Disubstituted azabicycloalkanes
AssigneeScience Union et Cie
InventorsLaszlo Beregi, Pierre Hugon, Xavier Pascaud, Jean-Claude Poignant
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AssigneeScience Union et Cie
InventorsLaszlo Beregi, Pierre Hugon, Xavier Pascaud, Jean-Claude Poignant
Estimating the term…
Disubstituted azabicycloalkanes of the formula ##STR1## wherein: N IS 0, 1 OR 2 R is saturated or unsaturated straight or branched (C.sub.1 -C.sub.5) aliphatic hydrocarbon, and X.sub.1, x.sub.2, x.sub.3, x.sub.4, x.sub.5, which are the same or different, are hydrogen, halogen, hydroxy, lower alkyl, lower alkoxy, trifluoromethyl, nitro, amino or sulfamoyl. These compounds are used as medicine especially in the treatment of gastroduodenal ulcers, gastric hypersecretion, nauseous syndromes of central origin and hypertension.
A compound selected from the group consisting of:
Dependencies are inferred from the claim text.
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From the US filing history. Foreign family members aren’t listed.
Condensed with one carbocyclic ring: condensed with a ring other than six-membered
Condensed with one carbocyclic ring: iso-indoles; Hydrogenated iso-indoles
Heterocyclic compounds
Term ended 13 Sep 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The present invention provides disubstituted azabicycloalkanes of the general formula I: ##STR2## wherein : N IS SELECTED FROM 0, 1 AND 2 ;
R is selected from the group consisting of saturated and unsaturated aliphatic hydrocarbon radical having from 1 to 5 carbon atoms inclusive in straight and branched chain and,
X.sub.1, x.sub.2, x.sub.3, x.sub.4, and X.sub.5, which are the same or different, are each selected from the group consisting of a hydrogen atom, halogen atoms, a hydroxy radical, alkyl and alkoxy radicals, each having from 1 to 5carbon atoms inclusive, trifluoromethyl, nitro, amino and sulfamoyl radicals.
N-ethyl-2-(2-methoxy-5-sulfamoyl benzamido methyl)-3-azabicyclo (3,3,0) octane ##STR10##
57.6 parts of sodium hydride at 50% (1.2 mole) in paraffine were introduced in 1500 parts of anhydrous xylene. To this suspension there was added portionwise in the course of 1 hour at room temperature, a solution of 150 parts (1.2 mole) of 3-azabicyclo (3,3,0)-2-octanone in 600 parts of anhydrous xylene. The mixture was refluxed for 45 minutes. After cooling, 187 parts (1.2 mole) of ethyl iodide were added in 30 minutes, then the reaction mixture was heated for 1 hour at 110.degree. C. After cooling, 400 parts of water were added. The organic layer separated and dried over anhydrous magnesium sulfate was concentrated in vacuo. Upon distillation, there were obtained 95,5 parts of N-ethyl-3-azabicyclo (3,3,0)-2-octanone B.P./0.2 mmHg = 76.degree.-79.degree. C n.sub.D.sup.25 = 1.4872.
After extraction of the aqueous layer with 500 parts of chloroform, followed by drying concentration, the distillation gave another 46 parts of N-ethyl-3-azabicyclo (3,3,0)-2-octanone, having the same B.P. and n.sub.D.sup.25 than the product obtained from the organic layer.