US5298622A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Spiroindane opiate analogs
Assignee: University of Minnesota System
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Filing: 1993-05-12
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Granted: 1994-03-29
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Expires: 2013-05-12
Abstract
Abstract The present invention provides biologically active compounds of the formulas (I) and (II): (* CHEMICAL STRUCTURE *) (I) (* CHEMICAL STRUCTURE *) (II) wherein R3 is H or a hydroxyl protecting group, R2 is OH, H or a protected hydroxyl group, R1 is alkyl, cycloalkylalkyl, aryl, aralkyl, cycloalkenylalkyl, alkenyl, allyl or furanylalkyl; and R4 and R5 are individually H, halo, NO2, NH2, (C1-C5)alkyl, (C1-C5)alkoxy, or together are methylene-dioxy or benzo; and the pharmaceutically acceptable salts thereof.
Inventors
- 👤 Philip S. Portoghese
- 👤 Shigenori Ohkawa
- 👤 Scott T. Moe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 06:12
CPC Classifications
C; C07; C07D; C07D489/00; C07D489/06; C07D489/08; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
119 words
A compound of the formula: ##STR20## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 (cycloalkenyl)alkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )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, (C 6 -C 12 )aralkyl, (C 1 -C 5 )alkyl; or (C 1 -C 5 )alkylCO; and R 4 and R 5 are individually H, F, Cl, Br, NO 2 , NH 2 , (C 1 -C 5 )alkyl, (C 1 -C 5 )alkoxy or together are dioxymethylene (--OCH 2 O--) or benzo; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
119 words
A compound of the formula: ##STR20## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 (cycloalkenyl)alkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )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, (C 6 -C 12 )aralkyl, (C 1 -C 5 )alkyl; or (C 1 -C 5 )alkylCO; and R 4 and R 5 are individually H, F, Cl, Br, NO 2 , NH 2 , (C 1 -C 5 )alkyl, (C 1 -C 5 )alkoxy or together are dioxymethylene (--OCH 2 O--) or benzo; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
10 words
The compound of claim 1 wherein R 3 is H.
Claim 4
Dependent Claim
12 words
The compound of claims 1 or 2 wherein R 2 is OH.
Claim 5
Dependent Claim
14 words
The compound of claim 1 wherein R 1 is C 3 -C 6 (cycloalkyl)alkyl.
Claim 6
Dependent Claim
19 words
The compound of claim 1 wherein R 4 is (C 1 -C 5 )alkoxy and R 5 is H.
Claim 7
Dependent Claim
15 words
The compound of claim 5 wherein R 4 is methoxy and R 5 is H.
Claim 8
Dependent Claim
14 words
The compound of claim 1 wherein R 4 and R 5 together are benzo.
Claim 9
Dependent Claim
19 words
The compound of claim 1 wherein R 3 is H, R 2 is OH and R 1 is cyclopropylmethyl.
Claim 10
Dependent Claim
17 words
The compound of claim 8 wherein R 4 is 4'-methoxy or 7'-methoxy and R 5 is H.
Claim 11
Dependent Claim
16 words
The compound of claim 8 wherein R 4 and R 5 together are 4,5-benzo or 5,6-benzo.
Claim 12
Dependent Claim
16 words
The compound of claim 8 wherein R 4 is NO 2 and R 5 is H.
Claim 13
Dependent Claim
134 words
A compound of the formula: ##STR21## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 -(cycloalkenyl)alkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )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, (C 6 -C 12 )aralkyl, (C 1 -C 5 )alkyl; or (C 1 -C 5 )alkylCO; and R 4 and R 5 are individually H, F, Cl, Br, NO 2 , NH 2 , (C 1 -C 5 )alkyl, (C 1 -C 5 )alkoxy or together are dioxymethylene (--OCH 2 O--) or benzo, wherein R 4 and R 5 can occupy any available site on the naphthyl ring; and the pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim
134 words
A compound of the formula: ##STR21## wherein R 1 is (C 1 -C 5 )alkyl, C 3 -C 6 (cycloalkyl)alkyl, C 5 -C 7 -(cycloalkenyl)alkyl, (C 6 -C 12 )aryl, (C 6 -C 12 )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, (C 6 -C 12 )aralkyl, (C 1 -C 5 )alkyl; or (C 1 -C 5 )alkylCO; and R 4 and R 5 are individually H, F, Cl, Br, NO 2 , NH 2 , (C 1 -C 5 )alkyl, (C 1 -C 5 )alkoxy or together are dioxymethylene (--OCH 2 O--) or benzo, wherein R 4 and R 5 can occupy any available site on the naphthyl ring; and the pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
10 words
The compound of claim 12 wherein R 3 is H.
Claim 16
Dependent Claim
10 words
The compound of claim 12 wherein R 2 is OH.
Claim 17
Dependent Claim
16 words
The compound of claims 13 or 14 wherein R 1 is C 3 -C 6 -(cycloalkyl)alkyl.
Claim 18
Dependent Claim
10 words
The compound of claim 15 wherein R 1 is cyclopropylmethyl.
Claim 19
Dependent Claim
15 words
The compound of claim 12 wherein R 4 is H and R 5 is H.
References Cited (Backward Citations)
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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) | 1997-03-28 | 1997-09-27 | 1998-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-03-28 | 2001-09-27 | 2002-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-03-28 | 2005-09-27 | 2006-03-29 | $7700.00 | Window Closed / Lapsed |