US4924624A
Expired / Lapsed
US
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2,',5'-phosphorothioate oligoadenylates and plant antiviral uses thereof
Assignee: Temple University
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Filing: 1987-10-22
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Granted: 1990-05-15
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Expires: 2007-10-22
Abstract
Abstract Optically active compounds of the formula ##STR1## wherein n is 1 or 2 and m is 0, 1, 2 or 3 have antiviral activity. Compounds of the formula wherein at least one of the internucleotide phosphorothioate linkages is of the Sp configuration possess increased antiviral activity and/or metabolic stability.
Inventors
- 👤 Robert J. Suhadolnik
- 👤 Wolfgang Pfleiderer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:48
CPC Classifications
C; C07; C07H; C07H21/00; A; A61; A61P; A61P31/00; A61P31/12
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
54 words
A compound which is an optical isomer of the formula: ##STR14## substantially free of contamination by other optical isomers of the same formula, wherein m is zero, 1,2 or 3; n is 1 or 2; and at least one of the internucleotide phosphorothioate groups ##STR15## is of the Sp configuration; or water-soluble salt thereof.
Claim 2
Dependent Claim
54 words
A compound which is an optical isomer of the formula: ##STR14## substantially free of contamination by other optical isomers of the same formula, wherein m is zero, 1,2 or 3; n is 1 or 2; and at least one of the internucleotide phosphorothioate groups ##STR15## is of the Sp configuration; or water-soluble salt thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1 wherein m is 1.
Claim 4
Dependent Claim
22 words
A compound according to claim 1 wherein the internucleotide phosphorothioate group adjacent the 2' terminal adenylate moiety is of the Sp configuration.
Claim 5
Dependent Claim
7 words
(Rp)-P-thioadenylyl-(2'5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, being a compound of claim 1.
Claim 6
Dependent Claim
7 words
(Sp)-P-thioadenylyl-(2'-5')-(Rp)-P-thioadenylyl-(2'-5')-adenosine, being a compound of claim 1.
Claim 7
Dependent Claim
8 words
(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, being a compound according to claim 1.
Claim 8
Dependent Claim
7 words
5'-O-phosphoryl-(Rp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, being a compound of claim 1.
Claim 9
Dependent Claim
7 words
5'-O-phosphoryl-(Sp)-P-thioadenylyl-(2'-5')-(Rp)-P-thioadenylyl-(2'-5')-adenosine, being a compound of claim 1.
Claim 10
Dependent Claim
8 words
5'-O-phosphoryl-(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, being a compound according to claim 1.
Claim 11
Dependent Claim
13 words
(Rp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-(Rp)-P-thioadenylyl-(2'-5')-adenosine, and 5'-mono-, di-, and triphosphates thereof, being compounds according to claim 1.
Claim 12
Dependent Claim
6 words
The 5'-monophosphate according to claim 10.
Claim 13
Dependent Claim
13 words
(Rp)-P-thioadenylyl-(2'-5')-(Rp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, and 5'-mono-, di-, and triphosphates thereof, being compounds according to claim 10.
Claim 14
Dependent Claim
6 words
The 5'-monophosphate according to claim 12.
Claim 15
Dependent Claim
13 words
(Rp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, and 5'-mono-, di-, and triphosphates thereof, being compounds according to claim 1.
Claim 16
Dependent Claim
6 words
The 5'-monophosphate according to claim 14.
Claim 17
Dependent Claim
13 words
(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-(Rp)-P-thioadenylyl-(2'-5')-adenosine, and 5'-mono-, di-, and triphosphates thereof, being compounds according to claim 1.
Claim 18
Dependent Claim
6 words
The 5'-monophosphate according to claim 16.
Claim 19
Dependent Claim
16 words
(Sp)-P-thioadenyl-(2'-5')-( Rp)- P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, and 5'- mono-, di-, and triphosphates thereof, being compounds according to claim 1.
Claim 20
Dependent Claim
6 words
The 5'-monophosphate according to claim 18.
Claim 21
Dependent Claim
14 words
(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, and 5'- mono-, di-, and triphosphates thereof, being compounds according to claim 1.
Claim 22
Dependent Claim
6 words
The 5'-monophosphate according to claim 20.
Claim 23
Dependent Claim
22 words
A method of inhibiting viral infection in plants comprising administering thereto an antiviral effective amount of a compound according to claim 1.
Claim 24
Dependent Claim
20 words
A method of inhibiting viral infection in plants comprising thereto an antiviral effective amount of compound according to claim 2.
Claim 25
Dependent Claim
15 words
A method according to claim 22, wherein the compound is (Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine or the 5'-monophosphate thereof.
Claim 26
Dependent Claim
11 words
A method according to claim 22, wherein the compound is (Rp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine.
Claim 27
Dependent Claim
15 words
A method according to claim 22, wherein the compound is (Rp)-P-thioadenylyl-(2'-5')-(Rp)-P-thioadenylyl-(2'-5')-adenosine or the 5'-monophosphate thereof.
Claim 28
Dependent Claim
11 words
A method according to claim 22 wherein the compound is (Rp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine.
Claim 29
Dependent Claim
11 words
A method according to claim 22 wherein the compound is (Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine.
Claim 30
Dependent Claim
10 words
A compound according to claim 1 where n is 2.
Claim 31
Dependent Claim
10 words
A compound according to claim 1 where m is 3.
Claim 32
Dependent Claim
12 words
A method according to claim 22 for inhibiting tobacco mosaic virus infection.
Claim 33
Dependent Claim
63 words
A pharmaceutical composition comprising a pharmaceutical carrier and a compound which is an optical iosmer of the formula: ##STR16## substantially free of contamination by other optical isomers of the same formula, wherein m is zero, 1, 2 or 3; n is 1 or 2; and at least one of the internucleotide phosphorothioate groups ##STR17## is of the Sp configuration; or water-soluble salt thereof.
Claim 34
Dependent Claim
63 words
A pharmaceutical composition comprising a pharmaceutical carrier and a compound which is an optical iosmer of the formula: ##STR16## substantially free of contamination by other optical isomers of the same formula, wherein m is zero, 1, 2 or 3; n is 1 or 2; and at least one of the internucleotide phosphorothioate groups ##STR17## is of the Sp configuration; or water-soluble salt thereof.
Claim 35
Dependent Claim
10 words
A composition according to claim 32 wherein m is 1.
Claim 36
Dependent Claim
15 words
A composition according to claim 32 wherein the compound is (Rp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, or the 5'-monophosphate thereof.
Claim 37
Dependent Claim
15 words
A composition according to claim 32 wherein the compound is (Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-(Sp)-P-thioadenylyl-(2'-5')-adenosine, or the 5'-monophosphate thereof.
References Cited (Backward Citations)
No citation records indexed.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-05-14 | 1993-11-13 | 1994-05-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-05-14 | 1997-11-13 | 1998-05-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-05-14 | 2001-11-13 | 2002-05-15 | $7700.00 | Window Closed / Lapsed |