JP5613168B2 - デオキシリボフラノース化合物の製造方法 - Google Patents
デオキシリボフラノース化合物の製造方法 Download PDFInfo
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- JP5613168B2 JP5613168B2 JP2011536559A JP2011536559A JP5613168B2 JP 5613168 B2 JP5613168 B2 JP 5613168B2 JP 2011536559 A JP2011536559 A JP 2011536559A JP 2011536559 A JP2011536559 A JP 2011536559A JP 5613168 B2 JP5613168 B2 JP 5613168B2
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- 0 CC(C)(O[C@@]12)O[C@]1O[C@](C*C(C)=O)C2(O)O Chemical compound CC(C)(O[C@@]12)O[C@]1O[C@](C*C(C)=O)C2(O)O 0.000 description 3
- JAUQZVBVVJJRKM-XZBKPIIZSA-N CC(C)(O[C@@H]12)O[C@H]1O[C@H](CO)[C@@H]2O Chemical compound CC(C)(O[C@@H]12)O[C@H]1O[C@H](CO)[C@@H]2O JAUQZVBVVJJRKM-XZBKPIIZSA-N 0.000 description 1
- WPLDJOXMDWWZCR-FTLITQJKSA-N CC(C)(O[C@@H]12)O[C@H]1O[C@H](COC(C)=O)C2=O Chemical compound CC(C)(O[C@@H]12)O[C@H]1O[C@H](COC(C)=O)C2=O WPLDJOXMDWWZCR-FTLITQJKSA-N 0.000 description 1
- AUYDCDFGKWMOKV-FNCVBFRFSA-N CC(C)(O[C@@H]12)O[C@H]1O[C@H](COC(C)=O)[C@H]2O Chemical compound CC(C)(O[C@@H]12)O[C@H]1O[C@H](COC(C)=O)[C@H]2O AUYDCDFGKWMOKV-FNCVBFRFSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
(iii)上記モノアシルで置換された化合物(6)及び(7)の混合物を平衡化して、化合物(6)を過剰とし、
(iv)上記化合物(6)及び(7)の混合物を酸化して、化合物(8)のケトン及び化合物(9)の水和ケトンの混合物:
1H NMR(400MHz,CDCl3)δ:5.92(1H,d,J=3.3Hz),4.51−4.56(2H,m),4.24−4.28(1H,m),4.13−4.19(2H,m),2.98(1H,d,J=4.0Hz),2.11(3H,s),1.51(3H,s),1.33(3H,s).
1H NMR(400MHz,CDCl3)δ:6.09(1H,d,J=4.4Hz,化合物8),5.84(1H,d,J=3.9Hz,化合物9),4.61(1H,dd,J1=11.7Hz,J2=6.3Hz,化合物9),4.56(1H,t,J=3.3Hz,化合物8),4.36−4.42(2H,m,化合物8及び9),4.20−4.24(2H,m,化合物8及び9),4.06−4.15(2H,m,化合物8及び9),2.11(3H,s,化合物9),2.05(3H,s,化合物8),1.58(3H,s,化合物9),1.50(3H,s,化合物8),1.43(3H,s,化合物8),1.36(3H,s,化合物9).
算出された収率:2370.5g(溶液)×0.243g(生成物)/5g(溶液)=115.2g(496.15mmol、62%)(化合物10)
1H NMRによって、上記物質が非常に純粋なサンプルであることが確認できた。
1H NMR(400MHz,CDCl3)δ:5.82(1H,d,J=3.9Hz),4.58(1H,t,J=4.3Hz),4.43(1H,dd,J1=12.4Hz,J2=2.4Hz),4.16−4.20(1H,m),3.93−3.97(1H,m),3.81−3.87(1H,m),2.45(1H,d,J=10.8Hz),2.10(3H,s),1.58(3H,s),1.38(3H,s).
1H NMR(400MHz,CDCl3)δ:1.43(3H,s),1.50(3H,s),2.05(3H,s),4.21(1H,dd,J1=11.9Hz,J2=3.9Hz),4.37(1H,d,J=4.7Hz),4.40(1H,dd,J1=12.5Hz,J2=3.2Hz),4.56(1H,t,J=3.1Hz),6.09(1H,d,J=3.8Hz).
