JPH0258279B2 - - Google Patents
Info
- Publication number
- JPH0258279B2 JPH0258279B2 JP5698982A JP5698982A JPH0258279B2 JP H0258279 B2 JPH0258279 B2 JP H0258279B2 JP 5698982 A JP5698982 A JP 5698982A JP 5698982 A JP5698982 A JP 5698982A JP H0258279 B2 JPH0258279 B2 JP H0258279B2
- Authority
- JP
- Japan
- Prior art keywords
- arabinofuranosylcytosine
- water
- derivative
- formula
- acrylic acid
- 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.)
- Expired
Links
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical class O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 claims description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- XWRBMHSLXKNRJX-UHFFFAOYSA-N 2-ethenyl-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC=CC=C1C=C XWRBMHSLXKNRJX-UHFFFAOYSA-N 0.000 description 1
- TZKAAJHHGXWOGK-UHFFFAOYSA-N 2-methylsulfinylethyl prop-2-enoate Chemical compound CS(=O)CCOC(=O)C=C TZKAAJHHGXWOGK-UHFFFAOYSA-N 0.000 description 1
- RHCAZYILHJYUKB-STUHELBRSA-N 6-[[(3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]amino]-1h-pyrimidin-2-one Chemical compound O[C@H]1[C@H](O)[C@@H](CO)OC1NC1=CC=NC(=O)N1 RHCAZYILHJYUKB-STUHELBRSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- -1 acrylic acid halides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Description
【発明の詳細な説明】
本発明は新規なアラビノフラノシルシトシン誘
導体及びその製造方法に関するものである。さら
に詳しくいえば、本発明は長い活性持続時間を有
する制がん剤の製造原料として有用な、一般式
（式中のＲは水素原子又はメチル基である）
で示される新規アラビノフラノシルシトシン誘導
体及びその製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel arabinofuranosylcytosine derivative and a method for producing the same. More specifically, the present invention provides a compound having the general formula The present invention relates to a novel arabinofuranosylcytosine derivative represented by the following formula (wherein R is a hydrogen atom or a methyl group) and a method for producing the same.
アラビノフラノシルシトシンＣは白血病に有効
な制がん剤として知られているが、これを投与す
ると体内で急速に分解しその効力を失うため、長
時間にわたつて効力を持続させるには、点滴など
により連続的に投与しなければならないという不
便さがある。 Arabinofuranosylcytosine C is known as an anticancer drug that is effective against leukemia, but when administered, it rapidly degrades in the body and loses its efficacy, so in order to maintain its efficacy over a long period of time, It has the inconvenience of having to be administered continuously through an intravenous drip or the like.
他方、医薬の効力を持続させる手段として、有
効成分を適当な重合体に結合し、これを体内で徐
徐に放出させる方法が知られている。そして、ア
ラビノフラノシルシトシンについても、これをカ
ルボキシル基をもつ重合体とカルボジイミドの存
在下で反応させ高分子化する方法が提案されてい
る。しかし、この方法ではアラビノフラノシルシ
トシンの導入率に制限があり、60％以上の導入率
を得ることは困難である上に、使用しうる重合体
も制限され、治療に応じて適した重合体を選ぶこ
とができないという欠点がある。 On the other hand, as a means for sustaining the efficacy of pharmaceuticals, a method is known in which an active ingredient is bound to a suitable polymer and the polymer is gradually released within the body. A method has also been proposed for arabinofuranosylcytosine, in which it is reacted with a polymer having a carboxyl group in the presence of carbodiimide to form a polymer. However, this method has limitations on the introduction rate of arabinofuranosylcytosine, making it difficult to achieve an introduction rate of 60% or more, and also limits the types of polymers that can be used. The drawback is that you cannot choose to combine.
他方、アラビノフラノシルシトシンをアシル化
した誘導体も知られている（特公昭53−5698号公
報）。しかしながら、このものは難水溶性のため
使用方法が制限されるのを免れないという欠点が
ある。 On the other hand, derivatives obtained by acylating arabinofuranosylcytosine are also known (Japanese Patent Publication No. 5698/1983). However, this product has the disadvantage that its usage is inevitably limited due to its poor water solubility.
