JPS5849361A - メルカプトエチル置換グアニジンの製法 - Google Patents
メルカプトエチル置換グアニジンの製法Info
- Publication number
- JPS5849361A JPS5849361A JP57148483A JP14848382A JPS5849361A JP S5849361 A JPS5849361 A JP S5849361A JP 57148483 A JP57148483 A JP 57148483A JP 14848382 A JP14848382 A JP 14848382A JP S5849361 A JPS5849361 A JP S5849361A
- Authority
- JP
- Japan
- Prior art keywords
- mercaptoethyl
- guanidine
- methyl
- cyano
- manufacture
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
め要約のデータは記録されません。
Description
【発明の詳細な説明】
本発明はメルカプトエチル置換グアニジン、さらに詳し
くは、N−シアノ−N−メチル−N−(2−メルカプト
エチル)グアニジンの製法番こ関する。
くは、N−シアノ−N−メチル−N−(2−メルカプト
エチル)グアニジンの製法番こ関する。
本発明の製法で得られるN−シアノ−N−メチル−N−
(2−メルカプトエチル)グアニジンは式: で示され、例えば、ヒスタミン1]2−拮抗剤として知
られるN−シアノ−N−メチル−N’ −[2−((5
−メチル−4−イミダゾリル)メチルチオ)エチル〕グ
アニジン(シメチジン)の製造、における出発物質とし
て有用である。
(2−メルカプトエチル)グアニジンは式: で示され、例えば、ヒスタミン1]2−拮抗剤として知
られるN−シアノ−N−メチル−N’ −[2−((5
−メチル−4−イミダゾリル)メチルチオ)エチル〕グ
アニジン(シメチジン)の製造、における出発物質とし
て有用である。
式[I]のメルカプトエチル置換グアニジンはシステア
ミン(2−メルカプトエチルアミン)をN−シアノ−N
、S−ジメチルイソチオウレアと反応させることにより
得られる。また、N−シアノジメチルジチオイミドカル
ボネートをメチルアミン、ついで、システアミンと連続
的に反応させてもよい。
ミン(2−メルカプトエチルアミン)をN−シアノ−N
、S−ジメチルイソチオウレアと反応させることにより
得られる。また、N−シアノジメチルジチオイミドカル
ボネートをメチルアミン、ついで、システアミンと連続
的に反応させてもよい。
本発明で得られる化合物および出発物質として用いる化
合物はその塩の形でも存在しつる。
合物はその塩の形でも存在しつる。
式[I]のメルカプトエチル置換グアニジンを、例えば
、塩基性条件下に5−メチル−4−クロロメチルイミダ
ゾールと反応させることにより、シメチシンが得られる
。
、塩基性条件下に5−メチル−4−クロロメチルイミダ
ゾールと反応させることにより、シメチシンが得られる
。
つきに、実施例および参考例を挙げて本発明をさらに詳
しぐ説明する。
しぐ説明する。
実施例
システアミン塩酸塩5゜689の水20m/溶液をN−
シアノ−N、S−ジメチルイソチオウレア6.462の
エタノール100−懸濁液に加える。水酸化ナトリウム
4.09の水2〇−溶液をこの混合液に加え、1時間加
熱還流する。−得られた清澄溶液を濃縮してエタノール
を除去し、少量の水を加え、このアルカリ性水溶液を酢
酸エチルで抽出する。
シアノ−N、S−ジメチルイソチオウレア6.462の
エタノール100−懸濁液に加える。水酸化ナトリウム
4.09の水2〇−溶液をこの混合液に加え、1時間加
熱還流する。−得られた清澄溶液を濃縮してエタノール
を除去し、少量の水を加え、このアルカリ性水溶液を酢
酸エチルで抽出する。
この水溶液を塩酸でPH4に調整し、酢酸エチルで抽出
する。この後者の抽出液を乾燥し、蒸発させて無色油状
