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US4122274A
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3-Tetrazolo-5,6,7,8-substituted-pyrido[1,2-a]pyrimidin-4-ones
Assignee: Bristol Myers Co
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Filing: 1977-05-25
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Granted: 1978-10-24
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Expires: 1997-05-25
Abstract
Abstract A novel series of optionally substituted 3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones is provided for use as inhibitors of allergic reactions. The compounds exhibit antiallergy activity by both oral and parenteral routes of administration.
Inventors
- 👤 Peter Frederick Juby
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 11:57
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; A; A61; A61P; A61P11/00; A61P11/08; A61P37/00; A61P37/08; C07D213/38; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
224 words
A compound of the formula ##STR73## wherein R 1 , R 2 , R 3 and R 4 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR74## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR75## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR76## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the provisos that (1) when two or more of R 1 , R 2 , R 3 and R 4 are tertiary alkyl groups, they are located on non-adjacent positions and (2) no more than two of R 1 , R 2 , R 3 and R 4 may be nitro groups.
Claim 2
Dependent Claim
224 words
A compound of the formula ##STR73## wherein R 1 , R 2 , R 3 and R 4 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR74## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR75## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR76## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the provisos that (1) when two or more of R 1 , R 2 , R 3 and R 4 are tertiary alkyl groups, they are located on non-adjacent positions and (2) no more than two of R 1 , R 2 , R 3 and R 4 may be nitro groups.
Claim 3
Dependent Claim
43 words
A compound of claim 1 wherein R 1 , R 2 , R 3 and R 4 which may be the same or different are each hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 4
Dependent Claim
215 words
A compound of the formula ##STR77## wherein R 1 , R 2 and R 3 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR78## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR79## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR80## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the provisos that (1) when two or more of R 1 , R 2 and R 3 are tertiary alkyl groups, they are located on non-adjacent positions and (2) no more than two of R 1 , R 2 and R 3 may be nitro groups.
Claim 5
Dependent Claim
215 words
A compound of the formula ##STR77## wherein R 1 , R 2 and R 3 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR78## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR79## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR80## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the provisos that (1) when two or more of R 1 , R 2 and R 3 are tertiary alkyl groups, they are located on non-adjacent positions and (2) no more than two of R 1 , R 2 and R 3 may be nitro groups.
Claim 6
Dependent Claim
34 words
A compound of claim 3 wherein R 1 , R 2 and R 3 are each independently hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 7
Dependent Claim
186 words
A compound of the formula ##STR81## wherein R 1 and R 2 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR82## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR83## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR84## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the proviso that when R 1 and R 2 are both tertiary alkyl groups, they are located on non-adjacent positions.
Claim 8
Dependent Claim
186 words
A compound of the formula ##STR81## wherein R 1 and R 2 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR82## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR83## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR84## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the proviso that when R 1 and R 2 are both tertiary alkyl groups, they are located on non-adjacent positions.
Claim 9
Dependent Claim
31 words
A compound of claim 5 wherein R 1 and R 2 are each independently hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 10
Dependent Claim
186 words
A compound of the formula ##STR85## wherein R 1 and R 2 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR86## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR87## in which R is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR88## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the proviso that when R 1 and R 2 are both tertiary alkyl groups, they are located on non-adjacent positions.
Claim 11
Dependent Claim
186 words
A compound of the formula ##STR85## wherein R 1 and R 2 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR86## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR87## in which R is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR88## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof, with the proviso that when R 1 and R 2 are both tertiary alkyl groups, they are located on non-adjacent positions.
Claim 12
Dependent Claim
31 words
A compound of claim 7 wherein R 1 and R 2 are each independently hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 13
Dependent Claim
165 words
A compound of the formula ##STR89## wherein R 1 and R 2 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR90## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR91## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR92## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
165 words
A compound of the formula ##STR89## wherein R 1 and R 2 which may be the same or different are each hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O-(lower)alkenyl, ##STR90## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR91## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 -(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR92## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
31 words
A compound of claim 9 wherein R 1 and R 2 are each independently hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 16
Dependent Claim
13 words
The compound of claim 9 named 7,9-dimethyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
154 words
A compound of the formula ##STR93## wherein R 1 is hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR94## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR95## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 --(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR96## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim
154 words
A compound of the formula ##STR93## wherein R 1 is hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR94## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR95## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 --(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR96## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
26 words
A compound of claim 12 wherein R 1 is hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 20
Dependent Claim
13 words
The compound of claim 12 named 8-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
154 words
A compound of the formula ##STR97## wherein R 1 is hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR98## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR99## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 --(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR100## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 22
Dependent Claim
154 words
A compound of the formula ##STR97## wherein R 1 is hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR98## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 (CH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR99## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 --(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR100## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 23
Dependent Claim
26 words
A compound of claim 15 wherein R 1 is hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 24
Dependent Claim
13 words
The compound of claim 15 named 7-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 25
Dependent Claim
13 words
The compound of claim 15 named 7-ethyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 26
Dependent Claim
13 words
The compound of claim 15 named 7-n-butyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 27
Dependent Claim
13 words
The compound of claim 15 named 7-phenyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 28
Dependent Claim
13 words
The compound of claim 15 named 7-chloro-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 29
Dependent Claim
154 words
A compound of the formula ##STR101## wherein R 1 is hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR102## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 CCH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR103## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 --(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR104## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 30
Dependent Claim
154 words
A compound of the formula ##STR101## wherein R 1 is hydrogen, halogen, (lower)alkyl, cyclo(lower)alkyl, cyclo(lower)alkyl(lower)alkyl, (lower)alkenyl, (lower)alkynyl, (lower)alkoxy, (lower)alkoxy(lower)alkyl, --O--(lower)alkenyl, ##STR102## in which m is 0 or an integer from 1 to 6 and n is an integer from 2 to 7, --OCH 2 CCH 2 ) x O(CH 2 ) y CH 3 in which x and y are each independently 0 or an integer from 1 to 6, CF 3 , hydroxy, hydroxymethyl, (lower)alkylthio, amino, nitro, ##STR103## in which r is 4 or 5, (lower)alkylamino, di(lower)alkylamino, carboxyl, --CO 2 --(lower)alkyl, phenyl, phenyl substituted by one or two (lower)alkyl, (lower)alkoxy or halogen radicals, benzyl, (lower)alkylsulfinyl, R c --CO-- in which R c is (lower)alkyl, R c --COO-- in which R c is (lower)alkyl, --O(CH 2 ) k OH in which k is an integer from 2 to 6, ##STR104## or --OCH 2 C 6 H 5 , or a pharmaceutically acceptable salt thereof.
Claim 31
Dependent Claim
26 words
A compound of claim 22 wherein R 1 is hydrogen, (lower)alkyl, (lower)alkenyl, (lower)alkoxy, hydroxy, carboxy, (lower)alkylthio, halogen, CF 3 , amino, (lower)alkylamino, di(lower)alkylamino, phenyl or benzyl.
Claim 32
Dependent Claim
13 words
The compound of claim 22 named 9-methyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 33
Dependent Claim
9 words
The sodium salt of the compound of claim 24.
Claim 34
Dependent Claim
13 words
The compound of claim 22 named 3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
Claim 35
Dependent Claim
13 words
The compound of claim 22 named 9-ethyl-3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one, or a pharmaceutically acceptable salt thereof.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-10-23 | 1982-04-24 | 1982-10-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-23 | 1986-04-24 | 1986-10-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-23 | 1990-04-24 | 1990-10-24 | $7700.00 | Window Closed / Lapsed |