JPH01175991A - Purifying method of dideoxyinosine - Google Patents
Purifying method of dideoxyinosineInfo
- Publication number
- JPH01175991A JPH01175991A JP33617187A JP33617187A JPH01175991A JP H01175991 A JPH01175991 A JP H01175991A JP 33617187 A JP33617187 A JP 33617187A JP 33617187 A JP33617187 A JP 33617187A JP H01175991 A JPH01175991 A JP H01175991A
- Authority
- JP
- Japan
- Prior art keywords
- ddi
- dideoxyinosine
- deoxyinosine
- porous resin
- column
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 19
- 229960002656 didanosine Drugs 0.000 title claims abstract description 5
- 239000011347 resin Substances 0.000 claims abstract description 16
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000012535 impurity Substances 0.000 claims abstract description 9
- UGQMRVRMYYASKQ-KQYNXXCUSA-N Inosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(O)=C2N=C1 UGQMRVRMYYASKQ-KQYNXXCUSA-N 0.000 claims abstract description 4
- 229930010555 Inosine Natural products 0.000 claims abstract description 4
- 229960003786 inosine Drugs 0.000 claims abstract description 4
- VGONTNSXDCQUGY-RRKCRQDMSA-N 2'-deoxyinosine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC2=O)=C2N=C1 VGONTNSXDCQUGY-RRKCRQDMSA-N 0.000 claims abstract description 3
- RPZDLTVHZJHPAW-BAJZRUMYSA-N 9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C(NC=NC2=O)=C2N=C1 RPZDLTVHZJHPAW-BAJZRUMYSA-N 0.000 claims abstract description 3
- 229920001577 copolymer Polymers 0.000 claims abstract description 3
- VGONTNSXDCQUGY-UHFFFAOYSA-N desoxyinosine Natural products C1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 VGONTNSXDCQUGY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000010189 synthetic method Methods 0.000 claims abstract description 3
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims abstract 4
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000007788 liquid Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 239000003443 antiviral agent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000006392 deoxygenation reaction Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- HIBWGGKDGCBPTA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 HIBWGGKDGCBPTA-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分封〕
本発明は、合W、法により生産された、又はそれ由来の
2 ?3 /−ジデオキシイノシン(以下、 DDIと
略丁。)の新規精製方法に関するものである。DDIは
抗ウイルス剤等医薬品として使用されるものである。[Detailed Description of the Invention] [Industrial Application Packaging] The present invention is directed to two types of products produced by, or derived from, the combined W method. The present invention relates to a new method for purifying 3/-dideoxyinosine (hereinafter abbreviated as DDI). DDI is used as a medicine such as an antiviral agent.
従来のDDIの製造方法としては、ヌクレオシド類の2
′位またti3’位の脱酸素反応が行われてhる( C
hew Pharm Bull 、 22.128(1
974))が以下の理由により、報告例は少ない。Conventional methods for producing DDI include two types of nucleosides:
The deoxygenation reaction at the ′ and ti3′ positions takes place (C
hew Pharm Bull, 22.128 (1
974)), but there are few reported cases for the following reasons.
■ 反応に先立ち保蒋基を導入しなけfiはならない。■ Fi must be introduced before the reaction.
■ 2′位、3′位は室体障害が大きく、反応が起きに
くい。■ The 2' and 3' positions have significant ventricular damage and are difficult to react with.
まへ別法として2 Is /−ソデオキシアデノシン(
以下、DDAと略す、)をi科にして酵素を利用したr
アミネーシ、ン罠よる方法も報告はれている (Bio
ehim Blophs Aeta566(2)2
59(1979ン)。Alternatively, 2Is/-sodeoxyadenosine (
(hereinafter abbreviated as DDA) was made into the i family using enzymes.
There have also been reports of methods using traps such as Amineshi (Bio
ehim Blophs Aeta566(2)2
59 (1979).
しかし、原料となるDDAも上記理由により製造が難し
くrアミネーシ、ンによる方法も報告は少ない。However, DDA, which is a raw material, is difficult to produce for the reasons mentioned above, and there are few reports on the method using r-aminase.
