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1. (WO1991009015) MUSCARINIC RECEPTOR ANTAGONISTS
Note: Text based on automatic Optical Character Recognition processes. Please use the PDF version for legal matters

CLAIMS
1. A compound of the formula:-


or a pharmaceutically acceptable salt thereof,
wherein Y is a direct link, -CH2-, -(CH2)2-, -CH2O- or -CH2S-; and R1 is a group of the formula:-


where R 2 and R3 are each andependently H, C1-C4 alkyl, C1-C4 alkoxy, -(CH2)nOH, halo, trifluoromethyl, cyano,
-(CH2)nNR4R5, -CO C(1-C4 alkyl), -OCO(C1-C4 alkyl),
-CH(OH) (C1-C4 alkyl), -C(OH)(C1-C4 alkyl)2, -SO2NH2,
-(CH2) CONR4R5 or -(CH2)nCOO(C1-C4 alkyl);
R 4 and R5 are each independently H or C1-C4 alkyl;
n is O, 1 or 2;
X and X1 are each independently O or CH2;

m is 1, 2 or 3;
and "Het" is pyridyl, pyrazinyl or thienyl.
2. A compound as claimed in claim 1 in which m is 1.
3. A compound as claimed in claim 1 or 2 in which R1 is a group of the formula:-


where R2 and R3 are each independently selected from H, halo and hydroxy, and X and X1 are as defined in claim 1.
4. A compound as claimed in claim 3 in which R1 is:-


5. A compound as claimed in any one of the preceding claims in which Y is a direct link, -CH2- or -(CH2)2-.
6. A compound as claimed in claim 5 in which Y is -CH2-.

7. A pharmaceutical composition comprising a compound of the formula (I) as claimed in any one of the preceding claims, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable diluent or carrier.
8. A compound of the formula (I) as claimed in any one of claims 1 to 6, or a pharmaceutically acceptable salt thereof, for use as a medicament.
9. The use of a compound of the formula (I) as claimed in any one of claims 1 to 6, or of a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for use as a muscarinic receptor antagonist.
10. A process for preparing a compound of the formula (I)


or a pharmaceutically acceptable salt thereof,
wherein Y is a direct link, -CH2-, -(CH2)2-, -CH2O- or -CH2S-; and R1 is a group of the formula:-

where R2 and R3 are each independently H, C1-C4 alkyl, C1-C4 alkoxy, -(CH2)nOH, halo, trifluoromethyl, cyano,
-(CH2)nNR4R5, -CO(C1-C4alkyl), -OCO(C1-C4 alkyl),
-CH(OH) (C1-C4 alkyl), -C(OH) (C1-C4 alkyl)2, -SO2NH2,

-(CH2)nCONR4R5 or -(CH2)nCOO(C1-C4 alkyl);
R4 and R5 are each independently H or C1-C4 alkyl;
n is O, 1 or 2;
X and X1 are each independently O or CH 2 ;
m is 1, 2 or 3 ;
and "Het" is pyridyl, pyrazinyl or thienyl,
characterised by (a) reacting a compound of the formula:-


with a compound of the formula:-

Q-CH2-Y-R1

where Y and R1 are as defined above and Q is a leaving group, (b) cyclising a compound of the formula (IV) by heating it with concentrated mineral acid:-

where Y and R1 are as defined above, or (c), to prepare compounds in which Y is OH2 and R1 is pyrazinyl or 2- or 4-pyridyl, reacting a compound of the formula (II) as defined above with
2-vinylpyrazine or 2- or 4- vinyl pyridine;
said processes (a) to (c) being followed by, optionally,
conversion of the product into a pharmaceutically acceptable salt.

11. A process as claimed in claim 10, characterised in that in part (a), Q is Cl, Br, I or methanesulfonyloxy and the reaction is carried cut in the presence of an acid acceptor, and in that in part (b), the concentrated mineral acid is concentrated
hydrochloric acid.
12. A method for treating irritable bowel disease in a patient in need of such treatment, characterised by administering to said patient an effective amount of a compound of the formula (I) or pharmaceutically aceptable salt thereof as claimed in any one of claims 1 to 6.