JPS6310160B2 - - Google Patents
Info
- Publication number
- JPS6310160B2 JPS6310160B2 JP56152488A JP15248881A JPS6310160B2 JP S6310160 B2 JPS6310160 B2 JP S6310160B2 JP 56152488 A JP56152488 A JP 56152488A JP 15248881 A JP15248881 A JP 15248881A JP S6310160 B2 JPS6310160 B2 JP S6310160B2
- Authority
- JP
- Japan
- Prior art keywords
- extract
- ether
- water
- dehydropregnenolone
- solvent
- 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
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 239000000284 extract Substances 0.000 claims description 18
- YLFRRPUBVUAHSR-RRPFGEQOSA-N 16,17-didehydropregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC=C(C(=O)C)[C@@]1(C)CC2 YLFRRPUBVUAHSR-RRPFGEQOSA-N 0.000 claims description 14
- YLFRRPUBVUAHSR-UHFFFAOYSA-N 16-dehydro-pregnenolone Natural products C1C=C2CC(O)CCC2(C)C2C1C1CC=C(C(=O)C)C1(C)CC2 YLFRRPUBVUAHSR-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000354 decomposition reaction Methods 0.000 claims description 7
- 239000003550 marker Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 238000005192 partition Methods 0.000 claims description 2
- 239000000419 plant extract Substances 0.000 claims 1
- 150000005856 steroid saponins Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 description 6
- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 241000234273 Dioscorea Species 0.000 description 3
- 235000005903 Dioscorea Nutrition 0.000 description 3
- 235000000504 Dioscorea villosa Nutrition 0.000 description 3
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000004879 dioscorea Nutrition 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- NHBDEADLHQSGDF-SGKAZYAESA-N (1S,2S,3'S,4S,6R,7S,8R,9S,12S,13R,16S)-3',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,6'-oxane]-3',16-diol Chemical compound C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CC[C@](C)(O)CO1 NHBDEADLHQSGDF-SGKAZYAESA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000007056 Dioscorea composita Nutrition 0.000 description 2
- 241000156497 Dioscorea composita Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NHBDEADLHQSGDF-UHFFFAOYSA-N Isonuatigenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)(O)CO1 NHBDEADLHQSGDF-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 230000004720 fertilization Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- NELZMZLNTYWIPD-MLBSDYKWSA-N nuatigenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@](C)(CO)O1 NELZMZLNTYWIPD-MLBSDYKWSA-N 0.000 description 2
- NELZMZLNTYWIPD-FTFHAVOMSA-N nuatigenin Natural products OC[C@@]1(C)O[C@]2([C@H](C)[C@@H]3[C@]4(C)[C@H]([C@H]5[C@@H]([C@]6(C)C(=CC5)C[C@@H](O)CC6)CC4)C[C@@H]3O2)CC1 NELZMZLNTYWIPD-FTFHAVOMSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 description 1
- 241001504639 Alcedo atthis Species 0.000 description 1
- 235000008499 Canella winterana Nutrition 0.000 description 1
- 235000010240 Paullinia pinnata Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 244000020282 Solanum aculeatissimum Species 0.000 description 1
- 235000004790 Solanum aculeatissimum Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 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
- 239000012345 acetylating agent Substances 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012364 cultivation method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- KKBVNPPUTWMILP-UHFFFAOYSA-N nuatigenin diacetate Chemical compound CC1C(C2(CCC3C4(C)CCC(CC4=CCC3C2C2)OC(C)=O)C)C2OC11CCC(C)(COC(C)=O)O1 KKBVNPPUTWMILP-UHFFFAOYSA-N 0.000 description 1
- 229940127234 oral contraceptive Drugs 0.000 description 1
- 239000003539 oral contraceptive agent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- QZDWODWEESGPLC-UHFFFAOYSA-N pyridin-3-yl acetate Chemical compound CC(=O)OC1=CC=CN=C1 QZDWODWEESGPLC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- -1 various corticoids Substances 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56152488A JPS5855500A (ja) | 1981-09-25 | 1981-09-25 | １６−デヒドロプレグネノロンの製造法 |
