JPS5919555B2 - Nitrosourea transparent conductor and its manufacturing method - Google Patents
Nitrosourea transparent conductor and its manufacturing methodInfo
- Publication number
- JPS5919555B2 JPS5919555B2 JP6345978A JP6345978A JPS5919555B2 JP S5919555 B2 JPS5919555 B2 JP S5919555B2 JP 6345978 A JP6345978 A JP 6345978A JP 6345978 A JP6345978 A JP 6345978A JP S5919555 B2 JPS5919555 B2 JP S5919555B2
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- JP
- Japan
- Prior art keywords
- chloroethyl
- group
- nitroso
- urea
- allyl
- 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.)
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Description
【発明の詳細な説明】
本発明は一般式
１１〔Ｉ〕
Ｃｌ−ＣＨ２ＣＨ２−Ｎ−Ｃｏ−Ｎ−Ｒ２（但し、Ｒ１
はアラビノース、ガラクトースまたはマルトースよりそ
れぞれ１位ヘミアセタール水酸基を除いた残基、Ｒ２は
分枝することもある炭素数３〜４個のアルケニル基また
はアルキニル基を表わす）で示されるニトロソ尿素誘導
体及びその製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula 11 [I] Cl-CH2CH2-N-Co-N-R2 (wherein R1
is a residue obtained by removing the hemiacetal hydroxyl group at the 1-position from arabinose, galactose or maltose, respectively, and R2 represents an alkenyl group or alkynyl group having 3 to 4 carbon atoms, which may be branched. Regarding the manufacturing method.
本発明のニトロソ尿素誘導体〔１〕は新規化合物であり
、すぐれた抗腫膓作用を有する有用な医薬化合物である
。The nitrosourea derivative [1] of the present invention is a new compound and is a useful pharmaceutical compound having excellent antitumor activity.
従来、抗腫瘍作用を有するニトロソ尿素類化合物は多数
合成されているが、それら化合物の殆んどは下記部分構
造Ｉ〕において、３位窒素原子上に水素原子を有する化
合物である〔例えば、・内科；３８巻、９１１〜９１６
頁（１９７６）：化学の領域；２９巻、７６５〜７７５
頁（１９７５）〕。Many nitrosourea compounds with antitumor effects have been synthesized to date, but most of these compounds have a hydrogen atom on the nitrogen atom at the 3-position in the substructure I below [for example, Internal medicine; vol. 38, 911-916
Page (1976): Area of Chemistry; Volume 29, 765-775
Page (1975)].
これに対する例外としては、ｌ−（２−クロロエチル）
−１−ニトロソー３−ｎ・プロピルウレア、１−（２−
クロロエチル）−１−ニトロソー３−メチルウレア及び
１−（２−クロロエチル）−１−ニトロソー３−シクロ
ヘキシルウレア等のニトロソ尿素化合物の３位窒素原子
上に更にメチル基を導入した化合物が近時報告されてい
る〔ブルンドレツト等；プロスイーデングス・オブ・ゼ
・アメリカン・アソシエーシヨン・フオ一・キヤンサ一
・リサーチ、１７巻、６７ミーテング、１０２頁（１９
７６）〕が、これら各化合物に於ても３位窒素原子に置
換基を導入したことによる抗腫瘍作用の改善は認められ
なかつた。しかるに本発明者らは種々研究を重ねた結果
、意外にも、例えば特開昭５１−２６８７６号、同５１
−５２１２８号及び同５１−１４１８１５号等により報
告されているニトロソ尿素誘導体の３位窒素原子上の水
素原子を記号Ｒ２で示される基で置換えたものに相当す
る新規二トロソ尿素化合物〔１〕が優れた抗腫瘍作用を
示すと共に安全性の面でも予想外に顕著な改善を示し、
抗腫瘍剤として優れた諸特性を具備するものであること
を見い出した。An exception to this is l-(2-chloroethyl)
-1-nitroso-3-n-propylurea, 1-(2-
Compounds in which a methyl group is further introduced on the nitrogen atom at the 3-position of nitrosourea compounds such as chloroethyl)-1-nitroso-3-methylurea and 1-(2-chloroethyl)-1-nitroso-3-cyclohexylurea have recently been reported. [Brundretz et al.; Pros. of the American Association Research, Volume 17, Meeting 67, Page 102 (19
76)], but in each of these compounds, no improvement in antitumor activity was observed due to the introduction of a substituent to the nitrogen atom at the 3-position. However, as a result of various researches, the present inventors unexpectedly discovered, for example, JP-A-51-26876;
-52128 and No. 51-141815, etc., a new nitrosourea compound [1] corresponds to a nitrosourea derivative in which the hydrogen atom on the nitrogen atom at the 3-position is replaced with a group represented by the symbol R2. In addition to exhibiting excellent antitumor effects, it also showed unexpectedly significant improvements in safety.
