US4766121A
Expired / Lapsed
US
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Pyridyl and pyridazinyl substituted thyronine compounds having selective thyromimetic activity
Assignee: Smith Kline & French Laboratories Ltd
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Filing: 1986-01-14
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Granted: 1988-08-23
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Expires: 2006-01-14
Abstract
Abstract This invention relates to chemical compounds which have selective thyromimetic activity. A compound of this invention is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]-thyronine.
Inventors
- 👤 David Ellis
- 👤 John C. Emmett
- 👤 Anthony H. Underwood
- 👤 Paul D. Leeson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 23:19
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/60; C07D213/62; C07D213/63; C07D213/64; A; A61; A61P; A61P3/00; A61P3/06; A61P5/00; A61P5/10; A61P5/12; C07C; C07C45/00; C07C45/61; C07C45/67; C07C45/673; C07C45/68; C07C45/70; C07C45/71; C07D213/65; C07D237/00; C07D237/02; C07D237/06; C07D237/10; C07D237/12; C07D237/14; C07D413/00; C07D413/02; C07D413/12
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
156 words
A compound of structure (I) ##STR50## in which, R 1 is --CH 2 CR 2 R 3 NR 4 R 5 or YCOR 6 ; R 2 is hydrogen or C 1-4 alkyl; R 3 is hydrogen or --COR 6 ; R 4 is hydrogen or C 1-4 alkyl; R 5 is hydrogen, C 1-4 alkyl or C 1-4 alkanoyl; R 6 is hydroxy, C 1-4 alkoxy, or --NR 4 R 5 ; Y is a bond or C 1-4 alkylene; R 7 and R 8 are the same or different and are each hydrogen, halogen, C 1-4 alkyl, nitro or amino, X is oxygen, sulphur, or CH 2 ; R 9 is hydroxy or C 1-4 alkoxy, aryl C 1-4 alkoxy, C 1-4 alkanoyloxy, aryl C 1-4 alkanoyloxy, arylsulphonyloxy, alkylsulphonyloxy, or O-glucuronide; R 10 is hydrogen or C 1-4 alkyl; and Ar is 5-hydroxy-2-pyridyl, 6-oxo-3(1H)-pyridyl, or a 6-oxo-3(1H)-pyridazinyl group, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
156 words
A compound of structure (I) ##STR50## in which, R 1 is --CH 2 CR 2 R 3 NR 4 R 5 or YCOR 6 ; R 2 is hydrogen or C 1-4 alkyl; R 3 is hydrogen or --COR 6 ; R 4 is hydrogen or C 1-4 alkyl; R 5 is hydrogen, C 1-4 alkyl or C 1-4 alkanoyl; R 6 is hydroxy, C 1-4 alkoxy, or --NR 4 R 5 ; Y is a bond or C 1-4 alkylene; R 7 and R 8 are the same or different and are each hydrogen, halogen, C 1-4 alkyl, nitro or amino, X is oxygen, sulphur, or CH 2 ; R 9 is hydroxy or C 1-4 alkoxy, aryl C 1-4 alkoxy, C 1-4 alkanoyloxy, aryl C 1-4 alkanoyloxy, arylsulphonyloxy, alkylsulphonyloxy, or O-glucuronide; R 10 is hydrogen or C 1-4 alkyl; and Ar is 5-hydroxy-2-pyridyl, 6-oxo-3(1H)-pyridyl, or a 6-oxo-3(1H)-pyridazinyl group, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
16 words
A compound as claimed in claim 1 in which Ar is a 6-oxo-3-(1H)-pyridyl or 6-oxo-3(1H)-pyridazinyl group.
Claim 4
Dependent Claim
34 words
A compound as claimed in claim 1 or claim 2 in which R 1 is ##STR51## and R 2 , R 4 , R 5 and R 6 are as defined in claim 1.
Claim 5
Dependent Claim
10 words
A compound as claimed in claim 1 which is 3,5-diiodo-3'-[6-oxo-3(1H)-pyridylmethyl]thyronine.
Claim 6
Dependent Claim
10 words
A compound as claimed in claim 1 which is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridylmethyl]thyronine.
Claim 7
Dependent Claim
10 words
A compound as claimed in claim 1 which is 3,5-dichloro-3'-[6-oxo-3(1H)-pyridylmethyl]thyronine.
Claim 8
Dependent Claim
10 words
A compound as claimed in claim 1 which is 3,5-diiodo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine.
Claim 9
Dependent Claim
10 words
A compound as claimed in claim 1 which is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine.
Claim 10
Dependent Claim
10 words
A compound as claimed in claim 1 which is 3,5-dichloro-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine.
Claim 11
Dependent Claim
21 words
A compound as claimed in claim 1 which is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine, in the form of the L-isomer substantially free of the D-isomer.
Claim 12
Dependent Claim
22 words
A pharmaceutical composition having selective thyromimetic activity comprising a compound as claimed in claim 1, in association with a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
22 words
A pharmaceutical composition having selective thyromimetic activity as claimed in claim 11 which comprises 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine in association with a pharmaceutically acceptable carrier.
Claim 14
Dependent Claim
31 words
A pharmaceutical composition having selective thyromimetic activity as claimed in claim 11 which comprises 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine in the form of the L-isomer substantially free of the D-isomer and a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
37 words
A method of producing selective thyromimetic activity in certain tissues except the heart which comprises administering to an animal in need thereof an effective amount to produce said activity of a compound as claimed in claim 1.
Claim 16
Dependent Claim
31 words
A method of lowering plasma lipid levels which comprises administering to an animal in need thereof an effective amount to produce said activity of a compound as claimed in claim 1.
Claim 17
Dependent Claim
34 words
A method of lowering the ratio of LDL-cholesterol to HDL-cholesterol which comprises administering to an animal in need thereof an effective amount to produce said activity of a compound as claimed in claim 1.
Claim 18
Dependent Claim
14 words
A method as claimed in claim 14 in which the compound administered is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine.
Claim 19
Dependent Claim
25 words
A method as claimed in claim 14 in which the compound administered is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine in the form of the L-isomer, substantially free of the D-isomer.
Claim 20
Dependent Claim
14 words
A method as claimed in claim 15 in which the compound administered is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine.
Claim 21
Dependent Claim
25 words
A method as claimed in claim 15 in which the compound administered is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine in the form of the L-isomer, substantially free of the D-isomer.
Claim 22
Dependent Claim
14 words
A method as claimed in claim 16 in which the compound administered is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine.
Claim 23
Dependent Claim
25 words
A method as claimed in claim 16 in which the compound administered is 3,5-dibromo-3'-[6-oxo-3(1H)-pyridazinylmethyl]thyronine in the form of the L-isomer, substantially free of the D-isomer.
References Cited (Backward Citations)
US3477954A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-08-23 | 1992-02-22 | 1992-08-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-08-23 | 1996-02-22 | 1996-08-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-08-23 | 2000-02-22 | 2000-08-23 | $7700.00 | Window Closed / Lapsed |