NO301325B1 - Organiske salter av N,N'-diacetylcystin, farmasöytisk preparat samt anvendelse av saltene - Google Patents
Organiske salter av N,N'-diacetylcystin, farmasöytisk preparat samt anvendelse av saltene Download PDFInfo
- Publication number
- NO301325B1 NO301325B1 NO941968A NO941968A NO301325B1 NO 301325 B1 NO301325 B1 NO 301325B1 NO 941968 A NO941968 A NO 941968A NO 941968 A NO941968 A NO 941968A NO 301325 B1 NO301325 B1 NO 301325B1
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- Prior art keywords
- salt
- pharmaceutical preparation
- salts
- diacetyl
- dinac
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
- C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
- C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9103572A SE9103572D0 (sv) | 1991-11-29 | 1991-11-29 | Organic salts of n,n'-diacetyl cystine |
| PCT/SE1992/000807 WO1993011104A1 (fr) | 1991-11-29 | 1992-11-25 | Sels organiques de cystine de n, n'-diacetyle |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO941968D0 NO941968D0 (no) | 1994-05-26 |
| NO941968L NO941968L (no) | 1994-05-26 |
| NO301325B1 true NO301325B1 (no) | 1997-10-13 |
Family
ID=20384494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO941968A NO301325B1 (no) | 1991-11-29 | 1994-05-26 | Organiske salter av N,N'-diacetylcystin, farmasöytisk preparat samt anvendelse av saltene |
Country Status (38)
| Country | Link |
|---|---|
| US (5) | US5385904A (fr) |
| EP (1) | EP0621862B1 (fr) |
| JP (1) | JP3302018B2 (fr) |
| KR (1) | KR100256185B1 (fr) |
| CN (1) | CN1039586C (fr) |
| AP (1) | AP350A (fr) |
| AT (1) | ATE141913T1 (fr) |
| AU (1) | AU657827B2 (fr) |
| CA (1) | CA2123516A1 (fr) |
| CZ (1) | CZ282085B6 (fr) |
| DE (1) | DE69213256T2 (fr) |
| DK (1) | DK0621862T3 (fr) |
| DZ (1) | DZ1637A1 (fr) |
| EE (1) | EE03025B1 (fr) |
| ES (1) | ES2090713T3 (fr) |
| FI (1) | FI942504A (fr) |
| GR (1) | GR3021546T3 (fr) |
| HK (1) | HK62297A (fr) |
| HR (1) | HRP921322B1 (fr) |
| HU (1) | HU215390B (fr) |
| IL (1) | IL103778A (fr) |
| IS (1) | IS1645B (fr) |
| LV (1) | LV11949B (fr) |
| MA (1) | MA22716A1 (fr) |
| MX (1) | MX9206851A (fr) |
| MY (1) | MY110523A (fr) |
| NO (1) | NO301325B1 (fr) |
| NZ (1) | NZ245077A (fr) |
| PL (2) | PL171336B1 (fr) |
| RU (1) | RU2135468C1 (fr) |
| SE (1) | SE9103572D0 (fr) |
| SG (1) | SG73962A1 (fr) |
| SI (1) | SI9200351A (fr) |
| SK (1) | SK281697B6 (fr) |
| TN (1) | TNSN92108A1 (fr) |
| WO (1) | WO1993011104A1 (fr) |
| YU (1) | YU48594B (fr) |
| ZA (1) | ZA928739B (fr) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3865463A (en) * | 1973-11-12 | 1975-02-11 | Busch & Co Inc Ag | Electrical adapter plug |
| EP0715853A1 (fr) * | 1991-01-10 | 1996-06-12 | Transcend Therapeutics, Inc. | Utilisation des esters de glutathione pour le traitement des désordres pulmonaires |
| US5747459A (en) * | 1991-02-04 | 1998-05-05 | Nestec, Ltd. | Method for insuring adequate intracellular glutathione in tissue |
| US5430045A (en) * | 1992-04-23 | 1995-07-04 | Free Radical Sciences, Inc. | Method of reducing or preventing bone marrow hypoplasia |
| US5447712A (en) * | 1993-12-09 | 1995-09-05 | Free Radical Sciences | Method of reducing cyclophosphamide induced hemorrhagic cystitis |
| SE9500897D0 (sv) * | 1995-03-14 | 1995-03-14 | Astra Ab | The pharmacological use of certain cystine derivatives |
| SE9602262D0 (sv) * | 1996-06-06 | 1996-06-06 | Astra Ab | New use of derivatives of cystine |
| AR007398A1 (es) * | 1996-06-18 | 1999-10-27 | Astrazeneca Ab | Proceso para preparar sales inorganicas de n-n'-diacetilcistina |
