CA2058632C - Oligonucleotides resistant a l'exonuclease et methodes de preparation - Google Patents

Oligonucleotides resistant a l'exonuclease et methodes de preparation Download PDF

Info

Publication number: CA2058632C
Authority: CA; Canada
Prior art keywords: oligonucleotide; carbon atoms; linkages; hydrogen; phosphoramidate
Prior art date: 1989-06-05
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

Application number

CA002058632A

Other languages

English (en)

Other versions

CA2058632A1 (fr

Inventor

Brian C. Froehler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ionis Pharmaceuticals Inc

Original Assignee

Isis Pharmaceuticals Inc

Priority date (The priority date 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 date listed.)

1989-06-05

Filing date

1990-06-05

Publication date

2004-08-24

1990-06-05 Application filed by Isis Pharmaceuticals Inc filed Critical Isis Pharmaceuticals Inc

1990-12-06 Publication of CA2058632A1 publication Critical patent/CA2058632A1/fr

2004-08-24 Application granted granted Critical

2004-08-24 Publication of CA2058632C publication Critical patent/CA2058632C/fr

2010-06-05 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 94
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 abstract description 28
238000000034 method Methods 0.000 title abstract description 23
108060002716 Exonuclease Proteins 0.000 title abstract description 13
102000013165 exonuclease Human genes 0.000 title abstract description 13
PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims abstract description 39
230000015556 catabolic process Effects 0.000 claims abstract description 14
238000006731 degradation reaction Methods 0.000 claims abstract description 14
230000000295 complement effect Effects 0.000 claims abstract description 12
NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 claims abstract description 9
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims abstract description 6
238000009396 hybridization Methods 0.000 claims abstract description 6
230000000694 effects Effects 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
230000004048 modification Effects 0.000 claims description 9
238000012986 modification Methods 0.000 claims description 9
125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
150000008298 phosphoramidates Chemical group 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
230000004962 physiological condition Effects 0.000 claims description 2
239000002777 nucleoside Substances 0.000 description 22
-1 phosphate triester Chemical class 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
229920000642 polymer Polymers 0.000 description 15
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150000005690 diesters Chemical class 0.000 description 13
230000003647 oxidation Effects 0.000 description 13
238000007254 oxidation reaction Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
150000004713 phosphodiesters Chemical class 0.000 description 12
108020004414 DNA Proteins 0.000 description 10
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102000040430 polynucleotide Human genes 0.000 description 10
239000002157 polynucleotide Substances 0.000 description 10
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UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical class [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 9
150000001412 amines Chemical class 0.000 description 8
239000002773 nucleotide Substances 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
230000008878 coupling Effects 0.000 description 7
238000010168 coupling process Methods 0.000 description 7
238000005859 coupling reaction Methods 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
125000003729 nucleotide group Chemical group 0.000 description 7
229940046166 oligodeoxynucleotide Drugs 0.000 description 7
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
241000700605 Viruses Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
108091032973 (ribonucleotides)n+m Proteins 0.000 description 4
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 4
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
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Classifications

- 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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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

CA002058632A 1989-06-05 1990-06-05 Oligonucleotides resistant a l'exonuclease et methodes de preparation Expired - Lifetime CA2058632C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US36104589A	1989-06-05	1989-06-05
US361,045		1989-06-05
PCT/US1990/003138 WO1990015065A1 (fr)	1989-06-05	1990-06-05	Oligonucleotides resistant a l'exonuclease, et procedes pour leur preparation

Publications (2)

Publication Number	Publication Date
CA2058632A1 CA2058632A1 (fr)	1990-12-06
CA2058632C true CA2058632C (fr)	2004-08-24

Family

ID=23420432

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002058632A Expired - Lifetime CA2058632C (fr)	1989-06-05	1990-06-05	Oligonucleotides resistant a l'exonuclease et methodes de preparation

Country Status (5)

Country	Link
EP (1)	EP0476071A4 (fr)
JP (1)	JPH05500799A (fr)
KR (1)	KR920701230A (fr)
CA (1)	CA2058632C (fr)
WO (1)	WO1990015065A1 (fr)

