WO2016154547A1 - Utilisation de chélateurs de métaux dans la gestion de maladies infectieuses - Google Patents
Utilisation de chélateurs de métaux dans la gestion de maladies infectieuses Download PDFInfo
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- WO2016154547A1 WO2016154547A1 PCT/US2016/024239 US2016024239W WO2016154547A1 WO 2016154547 A1 WO2016154547 A1 WO 2016154547A1 US 2016024239 W US2016024239 W US 2016024239W WO 2016154547 A1 WO2016154547 A1 WO 2016154547A1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/14—Alkali metal chlorides; Alkaline earth metal chlorides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- ROS reactive oxygen species
- Biofilms are complex communities of microorganisms that are commonly found on a variety of substrates or surfaces that are moist or submerged (Musk et al., Curr. Med. Chem., 2006, 13, 2163). Though primarily populated by bacteria, biofilms can also contain many different individual types of microorganisms, e.g., bacteria, archaea, protozoa, and algae. The formation of biofilms can be thought of as a developmental process in which a few free-swimming (planktonic) bacteria adhere to a solid surface and, in response to appropriate signals, initiate the formation of a complex sessile microcolony existing as a community of bacteria and other organisms.
- planktonic planktonic
- Biofilms Bacteria within biofilms are usually embedded within a matrix, which can consist of protein, polysaccharide, nucleic acids, or combinations of these macromolecules.
- the matrix is a critical feature of the biofilm that protects the inhabiting organisms from antiseptics, microbicides, and host cells. It has been estimated that bacteria within biofilms are upwards of 1,000-fold more resistant to conventional antibiotics
- Cystic fibrosis (CF), with 7 million asymptomatic heterozygous carriers, is one of the most common genetic diseases in the United States. Despite significant progress in the management of the symptoms of CF, virtually all CF patients succumb to chronic pulmonary infections. For reasons that are not entirely clear, the airways of CF patients are particularly susceptible to bacterial colonization. CF patients typically become infected with
- Pseudomona aeruginosa Staphylococcus aureus, Streptococcus pneumoniae, Haemophilus influenzae, Burkholderia cepacia complex, and nonmucoid Pseudomonas aeruginosa.
- Pseudomona aeruginosa becomes the predominant pulmonary pathogen, present in up to 85% of cultures from patients with advanced disease. Once colonized by Pseudomonas aeruginosa, the organism persists for many years or decades and is never eradicated.
- ROS reactive oxygen species
- free iron can contribute to the formation of reactive oxygen species.
- iron ions in biological systems react with oxygen species to produce highly reactive hydroxyl radicals via the Fenton reaction (see scheme below).
- the hydroxyl radical is a highly effective oxidizing agent, reacting at a diffusion-controlled rate with most organic species, such as nucleic acids, proteins, and lipids.
- superoxide anions or a biological reductant e.g., ascorbic acid
- microbial infections involve the possibility that reactive oxygen species will come in contact with iron ions to produce highly reactive and damaging hydroxyl radicals. That is, the iron released from red blood cells react with oxygen species produced by inflammatory cells such as neutrophils to produce hydroxyl radicals that cause cell and tissue injury (Lee, Acta Neurochir Suppl., 2011, 112, 101-106). Further, iron is usually a nutrient necessary for the growth of microorganisms. Depriving the organisms of iron by chelating and/or removing iron may contribute to the treatment and/or prevention of infectious diseases.
- the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising a compound capable of chelating a metal or a pharmaceutically acceptable salt, and a pharmaceutically acceptable carrier.
- the pharmaceutical composition further comprises an antimicrobial agent (e.g., antibiotics).
- the present invention provides methods to treat and/or prevent an infectious disease comprising administering to a subject in need thereof a therapeutically effective amount of a compound capable of chelating a metal (e.g., compounds of any one of Fomulae (I-A)-(III-A)), or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof, or a pharmaceutical composition as described herein.
- a compound capable of chelating a metal e.g., compounds of any one of Fomulae (I-A)-(III-A)
- a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof e.g., a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof, or a pharmaceutical composition as described herein.
- the present invention provides methods of treating and/or preventing an infectious disease comprising administering to a subject in need thereof a
- composition as described herein, and an antimicrobial agent as described herein, and an antimicrobial agent.
- the infectious disease is caused by bacteria, algae, fungi, parasites, or protozoa.
- the infectious disease is a bacterial infection.
- the bacterial infection is chronic bacterial infection.
- the bacterial infections include, but are not limited to, urinary tract infections, gastritis, respiratory infections (e.g., those in patient’s with cystic fibrosis), cystitis, pyelonephritis, osteomyelitis, bacteremia, skin infections, rosacea, acne, chronic wound infection, infectious kidney stones, bacterial endocarditis, ear infections, and sinus infections.
- the infectious disease is caused by Gram-negative bacteria such as Pseudomonas.
- the subject having or susceptible to the infectious disease also contracts another disease or condition.
- the subject is diagnosed with cystic fibrosis.
- the infectious disease is responsive to the chelation or sequestration of a metal.
- the metal is a monovalent, divalent, tetravalent, pentavalent, or hexavalent metal.
- the metal is a trivalent metal.
- the metal is aluminum, thallium, chromium, magnesium, calcium, strontium, nickel, manganese, cobalt, copper, zinc, silver, sodium, potassium, cadmium, mercury, lead, antimony, molybdenum, tungsten, a lanthanide (e.g., cerium), or an actinide (e.g., uranium).
- the metal being chelated or sequestered is iron (e.g., Fe(III)).
- the present invention provides methods to kill bacteria comprising contacting the bacteria with a compound capable of chelating a metal, or a pharmaceutically acceptable salt thereof.
- the present invention provides methods for inhibiting bacterial cell growth comprising contacting the bacteria with a compound capable of chelating a metal, or a pharmaceutically acceptable salt thereof.
- the present invention provides methods for inducing bacterial hypersusceptibility comprising contacting a bacterium with a compound capable of chelating a metal, or a pharmaceutically acceptable salt thereof.
- the present invention provides methods of treating or preventing biofilm formation comprising administering to a subject in need thereof a therapeutically effective amount of a compound capable of chelating a metal (e.g., compounds of any one of Fomulae (I-A)-(III-A)), or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof, or a pharmaceutical composition as described herein.
- a compound capable of chelating a metal e.g., compounds of any one of Fomulae (I-A)-(III-A)
- a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof e.g., a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof, or a pharmaceutical composition as described herein.
- the present invention provides methods of treating or preventing biofilm formation comprising administering to a subject in need thereof a therapeutically effective
- the biofilms include one or more microorganisms selected from the group consisting of bacteria, archaea, protozoa, fungi and algae. In some embodiments, the biofilms include bacteria.
- the present invention provides compositions for treating or preventing biofilm formation comprising a compound capable of chelating a metal and a carrier.
- the composition is a cleaning composition.
- the present invention provides methods of treating or preventing biofilm formation comprising contacting an object with an effective amount of a compound capable of chelating a metal or the composition as described herein. In certain embodiments, the provided method is to inhibit or remove the biofilm on the surface of the object.
- the biofilm is produced by an organism selected from the group consisting of bacteria, algae, fungi and protozoa. In some embodiments, the biofilm is bacterial biofilm.
- the compound useful in the present invention is of any one of Formulae (I-A)-(III-A), or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof.
- the compound is of Formula (I-A):
- the compound is of Formula (II-A):
- the compound is of Formula (III-A):
- the compounds provided herein may chelate iron and/or other metals (e.g., aluminum, thallium, chromium, magnesium, calcium, strontium, nickel, manganese, cobalt, copper, zinc, silver, sodium, potassium, cadmium, mercury, lead, antimony, molybdenum, tungsten, a lanthanide (e.g., cerium), or an actinide (e.g., uranium)).
- the compounds chelate iron and one or more metals important for bacterial growth, e.g., K, Mg, Ca, Mn, Zn, Co, Cu, and Mo.
- the invention provides a kit for treating and/or preventing an infectious disease.
- the invention provides a kit for treating and/or preventing formation of biofilms.
- the kit is to treat or prevent biofilm formation in a subject.
- the kit is to treat or prevent biofilm formation on an object (e.g., surface).
- the kit further comprises an
- the inventive kits include a first container containing a therapeutically effective amount of a compound capable of chelating a metal (e.g., a compound of any one of Formulae (I-A)-(III-A)), or a
- the inventive kits include a first container containing a therapeutically effective amount of a compound capable of chelating a metal (e.g., a compound of any one of Formulae (I-A)-(III- A)), or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof; and an antimicrobial agent; and a second container containing a compound capable of chelating a metal (e.g., a compound of any one of Formulae (I-A)-(III- A)), or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof; and an antimicrobial agent; and a second container containing a compound capable of chelating a metal (e.g., a compound of any one of Formulae (I-A)-(III- A)), or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof; and an antimicrobial
- kits include a first container containing a therapeutically effective amount of a compound capable of chelating a metal (e.g., a compound of any one of Formulae (I-A)-(III-A)), or a salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof; and instructions for contacting the compound with an object to treat and/or prevent biofilm formation.
- a compound capable of chelating a metal e.g., a compound of any one of Formulae (I-A)-(III-A)
- a salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof e.g., a compound of any one of Formulae (I-A)-(III-A)
- a salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof e.g., a salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof.
- An enantiomer can be characterized by the absolute configuration of its asymmetric center and is described by the R- and S-sequencing rules of Cahn and Prelog, or by the manner in which the molecule rotates plane polarized light and designated as dextrorotatory or levorotatory (i.e., as (+) or (-)-isomers respectively).
- a chiral compound can exist as either individual enantiomer or as a mixture thereof.
- a mixture containing equal proportions of the enantiomers is called a“racemic mixture.”
- the compounds described herein can be in the form of an individual enantiomer, diastereomer or geometric isomer, or can be in the form of a mixture of stereoisomers, including racemic mixtures and mixtures enriched in one or more stereoisomer.
- Isomers can be isolated from mixtures by methods known to those skilled in the art, including chiral high pressure liquid chromatography (HPLC) and the formation and crystallization of chiral salts; or preferred isomers can be prepared by asymmetric syntheses. See, for example, Jacques et al., Enantiomers, Racemates and
- an isomer/enantiomer may, in some embodiments, be provided substantially free of the corresponding enantiomer, and may also be referred to as “optically enriched” or“enantiomerically enriched.”“Optically enriched” and
- “enantiomerically enriched” means that a provided compound is made up of a significantly greater proportion of one enantiomer.
- a compound of the present invention is made up of at least about 70% by weight of a preferred enantiomer.
- a compound of the present invention is made up of at least about 80% by weight of a preferred enantiomer.
- a compound of the present invention is made up of at least about 90% by weight of a preferred enantiomer.
- the compound is made up of at least about 95%, 98%, or 99% by weight of a preferred enantiomer.
- Preferred enantiomers may be isolated from racemic mixtures by any method known to those skilled in the art, including chiral high pressure liquid
- structures depicted herein are also meant to include compounds that differ only in the presence of one or more isotopically enriched atoms.
- compounds having the depicted structures that differ only in the replacement of hydrogen by deuterium or tritium, or the replacement of a carbon by 13 C or 14 C are within the scope of this invention.
- Such compounds are useful, for example, as analytical tools, as probes in biological assays, or as therapeutic agents in accordance with the present invention.
- C 1–6 is intended to encompass, C 1 , C 2 , C 3 , C 4 , C 5 , C 6 , C 1–6 , C 1–5 , C 1–4 , C 1–3 , C 1–2 , C 2–6 , C 2–5 , C 2–4 , C 2–3 , C 3–6 , C 3–5 , C 3–4 , C 4–6 , C 4–5 , and C 5–6 .
- the terms“purified,”“substantially purified,” and“isolated” refer to a compound useful in the present invention being free of other, dissimilar compounds with which the compound is normally associated in its natural state, so that the compound comprises at least 0.5%, 1%, 5%, 10%, 20%, 50%, 75%, 80%, 85%, 90%, 95%, 96%, 97%, 98%, 99%, 99.5%, 99.9% of the mass, by weight, of a given sample or composition. In one embodiment, these terms refer to the compound comprising at least 95%, 98%, 99%, or 99.9% of the mass, by weight, of a given sample or composition.
- R X1 is hydrogen; halogen; substituted or unsubstituted hydroxyl; substituted or unsubstituted thiol; substituted or unsubstituted amino; substituted or unsubstituted acyl, cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic; cyclic or acyclic, substituted or unsubstituted, branched or unbranched
- heteroaliphatic cyclic or acyclic, substituted or unsubstituted, branched or unbranched alkyl; cyclic or acyclic, substituted or unsubstituted, branched or unbranched alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, aliphaticoxy, heteroaliphaticoxy, alkyloxy, heteroalkyloxy, aryloxy,
- heteroaryloxy aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalkylthioxy, arylthioxy, heteroarylthioxy, mono- or di- aliphaticamino, mono- or di- heteroaliphaticamino, mono- or di- alkylamino, mono- or di- heteroalkylamino, mono- or di-arylamino, or mono- or di-heteroarylamino; or two R X1 groups taken together form a 5- to 6-membered heterocyclic ring.
- acyl groups include aldehydes (–CHO), carboxylic acids (–CO 2 H), ketones, acyl halides, esters, amides, imines, carbonates, carbamates, and ureas.
- Acyl substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyl
- acyloxy refers to a“substituted hydroxyl” of the formula (–OR i ), wherein R i is an optionally substituted acyl group, as defined herein, and the oxygen moiety is directly attached to the parent molecule.
- R i is an optionally substituted acyl group, as defined herein, and the oxygen moiety is directly attached to the parent molecule.
- aliphatic includes both saturated and unsaturated, nonaromatic, straight chain (i.e., unbranched), branched, acyclic, and cyclic (i.e., carbocyclic)
- hydrocarbons which are optionally substituted with one or more functional groups.
- “aliphatic” is intended herein to include, but is not limited to, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkynyl moieties.
- the term“alkyl” includes straight, branched and cyclic alkyl groups. An analogous convention applies to other generic terms such as“alkenyl”,“alkynyl”, and the like.
- “alkyl”,“alkenyl”,“alkynyl”, and the like encompass both substituted and unsubstituted groups.
- “aliphatic” is used to indicate those aliphatic groups (cyclic, acyclic, substituted, unsubstituted, branched or unbranched) having 1–20 carbon atoms.
- Aliphatic group substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy, heteroalkyloxy, aryloxy, heteroaryloxy, aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalkylthioxy, arylthioxy,
- heteroarylthioxy acyloxy, and the like, each of which may or may not be further substituted).
- alkyl refers to saturated, straight- or branched-chain hydrocarbon radicals derived from a hydrocarbon moiety containing between one and twenty carbon atoms by removal of a single hydrogen atom.
- the alkyl group employed in the invention contains 1–20 carbon atoms.
- the alkyl group employed contains 1–15 carbon atoms.
- the alkyl group employed contains 1–10 carbon atoms.
- the alkyl group employed contains 1–8 carbon atoms.
- the alkyl group employed contains 1–5 carbon atoms.
- alkyl radicals include, but are not limited to, methyl (e.g., unsubstituted methyl (Me)), ethyl (e.g., unsubstituted ethyl (Et)), propyl (e.g., unsubstituted propyl (Pr)), n-propyl, isopropyl, butyl (e.g., unsubstituted butyl (Bu)), n-butyl, iso-butyl, sec-butyl, sec-pentyl, iso-pentyl, tert- butyl, n-pentyl, neopentyl, n-hexyl, sec-hexyl, n-heptyl, n-octyl, n-decyl, n-undecyl, dodecyl, and the like, which may bear one or more sustitutents.
