JP2002522446A5 - - Google Patents
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- JP2002522446A5 JP2002522446A5 JP2000563674A JP2000563674A JP2002522446A5 JP 2002522446 A5 JP2002522446 A5 JP 2002522446A5 JP 2000563674 A JP2000563674 A JP 2000563674A JP 2000563674 A JP2000563674 A JP 2000563674A JP 2002522446 A5 JP2002522446 A5 JP 2002522446A5
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- JP
- Japan
- Prior art keywords
- group
- compound
- hydrogen
- protecting
- hydroxyl
- 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.)
- Granted
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- -1 halogenoacyl Chemical compound 0.000 description 52
- 150000001875 compounds Chemical class 0.000 description 41
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 26
- 125000003118 aryl group Chemical group 0.000 description 17
- 150000002431 hydrogen Chemical class 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 239000000126 substance Substances 0.000 description 13
- 125000006239 protecting group Chemical group 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000006575 electron-withdrawing group Chemical group 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002777 nucleoside Substances 0.000 description 6
- 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 5
- 239000012038 nucleophile Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 3
- 150000003833 nucleoside derivatives Chemical class 0.000 description 3
- 230000002194 synthesizing effect Effects 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
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000003835 nucleoside group Chemical group 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 125000006245 phosphate protecting group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- IEPBPSSCIZTJIF-UHFFFAOYSA-N bis(2,2,2-trichloroethyl) carbonate Chemical compound ClC(Cl)(Cl)COC(=O)OCC(Cl)(Cl)Cl IEPBPSSCIZTJIF-UHFFFAOYSA-N 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/130,373 | 1998-08-07 | ||
| US09/130,373 US6335432B1 (en) | 1998-08-07 | 1998-08-07 | Structural analogs of amine bases and nucleosides |
| PCT/US1999/017587 WO2000008041A1 (en) | 1998-08-07 | 1999-08-04 | Structural analogs of amine bases and nucleosides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002522446A JP2002522446A (ja) | 2002-07-23 |
| JP2002522446A5 true JP2002522446A5 (enExample) | 2006-07-20 |
| JP4623828B2 JP4623828B2 (ja) | 2011-02-02 |
Family
ID=22444397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000563674A Expired - Lifetime JP4623828B2 (ja) | 1998-08-07 | 1999-08-04 | アミン塩基及びヌクレオシドの構造的類似体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6335432B1 (enExample) |
| EP (1) | EP1102782B1 (enExample) |
| JP (1) | JP4623828B2 (enExample) |
| CA (1) | CA2339967C (enExample) |
| DE (1) | DE69930647T2 (enExample) |
| WO (1) | WO2000008041A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7812149B2 (en) * | 1996-06-06 | 2010-10-12 | Isis Pharmaceuticals, Inc. | 2′-Fluoro substituted oligomeric compounds and compositions for use in gene modulations |
| WO2005121370A2 (en) * | 2004-06-03 | 2005-12-22 | Isis Pharmaceuticals, Inc. | Oligomeric compounds that facilitate risc loading |
| US20050119470A1 (en) * | 1996-06-06 | 2005-06-02 | Muthiah Manoharan | Conjugated oligomeric compounds and their use in gene modulation |
| US20040203024A1 (en) * | 1996-06-06 | 2004-10-14 | Baker Brenda F. | Modified oligonucleotides for use in RNA interference |
| US5898031A (en) * | 1996-06-06 | 1999-04-27 | Isis Pharmaceuticals, Inc. | Oligoribonucleotides for cleaving RNA |
| US20040147022A1 (en) * | 1996-06-06 | 2004-07-29 | Baker Brenda F. | 2'-methoxy substituted oligomeric compounds and compositions for use in gene modulations |
| US9096636B2 (en) | 1996-06-06 | 2015-08-04 | Isis Pharmaceuticals, Inc. | Chimeric oligomeric compounds and their use in gene modulation |