It has been found that it has various excellent properties as an antitumor agent.
本発明の新規二トロソ尿素誘導体は、たとえば特開昭５
１−２６８７６号、同５１−５２１２８？ｎψｖ口Ｐ●
●Ａ●＾−ｎ口鋳Ｔ，ｌ）＾↓ｉ↓１１１１ている
ニトロソ尿素誘導体の３位窒素原子上に存在する水素原
子を、前記従来の知見に反して低級アルケニル基あるい
は低級アルキニル基で置換えたものに相当するもので、
抗腫瘍作用ではほぼ同等の効力を有しながら、しかも、
安全性の面においては予想外に顕著な改善が認められた
ものである。The novel nitrosourea derivative of the present invention is disclosed in, for example, JP-A No. 5
No. 1-26876, No. 51-52128? nψvmouthP●
●A●＾−n口口T,l)＾↓i↓1111Contrary to the conventional knowledge, the hydrogen atom present on the nitrogen atom at the 3-position of the nitrosourea derivative is replaced by a lower alkenyl group or a lower alkynyl group. It is equivalent to the replaced one,
While having almost the same efficacy in terms of antitumor action,
In terms of safety, an unexpectedly significant improvement was observed.
本発明のニトロソ尿素誘導体は前記一般式〔１〕で示さ
れる化合物であるが、その代表的な例としては、たとえ
ば一般式〔〕において記号Ｒ１で示される基がアラビノ
ース、ガラクトースまたはマルトースより１位ヘミアセ
タール水酸基を除いた残基であり、記号Ｒ２で示される
基が、たとえばアリル基、２−プロピニル基、２−ブテ
ニル基、３−ブテニル基、イソブテニル基、ｌ−メチル
アリル基、２−ブチニル基、３−ブチニル基、ｌ−メチ
ル−２−プロピニル基等である化合物があげられる。The nitrosourea derivative of the present invention is a compound represented by the above general formula [1]. As a typical example, the group represented by the symbol R1 in the general formula [] is placed at the 1st position relative to arabinose, galactose or maltose. Hemiacetal is a residue excluding a hydroxyl group, and the group represented by the symbol R2 is, for example, an allyl group, 2-propynyl group, 2-butenyl group, 3-butenyl group, isobutenyl group, l-methylallyl group, 2-butynyl group. , 3-butynyl group, l-methyl-2-propynyl group, and the like.
更に好適な化合物をあげれば、たとえば１−（２−クロ
ロエチル）−１−ニトロソー３−アリル−３−Ｌ−アラ
ビノピラノシル尿素、１−（２−クロロエチル）−１−
ニトロソー３−アリル−３−Ｄ−ガラクトピラノシル尿
素、１−（２−クロロエチル）−１−ニトロソー３−（
２−プロピニル）−３−Ｄ−ガラクトピラノシル尿素、
１−（２−クロロエチル）−１−ニトロソー３−アリル
−３−Ｄ−マルトシル尿素、１−（２−クロロエチル）
−１−ニトロソー３−イソブテニル一３一Ｄ−マルトシ
ル尿素、１−（２−クロロエチル）−１−ニトロソー３
−（２−ブテニル）−３−Ｄ−マルトシル尿素等がある
。More suitable compounds include, for example, 1-(2-chloroethyl)-1-nitroso-3-allyl-3-L-arabinopyranosylurea, 1-(2-chloroethyl)-1-
Nitroso-3-allyl-3-D-galactopyranosylurea, 1-(2-chloroethyl)-1-nitroso-3-(
2-propynyl)-3-D-galactopyranosyl urea,
1-(2-chloroethyl)-1-nitroso-3-allyl-3-D-maltosylurea, 1-(2-chloroethyl)
-1-nitroso-3-isobutenyl-3-D-maltosylurea, 1-(2-chloroethyl)-1-nitroso-3
-(2-butenyl)-3-D-maltosyl urea and the like.
