WO2006080326A1 - ヌクレオシド誘導体の製造方法 - Google Patents
ヌクレオシド誘導体の製造方法 Download PDFInfo
- Publication number
- WO2006080326A1 WO2006080326A1 PCT/JP2006/301096 JP2006301096W WO2006080326A1 WO 2006080326 A1 WO2006080326 A1 WO 2006080326A1 JP 2006301096 W JP2006301096 W JP 2006301096W WO 2006080326 A1 WO2006080326 A1 WO 2006080326A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- noble metal
- catalyst
- group
- surface area
- particle size
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Definitions
- the present invention provides a method for producing 2 ', 3'-dideoxyinosine (didanocin, hereinafter referred to as "DDI”) represented by the following formula (4) useful as an antiviral drug,
- the present invention relates to a method for producing 2 ′, 3′-dideoxyadenosine (hereinafter referred to as “DDA”) represented by the following formula (2), which is an important intermediate compound.
- DDI is useful as an antiviral drug, and has already been approved as an anti-AIDS (AIDS) drug in many countries including the United States, Japan and Europe.
- AIDS anti-AIDS
- DD didehydro
- a reduction catalyst When synthesizing a didehydro form from a nucleoside, a reduction catalyst is used. When a noble metal-supported catalyst is used, the target compound can be obtained in good yield, but the catalyst itself is expensive and cannot be used in large quantities. .
- Non-Patent Document 1 Chu, CK et al. J. Org. Chem. 1989, 54, 2217-2225 Disclosure of the invention
- the object of the present invention is to provide an industrially advantageous method for producing a nucleoside derivative that can achieve an equivalent yield even with a small amount of catalyst compared to conventional products. Means to solve
- the present invention provides a nucleoside represented by the following formula (1):
- R is hydrogen or a protecting group, R is NH or OH, R is an acyl group,
- X is a chlorine atom or a bromine atom.
- Noble metal specific surface area is 56. Om 2 / g or more and noble metal particle size is 8. Onm or less.
- the present invention also provides a nucleoside represented by the following formula (1): [0011]
- a method for producing a nucleoside derivative represented by the following formula (2) is provided.
- the present invention also includes a 2 ′, 3 represented by the following formula (4), which comprises reacting a nucleoside derivative represented by the formula (2) obtained by the production method of the present invention with an enzyme to cause a deamino reaction.
- a method for producing '-dideoxyinosine is provided.
- DDA and DDI can be produced with an equivalent yield even when the amount of catalyst is smaller than that of conventional products.
- DDA and DDI can be produced in a short reaction time despite the fact that the amount of catalyst is smaller than that of conventional products.
- a first aspect of the present invention is a method for producing a nucleoside derivative represented by the above formula (2) by reducing the nucleoside represented by the above formula (1) using the above-mentioned specific noble metal catalyst. It is.
- the nucleoside represented by the above formula (1) is converted into a compound represented by the above formula (3), and then reduced using the above-mentioned specific noble metal catalyst.
- This is a method for producing a nucleoside derivative represented by the formula (2).
- the protecting group include an acyl group, a substituted or unsubstituted benzyl group, a silyl group, a benzhydryl group, and a trityl group.
- substituent for the benzyl group include alkyl groups having 1 to 12 carbon atoms such as a methyl group, an ethyl group, an n-propyl group, and an i-propyl group; a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like
- examples of the isyl group include a acetyl group, a propionyl group, and a butyryl group.
- R is preferably a protecting group, more preferably an acyl group.
- R is preferably ⁇
- R is preferably an acetyl group.
- R is a acetyl group
- R is ⁇
- R is a acetyl group
- X is Bromine atom
- the nucleoside represented by the above formula (1) used in the production method of the present invention can be produced by using a known method described in, for example, JP-A-3-227997. Specifically, a mixture of adenosine suspended in acetic acid and trimethylorthoacetate added thereto was stirred at a predetermined temperature and time, and then methanol was distilled off under reduced pressure. It can be produced by gradually adding to a mixed solution of acetic acid and acetyl chloride and stirring at a predetermined temperature.
