Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-07-21
2003-05-13
Raymond, Richard L. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C546S300000, C546S271400, C546S272100, C546S272400, C546S272700, C546S275400, C546S276100, C546S261000, C546S257000, C544S114000, C544S124000, C544S135000, C544S140000, C544S139000, C544S357000, C544S238000, C544S405000, C544S409000, C544S410000, C514S235800, C514S236500, C514S238800, C514S252060, C514S252190, C514S253010, C514S338000, C514S255050, C514S252020
Reexamination Certificate
active
06562817
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel tricyclic compound and a pharmaceutical composition for use as an immunosuppressant, an anti-allergic agent or a suppressant of the IgE production comprising the same.
BACKGROUND ART
A serious problem of a transplantation of a tissue or an organ which is frequently performed in recent years is a rejection symptom for excluding a transplanted part after an operation. Prevention of the rejection symptom is very important for a success of the transplantation.
Various immunosuppressants such as azathioprine, corticoid, Cyclosporin A, Tacrolimus and the like are developed and come into practical use for prevention and a treatment of a rejection symptom against a transplantation of an organ or a tissue or a graft-versus-host reaction which is caused by a bone marrow transplantation. But they are not so satisfactory in view of their effects and side effects.
Allergic diseases such as atopic dermatitis, allergic rhinitis, bronchial asthma, allergic conjunctivitis and the like tend to globally increase in recent years and become serious problems. The conventional antiinflammatory agents are suppressants of releasing chemical mediators from mast cells, receptor inhibitors of the released chemical mediators, suppressants of allergic inflammation response or the like. All of these are agents for symptomatic therapy and are not fundamental therapeutic agents for allergic diseases.
Therefore, the development of a more effective and safer medicinal agent has been expected.
The compounds having a similar structure to a compound of the present invention and exhibiting an immunosuppressive or anti-allergic effect are described in WO94/27980, WO95/13067, WO96/40659, WO96/40143, WO96/38412, WO97/24356, WO97/24324, WO97/46524, JP-A 8-3163, JP-A 9-12457, JP-A 9-71564, JP-A 9-124571 and the like. The liquid crystal compounds are described in JP-A 9-87253, JP-A 63-253065, JP-A 1-106864, JP-A 1-106871, JP-A 2-83346, JP-A 9-48760, JP-A 9-31063 and the like, the compounds exhibiting an insecticide or acaricide activity are described in JP-A 8-193067 and the compounds having a therapeutic activity for circulatory system or psychopathy diseases are described in EP0600717 A1, all of which have a similar structure to a compound of the present invention.
DISCLOSURE OF THE INVENTION
The present invention provides a compound of the formula (I):
wherein A ring, B ring and C ring are each independently optionally substituted aromatic carbocycle or optionally substituted 5- or 6-membered heterocycle which may fuse with benzene ring,
W
1
, W
2
and/or W
3
represents a bond when A ring, B ring and/or C ring is optionally substituted 5-membered heterocycle,
X is —O—, —CH
2
—, —NR
1
— wherein R
1
is hydrogen, optionally substituted lower alkyl, lower alkenyl, lower alkylcarbonyl or optionally substituted lower alkoxycarbonyl or —S(O)p— wherein p is an integer of 0 to 2,
Y is hydrogen, optionally substituted lower alkyl, optionally substituted lower alkenyl, optionally substituted lower alkynyl, optionally substituted acyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted lower alkoxycarbonyl, optionally substituted sulfamoyl, optionally substituted amino, optionally substituted aryl or optionally substituted 5- or 6-membered heterocycle,
Y may be optionally substituted lower alkoxy when X is —CH
2
—,
Y may be optionally substituted lower alkoxycarbonyl; optionally substituted lower alkylsulfonyl or optionally substituted arylsulfonyl when X is —O— or —NR
1
—, one of V
1
and V
2
is a bond and the other is a bond, —O—, —NH—, —OCH
2
—, —CH
2
O—, —CH═CH—, —C≡—C—, —CH(OR
2
)— wherein R
2
is hydrogen or lower alkyl, —CO— or —NHCHR
3
— wherein R
3
is hydrogen or hydroxy, and
at least one of A ring, B ring and C ring is optionally substituted aromatic carbocycle and at least another one is optionally substituted 5- or 6-membered heterocycle which may fuse with benzene ring when both of V
1
and V
2
are single bonds,
pharmaceutically acceptable salt or hydrate thereof
The present invention provides a pharmaceutical composition for use as an immunosuppressant, an anti-allergic agent or a suppressant of the IgE production comprising the compound (I), pharmaceutically acceptable salt or hydrate thereof.