- methyl
- Alkyl group substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy, heteroalkyloxy, aryloxy, heteroaryloxy, aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalkylthioxy, arylthioxy, heteroarylthioxy,
- alkenyl denotes a monovalent group derived from a straight- or branched-chain hydrocarbon moiety having at least one carbon-carbon double bond by the removal of a single hydrogen atom.
- the alkenyl group employed in the invention contains 2–20 carbon atoms. In some embodiments, the alkenyl group employed in the invention contains 2–15 carbon atoms. In another embodiment, the alkenyl group employed contains 2–10 carbon atoms. In still other embodiments, the alkenyl group contains 2–8 carbon atoms. In yet other embodiments, the alkenyl group contains 2–5 carbons.
- Alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1-methyl-2-buten- 1-yl, and the like, which may bear one or more substituents.
- Alkenyl group substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy, hetero
- alkynyl refers to a monovalent group derived from a straight- or branched-chain hydrocarbon having at least one carbon-carbon triple bond by the removal of a single hydrogen atom.
- the alkynyl group employed in the invention contains 2–20 carbon atoms. In some embodiments, the alkynyl group employed in the invention contains 2–15 carbon atoms. In another embodiment, the alkynyl group employed contains 2–10 carbon atoms. In still other embodiments, the alkynyl group contains 2–8 carbon atoms. In still other embodiments, the alkynyl group contains 2–5 carbon atoms.
- Representative alkynyl groups include, but are not limited to, ethynyl, 2-propynyl
- Alkynyl group substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy,
- heteroaliphaticoxy alkyloxy, heteroalkyloxy, aryloxy, heteroaryloxy, aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalkylthioxy, arylthioxy, heteroarylthioxy, acyloxy, and the like, each of which may or may not be further substituted).
- Exemplary carbon atom substituents include, but are not limited to, halogen,–CN, –NO 2 ,–N 3 ,–SO 2 H,–SO 3 H,–OH,–OR aa ,–ON(R bb ) 2 ,–N(R bb ) 2 ,–N(R bb ) +
- heteroaryl wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R dd groups;
- R aa is, independently, selected from C 1–10 alkyl, C 1–10 perhaloalkyl, C 2–10 alkenyl, C 2–10 alkynyl, C 3–10 carbocyclyl, 3–14 membered heterocyclyl, C 6–14 aryl, and 5–14 membered heteroaryl, or two R aa groups are joined to form a 3–14 membered
- heterocyclyl or 5–14 membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R dd groups;
- each instance of R cc is, independently, selected from hydrogen, C 1–10 alkyl, C 1–10 perhaloalkyl, C 2–10 alkenyl, C 2–10 alkynyl, C 3–10 carbocyclyl, 3–14 membered heterocyclyl, C 6–14 aryl, and 5–14 membered heteroaryl, or two R cc groups are joined to form a 3–14 membered heterocyclyl or 5–14 membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R dd groups;
- each instance of R dd is, independently, selected from halogen,–CN,–NO 2 ,–N 3 ,– SO 2 H,–SO 3 H,–OH,–OR ee ,–ON(R ff ) 2 ,–N(R ff ) 2 ,–N(R ff ) +
- each instance of R ee is, independently, selected from C 1–6 alkyl, C 1–6 perhaloalkyl, C 2– 6 alkenyl, C 2–6 alkynyl, C 3–10 carbocyclyl, C 6–10 aryl, 3–10 membered heterocyclyl, and 3–10 membered heteroaryl, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R gg groups;
- each instance of R ff is, independently, selected from hydrogen, C 1–6 alkyl, C 1–6 perhaloalkyl, C 2–6 alkenyl, C 2–6 alkynyl, C 3–10 carbocyclyl, 3–10 membered heterocyclyl, C 6– 10 aryl and 5–10 membered heteroaryl, or two R ff groups are joined to form a 3–14 membered heterocyclyl or 5–14 membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R gg groups; and each instance of R gg is, independently, halogen,–CN,–NO 2 ,–N 3 ,–SO 2 H,–SO 3 H,– OH,–OC 1–6 alkyl,–ON(C 1–6 alkyl) 2 ,–N(C 1–6
- exemplary carbon atom substituents include, but are not limited to, halogen, ⁇ CN, ⁇ NO 2 , ⁇ N 3 , ⁇ SO 2 H, ⁇ SO 3 H, ⁇ OH, ⁇ OR aa , ⁇ ON(R bb ) 2 , ⁇ N(R bb ) 2 , ⁇ N(R bb ) +
- R aa is, independently, selected from C 1-10 alkyl, C 1-10 perhaloalkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroC 1-10 alkyl, heteroC 2-10 alkenyl, heteroC 2-10 alkynyl, C 3-10 carbocyclyl, 3-14 membered heterocyclyl, C 6-14 aryl, and 5-14 membered heteroaryl, or two R aa groups are joined to form a 3-14 membered heterocyclyl or 5-14 membered heteroaryl ring, wherein each alkyl, alken
- each instance of R cc is, independently, selected from hydrogen, C 1-10 alkyl, C 1-10 perhaloalkyl, C 2-10 alkenyl, C 2-10 alkynyl, heteroC 1-10 alkyl, heteroC 2-10 alkenyl, heteroC 2-10 alkynyl, C 3-10 carbocyclyl, 3-14 membered heterocyclyl, C 6-14 aryl, and 5-14 membered heteroaryl, or two R cc groups are joined to form a 3-14 membered heterocyclyl or 5-14 membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R dd groups;
- each instance of R dd is, independently, selected from halogen, ⁇ CN, ⁇ NO 2 , ⁇ N 3 , ⁇ SO 2 H, ⁇ SO 3 H, ⁇ OH, ⁇ OR ee , ⁇ ON(R ff ) 2 , ⁇ N(R ff ) 2 , ⁇ N(R ff ) +
- each instance of R ee is, independently, selected from C 1-6 alkyl, C 1-6 perhaloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, heteroC 1-6 alkyl, heteroC 2-6 alkenyl, heteroC 2-6 alkynyl, C 3-10
- each alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl, heteroalkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R gg groups;
- each instance of R ff is, independently, selected from hydrogen, C 1-6 alkyl, C 1-6 perhaloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, heteroC 1-6 alkyl, heteroC 2-6 alkenyl, heteroC 2-6 alkynyl, C 3-10 carbocyclyl, 3-10 membered heterocyclyl, C 6-10 aryl and 5-10 membered heteroaryl, or two R ff groups are joined to form a 3-10 membered heterocyclyl or 5-10 membered heteroaryl ring, wherein each alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl,
- heteroalkynyl, carbocyclyl, heterocyclyl, aryl, and heteroaryl is independently substituted with 0, 1, 2, 3, 4, or 5 R gg groups;
- each instance of R gg is, independently, halogen, ⁇ CN, ⁇ NO 2 , ⁇ N 3 , ⁇ SO 2 H, ⁇ SO 3 H, ⁇ OH, ⁇ OC 1-6 alkyl, ⁇ ON(C 1-6 alkyl) 2 , ⁇ N(C 1-6 alkyl) 2 , ⁇ N(C 1-6 alkyl) +
- amino refers to a group of the formula (–NH 2 ).
- A“substituted amino” refers either to a mono-substituted amine (–NHR h ) of a disubstituted amine (–NR h
- R h substituent is any substituent as described herein that results in the formation of a stable moiety (e.g., a suitable amino protecting group; aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, amino, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino,
- a suitable amino protecting group aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, amino, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino,
- heteroarylamino alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy,
- R h substituents of the di- substituted amino group(–NR h
- alkoxy refers to a“substituted hydroxyl” of the formula (–OR i ), wherein R i is an optionally substituted alkyl group as defined herein, and the oxygen moiety is directly attached to the parent molecule.
- alkylthioxy refers to a“substituted thiol” of the formula (–SR r ), wherein R r is an optionally substituted alkyl group as defined herein, and the sulfur moiety is directly attached to the parent molecule.
- alkylamino refers to a“substituted amino” of the formula (–NR h
- R h is, independently, a hydrogen or an optionally substituted alkyl group as defined herein, and the nitrogen moiety is directly attached to the parent molecule.
- aryl refers to stable aromatic mono- or polycyclic ring system having 3–20 ring atoms, of which all the ring atoms are carbon, and which may be substituted or unsubstituted.
- “aryl” refers to a mono, bi, or tricyclic C 4 –C 20 aromatic ring system having one, two, or three aromatic rings which include, but not limited to, phenyl, biphenyl, naphthyl, and the like, which may bear one or more substituents.
- Aryl substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy, heteroalkyloxy, aryloxy, heteroaryloxy, aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalkylthioxy, arylthioxy, heteroarylthioxy, acyl
- arylalkyl refers to an aryl substituted alkyl group, wherein the terms “aryl” and“alkyl” are defined herein, and wherein the aryl group is attached to the alkyl group, which in turn is attached to the parent molecule.
- exemplary arylalkyl groups are benzyl and phenethyl.
- aryloxy refers to a“substituted hydroxyl” of the formula (–OR i ), wherein R i is an optionally substituted aryl group as defined herein, and the oxygen moiety is directly attached to the parent molecule.
- arylamino refers to a“substituted amino” of the formula (–NR h
- R h is, independently, a hydrogen or an optionally substituted aryl group as defined herein, and the nitrogen moiety is directly attached to the parent molecule.
- arylthioxy refers to a“substituted thiol” of the formula (–SR r ), wherein R r is an optionally substituted aryl group as defined herein, and the sulfur moiety is directly attached to the parent molecule.
- halo and“halogen” refer to an atom selected from fluorine (fluoro,– F), chlorine (chloro,–Cl), bromine (bromo,–Br), and iodine (iodo,–I).
- heteroaliphatic refers to an aliphatic moiety, as defined herein, which includes both saturated and unsaturated, nonaromatic, straight chain (i.e., unbranched), branched, acyclic, cyclic (i.e., heterocyclic), or polycyclic hydrocarbons, which are optionally substituted with one or more functional groups, and that contain one or more oxygen, sulfur, nitrogen, phosphorus, or silicon atoms, e.g., in place of carbon atoms.
- straight chain i.e., unbranched
- acyclic i.e., heterocyclic
- polycyclic hydrocarbons which are optionally substituted with one or more functional groups, and that contain one or more oxygen, sulfur, nitrogen, phosphorus, or silicon atoms, e.g., in place of carbon atoms.
- heteroaliphatic moieties are substituted by independent replacement of one or more of the hydrogen atoms thereon with one or more substituents.
- “heteroaliphatic” is intended herein to include, but is not limited to, heteroalkyl, heteroalkenyl, heteroalkynyl, heterocycloalkyl, heterocycloalkenyl, and heterocycloalkynyl moieties.
- the term“heteroaliphatic” includes the terms “heteroalkyl,”“heteroalkenyl”,“heteroalkynyl”, and the like.
- heteroalkyl “heteroalkenyl”,“heteroalkynyl”, and the like encompass both substituted and unsubstituted groups.
- “heteroaliphatic” is used to indicate those heteroaliphatic groups (cyclic, acyclic, substituted, unsubstituted, branched or unbranched) having 1–20 carbon atoms.
- Heteroaliphatic group substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, sulfinyl, sulfonyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino,
- a stable moiety e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, sulfinyl, sulfonyl, o
- heteroarylamino alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy,
- heteroalkyloxy aryloxy, heteroaryloxy, aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalkylthioxy, arylthioxy, heteroarylthioxy, acyloxy, and the like, each of which may or may not be further substituted).
- heteroalkyl refers to an alkyl moiety, as defined herein, which contain one or more oxygen, sulfur, nitrogen, phosphorus, or silicon atoms, e.g., in place of carbon atoms.
- heteroalkenyl refers to an alkenyl moiety, as defined herein, which contain one or more oxygen, sulfur, nitrogen, phosphorus, or silicon atoms, e.g., in place of carbon atoms.
- heteroalkynyl refers to an alkynyl moiety, as defined herein, which contain one or more oxygen, sulfur, nitrogen, phosphorus, or silicon atoms, e.g., in place of carbon atoms.
- heteroalkylamino refers to a“substituted amino” of the formula (– NR h
- R h is, independently, a hydrogen or an optionally substituted heteroalkyl group, as defined herein, and the nitrogen moiety is directly attached to the parent molecule.
- heteroalkyloxy refers to a“substituted hydroxyl” of the formula (– OR i ), wherein R i is an optionally substituted heteroalkyl group, as defined herein, and the oxygen moiety is directly attached to the parent molecule.
- heteroalkylthioxy refers to a“substituted thiol” of the formula (–SR r ), wherein R r is an optionally substituted heteroalkyl group, as defined herein, and the sulfur moiety is directly attached to the parent molecule.
- carbocyclyl or“carbocyclic” refers to a radical of a non–aromatic cyclic hydrocarbon group having from 3 to 14 ring carbon atoms (“C 3–14 carbocyclyl”) and zero heteroatoms in the non–aromatic ring system.
- a carbocyclyl group has 3 to 10 ring carbon atoms (“C 3–10 carbocyclyl”).
- a carbocyclyl group has 3 to 8 ring carbon atoms (“C 3–8 carbocyclyl”).
- a carbocyclyl group has 3 to 7 ring carbon atoms (“C 3–7 carbocyclyl”).
- a carbocyclyl group has 3 to 6 ring carbon atoms (“C 3–6 carbocyclyl”). In some embodiments, a carbocyclyl group has 4 to 6 ring carbon atoms (“C 4–6 carbocyclyl”). In some embodiments, a carbocyclyl group has 5 to 6 ring carbon atoms (“C 5–6 carbocyclyl”). In some embodiments, a carbocyclyl group has 5 to 10 ring carbon atoms (“C 5–10 carbocyclyl”).
- Exemplary C 3–6 carbocyclyl groups include, without limitation, cyclopropyl (C 3 ), cyclopropenyl (C 3 ), cyclobutyl (C 4 ), cyclobutenyl (C 4 ), cyclopentyl (C 5 ), cyclopentenyl (C 5 ), cyclohexyl (C 6 ), cyclohexenyl (C 6 ), cyclohexadienyl (C 6 ), and the like.
- Exemplary C 3–8 carbocyclyl groups include, without limitation, the aforementioned C 3–6 carbocyclyl groups as well as cycloheptyl (C 7 ), cycloheptenyl (C 7 ), cycloheptadienyl (C 7 ), cycloheptatrienyl (C 7 ), cyclooctyl (C 8 ), cyclooctenyl (C 8 ), bicyclo[2.2.1]heptanyl (C 7 ), bicyclo[2.2.2]octanyl (C 8 ), and the like.
- Exemplary C 3–10 carbocyclyl groups include, without limitation, the
- the carbocyclyl group is either monocyclic (“monocyclic carbocyclyl”) or polycyclic (e.g., containing a fused, bridged or spiro ring system such as a bicyclic system (“bicyclic carbocyclyl”) or tricyclic system (“tricyclic carbocyclyl”)) and can be saturated or can contain one or more carbon–carbon double or triple bonds.
- “Carbocyclyl” also includes ring systems wherein the carbocyclyl ring, as defined above, is fused with one or more aryl or heteroaryl groups wherein the point of attachment is on the carbocyclyl ring, and in such instances, the number of carbons continue to designate the number of carbons in the carbocyclic ring system.
- each instance of a carbocyclyl group is independently unsubstituted (an“unsubstituted carbocyclyl”) or substituted (a“substituted carbocyclyl”) with one or more substituents.
- the carbocyclyl group is an unsubstituted C 3–14 carbocyclyl.
