US4415732A
Expired / Lapsed
US
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Phosphoramidite compounds and processes
Assignee: University Patents Inc
•
Filing: 1981-03-27
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Granted: 1983-11-15
•
Expires: 2001-03-27
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
2026-10-23 20:05
CPC Classifications
C; C07; C07H; C07H21/00
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
172 words
A compound represented by one of the formulae: ##STR4## wherein B is a nucleoside or deoxynucleoside base; A is H, OH or OR 2 in which R 2 is a blocking group; R is a blocking group; R 1 is a hydrocarbyl radical containing up to about 10 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
172 words
A compound represented by one of the formulae: ##STR4## wherein B is a nucleoside or deoxynucleoside base; A is H, OH or OR 2 in which R 2 is a blocking group; R is a blocking group; R 1 is a hydrocarbyl radical containing up to about 10 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
170 words
A compound represented by the formula: ##STR5## wherein B is a nucleoside or deoxynucleoside base; A is H, OH or OR 2 in which R 2 is a blocking group; R is a blocking group; R 1 is a hydrocarbyl radical containing up to about 10 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 4
Dependent Claim
170 words
A compound represented by the formula: ##STR5## wherein B is a nucleoside or deoxynucleoside base; A is H, OH or OR 2 in which R 2 is a blocking group; R is a blocking group; R 1 is a hydrocarbyl radical containing up to about 10 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 5
Dependent Claim
14 words
A compound according to claim 1 or 2 wherein R is a trityl group.
Claim 6
Dependent Claim
14 words
A compound according to claim 1 or 2 wherein R is a di-p-anisylphenylmethyl group.
Claim 7
Dependent Claim
14 words
A compound according to claim 1 or 2 wherein R is a p-anisyldiphenylmethyl group.
Claim 8
Dependent Claim
14 words
A compound according to claim 1 or 2 wherein R 1 is lower alkyl.
Claim 9
Dependent Claim
13 words
A compound according to claim 1 or 2 wherein x is di-lower alkylamino.
Claim 10
Dependent Claim
10 words
A compound according to claim 7 wherein X is dimethylamino.
Claim 11
Dependent Claim
15 words
A compound according to claim 1 or 2 wherein X is a saturated nitrogen heterocyclic.
Claim 12
Dependent Claim
15 words
A compound according to claim 9 wherein the nitrogen heterocyclic is piperidine, morpholine, or piperazine.
Claim 13
Dependent Claim
17 words
A compound according to claim 1 or 2 wherein B is adenine, guanine, cytosine, uracil and thymine.
Claim 14
Dependent Claim
24 words
The compound according to claim 2 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R 1 is methyl, A is H and X is dimethylamino.
Claim 15
Dependent Claim
24 words
The compound according to claim 2 wherein R is di-p-anisylphenylmethyl, B is thyminyl, R 1 is methyl, A is H and X is dimethylamino.
Claim 16
Dependent Claim
24 words
The compound according to claim 2 wherein R is di-p-anisylphenylmethyl, B is 1-(N-4-benzoylcytosinyl), R 1 is methyl, A is H and X is dimethylamino.
Claim 17
Dependent Claim
24 words
The compound according to claim 2 wherein R is di-p-anisylphenylmethyl, B is 9-(N-6-benzoyladeninyl), R 1 is methyl, A is H and X is piperidino.
Claim 18
Dependent Claim
24 words
The compound according to claim 2 wherein R is di-p-anisylphenylmethyl, B is 9-(N-2-isobutyrylguaninyl), R 1 is methyl, A is H and X is dimethylamino.
Claim 19
Dependent Claim
33 words
A compound according to claim 1 wherein X is selected from the class consisting of dimethylamino, diethylamino, diisopropylamino, dibutylamino, methylpropylamino, methylhexylamino, methylcyclopropylamino, ethylcyclohexylamino, methylbenzylamino, methylcyclohexylmethylamino, butylcyclohexylamino, morpholino, thiomorpholino, pyrrolidino, piperidino, 2,6-dimethylpiperidino and piperazino.
Claim 20
Dependent Claim
10 words
A compound according to claim 1 wherein X is diisopropylamino.
Claim 21
Dependent Claim
33 words
A compound according to claim 2 wherein X is selected from the class consisting of dimethylamino, diethylamino, diisopropylamino, dibutylamino, methylpropylamino, methylhexylamino, methylcyclopropylamino, ethylcyclohexylamino, methylbenzylamino, methylcyclohexylmethylamino, butylcyclohexylamino, morpholino, thiomorpholino, pyrrolidino, piperidino, 2,6-dimethylpiperidino and piperazino.
Claim 22
Dependent Claim
10 words
A compound according to claim 2 wherein X is diisopropylamino.
References Cited (Backward Citations)
US3534017A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-11-14 | 1987-05-16 | 1987-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-14 | 1991-05-16 | 1991-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-14 | 1995-05-16 | 1995-11-15 | $7700.00 | Window Closed / Lapsed |