NL8700724A - Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden). - Google Patents

Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden). Download PDF

Info

Publication number: NL8700724A
Authority: NL; Netherlands
Prior art keywords: group; poly; deoxyribonucleotides; formula; protecting
Prior art date: 1987-03-27

Application number

NL8700724A

Other languages

English (en)

Dutch (nl)

Original Assignee

Univ Eindhoven Tech

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.)

1987-03-27

Filing date

1987-03-27

Publication date

1988-10-17

1987-03-27 Application filed by Univ Eindhoven Tech filed Critical Univ Eindhoven Tech

1987-03-27 Priority to NL8700724A priority Critical patent/NL8700724A/nl

1988-03-25 Priority to AT88903410T priority patent/ATE90354T1/de

1988-03-25 Priority to PCT/NL1988/000013 priority patent/WO1988007542A1/en

1988-03-25 Priority to EP88903410A priority patent/EP0358657B1/de

1988-03-25 Priority to DE88903410T priority patent/DE3881691T2/de

1988-03-25 Priority to JP63503102A priority patent/JPH02503911A/ja

1988-10-17 Publication of NL8700724A publication Critical patent/NL8700724A/nl

Links

239000005547 deoxyribonucleotide Substances 0.000 title claims description 30
238000002360 preparation method Methods 0.000 title claims description 9
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 28
239000005549 deoxyribonucleoside Substances 0.000 claims abstract description 13
238000009396 hybridization Methods 0.000 claims abstract description 7
-1 poly(deoxyribonucleotides) Polymers 0.000 claims abstract description 6
230000001580 bacterial effect Effects 0.000 claims abstract description 4
238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
210000004881 tumor cell Anatomy 0.000 claims abstract description 4
125000002637 deoxyribonucleotide group Chemical group 0.000 claims description 26
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 22
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 22
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 22
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 20
238000000034 method Methods 0.000 claims description 17
125000000320 amidine group Chemical group 0.000 claims description 13
CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 13
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 12
229930024421 Adenine Natural products 0.000 claims description 12
229960000643 adenine Drugs 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
229940104302 cytosine Drugs 0.000 claims description 11
229940113082 thymine Drugs 0.000 claims description 11
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
238000007254 oxidation reaction Methods 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
230000003647 oxidation Effects 0.000 claims description 6
244000045947 parasite Species 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 claims description 4
206010012289 Dementia Diseases 0.000 claims description 4
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
208000027760 Muscular autoimmune disease Diseases 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 claims description 4
201000006938 muscular dystrophy Diseases 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
150000003536 tetrazoles Chemical class 0.000 claims description 4
229940104230 thymidine Drugs 0.000 claims description 4
241000894006 Bacteria Species 0.000 claims description 3
206010028980 Neoplasm Diseases 0.000 claims description 3
208000036142 Viral infection Diseases 0.000 claims description 3
241000700605 Viruses Species 0.000 claims description 3
201000011510 cancer Diseases 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
230000008878 coupling Effects 0.000 claims description 3
238000010168 coupling process Methods 0.000 claims description 3
238000005859 coupling reaction Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
230000009385 viral infection Effects 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
230000004913 activation Effects 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
FBZVZUSVGKOWHG-UHFFFAOYSA-N 1,1-dimethoxy-n,n-dimethylethanamine Chemical compound COC(C)(OC)N(C)C FBZVZUSVGKOWHG-UHFFFAOYSA-N 0.000 claims 1
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical group OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
238000003745 diagnosis Methods 0.000 abstract 1
230000003071 parasitic effect Effects 0.000 abstract 1
230000003612 virological effect Effects 0.000 abstract 1
108020004414 DNA Proteins 0.000 description 24
102000053602 DNA Human genes 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
125000003835 nucleoside group Chemical group 0.000 description 8
239000000126 substance Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 5
