JP3019235B2 - スフェロイド製剤 - Google Patents
スフェロイド製剤Info
- Publication number
- JP3019235B2 JP3019235B2 JP4234295A JP23429592A JP3019235B2 JP 3019235 B2 JP3019235 B2 JP 3019235B2 JP 4234295 A JP4234295 A JP 4234295A JP 23429592 A JP23429592 A JP 23429592A JP 3019235 B2 JP3019235 B2 JP 3019235B2
- Authority
- JP
- Japan
- Prior art keywords
- controlled release
- weight
- spheroid
- diltiazem
- release coating
- 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
Links
Classifications
-
- 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
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/501—Inorganic compounds
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5015—Organic compounds, e.g. fats, sugars
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
- A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fertilizers (AREA)
- Compounds Of Unknown Constitution (AREA)
Description
係る。特に、本発明はジルチアゼム(diltiaze
m)を含有する制御放出製剤に係る。
な慢性心臓疾患を治療するのに有用であることが認めら
れているカルシウムアンタゴニストである。
用として1日1回投与するのに適切な制御放出ジルチア
ゼム製剤を提供することである。
学的に許容可能な塩と、場合によりスフェロイド形成物
質とから構成され、制御放出層でコーティングされたス
フェロイドコアを含む制御放出組成物を提供する。
アゼムの薬学的に許容可能な塩は、薬学的に許容可能な
酸付加塩を含む。塩酸塩が特に好適である。
わたって薬剤をゆっくりと放出し、従来の薬剤よりも薬
剤作用時間を延長する組成物である。
用通り、0.1mm〜2.5mm、特に0.5mm〜2
mmの直径を有する球形顆粒を意味する。
アは、好ましくは40〜98重量%、より好ましくは6
0〜85重量%、特に70〜85重量%のジルチアゼム
又はその薬学的に許容可能な塩を含有する。
スフェロイド化してスフェロイドコアを形成し得る薬学
的に許容可能な任意の材料であり得る。。好適なスフェ
ロイド形成物質は微結晶セルロースである。使用される
微結晶セルロースは例えばAvicel PH 101
又はAvicel PH 102(登録商標、FMCコ
ーポレーション)であり得る。スフェロイド形成物質が
存在するとき、その配合量は通常スフェロイドコアの1
〜60重量%、好ましくは15〜40重量%である。
えばショ糖、ブドウ糖、麦芽糖又は乳糖)又は糖アルコ
ール類(例えばマンニトール、キシリトール又はソルビ
トール)のようにスフェロイド形成を助長する他の薬学
的に許容可能な賦形剤及び希釈剤も含有し得る。着色剤
もスフェロイドコアに含めてもよい。
れた速度でジルチアゼムを放出し得る材料でコーティン
グされている。適切な制御放出コーティング材料は、非
水溶性ワックス及びポリマー、例えばポリメタリレート
(例えばEudragitポリマー、登録商標)、又は
好ましくは非水溶性セルロース、特にエチルセルロース
など製薬業界で公知の材料を含む。コーティングは更に
ポリビニルピロリドンのような水溶性ポリマー、又は好
ましくはヒドロキシプロピルメチルセルロース及びヒド
ロキシプロピルセルロースのような水溶性セルロースも
含み得る。非水溶性材料と水溶性材料との比は、所要の
放出速度と選択された材料の溶解度とに依存する。水溶
性ポリマーと非水溶性ポリマーとの比は好ましくは1:
20〜1:2である。
界で慣用の1種以上の可塑剤(例えばジエチルフタレー
ト、特にセバシン酸ジブチル)、界面活性剤(例えばソ
ルビタントリオレエート、ソルビタンモノラウレート、
又は好ましくはポリソルベート80(Tween 8
0、登録商標))及び粘着調節剤(例えばタルク、又は
好ましくはコロイド無水シリカ)を含む。
される可塑剤の種類に依存する。一般に、可塑剤の配合
量は制御放出フィルムコートの1〜25重量%である。
界面活性剤が存在する場合、その配合量は制御放出フィ
ルムコートの1〜25重量%が適切である。粘着調節剤
が存在する場合、同様に制御放出フィルムコートの1〜
25重量%が適切である。
50〜95%のエチルセルロース、5〜15%のコロイ
ド無水シリカ、5〜15%のセバシン酸ジブチル及び5
〜15%のポリソルベート80(Tween80、登録
商標)を含有する。
ば流動床又はパンコーティングのような通常のコーティ
ング方法を使用して、ジルチアゼムを含むスフェロイド
コアの表面に形成され得る。コーティング材料は溶液又
は懸濁液として塗布され得る。適切な溶媒系は水、ジク
ロロメタン、エタノール、メタノール、イソプロピルア
ルコール及びアセトン又はその混合物を含む。コーティ
ング溶液又は懸濁液は好ましくは2〜60重量%、好ま
しくは2〜20重量%のコーティング材料を含有する。
出速度に依存するが、一般に組成物の1〜25重量%、
好ましくは2〜8重量%である。
アゼム又はその薬学的に許容可能な塩、水及び場合によ
りスフェロイド形成物質を含有する混合物を顆粒化し、
(b)顆粒化した混合物を押出して押出物を得、(c)
スフェロイドコアが形成されるまで押出物をスフェロイ
ド化し、(d)スフェロイドコアを乾燥させ、(e)ス
フェロイドコアをフィルムコーティングすることにより
製造され得る。
てカプセルもしくはサッシェに充填するか又はタブレッ
トに圧縮することができる。
切である。1日1回投与する場合、製剤は通常120m
g〜300mgのジルチアゼム又はその薬学的に許容可
能な塩、好ましくはジルチアゼム塩酸塩を含有する。
明する。
微結晶セルロースをブレンドした。混合物を湿潤顆粒化
し、押出し、スフェロイド状の押出物を得、流動床ドラ
イヤーで乾燥させた。スフェロイドを粒径0.85〜
1.7mmに篩別した。
ロロメタン/メタノール溶媒系に分散し、流動床コータ