| SE9602416D0 (sv) * | 1996-06-18 | 1996-06-18 | Astra Ab | New forms of an organic salt of N'N-diacetylcystine |
| US6017959A (en) * | 1996-06-18 | 2000-01-25 | Astra Aktiebolag | Forms of organic salts of N,N'-diacetylcystine |
| CN1059907C (zh) * | 1997-05-23 | 2000-12-27 | 中国石油化工集团公司巴陵石化岳阳石油化工总厂 | 一种含共轭二烯轻聚合物的选择氢化方法 |
| US20030203006A1 (en) * | 1997-10-29 | 2003-10-30 | Ajinomoto Co. Inc. | Immunomodulator |
| US6197749B1 (en) * | 1997-10-29 | 2001-03-06 | Ajinomoto Co., Inc. | Method of suppressing immune responses by reducing intracellular content of glutathione in macrophages and monocytes |
| SE9800932D0 (sv) | 1998-03-20 | 1998-03-20 | Astra Ab | New compunds |
| EP1004302A3 (fr) * | 1998-10-29 | 2003-06-04 | Ajinomoto Co., Inc. | Immunomodulateur |
| SE9900438D0 (sv) * | 1999-02-10 | 1999-02-10 | Astra Ab | The pharmacological use of certian cystine derivatives |
| US9006175B2 (en) | 1999-06-29 | 2015-04-14 | Mannkind Corporation | Potentiation of glucose elimination |
| SE518784C2 (sv) * | 2000-12-27 | 2002-11-19 | Nactilus Ab | "N-Acetyl-L-cystein med kompositioner för behandling av neoplasier" |
| JPWO2002072040A1 (ja) * | 2001-03-13 | 2004-07-02 | 味の素株式会社 | 化粧料または皮膚外用剤 |
| ES2300568T3 (es) | 2002-03-20 | 2008-06-16 | Mannkind Corporation | Aparato de inhalacion. |
| CA2575692C (fr) | 2004-08-20 | 2014-10-14 | Mannkind Corporation | Catalyse de la synthese de dicetopiperazine |
| BR122019022692B1 (pt) | 2004-08-23 | 2023-01-10 | Mannkind Corporation | Composição terapêutica em pó seco contendo dicetopiperazina, pelo menos um tipo de cátion e um agente biologicamente ativo |
| HUE028691T2 (en) | 2005-09-14 | 2016-12-28 | Mannkind Corp | A method for formulating a drug based on increasing the affinity of crystalline microparticle surfaces towards active ingredients |
| EP1986679B1 (fr) | 2006-02-22 | 2017-10-25 | MannKind Corporation | Procédé pour améliorer les propriétés pharmaceutiques de microparticules comprenant de la dicétopipérazine et un agent actif |
| US8438729B2 (en) * | 2006-03-09 | 2013-05-14 | Canon Kabushiki Kaisha | Method of producing liquid discharge head |
| AR072114A1 (es) | 2008-06-13 | 2010-08-04 | Mannkind Corp | Un inhalador de polvo seco y sistema para suministro de farmacos |
| US8485180B2 (en) | 2008-06-13 | 2013-07-16 | Mannkind Corporation | Dry powder drug delivery system |
| BRPI0914308B8 (pt) * | 2008-06-20 | 2021-06-22 | Mannkind Corp | sistema de inalação |
| TWI614024B (zh) | 2008-08-11 | 2018-02-11 | 曼凱公司 | 超快起作用胰島素之用途 |
| US8314106B2 (en) | 2008-12-29 | 2012-11-20 | Mannkind Corporation | Substituted diketopiperazine analogs for use as drug delivery agents |
| CA2754595C (fr) | 2009-03-11 | 2017-06-27 | Mannkind Corporation | Appareil, systeme et procede de mesure de resistance d'un inhalateur |
| KR101875969B1 (ko) | 2009-06-12 | 2018-07-06 | 맨카인드 코포레이션 | 한정된 비표면적을 갖는 디케토피페라진 마이크로입자 |
| EP2496295A1 (fr) | 2009-11-03 | 2012-09-12 | MannKind Corporation | Appareil et méthode de simulation d'efforts d'inhalation |
| RU2571331C1 (ru) | 2010-06-21 | 2015-12-20 | Маннкайнд Корпорейшн | Системы и способы доставки сухих порошковых лекарств |
| JP6133270B2 (ja) | 2011-04-01 | 2017-05-24 | マンカインド コーポレイション | 薬剤カートリッジのためのブリスター包装 |
| WO2012174472A1 (fr) | 2011-06-17 | 2012-12-20 | Mannkind Corporation | Microparticules de dicétopipérazine de capacité élevée |
| JP6018640B2 (ja) | 2011-10-24 | 2016-11-02 | マンカインド コーポレイション | 疼痛を緩和するのに有効な鎮痛組成物並びに当該組成物を含む乾燥粉末及び乾燥粉末薬剤輸送システム |
