WO1981000255A1 - Imino-alkyle et amino-nitrile cyano-guanidines - Google Patents

Imino-alkyle et amino-nitrile cyano-guanidines Download PDF

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Publication number
WO1981000255A1
WO1981000255A1 PCT/CH1980/000087 CH8000087W WO8100255A1 WO 1981000255 A1 WO1981000255 A1 WO 1981000255A1 CH 8000087 W CH8000087 W CH 8000087W WO 8100255 A1 WO8100255 A1 WO 8100255A1
Authority
WO
WIPO (PCT)
Prior art keywords
methyl
cyano
imino
par
guanidine
Prior art date
Application number
PCT/CH1980/000087
Other languages
German (de)
English (en)
Inventor
P Baudet
Original Assignee
Rech Syntheses Organ
P Baudet
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 Rech Syntheses Organ, P Baudet filed Critical Rech Syntheses Organ
Publication of WO1981000255A1 publication Critical patent/WO1981000255A1/fr

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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
    • C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
    • C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Definitions

  • La stabilite molecule des cyano-guanidines des Formules A 1 ),A 2 ) and A 3 ) reside ( 1 ) in the basicite de the function imino-alkyle de la guanidine, celle-çi supplier des sels stables, comme cniorliydrate par ex . ; ( 2 ) La. Stabilite molé Diagram des cyano-guanidines of the Formule A, reside in an interaction of the amino-nitrile function with the possibility of the imino-alkyl function, as the interior of a plane structure. This interaction120e a diminution considerable du moment di coins de latreatment NHO ⁇ N, diminution quezelt la disparition de l'absorption infra-rouge de cetterent.
  • the fixation de in configuration iminoalkyle et amino-nitrile is realized by the transformation de la N ethyl-N'-imino-cyano-N'-(2-hydroxy-ethyl)-guanidine par ex, qui apres formation d'un ester intermediaire comme par ex.un methane-sulfonate aboutit par cyclization ä uneéthylene-imine. This cyclization is accompanied by the displacement of the double liaison of imino-nitrile and iminométhyle. If the isomerization is irreversible, it is adopt that the actual sterility does not depend on the possibility of the cyclization. C'est pour la premiere press que cette transformation est decrite.
  • Confor mement aux structures s tabl es des cyano-guanidines de la formula A 1 , la N-imino-methyl-N'-cyano-N''-[2-((4-methyle-5-imidazolyl)-methylthio)-ethyl]-guanidine ne presente pas d'absorption infra -rouge de satreatment nitrile.
  • ll est deje gag. composes organicfues possedant unetreatment nitrile, l'absorption infra-rouge de cettetreatment est fortement diminuee en intensite ou absente(RE Kitson et NE Griffith Anal. Chem.24.
  • Le dit compose de l'invention et ses sels therapeutiquement convenables peuvent ötre utilises tnerapeutiqueraent pour lenote de l'ulcere gastrique et duodenal. Les excipients convenables pour la raisc en oeuvre pjarmaceutique thank par ex.le lactose,le saccnarose, ie talc,la gelatine,la gomme arabique, l'huil e d'olive.
  • the base is prepared on part of the chlorine hydrate for the action of the triethylamine in the tetrahydrofuran, on the part of the fitrate for the elimination of the chlorine hydrate of the triethylamine, elle cristallise;F, 100-102°.
  • IR de -C ⁇ X absente en des conforma tions characterisces par les absorptions IR de 2050 et 2150 cm - 1 (from formula A 2 et C)

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cyano-guanidines de formule (FORMULE) dans laquelle (a) R1=H; Rs=-CH2CH2SH et R3=CH3, (b) (FORMULE) (c) R1=H; Rs= (FORMULE) et R3=CH3, et cyano-guanidines de formule: (FORMULE) dans laquelle: (d) R1=H; Rs=-CH2CH2-OH et R3=CH3, (e) R1=H; Rs=-CH2CH2-O-(Alpha)-S-CH3 et R3=CH3, (f) R1=H; Rs=-CH2CH2-O-(Alpha)-S-C2H5 et R3=CH3 et plusieurs procedes de leur preparation respective. Le compose (C) possede une activite antihistaminique.
PCT/CH1980/000087 1979-07-16 1980-07-16 Imino-alkyle et amino-nitrile cyano-guanidines WO1981000255A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH659179 1979-07-16
CH6591/79 1979-07-16

Publications (1)

Publication Number Publication Date
WO1981000255A1 true WO1981000255A1 (fr) 1981-02-05

Family

ID=4311996

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH1980/000087 WO1981000255A1 (fr) 1979-07-16 1980-07-16 Imino-alkyle et amino-nitrile cyano-guanidines

Country Status (2)

Country Link
EP (1) EP0032143A1 (fr)
WO (1) WO1981000255A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0058286A1 (fr) * 1981-02-12 1982-08-25 Société de Recherches et de Synthèses Organiques SA Isomères géométriques de cyano-guanidines et leurs procédés de préparation
WO1983000692A1 (fr) * 1981-08-14 1983-03-03 Baudet, Pierre Sels de l'acide amido-sulfonique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230349922A1 (en) 2020-08-11 2023-11-02 Université De Strasbourg H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1979000466A1 (fr) * 1977-12-30 1979-07-26 Crc Ricerca Chim Procede d'alkylation du 4(5)-mercaptomethyl-imidazole avec des derives d'aziridine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1979000466A1 (fr) * 1977-12-30 1979-07-26 Crc Ricerca Chim Procede d'alkylation du 4(5)-mercaptomethyl-imidazole avec des derives d'aziridine

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0058286A1 (fr) * 1981-02-12 1982-08-25 Société de Recherches et de Synthèses Organiques SA Isomères géométriques de cyano-guanidines et leurs procédés de préparation
WO1983000692A1 (fr) * 1981-08-14 1983-03-03 Baudet, Pierre Sels de l'acide amido-sulfonique
EP0079297A1 (fr) * 1981-08-14 1983-05-18 Société de Recherches et de Synthèses Organiques SA Sels de l'acide amido-sulfonique

Also Published As

Publication number Publication date
EP0032143A1 (fr) 1981-07-22

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