US4288452A
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1-Aryloxy-3-nitratoalkylamino-2-propanols and use as β-receptor blocker
Assignee: Merck Patent GmbH
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Filing: 1979-02-09
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Granted: 1981-09-08
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Expires: 1999-02-09
Abstract
Abstract Compounds of the formula Ar--O--CH.sub.2 --CHOH--CH.sub.2 --NH--R wherein Ar is phenyl; phenyl monosubstituted or polysubstituted by halogen, cyano, acylamino (in which the acyl group has 1-7 carbon atoms), alkanoyl of 1-4 carbon atoms, alkyl (in which the chain can be interrupted by 1 or 2 oxygen atoms or by one sulfur atom and/or in which a multiple bond can be present) of a total of 1-10 carbon atoms, cycloalkyl of 3-8 carbon atoms, and/or cycloalkoxy of 3-8 carbon atoms; naphthyl; indanyl; indenyl; tetralyl; indolyl; indolyl monosubstituted or polysubstituted by alkyl, each of 1-4 carbon atoms; carbazolyl; or 1,2,3,4-tetrahydro-2-oxoquinolyl; and R is nitratoalkyl of 2-10 carbon atoms, and the physiologically acceptable acid addition salts thereof have valuable pharmacological properties, e.g., which make them useful for prophylaxis and treatment of heart problems, e.g., as β-receptor blockers.
Inventors
- 👤 Johannes Sombroek
- 👤 Karl-Heinz Becker
- 👤 Klaus O. Minck
- 👤 Hans-Joachim Enenkel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 05:06
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/08; A; A61; A61P; A61P25/00; A61P25/02
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
147 words
A 1-aryloxy-3-nitratoalkylamino-2-propanol of the formula Ar--O--CH.sub.2 --CHOH--CH.sub.2 --NH--R wherein Ar is phenyl; phenyl substituted by (a) halogen, (b) cyano, (c) C 1-7 alkanoylamino, (d) benzoylamino, (e) alkanoyl of 1-4 carbon atoms, (f) C 1-10 alkyl, (g) C 1-10 alkoxy, C 1-10 alkoxy in which the carbon chain contains one ether oxygen atom, C 1-10 alkyl in which the carbon chain contains 1 or 2 ether oxygen atoms, C 1-10 alkylthio or C 1-10 alkyl in which the carbon chain contains one thioether sulfur atom, (h) C 1-10 alkenyl or C 1-10 alkynyl, (i) the residues (g) containing a double or triple bond, (j) cycloalkyl of 3-8 carbon atoms or (k) cycloalkoxy of 3-8 carbon atoms; naphthyl; indanyl; indenyl; 1,2,3,4-tetrahydronaphthyl; indolyl; indolyl substituted by alkyl of 1-4 carbon atoms; carbazolyl; or 1,2,3,4-tetrahydro-2-oxoquinolyl, and R is nitratoalkyl of 2-10 carbon atoms, and the physiologically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
147 words
A 1-aryloxy-3-nitratoalkylamino-2-propanol of the formula Ar--O--CH.sub.2 --CHOH--CH.sub.2 --NH--R wherein Ar is phenyl; phenyl substituted by (a) halogen, (b) cyano, (c) C 1-7 alkanoylamino, (d) benzoylamino, (e) alkanoyl of 1-4 carbon atoms, (f) C 1-10 alkyl, (g) C 1-10 alkoxy, C 1-10 alkoxy in which the carbon chain contains one ether oxygen atom, C 1-10 alkyl in which the carbon chain contains 1 or 2 ether oxygen atoms, C 1-10 alkylthio or C 1-10 alkyl in which the carbon chain contains one thioether sulfur atom, (h) C 1-10 alkenyl or C 1-10 alkynyl, (i) the residues (g) containing a double or triple bond, (j) cycloalkyl of 3-8 carbon atoms or (k) cycloalkoxy of 3-8 carbon atoms; naphthyl; indanyl; indenyl; 1,2,3,4-tetrahydronaphthyl; indolyl; indolyl substituted by alkyl of 1-4 carbon atoms; carbazolyl; or 1,2,3,4-tetrahydro-2-oxoquinolyl, and R is nitratoalkyl of 2-10 carbon atoms, and the physiologically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
12 words
1-o-Allyloxy-phenoxy-3-(1-methyl-3-nitratopropylamino)-2-propanol; 1-(1-naphthyloxy)-3-(1-methyl-3-nitratopropylamino)-2-propanol; 1-o-isopropylphenoxy-3-(1-methyl-3-nitratopropylamino)-2-propanol; 1-o-methoxyphenoxy-3-(1-methyl-3-nitratopropylamino)-2-propanol; 1-(4-indolyloxy)-3-(1-methyl-3-nitratopropylamino)-2-propanol; 1-o-cyanophenoxy-3-(1,1-dimethyl-3-nitratopropylamino)-2-propanol; or 1-(4-carbazolyloxy)-3-(1,1-dimethyl-3-nitratopropylamino)-2-propanol; compounds of claim 1.
Claim 4
Dependent Claim
38 words
A compound of claim 1, wherein R is --CZ 1 Z 2 --(CH 2 ) m --CZ 3 Z 4 --O--NO 2 wherein Z 1 to Z 4 are each H or CH 3 and m is 0-2.
Claim 5
Dependent Claim
22 words
A pharmaceutical composition comprising an amount of a compound of claim 1 effective as a β-receptor blocker and a pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
25 words
A method of achieving blockage of β-receptors in mammals which comprises administering an amount of a compound of claim 1 effective as a β-receptor blocker.
Claim 7
Dependent Claim
6 words
1-o-allyloxy-phenoxy-3-(1,1-dimethyl-3-nitratopropylamino)-2-propanol, a compound of claim 1.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1984-09-07 | 1985-03-09 | 1985-09-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-09-07 | 1989-03-09 | 1989-09-08 | $3760.00 | Window Closed / Lapsed |
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