JPS636063B2 - - Google Patents
Info
- Publication number
- JPS636063B2 JPS636063B2 JP55085532A JP8553280A JPS636063B2 JP S636063 B2 JPS636063 B2 JP S636063B2 JP 55085532 A JP55085532 A JP 55085532A JP 8553280 A JP8553280 A JP 8553280A JP S636063 B2 JPS636063 B2 JP S636063B2
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- hydroxyethyl
- present
- guanidine
- methyl
- 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
- 238000004519 manufacturing process Methods 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- IWDXEQQPYYDWDM-UHFFFAOYSA-N 1-cyano-3-(2-hydroxyethyl)-2-methylguanidine Chemical compound N#CNC(=NC)NCCO IWDXEQQPYYDWDM-UHFFFAOYSA-N 0.000 claims description 3
- LRECNVISJXSIRD-UHFFFAOYSA-N methyl n-cyano-n'-(2-hydroxyethyl)carbamimidothioate Chemical compound N#CNC(SC)=NCCO LRECNVISJXSIRD-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 3
- 229960001380 cimetidine Drugs 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- UESSEMPSSAXQJC-UHFFFAOYSA-N ethanol;methanamine Chemical compound NC.CCO UESSEMPSSAXQJC-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は下記（）式で示される新規化合物Ｎ
−シアノ−N′−メチル−N″−（２−ヒドロキシエ
チル）−グアニジン及びその製造法を提供するこ
とに関する：
本発明により提供された新規グアニジン誘導体
は、例えばヒスタミンH2の受容体を遮断するこ
とにより胃及び十二指腸潰瘍の治療に有効に使用
される一般名をシメチジン（Cimetidine）で知
られる医薬品の合成中間体として有用なものであ
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound N represented by the following formula ().
-Cyano-N'-methyl-N''-(2-hydroxyethyl)-guanidine and a method for producing the same: The novel guanidine derivatives provided by the present invention are intermediates for the synthesis of drugs known by the generic name Cimetidine, which are effectively used in the treatment of gastric and duodenal ulcers by blocking the receptors of histamine H2 , for example. It is useful as a.
すなわち、従来までのシメチジンの製造は比較
的高価なシステアミン（HSCH2CH2NH2）を原
料として使用し、多行程を必要とし、さらに目的
物の精製に煩雑さが避けられないものであつた
が、比較的安価かつ容易に入手できる本発明新規
化合物をシメチジン製造の中間原料として使用す
れば、前記の製造上の難点を著しく改善させるこ
とが可能になるのである。 In other words, the conventional production of cimetidine used relatively expensive cysteamine (HSCH 2 CH 2 NH 2 ) as a raw material, required multiple steps, and was unavoidably complicated in purifying the target product. However, if the novel compound of the present invention, which is relatively inexpensive and easily available, is used as an intermediate raw material for the production of cimetidine, it becomes possible to significantly improve the above-mentioned production difficulties.
本発明の新規化合物Ｎ−シアノ−N′−メチル
−N″−（２−ヒドロキシエチル）−グアニジンを
製造するには、下式（）で示されるＮ−シアノ
−N′−（２−ヒドロキシエチル）−Ｓ−メチルイ
ソチオ尿素：
をアルコール系溶媒下でメチルアミンと反応させ
ることで得られる。 In order to produce the novel compound N-cyano-N'-methyl-N''-(2-hydroxyethyl)-guanidine of the present invention, N-cyano-N'-(2-hydroxyethyl )-S-methylisothiourea: can be obtained by reacting with methylamine in an alcoholic solvent.
この反応に用いられるアルコール系溶媒として
は、エタノール、メタノール、イソプロピルアル
コール等であり、反応温度は室温ないし80℃、好
ましくは40ないし60℃の範囲である。反応時間は
２ないし５時間で十分である。 The alcoholic solvent used in this reaction includes ethanol, methanol, isopropyl alcohol, etc., and the reaction temperature ranges from room temperature to 80°C, preferably from 40 to 60°C. A reaction time of 2 to 5 hours is sufficient.
なお、上記式（）で示される化合物も本発明
者らによつて初めて得られた新規化合物であつ
て、エタノールとジメチルシアノイミドジチオカ
ーボネートから製造できることは、本願と同日付
けをもつて特許出願されたところである。 The compound represented by the above formula () is also a new compound obtained for the first time by the present inventors, and the fact that it can be produced from ethanol and dimethylcyanoimide dithiocarbonate is a patent application filed on the same date as the present application. That's where it was.