239000002777 nucleoside Substances 0.000 description 5
150000003833 nucleoside derivatives Chemical class 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
108091034117 Oligonucleotide Proteins 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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 description 4
238000006642 detritylation reaction Methods 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical group CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 4
238000001308 synthesis method Methods 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000295 complement effect Effects 0.000 description 3
239000005289 controlled pore glass Substances 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
102000040430 polynucleotide Human genes 0.000 description 3
108091033319 polynucleotide Proteins 0.000 description 3
239000002157 polynucleotide Substances 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
230000036760 body temperature Effects 0.000 description 2
210000000170 cell membrane Anatomy 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000523 sample Substances 0.000 description 2
125000006850 spacer group Chemical group 0.000 description 2
230000007704 transition Effects 0.000 description 2
YQMUORJJDBQCOV-UHFFFAOYSA-N $l^{1}-phosphanylmethane Chemical compound [P]C YQMUORJJDBQCOV-UHFFFAOYSA-N 0.000 description 1
SBKCKZYFAIFJPV-UHFFFAOYSA-N (6-amino-7h-purin-2-yl)-phenylmethanone Chemical compound N=1C=2N=CNC=2C(N)=NC=1C(=O)C1=CC=CC=C1 SBKCKZYFAIFJPV-UHFFFAOYSA-N 0.000 description 1
KHWCHTKSEGGWEX-RRKCRQDMSA-N 2'-deoxyadenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(O)=O)O1 KHWCHTKSEGGWEX-RRKCRQDMSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
CFIBTBBTJWHPQV-UHFFFAOYSA-N 2-methyl-n-(6-oxo-3,7-dihydropurin-2-yl)propanamide Chemical group N1C(NC(=O)C(C)C)=NC(=O)C2=C1N=CN2 CFIBTBBTJWHPQV-UHFFFAOYSA-N 0.000 description 1
ZTRXFCGYDLPIDD-UHFFFAOYSA-N 4-amino-1-benzoylpyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1C(=O)C1=CC=CC=C1 ZTRXFCGYDLPIDD-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
108020004635 Complementary DNA Proteins 0.000 description 1
241000557626 Corvus corax Species 0.000 description 1
102000006947 Histones Human genes 0.000 description 1
108010033040 Histones Proteins 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
108091028043 Nucleic acid sequence Proteins 0.000 description 1
101710093543 Probable non-specific lipid-transfer protein Proteins 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
238000010804 cDNA synthesis Methods 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
230000004663 cell proliferation Effects 0.000 description 1
239000002299 complementary DNA Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000009881 electrostatic interaction Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical group CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002605 large molecules Chemical class 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
239000000155 melt Substances 0.000 description 1
DGVNWNYQSOYWKZ-UHFFFAOYSA-N methyl dihydrogen phosphite Chemical group COP(O)O DGVNWNYQSOYWKZ-UHFFFAOYSA-N 0.000 description 1
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
150000008300 phosphoramidites Chemical class 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000010076 replication Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
239000013598 vector 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
- A61P31/04—Antibacterial agents
- 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
- A61P35/00—Antineoplastic agents

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Virology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL8700724A 1987-03-27 1987-03-27 Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden). NL8700724A (nl)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
NL8700724A NL8700724A (nl)	1987-03-27	1987-03-27	Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden).
AT88903410T ATE90354T1 (de)	1987-03-27	1988-03-25	Polydeoxyribonukleotide, pharmazeutische zusammensetzungen, verwendung und herstellung von polydeoxyribonukleotiden.
PCT/NL1988/000013 WO1988007542A1 (en)	1987-03-27	1988-03-25	Poly(deoxyribonucleotides), pharmaceutical compositions, use and preparation of the poly(deoxyribonucleotides)
EP88903410A EP0358657B1 (de)	1987-03-27	1988-03-25	Polydeoxyribonukleotide, pharmazeutische zusammensetzungen, verwendung und herstellung von polydeoxyribonukleotiden
DE88903410T DE3881691T2 (de)	1987-03-27	1988-03-25	Polydeoxyribonukleotide, pharmazeutische zusammensetzungen, verwendung und herstellung von polydeoxyribonukleotiden.
JP63503102A JPH02503911A (ja)	1987-03-27	1988-03-25	ポリ（デオキシリボヌクレオチド）、及びその医薬組成物、用途及び製造方法

