US 7,592,456 B2
Arylsulfonylnaphthalene derivatives as 5HT2A antagonists
Mark Stuart Chambers, Puckeridge (United Kingdom); Neil Roy Curtis, Buntingford (United Kingdom); Emanuela Gancia, Royston (United Kingdom); Myra Gilligan, Hoddesdon (United Kingdom); Alexander Charles Humphries, Stevenage (United Kingdom); Tamara Ladduwahetty, London (United Kingdom); Robert James Maxey, Amersham (United Kingdom); and Kevin John Merchant, Ware (United Kingdom)
Assigned to Merck Sharp & Dohme Limited, Hoddesdon, Hertfordshire (United Kingdom)
Appl. No. 11/791,195
PCT Filed Nov. 28, 2005, PCT No. PCT/GB2005/050215
§ 371(c)(1), (2), (4) Date May 18, 2007,
PCT Pub. No. WO2006/059149, PCT Pub. Date Jun. 08, 2006.
Claims priority of application No. 0426313.3 (GB), filed on Dec. 01, 2004.
Prior Publication US 2007/0281952 A1, Dec. 06, 2007
Int. Cl. C07D 215/00 (2006.01); C07D 401/02 (2006.01); C07D 401/00 (2006.01); C07D 401/10 (2006.01); C07C 305/00 (2006.01)
U.S. Cl. 546—153  [546/157; 546/18; 558/37] 10 Claims
 
1. A compound of the formula I:

OG Complex Work Unit Drawing
wherein:
t is 2;
each of X1, X3, and Y1 represents CH or N and each of X2, Y2, and Y3 represents CH, provided that X1 and X3 do not both represent N and provided that X1 and Y1 do not both represent N;
Ar1 represents phenyl, said phenyl bearing 0 to 3 substituents selected from halogen, CN, CF3, OCF3, C1-6alkyl, OH, C1-6alkoxy or hydroxyC1-6alkyl;
Ar2 represents phenyl, pyridyl or thienyl, said phenyl, pyridyl or thienyl bearing 0 to 3 substituents selected from halogen, CN, nitro, Ra, ORa, SRa, SORa, SO2Ra, SO2NRaRb, (CH2)xNRaRb, (CH2)xNRaCORb, (CH2)xNRaCO2Rb, (CH2)xNRaCONRaRb (CH2)xNRaSORb, (CH2)xNRaSO2Rb, (CH2)xNRaSO2NRaRb, (CH2)xCORa, (CH2)xCO2Ra, (CH2)xCONRaRb, N═CHN(CH3)2 or (CH2)xCRa═NORb, where x is 0 or 1, or said phenyl, pyridyl or thienyl may be substituted with (CH2)xAr3, COAr3 or CH(OH)Ar3 where Ar3 represents a five- or six-membered heteroaromatic ring optionally bearing up to 2 substituents selected from halogen, CN, CF3, OH, C1-6alkyl, C1-6alkoxy, C1-6alkylthio, amino, C1-6alkylamino or di(C1-6)alkylamino;
Ra and Rb independently represent H or a hydrocarbon group of up to 7 carbon atoms which is optionally substituted with up to 3 halogen atoms or with up to 2 substituents selected from CN, OH, C1-4alkoxy, C1-4alkylthio, amino, C1-4alkylamino and di(C1-4)alkylamino; or Ra or Rb, when linked through a nitrogen atom, together represent the residue of a heterocyclic ring of 4, 5 or 6 members, optionally bearing up to 3 substituents selected from halogen, CN, CF3, oxo, OH, C1-4alkyl or C1-4alkoxy; or two Ra groups, when attached to adjacent carbon atoms of Ar2, may form a fused ring of 5 or 6 members, 0-3 of which are selected from N, O or S while the remainder are carbon, said ring optionally bearing up to 3 substituents selected from halogen CN, CF3, oxo, OH, C1-4alkyl or C1-4alkoxy;
and wherein any nitrogen atom forming part of a heteroaromatic ring may be in the form of the N-oxide;
or a pharmaceutically acceptable salt thereof.