ーでジルチアゼムスフェロイドコアに塗布した。得られ
たフィルムコートスフェロイドを篩別した。コートした
スフェロイドをゼラチンカプセルシェルに充填した。
ン酸緩衝液中100rpmでEPバスケット装置により
測定した。得られた結果を以下に記録する。
Claims (8)
- 【請求項1】 60〜98重量%のジルチアゼム又はそ
の薬学的に許容可能な塩と微結晶セルロースとから実質
的に成るスフェロイドコアを有し、前記スフェロイドコ
アが制御放出コーティング材料として1〜25重量%の
エチルセルロースでコーティングされていることを特徴
とする制御放出組成物。 - 【請求項2】 スフェロイドコアが70〜85重量%の
ジルチアゼム又はその薬学的に許容可能な塩を含有する
ことを特徴とする請求項1に記載の組成物。 - 【請求項3】 微結晶セルロースの配合量がスフェロイ
ドコアの15〜40重量%であることを特徴とする請求
項1または2に記載の組成物。 - 【請求項4】 制御放出コーティング材料が更に、1種
以上の可塑剤、界面活性剤及び粘着調節剤を含有するこ
とを特徴とする請求項1から3のいずれか一項に記載の
組成物。 - 【請求項5】 制御放出コーティングが50〜95%の
エチルセルロース、5〜15%のコロイド無水シリカ、
5〜15%のセバシン酸ジブチル及び5〜15%のポリ
ソルベート80を含有することを特徴とする請求項4に
記載の組成物。 - 【請求項6】 制御放出コーティング材料の配合量が組
成物の2〜8重量%であることを特徴とする請求項1か
ら5のいずれか一項に記載の組成物。 - 【請求項7】 請求項1から6のいずれか一項に記載の
制御放出コーティング材料被覆スフェロイドコアを含む
カプセル。 - 【請求項8】 請求項1から6のいずれか一項に記載の
組成物の製造方法であって、(a)ジルチアゼム及びそ
の薬学的に許容可能な塩、水及び微結晶セルロースを含
有する混合物を顆粒化する段階と、(b)顆粒化した混
合物を押出し、押出物を得る段階と、(c)スフェロイ
ドコアが形成されるまで押出物をスフェロイド化する段
階と、(d)スフェロイドコアを乾燥させる段階と、
(e)スフェロイドコアを制御放出コーティング材料で
コーティングする段階とを含むことを特徴とする方法。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB919117361A GB9117361D0 (en) | 1991-08-12 | 1991-08-12 | Oral dosage form |
GB9117361.7 | 1991-08-12 | ||
GB919122967A GB9122967D0 (en) | 1991-10-29 | 1991-10-29 | Pharmaceutical composition |
GB9122967.4 | 1991-10-29 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH05201867A JPH05201867A (ja) | 1993-08-10 |
JP3019235B2 true JP3019235B2 (ja) | 2000-03-13 |
Family
ID=26299395
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4234295A Expired - Lifetime JP3019235B2 (ja) | 1991-08-12 | 1992-08-10 | スフェロイド製剤 |
Country Status (14)
Country | Link |
---|---|
US (2) | US5670172A (ja) |
EP (1) | EP0527637B1 (ja) |
JP (1) | JP3019235B2 (ja) |
KR (1) | KR100221695B1 (ja) |
CN (1) | CN1052398C (ja) |
AT (1) | ATE165513T1 (ja) |
AU (1) | AU651715B2 (ja) |
CA (1) | CA2075356A1 (ja) |
DE (1) | DE69225278D1 (ja) |
ES (1) | ES2115643T3 (ja) |
FI (1) | FI923582A (ja) |
IL (1) | IL102778A (ja) |
NO (1) | NO304406B1 (ja) |
PH (1) | PH31288A (ja) |
Families Citing this family (92)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5266331A (en) * | 1991-11-27 | 1993-11-30 | Euroceltique, S.A. | Controlled release oxycodone compositions |
US5681585A (en) * | 1991-12-24 | 1997-10-28 | Euro-Celtique, S.A. | Stabilized controlled release substrate having a coating derived from an aqueous dispersion of hydrophobic polymer |
US20080075781A1 (en) * | 1992-11-25 | 2008-03-27 | Purdue Pharma Lp | Controlled release oxycodone compositions |
FR2702160B1 (fr) * | 1993-03-02 | 1995-06-02 | Biovecteurs As | Vecteurs particulaires synthétiques et procédé de préparation. |
SE9301220D0 (sv) * | 1993-04-14 | 1993-04-14 | Kabi Pharmacia Ab | Manufacturing matrices |
US20070275062A1 (en) * | 1993-06-18 | 2007-11-29 | Benjamin Oshlack | Controlled release oxycodone compositions |
US7740881B1 (en) | 1993-07-01 | 2010-06-22 | Purdue Pharma Lp | Method of treating humans with opioid formulations having extended controlled release |