のN−シアノ−N−メチル−N″−(2−メルカプトエ
チル)グアニジン6.12yを得る。
する。この後者の抽出液を乾燥し、蒸発させて無色油状
のN−シアノ−N−メチル−N″−(2−メルカプトエ
チル)グアニジン6.12yを得る。
この生成物を特徴つける(確認する)ため、2゜4−ジ
ニトロクロロベンゼン7.79の−95%エタノール5
〇−溶液をN−シアノ−N−メチル−N−(2−メルカ
プトエチル)グアニジン6.09の95%エタノール溶
液に加え、1時間還流し、冷却する。得られた結晶質固
形物773グを集め、大容量のエーテルでトリチュレー
トL、アセトニトリルから再結晶させてN−シアノ−N
′−メチル−N−(S−(2,4−ジニトロフェニル)
−2−メルカプトエチル〕グアニジンを得る。融点21
0〜211℃、元素分析(%)実測値: C,41,0
;H,3,7; N、26.0 ; S、l O,0;
C111(12N604Sとして理論値二C,40,7
; 11,3.7 ; N、25.9 ; S。
ニトロクロロベンゼン7.79の−95%エタノール5
〇−溶液をN−シアノ−N−メチル−N−(2−メルカ
プトエチル)グアニジン6.09の95%エタノール溶
液に加え、1時間還流し、冷却する。得られた結晶質固
形物773グを集め、大容量のエーテルでトリチュレー
トL、アセトニトリルから再結晶させてN−シアノ−N
′−メチル−N−(S−(2,4−ジニトロフェニル)
−2−メルカプトエチル〕グアニジンを得る。融点21
0〜211℃、元素分析(%)実測値: C,41,0
;H,3,7; N、26.0 ; S、l O,0;
C111(12N604Sとして理論値二C,40,7
; 11,3.7 ; N、25.9 ; S。
9.9
参考例
窒素雰囲気下、攪拌しながらナトリウム1,432を乾
燥エタノール100m/に加える。ナトリウムが溶解し
た後、N−シアノ−N′−メチル−N’−(2−メルカ
プトエチル)グアニジン4.909の乾燥エタノール5
0i溶液を加え、この混合液を室温で1時間攪拌する。
燥エタノール100m/に加える。ナトリウムが溶解し
た後、N−シアノ−N′−メチル−N’−(2−メルカ
プトエチル)グアニジン4.909の乾燥エタノール5
0i溶液を加え、この混合液を室温で1時間攪拌する。
5−メチル−4−クロロメチルイミダゾール塩酸塩5.
189を室温で1時間を要し、数回に分けて加える。こ
の混合液を室温でさらに1時間攪拌し、0.5時間加熱
還流する。
189を室温で1時間を要し、数回に分けて加える。こ
の混合液を室温でさらに1時間攪拌し、0.5時間加熱
還流する。
冷却後、混合液を沖過し、r液を蒸発させてガラス状固
形物8.89を得る。この粗生成物をシリカゲルFてク
ロマトグラフィーに付し、アセトニトリルで溶出し、得
られた固形の生成物3.609をアセトニトリルから再
結晶させてN−シアノ−N′−メチル−N−[2−((
5−メチル−4−イミダゾリル)メチルチオ)エチル〕
グアニジンを得る。融点140〜142℃、元素分析(
%)実測値:C,47,9;)(,6,3; N、33
.3 ; S、12.5 ;C1oH16N6sとして
理論値: C,47,6; H,6,4; N、33.
3 ; S、12.7 第1頁の続き 0発 明 者 ジョン・コリン・エメットイギチス国イ
ングランド・ハー トフォードシャー・コディコー ト・タイス・クローズ21番 0発 明 者 チャーロン・ロビン・ガネリンイギリス
国イングランド・ハー トフォードシャー・ウニリン・ ガーデン・シティ・ナイフフィ ールド389番
形物8.89を得る。この粗生成物をシリカゲルFてク
ロマトグラフィーに付し、アセトニトリルで溶出し、得
られた固形の生成物3.609をアセトニトリルから再
結晶させてN−シアノ−N′−メチル−N−[2−((
5−メチル−4−イミダゾリル)メチルチオ)エチル〕
グアニジンを得る。融点140〜142℃、元素分析(
%)実測値:C,47,9;)(,6,3; N、33
.3 ; S、12.5 ;C1oH16N6sとして
理論値: C,47,6; H,6,4; N、33.
