US4234726A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Heterocyclic containing chromans
Assignee: Beecham Group PLC
•
Filing: 1979-05-09
•
Granted: 1980-11-18
•
Expires: 1999-05-09
Abstract
Abstract Compounds of the formula (I): ##STR1## or a pharmaceutically acceptable salt thereof wherein the NR 1 R 2 moiety is a 5-, 6-, or 7-membered saturated heterocyclic ring; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 1 to 4 carbon atoms; R 4 is naphthyl or phenyl unsubstituted or substituted by one or two substituents selected from the group consisting of fluorine, chlorine, bromine, methoxyl, benzyloxyl, trifluoromethyl, methyl, cyano, nitro, acetoxyl, amino, methylamino, ethylamino, dimethylamino, diethylamino, acetamide, hydroxyl, methoxycarbonyl, ethoxycarbonyl, carboxamido, sulphonamido, carboxy, trifluoromethylthio, trifluoromethoxyl, methylsulphonyl, trifluomethylsulphonyl and methylthio; R 5 is hydrogen or alkyl of 1 to 4 carbon atoms; R 6 is hydrogen or alkyl of 1 to 4 carbon atoms; X is oxygen and the dotted line represents a single or double bond.
Inventors
- 👤 Derek V. Gardner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 01:00
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/06; C07D311/08; C07D311/16; C07D311/20; C07D311/58
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
133 words
A compound of the formula (I): ##STR21## or a pharmaceutically acceptable salt thereof wherein the NR 1 R 2 moiety is a 5-, 6-, or 7-membered saturated heterocyclic ring; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 1 to 4 carbon atoms; R 4 is naphthyl or phenyl unsubstituted or substituted by one or two substituents selected from the group consisting of fluorine, chlorine, bromine, methoxyl, benzyloxyl, trifluoromethyl, methyl, cyano, nitro, acetoxyl, amino, methylamino, ethylamino, dimethylamino, diethylamino, acetamido, hydroxyl, methoxycarbonyl, ethoxycarbonyl, carboxamido, sulphonamido, carboxy, trifluoromethylthio, trifluoromethoxyl, methylsulphonyl, trifluoromethylsulphonyl and methylthio; R 5 is hydrogen or alkyl of 1 to 4 carbon atoms; R 6 is hydrogen or alkyl of 1 to 4 carbon atoms; X is oxygen and the dotted line represents a single or double bond.
Claim 2
Dependent Claim
133 words
A compound of the formula (I): ##STR21## or a pharmaceutically acceptable salt thereof wherein the NR 1 R 2 moiety is a 5-, 6-, or 7-membered saturated heterocyclic ring; R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 1 to 4 carbon atoms; R 4 is naphthyl or phenyl unsubstituted or substituted by one or two substituents selected from the group consisting of fluorine, chlorine, bromine, methoxyl, benzyloxyl, trifluoromethyl, methyl, cyano, nitro, acetoxyl, amino, methylamino, ethylamino, dimethylamino, diethylamino, acetamido, hydroxyl, methoxycarbonyl, ethoxycarbonyl, carboxamido, sulphonamido, carboxy, trifluoromethylthio, trifluoromethoxyl, methylsulphonyl, trifluoromethylsulphonyl and methylthio; R 5 is hydrogen or alkyl of 1 to 4 carbon atoms; R 6 is hydrogen or alkyl of 1 to 4 carbon atoms; X is oxygen and the dotted line represents a single or double bond.
Claim 3
Dependent Claim
21 words
A compound according to claim 1 wherein the NR 1 R 2 moiety forms a piperidino, morpholino, pyrrolidino or piperazino ring.
Claim 4
Dependent Claim
14 words
A compound according to claim 1 wherein the dotted line represents a single bond.
Claim 5
Dependent Claim
24 words
A compound according to claim 1 wherein R 3 is hydrogen, R 4 is naphthyl and R 5 and R 6 are each methyl.
Claim 6
Dependent Claim
11 words
A compound according to claim 1 wherein R 3 is hydrogen.
Claim 7
Dependent Claim
25 words
A compound according to claim 1 wherein R 4 is phenyl, naphthyl or phenyl substituted by fluorine, chlorine, bromine, methoxyl, benzyloxyl, trifluormethyl, methyl or nitro.
Claim 8
Dependent Claim
15 words
A compound according to claim 1 wherein R 5 and R 6 are each methyl.
Claim 9
Dependent Claim
86 words
A compound according to claim 1 of the formula (II): ##STR22## or a pharmaceutically acceptable salt thereof, wherein R 8 is linked to R 7 so that the moiety NR 7 R 8 forms a 5- or 6- membered saturated heterocyclic ring; R 9 is hydrogen or acetyl; and R 10 is phenyl, naphthyl, or phenyl substituted by fluorine, chlorine, bromine, methoxyl, benzyloxyl, trifluoromethyl, methyl, cyano, nitro, acetoxyl, amino, methylamino, ethylamino, dimethylamino, diethylamino, acetamido, hydroxyl, methoxycarbonyl, ethoxycarbonyl, carboxamido, sulphonamido, carboxy, trifluoromethylthio, trifluoromethoxyl, methylsulphonyl, trifluoromethylsulphonyl or methylthio.