本発明の化合物〔１〕は一般式
（但し、Ｒ１及びＲ２は前記と同一意味を有する）で示
される尿素誘導体〔〕を適当な溶媒中でニトロソ化する
ことにより製することができる。Compound [1] of the present invention can be produced by nitrosating a urea derivative [] represented by the general formula (wherein R1 and R2 have the same meanings as above) in an appropriate solvent.
ニトロソ化剤としては、たとえば四酸化窒素、三酸化窒
素、亜硝酸等を使用するのが好ましい。四酸化窒素、三
酸化窒素等を使用する場合は、原料化合物〔〕を適当な
溶媒にとかし、この溶液へ脱酸剤の存在下もしくは非存
在下に、四酸化窒素もしくは三酸化窒素等を導入するか
、または適当な溶媒にこれらのニトロソ化剤を導入溶解
せしめた液を加えることによりニトロソ化するのが便利
である。脱酸剤としてはたとえば、重炭酸ソーダ、重炭
酸カリウム、炭酸ソーダ、炭酸カリウム、酢酸ソーダ、
酢酸カリウム等を有利に使用することができる。一方、
ニトロソ化剤として亜硝酸を使用する場合には、通常反
応容器内において、亜硝酸根含有物質と酸とを反応させ
て亜硝酸を製し、これを直ちに原料化合物〔〕と反応さ
せてニトロソ化するのが便利である。亜硝酸根含有物質
としてはたとえば亜硝酸ナトリウム、亜硝酸カリウム等
の亜硝酸金属塩もしくは亜硝酸ブチル、亜硝酸アミルの
如き亜硝酸エステルを使用することができ、また、酸と
してはギ酸、酢酸等の有機酸、希塩酸、希硫酸等の鉱酸
などを有利に使用できる。本発明のニトロソ化反応は、
特に加温もしくは冷却を要することなく室温でも実施可
能であるが、冷却下殊に０〜５℃附近で実施するのが収
率その他の見地からもつとも好ましい。かくして得られ
る本発明化合物〔１〕は、前記した如く、すぐれた抗腫
瘍作用を有すると共に、毒性の極めて低い有用な医薬化
合物である。As the nitrosating agent, it is preferable to use, for example, nitrogen tetroxide, nitrogen trioxide, nitrous acid, or the like. When using nitrogen tetroxide, nitrogen trioxide, etc., dissolve the raw material compound [ ] in an appropriate solvent, and introduce nitrogen tetroxide or nitrogen trioxide, etc. into this solution in the presence or absence of a deoxidizing agent. It is convenient to carry out nitrosation by adding a solution prepared by introducing and dissolving these nitrosating agents into a suitable solvent. Examples of deoxidizers include sodium bicarbonate, potassium bicarbonate, soda carbonate, potassium carbonate, sodium acetate,
Potassium acetate and the like can advantageously be used. on the other hand,
When using nitrous acid as a nitrosating agent, nitrous acid is usually produced by reacting a nitrite group-containing substance with an acid in a reaction vessel, and then immediately reacted with the raw material compound [ ] to nitrosate. It is convenient to do so. As the nitrite group-containing substance, for example, nitrite metal salts such as sodium nitrite and potassium nitrite, or nitrite esters such as butyl nitrite and amyl nitrite can be used, and as acids, formic acid, acetic acid and the like can be used. Organic acids, mineral acids such as dilute hydrochloric acid, dilute sulfuric acid, etc. can be advantageously used. The nitrosation reaction of the present invention is
Although it is possible to carry out the process at room temperature without particularly requiring heating or cooling, it is preferable to carry out the process under cooling, particularly around 0 to 5°C, from the viewpoint of yield and other aspects. The compound of the present invention [1] thus obtained is a useful pharmaceutical compound that has excellent antitumor activity and extremely low toxicity, as described above.