| CN102491926B (zh) * | 2011-12-15 | 2013-09-25 | 青岛市药品检验所 | 一种硫普罗宁二硫化物的制备和纯化方法 |
| SG11201500218VA (en) | 2012-07-12 | 2015-03-30 | Mannkind Corp | Dry powder drug delivery systems and methods |
| US10159644B2 (en) | 2012-10-26 | 2018-12-25 | Mannkind Corporation | Inhalable vaccine compositions and methods |
| WO2014144895A1 (fr) | 2013-03-15 | 2014-09-18 | Mannkind Corporation | Compositions de dicétopipérazine microcristallines et procédés |
| AU2014290438B2 (en) | 2013-07-18 | 2019-11-07 | Mannkind Corporation | Heat-stable dry powder pharmaceutical compositions and methods |
| WO2015021064A1 (fr) | 2013-08-05 | 2015-02-12 | Mannkind Corporation | Appareil d'insufflation et procédés |
| US10307464B2 (en) | 2014-03-28 | 2019-06-04 | Mannkind Corporation | Use of ultrarapid acting insulin |
| US10561806B2 (en) | 2014-10-02 | 2020-02-18 | Mannkind Corporation | Mouthpiece cover for an inhaler |
| US20230157939A1 (en) * | 2020-04-28 | 2023-05-25 | Conopco, Inc., D/B/A Unilever | Personal care compositions with enhanced solubility actives |
| EP4216939A1 (fr) * | 2020-09-28 | 2023-08-02 | Georgia Tech Research Corporation | Utilisation de cystéine et de ses dérivés comme agents anti-thrombotiques et thrombolytiques |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB592631A (en) * | 1945-04-04 | 1947-09-24 | Du Pont | Cysteine and cystine |
| GB954268A (en) | 1962-02-26 | 1964-04-02 | Mead Johnson & Co | Decongestant compositions comprising n-acylated sulphydryl compounds |
| FR8205M (fr) * | 1968-12-20 | 1970-09-14 | ||
| US3647834A (en) * | 1969-08-11 | 1972-03-07 | Mead Johnson & Co | Zinc mercaptide n-acetylcysteine carboxylate salts |
| US3878305A (en) * | 1972-05-25 | 1975-04-15 | Procter & Gamble | Fortification of foodstuffs with n-acyl derivatives of sulphur-containing l-amino acids |
| US3952115A (en) * | 1975-04-02 | 1976-04-20 | The Procter & Gamble Company | Fortification of foodstuffs with N-acyl derivatives of sulfur-containing L-amino acid esters |
| US4141734A (en) * | 1975-09-11 | 1979-02-27 | Ciba-Geiby Ag | Photographic developing process |
| US4093739A (en) * | 1977-06-15 | 1978-06-06 | Mead Johnson & Company | Mercaptoacylamidobenzoyl glycine and mucolytic process |
| JPS6011888B2 (ja) * | 1978-10-11 | 1985-03-28 | 参天製薬株式会社 | リウマチ疾患治療薬 |
| JPS56155298A (en) | 1980-05-02 | 1981-12-01 | Tanabe Seiyaku Co | Shampoo composition |
| GB2097256B (en) * | 1981-04-02 | 1985-05-30 | Morelle Jean V | Compositions containing n-butyryl alphaaminoacids |
| FR2503151A1 (fr) * | 1981-04-02 | 1982-10-08 | Morelle Jean | Butyryminoacides soufres. mode de preparation. emploi comme element keratogenique chez l'homme et l'animal et comme agent de fertilisation chez les vegetaux |
| JPS58164566A (ja) * | 1982-03-09 | 1983-09-29 | Kenji Okawa | シスチン類の製造法 |
| US4827016A (en) * | 1985-09-16 | 1989-05-02 | Morgan Lee R | Method and compounds for reducing dermal inflammations |
| US4708965A (en) | 1985-09-16 | 1987-11-24 | Morgan Lee R | Method of treating herpes virus infections with N,N'-diacetylcystine and derivatives |
| US4724239A (en) * | 1985-09-16 | 1988-02-09 | Morgan Lee R | Method of treating chemical ulcers with N,N'-diacetylcystine, N-acetyl homocysteine and N-acetyl cysteine |
| JPH0660157B2 (ja) * | 1985-11-20 | 1994-08-10 | 三井東圧化学株式会社 | システインからシスチンを製造する方法 |
| JPS62195356A (ja) * | 1986-02-20 | 1987-08-28 | Seiwa Kasei:Kk | シスチン誘導体及びその塩 |
| AT402931B (de) * | 1986-11-07 | 1997-09-25 | Pharmacia Gmbh | Verfahren zur herstellung von neuen cystinverbindungen und derenverwendung |