1H−NMRによって、化合物8だけが存在する(化合物9は存在しない)ことが分かった。
1H NMR(400MHz,CDCl3)δ:5.85(1H,d,J=3.9Hz),,4.85(1H,dd,J1=8.6Hz,J2=4.6Hz),4.77(1H,t,J=4.3Hz),4.37−4.42(2H,m),4.22−4.26(1H,m),2.11(3H,s),1.61(3H,s),1.40(3H,s).
1H NMR(400MHz,CDCl3)δ:6.02(1H,d,J=2.9Hz),5.04(1H,d,J=2.9Hz),4.35(1H,d,J=3.1Hz),4.15−4.24(2H,m),3.77−3.80(1H,m),2.10(3H,s),1.52(3H,s),1.33(3H,s).
1H NMR(400MHz,CDCl3)δ:5.83(1H,d,J=3.7Hz),4.74(1H,t,J=4.2Hz),4.39−4.45(1H,m),4.28(1H,dd,J1=11.8Hz,J2=3.1Hz),4.08(1H,dd,J1=12.5Hz,J2=6.2Hz),2.07−2.12(4H,m),1.62−1.69(1H,m),1.52(3H,s),1.33(3H,s).
Claims (20)
- 化合物(2):
(i)化合物(4):
(ii)式(5)の化合物を、水、及び、触媒量又は理論量の酸で加水分解して、モノアシルで置換された化合物(6)及び(7)の混合物:
(iii)前記モノアシルで置換された化合物(6)及び(7)の混合物を加熱して、化合物(6)を過剰とし、
(iv)前記化合物(6)及び(7)の混合物を酸化して、化合物(8)のケトン及び化合物(9)の水和ケトンの混合物:
(v)前記化合物(8)のケトン及び化合物(9)の水和ケトンの混合物を還元して、化合物(10):
(vi)化合物(10)を、塩基の存在下、スルホン化剤でスルホン化して、式(11)の化合物:
(vii)前記式(11)のスルホン酸エステル化合物をハロゲン原子で置換して、式(12)のハロゲン化合物:
(viii)式(12)の化合物のハロゲンを水素原子へと還元して、化合物(13):
(ix)化合物(13)を酸触媒及びアシル化剤で処理して、化合物(2)を形成する、方法。 - R1は−CH3又は−CH2CH3である、請求項1に記載の方法。
- R2は−CF3、−CH3又は−C6H4CH3である、請求項1に記載の方法。
- 工程(iii)において、前記化合物(6)及び(7)の混合物を70℃よりも高温で加熱することにより、化合物(6)を過剰とする、請求項1に記載の方法。
- 化合物(6)及び(7)の混合物の加熱によって、化合物(6)が化合物(7)に対して90%超過剰となる、請求項5に記載の方法。
- 工程(iv)において、前記化合物(6)及び(7)の混合物を、TEMPO、及び、酢酸イソプロピルとの2相系の酢酸ナトリウムの存在下、次亜塩素酸ナトリウムにより酸化する、請求項1に記載の方法。
- 工程(v)において、ナトリウムトリアセトキシボロヒドリドを使用して、化合物(10)を単一の異性体として形成する、請求項1に記載の方法。
- 工程(vi)において、前記塩基はDMAPである、請求項1に記載の方法。
- 工程(viii)において、前記式(12)の化合物の還元は、水素の存在下、炭素担持水酸化パラジウム(パールマン触媒)を使用する、請求項1に記載の方法。
- R2は−CF3、−CH3又は−C6H4CH3である、請求項11に記載の方法。
- 化合物(6)を、TEMPO、及び、酢酸イソプロピルとの2相系の酢酸ナトリウムの存在下、次亜塩素酸ナトリウムにより酸化する、請求項11に記載の方法。
- 前記化合物(8)の還元によって、化合物(10)の単一の異性体を形成する、請求項11に記載の方法。
- 前記還元は、水素の存在下、炭素担持白金触媒を使用して行う、請求項12に記載の方法。
- 前記スルホン化剤はトリフルオロメタンスルホン酸無水物であり、前記塩基はDMAPである、請求項11に記載の方法。
- 前記式(12)の化合物の還元は、水素の存在下、炭素担持水酸化パラジウム(パールマン触媒)を使用する、請求項17に記載の方法。
- 前記酸触媒は硫酸であり、前記アシル化剤は無水酢酸である、請求項17に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11513408P | 2008-11-17 | 2008-11-17 | |
US61/115,134 | 2008-11-17 | ||
PCT/US2009/064605 WO2010057103A1 (en) | 2008-11-17 | 2009-11-16 | Method of preparing deoxyribofuranose compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012509268A JP2012509268A (ja) | 2012-04-19 |
JP5613168B2 true JP5613168B2 (ja) | 2014-10-22 |
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Application Number | Title | Priority Date | Filing Date |
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JP2011536559A Expired - Fee Related JP5613168B2 (ja) | 2008-11-17 | 2009-11-16 | デオキシリボフラノース化合物の製造方法 |
Country Status (21)
Country | Link |
---|---|
US (2) | US8829168B2 (ja) |
EP (1) | EP2365753B1 (ja) |
