US4478849A
Expired / Lapsed
US
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Secondary amines, their preparation and use in pharmaceutical compositions
Assignee: Beecham Group PLC
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Filing: 1983-03-10
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Granted: 1984-10-23
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Expires: 2003-03-10
Abstract
Abstract The compounds of the formula (II): ##STR1## and their pharmaceutically acceptable salts wherein R 1 is a hydrogen, fluorine or chlorine atom or a hydroxyl, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino group; R 2 is a hydrogen, fluorine or chlorine atom or a hydroxyl group; R 3 is a hydrogen or chlorine atom or a hydroxyl group; R 4 is a carboxylic acid group or a salt, ester or amide thereof; R 5 is a hydrogen, chlorine or fluorine atom or a methyl, methoxyl or hydroxyl group or a carboxylic acid group or a salt, ester or amide thereof; R 6 is a hydrogen atom or a methyl, or propyl group; X is an oxygen atom or a bond; and Y is an alkylene group of up to 6 carbon atoms or a bond have been found to possess anti-obesity and/or antihyperglycaemic activity.
Inventors
- 👤 Anthony T. Ainsworth
- 👤 David G. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 06:22
CPC Classifications
C; C07; C07C; C07C275/00; C07C275/28; C07C275/32; C07C275/34; C07C205/00; C07C205/45; C07C205/49; C07C205/54; C07C45/00; C07C45/27; C07C45/28; C07C49/00; C07C49/76; C07C49/86; C07C65/00; C07C65/32
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
151 words
A pharmaceutical composition useful for the treatment of obesity or hyperglycaemia in humans and animals which comprises an anti-obesity effective amount or an anti-hyperglycaemically effective amount of a compound of the formula (II): ##STR21## or a pharmaceutically acceptable salt thereof, wherein R 1 is hydrogen, fluorine, chlorine, hydroxy, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino; R 2 is hydrogen, fluorine, chlorine or hydroxyl; R 3 is hydrogen, chlorine or methoxyl; R 4 is carboxylic acid or a salt, ester or amide thereof; R 5 is hydrogen, chlorine, fluorine, methyl, ethyl, methoxyl or hydroxyl or carboxylic acid or a salt, ester or amide thereof; R 6 is hydrogen, methyl, or propyl; X is oxygen or a bond; R 7 is hydrogen, methyl, ethyl or propyl and Y is alkylene of up to 6 carbon atoms or a bond, in combination with a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim
151 words
A pharmaceutical composition useful for the treatment of obesity or hyperglycaemia in humans and animals which comprises an anti-obesity effective amount or an anti-hyperglycaemically effective amount of a compound of the formula (II): ##STR21## or a pharmaceutically acceptable salt thereof, wherein R 1 is hydrogen, fluorine, chlorine, hydroxy, hydroxymethyl, methyl, methoxyl, amino, formamido, acetamido, methylsulphonylamido, nitro, benzyloxy, methylsulphonylmethyl, ureido, trifluoromethyl or p-methoxybenzylamino; R 2 is hydrogen, fluorine, chlorine or hydroxyl; R 3 is hydrogen, chlorine or methoxyl; R 4 is carboxylic acid or a salt, ester or amide thereof; R 5 is hydrogen, chlorine, fluorine, methyl, ethyl, methoxyl or hydroxyl or carboxylic acid or a salt, ester or amide thereof; R 6 is hydrogen, methyl, or propyl; X is oxygen or a bond; R 7 is hydrogen, methyl, ethyl or propyl and Y is alkylene of up to 6 carbon atoms or a bond, in combination with a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
15 words
A composition according to claim 1 wherein C(R 6 )R 7 is CH(CH 3 ).
Claim 4
Dependent Claim
16 words
A composition according to claim 1 wherein n is alkylene having 1 to 3 carbon atoms.
Claim 5
Dependent Claim
57 words
A composition according to claim 1 wherein R 4 is a group of the sub-formula (a), (b) or (c): --CO.sub.2 H (a) --CO.sub.2.sup.1 /.sub.q A.sup.q+ (b) --CO.sub.2 R.sub.8 (c) where A q+ is an ion wherein q is 1 or 2; and R 8 is a group such that CO 2 R 8 is an ester group.
Claim 6
Dependent Claim
17 words
A composition according to claim 1 wherein the compound is in the form of a single stereoisomer.
Claim 7
Dependent Claim
18 words
A composition according to claim 1 wherein the compound is in the form of a mixture of stereoisomers.
Claim 8
Dependent Claim
25 words
A composition according to claim 1 wherein the compound contains two centres of asymmetry and is used as a diasterioisomer free of the other diastereoisomer.
Claim 9
Dependent Claim
11 words
A composition according to claim 1 wherein R 6 is hydrogen.
Claim 10
Dependent Claim
11 words
A composition according to claim 1 wherein R 6 is methyl.
Claim 11
Dependent Claim
11 words
A composition according to claim 1 wherein R 7 is hydrogen.
Claim 12
Dependent Claim
11 words
A composition according to claim 1 wherein R 7 is methyl.
Claim 13
Dependent Claim
11 words
A composition according to claim 1 wherein R 5 is hydrogen.
Claim 14
Dependent Claim
15 words
A composition according to claim 1 wherein R 5 is a lower alkyl ester group.
