CN1019806B - 利拜卡霉素类似物的制备方法 - Google Patents
利拜卡霉素类似物的制备方法Info
- Publication number
- CN1019806B CN1019806B CN87107928A CN87107928A CN1019806B CN 1019806 B CN1019806 B CN 1019806B CN 87107928 A CN87107928 A CN 87107928A CN 87107928 A CN87107928 A CN 87107928A CN 1019806 B CN1019806 B CN 1019806B
- Authority
- CN
- China
- Prior art keywords
- compound
- profit
- rebeccamycin
- formula
- group
- 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
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- CZDBNBLGZNWKMC-MWQNXGTOSA-N olivomycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1)O[C@H]1O[C@@H](C)[C@H](O)[C@@H](OC2O[C@@H](C)[C@H](O)[C@@H](O)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@H](O)[C@H](OC)[C@H](C)O1 CZDBNBLGZNWKMC-MWQNXGTOSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007885 tablet disintegrant 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
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- 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
- C07H19/044—Pyrrole radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07H19/23—Heterocyclic radicals containing two or more heterocyclic rings condensed among themselves or condensed with a common carbocyclic ring system, not provided for in groups C07H19/14 - C07H19/22
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US933,428 | 1986-11-21 | ||
| US06/933,428 US4785085A (en) | 1986-11-21 | 1986-11-21 | Rebeccamycin analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN87107928A CN87107928A (zh) | 1988-08-10 |
| CN1019806B true CN1019806B (zh) | 1992-12-30 |
Family
ID=25463937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN87107928A Expired CN1019806B (zh) | 1986-11-21 | 1987-11-20 | 利拜卡霉素类似物的制备方法 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4785085A (https=) |
| EP (1) | EP0269025B1 (https=) |
| JP (1) | JPS63198695A (https=) |
| KR (1) | KR910000897B1 (https=) |
| CN (1) | CN1019806B (https=) |
| AT (1) | ATE84539T1 (https=) |
| AU (1) | AU614068B2 (https=) |
| CA (1) | CA1287349C (https=) |
| CS (1) | CS265248B2 (https=) |
| CY (1) | CY1701A (https=) |
| DE (1) | DE3783577T2 (https=) |
| DK (1) | DK165986C (https=) |
| EG (1) | EG18409A (https=) |
| ES (1) | ES2053510T3 (https=) |
| FI (1) | FI86189C (https=) |
| GR (1) | GR3006776T3 (https=) |
| HK (1) | HK49093A (https=) |
| HU (1) | HU201773B (https=) |
| IE (1) | IE60595B1 (https=) |
| IL (1) | IL84515A (https=) |
| MX (1) | MX9202849A (https=) |
| MY (1) | MY102722A (https=) |
| NO (1) | NO167741C (https=) |
| NZ (1) | NZ222544A (https=) |
| PT (1) | PT86188B (https=) |
| SG (1) | SG25193G (https=) |
| YU (1) | YU46087B (https=) |
| ZA (1) | ZA878714B (https=) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07113027B2 (ja) * | 1987-12-24 | 1995-12-06 | 協和醗酵工業株式会社 | Ｋ−２５２誘導体 |
| DE3835842A1 (de) * | 1988-10-21 | 1990-04-26 | Goedecke Ag | Indolocarbazol-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel |
| US5438050A (en) * | 1988-02-06 | 1995-08-01 | Godecke Aktiengesellschaft | Indolocarbazole derivatives, processes for their preparation and compositions containing them |
| US5015578A (en) * | 1989-03-23 | 1991-05-14 | Bristol-Myers Squibb Company | BMY-41950 antitumor antibiotic |
| CA2015996C (en) * | 1989-05-05 | 2001-08-28 | Hartmut Osswald | Bis-(1h-indol-3-yl)-maleinimide derivatives and their use as pharmaceuticals |
| US5496809A (en) * | 1989-05-10 | 1996-03-05 | Bristol-Myers Squibb Co | Stable solutions of rebeccamycin analog |
| US5344823A (en) * | 1990-03-06 | 1994-09-06 | Bristol-Myers Squibb Company | Antitumor antibiotic BMY-41219 |
| CA2037596C (en) * | 1990-03-06 | 1995-07-18 | Kin Sing Lam | Rebeccamycin analog by bromide precursor feeding |
| IL97233A (en) * | 1990-03-06 | 1995-03-30 | Bristol Myers Squibb Co | Rebeccamycin analogs, their production and pharmaceutical compositions containing them |
