C-halogen bond formation
AssigneeThe Trustees of Princeton University
InventorsJohn T. Groves, Wei Liu, Xiongyi Huang
Life of this patent
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Abstract
Methods of halogenating a carbon containing compound having an sp3 C—H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond are provided. The halogenated products of the methods are provided.
Claims24
A composition comprising a product of a method direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond including combining the carbon containing compound, a fluorinating agent, a fluorinating catalyst, and an oxidant.
A composition comprising at least one compound selected from the group consisting of fluoro-ibuprofen or the methyl ester thereof, fluoro-rasagiline, fluoro-nabumetone, fluoro-celestolide, fluoro-celecoxib analog, fluoro-papaverine, fluoro-protected enalaprilat, fluoro-protected fingolimod, fluoro-protected dopamine, fluoro-N-Boc-cinacalcet, fluoro-JNJ41510417, fluoro-5-OH-FPPAT, fluoro-FEP, fluoro-Acl703. fluoro-BMIPP, fluoro-HAR, fluoro-flutemetamol, fluoro-MK-9470, fluoro-FACPC, fluoro-CURB, fluoro-MFES, FES, fluoro-2-ME, fluoro-PHNO, fluoro-PHNO, fluoro-fallypride, DMFP, fluoro-5-OH-FPPAT, fluoro-5-OH-DPAT, fluoro-NPA, fluoro-NNC112, fluoro-SCH, fluoro-FDA, fluoro-MNPA, fluoro-MC113, fluoro-SA4503, fluoro-SA6298, fluoro-BMS-747158-01, fluoro-PBR28, fluoro-PBR06, fluoro-FMPEP, fluoro-MePPEP, fluoro-FBzBMS, fluoro-FBFPA, fluoro-FEPPA, fluoro-telmisartan, fluoro-tacrine, fluoro-desloratadine, fluoro-etodolac, fluoro-cinacalcet, fluoro-tanshinone IIA, fluoro-indomethacin, fluoro-trimethoprim, fluoro-masoprocol, fluoro-dubutamine, fluoro-duloxetine, fluoro-ondansetron, and fluoro-benzbromarone, or pharmaceutically acceptable salts or solvates thereof.
A method of treatment comprising administering a fluorinated derivative of a drug to a subject in need thereof, wherein the fluorinated derivative is a product of a method direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond including combining the carbon containing compound, a fluorinating agent, a fluorinating catalyst, and an oxidant, and the carbon containing compound is the drug.
A composition comprising at least one 19-F containing compound selected from the group consisting of
- or pharmaceutically acceptable salts or solvates thereof.
A method of treatment comprising administering to a subject in need thereof a compound selected from the group consisting of fluoro-ibuprofen or the methyl ester thereof, fluoro-rasagiline, fluoro-nabumetone, fluoro-celecoxib analog, fluoro-papaverine, fluoro-protected enalaprilat, fluoro-protected fingolimod, fluoro-protected dopamine, fluoro-N-Boc-cinacalcet, fluoro-JNJ41510417, fluoro-5-OH-FPPAT, fluoro-FEP, fluoro-Acl703. fluoro-BMIPP, fluoro-HAR, fluoro-flutemetamol, fluoro-MK-9470, fluoro-FACPC, fluoro-CURB, fluoro-MFES, FES, fluoro-2-ME, fluoro-PHNO, fluoro-PHNO, fluoro-fallypride, DMFP, fluoro-5-OH-FPPAT, fluoro-5-OH-DPAT, fluoro-NPA, fluoro-NNC112, fluoro-SCH, fluoro-FDA, fluoro-MNPA, fluoro-MC113, fluoro-SA4503, fluoro-SA6298, fluoro-BMS-747158-01, fluoro-PBR28, fluoro-PBR06, fluoro-FMPEP, fluoro-MePPEP, fluoro-FBzBMS, fluoro-FBFPA, fluoro-FEPPA, fluoro-telmisartan, fluoro-tacrine, fluoro-desloratadine, fluoro-etodolac, fluoro-cinacalcet, fluoro-tanshinone IIA, fluoro-indomethacin, fluoro-trimethoprim, fluoro-masoprocol, fluoro-dubutamine, fluoro-duloxetine, fluoro-ondansetron, and fluoro-benzbromarone, or pharmaceutically acceptable salts or solvates thereof.
Dependencies are inferred from the claim text.