JPS5940829B2 - 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
JPS5940829B2
JPS5940829B2 JP57148483A JP14848382A JPS5940829B2 JP S5940829 B2 JPS5940829 B2 JP S5940829B2 JP 57148483 A JP57148483 A JP 57148483A JP 14848382 A JP14848382 A JP 14848382A JP S5940829 B2 JPS5940829 B2 JP S5940829B2
Authority
JP
Japan
Prior art keywords
mercaptoethyl
guanidine
methyl
cyano
producing
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
Application number
JP57148483A
Other languages
English (en)
Other versions
JPS5849361A (ja
Inventor
ト−マス・ヘンリ−・ブラウン
グラハム・ジヨン・デユラント
ジヨン・コリン・エメツト
チヤ−ロン・ロビン・ガネリン
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SUMISU KURAIN Ltd
Original Assignee
SUMISU KURAIN Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by SUMISU KURAIN Ltd filed Critical SUMISU KURAIN Ltd
Publication of JPS5849361A publication Critical patent/JPS5849361A/ja
Publication of JPS5940829B2 publication Critical patent/JPS5940829B2/ja
Expired legal-status Critical Current

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)
  • 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)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

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−シアノー Ｎ’−メチルーＮ′−（２−メル
カプトエチル）グアニジンの製法に関すする。
本発明の製法で得られるＮ−シアノー Ｎ ′−メチル
ーＮ’−（２−メルカプトエチル）グアニジンは式：Ｈ
Ｓ−（ＣＨ２）２−ＮＨ−Ｃ’ 〔Ｉ〕＼ で示され、例えば、ヒスタミンＨ２−拮抗剤として知ら
れるＮ−シアノーＮ′−メチルー Ｎ ′ −〔２−（
（５−メチルー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−シアノーＮ
−５−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。なお、後者の場合、Ｎ−シアノジメチルジチ
オイミドカルボネートとメチルアミンとの反応により、
Ｎ−シアノーＮ −５−ジメチルイソチオウレアが生成
する。これは、例えば、ダビツドソン〔Ｄａｖｉｄｓｏ
ｎ、、Ｃｈｅｍｉｓｔｒｙａｎｄｌｎｄｕｓｔｒｙ）ｐ
ｐ１９７７〜１９７８（１９６５）〕によつて報告され
ている。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うる。
式〔１〕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、シメチジンが得られる
。つぎに、実施例および参考例を挙げて本発明をさらに
詳しく説明する。
実施例 システアミン塩酸塩５、６８ｆ７の水２０ｍノ溶液をＮ
−シアノ−Ｎ・Ｓ−ジメチルイソチオウレア６．４６７
のエタノール１００ｍ１懸濁液に加える。
水酸化ナトリウム４．０７の水２０ｍ１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″一（２−メルカプトエチル）グアニ
ジン６．１２ｙを得る。この生成物を特徴づける（確認
する）ため、２・４−ジニトロクロロベンゼン７．７７
の９５％エタノール５０ｍ′溶液をＮ−シアノ−Ｎ′−
メチル−Ｎｌ−（２−メルカプトエチル）グアニジン６
．０ｙ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７．７３ｙを集め、大容量のエー
テルでトリチユレートし、アセトニトリルから再結晶さ
せてＮ−シアノ−Ｎ′−メチルーＮ仁〔Ｓ−（２・４−
ジニトロフエニル）−２メルカプトエチル〕グアニジン
を得る。融点２１０〜２１１℃、元素分析（％）実測値
：Ｃ、４１．０；Ｈｌ３，７；Ｎｌ２６．Ｏ：ＳｌｌＯ
．Ｏ；ＣｌｌＨｌ２Ｎ６Ｏ４Ｓとして理論値：Ｃ、４０
．７；Ｈｌ３．７；Ｎｌ２５．９：Ｓｌ９．９。参考例 窒素雰囲気下、攪拌しながらナトリウム１．４３ｙを乾
燥エタノール１００ｍ１に加える。
ナトリウムが溶解した後、Ｎ−シアノ−Ｎ′−メチル−
Ｎｌ′（２−メルカプトエチル）グアニジン４．９０７
の乾燥エタノール５０ｍ１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５．１８７を室温で１時間を要し、数
回に分けて加える。

Claims (1)

    【特許請求の範囲】
  1. 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。
JP57148483A 1974-09-02 1982-08-25 メルカプトエチル置換グアニジンの製法 Expired JPS5940829B2 (ja)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB38257/74 1974-09-02
GB38257/74A GB1533380A (en) 1974-09-02 1974-09-02 Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines

Publications (2)

Publication Number Publication Date
JPS5849361A JPS5849361A (ja) 1983-03-23
JPS5940829B2 true 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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0373817A (ja) * 1989-08-16 1991-03-28 Shinko Electric Co Ltd 温度計測方法及び装置

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4189488A (en) * 1976-03-11 1980-02-19 Smith Kline & French Laboratories Limited Amidinoformic and amidinosulphinic acids
GB1574214A (en) 1976-03-11 1980-09-03 Smith Kline French Lab Amidines
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
US4165378A (en) 1977-04-20 1979-08-21 Ici Americas Inc. Guanidine derivatives of imidazoles and thiazoles
NZ186965A (en) 1977-04-20 1980-02-21 Ici Ltd Guanidino derivatives and pharmaceutical compositions
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
EP0006679B1 (en) 1978-05-24 1982-07-21 Imperial Chemical Industries 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
CA1140925A (en) * 1978-10-16 1983-02-08 Derrick F. Jones Antisecretory branched chain heterocyclic derivatives, processes for their manufacture and pharmaceutical compositions containing them
CH645098A5 (de) * 1978-11-02 1984-09-14 Pliva Pharm & Chem Works Verfahren zur herstellung von n-cyan-n'-methyl-n''-(2-mercaptoaethyl)guanidin.
US4276421A (en) * 1978-11-18 1981-06-30 Societe De Recherches Et De Syntheses Organiques S.A. Cyano-guanidine geometrical isomers
EP0014057B1 (en) 1979-01-18 1985-01-02 Imperial Chemical Industries Plc Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them
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
JPS57120574A (en) * 1981-01-21 1982-07-27 Fujimoto Seiyaku Kk Production of guanidine derivative
JPS57120572A (en) * 1981-01-21 1982-07-27 Fujimoto Seiyaku Kk Guanidine derivative and its preparation
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
JPH0655711B2 (ja) * 1986-09-12 1994-07-27 三井石油化学工業株式会社 シアノグアニジン誘導体の製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0373817A (ja) * 1989-08-16 1991-03-28 Shinko Electric Co Ltd 温度計測方法及び装置

Also Published As

Publication number Publication date
JPS5849361A (ja) 1983-03-23
CH608232A5 (ja) 1978-12-29
US4013678A (en) 1977-03-22
JPS635389B2 (ja) 1988-02-03
BE832663A (fr) 1976-02-23
JPS51125074A (en) 1976-11-01
GB1533380A (en) 1978-11-22
NL7510344A (nl) 1976-03-04
IE41856L (en) 1976-03-02
IE41856B1 (en) 1980-04-09
CA1063119A (en) 1979-09-25

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