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8700724A NL8700724A (nl)	1987-03-27	1987-03-27	Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden).
NL8700724		1987-03-27

Publications (1)

Publication Number	Publication Date
NL8700724A true NL8700724A (nl)	1988-10-17

Family

ID=19849775

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8700724A NL8700724A (nl)	1987-03-27	1987-03-27	Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden).

Country Status (6)

Country	Link
EP (1)	EP0358657B1 (de)
JP (1)	JPH02503911A (de)
AT (1)	ATE90354T1 (de)
DE (1)	DE3881691T2 (de)
NL (1)	NL8700724A (de)
WO (1)	WO1988007542A1 (de)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996039414A1 (en) *	1995-06-01	1996-12-12	Hybridon, Inc.	Novel base protecting groups for oligonucleotide synthesis
WO1996039413A1 (en) *	1995-05-23	1996-12-12	Hybridon, Inc.	Methods and compounds for the synthesis of oligonucleotides and the oligonucleotides thereby produced
US5750674A (en) *	1995-05-23	1998-05-12	Hybridon, Inc.	Methods and compounds for the stereoselective enrichment of oligonucleotide diastereomers and oligonucleotides thereby produced
WO1998033806A1 (en) *	1997-02-04	1998-08-06	Hybridon, Inc.	Base protecting groups and process for oligonucleotide synthesis
US5962674A (en) *	1995-06-01	1999-10-05	Hybridon, Inc.	Synthesis of oligonucleotides containing alkylphosphonate internucleoside linkages
US6531589B1 (en)	1995-06-01	2003-03-11	Hybridon, Inc.	Base protecting groups and synthons for oligonucleotide synthesis

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1992020697A1 (en) *	1991-05-10	1992-11-26	Hybridon, Inc.	3'-end blocked oligonucleotides
US5502177A (en) *	1993-09-17	1996-03-26	Gilead Sciences, Inc.	Pyrimidine derivatives for labeled binding partners
US9481905B2 (en) *	2013-02-19	2016-11-01	Orizhan Bioscience Limited	Method of using neutrilized DNA (N-DNA) as surface probe for high throughput detection platform
EP3943500A1 (de)	2014-04-30	2022-01-26	Agilent Technologies, Inc.	Phosphorschutzgruppen und verfahren zu ihrer herstellung und ihre verwendung

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0090789A1 (de) *	1982-03-26	1983-10-05	Monsanto Company	Chemische DNA-Synthese
EP0108387B1 (de) *	1982-11-04	1990-05-16	F. Hoffmann-La Roche Ag	Hestellung von rekombinanten wachstumsauslösenden Faktoren

1987
- 1987-03-27 NL NL8700724A patent/NL8700724A/nl not_active Application Discontinuation
1988
- 1988-03-25 EP EP88903410A patent/EP0358657B1/de not_active Expired - Lifetime
- 1988-03-25 JP JP63503102A patent/JPH02503911A/ja active Pending
- 1988-03-25 WO PCT/NL1988/000013 patent/WO1988007542A1/en not_active Ceased
- 1988-03-25 DE DE88903410T patent/DE3881691T2/de not_active Expired - Fee Related
- 1988-03-25 AT AT88903410T patent/ATE90354T1/de not_active IP Right Cessation

