JP3576180B2 - 改良イフォスファミド凍結乾燥組成物 - Google Patents
改良イフォスファミド凍結乾燥組成物 Download PDFInfo
- Publication number
- JP3576180B2 JP3576180B2 JP32457092A JP32457092A JP3576180B2 JP 3576180 B2 JP3576180 B2 JP 3576180B2 JP 32457092 A JP32457092 A JP 32457092A JP 32457092 A JP32457092 A JP 32457092A JP 3576180 B2 JP3576180 B2 JP 3576180B2
- Authority
- JP
- Japan
- Prior art keywords
- ifosfamide
- urea
- weight
- lyophilized
- lyophilized composition
- 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
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 229960001101 ifosfamide Drugs 0.000 title claims abstract description 86
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000004202 carbamide Substances 0.000 claims abstract description 40
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 23
- XOGTZOOQQBDUSI-UHFFFAOYSA-M Mesna Chemical compound [Na+].[O-]S(=O)(=O)CCS XOGTZOOQQBDUSI-UHFFFAOYSA-M 0.000 claims abstract description 21
- 229960004635 mesna Drugs 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000003860 storage Methods 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 2
- 238000000859 sublimation Methods 0.000 claims 1
- 230000008022 sublimation Effects 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 abstract description 12
- 230000008569 process Effects 0.000 abstract description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 16
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 15
- 229930195725 Mannitol Natural products 0.000 description 15
- 239000000594 mannitol Substances 0.000 description 15
- 235000010355 mannitol Nutrition 0.000 description 15
- 239000004471 Glycine Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 6
- 239000008194 pharmaceutical composition Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZZVDXRCAGGQFAK-UHFFFAOYSA-N 2h-oxazaphosphinine Chemical compound N1OC=CC=P1 ZZVDXRCAGGQFAK-UHFFFAOYSA-N 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 4
- 229960004397 cyclophosphamide Drugs 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229940056193 ifosfamide / mesna Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- PMHOWXRNJXWYIP-UHFFFAOYSA-N 4,5-dihydrooxazaphosphole Chemical group C1CP=NO1 PMHOWXRNJXWYIP-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000004383 yellowing Methods 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
-
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (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)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Materials For Medical Uses (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US781,436 | 1991-10-23 | ||
| US07/781,436 US5227373A (en) | 1991-10-23 | 1991-10-23 | Lyophilized ifosfamide compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05246856A JPH05246856A (ja) | 1993-09-24 |
| JP3576180B2 true JP3576180B2 (ja) | 2004-10-13 |
Family
ID=25122737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32457092A Expired - Lifetime JP3576180B2 (ja) | 1991-10-23 | 1992-10-22 | 改良イフォスファミド凍結乾燥組成物 |
Country Status (24)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995007083A1 (en) * | 1993-09-10 | 1995-03-16 | F.H. Faulding & Co. Limited | Ifosfamide lyophilisate composition |
| US5789000A (en) * | 1994-11-14 | 1998-08-04 | Bionumerik Pharmaceuticals, Inc. | Sterile aqueous parenteral formulations of cis-diammine dichloro platinum |
| DE19529057B4 (de) * | 1995-08-08 | 2007-12-13 | Baxter Healthcare S.A. | Ifosfamid-Lyophilisat-Zubereitungen |