JP (1) | JP5613168B2 (ja) |
KR (1) | KR101643661B1 (ja) |
CN (1) | CN102300464B (ja) |
AU (1) | AU2009313842B2 (ja) |
BR (1) | BRPI0922008A2 (ja) |
CA (1) | CA2743796C (ja) |
DK (1) | DK2365753T3 (ja) |
EA (1) | EA020552B1 (ja) |
ES (1) | ES2431269T3 (ja) |
HK (1) | HK1162856A1 (ja) |
IL (1) | IL212902A0 (ja) |
MX (1) | MX2011005170A (ja) |
MY (1) | MY159745A (ja) |
NZ (1) | NZ593021A (ja) |
PL (1) | PL2365753T3 (ja) |
SI (1) | SI2365753T1 (ja) |
TW (1) | TWI450904B (ja) |
UA (1) | UA103637C2 (ja) |
WO (1) | WO2010057103A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2658933B1 (en) * | 2010-12-29 | 2017-03-01 | Akzo Nobel Coatings International B.V. | Latex emulsions and coating compositions formed from latex emulsions |
CN103172682B (zh) * | 2013-03-14 | 2015-11-18 | 北京瑞博奥生物科技有限公司 | 2-脱氧-l-呋喃核糖的制备方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
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CA2226363C (en) * | 1996-05-16 | 2001-03-13 | Taiho Pharmaceutical Co., Ltd. | D-pentofuranose derivatives and process for preparing the same |
TR200601782T2 (tr) * | 1999-11-12 | 2006-09-21 | Pharmasset Ltd. | 2'-Deoksi-L-Nükleositlerin sentezi. |
US6863782B2 (en) * | 2002-11-15 | 2005-03-08 | A.P. Pharma, Inc. | Method of preparing di(ketene acetals) |
US7034167B2 (en) * | 2002-12-06 | 2006-04-25 | Merck & Co., Inc. | Process to ribofuranose sugar derivatives as intermediates to branched-chain nucleosides |
DE602004030239D1 (de) * | 2003-06-17 | 2011-01-05 | Schering Corp | Verfahren und zwischenprodukte zur herstellung von (1r,2s,5s)-6,6-dimethyl-3-azabicycloä3,1,0 ühexan-2-carboxylaten oder salzen davon |
CA2537849A1 (en) | 2003-09-11 | 2005-03-17 | F. Hoffmann-La Roche Ag | Process for preparing antiviral nucleoside derivatives |
JP2007137843A (ja) * | 2005-11-21 | 2007-06-07 | Sumitomo Chemical Co Ltd | リボフラノース化合物およびプリンヌクレオシド化合物の製造方法 |
US20070225246A1 (en) * | 2006-03-27 | 2007-09-27 | Denu John M | O-acetyl-ADP-ribose non-hydrolyzable analogs |
CN101172989B (zh) * | 2006-11-03 | 2012-06-06 | 上海睿智化学研究有限公司 | 5-O-乙酰基-3-脱氧-1,2-异亚丙基-α-D-呋喃木糖的制备方法及一种中间体 |
BRPI0906448A2 (pt) * | 2008-01-10 | 2015-07-14 | Sun Pharma Advanced Res Co Ltd | Novos derivados do acil cyanopyrrolidines |
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2009
- 2009-11-16 DK DK09826915.2T patent/DK2365753T3/da active
- 2009-11-16 SI SI200930720T patent/SI2365753T1/sl unknown
- 2009-11-16 US US13/129,730 patent/US8829168B2/en not_active Expired - Fee Related
- 2009-11-16 TW TW098138837A patent/TWI450904B/zh active
- 2009-11-16 JP JP2011536559A patent/JP5613168B2/ja not_active Expired - Fee Related
