EP0032143A1 - Imino-alkyle et amino-nitrile cyano-guanidines - Google Patents

Imino-alkyle et amino-nitrile cyano-guanidines

Info

Publication number
EP0032143A1
EP0032143A1 EP19800901263 EP80901263A EP0032143A1 EP 0032143 A1 EP0032143 A1 EP 0032143A1 EP 19800901263 EP19800901263 EP 19800901263 EP 80901263 A EP80901263 A EP 80901263A EP 0032143 A1 EP0032143 A1 EP 0032143A1
Authority
EP
European Patent Office
Prior art keywords
methyl
cyano
imino
par
guanidine
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.)
Withdrawn
Application number
EP19800901263
Other languages
German (de)
English (en)
Inventor
Pierre Baudet
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.)
Recherches Et De Syntheses Organiques SA Ste
Original Assignee
Recherches Et De Syntheses Organiques SA Ste
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 Recherches Et De Syntheses Organiques SA Ste filed Critical Recherches Et De Syntheses Organiques SA Ste
Publication of EP0032143A1 publication Critical patent/EP0032143A1/fr
Withdrawn legal-status Critical Current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
    • 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)

Landscapes

  • 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.
EP19800901263 1979-07-16 1981-02-09 Imino-alkyle et amino-nitrile cyano-guanidines Withdrawn EP0032143A1 (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
EP0032143A1 true EP0032143A1 (fr) 1981-07-22

Family

ID=4311996

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19800901263 Withdrawn EP0032143A1 (fr) 1979-07-16 1981-02-09 Imino-alkyle et amino-nitrile cyano-guanidines

Country Status (2)

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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022034121A1 (fr) 2020-08-11 2022-02-17 Université De Strasbourg Bloqueurs de h2 ciblant des macrophages du foie pour la prévention et le traitement d'une maladie du foie et du cancer

Families Citing this family (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
ES514937A0 (es) * 1981-08-14 1983-10-16 Chemistar Sa "procedimiento de preparar derivados del acido sulfamico y similares".

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO784350L (no) * 1977-12-30 1979-07-03 Crc Ricerca Chim Fremgangsmaate til alkylering av 4(5)-merkaptometyl-imidazoler med aziridinderivater

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8100255A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022034121A1 (fr) 2020-08-11 2022-02-17 Université De Strasbourg Bloqueurs de h2 ciblant des macrophages du foie pour la prévention et le traitement d'une maladie du foie et du cancer

Also Published As

Publication number Publication date
WO1981000255A1 (fr) 1981-02-05

Similar Documents

Publication Publication Date Title
JPH11508911A (ja) 新規ファルネシルトランスフェラーゼ阻害剤、それらの製造および該阻害剤を含む医薬組成物
JPH08511777A (ja) 二硫化物
CH622503A5 (en) Processes for the preparation of proline derivatives and of related compounds
EP0124502A2 (fr) Nouveaux conjugués de la vinblastine et de ses dérivés, procédé pour leur préparation et compositions pharmaceutiques contenant ces conjugués
FR2663845A1 (fr) Composition cosmetique reductrice pour permanente contenant un derive d'acide n-(mercapto alkyl) succinamique ou de n-(mercapto alkyl) succinimide, et son utilisation dans un procede de deformation permanente des cheveux.
WO1993003013A1 (fr) Derives d'indoline portant une fonction amidique, leur preparation, les compositions pharmaceutiques en contenant
DE69305492T2 (de) Im intracerebralen bereich verweisende verbindungen und deren anwendung
FR2663633A1 (fr) Nouvelles chalcones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
EP0001193B1 (fr) Amino-acides cycliques, leurs procédés d'obtention et compositions pharmaceutiques les contenant
FR2515182A1 (fr) Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine 1-sulfamique, leur procede de preparation, leur application comme medicaments et les produits intermediaires necessaires a leur preparation
FR2579461A1 (fr) Amides de l'acide para-methoxycinnamique et de l'acide urocanique utilises comme filtres solaires; procedes d'obtention, compositions dermo-pharmaceutiques et cosmetiques les contenant et applications
EP0015038A1 (fr) Composition pharmaceutique comprenant un dérivé de diphénylhydantoine, dérivés mis en oeuvre et leur préparation
CH651018A5 (fr) Dihydroxy-1,8 anthrones-9 substituees en position 10 et compositions destinees a la medecine humaine ou veterinaire et a la cosmetique les contenant.
EP0465369B1 (fr) Nouveaux dérivés N-substitués d'alpha-mercapto alkylamines, leur procédé de préparation et les intermédiaires obtenus, leur application à titre de médicaments et les compositions les renfermant
CA2264985C (fr) Derives de l'acide 6,8-dimercarptooctanoique substitues en 6-s et/ou 8-s par le radical (3-methylthiopropanoyl) et compositions pharmaceutiques destinees au traitement de tumeurs cancereuses
CA1334850C (fr) Derives d'ureylene triamino-2,4,6 pyrimidine oxyde-3, leur preparation et leur utilisation en cosmetique et dermopharmacie
EP0032143A1 (fr) Imino-alkyle et amino-nitrile cyano-guanidines
FR2560195A1 (fr) Derives d'alanyl-proline, leur procede de preparation et leurs applications pharmaceutiques
FR2594332A1 (fr) Derives d'acides amino-benzoiques, d'acides hydroxy-benzoiques, d'acides cinnamiques, d'acide urocanique et de benzimidazole presentant ou non un groupement d'acide amine absorbant les uvb et/ou les uva et permettant d'eviter les photodermatoses, chez l'homme, consecutives a l'administration de medicaments, a l'emploi de cosmetiques parfumes ou de parfums
FR2556721A1 (fr) Nouveaux derives de o-mercaptopropanamide d'o amino-acides, leur procede de preparation, leur application comme medicaments et les compositions les renfermant
FR2658195A1 (fr) Nouveaux derives de la 20, 21-dinoreburnamenine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et les compositions les renfermant.
EP0022017B1 (fr) Nouveaux dérivés de benzoyl-2 nitro-4 anilides, leur préparation et leur application en tant que médicaments
FI93442C (fi) Menetelmä uusien kysteiinijohdannaisten valmistamiseksi
FR2525221A1 (fr) Derives du furanne et sels d'addition de ces derives, leurs procedes de preparation et leurs applications en therapeutique
FR2516509A1 (fr) Derives benzylideniques, leur preparation et leur application en therapeutique

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT DE FR GB NL SE

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 19810728

RIN1 Information on inventor provided before grant (corrected)

Inventor name: BAUDET, PIERRE