DE3536896C2 - Lyophilisiertes, ein Anthracyclinglycosid enthaltendes pharmazeutisches Präparat und Verfahren zur Herstellung einer sterilen injizierbaren Lösung hieraus - Google Patents
Lyophilisiertes, ein Anthracyclinglycosid enthaltendes pharmazeutisches Präparat und Verfahren zur Herstellung einer sterilen injizierbaren Lösung hierausInfo
- Publication number
- DE3536896C2 DE3536896C2 DE3536896A DE3536896A DE3536896C2 DE 3536896 C2 DE3536896 C2 DE 3536896C2 DE 3536896 A DE3536896 A DE 3536896A DE 3536896 A DE3536896 A DE 3536896A DE 3536896 C2 DE3536896 C2 DE 3536896C2
- Authority
- DE
- Germany
- Prior art keywords
- doxorubicin
- preparation according
- acid
- lyophilized preparation
- anthracycline glycoside
- 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
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- 231100000614 poison Toxicity 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 208000013077 thyroid gland carcinoma Diseases 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 239000011123 type I (borosilicate glass) Substances 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 description 1
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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- 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
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- 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
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- 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
-
- 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
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MYPI88001588A MY103956A (en) | 1984-10-22 | 1988-12-30 | Pharmaceutical compositions containing anthracycline glycosides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848426672A GB8426672D0 (en) | 1984-10-22 | 1984-10-22 | Pharmaceutical compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3536896A1 DE3536896A1 (de) | 1986-04-24 |
| DE3536896C2 true DE3536896C2 (de) | 1996-11-14 |
Family
ID=10568553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3536896A Expired - Lifetime DE3536896C2 (de) | 1984-10-22 | 1985-10-16 | Lyophilisiertes, ein Anthracyclinglycosid enthaltendes pharmazeutisches Präparat und Verfahren zur Herstellung einer sterilen injizierbaren Lösung hieraus |
Country Status (35)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5124318A (en) * | 1985-08-02 | 1992-06-23 | Farmitalia Carlo Erba S.R.L. | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| US5124317A (en) * | 1985-08-02 | 1992-06-23 | Farmitalia Carlo Erba S.P.A. | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| US5977082A (en) * | 1985-08-02 | 1999-11-02 | Pharmacia & Upjohn Company | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| DE3741037A1 (de) * | 1986-12-05 | 1988-06-09 | Erba Farmitalia | Injizierbare, gebrauchsfertige loesungen, welche ein antitumor-anthracyclinglycosid enthalten |
| JP2603480B2 (ja) * | 1987-08-05 | 1997-04-23 | 住友製薬株式会社 | 安定化されたアンスラサイクリン系製剤 |
| DE3801178A1 (de) * | 1988-01-18 | 1989-07-27 | Hoechst Ag | Stabilisierte trockenzubereitung zytostatisch wirksamer anthracyclin-antibiotika und verfahren zu ihrer herstellung |
| US6300362B1 (en) | 1990-07-25 | 2001-10-09 | Novartis Ag (Formerly Sandoz Ltd.) | Stabilized pharmaceutical compositions comprising acid donors |
| DE69737510T2 (de) | 1996-12-30 | 2007-12-06 | Battelle Memorial Institute, Columbus | Verwendung eines unverkapselten Antikrebs-Arzneimittels zur Herstellung einer Zubereitung zur Behandlung von Neoplasmen durch Inhalation |
| US5942508A (en) * | 1997-02-04 | 1999-08-24 | Senju Pharmaceutical Co., Ltd. | Method for solubilizing pyridonecarboxylic acid solubilizer thereof and aqueous solution containing solubilized pyridonecarboxylic acid |
| RU2292216C2 (ru) * | 2000-10-31 | 2007-01-27 | Фарма Мар, С.А. | Кахалалид f |
| KR100970528B1 (ko) | 2002-02-22 | 2010-07-16 | 쉐링 코포레이션 | 항신생물제, 특히 테모졸로마이드의 약제학적 제형, 이의제조 및 사용 방법 |
| DK1474995T3 (da) * | 2003-05-06 | 2013-02-18 | Gumlink As | Fremgangsmåde til fremstilling af tyggegummigranulater, et gummisammensætningsekstruder- og granuleringssystem og et tyggegummiprodukt |
