US4079066A
Expired / Lapsed
US
⏱️ 0.0 years remaining
4-Naphthyl derivatives of 7-aminoalkylenoxy-2H-chromene
Assignee: Beecham Group PLC
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Filing: 1976-01-26
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Granted: 1978-03-14
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Expires: 1996-01-26
Abstract
Abstract Compounds of the formula (I): ##STR1## and pharmaceutically acceptable salts thereof wherein X is an alkylene group of 2 - 4 carbon atoms; Y is CH 2 or 0; R 1 is a hydrogen atom or a C 1-6 alkyl group; R 2 is a hydrogen atom or a C 1-6 alkyl or benzyl group or is joined to R 1 so that NR 1 R 1 is a 5-, 6- or 7- membered saturated ring; R 3 is a naphthyl group or a naphthyl group substituted by a fluorine, chlorine or bromine atom or a methyl, methoxyl, trifluoromethyl, hydroxy or acetoxy group; R 4 is a hydrogen atom or a C 1-4 alkyl group; and R 5 is a hydrogen atom or a C 1-4 alkyl group; have been found to be mood modifying agents.
Inventors
- 👤 Derek Victor Gardner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 02:06
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/06; C07D311/08; C07D311/16; C07D311/58
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
110 words
A compound of the formula (I): ##STR16## or a pharmaceutically acceptable salt thereof wherein X is --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --, --CH(CH 3 )--CH 2 --, --ch 2 ch(ch) 3 --ch 2 -- or --CH 2 --CH(CH 3 )--; Y is O; R 1 is hydrogen or alkyl of 1 to 6 carbon atoms; R 2 is hydrogen, alkyl of 1 to 6 carbon atoms or benzyl; R 3 is 1-naphthyl, 4-chloro-1-naphthyl, 3-chloro-1-naphthyl, 4-fluoro-1-naphthyl, 4-methyl-1-naphthyl, 2-naphthyl or 6-methoxy-2-naphthyl; R 4 is hydrogen or alkyl of 1 to 4 carbon atoms; and R 5 is hydrogen or alkyl of 1 to 4 carbon atoms.
Claim 2
Dependent Claim
110 words
A compound of the formula (I): ##STR16## or a pharmaceutically acceptable salt thereof wherein X is --CH 2 --CH 2 --, --CH 2 --CH 2 --CH 2 --, --CH(CH 3 )--CH 2 --, --ch 2 ch(ch) 3 --ch 2 -- or --CH 2 --CH(CH 3 )--; Y is O; R 1 is hydrogen or alkyl of 1 to 6 carbon atoms; R 2 is hydrogen, alkyl of 1 to 6 carbon atoms or benzyl; R 3 is 1-naphthyl, 4-chloro-1-naphthyl, 3-chloro-1-naphthyl, 4-fluoro-1-naphthyl, 4-methyl-1-naphthyl, 2-naphthyl or 6-methoxy-2-naphthyl; R 4 is hydrogen or alkyl of 1 to 4 carbon atoms; and R 5 is hydrogen or alkyl of 1 to 4 carbon atoms.
Claim 3
Dependent Claim
32 words
A compound according to claim 1 wherein R 1 is hydrogen or alkyl of 1 to 6 carbon atoms and R 2 is hydrogen or alkyl of 1 to 6 carbon atoms.
Claim 4
Dependent Claim
14 words
A compound according to claim 1 wherein X is --CH 2 --CH 2 .
Claim 5
Dependent Claim
23 words
A compound according to claim 1 wherein R 1 is hydrogen, methyl, ethyl or propyl and R 2 is hydrogen, methyl or ethyl.
Claim 6
Dependent Claim
18 words
A compound according to claim 1 wherein R 1 is hydrogen or methyl and R 2 is methyl.
Claim 7
Dependent Claim
20 words
A compound according to claim 1 wherein R 4 is hydrogen or methyl and R 5 is hydrogen or methyl.
Claim 8
Dependent Claim
15 words
A compound according to claim 1 wherein R 4 and R 5 are each methyl.
Claim 9
Dependent Claim
43 words
A compound according to claim 1 in the form of a pharmaceutically acceptable salt wherein said salt is selected from the group consisting of the citrate, acetate, propionate, lactate, tartrate, mandelate, succinate, fumarate, oleate, glutamate, gluconate, methanesulphonate, toluenesulphonate, sulphate, phosphate, hydrobromide and hydrochloride.
Claim 10
Dependent Claim
9 words
A compound according to claim 1 in monohydrate form.
Claim 11
Dependent Claim
11 words
A compound according to claim 1 wherein R 3 is 1-naphthyl.
Claim 12
Dependent Claim
15 words
The compound according to claim 1 which is 2,2-dimethyl-7(2-dimethylaminoethoxy)-4(1-naphthyl)-2H-chromene or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
14 words
The compound according to claim 1 which is 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4-(1-naphthyl)-2H-chromene or the hydrochloride salt thereof.
Claim 14
Dependent Claim
14 words
The compound according to claim 1 which is 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4-(2-naphthyl)-2H-chromene or the hydrochloride salt thereof.
Claim 15
Dependent Claim
9 words
The compound according to claim 1 which is 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4-(4-methyl-1-naphthyl)-2H-chromene.
Claim 16
Dependent Claim
9 words
The compound according to claim 1 which is 4-(4-fluoro-1-naphthyl)-2,2-dimethyl-7-(2-dimethylaminoethoxy)-2H-chromene.
Claim 17
Dependent Claim
9 words
The compound according to claim 1 which is 2,2-dimethyl-7-(2-dimethylaminoethoxy)-4(6-methoxy-2-naphthyl-2H-chromene.
Claim 18
Dependent Claim
9 words
The compound according to claim 1 which is 7-[2-(N-benzyl-N-methylamino)ethoxy]-2,2-dimethyl-4-(2-naphthyl)-2H-chromene.
Claim 19
Dependent Claim
9 words
The compound according to claim 1 which is 7-(2-dimethylaminoethoxy)-2,2-dimethyl-4-(2-naphthyl)-2H-chromene.
Claim 20
Dependent Claim
32 words
A compound of the formula (III): ##STR17## or a pharmaceutically acceptable salt thereof wherein R 3 is 1-naphthyl, 4-chloro-1-naphthyl, 3-chloro-1-naphthyl, 4-fluoro-1-naphthyl, 4-methyl-1-naphthyl, 2-naphthyl or 6-methoxy-2-naphthyl; and R 6 is hydrogen or methyl.
Claim 21
Dependent Claim
32 words
A compound of the formula (III): ##STR17## or a pharmaceutically acceptable salt thereof wherein R 3 is 1-naphthyl, 4-chloro-1-naphthyl, 3-chloro-1-naphthyl, 4-fluoro-1-naphthyl, 4-methyl-1-naphthyl, 2-naphthyl or 6-methoxy-2-naphthyl; and R 6 is hydrogen or methyl.
Claim 22
Dependent Claim
11 words
A compound according to claim 19 wherein R 3 is 1-naphthyl.
References Cited (Backward Citations)
US3159634A
Cited
US3388121A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-03-13 | 1981-09-12 | 1982-03-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-13 | 1985-09-12 | 1986-03-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-13 | 1989-09-12 | 1990-03-14 | $7700.00 | Window Closed / Lapsed |