US3965095A
Expired / Lapsed
US
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Oxindole derivatives
Assignee: Sandoz AG
•
Filing: 1973-06-18
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Granted: 1976-06-22
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Expires: 1993-06-18
Abstract
Abstract The present invention concerns novel oxindole derivatives of the formula, ##SPC1## Wherein R 1 and R 2 are saturated or unsaturated substituted or unsubstituted hydrocarbon radicals, useful as antiarrhythmic and β-blocking agents.
Inventors
- 👤 Fritz Seemann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 08:36
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/32; C07D209/34
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
308 words
A compound of the formula: ##SPC8## wherein R 1 is (i) alkyl of 1 to 4 carbon atoms, (ii) cycloalkyl of 3 to 8 carbon atoms, (iii) phenylalkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms, (iv) phenyl alkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms and being monosubstituted by alkoxy or alkyl of 1 to 4 carbon atoms, (v) alkenyl or alkinyl of 3 to 7 carbon atoms, or (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, and R 2 is (i) phenyl, (ii) phenyl monosubstituted by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, (iii) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, (iv) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, monosubstituted in the phenyl ring thereof by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, (v) pyridyl or thienyl (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, (vii) adamantyl, (viii) haloalkyl of 2 to 12 carbon atoms, the halogen thereof being located in other than the α position, or, when R 1 is alkenyl of 3 to 7 carbon atoms (ix) alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, or cycloalkyl of 3 to 6 carbon atoms mono- or poly-substituted by alkyl of 1 to 4 carbon atoms, furyl or tetrahydropyranyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
308 words
A compound of the formula: ##SPC8## wherein R 1 is (i) alkyl of 1 to 4 carbon atoms, (ii) cycloalkyl of 3 to 8 carbon atoms, (iii) phenylalkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms, (iv) phenyl alkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms and being monosubstituted by alkoxy or alkyl of 1 to 4 carbon atoms, (v) alkenyl or alkinyl of 3 to 7 carbon atoms, or (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, and R 2 is (i) phenyl, (ii) phenyl monosubstituted by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, (iii) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, (iv) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, monosubstituted in the phenyl ring thereof by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, (v) pyridyl or thienyl (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, (vii) adamantyl, (viii) haloalkyl of 2 to 12 carbon atoms, the halogen thereof being located in other than the α position, or, when R 1 is alkenyl of 3 to 7 carbon atoms (ix) alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, or cycloalkyl of 3 to 6 carbon atoms mono- or poly-substituted by alkyl of 1 to 4 carbon atoms, furyl or tetrahydropyranyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
8 words
The compound of claim 1, which is 4-[2-(1-adamantylcarbonyloxy)-3-allylaminopropoxy]oxindole.
Claim 4
Dependent Claim
8 words
The compound of claim 1, which is 4-(3-tert-butylamino-2-nicotinoyloxypropoxy)oxindole.
Claim 5
Dependent Claim
8 words
The compound of claim 1, which is 4-[3-tert-butylamino-2-(2-thenoyloxy)propoxy]oxindole.
Claim 6
Dependent Claim
8 words
The compound of claim 1, which is 4-(3-tert-butylamino-2-cinnamoyloxypropoxy)oxindole.
Claim 7
Dependent Claim
8 words
The compound of claim 1, which is 4-(2-benzoyloxy-3-tert-butylaminopropoxy)oxindole.
Claim 8
Dependent Claim
10 words
The compound of claim 1, which is Malonic acid ethyl-[3-tert-butylamino-1-(2-oxo-4-indolyloxy)propyl]ester.
Claim 9
Dependent Claim
8 words
The compound of claim 1, which is 4-(3-tert-butylamino-2-phenylacetoxypropoxy)oxindole.
Claim 10
Dependent Claim
9 words
The compound of claim 1, which is 4-[3-tert-butylamino-2-( 4-chlorobutyryloxy)propoxy]oxindole.
Claim 11
Dependent Claim
8 words
The compound of claim 1, which is 4-[2-(2-chlorobenzoyloxy)-3-(2-methyl-3-butin-2-ylamino)propoxy]oxindole.
Claim 12
Dependent Claim
8 words
The compound of claim 1, which is 4-[2-(4-methylbenzoyloxy)-3-(2-methyl-4-phenyl-2-butylamino)propoxy]oxindole.
Claim 13
Dependent Claim
11 words
The compound of claim 1, which is 2-methyl-2-[2-(3-methoxybenzoyloxy)-3-(2-oxo-4-indolyloxy)propylamino]propionic acid ethyl ester.
Claim 14
Dependent Claim
8 words
The compound of claim 1, which is 4-[3-cyclohexylamino-2-(2-thenoyloxy)propoxy]oxindole.
Claim 15
Dependent Claim
8 words
The compound of claim 1, which is 4-(3-allylamino-2-pivaloyloxypropoxy)oxindole.
Claim 16
Dependent Claim
8 words
The compound of claim 1, which is 4-[3-allylamino-2-(1-methylcyclohexylcarbonyloxy)propoxy]oxindole.