例えば１−（２−クロロエチル）−１−ニトロソー３−
イソブテニル一３−Ｄ−マルトシル尿素は、強力な抗腫
瘍作用を有していることが知られているｌ−（２−クロ
ロエチル）−１−ニトロソー３−（β−Ｄ−グルコピラ
ノシル）尿素と比べ、抗腫瘍効力（エーリツヒ腹水性腫
瘍）ではほぼ同等であるが、毒性が約１０分の１以下に
軽減されている。本発明の化合物〔１〕は医薬として使
用する場合には、経口もしくは非経口にて投与すること
ができる。For example, 1-(2-chloroethyl)-1-nitroso3-
Compared to l-(2-chloroethyl)-1-nitroso-3-(β-D-glucopyranosyl)urea, isobutenyl-3-D-maltosyl urea is known to have strong antitumor effects. The antitumor efficacy (Ehritz ascites tumor) is almost the same, but the toxicity is reduced to about one-tenth or less. When the compound [1] of the present invention is used as a medicine, it can be administered orally or parenterally.
経口的に投与する場合には、たとえば錠剤、散剤、カプ
セル、顆粒剤等とすることができ、また、非経口的に投
与する場合にはたとえば注射用製剤、坐剤等として使用
することができる。尚、本発明の原料化合物〔〕も全て
新規化合物であり、たとえばそれぞれ対応する糖とアミ
ンとを反応させてアミノ糖を製し、次いでこのアミノ糖
と２−クロロエチルイソシアナートとを反応させること
により製することができる。（後記参考例参照）実施例
１
Ｌ−アラビノピラノシル尿素３．２９をテトラヒドロフ
ラン６０ｍ１と塩化メチレン６０−の混液に溶解し、無
水炭酸ナトリウム１５９を加える。When administered orally, it can be used as a tablet, powder, capsule, granule, etc. When administered parenterally, it can be used as an injection preparation, suppository, etc. . Note that the raw material compounds [ ] of the present invention are all new compounds, and for example, amino sugars are produced by reacting the corresponding sugars and amines, and then reacting the amino sugars with 2-chloroethyl isocyanate. It can be manufactured by (See Reference Examples below) Example 1 3.29 ml of L-arabinopyranosyl urea is dissolved in a mixture of 60 ml of tetrahydrofuran and 60 ml of methylene chloride, and 159 ml of anhydrous sodium carbonate is added.
この液にかくはん氷冷下四酸化窒素ガス５９を１０分を
要して導入する。同温度で１０分間かくはん後、反応液
にメタノール１０ｍ１１ついで水３ｄを加え、１０分間
激しくかくはんする。この液を乾燥後、減圧下に溶媒を
留去し、得られる残査をシリカゲルカラムクロマトグラ
フイ一（溶媒；酢酸エチル；クロロホルムリメタノール
＝５：２：ｌ）で精製することにより、１−（２−クロ
ロエチル）−１−ニトロソー３−アリル−３−Ｌ−アラ
ビノピラノシル尿素を黄色カラメルとして２．３ｆＩ得
る。実施例 ２〜３実施例１と同様にして、それぞれ対
応する尿素誘導体より下記化合物を製した。Nitrogen tetroxide gas 59 is introduced into this solution over a period of 10 minutes while stirring and cooling with ice. After stirring at the same temperature for 10 minutes, 10 ml of methanol and 3 d of water were added to the reaction solution, followed by vigorous stirring for 10 minutes. After drying this liquid, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (solvent: ethyl acetate; chloroformrimethanol = 5:2:l). 2.3 fI of (2-chloroethyl)-1-nitroso-3-allyl-3-L-arabinopyranosyl urea are obtained as yellow caramel. Examples 2 to 3 In the same manner as in Example 1, the following compounds were prepared from the corresponding urea derivatives.
