JPS5855485A - Purification of guanine - Google Patents
Purification of guanineInfo
- Publication number
- JPS5855485A JPS5855485A JP15215581A JP15215581A JPS5855485A JP S5855485 A JPS5855485 A JP S5855485A JP 15215581 A JP15215581 A JP 15215581A JP 15215581 A JP15215581 A JP 15215581A JP S5855485 A JPS5855485 A JP S5855485A
- Authority
- JP
- Japan
- Prior art keywords
- guanine
- aqueous solution
- alkali
- crude
- solution
- 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.)
- Pending
Links
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 238000000746 purification Methods 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 20
- 239000007864 aqueous solution Substances 0.000 claims abstract description 14
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 239000012535 impurity Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
- 239000000243 solution Substances 0.000 abstract description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 6
- 238000001816 cooling Methods 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000003463 adsorbent Substances 0.000 abstract description 2
- 239000007769 metal material Substances 0.000 abstract description 2
- 238000001953 recrystallisation Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000004675 formic acid derivatives Chemical class 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-IGMARMGPSA-N Carbon-12 Chemical class [12C] OKTJSMMVPCPJKN-IGMARMGPSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- -1 guanine salt Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、粗製グアニンから高品質のグアニンを高収率
で潜るグアニ/の精製法に関する〇グアニンは核l11
!2堪基の一つで、医薬品原料等。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for purifying guanine to obtain high quality guanine from crude guanine in high yield.
! One of the two basic ingredients, such as pharmaceutical raw materials.
いろいろな分野で利用できる0
グアニンの製造法としては、 2.4.5−トリアミ
ノ−6−オキシ−ピリミジンをギ酸等で閉環する方法〔
ペリヒテ8B、 1871.8085(1900))ア
リールアゾシアノアセチル誘導体と尿素、チオ尿素、ギ
#Iまたはギ酸誘導体から合成する方法〔特公昭42−
20067号〕2−アリールアゾシアノアセチルグアニ
ジンを還元条件下ギ酸またはギ酸誘導体と反応して合成
する方法〔特開昭51−141894号〕等があるがい
ずれも若干量の副生物の生成は避けられず、精製を行う
必要がある。A method for producing 0-guanine that can be used in various fields is a method of ring-closing 2.4.5-triamino-6-oxy-pyrimidine with formic acid, etc.
Perichte 8B, 1871.8085 (1900)) Method of synthesis from arylazocyanoacetyl derivatives and urea, thiourea, formic acid derivatives
No. 20067] There is a method of synthesizing 2-arylazocyanoacetylguanidine by reacting it with formic acid or a formic acid derivative under reducing conditions [Japanese Patent Application Laid-Open No. 141894/1989], but in all of these methods, the generation of a small amount of by-products can be avoided. First, it is necessary to purify it.
しかし、従来、グアニンの精製法としては優れたものが
なく高純度品は工業的に生産されていない0
グアニン−は強酸2強塩基以外に適当な溶媒がなく。However, to date, there has been no excellent purification method for guanine, and high-purity products have not been produced industrially.There are no suitable solvents for guanine other than strong acids and strong bases.
精製法として、これら溶媒中で、活性炭の様な吸宥剤に
より不純物を吸着除去する方法、鉱酸埴として再結晶す
る方法が用いられて来たが、一度を上げようとすると精
製収率が低下し、経済的に高品質のグアニンを得る事は
できなかった。As purification methods, methods have been used in which impurities are adsorbed and removed using an absorbent such as activated carbon in these solvents, and methods are recrystallized using mineral acid clay. Therefore, it was not possible to economically obtain high quality guanine.
発明者等は、グアニンの精製法t−鋭意検討の結果、グ
アニンが高濃度のアルカリ水溶液中で蝶溶性の項として
結晶を形成するφを発見した〇この性質を利用して、粗
製グアニンを高濃度のアルカリ水溶液中に加熱溶解し冷
却晶析する事により、原料粗製グアニンより、はるかに
少量の不純物しか含まないグアニンの金属塩を形成させ
。As a result of extensive research into guanine purification methods, the inventors discovered that guanine forms crystals as a butterfly-soluble term in a highly concentrated alkaline aqueous solution. Utilizing this property, crude guanine can be purified to a high purity. By heating and dissolving in a concentrated alkaline aqueous solution and cooling and crystallizing, a metal salt of guanine is formed that contains far less impurities than the crude guanine raw material.
