US5470967A
Expired / Lapsed
US
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Oligonucleotide analogs with sulfamate linkages
Assignee: Bristol Myers Squibb Pharma Co
•
Filing: 1990-04-10
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Granted: 1995-11-28
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Expires: 2010-04-10
Abstract
Abstract Oligonucleotides possessing at least one sulfamate or sulfamide internucleotides linkages. These compounds can be used as specific hybridization probes to detect complementary nucleic acid sequences.
Inventors
- 👤 Edward M. Huie
- 👤 George L. Trainor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 08:56
CPC Classifications
C; C07; C07H; C07H21/00; A; A61; A61P; A61P31/00; A61P31/12
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
283 words
A compound of the formula: ##STR14## wherein: A is H, OH, OR 8 , OQ or halogen; B is a naturally occurring nucleic acid base or modified nucleic acid base; Y is --N(R)-- or O; Z is --N(R 7 )-- or O; wherein Y, OR 2 , and A are independently bonded to the 2' or 3' position and provided further that A is bonded to a position different from that of Y or OR 2 ; wherein each M is independently selected from ##STR15## provided at least one M is S(═O)═O; and provided that when M is S(═O)═O, Y and Z cannot both be O; n is 1 to 75; R is H or alkyl of 1 to 6 carbon atoms; R 1 is H 2 PO 3 , H 3 P 2 O 5 , H 4 P 3 O 7 and their suitable salts, H or an hydroxyl protecting group; R 2 is H 2 PO 3 , H 3 P 2 O 5 , H 4 P 3 O 7 and their suitable salts, H or an hydroxyl protecting group; R 3 is alkyl or cyanoethyl; R 4 is H or alkyl of 1 to 6 carbon atoms; R 5 is H or alkyl of 1 to 6 carbon atoms; R 6 is H or alkyl of 1 to 6 carbon atoms; R 7 is H or alkyl of 1 to 6 carbon atoms; R 8 is alkyl of 1 to 6 carbon atoms; R 9 is alkyl of 1 to 6 carbon atoms or cyanoethyl; and Q is an hydroxyl protecting group; provided that when each M is S(═O)═O, then at least one B group is not thymine.
Claim 2
Dependent Claim
283 words
A compound of the formula: ##STR14## wherein: A is H, OH, OR 8 , OQ or halogen; B is a naturally occurring nucleic acid base or modified nucleic acid base; Y is --N(R)-- or O; Z is --N(R 7 )-- or O; wherein Y, OR 2 , and A are independently bonded to the 2' or 3' position and provided further that A is bonded to a position different from that of Y or OR 2 ; wherein each M is independently selected from ##STR15## provided at least one M is S(═O)═O; and provided that when M is S(═O)═O, Y and Z cannot both be O; n is 1 to 75; R is H or alkyl of 1 to 6 carbon atoms; R 1 is H 2 PO 3 , H 3 P 2 O 5 , H 4 P 3 O 7 and their suitable salts, H or an hydroxyl protecting group; R 2 is H 2 PO 3 , H 3 P 2 O 5 , H 4 P 3 O 7 and their suitable salts, H or an hydroxyl protecting group; R 3 is alkyl or cyanoethyl; R 4 is H or alkyl of 1 to 6 carbon atoms; R 5 is H or alkyl of 1 to 6 carbon atoms; R 6 is H or alkyl of 1 to 6 carbon atoms; R 7 is H or alkyl of 1 to 6 carbon atoms; R 8 is alkyl of 1 to 6 carbon atoms; R 9 is alkyl of 1 to 6 carbon atoms or cyanoethyl; and Q is an hydroxyl protecting group; provided that when each M is S(═O)═O, then at least one B group is not thymine.
Claim 3
Dependent Claim
28 words
The compound of claim 1 wherein when M is S(═O)═O, one of Y or Z is --N(R)-- or --N(R 7 )-- and R or R 7 is H.
Claim 4
Dependent Claim
16 words
The compound of claim 1 wherein R is an alkyl of less than 5 carbon atoms.
Claim 5
Dependent Claim
17 words
The compound of claim 1 wherein R 3 is an alkyl of less than 5 carbon atoms.
Claim 6
Dependent Claim
17 words
The compound of claim 1 wherein R 4 is an alkyl of less than 5 carbon atoms.
Claim 7
Dependent Claim
17 words
The compound of claim 1 wherein R 5 is an alkyl of less than 5 carbon atoms.
