodel Inc. | Insulin with a stable basal release profile |
AU2011202239C1 (en) * | 2010-05-19 | 2017-03-16 | Sanofi | Long-acting formulations of insulins |
WO2011156476A2 (en) * | 2010-06-08 | 2011-12-15 | Biodel Inc. | Insulin with a basal release profile |
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- 2003-06-05 ME MEP-2008-287A patent/ME00180B/me unknown
- 2003-06-05 RS YU105704A patent/RS52388B/sr unknown
- 2003-06-05 PL PL372072A patent/PL208773B1/pl unknown
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- 2003-06-05 BR BRPI0311877A patent/BRPI0311877B8/pt active IP Right Grant
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