本発明者らは、このような従来のアラビノフラ
ノシルシトシンの持続性誘導体のもつ欠点を克服
するために、鋭意研究を重ねた結果、先ずアラビ
ノフラノシルシトシンの重合性誘導体を製造し、
これを単独もしくは他の共重合しうる単量体と組
み合わせて重合させれば、活性成分の導入率を高
めたり、任意に制御しうること及び可溶性官能基
を有する単量体と共重合させて使用すれば高い水
溶性を有するアラビノフラノシルシトシン高分子
誘導体が得られることを見出し、この知見に基づ
いて本発明をなすに至つた。 In order to overcome the drawbacks of such conventional long-lasting derivatives of arabinofuranosylcytosine, the present inventors have conducted extensive research and have first produced a polymerizable derivative of arabinofuranosylcytosine,
If this is polymerized alone or in combination with other copolymerizable monomers, the introduction rate of the active ingredient can be increased or controlled as desired, and if it is copolymerized with a monomer having a soluble functional group. It was discovered that an arabinofuranosylcytosine polymer derivative having high water solubility can be obtained by using this method, and based on this finding, the present invention was accomplished.
すなわち、本発明は前記一般式（）で示され
るアラビノフラノシルシトシン誘導体を提供する
ものである。 That is, the present invention provides an arabinofuranosylcytosine derivative represented by the general formula ().
このアラビノフラノシルシトシン誘導体は、文
献未載の新規化合物であつて、例えばアクリル酸
又はメタクリル酸あるいはそれらの反応性誘導体
と、アラビノフラノシルシトシンとを反応させる
ことにより効率よく製造することができる。 This arabinofuranosylcytosine derivative is a new compound that has not been described in any literature, and can be efficiently produced by, for example, reacting acrylic acid or methacrylic acid or a reactive derivative thereof with arabinofuranosylcytosine. can.
この際使用されるアクリル酸又はメタクリル酸
の反応性誘導体としては、例えば無水アクリル
酸、アクリル酸ハライド、アクリル酸の活性エス
テル及び対応するメタクリル酸誘導体をあげるこ
とができる。遊離のアクリル酸又はメタクリル酸
を用いることができ、この場合はカルボジイミド
のような縮合剤の存在下で反応させる。 Examples of reactive derivatives of acrylic acid or methacrylic acid used in this case include acrylic anhydride, acrylic acid halides, active esters of acrylic acid, and corresponding methacrylic acid derivatives. Free acrylic or methacrylic acid can be used, in which case it is reacted in the presence of a condensing agent such as a carbodiimide.
これらのアクリル酸又はメタクリル酸成分とア
ラビノフラノシルシトシンとの反応は、適当な溶
媒例えば水、アルコール、テトラヒドロフラン、
ジオキサン、ジメチルホルムアミドなどの中で、
かきまぜながら行うのが有利である。この場合、
必要に応じあまり高くない温度に加熱して行うこ
ともできる。このようにして得た目的化物合は、
溶媒をある程度留去して濃縮後これを不溶性溶剤
中に注加し、沈殿を析出させたもの、この沈殿を
常法に従つて精製すれば、目的生成物が白色針状
結晶として得られる。 The reaction between these acrylic acid or methacrylic acid components and arabinofuranosylcytosine can be carried out using a suitable solvent such as water, alcohol, tetrahydrofuran,
Among dioxane, dimethylformamide, etc.
It is advantageous to do this while stirring. in this case,
It can also be carried out by heating to a not very high temperature if necessary. The target compound obtained in this way is
After distilling off some of the solvent and concentrating, this is poured into an insoluble solvent to form a precipitate. If this precipitate is purified according to a conventional method, the desired product is obtained as white needle-like crystals.
このようにして得られる本発明化物合は、これ
を水溶性重合体を形成する単量体例えばＮ−ビニ
ルピロリドン、２−ビニルピリジン−Ｎ−オキシ
ド、２−（メチルスルフイニル）エチルアクリレ
ート、アクリルアミド、ヒドロキシルエチルメタ
クリレートなどと共重合させることにより持続性
制がん剤として有用な重合体とすることができ
る。 The compound of the present invention obtained in this way can be combined with monomers forming water-soluble polymers such as N-vinylpyrrolidone, 2-vinylpyridine-N-oxide, 2-(methylsulfinyl)ethyl acrylate, By copolymerizing with acrylamide, hydroxylethyl methacrylate, etc., it can be made into a polymer useful as a long-lasting anticancer agent.
