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US 2022/0024899 A1Published application
Bi-functional nanohybrids
AssigneeSon Corporation
InventorsRichard DECREAU, Pierre-Emmanuel DOULAIN, Jérémy PARIS
Life of this patent
Estimating the term…
Abstract
Bi-functional nanohybrids including a nanoparticle to the surface of which are covalently coupled chemical functions, one of which being biorthogonal, and their use as support for catalysts.
Claims8
A bi-functional nanohybrid comprising a nanoparticle to the surface of which are covalently coupled one or more, identical or different, groups selected from:
- either a group of formula (1) or (1′)
- where
- Ra represents a bioorthogonal function selected from:
- 1,2,4-triazines of formula (al)
- wherein
- R3 is a hydrogen atom and is in position 5 of the said 1,2,4-triazine
- R1 is selected from
- R2 is selected from:
- a hydrogen atom
- a bromine atom, a fluorine atom
- a —CF3 group, a —CN group
- a phenyl group optionally mono- or poly- substituted by a fluorine atom, —OCH3 group, —CF3 group, —NO2 group
- R1 and R2 being independently either in position 3 or 6 of said 1,2,4-triazine;
- 1,2,4,5-tetrazines of formula (b1)
- wherein
- R5 is selected from:
- an oxygen atom, a sulphur atom
- a —NRp— group with Rp being a hydrogen atom or a (C1-C4)alkyl group
- one of the following groups
- R6 is selected from:
- a hydrogen atom,
- a chlorine atom,
- a methyl group,
- a —OR or —SR group with R being a (C1-C4)alkyl group,
- —N(CH3)2 and
- a phenyl group optionally mono- or poly- substituted with a fluorine atom, —OCH3 group, —CF3 group, —NO2 group,
- Rb represents
- an halogen atom,
- a —ORc or —SRc group with Rc being a hydrogen atom,
- a —COORc group with Rc being a hydrogen atom,
- a —NRnRz with Rn and Rz being independently from each other a hydrogen atom, a (C1-C4)alkyl group, a phenyl group or a pyridinyl group
- an azide group,
- a maleimidyl group,
- a (C1-C4)alkynyl group,
- an imidazolyl group,
- a pyridinyl group,
- a 1,2,4-triazine of formula (a2), when Ra is a 1,2,4,5-tetrazine of formula (bi)
- with R8 being either in position 3 or 6 of said 1,2,4-triazine of formula (a2) is selected from
- a 1,2,4,5-tetrazine of formula (b2), when Ra is a 1,2,4-triazine of formula (a1)
- with R9 selected from:
- an oxygen atom, a sulphur atom and
- a —NH— group
- and with R10 selected from:
- a chlorine atom
- —OCH3 and —SCH3 and
- —N(CH3)2
- X1, X2 and X3, same or different, may be absent or when present when present represent a spacer selected from (C1-C6)alkyl groups;
- said groups may comprise one or more oxygen atoms and/or one or more groups
- with s, t and u, same or different being integers between 0 and 10,
- Z represents an C6-aryl group or a 5-6-membered N-heteroaryl group that is at least tri-substituted by substituents allowing the attachment to X1, X2, and X3 respectively,
- either a group of formula (2)
- where
- Rai represents a bioorthogonal function selected from:
- 1,2,4-triazine of formula (el)
- wherein
- R1 is selected from
- and R3 is a hydrogen atom and is in position 5 of the said 1,2,4-triazine
- R4 is selected from
- R1and R4 being independently either in position 3 or 6 of said 1,2,4-triazine
- R1 and R4 being the same or different;
- 1,2,4,5-tetrazine of formula (f1)
- wherein
- R5 is selected from:
- an oxygen atom, a sulphur atom
- a —NRp— group with Rp being a hydrogen atom or a (C1-C4)alkyl group
- one of the following groups
- R7 may be absent or when present is selected from:
- an oxygen atom, a sulphur atom
- a —NRp— group with Rp being a hydrogen atom or a (C1-C4)alkyl group
- one of the following groups
- R5 and R7 being the same or different;
- Rb, X1 and X2 are as defined above
- with the proviso that Ra and Rb are mutually compatible and that the ratio between Ra and Rb or between Ra1 and Rb is equal to 1/1.
