BRPI0507363A - métodos para manufatura de 1,3-dioxolano nucleosìdeos - Google Patents
métodos para manufatura de 1,3-dioxolano nucleosìdeosInfo
- Publication number
- BRPI0507363A BRPI0507363A BRPI0507363-4A BRPI0507363A BRPI0507363A BR PI0507363 A BRPI0507363 A BR PI0507363A BR PI0507363 A BRPI0507363 A BR PI0507363A BR PI0507363 A BRPI0507363 A BR PI0507363A
- Authority
- BR
- Brazil
- Prior art keywords
- dioxolane
- lactone
- substantially pure
- nucleoside
- manufacturing
- Prior art date
Links
- 239000002777 nucleoside Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000003833 nucleoside derivatives Chemical class 0.000 title abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- -1 1,3-dioxolane lactone Chemical class 0.000 abstract 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- VZQXUWKZDSEQRR-UHFFFAOYSA-N Nucleosid Natural products C12=NC(SC)=NC(NCC=C(C)C)=C2N=CN1C1OC(CO)C(O)C1O VZQXUWKZDSEQRR-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 230000004913 activation Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003212 purines Chemical class 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
MéTODOS PARA MANUFATURA DE 1,3-DIOXOLANO NUCLEOSìDEOS Esse pedido fornece um processo para a preparação de <225>-D-dioxolano nucleosídeos enantiomericamente puros. Em particular, uma nova síntese, de (-)-DAPD, adequada para desenvolvimento em ampla escala, é descrita. Em uma modalidade a invenção fornece um processo para a preparação de <225>-D ou <225>-L-1,3-dioxolano nucleosídeos substancialmente puros que compreende a) a preparação ou obtenção de um 2,2-di-alcoxi etanol esterificado; b) ciclização do 2,2-dialcoxi etanol esterificado com ácido glicólico para obter uma 1,3-dioxolano lactona; c) separação da 1,3-dioxolano lactona para obter uma D- ou L-lactona substancialmente pura; d) redução seletiva e ativação da D-ou L-lactona quiral para obter um D- ou L-1,3-dioxolano substancialmente puro; e) ligação do D- ou L-1,3-dioxolano a uma base de purina ou pirimidina ativada e/ou protegida; e f) purificação opcional do nucleosídeo para obter um <225>-D ou <225>-L-1,3-dioxolano nucleosídeo protegido substancialmente puro.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54154504P | 2004-02-03 | 2004-02-03 | |
| PCT/US2005/003620 WO2005074654A2 (en) | 2004-02-03 | 2005-02-03 | Methods to manufacture 1,3-dioxolane nucleosides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0507363A true BRPI0507363A (pt) | 2007-07-03 |
Family
ID=34837503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0507363-4A BRPI0507363A (pt) | 2004-02-03 | 2005-02-03 | métodos para manufatura de 1,3-dioxolano nucleosìdeos |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7785839B2 (pt) |
| EP (1) | EP1720840B1 (pt) |
| KR (1) | KR101157468B1 (pt) |
| CN (2) | CN105039489A (pt) |
| BR (1) | BRPI0507363A (pt) |
| CA (1) | CA2554782C (pt) |
| ES (1) | ES2568467T3 (pt) |
| HK (1) | HK1216432A1 (pt) |
| WO (1) | WO2005074654A2 (pt) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050085638A1 (en) * | 2002-01-25 | 2005-04-21 | Shire Biochem Inc | Process for producing dioxolane nucleoside analogues |
| CA2554782C (en) * | 2004-02-03 | 2013-08-13 | Emory University | Methods to manufacture 1,3-dioxolane nucleosides |
| CN105385621B (zh) * | 2015-11-20 | 2018-10-02 | 浙江昌明药业有限公司 | 琼氏不动杆菌zjutfet-1及其应用 |
| WO2019232067A1 (en) * | 2018-05-29 | 2019-12-05 | Centrillion Technologies, Inc. | Increasing efficiency of photochemical reactions on substrates |
| WO2019245444A1 (en) | 2018-06-21 | 2019-12-26 | Medivir Ab | Base-modified cytidine nucleotides for leukemia therapy |
| WO2020117715A1 (en) | 2018-12-03 | 2020-06-11 | Board Of Regents, The University Of Texas System | Oligo-benzamide analogs and their use in cancer treatment |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5041449A (en) | 1988-04-11 | 1991-08-20 | Iaf Biochem International, Inc. | 4-(nucleoside base)-substituted-1,3-dioxolanes useful for treatment of retroviral infections |
| NZ228645A (en) | 1988-04-11 | 1991-09-25 | Iaf Biochem Int | 1,3-dioxolane derivatives substituted in the 5th position by a purine or pyrimidine radical; treatment of viral infections |
| US5270315A (en) | 1988-04-11 | 1993-12-14 | Biochem Pharma Inc. | 4-(purinyl bases)-substituted-1,3-dioxlanes |
| US6175008B1 (en) | 1988-04-11 | 2001-01-16 | Biochem Pharma Inc. | Processes for preparing substituted 1,3-oxathiolanes with antiviral properties |
| US5914331A (en) * | 1990-02-01 | 1999-06-22 | Emory University | Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane |
| US5276151A (en) | 1990-02-01 | 1994-01-04 | Emory University | Method of synthesis of 1,3-dioxolane nucleosides |
| US5728575A (en) * | 1990-02-01 | 1998-03-17 | Emory University | Method of resolution of 1,3-oxathiolane nucleoside enantiomers |
