NO301982B1 - Krystallinske syreaddisjonssalter av diastereomerrene 3-cefem-4-karboksylsyre-1-(2,2-dimetylpropionyloksy)-etylestere, anvendelse av forbindelsene samt farmasöytiske preparater inneholdende disse - Google Patents
Krystallinske syreaddisjonssalter av diastereomerrene 3-cefem-4-karboksylsyre-1-(2,2-dimetylpropionyloksy)-etylestere, anvendelse av forbindelsene samt farmasöytiske preparater inneholdende disse Download PDFInfo
- Publication number
- NO301982B1 NO301982B1 NO922023A NO922023A NO301982B1 NO 301982 B1 NO301982 B1 NO 301982B1 NO 922023 A NO922023 A NO 922023A NO 922023 A NO922023 A NO 922023A NO 301982 B1 NO301982 B1 NO 301982B1
- Authority
- NO
- Norway
- Prior art keywords
- diastereomer
- acid
- cephem
- carboxylic acid
- dimethylpropionyloxy
- Prior art date
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- 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
- 241001465754 Metazoa Species 0.000 description 1
- QCYOIFVBYZNUNW-BYPYZUCNSA-N N,N-dimethyl-L-alanine Chemical compound CN(C)[C@@H](C)C(O)=O QCYOIFVBYZNUNW-BYPYZUCNSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 108010073038 Penicillin Amidase Proteins 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- ACBDNFPUXYGKPT-UHFFFAOYSA-N bromomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCBr ACBDNFPUXYGKPT-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229950010227 cefotiam hexetil Drugs 0.000 description 1
- VVFDMWZLBPUKTD-ZKRNHDOASA-N cefotiam hexetil ester Chemical compound O=C([C@@H](NC(=O)CC=1N=C(N)SC=1)[C@H]1SCC=2CSC=3N(N=NN=3)CCN(C)C)N1C=2C(=O)OC(C)OC(=O)OC1CCCCC1 VVFDMWZLBPUKTD-ZKRNHDOASA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 150000001782 cephems Chemical class 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- VMWRXTLCJPKMEB-SJECBDQJSA-M sodium;(6r)-3-(methoxymethyl)-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].C1([C@@H]2N(C1=O)C(=C(CS2)COC)C([O-])=O)NC(=O)COC1=CC=CC=C1 VMWRXTLCJPKMEB-SJECBDQJSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- VNCOOYOSWRJWMZ-IDVGRLRUSA-N triethylazanium;(2z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetate Chemical compound CC[NH+](CC)CC.C=1SC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1/C(C(=O)[O-])=N/OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNCOOYOSWRJWMZ-IDVGRLRUSA-N 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4116937 | 1991-05-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO922023D0 NO922023D0 (no) | 1992-05-22 |
| NO922023L NO922023L (no) | 1992-11-25 |
| NO301982B1 true NO301982B1 (no) | 1998-01-05 |
Family
ID=6432313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO922023A NO301982B1 (no) | 1991-05-24 | 1992-05-22 | Krystallinske syreaddisjonssalter av diastereomerrene 3-cefem-4-karboksylsyre-1-(2,2-dimetylpropionyloksy)-etylestere, anvendelse av forbindelsene samt farmasöytiske preparater inneholdende disse |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US5594133A (sh) |
| EP (1) | EP0514791B1 (sh) |
| JP (1) | JPH0680065B2 (sh) |
| KR (1) | KR100198908B1 (sh) |
| CN (1) | CN1037608C (sh) |
| AT (1) | ATE164377T1 (sh) |
| AU (1) | AU652635B2 (sh) |
| BR (1) | BR9201939A (sh) |
| CA (1) | CA2069200C (sh) |
| CZ (1) | CZ282299B6 (sh) |
| DE (1) | DE59209246D1 (sh) |
| DK (1) | DK0514791T3 (sh) |
| EG (1) | EG20121A (sh) |
| ES (1) | ES2115625T3 (sh) |
| FI (1) | FI108435B (sh) |
| GR (1) | GR3026625T3 (sh) |
| HR (1) | HRP940842B1 (sh) |
| HU (1) | HU220065B (sh) |
| IE (1) | IE921660A1 (sh) |
| IL (1) | IL101970A (sh) |
| MA (1) | MA22532A1 (sh) |
| MX (1) | MX9202460A (sh) |
| NO (1) | NO301982B1 (sh) |
| PH (1) | PH31070A (sh) |
| PL (3) | PL170798B1 (sh) |
| RU (1) | RU2073680C1 (sh) |
| SK (1) | SK280291B6 (sh) |
| UY (1) | UY23418A1 (sh) |
| YU (1) | YU48484B (sh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW212181B (sh) * | 1992-02-14 | 1993-09-01 | Hoechst Ag | |
| ES2117066T3 (es) * | 1992-05-21 | 1998-08-01 | Hoechst Ag | Procedimiento para la disociacion de esteres profarmacos de cefalosporina para dar acido 7-amino-3-metoximetil-cef-3-em-4-carboxilico. |
| AT401651B (de) * | 1994-06-14 | 1996-11-25 | Biochemie Gmbh | 7-(2-(2-aminothiazol-4-yl)-2-(z)- hydroximinoacetamido)-3-n,n- dimethylcarbamoyloxymethyl-3-cephem-4- |
| AT408226B (de) * | 1999-05-05 | 2001-09-25 | Biochemie Gmbh | Kristalliner 7-(2-(2-formylaminothiazol-4-yl)-2 |