| SE8704542D0 (sv) * | 1987-11-19 | 1987-11-19 | Draco Ab | New derivatives of cysteine |
| IL98310A (en) * | 1990-06-08 | 1996-08-04 | Astra Ab | Medicinal preparations containing a history of cystine |
| TW221376B (fr) * | 1990-06-28 | 1994-03-01 | Astra Ab | |
| GB9111885D0 (en) * | 1991-06-03 | 1991-07-24 | Erba Carlo Spa | Nerve growth factor for use in the prevention and treatment of viral infections |
-
1991
- 1991-11-29 SE SE9103572A patent/SE9103572D0/xx unknown
-
1992
- 1992-11-10 NZ NZ245077A patent/NZ245077A/en unknown
- 1992-11-12 ZA ZA928739A patent/ZA928739B/xx unknown
- 1992-11-17 IL IL10377892A patent/IL103778A/xx not_active IP Right Cessation
- 1992-11-18 YU YU99092A patent/YU48594B/sh unknown
- 1992-11-20 AP APAP/P/1992/000448A patent/AP350A/en active
- 1992-11-23 TN TNTNSN92108A patent/TNSN92108A1/fr unknown
- 1992-11-23 HR HR9103572-5A patent/HRP921322B1/xx not_active IP Right Cessation
- 1992-11-24 MA MA23006A patent/MA22716A1/fr unknown
- 1992-11-24 IS IS3949A patent/IS1645B/is unknown
- 1992-11-25 HU HU9401473A patent/HU215390B/hu not_active IP Right Cessation
- 1992-11-25 SK SK632-94A patent/SK281697B6/sk unknown
- 1992-11-25 KR KR1019940701815A patent/KR100256185B1/ko not_active IP Right Cessation
- 1992-11-25 EP EP92924975A patent/EP0621862B1/fr not_active Expired - Lifetime
- 1992-11-25 MY MYPI92002155A patent/MY110523A/en unknown
- 1992-11-25 US US07/981,373 patent/US5385904A/en not_active Expired - Lifetime
- 1992-11-25 AU AU30996/92A patent/AU657827B2/en not_active Ceased
- 1992-11-25 WO PCT/SE1992/000807 patent/WO1993011104A1/fr active IP Right Grant
- 1992-11-25 PL PL92314567A patent/PL171336B1/pl unknown
- 1992-11-25 RU RU94027569/04A patent/RU2135468C1/ru not_active IP Right Cessation
- 1992-11-25 ES ES92924975T patent/ES2090713T3/es not_active Expired - Lifetime
- 1992-11-25 CZ CZ941297A patent/CZ282085B6/cs not_active IP Right Cessation
- 1992-11-25 DZ DZ920148A patent/DZ1637A1/fr active
- 1992-11-25 AT AT92924975T patent/ATE141913T1/de not_active IP Right Cessation
- 1992-11-25 JP JP51003993A patent/JP3302018B2/ja not_active Expired - Fee Related
- 1992-11-25 CA CA002123516A patent/CA2123516A1/fr not_active Abandoned
- 1992-11-25 DK DK92924975.3T patent/DK0621862T3/da active
- 1992-11-25 SG SG1996004497A patent/SG73962A1/en unknown
- 1992-11-25 PL PL92303924A patent/PL170787B1/pl unknown
- 1992-11-25 DE DE69213256T patent/DE69213256T2/de not_active Expired - Fee Related
- 1992-11-27 MX MX9206851A patent/MX9206851A/es not_active IP Right Cessation
- 1992-11-28 CN CN92113666A patent/CN1039586C/zh not_active Expired - Fee Related
- 1992-11-30 SI SI19929200351A patent/SI9200351A/sl unknown
-
1994
- 1994-05-26 NO NO941968A patent/NO301325B1/no not_active IP Right Cessation
- 1994-05-27 FI FI942504A patent/FI942504A/fi unknown
- 1994-11-08 US US08/335,941 patent/US5693858A/en not_active Expired - Fee Related
- 1994-11-17 EE EE9400378A patent/EE03025B1/xx not_active IP Right Cessation
-
1995
- 1995-06-07 US US08/484,143 patent/US5824681A/en not_active Expired - Fee Related
- 1995-06-07 US US08/477,387 patent/US5804582A/en not_active Expired - Fee Related
- 1995-06-07 US US08/476,218 patent/US5650538A/en not_active Expired - Lifetime
-
1996
- 1996-11-06 GR GR960402920T patent/GR3021546T3/el unknown
-
1997
- 1997-05-08 HK HK62297A patent/HK62297A/xx not_active IP Right Cessation
- 1997-08-28 LV LVP-97-158A patent/LV11949B/en unknown
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| MM1K | Lapsed by not paying the annual fees |