Imide derivatives, their production and use

Claim 2

A compound of the formula: wherein A is a carbonyl group or a sulfonyl group; B is either one of the formulas: (in which R, and R 2 are each a hydrogen atom, or either one of them is a hydrogen atom and the other is a hydroxyl group, a C 1 -C 5 alkyl group or a C 2 -C 6 alkanoyloxy group, or R, and R 2 are combined together to represent an oxo group, E is a methylene group, an ethylene group or an oxygen atom and the full line accompanying a broken line (-----) indicates a single bond or a double bond), (in which F is a methylene group or an ethylene group and R 1 , R 2 and the full line accompanying a broken line (-----) are each as defined above), (in which R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each a hydrogen atom or a C 1 -C 5 alkyl group and R 1 , R 2 and the full line accompanying a broken line (-----) are each as defined above), (in which R 9 and R 10 are each a C 1 -C 5 alkyl group), or (in which R 11 and R 12 are each a C 1 -C 5 alkyl group, or they are combined together to form a C 3 -C 5 alkylene group and n is an integer of 0, 1 or 2) when A represents a carbonyl group, or B is a 1.2-phenylene group when A represents a sulfonyl group; W is a C 1 -C 6 alkylene group, a C 2 -C 6 alkenylene group, a C 2 -C 6 alkynylene group or a C 2 -C 6 alkylene group substituted with hydroxyl; and G is a hydrogen atom, a C 1 -C 5 alkyl group, a C 1 -C 5 alkoxy group, a halogen atom or a hydroxyl group, or its pharmaceutically acceptable salt.

Claim 3

The compound according to claim 1, wherein A is a carbonyl group and B is a group of the formula: (in which R 1 and R 2 are each as defined in claim 1), or its pharmaceutically acceptable salt.

Claim 4

The compound according to claim 1, wherein A is a carbonyl group and B is a group of the formula: (in which F, R, and R 2 are each as defined in claim 1), or its pharmaceutically acceptable salt.

Claim 5

The compound according to claim 1, wherein A is a carbonyl group and B is a group of the formula: (in which R 3 , R 4 , Rs, Rs, R 7 and R 8 are each as defined in claim 1), or its pharmaceutically acceptable salt.

Claim 6

The compound according to claim 1, wherein A is a carbonyl group and B is a group of the formula: (in which R s and R 1 are each as defined in claim 1), or its pharmaceutically acceptable salt.

Claim 7

The compound according to claim 1, wherein A is a carbonyl group and B is a group of the formula: (in which R 11 , R 12 and n are each as defined in claim 1), or its pharmaceutically acceptable salt.

Claim 8

The compound according to claim 1, wherein A is a sulfonyl group and B is a 1,2-phenylene group. or its pharmaceutically acceptable salt.

Claim 9

The compound according to claim 1, wherein W is -(CH 2 ) 4 -, -CH 2 CH=CHCH 2 -, -CH 2 C≡CCH 2 -, -CH 2 CH(OH)CH 2 CH 2 -or -CH 2 CH 2 CH(OH)CH 2 - and G is a hydrogen atom, a C 1 -C 5 alkyl group, a C 1 -C 5 alkoxy group, a halogen atom or a hydroxyl group, or its pharmaceutically acceptable salt.

Claim 10

The compound according to claim 1, which is the one representable by the formula: wherein E is a methylene group or an ethylene group and the full line accompanying a broken line (-----) is as defined in claim 1, or its pharmaceutically acceptable salt.

Claim 11

The compound according to claim 1, which is the one representable by the formula: wherein the full line accompanying a broken line (------) is as defined in claim 1, or its pharmaceutically acceptable salt.

