SE508043C2 - Förfarande för framställning och användning av 2-amino-2,4,4- trimetylpentansaltet av klavulansyra som mellanprodukt vid framställning av farmaceutiskt godtagbara salter av klavulansyra - Google Patents
Förfarande för framställning och användning av 2-amino-2,4,4- trimetylpentansaltet av klavulansyra som mellanprodukt vid framställning av farmaceutiskt godtagbara salter av klavulansyraInfo
- Publication number
- SE508043C2 SE508043C2 SE9300758A SE9300758A SE508043C2 SE 508043 C2 SE508043 C2 SE 508043C2 SE 9300758 A SE9300758 A SE 9300758A SE 9300758 A SE9300758 A SE 9300758A SE 508043 C2 SE508043 C2 SE 508043C2
- Authority
- SE
- Sweden
- Prior art keywords
- clavulanic acid
- salt
- amino
- pharmaceutically acceptable
- trimethylpentane
- Prior art date
Links
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title claims abstract description 61
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 title claims abstract description 61
- 229960003324 clavulanic acid Drugs 0.000 title claims abstract description 61
- 150000003839 salts Chemical class 0.000 title claims abstract description 28
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical class CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- 239000003960 organic solvent Substances 0.000 claims description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical group CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 6
- 238000000855 fermentation Methods 0.000 claims description 5
- 230000004151 fermentation Effects 0.000 claims description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 claims 1
- -1 alkali metal salts Chemical class 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical class CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- TWUUDIAVXATXSA-UHFFFAOYSA-N 2,4,4-trimethylpentan-1-amine Chemical compound NCC(C)CC(C)(C)C TWUUDIAVXATXSA-UHFFFAOYSA-N 0.000 description 1
- AXJOZFAYYBUILC-UHFFFAOYSA-N 3,5-dimethylhexan-3-amine Chemical class CCC(C)(N)CC(C)C AXJOZFAYYBUILC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ABVRVIZBZKUTMK-JSYANWSFSA-M potassium clavulanate Chemical compound [K+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 ABVRVIZBZKUTMK-JSYANWSFSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0047292A AT400033B (de) | 1992-03-10 | 1992-03-10 | Neues verfahren zur isolierung und reinigung von clavulansäure und zur herstellung von pharmakologisch verträglichen salzen derselben |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE9300758D0 SE9300758D0 (sv) | 1993-03-08 |
| SE9300758L SE9300758L (sv) | 1993-09-11 |
| SE508043C2 true SE508043C2 (sv) | 1998-08-17 |
Family
ID=3491521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE9300758A SE508043C2 (sv) | 1992-03-10 | 1993-03-08 | Förfarande för framställning och användning av 2-amino-2,4,4- trimetylpentansaltet av klavulansyra som mellanprodukt vid framställning av farmaceutiskt godtagbara salter av klavulansyra |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US20010036940A1 (de) |
| JP (2) | JP2817563B2 (de) |
| CN (3) | CN1045604C (de) |
| AT (1) | AT400033B (de) |
| AU (1) | AU659282B2 (de) |
| CH (1) | CH685054A5 (de) |
| CY (1) | CY1995A (de) |
| DE (1) | DE4307422B4 (de) |
| DK (1) | DK26093A (de) |
| ES (1) | ES2058029B1 (de) |
| FI (1) | FI101965B (de) |
| FR (1) | FR2688506B1 (de) |
| GB (1) | GB2264944B (de) |
| GR (1) | GR1002329B (de) |
| HK (1) | HK42696A (de) |
| IE (1) | IE70926B1 (de) |
| IT (1) | IT1261213B (de) |
| NL (1) | NL9300430A (de) |
| NO (1) | NO301372B1 (de) |
| SE (1) | SE508043C2 (de) |
| TW (1) | TW364907B (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT399155B (de) * | 1992-03-26 | 1995-03-27 | Lek Tovarna Farmacevtskih | Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung |
| SI9300296B (sl) * | 1992-06-11 | 1998-06-30 | Smithkline Beecham P.L.C. | Postopek in intermedianti za pripravo klavulanske kisline |
