IL93670A - Sodium N-acetylneuramine trihydrate - Google Patents
Sodium N-acetylneuramine trihydrateInfo
- Publication number
- IL93670A IL93670A IL9367090A IL9367090A IL93670A IL 93670 A IL93670 A IL 93670A IL 9367090 A IL9367090 A IL 9367090A IL 9367090 A IL9367090 A IL 9367090A IL 93670 A IL93670 A IL 93670A
- Authority
- IL
- Israel
- Prior art keywords
- sodium
- acetylneuraminate
- trihydrate
- solution
- ethanol
- Prior art date
Links
- SGVNUGVAEIADTR-CPSXCUFQSA-M O.O.O.[Na+].CC(=O)N[C@@H]1[C@@H](O)CC(O)(C([O-])=O)O[C@H]1[C@H](O)[C@H](O)CO Chemical compound O.O.O.[Na+].CC(=O)N[C@@H]1[C@@H](O)CC(O)(C([O-])=O)O[C@H]1[C@H](O)[C@H](O)CO SGVNUGVAEIADTR-CPSXCUFQSA-M 0.000 title abstract description 8
- 150000004684 trihydrates Chemical class 0.000 claims abstract description 23
- QKFTYFYIYXTFBX-BKSOAOGQSA-M sodium;(2s,4s,5r,6r)-5-acetamido-2,4-dihydroxy-6-[(1r,2r)-1,2,3-trihydroxypropyl]oxane-2-carboxylate Chemical compound [Na+].CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C([O-])=O)O[C@H]1[C@H](O)[C@H](O)CO QKFTYFYIYXTFBX-BKSOAOGQSA-M 0.000 claims abstract description 21
- 239000000843 powder Substances 0.000 claims abstract description 9
- 239000011734 sodium Substances 0.000 claims description 18
- 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 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- SQVRNKJHWKZAKO-LUWBGTNYSA-N N-acetylneuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)CC(O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-LUWBGTNYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 241001310793 Podium Species 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 238000001035 drying Methods 0.000 abstract description 3
- 230000001376 precipitating effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 9
- 239000012047 saturated solution Substances 0.000 description 7
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000004254 Ammonium phosphate Substances 0.000 description 2
- 229930186217 Glycolipid Natural products 0.000 description 2
- 102000003886 Glycoproteins Human genes 0.000 description 2
- 108090000288 Glycoproteins Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 2
- 235000019289 ammonium phosphates Nutrition 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000003172 expectorant agent Substances 0.000 description 2
- 230000003419 expectorant effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 125000005629 sialic acid group Chemical group 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 210000004102 animal cell Anatomy 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 238000002447 crystallographic data Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- BQINXKOTJQCISL-GRCPKETISA-N keto-neuraminic acid Chemical compound OC(=O)C(=O)C[C@H](O)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)CO BQINXKOTJQCISL-GRCPKETISA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
- C07H5/06—Aminosugars
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1055388A JP2745059B2 (ja) | 1989-03-08 | 1989-03-08 | Ｎ―アセチルノイラミン酸ナトリウム・三水和物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL93670A true IL93670A (en) | 1994-08-26 |
Family
ID=12997127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9367090A IL93670A (en) | 1989-03-08 | 1990-03-06 | Sodium N-acetylneuramine trihydrate |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5231177A (es) |
| EP (1) | EP0386721B1 (es) |
| JP (1) | JP2745059B2 (es) |
| KR (1) | KR0128369B1 (es) |
| CN (1) | CN1026982C (es) |
| AT (1) | ATE118217T1 (es) |
| AU (1) | AU621203B2 (es) |
| CA (1) | CA2011468C (es) |
| DE (1) | DE69016683T2 (es) |
| DK (1) | DK0386721T3 (es) |
| ES (1) | ES2067580T3 (es) |
| FI (1) | FI95267C (es) |
| HU (1) | HU203247B (es) |
| IL (1) | IL93670A (es) |
| NO (1) | NO173701C (es) |
| NZ (1) | NZ232806A (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI291462B (en) * | 2000-04-25 | 2007-12-21 | Daiichi Sankyo Co Ltd | Hydrate crystal of neuraminic acid compound |
| US8999954B2 (en) * | 2007-07-03 | 2015-04-07 | Childern's Hospital & Research Center at Oakland | Inhibitors of polysialic acid de-N-acetylase and methods for using the same |
| EP2173759A4 (en) | 2007-07-03 | 2014-01-29 | Childrens Hosp & Res Ct Oak | OLIGOSIAL INSERTS, PROCESS FOR THEIR PREPARATION AND ITS IMMUNOLOGICAL USE |
