Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
1998-06-08
2001-10-02
Killos, Paul J. (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C560S255000, C564S222000, C564S308000, C564S428000, C552S008000, C568S327000, C568S808000, C514S530000, C514S621000
Reexamination Certificate
active
06297399
ABSTRACT:
The invention relates to indane compounds, processes for their production, compositions containing them and their pharmacological use.
According to the invention there is provided a compound of any of the formulae:
wherein
in Formula 7 R
2
to R
13
in Formula 8 R
1
and R
3
to R
13
are selected from one or more of the same or different of:
H, halo, hydroxy, alkoxy, aryloxy, acetoxy, carboxy, alkyl carbonyl, hydro carbonyl, amino, amido, alkylamino, hydroxylamino, amine oxide groups, azo groups, cyano, hydrazino groups, hydrazide groups, hydrazone groups, imide groups, iminoether groups, ureyl groups, oxime, nitro, nitrate, nitrite, nitroso groups, nitrile, heterocyclic groups containing hetero atoms selected from one or more of N, O or S, aralkyl groups, mono and polybenzoid aryl groups, substituted aryl groups, thiol, thioureyl, phenylthiol groups, sulphonic acid groups, sulphoxide gruops, sulphone groups, alkyl containing 1 to 10 carbon atoms or cycloalkyl groups containing 3 to 8 carbon atoms which may be saturated or unsaturated, substituted alkyl or cycloalkyl groups which may be saturated or unsaturated
X is a bond, O, or NR (wherein R is acyl, alkyl or sulphonate groups), S, SO or SO
2
when X is a bond any of: R
8
and R
13
; R
8
and R
12
; or R
8
and R
9
may together represent a double bond
in formula 7 any one or more of R
2
,
1
R
2
R
3
,
1
R
3
; R
9
,
1
R
9
; R
10
,
1
R
10
; R
11
,
1
R
11
; R
12
,
1
R
12
may together represent oxo, and
in formula 8 any one or more of R
1
,
1
R
1
; R
3
,
1
R
3
; R
9
,
1
R
9
; R
10
,
1
R
10
; R
11
,
1
R
11
; R
12
,
1
R
12
may together represent oxo
pharmacologically acceptable salts, esters, amides, solvates and isomers thereof.
In one embodiment of the invention the alkyl or cycloalkyl are substituted with one or more of the same or different of halo, oxo, hydroxy, alkoxy, aryloxy, acetoxy, carboxy, carbonyl, amino, amido, alkylamino, hydroxyamino, amine oxide groups, azo groups, cyano, hydrazino groups, hydrazide groups, hydrazone groups, imide groups, imino ether groups, ureyl groups, oxime, nitro, nitrate, nitrite, nitroso groups, nitrile, heterocyclic groups, aralkyl groups, mono and polybenzoid aryl groups, substituted aryl groups, thiol, thioureyl, phenyl thiol groups, sulphonic acid groups, sulphoxide groups and sulphone groups.
In one embodiment of the invention the heterocyclic groups are selected from herteroatoms containing one or more of N, O or S.
In Formula 7 preferably R
4
to R
7
and preferably R
10
and R
11
represent hydrogen.
In Formula 7 preferred particularly because of pharmacological activity as mast cell stabilisers are those compounds in which:
R
2,
1
R
2
represent H, OH;
X is a bond;
R
13
is benzyl; and
R
8
and R
9
or R
8
and R
12
together represent a double bond;
or R
3
,
1
R
3
together represent O; and
X is NR wherein R is alkyl.
In Formula 7 preferred particularly because of pharmacological activity as anti-inflammatory agents are those compounds in which:
X represents a double bond; and
R
2
,
1
R
2
together represent O;
or X is NR wherein R is acyl and R
3
,
1
R
3
togetheer represent O.
In Formula 8 preferably R
4
to R
7
and preferably R
11
and R
12
represent hydrogen.
In Formula 8 preferred particularly because of pharmacological activity as mast cell stabilisers are those compounds in which:
R
1
,
1
R
1
represent H, OH.
X is a bond;
R
13
is benzyl; and
R
8
and R
9
or R
8
and R
12
together represent a double bond
or R
1
,
1
R
1
together represent O; and
X is NR wherein R is alkyl.
In Formula 8 preferred particularly because of pharmacological activity as antiinflammatory agents are those compounds in which:
X represents a double bond; and
R
1
,
1
R
1
together represent O
or X is NR wherein R is acyl; and
R
1
,
1
R
1
together represent O.
In invention relates to the compounds above for use particularly as smooth muscle relaxants and/or as mast cell stabilising agents and/or as anti-inflammatory agents.
The invention also relates to pharmaceutical compositions containing the compounds and to their use in methods of prophylaxis or treatment particularly to achieve smooth muscle relaxant activity and/or mast cell stabilising activity and/or anti-inflammatory activity.
The invention also relates to the compounds per se given in Appendix 2.
The invention also provides various processes for preparing the indane compounds as outlines in the Claims. These processes are described in more detail below.
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Byrne William
Frankish Neil
Sheridan Helen
Walsh John
Jacobson Price Holman & Stern PLLC
Killos Paul J.
Venantius Limited
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