3 ; S、12.7 第1頁の続き 0発 明 者 ジョン・コリン・エメットイギチス国イ
ングランド・ハー トフォードシャー・コディコー ト・タイス・クローズ21番 0発 明 者 チャーロン・ロビン・ガネリンイギリス
国イングランド・ハー トフォードシャー・ウニリン・ ガーデン・シティ・ナイフフィ ールド389番
Claims (2)
- (1) システアミンをN−シアノ−N、S−ジメチ
ルイソチオウレアと反応させることを特徴とするN−シ
アノ−N−メチル−N−(2−メルカプトエチル)グア
ニジンの製法。 - (2)N−シアノジメチルジチオイミドカルボネートを
メチルアミンと反応させ、ついで、システアミンと反応
させることを特徴とするN−シアノ−N−メチル−N−
(2−メルカプトエチル)グアニジンの製法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB38257/74A GB1533380A (en) | 1974-09-02 | 1974-09-02 | Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines |
GB38257/74 | 1974-09-02 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5849361A true JPS5849361A (ja) | 1983-03-23 |
JPS5940829B2 JPS5940829B2 (ja) | 1984-10-03 |
Family
ID=10402297
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50106460A Granted JPS51125074A (en) | 1974-09-02 | 1975-09-01 | Production of heterocyclic compound |
JP57148483A Expired JPS5940829B2 (ja) | 1974-09-02 | 1982-08-25 | メルカプトエチル置換グアニジンの製法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50106460A Granted JPS51125074A (en) | 1974-09-02 | 1975-09-01 | Production of heterocyclic compound |
Country Status (8)
Country | Link |
---|---|
US (1) | US4013678A (ja) |
JP (2) | JPS51125074A (ja) |
BE (1) | BE832663A (ja) |
CA (1) | CA1063119A (ja) |
CH (1) | CH608232A5 (ja) |
GB (1) | GB1533380A (ja) |
IE (1) | IE41856B1 (ja) |
NL (1) | NL7510344A (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63190872A (ja) * | 1986-09-12 | 1988-08-08 | Mitsui Petrochem Ind Ltd | シアノグアニジン誘導体の製造方法 |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1574214A (en) | 1976-03-11 | 1980-09-03 | Smith Kline French Lab | Amidines |
US4189488A (en) * | 1976-03-11 | 1980-02-19 | Smith Kline & French Laboratories Limited | Amidinoformic and amidinosulphinic acids |
ZA774220B (en) * | 1976-07-28 | 1978-06-28 | Smith Kline French Lab | Pharmacologically active compounds |
NZ184893A (en) * | 1976-09-21 | 1980-11-28 | Smith Kline French Lab | Pure crystalline form of cimetidine a(n-methyl-n-cyano-n-(-2-(5-methyl-4imidazolyl) methylthio) ethyl)-guanidine andpharmaceutical compositions containing it |
NZ186965A (en) | 1977-04-20 | 1980-02-21 | Ici Ltd | Guanidino derivatives and pharmaceutical compositions |
US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
US4158013A (en) * | 1977-06-03 | 1979-06-12 | Bristol-Myers Company | N-Cyano-N'-alkynyl-N"-2-mercaptoethylguanidines |
NZ187376A (en) * | 1977-06-03 | 1981-05-29 | Bristol Myers Co | N-cyano-n-(2-(4-methyl-5-imidazolyl)methylthio)ethyl)-n-alkynyl guanidines intermediates pharmaceutical compositions |
IL56265A (en) * | 1977-12-28 | 1982-08-31 | Om Lab Sa | Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor |
GR65283B (en) * | 1977-12-30 | 1980-08-01 | Crc Ricerca Chim | Method for the alkyliosis of 4(5)-merka ptomethyl-imidazoles with aziridin derivatives |
YU40332B (en) * | 1978-04-26 | 1985-12-31 | Lek Tovarna Farmacevtskih | Process for preparing n-cyano-n'-methyl-n''-((2-((4-methyl-5-imidazolyl)-methylthio)ethyl)-guanidine |
DE2963363D1 (en) | 1978-05-24 | 1982-09-09 | Ici Plc | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
US4157340A (en) * | 1978-06-27 | 1979-06-05 | Bristol-Meyers Company | N,N'-[Bis(N-cyanoguanyl)]cystamine derivatives |
YU40716B (en) * | 1978-07-19 | 1986-04-30 | Pliva Pharm & Chem Works | Process for obtaining n-cyano-n'-methyl-n'-û2-|5-metylimidazole4-yl)-methyl¨-thioethylù guanidine |
