Patent US2361906A successfully refreshed from Google Patents.
Patent US4066766A successfully refreshed from Google Patents.
US4066766A
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US
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1-Oxo-6-substituted pyrimido [1,2-a]quinoline-2-carboxylic acids and derivatives thereof and their use as antiallergy agents
Assignee: Pfizer Inc
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Filing: 1976-01-20
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Granted: 1978-01-03
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Expires: 1996-01-20
Abstract
Abstract A novel series of 1-oxo-1H-6-substitutedpyrimido[1,2-a]quinoline-2-carboxylic acids of the formula <IMAGE> I wherein each of R1, R2 and R3 is hydrogen, alkyl having from 1 to 5 carbon atoms, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio or methylsulfinyl; with the proviso that no more than two of R1, R2 and R3 are bulky groups; i.e., branched-chain alkyl or branched-chain alkoxy, and when two of said R1, R2 and R3 are bulky groups they are located on non-adjacent positions; R4 is selected from the group consisting of chloro and bromo and -OR4' wherein OR4' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; R5 is hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; R2 and R3 when taken together are 1,3-butadienyl or alkylenedioxy of one to two carbon atoms; and the pharmaceutically-acceptable cationic salts of those compounds wherein R5 is hydroxy; compositions thereof; and their use as antiallergy agents.
Inventors
- 👤 Saul B. Kadin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 04:17
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/38; C07D215/48
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
226 words
A compound of the formula ##STR11## wherein each of the benzenoid substituents R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R 1 , R 2 and R 3 are bulky branched chain alkyl or branched chain alkoxy groups and when two of said R 1 , R 2 and R 3 are bulky groups they are located on non-adjacent positions; R 2 and R 3 when taken together are selected from the group consisting of 1,3-butadienyl and alkylenedioxy of 1 to 2 carbon atoms; R 4 is selected from the group consisting of chloro, bromo and OR 4 ' wherein OR 4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; R 5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 2
Dependent Claim
226 words
A compound of the formula ##STR11## wherein each of the benzenoid substituents R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R 1 , R 2 and R 3 are bulky branched chain alkyl or branched chain alkoxy groups and when two of said R 1 , R 2 and R 3 are bulky groups they are located on non-adjacent positions; R 2 and R 3 when taken together are selected from the group consisting of 1,3-butadienyl and alkylenedioxy of 1 to 2 carbon atoms; R 4 is selected from the group consisting of chloro, bromo and OR 4 ' wherein OR 4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; R 5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 3
Dependent Claim
66 words
A compound according to claim 1 wherein each of R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy, fluoro and alkyl; R 5 is selected from the group consisting of hydroxy and alkoxy; R 4 is OR 4 ' wherein OR 4 ' is alkoxy; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 4
Dependent Claim
66 words
A compound according to claim 1 wherein each of R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy, fluoro and alkyl; R 5 is selected from the group consisting of hydroxy and alkoxy; R 4 is selected from the group consisting of chloro and bromo; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 5
Dependent Claim
28 words
A compound according to claim 2 wherein each of R 1 , R 2 and R 3 is hydrogen; R 5 is alkoxy; and R 4 is methoxy.
Claim 6
Dependent Claim
28 words
A compound according to claim 2 wherein each of R 1 , R 2 and R 3 is hydrogen; R 5 is hydroxy; and R 4 is alkoxy.
Claim 7
Dependent Claim
44 words
A compound according to claim 2 wherein at least one and not more than two of the benzenoid substituents R 1 , R 2 and R 3 is alkoxy, the remaining benzenoid substituents being hydrogen; R 5 is alkoxy and R 4 is methoxy.
Claim 8
Dependent Claim
28 words
A compound according to claim 2 wherein R 1 is hydrogen, R 2 is 8-alkoxy, R 3 is 9-alkoxy, R 5 is alkoxy and R 4 is methoxy.
Claim 9
Dependent Claim
30 words
A compound according to claim 1 wherein R 2 and R 3 when taken together are alkylenedioxy; R 1 is hydrogen; R 5 is alkoxy and R 4 is methoxy.
Claim 10
Dependent Claim
11 words
The compound according to claim 4 wherein R 5 is ethoxy.
Claim 11
Dependent Claim
11 words
The compound according to claim 5 wherein R 4 is methoxy.
Claim 12
Dependent Claim
11 words
The compound according to claim 5 wherein R 4 is ethoxy.
Claim 13
Dependent Claim
25 words
The compound according to claim 6 wherein R 2 is 8-methoxy; each of R 1 and R 3 is hydrogen; and R 5 is ethoxy.
Claim 14
Dependent Claim
22 words
The compound according to claim 8 wherein R 2 and R 3 when taken together are 8,9-methylenedioxy; and R 5 is ethoxy.