| US20090099346A1 (en) * | 2003-07-02 | 2009-04-16 | Victor Matvienko | Thermally stable crystalline epirubicin hydrochloride |
| CN100412084C (zh) * | 2003-07-02 | 2008-08-20 | 獀洛克斯股份有限公司 | 热稳定的结晶盐酸表柔比星及其制造方法 |
| SI2263694T1 (sl) * | 2003-09-25 | 2013-09-30 | Astellas Pharma Inc. | Antitumorsko sredstvo, ki obsega inhibitor histon-deacetilaze FK228 in inhibitor topoizomeraze II doksorubicin |
| RU2262923C2 (ru) * | 2003-12-25 | 2005-10-27 | Государственное образовательное учреждение высшего профессионального образования Курский государственный медицинский университет Министерства здравоохранения Российской Федерации | Иммобилизованная форма доксорубицина |
| US7388083B2 (en) * | 2005-03-07 | 2008-06-17 | Solux Corporation | Epimerization of 4′-C bond and modification of 14-CH3-(CO)-fragment in anthracyclin antibiotics |
| JP2008513519A (ja) * | 2005-05-11 | 2008-05-01 | シコール インコーポレイティド | 安定した凍結乾燥されたアントラサイクリングリコシド |
| EP1921919B1 (en) | 2005-07-14 | 2012-04-04 | Lithera, Inc. | Sustained release enhanced lipolytic formulation for regional adipose tissue treatment |
| CN101331147B (zh) * | 2005-12-13 | 2011-11-30 | 苏洛克股份有限公司 | 用于制备4-脱甲基柔红霉素的方法 |
| US8802830B2 (en) * | 2005-12-20 | 2014-08-12 | Solux Corporation | Synthesis of epirubicin from 13-dihydrodaunorubicine |
| US8148338B2 (en) * | 2006-02-22 | 2012-04-03 | Supratek Pharma Inc. | Doxorubicin formulations for anti-cancer use |
| US7470672B2 (en) * | 2006-07-31 | 2008-12-30 | Savvipharm Inc. | Compositions and methods of reducing tissue levels of drugs when given as orotate derivatives |
| EP2152312B1 (en) * | 2007-05-16 | 2014-12-31 | KTB Tumorforschungsgesellschaft mbH | Low-viscous anthracycline formulation |
| US8227430B2 (en) | 2007-09-04 | 2012-07-24 | Meiji Seika Pharma Co., Ltd | Injectable, injection solution, and injection kit preparation |
| US20100234314A1 (en) * | 2007-10-26 | 2010-09-16 | Pfizer Inc. | Idarubicin for the treatment of lymphoma in a dog |
| US8357785B2 (en) * | 2008-01-08 | 2013-01-22 | Solux Corporation | Method of aralkylation of 4′-hydroxyl group of anthracylins |
| US9132084B2 (en) | 2009-05-27 | 2015-09-15 | Neothetics, Inc. | Methods for administration and formulations for the treatment of regional adipose tissue |
| CN102869363A (zh) * | 2010-01-15 | 2013-01-09 | 利赛拉公司 | 冻干的块状制剂 |
| UA111822C2 (uk) | 2010-11-24 | 2016-06-24 | Общєство С Огранічєнной Отвєтствєнностью "Новамедіка" | Монотерапевтичий препарат селективного ліпофільного бета-агоніста тривалої дії і спосіб косметичного лікування ожиріння і контурного випинання |
| DE102011103751A1 (de) | 2011-05-31 | 2012-12-06 | Heraeus Precious Metals Gmbh & Co. Kg | Kristallisierung von Epirubicinhydrochlorid |
| DE102011111991A1 (de) * | 2011-08-30 | 2013-02-28 | Lead Discovery Center Gmbh | Neue Cyclosporin-Derivate |
| DK2931042T3 (da) | 2012-12-13 | 2021-06-07 | Cytrx Corp | Anthracyclinformuleringer |
| CA2912908C (en) | 2013-06-05 | 2021-06-08 | Cytrx Corporation | Cytotoxic agents comprising covalently protein binding groups for treating brain cancer |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU33730B (en) * | 1967-04-18 | 1978-02-28 | Farmaceutici Italia | Process for preparing a novel antibiotic substance and salts thereof |
| US4039663A (en) * | 1975-03-19 | 1977-08-02 | Societa' Farmaceutici Italia S.P.A. | Daunomycins, process for their uses and intermediates |
| GB1506200A (en) * | 1975-04-30 | 1978-04-05 | Farmaceutici Italia | Glycosides |
| GB1567456A (en) * | 1976-11-16 | 1980-05-14 | Farmaceutici Italia | Daunomycin derivatives |
| US4177264A (en) * | 1977-10-17 | 1979-12-04 | Sri International | N-benzyl anthracyclines |
| GB2007645B (en) * | 1977-10-17 | 1982-05-12 | Stanford Res Inst Int | Benzyl anthracyclines and pharmaceutical compositions containing them |
| JPS563851A (en) * | 1979-06-22 | 1981-01-16 | Matsushita Electric Works Ltd | Fireplace in floor |
| JPS5756494A (en) * | 1980-09-22 | 1982-04-05 | Microbial Chem Res Found | New anthracyclin derivative |
