CN1212624A - 含有咪唑拉汀的缓释药物制剂 - Google Patents

含有咪唑拉汀的缓释药物制剂 Download PDF

Info

Publication number
CN1212624A
CN1212624A CN97192804A CN97192804A CN1212624A CN 1212624 A CN1212624 A CN 1212624A CN 97192804 A CN97192804 A CN 97192804A CN 97192804 A CN97192804 A CN 97192804A CN 1212624 A CN1212624 A CN 1212624A
Authority
CN
China
Prior art keywords
acid
mizolastine
release pharmaceutical
pharmaceutical formulation
sustained release
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
Application number
CN97192804A
Other languages
English (en)
Other versions
CN1112929C (zh
Inventor
M·查里奥特
G·勒维斯
J·蒙特尔
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.)
Sanofi Aventis France
Original Assignee
SYNTHETIC LABORATORY CORP
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
Application filed by SYNTHETIC LABORATORY CORP filed Critical SYNTHETIC LABORATORY CORP
Publication of CN1212624A publication Critical patent/CN1212624A/zh
Application granted granted Critical
Publication of CN1112929C publication Critical patent/CN1112929C/zh
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
    • A61K9/2806—Coating materials
    • A61K9/2833—Organic macromolecular compounds
    • A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin
    • A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/14—Decongestants or antiallergics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pulmonology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Immunology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

