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US4080463A
Expired / Lapsed
US
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2-Substituted-aminopropoxy indoles
Assignee: Sandoz AG
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Filing: 1976-08-05
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Granted: 1978-03-21
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Expires: 1996-08-05
Abstract
Abstract This invention provides compounds of formula I, <IMAGE> I wherein R1 is alkyl, alkenyl or alkinyl of up to 9 carbon atoms, or 1-ethinylcycloalkyl, R2 is hydrogen, halogen of atomic number from 17 to 35 or methyl, R3 is halogen of atomic number from 17 to 35 when R2 is hydrogen or methyl, and is methyl when R2 is halogen of atomic number from 17 to 35, and R4 is hydrogen or a R5Co- group wherein R5 is alkyl of 1 to 6 carbon atoms, phenoxy-alkyl, phenyl or substituted phenyl, WHICH ARE USEFUL, FOR EXAMPLE, FOR TREATING CORONARY CONDITIONS.
Inventors
- 👤 Franz Troxler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 05:05
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C07D209/30
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
171 words
A compound of formula I, ##STR32## wherein R 1 is alkyl, alkenyl or alkinyl of up to 9 carbon atoms, in which any multiple bond is in a position other than α,β to the nitrogen atom, or a 1-ethinylcycloalkyl of 5 or 6 ring carbon atoms, either R 2 is hydrogen or methyl, and R 3 is halogen of atomic number from 17 to 35, or R 2 is halogen of atomic number from 17 to 35, and R 3 is methyl, R 4 is hydrogen or R 5 CO--, wherein R 5 is alkyl of 1 to 6 carbon atoms; phenoxyalkyl, the alkyl residue of which is of 2 to 6 carbon atom and in which the phenyl residue is unsubstituted or monosubstituted with chlorine; phenyl; phenyl mono-, di- or trisubstituted with alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; or phenyl mono- or disubstituted with halogen of atomic number from 9 to 35, or a pharmaceutically acceptable acid addition salt form thereof.
Claim 2
Dependent Claim
171 words
A compound of formula I, ##STR32## wherein R 1 is alkyl, alkenyl or alkinyl of up to 9 carbon atoms, in which any multiple bond is in a position other than α,β to the nitrogen atom, or a 1-ethinylcycloalkyl of 5 or 6 ring carbon atoms, either R 2 is hydrogen or methyl, and R 3 is halogen of atomic number from 17 to 35, or R 2 is halogen of atomic number from 17 to 35, and R 3 is methyl, R 4 is hydrogen or R 5 CO--, wherein R 5 is alkyl of 1 to 6 carbon atoms; phenoxyalkyl, the alkyl residue of which is of 2 to 6 carbon atom and in which the phenyl residue is unsubstituted or monosubstituted with chlorine; phenyl; phenyl mono-, di- or trisubstituted with alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; or phenyl mono- or disubstituted with halogen of atomic number from 9 to 35, or a pharmaceutically acceptable acid addition salt form thereof.
Claim 3
Dependent Claim
8 words
A compound of claim 1 which is 4-(2-benzoyloxy-3-tert.butylaminopropoxy)-3-chloro-2-methylindole.
Claim 4
Dependent Claim
42 words
A pharmaceutical composition for the treatment of heart rhythm disorders comprising an antiarrhythmic effective amount of a compound of claim 1, in free base form or in pharmaceutically acceptable acid addition salt form, in association with a pharmaceutically acceptable diluent or carrier.
Claim 5
Dependent Claim
32 words
A method of treating heart rhythm disorders in animals which comprises administering to an animal in need of such treatment a anti-heart rhythm disorder effective amount of a compound of claim 1.
Claim 6
Dependent Claim
8 words
A compound of claim 1 which is 3-tert.butylamino-1-(3-chloro-4-indolyloxy)-2-propanol.
Claim 7
Dependent Claim
28 words
A compound of claim 1 wherein R 1 is --C(CH 3 ) 3 , R 2 is Br, R 3 is CH 3 and R 4 is hydrogen.
Claim 8
Dependent Claim
28 words
A compound of claim 1 wherein R 1 is --C(CH 3 ) 3 , R 2 is Cl, R 3 is CH 3 and R 4 is hydrogen.
Claim 9
Dependent Claim
29 words
A compound of claim 1 wherein R 1 is --C(CH 3 ) 3 , R 2 is CH 3 , R 3 is Br and R 4 is hydrogen.
Claim 10
Dependent Claim
25 words
A compound of claim 1 wherein R 1 is ##STR33## R 2 is CH 3 , R 3 is Br and R 4 is hydrogen.
Claim 11
Dependent Claim
25 words
A compound of claim 1 wherein R 1 is ##STR34## R 2 is CH 3 , R 3 is Cl and R 4 is hydrogen.
Claim 12
Dependent Claim
25 words
A compound of claim 1 wherein R 1 is ##STR35## R 2 is CH 3 , R 3 is Cl and R 4 is hydrogen.
Claim 13
Dependent Claim
22 words
A compound of the formula ##STR36## wherein R 1 , R 2 , and R 3 are as defined in claim 1.
Claim 14
Dependent Claim
86 words
A compound of the formula ##STR37## wherein R 1 , R 2 , and R 3 are as defined in claim 1; and R 5 represents alkyl of 1-6 carbon atoms; phenoxyalkyl, the alkyl residue of which is of 2-6 carbon atoms and in which the phenyl residue is unsubstituted or mono-substituted with chlorine; phenyl; phenyl mono-, di- or tri-substituted with alkyl of 1-4 carbon atoms or alkoxy of 1-4 carbon atoms; or phenyl mono- or di-substituted with halogen of atomic number from 9 to 35.
Claim 15
Dependent Claim
33 words
A compound of claim 13 wherein R 1 is --C(CH 3 ) 3 , R 2 is CH 3 , R 3 is Br and R 5 is --C(CH 3 ) 3 .
Claim 16
Dependent Claim
29 words
A compound of claim 13 wherein R 1 is ##STR38## R 2 is CH 3 , R 3 is Cl and R 5 is --C(CH 3 ) 3 .
Claim 17
Dependent Claim
33 words
A compound of claim 13 wherein R 1 is --C(CH 3 ) 3 , R 2 is CH 3 , R 3 is Cl and R 5 is --C(CH 3 ) 3 .
Claim 18
Dependent Claim
28 words
A compound of claim 13 wherein R 1 is --C(CH 3 ) 3 , R 2 is Cl, R 3 is CH 3 and R 5 is ##STR39##
Claim 19
Dependent Claim
32 words
A compound of claim 13 wherein R 1 is --C(CH 3 ) 3 , R 2 is Br, R 3 is CH 3 and R 5 is --C(CH 3 ) 3 .
References Cited (Backward Citations)
US3471515A
Cited
US3751429A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-03-20 | 1981-09-19 | 1982-03-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-20 | 1985-09-19 | 1986-03-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-20 | 1989-09-19 | 1990-03-21 | $7700.00 | Window Closed / Lapsed |