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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| CN101138247B (zh) | 2004-11-16 | 2010-05-26 | 汤姆森特许公司 | 位精度仿真的胶片颗粒补充增强信息消息插入方法及系统 |
| MX2007005651A (es) | 2004-11-17 | 2007-06-05 | Thomson Licensing | Metodo de simulacion de grano de pelicula exacto de bits con base en coeficientes transformados pre-computados. |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| US10715834B2 (en) | 2007-05-10 | 2020-07-14 | Interdigital Vc Holdings, Inc. | Film grain simulation based on pre-computed transform coefficients |
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| US8551973B2 (en) | 2008-12-23 | 2013-10-08 | Gilead Pharmasset Llc | Nucleoside analogs |
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| 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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| ES2624353T3 (es) | 2002-11-15 | 2017-07-13 | Idenix Pharmaceuticals Llc | 2'-Metil nucleósidos en combinación con interferón y mutación de Flaviviridae |
| TWI332507B (en) | 2002-11-19 | 2010-11-01 | Hoffmann La Roche | Antiviral nucleoside derivatives |
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-
2007
- 2007-10-05 WO PCT/US2007/021548 patent/WO2008045419A1/en not_active Ceased
- 2007-10-05 RU RU2009117396/04A patent/RU2421461C2/ru not_active IP Right Cessation
- 2007-10-05 SI SI200731311T patent/SI2084174T1/sl unknown
- 2007-10-05 EP EP07839369.1A patent/EP2084174B1/en active Active
- 2007-10-05 AU AU2007307057A patent/AU2007307057B2/en active Active
- 2007-10-05 CN CN200780037855.XA patent/CN101600725B/zh active Active
- 2007-10-05 PT PT78393691T patent/PT2084174E/pt unknown
- 2007-10-05 BR BRPI0719174A patent/BRPI0719174A2/pt not_active IP Right Cessation
- 2007-10-05 ES ES07839369T patent/ES2429290T3/es active Active
- 2007-10-05 MX MX2009003795A patent/MX2009003795A/es active IP Right Grant
- 2007-10-05 CA CA2666098A patent/CA2666098C/en active Active
- 2007-10-05 DK DK07839369.1T patent/DK2084174T3/da active
- 2007-10-05 PL PL07839369T patent/PL2084174T3/pl unknown
- 2007-10-05 US US12/444,608 patent/US8912321B2/en active Active
- 2007-10-05 KR KR1020097008991A patent/KR101057239B1/ko active Active
- 2007-10-05 JP JP2009532372A patent/JP5252459B2/ja active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| ES2429290T3 (es) | 2013-11-14 |
| IL198086A0 (en) | 2009-12-24 |
| EP2084174B1 (en) | 2013-07-31 |
| HK1133889A1 (en) | 2010-04-09 |
| BRPI0719174A2 (pt) | 2017-06-13 |
| US8912321B2 (en) | 2014-12-16 |
| CN101600725B (zh) | 2014-11-26 |
| PT2084174E (pt) | 2013-10-08 |
| KR101057239B1 (ko) | 2011-08-16 |
| GT200900080A (es) | 2012-04-10 |
| US20080139802A1 (en) | 2008-06-12 |
| MX2009003795A (es) | 2009-06-18 |
| SI2084174T1 (sl) | 2013-10-30 |
| KR20090060460A (ko) | 2009-06-12 |
| JP2010505954A (ja) | 2010-02-25 |
| RU2421461C2 (ru) | 2011-06-20 |
| CN101600725A (zh) | 2009-12-09 |
| CA2666098A1 (en) | 2008-04-17 |
| RU2009117396A (ru) | 2010-11-20 |
| AU2007307057B2 (en) | 2011-09-15 |
| PL2084174T3 (pl) | 2013-12-31 |
| DK2084174T3 (da) | 2013-11-04 |
| US20100056770A1 (en) | 2010-03-04 |
| AU2007307057A1 (en) | 2008-04-17 |
| CA2666098C (en) | 2012-09-25 |
| WO2008045419A1 (en) | 2008-04-17 |
| EP2084174A1 (en) | 2009-08-05 |
| JP5252459B2 (ja) | 2013-07-31 |
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