次に実施例により本発明をさらに詳細に説明す
る。 Next, the present invention will be explained in more detail with reference to Examples.
実施例 １
水20ml中にアラビノフラノシルシトシンC2.2ｇ
を溶解し、さらにジオキサン60mlを加える。次に
この混合物中へ無水メタクリル酸2.8ｇを加え、
室温下、48時間かきまぜ、反応を完了させる。次
いで反応混合物を室温下で減圧濃縮後、濃縮液を
ｎ−ヘキサン中に滴下し、析出した沈殿をろ別す
る。この沈殿を水100mlに溶解し、陽イオン交換
樹脂を通して不純分を除いたのち、通過液を凍結
乾燥する。残留物をメタノールとエーテルの混合
物から再結晶することにより、Ｎ−メタクリロイ
ル−１，β，Ｄ−アラビノフラノシルシトシンが
融点144〜146℃の白色針状結晶として得られる。
収率は70％であつた。このものの物性は以下のと
おりである。Example 1 2.2 g of arabinofuranosylcytosine C in 20 ml of water
Dissolve and add 60ml of dioxane. Next, 2.8g of methacrylic anhydride was added to this mixture,
Stir at room temperature for 48 hours to complete the reaction. Next, the reaction mixture was concentrated under reduced pressure at room temperature, and the concentrated solution was added dropwise into n-hexane, and the precipitate deposited was filtered off. This precipitate is dissolved in 100 ml of water, passed through a cation exchange resin to remove impurities, and the passed liquid is freeze-dried. By recrystallizing the residue from a mixture of methanol and ether, N-methacryloyl-1,β,D-arabinofuranosylcytosine is obtained as white needle-like crystals with a melting point of 144-146°C.
The yield was 70%. The physical properties of this product are as follows.
元素分析値：C13H17N3O6（分子量311.3）とし
て
Ｃ Ｈ Ｎ
計算値(%) 50.15 5.51 13.50
実測値(%) 50.35 5.61 13.40
紫外線吸収スペクトル：ε＝8.5×103（302nｍ）、
1.3×104（255nｍ）
核磁気共鳴スペクトル：8.3（ｍ）、7.4（ｍ）、6.0
（ｔ）、4.5（ｔ）、4.1、3.9、2.0（Ｓ）
薄層クロマトグラフ：ブタノール／酢酸／水
（５：２：３）の混合溶媒で展開したときのRf
＝0.33
溶解性：可溶 水（1.2ｇ／ml）、エタノール、メ
タノール
不溶 アセトン、エーテル
また、このものの赤外線吸収スペクトルを第１
図に示す。 Elemental analysis value: C 13 H 17 N 3 O 6 (molecular weight 311.3) C H N Calculated value (%) 50.15 5.51 13.50 Actual value (%) 50.35 5.61 13.40 Ultraviolet absorption spectrum: ε = 8.5 × 10 3 (302 nm),
1.3×10 4 (255nm) Nuclear magnetic resonance spectrum: 8.3 (m), 7.4 (m), 6.0
(t), 4.5 (t), 4.1, 3.9, 2.0 (S) Thin layer chromatography: Rf when developed with a mixed solvent of butanol/acetic acid/water (5:2:3)
=0.33 Solubility: Soluble Water (1.2g/ml), ethanol, methanol Insoluble Acetone, ether Also, the infrared absorption spectrum of this product is
As shown in the figure.
実施例 ２
無水メタクリル酸2.8ｇの代りに無水アクリル
酸2.3ｇを用い、実施例１と全く同様に操作し、
融点121〜123℃の白色針状結晶として、Ｎ−アク
リロイル−１，β，Ｄ−アラビノフラノシルシト
シンを得た。収率は85％であつた。Example 2 The procedure was carried out in exactly the same manner as in Example 1, using 2.3 g of acrylic anhydride instead of 2.8 g of methacrylic anhydride.
N-acryloyl-1,β,D-arabinofuranosylcytosine was obtained as white needle-like crystals with a melting point of 121-123°C. The yield was 85%.
