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US4146638A
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US
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N-(3-phenoxy-2-hydroxy-propyl)-n-(2-phenyl-2-hydroxy-ethyl)-amines
Assignee: Boehringer Ingelheim GmbH
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Filing: 1978-05-15
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Granted: 1979-03-27
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Expires: 1998-05-15
Abstract
Abstract Compounds of the formula ##STR1## wherein R 1 is halogen, hydroxyl, amino, alkyl, alkoxy or acylamido, R 2 is hydrogen, hydroxyl, alkyl, alkoxy or carboxamido, R 3 is hydrogen, halogen, alkyl or alkoxy, R 4 is hydrogen, methyl or ethyl, and R 5 and R 6 are each hydrogen, halogen, alkyl, alkoxy, benzyloxy, hydroxyl, amino, cyano, carboxyl, carbalkoxy, carboxamido, alkylenecarboxamido or acylamido, Provided, however, that, when R 1 is 4-hydroxyl or 4-chloro, R 2 and R 3 are hydrogen, R 4 is methyl and R 5 is halogen or 2-halo, R 6 is other than 4-hydroxyl or 4-benzyloxy; and nontoxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as cardiotonics, vasodilators, hypotensives and antiarrhythmics.
Inventors
- 👤 Ernst-Otto Renth
- 👤 Anton Mentrup
- 👤 Kurt Schromm
- 👤 Herbert Koppe
- 👤 Richard Reichl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:24
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/21; A61K31/215; A61K31/235; A61K31/24; A61K31/245; C; C07; C07C; C07C233/00; C07C233/01; C07C233/16
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
194 words
A compound of the formula ##STR21## wherein R 1 is halogen, hydroxyl, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkanoylamido of 1 to 5 carbon atoms or (alkane of 1 to 4 carbon atoms)sulfonamido, R 2 is hydrogen, hydroxyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or carboxamido, R 3 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, --R 4 is hydrogen, methyl or ethyl, and R 5 and R 6 are each hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzyloxy, hydroxyl, amino, cyano, carboxyl, carbalkoxy of 1 to 5 carbon atoms, carboxamido, alkylenecarboxamido of 1 to 5 carbon atoms, alkanoylamido of 1 to 5 carbon atoms or (alkane of 1 to 4 carbon atoms)sulfonamido, provided, however, that, when R 1 is 4-hydroxyl or 4-chloro, R 2 and R 3 are hydrogen, R 4 is methyl and R 5 is halogen or 2-halo, R 6 is other than 4-hydroxyl or 4-benzyloxy; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
194 words
A compound of the formula ##STR21## wherein R 1 is halogen, hydroxyl, amino, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkanoylamido of 1 to 5 carbon atoms or (alkane of 1 to 4 carbon atoms)sulfonamido, R 2 is hydrogen, hydroxyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or carboxamido, R 3 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, --R 4 is hydrogen, methyl or ethyl, and R 5 and R 6 are each hydrogen, halogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzyloxy, hydroxyl, amino, cyano, carboxyl, carbalkoxy of 1 to 5 carbon atoms, carboxamido, alkylenecarboxamido of 1 to 5 carbon atoms, alkanoylamido of 1 to 5 carbon atoms or (alkane of 1 to 4 carbon atoms)sulfonamido, provided, however, that, when R 1 is 4-hydroxyl or 4-chloro, R 2 and R 3 are hydrogen, R 4 is methyl and R 5 is halogen or 2-halo, R 6 is other than 4-hydroxyl or 4-benzyloxy; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
132 words
A compound of claim 1, where R 1 is chlorine, bromine, hydroxyl, alkyl of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms, acetylamido, propionylamido or methanesulfonamido; R 2 is hydrogen, hydroxyl, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms; R 3 is hydrogen, chlorine, bromine, hydroxyl, alkyl of 1 to 2 carbon atoms or alkoxy of 1 to 2 carbon atoms; R 4 is hydrogen or methyl; R 5 is hydrogen, fluorine, chlorine, bromine, alkyl of 1 to 2 carbon atoms, alkoxy of 1 to 2 carbon atoms, hydroxyl, cyano, carboxyl, carboxamido, benzyloxy, amino, carb(alkoxy of 1 to 2 carbon atoms), (alkylene of 1 to 2 carbon atoms)carboxamido or alkanoylamido of 1 to 3 carbon atoms; and R 6 is hydrogen.
Claim 4
Dependent Claim
17 words
A compound of claim 1, which is 1-[2-(p-hydroxy-phenyl)-2-hydroxy-ethylamino]-3-(p-cyano-phenoxy)-propanol-2 or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 5
Dependent Claim
17 words
A compound of claim 1, which is 1-[2-(m,m'-dihydroxy-phenyl)-2-hydroxy-ethylamino]-3-(p-tolyloxy)-propanol-2 or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
24 words
A cardiotonic pharmaceutical dosage unit comosition consisting essentially of an inert pharmaceutical carrier and an effective cardiotonic amount of a compound of claim 1.
Claim 7
Dependent Claim
36 words
The method of selectively increasing the strength of contraction of the heart muscle of a warm-blooded animal, which comprises perorally or parenterally administering to said animal an effective cardiotonic amount of a compound of claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-03-26 | 1982-09-25 | 1983-03-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-03-26 | 1986-09-25 | 1987-03-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-03-26 | 1990-09-25 | 1991-03-27 | $7700.00 | Window Closed / Lapsed |