EP0093534A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Novel chromanols
Assignee: Beecham Group PLC
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Filing: 1983-04-18
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Granted: —
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Expires: 2003-04-18
Abstract
Abstract Compounds of formula (I): wherein: either one of R, and R 2 is hydrogen and the other is selected from the class of C 1-6 alkylcarbonyl, benzoyl, C 1-6 alkoxycarbonyl, C 1-6 alkylcarbonyloxy, C 1-6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C 1-6 alkylsulphinyl, C 1-6 alkylsulphonyl, C 1-6 alkoxysulphinyl, C 1-6 alkoxysulphonyl, C 1-6 alkylcarbonylamino, C 1-6 alkoxycarbonylamino, C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkyl-thiocarbonyloxy, C 1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety beingoptionally substituted by one or two C 1-6 alkyl groups, or C 1-6 alkylsulphinylamino, C 1-6 alkylsulphonylami- noC 1-6 alkoxysulphinylamino or C 1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C 1-6 alkylcarbonyl, nitro or cyano, or -C(C 1-6 alkyl)NOH or -C(C 1-6 alkyl)NNH 2 , or one of R, and R 2 is nitro, cyano or C 1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C 1-6 alkyl or by C 2-7 alkanoyl; one of R 3 and R 4 is hydrogen or C 1-4 alkyl and the other is C 1-4 alkyl or R 3 and R 4 together are C 2-5 polymethylene having anti-hypertensive activity.
Inventors
- 👤 Kenneth Willcocks
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-24 05:31
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; C07D311/00; C07D311/02; C07D311/04; C07D311/58; C07D311/68
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
214 words
A compound of formula (I): wherein: either one of R 1 and R 2 is hydrogen and the other is selected from the class of C l - 6 alkylcarbonyl, benzoyl, C l - 6 alkoxycarbonyl, C l - 6 alkylcarbonyloxy, C l - 6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C l - 6 alkylsulphinyl, Cl-6 alkylsulphonyl, C 1-6 alkoxysulphipyl,C 1-6 alkoxysulphonyl, C l - 6 alkylcarbonylamino, C 1-6 alkoxycarbonylamino, C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkyl-thiocarbonyloxy, C 1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety beingoptionally substituted by one or two C l - 6 alkyl groups, or C 1-6 alkylsulphinylamino, C 1-6 alkylsulphonylaminoC 1-6 alkoxysulphinylamino or C 1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C l - 6 alkylcarbonyl, nitro or cyano, or -C(C 1-6 alkyl)NOH or -C(C 1-6 alkyl)NNH 2 , or one of R 1 and R 2 is nitro, cyano or C 1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C l - 6 alkyl or by C 2 - 7 alkanoyl; one of R 3 and R 4 is hydrogen or C 1-4 alkyl and the other is C l - 4 alkyl or R 3 and R 4 together are C 2 - 5 polymethylene;
Claim 2
Dependent Claim
214 words
A compound of formula (I): wherein: either one of R 1 and R 2 is hydrogen and the other is selected from the class of C l - 6 alkylcarbonyl, benzoyl, C l - 6 alkoxycarbonyl, C l - 6 alkylcarbonyloxy, C l - 6 alkylhydroxymethyl, nitro, cyano, chloro, trifluoromethyl, C l - 6 alkylsulphinyl, Cl-6 alkylsulphonyl, C 1-6 alkoxysulphipyl,C 1-6 alkoxysulphonyl, C l - 6 alkylcarbonylamino, C 1-6 alkoxycarbonylamino, C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkyl-thiocarbonyloxy, C 1-6 alkyl-thiolmethyl, formyl or aminosulphinyl, aminosulphonyl or aminocarbonyl, the amino moiety beingoptionally substituted by one or two C l - 6 alkyl groups, or C 1-6 alkylsulphinylamino, C 1-6 alkylsulphonylaminoC 1-6 alkoxysulphinylamino or C 1-6 alkoxysulphonylamino or ethylenyl terminally substituted by C l - 6 alkylcarbonyl, nitro or cyano, or -C(C 1-6 alkyl)NOH or -C(C 1-6 alkyl)NNH 2 , or one of R 1 and R 2 is nitro, cyano or C 1-3 alkylcarbonyl and the other is methoxy or amino optionally substituted by one or two C l - 6 alkyl or by C 2 - 7 alkanoyl; one of R 3 and R 4 is hydrogen or C 1-4 alkyl and the other is C l - 4 alkyl or R 3 and R 4 together are C 2 - 5 polymethylene;
Claim 3
Dependent Claim
45 words
A compound according to claims 1 wherein one of R 1 and R 2 is hydrogen and the other is selected from the class of C l-6 alkylcarbonyl, C l - 6 alkoxycarbonyl, C 1-6 alkoxycarbonyloxy, C l - 6 alkylhydroxymethyl, nitro, cyano or chloro.
Claim 4
Dependent Claim
37 words
A compound according to claim of formula (II): wherein one of R 1 ' and R 2 ' is hydrogen and the other is cyano or nitro and the remaining variables are as defined in claim 1.
Claim 5
Dependent Claim
4 words
6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-(2-hydroxy -1-pyrrolidinyl)-2H-benzo[b]-pyran-3-ol or 6-acetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-hydroxy-l-pyrrolidinyl)-2H-benzo[b]pyran-3-ol.
Claim 6
Dependent Claim
4 words
6-cyano-3,4-dihydro-2,2-dimethyl-trans-4-(2-hydroxy -1-pyrrolidinyl)-2H-benzo[b]-pyran-3-ol or 6-acetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-hydroxy-l-pyrrolidinyl)-2H-benzo[b]pyran-3-ol.
Claim 7
Dependent Claim
45 words
A compound according to claim 1 of formula (IV): wherein one of R 1 2 and R 2 2 is cyano or nitro and the other is optionally substituted amino as defined in claim 1 and the remaining variables are as defined in claim 1.
Claim 8
Dependent Claim
18 words
A compound according to any one of the claims 1 to 5 when isolated in substantially pure form.
Claim 9
Dependent Claim
101 words
A process for the preparation of a compound according to any one of the claims 1 to 6 which process comprises the cyclisation of a compound of the formula (V) or a salt thereof: wherein R 1 ' and R 2 ' are R 1 and R 2 respectively or a group or atom convertible thereto; and thereafter optionally converting R 1 ' or R 2 ' to R 1 or R 2 respectively and, when one of R 2 and R 2 in the compound of formula (I) is an amino containing group, optionally forming a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
54 words
A process according to claim 7 wherein the compound of formula (V) is generated in situ by the hydrolysis of a compound of formula (V): wherein R 5 is a group readily hydrolysable to a -CH 2 CHO group; and optionally thereafter converting R 1 '/R 2 ' to R 1 /R 2 .
Claim 11
Dependent Claim
26 words
A pharmaceutical composition comprising a compound according to any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
21 words
A compound according to any one of the claims 1 to 6 for use in the treatment of hypertension in mammals.
References Cited (Backward Citations)
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