KR920012107A - 3'-(2')-아미노- 또는 티올-변형되고 형광 염료-결합된 뉴클레오사이드, 뉴클레오타이드 및 올리고뉴클레오타이드, 및 이의 제조방법 및 용도 - Google Patents
3'-(2')-아미노- 또는 티올-변형되고 형광 염료-결합된 뉴클레오사이드, 뉴클레오타이드 및 올리고뉴클레오타이드, 및 이의 제조방법 및 용도 Download PDFInfo
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- KR920012107A KR920012107A KR1019910022614A KR910022614A KR920012107A KR 920012107 A KR920012107 A KR 920012107A KR 1019910022614 A KR1019910022614 A KR 1019910022614A KR 910022614 A KR910022614 A KR 910022614A KR 920012107 A KR920012107 A KR 920012107A
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- 108091034117 Oligonucleotide Proteins 0.000 title claims 5
- 239000007850 fluorescent dye Substances 0.000 title claims 5
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 title claims 4
- 125000003835 nucleoside group Chemical group 0.000 title claims 4
- 239000002773 nucleotide Substances 0.000 title claims 4
- 125000003729 nucleotide group Chemical group 0.000 title claims 4
- 238000000034 method Methods 0.000 title claims 3
- 239000002777 nucleoside Substances 0.000 title claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 3
- -1 fluoro Methylene, difluoromethylene Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims 1
- 235000011180 diphosphates Nutrition 0.000 claims 1
- ZFKJVJIDPQDDFY-UHFFFAOYSA-N fluorescamine Chemical compound C12=CC=CC=C2C(=O)OC1(C1=O)OC=C1C1=CC=CC=C1 ZFKJVJIDPQDDFY-UHFFFAOYSA-N 0.000 claims 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims 1
- 238000001917 fluorescence detection Methods 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 claims 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- MPLHNVLQVRSVEE-UHFFFAOYSA-N texas red Chemical compound [O-]S(=O)(=O)C1=CC(S(Cl)(=O)=O)=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 MPLHNVLQVRSVEE-UHFFFAOYSA-N 0.000 claims 1
- 235000011178 triphosphate Nutrition 0.000 claims 1
- 239000001226 triphosphate Substances 0.000 claims 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- 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
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
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- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
- C12Q1/6816—Hybridisation assays characterised by the detection means
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- 일반식(I)와 3′-및/또는 2′-아미노- 및 티올-변형된 뉴클레오사이드, 뉴클레오타이드 또는 올리고뉴클레오타이드.상기 식에서, R1은 퓨린 또는 피리미딘 염기이고, 라디칼 R2및 R3중 적어도 하나는 아미노 또는 티올 그룹을 통해 결합되는 α 또는 β위치에 존재하는 형광 염료이고, 다른 라디칼은 α 또는 β위치에 존재하는 임의의 수소, 하이드록실, 보호된 하이드록실 또는 메톡시 그룹이며, n은 0 이상의 수이고, R4는 5′ 보호그룹 또는 포스페이트, 피로포스페이트, 트리포스페이트이며, R5는 산소, 플루오로메틸렌, 디플루오로메틸렌 또는 메틸렌이고, R6는 α 또는 β위치에 존재하는 하이드록실 또는 메톡시 그룹 또는 수소(이때, R1, R5및 R6는 각각의 경우에 동일하거나 상이할 수 있다)이며, X 및 Y는 산소, 황, NH 또는 메틸렌(이때, X 및 Y는 각각의 경우에 동일하거나 상이할 수 있다)이다.
- 뉴클레오사이드, 뉴클레오타이드 또는 올리고뉴클레오타이드의 3′및/또는 2′위치에 존재하는 OH그룹을 아미노 또는 티올 그룹으로 유도체화시킨 후 형광 염료상에 결합시킴을 특징으로 하여, 제1항에 따른 일반식(I)의 화합물을 제조하는 방법.
- (a) 일반식(II)의 화합물에 친핵성 공격에 의해 3′ 및/또는 2′ 위치에 보호되거나 보호되지 않는 상태의 아지드 또는 티올을 도입시키고, 필요한 경우 아지드를 아민으로 환원시키고, (b) 아미노 그룹 또는 티올 그룹을 통해 형광 염료를 결합시킴을 특징으로 하여, 일반식(I)의 화합물을 제조하는 방법.상기 식에서, R1내지 R6, X, Y 및 n은 제1항에서 정의한 바와 같고, R1, R5및 R6는 각각의 경우에서 동일하거나 상이한 의미를 가지며, R7및 R8은 수소, 하이드록실 또는 보호된 하이드록실 또는 메톡시 그룹이다.
- 제3항에 있어서, 형광 염료로서 플루오레세인, 로다민, 텍사스 레드(Texas red), NBD, 코우마린, 플루오레스카민, 숙시닐 플루오레세인 및 단실을 사용하는 방법.
- (a) DAN 및 RNA 뉴클레오사이드, 뉴클레오타이드 및 올리뉴클레오타이드의 합성, 및 (b) 생체내 및 시험관내에서 현미경적 및 육안적 형광검출을 위한 제1항에 따른 일반식(I)의 화합물의 용도.
