US4605659A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Purinyl or pyrimidinyl substituted hydroxycyclopentane compounds useful as antivirals
Assignee: Syntex USA LLC
•
Filing: 1985-04-30
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Granted: 1986-08-12
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Expires: 2005-04-30
Abstract
Abstract Novel 4-substituted-5-hydroxymethyl-1,2-cyclopentanediols or 1-cyclopentanol substituted at the 3-position by various heterocyclic groups are useful as antiviral agents.
Inventors
- 👤 Julien P. H. Verheyden
- 👤 John C. Martin
- 👤 G. V. Bindu Madhaven
- 👤 Daniel P. C. McGee
- 👤 Ernest J. Prisbe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 11:09
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/52; C07D239/54; C07D239/545; C07D239/553; C07D473/00
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
103 words
A compound of the formula ##STR8## wherein A is hydroxy; and C is hydrogen or hydroxy; B is a heterocyclic ring selected from the group consisting of 2-amino-6-hydroxypurin-9-yl, 6-aminopurin-9-yl, 2,4-dioxopyrimidin-1-yl optionally substituted at the 5-position by fluoro, methyl, iodo, trifluoromethyl, 2-bromovinyl, 2-chlorovinyl or 2-iodovinyl, and 4-amino-2-oxopyrimidin-1-yl optionally substituted at position-5 by iodo or trifluoromethyl; Z is hydrogen and Z' is hydroxy or fluoro; or Z and Z' are both fluoro; or Z together with Z' is oxo; and the wavy line indicates that the group may be above or below the plane of the ring; and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
103 words
A compound of the formula ##STR8## wherein A is hydroxy; and C is hydrogen or hydroxy; B is a heterocyclic ring selected from the group consisting of 2-amino-6-hydroxypurin-9-yl, 6-aminopurin-9-yl, 2,4-dioxopyrimidin-1-yl optionally substituted at the 5-position by fluoro, methyl, iodo, trifluoromethyl, 2-bromovinyl, 2-chlorovinyl or 2-iodovinyl, and 4-amino-2-oxopyrimidin-1-yl optionally substituted at position-5 by iodo or trifluoromethyl; Z is hydrogen and Z' is hydroxy or fluoro; or Z and Z' are both fluoro; or Z together with Z' is oxo; and the wavy line indicates that the group may be above or below the plane of the ring; and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
12 words
A compound of claim 1 wherein A and C are both hydroxy.
Claim 4
Dependent Claim
8 words
The compound of claim 2 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4α-hydroxy-5.beta.-hydroxymethylcyclopentane-1,2-diol.
Claim 5
Dependent Claim
8 words
The compound of claim 2 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4β-hydroxy-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 6
Dependent Claim
8 words
The compound of claim 2 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4α-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 7
Dependent Claim
8 words
The compound of claim 2 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4β-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 8
Dependent Claim
8 words
The compound of claim 2 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4α,4β-difluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 9
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-trifluoromethylpyrimidin-1-yl)-4α-hydroxy-5.beta.-hydroxymethylcyclopentane-1,2-diol.
Claim 10
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-trifluoromethylpyrimidin-1-yl)-4β-hydroxy-5.beta.-hydroxymethylcyclopentane-1,2-diol.
Claim 11
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-trifluoromethylpyrimidin-1-yl)-4α-fluoro-5.beta.-hydroxymethylcyclopentane-1,2-diol.
Claim 12
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-trifluoromethylpyrimidin-1-yl)-4β-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 13
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-trifluoromethylpyrimidin-1-yl)-4α,4β-difluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 14
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4α-hydroxy-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 15
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4β-hydroxy-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 16
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4α-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 17
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4β-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 18
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4α,4β-difluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 19
Dependent Claim
8 words
The compound of claim 2 which is 3β-(6-aminopurin-9-yl)-4α-hydroxy-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 20
Dependent Claim
8 words
The compound of claim 2 which is 3β-(6-aminopurin-9-yl)-4β-hydroxy-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 21
Dependent Claim
8 words
The compound of claim 2 which is 3β-(6-aminopurin-9-yl)-4α-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 22
Dependent Claim
8 words
The compound of claim 2 which is 3β-(6-aminopurin-9-yl)-4β-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 23
Dependent Claim
8 words
The compound of claim 2 which is 3β-(6-aminopurin-9-yl)-4α,4β-difluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 24
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2-amino-6-oxopurin-9-yl)-4α-hydroxy-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 25
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2-amino-6-oxopurin-9-yl)-4β-hydroxy-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 26
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2-amino-6-oxopurin-9-yl)-4α-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 27
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2-amino-6-oxopurin-9-yl)-4β-fluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 28
Dependent Claim
8 words
The compound of claim 2 which is 3β-(2-amino-6-oxopurin-9-yl)-4α,4β-difluoro-5β-hydroxymethylcyclopentane-1,2-diol.
Claim 29
Dependent Claim
13 words
A compound of claim 1 wherein A is hydroxy and C is hydrogen.
Claim 30
Dependent Claim
8 words
The compound of claim 28 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4α-hydroxy-5.beta.-hydroxymethylcyclopentan-1α-ol.
Claim 31
Dependent Claim
8 words
The compound of claim 28 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4β-hydroxy-5β-hydroxymethylcyclopentan-1α-ol.
Claim 32
Dependent Claim
8 words
The compound of claim 28 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4α-fluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 33
Dependent Claim
8 words
The compound of claim 28 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4β-fluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 34
Dependent Claim
8 words
The compound of claim 28 which is 3β-[2,4-dioxo-5-(2-bromovinyl)pyrimidin-1-yl]-4α,4β-difluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 35
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-trifluoropyrimidin-1-yl)-4α-hydroxy-5β-hydroxymethylcyclopentan-1α-ol.
Claim 36
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-trifluoropyrimidin-1-yl)-4β-hydroxy-5β-hydroxymethylcyclopentan-1α-ol.
Claim 37
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-trifluoropyrimidin-1-yl)-4α-fluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 38
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-trifluoropyrimidin-1-yl)-4β-fluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 39
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-trifluoropyrimidin-1-yl)-4α,4β-difluoro-5.beta.-hydroxymethylcyclopentan-1α-ol.
Claim 40
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4α-hydroxy-5β-hydroxymethylcyclopentan-1α-ol.
Claim 41
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4β-hydroxy-5β-hydroxymethylcyclopentan-1α-ol.
Claim 42
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4α-fluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 43
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4β-fluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 44
Dependent Claim
8 words
The compound of claim 28 which is 3β-(2,4-dioxo-5-iodopyrimidin-1-yl)-4α,4β-difluoro-5β-hydroxymethylcyclopentan-1α-ol.
Claim 45
Dependent Claim
36 words
A pharmaceutical composition useful for treating viral infections in mammals which comprises an effective amount of at least one compound of claim 1 or a pharmaceutically acceptable acid addition salt thereof and a pharmaceutically acceptable excipient.
Claim 46
Dependent Claim
21 words
A method for treating mammals for viral infections which comprises administering an effective amount of a pharmaceutical composition of claim 44.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-08-11 | 1990-02-10 | 1990-08-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-11 | 1994-02-10 | 1994-08-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-11 | 1998-02-10 | 1998-08-12 | $7700.00 | Window Closed / Lapsed |