IL96982A - ייצור גליקוסידים הידרוקסי- סטרואידיים מהידרוקסי-סטרואידים בנוכחות יוד יסודי בכמות מזרזת גליקוסיד חדש של כולסטין ותכשירי רוקחות המכ - Google Patents
ייצור גליקוסידים הידרוקסי- סטרואידיים מהידרוקסי-סטרואידים בנוכחות יוד יסודי בכמות מזרזת גליקוסיד חדש של כולסטין ותכשירי רוקחות המכInfo
- Publication number
- IL96982A IL96982A IL9698291A IL9698291A IL96982A IL 96982 A IL96982 A IL 96982A IL 9698291 A IL9698291 A IL 9698291A IL 9698291 A IL9698291 A IL 9698291A IL 96982 A IL96982 A IL 96982A
- Authority
- IL
- Israel
- Prior art keywords
- cholesten
- dideoxy
- erythro
- hexyl
- delta5
- Prior art date
Links
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- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- JXCOSKURGJMQSG-NGNMYJGKSA-N alpha-Allocortolone Chemical compound C[C@]12CC(=O)[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC[C@]2(O)[C@@H](O)CO JXCOSKURGJMQSG-NGNMYJGKSA-N 0.000 description 1
- JXCOSKURGJMQSG-UHFFFAOYSA-N alpha-Cortolone Natural products C1C(O)CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(O)CO)C4C3CCC21 JXCOSKURGJMQSG-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940061641 androsterone Drugs 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000002016 colloidosmotic effect Effects 0.000 description 1
- 229940124301 concurrent medication Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 210000001151 cytotoxic T lymphocyte Anatomy 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 229960003654 desoxycortone Drugs 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010218 electron microscopic analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- XUPLQGYCPSEKNQ-UHFFFAOYSA-H hexasodium dioxido-oxo-sulfanylidene-lambda6-sulfane Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=S.[O-]S([O-])(=O)=S.[O-]S([O-])(=O)=S XUPLQGYCPSEKNQ-UHFFFAOYSA-H 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229960002899 hydroxyprogesterone Drugs 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- AODPIQQILQLWGS-GXBDJPPSSA-N tetrahydrocortisol Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CC[C@@H]21 AODPIQQILQLWGS-GXBDJPPSSA-N 0.000 description 1
- 229940034252 thymus extracts Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 125000002640 tocopherol group Chemical group 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4001895A DE4001895A1 (de) | 1990-01-23 | 1990-01-23 | Herstellung von insbesondere steroidglykosiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL96982A0 IL96982A0 (en) | 1992-03-29 |
| IL96982A true IL96982A (he) | 1996-01-31 |
Family
ID=6398603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9698291A IL96982A (he) | 1990-01-23 | 1991-01-21 | ייצור גליקוסידים הידרוקסי- סטרואידיים מהידרוקסי-סטרואידים בנוכחות יוד יסודי בכמות מזרזת גליקוסיד חדש של כולסטין ותכשירי רוקחות המכ |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5278296A (he) |
| EP (1) | EP0594581B1 (he) |
| JP (2) | JP2612123B2 (he) |
| KR (1) | KR100192005B1 (he) |
| CN (1) | CN1050365C (he) |
| AT (1) | ATE167868T1 (he) |
| AU (1) | AU7148991A (he) |
| CA (1) | CA2073692A1 (he) |
| DE (2) | DE4001895A1 (he) |
| HU (1) | HU214873B (he) |
| IL (1) | IL96982A (he) |
| WO (1) | WO1991011452A1 (he) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5496806A (en) * | 1990-01-23 | 1996-03-05 | R. Erich Klemke | Glycoside compounds and production and use thereof |
| US5693767A (en) * | 1991-01-22 | 1997-12-02 | Harrier Inc. | Glycoside derivatives of acetaminophen |
| IL102566A0 (en) * | 1991-07-22 | 1993-01-14 | Harrier Inc | Glycoside compounds and production and use thereof |
| US5677286A (en) * | 1995-04-27 | 1997-10-14 | The University Of Michigan | Glycosylated analogs of camptothecin |
| KR0169536B1 (ko) * | 1996-02-27 | 1999-01-15 | 손경식 | 신규한 인삼 사포닌, 그의 제조방법 및 이를 유효성분으로 하는 항종양제 |
| US6103884A (en) * | 1996-03-27 | 2000-08-15 | The University Of Michigan | Glycosylated analogs of fusidic acid |
