JP2009057388A5 - - Google Patents
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- Publication number
- JP2009057388A5 JP2009057388A5 JP2008262208A JP2008262208A JP2009057388A5 JP 2009057388 A5 JP2009057388 A5 JP 2009057388A5 JP 2008262208 A JP2008262208 A JP 2008262208A JP 2008262208 A JP2008262208 A JP 2008262208A JP 2009057388 A5 JP2009057388 A5 JP 2009057388A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrimidine
- purine
- compound
- palladium catalyst
- Prior art date
- 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.)
- Pending
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- 238000000034 method Methods 0.000 claims 38
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 229910052763 palladium Inorganic materials 0.000 claims 14
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims 13
- 150000001413 amino acids Chemical class 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 10
- 239000003054 catalyst Substances 0.000 claims 10
- 239000007858 starting material Substances 0.000 claims 9
- 239000012038 nucleophile Substances 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims 6
- 229960000643 adenine Drugs 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 5
- 150000001298 alcohols Chemical class 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 230000004048 modification Effects 0.000 claims 4
- 238000012986 modification Methods 0.000 claims 4
- 239000002718 pyrimidine nucleoside Substances 0.000 claims 4
- 150000003573 thiols Chemical class 0.000 claims 4
- 229940045145 uridine Drugs 0.000 claims 4
- LFRDGHVRPSURMV-YFKPBYRVSA-N (4s)-4,5-dihydroxypentanal Chemical compound OC[C@@H](O)CCC=O LFRDGHVRPSURMV-YFKPBYRVSA-N 0.000 claims 3
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 claims 3
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims 3
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 3
- 229930024421 Adenine Natural products 0.000 claims 3
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 claims 3
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims 3
- 108091034117 Oligonucleotide Proteins 0.000 claims 3
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 3
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 claims 3
- 150000001913 cyanates Chemical class 0.000 claims 3
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 150000002170 ethers Chemical class 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 150000004820 halides Chemical class 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims 3
- 239000002212 purine nucleoside Substances 0.000 claims 3
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- -1 5'-protected 5-iodo-uridine Chemical class 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 2
- 241000701022 Cytomegalovirus Species 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- RKSLVDIXBGWPIS-UAKXSSHOSA-N 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 RKSLVDIXBGWPIS-UAKXSSHOSA-N 0.000 claims 1
- SXGFECRAKVVEJT-UHFFFAOYSA-N 2-amino-8-iodo-3,7-dihydropurin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N=C(I)N2 SXGFECRAKVVEJT-UHFFFAOYSA-N 0.000 claims 1
- LQQGJDJXUSAEMZ-UAKXSSHOSA-N 4-amino-1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one Chemical compound C1=C(I)C(N)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 LQQGJDJXUSAEMZ-UAKXSSHOSA-N 0.000 claims 1
- XUMSFQKCBNKNCE-UHFFFAOYSA-N 8-iodo-7h-purin-6-amine Chemical compound NC1=NC=NC2=C1NC(I)=N2 XUMSFQKCBNKNCE-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- 108020004414 DNA Proteins 0.000 claims 1
- 102000053602 DNA Human genes 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 150000003834 purine nucleoside derivatives Chemical class 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 229920002477 rna polymer Polymers 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 0 C*1OC(C(*(C=C(C(C)=O)C(*2)=O)C2=*)O)C(*CO)O1 Chemical compound C*1OC(C(*(C=C(C(C)=O)C(*2)=O)C2=*)O)C(*CO)O1 0.000 description 9
- DDIYNLIVSJFJLB-XQRVVYSFSA-N CCC/C(/N)=C/C Chemical compound CCC/C(/N)=C/C DDIYNLIVSJFJLB-XQRVVYSFSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45907395A | 1995-06-02 | 1995-06-02 | |
| US08/458,421 US5719273A (en) | 1993-06-14 | 1995-06-02 | Palladium catalyzed nucleoside modifications methods using nucleophiles and carbon monoxide |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53665296A Division JP4899014B2 (ja) | 1995-06-02 | 1996-05-30 | 求核試薬および一酸化炭素を用いるパラジウム触媒ヌクレオシド修飾方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009057388A JP2009057388A (ja) | 2009-03-19 |
| JP2009057388A5 true JP2009057388A5 (enExample) | 2009-09-03 |
Family
ID=40553446
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53665296A Expired - Lifetime JP4899014B2 (ja) | 1995-06-02 | 1996-05-30 | 求核試薬および一酸化炭素を用いるパラジウム触媒ヌクレオシド修飾方法 |
| JP2008262208A Pending JP2009057388A (ja) | 1995-06-02 | 2008-10-08 | 求核試薬および一酸化炭素を用いるパラジウム触媒ヌクレオシド修飾方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53665296A Expired - Lifetime JP4899014B2 (ja) | 1995-06-02 | 1996-05-30 | 求核試薬および一酸化炭素を用いるパラジウム触媒ヌクレオシド修飾方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JP4899014B2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5993279A (ja) * | 1982-11-17 | 1984-05-29 | 富士通株式会社 | ロボツトによるカ−ド，レシ−ト分離取出し方法 |
| JP4899014B2 (ja) * | 1995-06-02 | 2012-03-21 | イーシー・テクノロジー・エルエルシー | 求核試薬および一酸化炭素を用いるパラジウム触媒ヌクレオシド修飾方法 |
| US7947447B2 (en) | 2007-01-16 | 2011-05-24 | Somalogic, Inc. | Method for generating aptamers with improved off-rates |
| CA2696431C (en) * | 2007-07-17 | 2021-01-05 | Somalogic, Inc. | Method for generating aptamers with improved off-rates |
| US20110275794A1 (en) * | 2010-04-12 | 2011-11-10 | Somalogic, Inc. | 5-position modified pyrimidines and their use |
| EP3330277A3 (en) * | 2013-11-21 | 2018-09-26 | Somalogic, Inc. | Cytidine-5-carboxamide modified nucleotide compositions and methods related thereto |
| RU2750989C2 (ru) * | 2016-03-14 | 2021-07-07 | Сомалоджик, Инк. | Композиции и способы синтеза 5-(n-защищенного триптаминкарбоксамида)-2'-дезоксиуридинфосфорамидита для включения в нуклеиновую кислоту |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5536418A (en) * | 1978-09-08 | 1980-03-14 | Yamasa Shoyu Co Ltd | 8-substituted adenosine derivative and its preparation |
| JPS5862190A (ja) * | 1981-10-07 | 1983-04-13 | Yamasa Shoyu Co Ltd | オロチジン誘導体の製造法 |
| US5428149A (en) * | 1993-06-14 | 1995-06-27 | Washington State University Research Foundation | Method for palladium catalyzed carbon-carbon coulping and products |
| JP4899014B2 (ja) * | 1995-06-02 | 2012-03-21 | イーシー・テクノロジー・エルエルシー | 求核試薬および一酸化炭素を用いるパラジウム触媒ヌクレオシド修飾方法 |
-
1996
- 1996-05-30 JP JP53665296A patent/JP4899014B2/ja not_active Expired - Lifetime
-
2008
- 2008-10-08 JP JP2008262208A patent/JP2009057388A/ja active Pending
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