グアニンを精製する事ができる事を見出し本発明を完成
した。They discovered that guanine can be purified and completed the present invention.
即ち1本発明は、粗製グアニンを高濃度のアルカリ水溶
液中に加熱溶解し1次いで冷却して、#媒に難溶のグア
ニンの金属塩を晶析する事により。That is, in the present invention, crude guanine is heated and dissolved in a highly concentrated alkaline aqueous solution, and then cooled to crystallize a metal salt of guanine that is sparingly soluble in # medium.
水酸化す) IJウム、水酸化カリウム等の水酸化アル
カリ金属が有効であり、1.・その濃度が15重普嘩以
上である水層液が好ましい。1゜
本発明はバッチ′式に粗製グアニンのアルカリ溶液での
溶解、冷却晶析を行うことによって実施しうる。また1
本発明出願人が出願中の〔特願昭56−128165号
〕多段再結晶法を利用すれば他の精製助剤1例えば活性
炭を全く用いる事なく、極6て高収率で高品質のグアニ
ンを得る事ができる。Alkali metal hydroxides such as IJum and potassium hydroxide are effective; 1. - An aqueous phase liquid whose concentration is 15 times higher than or equal to 15 times higher than that is preferable. 1. The present invention can be carried out by dissolving crude guanine in an alkaline solution and crystallizing it by cooling. Also 1
By using the multi-stage recrystallization method (Japanese Patent Application No. 128165/1989) currently filed by the applicant of the present invention, high yield and high quality guanine can be produced without using any other refining aids, such as activated carbon. can be obtained.
また、活性炭等の吸着剤による精製法と併用する事も可
能で粗製グアニンの品質によりいろいろな組合せを用い
る事ができる。It is also possible to use it in combination with a purification method using an adsorbent such as activated carbon, and various combinations can be used depending on the quality of the crude guanine.
本発明の方法によると高純度のグアニンを高精製収率で
得ることが容易にできる。According to the method of the present invention, highly pure guanine can be easily obtained with a high purification yield.
本発明は、アルカリ水溶液を用いるので設備に一般の金
属材料を用いる事ができる事も工業的に利用する際の利
点となる。Since the present invention uses an alkaline aqueous solution, it is possible to use general metal materials for the equipment, which is an advantage when used industrially.
グアニンの合成
2.4.5− )リアミノ−6−オキシ−ピリミジン・
硫酸塩802をホルムアミド200f中で160−C8
時間加熱閉環し、粗製グアニン49?を得た。純度98
%(液体クロマトグラフィー)白色度70%。Synthesis of guanine 2.4.5-) Liamino-6-oxy-pyrimidine
Sulfate 802 in formamide 200f 160-C8
Crude guanine 49? I got it. Purity 98
% (liquid chromatography) whiteness 70%.
グアニンの精製
上記により合成した粗製グアニン10Fを20重量%水
酸化ナトリウム水溶液100−に入れ70”Cに加熱、
溶解した後、徐々に冷却し、最終的に15℃以下に冷却
し、グアニンのナトリウム塩(以下グアニン塩と称する
)を析出する。Purification of guanine The crude guanine 10F synthesized as above was placed in a 20% by weight aqueous sodium hydroxide solution 100°C and heated to 70"C.
After dissolving, the solution is gradually cooled and finally cooled to 15° C. or below to precipitate the sodium salt of guanine (hereinafter referred to as guanine salt).
結晶を戸別したp液中のグアニンは0.4fであった。The guanine content in the p-liquid from which the crystals were separated was 0.4f.
このν液は廃棄する。以上を第1段晶析と称する。This ν liquid is discarded. The above process is referred to as first stage crystallization.
第1段晶析で戸別したグアニン塩を再び20重11i%
水酸化す) +7ウム水溶液に加熱溶解1次いで冷却し
てグアニン塩を晶析する。(第2段晶析)結晶を戸別し
p液は次のバッチの第1段晶析溶媒として用いる。The guanine salt separated in the first stage crystallization is reused at 20% by weight and 11i%.
