US4816586A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Delta opioid receptor antagonists
Assignee: University of Minnesota System
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Filing: 1987-07-29
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Granted: 1989-03-28
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Expires: 2007-07-29
Abstract
Abstract Delta-opioid receptor antagonists are disclosed of the formula: <IMAGE> OR <IMAGE> wherein R1 is (C1-C5)alkyl, C3-C6(cycloalkyl)alkyl, C5-C7(cycloalkenyl)alkyl, aryl, aralkyl, trans-(C4-C5)alkenyl, allyl or furan-2-ylalkyl, R2 is H, OH or O2CR, wherein R is (C1-C5)alkyl; R3 is H, (C1-C5)alkyl or RCO; X is O, S or NY, wherein Y is H or (C1-C5)alkyl; M is N or CH; and R4 and R5 are individually H, F, Cl, Br, NO2, NH2, (C1-C5)alkyl or (C1-C5)alkoxy or R4 and R5 together are benzo; and the pharmaceutically acceptable salts thereof.
Inventors
- 👤 Philip S. Portoghese
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:14
CPC Classifications
C; C07; C07D; C07D489/00; C07D489/06; C07D489/08
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
118 words
A compound of the formula: ##STR6## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 (cycloalkenyl)alkyl, aryl, aralkyl, trans(C 4 -C 5 )alkenyl, allyl or furan-2-ylalkyl, R 2 is H, OH or O 2 C(C 1 -C 5 )alkyl; R 3 is H or ((C 1 -C 5 )alkyl)C═O; X is O, S or NY, wherein Y is H or (C 1 -C 5 )alkyl; and R 4 and R 5 are individually H, F, Cl, Br, NH 2 , NO 2 , (C 1 -C 5 )alkyl or (C 1 -C 5 )alkoxy or R 4 and R 5 together are benzo; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
118 words
A compound of the formula: ##STR6## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 (cycloalkenyl)alkyl, aryl, aralkyl, trans(C 4 -C 5 )alkenyl, allyl or furan-2-ylalkyl, R 2 is H, OH or O 2 C(C 1 -C 5 )alkyl; R 3 is H or ((C 1 -C 5 )alkyl)C═O; X is O, S or NY, wherein Y is H or (C 1 -C 5 )alkyl; and R 4 and R 5 are individually H, F, Cl, Br, NH 2 , NO 2 , (C 1 -C 5 )alkyl or (C 1 -C 5 )alkoxy or R 4 and R 5 together are benzo; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
20 words
The compound of claim 1 wherein R 1 is C 3 -C 6 (cycloalkyl)alkyl or (C 1 -C 5 )alkyl.
Claim 4
Dependent Claim
12 words
The compound of claim 2 wherein R 1 is cyclopropylmethyl or methyl.
Claim 5
Dependent Claim
10 words
The compound of claim 1 wherein R 1 is cyclopropylmethyl.
Claim 6
Dependent Claim
16 words
The compound of claim 1 wherein R 2 is OH or OC═O(C 1 -C 5 )alkyl.
Claim 7
Dependent Claim
10 words
The compound of claim 1 wherein R 3 is H.
Claim 8
Dependent Claim
11 words
The compound of claim 1 wherein X is NH or O.
Claim 9
Dependent Claim
10 words
The compound of claim 1 wherein R 4 is F.
Claim 10
Dependent Claim
10 words
The compound of claim 1 wherein R 5 is H.
Claim 11
Dependent Claim
15 words
The compound of claim 1 wherein R 4 is H and R 5 is H.
Claim 12
Dependent Claim
17 words
The compound of claim 1 wherein R 4 is H and R 5 is CH 3 .
Claim 13
Dependent Claim
14 words
The compound of claim 1 wherein R 4 is OH or OCH 3 .
Claim 14
Dependent Claim
14 words
The compound of claim 1 wherein R 4 and R 5 together are benzo.
Claim 15
Dependent Claim
107 words
A compound of the formula: ##STR7## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 (cycloalkenyl)alkyl, aryl, aralkyl, trans(C 4 -C 5 )alkenyl, allyl or furan-2-ylalkyl, R 2 is H, OH or O 2 C(C 1 -C 5 )alkyl; R 3 is H or ((C 1 -C 5 )alkyl)C═O; M is N or CH and R 4 and R 5 are individually H, F, Cl, Br, NO 2 , NH 2 , (C 1 -C 5 )alkyl or (C 1 -C 5 )alkoxy or R 4 and R 5 together are benzo; and the pharmaceutically acceptable salts thereof.
Claim 16
Dependent Claim
107 words
A compound of the formula: ##STR7## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 (cycloalkenyl)alkyl, aryl, aralkyl, trans(C 4 -C 5 )alkenyl, allyl or furan-2-ylalkyl, R 2 is H, OH or O 2 C(C 1 -C 5 )alkyl; R 3 is H or ((C 1 -C 5 )alkyl)C═O; M is N or CH and R 4 and R 5 are individually H, F, Cl, Br, NO 2 , NH 2 , (C 1 -C 5 )alkyl or (C 1 -C 5 )alkoxy or R 4 and R 5 together are benzo; and the pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim
20 words
The compound of claim 14 wherein R 1 is C 3 -C 6 (cycloalkyl)alkyl or (C 1 -C 5 )alkyl.
Claim 18
Dependent Claim
12 words
The compound of claim 15 wherein R 1 is cyclopropylmethyl or methyl.
Claim 19
Dependent Claim
10 words
The compound of claim 14 wherein R 1 is cyclopropylmethyl.
Claim 20
Dependent Claim
18 words
The compound of claim 14 wherein R 2 is OH or O 2 C(C 1 -C 5 )alkyl.
Claim 21
Dependent Claim
16 words
The compound of claim 14 wherein R 3 is H or ((C 1 -C 5 )alkyl)C═O.
Claim 22
Dependent Claim
10 words
The compound of claim 14 wherein R 3 is H.
Claim 23
Dependent Claim
10 words
The compound of claim 14 wherein R 4 is H.
Claim 24
Dependent Claim
10 words
The compound of claim 21 wherein R 5 is H.
Claim 25
Dependent Claim
9 words
The compound of claim 14 wherein M is N.
Claim 26
Dependent Claim
9 words
The compound of claim 14 wherein M is CH.
Claim 27
Dependent Claim
14 words
The compound of claim 14 wherein R 4 and R 5 together are benzo.
References Cited (Backward Citations)
US4649200A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-03-27 | 1992-09-26 | 1993-03-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-03-27 | 1996-09-26 | 1997-03-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-03-27 | 2000-09-26 | 2001-03-28 | $7700.00 | Window Closed / Lapsed |