Patent US4405635A successfully refreshed from Google Patents.
US4405635A
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4-Aroylimidazol-2-ones and their use as pharmaceuticals
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1982-09-13
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Granted: 1983-09-20
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Expires: 2002-09-13
Abstract
Abstract Novel 4-aroylimidazol-2-ones of the following general structure which are useful as antihypertensives, cardiotonics, antithrombotics, bronchodilators and uterospasmolytics ##STR1## wherein Ar is 2-furyl, 2-thienyl or phenyl, the latter of which may optionally be substituted with one or two X groups; X is halogen, hydroxy, C 1-4 alkyl, C 1-4 alkoxy, methylenedioxy, C 1-4 alkylthio, C 1-4 alkylsulfoxide, C 1-4 alkylsulfone, CF 3 , --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino, R is hydrogen, C 1-4 alkyl, C 1-4 alkylcarbonyl or benzyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or C 1-4 alkyl; and the pharmaceutically acceptable salts thereof.
Inventors
- 👤 Richard A. Schnettler
- 👤 Richard C. Dage
- 👤 Johann M. Grisar
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 09:19
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/70
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
283 words
A compound of the formula ##STR11## wherein Ar is 2-furyl, 2-thienyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkyl of from 2 to 4 carbon atoms, or when X 3 is at the meta position X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms with the proviso that both R 3 and R 4 cannot be hydrogen; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
283 words
A compound of the formula ##STR11## wherein Ar is 2-furyl, 2-thienyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkyl of from 2 to 4 carbon atoms, or when X 3 is at the meta position X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms with the proviso that both R 3 and R 4 cannot be hydrogen; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
29 words
A compound of claim 1 wherein R is hydrogen and R 1 is hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms.
Claim 4
Dependent Claim
17 words
A compound of claim 1 wherein R is hydrogen and R 1 is hydrogen, methyl or ethyl.
Claim 5
Dependent Claim
14 words
A compound of claim 3 wherein Ar is phenyl monosubstituted with X 1 .
Claim 6
Dependent Claim
53 words
A compound of claim 4 wherein X 1 is a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, or a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms or a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms.
Claim 7
Dependent Claim
13 words
A compound of claim 5 wherein X 1 is at the para position.
Claim 8
Dependent Claim
15 words
A compound of claim 6 wherein X 1 is methylthio and R 1 is methyl.
Claim 9
Dependent Claim
29 words
A compound of claim 3 wherein Ar is disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 .
Claim 10
Dependent Claim
13 words
A compound of claim 8 wherein X 3 is at the meta position.
Claim 11
Dependent Claim
38 words
A compound of claim 9 wherein X 2 and X 3 are straight or branched chain lower alkoxy of from 1 to 4 carbon atoms or together may be methylenedioxy optionally substituted by one or two methyl groups.
Claim 12
Dependent Claim
18 words
A compound of claim 10 wherein R 1 is methyl and X 2 and X 3 are methoxy.
Claim 13
Dependent Claim
19 words
A compound of claim 11 wherein R 1 is methyl and X 2 and X 3 together are methylenedioxy.
Claim 14
Independent Claim
299 words
A method for the treatment of cardiac failure in a patient in need thereof which comprises administering to said patient a cardiotonically effective amount of a compound of the formula ##STR12## wherein Ar is 2-furyl, 2-thienyl, phenyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, or a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, or when X 3 is at the meta position, X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
Claim 15
Independent Claim
299 words
A method for the treatment of cardiac failure in a patient in need thereof which comprises administering to said patient a cardiotonically effective amount of a compound of the formula ##STR12## wherein Ar is 2-furyl, 2-thienyl, phenyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, or a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, or when X 3 is at the meta position, X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
Claim 16
Independent Claim
299 words
A method for the treatment of bronchial asthma in a patient in need thereof which conprises administering to said patient a bronchodilitory effective amount of a compound of the formula ##STR13## wherein Ar is 2-furyl, 2-thienyl, phenyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, or a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, or when X 3 is at the meta position, X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
Claim 17
Independent Claim
299 words
A method for the treatment of bronchial asthma in a patient in need thereof which conprises administering to said patient a bronchodilitory effective amount of a compound of the formula ##STR13## wherein Ar is 2-furyl, 2-thienyl, phenyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, or a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, or when X 3 is at the meta position, X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
Claim 18
Independent Claim
299 words
A method for the treatment of premature labor in a patient in need thereof which comprises administering to said patient a uterospasmolytically effective amount of a compound of the formula ##STR14## wherein Ar is 2-furyl, 2-thienyl, phenyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, or a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, or when X 3 is at the meta position, X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
Claim 19
Independent Claim
299 words
A method for the treatment of premature labor in a patient in need thereof which comprises administering to said patient a uterospasmolytically effective amount of a compound of the formula ##STR14## wherein Ar is 2-furyl, 2-thienyl, phenyl, phenyl monosubstituted at the ortho, meta or para position with X 1 , or disubstituted phenyl substituted at the para position with X 2 and at the ortho or meta position with X 3 ; X 1 is halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, a straight or branched chain lower alkylthio of from 1 to 4 carbon atoms, a straight or branched chain lower alkylsulfoxide of from 1 to 4 carbon atoms, or a straight or branched chain lower alkylsulfone of from 1 to 4 carbon atoms, trifluoromethyl, --SO 2 N(R 2 ) 2 , NR 3 R 4 , pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino; X 2 and X 3 are halogen, hydroxy, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkoxy of from 1 to 4 carbon atoms, or when X 3 is at the meta position, X 2 and X 3 together may be methylenedioxy optionally substituted by one or two methyl groups; R is hydrogen, a straight or branched chain lower alkyl of from 1 to 4 carbon atoms, a straight or branched chain lower alkylcarbonyl of from 1 to 4 carbon atoms, or a benzoyl; each of R 1 , R 2 , R 3 and R 4 are hydrogen or a straight or branched chain lower alkyl of from 1 to 4 carbon atoms; or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
32 words
A method of claim 13 wherein R is hydrogen, R 1 is a methyl group, and Ar is a 4-(methylthio)-phenyl group, that is the compound, 1,3-dihydro-4-methyl-5-[4-(methylthio)benzoyl]-2H-imidazol-2-one or a pharmaceutically acceptable salt thereof.
References Cited (Backward Citations)
US2441933A
Cited
US2514380A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-09-19 | 1987-03-21 | 1987-09-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-09-19 | 1991-03-21 | 1991-09-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-09-19 | 1995-03-21 | 1995-09-20 | $7700.00 | Window Closed / Lapsed |