US4053600A
Expired / Lapsed
US
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Tricyclic 1,2,4-triazolo-quinazolines
Assignee: Sandoz Inc
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Filing: 1975-06-25
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Granted: 1977-10-11
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Expires: 1995-06-25
Abstract
Abstract The invention discloses 5-substituted-1,2,4-triazolo[4,3-c]quinazolines and 1,2,4-triazolo[1,5-c]quinazolines having pharmacological activity in animals and useful, for example, as hypotensive and anti-inflammatory agents. The compounds may be prepared, for example, by reacting a 5-halo-1,2,4-triazolo-quinazoline with a compound representing the function to be introduced at the 5-position. The 5-halo-1,2,4-triazolo[4,3-c]quinazolines also have pharmacological activity, e.g., hypotensive and anti-inflammatory activity, and may be prepared by reacting a 4-hydrazino-quinazoline with trimethoxy methane. The 5-halo-1,2,4-triazolo[1,5-c]quinazolines also have hypotensive and anti-inflammatory activity and are prepared from the corresponding 1,2,4-triazolo-[1,5-c]quinazolin-5(1H)-one using phosphorus oxychloride, the quinazolin-5(1H)-one being in turn prepared from the 5-halo-1,2,4-triazolo[4,3-c]quinazoline.
Inventors
- 👤 Goetz E. Hardtmann
- 👤 Faizulla G. Kathawala
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 16:19
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D239/00; C07D239/70; C07D239/72; C07D239/95
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
250 words
A compound of the formula ##STR25## wherein Q and R a are different and either a nitrogen atom or a =CR'"-function, R° represents ##STR26## R' represents hydrogen, and R" represents hydrogen; lower alkyl of 1 to 5 carbon atoms; allyl; methylallyl; propargyl; cycloalkyl of 3 to 6 carbon atoms; or di(lower of 1 to 3 carbon atoms)alkylamino(lower of 1 to 4 carbon atoms)alkyl; or lower alkoxy of 1 to 4 carbon atoms (lower of 1 to 4 carbon atoms)alkyl; or R' and R" together with the nitrogen attached to the ring represent di(lower of 1 to 3 carbon atoms)alkylamino; diallylamino; di(methylallyl)amino; or dipropargylamino; or R' and R" together with the nitrogen attached to the tricyclic ring system form a 3 to 6 membered saturated heterocyclic group represented by: ##STR27## wherein X is (a) direct bond or (b) methylene, and y and z are 0 or 1, provided that X is a direct bond when either y or z is 0; R'" represents hydrogen or lower alkyl of 1 to 4 carbon atoms; R 1 represents fluoro, chloro, bromo, lower alkyl of 1 to 3 carbon atoms, lower alkoxy of 1 to 3 carbon atoms, nitro, trifluoromethyl or, when n 2, the two R 1 's together form methylenedioxy, and n is 0, 1, 2 or 3, and when 2, then R 1 may be the same or different, and when 3, then all R 1 's are alkoxy; provided that n is 1 when R 1 is nitro or trifluoromethyl.
Claim 2
Dependent Claim
250 words
A compound of the formula ##STR25## wherein Q and R a are different and either a nitrogen atom or a =CR'"-function, R° represents ##STR26## R' represents hydrogen, and R" represents hydrogen; lower alkyl of 1 to 5 carbon atoms; allyl; methylallyl; propargyl; cycloalkyl of 3 to 6 carbon atoms; or di(lower of 1 to 3 carbon atoms)alkylamino(lower of 1 to 4 carbon atoms)alkyl; or lower alkoxy of 1 to 4 carbon atoms (lower of 1 to 4 carbon atoms)alkyl; or R' and R" together with the nitrogen attached to the ring represent di(lower of 1 to 3 carbon atoms)alkylamino; diallylamino; di(methylallyl)amino; or dipropargylamino; or R' and R" together with the nitrogen attached to the tricyclic ring system form a 3 to 6 membered saturated heterocyclic group represented by: ##STR27## wherein X is (a) direct bond or (b) methylene, and y and z are 0 or 1, provided that X is a direct bond when either y or z is 0; R'" represents hydrogen or lower alkyl of 1 to 4 carbon atoms; R 1 represents fluoro, chloro, bromo, lower alkyl of 1 to 3 carbon atoms, lower alkoxy of 1 to 3 carbon atoms, nitro, trifluoromethyl or, when n 2, the two R 1 's together form methylenedioxy, and n is 0, 1, 2 or 3, and when 2, then R 1 may be the same or different, and when 3, then all R 1 's are alkoxy; provided that n is 1 when R 1 is nitro or trifluoromethyl.
Claim 3
Dependent Claim
23 words
A compound of claim 1 having the formula: ##STR28## wherein R', R", R'", R 1 and n are as defined in claim 1.