(Hydroxide) + 7 um aqueous solution by heating and then cooling to crystallize the guanine salt. (Second stage crystallization) The crystals are separated from each other and the p liquid is used as the first stage crystallization solvent for the next batch.
別様に第8段の晶析を行いF液は第2段の晶析溶媒に用
いる0晶析操作を6段行い、第6段でP9したグアニン
塩を酸で中和して、1nII製グアニンを得た〇
以上の操作を数バッチ繰り返すと、各段の晶析溶媒の組
成は定常状態となる。Separately, the 8th stage of crystallization is carried out, and the F solution is used as the crystallization solvent of the 2nd stage. 0 crystallization operation is performed in 6 stages, and the P9 guanine salt is neutralized with acid in the 6th stage. After repeating the above procedure for several batches to obtain guanine, the composition of the crystallization solvent in each stage becomes steady state.
定常状態での6段の晶析により精製グアニア8.62を
得た。収率86慢。Purified guania 8.62 was obtained by six stages of steady-state crystallization. Yield: 86%.
精製グアニンの純度99.6%(液体クロマトグラフィ
ー)、白色度94%、 (分光光電光度計480rM1
1)
実施例 2
実施例1と同様にして合成した粗製グアニンlO2を2
0%水酸化ナトリウム100−に加熱溶解し、冷却晶析
してグアニン塩を析出し、結晶を炉取した0得られたグ
アニン塩を1%水酸化ナトリウム水溶液200艷に溶解
し、活性炭0.8Fを入江て攪拌脱色した後、活性炭を
除去し、溶液を酸で中和し、精製グアニン8.12を得
た□純度99.5係、白色度89チであった。Purified guanine purity 99.6% (liquid chromatography), whiteness 94%, (spectrophotometer 480 rM1
1) Example 2 Crude guanine lO2 synthesized in the same manner as in Example 1 was
The guanine salt was heated and dissolved in 100% of 0% sodium hydroxide solution, cooled and crystallized to precipitate the guanine salt, and the crystals were collected in a furnace. After stirring and decolorizing 8F, the activated carbon was removed and the solution was neutralized with acid to obtain purified guanine 8.12.□ Purity was 99.5 and whiteness was 89.
比較例
実施例1と同様に合成した粗製グアニン102を1%水
酸化す) IJウム水溶液200−に溶解し。Comparative Example Crude guanine 102 synthesized in the same manner as in Example 1 was dissolved in a 1% hydroxylated IJum aqueous solution 200-.
活性炭12を入れ攪拌脱色した鎌、活性炭を除去し、浴
液を酸で中和して精製グアニン7.52を得た0純度9
9.5チ、白色度81チ。Activated carbon 12 was added to the sickle, stirred and decolorized, the activated carbon was removed, and the bath liquid was neutralized with acid to obtain purified guanine 7.52.0 Purity 9
9.5 inches, whiteness 81 inches.
実施例 8
グアニンの合成
2−クエニルアゾシアノアセチルグアニジン98fをホ
ルムアミド5502に入れ48%ニッケル含有合金14
Fから調整したラネーニッケル触媒、活性炭14fを加
えオートクレーブ中、 80 h/cri水素を圧入
し、150℃5時間反応した後ホルムアミドを減圧留去
し、得られた濃縮残渣をアルカリ処理して粗製グアニン
52Vを得た。Example 8 Synthesis of guanine 2-Quenylazocyanoacetylguanidine 98f was added to formamide 5502 to prepare 48% nickel-containing alloy 14.
Add the Raney nickel catalyst prepared from F and 14f of activated carbon, pressurize hydrogen at 80 h/cri in an autoclave, react at 150°C for 5 hours, then distill off formamide under reduced pressure, and treat the resulting concentrated residue with alkali to obtain crude guanine 52V. I got it.
グアニンの精製
上記合成法により得られた粗製グアニン10tを実施例
1の精製法と同様の条件で8段晶析して精製グアニン8
.Ofを得た。純度99.61白色度87優であった。Purification of guanine 10 tons of crude guanine obtained by the above synthesis method was crystallized in 8 steps under the same conditions as the purification method of Example 1.