| US4325947A (en) * | 1981-05-12 | 1982-04-20 | Farmitalia Carlo Erba S.P.A. | 4-Demethoxy-4'-deoxydoxorubicin |
| IT1210476B (it) * | 1981-05-28 | 1989-09-14 | Erba Farmitalia | Antracicline. |
| US4438105A (en) * | 1982-04-19 | 1984-03-20 | Farmaitalia Carlo Erba S.P.A | 4'-Iododerivatives of anthracycline glycosides |
| FI75834C (fi) * | 1982-05-24 | 1988-08-08 | Erba Farmitalia | Foerfarande foer framstaellning av antracyklinglykosidfoereningar. |
| US4464529A (en) * | 1982-07-20 | 1984-08-07 | Sri International | Analogues of morpholinyl daunorubicin and morpholinyl doxorubicin |
| CA1248944A (en) * | 1982-09-28 | 1989-01-17 | Gareth J. Thomas | Anthracycline glycosides |
| JPS5982395A (ja) * | 1982-11-02 | 1984-05-12 | Microbial Chem Res Found | アントラサイクリン化合物、その製造法およびその用途 |
| GR79729B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1982-12-20 | 1984-10-31 | Univ Ohio State Res Found | |
| JPS6092212A (ja) * | 1983-10-26 | 1985-05-23 | Kyowa Hakko Kogyo Co Ltd | ドキソルビシン塩の製剤 |
| US4537882A (en) * | 1984-05-10 | 1985-08-27 | Ohio State University | 4-Demethoxy-3'-desamino-2'-halo-anthracycline and pharmaceutical composition containing same |
-
1984
- 1984-10-22 GB GB848426672A patent/GB8426672D0/en active Pending
-
1985
- 1985-10-03 ES ES547578A patent/ES8605374A1/es not_active Expired
- 1985-10-08 FI FI853913A patent/FI853913A7/fi not_active Application Discontinuation
- 1985-10-15 HU HU853988A patent/HU197988B/hu unknown
- 1985-10-15 CN CN85107562A patent/CN85107562B/zh not_active Expired
- 1985-10-16 US US06/788,158 patent/US4675311A/en not_active Expired - Lifetime
- 1985-10-16 IT IT22507/85A patent/IT1186779B/it active Protection Beyond IP Right Term
- 1985-10-16 FI FI854035A patent/FI86252C/fi not_active IP Right Cessation
- 1985-10-16 DE DE3536896A patent/DE3536896C2/de not_active Expired - Lifetime
- 1985-10-16 YU YU164485A patent/YU46160B/sh unknown
- 1985-10-17 AU AU48805/85A patent/AU572003B2/en not_active Expired
- 1985-10-17 JP JP60230055A patent/JPH0611700B2/ja not_active Expired - Lifetime
- 1985-10-17 IL IL76732A patent/IL76732A/xx not_active IP Right Cessation
- 1985-10-17 CH CH4476/85A patent/CH667594A5/de not_active IP Right Cessation
- 1985-10-18 GB GB08525709A patent/GB2165751B/en not_active Expired
- 1985-10-18 PH PH32947A patent/PH23982A/en unknown
- 1985-10-18 RU SU853964940A patent/RU1836088C/ru active
- 1985-10-18 UA UA3964940A patent/UA19169A/uk unknown
- 1985-10-18 UA UA5010680A patent/UA34419C2/uk unknown
- 1985-10-18 ZA ZA858033A patent/ZA858033B/xx unknown
- 1985-10-18 AT AT0303285A patent/AT401345B/de not_active IP Right Cessation
- 1985-10-18 NZ NZ213885A patent/NZ213885A/en unknown
- 1985-10-21 KR KR1019850007740A patent/KR920005813B1/ko not_active Expired
- 1985-10-21 NO NO854194A patent/NO170616C/no not_active IP Right Cessation
- 1985-10-21 CA CA000493459A patent/CA1248453A/en not_active Expired
- 1985-10-21 PT PT81347A patent/PT81347B/pt unknown
- 1985-10-21 DK DK481585A patent/DK165620C/da not_active IP Right Cessation
- 1985-10-21 IE IE2593/85A patent/IE56992B1/en not_active IP Right Cessation
- 1985-10-21 BE BE0/215752A patent/BE903484A/fr not_active IP Right Cessation
- 1985-10-21 FR FR8515596A patent/FR2571966B1/fr not_active Expired
- 1985-10-21 NL NL8502869A patent/NL191308C/xx not_active IP Right Cessation
- 1985-10-21 SE SE8504945A patent/SE467520B/sv not_active IP Right Cessation
- 1985-10-22 CS CS857565A patent/CS270421B2/cs not_active IP Right Cessation
- 1985-10-22 GR GR852549A patent/GR852549B/el unknown
-
1986
- 1986-08-06 US US06/893,613 patent/US4840938A/en not_active Expired - Lifetime
-
1988
- 1988-12-30 MY MYPI88001588A patent/MY103956A/en unknown
-
1990
- 1990-09-26 US US07/588,526 patent/US5091372A/en not_active Expired - Lifetime
- 1990-09-28 US US07/590,536 patent/US5091373A/en not_active Expired - Lifetime
- 1990-10-03 SG SG802/90A patent/SG80290G/en unknown
- 1990-11-15 HK HK943/90A patent/HK94390A/xx not_active IP Right Cessation
-
1992
- 1992-01-30 RU SU5010680A patent/RU2101018C1/ru active
-
1994
- 1994-02-23 BG BG098530A patent/BG60934B2/bg unknown
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