IL110014A (en) * | 1993-07-01 | 1999-11-30 | Euro Celtique Sa | Solid controlled-release oral dosage forms of opioid analgesics |
US5834024A (en) | 1995-01-05 | 1998-11-10 | Fh Faulding & Co. Limited | Controlled absorption diltiazem pharmaceutical formulation |
GB9519363D0 (en) | 1995-09-22 | 1995-11-22 | Euro Celtique Sa | Pharmaceutical formulation |
US5914134A (en) * | 1997-01-27 | 1999-06-22 | Wockhardt Europe Limited | Process for the pulsatile delivery of diltiazem HCL and product produced thereby |
ES2232021T3 (es) * | 1997-09-09 | 2005-05-16 | Alza Corporation | Composicion para recubrimiento farmaceutico y procedimiento de utilizacion. |
US7060734B1 (en) | 1997-09-09 | 2006-06-13 | Alza Corporation | Pharmaceutical coating composition and method of use |
US5891845A (en) * | 1997-11-21 | 1999-04-06 | Fuisz Technologies Ltd. | Drug delivery systems utilizing liquid crystal structures |
BR9813826A (pt) * | 1997-12-22 | 2000-10-10 | Euro Celtique Sa | Potencial de uso abusivo de administração oral de opióide analgésico |
JP2001526228A (ja) | 1997-12-22 | 2001-12-18 | ユーロ−セルティーク,エス.エイ. | オピオイド作動薬/拮抗薬の併用 |
US6524620B2 (en) | 1998-07-20 | 2003-02-25 | Andrx Pharmaceuticals, Inc. | Diltiazem controlled release formulation and method of manufacture |
US6806294B2 (en) | 1998-10-15 | 2004-10-19 | Euro-Celtique S.A. | Opioid analgesic |
US6432448B1 (en) | 1999-02-08 | 2002-08-13 | Fmc Corporation | Edible coating composition |
US6723342B1 (en) | 1999-02-08 | 2004-04-20 | Fmc Corporation | Edible coating composition |
US6410255B1 (en) * | 1999-05-05 | 2002-06-25 | Aurora Biosciences Corporation | Optical probes and assays |
KR20060110013A (ko) | 1999-05-14 | 2006-10-23 | 니리어스 파마슈티컬즈, 인크. | 신규한 인터루킨-1 및 종양사멸인자-α의 조절인자들, 상기조절인자들의 합성 및 상기 조절인자들의 사용 방법 |
GB9913979D0 (en) | 1999-06-17 | 1999-08-18 | Univ Wales Medicine | Spheroid preparation |
EP2295043A1 (en) | 1999-10-29 | 2011-03-16 | Euro-Celtique S.A. | Controlled release hydrocodone formulations |
US10179130B2 (en) | 1999-10-29 | 2019-01-15 | Purdue Pharma L.P. | Controlled release hydrocodone formulations |
US6500462B1 (en) | 1999-10-29 | 2002-12-31 | Fmc Corporation | Edible MCC/PGA coating composition |
US7108866B1 (en) | 1999-12-10 | 2006-09-19 | Biovall Laboratories International Srl | Chronotherapeutic diltiazem formulations and the administration thereof |
US20060153914A1 (en) * | 1999-12-10 | 2006-07-13 | Biovail Laboratories International S.R.L. | Chronotherapeutic diltiazem formulations and the administration thereof |
WO2001058451A1 (en) | 2000-02-08 | 2001-08-16 | Euro-Celtique, S.A. | Tamper-resistant oral opioid agonist formulations |
DE60139544D1 (de) | 2000-02-23 | 2009-09-24 | Life Technologies Corp | Veränderte, fluoreszierende proteine |
US6852031B1 (en) * | 2000-11-22 | 2005-02-08 | Igt | EZ pay smart card and tickets system |
US6635277B2 (en) | 2000-04-12 | 2003-10-21 | Wockhardt Limited | Composition for pulsatile delivery of diltiazem and process of manufacture |