- the carbocyclyl group is a substituted C 3–14 carbocyclyl.
- “carbocyclyl” is a monocyclic, saturated carbocyclyl group having from 3 to 14 ring carbon atoms (“C 3–14 cycloalkyl”). In some embodiments, a cycloalkyl group has 3 to 10 ring carbon atoms (“C 3–10 cycloalkyl”). In some embodiments, a cycloalkyl group has 3 to 8 ring carbon atoms (“C 3–8 cycloalkyl”). In some embodiments, a cycloalkyl group has 3 to 6 ring carbon atoms (“C 3–6 cycloalkyl”).
- a cycloalkyl group has 4 to 6 ring carbon atoms (“C 4–6 cycloalkyl”). In some embodiments, a cycloalkyl group has 5 to 6 ring carbon atoms (“C 5–6 cycloalkyl”). In some embodiments, a cycloalkyl group has 5 to 10 ring carbon atoms (“C 5–10 cycloalkyl”). Examples of C 5–6 cycloalkyl groups include cyclopentyl (C 5 ) and cyclohexyl (C 5 ).
- C 3–6 cycloalkyl groups include the aforementioned C 5–6 cycloalkyl groups as well as cyclopropyl (C 3 ) and cyclobutyl (C 4 ).
- C 3–8 cycloalkyl groups include the aforementioned C 3–6 cycloalkyl groups as well as cycloheptyl (C 7 ) and cyclooctyl (C 8 ).
- each instance of a cycloalkyl group is independently unsubstituted (an“unsubstituted cycloalkyl”) or substituted (a“substituted cycloalkyl”) with one or more substituents.
- the cycloalkyl group is an unsubstituted C 3–14 cycloalkyl.
- the cycloalkyl group is a substituted C 3–14 cycloalkyl.
- heterocyclic refers to a cyclic heteroaliphatic group.
- a heterocyclic group refers to a non-aromatic, partially unsaturated or fully saturated, 3- to 12-membered ring system, which includes single rings of 3 to 8 atoms in size, and bi- and tri-cyclic ring systems which may include aromatic five- or six-membered aryl or heteroaryl groups fused to a non-aromatic ring.
- These heterocyclic rings include those having from one to three heteroatoms independently selected from oxygen, sulfur, and nitrogen, in which the nitrogen and sulfur heteroatoms may optionally be oxidized and the nitrogen heteroatom may optionally be quaternized.
- heterocyclic refers to a non-aromatic 5-, 6-, or 7-membered ring or polycyclic group wherein at least one ring atom is a heteroatom selected from O, S, and N (wherein the nitrogen and sulfur heteroatoms may be optionally oxidized), and the remaining ring atoms are carbon, the radical being joined to the rest of the molecule via any of the ring atoms.
- Heterocyclyl groups include, but are not limited to, a bi- or tri-cyclic group, comprising fused five, six, or seven- membered rings having between one and three heteroatoms independently selected from the oxygen, sulfur, and nitrogen, wherein (i) each 5-membered ring has 0 to 2 double bonds, each 6-membered ring has 0 to 2 double bonds, and each 7-membered ring has 0 to 3 double bonds, (ii) the nitrogen and sulfur heteroatoms may be optionally oxidized, (iii) the nitrogen heteroatom may optionally be quaternized, and (iv) any of the above heterocyclic rings may be fused to an aryl or heteroaryl ring.
- heterocycles include azacyclopropanyl, azacyclobutanyl, 1,3-diazatidinyl, piperidinyl, piperazinyl, azocanyl, thiaranyl, thietanyl, tetrahydrothiophenyl, dithiolanyl, thiacyclohexanyl, oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropuranyl, dioxanyl, oxathiolanyl, morpholinyl, thioxanyl, tetrahydronaphthyl, and the like, which may bear one or more substituents.
- Substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, sulfinyl, sulfonyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy, heteroalkyloxy, aryloxy, heteroaryloxy, aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalkylthi
- heteroaryl refers to stable aromatic mono- or polycyclic ring system having 3-20 ring atoms, of which one ring atom is selected from S, O, and N; zero, one, or two ring atoms are additional heteroatoms independently selected from S, O, and N; and the remaining ring atoms are carbon, the radical being joined to the rest of the molecule via any of the ring atoms.
- heteroaryls include, but are not limited to pyrrolyl, pyrazolyl, imidazolyl, pyridinyl (pyridyl), pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyyrolizinyl, indolyl, quinolinyl, isoquinolinyl, benzoimidazolyl, indazolyl, quinolinyl, isoquinolinyl, quinolizinyl, cinnolinyl, quinazolynyl, phthalazinyl, naphthridinyl, quinoxalinyl, thiophenyl, thianaphthenyl, furanyl, benzofuranyl, benzothiazolyl, thiazolynyl, isothiazolyl, thiadiazolynyl, oxazolyl, isoxazolyl,
- Heteroaryl substituents include, but are not limited to, any of the substituents described herein, that result in the formation of a stable moiety (e.g., aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, sulfinyl, sulfonyl, oxo, imino, thiooxo, cyano, isocyano, amino, azido, nitro, hydroxyl, thiol, halo, aliphaticamino, heteroaliphaticamino, alkylamino, heteroalkylamino, arylamino, heteroarylamino, alkylaryl, arylalkyl, aliphaticoxy, heteroaliphaticoxy, alkyloxy, heteroalkyloxy, aryloxy, heteroaryloxy, aliphaticthioxy, heteroaliphaticthioxy, alkylthioxy, heteroalky
- heteroarylamino refers to a“substituted amino” of the (–NR h
- R h is, independently, hydrogen or an optionally substituted heteroaryl group, as defined herein, and the nitrogen moiety is directly attached to the parent molecule.
- heteroaryloxy refers to a“substituted hydroxyl” of the formula (– OR i ), wherein R i is an optionally substituted heteroaryl group, as defined herein, and the oxygen moiety is directly attached to the parent molecule.
- heteroarylthioxy refers to a“substituted thiol” of the formula (–SR r ), wherein R r is an optionally substituted heteroaryl group, as defined herein, and the sulfur moiety is directly attached to the parent molecule.
- hydroxy refers to a group of the formula (–OH).
- a “substituted hydroxyl” refers to a group of the formula (–OR i ), wherein R i can be any substituent which results in a stable moiety (e.g., a suitable hydroxyl protecting group; aliphatic, alkyl, alkenyl, alkynyl, heteroaliphatic, heterocyclic, aryl, heteroaryl, acyl, nitro, alkylaryl, arylalkyl, and the like, each of which may or may not be further substituted).
- nitro refers to a group of the formula (–NO 2 ).
- A“protecting group” is well known in the art and include those described in detail in Greene’s Protective Groups in Organic Synthesis, P. G. M. Wuts and T. W. Greene, 4 th edition, Wiley-Interscience, 2006, the entirety of which is incorporated herein by reference.
- Suitable“amino-protecting groups” include methyl carbamate, ethyl carbamante, 9-fluorenylmethyl carbamate (Fmoc), 9-(2- sulfo)fluorenylmethyl carbamate, 9-(2,7-dibromo)fluoroenylmethyl carbamate, 2,7-di-t-butyl- [9-(10,10-dioxo-10,10,10,10-tetrahydrothioxanthyl)]methyl carbamate (DBD-Tmoc), 4- methoxyphenacyl carbamate (Phenoc), 2,2,2-trichloroethyl carbamate (Troc), 2- trimethylsilylethyl carbamate (Teoc), 2-phenylethyl carbamate (hZ), 1-(1-adamantyl)-1- methylethyl carbamate (Adpoc), 1,1-di
- TLBOC 1-methyl-1-(4-biphenylyl)ethyl carbamate (Bpoc), 1-(3,5-di-t-butylphenyl)-1- methylethyl carbamate (t-Bumeoc), 2-(2′- and 4′-pyridyl)ethyl carbamate (Pyoc), 2-(N,N- dicyclohexylcarboxamido)ethyl carbamate, t-butyl carbamate (BOC or Boc), 1-adamantyl carbamate (Adoc), vinyl carbamate (Voc), allyl carbamate (Alloc), 1-isopropylallyl carbamate (Ipaoc), cinnamyl carbamate (Coc), 4-nitrocinnamyl carbamate (Noc), 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate, alkyldithio carbamate, benzyl carbamate (C
- tungsten)carbonyl]amine N-copper chelate, N-zinc chelate, N-nitroamine, N-nitrosoamine, amine N-oxide, diphenylphosphinamide (Dpp), dimethylthiophosphinamide (Mpt), diphenylthiophosphinamide (Ppt), dialkyl phosphoramidates, dibenzyl phosphoramidate, diphenyl phosphoramidate, benzenesulfenamide, o-nitrobenzenesulfenamide (Nps), 2,4- dinitrobenzenesulfenamide, pentachlorobenzenesulfenamide, 2-nitro-4- methoxybenzenesulfenamide, triphenylmethylsulfenamide, 3-nitropyridinesulfenamide (Npys), p-toluenesulfonamide (Ts), benzenesulfonamide, 2,3,6,-trimethyl-4- methoxybenzenesul
- A“hydroxyl protecting group” (also referred to as an“oxygen protecting group”) is well known in the art and includes those described in detail in Greene (1999). Suitable hydroxyl protecting groups include methyl, methoxylmethyl (MOM), methylthiomethyl (MTM), t-butylthiomethyl, (phenyldimethylsilyl)methoxymethyl (SMOM), benzyloxymethyl (BOM), p-methoxybenzyloxymethyl (PMBM), (4-methoxyphenoxy)methyl (p-AOM), guaiacolmethyl (GUM), t-butoxymethyl, 4-pentenyloxymethyl (POM), siloxymethyl, 2- methoxyethoxymethyl (MEM), 2,2,2-trichloroethoxymethyl, bis(2-chloroethoxy)methyl, 2- (trimethylsilyl)ethoxymethyl (SEMOR), tetrahydropyranyl (THP), 3- bromotetrahydropyranyl, tetrahydropyr
- DEIPS diethylisopropylsilyl
- TDMS t-butyldimethylsilyl
- TDPS t- butyldiphenylsilyl
- tribenzylsilyl tri-p-xylylsilyl, triphenylsilyl
- DPMS diphenylmethylsilyl
- TMPS t-butylmethoxyphenylsilyl
- formate benzoylformate, acetate, chloroacetate, dichloroacetate, trichloroacetate, trifluoroacetate, methoxyacetate, triphenylmethoxyacetate, phenoxyacetate, p-chlorophenoxyacetate, 3-phenylpropionate, 4- oxopentanoate (levulinate), 4,4-(ethylenedithio)pentanoate (levulinoyldithioacetal), pivaloate, adamantoate, crotonate, 4-methoxycrotonate, benzoate, p-phenylbenzoate, 2,4,6- trimethylbenzoate (mesitoate), alkyl methyl carbonate, 9-fluorenylmethyl carbonate (Fmoc), alkyl ethyl carbonate, alkyl 2,2,2-t
- protecting groups include methylene acetal, ethylidene acetal, 1-t-butylethylidene ketal, 1-phenylethylidene ketal, (4- methoxyphenyl)ethylidene acetal, 2,2,2-trichloroethylidene acetal, acetonide,
- cyclopentylidene ketal cyclohexylidene ketal, cycloheptylidene ketal, benzylidene acetal, p- methoxybenzylidene acetal, 2,4-dimethoxybenzylidene ketal, 3,4-dimethoxybenzylidene acetal, 2-nitrobenzylidene acetal, methoxymethylene acetal, ethoxymethylene acetal, dimethoxymethylene ortho ester, 1-methoxyethylidene ortho ester, 1-ethoxyethylidine ortho ester, 1,2-dimethoxyethylidene ortho ester, ⁇ -methoxybenzylidene ortho ester, 1-(N,N- dimethylamino)ethylidene derivative, ⁇ -(N,N′-dimethylamino)benzylidene derivative, 2- oxacyclopentylidene ortho ester, di-t
- the substituent present on an sulfur atom is a sulfur protecting group (also referred to as a“thiol protecting group”).
- carbohydrate or“saccharide” refers to an aldehydic or ketonic derivative of polyhydric alcohols.
- Carbohydrates include compounds with relatively small molecules (e.g., sugars) as well as macromolecular or polymeric substances (e.g., starch, glycogen, and cellulose polysaccharides).
- saccharide refers to monosaccharides, disaccharides, or polysaccharides. Monosaccharides are the simplest carbohydrates in that they cannot be hydrolyzed to smaller carbohydrates.
- monosaccharides can be represented by the general formula C y H 2y O y (e.g., C 6 H 12 O 6 (a hexose such as glucose)), wherein y is an integer equal to or greater than 3.
- C y H 2y O y e.g., C 6 H 12 O 6 (a hexose such as glucose)
- y is an integer equal to or greater than 3.
- Certain polyhydric alcohols not represented by the general formula described above may also be considered monosaccharides.
- deoxyribose is of the formula C 5 H 10 O 4 and is a monosaccharide.
- Monosaccharides usually consist of five or six carbon atoms and are referred to as pentoses and hexoses, receptively.
- the monosaccharide contains an aldehyde it is referred to as an aldose; and if it contains a ketone, it is referred to as a ketose.
- Monosaccharides may also consist of three, four, or seven carbon atoms in an aldose or ketose form and are referred to as trioses, tetroses, and heptoses, respectively.
- Glyceraldehyde and dihydroxyacetone are considered to be aldotriose and ketotriose sugars, respectively.
- aldotetrose sugars include erythrose and threose
- ketotetrose sugars include erythrulose.
- Aldopentose sugars include ribose, arabinose, xylose, and lyxose; and ketopentose sugars include ribulose, arabulose, xylulose, and lyxulose.
- aldohexose sugars include glucose (for example, dextrose), mannose, galactose, allose, altrose, talose, gulose, and idose; and ketohexose sugars include fructose, psicose, sorbose, and tagatose.
- Ketoheptose sugars include sedoheptulose.
- the aldohexose D -glucose for example, has the formula C 6 H 12 O 6 , of which all but two of its six carbons atoms are stereogenic, making D-glucose one of the 16 (i.e., 2 4 ) possible stereoisomers.
- the assignment of D or L is made according to the orientation of the asymmetric carbon furthest from the carbonyl group: in a standard Fischer projection if the hydroxyl group is on the right the molecule is a D sugar, otherwise it is an L sugar.
- the aldehyde or ketone group of a straight- chain monosaccharide will react reversibly with a hydroxyl group on a different carbon atom to form a hemiacetal or hemiketal, forming a heterocyclic ring with an oxygen bridge between two carbon atoms. Rings with five and six atoms are called furanose and pyranose forms, respectively, and exist in equilibrium with the straight-chain form.
- the carbon atom containing the carbonyl oxygen becomes a stereogenic center with two possible configurations: the oxygen atom may take a position either above or below the plane of the ring.
- the resulting possible pair of stereoisomers is called anomers.
- an ⁇ anomer the–OH substituent on the anomeric carbon rests on the opposite side (trans) of the ring from the– CH 2 OH side branch.
- the alternative form, in which the–CH 2 OH substituent and the anomeric hydroxyl are on the same side (cis) of the plane of the ring, is called a ⁇ anomer.
- a carbohydrate including two or more joined monosaccharide units is called a disaccharide or polysaccharide (e.g., a trisaccharide), respectively.
- Exemplary disaccharides include sucrose, lactulose, lactose, maltose, isomaltose, trehalose, cellobiose, xylobiose, laminaribiose, gentiobiose, mannobiose, melibiose, nigerose, and rutinose.
- Exemplary trisaccharides include, but are not limited to, isomaltotriose, nigerotriose, maltotriose, melezitose, maltotriulose, raffinose, and kestose.
