US 4,069,334 A · Pyrazole derivatives

Abstract

Pyrazole derivatives of the formula: ##STR1## and pharmaceutically acceptable nontoxic salts thereof WHEREIN R is hydrogen, trifluoromethyl or alkyl; R.sup.1 is hydrogen or alkyl; R.sup.2 is alkyl; R.sup.3 is aryl substituted by: A. one or two of the same or different substituents selected from the group consisting of halogen, trifluoromethyl, alkyl, alkenyl and alkoxy; B. one substituent selected from the group consisting of alkylamino, dialkylamino wherein the alkyl moieties may form a heterocyclic ring with the nitrogen atom to which they are attached, cycloalkyl, cycloalkenyl, trifluoromethoxy, nitro, cyano, carbonamido unsubstituted or substituted by 1 or 2 alkyl moieties, sulphonamido unsubstituted or substituted by 1 or 2 alkyl moieties, and SO.sub.n -alkyl wherein n is 0, 1 or 2; C. one substituent selected from the group consisting of alkylamino, dialkylamino wherein the alkyl moieties may form a heterocyclic ring with the nitrogen atom to which they are attached, cycloalkyl, cycloalkenyl, trifluoromethoxy, nitro, cyano, carbonamido unsubstituted or substituted by 1 or 2 alkyl moieties, sulphonamido unsubstituted or substituted by 1 or 2 alkyl moieties, and SO.sub.n -alkyl wherein n is 0, 1 or 2, and by one or two substituents selected from the group consisting of alkyl, alkenyl, alkoxy, halogen and trifluoromethyl; or D. two substituents on the aryl moiety form a branched or unbranched saturated or unsaturated 5- to 7-membered isocyclic or heterocyclic ring, which ring can also have 1 or 2 oxygen atoms or sulfur atoms; or SO.sub.n -alkyl wherein n is 0, 1 or 2; or R.sup.3 is naphthyl or pyridyl; and R.sup.4 is R.sup.5 CO wherein R.sup.5 is alkyl unsubstituted or substituted by 1, 2 or 3 halogen moieties, by alkoxy, or by mono- or dialkylamino; lower alkoxy; dialkylamino; thiophene; phenyl unsubstituted or substituted by 1 or 2 alkyl, trifluoromethyl, alkoxy, nitro or halogen moieties; or a 5- to 7-membered heterocycle unsubstituted or substituted by 1 or 2 halogen, alkyl or nitro moieties; or R.sup.4 is Z-SO.sub.2 wherein Z is alkyl, phenyl or phenyl substituted by 1 or 2 alkyl, halogen, nitro, trifluoromethyl or trifluoromethylsulphonyl moieties; or dichloroquinoxalinyl. The pyrazole derivatives and their salts are useful as diuretics, saluretics and antihypertensives.

Claims23

Dependent claims

A pharmaceutical composition useful for effecting diuresls and saluresis and for treating hypertension in humans and animals which comprises a diuretically effective amount, a saluretically effective amount or an antihypertensive amount of a compound of the formula:

##STR38## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen, trifluoromethyl or lower alkyl;
R.sup.1 is hydrogen, trifluoromethyl or lower alkyl;
R.sup.2 is lower alkyl;
R.sup.3 is phenyl substituted by:
a. one or two of the same or different substituents selected from the group consisting of halogen, trifluoromethyl, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, and alkoxy of 1 to 6 carbon atoms;
b. cycloalkyl of 5 to 7 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms or nitro;
c. one substituent selected from the group consisting of cycloalkyl of 5 to 7 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms and nitro and one or two substituents selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and trifluoromethyl;
or
R.sup.3 is naphthyl;
and
R.sup.4 is R.sup.5 CO wherein R.sup.5 is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, trifluoromethyl, nitro and halogen,
in combination with a phamaceutically acceptable non-toxic inert diluent or carrier.

9 more elements

A method of effecting diuresis or saluresis in humans and animals or treating hypertension in humans and animals which comprises administering to a human or animal in need thereof a diuretically effective amount, a saluretically effective amount or an antihypertensive amount of a compound of the formula:

##STR43## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen, trifluoromethyl or lower alkyl;
R.sup.1 is hydrogen or lower alkyl;
R.sup.2 is lower alkyl;
R.sup.3 is phenyl substituted by:
a. one or two of the same or different substituents selected from the group consisting of halogen, trifluoromethyl, alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, and alkoxy of 1 to 6 carbon atoms;
b. cycloalkyl of 5 to 7 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms or nitro;
c. one substituent selected from the group consisting of cycloalkyl of 5 to 7 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms and nitro and one or two substituents selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl of 2 to 8 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and trifluoromethyl;
or
R.sup.3 is naphthyl;
and
R.sup.4 is R.sup.5 CO wherein R.sup.5 is phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkyl of 1 to b 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, trifluoromethyl, nitro and halogen,
in combination with a pharmaceutically acceptable non-toxic inert diluent or carrier

9 more elements

Dependencies are inferred from the claim text.

Pyrazole derivatives

Life of this patent

Pyrazole derivatives

Life of this patent

Abstract

Claims23