| US06/491,964 US4482706A (en) | 1981-09-25 | 1982-09-24 | Steroid saponins |
| DE8282902830T DE3269846D1 (en) | 1981-09-25 | 1982-09-24 | Novel steroid saponins, process for their extraction, and process for preparing 16-dehydropregnenolone therefrom |
| PCT/JP1982/000384 WO1983001065A1 (fr) | 1981-09-25 | 1982-09-24 | Nouvelles saponines steroides, leur procede d'extraction, et procede de preparation de 16-dehydropregnenolone a partir de ces nouvelles saponines |
| EP82902830A EP0089377B1 (en) | 1981-09-25 | 1982-09-24 | Novel steroid saponins, process for their extraction, and process for preparing 16-dehydropregnenolone therefrom |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56152488A JPS5855500A (ja) | 1981-09-25 | 1981-09-25 | １６−デヒドロプレグネノロンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5855500A JPS5855500A (ja) | 1983-04-01 |
| JPS6310160B2 true JPS6310160B2 (enExample) | 1988-03-04 |
Family
ID=15541570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56152488A Granted JPS5855500A (ja) | 1981-09-25 | 1981-09-25 | １６−デヒドロプレグネノロンの製造法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4482706A (enExample) |
| EP (1) | EP0089377B1 (enExample) |
| JP (1) | JPS5855500A (enExample) |
| DE (1) | DE3269846D1 (enExample) |
| WO (1) | WO1983001065A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5862200A (ja) * | 1981-10-07 | 1983-04-13 | Tokiwa Yakuhin Kogyo Kk | １６−デヒドロプレグノロンの製造法 |
| JP2562134B2 (ja) * | 1986-09-19 | 1996-12-11 | 喜徳 喜谷 | 新規な白金−ステロイド錯体 |
| US5808117A (en) * | 1996-01-22 | 1998-09-15 | Chowdhury; Pritish Kumar | Process for the production of 16-Dehydropregenolone acetate form diosgenin |
| GB9923076D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| KR20070007214A (ko) * | 1998-03-26 | 2007-01-12 | 파이토팜 피엘씨 | 알츠하이머병을 치료하기 위한 스밀라게닌 및안주로게닌-ｄ |
| GB9923078D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB9923077D0 (en) * | 1999-09-29 | 1999-12-01 | Phytopharm Plc | Sapogenin derivatives and their use |
| GB0000228D0 (en) * | 2000-01-06 | 2000-03-01 | Phytopharm Plc | Fluoro substituted sapogenins and their use |
| GB0107822D0 (en) * | 2001-03-28 | 2001-05-23 | Phytopharm Plc | Sapogenin derivatives their synthesis and use methods based upon their use |
| US20050130948A1 (en) * | 2002-03-27 | 2005-06-16 | Daryl Rees | Therapeutic methods and uses of sapogenins and their derivatives |
| CN102727501A (zh) * | 2002-03-27 | 2012-10-17 | 菲特法姆股份有限公司 | 皂角苷配基及其衍生物的用途 |
| JP2010535758A (ja) * | 2008-01-04 | 2010-11-25 | ビオスペクトルム，インコーポレイテッド | ジオスゲニンを含む皮膚美白用組成物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3294785A (en) * | 1963-07-29 | 1966-12-27 | Schering Corp | Novel process for the conversion of a sapogenin to a 16-dehydro steroid and intermediates produced thereby |
| GB1503388A (en) * | 1975-07-01 | 1978-03-08 | Inverni Della Beffa Spa | Pharmaceutically active complexes and pharmaceutical compositions containing them |
| GB2019407B (en) * | 1978-04-14 | 1982-10-06 | Yamasa Shoyu Kk | Glycosides of compounds of the 3-hydroxy oleanane series and their extraction from plants of genus periandra |
| DE2926463A1 (de) * | 1978-07-05 | 1980-01-24 | Roecar Holdings Nv | Spiroketaline und ihre verwendung |
| JPS5943960B2 (ja) * | 1979-10-29 | 1984-10-25 | 株式会社大阪薬品研究所 | 新規サポニン物質 |
-
1981
- 1981-09-25 JP JP56152488A patent/JPS5855500A/ja active Granted
-
1982
- 1982-09-24 US US06/491,964 patent/US4482706A/en not_active Expired - Fee Related
- 1982-09-24 DE DE8282902830T patent/DE3269846D1/de not_active Expired
- 1982-09-24 EP EP82902830A patent/EP0089377B1/en not_active Expired
- 1982-09-24 WO PCT/JP1982/000384 patent/WO1983001065A1/ja not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0089377A4 (en) | 1984-11-23 |
| DE3269846D1 (en) | 1986-04-17 |
| JPS5855500A (ja) | 1983-04-01 |
| EP0089377A1 (en) | 1983-09-28 |
| WO1983001065A1 (fr) | 1983-03-31 |
| EP0089377B1 (en) | 1986-03-12 |
| US4482706A (en) | 1984-11-13 |
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