- the reduction catalyst used in the present invention is supported on a carrier selected from the group consisting of (i) and (ii) below! It is a noble metal catalyst containing a noble metal.
- a uniform supported catalyst having a noble metal specific surface area of 95. Om 2 / g or more and a noble metal particle size of 4.3 nm or less;
- (B) A surface-supported catalyst having a noble metal specific surface area of 56. Om 2 / g or more and a noble metal particle size of 8. Onm or less.
- the “homogeneously supported catalyst” refers to a catalyst in which a catalyst component is uniformly distributed to the inside of the carrier.
- the “surface-supported catalyst” refers to a catalyst in which a large amount of catalyst components are distributed in the surface layer portion of the carrier.
- the catalyst component is prepared by adding a noble metal-containing compound corresponding to a predetermined loading amount to a carrier suspended in water, adsorbing the noble metal-containing compound on the carrier, performing a reduction treatment, and then drying.
- the method for controlling the distribution of the catalyst component is not particularly limited, but a competitive adsorption method can be mentioned. Specifically, by adding organic acid or inorganic acid to the noble metal-containing compound, and controlling the addition amount, pH, impregnation time, support surface area, pore diameter, etc., the uniform support type and surface support It is possible to make different holding types.
- Strong homogeneous supported palladium catalysts and surface supported palladium catalysts are produced according to the above-mentioned methods, or commercially available catalysts having a predetermined specific surface area and palladium distribution, for example, uniformly supported 10% palladium carbon catalyst (Kawaken) Fine chemicals) and surface-supported 10% palladium carbon catalyst (made by Kawaken Fine Chemicals) can be used as they are.
- uniformly supported 10% palladium carbon catalyst Kawaken
- surface-supported 10% palladium carbon catalyst made by Kawaken Fine Chemicals
- the catalyst (A) used in the present invention is preferably a homogeneous supported catalyst having a noble metal specific surface area of 115. Om 2 / g or more and a noble metal particle size of 3.5 nm or less. Use of such a catalyst is preferable because the reduction can be completed in a short time and the reduction reaction can be carried out efficiently even when the amount of the catalyst is small.
- the catalyst (B) used in the present invention is preferably a surface-supported catalyst having a noble metal specific surface area of 65. Om 2 / g or more and a noble metal particle size of 7.5 nm or less. Use of such a catalyst is preferable because the reduction can be completed in a short time and the reduction reaction can be performed even if the amount of the catalyst is reduced.
- the catalyst (A) is more preferably a homogeneous supported catalyst having a noble metal dispersion of 21.5% or more.
- the catalyst (B) is preferably a surface-supported catalyst having a noble metal dispersion degree of 15.0% or more. Use of such a catalyst is preferable because the reduction can be completed in a shorter time and the reduction reaction can be carried out even if the amount of the catalyst is further reduced.
- the catalyst (A) and the catalyst (B) may be dried or may contain moisture.
- the most preferred uniform supported catalyst has a noble metal specific surface area of 120. Om 2 / g or more, The genus particle size is 3.5 nm or less. More particularly, the precious metal dispersion is preferably 25.0% or more.
- the most preferred surface-supported catalyst has a noble metal specific surface area of 70. Om 2 / g or more and a noble metal particle size of 6. Onm or less. Use of such a catalyst is preferable because the reduction reaction can be completed in a short time even if the amount of the catalyst is reduced. More particularly, the precious metal dispersion is preferably 15.5% or more.
- the noble metal specific surface area, the noble metal particle size, and the noble metal dispersion of the catalyst used in the present invention can be measured by a CO gas adsorption method.
- the CO gas adsorption amount was measured by a pulse method after pretreatment by hydrogen reduction using a fully automatic catalytic gas adsorption amount measuring device R-6015 (manufactured by Okura Riken).
- the noble metal specific surface area, the noble metal particle size, and the noble metal dispersion can be appropriately increased or decreased by controlling the catalyst preparation conditions. Specifically, it can be controlled by changing the type of the carrier and the impregnation conditions.
- Examples of the noble metal constituting the catalyst used in the present invention include nodium, platinum, ruthenium, zinc, iridium and the like. Of these, palladium, which is preferably radium or platinum, is most preferred.
