US4927836A
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Amide derivatives
Assignee: AstraZeneca UK Ltd
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Filing: 1988-06-29
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Granted: 1990-05-22
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Expires: 2008-06-29
Abstract
Abstract The invention concerns novel phenoxyacetic acid amide derivatives of the formula I (and pharmaceutically acceptable salts thereof) in which R 1 is hydrogen or fluoro, R 2 is phenyl, cycloalkyl, alkyl or alkenyl as defined herein, and R 3 is hydrogen, methyl or ethyl, or R 2 and R 3 together form polymethylene as defined herein. The invention also includes pharmaceutical compositions containing the amide derivatives, means for the manufacture of the said derivatives and for their use in the treatment of obesity and related conditions and/or in the manufacture of novel medicaments.
Inventors
- 👤 Brian R. Holloway
- 👤 Ralph Howe
- 👤 Balbir S. Rao
- 👤 Donald Stribling
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 06:00
CPC Classifications
C; C07; C07C; C07C215/00; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; A; A61; A61P; A61P3/00; A61P3/04; C07D217/00; C07D217/02; C07D217/04
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
97 words
An amide derivative of the formula I set out below: wherein R 1 is hydrogen or fluoro; R 2 is phenyl optionally bearing a substituent selected from the group consisting of halogeno, (1-4C)alkyl, (1-4C)alkoxy, trifluoromethyl, and nitro, (3-6C)cycloalkyl, (1-4C)alkyl in which the carbon atom linked to the nitrogen of NR 2 R 3 bears one or two hydrogens, or is (3-4C)alkenyl, either of which latter groups may optionally bear a substituent selected from the group consisting of hydroxy, (1-4C)alkoxy, phenyl and chlorophenyl; and R 3 is hydrogen, methyl or ethyl; or a pharmaceutically acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
97 words
An amide derivative of the formula I set out below: wherein R 1 is hydrogen or fluoro; R 2 is phenyl optionally bearing a substituent selected from the group consisting of halogeno, (1-4C)alkyl, (1-4C)alkoxy, trifluoromethyl, and nitro, (3-6C)cycloalkyl, (1-4C)alkyl in which the carbon atom linked to the nitrogen of NR 2 R 3 bears one or two hydrogens, or is (3-4C)alkenyl, either of which latter groups may optionally bear a substituent selected from the group consisting of hydroxy, (1-4C)alkoxy, phenyl and chlorophenyl; and R 3 is hydrogen, methyl or ethyl; or a pharmaceutically acceptable acid-addition salt thereof.
Claim 3
Dependent Claim
66 words
A compound as claimed in claim 1 wherein R 2 is phenyl optionally bearing a substituent selected from the group consisting of fluoro, chloro, bromo, methoxy, ethoxy, methyl, ethyl, trifluoromethyl, and nitro substituents; cyclobutyl, cyclopentyl or cyclohexyl; or R 2 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, allyl or 2-methyl-2-propenyl, optionally bearing a substituent selected from the group consisting of hydroxy, methoxy, ethoxy, phenyl and p-chlorophenyl.
Claim 4
Dependent Claim
37 words
A compound as claimed in claim 1 wherein the group NR 2 R 3 is selected from the group consisting of anilino, allylamino, cyclohexylamino, cyclopentylamino, dimethylamino, diethylamino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, (2-hydroxyethyl)amino, (3-hydroxypropyl)amino and (2-methoxyethyl)amino.
Claim 5
Dependent Claim
27 words
A compound as claimed in claim 1 wherein the the groups--OCH 2 .CO.NR 2 R 3 and --O.CH 2 CH 2 .NH-- are attached in para relationship.
Claim 6
Dependent Claim
69 words
A compound of the formula I as depicted in claim 1 wherein R 1 is hydrogen; the group NR 2 R 3 selected from (3-4C)alkenylamino, and (1-4C)alkylamino, in which latter group the carbon atom linked to the nitrogen bears one or two hydrogens; and the groups --OCH 2 .CO.NR 2 R 3 and --O.CH 2 CH 2 .NH-- are attached in para-relationship; or a pharmaceutically acceptable acid-addition salt thereof.
Claim 7
Dependent Claim
60 words
A compound of the formula I as depicted in claim 1 wherein R 1 is hydrogen; the group --NR 2 R 3 is selected from methylamino, ethylamino, propylamino, isopropylamino, (2-hydroxyethyl)amino, (3-hydroxypropyl)amino, (2-methoxyethyl)amino and (3-methoxypropylamino; and the groups --OCH 2 .CO.NR 2 R 3 and --O.CH 2 CH 2 .NH-- are attached in para-relationship; or a pharmaceutically acceptable acid-addition salt thereof.
Claim 8
Dependent Claim
21 words
A compound selected from the group consisting of N-methyl- , N-propyl-, N-(2-hydroxyethyl)- and N-allyl-2-p-(2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy)phenoxyacetamide, and the pharmaceutically acceptable acid-addition salts thereof.
Claim 9
Dependent Claim
21 words
A compound selected from the group consisting of N-methyl- , N-propyl-, N-(2-hydroxyethyl)- and N-allyl-2-p-(2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy)phenoxyacetamide, and the pharmaceutically acceptable acid-addition salts thereof.
Claim 10
Dependent Claim
14 words
The laevotatory optically active form of N-methyl-2-p-(2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy)phenoxyacetamide or a pharmaceutically acceptable acid-addition salt thereof.
Claim 11
Dependent Claim
14 words
The laevotatory optically active form of N-methyl-2-p-(2-[(2-hydroxy-3-phenoxypropyl)amino]ethoxy)phenoxyacetamide or a pharmaceutically acceptable acid-addition salt thereof.
Claim 12
Dependent Claim
9 words
4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Dependent Claim
9 words
4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 14
Dependent Claim
9 words
(S)-4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
9 words
(S)-4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
2 words
(S)-4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide hydrochloride.
Claim 17
Dependent Claim
2 words
(S)-4-[2-(2-Hydroxy-3-phenoxypropylamino)ethoxy]-N-(2-methoxyethyl)phenoxyacetamide hydrochloride.
Claim 18
Dependent Claim
20 words
A salt as claimed in claim 1 which is with an inorganic or organic acid affording a pharmaceutically acceptable anion.
Claim 19
Dependent Claim
37 words
A thermogenic pharmaceutical composition comprising a thermogenically effective amount of a compound of the formula I, or of a pharmaceutically acceptable acid-addition salt thereof, as defined in claim 1, together with a pharmaceutically acceptable diluent or carrier.
Claim 20
Dependent Claim
44 words
A method for producing a thermogenic effect in a warm-blooded animal requiring such treatment which comprises administering to said animal a thermogenically effective amount of a compound of the formula I, or of a pharmaceutically acceptable acid-addition salt thereof, as defined in claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-05-21 | 1993-11-20 | 1994-05-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-05-21 | 1997-11-20 | 1998-05-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-05-21 | 2001-11-20 | 2002-05-22 | $7700.00 | Window Closed / Lapsed |