UA77291C2 - A method of synthesizing -fluoro-2',3'-dideoxy-2",3"-didehydrocytidine () - Google Patents
A method of synthesizing -fluoro-2',3'-dideoxy-2",3"-didehydrocytidine () Download PDFInfo
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- UA77291C2 UA77291C2 UA20041109254A UA20041109254A UA77291C2 UA 77291 C2 UA77291 C2 UA 77291C2 UA 20041109254 A UA20041109254 A UA 20041109254A UA 20041109254 A UA20041109254 A UA 20041109254A UA 77291 C2 UA77291 C2 UA 77291C2
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- 238000000034 method Methods 0.000 title claims abstract description 52
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
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- 238000006243 chemical reaction Methods 0.000 claims description 57
- 150000001875 compounds Chemical class 0.000 claims description 54
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- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 240000005373 Panax quinquefolius Species 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
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- 239000002612 dispersion medium Substances 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- 239000001257 hydrogen Substances 0.000 description 1
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- 230000000977 initiatory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 201000007270 liver cancer Diseases 0.000 description 1
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- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 description 1
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- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07H19/048—Pyridine radicals
-
- 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
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37200602P | 2002-04-12 | 2002-04-12 | |
PCT/US2003/011445 WO2003087119A1 (en) | 2002-04-12 | 2003-04-11 | METHOD FOR SYNTHESIZING β-L-FLUORO-2´,3´DIDEHYDROCYTIDINE (β-L-FD4C) |
Publications (1)
Publication Number | Publication Date |
---|---|
UA77291C2 true UA77291C2 (en) | 2006-11-15 |
Family
ID=29250776
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA20041109254A UA77291C2 (en) | 2002-04-12 | 2003-11-04 | A method of synthesizing -fluoro-2',3'-dideoxy-2",3"-didehydrocytidine () |
Country Status (14)
Country | Link |
---|---|
US (1) | US6897302B2 (zh) |
EP (1) | EP1495040A4 (zh) |
JP (1) | JP2005527589A (zh) |
KR (1) | KR20050005442A (zh) |
CN (1) | CN1329407C (zh) |
AU (1) | AU2003234737B2 (zh) |
BR (1) | BR0309111A (zh) |
CA (1) | CA2481572A1 (zh) |
MX (1) | MXPA04009986A (zh) |
NO (1) | NO20044927L (zh) |
PL (1) | PL371913A1 (zh) |
RU (1) | RU2310661C2 (zh) |
UA (1) | UA77291C2 (zh) |
WO (1) | WO2003087119A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5653213B2 (ja) * | 2007-07-26 | 2015-01-14 | レクシコン ファーマシューティカルズ インコーポレイテッド | ナトリウム・グルコース共輸送体2阻害剤の調製に有用な方法及び化合物 |
CN101977900B (zh) | 2008-01-22 | 2013-11-27 | 陶氏益农公司 | 5-氟嘧啶衍生物 |
CA2871547C (en) | 2012-05-25 | 2021-05-25 | Janssen R&D Ireland | Uracyl spirooxetane nucleosides |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
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US5204466A (en) * | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
NZ250842A (en) * | 1991-02-22 | 1996-03-26 | Univ Emory | Resolution of a racemic mixture of nucleoside enantiomers such as 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane (ftc) |
US5627160A (en) * | 1993-05-25 | 1997-05-06 | Yale University | L-2',3'-dideoxy nucleoside analogs as anti-hepatitis B (HBV) and anti-HIV agents |
TW374087B (en) * | 1993-05-25 | 1999-11-11 | Univ Yale | L-2',3'-dideoxy nucleotide analogs as anti-hepatitis B(HBV) and anti-HIV agents |
US5703058A (en) * | 1995-01-27 | 1997-12-30 | Emory University | Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent |
US5869461A (en) * | 1995-03-16 | 1999-02-09 | Yale University | Reducing toxicity of L-nucleosides with D-nucleosides |
US6005097A (en) | 1996-06-14 | 1999-12-21 | Vion Pharmaceuticals, Inc. | Processes for high-yield diastereoselective synthesis of dideoxynucleosides |
US6280940B1 (en) * | 1998-08-05 | 2001-08-28 | Agouron Pharmaceuticals, Inc. | Reporter gene system for use in cell-based assessment of inhibitors of the Hepatitis C virus protease |
BR9913333A (pt) * | 1998-08-25 | 2001-05-15 | Univ Yale | Inibição e tratamento do vìrus da hepatite b e flavivìrus com helioxatina e seus análogos |
EP1337550B1 (en) * | 2000-11-20 | 2006-05-24 | Bristol-Myers Squibb Company | Hepatitis c tripeptide inhibitors |
KR100828453B1 (ko) * | 2001-01-22 | 2008-05-13 | 머크 앤드 캄파니 인코포레이티드 | Rna 의존성 rna 바이러스 폴리머라제의억제제로서의 뉴클레오시드 유도체 |
US6689559B2 (en) * | 2001-11-29 | 2004-02-10 | The Research Foundation Of The State University Of New York | Efficient hepatitis C virus replicon and its use in identifying antiviral compounds |
-
2003
- 2003-04-11 CA CA002481572A patent/CA2481572A1/en not_active Abandoned
- 2003-04-11 MX MXPA04009986A patent/MXPA04009986A/es active IP Right Grant
- 2003-04-11 EP EP03728393A patent/EP1495040A4/en not_active Withdrawn
- 2003-04-11 PL PL03371913A patent/PL371913A1/xx not_active Application Discontinuation
- 2003-04-11 JP JP2003584075A patent/JP2005527589A/ja active Pending
- 2003-04-11 WO PCT/US2003/011445 patent/WO2003087119A1/en active Application Filing
- 2003-04-11 KR KR10-2004-7016211A patent/KR20050005442A/ko active IP Right Grant
- 2003-04-11 BR BR0309111-2A patent/BR0309111A/pt not_active IP Right Cessation
- 2003-04-11 RU RU2004133062/04A patent/RU2310661C2/ru not_active IP Right Cessation
- 2003-04-11 US US10/411,929 patent/US6897302B2/en not_active Expired - Lifetime
- 2003-04-11 CN CNB038113155A patent/CN1329407C/zh not_active Expired - Lifetime
- 2003-04-11 AU AU2003234737A patent/AU2003234737B2/en not_active Ceased
- 2003-11-04 UA UA20041109254A patent/UA77291C2/uk unknown
-
2004
- 2004-11-11 NO NO20044927A patent/NO20044927L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
AU2003234737B2 (en) | 2009-08-27 |
WO2003087119A1 (en) | 2003-10-23 |
CA2481572A1 (en) | 2003-10-23 |
CN1329407C (zh) | 2007-08-01 |
EP1495040A1 (en) | 2005-01-12 |
RU2004133062A (ru) | 2005-06-10 |
KR20050005442A (ko) | 2005-01-13 |
PL371913A1 (en) | 2005-07-11 |
US20040147479A1 (en) | 2004-07-29 |
BR0309111A (pt) | 2005-02-01 |
JP2005527589A (ja) | 2005-09-15 |
CN1653078A (zh) | 2005-08-10 |
AU2003234737A1 (en) | 2003-10-27 |
MXPA04009986A (es) | 2005-08-16 |
US6897302B2 (en) | 2005-05-24 |
RU2310661C2 (ru) | 2007-11-20 |
EP1495040A4 (en) | 2006-01-25 |
NO20044927L (no) | 2005-01-10 |
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