US4980460A
Expired / Lapsed
US
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Protected nucleosides which permit more efficient oligonucleotide syntheses
Assignee: Commissariat à l'Énergie Atomique et Aux Énergies Alternatives
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Filing: 1987-03-30
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Granted: 1990-12-25
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Expires: 2007-03-30
Abstract
Abstract The invention relates to derivatives of nucleosides and their use for the synthesis of oligonucleotides. These derivatives are in accordance with the formula: <IMAGE> (I) in which B represents a radical derived from guanine, cytosine or adenine, whose exocylic NH group is protected by the group <IMAGE> with R1 representing a hydrogen atom or an alkyl radical and R2 a hydrogen atom, and alkyl radical, an alkoxy radical and optionally substituted aryloxy radical, R3 represents a hydrogen atom, the dimethoxytrityl radical or the radical <IMAGE> R4 represents a hydrogen atom, the radical of formula: <IMAGE> or a radical suitable for the synthesis of polynucleotides and R5 represents a hydrogen atom or the protected or unprotected hydroxyl OH radical.
Inventors
- 👤 Didier Molko
- 👤 Jean-Claude Schulhof
- 👤 Robert Teoule
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 00:53
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C07H21/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
138 words
A nucleoside having the formula: wherein B is a divalent group chosen from among; ##STR33## connected to the CO group by its exocyclic NH group; R 1 is hydrogen, R 2 is a group selected from the group consisting of methoxy, phenoxy, chlorophenoxy and fluorophenoxy, R 3 is selected from the group consisting of hydrogen, 9-phenyl xanthenyl, trityl of formula; ##STR34## wherein R 6 , R 7 and R 8 , which may be the same or different, are hydrogen, methyl, ethyl or methoxy, and the group ##STR35## wherein R 1 and R 2 have the meanings given above; R 4 is a hydrogen, a phosphorylated group selected from the group consisting of ##STR36## or the group ##STR37## wherein R 1 and R 2 have the meanings given above; and R 5 is a hydrogen or hydroxyl group.
Claim 2
Dependent Claim
138 words
A nucleoside having the formula: wherein B is a divalent group chosen from among; ##STR33## connected to the CO group by its exocyclic NH group; R 1 is hydrogen, R 2 is a group selected from the group consisting of methoxy, phenoxy, chlorophenoxy and fluorophenoxy, R 3 is selected from the group consisting of hydrogen, 9-phenyl xanthenyl, trityl of formula; ##STR34## wherein R 6 , R 7 and R 8 , which may be the same or different, are hydrogen, methyl, ethyl or methoxy, and the group ##STR35## wherein R 1 and R 2 have the meanings given above; R 4 is a hydrogen, a phosphorylated group selected from the group consisting of ##STR36## or the group ##STR37## wherein R 1 and R 2 have the meanings given above; and R 5 is a hydrogen or hydroxyl group.
Claim 3
Dependent Claim
14 words
The nucleoside of claim 1 wherein B is the divalent group of formula (II).
Claim 4
Dependent Claim
14 words
The nucleoside of claim 1 wherein B is the divalent group of formula (IV).
Claim 5
Dependent Claim
10 words
The nucleoside of claim 2 wherein R 2 is ##STR38##
Claim 6
Dependent Claim
10 words
The nucleoside of claim 3 wherein R 2 is phenoxy.
Claim 7
Dependent Claim
13 words
The nucleoside of claim 4 or claim 5 wherein R 5 is hydrogen.
Claim 8
Dependent Claim
16 words
The nucleoside of claim 6 wherein R 3 is ##STR39## and wherein R 4 is ##STR40##
Claim 9
Dependent Claim
16 words
The nucleoside of claim 6 wherein R 3 is ##STR41## and wherein R 4 is ##STR42##
Claim 10
Dependent Claim
16 words
The nucleoside of claim 6 wherein R 3 is ##STR43## and wherein R 4 is ##STR44##
Claim 11
Dependent Claim
13 words
The nucleoside of claim 6 wherein R 3 and R 4 are hydrogen.
Claim 12
Dependent Claim
20 words
The nucleoside of claim 2 wherein R 2 is chlorophenoxy, R 3 , R 4 and R 5 are hydrogen.
Claim 13
Dependent Claim
15 words
The nucleoside of claim 6, wherein R 3 is 4,4'-dimethoxytrityl and R 4 is hydrogen.
References Cited (Backward Citations)
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| 3.5 Years (Year 4) | 1993-12-24 | 1994-06-25 | 1994-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-24 | 1998-06-25 | 1998-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-24 | 2002-06-25 | 2002-12-25 | $7700.00 | Window Closed / Lapsed |