.. I got Of. The purity was 99.61 and the whiteness was 87.
特許出願人 株式会社 興 人Patent applicant: Kojin Co., Ltd.
Claims (2)
リ水溶液に加熱溶解し次いで冷却して嶋濃度アAカリ水
溶液に難溶のグアニ/の金属塩を晶析する事により、不
純物を分離するグアニンの精製法0(1) Crude guanine containing impurities is heated and dissolved in a highly concentrated alkaline aqueous solution, and then cooled to crystallize a metal salt of guani, which is sparingly soluble in a Shima-concentrated alkali aqueous solution, to separate impurities from guanine. Purification method 0
上の水酸化アルカリ金稿水溶液である特許It#求の範
囲第1項のグアニンの精製法。(2) The method for purifying guanine according to Item 1, wherein the highly concentrated alkali aqueous solution is an alkali hydroxide aqueous solution having a concentration of 15% by weight or more.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15215581A JPS5855485A (en) | 1981-09-28 | 1981-09-28 | Purification of guanine |
GB08227127A GB2109369B (en) | 1981-09-28 | 1982-09-23 | Process for purifying guanine |
DE19823235372 DE3235372A1 (en) | 1981-09-28 | 1982-09-24 | METHOD FOR PURIFYING GUANINE |
CH565682A CH651834A5 (en) | 1981-09-28 | 1982-09-24 | METHOD FOR PURIFYING GUANINE. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15215581A JPS5855485A (en) | 1981-09-28 | 1981-09-28 | Purification of guanine |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS5855485A true JPS5855485A (en) | 1983-04-01 |
Family
ID=15534220
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP15215581A Pending JPS5855485A (en) | 1981-09-28 | 1981-09-28 | Purification of guanine |
Country Status (4)
Country | Link |
---|---|
JP (1) | JPS5855485A (en) |
CH (1) | CH651834A5 (en) |
DE (1) | DE3235372A1 (en) |
GB (1) | GB2109369B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3727508A1 (en) * | 1987-08-18 | 1989-03-02 | Boehringer Ingelheim Kg | METHOD FOR PRODUCING SODIUM PURINE |
DE3729471A1 (en) * | 1987-09-03 | 1989-03-16 | Huels Troisdorf | Process for the preparation of guanine |
US6207650B1 (en) * | 1989-05-15 | 2001-03-27 | Bristol-Myers Squibb Company | Antiviral, highly water soluble, stable, crystalline salts of 2′, 3′-dideoxyinosine, 2′, 3′-dideoxy-2′, 3′-didehydrothymidine and 2′, 3′-dideoxy-2′-fluoroinosine |
DE3928365A1 (en) * | 1989-08-28 | 1991-03-07 | Huels Chemische Werke Ag | METHOD FOR PRODUCING PURE GUANINE |
DE4022314A1 (en) * | 1990-07-13 | 1992-01-16 | Boehringer Ingelheim Kg | METHOD FOR PRODUCING 2-CHLORINE-1,7-DIHYDROPURIN-6-ON AND METHOD FOR CLEANING IT |
DE4136114C2 (en) * | 1991-11-02 | 1995-05-24 | Boehringer Ingelheim Kg | Improved process for the production of guanine and its alkali metal salts |
DE4422587C2 (en) * | 1994-06-28 | 2000-11-30 | Sueddeutsche Kalkstickstoff | Process for the production of purines |
-
1981
- 1981-09-28 JP JP15215581A patent/JPS5855485A/en active Pending
-
1982
- 1982-09-23 GB GB08227127A patent/GB2109369B/en not_active Expired
- 1982-09-24 CH CH565682A patent/CH651834A5/en not_active IP Right Cessation
- 1982-09-24 DE DE19823235372 patent/DE3235372A1/en active Granted
Also Published As
Publication number | Publication date |
---|---|
CH651834A5 (en) | 1985-10-15 |
GB2109369B (en) | 1985-06-12 |
DE3235372C2 (en) | 1990-09-06 |
GB2109369A (en) | 1983-06-02 |
DE3235372A1 (en) | 1983-04-14 |
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