Imide derivatives, and their production and use

• US 5,532,372 A
• Filed: 08/30/1993
• Issued: 07/02/1996
• Est. Priority Date: 07/06/1990
• Status: Expired due to Term

• Current Assignee: Sumitomo Dainippon Pharma Company Limited (Sumitomo Chemical Company Limited)
• Original Assignee: Sumitomo Pharmaceuticals Company Limited (Sumitomo Chemical Company Limited)
• Inventors: Muto, Masayuki, Saji, Ikutaro, Tanno, Norihiko, Yoshigi, Mayumi
• Primary Examiner(s): BOND, ROBERT
• Application Number:
  US08/113,320
• Time in Patent Office: 1,037 Days
• Field of Search: 544/368
• US Class Current: 544/368
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• CPC Class Codes: A61P 25/20 Hypnotics; Sedatives
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C07D 275/06 with hetero atoms directly attached to the ring sulfur atom
• CPC Class Codes: C07D 401/08 linked by a carbon chain containing alicyclic rings
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 403/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 493/08 Bridged systems

Abstract

An imide compound of the formula: ##STR1## wherein Z is a group of the formula: ##STR2## in which the substituents are defined herein, and n is an integer of 0 to 1;

D is a group of the formula:

--(CH.sub.2).sub.p --A--(CH.sub.2).sub.q --

in which A is a non-aromatic hydrocarbon ring optionally bridged with a lower alkylene group or an oxygen atom, said non-aromatic hydrocarbon ring and said lower alkylene group being each optionally substituted with at least one lower alkyl, and p and q are each an integer of 0, 1 or 2; and

Ar is an aromatic group, a heterocyclic aromatic group, a benzoyl group, a phenoxy group or a phenylthio group and G is >N--, >CH-- or >COH-- or Ar is a biphenylmethylidene group and G is >C═, all of the above groups being each optionally substituted with at least one of lower alkyl, lower alkoxy and halogen; and its acid addition salts, useful as an antipsycotic agent.

Claims

1. An imide compound of the formula:

##STR144## wherein Z is a group of the formula;

##STR145## in which B is a carbonyl group or a sulfonyl group, R¹, R², R³ and R⁴ are each a hydrogen atom or an alkyl group having 1-4 carbon atoms with a proviso that R¹ and R² or R¹ and R³ are combined together to make a non-aromatic hydrocarbon ring having at most 7 carbon atoms and being un-substituted or substituted with at least one alkyl group having 1-4 carbon atoms, and n is an integer of 0 or 1;

D is a group of the formula;

space="preserve" listing-type="equation">--(CH.sub.2).sub.p --A--(CH.sub.2).sub.q --

in which A is a non-aromatic hydrocarbon ring having at most 7 carbon atoms or a non-aromatic hydrocarbon ring having at most 7 carbon atoms which is bridged with an alkylene group having not more than 3 carbon atoms or an oxygen atom, and p and q are each an integer of 0, 1 or 2;

Ar is a benzisothiazolyl group being unsubstituted or substituted with at least one of an alkyl group having 1-4 carbon atoms, an alkoxy group having 1-4 carbon atoms and a halogen atom; and

G is >

N--;

or an acid addition salt thereof.

2. The imide compound according to claim 1, wherein said non-aromatic hydrocarbon ring in Z is further bridged with an alkylene group having 1-3 carbon atoms and being un-substituted or substituted with at least one alkyl group having 1-4 carbon atoms, or an oxygen atom;

or an acid addition salt thereof.

3. The imide compound according to claim 1, wherein said non-aromatic hydrocarbon ring in D is further bridged with an alkylene group having 1-3 carbon atoms and being unsubstituted or substituted with at least one alkyl group having 1-4 carbon atoms, or an oxygen atom;

or an acid addition salt thereof.

4. The imide compound according to claim 1, wherein said non-aromatic hydrocarbon rings in Z and D are further bridged with an alkylene group having 1-3 carbon atoms and being unsubstituted or substituted with at least one alkyl group having 1-4 carbon atoms, or an oxygen atom;

or an acid addition salt thereof.

