NO328646B1 - Fosfonomononukleinsyrer, anvendelse samt fremgangsmater for fremstilling - Google Patents

Fosfonomononukleinsyrer, anvendelse samt fremgangsmater for fremstilling Download PDF

Info

Publication number: NO328646B1
Authority: NO; Norway
Prior art keywords: formula; compounds; alkyl; stands; onpe
Prior art date: 1995-03-13

Application number

NO19961006A

Other languages

English (en)

Norwegian (no)

Other versions

NO961006D0 (no

NO961006L (no

Inventor

Anuschirwan Peyman

Eugen Uhlmann

Gerhard Breipohl

Holger Wallmeier

Original Assignee

Hoechst Ag

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.)

1995-03-13

Filing date

1996-03-12

Publication date

2010-04-19

1995-03-13 Priority claimed from DE19508923A external-priority patent/DE19508923A1/de

1995-11-24 Priority claimed from DE1995143865 external-priority patent/DE19543865A1/de

1996-03-12 Application filed by Hoechst Ag filed Critical Hoechst Ag

1996-03-12 Publication of NO961006D0 publication Critical patent/NO961006D0/no

1996-09-16 Publication of NO961006L publication Critical patent/NO961006L/no

2010-04-19 Publication of NO328646B1 publication Critical patent/NO328646B1/no

Links

238000000034 method Methods 0.000 title claims description 44
238000002360 preparation method Methods 0.000 title claims description 14
239000002253 acid Substances 0.000 title description 43
150000007513 acids Chemical class 0.000 title description 7
-1 (Ci—Cg)-alkoxy Chemical group 0.000 claims description 137
150000001875 compounds Chemical class 0.000 claims description 120
238000003786 synthesis reaction Methods 0.000 claims description 71
230000015572 biosynthetic process Effects 0.000 claims description 68
108091034117 Oligonucleotide Proteins 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 48
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 claims description 38
239000001257 hydrogen Substances 0.000 claims description 38
125000006239 protecting group Chemical group 0.000 claims description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
229940104302 cytosine Drugs 0.000 claims description 24
239000002904 solvent Substances 0.000 claims description 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
229940035893 uracil Drugs 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
150000007523 nucleic acids Chemical class 0.000 claims description 15
229910052794 bromium Inorganic materials 0.000 claims description 14
239000003153 chemical reaction reagent Substances 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 13
230000008878 coupling Effects 0.000 claims description 13
238000010168 coupling process Methods 0.000 claims description 13
238000005859 coupling reaction Methods 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 13
108020004707 nucleic acids Proteins 0.000 claims description 13
102000039446 nucleic acids Human genes 0.000 claims description 13
239000007787 solid Substances 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
PNWOYKVCNDZOLS-UHFFFAOYSA-N 6-amino-5-chloro-1h-pyrimidin-2-one Chemical compound NC=1NC(=O)N=CC=1Cl PNWOYKVCNDZOLS-UHFFFAOYSA-N 0.000 claims description 10
239000000074 antisense oligonucleotide Substances 0.000 claims description 10
238000012230 antisense oligonucleotides Methods 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
108020000948 Antisense Oligonucleotides Proteins 0.000 claims description 9
239000002777 nucleoside Substances 0.000 claims description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
241000208140 Acer Species 0.000 claims description 7
239000004305 biphenyl Substances 0.000 claims description 7
235000010290 biphenyl Nutrition 0.000 claims description 7
150000003833 nucleoside derivatives Chemical class 0.000 claims description 7
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 7
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
238000009396 hybridization Methods 0.000 claims description 6
108090000765 processed proteins & peptides Proteins 0.000 claims description 6
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
LQLQRFGHAALLLE-UHFFFAOYSA-N 5-bromouracil Chemical compound BrC1=CNC(=O)NC1=O LQLQRFGHAALLLE-UHFFFAOYSA-N 0.000 claims description 5
ZFTBZKVVGZNMJR-UHFFFAOYSA-N 5-chlorouracil Chemical compound ClC1=CNC(=O)NC1=O ZFTBZKVVGZNMJR-UHFFFAOYSA-N 0.000 claims description 5
QFVKLKDEXOWFSL-UHFFFAOYSA-N 6-amino-5-bromo-1h-pyrimidin-2-one Chemical compound NC=1NC(=O)N=CC=1Br QFVKLKDEXOWFSL-UHFFFAOYSA-N 0.000 claims description 5
239000003298 DNA probe Substances 0.000 claims description 5
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 5
ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims description 5
229960004413 flucytosine Drugs 0.000 claims description 5
229960002949 fluorouracil Drugs 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
102000004196 processed proteins & peptides Human genes 0.000 claims description 5
125000001725 pyrenyl group Chemical group 0.000 claims description 5
125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
238000010532 solid phase synthesis reaction Methods 0.000 claims description 4
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical group [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 4
TUFMBCUUDJKPJB-UHFFFAOYSA-N 5-hex-1-ynyl-1h-pyrimidine-2,4-dione Chemical group CCCCC#CC1=CNC(=O)NC1=O TUFMBCUUDJKPJB-UHFFFAOYSA-N 0.000 claims description 3
WFBPQIPZIJSURG-UHFFFAOYSA-N 6-amino-5-hex-1-ynyl-1h-pyrimidin-2-one Chemical group CCCCC#CC1=CNC(=O)N=C1N WFBPQIPZIJSURG-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
108020003215 DNA Probes Proteins 0.000 claims description 3