- carbohydrate also includes other natural or synthetic stereoisomers of the carbohydrates described herein.
- pharmaceutically acceptable salt refers to those salts which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of humans and other animals without undue toxicity, irritation, allergic response, and the like, and are commensurate with a reasonable benefit/risk ratio.
- Pharmaceutically acceptable salts are well known in the art. For example, Berge et al. describe pharmaceutically acceptable salts in detail in J. Pharmaceutical Sciences, 1977, 66, 1–19, incorporated herein by reference.
- salts of the compounds of this invention include those derived from suitable inorganic and organic acids and bases.
- the salts can be prepared during the final isolation and purification of the compounds or separately by reacting the appropriate compound in the form of the free base with a suitable acid.
- Representative acid addition salts include acetate, adipate, alginate, L-ascorbate, aspartate, benzoate, benzenesulfonate
- basic groups in the compounds disclosed herein can be quaternized with methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides; dimethyl, diethyl, dibutyl, and diamyl sulfates; decyl, lauryl, myristyl, and steryl chlorides, bromides, and iodides; and benzyl and phenethyl bromides.
- acids which can be employed to form therapeutically acceptable salts include inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, and phosphoric acid; and organic acids such as oxalic acid, maleic acid, succinic acid, and citric acid.
- “Basic addition salts” refer to salts derived from appropriate bases, these salts including alkali metal, alkaline earth metal, and quaternary amine salts.
- the present invention contemplates sodium, potassium, magnesium, and calcium salts of the compounds disclosed herein, and the like.
- Basic addition salts can be prepared during the final isolation and purification of the compounds, often by reacting a carboxyl group with a suitable base such as the hydroxide, carbonate, or bicarbonate of a metal cation or with ammonia or an organic primary, secondary, or tertiary amine.
- a suitable base such as the hydroxide, carbonate, or bicarbonate of a metal cation or with ammonia or an organic primary, secondary, or tertiary amine.
- the cations of therapeutically acceptable salts include lithium, sodium (by using, e.g., NaOH), potassium (by using, e.g., KOH), calcium (by using, e.g., Ca(OH) 2 ), magnesium (by using, e.g., Mg(OH) 2 and magnesium acetate), zinc, (by using, e.g., Zn(OH) 2 and zinc acetate), and aluminum, as well as nontoxic quaternary amine cations such as ammonium,
- tetramethylammonium tetraethylammonium
- methylamine dimethylamine, trimethylamine, triethylamine, diethylamine, ethylamine, tributylamine, pyridine, N,N-dimethylaniline, N- methylpiperidine, N-methylmorpholine, dicyclohexylamine, procaine, dibenzylamine, N,N- dibenzylphenethylamine, 1-ephenamine, and N,N-dibenzylethylenediamine.
- organic amines useful for the formation of base addition salts include ethylenediamine, ethanolamine, diethanolamine, piperidine, piperazine, choline hydroxide, hydroxyethyl morpholine, hydroxyethyl pyrrolidone, imidazole, n-methyl-d-glucamine, N,N'- dibenzylethylenediamine, N,N'-diethylethanolamine, N,N'-dimethylethanolamine, triethanolamine, and tromethamine.
- Basic amino acids e.g., 1-glycine and 1-arginine
- amino acids which may be zwitterionic at neutral pH e.g., betaine (N,N,N-trimethylglycine) are also contemplated.
- tautomer refers to a particular isomer of a compound in which a hydrogen and double bond have changed position with respect to the other atoms of the molecule.
- tautomers include keto-enol forms, imine-enamine forms, amide-imino alcohol forms, amidine-aminidine forms, nitroso-oxime forms, thio ketone-enethiol forms, N-nitroso- hydroxyazo forms, nitro-aci-nitro forms, lactam-lactim forms, ketene-ynol forms, enamine- enamine forms, and pyridione-hydroxypyridine forms.
- polymorphs refers to a crystalline form of a compound (or a salt, hydrate, or solvate thereof). All polymorphs have the same elemental composition. Different crystalline forms usually have different X-ray diffraction patterns, infrared spectra, melting points, density, hardness, crystal shape, optical and electrical properties, stability, and solubility. Recrystallization solvent, rate of crystallization, storage temperature, and other factors may cause one crystal form to dominate. Various polymorphs of a compound can be prepared by crystallization under different conditions.
- solvate refers to forms of the compound, or a salt thereof, that are associated with a solvent, usually by a solvolysis reaction. This physical association may include hydrogen bonding.
- solvents include water, methanol, ethanol, acetic acid, DMSO, THF, diethyl ether, and the like.
- the compounds of the invention may be prepared, e.g., in crystalline form, and may be solvated. Suitable solvates include
- solvates and further include both stoichiometric solvates and non-stoichiometric solvates.
- the solvate will be capable of isolation, for example, when one or more solvent molecules are incorporated in the crystal lattice of a crystalline solid.“Solvate” encompasses both solution-phase and isolable solvates.
- Representative solvates include hydrates, ethanolates, and methanolates.
- hydrate refers to a compound that is associated with water.
- the number of the water molecules contained in a hydrate of a compound is in a definite ratio to the number of the compound molecules in the hydrate. Therefore, a hydrate of a compound may be represented, for example, by the general formula R ⁇ xH 2 O, wherein R is the compound and wherein x is a number greater than 0.
- a given compound may form more than one type of hydrates, including, e.g., monohydrates (x is 1), lower hydrates (x is a number greater than 0 and smaller than 1, e.g., hemihydrates (R ⁇ 0.5H 2 O)), and polyhydrates (x is a number greater than 1, e.g., dihydrates (R ⁇ 2H 2 O) and hexahydrates (R ⁇ 6H 2 O)).
- monohydrates x is 1
- lower hydrates x is a number greater than 0 and smaller than 1, e.g., hemihydrates (R ⁇ 0.5H 2 O)
- polyhydrates x is a number greater than 1, e.g., dihydrates (R ⁇ 2H 2 O) and hexahydrates (R ⁇ 6H 2 O)
- the term“subject” refers to any animal.
- the subject is a mammal.
- the subject is a human (e.g., a man, a woman, or a child).
- the human may be of either sex and may be at any stage of development.
- the subject has been diagnosed with the condition or disease to be treated.
- the subject is at risk of developing the condition or disease.
- the subject is an experimental animal (e.g., mouse, rat, rabbit, dog, pig, or primate).
- the experimental animal may be genetically engineered.
- the subject is a domesticated animal (e.g., dog, cat, bird, horse, cow, goat, sheep).
- the terms“administer,”“administering,” or“administration” refers to implanting, absorbing, ingesting, injecting, or inhaling an inventive compound, or a pharmaceutical composition thereof.
- treatment refers to reversing, alleviating, delaying the onset of, or inhibiting the progress of a“pathological condition” (e.g., a disease, disorder, or condition, or one or more signs or symptoms thereof) described herein.
- a“pathological condition” e.g., a disease, disorder, or condition, or one or more signs or symptoms thereof
- treatment may be administered after one or more signs or symptoms have developed or have been observed.
- treatment may be administered in the absence of signs or symptoms of the disease or condition.
- treatment may be administered to a susceptible individual prior to the onset of symptoms (e.g., in light of a history of symptoms and/or in light of genetic or other susceptibility factors). Treatment may also be continued after symptoms have resolved, for example, to delay or prevent recurrence.
- an effective amount of a compound of the invention refers to an amount sufficient to elicit the desired biological response, i.e., treating the condition.
- the effective amount of a compound of the invention may vary depending on such factors as the desired biological endpoint, the pharmacokinetics of the compound, the condition being treated, the mode of administration, and the age and health of the subject.
- an effective amount is a therapeutically effective amount.
- an effective amount is a prophylactically effective amount.
- an effective amount is the amount of a compound described herein in a single dose.
- an effective amount is the combined amounts of a compound described herein in multiple doses.
- an effective amount is a cleaning-effective amount.
- the “cleaning-effective” amount of the compound refers to an amount of the compound as described herein which is necessary to remove at least 10% of bacteria from a biofilm as determined by a reduction in numbers of bacteria within the biofilm when compared with a biofilm not exposed to the compound.
- the effective amount is a prophylactically effective amount to prevent normal biofilm formation between normal cleaning times as determined by a statistically significant increase in the number of cells within a biofilm or upon a clean surface. Prevention of normal biofilm formation is determined by the ability to disperse a biofilm using surfactants and or detergents or other chemical treatments which will result in the removal of bacterial cells from a biofilm.
- the treated biofilm must be shown to release 10% or more of its bacteria when compared with a similar biofilm that is not treated when both biofilms are exposed to surfactants and or detergents or other chemical treatments which will result in the removal of bacterial cells from a biofilm.
- A“therapeutically effective amount” of a compound of the present invention or a pharmaceutical composition thereof is an amount sufficient to provide a therapeutic benefit in the treatment of a condition, e.g., iron overload, or to delay or minimize one or more symptoms associated with the condition.
- a therapeutically effective amount of a compound means an amount of therapeutic agent, alone or in combination with other therapies, which provides a therapeutic benefit in the treatment of the condition.
- the term“therapeutically effective amount” can encompass an amount that improves overall therapy, reduces or avoids symptoms or causes of the condition, and/or enhances the therapeutic efficacy of another therapeutic agent.
- a therapeutically effective amount is an amount sufficient for chelating a metal described herein.
- a therapeutically effective amount is an amount sufficient for treating a pathological condition described herein.
- a therapeutically effective amount is an amount sufficient for chelating a metal described herein and for treating a pathological condition described herein.
- A“prophylactically effective amount” of a compound of the present invention is an amount sufficient to prevent a condition, e.g., iron overload, or one or more symptoms associated with the condition or prevent its recurrence.
- a prophylactically effective amount of a compound means an amount of a therapeutic agent, alone or in combination with other agents, which provides a prophylactic benefit in the prevention of the condition.
- the term “prophylactically effective amount” can encompass an amount that improves overall prophylaxis or enhances the prophylactic efficacy of another prophylactic agent.
- a prophylactically effective amount is an amount sufficient for chelating a metal described herein.
- a prophylactically effective amount is an amount sufficient for preventing a pathological condition described herein. In certain embodiments, a prophylactically effective amount is an amount sufficient for chelating a metal described herein and for preventing a pathological condition described herein.
- tissue samples such as tissue sections and needle biopsies of a tissue
- cell samples e.g., cytological smears (such as Pap or blood smears) or samples of cells obtained by microdissection); samples of whole organisms (such as samples of yeasts or bacteria); or cell fractions, fragments or organelles (such as obtained by lysing cells and separating the components thereof by centrifugation or otherwise).
- biological samples include blood, serum, urine, semen, fecal matter, cerebrospinal fluid, interstitial fluid, mucous, tears, sweat, pus, biopsied tissue (e.g., obtained by a surgical biopsy or needle biopsy), nipple aspirates, milk, vaginal fluid, saliva, swabs (such as buccal swabs), or any material containing biomolecules that is derived from a first biological sample.
- “Chelation,”“chelating,”“sequestration,” or“sequestering” is the formation or presence of two or more separate coordinate bonds between a polydentate (multiple-bonded) compound and a single central atom.
- the polydentate compound is typically an organic compound and referred to as a“chelator,”“chelant,”“chelating agent,”“sequestrator,” “sequestering agent,” or“ligand.”
- the central atom is usually a metal atom or metal ion (e.g., a metal atom or metal ion described herein, such as iron (e.g., Fe(III)), Al(III), chromium (e.g., Cr(VI)), and uranium (e.g., U(VI)), etc.).
- the chelator may form a stable complex with the central atom through coordinate bonds, inactivating the central atom so that the central atom is less likely to react with other molecules or atoms.
- Reactive oxygen species refers to molecules or ions formed by the incomplete reduction of oxygen.
- Reactive oxygen species include superoxide anion (O •- 2 ), peroxides such as hydrogen peroxide (H 2 O 2 ), hydroxyl radical (HO • ), and
- hypochlorous acid H 2 O
- Reactive oxygen species may be formed by any number of mechanisms (e.g., enzymatically, by ionizing radiation, by reaction oxygen with a metal).
- the reactive oxygen species are formed by the reduction of oxygen by an iron ion, such as Fe +2 .
- antimicrobial refers to a compound having a destructive killing action upon microbes or microorganisms.
- microorganism refer to very minute, microscopic life forms or organisms, which may be either plant or animal, and which may include, but are not limited to, algae, bacteria, fungi, protozoae, and parasites.
- biofilm formation refers to the attachment of microorganisms to surfaces and the subsequent development of multiple layers of cells.
- the biofilm is bacterial biofilm.
- biocide refers to a chemical substance or microorganism (e.g., bacteria, fungal cells, protozoa, etc.), which can deter, render harmless, or exert a controlling effect on any harmful organism by chemical or biological means.
- the biocides are pesticides such as fungicides, herbicides, insecticides, algicides, molluscicides, miticides and rodenticides.
- the biocides are antimicrobials such as germicides, antibiotics, antibacterials, antivirals, antifungals, antiprotozoals and antiparasites.
- fungicide refers to a compound having either a fungicidal or fungistatic effect upon fungi contacted by the compound.
- Infectious diseases are caused by microbes such as bacteria, fungi, and parasites. These pathogenic micobes typically require one or more metals (e.g., iron, calcium, magnesium, strontium, potassium, sodium, chromium, copper, manganese, molybdenum, zinc, and tungsten) to sustain life.
- metals e.g., iron, calcium, magnesium, strontium, potassium, sodium, chromium, copper, manganese, molybdenum, zinc, and tungsten
- iron is used by cytochromes and as a cofactor for enzymes in electron-transport proteins.
- inventive methods use desferrithiocin analogs, desazadesferrithiocin analogs, and N,N′-di(2-hydroxybenzyl)ethylenediamine-N,N′-diacetic acid monohydrochloride (HBED) analogs as metal chelators in the treatment and/or prevention infectious diseases and the inhibition of biofilm formation.
- desferrithiocin analogs desazadesferrithiocin analogs
- HBED N,N′-di(2-hydroxybenzyl)ethylenediamine-N,N′-diacetic acid monohydrochloride
- the inventive methods for preventing and/or treating an infectious disease comprise administering to a subject in need thereof a compound of any one of Formulae (I-A)-(III-A), or a salt, tautomer, stereoisomer, solvate, hydrate, or a polymorph thereof.
- the infectious disease is responsive to the chelation or sequestration of a metal.
- the metal is a monovalent, divalent, tetravalent, pentavalent, or hexavalent metal.
- the metal is a trivalent metal.
- the metal is iron (e.g., Fe(III)).
- the metal is aluminum, thallium, chromium, magnesium, calcium, strontium, nickel, manganese, cobalt, copper, zinc, silver, sodium, potassium, cadmium, mercury, lead, antimony, molybdenum, tungsten, a lanthanide (e.g., cerium), or an actinide (e.g., uranium).
- a lanthanide e.g., cerium
- an actinide e.g., uranium
- the infectious disease being treated and/or prevented is a bacterial infection.
- the bacterial infection is caused by a Gram- positive bacterium.
- Exemplary Gram-positive bacteria include, but are not limited to, species of the genera Staphylococcus, Streptococcus, Micrococcus, Peptococcus, Peptostreptococcus, Enterococcus, Bacillus, Clostridium, Lactobacillus, Listeria, Erysipelothrix,
- the Gram- positive bacterium is a bacterium of the phylum Firmicutes.
- the bacterium is a member of the phylum Firmicutes and the genus Enterococcus, i.e., the bacterial infection is an Enterococcus infection.