| KR100246757B1 (ko) | 1997-05-09 | 2000-03-15 | 윤종용 | 트랜스컨덕턴스 가변방법 및 회로와 그를 이용한 가변 대역 필터 및 가변 이득 증폭기 |
| DE19733305A1 (de) * | 1997-08-01 | 1999-02-04 | Asta Medica Ag | Pharmazeutische Zusammensetzung enthaltend Ifosfamid und Carnitin |
| DE59813853D1 (de) * | 1997-10-13 | 2007-02-01 | Stada Arzneimittel Ag | Flüssige darreichungsformen oxazaphosphorinhaltiger pharmazeutischer produkte |
| US5972912A (en) * | 1998-12-17 | 1999-10-26 | S.P. Pharmaceuticals | Method for lyophilizing ifosfamide |
| CN1126547C (zh) * | 2000-07-19 | 2003-11-05 | 南京振中生物工程有限公司 | 香菇多糖冻干粉针剂及其制备方法 |
| US6613927B1 (en) | 2002-02-08 | 2003-09-02 | American Pharmaceutical Partners, Inc. | Sterile lyophilized ifosfamide and associated methods |
| KR100970528B1 (ko) * | 2002-02-22 | 2010-07-16 | 쉐링 코포레이션 | 항신생물제, 특히 테모졸로마이드의 약제학적 제형, 이의제조 및 사용 방법 |
| NZ538584A (en) * | 2002-09-05 | 2007-05-31 | Bharat Serums & Vaccines Ltd | Stable liquid composition of oxazaphosphorine, mesna and etherified beta-cyclodextrin |
| KR101066181B1 (ko) * | 2002-12-02 | 2011-09-20 | 바라트 쎄럼스 앤드 백신스 리미티드 | 비경구 투여용 아이포스파마이드 조성물 및 이의 제조방법 |
| US7199111B2 (en) * | 2002-12-02 | 2007-04-03 | Bharat Serums & Vaccines Ltd. | Aqueous ifosfamide compositions for parenteral administration and a process for their preparations |
| ATE516014T1 (de) * | 2003-10-01 | 2011-07-15 | Baxter Int | Neue verwendung, pharmazeutische präparate und verfahren zu ihrer herstellung |
| MX2007005361A (es) * | 2004-11-05 | 2008-01-11 | Cephalon Inc | Tratamientos para cancer. |
| US8436190B2 (en) | 2005-01-14 | 2013-05-07 | Cephalon, Inc. | Bendamustine pharmaceutical compositions |
| US8968721B2 (en) | 2005-12-28 | 2015-03-03 | Advanced Bionutrition Corporation | Delivery vehicle for probiotic bacteria comprising a dry matrix of polysaccharides, saccharides and polyols in a glass form and methods of making same |
| EP1973406B1 (en) | 2005-12-28 | 2014-03-12 | Advanced Bionutrition Corporation | A delivery vehicle for probiotic bacteria comprising a dry matrix of polysaccharides, saccharides and polyols in a glass form |
| US8721616B2 (en) * | 2006-09-29 | 2014-05-13 | Infa S.A. | Packaging system for pharmaceutical compositions and kit for intravenous administration |
| WO2008076975A1 (en) | 2006-12-18 | 2008-06-26 | Advanced Bionutrition Corporation | A dry food product containing live probiotic |
| CL2008001332A1 (es) * | 2007-05-08 | 2009-01-02 | Merck Sharp & Dohme | Uso de temozolomida para preparar un medicamento util para el tratamiento de un desorden proliferativo. |
| AR072777A1 (es) | 2008-03-26 | 2010-09-22 | Cephalon Inc | Formas solidas de clorhidrato de bendamustina |
| EP2889029A1 (en) | 2008-09-25 | 2015-07-01 | Cephalon, Inc. | Liquid formulations of bendamustine |
| CN103554030A (zh) * | 2009-01-15 | 2014-02-05 | 赛福伦公司 | 苯达莫司汀游离碱的新颖形式 |
| EP3266448B1 (en) | 2009-03-27 | 2022-02-16 | Intervet International B.V. | Microparticulated vaccines for the oral or nasal vaccination and boostering of animals including fish |
| JP5841527B2 (ja) * | 2009-05-26 | 2016-01-13 | アドバンスド バイオニュートリション コーポレーション | 生物学的に活性な微生物および／または生物活性材料を含む安定な乾燥粉末組成物およびその製造方法 |
| US9504750B2 (en) | 2010-01-28 | 2016-11-29 | Advanced Bionutrition Corporation | Stabilizing composition for biological materials |
| PH12012501410A1 (en) | 2010-01-28 | 2012-10-22 | Advanced Bionutrition Corp | Dry glassy composition comprising a bioactive material |
