US 6,448,290 B1Granted

Sulfonamide and carboxamide derivatives and drugs containing the same as the active ingredient

AssigneeOno Pharmaceutical Co., Ltd.

InventorsShuichi Ohuchida, Yuuki Nagao

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Abstract

The sulfonamide or carboamide derivatives of the formula (I) and a pharmaceutical composition which comprise them as an active ingredient: (wherein A ring, B ring is carbocyclic ring, heterocyclic ring; Z1 is —COR1, —CH═CH—COR1 etc.; Z2 is H, alkyl etc.; Z3 is single bond, alkylene; Z4 is SO2, CO; Z5 is alkyl, phenyl, heterocyclic ring etc.; R2 is CONR8, O, S, NZ6, Z7-alkylene, alkylene etc.; R3 is H, alkyl, halogen, CF3 etc.; R4 is H, (substituted) alkyl etc.; n, t is 1-4). The compounds of the formula (I) can bind to receptors of PGE2 and show antagonistic activity against the action thereof or agonistic activity. Therefore, they are considered to be useful as medicine for inhibition of uterine contraction, analgesics, antidiarrheals, sleep inducers, medicine for increase of vesical capacity or medicine for uterine contraction, cathartic, suppression of gastric acid secretion, antihypertensive or diuretic agents.

A sulfonamide or carbonamide derivative of the formula (I)

(wherein
each, independently, is a C5-15 carbocyclic ring,
Z1 is
—COR1,
—C1-4 alkylene-COR1,
—CH═CH—COR1,
—C≡COR1, or
—O—C1-3 alkylene-COR1,
(wherein, R1 is hydroxy, C1-4 alkoxy or formula
NR6R7
(wherein, R6 and R7 each, independently, is H or C1-4 alkyl), or
—C1-5 alkylene-OH,
Z2 is H, C1-4 alkyl, C1-4 alkoxy, nitro, halogen, trifluoromethyl, trifluoromethoxy, hydroxy or COR1 (wherein R1 is as defined hereinbefore)),
Z3 is single bond or C1-4 alkylene,
Z4is SO2or CO,
Z5 is
(1) C1-8 alkyl, C2-8 alkenyl, or C2-8 alkynyl,
(2) phenyl, C3-7 cycloalkyl, or 5-7 membered heterocyclic ring containing one or two oxygen, sulfur or nitrogen atom(s), or
(3) C1-4 alkyl, C2-4 alkenyl or C2-4 alkynyl substituted by phenyl or C3-7 cycloalkyl (phenyl, C3-7 cycloalkyl and 5-7 membered heterocyclic ring containing one or two oxygen, sulfur or nitrogen atom(s) mentioned in the above (2) and (3) may be substituted by 1-5 of R5 (wherein R5 (if two or more R5, each independently) is H, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, nitro, halogen trifluoromethyl, trifluoromethoxy or hydroxy)),
R2 is
alkoxy or C(O)NH,
R3 is H, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, nitro, halogen, trifluoromethyl, trifluoromethoxy, hydroxy or hydroxymethyl,
R4is
(1) H,
(2) C1-18 alkyl, C2-8 alkenyl, or C2-8 alkynyl,
(3) C1-6 alkyl substituted by one or two substituent(s) selected from the group consisting of COOZ8, CONZ9Z0, and OZ8 (wherein Z8, Z9 and Z10 each, independently, is H or C1-4 alkyl) and C1-4 alkoxy-C1-4 alkoxy,
(4) C3-7 cycloalkyl, or
(5) C1-4 alkyl, C2-4 alkenyl or C2-4 alkynyl substituted by phenyl or C3-7 cycloalkyl (phenyl and C3-7 cycloalkyl mentioned in the above (4) and (5) may be substituted by 1-5 of R5 (wherein R5 is as defined hereinbefore)), and
n and t each, independently, is an integer of 1-4,
with the proviso that (1) R2 and Z3 should be connected at the 1- or 2-position of
(2) when
is a benzene ring and (Z2)t is other than COR1, Z1 should be connected at the 3- or 4-position of the benzene ring and (3) the compounds wherein
are excluded, or a non-toxic salt thereof.

30 more elements

Abstract

Claims7