| US5204466A (en) * | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
| US5700937A (en) * | 1990-02-01 | 1997-12-23 | Emory University | Method for the synthesis, compositions and use of 2'-deoxy-5-fluoro-3'-thiacytidine and related compounds |
| US6703396B1 (en) * | 1990-02-01 | 2004-03-09 | Emory University | Method of resolution and antiviral activity of 1,3-oxathiolane nuclesoside enantiomers |
| US5179104A (en) | 1990-12-05 | 1993-01-12 | University Of Georgia Research Foundation, Inc. | Process for the preparation of enantiomerically pure β-D-(-)-dioxolane-nucleosides |
| US5925643A (en) | 1990-12-05 | 1999-07-20 | Emory University | Enantiomerically pure β-D-dioxolane-nucleosides |
| US5444063A (en) | 1990-12-05 | 1995-08-22 | Emory University | Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity |
| ZA923640B (en) | 1991-05-21 | 1993-02-24 | Iaf Biochem Int | Processes for the diastereoselective synthesis of nucleosides |
| GB9311709D0 (en) | 1993-06-07 | 1993-07-21 | Iaf Biochem Int | Stereoselective synthesis of nucleoside analogues using bicycle intermediate |
| JP3524606B2 (ja) * | 1994-12-28 | 2004-05-10 | 三洋電機株式会社 | 固形製剤充填装置 |
| GB9525606D0 (en) * | 1995-12-14 | 1996-02-14 | Iaf Biochem Int | Method and compositions for the synthesis of dioxolane nucleosides with - configuration |
| US5792773A (en) | 1996-11-15 | 1998-08-11 | Yale University | L-β-dioxolane uridine analog administration for treating Epstein-Barr virus infection |
| AU739240B2 (en) * | 1997-03-19 | 2001-10-04 | Emory University | Synthesis, anti-human immunodeficiency virus and anti-hepatitis B virus activities of 1,3-oxaselenolane nucleosides |
| ATE292631T1 (de) | 1998-08-12 | 2005-04-15 | Gilead Sciences Inc | Verfahren zu herstellung von 1,3-oxathiolane nukleosiden |
| MXPA01006425A (es) | 1998-12-23 | 2002-06-04 | Iaf Biochem Int | Analogos de nucleosido antivirales. |
| CA2362570A1 (en) | 1999-02-11 | 2000-08-17 | Shire Biochem Inc. | Stereoselective synthesis of nucleoside analogues |
| US6512845B1 (en) * | 1999-07-20 | 2003-01-28 | Canon Kabushiki Kaisha | Iterative approximation of color patch area |
| ATE360016T1 (de) | 2000-02-11 | 2007-05-15 | Shire Biochem Inc | Ein stereoselektives verfahren zur herstellung von nukleosidanalogen |
| AU2002212015B2 (en) * | 2000-10-13 | 2007-01-25 | Shire Canada Inc. | Dioxolane analogs for improved inter-cellular delivery |
| US20050085638A1 (en) | 2002-01-25 | 2005-04-21 | Shire Biochem Inc | Process for producing dioxolane nucleoside analogues |
| AU2003294212B2 (en) * | 2002-08-06 | 2010-01-07 | Pharmasset Inc. | Processes for preparing 1,3-dioxolane nucleosides |
| CA2554782C (en) * | 2004-02-03 | 2013-08-13 | Emory University | Methods to manufacture 1,3-dioxolane nucleosides |
-
2005
- 2005-02-03 CA CA2554782A patent/CA2554782C/en not_active Expired - Fee Related
- 2005-02-03 CN CN201510291744.8A patent/CN105039489A/zh active Pending
- 2005-02-03 KR KR1020067017856A patent/KR101157468B1/ko not_active Expired - Fee Related
- 2005-02-03 ES ES05722747.2T patent/ES2568467T3/es not_active Expired - Lifetime
- 2005-02-03 US US11/051,287 patent/US7785839B2/en active Active
- 2005-02-03 WO PCT/US2005/003620 patent/WO2005074654A2/en not_active Ceased
- 2005-02-03 CN CNA2005800119950A patent/CN101044122A/zh active Pending
- 2005-02-03 EP EP05722747.2A patent/EP1720840B1/en not_active Expired - Lifetime
- 2005-02-03 BR BRPI0507363-4A patent/BRPI0507363A/pt active Search and Examination
-
2010
- 2010-08-27 US US12/870,319 patent/US8420354B2/en not_active Expired - Lifetime
-
2016
- 2016-04-15 HK HK16104317.0A patent/HK1216432A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8420354B2 (en) | 2013-04-16 |
| KR101157468B1 (ko) | 2012-07-06 |
| CA2554782C (en) | 2013-08-13 |
| WO2005074654A3 (en) | 2005-09-22 |
| CA2554782A1 (en) | 2005-08-18 |
| WO2005074654A2 (en) | 2005-08-18 |
| CN101044122A (zh) | 2007-09-26 |
| US20110130559A1 (en) | 2011-06-02 |
| HK1216432A1 (zh) | 2016-11-11 |
| EP1720840A2 (en) | 2006-11-15 |
| CN105039489A (zh) | 2015-11-11 |
| KR20070085075A (ko) | 2007-08-27 |
| EP1720840A4 (en) | 2009-01-21 |
| EP1720840B1 (en) | 2016-02-03 |
| ES2568467T3 (es) | 2016-04-29 |
| US20060036092A1 (en) | 2006-02-16 |
| US7785839B2 (en) | 2010-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B06F | Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette] | ||
| B07D | Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette] | ||
| B07G | Grant request does not fulfill article 229-c lpi (prior consent of anvisa) [chapter 7.7 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
| B09A | Decision: intention to grant [chapter 9.1 patent gazette] | ||
| B11D | Dismissal acc. art. 38, par 2 of ipl - failure to pay fee after grant in time |