US4200760A (en) * | 1978-09-26 | 1980-04-29 | Bristol-Myers Company | Imidazolylalkylthioalkylamino-ethylene derivatives |
EP0010893B1 (en) * | 1978-10-16 | 1984-02-08 | Imperial Chemical Industries Plc | Antisecretory branched-chain heterocyclic guanidine derivatives, processes for their manufacture, intermediates, and pharmaceutical compositions containing said derivatives |
GB2035313B (en) * | 1978-11-02 | 1983-01-06 | Pliva Pharm & Chem Works | Preparation of n-cyano-n'-methyl-n''-(2-mercaptoethyl)-guanidine |
US4276421A (en) * | 1978-11-18 | 1981-06-30 | Societe De Recherches Et De Syntheses Organiques S.A. | Cyano-guanidine geometrical isomers |
JPS56500174A (ja) * | 1979-02-14 | 1981-02-19 | ||
US4242351A (en) * | 1979-05-07 | 1980-12-30 | Imperial Chemical Industries Limited | Antisecretory oxadiazoles and pharmaceutical compositions containing them |
JPS6056139B2 (ja) * | 1980-11-26 | 1985-12-09 | 藤本製薬株式会社 | シアノグアニジン誘導体の製造法 |
JPS57120572A (en) * | 1981-01-21 | 1982-07-27 | Fujimoto Seiyaku Kk | Guanidine derivative and its preparation |
JPS57120574A (en) * | 1981-01-21 | 1982-07-27 | Fujimoto Seiyaku Kk | Production of guanidine derivative |
US4374996A (en) * | 1981-06-03 | 1983-02-22 | Sk & F Lab Co. | Disulfide intermediate for cimetidine |
US4447621A (en) * | 1981-06-03 | 1984-05-08 | Sk&F Lab Co. | Use of N-cyano-N'-methyl-N"-[2-(5-methyl-4-imidazolylmethyldithio)ethyl]guanidine in the preparation of cimetidine |
JPS5888366A (ja) * | 1981-11-19 | 1983-05-26 | Fujimoto Seiyaku Kk | グアニジン誘導体の製造法 |
IE55946B1 (en) * | 1982-10-08 | 1991-02-27 | Gea Farmaceutisk Fabrik As | Thioethercyanoguanidines and their use as intermediates in producing imidazoles |
JPS59128375A (ja) * | 1983-01-10 | 1984-07-24 | Tokawa Tetsuo | イミダゾ−ル系化合物の製法 |
JPS59130274A (ja) * | 1983-01-14 | 1984-07-26 | Tokawa Tetsuo | イミダゾ−ル系化合物の製法 |
JPH0373817A (ja) * | 1989-08-16 | 1991-03-28 | Shinko Electric Co Ltd | 温度計測方法及び装置 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3905984A (en) * | 1971-03-09 | 1975-09-16 | Smith Kline French Lab | Pyridyl substituted thioalkyl-and oxyalkyl-thioureas and ureas |
GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
-
1974
- 1974-09-02 GB GB38257/74A patent/GB1533380A/en not_active Expired
-
1975
- 1975-08-12 IE IE1797/75A patent/IE41856B1/en unknown
- 1975-08-20 CA CA233,788A patent/CA1063119A/en not_active Expired
- 1975-08-20 US US05/606,269 patent/US4013678A/en not_active Expired - Lifetime
- 1975-08-22 BE BE159393A patent/BE832663A/xx not_active IP Right Cessation
- 1975-08-26 CH CH1104975A patent/CH608232A5/xx unknown
- 1975-09-01 JP JP50106460A patent/JPS51125074A/ja active Granted
- 1975-09-02 NL NL7510344A patent/NL7510344A/xx not_active Application Discontinuation
-
1982
- 1982-08-25 JP JP57148483A patent/JPS5940829B2/ja not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63190872A (ja) * | 1986-09-12 | 1988-08-08 | Mitsui Petrochem Ind Ltd | シアノグアニジン誘導体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
JPS5940829B2 (ja) | 1984-10-03 |
US4013678A (en) | 1977-03-22 |
JPS51125074A (en) | 1976-11-01 |
IE41856L (en) | 1976-03-02 |
IE41856B1 (en) | 1980-04-09 |
NL7510344A (nl) | 1976-03-04 |
GB1533380A (en) | 1978-11-22 |
CH608232A5 (ja) | 1978-12-29 |
CA1063119A (en) | 1979-09-25 |
BE832663A (fr) | 1976-02-23 |
JPS635389B2 (ja) | 1988-02-03 |
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