Claim 12

A process for preparing a compound of the formula: wherein A is a carbonyl group or a sulfonyl group; B is either one of the formulas: (in which R. and R 2 are each a hydrogen atom, or either one of them is a hydrogen atom and the other is a hydroxyl group. a C 1 -C 5 alkyl group or a C 2 -C 6 alkanoyloxy group, or R 1 and R 2 are combined together to represent an oxo group, E is a methylene group, an ethylene group or an oxygen atom and the full line accompanying a broken line (-----) indicates a single bond or a double bond), (in which F is a methylene group or an ethylene group and R 1 , R 2 and the full line accompanying a broken line (-----) are each as defined above), (in which R 3 , R 4 , R s , R 6 , R 7 and R s are each a hydrogen atom or a C 1 -C 5 alkyl group and R,, R 2 and the full line accompanying a broken line (-----) are each as defined above), (in which R 9 and R 10 are each a C 1 -C 5 alkyl group), or (in which R 11 and R 12 are each a C 1 -C 5 alkyl group, or they are combined together to form a C 3 -C 5 alkylene group and n is an integer of 0, 1 or 2) when A represents a carbonyl group, or B is a 1.2-phenylene group when A represents a sulfonyl group; W is a C 1 -C 6 alkylene group, a C 2 -C 6 alkenylene group, a C 2 -C 6 alkynylene group or a C 2 -C 6 alkylene group substituted with hydroxyl; and G is a hydrogen atom, a C 1 -C 5 alkyl group, a C 1 -C 5 alkoxy group, a halogen atom or a hydroxyl group, or its pharmaceutically acceptable salt, which comprises: (a) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G and W are each as defined above to give the compound (I); (b) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G and W are each as defined above and X is a leaving group in the presence of an acid binding agent to give the compound (I); (c) reacting a compound of the formula: wherein A, B, X and W are each as defined above with a compound of the formula: wherein G is as defined above in the presence of an acid binding agent to give the compound (I); (d) subjecting a compound of the formula: wherein A, B and G are each as defined above and W' is a C 2 -C 6 alkenylene group or a C 2 -C 6 alkynylene group to hydrogenation to give a compound of the formula: wherein A, B and G are each as defined above; (e) subjecting a compound of the formula: wherein A and B are each as defined above, formaldehyde and a compound of the formula: wherein G is as defined above to the Mannich reaction to give a compound of the formula: wherein A, B and G are each as defined above; (f) subjecting a compound of the formula: wherein A, B and G are each as defined above to hydrogention to give a compound of the formula: wherein A, B and G are each as defined above; (g) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G is as defined above to give a compound of the formula: wherein A, B and G are each as defined above; or (h) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G is as defined above to give a compound of the formula: wherein A, B and G are each as defined above.

Claim 13

A process for preparing a compound of the formula: wherein A is a carbonyl group or a sulfonyl group; B is either one of the formulas: (in which R. and R 2 are each a hydrogen atom, or either one of them is a hydrogen atom and the other is a hydroxyl group. a C 1 -C 5 alkyl group or a C 2 -C 6 alkanoyloxy group, or R 1 and R 2 are combined together to represent an oxo group, E is a methylene group, an ethylene group or an oxygen atom and the full line accompanying a broken line (-----) indicates a single bond or a double bond), (in which F is a methylene group or an ethylene group and R 1 , R 2 and the full line accompanying a broken line (-----) are each as defined above), (in which R 3 , R 4 , R s , R 6 , R 7 and R s are each a hydrogen atom or a C 1 -C 5 alkyl group and R,, R 2 and the full line accompanying a broken line (-----) are each as defined above), (in which R 9 and R 10 are each a C 1 -C 5 alkyl group), or (in which R 11 and R 12 are each a C 1 -C 5 alkyl group, or they are combined together to form a C 3 -C 5 alkylene group and n is an integer of 0, 1 or 2) when A represents a carbonyl group, or B is a 1.2-phenylene group when A represents a sulfonyl group; W is a C 1 -C 6 alkylene group, a C 2 -C 6 alkenylene group, a C 2 -C 6 alkynylene group or a C 2 -C 6 alkylene group substituted with hydroxyl; and G is a hydrogen atom, a C 1 -C 5 alkyl group, a C 1 -C 5 alkoxy group, a halogen atom or a hydroxyl group, or its pharmaceutically acceptable salt, which comprises: (a) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G and W are each as defined above to give the compound (I); (b) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G and W are each as defined above and X is a leaving group in the presence of an acid binding agent to give the compound (I); (c) reacting a compound of the formula: wherein A, B, X and W are each as defined above with a compound of the formula: wherein G is as defined above in the presence of an acid binding agent to give the compound (I); (d) subjecting a compound of the formula: wherein A, B and G are each as defined above and W' is a C 2 -C 6 alkenylene group or a C 2 -C 6 alkynylene group to hydrogenation to give a compound of the formula: wherein A, B and G are each as defined above; (e) subjecting a compound of the formula: wherein A and B are each as defined above, formaldehyde and a compound of the formula: wherein G is as defined above to the Mannich reaction to give a compound of the formula: wherein A, B and G are each as defined above; (f) subjecting a compound of the formula: wherein A, B and G are each as defined above to hydrogention to give a compound of the formula: wherein A, B and G are each as defined above; (g) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G is as defined above to give a compound of the formula: wherein A, B and G are each as defined above; or (h) reacting a compound of the formula: wherein A and B are each as defined above with a compound of the formula: wherein G is as defined above to give a compound of the formula: wherein A, B and G are each as defined above.

Claim 14

A pharmaceutical composition for treatment of psychosis which comprises as an active ingredient a pharma ceutically effective amount of the compound (I) or its pharmaceutically acceptable acid addition salt according to claim 1, and at least one pharmaceutically acceptable inert carrier or diluent.

Claim 15

Use of the compound (I) or its pharmaceutically acceptable acid addition salt according to claim 1 for the preparation of a pharmaceutical composition having anti-psychotic activity.

Claim 16

A compound (I) or its pharmaceutically acceptable acid addition salt according to claim 1 for use in a method for treatment of psychosis which comprises administering a pharmaceutically effective amount to a human being in psychosis.