含有咪唑拉汀的缓释药物制剂,其特征在于该制剂包括由缓释药片构成的芯,该缓释药片含有与脂肪基料和有机酸配合的咪唑拉汀,所述的药片被涂敷。

Description

含有咪唑拉汀的缓释药物制剂
本发明涉及含有2-[[1-[1-[(4-氟苯基)甲基]-1H-苯并咪唑-2-基]哌啶-4-基]甲基氨基]嘧啶-4-醇或2-[[1-[1-[(4-氟苯基)甲基]-1H-苯并咪唑-2-基]哌啶-4-基]甲基氨基]嘧啶-4(1H)-酮或咪唑拉汀作为活性组分的新的缓释药物制剂。
咪唑拉汀(mizolastine)在欧洲专利EP 0217700中作过描述。
咪唑拉汀与组胺受体H1相结合，可在体外和体内抑制肥大细胞的去粒作用。因此，它可用来治疗呼吸、皮肤或眼的变态反应和各种变态反应症状。
当口服即刻释放的含有咪唑拉汀的制剂时，观察到不希望有的与存在高的血浆峰相关的镇静作用。
因此，必须寻找口服制剂，这些制剂具有的活性组分释放曲线能够达到不高的血浆峰又不降低生物利用率。
本申请人根据咪唑拉汀溶解动力学研究结果寻找过这样一些制剂。事实上，咪唑拉汀是一种弱碱(pK5.6)，它在水中不太溶解(在中性pH,13毫克/升)而在酸性pH溶解高得多(在pH3时11克/升)；头等胶囊剂在pH2溶解介质中在30分钟内释放100％咪唑拉汀，而在pH6.8仅溶解40％。
另外，由本发明的缓释药物形式释放咪唑拉汀不应受到胃-肠道中pH不同的影响。
本发明的目的是提供含有咪唑拉汀的制剂，其溶解曲线如下：
-在1小时溶解约30-70％咪唑拉汀，
-在3-5小时溶解100％咪唑拉汀，
-曲线与pH无关。
本申请人指出，包含一种由缓释药片构成的芯的片剂特别满意，而所述缓释药片含有与脂肪基料和有机酸配合的咪唑拉汀，所述药片被涂敷，以避免产品在光的作用下发生降解。
本发明的片剂含有1-25毫克咪唑拉汀。这些剂量相应于浓度为0.5-12％(重量)咪唑拉汀。
脂肪基料是用氢化蓖麻油或用氢化卵磷脂或长链脂肪酸(例如C12-C28脂肪酸，像山嵛酸)，或用如C8-C18脂肪酸之类的中等链的脂肪酸酯化的三甘油酯制备的。
有机酸的pK优选地等于或高于2，它可选自呈外消旋物或异构体状的马来酸、酒石酸、苹果酸、富马酸、乳酸、柠檬酸、己二酸、琥珀酸。根据本发明，特别优选的酸是L-酒石酸。
咪唑拉汀与有机酸的重量比应该是0.3-1。使用L-酒石酸时，这个比例优选地是等于0.5。
这些片剂可由活性组分、脂肪基料的组成剂、有机酸和其他赋形剂经制粒而制成，所述赋形剂例如像乳糖、甘露糖醇和蔗糖或类似的糖-醇、微晶纤维素、淀粉、磷酸钙和硫酸钙、聚乙烯吡咯烷酮、取代的纤维素，如羟丙基纤维素、羟丙基甲基纤维素或甲基纤维素。
可以例如在水或醇存在下以潮湿相进行制粒，或者采用熔融或采用压实制粒。制粒步骤可以任选地缩减，也可以采用直接压制咪唑拉汀和赋形剂的混合物制备片剂。
可以往所得到的颗粒中添加无水硅胶和硬脂酸镁，并压制该混合物。然后这些片在一种空气流化床设备中或者在涂敷涡轮机中通过喷洒涂层溶液而包一层涂层薄膜。
下述实施例说明本发明而不限制其保护范围：
片剂                ％(重量)
咪唑拉汀              4.8
氢化蓖麻油            12.0
乳糖                  60.0
微晶纤维素            9.6
L-酒石酸              9.6
聚乙烯吡咯烷酮        2.9
无水硅胶              0.2
硬脂酸镁              0.9
已纯化的水            适量
总量                  100.0
涂层液
甲基羟丙基纤维素      74.0
二氧化钛(E171)        18.5
丙二醇        7.5
已纯化的水    适量
总量         100.0
用本发明制剂所得到的溶解曲线示于图1中。
该曲线给出在1小时约50％产品溶解，在3-5小时100％产品溶解，其产品溶解与pH无关。
与本发明相同制剂但不含有L-酒石酸的溶解曲线示于图2。
与含有10毫克即刻释放的标准胶囊剂相比，研究过健康志愿者一次口服含有10毫克本发明药剂后的血浆动力学。
表1列出了动力学参数，而图3给出了分别用每个制剂得到的血浆动力学曲线；用本发明药物形式得到的血浆动力学能够避免任何血浆峰又不损失生物利用率。
还研究了与没有L-酒石酸的同样制剂相比的本发明药物形式的血浆动力学。
研究了十二位健康志愿者在一次口服含有10毫克咪唑拉汀的本发明片剂或没有L-酒石酸的同样片剂后的情况。
表2表明不含有L-酒石酸制剂的生物利用率仅仅是用含有L-酒石酸的本发明制剂所观察到的生物利用率的43％。含有L-酒石酸制剂的Cmax和AUC值(0-∞)比不含有L-酒石酸的制剂分别高1.5与2倍。
另外，对于含有L-酒石酸的制剂，极小-极大可变性指数小得多，这可认为释放非常有规律。
全部结果表明本发明的制剂具有：
-溶解曲线与pH无关，
-体内释放避免任何血浆蜂，
-与即刻释放的制剂相比生物利用率没有降低，
-血浆动力学结果可变性比较低。

Claims (7)