Claim 17
Dependent Claim
9 words
The compound of claim 1, which is 4-{3-[2-(4-methoxyphenyl)ethylamino]-2-pivaloyloxypropoxy} oxindole.
Claim 18
Dependent Claim
8 words
The compound of claim 1, which is 4-[3-(2-methyl-3-buten-2-ylamino)-2-(4-tetrahydropyranylcarbonyloxy)propoxy]oxindole.
Claim 19
Dependent Claim
8 words
The compound of claim 1, which is 4-(2-benzoyloxy-3-isopropylaminopropoxy)oxindole.
Claim 20
Dependent Claim
8 words
The compound of claim 1, which is 4-[3-(3-pentylamino)-2-(2-thenoyloxy)propoxy]oxindole.
Claim 21
Dependent Claim
26 words
A compound of the formula, ##SPC9## wherein R 1 " is alkenyl of 3 to 7 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
26 words
A compound of the formula, ##SPC9## wherein R 1 " is alkenyl of 3 to 7 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 23
Dependent Claim
8 words
The compound of claim 20, which is 4-(3-allylamino-2-hydroxypropoxy)oxindole.
Claim 24
Dependent Claim
8 words
The compound of claim 20, which is 4-[2-hydroxy-3-(2-methyl-3-buten-2-ylamino)propoxy]oxindole.
Claim 25
Dependent Claim
10 words
A compound of claim 1, wherein R 1 is alkenyl.
Claim 26
Dependent Claim
14 words
A compound of claim 1, wherein R 1 is branched in the α position.
Claim 27
Dependent Claim
10 words
A compound of claim 24, wherein R 1 is alkyl.
Claim 28
Dependent Claim
27 words
A compound of claim 25, wherein R 2 is phenyl, phenyl monosubstituted by halogen of atomic number from 9 to 35, alkyl or alkoxy, pyridyl or thienyl.
Claim 29
Dependent Claim
12 words
A compound of claim 26, wherein R 2 is phenyl or thienyl.
Claim 30
Dependent Claim
33 words
A compound of claim 1, wherein R 1 is alkenyl or alkyl, and R 2 is phenyl, pyridyl, thienyl, adamantyl, styryl, or haloalkyl, the halogen being of atomic number from 17 to 35.
Claim 31
Dependent Claim
20 words
A compound of claim 1, wherein R 2 is thienyl or pyridyl or, when R is alkenyl, furyl or tetrahydropyranyl.
Claim 32
Dependent Claim
306 words
A compound of the formula: ##SPC10## wherein R 1 is (i) alkyl of 3 to 5 carbon atoms, (ii) cycloalkyl of 3 to 8 carbon atoms, (iii) phenylalkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms, (iv) phenyl alkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms and being monsubstituted by alkoxy or alkyl of 1 to 4 carbon atoms, (v) alkenyl or alkinyl of 3 to 7 carbon atoms, or (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, and is (i) phenyl, (ii) phenyl monosubstituted by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, (iii) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, (iv) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, monosubstituted in the phenyl ring thereof by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms (v) pyridyl or thienyl (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, (vii) adamantyl, (viii) haloalkyl of 2 to 12 carbon atoms, the halogen thereof being located in other than the α position, or, when R 1 is alkenyl of 3 to 7 carbon atoms (ix) alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, or cycloalkyl of 3 to 6 carbon atoms mono- or poly-substituted by alkyl of 1 to 4 carbon atoms, furyl or tetrahydropyranyl or a pharmaceutically acceptable acid addition salt thereof.
Claim 33
Dependent Claim
306 words
A compound of the formula: ##SPC10## wherein R 1 is (i) alkyl of 3 to 5 carbon atoms, (ii) cycloalkyl of 3 to 8 carbon atoms, (iii) phenylalkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms, (iv) phenyl alkyl of 8 to 12 carbon atoms in the aggregate thereof, the phenyl ring thereof being separated from the nitrogen atom by at least two carbon atoms and being monsubstituted by alkoxy or alkyl of 1 to 4 carbon atoms, (v) alkenyl or alkinyl of 3 to 7 carbon atoms, or (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, and is (i) phenyl, (ii) phenyl monosubstituted by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, (iii) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, (iv) phenylalkyl of 7 to 12 carbon atoms in the aggregate thereof or styryl, monosubstituted in the phenyl ring thereof by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms (v) pyridyl or thienyl (vi) alkoxycarbonylalkyl, the alkyl moiety having 1 to 6 carbon atoms and the alkoxy moiety having 1 to 4 carbon atoms, (vii) adamantyl, (viii) haloalkyl of 2 to 12 carbon atoms, the halogen thereof being located in other than the α position, or, when R 1 is alkenyl of 3 to 7 carbon atoms (ix) alkyl of 1 to 12 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, or cycloalkyl of 3 to 6 carbon atoms mono- or poly-substituted by alkyl of 1 to 4 carbon atoms, furyl or tetrahydropyranyl or a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
US3705907A
Cited
US3825558A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-22 | 1979-12-22 | 1980-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-22 | 1983-12-22 | 1984-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-22 | 1987-12-22 | 1988-06-22 | $7700.00 | Window Closed / Lapsed |