Patent US4022897A successfully refreshed from Google Patents.
US4022897A
Expired / Lapsed
US
⏱️ 0.0 years remaining
CNS active compounds
Assignee: ER Squibb and Sons LLC
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Filing: 1975-04-17
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Granted: 1977-05-10
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Expires: 1995-04-17
Abstract
Abstract Compounds of the formula ##STR1## wherein R may be hydrogen or a straight or branched chain alkyl radical of from 1 to 10 carbon atoms, aryl of from 6 to 10 carbon atoms, or aralkyl of from 7 to 10 carbon atoms; Y may be hydrogen, alkyl of from 1 to 4 carbons, CF 3 , F, Cl, or Br; and Z may be hydrogen or as defined hereinafter. These compounds are useful as central nervous system stimulants or more specifically in enhancing performance or as mood elevators.
Inventors
- 👤 Harry Louis Yale
- 👤 John T. Sheehan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 13:58
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/73; C07D213/78; C07D213/81; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
126 words
A compound of the formula ##STR29## wherein Y is hydrogen, alkyl of from 1 to 4 carbon atoms, CF 3 , F, Cl or Br provided each Y may be hydrogen and R is a straight or branched chain alkyl radical of from 1 to 10 carbon atoms, and pharmaceutically acceptable acid addition salts thereof and amine salts of the formula NH(R 1 ) (R 2 ) wherein R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen, alkyl of 1-4 carbons, or ##STR30## wherein X is H, or OH, provided only one of R 1 and R 2 is H, and provided when one of R 1 and R 2 is ##STR31## the other is H.
Claim 2
Dependent Claim
126 words
A compound of the formula ##STR29## wherein Y is hydrogen, alkyl of from 1 to 4 carbon atoms, CF 3 , F, Cl or Br provided each Y may be hydrogen and R is a straight or branched chain alkyl radical of from 1 to 10 carbon atoms, and pharmaceutically acceptable acid addition salts thereof and amine salts of the formula NH(R 1 ) (R 2 ) wherein R 1 and R 2 are the same or different and are selected from the group consisting of hydrogen, alkyl of 1-4 carbons, or ##STR30## wherein X is H, or OH, provided only one of R 1 and R 2 is H, and provided when one of R 1 and R 2 is ##STR31## the other is H.
Claim 3
Dependent Claim
11 words
A compound as defined in claim 1 wherein R is alkyl.
Claim 4
Dependent Claim
11 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one.
Claim 5
Dependent Claim
13 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-one, diethylamine salt.
Claim 6
Dependent Claim
13 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 2-amino-6-pyridinol salt.
Claim 7
Dependent Claim
13 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 2-aminopyridine salt.
Claim 8
Dependent Claim
14 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, maleic acid salt.
Claim 9
Dependent Claim
14 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, tartaric acid salt.
Claim 10
Dependent Claim
15 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, salt with fumaric acid.
Claim 11
Dependent Claim
15 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, salt with malic acid.
Claim 12
Dependent Claim
13 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, n-butylamine salt.
Claim 13
Dependent Claim
13 words
A compound as defined in claim 2 having the name 9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one, 2-amino-3-pyridinol salt.
Claim 14
Dependent Claim
11 words
A compound as defined in claim 2 having the name 9-hydroxy-2-propyl-4H-pyrido[1,2-a]pyrimidin-4-one.
Claim 15
Dependent Claim
15 words
A compound as defined in claim 2 having the name 9-hydroxy-2-propyl-4H-pyrido[1,2-a]pyrimidin-4-one, salt with p-toluenesulfonic acid.
Claim 16
Dependent Claim
24 words
A method of stimulating the central nervous system of mammals, which comprises administering a therapeutic amount of a compound as defined in claim 1.
Claim 17
Dependent Claim
22 words
A method of elevating the mood of animals, which comprises administering a therapeutic amount of a compound as defined in claim 1.
Claim 18
Dependent Claim
55 words
A compound of the structure ##STR32## wherein Z is selected from the group consisting of o-bromobenzyl, allyl, 2,4-dichlorobenzyl, 2-bromo-4-chlorobenzyl, 2-phenethyl, cinnamyl, m-(trifluoromethyl)benzyl, o-cyanobenzyl, p-methoxybenzyl, p-(N,N-dimethylsulfamoyl)cinnamyl, 3-chloro-2-butenyl, p-(methylthio)benzyl, o-(carbomethoxy)benzyl, o-(trifluoromethyl)benzyl, p-(trifluoromethyl)benzyl, o-chlorobenzyl, 2-propynyl, or benzyl, Y 1 and Y 2 are hydrogen except in the case where Z is cinnamyl, Y 1 is hydrogen or methyl.
Claim 19
Dependent Claim
55 words
A compound of the structure ##STR32## wherein Z is selected from the group consisting of o-bromobenzyl, allyl, 2,4-dichlorobenzyl, 2-bromo-4-chlorobenzyl, 2-phenethyl, cinnamyl, m-(trifluoromethyl)benzyl, o-cyanobenzyl, p-methoxybenzyl, p-(N,N-dimethylsulfamoyl)cinnamyl, 3-chloro-2-butenyl, p-(methylthio)benzyl, o-(carbomethoxy)benzyl, o-(trifluoromethyl)benzyl, p-(trifluoromethyl)benzyl, o-chlorobenzyl, 2-propynyl, or benzyl, Y 1 and Y 2 are hydrogen except in the case where Z is cinnamyl, Y 1 is hydrogen or methyl.
Claim 20
Dependent Claim
30 words
A pharmaceutical composition for use in stimulating the central nervous system comprising an effective amount of a compound as defined in claim 17 in combination with a pharmaceutically acceptable carrier.
Claim 21
Dependent Claim
22 words
A method for stimulating the central nervous system which comprises administering an effective amount of a composition as defined in claim 18.
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) | 1980-05-09 | 1980-11-08 | 1981-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-09 | 1984-11-08 | 1985-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-09 | 1988-11-08 | 1989-05-10 | $7700.00 | Window Closed / Lapsed |