- 제5항에 있어서, 일반식(I)의 화합물의 (a)주형 본쇄의 존재하에서 상보적 본쇄의 합성, 및 (b) 올리고뉴클레오타이드의 합성을 위한 용도.※ 참고사항: 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4039488 | 1990-12-11 | ||
| DEP4039488.3 | 1990-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920012107A true KR920012107A (ko) | 1992-07-25 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910022614A KR920012107A (ko) | 1990-12-11 | 1991-12-11 | 3'-(2')-아미노- 또는 티올-변형되고 형광 염료-결합된 뉴클레오사이드, 뉴클레오타이드 및 올리고뉴클레오타이드, 및 이의 제조방법 및 용도 |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US5679785A (ko) |
| EP (1) | EP0490281B1 (ko) |
| JP (1) | JP3140127B2 (ko) |
| KR (1) | KR920012107A (ko) |
| AT (1) | ATE142222T1 (ko) |
| AU (1) | AU643856B2 (ko) |
| BG (1) | BG61484B1 (ko) |
| BR (1) | BR9105335A (ko) |
| CA (1) | CA2057475A1 (ko) |
| CS (1) | CS374391A3 (ko) |
| DE (1) | DE59108143D1 (ko) |
| DK (1) | DK0490281T3 (ko) |
| ES (1) | ES2093671T3 (ko) |
| FI (1) | FI915779A (ko) |
| GR (1) | GR3021041T3 (ko) |
| HU (1) | HUT60505A (ko) |
| IE (1) | IE75726B1 (ko) |
| IL (1) | IL100298A (ko) |
| MX (1) | MX9102468A (ko) |
| NO (1) | NO914859L (ko) |
| NZ (1) | NZ240900A (ko) |
| PL (1) | PL168874B1 (ko) |
| PT (1) | PT99747A (ko) |
| RO (1) | RO111575B1 (ko) |
| RU (1) | RU2073682C1 (ko) |
| TR (1) | TR27715A (ko) |
| YU (1) | YU187991A (ko) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5476925A (en) * | 1993-02-01 | 1995-12-19 | Northwestern University | Oligodeoxyribonucleotides including 3'-aminonucleoside-phosphoramidate linkages and terminal 3'-amino groups |
| US5599922A (en) * | 1994-03-18 | 1997-02-04 | Lynx Therapeutics, Inc. | Oligonucleotide N3'-P5' phosphoramidates: hybridization and nuclease resistance properties |
| CA2184375C (en) * | 1994-03-18 | 2006-05-02 | Sergei M. Gryaznov | Oligonucleotide n3'-p5' phosphoramidates: synthesis and compounds; hybridization and nuclease resistance properties |
| US5726297A (en) * | 1994-03-18 | 1998-03-10 | Lynx Therapeutics, Inc. | Oligodeoxyribonucleotide N3' P5' phosphoramidates |
| DE4418691A1 (de) * | 1994-05-28 | 1996-02-22 | Boehringer Mannheim Gmbh | 3'-(4'-) nicht-radioaktiv markierte Nukleoside und Nukleotide mit Aminocarbonsäure-, Peptid- oder Carbonsäure-Spacer |
| US5962271A (en) * | 1996-01-03 | 1999-10-05 | Cloutech Laboratories, Inc. | Methods and compositions for generating full-length cDNA having arbitrary nucleotide sequence at the 3'-end |
| US5859233A (en) * | 1996-02-21 | 1999-01-12 | Lynx Therapeutics, Inc. | Synthons for synthesis of oligonucleotide N3-P5 phosphoramidates |
| US5684143A (en) * | 1996-02-21 | 1997-11-04 | Lynx Therapeutics, Inc. | Oligo-2'-fluoronucleotide N3'->P5' phosphoramidates |
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1991
- 1991-12-02 YU YU187991A patent/YU187991A/sh unknown
- 1991-12-04 BG BG95575A patent/BG61484B1/bg unknown
- 1991-12-06 DK DK91120935.1T patent/DK0490281T3/da active
- 1991-12-06 ES ES91120935T patent/ES2093671T3/es not_active Expired - Lifetime
- 1991-12-06 DE DE59108143T patent/DE59108143D1/de not_active Expired - Fee Related
- 1991-12-06 EP EP91120935A patent/EP0490281B1/de not_active Expired - Lifetime
- 1991-12-06 AT AT91120935T patent/ATE142222T1/de not_active IP Right Cessation
- 1991-12-09 TR TR01195/91A patent/TR27715A/xx unknown
- 1991-12-09 IL IL100298A patent/IL100298A/xx not_active IP Right Cessation
- 1991-12-09 RO RO148926A patent/RO111575B1/ro unknown
- 1991-12-09 FI FI915779A patent/FI915779A/fi unknown
- 1991-12-09 NZ NZ24090091A patent/NZ240900A/en unknown
- 1991-12-10 CA CA002057475A patent/CA2057475A1/en not_active Abandoned
- 1991-12-10 MX MX9102468A patent/MX9102468A/es unknown
- 1991-12-10 IE IE430191A patent/IE75726B1/en not_active IP Right Cessation
- 1991-12-10 PT PT99747A patent/PT99747A/pt not_active Application Discontinuation
- 1991-12-10 AU AU88927/91A patent/AU643856B2/en not_active Ceased
- 1991-12-10 NO NO91914859A patent/NO914859L/no unknown
- 1991-12-10 HU HU913885A patent/HUT60505A/hu unknown
- 1991-12-10 CS CS913743A patent/CS374391A3/cs unknown
- 1991-12-10 RU SU915010267A patent/RU2073682C1/ru active
- 1991-12-10 PL PL91292701A patent/PL168874B1/pl unknown
- 1991-12-11 KR KR1019910022614A patent/KR920012107A/ko not_active Application Discontinuation
- 1991-12-11 BR BR919105335A patent/BR9105335A/pt unknown
- 1991-12-11 JP JP03350821A patent/JP3140127B2/ja not_active Expired - Fee Related
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1994
- 1994-01-18 US US08/184,759 patent/US5679785A/en not_active Expired - Fee Related
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1995
- 1995-06-01 US US08/456,734 patent/US5668269A/en not_active Expired - Fee Related
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1996
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