- Exemplary Enterococci bacteria include, but are not limited to, E. avium, E. durans, E. faecalis, E. faecium, E. gallinarum, E. solitarius, E. casseliflavus, and E. raffinosus.
- the Enterococcus infection is an E.
- the Enterococcus infection is an E. faecium infection.
- the bacteria is a member of the phylum Firmicutes and the genus Staphylococcus, i.e., the bacterial infection is a Staphylococcus infection.
- Exemplary Staphylococci bacteria include, but are not limited to, S. arlettae, S. aureus, S. auricularis, S. capitis, S. caprae, S. carnous, S. chromogenes, S. cohii, S. condimenti, S. croceolyticus, S. delphini, S. devriesei, S. epidermis, S. equorum, S. felis, S. fluroettii, S. gallinarum, S.
- the Staphylococcus infection is an S. aureus infection.
- the Staphylococcus infection is an S. aureus infection.
- Staphylococcus infection is an S. epidermis infection.
- the Gram- positive bacterium is selected from the group consisting of Staphylococcus aureus,
- Mycobacterium marinum Mycobacterium scrofulaceum, Mycobacterium smegmatis, Mycobacterium terrae, Mycobacterium tuberculosis, Mycobacterium ulcerans, and
- the bacterial infection being treated and/or prevented is an infection caused by a Gram-negative bacterium.
- Gram-negative bacteria include, but are not limited to, Escherchia coli, Caulobacter crescentus, Pseudomonas, Agrobacterium tumefaciens, Branhamella catarrhalis, Citrobacter diversus, Enterobacter aerogenes, Klebsiella pneumoniae, Proteus mirabilis, Salmonella typhimurium, Neisseria meningitidis, Serratia marcescens, Shigella sonnei, Neisseria gonorrhoeae, Acinetobacter baumannii, Salmonella enteriditis, Fusobacterium nucleatum, Veillonella parvula,
- the Gram-negative bacteria species is Pseudomonas. In certain embodiments, the Gram-negative bacteria species is Pseudomonas aeruginosa.
- the bacterial infection being treated and/or prevented is a chronic bacterial infection.
- a“chronic bacterial infection” is a bacterial infection that is of a long duration or frequent recurrence.
- a chronic middle ear infection, or otitis media can occur when the Eustachian tube becomes blocked repeatedly due to allergies, multiple infections, ear trauma, or swelling of the adenoids.
- the definition of “long duration” will depend upon the particular infection. For example, in the case of a chronic middle ear infection, it may last for weeks to months.
- Exemplary chronic bacterial infections include, but are not limited to, urinary tract infection (most commonly caused by Escherichia coli and/or Staphylococcus saprophyticus), gastritis (most commonly caused by Helicobacter pylori), respiratory infection (such as those commonly afflicting patents with cystic fibrosis, most commonly caused by Pseudomonas aeuroginosa), cystitis (most commonly caused by Escherichia coli), pyelonephritis (most commonly caused by Proteus species, Escherichia coli and/or Pseudomonas sp), osteomyelitis (most commonly caused by Staphylococcus aureus, but also by Escherichia coli), bacteremia, skin infection, rosacea, acne, chronic wound infection, infectious kidney stones (can be caused by Proteus mirabilis), bacterial endocarditis, and sinus infection.
- urinary tract infection most commonly caused by Escherichia
- the bacterial infection being treated and/or prevented is caused by an organism resistant to one or more antibiotics.
- the bacterial infection is caused by an organism resistant to penicillin.
- the bacterial infection is caused by an organism resistant to vancomycin (VR).
- the bacterial infection is caused by vancomycin- resistant E. faecalis.
- the bacterial infection is caused by
- the bacterial infection is caused by vancomycin-resistant Staphylococcus aureus (VRSA). In certain embodiments, the bacterial infection is caused by vancomycin-resistant Enterococci (VRE). In certain embodiments, the bacterial infection is caused by a methicillin-resistant (MR) organism. In certain embodiments, the bacterial infection is caused by methicillin-resistant S. aureus (MRSA). In certain embodiments, the bacterial infection is caused by methicillin-resistant Staphylococcus epidermidis (MRSE). In certain embodiments, the bacterial infection is caused by penicillin-resistant Streptococcus pneumonia. In certain embodiments, the bacterial infection is caused by quinolone-resistant Staphylococcus aureus (QRSA). In certain embodiments, the bacterial infection is caused by multi-drug resistant Mycobacterium tuberculosis.
- VRSA vancomycin-resistant Staphylococcus aureus
- VRE vancomycin-resistant Enterococci
- the bacterial infection is caused by
- the present invention provides methods of inhibiting the formation of biofilms comprising administering to a subject in need thereof a therapeutically effective amount of a compound capable of chelating a metal (e.g., compounds of any one of Fomulae (I-A)-(III-A)).
- a compound capable of chelating a metal e.g., compounds of any one of Fomulae (I-A)-(III-A)
- the present invention provides methods of inhibiting the formation of biofilms comprising administering to a subject in need thereof a
- the biofilms are produced by one or more microorganisms selected from the group consisting of bacteria, archaea, protozoa, fungi and algae.
- the biofilms are produced by bacteria.
- the biofilms are produced by Gram-negative bacteria.
- the biofilms are produced by microbial species such as S. epidermidis, E. faecalis, E. coli, P. mirabilis, P. aeruginosa, K. pneumoniae, S. aureus, S. viridans, K. oxytoca, S. saprophyticus, L.
- the biofilms are produced by Gram-positive bacteria.
- the bacterial infection is one or more infections selected from the group consisting of urinary tract infection, gastritis, respiratory infection, cystitis, pyelonephritis, osteomyelitis, bacteremia, skin infection, rosacea, acne, chronic wound infection, infectious kidney stones, bacterial endocarditis, and sinus infection.
- the infectious diseases is pneumonia, urinary tract infection, complicated intra- abdominal infection, or complicated skin/skin structure infection.
- the infectious diseases is nosocomial pneumonia, community-acquired pneumonia, urinary tract infection, complicated intra-abdominal infection, complicated skin/skin structure infection, infectious exacerbations of cystic fibrosis, sepsis, or melioidosis.
- the bacterial infection is respiratory infection. In certain embodiments, the bacterial infection is upper respiratory infection. In certain embodiments, the bacterial infection is pneumonia. In certain embodiments, the bacterial infection is bronchitis.
- a method for inhibiting bacterial cell growth comprising contacting bacteria with a compound capable of chelating a metal as described herein, or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition thereof.
- hypersusceptibility comprising contacting a bacterium with a compound capable of chelating a metal as described herein, or a pharmaceutically acceptable salt thereof, or a composition thereof.
- Hypersusceptibility refers to a condition of abnormal susceptibility to poisons, infective agents, or agents that are entirely innocuous in the normal individual.
- the bacterium/a is contacted with the compound in vitro. In certain embodiments, the bacterium/a is contacted with the compound in vivo. In certain embodiments, the bacterium is subsequently contacted with an antibiotic.
- the compound is administered with one or more additional therapeutically active agents.
- the additional therapeutically active agents are biocides.
- the biocides are antimicrobials.
- the antimicrobials are antibiotics.
- the compounds of Formulae (I-A)-(III-A) can be typically formulated in dosage unit form for ease of administration and uniformity of dosage. It will be understood, however, that the total daily dosage of the compositions of the present invention will be decided by an attending physician within the scope of sound medical judgment.
- the specific therapeutically effective dose level for any particular subject or organism will depend upon a variety of factors including the disease, disorder, or condition being treated and the severity of the disorder; the activity of the specific active ingredient employed; the specific composition employed; the age, body weight, general health, sex and diet of the subject; the time of administration, route of administration, and rate of excretion of the specific active ingredient employed; the duration of the treatment; drugs used in combination or coincidental with the specific active ingredient(s) employed; and like factors well known in the medical arts.
- the compound or pharmaceutical composition can be administered concurrently with, prior to, or subsequent to, one or more additional therapeutically active agents (e.g., antibiotics, anti-inflammatory agents).
- each agent will be administered at a dose and/or on a time schedule determined for that agent.
- the additional therapeutically active agent utilized in this combination can be administered together in a single composition or administered separately in different compositions.
- the particular combination to employ in a regimen will take into account compatibility of the inventive compound with the additional therapeutically active agent and/or the desired therapeutic effect to be achieved.
- additional therapeutically active agents utilized in combination be utilized at levels that do not exceed the levels at which they are utilized individually. In some embodiments, the levels utilized in
- the subject administered the chelating agent as provided herein or pharmaceutical composition is a mammal.
- the subject is a human.
- the subject is a patient diagnosed with cystic fibrosis.
- the subject is an immunocompromised subject.
- the subject is a domesticated animal, such as a dog, cat, cow, pig, horse, sheep, or goat.
- the subject is a companion animal such as a dog or cat.
- the subject is a livestock animal such as a cow, pig, horse, sheep, or goat.
- the subject is a zoo animal.
- the subject is an experimental animal such as a rodent or non-human primate.
- the present invention provides methods to treat or prevent biofilm formation comprising administering to a subject in need thereof a therapeutically effective amount of a compound capable of chelating a metal or pharmaceutical composition thereof as described herein.
- the provided method treats, cleans, or disinfects a wound by administering the compound or composition as described herein.
- the wounds are chronic wounds, acute wounds, surgical wounds, surgical sites, second and third degree burns, stasis ulcers, tropic lesions, decubitus ulcers, severe cuts, or abrasions.
- the present invention provides methods to treat or prevent biofilm formation comprising contacting an object with an effective amount of a compound capable of chelating a metal or the composition as described herein.
- the provided methods inhibit, reduce, or remove biofilms on an object.
- the provided method is to inhibit or remove the biofilm on the surface of the object.
- the surface is a hard, rigid surface.
- the surface is selected from the group consisting of a drainpipe, glaze ceramic, porcelain, glass, metal, wood, chrome, plastic, vinyl, and formica.
- the surface is a soft, flexible surface.
- the surface is selected from the group consisting of shower curtains or liners, upholstery, laundry, and carpeting.
- the surface is a food preparation surface, such as kitchen counters, cutting boards, sinks, stoves, refrigerator surfaces, or on sponges.
- the surface is a bathroom surface such as toilets, sinks, bathtubs, showers, and drains.
- the surface is a medical device surface.
- the contacting of the compound or composition as described herein with the object is carried out by wiping, sponging, or soaking, or laundering means.
- the provided method is used to prevent or remove biofilm as a dentifrice, a mouthwash, a compound for the treatment of dental caries, acne treatment, cleaning and disinfecting contact lenses, and medically implanted devices that are permanent such as an artificial heart valve or hip joint, and those that are not permanent such as indwelling catheters, pacemakers, surgical pins etc.
- the provided method is used to prevent or remove biofilm in situations involving bacterial infection of a host, either human or animal, for example in a topical dressing for burn patients. An example of such a situation would be the infection by P. aeruginosa of superficial wounds such as are found in burn patients or in the lung of a cystic fibrosis patient.
- the provided method can be used to control or prevent the development of biofilm in the process of manufacturing integrated circuits, circuit boards or other electronic or microelectronic devices.
- Metal chelators useful in the present invention are useful in the present invention.
- Compounds provided herein have been found capble of chelating metals, for example, iron. These metal chelators are in useful in treating or preventing diseases and conditions associated microbialn infections that re caused by pathogenic micobes typically requiring one or more metals (e.g., iron, calcium, magnesium, strontium, potassium, sodium, chromium, copper, manganese, molybdenum, zinc, and tungsten) to sustain life. Some of those compounds have been previously described in U.S.
- metals e.g., iron, calcium, magnesium, strontium, potassium, sodium, chromium, copper, manganese, molybdenum, zinc, and tungsten
- the compound used in the inventive methods, compositions, and kits is a compound of Formula (I-A):
- R 1 is hydrogen, optionally substituted alkyl, optionally substituted acyl, an oxygen
- each occurrence of R 3 is independently optionally substituted alkyl, optionally substituted arylalkyl, or–OR 8 ;
- R 4 , R 5 , and R 6 are each independently hydrogen or optionally substituted alkyl;
- R 7 is–OR 9 ,–SR 9 , or–N(R N1 ) 2 ;
- each instance of R N1 is independently hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, -OR O1 , or a nitrogen protecting group;
- R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group
- R 8 is hydrogen, optionally substituted alkyl, optionally substituted acyl, an oxygen
- R 9 is hydrogen, optionally substituted alkyl, ,
- R 10 is hydrogen, optionally substituted alkyl, optionally substituted acyl, or a nitrogen protecting group
- each instance of R′ is independently hydrogen, optionally substituted C 1-6 alkyl, optionally substituted acyl, or an oxygen protecting group;
- R′′ is hydrogen, optionally substituted alkyl, optionally substituted acyl, optionally substituted aryl, optionally substituted heteroaryl, an oxygen protecting group,
- R 1 , R 8 , R 9 , and R′′ is each occurrence of n is independently an integer from 1 to 8, inclusive; m is an integer from 0 to 1, inclusive;
- k is an integer from 0 to 4, inclusive
- x is an integer from 1 to 8, inclusive
- y is an integer from 0 to 8, inclusive.
- the metal chelator used in the inventive methods, compositions, and kits is a compound of Formula (II-A):
- R 1 is hydrogen, optionally substituted alkyl, optionally substituted acyl, an oxygen
- each occurrence of R 3 is independently optionally substituted alkyl, optionally substituted arylalkyl, or–OR 8 ;
- R 4 , R 5 , and R 6 are each independently hydrogen or optionally substituted alkyl, ;
- R 7 is–OR 9 ,–SR 9 , or–N(R N1 ) 2 ;
- each instance of R N1 is independently hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, -OR O1 , or a nitrogen protecting group;
- R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group
- R 8 is hydrogen, optionally substituted alkyl, optionally substituted acyl, an oxygen
- R 9 is hydrogen, optionally substituted alkyl
- an oxygen protecting group when attached to an oxygen atom or a sulfur protecting group when attached to a sulfur atom;
- R 10 is hydrogen, optionally substituted alkyl, optionally substituted acyl, or a nitrogen protecting group
- R′ is hydrogen or an oxygen protecting group
- R′′ is hydrogen, optionally substituted alkyl, optionally substituted acyl, optionally substituted aryl, optionally substituted heteroaryl, an oxygen protecting group,
- n is independently an integer from 1 to 8, inclusive;
- k1 is an integer from 0 to 3, inclusive, as valency permits;
- n1 is an integer from 0 to 3, inclusive, as valency permits;
- x is an integer from 1 to 8, inclusive
- y is an integer from 0 to 8, inclusive. [00117] In certain embodiments, at least one of R 1 and R 9 is or
- R 2 is–[(CH 2 ) n –O] x –[(CH 2 ) n –O] y –R′′ or–[(CH 2 ) n –O] x –[(CH 2 ) n –O] y –
- R 8 is and k is 1, 2, 3, or 4.
- R 1 is hydrogen, optionally substituted alkyl, optionally substituted acyl, or an oxygen protecting group;
- each occurrence of R 3 is independently optionally substituted alkyl, optionally substituted arylalkyl, or–OR 8 ;
- R 4 , R 5 , and R 6 are each independently hydrogen or optionally substituted alkyl
- R 7 is–OR 9 ,–SR 9 , or–N(R N1 ) 2 ;
- each instance of R N1 is independently hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, -OR O1 , or a nitrogen protecting group;
- R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group
- R 8 is hydrogen, optionally substituted alkyl, acyl, or an oxygen protecting group
- R 9 is hydrogen, optionally substituted alkyl, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom
- R 10 is hydrogen, optionally substituted alkyl, optionally substituted acyl, or a nitrogen protecting group
- R′ is hydrogen or an oxygen protecting group
- R′′ is hydrogen, optionally substituted alkyl, optionally substituted acyl, optionally substituted aryl, optionally substituted heteroaryl, or an oxygen protecting group;
- n is independently an integer from 1 to 8, inclusive;
- k is an integer from 0 to 4, inclusive
- x is an integer from 1 to 8, inclusive
- y is an integer from 0 to 8, inclusive.