Claim 8
Dependent Claim
17 words
The compound of claim 1 wherein R 6 is an alkyl of less than 5 carbon atoms.
Claim 9
Dependent Claim
17 words
The compound of claim 1 wherein R 7 is an alkyl of less than 5 carbon atoms.
Claim 10
Dependent Claim
17 words
The compound of claim 1 wherein R 8 is an alkyl of less than 5 carbon atoms.
Claim 11
Dependent Claim
17 words
The compound of claim 1 wherein R 9 is an alkyl of less than 5 carbon atoms.
Claim 12
Dependent Claim
13 words
The compound of claim 1 wherein the A substituent is in the 2'-position.
Claim 13
Dependent Claim
17 words
The compound of claim 1 wherein A is selected from the group consisting of H and OH.
Claim 14
Dependent Claim
14 words
The compound of claim 1 wherein B is adenine, guanine, cytosine, thymine or uracil.
Claim 15
Dependent Claim
32 words
The compound of claim 1 wherein M is S(═O)═O for the internucleotide linkage at the 3' terminus or 5' terminus, or both the 3' terminus and the 5' terminus of the compound.
Claim 16
Dependent Claim
9 words
The compound of claim 1 wherein M is S(═O)═O.
Claim 17
Dependent Claim
11 words
The compound of claim 1 wherein M is S(═O)═O or P(═O)--OH.
Claim 18
Dependent Claim
22 words
The compound of claim 16 wherein Y or Z is --N(R)-- or --N(R 7 )--, and R or R 7 is H.
Claim 19
Dependent Claim
153 words
A compound of the formula: ##STR16## wherein: A is H, OH, OR 4 , OQ, or halogen; B is a naturally occurring nucleic acid base or modified nucleic acid base; n is 1 to 75; R 1 is alkyl of 1 to 6 carbon atoms; R 2 is dialkylamino, morpholino, piperidino, or pyrrolidono; R 3 is alkyl of 1 to 6 carbon atoms; R 4 is alkyl of 1 to 6 carbon atoms; Y is --N(R)-- or O; Z is --N(R)-- or O; wherein Y, OP(R 2 )(OV), and A are independently bonded to the 2' or 3' position and provided further that A is bonded to a position different from that of Y or OP(R 2 ) (OV); R is H or alkyl of 1 to 6 carbon atoms; Q is an hydroxyl protecting group; and V is an hydroxyl protecting group; provided that at least one B group is not thymine.
Claim 20
Dependent Claim
153 words
A compound of the formula: ##STR16## wherein: A is H, OH, OR 4 , OQ, or halogen; B is a naturally occurring nucleic acid base or modified nucleic acid base; n is 1 to 75; R 1 is alkyl of 1 to 6 carbon atoms; R 2 is dialkylamino, morpholino, piperidino, or pyrrolidono; R 3 is alkyl of 1 to 6 carbon atoms; R 4 is alkyl of 1 to 6 carbon atoms; Y is --N(R)-- or O; Z is --N(R)-- or O; wherein Y, OP(R 2 )(OV), and A are independently bonded to the 2' or 3' position and provided further that A is bonded to a position different from that of Y or OP(R 2 ) (OV); R is H or alkyl of 1 to 6 carbon atoms; Q is an hydroxyl protecting group; and V is an hydroxyl protecting group; provided that at least one B group is not thymine.
Claim 21
Dependent Claim
11 words
The compound of claim 18 wherein V is cyanoethyl or methyl.
Claim 22
Dependent Claim
28 words
The compound of claim 18 wherein Q is selected from the group consisting of C 1 -C 5 trialkylsilyl, C 1 -C 5 alkyl, acyl, cyanoethyl or tetrahydropyran.
Claim 23
Dependent Claim
16 words
The compound of claim 18 wherein R is an alkyl of less than 5 carbon atoms.
Claim 24
Dependent Claim
17 words
The compound of claim 18 wherein R 1 is an alkyl of less than 5 carbon atoms.
Claim 25
Dependent Claim
17 words
The compound of claim 18 wherein R 3 is an alkyl of less than 5 carbon atoms.
Claim 26
Dependent Claim
17 words
The compound of claim 18 wherein R 4 is an alkyl or less than 5 carbon atoms.
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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) | 1998-11-27 | 1999-05-29 | 1999-11-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-11-27 | 2003-05-29 | 2003-11-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-11-27 | 2007-05-29 | 2007-11-28 | $7700.00 | Window Closed / Lapsed |