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AssigneeHoffmann-La Roche Inc.
InventorsCedric Herbert Hassall, William Henry Johnson, Antonin Krohn, Carey Ernest Smithen, William Anthony Thomas
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This invention is directed toward pharmacologically active compounds of the formula ##STR1## wherein A represents a nitrogen atom which may be substituted by a methyl, cyclopropylmethyl, di(C.sub.1-4 alkyl)aminoethyl, methoxymethyl or hydroxyethyl group and B represents a carbonyl group or A and B together represent a grouping of the formula ##STR2## in which R.sup.a represents a hydrogen atom or a lower alkyl or hydroxymethyl group and X represents a nitrogen atom or C-R.sup.b wherein R.sup.b represents a hydrogen atom or a lower alkyl or hydroxymethyl group; R represents a halogen atom or a nitro or trifluoromethyl group; R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents an acyl group derived from a naturally occurring amino acid (all such groups which contain an asymmetric carbon atom having the L- or D,L-configuration) and R.sup.3 represents a phenyl, halophenyl or 2-pyridyl group and acid addition salts thereof. Also provided are methods for their preparation and intermediates thereof. These compounds exhibit activity as anticonvulsants, muscle relaxants and sedatives.
A compound of the general formula ##STR24## wherein R is selected from the group consisting of a halogen atom, nitro and a trifluoromethyl group;
Dependencies are inferred from the claim text.
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From the US filing history. Foreign family members aren’t listed.
Dipeptides: containing heteroatoms different from O, S, or N
Oxygen atoms: ketonic radicals
Substituted in position 2 by nitrogen, oxygen or sulfur atoms: oxygen atoms
Not condensed with other rings: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Term ended 6 Sep 1994 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
The present invention is concerned with substituted phenyl ketones and a process for the manufacture thereof.
The substituted phenyl ketones provided by the present invention are compounds of the general formula ##STR3## wherein A represents a nitrogen atom which may be substituted by a methyl, cyclopropylmethyl, di(C.sub.1-4 alkyl)aminoethyl, methoxymethyl or hydroxyethyl group and B represents a carbonyl group or A and B together represent a grouping of the formula ##STR4## in which R.sup.a represents a hydrogen atom or a lower alkyl or hydroxymethyl group and X represents a nitrogen atom or C--R.sup.b wherein R.sup.b represents a hydrogen atom or a lower alkyl or hydroxymethyl group; R represents a halogen atom or a nitro or trifluoromethyl group; R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents an acyl group derived from a naturally occurring amino acid (all such groups which contain an asymmetric carbon atom having the L- or D,L-configuration) and R.sup.3 represents a phenyl, halophenyl or 2-pyridyl group and acid addition salts thereof.
It will be appreciated that formula I hereinbefore embraces compounds of the general formulae ##STR5## wherein R, R.sup.1, R.sup.2, R.sup.3, R.sup.a and R.sup.b have the significance given earlier and R.sup.4 represents a hydrogen atom or a methyl, cyclopropylmethyl, di(C.sub.1-4 alkyl)aminoethyl, methoxymethyl or hydroxyethyl group.
A. The Preparation of the Starting Material
i. 100 g. of 7-bromo-1,3-dihydro-5-(2-pyridyl)-2H-1,4-benzodiazepin-2-one were dissolved in 750 ml. of 2-N hydrochloric acid and left at room temperature overnight. The solution was evaporated to an oil which was dissolved in water and re-evaporated. The final traces of water were removed by shaking the oil with 50% methanol/toluene followed by evaporation. This treatment was repeated three times with 50% methanol/toluene and twice with toluene. There was obtained a pale-yellow to orange solid which was dried at 50.degree. C. under a vacuum. The product was characterised by its spectral data and was shown by titration to contain 2.5 moles of hydrogen chloride to one mole of 2-amino-N--(4-bromo-2-picolinoylphenyl)acetamide (133.5 g; 99%). After prolonged drying over sodium hydroxide, there was obtained an analytical sample which was stoichiometric.
Analysis for C.sub.14 H.sub.14 BrCl.sub.2 N.sub.3 O.sub.2 (407.11): Calculated: C: 41.31, H: 3.47; N: 10.32; Br: 19.63; Cl: 17.42 Found: C: 41.02; H: 3.61; N: 10.11; Br: 20.08; Cl: 17.82.