Protecting group for synthesizing oligonucleotide analogs
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IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07H-001/02
C07H-021/04
C07H-021/02
출원번호
US-0811232
(1997-03-03)
발명자
/ 주소
Cheruvallath Zacharia S.
Capaldi Daniel C.
Ravikumar Vasulinga T.
Cole Douglas L.
출원인 / 주소
ISIS Pharmaceuticals, Inc.
대리인 / 주소
Oblon, Spivak, McClelland, Maier & Neustadt, P.C.
인용정보
피인용 횟수 :
27인용 특허 :
40
초록▼
Nucleoside analog phosphoramidites are provided in which the 3'-hydroxyl group is protected with an 2-N-amidoethyl group. The 2-N-amidoethyl protected nucleoside analogs are useful in the synthesis of a wide variety of oligonucleotide analogs. Coupling yields with the protected phosphoramidites in s
Nucleoside analog phosphoramidites are provided in which the 3'-hydroxyl group is protected with an 2-N-amidoethyl group. The 2-N-amidoethyl protected nucleoside analogs are useful in the synthesis of a wide variety of oligonucleotide analogs. Coupling yields with the protected phosphoramidites in solution or solid phase oligonucleotide analog synthesis are high and the 2-N-amidoethyl group can be removed easily under standard conditions.
대표청구항▼
[ What is claimed as new and desired to be secured by Letters Patent of the United States is:] [1.] A nucleoside analog phosphoramidite of formula (1): [ STR 21 ] wherein R.sup.1 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 het
[ What is claimed as new and desired to be secured by Letters Patent of the United States is:] [1.] A nucleoside analog phosphoramidite of formula (1): [ STR 21 ] wherein R.sup.1 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, substituted C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, C.sub.6 -C.sub.14 aryl, substituted C.sub.6 -C.sub.14 aryl, C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, substituted C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, C.sub.7 -C.sub.18 aralkyl, substituted C.sub.7 -C.sub.18 aralkyl, C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms and substituted C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms;R.sup.2, R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, substituted C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, C.sub.6 -C.sub.14 aryl, substituted C.sub.6 -C.sub.14 aryl, C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, substituted C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, C.sub.7 -C.sub.18 aralkyl, substituted C.sub.7 -C.sub.18 aralkyl, C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms and substituted C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms, orR.sup.3 and R.sup.4 together with the carbon atoms they are bonded to form a C.sub.3 -C.sub.8 cycloalkyl group, a substituted C.sub.3 -C.sub.8 cycloalkyl group, a C.sub.2 -C.sub.8 heterocycloalkyl group containing up to three heteroatoms or a substituted C.sub.2 -C.sub.8 heterocycloalkyl group containing up to three heteroatoms;each R.sup.5 is independently selected from the group consisting of C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, substituted C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, C.sub.6 -C.sub.14 aryl, substituted C.sub.6 -C.sub.14 aryl, C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, substituted C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, C.sub.7 -C.sub.18 aralkyl, substituted C.sub.7 -C.sub.18 aralkyl, C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms, and substituted C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms; or both R.sup.5 groups together with the nitrogen atom they are bonded to form a member selected from the group consisting of a C.sub.2 -C.sub.8 heterocycloalkyl group containing up to three heteroatoms, a substituted a C.sub.2 -C.sub.8 heterocycloalkyl group containing up to three heteroatoms, a C.sub.3 -C.sub.11 hetaryl group containing up to three heteroatoms and a substituted C.sub.3 -C.sub.11 hetaryl group containing up to three heteroatoms;R.sup.6 is a labile blocking group;B is an unprotected or protected heterocyclic base;X is selected from the group consisting of hydrogen, hydroxyl, F, Cl, Br, C.sub.1 -C.sub.8 alkyl, substituted C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, substituted C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, C.sub.6 -C.sub.14 aryl, substituted C.sub.6 -C.sub.14 aryl, C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, substituted C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, C.sub.7 -C.sub.18 aralkyl, substituted C.sub.7 -C.sub.18 aralkyl, C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms, substituted C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms, O--C.sub.1 -C.sub.8 alkyl, substituted O--C.sub.1 -C.sub.8 alkyl, O--C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, substituted O--C.sub.2 -C.sub.8 heterocycloalkyl containing up to three heteroatoms, O--C.sub.6 -C.sub.14 aryl, substituted O--C.sub.6 -C.sub.14 aryl, O--C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, substituted O--C.sub.3 -C.sub.11 hetaryl containing up to three heteroatoms, O--C.sub.7 -C.sub.18 aralkyl, substituted O--C.sub.7 -C.sub.18 aralkyl, O--C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms, substituted O--C.sub.4 -C.sub.15 heterocycloaralkyl containing up to three heteroatoms, O--C.sub.1 -C.sub.8 -alkyl-O--C.sub.1 -C.sub.8 -alkyl, O--C.sub.1 -C.sub.8 alkenyl, O--C.sub.1 -C.sub.8 alkoxyamino, O-tri-C.sub.1 -C.sub.8 -alkyl silyl, substituted O-tri-C.sub.1 -C.sub.8 -alkyl silyl, NH--C.sub.1 -C.sub.8 alkyl, N-(C.sub.1 -C.sub.8).sub.2, NH--C.sub.1 -C.sub.8 alkenyl, N-(C.sub.1 -C.sub.8).sub.2 alkenyl, S--C.sub.1 -C.sub.8 alkyl, S--C.sub.1 -C.sub.8 alkenyl, NH.sub.2, N.sub.3, NH--C.sub.1 -C.sub.8 -alkyl-NH.sub.2, polyalkylamino and an RNA cleaving group; andY is oxygen or sulfur.
