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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 206010011469 Crying Diseases 0.000 description 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- 240000005373 Panax quinquefolius Species 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
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- 239000012445 acidic reagent Substances 0.000 description 1
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- 238000005917 acylation reaction Methods 0.000 description 1
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- 230000036436 anti-hiv Effects 0.000 description 1
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- 239000012300 argon atmosphere Substances 0.000 description 1
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- 238000005352 clarification Methods 0.000 description 1
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- 239000012141 concentrate Substances 0.000 description 1
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- 238000004132 cross linking Methods 0.000 description 1
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- 229960002656 didanosine Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 238000001511 high performance liquid chromatography nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 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
- 231100001231 less toxic Toxicity 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 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
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
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- 239000011550 stock solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 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
- 238000012360 testing method Methods 0.000 description 1
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- 125000003944 tolyl group Chemical group 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)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (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 (no) |
| EP (1) | EP1495040A4 (no) |
| JP (1) | JP2005527589A (no) |
| KR (1) | KR20050005442A (no) |
| CN (1) | CN1329407C (no) |
| AU (1) | AU2003234737B2 (no) |
| BR (1) | BR0309111A (no) |
| CA (1) | CA2481572A1 (no) |
| MX (1) | MXPA04009986A (no) |
| NO (1) | NO20044927L (no) |
| PL (1) | PL371913A1 (no) |
| RU (1) | RU2310661C2 (no) |
| UA (1) | UA77291C2 (no) |
| WO (1) | WO2003087119A1 (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2694029C (en) * | 2007-07-26 | 2016-10-04 | Lexicon Pharmaceuticals, Inc. | Methods and compounds useful for the preparation of sodium glucose co-transporter 2 inhibitors |
| JP5749017B2 (ja) | 2008-01-22 | 2015-07-15 | ダウ アグロサイエンシィズ エルエルシー | ５−フルオロピリミジン誘導体 |
| PL2861611T3 (pl) | 2012-05-25 | 2017-08-31 | Janssen Sciences Ireland Uc | Nukleozydy uracylowe spirooksetanu |
Family Cites Families (12)
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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 |
| IL100965A (en) * | 1991-02-22 | 1999-12-31 | Univ Emory | 2 - Hydroxymethyl - 5 -) 5 - Fluorocytocin - 1 - Eyal (- 1, 3 - Oxathiolane, its resolution and pharmaceuticals containing it |
| 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 |
| 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 |
| 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 |
| CN1342156A (zh) | 1998-08-25 | 2002-03-27 | 耶鲁大学 | 用赛菊宁黄质及其类似物抑制和治疗乙型肝炎病毒和黄病毒 |
| JP3889708B2 (ja) | 2000-11-20 | 2007-03-07 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ型肝炎トリペプチド阻害剤 |
| CN1267446C (zh) | 2001-01-22 | 2006-08-02 | 默克公司 | 作为依赖于rna的rna病毒聚合酶的抑制剂的核苷衍生物 |
| 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 US US10/411,929 patent/US6897302B2/en not_active Expired - Lifetime
- 2003-04-11 AU AU2003234737A patent/AU2003234737B2/en not_active Ceased
- 2003-04-11 CN CNB038113155A patent/CN1329407C/zh not_active Expired - Lifetime
- 2003-04-11 PL PL03371913A patent/PL371913A1/xx not_active Application Discontinuation
- 2003-04-11 RU RU2004133062/04A patent/RU2310661C2/ru not_active IP Right Cessation
- 2003-04-11 JP JP2003584075A patent/JP2005527589A/ja active Pending
- 2003-04-11 EP EP03728393A patent/EP1495040A4/en not_active Withdrawn
- 2003-04-11 CA CA002481572A patent/CA2481572A1/en not_active Abandoned
- 2003-04-11 BR BR0309111-2A patent/BR0309111A/pt not_active IP Right Cessation
- 2003-04-11 KR KR10-2004-7016211A patent/KR20050005442A/ko active IP Right Grant
- 2003-04-11 WO PCT/US2003/011445 patent/WO2003087119A1/en active Application Filing
- 2003-04-11 MX MXPA04009986A patent/MXPA04009986A/es active IP Right Grant
- 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 |
|---|---|
| CA2481572A1 (en) | 2003-10-23 |
| RU2310661C2 (ru) | 2007-11-20 |
| US20040147479A1 (en) | 2004-07-29 |
| KR20050005442A (ko) | 2005-01-13 |
| WO2003087119A1 (en) | 2003-10-23 |
| NO20044927L (no) | 2005-01-10 |
| EP1495040A1 (en) | 2005-01-12 |
| US6897302B2 (en) | 2005-05-24 |
| RU2004133062A (ru) | 2005-06-10 |
| JP2005527589A (ja) | 2005-09-15 |
| AU2003234737B2 (en) | 2009-08-27 |
| CN1329407C (zh) | 2007-08-01 |
| MXPA04009986A (es) | 2005-08-16 |
| AU2003234737A1 (en) | 2003-10-27 |
| EP1495040A4 (en) | 2006-01-25 |
| CN1653078A (zh) | 2005-08-10 |
| PL371913A1 (en) | 2005-07-11 |
| BR0309111A (pt) | 2005-02-01 |
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