- 2009-11-16 MY MYPI2011002192A patent/MY159745A/en unknown
- 2009-11-16 CN CN200980154858.0A patent/CN102300464B/zh not_active Expired - Fee Related
- 2009-11-16 PL PL09826915T patent/PL2365753T3/pl unknown
- 2009-11-16 EA EA201170702A patent/EA020552B1/ru not_active IP Right Cessation
- 2009-11-16 BR BRPI0922008A patent/BRPI0922008A2/pt not_active Application Discontinuation
- 2009-11-16 MX MX2011005170A patent/MX2011005170A/es active IP Right Grant
- 2009-11-16 UA UAA201106699A patent/UA103637C2/uk unknown
- 2009-11-16 WO PCT/US2009/064605 patent/WO2010057103A1/en active Application Filing
- 2009-11-16 KR KR1020117013874A patent/KR101643661B1/ko active IP Right Grant
- 2009-11-16 AU AU2009313842A patent/AU2009313842B2/en not_active Ceased
- 2009-11-16 NZ NZ593021A patent/NZ593021A/xx not_active IP Right Cessation
- 2009-11-16 CA CA2743796A patent/CA2743796C/en not_active Expired - Fee Related
- 2009-11-16 EP EP09826915.2A patent/EP2365753B1/en not_active Not-in-force
- 2009-11-16 ES ES09826915T patent/ES2431269T3/es active Active
-
2011
- 2011-05-16 IL IL212902A patent/IL212902A0/en not_active IP Right Cessation
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2012
- 2012-03-21 HK HK12102829.9A patent/HK1162856A1/xx not_active IP Right Cessation
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2014
- 2014-07-31 US US14/448,033 patent/US9227992B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
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NZ593021A (en) | 2013-04-26 |
US20140350231A1 (en) | 2014-11-27 |
KR101643661B1 (ko) | 2016-07-28 |
BRPI0922008A2 (pt) | 2016-05-10 |
EA201170702A1 (ru) | 2011-12-30 |
CA2743796A1 (en) | 2010-05-20 |
CN102300464A (zh) | 2011-12-28 |
UA103637C2 (uk) | 2013-11-11 |
CN102300464B (zh) | 2014-11-12 |
EP2365753A4 (en) | 2012-07-04 |
TW201028430A (en) | 2010-08-01 |
MX2011005170A (es) | 2011-05-30 |
PL2365753T3 (pl) | 2013-12-31 |
SI2365753T1 (sl) | 2014-01-31 |
EA020552B1 (ru) | 2014-12-30 |
JP2012509268A (ja) | 2012-04-19 |
TWI450904B (zh) | 2014-09-01 |
HK1162856A1 (en) | 2012-09-07 |
AU2009313842A1 (en) | 2010-05-20 |
US20110288282A1 (en) | 2011-11-24 |
US8829168B2 (en) | 2014-09-09 |
AU2009313842B2 (en) | 2015-08-20 |
MY159745A (en) | 2017-01-31 |
IL212902A0 (en) | 2011-07-31 |
US9227992B2 (en) | 2016-01-05 |
WO2010057103A1 (en) | 2010-05-20 |
CA2743796C (en) | 2016-10-25 |
ES2431269T3 (es) | 2013-11-25 |
DK2365753T3 (da) | 2013-10-21 |
EP2365753B1 (en) | 2013-07-17 |
EP2365753A1 (en) | 2011-09-21 |
KR20110084542A (ko) | 2011-07-25 |
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