| KR100200239B1 (ko) * | 1992-10-21 | 1999-06-15 | 김충환 | 클라불란산 칼륨염의 제조방법 |
| DK0658558T3 (da) | 1993-11-17 | 2001-04-17 | Biochemie Gmbh | Adskillelse af cephalosporinisomere |
| GB9426261D0 (en) * | 1994-12-24 | 1995-02-22 | Spurcourt Ltd | Clavulanic acid salts |
| NZ301765A (en) * | 1995-02-25 | 1999-10-28 | Spurcourt Ltd | Clavulanic acid salts with a benzhydrylamine |
| KR100200242B1 (ko) * | 1995-05-16 | 1999-06-15 | 김충환 | 클라불란산염의 제조 방법 |
| AT403375B (de) * | 1995-11-15 | 1998-01-26 | Biochemie Gmbh | Verfahren zur fällung von alkalisalzen der clavulansäure |
| WO2000004028A1 (en) * | 1998-07-16 | 2000-01-27 | Dsm N.V. | Improved process for the preparation of salts and esters of clavulanic acid |
| CN1209099C (zh) * | 1999-04-01 | 2005-07-06 | Dsm公司 | 结晶化附聚物 |
| CA2408853C (en) * | 2000-05-13 | 2012-01-10 | Smithkline Beecham P.L.C. | Process |
| EP1933857A2 (de) * | 2005-09-07 | 2008-06-25 | Jennerex Biotherapeutics ULC | Systemische behandlung von metastasierten und/oder systemisch dissemierten tumoren mit gm-csf-exprimierenden pockenviren |
| JP7028064B2 (ja) | 2018-05-30 | 2022-03-02 | 横河電機株式会社 | 機器保全装置、機器保全方法、機器保全プログラム及び記録媒体 |
| JP2023533544A (ja) | 2020-07-10 | 2023-08-03 | カーボン クリーン ソリューションズ リミテッド | 低位熱を使用して溶媒から二酸化炭素を除去するための方法およびシステム |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3288800A (en) * | 1962-05-29 | 1966-11-29 | Squibb & Sons Inc | Schiff's bases of 6-amino-penicillanic acid and purification of 6-aminopenicillanic acid by the use thereof |
| GB1508977A (en) | 1974-04-20 | 1978-04-26 | Beecham Group Ltd | Beta-lactam antibiotic from streptomyces clavuligerus |
| IE41109B1 (en) * | 1974-04-20 | 1979-10-24 | Beecham Group Ltd | Novel -lactam antibiotic from streptomyces clavuligerus |
| US4110165A (en) * | 1974-04-20 | 1978-08-29 | Beecham Group Limited | Process for the production of clavulanic acid |
| GB1543563A (en) | 1975-02-07 | 1979-04-04 | Glaxo Lab Ltd | Beta-lactam antibiotic in purified form |
| US4144242A (en) * | 1975-02-07 | 1979-03-13 | Glaxo Laboratories Limited | Process for the purification of clavulanic acid |
| GB1561395A (en) | 1976-02-26 | 1980-02-20 | Beecham Group Ltd | -lactam antibiotic |
| GB1578739A (en) * | 1976-07-23 | 1980-11-05 | Beecham Group Ltd | Amine salts of clavulanic acid methods for their preparation and compositions containing them |
| GB2003863B (en) | 1977-09-01 | 1982-03-31 | Beecham Group Ltd | Chemical process |
| DE2861607D1 (en) | 1977-11-26 | 1982-03-11 | Beecham Group Plc | Derivatives of clavulanic acid and pharmaceutical compositions containing them |
| BE862211A (fr) * | 1977-12-22 | 1978-06-22 | Beecham Group Ltd | Agents antibacteriens |
| US4454069A (en) * | 1979-08-24 | 1984-06-12 | Beecham Group Limited | Clavulanic acid salts and their preparation from the tertiary butyl amine salt |
| DE3063683D1 (en) * | 1979-08-24 | 1983-07-14 | Beecham Group Plc | Amine salt of clavulanic acid, its preparation and use |
| NZ213963A (en) | 1984-10-27 | 1989-01-06 | Antibioticos Sa | Production of clavulanic acid |
| GB8618888D0 (en) * | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| US5679789A (en) * | 1987-01-29 | 1997-10-21 | Beecham Group, P.L.C. | Pharmaceutical compositions comprising potassium clavulanate and methods of using them |
| PT86631B (pt) | 1987-01-29 | 1992-01-31 | Beecham Group Plc | Processo para a preparacao de uma nova forma cristalina de clavulanato de potassio |
| ES2010143A6 (es) * | 1989-03-01 | 1989-10-16 | Pharma Mar S A Pharmar | Un nuevo procedimiento de obtencion del acido z(2r,5r)-3-(2-hiadroxietiliden)-7- oxo-4-oxa-1-azabiciclo(3,2,0) -heptano-2-carboxilico y de sales estares farmaceutiacamente aceptables del mismo,a partir de caldos de fermentacion de streptomyces, sp. |
| US5210296A (en) * | 1990-11-19 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Recovery of lactate esters and lactic acid from fermentation broth |