この為、単1li1精尖についても液体又は薄層クセマ
ドグラフィーによる分取が実施されている程度で工業的
に利用できる精製技術は未だ確立していなかった。For this reason, an industrially usable purification technique has not yet been established for the single 1li1 fine apex, although fractionation by liquid or thin layer chromatography has been carried out.
Moffattらの方法(J*Am@raCh@mJo
e、、95 。Moffatt et al.'s method (J*Am@raCh@mJo
e,,95.
4025(1973))に従い、イノシンを原料とし、
2′位、3′位の脱酸素反応を行った場合、反応液中に
は、不純物として、副生物である2′−デオキシイノシ
ン(以下、2’−DIと略す。)3′−デオキシイノシ
ン(以下、3’−DIと略す。)の他、未反応原料のイ
ノシン(以下、Inoと略す、)、分解生成物であるヒ
ーキサンチン(以下s )Iypと略″f、 )が含ま
れる。4025 (1973)), using inosine as a raw material,
When the deoxygenation reaction at the 2' and 3' positions is carried out, the reaction solution contains the by-products 2'-deoxyinosine (hereinafter abbreviated as 2'-DI) and 3'-deoxyinosine as impurities. (hereinafter abbreviated as 3'-DI), an unreacted raw material inosine (hereinafter abbreviated as Ino), and a decomposition product heaxanthin (hereinafter s) Iyp and abbreviated ``f'').
この反応液からDDIを取得する際、晶析法では上記不
純物の溶解度が1よい為にr)DI結晶中に不純物が混
入してしまう。また、DDI自身が酸性域で分解し易い
為イオン交換樹脂による分離方法も困轟であった。When obtaining DDI from this reaction solution, r) impurities are mixed into the DI crystal because the solubility of the impurities is 1 better in the crystallization method. Furthermore, since DDI itself is easily decomposed in an acidic region, separation methods using ion exchange resins have also been difficult.
上記の欠点を解消するような工業的に優れたDDI f
)精製方法の開発がglまれでいる。An industrially superior DDI that eliminates the above drawbacks
) The development of purification methods is extremely rare.
〔間4点を解決するための手段〕
本発明考らは、前記問題点を解決すべく、鋭意検討した
結果、合成反応終了後のDDIまたはそれ由来の未精製
DDI を例えは水溶液として非極性多孔qm脂処理
することにより、DDIをH4F eIno 、 2’
−DI 、 3’−DI等の不M4物と分離できること
を見出し、これらの発見に基づいて本発明を完れ由来の
未精製DDIO稍爬に際し、DDIを非極性多孔質樹脂
に吸着せしめることを%徴とするDDIのn裏方法であ
る。[Means for solving the above four points] In order to solve the above-mentioned problems, the inventors of the present invention, as a result of intensive studies, found that DDI after the completion of the synthesis reaction or unpurified DDI derived therefrom is treated as a non-polar solution, for example, as an aqueous solution. By treating DDI with porous qm fat, H4F eIno, 2'
-DI, 3'-DI, and other non-M4 substances, and based on these findings, the present invention was developed to adsorb DDI on a non-polar porous resin when extracting unpurified DDIO. This is a method of calculating DDI as a percentage.
本発明の出発物質に用いるDDIは、合成法由来のもの
で不純物として少なくともHIP e Ino 。The DDI used as the starting material of the present invention is derived from a synthetic method and contains at least HIP e Ino as an impurity.
、拳
2’−DI 、 3’−DI若干の副生成する核酸類の
うち、いずれかを含有するものである。ま念、水溶液と
して使用する場合の溶液のDDI濃度は、 DDIの溶
解度以下であれば制限されるものではない。, 2'-DI, and 3'-DI contain some by-product nucleic acids. Please note that when used as an aqueous solution, the concentration of DDI in the solution is not limited as long as it is below the solubility of DDI.