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US5434257A (en) *	1992-06-01	1995-07-18	Gilead Sciences, Inc.	Binding compentent oligomers containing unsaturated 3',5' and 2',5' linkages
CA2140542A1 (fr) *	1992-07-27	1994-02-03	Abeysingle Padmapriya	Alkylphosphonothioates d'oligonucleotides
US5580972A (en) *	1993-06-14	1996-12-03	Nexstar Pharmaceuticals, Inc.	Purine nucleoside modifications by palladium catalyzed methods
US5719273A (en) *	1993-06-14	1998-02-17	Nexstar Pharmaceuticals, Inc.	Palladium catalyzed nucleoside modifications methods using nucleophiles and carbon monoxide
WO1995025180A1 (fr) *	1994-03-16	1995-09-21	Gen-Probe Incorporated	Amplification d'acide nucleique par deplacement de la souche isotherme
EP0830368A1 (fr)	1995-06-07	1998-03-25	Genta Incorporated	Nouveaux lipides cationiques a base de carbamate
US6111095A (en) *	1995-06-07	2000-08-29	Merck & Co., Inc.	Capped synthetic RNA, analogs, and aptamers
EP0932698A1 (fr) *	1996-03-26	1999-08-04	Lynx Therapeutics, Inc.	Traitements a base d'oligonucleotides et compositions contre les melanomes humains
US5959100A (en) *	1996-03-27	1999-09-28	Nexstar Pharmaceuticals, Inc.	Pyrimidine nucleosides as therapeutic and diagnostic agents
US5945527A (en) *	1996-05-30	1999-08-31	Nexstar Pharmaceuticals, Inc.	Palladium catalyzed nucleoside modification methods using nucleophiles and carbon monoxide
US6172209B1 (en)	1997-02-14	2001-01-09	Isis Pharmaceuticals Inc.	Aminooxy-modified oligonucleotides and methods for making same
US6127533A (en)	1997-02-14	2000-10-03	Isis Pharmaceuticals, Inc.	2'-O-aminooxy-modified oligonucleotides
US6576752B1 (en)	1997-02-14	2003-06-10	Isis Pharmaceuticals, Inc.	Aminooxy functionalized oligomers
US6028183A (en)	1997-11-07	2000-02-22	Gilead Sciences, Inc.	Pyrimidine derivatives and oligonucleotides containing same
US6007992A (en) *	1997-11-10	1999-12-28	Gilead Sciences, Inc.	Pyrimidine derivatives for labeled binding partners
US6867294B1 (en)	1998-07-14	2005-03-15	Isis Pharmaceuticals, Inc.	Gapped oligomers having site specific chiral phosphorothioate internucleoside linkages
US6043352A (en)	1998-08-07	2000-03-28	Isis Pharmaceuticals, Inc.	2'-O-Dimethylaminoethyloxyethyl-modified oligonucleotides
US6673912B1 (en)	1998-08-07	2004-01-06	Isis Pharmaceuticals, Inc.	2′-O-aminoethyloxyethyl-modified oligonucleotides
US6020483A (en)	1998-09-25	2000-02-01	Nexstar Pharmaceuticals, Inc.	Nucleoside modifications by palladium catalyzed methods
US6207819B1 (en) *	1999-02-12	2001-03-27	Isis Pharmaceuticals, Inc.	Compounds, processes and intermediates for synthesis of mixed backbone oligomeric compounds
AU2001262108A1 (en) *	2000-03-17	2001-09-24	Unilever Plc	Non-physiologic dna fragments for tanning skin
AU9475001A (en) *	2000-09-26	2002-04-08	Hybridon Inc	Modulation of immunostimulatory activity of immunostimulatory oligonucleotide analogs by positional chemical changes
US7129261B2 (en)	2001-05-31	2006-10-31	Medarex, Inc.	Cytotoxic agents
US7255874B1 (en)	2001-12-21	2007-08-14	Closure Medical Corporation	Biocompatible polymers and adhesives: compositions, methods of making and uses related thereto
US7002006B2 (en)	2003-02-12	2006-02-21	Isis Pharmaceuticals, Inc.	Protection of nucleosides
EP1660512A4 (fr)	2003-06-02	2009-12-23	Isis Pharmaceuticals Inc	Synthese d'oligonucleotides au moyen de solvants alternatifs
US7125945B2 (en)	2003-09-19	2006-10-24	Varian, Inc.	Functionalized polymer for oligonucleotide purification
JP4806680B2 (ja)	2004-05-19	2011-11-02	メダレックスインコーポレイテッド	自己犠牲リンカー及び薬剤複合体
WO2006023880A2 (fr)	2004-08-23	2006-03-02	Isis Pharmaceuticals, Inc.	Composes et procedes permettant de caracteriser les oligonucleotides
BRPI0617546A2 (pt)	2005-09-26	2011-07-26	Medarex Inc	conjugado de fÁrmaco-anticorpo, formulaÇço farmacÊutica, mÉtodo para matar uma cÉlula de tumor, mÉtodo para retardar ou interromper o crescimento de um tumor em um sujeito mamÍfero e composto
US7947447B2 (en)	2007-01-16	2011-05-24	Somalogic, Inc.	Method for generating aptamers with improved off-rates
US8583380B2 (en)	2008-09-05	2013-11-12	Aueon, Inc.	Methods for stratifying and annotating cancer drug treatment options
EP3345915B1 (fr)	2010-04-12	2021-11-24	Somalogic, Inc.	Pyramidines modifiés en position 5 et leur utilisation
BR112016010165A2 (pt)	2013-11-21	2017-12-05	Somalogic Inc	composições de nucleotídeos modificados de citidina-5-carboxamida e métodos relacionados às mesmas
WO2016011174A1 (fr) *	2014-07-15	2016-01-21	Life Technologies Corporation	Compositions et méthodes d'assemblage d'acides nucléiques
DK3236972T3 (en)	2014-12-26	2021-10-04	Univ Emory	Antivirale N4-hydroxycytidin-derivativer
JP6804790B1 (ja)	2017-12-07	2020-12-23	エモリーユニバーシティー	Ｎ４−ヒドロキシシチジンおよび誘導体ならびにそれらに関連する抗ウイルス用途
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US4415732A (en) *	1981-03-27	1983-11-15	University Patents, Inc.	Phosphoramidite compounds and processes
US4849513A (en) *	1983-12-20	1989-07-18	California Institute Of Technology	Deoxyribonucleoside phosphoramidites in which an aliphatic amino group is attached to the sugar ring and their use for the preparation of oligonucleotides containing aliphatic amino groups
WO1986007362A1 (fr) *	1985-06-14	1986-12-18	University Patents, Inc.	Methode de synthese de desoxyoligonucleotides
ATE151467T1 (de) *	1987-11-30	1997-04-15	Univ Iowa Res Found	Durch modifikationen an der 3'-terminalen phosphodiesterbindung stabilisierte dna moleküle, ihre verwendung als nukleinsäuresonden sowie als therapeutische mittel zur hemmung der expression spezifischer zielgene

