US4378361A
Expired / Lapsed
US
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Heterocyclic compounds
Assignee: Boehringer Ingelheim GmbH
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Filing: 1981-07-22
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Granted: 1983-03-29
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Expires: 2001-07-22
Abstract
Abstract Compounds of the formula <IMAGE> wherein Het is <IMAGE> <IMAGE> +TR <IMAGE> n is an integer from 1 to 4, inclusive, preferably 2 or 3, R1 is H or acyl, R2 is H, R1O, -NHSO2R7, -NHCOR8, -NHCONHR8, -NH-CH2-C6H4-R9, -CH2OH, -CH2SO2R7, -CONHR8, halogen or -CN, R3 is H, halogen, R7 or -OR7, R2 and R3 together with each other are <IMAGE> R4 is H, -CH3 or -C2H5, R5 and R6 are each H or -CH3, R7 is C1-C4 alkyl, R8 is H or C1-C4 alkyl, R9 is H, C1-C4 alkyl or C1-C4 alkoxy optionally interrupted by oxygen, R10 and R12 are each H, CH3, Cl or OCH3, or together methylenedioxy, X is <IMAGE> or N, and Z is -CH2 or -CO; in the form of racemates, enantiomers, diastereoisomeric antipode pairs, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as bronchospasmolytics, spasmolytics, muscle-relaxants, antiallergics and hypotensives.
Inventors
- 👤 Kurt Schromm
- 👤 Anton Mentrup
- 👤 Ernst-Otto Renth
- 👤 Armin Fugner
- 👤 Ilse Streller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:04
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; A; A61; A61P; A61P1/00; A61P1/04; A61P1/06; A61P11/00; A61P11/08; A61P13/00; A61P13/02; A61P15/00; A61P25/00; A61P25/24; A61P25/26; A61P27/00; A61P27/02; A61P27/14; A61P37/00; A61P37/08; A61P9/00; A61P9/06; A61P9/12; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/04; C07D233/28; C07D233/30; C07D233/32; C07D233/36; C07D233/56; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D235/08; C07D235/18; C07D239/00; C07D239/70; C07D239/72; C07D239/86; C07D239/88; C07D239/95; C07D239/96; C07D249/00; C07D249/02; C07D249/08; C07D249/16; C07D249/18
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
170 words
A compound of the formula ##STR105## wherein n is an integer from 1 to 4, inclusive; R 1 is hydrogen or carboxylic acid acyl; R 2 is hydrogen, --OR 1 , --NHSO 2 R 7 , --NHCOR 8 --NHCONHR 8 , --NH--CH 2 --C 6 H 4 --R 9 , --CH 2 OH, --CH 2 SO 2 R 7 , --CONHR 8 , halogen or --CN; R 3 is hydrogen, halogen, --R 7 or --OR 7 ; R 4 is hydrogen, methyl or ethyl; R 5 and R 6 are each hydrogen or methyl; R 7 is alkyl of 1 to 4 carbon atoms; R 8 is hydrogen or alkyl of 1 to 4 carbon atoms; R 9 is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, optionally interrupted by oxygen; R 10 is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or pyridyl; and Z is --CH 2 -- or --CO--; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
170 words
A compound of the formula ##STR105## wherein n is an integer from 1 to 4, inclusive; R 1 is hydrogen or carboxylic acid acyl; R 2 is hydrogen, --OR 1 , --NHSO 2 R 7 , --NHCOR 8 --NHCONHR 8 , --NH--CH 2 --C 6 H 4 --R 9 , --CH 2 OH, --CH 2 SO 2 R 7 , --CONHR 8 , halogen or --CN; R 3 is hydrogen, halogen, --R 7 or --OR 7 ; R 4 is hydrogen, methyl or ethyl; R 5 and R 6 are each hydrogen or methyl; R 7 is alkyl of 1 to 4 carbon atoms; R 8 is hydrogen or alkyl of 1 to 4 carbon atoms; R 9 is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, optionally interrupted by oxygen; R 10 is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or pyridyl; and Z is --CH 2 -- or --CO--; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
103 words
A compound of claim 1, where n is an integer from 1 to 4, inclusive; R 1 is hydrogen; R 2 is hydrogen, hydroxyl, --NHSO 2 CH 3 , --NHCOR 8 , --NHCONHR 8 , --NH--CH 2 --C 6 H 4 --R 9 , --CH 2 OH, --CH 2 SO 2 CH 3 , --CONHR 8 , chlorine or fluorine; R 3 is hydrogen, chlorine, methyl or methoxy; R 5 , R 6 , R 8 and R 10 are each hydrogen or methyl; R 9 is hydrogen or 4-methoxy; and Z is --CO--; or a non-toxic, pharmacologically acceptable acid addition salt thereof.
Claim 4
Dependent Claim
11 words
A compound of claim 1, wherein n is 2 or 3.
Claim 5
Dependent Claim
11 words
A compound of claim 2, wherein n is 2 or 3.
Claim 6
Dependent Claim
39 words
A broncholytic, uterus-relaxing or antiallergic pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective broncholytic, uterus-relaxing or antiallergic amount of a compound of claim 1 where R 2 is other than --CONHR 8 .
Claim 7
Dependent Claim
52 words
The method of relieving bronchial spasms, relaxing the uterus or suppressing allergic reactions in a warmblooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective broncholytic, uterus-relaxing or antiallergic amount of a compound of claim 1 where R 2 is other than --CONHR 8 .
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) | 1986-03-28 | 1986-09-27 | 1987-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-03-28 | 1990-09-27 | 1991-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-03-28 | 1994-09-27 | 1995-03-29 | $7700.00 | Window Closed / Lapsed |