1、含有咪唑拉汀的缓释药物制剂，其特征在于该制剂包括由缓释药片构成的芯，该缓释片剂含有与脂肪基料和有机酸配合的咪唑拉汀，所述的药片被涂敷。
2、根据权利要求1所述的缓释药物制剂，其特征在于咪唑拉汀与有机酸的重量比是0.3-1。
3、根据权利要求1和2中任一权利要求所述的缓释药物制剂，其特征在于脂肪基料是用氢化蓖麻油或氢化卵磷脂或长链脂肪酸或用中等链脂肪酸酯化的三甘油酯制备的。
4、根据权利要求1-3中任一权利要求所述的缓释药物制剂，其特征在于有机酸选自呈外消旋体或异构体状的马来酸、酒石酸、苹果酸、富马酸、乳酸、柠檬酸、己二酸、琥珀酸。
5、根据权利要求1-4中任一权利要求所述的缓释药物制剂，其特征在于有机酸是L-酒石酸。
6、根据权利要求5所述的缓释药物制剂，其特征在于咪唑拉汀与L-酒石酸的比是0.5。
7、根据权利要求1-6中任一权利要求所述的缓释药物制剂，其特征在于它含有1-25毫克咪唑拉汀。
CN97192804A 1996-03-04 1997-02-28 含有咪唑拉汀的缓释药物制剂 Expired - Lifetime CN1112929C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR96/02662 1996-03-04
FR9602662A FR2745500B1 (fr) 1996-03-04 1996-03-04 Formulations pharmaceutiques a liberation prolongee contenant de la mizolastine

Publications (2)

Publication Number Publication Date
CN1212624A true CN1212624A (zh) 1999-03-31
CN1112929C CN1112929C (zh) 2003-07-02

Family

ID=9489799

Family Applications (1)

Application Number Title Priority Date Filing Date
CN97192804A Expired - Lifetime CN1112929C (zh) 1996-03-04 1997-02-28 含有咪唑拉汀的缓释药物制剂

Country Status (35)

Country Link
US (2) US6165507A (zh)
EP (1) EP0906101B1 (zh)
JP (2) JP2000512617A (zh)
KR (1) KR100369888B1 (zh)
CN (1) CN1112929C (zh)
AR (1) AR006082A1 (zh)
AT (1) ATE219365T1 (zh)
AU (1) AU725494B2 (zh)
BG (1) BG63451B1 (zh)
BR (1) BR9707827A (zh)
CA (1) CA2247405C (zh)
CO (1) CO4780020A1 (zh)
CY (1) CY2293B1 (zh)
CZ (1) CZ291418B6 (zh)
DE (1) DE69713505T2 (zh)
DK (1) DK0906101T3 (zh)
EE (1) EE03511B1 (zh)
ES (1) ES2177942T3 (zh)
FR (1) FR2745500B1 (zh)
HK (1) HK1017999A1 (zh)
HU (1) HU227472B1 (zh)
IL (1) IL126050A (zh)
IN (1) IN187739B (zh)
NO (1) NO315841B1 (zh)
NZ (1) NZ331947A (zh)
OA (1) OA10854A (zh)
PL (1) PL189813B1 (zh)
PT (1) PT906101E (zh)
RU (1) RU2173997C2 (zh)
SK (1) SK282112B6 (zh)
TR (1) TR199801574T2 (zh)
TW (1) TW491711B (zh)
UA (1) UA49004C2 (zh)
WO (1) WO1997032584A1 (zh)
ZA (1) ZA971830B (zh)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002087960A (ja) * 2000-07-14 2002-03-27 Toyama Chem Co Ltd 徐放性錠剤
EP1322158B1 (en) * 2000-10-02 2012-08-08 USV Ltd. Sustained release pharmaceutical compositions containing metformin and method of their production
US7052706B2 (en) 2001-06-08 2006-05-30 Nostrum Pharmaceuticals, Inc. Control release formulation containing a hydrophobic material as the sustained release agent
US20030181488A1 (en) * 2002-03-07 2003-09-25 Boehringer Ingelheim Pharma Gmbh & Co. Kg Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof
NZ542176A (en) * 2003-03-04 2007-12-21 Nostrum Pharmaceuticals Inc Control release formulation containing a hydrophobic material as the sustained release agent
DE10337697A1 (de) * 2003-08-16 2005-03-24 Boehringer Ingelheim Pharma Gmbh & Co. Kg Tablette enthaltend 3-[(2-{[4-(Hexyloxycarbonylamino-imino-methyl)-phenyl-amino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionsäure-ethylester oder dessen Salze
EP2309985B1 (en) 2008-07-28 2018-03-14 Takeda Pharmaceutical Company Limited Pharmaceutical composition
JP5744412B2 (ja) * 2010-03-26 2015-07-08 テバ製薬株式会社 フロセミド製剤
US20140179712A1 (en) 2012-12-21 2014-06-26 Astrazeneca Ab Pharmaceutical formulation of n-[5-[2-(3,5-dimethoxyphenyl)ethyl]-2h-pyrazol-3-yl]-4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]benzamide