| CA2692417C (en) | 2007-07-03 | 2017-03-21 | Children's Hospital & Research Center At Oakland | Polysialic acid derivatives, methods of production, and uses in enhancing cancer antigen production and targeting |
| CN104926802B (zh) * | 2011-12-16 | 2018-02-13 | 第一三共株式会社 | 用于制备神经氨酸衍生物的方法 |
| WO2016017677A1 (ja) * | 2014-07-30 | 2016-02-04 | 協和発酵バイオ株式会社 | Ｎ－アセチルノイラミン酸アルカリ金属塩・無水和物の結晶及びその製造方法 |
| KR102646509B1 (ko) * | 2015-01-28 | 2024-03-11 | 교와 핫꼬 바이오 가부시키가이샤 | N-아세틸노이라민산암모늄염·무수화물의 결정 및 그 제조 방법 |
| CN109180749B (zh) * | 2018-10-18 | 2022-04-22 | 中国科学院合肥物质科学研究院 | 一种利用过饱和结晶法制备高纯度n-乙酰神经氨酸水合物的方法 |
| CN109265497B (zh) * | 2018-10-18 | 2022-04-19 | 武汉中科光谷绿色生物技术有限公司 | 一种利用有机溶剂转化n-乙酰神经氨酸水合物制备n-乙酰神经氨酸的方法 |
| CN109232677B (zh) * | 2018-10-18 | 2021-12-28 | 中国科学院合肥物质科学研究院 | 一种使n-乙酰神经氨酸水合物转化为n-乙酰神经氨酸的方法 |
| CN110606863B (zh) * | 2019-10-08 | 2023-05-30 | 中国科学院合肥物质科学研究院 | 一种n-乙酰神经氨酸二水合物的制备方法 |
| CN110627849B (zh) * | 2019-10-15 | 2023-02-17 | 中国科学院合肥物质科学研究院 | 一种n-乙酰神经氨酸标准物质的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8002823A (nl) * | 1980-05-14 | 1981-12-16 | Amsterdam Chem Comb | Lactitolmonohydraat, alsmede werkwijze voor het bereiden van kristallijn lactitol. |
| JPS6053039B2 (ja) * | 1981-06-26 | 1985-11-22 | メクト株式会社 | Ｎ−アセチル／イラミン酸誘導体およびその製造方法 |
| AU582758B2 (en) * | 1984-06-28 | 1989-04-13 | Mect Corporation | Sialic acid derivatives, galactose derivatives and method for producing the same |
| JPS61103889A (ja) * | 1984-10-24 | 1986-05-22 | Hayashibara Biochem Lab Inc | 結晶エルロ−ス及びそれを含有する含蜜結晶並びにそれらの製造方法及び用途 |
| JPS6344590A (ja) * | 1986-08-12 | 1988-02-25 | Mect Corp | シアル酸誘導体の製造方法 |
| IT1223398B (it) * | 1987-12-01 | 1990-09-19 | Sirac Spa | Procedimento per la preparazione di lattulosio cristallino ad alta purezza |
| JPH01299294A (ja) * | 1988-05-24 | 1989-12-04 | Mect Corp | ４，８−アンハイドロ−ｎ−アセチルノイラミン酸誘導体 |
| EP0369369B1 (en) * | 1988-11-16 | 1994-01-26 | Nippon Kayaku Kabushiki Kaisha | Dihydrate crystals of etoposide-2-dimethylamino compound hydrochloride and a process for production thereof |
-
1989
- 1989-03-08 JP JP1055388A patent/JP2745059B2/ja not_active Expired - Fee Related
-
1990
- 1990-03-05 US US07/488,860 patent/US5231177A/en not_active Expired - Lifetime
- 1990-03-06 IL IL9367090A patent/IL93670A/en not_active IP Right Cessation
- 1990-03-06 NZ NZ232806A patent/NZ232806A/xx unknown
- 1990-03-07 HU HU901346A patent/HU203247B/hu not_active IP Right Cessation
- 1990-03-07 NO NO901084A patent/NO173701C/no unknown
- 1990-03-07 ES ES90104335T patent/ES2067580T3/es not_active Expired - Lifetime
- 1990-03-07 EP EP90104335A patent/EP0386721B1/en not_active Expired - Lifetime
- 1990-03-07 DK DK90104335.6T patent/DK0386721T3/da active
- 1990-03-07 DE DE69016683T patent/DE69016683T2/de not_active Expired - Fee Related
- 1990-03-07 FI FI901150A patent/FI95267C/fi not_active IP Right Cessation
- 1990-03-07 AT AT90104335T patent/ATE118217T1/de not_active IP Right Cessation
- 1990-03-07 AU AU50776/90A patent/AU621203B2/en not_active Ceased
- 1990-03-07 CA CA002011468A patent/CA2011468C/en not_active Expired - Fee Related
- 1990-03-07 KR KR1019900002983A patent/KR0128369B1/ko not_active Expired - Fee Related
- 1990-03-08 CN CN90101959A patent/CN1026982C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO173701C (no) | 1994-01-19 |
| HUT53117A (en) | 1990-09-28 |
| KR0128369B1 (ko) | 1998-04-03 |
| NO173701B (no) | 1993-10-11 |
| FI95267B (fi) | 1995-09-29 |
| CA2011468C (en) | 1996-09-10 |
| JPH02235897A (ja) | 1990-09-18 |
| NO901084L (no) | 1990-09-10 |
| FI901150A0 (fi) | 1990-03-07 |
| FI95267C (fi) | 1996-01-10 |
| EP0386721B1 (en) | 1995-02-08 |
| NO901084D0 (no) | 1990-03-07 |
| CN1045584A (zh) | 1990-09-26 |
| JP2745059B2 (ja) | 1998-04-28 |
| CA2011468A1 (en) | 1990-09-08 |
| NZ232806A (en) | 1991-10-25 |
| CN1026982C (zh) | 1994-12-14 |
| US5231177A (en) | 1993-07-27 |
| DK0386721T3 (da) | 1995-07-10 |
| HU203247B (en) | 1991-06-28 |
| AU5077690A (en) | 1990-09-20 |
| DE69016683D1 (de) | 1995-03-23 |
| HU901346D0 (en) | 1990-05-28 |
| AU621203B2 (en) | 1992-03-05 |
| KR900014419A (ko) | 1990-10-23 |
| ES2067580T3 (es) | 1995-04-01 |
| DE69016683T2 (de) | 1995-06-08 |
| EP0386721A1 (en) | 1990-09-12 |
| ATE118217T1 (de) | 1995-02-15 |
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