Patent US3976695A successfully refreshed from Google Patents.
US3976695A
Expired / Lapsed
US
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Halogen substituted α-(aminoalkyl)-3,4-dihydroxybenzyl alcohols
Assignee: GlaxoSmithKline LLC
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Filing: 1970-01-13
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Granted: 1976-08-24
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Expires: 1990-01-13
Abstract
Abstract Halogen substituted α-(aminoalkyl)-3,4-dihydroxybenzyl alcohols having β-adrenergic stimulant activity, particularly as selective bronchodilators. The α-aminomethyl derivatives are prepared by the condensation of an appropriately substituted styrene oxide with a primary amine followed by removal of the ether protective group(s). The α-aminoethyl or α-aminopropyl derivatives are prepared by the condensation of an appropriately substituted α-bromoalkyl phenyl ketone with an N-benzyl secondary amine followed by reduction of the ketone moiety and removal of the ether protective group(s).
Inventors
- 👤 Carl Kaiser
- 👤 Stephen R. Ross
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 22:27
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/22; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/178; C07C43/1786; C07C45/00; C07C45/27; C07C45/29; C07C45/298; C07C45/56; C07C45/562; C07C45/565; C07C45/61; C07C45/63; C07C45/67; C07C45/673; C07C45/68; C07C45/70; C07C45/71; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
77 words
A chemical compound of the formula: ##SPC5## or a pharmaceutically acceptable acid addition salt C. said compound, wherein: R is hydrogen or methyl; R 1 is chlorine, bromine or fluorine; R 2 is branched chain lower alkyl of from 3 to 5 carbon atoms, cycloalkyl or cycloalkylmethyl, the cycloalkyl moiety having from 3 to 6 carbon atoms; or ##SPC6## R 3 is hydrogen, methyl or ethyl; and R 4 and R 5 are hydrogen, hydroxy or methoxy.
Claim 2
Dependent Claim
77 words
A chemical compound of the formula: ##SPC5## or a pharmaceutically acceptable acid addition salt C. said compound, wherein: R is hydrogen or methyl; R 1 is chlorine, bromine or fluorine; R 2 is branched chain lower alkyl of from 3 to 5 carbon atoms, cycloalkyl or cycloalkylmethyl, the cycloalkyl moiety having from 3 to 6 carbon atoms; or ##SPC6## R 3 is hydrogen, methyl or ethyl; and R 4 and R 5 are hydrogen, hydroxy or methoxy.
Claim 3
Dependent Claim
13 words
A chemical compound according to claim 1 in which R 1 is chlorine.
Claim 4
Dependent Claim
12 words
A chemical compound according to claim 2 in which R is hydrogen.
Claim 5
Dependent Claim
13 words
A chemical compound according to claim 3 in which R 3 is hydrogen.
Claim 6
Dependent Claim
13 words
A chemical compound according to claim 4 in which R 2 is isopropyl.
Claim 7
Dependent Claim
12 words
A chemical compound according to claim 5, being the compound 2-chloro-3,4-dihydroxy-α-(isopropylaminomethyl)-benzyl alcohol.
Claim 8
Dependent Claim
13 words
A chemical compound according to claim 4 in which R 2 is cyclopentyl.
Claim 9
Dependent Claim
12 words
A chemical compound according to claim 7, being the compound 6-chloro-α-(cyclopentylaminomethyl)-3,4-dihydroxybenzyl alcohol.
Claim 10
Dependent Claim
12 words
A chemical compound according to claim 7, being the compound 2-chloro-α-(cyclopentylaminomethyl)-3,4-dihydroxybenzyl alcohol.
Claim 11
Dependent Claim
12 words
A chemical compound according to claim 7, being the compound 5-chloro-α-(cyclopentylaminomethyl)-3,4-dihydroxybenzyl alcohol.
Claim 12
Dependent Claim
13 words
A chemical compound according to claim 4 in which R 2 is 3,4-dimethoxyphenylisopropyl.
Claim 13
Dependent Claim
12 words
A chemical compound according to claim 11, being the compound 5-chloro-α-[2-(3,4-dimethoxyphenyl)-1-methylethylaminomethyl]-3,4-dihydroxybenzyl alcohol.
Claim 14
Dependent Claim
17 words
A chemical compound according to claim 2 in which R is methyl and R 3 is hydrogen.
Claim 15
Dependent Claim
13 words
A chemical compound according to claim 13 in which R 2 is isopropyl.
Claim 16
Dependent Claim
12 words
A chemical compound according to claim 14, being the compound 5-chloro-α-(isopropylaminomethyl)-4-hydroxy-3-methoxybenzyl alcohol.
Claim 17
Dependent Claim
15 words
A chemical compound according to claim 3 in which R 3 is methyl or ethyl.
Claim 18
Dependent Claim
13 words
A chemical compound according to claim 16 in which R 2 is isopropyl.
Claim 19
Dependent Claim
17 words
A chemical compound according to claim 17 and R 3 is methyl, being the compound 2-chloro-3,4-dihydroxy-α-(1-isopropylaminoethyl)-benzyl alcohol.
Claim 20
Dependent Claim
17 words
A chemical compound according to claim 17 and R 3 is ethyl, being the compound 2-chloro-3,4-dihydroxy-α-(1-isopropylaminopropyl)-benzyl alcohol.
Claim 21
Dependent Claim
13 words
A chemical compound according to claim 2 in which R 1 is 2-chloro.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-08-24 | 1980-02-23 | 1980-08-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-08-24 | 1984-02-23 | 1984-08-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-08-24 | 1988-02-23 | 1988-08-24 | $7700.00 | Window Closed / Lapsed |