Claim 15
Dependent Claim
14 words
A composition according to claim 1 wherein R 5 is methyl, ethyl, or n-propyl.
Claim 16
Dependent Claim
17 words
A composition according to claim 1 wherein R 5 is alkyl of 1 to 4 carbon atoms.
Claim 17
Dependent Claim
10 words
A composition according to claim 1 in oral administration form.
Claim 18
Dependent Claim
14 words
A composition according to claim 1 in a form suitable for administration by injection.
Claim 19
Dependent Claim
23 words
A composition according to claim 1 in unit dosage form, wherein each dosage unit contains from 0.01 to 100 milligrams of said compound.
Claim 20
Dependent Claim
42 words
A method of treating obesity in humans and animals and treating hyperglycaemia in humans and animals, which comprises administering to a human or animal in need thereof, an anti-obesity effective amount or an anti-hyperglycaemically effective amount of a composition of claim 1.
Claim 21
Dependent Claim
16 words
A method according to claim 19 wherein R 1 R 2 R 3 are each hydrogen.
Claim 22
Dependent Claim
15 words
A method according to claim 19 wherein C(R 6 )R 7 is CH(CH 3 ).
Claim 23
Dependent Claim
16 words
A method according to claim 19 wherein n is alkylene of 1 to 3 carbon atoms.
Claim 24
Dependent Claim
57 words
A method according to claim 19 wherein R 4 is a group of the sub-formula (a), (b) or (c): --CO.sub.2 H (a) --CO.sub.2.sup.1 /.sub.q A.sup.q+ (b) --CO.sub.2 R.sub.8 (c) where A q+ is an ion wherein q is 1 or 2; and R 8 is a group such that CO 2 R 8 is an ester group.
Claim 25
Dependent Claim
61 words
A method according to claim 23 wherein R 8 is lower alkyl, lower alkyl substituted by hydroxyl not on the α-carbon atom or a group of the sub-formulae (q) or (r): ##STR22## wherein R 10 is hydrogen or methyl, R 11 is lower alkyl or phenyl; R 12 is hydrogen, methyl or methoxyl; and R 13 is hydrogen, methyl or methoxyl.
Claim 26
Dependent Claim
17 words
A method according to claim 23 wherein R 8 is methyl, ethyl, propyl, butyl, pentyl or hexyl.
Claim 27
Dependent Claim
13 words
A method according to claim 19 wherein R 4 is in the para-position.
Claim 28
Independent Claim
67 words
A method of treating obesity and hyperglycaemia in humans and animals, which comprises administering to a human or animal in need thereof, an anti-obesity effective amount or an anti-hyperglycaemically effective amount of a compound of the formula (III): ##STR23## or a pharmaceutically acceptable salt or ester thereof wherein R 15 is hydrogen or methyl; R 16 is hydrogen or methyl; and m is 1, 2 or 3.
Claim 29
Independent Claim
67 words
A method of treating obesity and hyperglycaemia in humans and animals, which comprises administering to a human or animal in need thereof, an anti-obesity effective amount or an anti-hyperglycaemically effective amount of a compound of the formula (III): ##STR23## or a pharmaceutically acceptable salt or ester thereof wherein R 15 is hydrogen or methyl; R 16 is hydrogen or methyl; and m is 1, 2 or 3.
Claim 30
Dependent Claim
11 words
A method according to claim 19 wherein R 6 is methyl.
Claim 31
Dependent Claim
17 words
A method according to claim 19 wherein the compound is in the form of a single stereoisomer.
Claim 32
Dependent Claim
18 words
A method according to claim 19 wherein the compound is in the form of a mixture of stereoisomers.
Claim 33
Dependent Claim
25 words
A method according to claim 19 wherein the compound contains two centres of asymmetry and is used as a diastereoisomer free of the other diastereoisomer.
Claim 34
Dependent Claim
11 words
A method according to claim 19 wherein R 6 is hydrogen.
Claim 35
Dependent Claim
11 words
A method according to claim 19 wherein R 7 is hydrogen.
Claim 36
Dependent Claim
11 words
A method according to claim 19 wherein R 7 is methyl.
Claim 37
Dependent Claim
11 words
A method according to claim 19 wherein R 5 is hydrogen.
Claim 38
Dependent Claim
27 words
A method according to claim 23 wherein R 8 is methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, t-butyl, pentyl, hexyl, benzyl, phenyl, acetoxymethyl, pivaloyloxymethyl, α-ethoxycarbonyloxyethyl or phthalidyl.
Claim 39
Dependent Claim
18 words
A method according to claim 23 wherein R 8 is methyl, ethyl, n-propyl, acetoxymethyl, pivaloyloxymethyl, α-ethoxycarbonyloxethyl or phthalidyl.
Claim 40
Dependent Claim
17 words
A method according to claim 23 wherein R 8 is alkyl of 1 to 4 carbon atoms.
Claim 41
Dependent Claim
11 words
A method according to claim 19 wherein the administration is oral.
Claim 42
Dependent Claim
12 words
A method according to claim 19 wherein the administration is by injection.
References Cited (Backward Citations)
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GB1301134A
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US4086272A
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US4146638A
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US4329358A
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US4385066A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-23 | 1988-04-23 | 1988-10-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-23 | 1992-04-23 | 1992-10-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-23 | 1996-04-23 | 1996-10-23 | $7700.00 | Window Closed / Lapsed |