| AR082682A1 (es) | 2010-08-13 | 2012-12-26 | Advanced Bionutrition Corp | Composicion estabilizadora de almacenamiento en seco para materiales biologicos |
| WO2015101665A1 (en) | 2014-01-06 | 2015-07-09 | Auxin Surgery Sa | Lyophilized mesna compositions |
| US10342769B2 (en) | 2014-11-14 | 2019-07-09 | Navinta Iii Inc | Carmustine pharmaceutical composition |
| WO2017019273A1 (en) | 2015-07-29 | 2017-02-02 | Advanced Bionutrition Corporation | Stable dry probiotic compositions for special dietary uses |
| JP6706988B2 (ja) * | 2016-07-20 | 2020-06-10 | 日本化薬株式会社 | ボルテゾミブを含有する医薬組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3732340A (en) * | 1966-07-11 | 1973-05-08 | Asta Werke Ag Chem Fab | N',o-propylene phosphoric acid ester diamides |
| US4537883A (en) * | 1982-11-12 | 1985-08-27 | Mead Johnson & Company | Lyophilized cyclophosphamide |
| ZA851062B (en) * | 1984-03-01 | 1985-11-27 | Asta Werke Ag Chem Fab | Salts of oxazaphosphorine derivatives and process for their production |
| DE3722043A1 (de) * | 1986-07-11 | 1988-01-14 | Asta Werke Ag Chem Fab | Loesungen von oxazaphosphorinen mit verbesserter stabilitaet und verfahren zu deren herstellung |
| NO873860L (no) * | 1986-10-31 | 1988-05-02 | Asta Pharma Ag | Ifosfamid-lyofilisat og fremgangsmaate til deres fremstilling. |
| EP0281832B1 (de) * | 1987-03-06 | 1991-05-02 | ASTA Pharma Aktiengesellschaft | Verfahren zur Herstellung von Ifosfamid mit verbesserten Eigenschaften |
| ATE65402T1 (de) * | 1988-03-19 | 1991-08-15 | Asta Pharma Ag | Ifosfamid-mesna-lyophilisat und verfahren zu dessen herstellung. |
| US5036060A (en) * | 1988-07-25 | 1991-07-30 | Fujisawa Usa, Inc. | Cyclophosphamide |
-
1991
- 1991-10-23 US US07/781,436 patent/US5227373A/en not_active Expired - Lifetime
-
1992
- 1992-10-20 ZA ZA928104A patent/ZA928104B/xx unknown
- 1992-10-20 NZ NZ244816A patent/NZ244816A/en not_active IP Right Cessation
- 1992-10-20 SK SK3176-92A patent/SK279869B6/sk not_active IP Right Cessation
- 1992-10-20 MY MYPI92001893A patent/MY109794A/en unknown
- 1992-10-20 CZ CS923176A patent/CZ282445B6/cs not_active IP Right Cessation
- 1992-10-20 KR KR1019920019270A patent/KR100247161B1/ko not_active Expired - Fee Related
- 1992-10-21 CA CA002081061A patent/CA2081061A1/en not_active Abandoned
- 1992-10-21 IL IL10349692A patent/IL103496A/en not_active IP Right Cessation
- 1992-10-21 TW TW081108396A patent/TW217987B/zh not_active IP Right Cessation
- 1992-10-21 AU AU27166/92A patent/AU658011B2/en not_active Ceased
- 1992-10-21 CN CN92111646A patent/CN1046202C/zh not_active Expired - Fee Related
- 1992-10-21 EG EG63992A patent/EG20114A/xx active
- 1992-10-21 HU HU9203306A patent/HU221428B/hu not_active IP Right Cessation
- 1992-10-22 DE DE69228105T patent/DE69228105T2/de not_active Expired - Lifetime
- 1992-10-22 AT AT92118093T patent/ATE175354T1/de not_active IP Right Cessation
- 1992-10-22 EP EP92118093A patent/EP0538858B1/en not_active Expired - Lifetime
- 1992-10-22 FI FI924797A patent/FI107701B/fi active
- 1992-10-22 RU RU92004463A patent/RU2106138C1/ru not_active IP Right Cessation
- 1992-10-22 ES ES92118093T patent/ES2125880T3/es not_active Expired - Lifetime
- 1992-10-22 DK DK92118093T patent/DK0538858T3/da active
- 1992-10-22 JP JP32457092A patent/JP3576180B2/ja not_active Expired - Lifetime
- 1992-10-23 MX MX9206105A patent/MX9206105A/es unknown
-
1995
- 1995-06-20 HU HU95P/P00276P patent/HU211293A9/hu unknown
-
1999
- 1999-03-31 GR GR990400929T patent/GR3029835T3/el unknown
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