US3969363A
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Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their production
Assignee: Cassella Farbwerke Mainkur AG
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Filing: 1974-12-10
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Granted: 1976-07-13
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Expires: 1994-12-10
Abstract
Abstract The present invention relates to new pharmacologically valuable derivatives of 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU1## and the aldehyde condensation products and acid addition salts thereof wherein X is selected from the group consisting of ##EQU2## wherein the phenyl ring I may have attached to it up to three similar or different substituents selected from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkinyloxy, benzyloxy, phenyl, halogen and --NR 1 R 2 , wherein R 1 is selected from alkyl and acyl, and R 2 is selected from hydrogen and alkyl and n is 1, 2 or 3; and to the production thereof by a method selected from (A) reacting 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU3## with a compound having the formula Y-X, wherein X has the above defined meaning and Y is selected from halogen, --OH, --OK or --ONa; (B) reacting a compound of the formula ##EQU4## with a compound of the formula H 2 N--X, wherein X has the above-defined meaning and Z is selected from ##EQU5## and ##EQU6## (C) reacting a phenol ##EQU7## with Z--CH 2 --NH--X, wherein X and Z have the meaning defined above.
Inventors
- 👤 Thomas Raabe
- 👤 Otto Grawinger
- 👤 Josef Scholtholt
- 👤 Rolf-Eberhard Nitz
- 👤 Eckhard Schraven
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 00:06
CPC Classifications
C; C07; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/24; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/38; C07D213/44; C07D213/46; C07D213/50; C07D213/60; C07D213/78; C07D213/84; C07D213/85
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
157 words
Derivative of 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU49## wherein X is selected from the group consisting of ##EQU50## and ##EQU51## wherein n is 1, 2 or 3 and the phenyl radical I can be monosubstituted, disubstituted or trisubstituted by alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in either case up to 6 carbon atoms, cycloalkyl or cycloalkenyl having in either case a ring having 5 to 8 carbon atoms, alkoxy having up to 8 carbon atoms, alkenyloxy or alkinyloxy having in either case up to 5 carbon atoms, phenyl, chlorine or bromine, or the radical --NR 1 R 2 , wherein R 1 represents alkyl having 1 to 4 carbon atoms or aryl-substituted or alkyl-substituted carbonyl radical derived from an aromatic or aliphatic carboxilic acid having up to 11 carbon atoms, and R 2 represents hydrogen or alkyl having up to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt of said derivative.
Claim 2
Dependent Claim
157 words
Derivative of 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU49## wherein X is selected from the group consisting of ##EQU50## and ##EQU51## wherein n is 1, 2 or 3 and the phenyl radical I can be monosubstituted, disubstituted or trisubstituted by alkyl having 1 to 4 carbon atoms, alkenyl or alkinyl having in either case up to 6 carbon atoms, cycloalkyl or cycloalkenyl having in either case a ring having 5 to 8 carbon atoms, alkoxy having up to 8 carbon atoms, alkenyloxy or alkinyloxy having in either case up to 5 carbon atoms, phenyl, chlorine or bromine, or the radical --NR 1 R 2 , wherein R 1 represents alkyl having 1 to 4 carbon atoms or aryl-substituted or alkyl-substituted carbonyl radical derived from an aromatic or aliphatic carboxilic acid having up to 11 carbon atoms, and R 2 represents hydrogen or alkyl having up to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt of said derivative.
Claim 3
Dependent Claim
26 words
Derivative according to claim 1, wherein the phenyl radical I is substituted by a substituent selected from the group consisting of vinyl, allyl, methallyl and crotyl.
Claim 4
Dependent Claim
14 words
Derivative according to claim 1, wherein the phenyl radical I is substituted by cyclopentenyl.
Claim 5
Dependent Claim
24 words
Derivative according to claim 1, wherein the phenyl radical I is substituted by a radical selected from the group consisting of cyclopentyl and cyclohexyl.
Claim 6
Dependent Claim
32 words
Derivative according to claim 1, wherein the phenyl radical I is substituted by a substituent selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, butoxy, n-pentyloxy, allyloxy, methallyloxy, propargyloxy and n-octyloxy.
Claim 7
Dependent Claim
49 words
Derivative according to claim 1, wherein the phenyl radical I is substituted by the radical --NR 1 R 2 , wherein R 1 is selected from the group consisting of methyl, ethyl, acetyl and benzoyl, and R 2 is selected from the group consisting of hydrogen, methyl and ethyl.
Claim 8
Dependent Claim
55 words
Derivative of 1-phenoxy-3-amino-propan-2-ol, having the structural formula ##EQU52## wherein, the nucleus I is selected from the group consisting of phenyl, chlorophenyl, bromophenyl, alkoxyphenyl having 1 to 8 carbon atoms in the alkoxy moiety, allyloxyphenyl, methallyloxyphenyl, benzyloxyphenyl and acetaminophenyl, and n is 1, 2, or 3, and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 9
Dependent Claim
55 words
Derivative of 1-phenoxy-3-amino-propan-2-ol, having the structural formula ##EQU52## wherein, the nucleus I is selected from the group consisting of phenyl, chlorophenyl, bromophenyl, alkoxyphenyl having 1 to 8 carbon atoms in the alkoxy moiety, allyloxyphenyl, methallyloxyphenyl, benzyloxyphenyl and acetaminophenyl, and n is 1, 2, or 3, and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 10
Dependent Claim
17 words
The compound having the structural formula ##EQU53## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 11
Dependent Claim
17 words
The compound having the structural formula ##EQU53## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 12
Dependent Claim
17 words
The compound having the structural formula ##EQU54## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 13
Dependent Claim
17 words
The compound having the structural formula ##EQU54## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 14
Dependent Claim
17 words
The compound having the structural formula ##EQU55## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 15
Dependent Claim
17 words
The compound having the structural formula ##EQU55## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 16
Dependent Claim
17 words
The compound having the structural formula ##EQU56## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 17
Dependent Claim
17 words
The compound having the structural formula ##EQU56## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 18
Dependent Claim
17 words
The compound having the structural formula ##EQU57## and the pharmaceutically acceptable acid addition salts of said derivative.
Claim 19
Dependent Claim
17 words
The compound having the structural formula ##EQU57## and the pharmaceutically acceptable acid addition salts of said derivative.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-07-13 | 1980-01-12 | 1980-07-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-07-13 | 1984-01-12 | 1984-07-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-07-13 | 1988-01-12 | 1988-07-13 | $7700.00 | Window Closed / Lapsed |