US4160098A
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Pyrazole derivatives
Assignee: Bayer AG
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Filing: 1977-04-28
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Granted: 1979-07-03
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Expires: 1997-04-28
Abstract
Abstract Pyrazole derivatives of the formula: ##STR1## and pharmaceutically acceptable nontoxic salts thereof wherein R is hydrogen, trifluoromethyl or alkyl; R 1 is hydrogen or alkyl; R 2 is alkyl; R 3 is an unsubstituted or substituted aryl moiety; R 3 is naphthyl or pyridyl; and R 4 is R 5 CO wherein R 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 4 is Z-SO 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.
Inventors
- 👤 Eike Moller
- 👤 Karl Meng
- 👤 Egbert Wehinger
- 👤 Harald Horstmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 10:56
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/18; C07D231/20
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
211 words
A compound of the formula: ##STR35## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen or lower alkyl; R 1 is hydrogen or lower alkyl; R 2 is lower alkyl; R 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) one substituent selected from the group consisting of cycloalkyl of 5 to 7 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms and 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 6 carbon atoms, halogen and trifluoromethyl; or R 3 is naphthyl; and R 4 is R 5 CO wherein R 5 is pyrryl, thienyl, furyl, dihydrofuryl, tetrahydrofuryl, tetrahydropyranyl or tetrahydrothiopyranyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of halogen, alkyl of 1 to 4 carbon atoms, and nitro.
Claim 2
Dependent Claim
211 words
A compound of the formula: ##STR35## or a pharmaceutically acceptable nontoxic salt thereof wherein R is hydrogen or lower alkyl; R 1 is hydrogen or lower alkyl; R 2 is lower alkyl; R 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) one substituent selected from the group consisting of cycloalkyl of 5 to 7 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms and 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 6 carbon atoms, halogen and trifluoromethyl; or R 3 is naphthyl; and R 4 is R 5 CO wherein R 5 is pyrryl, thienyl, furyl, dihydrofuryl, tetrahydrofuryl, tetrahydropyranyl or tetrahydrothiopyranyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of halogen, alkyl of 1 to 4 carbon atoms, and nitro.
Claim 3
Dependent Claim
177 words
A compound according to claim 1 wherein R is hydrogen or alkyl of 1 to 4 carbon atoms; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is alkyl of 1 to 4 carbon atoms; R 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 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, and alkoxy of 1 to 4 carbon atoms; (b) one substituent selected from the group consisting of cycloalkyl of 5 to 7 carbon atoms, cycloalkenyl of 5 to 7 carbon atoms and nitro; or (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 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen and trifluoromethyl; or R 3 is naphthyl.
Claim 4
Dependent Claim
33 words
A compound according to claim 2 wherein R 3 is phenyl substituted by 1 or 2 of the same or different substituents selected from the group consisting of chlorine, fluorine, methyl and trifluoromethyl.
Claim 5
Dependent Claim
47 words
A compound according to claim 3 wherein R is methyl; R 1 is hydrogen or methyl; R 2 is methyl; and R 3 is phenyl substituted by 1 or 2 of the same or different substituents selected from the group consisting of chlorine, fluorine, methyl and trifluoromethyl.
Claim 6
Dependent Claim
116 words
A compound according to claim 1 wherein R is hydrogen or alkyl of 1 to 4 carbon atoms; R 1 is hydrogen or alkyl of 1 to 4 carbon atoms; R 2 is alkyl of 1 to 4 carbon atoms; R 3 is phenyl substituted by 1 or 2 of the same or different substituents selected from the group consisting of halogen, alkyl of 1 or 2 carbon atoms and trifluoromethyl; or naphthyl; and R 4 is R 5 CO wherein R 5 is pyrryl, thienyl, furyl, dihydrofuryl, tetrahydrofuryl, tetrahydropyranyl or tetrahydrothiopyranyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of alkyl of 1 or 2 carbon atoms, halogen and nitro.
Claim 7
Dependent Claim
96 words
A compound according to claim 1 wherein R is hydrogen or alkyl of 1 to 3 carbon atoms; R 1 is hydrogen, methyl or ethyl; R 2 is alkyl of 1 to 3 carbon atoms; R 3 is phenyl substituted by 1 or 2 substituents selected from the group consisting of methyl, fluorine, chlorine and trifluoromethyl; or naphthyl; and R 4 is R 5 CO wherein R 5 is a heterocycle selected from the group consisting of pyrryl, thienyl, furyl, dihydrofuryl, tetra-hydrofuryl, tetratydropyranyl, tetrahydrothiopyranyl unsubstituted or substituted by methyl, ethyl, mono- or di-chloro, fluoro or nitro.
Claim 8
Dependent Claim
52 words
A compound according to claim 1 wherein R is methyl; R 1 is hydrogen; R 2 is methyl; R 3 is phenyl substituted by 1 or 2 members selected from the group consisting of methyl, chlorine or fluorine; and R 4 is R 5 CO wherein R 5 is thienyl or furyl.
Claim 9
Dependent Claim
40 words
A compound according to claim 1 wherein R is methyl; R 1 is hydrogen; R 2 is methyl; R 3 is phenyl substituted by fluorine, chlorine and methyl or by 2 chlorine atoms; and R 4 is thienylcarbonyl or furylcarbonyl.
Claim 10
Dependent Claim
9 words
The compound according to claim 1 which is ##STR36##
Claim 11
Dependent Claim
9 words
The compound according to claim 1 which is ##STR37##
References Cited (Backward Citations)
US2476986A
Cited
US3976658A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-07-02 | 1983-01-01 | 1983-07-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-07-02 | 1987-01-01 | 1987-07-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-07-02 | 1991-01-01 | 1991-07-03 | $7700.00 | Window Closed / Lapsed |