150000008575 L-amino acids Chemical class 0.000 claims description 3
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 claims description 3
238000004090 dissolution Methods 0.000 claims description 3
125000005519 fluorenylmethyloxycarbonyl group Chemical group 0.000 claims description 3
230000014509 gene expression Effects 0.000 claims description 3
125000001633 hexacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C12)* 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
238000002372 labelling Methods 0.000 claims description 3
239000003446 ligand Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 3
125000005561 phenanthryl group Chemical group 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
241000894007 species Species 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 3
125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 3
229910004013 NO 2 Inorganic materials 0.000 claims description 2
206010028980 Neoplasm Diseases 0.000 claims description 2
241000700605 Viruses Species 0.000 claims description 2
108010013985 adhesion receptor Proteins 0.000 claims description 2
102000019997 adhesion receptor Human genes 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000005336 allyloxy group Chemical group 0.000 claims description 2
125000000539 amino acid group Chemical group 0.000 claims description 2
150000001413 amino acids Chemical class 0.000 claims description 2
230000001588 bifunctional effect Effects 0.000 claims description 2
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125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
230000017455 cell-cell adhesion Effects 0.000 claims description 2
238000004132 cross linking Methods 0.000 claims description 2
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
108010044426 integrins Proteins 0.000 claims description 2
102000006495 integrins Human genes 0.000 claims description 2
QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 claims description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
230000001960 triggered effect Effects 0.000 claims description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical group OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims 1
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical group OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 218
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 198
150000002148 esters Chemical class 0.000 description 100
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 80
238000000746 purification Methods 0.000 description 65
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 64
239000000741 silica gel Substances 0.000 description 64
229910002027 silica gel Inorganic materials 0.000 description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
239000011734 sodium Substances 0.000 description 36
238000005160 1H NMR spectroscopy Methods 0.000 description 31
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 27
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 22
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 18
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
150000005690 diesters Chemical class 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
ALLRHJQTEHJAPD-UHFFFAOYSA-N 1-[(1-diethoxyphosphoryl-2-oxopropyl)-(2-hydroxyethyl)amino]-5-methylpyrimidine-2,4-dione Chemical compound CCOP(=O)(OCC)C(C(C)=O)N(CCO)N1C=C(C)C(=O)NC1=O ALLRHJQTEHJAPD-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
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229920006395 saturated elastomer Polymers 0.000 description 7
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 6
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000969 carrier Substances 0.000 description 5
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HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 5
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230000001717 pathogenic effect Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000007903 penetration ability Effects 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000006245 phosphate protecting group Chemical group 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
VNUORQWNUXXHLX-UHFFFAOYSA-N pyrazolidine-3-carboxylic acid Chemical compound OC(=O)C1CCNN1 VNUORQWNUXXHLX-UHFFFAOYSA-N 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
NDUWNWVXAYLZSO-UHFFFAOYSA-N pyrrolidin-2-ol Chemical compound OC1CCCN1 NDUWNWVXAYLZSO-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
102000016914 ras Proteins Human genes 0.000 description 1
108010014186 ras Proteins Proteins 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000010076 replication Effects 0.000 description 1
102000027483 retinoid hormone receptors Human genes 0.000 description 1
108091008679 retinoid hormone receptors Proteins 0.000 description 1
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
239000012146 running buffer Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
238000013519 translation Methods 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N tryptophan Chemical compound C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
241000712461 unidentified influenza virus Species 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4087—Esters with arylalkanols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
- C07K14/003—Peptide-nucleic acids (PNAs)

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Virology (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Gastroenterology & Hepatology (AREA)
Biophysics (AREA)
Bioinformatics & Cheminformatics (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Immunology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