- the catalyst used in the present invention may contain alkali metals such as sodium, potassium and lithium in addition to noble metals.
- the carrier constituting the catalyst used in the present invention may be any support that is inert under the reaction conditions.
- activated carbon silica, ⁇ -alumina, ⁇ -alumina, silica-alumina, and various metal oxides. Activated carbon is most preferred.
- the amount of noble metal supported in the catalyst used in the present invention is preferably 1 to 25% in terms of noble metal element, more preferably 5 to 15%, based on the mass of the support particles. I like it.
- the catalyst used in the present invention can be used repeatedly. When reusing, the catalyst is recovered by filtering the reaction solution after completion of the reduction reaction, either as it is or under reduced pressure. By doing so, it can be reused.
- the drying conditions at this time are preferably 105 ° C. for 2 hours. Only reused products may be used for the reduction reaction, or reused products and unused ones may be used in combination. When used together, reused and unused ones can be used in any ratio.
- the amount of the catalyst used is 0.001 equivalent or more in terms of noble metal element with respect to the nucleoside represented by the formula (1). It is more preferable that the amount is 0.005 equivalent or more. Use of a catalyst in such a range is preferable because the reaction is completed in a short time and production is efficient. When a reductive catalyst and an unused catalyst are used in combination for the reduction reaction, they can be used in any ratio, and at this time, an unused catalyst may or may not be added.
- the reduction reaction can be preferably carried out under normal pressure at a reaction temperature of from room temperature to 40 ° C, more preferably from room temperature to 30 ° C, within 50 hours, more preferably within 20 hours.
- the reaction solvent include a mixed solvent of acetonitrile and water, an ester solvent such as ethyl acetate and a mixed solvent of water, and the like. Of these, a mixed solvent of acetonitrile and water and a mixed solvent of ethyl acetate and water are preferable.
- the reaction is preferably carried out under basic conditions.
- the reagent for adjusting the reaction solvent to basic include conventional basic substances such as sodium hydroxide.
- the pH of the reaction solvent is preferably pH 8 or more, more preferably pH 8 or more and 11 or less, and further preferably pH 8.5 or more and 10.5 or less.
- the reduction reaction can be performed, for example, while blowing hydrogen in a container of 50 ml or more. At this time, the amount of hydrogen to be introduced is preferably 2 equivalents or more with respect to the nucleoside represented by the formula (1).
- the conversion from the nucleoside represented by the formula (1) to the compound represented by the formula (3) is carried out by reacting in the presence of zinc powder, zinc-copper complex or the like. I can do it.
- Zinc powder, zinc-copper complex, etc. are preferably used in a metal element equivalent concentration of 2 to 3 equivalents.
- the reaction solvent include dimethylformamide (DMF), acetonitrile, methanol, ethanol, THF and the like. Of these, DMF, acetonitrile, and methanol are preferable.
- the reaction is preferably carried out under neutrality or basicity.
- the reagent for adjusting the reaction solvent to neutral or basic include conventional basic substances such as sodium hydroxide.
- the pH of the reaction solvent is preferably pH 7 or more, more preferably pH 7 11 or less.
- reduction of the compound of formula (3) to obtain the nucleoside derivative of formula (1) can be carried out in the same manner as described in the first embodiment. .
- the reaction solution can be filtered and separated from the catalyst, if necessary, or can be added with a basic aqueous solution such as a sodium hydroxide aqueous solution.
- a basic aqueous solution such as a sodium hydroxide aqueous solution.
- the nucleoside derivative represented by the formula (2) obtained by the method of the present invention is further described in, for example, JP-A-2-291291, which uses an enzyme which is a known method.
- the DDI represented by the formula (4) can be produced by the conversion reaction.
- enzymes that can be used include deaminase. Of these, adenosine deaminase is preferred. Alternatively, cultured cells of microorganisms that produce enzymes may be used.
- the reaction is preferably carried out under normal pressure at a reaction temperature of 5 to 70 ° C., more preferably at 20 to 60 ° C., for 10 minutes to 10 days.
- the pH is preferably adjusted to a range of 3 to 10, more preferably 4 to 9.
