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US4251537A Expired / Lapsed US ⏱️ 0.0 years remaining

Hypotensive 3,4-dihydro-2,2-dimethyl-4-amino-2H-benzo[b]pyran-3-ols

Assignee: Beecham Group PLC
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Filing: 1978-12-18
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Granted: 1981-02-17
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Expires: 1998-12-18
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Abstract

Abstract Amino chromanols, their preparation and anti-hypertensive compositions containing the compounds in hypotensive amounts with a pharmaceutically acceptable carrier for oral or parenteral administration. Pharmaceutically acceptable salts and O-acyl, particularly O-acetyl, derivatives are described. The compounds exist as racemates and optically active isomers.

Inventors

  • 👤 John M. Evans

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 18:24
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04; A; A61; A61P; A61P9/00; A61P9/12; C07D311/00; C07D311/02; C07D311/04; C07D311/22; C07D311/58; C07D311/68

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 255 words
A compound selected from the group consisting of (a)a 3,4-dihydro-2H-benzo[b]pyran of the formula: ##STR8## wherein R 1 , when taken independently of R 2 , is hydrogen or alkyl of up to 4 carbon atoms, unsubstituted or substituted with chloro, bromo, hydroxy, alkoxy of up to 4 carbon atoms or alkanoyloxy of up to 4 carbon atoms; R 2 , when taken independently of R 1 , is hydrogen or alkyl of up to 4 carbon atoms; R 1 and R 2 taken together, together with the nitrogen atom to which they are bound, are pyrrolidino, piperidino or hexamethyleneimino, unsubstituted or substituted with one or two methyl groups; and Y is COR 3 , COOR 3 , SOR 3 , SO 2 R 3 , SOOR 3 , SO 2 OR 3 , CH(OH)R 3 , C(R 3 )═NOH, C(R 3 )═NNH 2 , CONH 2 , CONR 4 R 5 , SONR 4 R 5 or SO 2 NR 4 R 5 in which: each of R 3 and R 4 is independently alkyl of up to 8 carbon atoms, unsubstituted or substituted with chloro, bromo, hydroxy, alkoxy of up to 4 carbon atoms or alkanoyloxy of up to 4 carbon atoms or substituted with three fluoro on the same carbon atom and R 5 is hydrogen or alkyl of up to 4 carbon atoms, (b) an O-alkanoyl derivative thereof, said alkanoyl having up to 6 carbon atoms and being unsubstituted or substituted with phenyl, and (c) a pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim 255 words
A compound selected from the group consisting of (a)a 3,4-dihydro-2H-benzo[b]pyran of the formula: ##STR8## wherein R 1 , when taken independently of R 2 , is hydrogen or alkyl of up to 4 carbon atoms, unsubstituted or substituted with chloro, bromo, hydroxy, alkoxy of up to 4 carbon atoms or alkanoyloxy of up to 4 carbon atoms; R 2 , when taken independently of R 1 , is hydrogen or alkyl of up to 4 carbon atoms; R 1 and R 2 taken together, together with the nitrogen atom to which they are bound, are pyrrolidino, piperidino or hexamethyleneimino, unsubstituted or substituted with one or two methyl groups; and Y is COR 3 , COOR 3 , SOR 3 , SO 2 R 3 , SOOR 3 , SO 2 OR 3 , CH(OH)R 3 , C(R 3 )═NOH, C(R 3 )═NNH 2 , CONH 2 , CONR 4 R 5 , SONR 4 R 5 or SO 2 NR 4 R 5 in which: each of R 3 and R 4 is independently alkyl of up to 8 carbon atoms, unsubstituted or substituted with chloro, bromo, hydroxy, alkoxy of up to 4 carbon atoms or alkanoyloxy of up to 4 carbon atoms or substituted with three fluoro on the same carbon atom and R 5 is hydrogen or alkyl of up to 4 carbon atoms, (b) an O-alkanoyl derivative thereof, said alkanoyl having up to 6 carbon atoms and being unsubstituted or substituted with phenyl, and (c) a pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim 60 words
A compound according to claim 1 wherein Y is COR 3 , COOR 3 , SOR 3 , SO 2 R 3 , SOOR 3 , SO 2 OR 3 , CONR 4 R 5 , SONR 4 R 5 or SO 2 NR 4 R 5 , wherein each of R 3 and R 4 is methyl or ethyl.
Claim 4
Dependent Claim 20 words
A compound according to claim 2 wherein Y is COR 3 , COOR 3 or CONR 4 R 5 .
Claim 5
Dependent Claim 26 words
A compound according to claim 2 wherein Y is SO 2 R 3 , SO 2 OR 3 or SO 2 NR 4 R 5 .
Claim 6
Dependent Claim 21 words
A compound according to claim 1 wherein Y is CH(OH)R 3 , C(R 3 )═NOH or C(R 3 )═NNH 2 .
Claim 7
Dependent Claim 20 words
A compound according to claim 1 wherein R 1 is hydrogen and R 2 is methyl, ethyl, isopropyl or t-butyl.
Claim 8
Dependent Claim 26 words