Claim 10
Dependent Claim
30 words
A compound according to claim 8 wherein R 8 is linked to R 7 so that the moiety NR 7 R 8 forms a piperidino, morpholino, pyrrolidino or piperazino ring.
Claim 11
Dependent Claim
11 words
A compound according to claim 8 wherein R 9 is hydrogen.
Claim 12
Dependent Claim
25 words
A compound according to claim 8 wherein R 10 is phenyl, 2-naphthyl, or phenyl substituted by fluorine, chlorine, bromine, methyl, methoxy, hydroxy, trifluoromethyl or nitro.
Claim 13
Dependent Claim
37 words
A compound according to claim 1 of the formula (III): ##STR23## or a pharmaceutically acceptable salt thereof, wherein R 11 is hydrogen, fluorine, chlorine, bromine, methyl, methoxy, or trifluoromethyl and Z is morpholino, piperidino, pyrrolidino or N-methylpiperazino.
Claim 14
Dependent Claim
17 words
A compound according to claim 12 wherein R 11 is hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl.
Claim 15
Dependent Claim
11 words
A compound according to claim 12 wherein R 11 is trifluoromethyl.
Claim 16
Dependent Claim
11 words
A compound according to claim 14 wherein R 11 is 3-trifluoromethyl.
Claim 17
Dependent Claim
11 words
A compound according to claim 12 wherein R 11 is hydrogen.
Claim 18
Dependent Claim
21 words
A compound according to claim 1 of the formula (IV) or (V): ##STR24## wherein Z is morpholino, piperidino, pyrrolidino or N-methylpiperazino.
Claim 19
Dependent Claim
17 words
The compound according to claim 1 which is 7-[2-hydroxy-3-(1-piperidino)propoxy]-2,2-dimethyl-4-phenylchroman or a pharmaceutically acceptable acid addition salt thereof.
Claim 20
Dependent Claim
17 words
The compound according to claim 1 which is 7-[2-hydroxy-3-(1-morpholino)propoxy]-2,2-dimethyl-4-phenylchroman or a pharmaceutically acceptable acid addition salt thereof.
Claim 21
Dependent Claim
17 words
The compound according to claim 1 which is 7-[2-hydroxy-3(1-pyrrolidino)propoxy]-2,2-dimethyl-4-phenylchroman or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
17 words
The compound according to claim 1 which is 7-[2-hydroxy-3-(4-methyl-1-piperazino)propoxy]-2,2-dimethyl-4-phenylchroman or a pharmaceutically acceptable acid addition salt thereof.
Claim 23
Dependent Claim
16 words
A compound according to claim 14 in the form of a pharmaceutically acceptable acid addition salt.
Claim 24
Dependent Claim
116 words
A compound selected from the group consisting of a chroman derivative of the formula: ##STR25## and the pharmaceutically acceptable salts thereof wherein R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 1 to 4 carbon atoms; R 4 is naphthyl or phenyl unsubstituted or substituted with one or two members selected from the group consisting of fluoro, chloro, bromo, methoxy, benzyloxy, trifluoromethyl, methyl, cyano, nitro, acetoxy, amino, methylamino, ethylamino, dimethylamino, diethylamino, acetamido, hydroxy, carbomethoxy, carbethoxy, carboxamido, sulphonamido, carboxy, trifluoromethylthio, trifluoromethoxy, methylsulphonyl, trifluoromethylsulphonyl and methylthio; each of R 5 and R 6 is hydrogen or alkyl of 1 to 4 carbon atoms; and the dotted line is a single or double bond.
Claim 25
Dependent Claim
116 words
A compound selected from the group consisting of a chroman derivative of the formula: ##STR25## and the pharmaceutically acceptable salts thereof wherein R 3 is hydrogen, alkyl of 1 to 4 carbon atoms or acyl of 1 to 4 carbon atoms; R 4 is naphthyl or phenyl unsubstituted or substituted with one or two members selected from the group consisting of fluoro, chloro, bromo, methoxy, benzyloxy, trifluoromethyl, methyl, cyano, nitro, acetoxy, amino, methylamino, ethylamino, dimethylamino, diethylamino, acetamido, hydroxy, carbomethoxy, carbethoxy, carboxamido, sulphonamido, carboxy, trifluoromethylthio, trifluoromethoxy, methylsulphonyl, trifluoromethylsulphonyl and methylthio; each of R 5 and R 6 is hydrogen or alkyl of 1 to 4 carbon atoms; and the dotted line is a single or double bond.
References Cited (Backward Citations)
US4146539A
Cited
US4079066A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-11-18 | 1984-05-19 | 1984-11-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-18 | 1988-05-19 | 1988-11-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-18 | 1992-05-19 | 1992-11-18 | $7700.00 | Window Closed / Lapsed |