次に、ここで用いる非極性多孔質樹脂は、例えはその母
体が、スチレンーソビニルベンゼン糸の共重合体又は、
その籾導体例えばこれにハロゲン化し高比重化したポリ
マーである物質であれ、いずれも使用可能である0例え
ば、ダイヤイオン)(Pシリーズ、SPシリーズ(以上
、三菱化成工業)。Next, the non-polar porous resin used here is, for example, a matrix of styrene-vinylbenzene thread copolymer or
Any material can be used as the rice conductor, such as a polymer that has been halogenated and has a high specific gravity.
XAD−4(o−b # 7:/ ト−ハース社)、0
C1031(バイエル社)等が利用できるが、その他の
非極性多孔質樹脂であっても同等の性質を有するもので
あればいずれでありても良り、特に高比重化した5P2
07(三菱化成工業)がDDI溶液をフィードした時に
樹脂が浮上したりすることなく、操作性が良い点で逼し
てhる。XAD-4 (ob #7: / Tohaas), 0
C1031 (Bayer) etc. can be used, but any other non-polar porous resin with equivalent properties may be used, especially 5P2 with a high specific gravity.
07 (Mitsubishi Chemical Industries, Ltd.) is suitable because the resin does not float when feeding the DDI solution and has good operability.
非極性多孔質樹脂とDDX溶徹との接液方法鉱、パッチ
式とカラム式があるが、カラム式の万が操作上簡便で好
ましい。There are two methods for contacting the non-polar porous resin with DDX melting: a patch method and a column method, but the column method is preferred because it is easy to operate.
カラムへの通次速度は、特に制限はなく、通常8V−0
,!S 〜4.0、好ましくは5V=1〜28度がよい
。There is no particular restriction on the flow rate to the column, and it is usually 8V-0.
,! S ~4.0, preferably 5V = 1 ~ 28 degrees.
カラムにフィードするDDI溶液の体積負荷量はDDI
溶液の濃度によって異なり、同時にDDIの樹脂負荷t
(f!/l−n )は5〜309/1−R1好ましく
はlO〜2011/l−Rが分離性及び経済性の点で適
している。The volume loading amount of DDI solution fed to the column is DDI
It depends on the concentration of the solution and at the same time the resin loading t of DDI
(f!/l-n) is preferably 5 to 309/1-R1, preferably 10 to 2011/1-R from the viewpoint of separability and economy.
カラムへの接液温度については、10〜50℃であれば
特に制限されない。この温度ではDDIと濃縮液中の不
純物)(yp e Iれo 、 2’−DI 、 3’
−DIとの分離性の相違は殆んどない。The temperature of the liquid in contact with the column is not particularly limited as long as it is 10 to 50°C. At this temperature, DDI and impurities in the concentrate) (ypeIreo, 2'-DI, 3'
- There is almost no difference in separability from DI.
次に、カラムからのDDI溶離方法に関して記述する。Next, a method of elution of DDI from the column will be described.
溶離剤は、世級脂肪族アルコール水溶液が適している。A suitable eluent is an aqueous solution of a grade aliphatic alcohol.
例えは、メチルアルコール、エチルアルコール、イソプ
ロピルアルコール等の水溶液である。溶離速度は、通常
の5V=1〜28度が良い。Examples are aqueous solutions of methyl alcohol, ethyl alcohol, isopropyl alcohol, etc. The usual elution rate of 5V = 1 to 28 degrees is good.
実際の非極性多孔質樹脂を用いた精製操作は次のように
すると良い。すなわち、当該樹脂を充填したカラムにP
Hv!4整を行ったDDI反応液全一定慧フイード後、
直ちに低濃度アルコール水溶液を用いてI(yp s
Ino @ 2’DI @ 3’−DI f溶離し、次
にアルコール水溶液の濃度を上げることにより、DDI
を溶離する。The actual purification operation using a non-polar porous resin may be carried out as follows. In other words, P is added to the column filled with the resin.
Hv! After adjusting the DDI reaction solution for 4 times,
I(yps) immediately using a low concentration alcohol aqueous solution
Ino @ 2'DI @ 3'-DI f elution and then by increasing the concentration of the aqueous alcohol solution, DDI
elute.