- R 1 is hydrogen, optionally substituted
- alkyl optionally substituted acyl, an oxygen protecting group, , or
- R 1 is hydrogen. In certain embodiments, R 1 is optionally substituted alkyl. In certain embodiments, R 1 is optionally substituted C 1-6 alkyl. In certain embodiments, R 1 is unsubstituted C 1-6 alkyl. In certain embodiments, R 1 is methyl. In certain embodiments, R 1 is ethyl. In certain embodiments, R 1 is propyl. In certain
- R 1 is butyl. In certain embodiments, R 1 is optionally substituted acyl. In certain embodiments, R 1 is acetyl. In certain embodiments, R 1 is pivaloyl. In certain embodiments, R 1 is an oxygen protecting group. In certain embodiments, R 1 is silyl. In certain embodiments,
- R 1 is TBDPS, TBDMS, TIPS, TES, or TMS. In certain embodiments, R 1 is MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz. In certain embodiments, R 1 is In certain embodiments, R 1 is . In certain embodiments,
- R 1 is In certain embodiments, R 1 is In
- R 1 is . In certain embodiments, R 1 is
- R′ are oxygen protecting groups.
- R 1 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 1 is wherein all R' are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 1 is
- R 1 is . In certain embodiments, R 1 is . in certain embodiments, R 1 is . In certain embodiments, R 1 is . in certain embodiments, R 1 is . In certain embodiments, R 1 is . in certain embodiments, R 1 is
- R 1 is ; wherein all R' are oxygen protecting groups.
- R 1 is ; wherein all R' are oxygen protecting groups.
- R 1 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 1 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- Bn refers to–CH 2 Ph.
- R 2 is hydrogen.
- R 2 is optionally substituted alkyl.
- R 2 is C 1-12 alkyl optionally substituted with one or more substituents independently selected from the group consisting of hydroxyl, alkyloxy, and–CO 2 H.
- R 2 is– (CH 2 ) 2 –OH,–(CH 2 ) 3 –OH,–(CH 2 ) 4 –OH,–(CH 2 ) 5 –OH,–(CH 2 ) 6 –OH,–(CH 2 ) 7 –OH, or– (CH 2 ) 8 –OH.
- R 2 is–(CH 2 ) 2 –OCH 3 ,–(CH 2 ) 3 –OCH 3 ,–(CH 2 ) 4 –OCH 3 , –(CH 2 ) 5 –OCH 3 ,–(CH 2 ) 6 –OCH 3 ,–(CH 2 ) 7 –OCH 3 , or–(CH 2 ) 8 –OCH 3 .
- R 2 is–CH 2 –CO 2 H,–(CH 2 ) 2 –CO 2 H,–(CH 2 ) 3 –CO 2 H,–(CH 2 ) 4 –CO 2 H, or–(CH 2 ) 5 –CO 2 H.
- R 2 is C 1-12 alkyl substituted at least with–CO 2 R 31 , wherein R 31 is substituted or unsubstituted C 1-6 alkyl (e.g.,–CH 3 ).
- R 2 is–CH 2 – CO 2 R 31 ,–(CH 2 ) 2 –CO 2 R 31 ,–(CH 2 ) 3 –CO 2 R 31 ,–(CH 2 ) 4 –CO 2 R 31 , or–(CH 2 ) 5 –CO 2 R 31 .
- R 2 is optionally substituted C 1-6 alkyl.
- R 2 is unsubstituted C 1-6 alkyl.
- R 2 is methyl.
- R 2 is ethyl. In certain embodiments, R 2 is propyl. In certain embodiments, R 2 is butyl. In certain embodiments, R 2 is optionally substituted acyl. In certain embodiments, R 2 is acetyl. In certain embodiments, R 2 is pivaloyl. In certain embodiments, R 2 is an oxygen protecting group. In certain embodiments, R 2 is silyl. In certain embodiments, R 2 is TBDPS, TBDMS, TIPS, TES, or TMS. In certain embodiments, R 2 is MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is–[(CH 2 ) n –O] x –[(CH 2 ) n –O] y –R′′. In certain embodiments, R 2 is . In certain embodiments, R 2 is . In certain embodiments, R 2 is . In certain embodiments, R 2 is . In certain embodiments, R 2 is . In certain embodiments, R
- R 2 is . In certain embodiments, R 2 is
- R 2 is
- R 2 is , wherein R is optionally substituted aryl. In certain embodiments, R 2 is wherein R′′ is optionally substituted phenyl. In certain embodiments, R 2 is , wherein R′′ is optionally substituted phenyl. In certain embodiments,
- R′′ is of the formula:
- R 1 , R 3 , k, R 4 , R 5 , R 6 , and R 7 are as defined herein.
- R 2 is , wherein R′′ is of the formula: , wherein R 1 , R 4 , R 5 , R 6 , and R 7 are as defined herein.
- R 2 is , wherein R′′ is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is , wherein R′′ is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is , wherein R′′ is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is , wherein R′′ is of the formula: , wherein R 1 , R 6 , and R 7 are as defined herein.
- R 2 is , wherein R′′ is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is of the formula: In certain embodiments, R 2 is , wherein R′′ is optionally substituted heteroaryl. In certain embodiments, R 2 is , wherein R′′ is optionally substituted monocyclic heteroaryl. In certain embodiments, R 2 is , wherein R′′ is optionally substituted pyridinyl. In certain embodiments, R 2 is
- R′′ is of the formula:
- R 1 , R 3 , k, R 4 , R 5 , R 6 , and R 7 are as defined herein.
- R 2 is wherein R" is of the formula:
- R 1 , R 4 , R 5 , R 6 , and R 7 are as defined herein.
- R 2 is wherein R" is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is wherein R" is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is wherein R" is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is wherein R" is of the formula:
- R 1 , R 6 , and R 7 are as defined herein.
- R 2 is , wherein R′′ is of the formula: wherein R 1 , R 6 , and R 7 are as defined herein.
- R 2 is of the formula:
- R 2 is o . In certain embodiments, R 2 is or
- R 32 is substituted or unsubstituted C 1-6
- R 2 is . In certain embodiments, R
- R 2 is . In certain embodiments, R 2 is In certain embodiments, R 2 is In certain embodiments, R 2 is . In certain embodiments, R 2 is
- R 2 is ; wherein all R′ are oxygen protecting groups.
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is . In certain embodiments, R 2 is
- R 2 is In certain embodiments, R 2 is . In certain embodiments, R 2 is
- R 2 is
- R 2 is
- R′ are oxygen protecting groups.
- R 2 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is . In certain embodiments, R 2 is . In certain embodiments, R 2 is
- R 2 is
- R 2 is
- R 2 is In certain embodiments, R 2 is In certain embodiments, R 2 is In certain embodiments, R 2 is . In certain embodiments, R 2 is
- R 2 is
- R 2 is
- R 2 is ; wherein all R′ are oxygen protecting groups. In certain embodiments, R 2 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is .
- R 2 is .
- R 2 is In certain embodiments, R 2 is In certain
- R 2 is In certain embodiments,
- R 2 is In certain embodiments, R 2 is In certain embodiments, R 2 is
- R 2 is ; wherein all R′ are oxygen protecting groups. In certain embodiments, R 2 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 2 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 1 and all occurrences of R 2 are hydrogen.
- each occurrence of R 3 is independently optionally substituted alkyl, optionally substituted arylalkyl, or–OR 8 .
- R 3 is independently optionally substituted alkyl, optionally substituted arylalkyl, or–OR 8 .
- At least one occurrence of R 3 is optionally substituted alkyl. In certain embodiments, at least one occurrence of R 3 is optionally substituted C 1-6 alkyl. In certain embodiments, at least one occurrence of R 3 is methyl. In certain embodiments, at least one occurrence of R 3 is ethyl. In certain embodiments, at least one occurrence of R 3 is propyl. In certain embodiments, at least one occurrence of R 3 is butyl. In certain embodiments, at least one occurrence of R 3 is optionally substituted arylalkyl. In certain embodiments, at least one occurrence of R 3 is benzyl. In certain embodiments, at least one occurrence of R 3 is–OR 8 .
- R 3 is . In certain embodiments, at least one
- R 3 is In certain embodiments, at least one occurrence of
- R 3 is . In certain embodiments, at least one occurrence of R 3 is
- At least one occurrence of R 3 is In certain embodiments, at least one occurrence of R 3 is
- At least one occurrence of R 3 is wherein all R′ are oxygen protecting
- At least one occurrence of R 3 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz. In certain embodiments, at least one occurrence of R 3 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- at least one occurrence of R 3 is . In certain embodiments, at least one occurrence of R 3 is In certain embodiments, at least one occurrence of R 3 is
- At least one occurrence of R 3 is
- At least one occurrence of R 3 is
- At least one occurrence of R 3 is
- R′ are oxygen protecting groups.
- at least one occurrence of R 3 is ; wherein all R′ are oxygen protecting
- At least one occurrence of R 3 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz. In certain embodiments, at least one occurrence of R 3 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 4 is hydrogen or optionally substituted alkyl. In certain embodiments, R 4 is hydrogen. In certain embodiments, R 4 is optionally substituted alkyl. In certain embodiments, R 4 is optionally substituted C 1-6 alkyl. In certain embodiments, R 4 is unsubstituted C 1-6 alkyl. In certain embodiments, R 4 is methyl. In certain embodiments, R 4 is ethyl. In certain embodiments, R 4 is propyl. In certain embodiments, R 4 is butyl.
- R 5 is hydrogen or optionally substituted alkyl. In certain embodiments, R 5 is hydrogen. In certain embodiments, R 5 is optionally substituted alkyl. In certain embodiments, R 5 is optionally substituted C 1-6 alkyl. In certain embodiments, R 5 is unsubstituted C 1-6 alkyl. In certain embodiments, R 5 is methyl. In certain embodiments, R 5 is ethyl. In certain embodiments, R 5 is propyl. In certain embodiments, R 5 is butyl.
- R 4 and R 5 are each hydrogen. In certain embodiments, R 4 and R 5 are each independently optionally substituted alkyl. In certain embodiments, R 4 and R 5 are each independently optionally substituted C 1-6 alkyl. In certain embodiments, R 4 and R 5 are each independently unsubstituted C 1-6 alkyl. In certain embodiments, R 4 and R 5 are each methyl. In certain embodiments, R 4 and R 5 are each ethyl.
- R 6 is hydrogen or optionally substituted alkyl. In certain embodiments, R 6 is hydrogen. In certain embodiments, R 6 is optionally substituted alkyl. In certain embodiments, R 6 is optionally substituted C 1-6 alkyl. In certain embodiments, R 6 is unsubstituted C 1-6 alkyl. In certain embodiments, R 6 is methyl. In certain embodiments, R 6 is ethyl. In certain embodiments, R 6 is propyl. In certain embodiments, R 6 is butyl.
- R 4 and R 5 are each hydrogen; and R 6 is optionally substituted alkyl.
- R 4 and R 5 are each hydrogen; and R 6 is optionally substituted C 1-6 alkyl..
- R 4 and R 5 are each hydrogen; and R 6 is unsubstituted C 1-6 alkyl.
- R 4 and R 5 are each hydrogen; and R 6 is methyl.
- R 4 and R 5 are each hydrogen; and R 6 is ethyl.
- R 4 and R 5 are each hydrogen; and R 6 is propyl.
- R 4 and R 5 are each hydrogen; and R 6 is butyl.
- R 4 and R 5 are each optionally substituted alkyl; and R 6 is methyl.
- R 4 and R 5 are each optionally substituted C 1-6 alkyl; and R 6 is methyl.
- R 4 and R 5 are each methyl; and R 6 is methyl.
- R 4 and R 5 are each ethyl; and R 6 is methyl.
- R 4 and R 5 are each optionally substituted alkyl; and R 6 is hydrogen.
- R 4 and R 5 are each optionally substituted C 1-6 alkyl; and R 6 is hydrogen.
- R 4 and R 5 are each methyl; and R 6 is hydrogen.
- R 4 and R 5 are each ethyl; and R 6 is hydrogen.
- R 4 , R 5 , and R 6 are each hydrogen.
- R 7 is–OR 9 ,–SR 9 , or–N(R N1 ) 2 .
- R 7 is–N(R N1 ) 2, wherein each instance of R N1 is independently hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, -OR O1 , or a nitrogen protecting group; and R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group.
- R 7 is–N(R N1 ) 2 , wherein each instance of R N1 is independently hydrogen, optionally substituted alkyl, -OR O1 , or a nitrogen protecting group; and R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group.
- R 7 is– N(OR O1 )R N1 , wherein R N1 is hydrogen or optionally substituted alkyl; and R O1 is hydrogen or optionally substituted alkyl.
- R 7 is–N(OH)R N1 , wherein R N1 is hydrogen or optionally substituted alkyl.
- R 7 is–N(OH)CH 3 .
- R 7 is–OR 9 .
- R 7 is–OH.
- R 7 is–OH.
- R 7 is–O–alkyl. In certain embodiments, R 7 is–O–(C 1-6 alkyl). In certain embodiments, R 7 is–OMe. In certain embodiments, R 7 is–OEt. In certain embodiments, R 7
- R 7 is . In certain embodiments, R 7
- R 7 is In certain embodiments.
- R 7 is . In certain embodiments, R 7 is
- R 7 is wherein all R′
- R 7 is wherein all R′ are oxygen protecting groups. In certain embodiments, R 7 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl,
- R 7 is wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl,
- R 7 is . In certain embodiments, R 7 is
- R 7 is In certain embodiments, R 7 is In certain
- R 7 is . In certain embodiments, R 7 is
- R 7 is ; wherein all R′ are oxygen protecting groups. In certain embodiments, R 7 is ; wherein
- R 7 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl,
- R 7 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl,
- R 7 is . In certain embodiments, R 7 is
- R 7 is In certain embodiments, R 7 is In certain
- R 7 is . In certain embodiments, R 7 is In certain embodiments, R 7 is wherein all R′
- R 7 is ;
- R 7 is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl,
- R 7 is wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl,
- R 7 is . In certain embodiments, R 7 is
- R 7 is In certain embodiments, R 7 is . In certain embodiments, R 7 is
- R 7 is ; wherein all R′
- R 7 is ;
- R 7 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl,
- R 7 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 8 is hydrogen, optionally substituted
- alkyl optionally substituted acyl, an oxygen protecting group
- R 8 is hydrogen. In certain embodiments, R 8 is optionally substituted alkyl. In certain embodiments, R 8 is optionally substituted C 1-6 alkyl. In certain embodiments, R 8 is unsubstituted C 1-6 alkyl. In certain embodiments, R 8 is methyl. In certain embodiments, R 8 is ethyl. In certain embodiments, R 8 is propyl. In certain
- R 8 is butyl. In certain embodiments, R 8 is acyl. In certain embodiments, R 8 is acetyl. In certain embodiments, R 8 is pivaloyl. In certain embodiments, R 8 is an oxygen protecting group. In certain embodiments, R 8 is silyl. In certain embodiments, R 8 is TBDPS, TBDMS, TIPS, TES, or TMS. In certain embodiments, R 8 is MOM, THP, t-Bu, Bn, allyl,
- R 8 is In certain embodiments,
- R 8 is In certain embodiments, R 8 is In
- R 8 is In certain embodiments, R 8 is In certain embodiments, R 8 is ; wherein all R′ are
- R 8 is wherein all R′
- R 8 is wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl,
- R 8 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 8 is . In certain embodiments, R 8 is
- R 8 is In certain embodiments, R 8 is In certain embodiments, R 8 is In certain embodiments, R 8 is In certain embodiments, R 8 is In
- R 8 is ; wherein all R′ are oxygen protecting groups.
