IL198086A - Preparation of nucleosides ribofuranosyl pyrimidines - Google Patents
Preparation of nucleosides ribofuranosyl pyrimidinesInfo
- Publication number
- IL198086A IL198086A IL198086A IL19808609A IL198086A IL 198086 A IL198086 A IL 198086A IL 198086 A IL198086 A IL 198086A IL 19808609 A IL19808609 A IL 19808609A IL 198086 A IL198086 A IL 198086A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- aryl
- process according
- fluoro
- ester
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 3
- 239000002777 nucleoside Substances 0.000 title 1
- -1 nucleosides ribofuranosyl pyrimidines Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 7
- 230000009466 transformation Effects 0.000 claims 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 239000012320 chlorinating reagent Substances 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000001131 transforming effect Effects 0.000 claims 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 150000002596 lactones Chemical class 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims 1
- JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000005708 Sodium hypochlorite Substances 0.000 claims 1
- CKOUDKNBOOIYOF-UHFFFAOYSA-N [SiH3]N(C1=NC(NC=C1)=O)C(C1=CC=CC=C1)=O Chemical compound [SiH3]N(C1=NC(NC=C1)=O)C(C1=CC=CC=C1)=O CKOUDKNBOOIYOF-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims 1
- 229910001626 barium chloride Inorganic materials 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85096206P | 2006-10-10 | 2006-10-10 | |
| PCT/US2007/021548 WO2008045419A1 (en) | 2006-10-10 | 2007-10-05 | Preparation of nucleosides ribofuranosyl pyrimidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL198086A0 IL198086A0 (en) | 2009-12-24 |
| IL198086A true IL198086A (en) | 2012-03-29 |
Family
ID=39111500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL198086A IL198086A (en) | 2006-10-10 | 2009-04-07 | Preparation of nucleosides ribofuranosyl pyrimidines |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8912321B2 (enExample) |
| EP (1) | EP2084174B1 (enExample) |
| JP (1) | JP5252459B2 (enExample) |
| KR (1) | KR101057239B1 (enExample) |
| CN (1) | CN101600725B (enExample) |
| AU (1) | AU2007307057B2 (enExample) |
| BR (1) | BRPI0719174A2 (enExample) |
| CA (1) | CA2666098C (enExample) |
| DK (1) | DK2084174T3 (enExample) |
| ES (1) | ES2429290T3 (enExample) |
| GT (1) | GT200900080A (enExample) |
| IL (1) | IL198086A (enExample) |
| MX (1) | MX2009003795A (enExample) |
| PL (1) | PL2084174T3 (enExample) |
| PT (1) | PT2084174E (enExample) |
| RU (1) | RU2421461C2 (enExample) |
| SI (1) | SI2084174T1 (enExample) |
| WO (1) | WO2008045419A1 (enExample) |
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| BRPI0419345B8 (pt) | 2003-05-30 | 2021-05-25 | Gilead Pharmasset Llc | uso do (2r)-2-desoxi-2-flúor-2-c-metil nucleosídeo e de uma composição farmacêutica que o compreende |
| MX2007003085A (es) * | 2004-09-14 | 2007-08-02 | Pharmasset Inc | Preparacion de 2'-fluoro-2'-alquilo sustituido u otras ribofuranosil pirimidinas y purinas opcionalmente sustituidas y sus derivados. |
| WO2006055193A1 (en) | 2004-11-16 | 2006-05-26 | Thomson Licensing | Film grain simulation method based on pre-computed transform coefficients |
| KR101229942B1 (ko) | 2004-11-16 | 2013-02-06 | 톰슨 라이센싱 | 비디오 시스템에서 비트까지 정확한 시뮬레이션을 위한필름 그레인 ｓｅｉ 메시지 삽입 |
| ZA200703946B (en) | 2004-11-17 | 2008-08-27 | Thomson Licensing | Bit-accurate film grain simulation method based on pre-computed transformed coefficients |
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| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| PL3290428T3 (pl) | 2010-03-31 | 2022-02-07 | Gilead Pharmasset Llc | Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu |
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| CN111040010A (zh) * | 2019-12-23 | 2020-04-21 | 上海红蓝医药科技有限公司 | 一种索非布韦中间体的合成方法 |
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| KR850002973A (ko) * | 1983-10-03 | 1985-05-28 | 구라바야시 이꾸시로 | 시티딘 유도체의 제조방법 |
| JP2559917B2 (ja) * | 1990-06-15 | 1996-12-04 | 三共株式会社 | ピリミジンヌクレオシド誘導体 |
| US5637688A (en) * | 1994-12-13 | 1997-06-10 | Eli Lilly And Company | Process for preparing 1-(2'-deoxy-2'-difluoro-d-ribofuranosyl)-4-aminopyrimidin-2-one hydrochloride |
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| CN1678326A (zh) | 2002-06-28 | 2005-10-05 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2'－c－甲基－3'－o－l－缬氨酸酯核糖呋喃基胞苷 |
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| BRPI0419345B8 (pt) | 2003-05-30 | 2021-05-25 | Gilead Pharmasset Llc | uso do (2r)-2-desoxi-2-flúor-2-c-metil nucleosídeo e de uma composição farmacêutica que o compreende |
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| EP1741716B8 (en) * | 2004-04-30 | 2012-02-22 | Daiichi Sankyo Company, Limited | Process for producing pentacyclic taxane |
| PT1773856E (pt) * | 2004-07-21 | 2012-05-14 | Gilead Pharmasset Llc | Preparação de 2-desoxi-2-fluoro-d-ribofuranosilo pirimidinas e purinas substituídas com alquilo e seus derivados |
| MX2007003085A (es) * | 2004-09-14 | 2007-08-02 | Pharmasset Inc | Preparacion de 2'-fluoro-2'-alquilo sustituido u otras ribofuranosil pirimidinas y purinas opcionalmente sustituidas y sus derivados. |
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| GT200900080A (es) | 2012-04-10 |
| EP2084174B1 (en) | 2013-07-31 |
| US20100056770A1 (en) | 2010-03-04 |
| ES2429290T3 (es) | 2013-11-14 |
| PT2084174E (pt) | 2013-10-08 |
| US20080139802A1 (en) | 2008-06-12 |
| EP2084174A1 (en) | 2009-08-05 |
| JP2010505954A (ja) | 2010-02-25 |
| SI2084174T1 (sl) | 2013-10-30 |
| US8912321B2 (en) | 2014-12-16 |
| MX2009003795A (es) | 2009-06-18 |
| CA2666098A1 (en) | 2008-04-17 |
| CN101600725A (zh) | 2009-12-09 |
| DK2084174T3 (da) | 2013-11-04 |
| CA2666098C (en) | 2012-09-25 |
| KR101057239B1 (ko) | 2011-08-16 |
| CN101600725B (zh) | 2014-11-26 |
| KR20090060460A (ko) | 2009-06-12 |
| BRPI0719174A2 (pt) | 2017-06-13 |
| AU2007307057B2 (en) | 2011-09-15 |
| PL2084174T3 (pl) | 2013-12-31 |
| JP5252459B2 (ja) | 2013-07-31 |
| HK1133889A1 (en) | 2010-04-09 |
| AU2007307057A1 (en) | 2008-04-17 |
| IL198086A0 (en) | 2009-12-24 |
| RU2009117396A (ru) | 2010-11-20 |
| WO2008045419A1 (en) | 2008-04-17 |
| RU2421461C2 (ru) | 2011-06-20 |
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