（２） １−（２−クロロエチル）−１−ニトロソー３
−アリル−３−Ｄ−ガラクトピラノシル尿素、（３）
１−（２−クロロエチル）−１−ニトロソー３−（２−
プロピニル）−３−Ｄ−ガラクトピラノシル尿素、淡黄
色粉末、λＴ−ーリ一ｌ
実施例 ４
１−（２−クロロエチル）−３−アリル−３−Ｄ−マル
トシルウレア４．９９をテトラヒドロフラン１５０ｍ１
と酢酸２０ｍ１の混液に溶解し、無水酢酸ナトリウム２
０９を加える。(2) 1-(2-chloroethyl)-1-nitroso 3
-Allyl-3-D-galactopyranosyl urea, (3)
1-(2-chloroethyl)-1-nitroso 3-(2-
Example 4 4.99% of 1-(2-chloroethyl)-3-allyl-3-D-maltosylurea was dissolved in tetrahydrofuran. 150m1
Dissolved in a mixture of 20ml of acetic acid and 20ml of anhydrous sodium acetate.
Add 09.
この液にかくはん氷冷下、四酸化窒素ガス８９を１０分
を要して導入し、ついで同温で２０分間さらにかくはん
する。Nitrogen tetroxide gas 89 was introduced into this solution over a period of 10 minutes while stirring and cooling with ice, followed by further stirring at the same temperature for 20 minutes.
反応液にｎ・ヘキサン２００ｍ１を加え、不溶物を除き
、ろ液より溶媒を留去し、残査にエーテル・メタノール
（２０：ｌ）混液２００ＷＩＩを加える。析出した油状
物を分取し、シリカゲルカラムクロマトグラフイ一（溶
媒；酢酸エチルリクロロホルムリメタノール＝２：１：
１）で精製することにより、１−（２−クロロエチル）
−ｌ−ニトロソー３−アリル−３−Ｄ−マルトシル尿素
を淡黄色粉末として３．２９を得る。実施例５〜６実施
例４と同様にして、それぞれ対応する尿素誘導体より下
記化合物を製した。Add 200 ml of n-hexane to the reaction solution, remove insoluble materials, distill off the solvent from the filtrate, and add 200 WII of an ether/methanol (20:l) mixture to the residue. The precipitated oil was collected and subjected to silica gel column chromatography (solvent: ethyl acetate, ethyl chloroformrimethanol = 2:1:
By purifying in step 1), 1-(2-chloroethyl)
3.29 is obtained as -l-nitroso-3-allyl-3-D-maltosylurea as a pale yellow powder. Examples 5 to 6 In the same manner as in Example 4, the following compounds were prepared from the corresponding urea derivatives.
（５） １−（２−クロロエチル）−１−ニトロソー３
−イソブテニル一３−Ｄ−マルトシル尿素、淡黄色粉末
（６） ｌ−（２−クロロエチル）−１−ニトロソー３
−（２−ブテニル）−３−Ｄ−マルトシル尿素、淡黄色
粉末参考例 １
Ｌ−アラビノース４．５ｆ１及びアリルアミン２．５９
をメタノール２０７１Ｌｔに加え、この液を６０℃で３
０分間加熱かくはんする。(5) 1-(2-chloroethyl)-1-nitroso 3
-isobutenyl-3-D-maltosylurea, pale yellow powder (6) l-(2-chloroethyl)-1-nitroso3
-(2-Butenyl)-3-D-maltosyl urea, pale yellow powder Reference example 1 L-arabinose 4.5f1 and allylamine 2.59
was added to 2071Lt of methanol, and this liquid was heated at 60℃ for 3
Heat and stir for 0 minutes.