Claim 4
Dependent Claim
23 words
A compound of claim 2 in which R' and R" together with the nitrogen atom attached to the tricyclic ring system form ##STR29##
Claim 5
Dependent Claim
14 words
A compound of claim 3 in which each of y and z are 1.
Claim 6
Dependent Claim
24 words
A compound of claim 1 having the formula: ##STR30## wherein R 1 , n, R', R" and R'" are as defined in claim 1.
Claim 7
Dependent Claim
23 words
A compound of claim 5 in which R' and R" together with the nitrogen atom attached to the tricyclic ring system form ##STR31##
Claim 8
Dependent Claim
14 words
A compound of claim 6 in which each of y and z are 1.
Claim 9
Dependent Claim
16 words
A compound of claim 5 having the formula: ##STR32## in which q is 2 to 5.
Claim 10
Dependent Claim
9 words
A compound of claim 8 having the fomrula: ##STR33##
Claim 11
Dependent Claim
14 words
A compound of claim 9 in which (R 1 ) n - is 8,9-dimethoxy.
Claim 12
Dependent Claim
10 words
The compound of claim 10 in which R'" is hydrogen.
Claim 13
Dependent Claim
10 words
The compound of claim 10 in which R'" is methyl.
Claim 14
Dependent Claim
10 words
The compound of claim 10 in which R'" is ethyl.
Claim 15
Dependent Claim
10 words
The compound of claim 10 in which R'" is isopropyl.
Claim 16
Dependent Claim
14 words
A compound of claim 8 in which (R 1 ) n - is 8,9-dimethoxy.
Claim 17
Dependent Claim
14 words
The compound of claim 15 in which R'" is hydrogen and q is 3.
Claim 18
Dependent Claim
10 words
A compound of claim 9 in which R'" is methyl.
Claim 19
Dependent Claim
11 words
A compound of claim 5 in which R" is lower alkyl.
Claim 20
Dependent Claim
14 words
A compound of claim 18 in which (R 1 ) n - is 8,9-dimethoxy.
Claim 21
Dependent Claim
240 words
A compound of claim 1 having the formula ##STR34## wherein Q and R a are different and either a nitrogen atom or a =CR'"-function, R° represents ##STR35## R' represents hydrogen, and R" represents hydrogen; lower alkyl of 1 to 5 carbon atoms; allyl; methylallyl; propargyl; cycloalkyl of 3 to 6 carbon atoms; or di(lower of 1 to 3 carbon atoms)alkylamino(lower of 1 to 4 carbon atoms)alkyl; or R' and R" together with the nitrogen attached to the ring represent di(lower of 1 to 3 carbon atoms) alkylamino; diallylamino; di(methylallyl)amino; or dipropargylamino; or R' and R" together with the nitrogen attached to the tricyclic ring system form a 3 to 6 membered saturated heterocyclic group represented by: ##STR36## wherein X is (a) a direct bond or (b) methylene, and y and z are 0 or 1, provided that X is a direct bond when either y or z is 0; R'" represents hydrogen or lower alkyl of 1 to 4 carbon atoms; R 1 represents fluoro, chloro, bromo, lower alkyl of 1 to 3 carbon atoms, lower alkoxy of 1 to 3 carbon atoms, nitro, trifluoromethyl or, when n is 2, the two R 1 's together form methylenedioxy, and n is 0, 1, 2 or 3, and when 2, then R 1 may be the same or different, and when 3, then all R 1 's are alkoxy; provided that n is 1 when R 1 is nitro or trifluoromethyl.
Claim 22
Dependent Claim
8 words
The compound of claim 2 which is 5-cyclobutylamino-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline.
Claim 23
Dependent Claim
8 words
The compound of claim 2 which is 5-cyclohexylamino-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline.
Claim 24
Dependent Claim
8 words
The compound of claim 2 which is 5-cyclopentylamino-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline.
Claim 25
Dependent Claim
8 words
The compound of claim 2 which is 5-cyclopropylamino-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline.
Claim 26
Dependent Claim
8 words
The compound of claim 2 which is 5-cyclopropylamino-3-methyl-8,9-dimethoxy-1,2,4-triazolo[4,3-c]quinazoline
Claim 27
Dependent Claim
8 words
The compound of claim 2 which is 5-cyclopropylamino-3-ethyl-8,9-dimetoxy-1,2,4-triazolo[4,3-c]quinazoline.
Claim 28
Dependent Claim
25 words
A pharmaceutical composition for treating inflammation in mammals comprising an inert pharmaceutically acceptable carrier and an anti-inflammatory effective amount of a compound of claim 20.
Claim 29
Dependent Claim
27 words
A method of treating inflammation in mammals comprising administering to a mammal in need of such treatment an anti-inflammatory effective amount of a compound of claim 1.
References Cited (Backward Citations)
US3838126A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-10-10 | 1981-04-11 | 1981-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-10 | 1985-04-11 | 1985-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-10 | 1989-04-11 | 1989-10-11 | $7700.00 | Window Closed / Lapsed |