CA1267148A - PROCESS FOR THE PRODUCTION OF INDOLE-.alpha.-KETOACIDS FROM THE RELATIVE .alpha.-AMINOACID, PARTICULARLY FOR THE PRODUCTION OF INDOLEPYRUVIC ACID - Google Patents
PROCESS FOR THE PRODUCTION OF INDOLE-.alpha.-KETOACIDS FROM THE RELATIVE .alpha.-AMINOACID, PARTICULARLY FOR THE PRODUCTION OF INDOLEPYRUVIC ACIDInfo
- Publication number
- CA1267148A CA1267148A CA000511265A CA511265A CA1267148A CA 1267148 A CA1267148 A CA 1267148A CA 000511265 A CA000511265 A CA 000511265A CA 511265 A CA511265 A CA 511265A CA 1267148 A CA1267148 A CA 1267148A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- mixtures
- alpha
- group
- production
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 21
- RSTKLPZEZYGQPY-UHFFFAOYSA-N 3-(indol-3-yl)pyruvic acid Chemical compound C1=CC=C2C(CC(=O)C(=O)O)=CNC2=C1 RSTKLPZEZYGQPY-UHFFFAOYSA-N 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000003495 polar organic solvent Substances 0.000 claims description 5
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical group O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims 3
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 claims 1
- 229940000681 5-hydroxytryptophan Drugs 0.000 claims 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 claims 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 abstract description 11
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 abstract description 10
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract description 4
- 150000004716 alpha keto acids Chemical class 0.000 abstract description 3
- 238000005859 coupling reaction Methods 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 239000012024 dehydrating agents Substances 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 229960004799 tryptophan Drugs 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- ODUKZJKEVZCMRV-MERQFXBCSA-N (2s)-3-(1h-indol-3-yl)-2-(methylamino)propanoic acid;hydrochloride Chemical compound Cl.C1=CC=C2C(C[C@H](NC)C(O)=O)=CNC2=C1 ODUKZJKEVZCMRV-MERQFXBCSA-N 0.000 description 3
- 235000008206 alpha-amino acids Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940093499 ethyl acetate Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
- 229940091173 hydantoin Drugs 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 1
- 102000004625 Aspartate Aminotransferases Human genes 0.000 description 1
- 108010003415 Aspartate Aminotransferases Proteins 0.000 description 1
- 244000135860 Capparis spinosa subsp spinosa Species 0.000 description 1
- 150000007649 L alpha amino acids Chemical class 0.000 description 1
- HRXYCZSYPMMAPV-UHFFFAOYSA-N Methyl indole acetate Chemical compound CC(O)=O.C1=CC=C2NC(C)=CC2=C1 HRXYCZSYPMMAPV-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 241000287219 Serinus canaria Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006035 Tryptophane Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 210000001557 animal structure Anatomy 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- KCUNTYMNJVXYKZ-JTQLQIEISA-N methyl (2s)-2-amino-3-(1h-indol-3-yl)propanoate Chemical compound C1=CC=C2C(C[C@H](N)C(=O)OC)=CNC2=C1 KCUNTYMNJVXYKZ-JTQLQIEISA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 235000017103 tryptophane Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT48295A/85 | 1985-06-28 | ||
| IT48295/85A IT1184282B (it) | 1985-06-28 | 1985-06-28 | Procedimento per la produzione di alfa-chetoacidi indolici a partire da un rispettivo alfa-ammino-acido,particolarmente per produrre acido indolpiruvico |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1267148A true CA1267148A (en) | 1990-03-27 |
Family
ID=11265730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000511265A Expired - Lifetime CA1267148A (en) | 1985-06-28 | 1986-06-10 | PROCESS FOR THE PRODUCTION OF INDOLE-.alpha.-KETOACIDS FROM THE RELATIVE .alpha.-AMINOACID, PARTICULARLY FOR THE PRODUCTION OF INDOLEPYRUVIC ACID |