In one of the other embodiments, the present invention provides a method for suppressing an immune response or a method for treating and/or preventing allergic diseases comprising administering the compound (I). In another embodiment, the present invention provides use of the compound (I) for manufacturing a medicament for suppressing an immune response or treating and/or preventing allergic diseases.
In the present specification, the term “halogen” includes fluorine, chlorine, bromine and iodine. Fluorine or chlorine is preferable.
The term “lower alkyl” includes straight or branched chain alkyl having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, and most preferably 1 to 3 carbon atoms. For example, included are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, hexyl, isohexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, n-decyl and the like.
As substituents of “optionally substituted lower alkyl”, exemplified are halogen; hydroxy; lower alkoxy optionally substituted with lower alkoxy; acyl; acyloxy; carboxy; lower alkoxycarbonyl; mercapt; lower alkylthio; amino optionally substituted with hydroxy, lower alkyl or optionally substituted acyl; imino optionally substituted with hydroxy, lower alkoxy, carboxy(lower)alkoxy, aryl(lower)alkoxy or 5- or 6-membered heterocycle; hydrazono optionally substituted with carbamoyl or lower alkoxycarbonyl; carbamoyl optionally substituted with lower alkyl or amino; thiocarbamoyl optionally substituted with lower alkyl; cycloalkyl optionally substituted with lower alkyl or lower alkoxy; cycloalkenyl optionally substituted with lower alkyl; cyano; phenyl optionally substituted with at least one substituent selected from the group of hydroxy, lower alkyl, carboxy, lower alkoxycarbonyl and lower alkoxy; 5- or 6-membered heterocycle which may be substituted with lower alkyl and may fuse with benzene ring; and the like. The lower alkyl may be substituted with one or more of these substituents at any possible positions. Halogen; hydroxy; acyloxy; phenyl optionally substituted with lower alkyl or lower alkoxy; pyridyl or the like is preferable.
The part of lower alkyl in “lower alkoxy” is the same as the above “lower alkyl”.
As substituents for “optionally substituted lower alkoxy”, exemplified are halogen; hydroxy; lower alkoxy optionally substituted with acyloxy; acyl; acyloxy optionally substituted with hydroxy or carboxy; carboxy; lower alkoxycarbonyl; lower alkylthio; amino optionally substituted with lower alkyl; phenyl optionally substituted with lower alkyl or lower alkoxy; heterocycle; heterocyclylcarbonyloxy and the like.
The parts of lower alkyl in “lower alkoxycarbonyl”, “lower alkylsulfonyl”, “lower alkylsulfonyloxy”, “lower alkylthio”, “lower alkylamino” and “lower alkylenedioxy” are the same as the above “lower alkyl”. Substituents for “optionally substituted lower alkoxycarbonyl”, “optionally substituted lower alkylsulfonyl” and “optionally substituted lower alkylthio” are the same as those for the above “optionally substituted lower alkoxy”.
The term “lower alkenyl” includes straight or branched chain alkenyl of 2 to 10 carbon atoms, preferably 2 to 8 carbon atoms more preferably 3 to 6 carbon atoms having at least one double bond at any possible positions. For example, included are vinyl, propenyl such as 2-propenyl and the like, isopropenyl, butenyl, isobutenyl, prenyl, butadienyl, pentenyl, isopentenyl, pentadienyl, hexenyl, isohexenyl, hexadienyl, heptenyl, octenyl, nonenyl, decenyl and the like. Substituents for “optionally substituted lower alkenyl” are the same as those for the above “optionally substituted lower alkoxy” and alkenyl substitu
Haga Nobuhiro
Hasegawa Yasushi
Tanimoto Norihiko
Birch & Stewart Kolasch & Birch, LLP
Habte Kahsay
Raymond Richard L.
Shionogi & Co. Ltd.
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