1990
- 1990-06-05 KR KR1019910701767A patent/KR920701230A/ko not_active Withdrawn
- 1990-06-05 JP JP2509531A patent/JPH05500799A/ja active Pending
- 1990-06-05 CA CA002058632A patent/CA2058632C/fr not_active Expired - Lifetime
- 1990-06-05 EP EP19900913804 patent/EP0476071A4/en not_active Withdrawn
- 1990-06-05 WO PCT/US1990/003138 patent/WO1990015065A1/fr not_active Ceased

Also Published As

Publication number	Publication date
EP0476071A4 (en)	1992-11-04
JPH05500799A (ja)	1993-02-18
EP0476071A1 (fr)	1992-03-25
WO1990015065A1 (fr)	1990-12-13
CA2058632A1 (fr)	1990-12-06
KR920701230A (ko)	1992-08-11

Legal Events

Date	Code	Title	Description
1992-09-15	EEER	Examination request
2010-06-05	MKEX	Expiry

Publication	Publication Date	Title
CA2058632C (fr)	2004-08-24	Oligonucleotides resistant a l'exonuclease et methodes de preparation
US5256775A (en)	1993-10-26	Exonuclease-resistant oligonucleotides
US5264564A (en)	1993-11-23	Oligonucleotide analogs with novel linkages
CA2071483C (fr)	2001-04-17	Analogues d'oligonucleotides avec nouvelles liaisons
ES2516815T3 (es)	2014-10-31	Análogos de ácidos nucleicos bicíclicos modificados en la posición 6
US5434257A (en)	1995-07-18	Binding compentent oligomers containing unsaturated 3',5' and 2',5' linkages
AU762212C (en)	2004-02-12	Oligonucleotides having A-DNA form and B-DNA form conformational geometry
US5264562A (en)	1993-11-23	Oligonucleotide analogs with novel linkages
DE69126530T2 (de)	1998-02-05	Nuklease resistente, pyrimidin modifizierte oligonukleotide, die die gen-expression detektieren und modulieren
EP2173760B2 (fr)	2015-11-04	Analogues d'acide nucléique bicyclique carbocylique
DE69232699T2 (de)	2003-02-06	Über chirale phosphoratome gebundene oligonukleotide
DE69109100T2 (de)	1995-08-31	Oligonukleotid-analoge.
CA2092002A1 (fr)	1992-03-21	Liaisons internucleosidiques modifiees
JPH06507883A (ja)	1994-09-08	メチレンホスホネートヌクレオシド類似体およびそれから作られるオリゴヌクレオチド類似体
JP2004500330A (ja)	2004-01-08	グアニジニウム官能化オリゴマーとその製造法
WO2011017521A2 (fr)	2011-02-10	Analogues d'acides nucléiques cyclohexoses bicycliques
NO303018B1 (no)	1998-05-18	AnalogifremgangsmÕte for fremstilling av terapeutisk aktive oligonukleotider
US6017895A (en)	2000-01-25	Oligonucleotides possessing zwitterionic moieties
RU2088588C1 (ru)	1997-08-27	Олигонуклеотиды и способ их получения
JP3911703B2 (ja)	2007-05-09	アンチセンス核酸同族体
AU2002325599B2 (en)	2005-11-03	Oligonucleotide analogues
WO1993010140A1 (fr)	1993-05-27	Oligonucleotides a fractions anioniques modifiees
EP0641354A1 (fr)	1995-03-08	Oligonucleotides comprenant des fractions de phosphonate d'aminohydrocarbure