このDDI画分t−pHPs4整後濃縮し、晶析後、冷
却することにより高純度のDDIを分取することができ
る。Highly pure DDI can be fractionated by concentrating this DDI fraction t-pHPs4, crystallizing it, and then cooling it.
以下、実施例により本発明の詳細な説明する。 Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例51
Me f f a t tらの方法(J @ Am@r
、Ch@m、Soa、、95゜4025(1973))
に従い、Ino30.0gを出発厘料として、反応せし
め、DDI 2.99を含む混合溶iを得念。Example 51 Method of Me f at t et al. (J@Am@r
, Ch@m, Soa, 95°4025 (1973))
Accordingly, 30.0 g of Ino was used as a starting material and reacted to obtain a mixed solution containing DDI of 2.99.
このDDI含有溶液を300−迄濃縮後、非極性多孔質
吸着樹脂5p207(三菱化成工業(櫟)製ン290d
(カラムφXL=30■×410■)にS徊2でフィー
ド後、5%エチルアルコール水溶gsso。After concentrating this DDI-containing solution to 300°C, a non-polar porous adsorption resin 5p207 (manufactured by Mitsubishi Chemical Industries, Ltd.) 290d
(Column φXL=30×410×) was fed with S 2, then 5% ethyl alcohol aqueous GSSO.
−で溶1した(SV−2)*(画分−1とする)。次に
、20%エチルアルコール水溶櫃1100−で溶mr行
ツタ(SV=2)e(ii!i+分−2トYる)。以上
の樹脂操作は液温30℃で行った。- (SV-2)* (referred to as fraction-1). Next, dissolve mr row ivy (SV = 2) e (ii! i + min - 2 to Y) in a 20% ethyl alcohol aqueous solution 1100 m. The above resin operations were performed at a liquid temperature of 30°C.
谷画分’tff体クロマトグラフィー分析により、測定
した結果、両分−1に#i3’−I)I 、 2’−D
I 、H)FP等の不純物が検出でれ(各回収率:95
慢、95慢、99%)、両分−2にはDDIが検出され
た(回収率65%)。As a result of measurement by chromatography analysis of the valley fraction 'tff body, #i3'-I) I, 2'-D was found in both fractions-1.
I, H) Impurities such as FP were detected (each recovery rate: 95
DDI was detected in both fraction-2 (recovery rate 65%).
両分−2をINNaoHで−=8&0で調整後濃縮しD
DIt−晶析槽、10℃迄冷却し、高純度(99,8%
)のDDI結畠1.1gをP取した。Both fractions -2 were adjusted to -=8&0 with INNaoH and concentrated.
DIt-crystallization tank, cooled to 10℃, high purity (99.8%
P was removed from 1.1 g of the DDI grains of ).
実施例17
実施例舊1と同様の方法で取得したDDI含有溶液30
(ldを非極性多孔質吸着樹脂5P207(三菱化成工
業(株)製) 290j(カラムφXL−30諷X41
0鴫)に5V−2でフィード後、3%イソプロピルアル
コール水溶g、5200−で溶離し几(SV−2)、C
画分−1とする)0次に、20チイソデロビルアルコー
ル水溶液840−で溶離を行った(SV−2)、(画分
−2とする)。すべての樹脂処理は液温30℃で行りた
。Example 17 DDI-containing solution 30 obtained in the same manner as Example 1
(ld is non-polar porous adsorption resin 5P207 (manufactured by Mitsubishi Chemical Industries, Ltd.) 290j (column φXL-30 x 41
After feeding at 5V-2 to SV-2), eluting with 3% isopropyl alcohol aqueous solution, 5200-g (SV-2), C
(referred to as fraction-1) Next, elution was performed with an aqueous solution of 840% of 20-thioderobil alcohol (SV-2), (referred to as fraction-2). All resin treatments were performed at a liquid temperature of 30°C.
各両分を液体クロマトグラフィー分析により、測定した
れi朱、画分−1には3’−DI 、 2’−DI *
Hyp等の不純物が検出され(各回収率95%、96
%。Both fractions were measured by liquid chromatography analysis, and fraction-1 contained 3'-DI and 2'-DI*.