NO19961006A 1995-03-13 1996-03-12 Fosfonomononukleinsyrer, anvendelse samt fremgangsmater for fremstilling NO328646B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19508923A DE19508923A1 (de)	1995-03-13	1995-03-13	Phosphonomonoesternukleinsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung
DE1995143865 DE19543865A1 (de)	1995-11-24	1995-11-24	Phosphonomonoesternukleinsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung

Publications (3)

Publication Number	Publication Date
NO961006D0 NO961006D0 (no)	1996-03-12
NO961006L NO961006L (no)	1996-09-16
NO328646B1 true NO328646B1 (no)	2010-04-19

Family

ID=26013308

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19961006A NO328646B1 (no)	1995-03-13	1996-03-12	Fosfonomononukleinsyrer, anvendelse samt fremgangsmater for fremstilling

Country Status (22)

Country	Link
US (2)	US5874553A (ru)
EP (1)	EP0739898B1 (ru)
JP (1)	JP3917680B2 (ru)
KR (1)	KR100434213B1 (ru)
CN (1)	CN1060781C (ru)
AR (1)	AR002714A1 (ru)
AT (1)	ATE206131T1 (ru)
AU (1)	AU706470B2 (ru)
BR (1)	BR9600993B1 (ru)
CA (1)	CA2171589C (ru)
CZ (1)	CZ292037B6 (ru)
DE (1)	DE59607750D1 (ru)
DK (1)	DK0739898T3 (ru)
ES (1)	ES2165446T3 (ru)
HK (1)	HK1012398A1 (ru)
HU (1)	HUP9600647A3 (ru)
IL (1)	IL117423A (ru)
NO (1)	NO328646B1 (ru)
NZ (1)	NZ286150A (ru)
PL (1)	PL184920B1 (ru)
PT (1)	PT739898E (ru)
UA (1)	UA44253C2 (ru)

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US7704962B1 (en)	1997-10-03	2010-04-27	Board Of Regents, The University Of Texas System	Small oligonucleotides with anti-tumor activity
US7285288B1 (en)	1997-10-03	2007-10-23	Board Of Regents, The University Of Texas System	Inhibition of Bcl-2 protein expression by liposomal antisense oligodeoxynucleotides
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US6962906B2 (en) *	2000-03-14	2005-11-08	Active Motif	Oligonucleotide analogues, methods of synthesis and methods of use
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US9150606B2 (en) *	2002-11-05	2015-10-06	Isis Pharmaceuticals, Inc.	Compositions comprising alternating 2'-modified nucleosides for use in gene modulation
US9150605B2 (en)	2002-11-05	2015-10-06	Isis Pharmaceuticals, Inc.	Compositions comprising alternating 2′-modified nucleosides for use in gene modulation
EP1560839A4 (en)	2002-11-05	2008-04-23	Isis Pharmaceuticals Inc	CHIMERIC OLIGOMER COMPOUNDS AND THEIR USE IN GENE MODULATION
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1996
- 1996-03-07 EP EP96103533A patent/EP0739898B1/de not_active Expired - Lifetime
- 1996-03-07 AT AT96103533T patent/ATE206131T1/de active
- 1996-03-07 PT PT96103533T patent/PT739898E/pt unknown
- 1996-03-07 ES ES96103533T patent/ES2165446T3/es not_active Expired - Lifetime
- 1996-03-07 DE DE59607750T patent/DE59607750D1/de not_active Expired - Lifetime
- 1996-03-07 DK DK96103533T patent/DK0739898T3/da active
- 1996-03-10 IL IL117423A patent/IL117423A/en not_active IP Right Cessation
- 1996-03-11 CZ CZ1996743A patent/CZ292037B6/cs not_active IP Right Cessation
- 1996-03-11 US US08/613,417 patent/US5874553A/en not_active Expired - Lifetime
- 1996-03-11 AR ARP960101703A patent/AR002714A1/es unknown
- 1996-03-11 NZ NZ286150A patent/NZ286150A/en not_active IP Right Cessation
- 1996-03-12 CA CA2171589A patent/CA2171589C/en not_active Expired - Fee Related
- 1996-03-12 AU AU48028/96A patent/AU706470B2/en not_active Ceased
- 1996-03-12 PL PL96313207A patent/PL184920B1/pl unknown
- 1996-03-12 UA UA96030965A patent/UA44253C2/uk unknown
- 1996-03-12 NO NO19961006A patent/NO328646B1/no not_active IP Right Cessation
- 1996-03-12 BR BRPI9600993-4A patent/BR9600993B1/pt active IP Right Grant
- 1996-03-13 KR KR1019960006588A patent/KR100434213B1/ko not_active IP Right Cessation
- 1996-03-13 JP JP08480896A patent/JP3917680B2/ja not_active Expired - Fee Related
- 1996-03-13 HU HU9600647A patent/HUP9600647A3/hu unknown
- 1996-03-13 CN CN96100508A patent/CN1060781C/zh not_active Expired - Fee Related
1998
- 1998-11-20 US US09/196,132 patent/US6127346A/en not_active Expired - Lifetime
- 1998-12-15 HK HK98113422A patent/HK1012398A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR960034213A (ko)	1996-10-22
AU4802896A (en)	1996-09-26
CN1138588A (zh)	1996-12-25
DE59607750D1 (de)	2001-10-31
IL117423A (en)	2006-08-20
US6127346A (en)	2000-10-03
EP0739898A2 (de)	1996-10-30
AU706470B2 (en)	1999-06-17
US5874553A (en)	1999-02-23
PL313207A1 (en)	1996-09-16
ATE206131T1 (de)	2001-10-15
CA2171589C (en)	2011-05-10
CZ74396A3 (en)	1996-10-16
UA44253C2 (uk)	2002-02-15
JPH08259579A (ja)	1996-10-08
JP3917680B2 (ja)	2007-05-23
PT739898E (pt)	2002-03-28
HUP9600647A3 (en)	1998-04-28
HUP9600647A1 (en)	1997-05-28
PL184920B1 (pl)	2003-01-31
CZ292037B6 (cs)	2003-07-16
DK0739898T3 (da)	2001-12-10
BR9600993B1 (pt)	2010-05-18
KR100434213B1 (ko)	2004-09-10
NO961006D0 (no)	1996-03-12
AR002714A1 (es)	1998-04-29
IL117423A0 (en)	1996-07-23
BR9600993A (pt)	1997-12-30
ES2165446T3 (es)	2002-03-16
CA2171589A1 (en)	1996-09-14
EP0739898B1 (de)	2001-09-26
NZ286150A (en)	1998-07-28
NO961006L (no)	1996-09-16
HU9600647D0 (en)	1996-05-28
EP0739898A3 (de)	1998-09-16
HK1012398A1 (en)	1999-07-30
CN1060781C (zh)	2001-01-17

