JPH0544472B2 - - Google Patents
Info
- Publication number
- JPH0544472B2 JPH0544472B2 JP60000019A JP1985A JPH0544472B2 JP H0544472 B2 JPH0544472 B2 JP H0544472B2 JP 60000019 A JP60000019 A JP 60000019A JP 1985 A JP1985 A JP 1985A JP H0544472 B2 JPH0544472 B2 JP H0544472B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- addition salt
- acid addition
- acid
- vinblastine
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 13
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 10
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 10
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 229960003048 vinblastine Drugs 0.000 claims description 10
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 229930013930 alkaloid Natural products 0.000 claims description 6
- -1 chromic acid alcohol ester Chemical class 0.000 claims description 6
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims description 6
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 5
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- QEYLDKWOZQLWNL-UHFFFAOYSA-N CCC(C)(C)O[Cr](=O)(=O)OC(C)(C)CC Chemical compound CCC(C)(C)O[Cr](=O)(=O)OC(C)(C)CC QEYLDKWOZQLWNL-UHFFFAOYSA-N 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 229960004528 vincristine Drugs 0.000 description 16
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 16
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 239000007858 starting material Substances 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000001085 cytostatic effect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VDIWWRZMCKHBRD-UHFFFAOYSA-M CCC(C)(C)O[Cr](O)(=O)=O Chemical compound CCC(C)(C)O[Cr](O)(=O)=O VDIWWRZMCKHBRD-UHFFFAOYSA-M 0.000 description 1
- 240000001829 Catharanthus roseus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 241000863480 Vinca Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- WBGPNPZUWVTYAA-UHFFFAOYSA-N methane;dihydrochloride Chemical compound C.Cl.Cl WBGPNPZUWVTYAA-UHFFFAOYSA-N 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- OBEIXXHHUOSBLA-UQUCNHJPSA-N n-deformylvincristine Chemical compound C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 OBEIXXHHUOSBLA-UQUCNHJPSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/04—Dimeric indole alkaloids, e.g. vincaleucoblastine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ åŒïŒïŒ ïŒåŒäžãã¯ã¡ãã«åºãŸãã¯ãã«ãã«åºã§ããïŒ
ã§è¡šããããäºéäœã¢ã«ã«ãã€ãããã³ãã®é žä»
å å¡©ã補é ããã«ããããåŒïŒïŒ ã§è¡šãããããã³ãã©ã¹ãã³ããç¡é¢ä¿æº¶åªäž
ã§ãé žåã¯ãã ïŒïŒãŸãã¯éã¯ãã é žå¡©ãŸãã¯
ã¯ãã é žã¢ã«ã³ãŒã«ãšã¹ãã«ã«ãã€ãŠé žåããã
ãããŠåŸãããåŒïŒïŒãããã§ãã¯ã¡ãã«åº
ã§ãããã®ãšãããã§è¡šããããååç©ãé žä»å
å¡©ã«å€ãããããŠå Žåã«ãããåŸãããé žä»å å¡©
ãåèšé žåå€ã«ãã€ãŠæŽã«é žåãããããŠå Žåã«
ãããããããŠåŸãããåŒïŒïŒãããã§ãã¯
ãã«ãã«åºã§ãããã®ãšãããã§è¡šããããåå
ç©ãé žä»å å¡©ã«å€ããããšãããªãåèšåŒïŒïŒ
ã§è¡šããããäºéäœã¢ã«ã«ãã€ãããã³ãã®é žä»
å å¡©ã®è£œæ³ã ïŒ ç¡é¢ä¿æº¶åªãšããŠããã²ã³åçåæ°ŽçŽ ã䜿çš
ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ ççŽ ååïŒã10åã®èèªæã«ã«ãã³é žã䜿çš
ããŠæº¶è§£ãä¿é²ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ãŸãã¯
第ïŒé èšèŒã®æ¹æ³ã ïŒ ç¡æ°Žé ¢é žæº¶æ¶²äžã§é žåã¯ãã ïŒïŒã䜿çšã
ãç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ é žã®ååšäžã§éã¯ãã é žå¡©ã䜿çšããç¹èš±è«
æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ ã¯ãã é žã¢ã«ã³ãŒã«ãšã¹ãã«ãšããŠã¯ãã é ž
ãžïŒïœâããã«ïŒãŸãã¯ãžïŒïœâã¢ãã«ïŒã䜿çš
ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ ãã³ãã©ã¹ãã³ãéé¢å¡©åºã®åœ¢ã§äœ¿çšããç¹
èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®æ¹æ³ã ïŒ åŒïŒïŒ ïŒåŒäžãã¯ã¡ãã«åºãŸãã¯ãã«ãã«åºã§ããïŒ
ã§è¡šããããæ°èŠååç©ããã³ãã®é žä»å å¡©ã
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU8449A HU190219B (en) | 1984-01-06 | 1984-01-06 | Process for preparing in 3",7'-position cyclized dimer-cinca-alkaloid-derivatives |
HU2251/49/84 | 1984-01-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60174791A JPS60174791A (ja) | 1985-09-09 |
JPH0544472B2 true JPH0544472B2 (ja) | 1993-07-06 |
Family
ID=10947652
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60000019A Granted JPS60174791A (ja) | 1984-01-06 | 1985-01-04 | æ°èŠäºéäœã¢ã«ã«ãã€ãããã³ãã®è£œæ³ |
Country Status (10)
Country | Link |
---|---|
US (1) | US4659816A (ja) |
JP (1) | JPS60174791A (ja) |
BE (1) | BE901446A (ja) |
CA (1) | CA1242192A (ja) |
FR (1) | FR2557877B1 (ja) |
GB (1) | GB2152506B (ja) |
HU (1) | HU190219B (ja) |
IL (1) | IL73884A (ja) |
SE (1) | SE462685B (ja) |
ZA (1) | ZA849909B (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09314479A (ja) * | 1996-05-28 | 1997-12-09 | Fuji Tekunika:Kk | äœçœ®æ±ºããã³çšåŒãæãè£ çœ® |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2582651B1 (fr) * | 1985-06-03 | 1987-08-28 | Pf Medicament | Procede de preparation de vincristine |
JP5046356B2 (ja) * | 2006-01-12 | 2012-10-10 | æ ªåŒäŒç€ŸïŒ¬ïœïœïœïœ | éå£éšè£ 眮 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH434281A (de) * | 1964-03-04 | 1967-04-30 | Geigy Ag J R | Verfahren zur Herstellung von polycyclischen Indolderivaten |
US3899493A (en) * | 1972-12-29 | 1975-08-12 | Richter Gedeon Vegyeszet | Chromic acid oxidation of vinblastine sulfate to form vincristine |
US4303584A (en) * | 1980-04-02 | 1981-12-01 | Eli Lilly And Company | Method of preparing vincristine |
US4375432A (en) * | 1981-05-12 | 1983-03-01 | Eli Lilly And Company | Method of preparing vincristine |
-
1984
- 1984-01-06 HU HU8449A patent/HU190219B/hu not_active IP Right Cessation
- 1984-12-19 ZA ZA849909A patent/ZA849909B/xx unknown
- 1984-12-20 IL IL73884A patent/IL73884A/xx unknown
- 1984-12-28 CA CA000471111A patent/CA1242192A/en not_active Expired
-
1985
- 1985-01-04 US US06/688,932 patent/US4659816A/en not_active Expired - Fee Related
- 1985-01-04 JP JP60000019A patent/JPS60174791A/ja active Granted
- 1985-01-04 SE SE8500040A patent/SE462685B/sv not_active IP Right Cessation
- 1985-01-04 BE BE0/214292A patent/BE901446A/fr not_active IP Right Cessation
- 1985-01-04 FR FR858500076A patent/FR2557877B1/fr not_active Expired
- 1985-01-07 GB GB08500321A patent/GB2152506B/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09314479A (ja) * | 1996-05-28 | 1997-12-09 | Fuji Tekunika:Kk | äœçœ®æ±ºããã³çšåŒãæãè£ çœ® |
Also Published As
Publication number | Publication date |
---|---|
IL73884A0 (en) | 1985-03-31 |
GB2152506B (en) | 1987-12-23 |
FR2557877B1 (fr) | 1989-06-16 |
CA1242192A (en) | 1988-09-20 |
SE462685B (sv) | 1990-08-13 |
SE8500040D0 (sv) | 1985-01-04 |
BE901446A (fr) | 1985-07-04 |
GB8500321D0 (en) | 1985-02-13 |
FR2557877A1 (fr) | 1985-07-12 |
ZA849909B (en) | 1985-10-30 |
US4659816A (en) | 1987-04-21 |
SE8500040L (sv) | 1985-07-07 |
JPS60174791A (ja) | 1985-09-09 |
IL73884A (en) | 1988-09-30 |
GB2152506A (en) | 1985-08-07 |
HU190219B (en) | 1986-08-28 |
HUT36131A (en) | 1985-08-28 |
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