このものの物性は以下のとおりである。 The physical properties of this product are as follows.
元素分析値：C12H15N3O6（分子量297.3）とし
て
Ｃ Ｈ Ｎ
計算値(%) 48.48 5.10 14.13
実測値(%) 48.61 5.12 14.33
紫外線吸収スペクトル：ε＝8.5×103（302nｍ）、
1.3×104（255nｍ）
薄層クロマトグラフ：ブタノール／酢酸／水
（５：２：３）の混合溶媒で展開したときのRf
＝0.12
また、このものの赤外線吸収スペクトルを第２
図に示す。 Elemental analysis value: C 12 H 15 N 3 O 6 (molecular weight 297.3) C H N Calculated value (%) 48.48 5.10 14.13 Actual value (%) 48.61 5.12 14.33 Ultraviolet absorption spectrum: ε = 8.5 × 10 3 (302 nm),
1.3×10 4 (255nm) Thin layer chromatography: Rf when developed with a mixed solvent of butanol/acetic acid/water (5:2:3)
=0.12 Also, the infrared absorption spectrum of this material is
As shown in the figure.
参考例
実施例１で得たＮ−メタクリロイル−１，β，
Ｄ−アラビノフラノシルシトシン13.4ｇとＮ−ビ
ニルピロリドン6.3ｇとを水50ml中に溶解し、過
硫酸アンモニウム0.1ｇを加え、アルゴン雰囲気
中において70℃で５時間重合を行つた。反応混合
物を濃縮し、濃縮物をエタノール中に滴下し、得
られた共重合体を再び水に溶解してエタノール中
に再沈させることにより共重合体を製精した
（9.3ｇ）。この共重合体の重量平均分子量は1.6万
であり、250nｍの紫外部吸収からアラビノフラ
ノシルシトシンの含有量は43.2重量％であり、水
に易溶であつた。Reference example N-methacryloyl-1,β, obtained in Example 1
13.4 g of D-arabinofuranosylcytosine and 6.3 g of N-vinylpyrrolidone were dissolved in 50 ml of water, 0.1 g of ammonium persulfate was added, and polymerization was carried out at 70° C. for 5 hours in an argon atmosphere. The reaction mixture was concentrated, the concentrate was added dropwise to ethanol, and the resulting copolymer was dissolved in water again and reprecipitated in ethanol to purify the copolymer (9.3 g). The weight average molecular weight of this copolymer was 16,000, the content of arabinofuranosylcytosine was 43.2% by weight based on ultraviolet absorption at 250 nm, and it was easily soluble in water.
なお、Ｎ−メタクリロイル−１，β，Ｄ−アラ
ビノフラノシルシトシンに対応する飽和アシル基
を有するＮ−イソブチル−１，β，Ｄ−アラビノ
フラノシルシトシンは水に難溶であり、重合に必
要な二重結合を有していないのでＮ−ビニルピロ
リドンと共重合させることはできない。さらに既
知の不飽和アシル化誘導体（特公昭53−5698号）
のオレオイル基を有する１，β，Ｄ−アラビノフ
ラノシルシトシンは二重結合を有しているが、Ｎ
−ビニルピロリドンとは共重合しない。 Note that N-isobutyl-1,β,D-arabinofuranosylcytosine, which has a saturated acyl group corresponding to N-methacryloyl-1,β,D-arabinofuranosylcytosine, is poorly soluble in water and difficult to polymerize. Since it does not have the necessary double bond, it cannot be copolymerized with N-vinylpyrrolidone. Furthermore, known unsaturated acylated derivatives (Special Publication No. 53-5698)
1,β,D-arabinofuranosylcytosine with an oleoyl group has a double bond, but N
-Does not copolymerize with vinylpyrrolidone.
第１図はＮ−メタクリロイル−１，β，Ｄ−ア
ラビノフラノシルシトシンの赤外線吸収スペクト
ル図、第２図はＮ−アクリロイル−１，β，Ｄ−
アラビノフラノシルシトシンの赤外線吸収スペク
トル図である。
Figure 1 is an infrared absorption spectrum diagram of N-methacryloyl-1,β,D-arabinofuranosylcytosine, and Figure 2 is N-acryloyl-1,β,D-
It is an infrared absorption spectrum diagram of arabinofuranosylcytosine.