反応液を減圧下に濃縮乾固し、残査をメタノール５０ｄ
に溶解する。この溶液に、２−クロロエチルイソシアナ
ート３．５９のテトラヒドロフラン１０ｄ溶液を０〜５
℃で滴下し、同温度で１．５時間かくはんする。反応液
を減圧下に濃縮し、残査をギ酸２５７ｆ１１に溶解し室
温で２０分間放置する。この溶液にエーテル、ヘキサン
（３：１）混液１゜５０ｍ１を加え、析出した油状物を
分取し、シリカゲルカラムクロマトグラフイ一（溶媒；
クロロホルムリメタノール：酢酸エチル＝２：１：３）
で精製することにより、１−（２−クロロエチル）−３
−アリル−３−Ｌ−アラビノピラノシル尿素を無色カラ
メル状粉末として５．５９得る。参考例 ２〜３
参考例１と同様にして、それぞれ対応する糖及びアミン
より下記化合物を製した。The reaction solution was concentrated to dryness under reduced pressure, and the residue was mixed with 50 d of methanol.
dissolve in To this solution, add 0 to 5 d of a solution of 3.59 2-chloroethyl isocyanate in 10 d of tetrahydrofuran.
It was added dropwise at ℃ and stirred at the same temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in formic acid 257f11 and left at room temperature for 20 minutes. To this solution was added 1.50 ml of a mixture of ether and hexane (3:1), and the precipitated oil was collected and subjected to silica gel column chromatography (solvent;
chloroformrimethanol: ethyl acetate = 2:1:3)
1-(2-chloroethyl)-3
-Allyl-3-L-arabinopyranosyl urea is obtained as a colorless caramelized powder. Reference Examples 2 to 3 In the same manner as in Reference Example 1, the following compounds were prepared from the corresponding sugars and amines.
Claims (1)
＾１はアラビノース、ガラクトースまたはマルトースよ
りそれぞれ１位ヘミアセタール水酸基を除いた残基、Ｒ
＾２は分枝することもある炭素数３〜４個のアルケニル
基又はアルキニル基を表わす）で示されるニトロソ尿素
誘導体。 ２ 一般式〔 I 〕において、Ｒ＾２がアリル基、２−
プロピニル基、２−ブテニル基またはイソブテニル基で
ある特許請求の範囲第１項記載の化合物。 ３ １−（２−クロロエチル）−１−ニトロソ−３−ア
リル−３−Ｌ−アラビノピラノシル尿素である特許請求
の範囲第１項記載の化合物。 ４ １−（２−クロロエチル）−１−ニトロソ−３−ア
リル−３−Ｄ−ガラクトピラノシル尿素である特許請求
の範囲第１項記載の化合物。 ５ １−（２−クロロエチル）−１−ニトロソ−３−（
２−プロピニル）−３−Ｄ−ガラクトピラノシル尿素で
ある特許請求の範囲第１項記載の化合物。 ６ １−（２−クロロエチル）−１−ニトロソ−３−ア
リル−３−Ｄ−マルトシル尿素である特許請求の範囲第
１項記載の化合物。 ７ １−（２−クロロエチル）−１−ニトロソ−３−イ
ソブテニル−３−Ｄ−マルトシル尿素である特許請求の
範囲第１項記載の化合物。 ８ １−（２−クロロエチル）−１−ニトロソ−３−（
２−ブテニル）−３−Ｄ−マルトシル尿素である特許請
求の範囲第１項記載の化合物。 ９ 一般式 ▲数式、化学式、表等があります▼〔II〕（但し、Ｒ＾
１はアラビノース、ガラクトースまたはマルトースより
それぞれ１位ヘミアセタール水酸基を除いた残基、Ｒ＾
２は分枝することもある炭素数３〜４個のアルケニル基
またはアルキニル基を表わす）で示される尿素誘導体を
ニトロソ化することを特徴とする一般式▲数式、化学式
、表等があります▼〔 I 〕（但し、Ｒ＾１及びＲ＾２
は前記と同一意味を有する）で示されるニトロソ尿素誘
導体の製法。 １０ ニトロソ化剤が四酸化窒素である特許請求の範囲
第９項記載の製法。[Claims] 1. General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼[I] (However, R
^1 is a residue obtained by removing the hemiacetal hydroxyl group at the 1st position from arabinose, galactose or maltose, respectively, R
^2 represents an alkenyl group or alkynyl group having 3 to 4 carbon atoms which may be branched). 2 In the general formula [I], R^2 is an allyl group, 2-
The compound according to claim 1, which is a propynyl group, a 2-butenyl group, or an isobutenyl group. 3. The compound according to claim 1, which is 1-(2-chloroethyl)-1-nitroso-3-allyl-3-L-arabinopyranosyl urea. 4. The compound according to claim 1, which is 1-(2-chloroethyl)-1-nitroso-3-allyl-3-D-galactopyranosylurea. 5 1-(2-chloroethyl)-1-nitroso-3-(
