JPS6070097A - 安定なｓ−アデノシル−ｌ−メチオニン塩の製造方法 - Google Patents
安定なｓ−アデノシル−ｌ−メチオニン塩の製造方法Info
- Publication number
- JPS6070097A JPS6070097A JP59175326A JP17532684A JPS6070097A JP S6070097 A JPS6070097 A JP S6070097A JP 59175326 A JP59175326 A JP 59175326A JP 17532684 A JP17532684 A JP 17532684A JP S6070097 A JPS6070097 A JP S6070097A
- Authority
- JP
- Japan
- Prior art keywords
- carried out
- yeast
- reverse osmosis
- same
- eluate
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical class O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 238000001223 reverse osmosis Methods 0.000 claims description 19
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 239000013592 cell lysate Substances 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000012528 membrane Substances 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 238000001694 spray drying Methods 0.000 claims description 4
- 239000002250 absorbent Substances 0.000 claims description 3
- 230000002745 absorbent Effects 0.000 claims description 3
- 238000011033 desalting Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- 238000010612 desalination reaction Methods 0.000 claims description 2
- 229930182817 methionine Natural products 0.000 claims description 2
- 229960004452 methionine Drugs 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 229920001429 chelating resin Polymers 0.000 claims 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
- 239000011260 aqueous acid Substances 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- FVSFGYXQNHBRHP-TWBCTODHSA-N (2S)-2-[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl-sulfoamino]-4-methylsulfanylbutanoic acid Chemical compound O[C@@H]1[C@H](O)[C@@H](CN([C@@H](CCSC)C(O)=O)S(O)(=O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 FVSFGYXQNHBRHP-TWBCTODHSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000006166 lysate Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 238000010257 thawing Methods 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- RTQLMSZMCBAZIX-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;sulfuric acid Chemical compound OS(O)(=O)=O.CC1=CC=C(S(O)(=O)=O)C=C1 RTQLMSZMCBAZIX-UHFFFAOYSA-N 0.000 description 1
- WUUGFSXJNOTRMR-WOIOKPISSA-N 5'-deoxy-5'-methylthioadenosine Chemical compound O[C@@H]1[C@@H](O)[C@H](CSC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 WUUGFSXJNOTRMR-WOIOKPISSA-N 0.000 description 1
- WUUGFSXJNOTRMR-UHFFFAOYSA-N 5alpha-Hydroxy-3abeta,5beta,8-trimethyl-1-(1,5-dimethyl-hexen-(4)-yl)-4abetaH,7abetaH-dicyclopentano[a.d]cyclooctaen-(8) Natural products OC1C(O)C(CSC)OC1N1C2=NC=NC(N)=C2N=C1 WUUGFSXJNOTRMR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 241000235646 Cyberlindnera jadinii Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007791 dehumidification Methods 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-L disulfate(2-) Chemical compound [O-]S(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/26—Preparation of nitrogen-containing carbohydrates
- C12P19/28—N-glycosides
- C12P19/38—Nucleosides
- C12P19/40—Nucleosides having a condensed ring system containing a six-membered ring having two nitrogen atoms in the same ring, e.g. purine nucleosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Saccharide Compounds (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22622-A/83 | 1983-08-24 | ||
| IT22622/83A IT1169773B (it) | 1983-08-24 | 1983-08-24 | Processo per la produzione di sali stabili della solfo-adenosil-l-metionina |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6070097A true JPS6070097A (ja) | 1985-04-20 |
| JPH0421478B2 JPH0421478B2 (enExample) | 1992-04-10 |
Family
ID=11198536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59175326A Granted JPS6070097A (ja) | 1983-08-24 | 1984-08-24 | 安定なｓ−アデノシル−ｌ−メチオニン塩の製造方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4621056A (enExample) |
