Tricyclic compounds

Details Tricyclic compounds Tricyclic compounds

1999-10-14

2001-04-03

Lambkin, Deborah C. (Department: 1612)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S291000, C514S375000, C549S012000, C546S080000, C548S218000

Reexamination Certificate

active

06211227

ABSTRACT:

TECHNICAL FIELD
The present invention relates to tricyclic compounds having an activity to prolong the intervals between micturitions caused when a bladder becomes full, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment or alleviation of pollakiuria, urinary incontinence, urinary urgency or the sense of residual urine caused by various kinds of diseases or conditions such as neurogenic bladder and unstable bladder.
BACKGROUND ART
Japanese Published Unexamined Patent Application No. 286915/93 (EP524781) discloses N-substituted propanamide derivatives which are useful for the treatment of urinary incontinence.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide novel tricyclic compounds which are useful as therapeutic agents for pollakiuria and urinary incontinence.
The present invention relates to tricyclic compounds represented by general formula (I):
(wherein
R
1
represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkoxy or halogen;
X
1
—X
2
—X
3
represents CR
5
═CR
6
—CR
7
═CR
8
(wherein R
5
, R
6
, R
7
and R
8
, which may be the same or different, each represents hydrogen, substituted or unsubstituted lower alkyl, hydroxy, substituted or unsubstituted lower alkoxy, nitro, amino, lower monoalkyl-substituted amino, lower dialkyl-substituted amino, substituted or unsubstituted lower alkanoylamino or halogen), N(O)m═CR
5
—CR
6
═CR
7
(wherein R
5
, R
6
and R
7
have the same significances as defined above, and m represents 0 or 1), CR
5
═CR
6
—N(O)m═CR
7
(wherein R
5
, R
6
, R
7
and m have the same significances as defined above), CR
5
═CR
6
—CR
7
═N(O)m (wherein R
5
, R
6
, R
7
and m have the same significances as defined above), CR
5
═CR
6
—O (wherein R
5
and R
6
have the same significances as defined above), CR
5
═CR
6
—S (wherein R
5
and R
6
have the same significances as defined above), O—CR
7
═CR
8
(wherein R
7
and R
8
have the same significances as defined above), S—CR
7
═CR
8
(wherein R
7
and R
8
have the same significances as defined above) or O—CR
7
═N (wherein R
7
has the same significance as defined above);
and when R
2
represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkenyl, trifluoromethyl, substituted or unsubstituted lower alkoxy, amino, substituted or unsubstituted lower monoalkyl-substituted amino, substituted or unsubstituted lower dialkyl-substituted amino, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkylamino, substituted or unsubstituted arylamino, a substituted or unsubstituted alicyclic heterocyclic group, a substituted or unsubstituted N-substituted heterocyclic group or
(wherein
n is 0 or 1; R
3
and R
4
, which may be the same or different, each represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted cyclic alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl or trifluoromethyl, or R
3
and R
4
may be combined together to form cyclic alkyl; and Q represents hydroxy, substituted or unsubstituted lower alkoxy, amino or halogen);
Y represents —CH
2
SO
2
—, —SCH
2
—, —SOCH
2
— or —SO
2
CH
2
—, when R
2
represents hydrogen, substituted or unsubstituted lower alkenyl, trifluoromethyl, substituted or unsubstituted lower alkoxy, amino, substituted or unsubstituted lower monoalkyl-substituted amino, substituted or unsubstituted lower dialkyl-substituted amino, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkylamino, substituted or unsubstituted arylamino, a substituted or unsubstituted alicyclic heterocyclic group, a substituted or unsubstituted N-substituted heterocyclic group or
(wherein
n, R
3
, R
4
and Q have the same significances as defined above),
Y represents —OCH
2
—);
and pharmaceutically acceptable salts thereof.
Hereinafter, the compounds represented by general formula (I) are referred to as Compounds (I), and the same applies to the compounds of other formula numbers.
In the definitions of each group in general formula (I), the lower alkyl includes straight-chain or branched alkyl groups having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, 1,2,2-trimethylpropyl and the like. The halogen means fluorine, chlorine, bromine or iodine. The alkyl moiety of the lower alkoxy, the lower monoalkyl-substituted amino and the lower dialkyl-substituted amino has the same significance as the above lower alkyl. The lower alkanoyl of the lower alkanoylamino includes alkanoyl groups having 1 to 6 carbon atoms, such as formyl, acetyl, propanoyl, butanoyl, pentanoyl, 2,2-dimethylpropanoyl and the like. The lower alkenyl includes straight-chain or branched alkenyl groups having 2 to 6 carbon atoms, such as vinyl, allyl, 1-propenyl, methacryl, 1-butenyl, crotyl, pentenyl, hexenyl and the like. The aryl includes phenyl, naphthyl and the like, and the heteroaryl includes pyridyl, furyl, thienyl, quinolyl, imidazolyl, benzimidazolyl, thiazolyl and the like. The aralkyl includes aralkyl groups having 7 to 12 carbon atoms, such as benzyl, phenethyl, naphthylmethyl and the like. The alicyclic heterocyclic group includes tetrahydrofuryl, tetrahydrothienyl, chromanyl and the like. The N-substituted heterocyclic group is a heterocyclic ring containing 1 to 2 nitrogen atoms therein, which may contain hetero atoms such as O and S, said nitrogen atom being bonded to the adjoining carbonyl group. The N-substituted heterocyclic group includes, for example, pyrrolidinyl, piperazinyl, piperidino, morpholino, thiomorpholino and oxazolyl. The cyclic alkyl includes cyclic alkyl groups having 3 to 8 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like.
The substituted lower alkyl, the substituted lower alkoxy, the substituted lower monoalkyl-substituted amino, the substituted lower dialkyl-substituted amino, the substituted lower alkanoylamino, the substituted lower alkenyl and the substituted cyclic alkyl each has 1 to 3 substituents which are the same or different. Examples of the substituents are hydroxy, halogen, nitro, amino, lower monoalkyl-substituted amino, lower dialkyl-substituted amino and lower alkoxy. The halogen has the same significance as defined above. The alkyl group of the lower monoalkyl-substituted amino, the lower dialkyl-substituted amino and the lower alkoxy has the same significance as the above lower alkyl.
The substituted aryl, the substituted heteroaryl, the substituted aralkyl, the substituted aralkylamino and the substituted arylamino each has 1 to 3 substituents which are the same or different. Examples of the substituents are lower alkyl, hydroxy, amino and halogen. The lower alkyl and halogen have the same significances as the above lower alkyl and halogen, respectively.
The substituted alicyclic heterocyclic group and the substituted N-substituted heterocyclic group each has 1 to 3 substituents which are the same or different. Examples of the substituents are lower alkyl, hydroxy and halogen. The lower alkyl and halogen have the same significances as the above lower alkyl and halogen, respectively.
As R
1
, hydrogen, substituted or unsubstituted lower alkoxy and halogen are preferred. Particularly preferred is hydrogen.
As Y, —CH
2
SO
2
—, —SO
2
CH
2
— and —OCH
2
— are preferred. Particularly preferred is —CH
2
SO
2
—.
As X
1
—X
2
—X
3
, S—CR
7
═CR
8
(wherein R
7
and R
8
have the same significances as defined above) and CR
5
═CR
6
—CR
7
═CR
8
(wherein R
5
, R
6
, R
7
and R
8
have the same significances as defined above) are preferred. Particularly preferred is S—CR
7
═CR
8
(wherein R
7
and R
8
have the same significances as defined above).
As R
2
,
(wherein n, R
3
, R
4
and Q have the same significances as defined above) is preferred. Particularly preferred is
The p

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