2-Propynyl)-3-D-galactopyranosyl urea. 6. The compound according to claim 1, which is 1-(2-chloroethyl)-1-nitroso-3-allyl-3-D-maltosyl urea. 7. The compound according to claim 1, which is 1-(2-chloroethyl)-1-nitroso-3-isobutenyl-3-D-maltosyl urea. 8 1-(2-chloroethyl)-1-nitroso-3-(
2-Butenyl)-3-D-maltosyl urea. 9 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [II] (However, R^
1 is a residue obtained by removing the hemiacetal hydroxyl group at the 1st position from arabinose, galactose, or maltose, respectively, R^
2 represents an alkenyl group or alkynyl group with 3 to 4 carbon atoms, which may be branched) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [ I] (However, R^1 and R^2
has the same meaning as above). 10. The production method according to claim 9, wherein the nitrosating agent is nitrogen tetroxide.
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6345978A JPS5919555B2 (en) | 1978-05-26 | 1978-05-26 | Nitrosourea transparent conductor and its manufacturing method |
| US05/922,811 US4182757A (en) | 1977-07-29 | 1978-07-10 | Novel nitrosourea compounds and process for preparing the same |
| FI782215A FI65439C (en) | 1977-07-29 | 1978-07-11 | REFERENCE TO A NUTROSOURE DEFINITION WITH ANTI-TURMOERACTIVITY |
| MX10099078U MX5407E (en) | 1977-07-29 | 1978-07-20 | PROCEDURE FOR PREPARING NITROSOUREA COMPOUNDS |
| DE2858078A DE2858078C2 (en) | 1977-07-29 | 1978-07-21 | 2-chloroethylnitrosoureas, processes for their preparation and pharmaceutical preparations containing these compounds |
| DE19782857911 DE2857911C2 (en) | 1977-07-29 | 1978-07-21 | 1- (2-chloroethyl) -3-substituted-3-glycosylureas, processes for their production and their use for the production of 1- (2-chloroethyl) -1-nitroso-3-substituted-3-glycosylureas |
| DE2832127A DE2832127C2 (en) | 1977-07-29 | 1978-07-21 | 1- (2-chloroethyl) -1-nitroso-3-substituted-3-glycosylureas, processes for their preparation and pharmaceutical preparations containing these compounds |
| CA307,987A CA1097624A (en) | 1977-07-29 | 1978-07-24 | Nitrosourea compounds and process for preparing the same |
| PH21418A PH13936A (en) | 1977-07-29 | 1978-07-25 | Novel nitrosourea compounds and process for preparing the same |
| SE7808162A SE435501B (en) | 1977-07-29 | 1978-07-26 | NITROSOCARBAMIDE DERIVATIVES AND PHARMACOLOGICAL COMPOSITION CONTAINING THIS |
| DK331978A DK331978A (en) | 1977-07-29 | 1978-07-26 | NITROSOURIN INDUSTRIAL DERIVATIVES AND PROCEDURES FOR THE PREPARATION |
| CH809678A CH636626A5 (en) | 1977-07-29 | 1978-07-27 | NITROSO-UREA COMPOUNDS AND METHOD FOR THE PRODUCTION AND USE THEREOF IN THERAPEUTIC AGENTS. |
| HU78TA1491A HU176891B (en) | 1977-07-29 | 1978-07-27 | Process for preparing nitroso-carbamide derivatives |
| IT68797/78A IT1160450B (en) | 1977-07-29 | 1978-07-27 | NITROSUREIC COMPOUNDS AND PROCEDURE FOR THEIR PREPARATION |
| AT546178A AT360553B (en) | 1977-07-29 | 1978-07-27 | METHOD FOR PRODUCING NEW NITROSOURATE COMPOUNDS |