| EP (1) | EP0141914B1 (enExample) |
| JP (1) | JPS6070097A (enExample) |
| KR (1) | KR900009054B1 (enExample) |
| AT (1) | ATE31550T1 (enExample) |
| AU (1) | AU569107B2 (enExample) |
| CA (1) | CA1223535A (enExample) |
| DE (1) | DE3468234D1 (enExample) |
| DK (1) | DK162240C (enExample) |
| ES (1) | ES8506044A1 (enExample) |
| FI (1) | FI77043C (enExample) |
| IT (1) | IT1169773B (enExample) |
| MX (1) | MX7625E (enExample) |
| NO (1) | NO159669C (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6881837B2 (en) | 2001-06-07 | 2005-04-19 | Orchid Chemicals & Pharmaceuticals Ltd. | Chemical synthesis of S-adenosyl-L-methionine with enrichment of (S,S)-isomer |
| US7667034B2 (en) | 2004-06-23 | 2010-02-23 | Orchid Chemicals & Pharmaceuticals Limited | Chemical synthesis of S-adenosyl-L-methionine with enrichment of (S,S)-isomer |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1173992B (it) * | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente idonei per uso farmaceutico orale |
| IT1173990B (it) * | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente adatti per uso parenterale |
| US4794174A (en) * | 1987-02-10 | 1988-12-27 | Southern Research Institute | 5'deoxy-5'-substituted adenosines |
| US5180714A (en) * | 1990-10-31 | 1993-01-19 | Health Research, Inc. | Adenosine compounds for the treatment of diseases caused by parasitic protozoa |
| IT1315236B1 (it) * | 1999-10-05 | 2003-02-03 | Chementecno Srl | Processo per la purificazione di s-adenosil-l-metionina e per lapreparazione dei suoi sali farmaceuticamente accettabili. |
| IT1318535B1 (it) | 2000-05-25 | 2003-08-27 | Chementecno Srl | Processo per la preparazione di sali farmaceuticamente accettabili di(ss,rs)-s-adenosil-l-metionina. |
| IT1317920B1 (it) * | 2000-10-20 | 2003-07-15 | Univ Roma | S-adenosilmetionina e suoi derivati per il trattamento e laprevenzione della malattia di alzheimer. |
| US6649753B2 (en) * | 2001-06-07 | 2003-11-18 | Orchid Chemicals & Pharmaceuticals Ltd. | Stable salts of S-adenosyl-L-methionine (SAMe) and the process for their preparation |
| CN101374529B (zh) | 2006-01-17 | 2012-08-08 | 三菱瓦斯化学株式会社 | 使s-腺苷-l-甲硫氨酸稳定化的方法以及稳定化后的组合物 |
| US9080158B2 (en) | 2006-05-16 | 2015-07-14 | Mitsubishi Gas Chemical Company, Inc. | Method of producing S-adenosyl-L-methionine-containing dry yeast having excellent storage stability, the product thereof and composition for oral intake |
| AU2008208325B2 (en) | 2007-01-25 | 2013-02-07 | Mitsubishi Gas Chemical Company, Inc. | Method for production of dry yeast containing S-adenosyl-L-methionine and having excellent storage stability, product produced by the method, and molded composition of the dry yeast |
| CN102321136B (zh) * | 2011-09-19 | 2014-10-22 | 北京化工大学 | S-腺苷-l-甲硫氨酸对甲苯磺酸硫酸双盐的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE37913B1 (en) * | 1972-08-02 | 1977-11-09 | Bioresearch Sas | Salt of s-adenosyl-l-methionine |
| JPS5631897B2 (enExample) * | 1972-11-13 | 1981-07-24 | ||
| US3962034A (en) * | 1973-02-01 | 1976-06-08 | Ajinomoto Co., Inc. | Method for producing s-adenosylmethionine or methylthioadenosine by yeast |
| IE39517B1 (en) * | 1973-06-27 | 1978-10-25 | Bioresearch Sas | Double salts of s-adenosyl-l-methhionine |
| FR2275220A1 (fr) * | 1974-06-21 | 1976-01-16 | Merieux Inst | Procede d'obtention de sels organiques de la s.adenosyl-l-methionine. nouveaux sels organiques obtenus des medicaments comprenant un ou plusieurs nouveaux sels obtenus |
| AR221676A1 (es) * | 1974-07-12 | 1981-03-13 | Bioresearch Sas | Procedimiento para la preparacion de sales estables sulfonicas y/o sulfuricas de la s-adenosil-l-metionina,particularmente utiles como donadores especificos de metilo para las reacciones bioquimicas de transferencia del grupo ch3;asi como tambien las reacciones fundamentales en el metabolismo lipilico,protilico y glucidico |