| US5158938A (en) * | 1990-03-06 | 1992-10-27 | Bristol-Myers Squibb Company | Rebeccamycin |
| US5478813A (en) * | 1990-05-11 | 1995-12-26 | Banyu Pharmaceutical Co., Ltd. | Antitumor substance BE-13793C derivatives |
| JP3064416B2 (ja) * | 1990-05-11 | 2000-07-12 | 萬有製薬株式会社 | 抗腫瘍性物質ｂｅ―１３７９３ｃ誘導体 |
| US5589365A (en) * | 1991-11-29 | 1996-12-31 | Banyu Pharmaceutical Co., Ltd. | Process for producing glycosylated indolopyrrolocarbazole derivatives by culturing certain microorganisms |
| US5437996A (en) * | 1992-11-24 | 1995-08-01 | Banyu Pharmaceutical Co., Ltd. | Microtetraspora strain for preparation of indolopyrrolocarbazole derivatives |
| NZ245203A (en) * | 1991-11-29 | 1997-07-27 | Banyu Pharma Co Ltd | 5h-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6h)-dione derivatives substituted in position-13 by a pentose or hexose group; corresponding indolo-furano(anhydride)intermediates |
| US5591842A (en) * | 1991-11-29 | 1997-01-07 | Banyu Pharmaceutical Co., Ltd. | Indolopyrrolocarbazole derivatives |
| US5547976A (en) * | 1992-03-20 | 1996-08-20 | Burroughs Wellcome Co. | Further indole derivatives with antiviral activity |
| JP3603322B2 (ja) * | 1992-12-14 | 2004-12-22 | 萬有製薬株式会社 | インドロピロロカルバゾール誘導体の製造法 |
| US5843935A (en) * | 1993-12-07 | 1998-12-01 | Eli Lilly And Company | Protein kinase C inhibitors |
| US5541347A (en) * | 1993-12-07 | 1996-07-30 | Eli Lilly And Company | Synthesis of bisindolylmaleimides |
| DK0657411T3 (da) * | 1993-12-07 | 1999-11-15 | Lilly Co Eli | Forbedret syntese af bisindolylmaleimider |
| NO308798B1 (no) * | 1993-12-07 | 2000-10-30 | Lilly Co Eli | Proteinkinase-C-hemmere, anvendelse av samme for fremstilling av farmasøytika samt farmasøytisk formulering omfattende samme |
| US5723456A (en) * | 1993-12-07 | 1998-03-03 | Eli Lilly & Company | Therapeutic treatment for cardiovascular diseases |
| US5624949A (en) * | 1993-12-07 | 1997-04-29 | Eli Lilly And Company | Protein kinase C inhibitors |
| ES2236702T3 (es) * | 1993-12-23 | 2005-07-16 | Eli Lilly And Company | Inhibidores de la proteina quinasa c. |
| US5545636A (en) * | 1993-12-23 | 1996-08-13 | Eli Lilly And Company | Protein kinase C inhibitors |
| US5804564A (en) * | 1994-05-09 | 1998-09-08 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazole derivatives |
| WO1995030682A1 (en) * | 1994-05-09 | 1995-11-16 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyprolocarbazole derivative |
| US5922860A (en) * | 1994-05-09 | 1999-07-13 | Banyu Pharmaceutical Co., Ltd. | Antitumor indolopyrrolocarbazole derivatives |
| EP0769555B1 (en) * | 1994-06-13 | 2003-09-03 | Banyu Pharmaceutical Co., Ltd. | Gene coding for glycosyltransferase and use thereof |
| US5491242A (en) * | 1994-06-22 | 1996-02-13 | Eli Lilly And Company | Protein kinase C inhibitors |
| US5481003A (en) * | 1994-06-22 | 1996-01-02 | Eli Lilly And Company | Protein kinase C inhibitors |
| DK0695755T3 (da) * | 1994-08-04 | 1999-06-28 | Hoffmann La Roche | Pyrrolocarbazoler |
| WO1997009339A1 (fr) * | 1995-09-05 | 1997-03-13 | Banyu Pharmaceutical Co., Ltd. | Derives antitumoraux d'indolopyrrolocarbazole |
| EP0888339A4 (en) * | 1996-03-20 | 2001-02-28 | Lilly Co Eli | SYNTHESIS OF INDOLYLMALEINIMIDES |
| US5859261A (en) * | 1997-03-20 | 1999-01-12 | Eli Lilly And Company | Synthesis of indolylmaleimides |
| US6610727B2 (en) | 2000-10-06 | 2003-08-26 | Bristol-Myers Squibb Company | Anhydro sugar derivatives of indolocarbazoles |
| US6677450B2 (en) | 2000-10-06 | 2004-01-13 | Bristol-Myers Squibb Company | Topoisomerase inhibitors |
| US6653290B2 (en) * | 2000-10-06 | 2003-11-25 | Bristol-Myers Squibb Company | Tumor proliferation inhibitors |
| KR20030085035A (ko) | 2001-03-22 | 2003-11-01 | 브리스톨-마이어스스퀴브컴파니 | 토포아이소머라아제 ｉ 선택성 세포독성인돌로피롤로카바졸 당 유도체 |
| JP4202250B2 (ja) | 2001-07-25 | 2008-12-24 | バイオマリン ファーマシューティカル インコーポレイテッド | 血液脳関門輸送を調節するための組成物および方法 |
