US3969506A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pharmacologically active tricyclic quinazolinones
Assignee: Sandoz Inc
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Filing: 1975-02-26
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Granted: 1976-07-13
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Expires: 1995-02-26
Abstract
Abstract The compounds are biologically active tricyclic quinazolinones of the class of imidazo[2,1-b]quinazolin-5-ones, pyrimido[2,1-b]quinazolin-6-ones and diazepino[2,1-b]quinazolin-7-ones, useful, for example, as bronchodilator agents. Processes for preparation of said compounds include the reaction of a N-carboxy anthranilic anhydride (an isatoic anhydride) with a cyclic pseudothiourea such as 2-organomercapto-4,5-dihydroimidazole or 2-organomercapto-3,4,5,6-tetrahydropyrimidine.
Inventors
- 👤 Goetz E. Hardtmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:12
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D239/00; C07D239/70; C07D239/72; C07D239/95
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
231 words
The method of effecting bronchodilation in an animal in need of said treatment comprising administering to said animal a bronchodilating effective amount of a compound of the formula: ##SPC16## wherein each of R 1 and R 2 is, independently, hydrogen, halo of atomic weight not greater than 36 or alkyl of 1 to 3 carbon atoms, or are either both hydroxy or both are alkoxy of 1 to 2 carbon atoms, or one is hydrogen and the other bromo, hydroxy or lower alkoxy of 1 to 2 carbon atoms, n is 1 to 3, R is alkyl of 1 to 5 carbon atoms, ##SPC17## m is 1 or 2, each of Y and Y' is, independently, hydrogen, halo of atomic weight not greater than 36 or alkyl of 1 to 3 carbon atoms, or either both are hydroxy or both alkoxy of 1 to 2 carbon atoms, or one is hydrogen and the other bromo, hydroxy or alkoxy of 1 to 2 carbon atoms, provided that no more than two of R 1 , R 2 , Y and Y' are hydroxy, further provided that neither of R 1 and R 2 is hydroxy when either of Y and Y' is alkoxy and further provided that neither of Y and Y' is hydroxy when either of R 1 and R 2 is alkoxy, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Independent Claim
231 words
The method of effecting bronchodilation in an animal in need of said treatment comprising administering to said animal a bronchodilating effective amount of a compound of the formula: ##SPC16## wherein each of R 1 and R 2 is, independently, hydrogen, halo of atomic weight not greater than 36 or alkyl of 1 to 3 carbon atoms, or are either both hydroxy or both are alkoxy of 1 to 2 carbon atoms, or one is hydrogen and the other bromo, hydroxy or lower alkoxy of 1 to 2 carbon atoms, n is 1 to 3, R is alkyl of 1 to 5 carbon atoms, ##SPC17## m is 1 or 2, each of Y and Y' is, independently, hydrogen, halo of atomic weight not greater than 36 or alkyl of 1 to 3 carbon atoms, or either both are hydroxy or both alkoxy of 1 to 2 carbon atoms, or one is hydrogen and the other bromo, hydroxy or alkoxy of 1 to 2 carbon atoms, provided that no more than two of R 1 , R 2 , Y and Y' are hydroxy, further provided that neither of R 1 and R 2 is hydroxy when either of Y and Y' is alkoxy and further provided that neither of Y and Y' is hydroxy when either of R 1 and R 2 is alkoxy, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
17 words
The method of claim 1 in which the compound is a compound in which R is ##SPC18##
Claim 4
Dependent Claim
30 words
The method of claim 2 in which the compound is a compound in which each of R 1 and R 2 is hydrogen and n and m are each 1.
Claim 5
Dependent Claim
13 words
The method of claim 3 in which the compound is the compound 10-benzyl-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one.
Claim 6
Dependent Claim
14 words
The method of claim 4 in which the compound is in free base form.
Claim 7
Dependent Claim
13 words
The method of claim 3 in which the compound is the compound 10-(4'-fluorobenzyl)-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one.
Claim 8
Dependent Claim
14 words
The method of claim 6 in which the compound is in free base form.
Claim 9
Dependent Claim
18 words
The method of claim 6 in which the compound is in the form of hydrochloric acid addition salt.
Claim 10
Dependent Claim
41 words
The method of claim 2 in which the compound is a compound in which each of R 1 and R 2 is hydrogen, n is 1 or 2, m is 1, Y is halo at the 4-position and Y' is hydrogen.
Claim 11
Dependent Claim
17 words
The method of claim 9 in which the compound is a compound in which n is 1.
Claim 12
Dependent Claim
11 words
The method of claim 9 in which the compound is 10-(4'-chlorobenzyl)-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one.
Claim 13
Dependent Claim
11 words
The method of claim 9 in which the compound is 10-(4'-bromobenzyl)-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one.
Claim 14
Dependent Claim
11 words
The method of claim 9 in which the compound is 11-(4'-fluorobenzyl)-2,3,4,11-tetrahydropyrimido[2,1-b]quinazolin-6-one.
Claim 15
Dependent Claim
21 words
The method of claim 1 in which the compound is administered in a daily amount of from 20 to 3000 milligrams.
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) | 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 |