WO1982000462A1 - Imino-alkyl and amino-nitrile cyano-guanidines - Google Patents

Imino-alkyl and amino-nitrile cyano-guanidines Download PDF

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Publication number
WO1982000462A1
WO1982000462A1 PCT/CH1981/000090 CH8100090W WO8200462A1 WO 1982000462 A1 WO1982000462 A1 WO 1982000462A1 CH 8100090 W CH8100090 W CH 8100090W WO 8200462 A1 WO8200462 A1 WO 8200462A1
Authority
WO
WIPO (PCT)
Prior art keywords
imino
methyl
cyano
ethyl
acid
Prior art date
Application number
PCT/CH1981/000090
Other languages
English (en)
French (fr)
Inventor
Syntheses Organiques Sa Rech
Original Assignee
Rech Syntheses Organ
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 filed Critical Rech Syntheses Organ
Publication of WO1982000462A1 publication Critical patent/WO1982000462A1/en

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Classifications

    • 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
    • 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
    • C07D277/32—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 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen 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
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Definitions

  • the imino-alkyl and amino-nitrile cyano-guanidines claimed in application no. 1 404 / 79-7 and in the present application are not in equilibrium with the corresponding stable imino-nitrile and amino-alkyl cyano-guanidines.
  • our invention which makes it possible to obtain irreversibly, by a new reaction of organic chemistry and for the first time described in Swiss application No.
  • cyano-guanidines iminoalkyl and amino -nitrile basic by their guanidine function from cyano-guanidine imino-nitrile and amino-neutral alkyl function-Spar their guanidine function, we have prepared the following four new guanidines:
  • guanidines have a structure allowing a higher gastric anti-secretory activity (volume of secretion and gastric acidity) higher than the same activity of the cyano-guanidines imino-nitrile and amino-alkyl already known. In addition, their toxicity (anti-androgenic effect and prolactin effect) is significantly reduced.
  • R 1 -N ⁇ -NHCN NHCH 3 ,
  • Said compounds of the invention and their therapeutically suitable salts can be used for the treatment of gastric and duodenal ulcer.
  • excipients suitable for their pharmaceutical applications are, for example. lactose, sucrose, talc, gelatin, gum arabic, olive oil.
  • Example 3 N-methyl-N'-cyano-N '' - imino- [2 - ((5-dimethylamino-methyl-2-furanyl) -methylthio) -ethyl] -guanidine.dichlorhydrate. It is brought to reflux 21 ⁇ 2 h. a solution in ethanol containing 32.5 ml of HCl, 1 N, of 4.3 g of N-methyl-N'-iraino-cyano- N'- '2- ((5-dimethylamino-raethyl-2 -furanyl) -methylthto) -ethyl -guanidine. The solvent is evaporated off under reduced pressure; the residue, as oil, is dissolved in raethanol and the solvent is again evaporated; the residual oil is subjected to the vacuum 0.05 T, 3 hours,

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
PCT/CH1981/000090 1980-08-11 1981-08-10 Imino-alkyl and amino-nitrile cyano-guanidines WO1982000462A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH6049/80800811 1980-08-11
CH604980 1980-08-11

Publications (1)

Publication Number Publication Date
WO1982000462A1 true WO1982000462A1 (en) 1982-02-18

Family

ID=4303404

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH1981/000090 WO1982000462A1 (en) 1980-08-11 1981-08-10 Imino-alkyl and amino-nitrile cyano-guanidines

Country Status (3)

Country Link
EP (1) EP0057227A1 (ja)
JP (1) JPS57501379A (ja)
WO (1) WO1982000462A1 (ja)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4196793A1 (en) 2020-08-11 2023-06-21 Université de Strasbourg H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2387970A1 (fr) * 1977-04-20 1978-11-17 Ici Ltd Derives de la guanidine et medicament en contenant
EP0010893A1 (en) * 1978-10-16 1980-05-14 Imperial Chemical Industries Plc Antisecretory branched-chain heterocyclic guanidine derivatives, processes for their manufacture, intermediates, and pharmaceutical compositions containing said derivatives
EP0030092A1 (en) * 1979-11-13 1981-06-10 Imperial Chemical Industries Plc Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2387970A1 (fr) * 1977-04-20 1978-11-17 Ici Ltd Derives de la guanidine et medicament en contenant
EP0010893A1 (en) * 1978-10-16 1980-05-14 Imperial Chemical Industries Plc Antisecretory branched-chain heterocyclic guanidine derivatives, processes for their manufacture, intermediates, and pharmaceutical compositions containing said derivatives
EP0030092A1 (en) * 1979-11-13 1981-06-10 Imperial Chemical Industries Plc Guanidine derivatives, processes for their manufacture and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
EP0057227A1 (fr) 1982-08-11
JPS57501379A (ja) 1982-08-05

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