A compound according to claim 1 wherein R 1 and R 2 together with the nitrogen atom to which they are bound are pyrrolidino or piperidino.
Claim 9
Dependent Claim 20 words
A compound according to claim 7 wherein Y is COR 3 , COOR 3 or CONR 4 R 5 .
Claim 10
Dependent Claim 12 words
A compound according to claim 8 wherein Y is in the 6-position.
Claim 11
Dependent Claim 15 words
A compound according to claim 9, wherein Y is a CO 2 R 3 group.
Claim 12
Dependent Claim 11 words
A compound according to claim 10 wherein R 3 is methyl.
Claim 13
Dependent Claim 26 words
A compound according to claim 7 wherein Y is SO 2 R 3 , SO 2 OR 3 or SO 2 NR 3 R 4 .
Claim 14
Dependent Claim 14 words
A compound according to claim 1 wherein Y is in the 6- or 7-position.
Claim 15
Dependent Claim 12 words
A compound according to claim 1 wherein Y is in the 6-position.
Claim 16
Dependent Claim 14 words
A compound according to claim 1 which is the O-alkanoyl derivative as therein defined.
Claim 17
Dependent Claim 11 words
A compound according to claim 15 which is an O-acetyl derivative.
Claim 18
Dependent Claim 18 words
A compound according to claim 1 which is in the form of a pharmaceutically acceptable acid addition salt.
Claim 19
Dependent Claim 18 words
The compound according to claim 1 which is 6-acetyl-3,4-dihydro-2,2-dimethyl-trans-4-piperidino-2H-benzo [b]pyran-3-ol or a pharmaceutically acceptable acid addition salt thereof.
Claim 20
Dependent Claim 18 words
The compound according to claim 1 which is 6-acetyl-3,4-dihydro-2,2-dimethyl-trans-4-pyrrolidino-2H-benzo [b]pyran-3-ol or a pharmaceutically acceptable acid addition salt thereof.
Claim 21
Dependent Claim 18 words
The compound according to claim 1 which is 6-acetyl-3,4-dihydro-2,2-dimethyl-trans-4-isopropylamino-2H-benzo [b]pyran-3-ol or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim 17 words
The compound according to claim 1 which is 6-carbomethoxy-3,4-dihydro-2,2-dimethyl-trans-4-piperidino-2H-benzo[b]pyran-3-ol or a pharmaceutically acceptable acid addition salt thereof.
Claim 23
Dependent Claim 17 words
The compound according to claim 1 which is 6-carbomethoxy-3,4-dihydro-2,2-dimethyl-trans-4-pyrrolidino-2H-benzo[b]pyran-3-ol or a pharmaceutically acceptable acid addition salt thereof.
Claim 24
Dependent Claim 16 words
The compound according to claim 1 which is 6-carbomethoxy-3,4-dihydro-2,2-dimethyl-trans-4-isopropylamino-2H-benzo[b]pyran-3-ol or a pharmaceutically acceptable acid salt thereof.
Claim 25
Dependent Claim 18 words
The compound according to claim 1 which is 1-(2,2-dimethyl-trans-3-hydroxy-4-piperidinochroman-6-yl)ethanone oxime or a pharmaceutically acceptable acid addition salt thereof.
Claim 26
Dependent Claim 19 words
The compound according to claim 1 which is 1-(2,2-dimethyl-trans-3-hydroxy-4-isopropylaminochroman-6-yl) ethanone oxime or a pharmaceutically acceptable acid addition salt thereof.
Claim 27
Dependent Claim 17 words
The compound according to claim 1 which is 1-hydroxy-1-(2,2-dimethyl-trans-3-hydroxy-4-piperidinochroman-6-yl)ethane or a pharmaceutically acceptable acid addition salt thereof.
Claim 28
Dependent Claim 17 words
The compound according to claim 1 which is 1-hydroxy-1-(2,2-dimethyl-trans-3-hydroxy-4-pyrrolidinochroman-6-yl)ethane or a pharmaceutically acceptable acid addition salt thereof.
Claim 29
Dependent Claim 17 words
The compound according to claim 1 which is 6-carbamoyl-3,4-dihydro-2,2-dimethyl-trans-4-piperidino-2-H-benzo[b]pyran-3-ol or a pharmaceutically acceptable acid addition salt thereof.
Claim 30
Dependent Claim 17 words
The compound according to claim 1 which is 6-carbamoyl-3,4-dihydro-2,2-dimethyl-trans-4-isopropylamino-2H-benzo[b]-pyran-3-ol or a pharmaceutically acceptable acid addition salt thereof.
Claim 31
Dependent Claim 22 words
A hypotensive pharmaceutical composition comprising a hypotensive amount of a compound according to claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 32
Dependent Claim 25 words
The method of treating hypotension in a human or animal which comprises administering thereto a hypotensively effective amount of a compound according to claim 1.

References Cited (Backward Citations)

US4048317A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-02-17 1984-08-18 1985-02-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-02-17 1988-08-18 1989-02-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-02-17 1992-08-18 1993-02-17 $7700.00 Window Closed / Lapsed

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