Patent ID: 7176185
Filing Date: 2007-02-13
Classification: C07K,G01N

Abstract:
1. A compound for active agent delivery to cells of a subject of the formula: where C a is methylene or an L-carbon atom; R is hydrogen or if C a is niethylene then R is methyl; R 1 is independently in each occurrence is a side chain of glycine, alanine, isoleucine, leucine, methionine, valine, phenylalanine, tyrosine, tryptophan, lysine, threonine, serine, histidine, glutamic acid, glutamine, cysteine, aspartic acid, asparagine, arginine, sarcosine, ornithine, citrulline, kynurenine, 5-hydroxytryptophan, 3-hydroxykynurenine, 3-aminotyrosine, or quisqualic acid; j is 1 or 2; C b is a D or L-carbon; R 2 and R 3 are independently in each occurrence a group consisting of a side chain and at least one of R 2 and R 3 has an active agent coupled through an active agent moiety to the side chain; said active agent is floxuridine, gemcitabine, cladribine, dacarbazine, melphalan, mercaptopurine, thioguanine, cis-platin, cytarabine; fludarabine, cidofovir, tenofovir, pentostatin, adenocard, adriamycin, allopurinol, alprostadil, amifostine, aminohippurate, argatroban, benztropine, bisphosphinate, bortezomib, busulfan, calcitriol, carboplatin, daunorubicin, dexamethasone, topotecan, docetaxel, dolasetron, doxorubicin, epirubicin, estradiol, famotidine, foscarnet, flumazenil, fosphenytoin, fulvestrant, hemin, ibutilide fumarate, irinotecan, levocarnitine, idamycin, sumatriptan, granisetron, metaraminol, metaraminol, methohexital, mitoxantrone, morphine, nalbuphine hydrochloride, nesacaine, oxaliplatin, palonosetron, pamidronate, pemetrexed, phytonadione, ranitidine, testosterone, tirofiban, toradol, triostat, valproate, vinorelbine tartrate, visudyne, zemplar, zemuron, zinecard, a coumarin, a cyanine, or a magnetic contrast agent; k is 0 or 1; 1 is 0 or 1 such that j+l equals 1 or 2; Q is oxygen when l is 0 and Q is NH when l is 1; C c is a racemic or L-carbon; R 4 is a side chain of glycine, alanine, valine, leucine, isoleucine, serine, methionine, threonine, phenylalanine, tyrosine, tryptophan, cysteine, proline, histidine, aspartic acid, asparagine, glutamic acid, glutamine, γ-carboxyglutamic acid, arginine, omithine and lysine, hydroxylysine, citrulline, kynurenine, (4-aminophenyl)alanine, 3-(2′-naphthyl)alanine, 3-(1′-naphthyl) alanine, methionine sulfone, (t-butyl)alanine, (t-butyl)glycine, 4-hydroxyphenyl-glycine, aminoalanine, phenylglycine, vinylalanine, propargyl-glycine, 1,2,4-triazolo-3-alanine, thyronine, 6-hydroxytryptophan, 5-hydroxytryptophan, 3-hydroxykynurenine, 3-aminotyrosine, trifluoromethylalanine, 2-thienylalanine, (2-(4-pyridyl)ethyl)cysteine, 3,4-dimethoxy-phenylalanine, 3-(2′-thiazolyl)alanine, ibotenic acid, 1-amino-1-cyclopentane-carboxylic acid, 1-amino-1-cyclohexanecarboxylic acid, quisqualic acid, 3-(trifluoromethylphenyl)alanine, (cyclohexyl)glycine, thiohistidine, 3-methoxytyrosine, norleucine, norvaline, alloisoleucine, homoarginine, thioproline, dehydroproline, hydroxyproline, homoproline, indoline-2-carboxylic acid, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, 1,2,3,4-tetrahydroquinoline-2-carboxylic acid, α-amino-n-butyric acid, cyclohexylalanine, 2-amino-3-phenylbutyric acid, phenylalanine substituted at the ortho, meta, or para position of the phenyl moiety with one or two of the following groups: a (C 1 to C 4 )alkyl, a (C 1 to C 4 )alkoxy, a halogen or a nitro group, or substituted once with a methylenedioxy group; β-2- and 3-thienylalanine; β-2- and 3-furanylalanine; β-2-, 3- and 4-pyridylalanine; β-(benzothienyl-2- and 3-yl)alanine; β-(1- and 2-naphthyl)alanine; O-alkylated derivatives of serine, threonine or tyrosine; S-alkylated cysteine, S-alkylated homocysteine, the O-sulfate, O-phosphate and O-carboxylate esters of tyrosine; 3-(sulfo)tyrosine, 3-(carboxy)tyrosine, 3-(phospho)tyrosine, the 4-methane-sulfonic acid ester of tyrosine, 4-methanephosphonic acid ester of tyrosine, 3,5-diiodotyrosine, 3-nitrotyrosine, ε-alkyllysine, and delta-alkyl ornithine and a halogen substituent bonded via a phenyl where the halogen is fluorine, chlorine or bromine; and R 5 is hydrogen or C 1 –C 3 alkyl.