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1996039413A1 (en) *	1995-05-23	1996-12-12	Hybridon, Inc.	Methods and compounds for the synthesis of oligonucleotides and the oligonucleotides thereby produced
US5750674A (en) *	1995-05-23	1998-05-12	Hybridon, Inc.	Methods and compounds for the stereoselective enrichment of oligonucleotide diastereomers and oligonucleotides thereby produced
WO1996039414A1 (en) *	1995-06-01	1996-12-12	Hybridon, Inc.	Novel base protecting groups for oligonucleotide synthesis
US5962674A (en) *	1995-06-01	1999-10-05	Hybridon, Inc.	Synthesis of oligonucleotides containing alkylphosphonate internucleoside linkages
US6531589B1 (en)	1995-06-01	2003-03-11	Hybridon, Inc.	Base protecting groups and synthons for oligonucleotide synthesis
WO1998033806A1 (en) *	1997-02-04	1998-08-06	Hybridon, Inc.	Base protecting groups and process for oligonucleotide synthesis

Also Published As

Publication number	Publication date
WO1988007542A1 (en)	1988-10-06
ATE90354T1 (de)	1993-06-15
DE3881691D1 (de)	1993-07-15
EP0358657B1 (de)	1993-06-09
EP0358657A1 (de)	1990-03-21
JPH02503911A (ja)	1990-11-15
DE3881691T2 (de)	1993-09-30

Legal Events

Date	Code	Title	Description
1988-10-17	A1B	A search report has been drawn up
1991-11-01	BV	The patent application has lapsed

Publication	Publication Date	Title
CA2160016C (en)	2008-06-03	Method of forming oligonucleotides
AU2006317195B2 (en)	2010-04-01	Polynucleotide containing a phosphate mimetic
US6291188B1 (en)	2001-09-18	Metallic solid supports modified with nucleic acids
IL104461A (en)	2001-05-20	Oligonucleotide analogs, their preparation and pharmaceutical compositions containing them
JP2008013571A (ja)	2008-01-24	カチオン性オリゴヌクレオチド、ならびに関連の合成および使用の方法
JPH11500924A (ja)	1999-01-26	核酸分析の方法
JP2002527523A (ja)	2002-08-27	機能付与したピリミジン誘導体
JP3676388B2 (ja)	2005-07-27	非ヌクレオチド基を有する３′−誘導されたオリゴヌクレオチド類似体、その製法および使用
Herrlein et al.	1994	Selective chemical autoligation on a double-stranded DNA template
US5652350A (en)	1997-07-29	Complementary DNA and toxins
EP0358657B1 (de)	1993-06-09	Polydeoxyribonukleotide, pharmazeutische zusammensetzungen, verwendung und herstellung von polydeoxyribonukleotiden
EP2550368A1 (de)	2013-01-30	Kombinatorische bibliothek, verfahren zur herstellung dieser kombinatorischen bibliothek, verfahren zur sequenzidentifikation, verfahren zur sequenzierung der elemente kombinatorischer bibliotheken aus oligonucleotiden und/oder oligonucleotidanaloga, verwendung eines vernetzers zur erzeugung kombinatorischer bibliotheken und ein sequenzidentifikationssatz
JPH04503403A (ja)	1992-06-18	５′―結合アクリジンを有するホスホロチオエートおよび通常のオリゴデオキシヌクレオチド
Thuong et al.	1989	Oligodeoxynucleotides covalently linked to intercalating and reactive substances: synthesis, characterization and physicochemical studies
JP3593344B6 (ja)	2005-02-16	オリゴヌクレオチドの形成方法
JP2001524972A (ja)	2001-12-04	キメラオリゴヌクレオチド及びその使用
Noronha	1999	Synthesis Physicochemical and Biological Studies on Oligonucleotides Containing D-arabinose

NL8700724A - Poly(deoxyribonucleotiden), farmaceutische samenstellingen, gebruik en bereiding van de poly(deoxyribonucleotiden). - Google Patents

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Priority Applications (6)

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Publications (1)

Family

ID=19849775

Family Applications (1)

Country Status (6)

Cited By (6)

Families Citing this family (4)

Family Cites Families (2)

Cited By (6)

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