Impurities such as Hyp were detected (each recovery rate was 95%, 96%).
%.
99%)、両分−2には、DDKが検出された。99%), DDK was detected in both portions-2.
(回収率6096)。(Recovery rate 6096).
画分−2七lNNaOHによりpH−8,0に調整後濃
縮しDDI七晶析後、10℃迄酎卸耐高純度(99,9
%)のDDI結晶1.0g七戸取した。Fraction-27 was adjusted to pH-8.0 with 1N NaOH, concentrated, and after DDI crystallization, high purity (99.9
%) of DDI crystals were taken from Shichinohe.
そn由来のDDIを効率的に分離精製でき、工業化への
道が太めに期待されるものである。It is possible to efficiently separate and purify DDI derived from the soil, and there are high expectations for the path to industrialization.
特許出、ヴ入 味の素株式会社Patent issue and acquisition Ajinomoto Co., Inc.
Claims (3)
,3′−ジデオキシイノシンを精製するに際し、2′,
3′−ジデオキシイノシンを非極性多孔質樹脂に吸着せ
しめることを特徴とする2′,3′−ジデオキシイノシ
ンの精製方法。(1) 2' produced by a synthetic method or derived therefrom
, 3'-dideoxyinosine, 2',
A method for purifying 2',3'-dideoxyinosine, which comprises adsorbing 3'-dideoxyinosine onto a non-polar porous resin.
シン、2′−デオキシイノシン及び3′−デオキシイノ
シンの少なくとも一種を含有することを特徴とする特許
請求の範囲第(1)項記載の方法。(2) The method according to claim (1), wherein the product to be purified contains at least one of hypoxanthine, inosine, 2'-deoxyinosine, and 3'-deoxyinosine as an impurity.
の共重合体、又はその誘導体を含有するものである特許
請求の範囲第(1)項記載の方法。(3) The method according to claim (1), wherein the non-polar porous resin contains a styrene divinylbenzene copolymer or a derivative thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62336171A JPH0826020B2 (en) | 1987-12-29 | 1987-12-29 | Purification method of dideoxyinosine |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62336171A JPH0826020B2 (en) | 1987-12-29 | 1987-12-29 | Purification method of dideoxyinosine |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH01175991A true JPH01175991A (en) | 1989-07-12 |
JPH0826020B2 JPH0826020B2 (en) | 1996-03-13 |
Family
ID=18296401
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62336171A Expired - Lifetime JPH0826020B2 (en) | 1987-12-29 | 1987-12-29 | Purification method of dideoxyinosine |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0826020B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0582157A1 (en) * | 1992-07-27 | 1994-02-09 | Ajinomoto Co., Inc. | Method of purifying nucleoside derivatives |
JP2003072660A (en) * | 2001-08-31 | 2003-03-12 | Matsushita Electric Ind Co Ltd | Bicycle |
WO2008087839A1 (en) | 2007-01-19 | 2008-07-24 | Ajinomoto Co., Inc. | Process for production of crystal of purine nucleoside compound |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59147606A (en) * | 1983-02-10 | 1984-08-24 | Jgc Corp | Separation of organic substance by adsorption |
-
1987
- 1987-12-29 JP JP62336171A patent/JPH0826020B2/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59147606A (en) * | 1983-02-10 | 1984-08-24 | Jgc Corp | Separation of organic substance by adsorption |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0582157A1 (en) * | 1992-07-27 | 1994-02-09 | Ajinomoto Co., Inc. | Method of purifying nucleoside derivatives |
JP2003072660A (en) * | 2001-08-31 | 2003-03-12 | Matsushita Electric Ind Co Ltd | Bicycle |
WO2008087839A1 (en) | 2007-01-19 | 2008-07-24 | Ajinomoto Co., Inc. | Process for production of crystal of purine nucleoside compound |
Also Published As
Publication number | Publication date |
---|---|
JPH0826020B2 (en) | 1996-03-13 |
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