Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ketone doai
Reexamination Certificate
1998-06-08
2001-10-09
Padmanabhan, Sreeni (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ketone doai
C514S691000, C514S765000, C568S309000, C568S326000, C568S330000, C568S327000, C568S715000, C568S813000, C585S027000, C585S420000
Reexamination Certificate
active
06300376
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 pharmaceutical composition comprising a compound of any of the formulae:
wherein
in Formulae 1 and 3
R
1
and R
3
to R
15
in Formulae 2 and 4
R
2
to R
15
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 and/or S, aralkyl groups, mono and polybenzoid aryl groups, substituted aryl groups, thiol, thioureyl, phenylthiol groups, sulphonic acid groups, sulphoxide groups, 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 akyl or cycloalkyl groups which may be saturated or unsaturated
in Formulae 1 and 4
any of: R
8
and R
15
; or R
8
and R
9
may together represent a double bond
in Formulae 2 and 3
any of: R
8
and R
15
; or R
8
and R
9
; or R
8
and R
14
may together represent a double bond
in Formula 1
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
may together represent oxo;
in Formula 2
any one or more of R
2
,
1
R
2
; R
3
,
1
R
3
; R
9
,
1
R
9
; R
14
,
1
R
14
; may together represent oxo;
in Formula 3
any one or more of R
1
,
1
R
1
; R
3
,
1
R
3
; R
9
,
1
R
9
; R
14
,
1
R
14
; may together represent oxo;
in Formula 4
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
; may together represent oxo;
pharmacogically acceptable salts, esters, amides, solvates and isomers thereof.
The invention also provides compounds of Formulae 1 to 4 per se as defined above.
In Formula 1
R
1
,
1
R
1
, R
3
,
1
R
3
; and R
10
,
1
R
10
do not all together represent oxo.
In Formula 2
R
3
,
1
R
3
; R
9
,
1
R
9
; and R
14
,
1
R
14
do not all together represent oxo.
In Formula 3
any three or all four of R
1
,
1
R
1
; R
3
,
1
R
3
,
1
R
9
1
R
9
; and R
14
,
1
R
14
do not together represent oxo.
In Formula 4
any three or all four of R
1
,
1
R
1
; R
3
,
1
R
3
; R
9
,
1
R
9
; and R
14
,
1
R
14
do not together represent oxo.
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 heteroatoms containing one or more of N, O or S.
Preferably in Formula 1 R
3
to R
7
and preferably also R
10
to R
14
are hydrogen.
In Formula 1 preferred particularly because of pharmacological activity as mast cell stabilisers are those compounds in which:
R
8
and R
9
together represent a double bond;
R
1
,
1
R
1
represent H, OH; and
R
15
is benzyl.
Preferably in Formula 2 R
3
to R
7
and also preferably R
10
to R
13
are hydrogen.
In Formula 2 preferred particularly because of pharmacological activity as mast cell stablilisers are those compounds in which:
R
8
and R
9
or R
8
and R
14
together represent a double bond;
R
2
,
1
R
2
represent H, OH; and
R
15
is benzyl.
Preferably in Formula 3 R
4
to R
7
and preferably also R
10
to R
13
represent hydrogen.
In Formula 3 preferred particularly because of pharmacological activity as mast cell stabilisers and for anti-inflammatory activity are those compounds in which:
R
8
and R
9
or R
8
and R
14
together represent a double bond;
R
1
,
1
R
1
represents H, OH; and
R
15
is benzyl.
Preferably in Formula 4 R
4
to R
7
and also preferably R
10
to R
14
represent hydrogen.
The invention relates to the compounds above for use as smooth muscle relaxants and/or as mast cell stabilising agents and/or as anti-inflammatory agents.
The invention also relates to the use of the compounds 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.
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Byrne William
Farrell Ronan
Frankish Neil
Sheridan Helen
Walsh John
Jacobson & Holman PLLC
Padmanabhan Sreeni
Venantius Limited
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