- Acids used include mineral acids such as hydrochloric acid, phosphoric acid, sulfuric acid and nitric acid, and organic acids such as formic acid, acetic acid and citrate. According to the present invention, DDI represented by the formula (4) can be obtained in a yield of 70% or more.
- Catalyst B 10% noradium carbon catalyst Wet manufactured by Kawaken Fine Chemicals Co., Ltd. (Surface supported type, noble metal specific surface area 104 m 2 / g, noble metal particle size 4.0 nm, noble metal dispersion 23.3%)
- Catalyst C 10% NO ⁇ radium carbon catalyst Wet (Uniform support type, precious gold, manufactured by Kawaken Fine Chemical Co., Ltd. (Genus specific surface area 67m 2 / g, noble metal particle size 6.2, noble metal dispersion 15.1%)
- reaction solution after the reduction was separated from the catalyst by filtration, and saponified by adding an aqueous sodium hydroxide solution.
- 2 ′, 3′-dideoxyadenosine was produced in a yield of 80%.
- 0.4% of 2 ', 3' didehydroxy-2 ', 3' epoxy adenosine is contained as an impurity.
- the catalyst B 10 Og (0.028 equivalent as palladium) was used, and 9- (2,5-O diacetyl-3-bromo-3-deoxy- ⁇ - ⁇ -xylofuranosyl) adenine A reduction reaction was performed. The reduction reaction was completed in 4.5 hours.
- reaction solution after reduction was separated from the catalyst by filtration, and saponified by adding an aqueous sodium hydroxide solution. As determined by HPLC, 2,3′-dideoxyadenosine was produced in a yield of 84%.
- Example 1 As in Example 1, 4.7 g of catalyst C (0.03 equivalents as palladium) was used to reduce 9- (2,5-O-diacetyl-1-3-bromo-3-deoxy-13-D-xylofuranosyl) adenine. Reaction was performed. The reduction reaction was completed in 9 hours.
- reaction solution after the reduction is filtered to separate it from the catalyst.
- saponification was performed. As determined by HPLC, 2 ′, 3′-dideoxyadenosine was produced in a yield of 77%.
- reaction solution after the reduction was separated from the catalyst by filtration, and saponified by adding an aqueous sodium hydroxide solution.
- 2 ′, 3′-dideoxyadenosine was produced in a yield of 78%. It also contains 0.6% 2 ', 3' didehydroxy-2 ', 3' epoxyadenosine as an impurity.
- the catalyst ⁇ ⁇ once used for the reduction reaction in the same manner as in Example 1 was dried under reduced pressure. 6.4 g (0.028 equivalents of palladium) was used, and 19.4 wt% of 9- (2, 5-O diacetate was used. Reduction reaction was carried out in the same manner as in Example 1 on 368 g of a mixed solution of acetonitrile and water containing til-3-bromo-3-deoxy-j8-D xylofuranosyl) adenine (71.3 g, 17 2 mmol). . The reduction reaction was completed in 11.5 hours.
- reaction solution after the reduction was separated from the catalyst by filtration, and saponified by adding an aqueous sodium hydroxide solution. As determined by HPLC, 2 ′, 3′-dideoxyadenosine was produced in a yield of 8 1%! /.
- Catalyst B once used for the reduction reaction in the same manner as in Example 2 was dried under reduced pressure 6.7 g (0.028 equivalents as palladium) was used, and 9— (2,5-O diacetinol 1 3 bromide— 3 Deoxy- ⁇ -D xylofuranosyl) adenine was subjected to a reduction reaction in the same manner as in Example 2. The reduction reaction was completed in 7 hours.
- reaction solution after the reduction was separated from the catalyst by filtration, and saponified by adding an aqueous sodium hydroxide solution. As determined by HPLC, 2 ', 3'-dioxyadenosine was 8 It was produced in 2% yield.
- the catalyst C once used for the reduction reaction in the same manner as in Comparative Example 1 was dried under reduced pressure. 6.7 g (0.028 equivalents of palladium) was used, and 9— (2,5-O diacetinol 1 3 bromide—
- the reduction reaction was performed in the same manner as in Comparative Example 1 on 3 Deoxy- ⁇ -D Xylofuranosyl) adenine. The reduction reaction was completed in 15.5 hours.
