Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-07-25
2002-09-17
Bernhardt, Emily (Department: 1824)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S232800, C544S115000, C544S234000
Reexamination Certificate
active
06451795
ABSTRACT:
A subject-matter of the present invention is compounds of general formula (I)
in which
X represents a hydrogen or halogen atom,
Y represents one or more atoms or groups chosen from hydrogen, halogens and methyl, methoxy and nitro groups, R
1
represents a (C
1
-C
4
) alkyl group, R
2
and R
3
each represent, independently of one another, a hydrogen atom or a (C
1
-C
4
) alkyl group or else R
2
and R
3
form, with the nitrogen atom which carries them, a pyrrolidinyl, piperidinyl or morpholinyl group.
The preferred compounds are those in the general formula of which X represents a halogen atom, Y represents a hydrogen atom or a halogen atom, R
1
represents a methyl group, R
2
represents a hydrogen atom or a methyl group and R
3
represents a methyl group or else R
2
and R
3
form, with the nitrogen atom which carries them, a pyrrolidinyl ring.
The compounds of general formula (I) can be prepared by processes illustrated by the following scheme:
According to this scheme, a compound of general formula (II), in which X is as defined above and R′ represents a C
1
-C
4
) alkyl group, is subjected to an alkylation reaction with a halide of general formula HalR
1
, in which R
1
is as defined above, to result in a compound of general formula (III). This compound is subsequently reacted with a chlorooxoacetate of general formula ClCOCO
2
R″, in which R″ represents a (C
1
-C
4
) alkyl group, in a polar aprotic solvent, such as dichloroethane, at room temperature, in the presence of a Lewis acid, for example titanium tetrachloride, in order to obtain the diester of general formula (IV). The latter is subsequently treated in acetic acid, first at room temperature and then at the reflux temperature, with a phenylhydrazine optionally substituted by a Y group as defined above, in order to obtain an ester of general formula (V). Finally, this ester is converted to the secondary or tertiary amide of general formula (I) by the action of an amine of general formula HNR
2
R
3
, in which R
2
and R
3
are as defined above, for example in the presence of a trialkylaluminium derivative in a solvent such as toluene.
The starting compounds of general formula (II) are known to a person skilled in the art. By way of indication, mention will be made of the formation of 6-chloroindole-2-carboxylic acid derivatives according to Rydon et al.,
J. Chem. Soc
(1955), 3499.
The examples which will follow illustrate the preparation of some compounds according to the invention. The elemental microanalyses and the I.R. and N.M.R. spectra confirm the structures of the compounds obtained.
The numbers shown between brackets in the titles of the examples correspond to those in the 1
st
column of the table given later.
In the names of the compounds, the dash “-” forms part of the word and the dash “-” is only used for the break at the line end; it is to be omitted in the absence of a break and must not be replaced either by a normal dash or by a space.
REFERENCES:
patent: 98/15552 (1998-04-01), None
patent: 99/06406 (1999-02-01), None
Derwent Abstract 1998-240772 for WO 98/15552.
Derwant Abstract 1999-153682 for WO 99/06406.
Bartsch-Li Régine
Froissant Jacques
Marabout Benoît
Marguet Frank
Sevrin Mireille
Alexander Michael D.
Bernhardt Emily
Dupont Paul E.
Sanofi-Synthelabo
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