| FR7822477A FR2403994A1 (en) | 1977-07-29 | 1978-07-28 | NEWS 1- (2-CHLOROETHYL) -1-NITROSOUREES USEFUL IN PARTICULAR AS ANTITUMOR AGENTS AND THEIR PREPARATION PROCESS |
| SU782643999A SU908247A3 (en) | 1977-07-29 | 1978-07-28 | Process for preparing nitroso urea derivatives |
| BE189567A BE869352A (en) | 1977-07-29 | 1978-07-28 | NEW NITROSOUREES AND THEIR APPLICATION |
| PL1978208701A PL111784B1 (en) | 1977-07-29 | 1978-07-28 | Method of manufacture of novel derivatives of nitrosourea |
| PT68359A PT68359A (en) | 1977-07-29 | 1978-07-28 | Process for preparing novel nitrosourea derivatives |
| NL7808036A NL7808036A (en) | 1977-07-29 | 1978-07-28 | NITROSOUREUM DERIVATIVES. |
| AR273129A AR219331A1 (en) | 1977-07-29 | 1978-07-28 | NEW DERIVATIVE FROM UREA, PARTICULARLY USEFUL AS A NON-PHARMACOLOGICAL INTERMEDIARY IN THE PRODUCTION OF A NITROSOUREA COMPOUND AND PROCEDURE FOR THE PREPARATION OF THE NITROSOUREA COMPOUND |
| EG46478A EG13375A (en) | 1977-07-29 | 1978-07-29 | Nitrosourea compounds and process for preparing the same |
| GB8027528A GB2053918B (en) | 1977-07-29 | 1978-07-31 | Urea compounds |
| GB7831712A GB2002370B (en) | 1977-07-29 | 1978-07-31 | Nitrosourea compounds and process for preparing the same |
| AU38491/78A AU525239B2 (en) | 1977-07-29 | 1978-07-31 | Improvements in or relating to nitrosourea compounds |
| CS785045A CS216918B2 (en) | 1977-07-29 | 1978-07-31 | Method of preparation of the nitrurea |
| FR8105772A FR2475040B1 (en) | 1977-07-29 | 1981-03-23 | |
| FR8115054A FR2485541B1 (en) | 1977-07-29 | 1981-08-03 | |
| FR8205133A FR2499577A1 (en) | 1977-07-29 | 1982-03-25 | SUBSTITUTED 1- (2-CHLOROETHYL) -1-NITROSOUREES-3-SUBSTITUTED BY SUGAR REST, PARTICULARLY USEFUL AS ANTITUMOR AGENTS AND PROCESS FOR THE PREPARATION THEREOF |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6345978A JPS5919555B2 (en) | 1978-05-26 | 1978-05-26 | Nitrosourea transparent conductor and its manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS54154714A JPS54154714A (en) | 1979-12-06 |
| JPS5919555B2 true JPS5919555B2 (en) | 1984-05-07 |
Family
ID=13229834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6345978A Expired JPS5919555B2 (en) | 1977-07-29 | 1978-05-26 | Nitrosourea transparent conductor and its manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5919555B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0120301Y2 (en) * | 1984-11-15 | 1989-06-15 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8299035B2 (en) | 2008-05-15 | 2012-10-30 | Taisho Pharmaceutucal Co., Ltd. | 10a-azalide compound having 4-membered ring structure |
-
1978
- 1978-05-26 JP JP6345978A patent/JPS5919555B2/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0120301Y2 (en) * | 1984-11-15 | 1989-06-15 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54154714A (en) | 1979-12-06 |
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