以下に実施例をもつて本発明化合物の製造具体
例及び物性値を示す。 Examples of the production of the compounds of the present invention and physical property values are shown below in Examples.
実施例
エタノール300mlにＮ−シアノ−N′−（２−ヒ
ドロキシエチル）−Ｓ−メチルイソチオ尿素50ｇ
を加え、30％メチルアミン−エタノール溶液500
mlを加えて、50℃で４時間加熱撹拌する。反応後
溶媒を留去し、残査を酢酸エチルで洗浄すると白
色の結晶39.2ｇが得られた。収率＝92％。融点98
〜100℃。Example 50 g of N-cyano-N'-(2-hydroxyethyl)-S-methylisothiourea in 300 ml of ethanol
Add 30% methylamine-ethanol solution 500
ml and heat and stir at 50°C for 4 hours. After the reaction, the solvent was distilled off and the residue was washed with ethyl acetate to obtain 39.2 g of white crystals. Yield = 92%. melting point 98
~100℃.
IRνmax（KBr）：3250cm-1付近、2130cm-1、1050
cm-1
NMR（DMSO−d6）Sppm：2.65（Ｓ、3H）、3.28
（ｍ、4H）、6.10（broad、3H、D2Oで消失）
元素分析（C5H10N4Oとして）
理論値(%)：Ｃ、42.2；Ｈ、7.09；Ｎ、39.4
実測値(%)：Ｃ、41.9；Ｈ、7.02；Ｎ、39.0IRνmax (KBr): around 3250cm -1 , 2130cm -1 , 1050
cm -1 NMR (DMSO-d 6 ) Sppm: 2.65 (S, 3H), 3.28
(m, 4H), 6.10 (broad, 3H, disappears with D 2 O) Elemental analysis (as C 5 H 10 N 4 O) Theoretical value (%): C, 42.2; H, 7.09; N, 39.4 Actual value ( %): C, 41.9; H, 7.02; N, 39.0
Claims (1)
−N″−（２−ヒドロキシエチル）−グアニジン。 ２ 下記式で示されるＮ−シアノ−N′−（２−ヒ
ドロキシエチル）−Ｓ−メチルイソチオ尿素： をメチルアミンと反応させることを特徴とするＮ
−シアノ−N′−メチル−N″−（２−ヒドロキシエ
チル）−グアニジンの製造法。[Claims] 1. N-cyano-N'-methyl-N''-(2-hydroxyethyl)-guanidine represented by the following formula. 2 N-cyano-N'-(2-hydroxyethyl)-S-methylisothiourea represented by the following formula: N characterized by reacting with methylamine
-Production method of cyano-N'-methyl-N''-(2-hydroxyethyl)-guanidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8553280A JPS5711954A (en) | 1980-06-23 | 1980-06-23 | Novel nitroguanidine derivative and it preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8553280A JPS5711954A (en) | 1980-06-23 | 1980-06-23 | Novel nitroguanidine derivative and it preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5711954A JPS5711954A (en) | 1982-01-21 |
| JPS636063B2 true JPS636063B2 (en) | 1988-02-08 |
Family
ID=13861492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8553280A Granted JPS5711954A (en) | 1980-06-23 | 1980-06-23 | Novel nitroguanidine derivative and it preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5711954A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58157975A (en) * | 1982-03-10 | 1983-09-20 | Tokyo Ohka Kogyo Co Ltd | Plasma etching method |
| JPH0622212B2 (en) * | 1983-05-31 | 1994-03-23 | 株式会社東芝 | Dry etching method |
| KR970003885B1 (en) * | 1987-12-25 | 1997-03-22 | 도오교오 에레구토론 가부시끼 가이샤 | Etching method and apparatus thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54148724A (en) * | 1978-05-12 | 1979-11-21 | Crc Ricerca Chim | Nncyanoazomecins and their manufacture |
-
1980
- 1980-06-23 JP JP8553280A patent/JPS5711954A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54148724A (en) * | 1978-05-12 | 1979-11-21 | Crc Ricerca Chim | Nncyanoazomecins and their manufacture |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5711954A (en) | 1982-01-21 |
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