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이 특허에 인용된 특허 (40)
Ravikumar Vasulinga (Carlsbad CA) Andrade Mark (Carlsbad CA) Mulvey Dennis (Conroe TX) Cole Douglas L. (San Diego CA), Carbocation scavenging during oligonucleotide synthesis.
Stee Wojciech J. (Lodz PLX) Grajkowski Andrzej (Lodz PLX) Uznanski Bogdan (Lodz PLX), Chalcophospholanes useful in the synthesis of oligonucleoside phosphorothioates, phosphorodithioates and related selenat.
Andrus William A. (San Francisco CA) Efcavitch J. William (Belmont CA) McBride Lincoln J. (Redwood City CA), Chemical capping by phosphitylation during oligonucleotide synthesis.
Cook Phillip D. (Carlsbad CA) Guinosso Charles J. (Carlsbad CA) Bruice Thomas (Carlsbad CA), Compounds useful in the synthesis of nucleic acids capable of cleaning RNA.
Nelson Paul S. (Union City CA), Method for labeling the 3′terminus of a synthetic oligonucleotide using a unique multifunctional controlled pore glass.
Beaucage Serge L. (Silver Spring MD) Regan Judith B. (Annandale VA) Iyer Radhakrishnan P. (Rockville MD), Method for the sulfurization of phosphorous groups in compounds.
Stec Wojciech J. (Lodz PLX) Uznanski Bogdan (Lodz CA PLX) Bergot B. John (Redwood City CA) Hirschbein Bernard L. (San Francisco CA) Fearon Karen L. (Union City CA), Method of synethesizing sulfurized oligonucleotide analogs.
Woo Sam L. (Redwood City CA) Menchen Steven M. (Fremont CA) Fung Steven (Palo Alto CA), Method of synthesizing oligonucleotides labeled with ammonia-labile groups on solid phase supports.
Stec Wojciech J. (Lodz PLX) Uznanski Bogdan (Lodz CA PLX) Bergot B. John (Redwood City CA) Hirschbein Bernard L. (San Francisco CA) Fearson Karen L. (Union City CA), Method of synthesizing sulfurized oligonucleotide analogs.
Caruthers Marvin H. (Boulder CO) Ma Yun-Xi (Mississauga WA CAX) Yau Eric K. (Kirkland WA) Nielsen John (Horsholm DKX) Brill Wolfgang (Freiburg DEX), Nucleoside thiophosphoramidites.
Gorenstein David (Carmel IN) Farschtschi Nassar (West Lafayette IN), Process for preparing dithiophosphate oligonucleotide analogs via nucleoside thiophosphoramidite intermediates.
Ravikumar Vasulinga T. (Carlsbad CA) Mulvey Dennis (Vista CA) Cole Douglas L. (San Diego CA) Cook Phillip D. (Carlsbad CA), Process for preparing oligonucleotides using silyl-containing diamino phosphorous reagents.
Stec Wojciech J. (Lodz PLX) Grajkowski Andrzej (Lodz PLX) Uznanski Bogdan (Lodz PLX), Solid phase oligonucleotide synthesis using phospholane intermediates.
Prakash, Thazha P.; Baker, Brenda F.; Eldrup, Anne B.; Manoharan, Muthiah; Bhat, Balkrishen; Griffey, Richard; Swayze, Eric E.; Crooke, Stanley T., 2′-Fluoro substituted oligomeric compounds and compositions for use in gene modulations.
Allerson, Charles; Bhat, Balkrishen; Eldrup, Anne B.; Manoharan, Muthiah; Griffey, Richard H.; Baker, Brenda F.; Swayze, Eric E., Compositions comprising alternating 2'-modified nucleosides for use in gene modulation.
Allerson, Charles; Bhat, Balkrishen; Eldrup, Anne B.; Manoharan, Muthiah; Griffey, Richard H.; Baker, Brenda F.; Swayze, Eric E., Compositions comprising alternating 2′-modified nucleosides for use in gene modulation.
Allerson, Charles; Bhat, Balkrishen; Eldrup, Anne B.; Manoharan, Muthiah; Griffey, Richard H.; Baker, Brenda F.; Swayze, Eric E., Compositions comprising alternating 2′-modified nucleosides for use in gene modulation.
Swayze, Eric E.; Migawa, Michael T.; Wyrzykiewicz, Tadeusz Krzysztof, Gapped oligomeric compounds having linked bicyclic sugar moieties at the termini.
Esau, Christine; Swayze, Eric E.; Bhat, Balkrishen; Kinberger, Garth A., Oligomeric compounds and compositions for the use in modulation of target nucleic acids.
Bhat, Balkrishen; Dande, Prasad; Prakash, Thazha P.; Allerson, Charles; Swayze, Eric E.; Griffey, Richard H., Oligomeric compounds comprising 4′-thionucleosides for use in gene modulation.
Allerson, Charles; Bhat, Balkrishen; Swayze, Eric E.; Prakash, Thazha P., Polycyclic sugar surrogate-containing oligomeric compounds and compositions for use in gene modulation.
Allerson, Charles; Bhat, Balkrishen; Swayze, Eric E.; Prakash, Thazha P., Polycyclic sugar surrogate-containing oligomeric compounds and compositions for use in gene modulation.
Cheruvallath Zacharia S. ; Ravikumar Vasulinga T. ; Cole Douglas L. ; Capaldi Daniel C., Reagent useful for synthesizing sulfurized oligonucleotide analogs.
Zacharia S. Cheruvallath ; Vasulinga T. Ravikumar ; Douglas L. Cole ; Daniel C. Capaldi, Reagent useful for synthesizing sulfurized oligonucleotide analogs.
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