Publication	Publication Date	Title
CA2171589C (en)	2011-05-10	Phosphonomonoester nucleic acids, process for their preparation, and their use
AU698928B2 (en)	1998-11-12	Methylphosphonic acid ester, processes for their preperation, and their use
US6479651B1 (en)	2002-11-12	Modified oligonucleotides, their preparation and their use
JP4620810B2 (ja)	2011-01-26	ポリアミド−オリゴヌクレオチド誘導体、その製造及び使用
WO2002018388A1 (fr)	2002-03-07	Analogues de nucleosides et derives d'oligonucleotides renfermant ces analogues
KR100273824B1 (ko)	2000-12-15	비뉴클레오티드성 그룹을 갖는 3'-유도된 올리고뉴클레오티드 동족체, 이의 제조방법 및 이를 함유하는 약제학적 제제
KR20230119637A (ko)	2023-08-16	폴리-모르폴리노 올리고뉴클레오티드 갭머
WO1995024413A1 (en)	1995-09-14	Compositions and methods for use in the synthesis of oligonucleotides
ZA200208344B (en)	2003-08-21	Polyamide nucleic acid derivatives, agents and methods for producing them.
FI111265B (fi)	2003-06-30	Menetelmä lääkeaineina käyttökelpoisten modifioitujen oligodeoksiribonukleotidien valmistamiseksi ja niiden välituotteita
WO2022125984A1 (en)	2022-06-16	Tau-targeting oligonucleotide gapmers
AU2001246536B2 (en)	2007-02-15	Polyamide nucleic acid derivatives, agents and methods for producing the same
US20030203359A1 (en)	2003-10-30	Polyamide-oligonucleotide derivatives, their preparation and use
DE19508923A1 (de)	1996-09-19	Phosphonomonoesternukleinsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung
AU659078B2 (en)	1995-05-11	Polynucleotide phosphorodithioates as therapeutic agents for retroviral infections
EP1397377B1 (en)	2008-08-06	Calix (4) arene-nucleoside and calix (4) arene-oligonucleotide hybrids
DE19543865A1 (de)	1997-06-05	Phosphonomonoesternukleinsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung
US6509459B1 (en)	2003-01-21	Base protecting groups and rapid process for oligonucleotide synthesis
JPH10204097A (ja)	1998-08-04	Ｈ−ホスホネートオリゴヌクレオチド誘導体、及び該誘導体の製造方法
WO1998021226A1 (fr)	1998-05-22	Derive oligonucleotidique h-phosphonate et procede de production associe

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