- reaction solution after the reduction was separated from the catalyst by filtration, and saponified by adding an aqueous sodium hydroxide solution. As determined by HPLC, 2 ′, 3′-dideoxyadenosine was produced in a yield of 75%.
- the catalyst D once used for the reduction reaction in the same manner as in Comparative Example 2 was dried under reduced pressure. 11.
- Og (0.028 equivalent as palladium) 9- (2,5-O diacetinore 3 bromide— 3 Deoxy- ⁇ -D xylofuranosyl) adenine was subjected to a reduction reaction in the same manner as in Comparative Example 2. The reduction reaction was completed in 11.5 hours.
- reaction solution after the reduction was separated from the catalyst by filtration, and saponified by adding an aqueous sodium hydroxide solution. As determined by HPLC, 2 ′, 3′-dideoxyadenosine was produced in a yield of 62%.
- reaction solution after the reduction was filtered to recover 33.4 g of the catalyst.
- the filtration of the catalyst took 0.5 hour.
- a part of the filtrate was subjected to a quench by adding a sodium hydroxide aqueous solution.
- 2 ', 3'-dideoxyadenosine was produced in 83% yield. It was.
- reaction solution after the reduction was filtered to recover 28. lg of catalyst.
- the catalyst filtration took 1.5 hours.
- the filtrate was squeezed with an aqueous sodium hydroxide solution.
- 2 ′, 3′-dideoxyadenosine was produced in a yield of 78%.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06712291A EP1849786A4 (en) | 2005-01-25 | 2006-01-25 | PROCESS FOR PRODUCING NUCLEOSIDE DERIVATIVE |
JP2007500528A JP5187560B2 (ja) | 2005-01-25 | 2006-01-25 | ヌクレオシド誘導体の製造方法 |
US11/782,695 US8362244B2 (en) | 2005-01-25 | 2007-07-25 | Method for producing nucleoside derivatives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005016596 | 2005-01-25 | ||
JP2005-016596 | 2005-01-25 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/782,695 Continuation US8362244B2 (en) | 2005-01-25 | 2007-07-25 | Method for producing nucleoside derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006080326A1 true WO2006080326A1 (ja) | 2006-08-03 |
Family
ID=36740356
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2006/301096 WO2006080326A1 (ja) | 2005-01-25 | 2006-01-25 | ヌクレオシド誘導体の製造方法 |
Country Status (4)
Country | Link |
---|---|
US (1) | US8362244B2 (ja) |
EP (1) | EP1849786A4 (ja) |
JP (1) | JP5187560B2 (ja) |
WO (1) | WO2006080326A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8362244B2 (en) | 2005-01-25 | 2013-01-29 | Ajinomoto Co., Inc. | Method for producing nucleoside derivatives |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63185449A (ja) * | 1987-01-27 | 1988-08-01 | Tanaka Kikinzoku Kogyo Kk | パラジウム触媒の製造方法 |
JPH01224390A (ja) * | 1988-03-01 | 1989-09-07 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH02117689A (ja) * | 1988-07-11 | 1990-05-02 | Ajinomoto Co Inc | ジデオキシヌクレオシド類の製造方法 |
JPH02164895A (ja) * | 1988-12-19 | 1990-06-25 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH02291291A (ja) * | 1987-10-07 | 1990-12-03 | Ajinomoto Co Inc | ジデオキシイノシンの製造方法 |