Claims (1)
の反応性誘導体と、アラビノフラノシルシトシン
とを反応させることを特徴とする、一般式 （式中のＲは水素原子又はメチル基である） で示されるアラビノフラノシルシトシン誘導体の
製造方法。[Claims] 1. General formula (R in the formula is a hydrogen atom or a methyl group) An arabinofuranosylcytosine derivative represented by the following. 2 General formula characterized by reacting acrylic acid or methacrylic acid or a reactive derivative thereof with arabinofuranosylcytosine (R in the formula is a hydrogen atom or a methyl group) A method for producing an arabinofuranosylcytosine derivative represented by the following formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5698982A JPS58174399A (en) | 1982-04-06 | 1982-04-06 | Arabinofuranosylcytosine derivative having polymerizability and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5698982A JPS58174399A (en) | 1982-04-06 | 1982-04-06 | Arabinofuranosylcytosine derivative having polymerizability and preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58174399A JPS58174399A (en) | 1983-10-13 |
| JPH0258279B2 true JPH0258279B2 (en) | 1990-12-07 |
Family
ID=13042898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5698982A Granted JPS58174399A (en) | 1982-04-06 | 1982-04-06 | Arabinofuranosylcytosine derivative having polymerizability and preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58174399A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018080269A (en) * | 2016-11-17 | 2018-05-24 | キヤノン株式会社 | Polymer |
| JP6894747B2 (en) * | 2017-04-19 | 2021-06-30 | キヤノン株式会社 | Polymer |
-
1982
- 1982-04-06 JP JP5698982A patent/JPS58174399A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58174399A (en) | 1983-10-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6858694B2 (en) | Stimuli-responsive polymer utilizing keto-enol tautomerization and stimuli-responsive separating material and chemical-releasing capsule comprising the same | |
| JP2003506497A (en) | Temperature sensitive polymer | |
| JPH02281013A (en) | Diketone compound copolymer | |
| Gallardo et al. | Synthesis and characterization of a new poly (methacrylamide) bearing side groups of biomedical interest | |
| Otsu et al. | Vinyl polymerization. LXXIX. Effect of the alkyl group on the radical polymerization of alkyl methacrylates | |
| JP3180106B2 (en) | Method for producing organic polymer compound | |
| JPH0258279B2 (en) | ||
| JPWO1992007884A1 (en) | Method for producing organic polymer compounds | |
| US6100338A (en) | Fine grain carriers and medicinal composition prepared with the use of the same | |
| Nazarova et al. | Copolymerizations of N-vinylpyrrolidone and activated esters of unsaturated acids | |
| JP2000319304A (en) | Copolymer having reversible hydrophilicity- hydrophobicity transition and its production | |
| JPH0222312A (en) | Production of polymer containing crosslinking type carboxyl group | |
| JP3180818B2 (en) | Method for producing 1-substituted ethyl methacrylates | |
| JPH0613580B2 (en) | Hydrophilic-hydrophobic thermoreversible polymer compound and method for producing the same | |
| JP3904670B2 (en) | Method for producing lactone ring-containing polymer | |
| JPS58174409A (en) | Preparation of polymer compound having carcinostatic activity | |
| JP2819157B2 (en) | Radiation polymerizable liquid crystalline monomer and its polymer | |
| JP4069221B2 (en) | Expression method of upper critical solution temperature | |
| JP3200942B2 (en) | Boronic acid group-containing monomer and polymer thereof | |
| CN110734509A (en) | type pH-sensitive amphiphilic polymer capable of releasing 3-phenyl-2-acrolein, self-assembled nanoparticles thereof and application of self-assembled nanoparticles | |
| JPH06172426A (en) | Polymer having acetylsalicylic acid group on side chain | |
| JPH0613578B2 (en) | Hydrophilic-hydrophobic thermoreversible polymer compound and method for producing the same | |
| JPH0562884B2 (en) | ||
| JPH0762038A (en) | Thermoreversible polymer compound and its production | |
| JP3193836B2 (en) | Vinyl acetylsalicylic acid copolymer |