| US20050053976A1 (en) * | 1996-06-06 | 2005-03-10 | Baker Brenda F. | Chimeric oligomeric compounds and their use in gene modulation |
| US20040171031A1 (en) * | 1996-06-06 | 2004-09-02 | Baker Brenda F. | Sugar surrogate-containing oligomeric compounds and compositions for use in gene modulation |
| DE19935302A1 (de) | 1999-07-28 | 2001-02-08 | Aventis Pharma Gmbh | Konjugate und Verfahren zu deren Herstellung sowie deren Verwendung zum Transport von Molekülen über biologische Membranen |
| WO2004044136A2 (en) * | 2002-11-05 | 2004-05-27 | Isis Pharmaceuticals, Inc. | Compositions comprising alternating 2’-modified nucleosides for use in gene modulation |
| EP1636342A4 (en) * | 2003-06-20 | 2008-10-08 | Isis Pharmaceuticals Inc | OLIGOMER COMPOUNDS FOR USE IN THE MODULATION OF GENES |
| US8569474B2 (en) * | 2004-03-09 | 2013-10-29 | Isis Pharmaceuticals, Inc. | Double stranded constructs comprising one or more short strands hybridized to a longer strand |
| US8394947B2 (en) * | 2004-06-03 | 2013-03-12 | Isis Pharmaceuticals, Inc. | Positionally modified siRNA constructs |
| US7884086B2 (en) * | 2004-09-08 | 2011-02-08 | Isis Pharmaceuticals, Inc. | Conjugates for use in hepatocyte free uptake assays |
| US20100280098A1 (en) * | 2007-10-05 | 2010-11-04 | Juliano Rudolph L | Receptor targeted oligonucleotides |
| US9778188B2 (en) | 2009-03-11 | 2017-10-03 | Industrial Technology Research Institute | Apparatus and method for detection and discrimination molecular object |
| US9482615B2 (en) | 2010-03-15 | 2016-11-01 | Industrial Technology Research Institute | Single-molecule detection system and methods |
| US9670243B2 (en) | 2010-06-02 | 2017-06-06 | Industrial Technology Research Institute | Compositions and methods for sequencing nucleic acids |
| US8865078B2 (en) | 2010-06-11 | 2014-10-21 | Industrial Technology Research Institute | Apparatus for single-molecule detection |
| SG188666A1 (en) | 2010-09-30 | 2013-05-31 | Agency Science Tech & Res | Methods and reagents for detection and treatment of esophageal metaplasia |
| RU2015119411A (ru) | 2012-11-15 | 2017-01-10 | Рош Инновейшен Сентер Копенгаген А/С | Конъюгаты антисмысловых соединений, направленные на аполипопротеин в |
| WO2014118267A1 (en) | 2013-01-30 | 2014-08-07 | Santaris Pharma A/S | Lna oligonucleotide carbohydrate conjugates |
| WO2014118272A1 (en) | 2013-01-30 | 2014-08-07 | Santaris Pharma A/S | Antimir-122 oligonucleotide carbohydrate conjugates |
| SG10201908122XA (en) | 2013-06-27 | 2019-10-30 | Roche Innovation Ct Copenhagen As | Antisense oligomers and conjugates targeting pcsk9 |
| JP6226318B2 (ja) * | 2013-09-02 | 2017-11-08 | 株式会社 資生堂 | 光学分割用化合物、光学分割用試薬、光学分割する方法及び光学異性体 |
| GB201408623D0 (en) | 2014-05-15 | 2014-07-02 | Santaris Pharma As | Oligomers and oligomer conjugates |
| PL3430141T3 (pl) | 2016-03-14 | 2022-02-28 | F. Hoffmann-La Roche Ag | Oligonukleotydy do obniżenia ekspresji pd-l1 |
| CR20230308A (es) | 2020-12-11 | 2023-09-08 | Civi Biopharma Inc | Entrega oral de conjugados antisentido que tienen por blanco a pcsk9 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1219824A (en) * | 1981-04-17 | 1987-03-31 | David C. Ward | Modified nucleotides and methods of preparing and using same |
| JPH0725788B2 (ja) * | 1985-09-09 | 1995-03-22 | 帝人株式会社 | オリゴまたはポリヌクレオチド |
| JPH07165786A (ja) * | 1993-12-10 | 1995-06-27 | Hiroaki Sawai | ５位置換ウリジン類、その製造方法及びその用途 |
| JP2001524808A (ja) * | 1996-12-10 | 2001-12-04 | ジーントレイス・システムズ・インコーポレイテッド | 放出可能な不揮発性の質量標識分子 |
-
1998
- 1998-08-07 US US09/130,373 patent/US6335432B1/en not_active Expired - Lifetime
-
1999
- 1999-08-04 EP EP99940867A patent/EP1102782B1/en not_active Expired - Lifetime
- 1999-08-04 JP JP2000563674A patent/JP4623828B2/ja not_active Expired - Lifetime
- 1999-08-04 WO PCT/US1999/017587 patent/WO2000008041A1/en not_active Ceased
- 1999-08-04 CA CA2339967A patent/CA2339967C/en not_active Expired - Lifetime
- 1999-08-04 DE DE69930647T patent/DE69930647T2/de not_active Expired - Lifetime
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