| AT399155B (de) * | 1992-03-26 | 1995-03-27 | Lek Tovarna Farmacevtskih | Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung |
| SI9300296B (sl) | 1992-06-11 | 1998-06-30 | Smithkline Beecham P.L.C. | Postopek in intermedianti za pripravo klavulanske kisline |
| SI9200139A (en) * | 1992-07-08 | 1994-03-31 | Lek Tovarna Farmacevtskih | New inclusion complex of clavulanic acid with hydrophylyc and hydropholyc beta-cyclodextrin derivates for production of them |
| KR100200239B1 (ko) | 1992-10-21 | 1999-06-15 | 김충환 | 클라불란산 칼륨염의 제조방법 |
| GB9401969D0 (en) | 1994-02-02 | 1994-03-30 | Smithkline Beecham Plc | Process |
| SI9400107A (en) | 1994-03-02 | 1995-10-31 | Lek Tovarna Farmacevtskih | New process of the isolation of clavulanic acid and its pharmaceutical salts from fermented broth of streptomyces sp.p 6621 ferm p 2804. |
| NZ301765A (en) * | 1995-02-25 | 1999-10-28 | Spurcourt Ltd | Clavulanic acid salts with a benzhydrylamine |
| GB2298201B (en) | 1995-02-25 | 1997-05-28 | Spurcourt Ltd | Clavulanic acid salts |
| SI9500074A (en) | 1995-03-10 | 1996-10-31 | Lek Tovarna Farmacevtskih | Process for preparation of alkani salts of clavulanic acid. |
| SI9500134B (sl) | 1995-04-20 | 2004-04-30 | Lek, | Postopek za pripravo čistih alkalijskih soli klavulanske kisline |
| KR100200242B1 (ko) | 1995-05-16 | 1999-06-15 | 김충환 | 클라불란산염의 제조 방법 |
| GB9515809D0 (en) | 1995-08-02 | 1995-10-04 | Smithkline Beecham Plc | Process |
| SI9500265A1 (en) | 1995-08-28 | 1997-02-28 | Lek Tovarna Farmacevtskih | Process for purification of the aqueous fermented broth filtrate of streptomyces sp. p 6621 ferm p 2804 by ultrafiltration |
| US6414142B1 (en) | 1996-06-13 | 2002-07-02 | Smithkline Beecham Corporation | Process for preparing potassium clavulanate |
| CA2271847A1 (en) | 1996-11-11 | 1998-05-22 | Gist-Brocades B.V. | Process for the preparation of salts and esters of clavulanic acid |
-
1992
- 1992-03-10 AT AT0047292A patent/AT400033B/de not_active IP Right Cessation
-
1993
- 1993-03-05 CH CH670/93A patent/CH685054A5/de not_active IP Right Cessation
- 1993-03-08 SE SE9300758A patent/SE508043C2/sv not_active IP Right Cessation
- 1993-03-08 NO NO930829A patent/NO301372B1/no unknown
- 1993-03-08 JP JP5046691A patent/JP2817563B2/ja not_active Expired - Fee Related
- 1993-03-08 GB GB9304704A patent/GB2264944B/en not_active Expired - Fee Related
- 1993-03-09 FI FI931032A patent/FI101965B/fi active
- 1993-03-09 GR GR930100090A patent/GR1002329B/el not_active IP Right Cessation
- 1993-03-09 FR FR9302720A patent/FR2688506B1/fr not_active Expired - Fee Related
- 1993-03-09 DK DK026093A patent/DK26093A/da not_active Application Discontinuation
- 1993-03-09 AU AU34070/93A patent/AU659282B2/en not_active Ceased
- 1993-03-09 DE DE4307422A patent/DE4307422B4/de not_active Expired - Fee Related
- 1993-03-09 IE IE930172A patent/IE70926B1/en not_active IP Right Cessation
- 1993-03-09 CN CN93102897A patent/CN1045604C/zh not_active Expired - Fee Related
- 1993-03-10 IT ITRM930147A patent/IT1261213B/it active IP Right Grant
- 1993-03-10 ES ES09300483A patent/ES2058029B1/es not_active Expired - Fee Related
- 1993-03-10 NL NL9300430A patent/NL9300430A/nl active Search and Examination
- 1993-05-04 TW TW082103491A patent/TW364907B/zh not_active IP Right Cessation
-
1996
- 1996-03-14 HK HK42696A patent/HK42696A/xx not_active IP Right Cessation
- 1996-06-29 CN CN96108278A patent/CN1150153A/zh active Pending
- 1996-06-29 CN CN96108276A patent/CN1145906A/zh active Pending
-
1997
- 1997-08-13 JP JP9218732A patent/JPH1067785A/ja active Pending
- 1997-09-05 CY CY199597A patent/CY1995A/en unknown
-
2001
- 2001-06-26 US US09/892,179 patent/US20010036940A1/en not_active Abandoned
-
2002
- 2002-02-08 US US10/071,364 patent/US20020072513A1/en not_active Abandoned
- 2002-09-20 US US10/251,948 patent/US20030022882A1/en not_active Abandoned
-
2003
- 2003-05-13 US US10/437,097 patent/USH2158H1/en not_active Abandoned
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