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US 5,476,867 AGranted
Pharmaceutical compositions
AssigneeBritish Technology Group Limited
InventorsEdward A. Boyd, Brenda Costall, Mary E. Kelly, Philip J. Parsons
Life of this patent
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AssigneeBritish Technology Group Limited
InventorsEdward A. Boyd, Brenda Costall, Mary E. Kelly, Philip J. Parsons
Estimating the term…
Compounds of formula (I) ##STR1## in which R.sub.1 represents hydrogen, a C.sub.1-6 aliphatic hydrocarbyl group or a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group or by a phenyl group, which phenyl group is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.2 represents hydrogen, R.sub.3 represents hydrogen, a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur which is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is hydrogen, a phenyl group or a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur, which phenyl or heterocyclyl group R is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.4 and R.sub.5 each represent hydrogen or together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, or R.sub.4 represents hydrogen and two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 together represent the second bond of a double bond joining positions 4 and 5, 5 and 6 or 6 and 7 with the remaining two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 representing hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid, are of value for the treatment of anxiety and in the improvement of learning and/or the reversal of amnesia.
A compound of formula (I) ##STR6## in which R.sub.1 represents a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group or by a phenyl group, which phenyl group is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.2 represents hydrogen, R.sub.3 represents hydrogen, a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur which is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is hydrogen, a phenyl group or a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur, which phenyl or heterocyclyl group R is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.4 and R.sub.5 each represent hydrogen or together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, or R.sub.4 represents hydrogen and two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 together represent the second bond of a double bond joining positions 4 and 5, 5 and 5 or 6 and 7 with the remaining two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 representing hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
A compound of formula (I) ##STR7## in which R.sub.1 represents hydrogen, a C.sub.1-6 aliphatic hydrocarbyl group or a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group or by a phenyl group, which phenyl group is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.2 represents hydrogen, R.sub.3 represents a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur which is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is a phenyl group or a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur, which phenyl or heterocyclyl group R is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.4 and R.sub.5 each represent hydrogen or together represent an oxo group and R.sub.6, R.sub.7 and R.sub. 8 each represent hydrogen, or R.sub.4 represents hydrogen and two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 together represent the second bond of a double bond joining positions 4 and 5, 5 and 5 or 6 and 7 with the remaining two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 representing hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
A compound of formula (I) ##STR8## in which R.sub.1 represents hydrogen, a C.sub.1-6 aliphatic hydrocarbyl group or a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group or by a phenyl group, which phenyl group is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.2 represents hydrogen, R.sub.3 represents hydrogen, a 5-or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur which is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is hydrogen, a phenyl group or a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur, which phenyl or heterocyclyl group R is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.4 and R.sub.5 together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
A compound of formula (I) ##STR9## in which R.sub.1 represents a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group, R.sub.2 represents hydrogen, R.sub.3 represents hydrogen, or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is hydrogen, a phenyl group which is unsubstituted or substituted by a trifluoromethyl group, R.sub.4 and R.sub.5 each represent hydrogen or together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, or R.sub.4 represents hydrogen and two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 together represent the second bond of a double bond joining positions 4 and 5, 5 and 6 or 6 and 7 with the remaining two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 representing hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
A compound of formula (I) ##STR10## in which R.sub.1 represents hydrogen, a C.sub.1-6 aliphatic hydrocarbyl group or a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group, R.sub.2 represents hydrogen, R.sub.3 represents a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is a phenyl group which is unsubstituted or substituted by a trifluoromethyl group, R.sub.4 and R.sub.5 each represent hydrogen or together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, or R.sub.4 represents hydrogen and two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 together represent the second bond of a double bond joining positions 4 and 5, 5 and 6 or 6 and 7 with the remaining two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 representing hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
A compound of formula (I) ##STR11## in which R.sub.1 represents hydrogen, a C.sub.1-6 aliphatic hydrocarbyl group or a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group, R.sub.2 represents hydrogen, R.sub.3 represents hydrogen or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is hydrogen or a phenyl group which is unsubstituted or substituted by a trifluoromethyl group, R.sub.4 and R.sub.5 together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
A compound according to claim. 6, in which a group R.sub.3 which is not hydrogen is in the trans configuration relative to the hydrogen atoms at positions 3a and 7a.
A method of treatment of a patient suffering from anxiety which comprises administering to said patient a therapeutically effective amount of a compound of formula (I) ##STR12## in which R.sub.1 represents hydrogen, a C.sub.1-6 aliphatic hydrocarbyl group or a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group or by a phenyl group, which phenyl group is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.2 represents hydrogen, R.sub.3 represents hydrogen, a 5-or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur which is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is hydrogen, a phenyl group or a 5- or 6-membered ring aromatic heterocyclyl group containing one or two heteroatoms selected from nitrogen, oxygen and sulphur, which phenyl or heterocyclyl group R is unsubstituted or substituted by a halogeno or C.sub.1-3 halogenoalkyl group, R.sub.4 and R.sub.5 each represent hydrogen or together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, or R.sub.4 represents hydrogen and two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 together represent the second bond of a double bond joining positions 4 and 5, 5 and 5 or 6 and 7 with the remaining two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 representing hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
A method for the treatment of a patient suffering from anxiety which comprises administering to said patient a therapeutically effective amount of a compound of the formula (I) ##STR13## in which R.sub.1 represents hydrogen, a C.sub.1-6 aliphatic hydrocarbyl group or a C.sub.1-4 aliphatic hydrocarbyl group substituted by a C.sub.3-6 alicyclic hydrocarbyl group, R.sub.2 represents hydrogen, R.sub.3 represents hydrogen or a group AR wherein A is a straight chain C.sub.1-4 aliphatic hydrocarbyl group terminally substituted by R which is hydrogen or a phenyl group which is unsubstituted or substituted by a trifluoromethyl group, R.sub.4 and R.sub.5 each represent hydrogen or together represent an oxo group and R.sub.6, R.sub.7 and R.sub.8 each represent hydrogen, or R.sub.4 represents hydrogen and two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 together represent the second bond of a double bond joining positions 4 and 5, 5 and 5 or 6 and 7 with the remaining two of R.sub.5, R.sub.6, R.sub.7 and R.sub.8 representing hydrogen, the compound optionally being in the form of a salt thereof formed with a physiologically acceptable inorganic or organic acid.
Dependencies are inferred from the claim text.