Tricyclic compounds

Details Tricyclic compounds Tricyclic compounds

1997-06-06

1998-03-10

Richter, Johann

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549354, 549 12, 549 13, 549458, 546 89, 546 80, 546 93, 568326, C07D31302, C07D33380

Patent

active

057263256

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP96/02997 filed Oct. 16, 1996.


TECHNICAL FIELD

The present invention relates to tricyclic compounds which are useful as therapeutic agents for urinary incontinence.


BACKGROUND ART

Japanese Published Unexamined Patent Application No. 286915/93 discloses N-substituted propanamide derivatives which are useful for the treatment of urinary incontinence.


DISCLOSURE OF THE INVENTION

The present invention relates to tricyclic compounds represented by general formula (I): ##STR2## wherein R.sup.1 represents hydrogen, lower alkyl, lower alkoxy, or halogen; --X.sup.1 --X.sup.2 --X.sup.3 -- represents --CR.sup.2 .dbd.CR.sup.3 --CR.sup.4 .dbd.CR.sup.5 -- (wherein R.sup.2, R.sup.3, R.sup.4, and R.sup.5, which may be the same or different, each represents hydrogen, lower alkyl, lower alkoxy, or halogen), --CR.sup.2 .dbd.CR.sup.3 --CR.sup.4 .dbd.N-- (wherein R.sup.2, R.sup.3, and R.sup.4 have the same significances as defined above), --CR.sup.2 .dbd.CR.sup.3 --S-- (wherein R.sup.2 and R.sup.3 have the same significances as defined above), --CR.sup.2 .dbd.CR.sup.3 --O-- (wherein R.sup.2 and R.sup.3 have the same significances as defined above), --S--CR.sup.4 .dbd.CR.sup.5 -- (wherein R.sup.4 and R.sup.5 have the same significances as defined above), or --O--CR.sup.4 .dbd.CR.sup.5 -- (wherein R.sup.4 and R.sup.5 have the same significances as defined above); and Y represents --CH.sub.2 O--, --CH.sub.2 S--, --CH.sub.2 SO--, --CH.dbd.CH--, or --(CH.sub.2).sub.n -- Compound (I), and the same applies to the compounds of other formula numbers!.
In the definitions of the groups in general formula (I), the lower alkyl and the lower alkyl moiety of the lower alkoxy mean a straight-chain or branched alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl. The halogen includes fluorine, chlorine, bromine, and iodine.
The processes for preparing Compound (I) are described below.
Compound (I) can be prepared according to the following reaction step. ##STR3## (In the formulae, R.sup.1, --X.sup.1 --X.sup.2 --X.sup.3 --, and Y have the same significances as defined above.)
Compound (I) can be obtained by treating Compound (II) with an equivalent amount of halogenating agent such as thionyl chloride and oxalyl chloride in an inert solvent such as dichloromethane, dichloroethane, tetrachloroethane and dimethylacetamide at -30.degree. to 0.degree. C. for 5 minutes to 12 hours, and then subjecting the obtained substance to reaction with Compound (III) at a temperature between 0.degree. C. and the boiling point of the solvent used for 5 minutes to 24 hours. This reaction is preferably carried out under an atmosphere of dry inert gas such as argon gas and nitrogen gas.
The starting Compound (II) can be obtained according to the process described in J. Chem. Soc., 2329-2332 (1951). The starting Compound (III) may be commercially available, or can be prepared according to the processes described in the following Steps 2 through 4.
Compound (III) can be prepared according to the following reaction steps. ##STR4## (In the formulae, R.sup.1, --X.sup.1 --X.sup.2 --X.sup.3 --, and Y have the same significances as defined above.)
The starting Compound (IV) can be obtained according to the known methods (1977); ibid., 20, 1557 (1977); ibid., 21, 633 (1978); ibid., 22, 1357 (1979); ibid., 27, 372 (1984); ibid., 29, 2347 (1986); ibid., 29, 2074 (1992); ibid., 38, 496 (1995), etc.! or similar methods thereto.
Compound (V) can be obtained by treating Compound (IV) according to the methods described in Synthesis, 295 (1990), etc. in tert-butanol in the presence of an equivalent amount of diphenylphosphoryl azide under an atmosphere of dry inert gas such as argon gas and nitrogen gas.
Compound (III) can be obtained by hydrolyzing Compound (V) in an appropriate solvent such as trifluoroacetic acid, hydrochloric acid/dioxane and hydrobromic acid/acetic acid at a temperature between 0.degree. C. and the boiling point of the solvent used

REFERENCES:
patent: 4477465 (1984-10-01), Martin et al.
patent: 5116863 (1992-05-01), Oshima et al.
patent: 5272163 (1993-12-01), Russell et al.
J. Med. Chem., vol. 39, No. 23 (Nov. 1996) pp. 4592-4601.

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