| CN1064048C (zh) * | 1996-08-29 | 2001-04-04 | 中国科学院昆明植物研究所 | 青阳参甙丙至甙庚五个化合物及其制备方法和应用 |
| EP1742636B1 (de) * | 2004-05-05 | 2013-04-10 | Immunopharm Aktiengesellschaft | Präparat zur Behandlung von Krebs |
| FR2953154B1 (fr) * | 2009-11-30 | 2013-07-12 | Rhodia Operations | Procede de preparation d'un catalyseur de deperoxydation |
| US8921533B2 (en) | 2011-07-25 | 2014-12-30 | Chromatin Technologies | Glycosylated valproic acid analogs and uses thereof |
| WO2020097600A1 (en) * | 2018-11-09 | 2020-05-14 | Rmd Sciences Inc. | Compositions for the treatment of cancer and other conditions |
| KR102141656B1 (ko) | 2019-07-16 | 2020-08-05 | 선문대학교 산학협력단 | 글루코실트랜스퍼라제를 이용한 코르티코스테론의 생물 전환 방법 및 이로부터 얻어진 코르티코스테론 글루코시드 |
| CN119143829B (zh) * | 2024-11-06 | 2025-01-28 | 山东省食品药品检验研究院 | 一种c21甾体皂苷及其制备方法、应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI46067C (fi) * | 1968-04-06 | 1972-12-11 | Hoechst Ag | Menetelmä digitoksigeniiniglykosidien valmistamiseksi. |
| US3857832A (en) * | 1972-03-21 | 1974-12-31 | Warner Lambert Co | Process for the preparation of cardiotonic glycosides |
| US3859047A (en) * | 1973-05-29 | 1975-01-07 | Hoffmann La Roche | Standard for serum cholesterol determination |
| DE2523284B2 (de) * | 1975-05-26 | 1977-03-24 | Nippon Shiny aku Co., Ltd., Kyoto (Japan) | Haemostatische, gefaesstabilisierende und antischockmittel |
| GB1553540A (en) * | 1977-02-23 | 1979-09-26 | Green Cross Corp | Medicaments containing cholesterol derivatives |
| JPS56113799A (en) * | 1980-02-08 | 1981-09-07 | Nippon Shinyaku Co Ltd | Glucoside derivative |
| DE3127933A1 (de) * | 1980-07-18 | 1982-04-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (delta)- oder (beta)-o-glycosyimidaten |
| US4415731A (en) * | 1981-03-30 | 1983-11-15 | Merck & Co., Inc. | Process for the preparation of methyl 2,6-dideoxy-α-D-arabino-hexopyranoside |
| US4629768A (en) * | 1986-05-02 | 1986-12-16 | Olin Corporation | Thermally stable polyurethane elastomers containing glycoside polyols and a method of producing them |
-
1990
- 1990-01-23 DE DE4001895A patent/DE4001895A1/de not_active Withdrawn
-
1991
- 1991-01-21 IL IL9698291A patent/IL96982A/he not_active IP Right Cessation
- 1991-01-22 CA CA002073692A patent/CA2073692A1/en not_active Abandoned
- 1991-01-22 WO PCT/EP1991/000115 patent/WO1991011452A1/en not_active Ceased
- 1991-01-22 HU HU9202121A patent/HU214873B/hu not_active IP Right Cessation
- 1991-01-22 EP EP91902953A patent/EP0594581B1/en not_active Expired - Lifetime
- 1991-01-22 DE DE69129700T patent/DE69129700T2/de not_active Expired - Fee Related
- 1991-01-22 US US07/644,002 patent/US5278296A/en not_active Expired - Lifetime
- 1991-01-22 CN CN91100394A patent/CN1050365C/zh not_active Expired - Fee Related
- 1991-01-22 JP JP3503078A patent/JP2612123B2/ja not_active Expired - Lifetime
- 1991-01-22 AT AT91902953T patent/ATE167868T1/de not_active IP Right Cessation
- 1991-01-22 AU AU71489/91A patent/AU7148991A/en not_active Abandoned
-
1992
- 1992-07-22 KR KR1019920701739A patent/KR100192005B1/ko not_active Expired - Fee Related
-
1995
- 1995-07-18 JP JP7181812A patent/JP2636208B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH08109192A (ja) | 1996-04-30 |
| WO1991011452A1 (en) | 1991-08-08 |
| DE4001895A1 (de) | 1991-07-25 |
| US5278296A (en) | 1994-01-11 |
| ATE167868T1 (de) | 1998-07-15 |
| HUT61778A (en) | 1993-03-01 |
| JP2612123B2 (ja) | 1997-05-21 |
| EP0594581A1 (en) | 1994-05-04 |
| DE69129700T2 (de) | 1999-02-18 |
| IL96982A0 (en) | 1992-03-29 |
| JP2636208B2 (ja) | 1997-07-30 |
| JPH05504565A (ja) | 1993-07-15 |
| AU7148991A (en) | 1991-08-21 |
| EP0594581B1 (en) | 1998-07-01 |
| CN1053239A (zh) | 1991-07-24 |
| HU9202121D0 (en) | 1992-12-28 |
| KR100192005B1 (en) | 1999-06-15 |
| CA2073692A1 (en) | 1991-07-24 |
| DE69129700D1 (de) | 1998-08-06 |
| CN1050365C (zh) | 2000-03-15 |
| HU214873B (hu) | 1998-07-28 |
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