GB0025208D0 (en) * | 2000-10-13 | 2000-11-29 | Euro Celtique Sa | Delayed release pharmaceutical formulations |
AU2738302A (en) * | 2000-10-30 | 2002-05-15 | Euro Celtique Sa | Controlled release hydrocodone formulations |
US7144723B2 (en) * | 2000-11-16 | 2006-12-05 | The Regents Of The University Of California | Marine actinomycete taxon for drug and fermentation product discovery |
TR200300731T2 (tr) | 2000-11-28 | 2004-08-23 | Fmc Corporation | Yenebilir PGA kaplama bileşimi |
US20110104214A1 (en) | 2004-04-15 | 2011-05-05 | Purdue Pharma L.P. | Once-a-day oxycodone formulations |
UA81224C2 (uk) * | 2001-05-02 | 2007-12-25 | Euro Celtic S A | Дозована форма оксикодону та її застосування |
US20030065002A1 (en) | 2001-05-11 | 2003-04-03 | Endo Pharmaceuticals, Inc. | Abuse-resistant controlled-release opioid dosage form |
EP1416842B1 (en) | 2001-07-18 | 2008-12-31 | Euro-Celtique S.A. | Pharmaceutical combinations of oxycodone and naloxone |
WO2003013433A2 (en) | 2001-08-06 | 2003-02-20 | Euro-Celtique S.A. | Sequestered antagonist formulations |
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-
1992
- 1992-08-04 KR KR1019920013984A patent/KR100221695B1/ko not_active IP Right Cessation
- 1992-08-05 CA CA002075356A patent/CA2075356A1/en not_active Abandoned
- 1992-08-06 AU AU20880/92A patent/AU651715B2/en not_active Expired
- 1992-08-10 PH PH44791A patent/PH31288A/en unknown
- 1992-08-10 JP JP4234295A patent/JP3019235B2/ja not_active Expired - Lifetime
- 1992-08-10 IL IL10277892A patent/IL102778A/en not_active IP Right Cessation
- 1992-08-11 AT AT92307333T patent/ATE165513T1/de active
- 1992-08-11 DE DE69225278T patent/DE69225278D1/de not_active Expired - Lifetime
- 1992-08-11 ES ES92307333T patent/ES2115643T3/es not_active Expired - Lifetime
- 1992-08-11 EP EP92307333A patent/EP0527637B1/en not_active Expired - Lifetime
- 1992-08-11 FI FI923582A patent/FI923582A/fi unknown
- 1992-08-11 NO NO923128A patent/NO304406B1/no not_active IP Right Cessation
- 1992-08-12 CN CN92105698A patent/CN1052398C/zh not_active Expired - Lifetime
-
1995
- 1995-04-21 US US08/426,065 patent/US5670172A/en not_active Expired - Lifetime
-
1996
- 1996-06-18 US US08/666,636 patent/US5601845A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE69225278D1 (de) | 1998-06-04 |
EP0527637B1 (en) | 1998-04-29 |
NO923128L (no) | 1993-02-15 |
KR100221695B1 (ko) | 1999-09-15 |
JPH05201867A (ja) | 1993-08-10 |
FI923582A0 (fi) | 1992-08-11 |
PH31288A (en) | 1998-07-06 |
ATE165513T1 (de) | 1998-05-15 |
CN1069408A (zh) | 1993-03-03 |
ES2115643T3 (es) | 1998-07-01 |
NO304406B1 (no) | 1998-12-14 |
US5601845A (en) | 1997-02-11 |
FI923582A (fi) | 1993-02-13 |
IL102778A (en) | 1999-05-09 |
CN1052398C (zh) | 2000-05-17 |
KR930003906A (ko) | 1993-03-22 |
AU651715B2 (en) | 1994-07-28 |
CA2075356A1 (en) | 1993-02-13 |
IL102778A0 (en) | 1993-01-31 |
NO923128D0 (no) | 1992-08-11 |
US5670172A (en) | 1997-09-23 |
EP0527637A1 (en) | 1993-02-17 |
AU2088092A (en) | 1993-02-18 |
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