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US4973679A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for oligonucleo tide synthesis using phosphormidite intermediates

Assignee: University Patents Inc
•
Filing: 1986-09-18
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Granted: 1990-11-27
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Expires: 2006-09-18
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Abstract

Abstract A new class of nucleoside phosphoramidites which are relatively stable to permit isolation thereof and storage at room temperature. The phosphoramidites are derivatives of saturated secondary amines.

Inventors

  • 👤 Marvin H. Caruthers
  • 👤 Serge L. Beaucage

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 09:39
CPC Classifications
C; C07; C07H; C07H21/00

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 213 words
In a process for producing oligonucleotides which comprises the step of condensing the 3'-OH or 5'-OH group of a nucleoside or oligonucleotide with a nucleoside phosphite, the improvement being that the nucleoside phosphite is a compound of one of the formulae: ##STR24## wherein B is a nucleoside or deoxynucleoside base; A is H OH or OR 4 in which R 4 is a blocking group; R is a blocking group; R 1 ' is a hydrocarbyl radical containing up to about carbon atoms; and X is NR 2 'R 3 ', wherein R 2 ' and R 3 ' taken separately each represent alkyl, aryl, aralkyl, cycloalkyl and cycloalkylalkyl containing up to 10 carbon atoms; R 2 ' and R 3 ' when taken together form an alkylene chain containing up to 5 carbon atoms in the principal chain and a total of up to 10 carbon atoms with both terminal valence bonds of said chain being attached to the nitrogen atom to which R 2 ' and R 3 ' are attached; and R 2 ' and R 3 ' when taken together with the nitrogen atom to which they are attached form a saturated nitrogen heterocycle including at least one additional heteroatom from the group consisting of nitrogen, oxygen and sulfur.
Claim 2
Dependent Claim 213 words
In a process for producing oligonucleotides which comprises the step of condensing the 3'-OH or 5'-OH group of a nucleoside or oligonucleotide with a nucleoside phosphite, the improvement being that the nucleoside phosphite is a compound of one of the formulae: ##STR24## wherein B is a nucleoside or deoxynucleoside base; A is H OH or OR 4 in which R 4 is a blocking group; R is a blocking group; R 1 ' is a hydrocarbyl radical containing up to about carbon atoms; and X is NR 2 'R 3 ', wherein R 2 ' and R 3 ' taken separately each represent alkyl, aryl, aralkyl, cycloalkyl and cycloalkylalkyl containing up to 10 carbon atoms; R 2 ' and R 3 ' when taken together form an alkylene chain containing up to 5 carbon atoms in the principal chain and a total of up to 10 carbon atoms with both terminal valence bonds of said chain being attached to the nitrogen atom to which R 2 ' and R 3 ' are attached; and R 2 ' and R 3 ' when taken together with the nitrogen atom to which they are attached form a saturated nitrogen heterocycle including at least one additional heteroatom from the group consisting of nitrogen, oxygen and sulfur.
Claim 3
Dependent Claim 12 words
The process according to claim 1 wherein R is a trityl group.
Claim 4
Dependent Claim 11 words
The process according to claim 1 wherein R is a di-p-anisylphenylmethyl.
Claim 5
Dependent Claim 10 words
The process according to claim 1 wherein R is p-anisyldiphenylmethyl.
Claim 6
Dependent Claim 13 words
The process according to claim 1 wherein R 1 ' is lower alkyl.
Claim 7
Dependent Claim 11 words
The process according to claim 1 wherein X is di-lower alkylamino.
Claim 8
Dependent Claim 13 words
The process according to claim 1 wherein X is a saturated nitrogen heterocyclic.
Claim 9
Dependent Claim 15 words
The process according to claim 1 wherein B is adenine, guanine, cytosine, uracil or thymine.
Claim 10
Dependent Claim 25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R 1 ' is methyl, A is H and X is morpholino.
Claim 11
Dependent Claim 24 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is thyminyl, R 1 is methyl, A is H and X is dimethylamino.
Claim 12
Dependent Claim 25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 1-(N-4-benzoylcytosinyl), R 1 ' is methyl, A is H and X is dimethylamino.
Claim 13
Dependent Claim 25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R 1 ' is methyl, A is H and X is dimethylamino.
Claim 14
Dependent Claim 25 words
The process according to claim 1 wherein R is di-p-anisylphenylmethyl, B is 9-(N-2-isobutyrylguaninyl), R 1 ' is methyl, A is H and X is dimethylamino.
Claim 15
Dependent Claim 18 words
The process according to claim 1 wherein said nucleoside or oligonucleotide is covalently bonded to an inorganic polymer.
Claim 16
Dependent Claim 23 words
The process according to claim 14 wherein said nucleoside or oligonucleotide is linked to the inorganic polymer through a base hydrolyzable covalent bond.
Claim 17
Dependent Claim 16 words
The process according to claim 15 wherein the base hydrolyzable covalent bond is an ester linkage.

References Cited (Backward Citations)

US4458066A Cited
US4500707A Cited
US4415732A Cited
US4725677A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-11-26 1994-05-28 1994-11-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-11-26 1998-05-28 1998-11-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-11-26 2002-05-28 2002-11-27 $7700.00 Window Closed / Lapsed

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