- R 8 is ; wherein all R′ are oxygen protecting
- R 8 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 8 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 9 is hydrogen, optionally substituted
- R 9 is hydrogen. In certain embodiments, R 9 is optionally substituted alkyl. In certain embodiments, R 9 is optionally substituted C 1-6 alkyl. In certain embodiments, R 9 is unsubstituted C 1-6 alkyl. In certain embodiments, R 9 is methyl. In certain embodiments, R 9 is ethyl. In certain embodiments, R 9 is propyl. In certain embodiments, R 9 is butyl. In certain
- R 9 is In certain embodiments, R 9 is
- R 9 is . In certain embodiments, R 9 is
- R 9 is In certain embodiments,
- R 9 is ; wherein all R′ are oxygen protecting groups.
- R 9 is ; wherein all R′ are oxygen protecting groups. In certain embodiments, R 9 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz. In certain
- R 9 is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz. In certain embodiments, R 9
- R 9 is .
- R 9 is In certain embodiments, R 9 is In
- R 9 is . In certain embodiments, R 9 is
- R 9 is ; wherein all R′ are oxygen protecting groups.
- R 9 is wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz. In certain embodiments, R 9 is
- R 9 is an oxygen protecting group when attached to an oxygen atom.
- R 9 when attached to an oxygen atom, R 9 is silyl.
- R 9 when attached to an oxygen atom, R 9 is TBDPS, TBDMS, TIPS, TES, or TMS.
- R 9 when attached to an oxygen atom, R 9 is MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 9 is a sulfur protecting group when attached to a sulfur atom. In certain embodiments, when attached to a sulfur atom, R 9 is acetamidomethyl, t-Bu, 3-nitro-2-pyridine sulfenyl, 2- pyridine-sulfenyl, or triphenylmethyl.
- R 10 is hydrogen, optionally substituted alkyl, optionally substituted acyl, or a nitrogen protecting group. In certain embodiments, R 10 is hydrogen. In certain embodiments, R 10 is optionally substituted alkyl. In certain
- R 10 is optionally substituted C 1-6 alkyl. In certain embodiments, R 10 is unsubstituted C 1-6 alkyl. In certain embodiments, R 10 is methyl. In certain embodiments, R 10 is ethyl. In certain embodiments, R 10 is propyl. In certain embodiments, R 10 is butyl. In certain embodiments, R 10 is optionally substituted acyl. In certain embodiments, R 10 is acetyl. In certain embodiments, R 10 is pivaloyl. In certain embodiments, R 10 is a nitrogen protecting group. In certain embodiments, R 10 is Bn, Boc, Cbz, Fmoc, trifluoroacetyl, triphenylmethyl, or Ts.
- each instance of R' is independently hydrogen, optionally substituted C 1-6 alkyl, optionally substituted acyl, or an oxygen protecting group.
- R' is optionally substituted C 1-6 alkyl, optionally substituted acyl, or an oxygen protecting group.
- all R' are hydrogen.
- all R' are oxygen protecting group.
- R' is silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- At least one R′ is hydrogen or an oxygen protecting group. In certain embodiments, at least one R′ is hydrogen. In certain embodiments, at least one R′ is an oxygen protecting group. In certain embodiments, at least one R′ is silyl. In certain embodiments, at least one R′ is TBDPS. In certain embodiments, at least one R′ is TBDMS. In certain embodiments, at least one R′ is TIPS. In certain embodiments,
- At least one R′ is TES. In certain embodiments, at least one R′ is TMS. In certain embodiments, at least one R′ is MOM. In certain embodiments, at least one R′ is THP. In certain embodiments, at least one R′ is t-Bu. In certain embodiments, at least one R′ is Bn. In certain embodiments, at least one R′ is allyl. In certain embodiments, at least one R′ is acetyl. In certain embodiments, at least one R′ is pivaloyl. In certain embodiments, at least one R′ is Bz. In certain embodiments, all R′ are hydrogen. In certain embodiments, all R′ are oxygen protecting groups. In certain embodiments, all R′ are silyl.
- all R′ are TBDPS. In certain embodiments, all R′ are TBDMS. In certain embodiments, all R′ are TIPS. In certain embodiments, all R′ are TES. In certain embodiments, all R′ are TMS. In certain embodiments, all R′ are MOM. In certain embodiments, all R′ are THP. In certain embodiments, all R′ are t-Bu. In certain embodiments, all R′ are Bn. In certain embodiments, all R′ are allyl. In certain embodiments, all R′ are acetyl. In certain embodiments, all R′ are pivaloyl. In certain embodiments, all R′ are Bz.
- R′′ is hydrogen, optionally substituted
- R′′ is hydrogen. In certain embodiments, R′′ is optionally substituted alkyl. In certain embodiments, R′′ is optionally substituted C 1-6 alkyl. In certain embodiments, R′′ is unsubstituted C 1-6 alkyl. In certain embodiments, R′′ is methyl. In certain embodiments, R′′ is substituted methyl. In certain embodiments, R′′ is–CH 2 –CO 2 H. In certain embodiments, R′′ is–CH 2 –CO 2 (substituted or unsubstituted C 1-6 alkyl) (e.g.,–CH 2 – CO 2 Me). In certain embodiments, R′′ is ethyl. In certain embodiments, R′′ is propyl. In certain embodiments, R′′ is butyl. In certain embodiments, R′′ is acyl. In certain
- R′′ is acetyl. In certain embodiments, R′′ is pivaloyl. In certain embodiments, R′′ is an oxygen protecting group. In certain embodiments, R′′ is silyl. In certain embodiments,
- R′′ is TBDPS, TBDMS, TIPS, TES, or TMS.
- R′′ is MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R′′ is
- R′′ is In certain embodiments, R′′ is In certain
- R′′ is In certain embodiments, R′′ is In
- R′′ is In certain embodiments, R′′ is ; wherein all R′ are oxygen protecting groups. In certain embodiments, R′′
- R′ are oxygen protecting groups.
- R′′ is ; wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R′′ is
- R′′ is silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R′′ is silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R′′ is .
- R′′ is In certain embodiments, R′′ is In certain embodiments, R′′ is In certain embodiments, R′′ is In certain embodiments, R′′ is
- R′′ are oxygen protecting groups.
- R′ are oxygen protecting groups.
- R′′ is wherein all R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R′′ is
- R′ are silyl, TBDPS, TBDMS, TIPS, TES, TMS, MOM, THP, t-Bu, Bn, allyl, acetyl, pivaloyl, or Bz.
- R 1 , R 8 , R 9 , and R′′ are , , or . In certain embodiments, at least two of R 1 , R 8 , R 9 , and R′′ are
- R 9 , and R′′ are , , , or
- At least three of R 1 , R 8 , R 9 , and R′′ are . In certain embodiments, at least three of R 1 , R 8 , R 9 , and R′′ are , , , or
- R 1 , R 8 , R 9 , and R′′ are each
- R 1 , R 8 , R 9 , and R′′ are
- each occurrence of n is independently an integer from 1 to 8, inclusive. In certain embodiments, at least one occurrence of n is 1. In certain embodiments, at least one occurrence of n is 2. In certain embodiments, at least one occurrence of n is 3. In certain embodiments, at least one occurrence of n is 4. In certain embodiments, at least one occurrence of n is 5. In certain embodiments, at least one occurrence of n is 6. In certain embodiments, at least one occurrence of n is 7. In certain embodiments, at least one occurrence of n is 8.
- m is an integer from 0 to 1, inclusive. In certain embodiments, m is 0. In certain embodiments, m is 1.
- k is an integer from 0 to 4, inclusive. In certain embodiments, k is 0. In certain embodiments, k is 1. In certain embodiments, k is 2. In certain embodiments, k is 3. In certain embodiments, k is 4. [00142] In compounds of Formula (II-A), k1 is an integer from 0 to 3, inclusive. In certain embodiments, k1 is 0. In certain embodiments, k1 is 1. In certain embodiments, k1 is 2. In certain embodiments, k1 is 3.
- x is an integer from 1 to 8, inclusive. In certain embodiments, x is 1. In certain embodiments, x is 2. In certain embodiments, x is 3. In certain embodiments, x is 4. In certain embodiments, x is 5. In certain embodiments, x is 6. In certain embodiments, x is 7. In certain embodiments, x is 8.
- y is an integer from 0 to 8, inclusive. In certain embodiments, y is 0. In certain embodiments, y is 1. In certain embodiments, y is 2. In certain embodiments, y is 3. In certain embodiments, y is 4. In certain embodiments, y is 5. In certain embodiments, y is 6. In certain embodiments, y is 7. In certain embodiments, y is 8.
- n is 2; x is 0; and y is 1. In certain embodiments, n is 2; x is 0; and y is 2. In certain embodiments, n is 2; x is 0; and y is 3. In certain embodiments, n is 2; x is 0; and y is 4.
- the compound of Formula (I-A) may have one or more chiral centers.
- the compound of Formula (I-A) is of Formula (I-B):
- the compound of Formula (I-A) is of the formula:
- the group–OR 2 of Formula (I-A) may be at any position, as valency permits, of the phenyl ring of Formula (I-A).
- m is 1,–OR 2 of Formula (I-A) is at the 3′-position of the phenyl ring of Formula (I-A), and thus the compound of Formula (I-A) is of Formula (I-C):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- m is 1, -OR 2 of Formula (I-A) is at the 4'-position of the phenyl ring of Formula ( -A), and the compound of Formula (I-A) is of Formula (I-D):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (E-1) or (E-2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-E-3) or (I-E-4):
- the compound of Formula (A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-X-1):
- the compound of Formula (I-A) is of the formula:
- the com ound of Formula I-A is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-F-1) or (I-F-2):
- the com ound of Formula I-A is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-F-3) or (I-F-4 :
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-G-1) or (I-G-2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-H-1) or (I-H-2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-I-1) or (I-I-2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-J-1) or (I- -2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-K-1) or (I-K-2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-L-1) or (I-L-2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-M-1) or (I-M-2):
- the com ound of Formula I-A is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of Formula (I-N-1) or (I-N-2):
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compound of Formula (I-A) is of the formula:
- the compounds of Formula (II-A) is of Formula (II-A-x):
- the compounds of Formula (II-A) is of one of the following formula
- the compounds of Formula (II-A) is of one of the following formula
- the compounds of Formula (II-A) is of one of the following formulae:
- the compounds of Formula (II- A) is of one of the following formula
- the compounds of Formula (II- A) is of one of the following formula
- the compounds of Formula (II-A) is of the following formula:
- the compounds of Formula (II-A) is of one of the following formulae:
- the compounds of Formula (II-A) is of one of the following formulae:
- the compounds of Formula (II-A) is of one of the following formulae:
- the compounds of Formula (II-A) is of one of the following formulae:
- the com ounds of Formula II-A) is of Formula (II-A-a):
- the group–OR 2 of Formula (II-A-a) may be at any position, as valency permits, of the pyridyl ring of Formula (II-A-a). In certain embodiments,–OR 2 of Formula (II-A-a) is at the 3′-position of the pyridyl ring of Formula (II-A-a), and the compound of Formula (II- A-a) is of Formula (II-C):
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of the formula:
- the com ound of Formula II-A is of the formula:
- the compound of Formula (II-A) is of Formula (II-E):
- the compound of Formula (II-A) is of Formula (II-F):
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of Formula (II-G):
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (II-A) is of Formula (II-H):
- the compound of Formula (II-A) is of the formula:
- the compound of Formula (A) is of the formula:
- the com ound of Formula A is of the formula:
- the compound of Formula (A) is of the formula:
- R 30 is H, substituted or unsubstituted C 1-6 alkyl (e.g.,–CH 3 ), or an oxygen protecting group; and a is 2, 3, 4, 5, 6, 7, 8, 9, or 10 (e.g., 4, 5, 6, 7, or 8).
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- b is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 (e.g. , 1, 2, 3, 4, or 5).
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- the com ound of Formula A is of the formula:
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is of the formula:
- the compound of Formula (A) is not of the formula:
- R 7 when R 7 is–OH, R 2 is not H or–(CH 2 CH 2 O) 2 CH 3 . In certain embodiments, when R 7 is–OH, R 2 is not H or–[(CH 2 ) n –O] x –[(CH 2 ) n –O] y –R′′. In certain embodiments, when R 7 is–OH,–OR 2 is attached to the 5′-position of the pyridinyl ring. [00271] In certain embodiments, the compounds useful in the inventive methods are of Formula (II-J):
- W 1 -W 3 are independently CR 22 , CHR 22 , NR 23 , oxygen, or sulfur, provided that: when W 3 is nitrogen, R 23 is null, and
- W 4 is CHR 22 , CR 22 , or NR 23 , as valency permits;
- Z is–OR 11 ,–NR 12 R 13 , morpholine, or optionally substituted piperazinyl;
- R 11 is–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 ,–[(CH 2 ) p –NH] u –[(CH 2 ) q –NR 14 ] v –R 15 , or– [(CH 2 ) p –O] u –[(CH 2 ) q –NR 14 ] v –R 15 ;
- R 12 is hydrogen, optionally substituted alkyl,–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 ,– [(CH 2 ) p – NH] u –[(CH 2 ) q –NR 14 ] v –R 15 , or–[(CH 2 ) p –O] u –[(CH 2 ) q –NR 14 ] v –R 15 ;
- R 13 is hydrogen or optionally substituted alkyl
- p and q are independently an integer from 1 to 8, inclusive;
- u is an integer from 0 to 8, inclusive
- v is an integer from 1 to 8, inclusive;
- R 14 and R 15 are independently hydrogen, optionally substituted alkyl, or optionally substituted acyl;
- R 16 is hydrogen, optionally substituted alkyl, or optionally substituted alkoxyl;
- R 17 is–OR 18 or–N(R N1 ) 2 ;
- each instance of R N1 is independently hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, -OR O1 , or a nitrogen protecting group;
- R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group
- R 18 is hydrogen, optionally substituted alkyl, or optionally substituted arylalkyl
- s is an integer from 1 to 8, inclusive;
- R 20 is optionally substituted alkyl
- R 21 is hydrogen or optionally substituted alkyl
- each occurrence of R 22 is independently null, hydrogen, or optionally substituted alkyl
- each occurrence of R 23 is independently null, hydrogen, or optionally substituted alkyl; or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof.
- the compounds useful in the inventive methods are of Formula (II-J), and pharmaceutically acceptable salts thereof, wherein:
- each one of W 1 , W 2 , and W 3 is independently CR 22 , CHR 22 , NR 23 , oxygen, or sulfur, provided that:
- W 4 is CHR 22 , CR 22 , or NR 23 , as valency permits;
- Z is–OR 11 ,–NR 12 R 13 , morpholine, or optionally substituted piperazinyl;
- R 11 is–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 ,–[(CH 2 ) p –NH] u –[(CH 2 ) q –NR 14 ] v –R 15 , or–
- R 12 is hydrogen, optionally substituted alkyl,–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 , etc
- R 13 is hydrogen or optionally substituted alkyl
- p and q are independently an integer from 1 to 8, inclusive;
- u is an integer from 0 to 8, inclusive
- v is an integer from 1 to 8, inclusive;
- R 14 and R 15 are independently hydrogen, optionally substituted alkyl, or optionally substituted acyl;
- R 16 is hydrogen, optionally substituted alkyl, or optionally substituted alkoxyl
- R 17 is–OR 18 or–N(R N1 ) 2 ;
- R N1 is independently hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, -OR O1 , or a nitrogen protecting group;
- R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group
- R 18 is hydrogen, optionally substituted alkyl, or optionally substituted arylalkyl
- R 21 is hydrogen or optionally substituted alkyl; each occurrence of R 22 is independently null, hydrogen, or optionally substituted alkyl; and
- each occurrence of R 23 is independently null, hydrogen, or optionally substituted alkyl.
