US4296117A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-Aryloxy-2-hydroxy-3-[(Benzimidazolinone-substituted alkyl)-amino]propanes and salts thereof
Assignee: Boehringer Ingelheim GmbH
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Filing: 1980-01-16
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Granted: 1981-10-20
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Expires: 2000-01-16
Abstract
Abstract Compounds of the formula <IMAGE> wherein R1, R2 and R3 are hydrogen or substituents of various types; R4 is hydrogen; alkyl of 1 to 5 carbon atoms; or optionally substituted aralkyl of 7 to 14 carbon atoms; R5 is a heterocycle; D is alkylene of 1 to 12 carbon atoms; and A is hydrogen or acyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as alpha - and beta -adrenergic receptor blocking agents and antidepressants.
Inventors
- 👤 Herbert Koppe
- 👤 Anton Mentrup
- 👤 Ernst-Otto Renth
- 👤 Kurt Schromm
- 👤 Wolfgang Hoefke
- 👤 Gojko Muacevic
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:29
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/227; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26; A61P9/00; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/32; C07D209/34; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/32; C07D235/00; C07D235/02; C07D235/04; C07D235/24; C07D235/26; C07D265/00; C07D265/04; C07D265/12; C07D265/14; C07D265/18; C07D265/28
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
233 words
A compound of the formula ##STR95## wherein R 1 is hydrogen; halogen; trifluoromethyl; nitro; alkyl of 1 to 8 carbon atoms; alkoxy of 1 to 4 carbon atoms; alkoxyalkyl of 2 to 8 carbon atoms; alkenyl of 2 to 5 carbon atoms; alkynyl of 2 to 5 carbon atoms; alkenyloxy of 3 to 6 carbon atoms; alkynyloxy of 3 to 6 carbon atoms; --(CH 2 ) x --A', where x is 1, 2 or 3 and A' is cyano, amino, carboxamido or hydroxyl; phenoxy; benzyloxy; or --CH 2 --SO 2 --CH 3 ; R 2 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; aralkoxy of 7 to 14 carbon atoms; alkenyl of 2 to 4 carbon atoms; nitro; or, together with R 3 , --CH═CH--CH═CH--, which is attached to carbon atoms of the phenyl ring in o-position with respect to each other; R 3 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; or aralkoxy of 7 to 14 carbon atoms; R 4 is hydrogen; alkyl of 1 to 5 carbon atoms; or aralkyl of 7 to 14 carbon atoms; R 5 is ##STR96## where B is ##STR97## where R 12 is aryl; D is alkylene of 1 to 12 carbon atoms; and A is lower alkanoyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
233 words
A compound of the formula ##STR95## wherein R 1 is hydrogen; halogen; trifluoromethyl; nitro; alkyl of 1 to 8 carbon atoms; alkoxy of 1 to 4 carbon atoms; alkoxyalkyl of 2 to 8 carbon atoms; alkenyl of 2 to 5 carbon atoms; alkynyl of 2 to 5 carbon atoms; alkenyloxy of 3 to 6 carbon atoms; alkynyloxy of 3 to 6 carbon atoms; --(CH 2 ) x --A', where x is 1, 2 or 3 and A' is cyano, amino, carboxamido or hydroxyl; phenoxy; benzyloxy; or --CH 2 --SO 2 --CH 3 ; R 2 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; aralkoxy of 7 to 14 carbon atoms; alkenyl of 2 to 4 carbon atoms; nitro; or, together with R 3 , --CH═CH--CH═CH--, which is attached to carbon atoms of the phenyl ring in o-position with respect to each other; R 3 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; or aralkoxy of 7 to 14 carbon atoms; R 4 is hydrogen; alkyl of 1 to 5 carbon atoms; or aralkyl of 7 to 14 carbon atoms; R 5 is ##STR96## where B is ##STR97## where R 12 is aryl; D is alkylene of 1 to 12 carbon atoms; and A is lower alkanoyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
24 words
An α- and β-adrenolytic pharmaceutical dosage composition consisting essentially of an inert pharmaceutical carrier and an effective amount of a compound of claim 1.
Claim 4
Dependent Claim
35 words
The method of blocking the α- and β-adrenergic receptors in a warm-blooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective amount of a compound of claim 1.
Claim 5
Dependent Claim
222 words
A compound of the formula ##STR98## wherein R 1 is hydrogen; halogen; trifluoromethyl; nitro; alkyl of 1 to 8 carbon atoms; alkoxy of 1 to 4 carbon atoms; alkoxyalkyl of 2 to 8 carbon atoms; alkenyl of 2 to 5 carbon atoms; alkynyl of 2 to 5 carbon atoms; alkenyloxy of 3 to 6 carbon atoms; --(CH 2 ) x --A', where x is 1, 2 or 3 and A' is cyano, amino, carboxamido or hydroxyl; phenoxy; benzyloxy; or --CH 2 --SO 2 --CH 3 ; R 2 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; aralkoxy of 7 to 14 carbon atoms; alkenyl of 2 to 4 carbon atoms; nitro; or, together with R 3 , --CH═CH--CH═CH--, which is attached to carbon atoms of the phenyl ring in o-position with respect to each other; R 3 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; or aralkoxy of 7 to 14 carbon atoms; R 4 is hydrogen; alkyl of 1 to 5 carbon atoms; or aralkyl of 7 to 14 carbon atoms; R 5 is ##STR99## where B is ##STR100## where R 12 is aryl; and D is alkylene of 1 to 12 carbon atoms, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
222 words
A compound of the formula ##STR98## wherein R 1 is hydrogen; halogen; trifluoromethyl; nitro; alkyl of 1 to 8 carbon atoms; alkoxy of 1 to 4 carbon atoms; alkoxyalkyl of 2 to 8 carbon atoms; alkenyl of 2 to 5 carbon atoms; alkynyl of 2 to 5 carbon atoms; alkenyloxy of 3 to 6 carbon atoms; --(CH 2 ) x --A', where x is 1, 2 or 3 and A' is cyano, amino, carboxamido or hydroxyl; phenoxy; benzyloxy; or --CH 2 --SO 2 --CH 3 ; R 2 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; aralkoxy of 7 to 14 carbon atoms; alkenyl of 2 to 4 carbon atoms; nitro; or, together with R 3 , --CH═CH--CH═CH--, which is attached to carbon atoms of the phenyl ring in o-position with respect to each other; R 3 is hydrogen; halogen; alkyl of 1 to 4 carbon atoms; alkoxy of 1 to 4 carbon atoms; or aralkoxy of 7 to 14 carbon atoms; R 4 is hydrogen; alkyl of 1 to 5 carbon atoms; or aralkyl of 7 to 14 carbon atoms; R 5 is ##STR99## where B is ##STR100## where R 12 is aryl; and D is alkylene of 1 to 12 carbon atoms, or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
13 words
The compound of claim 4, wherein R 2 or R 3 is benzyloxy.
Claim 8
Dependent Claim
24 words
An α- and β-adrenolytic pharmaceutical dosage composition consisting essentially of an inert pharmaceutical carrier and an effective amount of a compound of claim 4.
Claim 9
Dependent Claim
35 words
The method of blocking the α- and β-adrenergic receptors in a warm-blooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective amount of a compound of claim 4.
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) | 1984-10-19 | 1985-04-20 | 1985-10-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-19 | 1989-04-20 | 1989-10-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-19 | 1993-04-20 | 1993-10-20 | $7700.00 | Window Closed / Lapsed |