JPH0390096A (ja) * | 1989-08-31 | 1991-04-16 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH03190876A (ja) * | 1989-12-21 | 1991-08-20 | Ajinomoto Co Inc | 選択的加水分解によるジデオキシヌクレオシド誘導体の製造方法 |
JPH03227997A (ja) * | 1990-01-30 | 1991-10-08 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH05219978A (ja) * | 1992-02-14 | 1993-08-31 | Yamasa Shoyu Co Ltd | 核酸関連物質の酵素的製造法及びそれに使用する酵素調製物 |
JPH0631181A (ja) * | 1992-07-06 | 1994-02-08 | Stonehard Assoc Inc | 高分散金属微粒子担持触媒の製造方法 |
JPH11513302A (ja) * | 1995-10-04 | 1999-11-16 | ビーエーエスエフ アクチェンゲゼルシャフト | 水素化触媒の製造法 |
JP2002535296A (ja) * | 1999-01-21 | 2002-10-22 | エイビービー ラマス グローバル インコーポレイテッド | 選択的水素添加プロセスとその触媒 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5466793A (en) * | 1988-03-01 | 1995-11-14 | Ajinomoto Co., Inc. | Process for preparing 2', 3'- dideoxyinosine |
US5290927A (en) * | 1988-03-01 | 1994-03-01 | Ajinomoto Co., Inc. | Process for preparing 2',3'-dideoxyadenosine |
US4916218A (en) * | 1988-06-09 | 1990-04-10 | Almond Merrick R | 1-(β-D-xylofuranosyl)thymine derivatives |
US5310895A (en) * | 1989-12-21 | 1994-05-10 | Ajinomoto Co., Inc. | Method for production of nucleoside derivatives by selective hydrolysis |
JPH09257687A (ja) * | 1996-01-16 | 1997-10-03 | Matsushita Electric Ind Co Ltd | 固体高分子型燃料電池の貴金属触媒の反応比表面積と利用率測定法および固体高分子型燃料電池用電極の触媒層 |
EP2251015B1 (en) * | 2000-10-18 | 2013-02-20 | Gilead Pharmasset LLC | Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation |
WO2006080326A1 (ja) | 2005-01-25 | 2006-08-03 | Ajinomoto Co., Inc. | ヌクレオシド誘導体の製造方法 |
-
2006
- 2006-01-25 WO PCT/JP2006/301096 patent/WO2006080326A1/ja active Application Filing
- 2006-01-25 JP JP2007500528A patent/JP5187560B2/ja not_active Expired - Fee Related
- 2006-01-25 EP EP06712291A patent/EP1849786A4/en not_active Withdrawn
-
2007
- 2007-07-25 US US11/782,695 patent/US8362244B2/en not_active Expired - Fee Related
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63185449A (ja) * | 1987-01-27 | 1988-08-01 | Tanaka Kikinzoku Kogyo Kk | パラジウム触媒の製造方法 |
JPH02291291A (ja) * | 1987-10-07 | 1990-12-03 | Ajinomoto Co Inc | ジデオキシイノシンの製造方法 |
JPH01224390A (ja) * | 1988-03-01 | 1989-09-07 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH02117689A (ja) * | 1988-07-11 | 1990-05-02 | Ajinomoto Co Inc | ジデオキシヌクレオシド類の製造方法 |
JPH02164895A (ja) * | 1988-12-19 | 1990-06-25 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH0390096A (ja) * | 1989-08-31 | 1991-04-16 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH03190876A (ja) * | 1989-12-21 | 1991-08-20 | Ajinomoto Co Inc | 選択的加水分解によるジデオキシヌクレオシド誘導体の製造方法 |
JPH03227997A (ja) * | 1990-01-30 | 1991-10-08 | Ajinomoto Co Inc | ヌクレオシド誘導体の製造方法 |
JPH05219978A (ja) * | 1992-02-14 | 1993-08-31 | Yamasa Shoyu Co Ltd | 核酸関連物質の酵素的製造法及びそれに使用する酵素調製物 |
JPH0631181A (ja) * | 1992-07-06 | 1994-02-08 | Stonehard Assoc Inc | 高分散金属微粒子担持触媒の製造方法 |
JPH11513302A (ja) * | 1995-10-04 | 1999-11-16 | ビーエーエスエフ アクチェンゲゼルシャフト | 水素化触媒の製造法 |
