US4757141A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Amino-derivatized phosphite and phosphate linking agents, phosphoramidite precursors, and useful conjugates thereof
Assignee: Applied Biosystems LLC
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Filing: 1985-08-26
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Granted: 1988-07-12
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Expires: 2005-08-26
Abstract
Abstract The compounds of the invention include novel linking agents comprising 2-substituted-3-protected-1,3,2-oxazaphosphacycloalkanes and their phosphoramidite precursors. The compounds of the invention further include conjugates of the above linking agents with oligonucleotides and polymer supports. The compounds of the present invention are useful for linking organic moieties, such as fluorescent or chromogenic dyes, to polymer supports and oligonucleotides, particularly single- and double-stranded DNA and RNA fragments.
Inventors
- 👤 Steven Fung
- 👤 Sam L. Woo
- 👤 Lloyd M. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:23
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/22; C07F9/24; C07F9/2404; C07F9/2416; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/545; A61K47/548; C07F9/2408; C07F9/547; C07F9/6564; C07F9/6581; C07F9/6584; C07F9/65842; C07H; C07H21/00; C08; C08B; C08B37/00; C08B37/0006; C08B37/0009; C08B37/0021; C08B37/0036; C08B37/0039
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
95 words
A compound of the formula: ##STR9## wherein: i is 0 or 1; j is in the range of 2 to 10; k is 1 when i is 0, or k is 0 or 1 when i is 1; R 1 is an amino protection group; R 2 and R 3 taken separately each represent hydrogen, lower alkyl, lower cycloalkyl, lower acyl, cyano, halo, or nitro; R 4 is alkyl, alkenyl, aryl, aralkyl, or cycloalkyl containing up to 10 carbon atoms; and W represents a hydroxylic polymer support, or an oligonucleotide linked to a polymer support.
Claim 2
Dependent Claim
95 words
A compound of the formula: ##STR9## wherein: i is 0 or 1; j is in the range of 2 to 10; k is 1 when i is 0, or k is 0 or 1 when i is 1; R 1 is an amino protection group; R 2 and R 3 taken separately each represent hydrogen, lower alkyl, lower cycloalkyl, lower acyl, cyano, halo, or nitro; R 4 is alkyl, alkenyl, aryl, aralkyl, or cycloalkyl containing up to 10 carbon atoms; and W represents a hydroxylic polymer support, or an oligonucleotide linked to a polymer support.
Claim 3
Dependent Claim
30 words
A compound according to claim 1 wherein R 2 and R 3 are hydrogens, and R 4 is lower alkyl, electron-withdrawing beta-substituted ethyl, electron-withdrawing substituted phenyl, or electron-withdrawing substituted phenylethyl.
Claim 4
Dependent Claim
16 words
A compound according to claim 2 wherein j is in the range of 2 to 4.
Claim 5
Dependent Claim
36 words
A compound according to claim 3 wherein R 1 taken together with the nitrogen atom to which it is attached is a base-labile carbamate or amide protection group, and wherein W is a hydroxylic polymer support.
Claim 6
Dependent Claim
15 words
A compound according to claim 4 wherein R 1 is trihaloacetyl, acetoacetyl, or fluorenylmethyl carbamate.
Claim 7
Dependent Claim
15 words
A compound according to claim 3 wherein R 1 is an acid-labile amino protection group.
Claim 8
Dependent Claim
15 words
A compound according to claim 6 wherein R 1 is trityl or lower alkoxy-substituted trityl.
Claim 9
Dependent Claim
15 words
A compound according to claim 4 wherein said hdyroxylic polymer support is a cross-linked polysaccharide.
Claim 10
Dependent Claim
21 words
A compound according to claim 8 wherein said cross-linked polysaccharide is selected from the group consisting of dextran, cellulose, and agarose
Claim 11
Dependent Claim
96 words
A compound of the formula: ##STR10## wherein: R 1 is an amino protection group; s is in the range of 0 to 8, t is in the range of 0 to 8, and s+t is in the range of 1 to 8; R 4 represents lower alkyl; electron-withdrawing beta-substituted ethyl; electron-electron-withrawing substituted phenyl; or electron-withdrawing substituted phenylethyl; i is O or l; k is l when i is O or k is O or l when i is l; and W is an oligonucleotide, a hydroxylic polymer support, or an oligonucleotide liked to a polymer support.
Claim 12
Dependent Claim
96 words
A compound of the formula: ##STR10## wherein: R 1 is an amino protection group; s is in the range of 0 to 8, t is in the range of 0 to 8, and s+t is in the range of 1 to 8; R 4 represents lower alkyl; electron-withdrawing beta-substituted ethyl; electron-electron-withrawing substituted phenyl; or electron-withdrawing substituted phenylethyl; i is O or l; k is l when i is O or k is O or l when i is l; and W is an oligonucleotide, a hydroxylic polymer support, or an oligonucleotide liked to a polymer support.
Claim 13
Dependent Claim
25 words
A compound according to claim 10 wherein t is in the range of 0 to 2, s is in the range of 1 to 3.
Claim 14
Dependent Claim
11 words
A compound according to claim 11 wherein W is an oligonucleotide.
Claim 15
Dependent Claim
36 words
A compound according to claim 11 wherein R 1 taken together with the nitrogen atom to which it is attached is a base-labile amide or carbamate protection group, and wherein W is a hydroxylic polymer support.
Claim 16
Dependent Claim
15 words
A compound according to claim 13 wherein R 1 is trihaloacetyl, acetoacetyl, or fluorenylmethyl carbamate.
Claim 17
Dependent Claim
19 words
A compound according to claim 14 wherein t is 0, s is in the range of 1 to 2.
Claim 18
Dependent Claim
34 words
A compound according to claim 11 wherein t is in the range of 0 to 2, s is in the range of 1 to 3, and R 1 is an acid-labile amino protection group.
Claim 19
Dependent Claim
15 words
A compound according to claim 16 wherein R 1 is trityl or lower alkoxy-substituted trityl.
References Cited (Backward Citations)
US4255566A
Cited
US4458066A
Cited
US4500707A
Cited
US4415732A
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US4401796A
Cited
US4605735A
Cited
FR2556726A1
Cited
GB2153356A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-07-12 | 1992-01-11 | 1992-07-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-07-12 | 1996-01-11 | 1996-07-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-07-12 | 2000-01-11 | 2000-07-12 | $7700.00 | Window Closed / Lapsed |