Country Status (13)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1206078B (it) * | 1987-06-03 | 1989-04-14 | Polifarma Spa | Procedimento per la produzione di acido 3-indolpiruvico e suoi derivati loro uso farmaceutico |
| IT1224546B (it) * | 1988-09-29 | 1990-10-04 | Polifarma Spa | Utilizzatore farmaceutica di acido 3 -indolpiruvico come agente inibitore di patologie degenerative |
| IT1232167B (it) * | 1989-08-08 | 1992-01-25 | Polifarma Spa | Uso cosmetico di acido 3-indolpiruvico |
| IT1237472B (it) * | 1989-10-04 | 1993-06-07 | Polifarma Spa | Derivati di acido 3-indolpiruvico, loro procedimento di produzione ed impiego terapeutico. |
| IT1261165B (it) * | 1993-01-25 | 1996-05-09 | Polifarma Spa | Agente attivo per ridurre il livello ematico di glucocorticoidi e prevenire disturbi cerebrali da stress e senilita'. |
| US7297800B2 (en) * | 2001-12-27 | 2007-11-20 | Ajinomoto Co., Inc. | Process of producing glutamate derivatives |
| CN101671707A (zh) | 2001-12-27 | 2010-03-17 | 味之素株式会社 | 谷氨酸衍生物的制备方法 |
| RU2307871C2 (ru) | 2002-08-26 | 2007-10-10 | Адзиномото Ко., Инк. | НОВАЯ АЛЬДОЛАЗА И СПОСОБ ПОЛУЧЕНИЯ ЗАМЕЩЕННЫХ α-КЕТОКИСЛОТ |
| CN1723281B (zh) | 2002-12-09 | 2012-08-15 | 味之素株式会社 | 突变的d-氨基转移酶和使用它们生产旋光性谷氨酸衍生物的方法 |
| US7180370B2 (en) * | 2004-09-01 | 2007-02-20 | Micron Technology, Inc. | CMOS amplifiers with frequency compensating capacitors |
| WO2009028338A1 (ja) | 2007-08-24 | 2009-03-05 | Ajinomoto Co., Inc. | 新規オキシダーゼ遺伝子、および該遺伝子を利用する３－インドールピルビン酸の製造方法 |
| CN102741406A (zh) | 2010-10-14 | 2012-10-17 | 味之素株式会社 | 用于产生莽那亭的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1148618B (it) * | 1982-10-11 | 1986-12-03 | Polifarma Spa | Procedimento enzimatico per la produzione di acido 3-indolpiruvico e utilizzazione farmaceutica di questo |
-
1985
- 1985-06-28 IT IT48295/85A patent/IT1184282B/it active
-
1986
- 1986-06-10 CA CA000511265A patent/CA1267148A/en not_active Expired - Lifetime
- 1986-06-24 JP JP61503721A patent/JPS62501912A/ja active Granted
- 1986-06-24 DE DE8686904336T patent/DE3673786D1/de not_active Expired - Lifetime
- 1986-06-24 KR KR1019870700175A patent/KR930008227B1/ko not_active Expired - Fee Related
- 1986-06-24 US US07/033,099 patent/US4808728A/en not_active Expired - Lifetime
- 1986-06-24 EP EP86904336A patent/EP0227787B1/en not_active Expired - Lifetime
- 1986-06-24 WO PCT/IT1986/000045 patent/WO1987000169A1/en active IP Right Grant
- 1986-06-24 BR BR8606750A patent/BR8606750A/pt not_active IP Right Cessation
- 1986-06-24 AU AU61313/86A patent/AU583648B2/en not_active Expired
- 1986-06-25 ES ES556673A patent/ES8800903A1/es not_active Expired
-
1987
- 1987-02-16 DK DK076687A patent/DK157921C/da not_active IP Right Cessation
- 1987-02-27 FI FI870869A patent/FI83772C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR870700603A (ko) | 1987-12-30 |
| DK157921C (da) | 1990-08-20 |
| DK76687D0 (da) | 1987-02-16 |
| ES556673A0 (es) | 1987-12-01 |
| EP0227787B1 (en) | 1990-08-29 |
| ES8800903A1 (es) | 1987-12-01 |
| IT1184282B (it) | 1987-10-22 |
| AU583648B2 (en) | 1989-05-04 |
| IT8548295A0 (it) | 1985-06-28 |
| EP0227787A1 (en) | 1987-07-08 |
| DK76687A (da) | 1987-02-16 |
| BR8606750A (pt) | 1987-10-13 |
| US4808728A (en) | 1989-02-28 |
| FI870869L (fi) | 1987-02-27 |
| DK157921B (da) | 1990-03-05 |
| DE3673786D1 (de) | 1990-10-04 |
| FI83772B (fi) | 1991-05-15 |
| FI83772C (fi) | 1991-08-26 |
| WO1987000169A1 (en) | 1987-01-15 |
| AU6131386A (en) | 1987-01-30 |
| KR930008227B1 (ko) | 1993-08-27 |
| JPH0422909B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-04-20 |
| JPS62501912A (ja) | 1987-07-30 |
| FI870869A0 (fi) | 1987-02-27 |
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