US3711545A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Alpha-aminoalkyl-4-hydroxy-3-sulfamoylaminobenzyl alcohols
Assignee: Smith Kline & French Laboratories Ltd
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Filing: 1971-02-23
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Granted: 1973-01-16
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Expires: 1991-02-23
Abstract
Abstract Alpha -Aminoalkyl-4-hydroxy-3-sulfamoylaminobenzyl alcohols having Beta -adrenergic stimulant activity, particularly as selective bronchodilators, are prepared generally from 3-amino-4benzyloxyphenones by, for example, reaction with a sulfamoyl chloride to give 3-sulfamoylaminophenones, bromination of these phenones and treatment of the resulting Alpha -bromo derivatives with an N-benzyl secondary amine, followed by catalytic hydrogenation to remove the benzyl groups and reduce the ketone moiety.
Inventors
- 👤 C Kaiser
- 👤 S Ross
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:47
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/16; A61K31/18; C; C07; C07C; C07C311/00; C07C311/30; C07C311/37
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
12 words
A chemical compound according to claim 1 in which R5 is hydrogen.
Claim 2
Dependent Claim
14 words
A chemical compound according to claim 2 in which R3 and R4 are methyl.
Claim 3
Dependent Claim
12 words
A chemical compound according to claim 3 in which R2 is hydrogen.
Claim 4
Dependent Claim
18 words
A chemical compound according to claim 4 in which R1 is t-butyl, being the compound Alpha -(t-butylaminomethyl)-4-hydroxy-3-(N,N-dimethylsulfamoylamino)-benzyl alcohol.
Claim 5
Dependent Claim
18 words
A chemical compound according to claim 4 in which R1 is cyclopentyl, being the compound Alpha -(cyclopentylaminomethyl)-4-hydroxy-3-(N,N-dimethylsulfamoylamino)-benzyl alcohol.
Claim 6
Dependent Claim
21 words
A chemical compound according to claim 1 in which R3 is hydrogen, R4 is methyl and R2 and R5 are hydrogen.
Claim 7
Dependent Claim
19 words
A chemical compound according to claim 7 in which R1 is isopropyl, being the compound 4-hydroxy- Alpha -(isopropylaminomethyl)-3-(N-methylsulfamoylamino)-benzyl alcohol.
Claim 8
Dependent Claim
14 words
A chemical compound according to claim 3 in which R2 is methyl or ethyl.
Claim 9
Dependent Claim
22 words
A chemical compound according to claim 9 in which R2 is ethyl and R1 is t-butyl, being the compound Alpha -(1-t-butylaminopropyl)-3-(N,N-dimethylsulfamoylamino)-4-hydroxybenzyl alcohol.
Claim 10
Dependent Claim
22 words
A chemical compound according to claim 9 in which R2 is methyl and R1 is t-butyl, being the compound Alpha -(1-t-butylaminoethyl)-3-(N,N-dimethylsulfamoylamino)-4-hydroxybenzyl alcohol.
Claim 11
Dependent Claim
83 words
A chemical compound of the formula: wherein: R1 is branched chain lower alkyl of from three to five carbon atoms, cycloalkyl or cycloalkylmethyl, the cycloalkyl moiety having from three to six carbon atoms, or R2 is hydrogen, methyl or ethyl; R3 and R4 are each hydrogen, methyl, ethyl or, taken together with the nitrogen atom to which they are attached, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl or N''-methyl-N-piperazinyl; R5 is hydrogen or methyl; and R6 and R7 are each hydrogen, hydroxy, methoxy or, taken together, methylenedioxy.
References Cited (Backward Citations)
US3634507A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1976-01-16 | 1976-07-17 | 1977-01-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-01-16 | 1980-07-17 | 1981-01-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-01-16 | 1984-07-17 | 1985-01-16 | $7700.00 | Window Closed / Lapsed |