Phosphonomonoester nucleic acids, methods for their preparation and their use

• Main Authors: BREIPOHL, GERHARD, WALLMEIER, HOLGER, UHLMANN, EUGEN, PEYMAN, ANUSCHIRWAN
• Format: Patent
• Language: English; French; German
• Published: 16.09.1998
• Edition: 6
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; AGRICULTURE; ANIMAL HUSBANDRY; BEER; BIOCHEMISTRY; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; CHEMISTRY; COMPOSITIONS OR TEST PAPERS THEREFOR; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL ORENZYMOLOGICAL PROCESSES; DERIVATIVES THEREOF; ENZYMOLOGY; FISHING; FORESTRY; HUMAN NECESSITIES; HUNTING; HYGIENE; MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEICACIDS OR MICROORGANISMS; MEDICAL OR VETERINARY SCIENCE; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; PEPTIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES; PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTSTHEREOF; PROCESSES OF PREPARING SUCH COMPOSITIONS; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS; SPIRITS; SUGARS; TRAPPING; VINEGAR; WINE

Oligonucleotide analogues and related cpds. of formula (I) are new, in which n = 0-100; B = H or OH; 1-20C alkyl, 1-20C alkoxy or 1-20C alkylthio opt. substd. by 6-20C aryl; or aryl or heterocyclyl; where alkyl, aryl and heterocyclyl are opt. substd.; or B = a natural or unnatural nucleobase or a label; A = a single bond, CH2, (CR R )pM(CR R )q or (CR R )rM(CR R )sCY'; or A-B = 1-5 D- or L-amino acids condensed on via the carboxyl group; L = N or R N<+>; R = H or 1-6C alkyl opt. substd. by OH, 1-6C alkoxy, 1-6C alkylthio or NH2; Y' = O, S, CH2, CMe2 or NR ; M = a single bond, O, S or NR ; R and R = H, OH, 1-6C alkoxy, 1-6C alkylthio, NH2, halogen, or 1-6C alkyl opt. substd. by OH, 1-6C alkoxy or 1-6C alkylthio; p, q, r and s = 0-5; D and G = CR R ; R and R = H, 1-6C alkyl, 6-20C aryl, (6-20C)aryl(1-6C)alkyl, OH, 1-6C alkoxy or 1-6C alkylthio, where alkyl and aryl are opt. substd. by SR or NR R ; X = O, S or NR ; Y = O or S; Z = OR , NR R or XQ; R = H, alkyl, alkenyl, alkynyl, aryl or arylalkyl, where alkyl and aryl are opt. substd.; R and R = H, alkyl, alkenyl, alkynyl, aryl or arylalkyl, where alkyl is opt. substd.; or NR R is a 4- to 7-membered ring; Q and Q' = H, R , opt. modified oligonucleotides or conjugates which (a) favourably affect the properties of antisense oligonucleotides, (b) affect the properties of triplex-forming oligonucleotides, (c) serve as DNA probe labels or (d) bind to or crosslink a target nucleic acid during hybridisation; or Q and Q' alone or together are a single bond in a cyclic molecule; or Q and Q', when neither is hydrogen, can be linked together to form a cyclic molecule.