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4364945A (en) * 1979-12-13 1982-12-21 Whittle Barry J Nasal composition for relieving nasal distress
US4421736A (en) * 1982-05-20 1983-12-20 Merrel Dow Pharmaceuticals Inc. Sustained release diethylpropion compositions
US4590062A (en) * 1984-04-16 1986-05-20 Tech Trade Corp. Dry direct compression compositions for controlled release dosage forms
FR2587029B1 (fr) * 1985-09-11 1987-10-30 Synthelabo Derives de benzimidazole, leur preparation et leur application en therapeutique
JPH0776172B2 (ja) * 1986-04-16 1995-08-16 藤沢薬品工業株式会社 マトリツクス錠
JPS62283926A (ja) * 1986-06-02 1987-12-09 Nippon Chemiphar Co Ltd 塩酸ニカルジピン持続性組成物
DE3812799A1 (de) * 1988-04-16 1989-10-26 Sanol Arznei Schwarz Gmbh Oral zu verabreichende pharmazeutische zubereitung mit kontrollierter wirkstofffreisetzung und verfahren zu deren herstellung
JP3195391B2 (ja) * 1991-11-14 2001-08-06 エスエス製薬株式会社 徐放性トラピジル錠
US5686105A (en) * 1993-10-19 1997-11-11 The Procter & Gamble Company Pharmaceutical dosage form with multiple enteric polymer coatings for colonic delivery
IT1264696B1 (it) * 1993-07-09 1996-10-04 Applied Pharma Res Forme farmaceutiche destinate alla somministrazione orale in grado di rilasciare sostanze attive a velocita' controllata e differenziata
JPH07112932A (ja) * 1993-08-27 1995-05-02 Mitsui Toatsu Chem Inc 徐放性医薬製剤

Also Published As

Publication number Publication date
TR199801574T2 (xx) 1998-11-23
HUP9902458A3 (en) 2002-11-28
ATE219365T1 (de) 2002-07-15
DE69713505T2 (de) 2003-02-13
CO4780020A1 (es) 1999-05-26
CA2247405C (en) 2004-04-20
WO1997032584A1 (fr) 1997-09-12
PL328763A1 (en) 1999-02-15
NZ331947A (en) 2000-03-27
JP2007182451A (ja) 2007-07-19
EP0906101B1 (fr) 2002-06-19
NO984035D0 (no) 1998-09-02
AU725494B2 (en) 2000-10-12
HUP9902458A2 (hu) 2000-05-28
FR2745500B1 (fr) 1998-04-03
SK282112B6 (sk) 2001-11-06
KR19990087387A (ko) 1999-12-27
BG102692A (en) 1999-04-30
IL126050A0 (en) 1999-05-09
CY2293B1 (en) 2003-07-04
EE03511B1 (et) 2001-10-15
TW491711B (en) 2002-06-21
NO984035L (no) 1998-10-22
AR006082A1 (es) 1999-08-11
UA49004C2 (uk) 2002-09-16
PL189813B1 (pl) 2005-09-30
IL126050A (en) 2004-05-12
HK1017999A1 (en) 1999-12-10
CA2247405A1 (en) 1997-09-12
AU1930097A (en) 1997-09-22
ES2177942T3 (es) 2002-12-16
DE69713505D1 (de) 2002-07-25
ZA971830B (en) 1997-09-04
FR2745500A1 (fr) 1997-09-05
DK0906101T3 (da) 2002-10-14
JP2000512617A (ja) 2000-09-26
SK121098A3 (en) 1999-01-11
PT906101E (pt) 2002-09-30
OA10854A (fr) 2003-02-05
RU2173997C2 (ru) 2001-09-27
US20050202089A1 (en) 2005-09-15
EP0906101A1 (fr) 1999-04-07
BR9707827A (pt) 1999-07-27
HU227472B1 (en) 2011-07-28
NO315841B1 (no) 2003-11-03
CN1112929C (zh) 2003-07-02
IN187739B (zh) 2002-06-15
EE9800275A (et) 1999-02-15
US6165507A (en) 2000-12-26
BG63451B1 (bg) 2002-02-28
CZ291418B6 (cs) 2003-03-12
KR100369888B1 (ko) 2003-05-17
CZ279198A3 (cs) 1999-01-13