Claim 15
Independent Claim
250 words
The method of treating bronchial asthma in a mammalian subject requiring such treatment which comprises administering to said subject an anti-bronchial effective amount of a compound having the formula ##STR12## wherein each of the benzenoid substituents R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R 1 , R 2 and R 3 are bulky branched chain alkyl or branched chain alkoxy groups and when two of said R 1 , R 2 and R 3 are bulky groups they are located on non-adjacent positions; R 2 and R 3 when taken together are selected from the group consisting of 1,3-butadienyl and alkylenedioxy of 1 to 2 carbon atoms; R 4 is selected from the group consisting of chloro, bromo and OR 4 ' wherein OR 4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; R 5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 16
Independent Claim
250 words
The method of treating bronchial asthma in a mammalian subject requiring such treatment which comprises administering to said subject an anti-bronchial effective amount of a compound having the formula ##STR12## wherein each of the benzenoid substituents R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R 1 , R 2 and R 3 are bulky branched chain alkyl or branched chain alkoxy groups and when two of said R 1 , R 2 and R 3 are bulky groups they are located on non-adjacent positions; R 2 and R 3 when taken together are selected from the group consisting of 1,3-butadienyl and alkylenedioxy of 1 to 2 carbon atoms; R 4 is selected from the group consisting of chloro, bromo and OR 4 ' wherein OR 4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; R 5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 17
Dependent Claim
28 words
The method according to claim 14 wherein each of R 1 , R 2 and R 3 is hydrogen; R 5 is alkoxy; and R 4 is methoxy.
Claim 18
Dependent Claim
28 words
The method according to claim 14 wherein each of R 1 , R 2 and R 3 is hydrogen; R 5 is hydroxy; and R 4 is alkoxy.
Claim 19
Dependent Claim
44 words
The method according to claim 14 wherein at least one and not more than two of the benzenoid substituents R 1 , R 2 and R 3 is alkoxy, the remaining benzenoid substituents being hydrogen; R 5 is hydroxy; and R 4 is methoxy.
Claim 20
Dependent Claim
11 words
The method according to claim 15 wherein R 5 is ethoxy.
Claim 21
Dependent Claim
11 words
The method according to claim 16 wherein R 4 is methoxy.
Claim 22
Dependent Claim
21 words
The method according to claim 17 wherein R 3 is 9-methoxy; and each of R 1 and R 2 is hydrogen.
Claim 23
Dependent Claim
247 words
A pharmaceutical composition useful in treating bronchial asthma in a mammalian subject requiring such treatment which comprises a pharmaceutically-acceptable carrier and a compound of the formula ##STR13## wherein each of the benzenoid substituents R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R 1 , R 2 and R 3 are bulky branched chain alkyl or branched chain alkoxy groups, and when two of said R 1 , R 2 and R 3 are bulky groups they are located on nonadjacent positions; R 2 and R 3 when taken together are selected from the group consisting of 1,3-butanediol and alkylenedioxy of 1 to 2 carbon atoms; R 5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms; and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; R 4 is selected from the group consisting of chloro, bromo and OR 4 ' wherein OR 4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 24
Dependent Claim
247 words
A pharmaceutical composition useful in treating bronchial asthma in a mammalian subject requiring such treatment which comprises a pharmaceutically-acceptable carrier and a compound of the formula ##STR13## wherein each of the benzenoid substituents R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, alkoxy having from 1 to 5 carbon atoms, carboalkoxy having from 1 to 5 carbon atoms in the alkoxy group, fluoro, chloro, bromo, methylthio, methylsulfinyl and alkyl having from 1 to 5 carbon atoms; with the proviso that no more than two of R 1 , R 2 and R 3 are bulky branched chain alkyl or branched chain alkoxy groups, and when two of said R 1 , R 2 and R 3 are bulky groups they are located on nonadjacent positions; R 2 and R 3 when taken together are selected from the group consisting of 1,3-butanediol and alkylenedioxy of 1 to 2 carbon atoms; R 5 is selected from the group consisting of hydroxy, alkoxy having from 1 to 5 carbon atoms; and hydroxy substituted alkoxy having from 2 to 5 carbon atoms; R 4 is selected from the group consisting of chloro, bromo and OR 4 ' wherein OR 4 ' is selected from the group consisting of alkoxy having from 1 to 5 carbon atoms, alkenyloxy of 3 to 4 carbon atoms and alkynyloxy of 3 to 4 carbon atoms; and the pharmaceutically-acceptable cationic salts of those compounds wherein R 5 is hydroxy.
Claim 25
Dependent Claim
28 words
A composition according to claim 21 wherein each of R 1 , R 2 and R 3 is hydrogen; R 5 is alkoxy and R 4 is methoxy.
Claim 26
Dependent Claim
28 words
A composition according to claim 21 wherein each of R 1 , R 2 and R 3 is hydrogen; R 5 is hydroxy and R 4 is alkoxy.
Claim 27
Dependent Claim
44 words
A composition according to claim 21 wherein R 5 is alkoxy; R 4 is methoxy; and at least one and not more than two of the benzenoid substituents R 1 , R z and R 3 is alkoxy, the remaining benzenoid substituents being hydrogen.
Claim 28
Dependent Claim
16 words
A pharmaceutical composition as claimed in claim 21 in a form suitable for administration by inhalation.
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) | 1981-01-02 | 1981-07-04 | 1982-01-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-02 | 1985-07-04 | 1986-01-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-02 | 1989-07-04 | 1990-01-03 | $7700.00 | Window Closed / Lapsed |