- the compounds useful in the inventive methods are of Formula (II-J′):
- W 1 -W 3 are independently CR 22 , CHR 22 , NR 23 , oxygen, or sulfur, provided that:
- W 4 is CHR 22 , CR 22 , or NR 23 , as valency permits;
- Z is–OR 11 ,–NR 12 R 13 , morpholine, or optionally substituted piperazinyl;
- R 11 is–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 ,–[(CH 2 ) p –NH] u –[(CH 2 ) q –NR 14 ] v –R 15 , or–
- R 12 is hydrogen, optionally substituted alkyl,–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 , etc
- R 13 is hydrogen or optionally substituted alkyl
- p and q are independently an integer from 1 to 8, inclusive;
- u is an integer from 0 to 8, inclusive
- v is an integer from 1 to 8, inclusive;
- R 14 and R 15 are independently hydrogen, optionally substituted alkyl, or optionally substituted acyl;
- R 16 is hydrogen, optionally substituted alkyl, or optionally substituted alkoxyl
- R 17 is–OR 18 or–N(R N1 ) 2 ;
- R N1 is independently hydrogen, optionally substituted alkyl, optionally substituted carbocyclyl, optionally substituted aryl, optionally substituted heteroaryl, -OR O1 , or a nitrogen protecting group;
- R O1 is hydrogen, optionally substituted alkyl, or an oxygen protecting group
- R 18 is hydrogen, optionally substituted alkyl, or optionally substituted arylalkyl
- s is an integer from 1 to 8, inclusive;
- R 20 is optionally substituted alkyl
- R 21 is hydrogen or optionally substituted alkyl
- each occurrence of R 22 is independently null, hydrogen, or optionally substituted alkyl
- each occurrence of R 23 is independently null, hydrogen, or optionally substituted alkyl; or a pharmaceutically acceptable salt, tautomer, stereoisomer, solvate, hydrate, or polymorph thereof.
- Z is–OR 11 ,–NR 12 R 13 , optionally substituted heteroaryl, or optionally substituted heterocyclyl. In certain embodimetns, Z is– OR 11 ,–NR 12 R 13 , morpholine, or optionally substituted piperazinyl. In compounds of Formula (II-J), Z is–OR 11 ,–NR 12 R 13 , morpholine, or optionally substituted piperazinyl. In certain embodiments, Z is–OR 11 . In certain embodiments, Z is aboutO–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 .
- Z is In certain embodiments, Z is In certain embodiments, Z is In certain embodiments, Z is In certain embodiments, Z is In certain embodiments, Z is . In certain embodiments, Z is In certain embodiments, Z is . In certain embodiments, Z is In certain embodiments, Z is . In certain embodiments, Z is . In certain embodiments, Z is . In certain embodiments, Z is . In certain embodiments, Z is . In certain embodiments, Z is aboutO–[(CH 2 ) p – NH] u –[(CH 2 ) q –NR 14 ] v –R 15 . In certain embodiments, Z is–O–[(CH 2 ) p –O] u –[(CH 2 ) q –NR 14 ] v – R 15 . In certain embodiments, Z is–NR 12 R 13 . In certain embodiments, Z is morpholine.
- Z is unsubstituted piperazinyl. In certain embodiments, Z is substituted piperazinyl. In certain embodiments, Z is piperazinyl substituted at the 4-position with an optionally substituted alkyl. In certain embodiments, Z is 4-(2-hydroxyethyl)-piperazin-1-yl.
- R 11 is–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 , –[(CH 2 ) p –NH] u –[(CH 2 ) q –NR 14 ] v –R 15 , or–[(CH 2 ) p –O] u –[(CH 2 ) q –NR 14 ] v –R 15 .
- R 11 is–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 .
- R 11 is In certain embodiments, R 11 is In certain embodiments, R 11 is In certain embodiments, R 11 is . In certain embodiments, R 11 is . In certain embodiments, R 11 is . In certain embodiments, R 11 is In certain embodiments, R 11 is In certain embodiments, R 11 is In certain embodiments, R 11 is R 11 is R 11 is about[(CH 2 ) p – NH] u –[(CH 2 ) q –NR 14 ] v –R 15 . In certain embodiments, R 11 is–[(CH 2 ) p –O] u –[(CH 2 ) q –NR 14 ] v – R 15 .
- R 12 is hydrogen, optionally substituted alkyl,–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 ,–[(CH 2 ) p – NH] u –[(CH 2 ) q –NR 14 ] v –R 15 , or–[(CH 2 ) p – O] u –[(CH 2 ) q –NR 14 ] v –R 15 .
- R 12 is hydrogen.
- R 12 is optionally substituted alkyl.
- R 12 is optionally substituted C 1-6 alkyl. In certain embodiments, R 12 is unsubstituted C 1-6 alkyl. In certain embodiments, R 12 is methyl. In certain embodiments, R 12 is ethyl. In certain embodiments, R 12 is propyl. In certain embodiments, R 12 is butyl. In certain embodiments, R 12 is–[(CH 2 ) p –O] u –[(CH 2 ) q –O] v –R 14 . In certain embodiments, R 12 is In certain embodiments, R 12 is . In certain embodiments, R 12 is In certain embodiments, R 12 is . In certain embodiments, R 12 is . In certain embodiments, R 12 is . In certain embodiments, R 12 is .
- R 12 is In certain embodiments, R 12 is In certain embodiments, R 12 is In certain embodiments, R 12 is In certain embodiments, R 12 is about[(CH 2 ) p – NH] u –[(CH 2 ) q –NR 14 ] v –R 15 . In certain embodiments, R 12 is– [(CH 2 ) p –O] u –[(CH 2 ) q –NR 14 ] v –R 15 .
- R 13 is hydrogen or optionally substituted alkyl. In certain embodiments, R 13 is hydrogen. In certain embodiments, R 13 is optionally substituted alkyl. In certain embodiments, R 13 is optionally substituted C 1-6 alkyl. In certain embodiments, R 13 is unsubstituted C 1-6 alkyl. In certain embodiments, R 13 is methyl. In certain embodiments, R 13 is ethyl. In certain embodiments, R 13 is propyl. In certain embodiments, R 13 is butyl.
- p is an integer from 1 to 8, inclusive. In certain embodiments, p is 1. In certain embodiments, p is 2. In certain embodiments, p is 3. In certain embodiments, p is 4. In certain embodiments, p is 5. In certain embodiments, p is 6. In certain embodiments, p is 7. In certain embodiments, p is 8.
- q is an integer from 1 to 8, inclusive. In certain embodiments, q is 1. In certain embodiments, q is 2. In certain embodiments, q is 3. In certain embodiments, q is 4. In certain embodiments, q is 5. In certain embodiments, q is 6. In certain embodiments, q is 7. In certain embodiments, q is 8.
- u is an integer from 0 to 8, inclusive. In certain embodiments, u is 0. In certain embodiments, u is 1. In certain embodiments, u is 2. In certain embodiments, u is 3. In certain embodiments, u is 4. In certain embodiments, u is 5. In certain embodiments, u is 6. In certain embodiments, u is 7. In certain embodiments, u is 8.
- v is an integer from 1 to 8, inclusive. In certain embodiments, v is 1. In certain embodiments, v is 2. In certain embodiments, v is 3. In certain embodiments, v is 4. In certain embodiments, v is 5. In certain embodiments, v is 6. In certain embodiments, v is 7. In certain embodiments, v is 8.
- R 14 is hydrogen, optionally substituted alkyl, or optionally substituted acyl. In certain embodiments, R 14 is hydrogen. In certain embodiments, R 14 is optionally substituted alkyl. In certain embodiments, R 14 is optionally substituted C 1-6 alkyl. In certain embodiments, R 14 is unsubstituted C 1-6 alkyl. In certain embodiments, R 14 is methyl. In certain embodiments, R 14 is ethyl. In certain embodiments, R 14 is propyl. In certain embodiments, R 14 is butyl. In certain embodiments, R 14 is acyl. In certain embodiments, R 14 is acetyl.
- R 15 is hydrogen, optionally substituted alkyl, or optionally substituted acyl. In certain embodiments, R 15 is hydrogen. In certain embodiments, R 15 is optionally substituted alkyl. In certain embodiments, R 15 is optionally substituted C 1-6 alkyl. In certain embodiments, R 15 is unsubstituted C 1-6 alkyl. In certain embodiments, R 15 is methyl. In certain embodiments, R 15 is ethyl. In certain embodiments, R 15 is propyl. In certain embodiments, R 15 is butyl. In certain embodiments, R 15 is optionally substituted acyl. In certain embodiments, R 15 is acetyl.
- R 16 is hydrogen, optionally substituted alkyl, or optionally substituted alkoxyl. In certain embodiments, R 16 is hydrogen. In certain embodiments, R 16 is optionally substituted alkyl. In certain embodiments, R 16 is optionally substituted C 1-6 alkyl. In certain embodiments, R 16 is unsubstituted C 1-6 alkyl. In certain embodiments, R 16 is methyl. In certain embodiments, R 16 is ethyl. In certain embodiments, R 16 is propyl. In certain embodiments, R 16 is butyl. In certain embodiments, R 16 is optionally substituted alkoxyl.
- R 16 is C 1-6 alkoxyl. In certain embodiments, R 16 is methoxyl. In certain embodiments, R 16 is ethoxyl. In certain embodiments, R 16 is propoxyl. In certain embodiments, R 16 is butoxyl.
- R 17 is–OR 18 or–N(R N1 ) 2 . In certain embodiments, R 17 is–OR 18 . In certain embodiments, R 17 is–OH. In certain embodiments, R 17 is–O–alkyl. In certain embodiments, R 17 is–O–(C 1-6 alkyl). In certain embodiments, R 17 is– OMe. In certain embodiments, R 17 is–OEt. In certain embodiments, R 17 is–OPr. In certain embodiments, R 17 is–OBu. In certain embodiments, R 17 is–O–arylalkyl. In certain embodiments, R 17 is–O–phenalkyl. In certain embodiments, R 17 is–O–Bn.
- R 18 is hydrogen, optionally substituted alkyl, or optionally substituted arylalkyl. In certain embodiments, R 18 is hydrogen. In certain embodiments, R 18 is optionally substituted alkyl. In certain embodiments, R 18 is optionally substituted C 1-6 alkyl. In certain embodiments, R 18 is unsubstituted C 1-6 alkyl. In certain embodiments, R 18 is methyl. In certain embodiments, R 18 is ethyl. In certain embodiments, R 18 is propyl. In certain embodiments, R 18 is butyl. In certain embodiments, R 18 is arylalkyl.
- R 18 is aryl–(C 1-6 alkyl). In certain embodiments, R 18 is phenyl–(C 1-6 alkyl). In certain embodiments, R 18 is Bn. In certain embodiments, R 18 is phenethyl.
- R 19 is alkyl or–(CH 2 ) s –
- R 19 is optionally substituted alkyl.
- s is an integer from 1 to 8, consistise. In certain embodiments, s is 1. In certain embodiments, s is 2. In certain embodiments, s is 3. In certain embodiments, s is 4. In certain embodiments, s is 5. In certain embodiments, s is 6. In certain embodiments, s is 7. In certain embodiments, s is 8.
- R 20 is optionally substituted alkyl. In certain embodiments, R 20 is optionally substituted C 1-6 alkyl. In certain embodiments, R 20 is unsubstituted C 1-6 alkyl. In certain embodiments, R 20 is methyl. In certain embodiments, R 20 is ethyl. In certain embodiments, R 20 is propyl. In certain embodiments, R 20 is butyl.
- R 21 is hydrogen or optionally substituted alkyl. In certain embodiments, R 21 is hydrogen. In certain embodiments, R 21 is optionally substituted alkyl. In certain embodiments, R 21 is optionally substituted C 1-6 alkyl. In certain embodiments, R 21 is unsubstituted C 1-6 alkyl. In certain embodiments, R 21 is methyl. In certain embodiments, R 21 is ethyl. In certain embodiments, R 21 is propyl. In certain embodiments, R 21 is butyl.
- At least one R 22 is null. In certain embodiments, at least one R 22 is hydrogen. In certain embodiments, at least one R 22 is optionally substituted alkyl. In certain embodiments, at least one R 22 is optionally substituted C 1-6 alkyl. In certain embodiments, at least one R 22 is unsubstituted C 1-6 alkyl. In certain embodiments, at least one R 22 is methyl. In certain embodiments, at least one R 22 is ethyl. In certain embodiments, at least one R 22 is propyl. In certain embodiments, at least one R 22 is butyl.
- At least one R 23 is null. In certain embodiments, at least one R 23 is hydrogen. In certain embodiments, at least one R 23 is optionally substituted alkyl. In certain embodiments, at least one R 23 is optionally substituted C 1-6 alkyl. In certain embodiments, at least one R 23 is unsubstituted C 1-6 alkyl. In certain embodiments, at least one R 23 is methyl. In certain embodiments, at least one R 23 is ethyl. In certain embodiments, at least one R 23 is propyl. In certain embodiments, at least one R 23 is butyl. [00295] In certain embodiments, the compound of Formula (II-J) is of the formula:
- the compound of Formula (II-J) is of the formula:
- the compound of Formula (II-J) may have one or more chiral centers.
- the compound of Formula (II-J) is of Formula (II-K):
- the compound of Formula (II-J) is of the formula:
- the compound of Formula (II-J) is of the formula:
- the compound of Formula (II-J) is of the formula:
- the compound of Formula (II-J) is of the formula:
- the compound of Formula (II-J) is of the formula:
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention concerne des méthodes utilisant un composé apte à chélater un métal (par exemple du fer) pour traiter et/ou prévenir des maladies infectieuses. En particulier, les chélateurs de métaux sont des analogues de la desferrithiocine, des analogues de la désaza-desfemthiocine, et les analogues de l'HBED de Formule (I-A)-(III-A). L'invention concerne également des méthodes utilisables pour inhiber la formation de biofilm. Les méthodes de l'invention comprennent également des traitements d'association comprenant un chélateur de métal et un autre agent thérapeutique (par exemple un antibiotique). Les maladies infectieuses et/ou la formation de biofilm peuvent survenir chez un sujet chez qui a été diagnostiquée une mucoviscidose.
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US201562138862P | 2015-03-26 | 2015-03-26 | |
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WO2016154547A1 true WO2016154547A1 (fr) | 2016-09-29 |
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Cited By (2)
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WO2019118311A1 (fr) * | 2017-12-13 | 2019-06-20 | Merck Sharp & Dohme Corp. | Compositions pharmaceutiques de tedizolid phosphate |
CN109999031A (zh) * | 2019-04-16 | 2019-07-12 | 周锡明 | 一种含有苯唑西林的医药组合物 |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2019118311A1 (fr) * | 2017-12-13 | 2019-06-20 | Merck Sharp & Dohme Corp. | Compositions pharmaceutiques de tedizolid phosphate |
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CN109999031A (zh) * | 2019-04-16 | 2019-07-12 | 周锡明 | 一种含有苯唑西林的医药组合物 |
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