| DE2646269A1 (de) * | 1975-10-16 | 1977-04-28 | Yamasa Shoyu Kk | Stabilisierte s-adenosyl-l-methionin- zubereitung und verfahren zur herstellung derselben |
| JPS53107485A (en) * | 1977-02-28 | 1978-09-19 | Yamasa Shoyu Co Ltd | Preparation of s-adenosyl-l-methionine salt |
| GB2001976B (en) * | 1977-08-03 | 1982-03-10 | Yamasa Shoyu Kk | S-adenosyl-l-methionine compositions and production thereof |
| JPS5699499A (en) * | 1980-01-10 | 1981-08-10 | Kanegafuchi Chem Ind Co Ltd | Composition containing s-adenosyl-l-methionine, and its preparation |
| IT1137892B (it) * | 1981-08-24 | 1986-09-10 | Bioresearch Srl | Sali stabili della s-adenosilmetionina,processo per la loro preparazione e composizioni terapeutiche che li comprendono come principio attivo |
| IT1137640B (it) * | 1981-08-24 | 1986-09-10 | Bioresearch Srl | Sali stabili della s-adenosilmetionina,processo per la loro preparazione e composizioni terapeutiche che li comprendono come principio attivo |
| IT1139974B (it) * | 1981-09-11 | 1986-09-24 | Bioresearch Srl | Derivati della s-adenosilmetionina,processo per la preparazione e composizioni terapeutiche che li contengono come principio attivo |
| GB2116172B (en) * | 1982-02-25 | 1986-07-09 | Nippon Zeon Co | Microbial cells containing s-adenosyl methionine in high concentrations and process for production of s adenosyl methionine |
-
1983
- 1983-08-24 IT IT22622/83A patent/IT1169773B/it active
-
1984
- 1984-08-01 DE DE8484109109T patent/DE3468234D1/de not_active Expired
- 1984-08-01 AT AT84109109T patent/ATE31550T1/de not_active IP Right Cessation
- 1984-08-01 EP EP84109109A patent/EP0141914B1/en not_active Expired
- 1984-08-02 US US06/637,051 patent/US4621056A/en not_active Expired - Lifetime
- 1984-08-03 CA CA000460362A patent/CA1223535A/en not_active Expired
- 1984-08-22 MX MX8411264U patent/MX7625E/es unknown
- 1984-08-22 FI FI843315A patent/FI77043C/fi not_active IP Right Cessation
- 1984-08-23 NO NO843366A patent/NO159669C/no unknown
- 1984-08-23 KR KR1019840005106A patent/KR900009054B1/ko not_active Expired
- 1984-08-23 ES ES535378A patent/ES8506044A1/es not_active Expired
- 1984-08-23 DK DK402884A patent/DK162240C/da not_active IP Right Cessation
- 1984-08-23 AU AU32328/84A patent/AU569107B2/en not_active Ceased
- 1984-08-24 JP JP59175326A patent/JPS6070097A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6881837B2 (en) | 2001-06-07 | 2005-04-19 | Orchid Chemicals & Pharmaceuticals Ltd. | Chemical synthesis of S-adenosyl-L-methionine with enrichment of (S,S)-isomer |
| US7667034B2 (en) | 2004-06-23 | 2010-02-23 | Orchid Chemicals & Pharmaceuticals Limited | Chemical synthesis of S-adenosyl-L-methionine with enrichment of (S,S)-isomer |
Also Published As
| Publication number | Publication date |
|---|---|
| NO843366L (no) | 1985-02-25 |
| ATE31550T1 (de) | 1988-01-15 |
| ES535378A0 (es) | 1985-06-16 |
| FI843315A7 (fi) | 1985-02-25 |
| NO159669C (no) | 1989-01-25 |
| NO159669B (no) | 1988-10-17 |
| MX7625E (es) | 1990-03-27 |
| IT1169773B (it) | 1987-06-03 |
| US4621056A (en) | 1986-11-04 |
| FI843315A0 (fi) | 1984-08-22 |
| DK402884A (da) | 1985-02-25 |
| KR900009054B1 (ko) | 1990-12-17 |
| IT8322622A0 (it) | 1983-08-24 |
| AU3232884A (en) | 1985-02-28 |
| KR850001750A (ko) | 1985-04-01 |
| DK402884D0 (da) | 1984-08-23 |
| ES8506044A1 (es) | 1985-06-16 |
| FI77043C (fi) | 1989-01-10 |
| DE3468234D1 (en) | 1988-02-04 |
| DK162240C (da) | 1992-03-02 |
| FI77043B (fi) | 1988-09-30 |
| DK162240B (da) | 1991-09-30 |
| IT8322622A1 (it) | 1985-02-24 |
| CA1223535A (en) | 1987-06-30 |
| EP0141914A1 (en) | 1985-05-22 |
| EP0141914B1 (en) | 1987-12-23 |
| JPH0421478B2 (enExample) | 1992-04-10 |
| AU569107B2 (en) | 1988-01-21 |
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