| CA2393720C (en) * | 2002-07-12 | 2010-09-14 | Eli Lilly And Company | Crystalline 2,5-dione-3-(1-methyl-1h-indol-3-yl)-4-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1h-indol-3-yl]-1h-pyrrole mono-hydrochloride |
| EP1666485A1 (en) * | 2003-09-16 | 2006-06-07 | Banyu Pharmaceutical Co., Ltd. | Novel indolopyrrolocarbazole derivative with antitumor activity |
| EP2671507A3 (en) | 2005-04-28 | 2014-02-19 | Proteus Digital Health, Inc. | Pharma-informatics system |
| MX2009002893A (es) | 2006-09-18 | 2009-07-10 | Raptor Pharmaceutical Inc | Tratamiento de trastornos hepaticos mediante la administracion de conjugados de la proteina asociada al receptor (rap). |
| ES2326459B1 (es) | 2008-04-08 | 2010-05-28 | Universidad De Oviedo | Indolocarbazoles glicosilados, su procedimiento de obtencion y sus usos. |
| CA2752373C (en) | 2009-02-20 | 2017-10-10 | To-Bbb Holding B.V. | Glutathione-based drug delivery system |
| IL255113B (en) | 2009-05-06 | 2022-09-01 | Laboratory Skin Care Inc | Dermal delivery compositions comprising active agent-calcium phosphate particle complexes and methods of using the same |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| CN102125578B (zh) * | 2010-11-24 | 2013-03-27 | 河南师范大学 | 具有抗癌活性的蝴蝶霉素类似物及合成方法 |
| CN102898489B (zh) * | 2010-11-24 | 2014-04-02 | 河南师范大学 | 具有抗癌活性的蝴蝶霉素类似物及合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4487925A (en) * | 1983-01-28 | 1984-12-11 | Bristol-Myers Company | Rebeccamycin and process for its preparation |
| US4552842A (en) * | 1983-01-28 | 1985-11-12 | Bristol-Myers Company | Process for producing rebeccamycin |
| US4524145A (en) * | 1984-09-04 | 1985-06-18 | Bristol-Myers Company | 4'-Deschlororebeccamycin pharmaceutical composition and method of use |
| JPS62220196A (ja) * | 1986-03-20 | 1987-09-28 | Kyowa Hakko Kogyo Co Ltd | 新規物質ｕｃｎ―０１ |
-
1986
- 1986-11-21 US US06/933,428 patent/US4785085A/en not_active Expired - Lifetime
-
1987
- 1987-11-12 AU AU81148/87A patent/AU614068B2/en not_active Expired
- 1987-11-13 NZ NZ222544A patent/NZ222544A/en unknown
- 1987-11-17 CS CS878249A patent/CS265248B2/cs not_active IP Right Cessation
- 1987-11-17 EG EG656/87A patent/EG18409A/xx active
- 1987-11-18 YU YU208687A patent/YU46087B/sh unknown
- 1987-11-18 FI FI875091A patent/FI86189C/fi not_active IP Right Cessation
- 1987-11-18 IL IL84515A patent/IL84515A/xx not_active IP Right Cessation
- 1987-11-20 PT PT86188A patent/PT86188B/pt unknown
- 1987-11-20 ES ES87117167T patent/ES2053510T3/es not_active Expired - Lifetime
- 1987-11-20 CN CN87107928A patent/CN1019806B/zh not_active Expired
- 1987-11-20 NO NO874857A patent/NO167741C/no not_active IP Right Cessation
- 1987-11-20 ZA ZA878714A patent/ZA878714B/xx unknown
- 1987-11-20 EP EP87117167A patent/EP0269025B1/en not_active Expired - Lifetime
- 1987-11-20 AT AT87117167T patent/ATE84539T1/de not_active IP Right Cessation
- 1987-11-20 DE DE8787117167T patent/DE3783577T2/de not_active Expired - Lifetime
- 1987-11-20 JP JP62293854A patent/JPS63198695A/ja active Granted
- 1987-11-20 KR KR1019870013102A patent/KR910000897B1/ko not_active Expired
- 1987-11-20 CA CA000552337A patent/CA1287349C/en not_active Expired - Lifetime
- 1987-11-20 MY MYPI87003080A patent/MY102722A/en unknown
- 1987-11-20 DK DK612987A patent/DK165986C/da not_active IP Right Cessation
- 1987-11-20 IE IE315287A patent/IE60595B1/en not_active IP Right Cessation
- 1987-11-20 HU HU875164A patent/HU201773B/hu unknown
-
1992
- 1992-06-12 MX MX9202849A patent/MX9202849A/es unknown
-
1993
- 1993-01-14 GR GR920402547T patent/GR3006776T3/el unknown
- 1993-03-06 SG SG251/93A patent/SG25193G/en unknown
- 1993-05-20 HK HK490/93A patent/HK49093A/en not_active IP Right Cessation
-
1994
- 1994-01-14 CY CY170194A patent/CY1701A/xx unknown
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