Nucleosidic and non-nucleosidic folate conjugates
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C12Q-001/68
C07H-019/00
C07H-021/00
C07H-021/02
C07H-021/04
출원번호
US-0275505
(1999-03-24)
발명자
/ 주소
Andrei P. Guzaev
Phillip Dan Cook
Muthiah Manoharan
Balkrishen Bhat
출원인 / 주소
ISIS Pharmaceuticals, Inc.,
대리인 / 주소
Woodcock Washburn Kurtz Mackiewicz & Norris LLP
인용정보
피인용 횟수 :
196인용 특허 :
184
초록▼
Oligonucleotide-folate conjugates are described wherein folates are conjugated to one or more sites on an oligonucleotide including the 2'-, 3'-, 5'-, nucleobase and internucleotide linkage sites. The folate can be attached via the .alpha.- or .gamma.-carboxylate, optionally through a linking group.
Oligonucleotide-folate conjugates are described wherein folates are conjugated to one or more sites on an oligonucleotide including the 2'-, 3'-, 5'-, nucleobase and internucleotide linkage sites. The folate can be attached via the .alpha.- or .gamma.-carboxylate, optionally through a linking group. Methods for the regiospecific synthesis of the conjugates are diclosed. Also disclosed are nucleosidic and non-nucleosidic linkers conjugated to folic acid and related folates.
대표청구항▼
1. a compound having formula XVIA, XVIB, XVIC or XVID: [EQU114]wherein:W14 has the formula: [EQU115]wherein:X4 is -CH(X4') or a group of formula: [EQU116]X4' is the side chain of a naturally-occuning amino acid or analog thereof, or a protected side chain of a naturally-occurring amino acid or analo
1. a compound having formula XVIA, XVIB, XVIC or XVID: [EQU114]wherein:W14 has the formula: [EQU115]wherein:X4 is -CH(X4') or a group of formula: [EQU116]X4' is the side chain of a naturally-occuning amino acid or analog thereof, or a protected side chain of a naturally-occurring amino acid or analog thereof; t is 1 or 2; X5 is -N(X6')C(O)-, -C(O)NH-, -NHC(O)-, -OC(O)NH-, -C(S)NH-, -SC(S)NH-, -SC(O)NH-, -OC(S)NH-, -C(O)O-, -C(O)(CH2)n- or a bond; n is an integer from 1 to 50; each X6, X6' and X9 is, independently, a bond, hydrogen or a hydrocarbyl group selected from C1-C10 alkyl, C2-C10 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C6-C14 aralkyl, C3-C14 cycloalkyl, C5-C14 fused cycloalkyl, C4-C14 heterocycle, C4-C14 heterocyclylalkyl, C4-C14 heteroaryl and C4-C14 heteroarylalkyl; wherein said hydrocarbyl group is substituted with at least two hydroxyl groups, and is optionally substituted with oxo, acyl, alkoxy, alkoxycarbonyl, alkyl, alkenyl, alkynyl, amino, amido, azido, aryl, heteroaryl, carboxylic acid, cyano, guanidino, halo, haloalkyl, haloalkoxy, hydrazino, ODMT, alkylsulfonyl, nitro, sulfide, disulfide, sulfone, sulfonate, sulfonamide, thiol, and thioalkoxy; provided that each X6 and X9 is not hydrogen and X6' is not a bond; R1 is hydrogen or a hydroxyl protecting group; R4 is a hydroxyl group or a protected hydroxyl group; each R5' and R40 is, independently, hydrogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C20 alkynyl, C6-C14 aryl or an amino-protecting group R5′ is hydrogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C20 alkynyl, C6-C14 aryl, C6-C14 aralkyl, C3-C14 cycloalkyl, formyl, aminoalkyl or hydroxymethyl; R6 is hydrogen or an amino protecting group; R20 is hydrogen or a group of formula: [EQU117]R2 is -N(R7)2, or a heterocycloalkyl or heterocycloalkenyl ring containing from 4 to 7 atoms, and having up to 3 heteroatoms selected from nitrogen, sulfur, and oxygen; R7 is straight or branched chain alkyl having from 1 to 10 carbons; R3 is a phosphorus protecting group; R21 is hydrogen, hydroxyl, fluoro or a group of formula Z-R22-(R23)v; Z is O, S, NH or N-R22-(R23)v; R22 is C1-C20 alkyl, C2-C20 alkenyl, or C2-C20 alkynyl; R23 is hydrogen, amino, halogen, hydroxyl, thiol, keto, carboxyl, nitro, nitroso, nitrile, trifluoromethyl, trifluoromethoxy, O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aryl, S-aryl, NH-aryl, O-aralkyl, S-aralkyl, NH-aralkyl, amino, N-phthalimido, imidazole, azido, hydrazino, hydroxylamino, isocyanato, sulfoxide, sulfone, sulfide, disulfide, silyl, aryl, heterocycle, carbocycle, intercalator, reporter molecule, conjugate, polyamine, polyamide, polyalkylene glycol, or a polyether; or R21 has one of the formulas: [EQU118]wherein:y1 is 0 or 1; each y2 is, independently, 0 to 10; y3 is 1 to 10; E is N(R41)(R42) or N.dbd.C(R41)(R42); each R41 and each R42 is independently H, C1-C10 alkyl, a nitogen protecting group, or R41 and R42 taken together form a nitrogen protecting group; or R41 and R42 taken together with the N or C atom to which they are attached form a ring structure that can include at least one heterotom selected from N and O; B is a nucleobase; M is an optionally protected internucleoside linkage; q is from zero to about 50; and v is from zero to about 10; provided that when said compound has formula XVIC, at least one R21 is a group other than hydrogen, and when said compound has formula XVIC or XVID, q is at least 1.
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Collard, Joseph; Khorkova Sherman, Olga; Coito, Carlos, Treatment of ‘C terminus of HSP70-interacting protein’ (CHIP)related diseases by inhibition of natural antisense transcript to CHIP.
Collard, Joseph; Khorkova Sherman, Olga; Coito, Carlos, Treatment of ‘C terminus of HSP7O-interacting protein’ (CHIP) related diseases by inhibition of natural antisense transcript to CHIP.
Vlahov, Iontcho R.; Leamon, Christopher P.; Parker, Matthew A.; Howard, Stephen J.; Santhapuram, Hari Krishna R.; Satyam, Apparao; Reddy, Joseph A., Vitamin receptor binding drug delivery conjugates.
Vlahov, Iontcho R.; Leamon, Christopher P.; Parker, Matthew A.; Howard, Stephen J.; Santhapuram, Hari Krishna; Satyam, Apparao; Reddy, Joseph Anand, Vitamin receptor binding drug delivery conjugates.
Leamon, Christopher Paul; Vlahov, Iontcho Radoslavov; Lu, Yingjuan June; Wang, Kevin Yu; Yu, Fei; Kleindl, Paul Joseph; Santhapuram, Hari Krishna R., Vitamin receptor drug delivery conjugates for treating inflammation.
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