Similar Documents

Publication Publication Date Title
KR101573889B1 (ko) 속효성과 지속성을 동시에 갖는 약제학적 조성물
US20030096791A1 (en) Taste masking of highly water-soluble drugs
US20060039968A1 (en) Gabapentin tablets and method for their preparation
AU2003245736A1 (en) Formulations of atorvastatin stabilized with alkali metal additions
EP1112738A2 (en) Stable extended release oral dosage composition comprising pseudoephedrine and desloratadine
CN1324233A (zh) 含有cGMP PDE－5抑制剂的控释药物制剂
MX2008015736A (es) Composiciones farmaceuticas estabilizadas que contienen fesoterodina.
CN1112929C (zh) 含有咪唑拉汀的缓释药物制剂
RU2401110C2 (ru) Препарат в форме пеллет с замедленным высвобождением для вертиго
EP1404304B1 (en) Tablet comprising cetirizine and pseudoephedrine
US20090269402A1 (en) Modified release composition of at least one form of venlafaxine
EP1473030B1 (en) Extended release Venlafaxine tablet formulation
WO2005077332A2 (en) Stable sustained-release oral dosage forms of gabapentin and process for preparation thereof
CN1832736A (zh) 加巴喷丁的稳定缓释口服剂型
US20220241222A1 (en) Atomoxetine hydrochloride extended release compositions and methods of use
KR20210012082A (ko) 미라베그론 및 탐스로신을 포함하는 약학 조성물
US5817336A (en) Composition containing selegiline
EA011579B1 (ru) Композиция с пролонгированным высвобождением венлафаксина
WO2005020978A1 (en) Sustained release oral tablets of gabapentin and process for their preparation
CA2654361A1 (en) Delayed-release compositions of extended release forms of venlafaxine
US20050074494A1 (en) Itraconazole immediate release formulation
EP1911441A2 (en) Controlled release color stable pharmaceutical dosage form of HMG-COA reductase inhibitors, free of alkalizing or buffering agents

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C53 Correction of patent of invention or patent application
COR Change of bibliographic data

Free format text: CORRECT: APPLICANT; FROM: SYNTHELABO TO: ST. SANOFI - SYNTHELABO CORPORATION

CP03 Change of name, title or address

Address after: France

Applicant after: Sanofi-Synthelabo

Address before: French Laixi - Luo Bansong Lepp

Applicant before: Synthetic Laboratory Corp.

C14 Grant of patent or utility model
GR01 Patent grant
C56 Change in the name or address of the patentee

Owner name: SANOFI - AVENTIS

Free format text: FORMER NAME OR ADDRESS: ST. SANOFI - SYNTHELABO CORPORATION

CP03 Change of name, title or address

Address after: France

Patentee after: Sanofi-Aventis

Address before: France

Patentee before: Sanofi-Synthelabo

CX01 Expiry of patent term
CX01 Expiry of patent term

Granted publication date: 20030702