JP2002535296A (ja) * | 1999-01-21 | 2002-10-22 | エイビービー ラマス グローバル インコーポレイテッド | 選択的水素添加プロセスとその触媒 |
Non-Patent Citations (4)
Title |
---|
DILLON J.L.: "IN SITU ACTIVATED ZINC-COPPER COUPLE FOR THE PREPARATION OF A KEY INTERMEDIATE IN THE SYNTHESIS OF DIDEOXYINOSINE(DDI)", SYNTHETIC COMMUNICATIONS, vol. 27, no. 24, 1997, pages 4367 - 4371, XP001097418 * |
ROBINS M.J. ET AL.: "A MILD CONVERSION OF VICINAL DIOLS TO ALKENES. EFFICIENT TRANSFORMATION OF RIBONUCLEOSIDES INTO 2' -ENE AND 2', 3'-DIDEOXYNUCLEOSIDES", TETRAHEDRON LETTERS, vol. 25, no. 4, 1984, pages 367 - 370, XP000569322 * |
See also references of EP1849786A4 * |
SHIRAGAMI H. ET AL.: "SYNTHESIS OF 2', 3'-DIDEOXYPURINENUCLEOSIDES VIA THE PALLADIUM CATALYZED REDUCTION OF 9-(2,5-DI-O-ACETYL-3-BROMO-3-DEOXY-BETA-D-XYLOFURANOSYL)PURINE DERIVATIVES", NUCLEOSIDES & NUCLEOTIDES, vol. 15, no. 1-3, 1996, pages 31 - 45, XP002999155 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8362244B2 (en) | 2005-01-25 | 2013-01-29 | Ajinomoto Co., Inc. | Method for producing nucleoside derivatives |
Also Published As
Publication number | Publication date |
---|---|
US8362244B2 (en) | 2013-01-29 |
EP1849786A1 (en) | 2007-10-31 |
JP5187560B2 (ja) | 2013-04-24 |
US20070282104A1 (en) | 2007-12-06 |
JPWO2006080326A1 (ja) | 2008-06-19 |
EP1849786A4 (en) | 2011-03-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES2746801T3 (es) | Proceso de preparación de agonistas beta-3 y productos intermedios | |
JPS5951289A (ja) | 新規な9−置換−カンプトテシン誘導体 | |
JP2018502909A5 (ja) | ||
JP2011001372A (ja) | イノシン誘導体及びその製造方法 | |
JP2009504800A (ja) | バルサルタンの調製方法 | |
JPH0310630B2 (ja) | ||
CA2773012A1 (en) | Process for the preparation of lenalidomide | |
WO2013168693A1 (ja) | セピアプテリン及びテトラヒドロラクトイルプテリンの製造法 | |
WO2014166324A1 (zh) | 替格瑞洛的中间体及其制备方法和替格瑞洛的制备方法 | |
TW200906845A (en) | Gemcitabine production process | |
WO2006080326A1 (ja) | ヌクレオシド誘導体の製造方法 | |
JPH029032B2 (ja) | ||
CN108623602B (zh) | 一种制备和纯化依鲁替尼的方法 | |
WO2019165802A1 (zh) | 一种制备2-氨基吲哚衍生物的方法 | |
JP2015526507A (ja) | フルボキサミン遊離塩基の精製方法およびそれを用いた高純度フルボキサミンマレイン酸塩の製造方法 | |
JP4603274B2 (ja) | 2’−デオキシ−5−トリフルオロメチルウリジンの製造方法 | |
JP2006516249A (ja) | 2−デオキシ−d−グルコースの合成方法 | |
JPS60239496A (ja) | N↑6−置換−アデノシン−3′,5′−環状リン酸及びその塩の製法 | |
CN1268633C (zh) | 吲哚并咔唑苷的制备和分离 | |
JP2009530251A (ja) | L−核酸誘導体の製造方法およびその中間体 | |
JP5614153B2 (ja) | カンデサルタンシレキセチルの製造法 | |
JPH03227997A (ja) | ヌクレオシド誘導体の製造方法 | |
JP3070863B2 (ja) | 2´,3´−ジデオキシピリミジンヌクレオシド類の製造方法 | |
JP2006199652A (ja) | 2’−デオキシグアノシン化合物の製造方法 | |
US20120197010A1 (en) | Process of making cladribine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2007500528 Country of ref document: JP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 11782695 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006712291 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 3721/CHENP/2007 Country of ref document: IN |
|
WWP | Wipo information: published in national office |
Ref document number: 2006712291 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 11782695 Country of ref document: US |