| AU2002368494A1 (en) * | 2002-12-20 | 2004-07-14 | Lupin Limited | A process for the preparation of cefpodoxime proxetil |
| WO2004060896A1 (en) * | 2003-01-06 | 2004-07-22 | Lupin Limited | A process for the manufacture of cefpodoxime proxetil |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4203899A (en) * | 1974-12-19 | 1980-05-20 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| US4668783A (en) * | 1974-12-19 | 1987-05-26 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido cephalosporin compounds |
| JPS5760345B2 (sh) * | 1974-12-19 | 1982-12-18 | Takeda Chemical Industries Ltd | |
| DK154939C (da) * | 1974-12-19 | 1989-06-12 | Takeda Chemical Industries Ltd | Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf |
| US4298606A (en) * | 1974-12-19 | 1981-11-03 | Takeda Chemical Industries, Ltd. | Thiazolylacetamido compounds |
| DE2760123C2 (de) * | 1976-01-23 | 1986-04-30 | Roussel-Uclaf, Paris | 7-Aminothiazolyl-syn-oxyiminoacetamidocephalosporansäuren, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
| JPS6011713B2 (ja) * | 1976-09-08 | 1985-03-27 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| DE2714880A1 (de) * | 1977-04-02 | 1978-10-26 | Hoechst Ag | Cephemderivate und verfahren zu ihrer herstellung |
| US4409215A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical Co., Ltd. | 7-Acylamino-3-substituted cephalosporanic acid derivatives and processes for the preparation thereof |
| FR2476087A1 (fr) * | 1980-02-18 | 1981-08-21 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-alkyloxy ou 3-alkyl-thiomethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| JPS5759894A (en) * | 1980-09-30 | 1982-04-10 | Sankyo Co Ltd | Cephalosporin for oral administration |
| US4486425A (en) * | 1980-09-30 | 1984-12-04 | Sankyo Company Limited | 7-[2-(2-Aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylates |
| DE3804841A1 (de) * | 1988-02-17 | 1989-08-31 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| DE3919259A1 (de) * | 1989-06-13 | 1990-12-20 | Hoechst Ag | Kristalline cephem-saeureadditionssalze und verfahren zu ihrer herstellung |
-
1992
- 1992-03-30 YU YU33592A patent/YU48484B/sh unknown
- 1992-05-12 PH PH44394A patent/PH31070A/en unknown
- 1992-05-15 DE DE59209246T patent/DE59209246D1/de not_active Expired - Lifetime
- 1992-05-15 DK DK92108252T patent/DK0514791T3/da active
- 1992-05-15 EP EP92108252A patent/EP0514791B1/de not_active Expired - Lifetime
- 1992-05-15 ES ES92108252T patent/ES2115625T3/es not_active Expired - Lifetime
- 1992-05-15 AT AT92108252T patent/ATE164377T1/de active
- 1992-05-21 EG EG26792A patent/EG20121A/xx active
- 1992-05-21 UY UY23418A patent/UY23418A1/es not_active IP Right Cessation
- 1992-05-21 FI FI922310A patent/FI108435B/fi not_active IP Right Cessation
- 1992-05-22 MX MX9202460A patent/MX9202460A/es unknown
- 1992-05-22 RU SU925011790A patent/RU2073680C1/ru active
- 1992-05-22 JP JP4130688A patent/JPH0680065B2/ja not_active Expired - Lifetime
- 1992-05-22 IL IL10197092A patent/IL101970A/en not_active IP Right Cessation
- 1992-05-22 AU AU17062/92A patent/AU652635B2/en not_active Expired
- 1992-05-22 SK SK1547-92A patent/SK280291B6/sk not_active IP Right Cessation
- 1992-05-22 BR BR929201939A patent/BR9201939A/pt not_active Application Discontinuation
- 1992-05-22 CZ CS921547A patent/CZ282299B6/cs not_active IP Right Cessation
- 1992-05-22 PL PL92294651A patent/PL170798B1/pl unknown
- 1992-05-22 PL PL92311553A patent/PL170962B1/pl unknown
- 1992-05-22 HU HU9201716A patent/HU220065B/hu unknown
- 1992-05-22 KR KR1019920008671A patent/KR100198908B1/ko not_active IP Right Cessation
- 1992-05-22 NO NO922023A patent/NO301982B1/no not_active IP Right Cessation
- 1992-05-22 CA CA002069200A patent/CA2069200C/en not_active Expired - Lifetime
- 1992-05-22 MA MA22819A patent/MA22532A1/fr unknown
- 1992-05-22 PL PL92311554A patent/PL170403B1/pl unknown
- 1992-05-23 CN CN92103911A patent/CN1037608C/zh not_active Expired - Lifetime
- 1992-07-01 IE IE166092A patent/IE921660A1/en not_active IP Right Cessation
-
1994
- 1994-10-26 HR HRP-335/92 patent/HRP940842B1/xx not_active IP Right Cessation
-
1995
- 1995-05-22 US US08/447,045 patent/US5594133A/en not_active Expired - Lifetime
- 1995-05-23 US US08/447,635 patent/US5556850A/en not_active Expired - Lifetime
-
1998
- 1998-04-14 GR GR980400821T patent/GR3026625T3/el unknown
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