CA1202254A - Oligonucleotide derivatives and production thereof - Google Patents

Oligonucleotide derivatives and production thereof

Info

Publication number: CA1202254A
Authority: CA; Canada
Prior art keywords: group; oligonucleotide; phospho; shown below; compound
Prior art date: 1982-08-09
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

Application number

CA000434126A

Other languages

English (en)

French (fr)

Inventor

Toru Fuwa

Kenichi Miyoshi

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.)

Wakunaga Pharmaceutical Co Ltd

Original Assignee

Wakunaga Pharmaceutical Co Ltd

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.)

1982-08-09

Filing date

1983-08-08

Publication date

1986-03-25

1983-08-08 Application filed by Wakunaga Pharmaceutical Co Ltd filed Critical Wakunaga Pharmaceutical Co Ltd

1986-03-25 Application granted granted Critical

1986-03-25 Publication of CA1202254A publication Critical patent/CA1202254A/en

Status Expired legal-status Critical Current

Links

108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 73
238000004519 manufacturing process Methods 0.000 title abstract description 7
238000000034 method Methods 0.000 claims abstract description 46
229920002684 Sepharose Polymers 0.000 claims abstract description 40
125000006239 protecting group Chemical group 0.000 claims abstract description 32
125000003277 amino group Chemical group 0.000 claims abstract description 31
239000002773 nucleotide Substances 0.000 claims abstract description 17
125000003729 nucleotide group Chemical group 0.000 claims abstract description 16
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 10
125000006850 spacer group Chemical group 0.000 claims abstract description 9
150000001875 compounds Chemical class 0.000 claims description 121
230000015572 biosynthetic process Effects 0.000 claims description 22
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical group O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 22
238000003786 synthesis reaction Methods 0.000 claims description 21
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 20
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical group NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 18
-1 o-nitrophenyl-sulphenyl group Chemical group 0.000 claims description 18
GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 14
229930024421 Adenine Natural products 0.000 claims description 13
229960000643 adenine Drugs 0.000 claims description 13
239000002777 nucleoside Substances 0.000 claims description 13
150000003833 nucleoside derivatives Chemical class 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
150000008223 ribosides Chemical class 0.000 claims description 10
229940113082 thymine Drugs 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
229940104302 cytosine Drugs 0.000 claims description 9
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
239000000969 carrier Substances 0.000 claims description 7
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 7
238000010532 solid phase synthesis reaction Methods 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
101100295741 Gallus gallus COR4 gene Proteins 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
230000008030 elimination Effects 0.000 claims description 5
238000003379 elimination reaction Methods 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical group CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
239000004793 Polystyrene Substances 0.000 claims description 4
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 4
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
230000000865 phosphorylative effect Effects 0.000 claims description 4
229920002401 polyacrylamide Chemical class 0.000 claims description 4
229920002223 polystyrene Polymers 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 claims description 2
WPPONCHFOIIFIJ-UHFFFAOYSA-N N1N=NN=[C-]1 Chemical compound N1N=NN=[C-]1 WPPONCHFOIIFIJ-UHFFFAOYSA-N 0.000 claims description 2
FTAJFJHHNHPSBP-UHFFFAOYSA-N [N+](=O)([O-])C1=[C-]N=NN1 Chemical compound [N+](=O)([O-])C1=[C-]N=NN1 FTAJFJHHNHPSBP-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 8
125000004432 carbon atom Chemical group C* 0.000 claims 4
239000007787 solid Chemical class 0.000 claims 4
GJBVFACNLHJXCO-UHFFFAOYSA-N 2,4-dihydrobenzotriazol-4-id-5-yl-oxido-oxophosphanium Chemical compound P(=O)(=O)C1=[C-]C2=C(NN=N2)C=C1 GJBVFACNLHJXCO-UHFFFAOYSA-N 0.000 claims 1
AJZZHFTYVKGGRN-UHFFFAOYSA-N P(=O)(=O)C1=[C-]N=NN1 Chemical group P(=O)(=O)C1=[C-]N=NN1 AJZZHFTYVKGGRN-UHFFFAOYSA-N 0.000 claims 1
125000003835 nucleoside group Chemical group 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 37
238000001179 sorption measurement Methods 0.000 description 34
239000002585 base Substances 0.000 description 25
239000011347 resin Substances 0.000 description 20
229920005989 resin Polymers 0.000 description 20
239000000243 solution Substances 0.000 description 20
239000001913 cellulose Substances 0.000 description 15
229920002678 cellulose Polymers 0.000 description 15
108020004707 nucleic acids Proteins 0.000 description 15
150000007523 nucleic acids Chemical class 0.000 description 15
102000039446 nucleic acids Human genes 0.000 description 15
238000003556 assay Methods 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 11
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
238000011160 research Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
229910001868 water Inorganic materials 0.000 description 10
101150073006 HOT13 gene Proteins 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
238000010828 elution Methods 0.000 description 9
238000000746 purification Methods 0.000 description 9
238000001042 affinity chromatography Methods 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
125000000524 functional group Chemical group 0.000 description 6
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 5
YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 5
SFYDWLYPIXHPML-UHFFFAOYSA-N 3-nitro-1-(2,4,6-trimethylphenyl)sulfonyl-1,2,4-triazole Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)N1N=C([N+]([O-])=O)N=C1 SFYDWLYPIXHPML-UHFFFAOYSA-N 0.000 description 5
CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 5
229920000936 Agarose Polymers 0.000 description 5
229920005654 Sephadex Polymers 0.000 description 5
239000012507 Sephadex™ Substances 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
230000000875 corresponding effect Effects 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
239000000872 buffer Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000007790 solid phase Substances 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
238000012360 testing method Methods 0.000 description 4
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003446 ligand Substances 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
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 description 3
238000005406 washing Methods 0.000 description 3
NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 description 2
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
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125000002103 4,4'-dimethoxytriphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)(C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 2
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230000000052 comparative effect Effects 0.000 description 2
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DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
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150000003839 salts Chemical class 0.000 description 2
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108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
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VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
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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 1
239000003513 alkali Substances 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
MTFJSAGADRTKCI-VMPITWQZSA-N chembl77510 Chemical compound O\N=C\C1=CC=CC=N1 MTFJSAGADRTKCI-VMPITWQZSA-N 0.000 description 1
150000005829 chemical entities Chemical class 0.000 description 1
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238000012790 confirmation Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000011033 desalting Methods 0.000 description 1
BLEBFDYUDVZRFG-UHFFFAOYSA-N dichloromethane;propan-2-ol Chemical compound ClCCl.CC(C)O BLEBFDYUDVZRFG-UHFFFAOYSA-N 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
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239000012847 fine chemical Substances 0.000 description 1
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239000005556 hormone Substances 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
AFQIYTIJXGTIEY-UHFFFAOYSA-N hydrogen carbonate;triethylazanium Chemical compound OC(O)=O.CCN(CC)CC AFQIYTIJXGTIEY-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
238000001668 nucleic acid synthesis Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical group NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
229920006122 polyamide resin Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000002356 skeleton Anatomy 0.000 description 1
229940116591 skeleton diagnostic radiopharmaceuticals Drugs 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
150000005691 triesters Chemical class 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000003643 water by type Substances 0.000 description 1
229940102001 zinc bromide Drugs 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Saccharide Compounds (AREA)
Treatment Of Liquids With Adsorbents In General (AREA)