5. The imide compound according to claim 1, wherein Z is one of the following formulas:

##STR146## wherein L is --CH₂ --CH₂ --or --CH═

CH--, E is an alkylene group having not more than 3 carbon atoms and being un-substituted or substituted with an alkyl group having not more than 4 carbon atoms or an oxygen atom, R⁵ is a hydrogen atom or an alkyl group having not more than 4 carbon atoms and B is a carbonyl group or a sulfonyl group;

##STR147## wherein L, E, R⁵ and B are each as defined above;

##STR148## wherein R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are each a hydrogen atom or an alkyl group having not more than 4 carbon atoms, or two of those present at the neighboring positions each other may be combined together to make a bond and B is as defined above; and

##STR149## wherein R⁴ is a hydrogen atom or an alkyl group having not more than 4 carbon atoms, R¹⁶ and R¹⁷ are combined together to make a saturated hydrocarbon ring having not more than 7 carbon atoms, and B is as defined above;

or an acid addition salt thereof.

20. The imide compound according to claim 1, wherein said non-aromatic hydrocarbon ring and said alkylene group in the definition of A are each substituted with at least one alkyl group having 1-4 carbon atoms.

6. An imide compound of the formula:

##STR150## wherein Z is a group of the formula;

##STR151## wherein L is --CH₂ --CH₂ --or --CH═

CH--, E is an alkylene group having not more than 3 carbon atoms;

D is a group of the formula;

space="preserve" listing-type="equation">--(CH.sub.2).sub.p --A--(CH.sub.2).sub.q --

wherein A is a cycloalkane ring having not more than 7 carbon atoms or a cycloalkane ring having not more than 7 carbon atoms which is bridged with an alkylene group having not more than 3 carbon atoms, or an oxygen atom, p and q are each an integer of 0, 1 or 2;

Ar is a benzisothiazolyl group; and

G is >

N--

or an acid addition salt thereof.

7. The imide compound according to claim 7, wherein said cycloalkane ring in D is further bridged with an alkylene group having 1-3 carbon atoms;

or an acid addition salt thereof.

8. The imide compound according to claim 7 or 8, wherein Z is a group of the formula:

##STR152## wherein E is a methylene group or an ethylene group;

or an acid addition salt thereof.

9. The imide compound according to claim 7 or 8, wherein D is a group of the formula:

space="preserve" listing-type="equation">--CH.sub.2 --A--CH.sub.2 --

wherein A is as defined above;

or an acid addition salt thereof.

10. The imide compound according to claim 10, wherein A is a cyclohexane ring;

or an acid addition salt thereof.

11. The imide compound of the formula:

##STR153## wherein Z is a group of the formula;

##STR154## wherein E is a methylene group or an ethylene group;

D is a group of the formula;

space="preserve" listing-type="equation">--CH.sub.2 --A--CH.sub.2 --

wherein A is a cycloalkane ring having not more than 7 carbon atoms or a cycloalkane ring having not more than 7 carbon atoms which is bridged with an alkylene group having not more than 3 carbon atoms, or an oxygen atom;

Ar is a benzisothiazolyl group; and

G is >

N--;

or an acid addition salt thereof.

14. The imide compound of the formula:

##STR155## or an acid addition salt thereof.

12. The imide compound according to claim 14, wherein E is a methylene group;

or an acid addition salt thereof.

13. The imide compound according to claim 14 or 15, wherein A is a 1,2-cyclohexane-diyl group;

or an acid addition salt thereof.

15. The imide compound of the formula:

##STR156##

16. The imide compound of one of the following formulae:

##STR157##

17. The imide compound of the formula:

##STR158## or an acid addition salt thereof.

18. The imide compound of the formula:

##STR159## or an acid additional salt thereof.

19. The imide compound of the formula:

##STR160## or an acid addition salt thereof.