CA000434126A 1982-08-09 1983-08-08 Oligonucleotide derivatives and production thereof Expired CA1202254A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP57138136A JPS5927900A (ja)	1982-08-09	1982-08-09	固定化オリゴヌクレオチド
JP138136/1982		1982-08-09

Publications (1)

Publication Number	Publication Date
CA1202254A true CA1202254A (en)	1986-03-25

Family

ID=15214830

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000434126A Expired CA1202254A (en)	1982-08-09	1983-08-08	Oligonucleotide derivatives and production thereof

Country Status (5)

Country	Link
US (3)	US4667025A (2)
EP (1)	EP0101985B1 (2)
JP (1)	JPS5927900A (2)
CA (1)	CA1202254A (2)
DE (1)	DE3373817D1 (2)

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1982
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1983
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- 1983-08-05 EP EP83107730A patent/EP0101985B1/en not_active Expired
- 1983-08-08 CA CA000434126A patent/CA1202254A/en not_active Expired
1985
- 1985-10-24 US US06/790,658 patent/US4667025A/en not_active Expired - Lifetime
1987
- 1987-02-20 US US07/016,835 patent/US4789737A/en not_active Expired - Lifetime
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Also Published As

Publication number	Publication date
DE3373817D1 (en)	1987-10-29
US4667025A (en)	1987-05-19
US4789737A (en)	1988-12-06
JPS5927900A (ja)	1984-02-14
JPH0372639B2 (2)	1991-11-19
EP0101985A1 (en)	1984-03-07
EP0101985B1 (en)	1987-09-23
US4820812A (en)	1989-04-11

Legal Events

Date	Code	Title	Description
2003-08-08	MKEX	Expiry

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