70 more elements
A compound of formulas (Ia), (Ib), (Ic), (Id) or (Ie)
- wherein
- Ra represents a 1,2,4-triazine of formula (a1)
- or a 1,2,4,5-tetrazine of formula (b1),
- Rb represents
- an halogen atom,
- a —ORc or —SRc group with Rc being a hydrogen atom,
- a —COORc group with Rc being a hydrogen atom,
- a —NRnRz with Rn and Rz being independently from each other a hydrogen atom, a (C1-C4)alkyl group, a a phenyl group or a pyridyl group,
- an azide group,
- a maleimidyl group,
- a (C1-C4)alkynyl group,
- an imidazolyl group,
- a pyridinyl group,
- a 1,2,4-triazine of formula (a2), when Ra is a 1,2,4,5-tetrazine of formula (b1)
- with R8 being either in position 3 or 6 of said 1,2,4-triazine of formula (a2) is selected from
- a 1,2,4,5-tetrazine of formula (b2), when Ra is a 1,2,4-triazine of formula (a1)
- with R9 selected from:
- an oxygen atom, a sulphur atom and
- a —NH— group
- and with R10 selected from:
- a chlorine atom
- —OCH3 and —SCH3 and
- —N(CH3)2,
- s1, t1, u1, s2, t2 and u2 same or different are integers between 0 and 10,
21 more elements
A compound of formula (II)
- Y-X1-Ra1-X2-Rb
- wherein Ra1 is a 1,2,4-triazine corresponds to formula (e1)
- and corresponding to formula (IIa)
- wherein
- Y represents
- either a chlorine, bromine, iodine atoms
- either a —COOH group,
- either a maleimidyl group,
- either a —OH, —SH or —NH2 group
- R1 is selected from
- R3 is a hydrogen atom and is in position 5 of the said 1,2,4-triazine
- R4 is selected from
- R1 and R4 being independently either in position 3 or 6 of said 1,2,4-triazine
- R1 and R4 being the same or different
- Rb represents
- an halogen atom,
- a —ORc or —SRc group with Rm being a hydrogen atom,
- a —COORc group with Rm being a hydrogen atom,
- a —NRnRz with Rn and Roz being independently from each other a hydrogen atom, a (C1-C4)alkyl group, a phenyl group or a pyridinyl group
- an azide group,
- a maleimidyl group,
- a (C1-C4)alkynyl group,
- an imidazolyl group,
- a pyridinyl group,
- a 1,2,4-triazine of formula (a2), when Ra is a 1,2,4,5-tetrazine of formula (b1)
- with R8 being either in position 3 or 6 of said 1,2,4-triazine of formula (a2) is selected from
- a 1,2,4,5-tetrazine of formula (b2), when Ra is a 1,2,4-triazine of formula (al)
- with R9 selected from:
- an oxygen atom, a sulphur atom and
- a —NH— group
- and with R10 selected from:
- a chlorine atom
- —OCH3 and —SCH3 and
- —N(CH3)2, and
- s1, t1, u1, s2, t2 and u2 same or different are integers between 0 and 10.
32 more elements
A compound of formula (II)
- Y-X1-Ra1-X2-Rb
- wherein Ra1 is a 1,2,4,5-tetrazine corresponds to formula (f1)
- and corresponding to formula (IIb)
- wherein
- Y represents
- either a chlorine, bromine, iodine atoms
- either a —COOH group,
- either a maleimidyl group,
- either a —OH, —SH or —NH2 group R5 is selected from:
- an oxygen atom, a sulphur atom
- a —NRp- group with Rp being a hydrogen atom or a (C1-C4)alkyl group
- one of the following groups
- R7 may be absent or when present is selected from:
- an oxygen atom, a sulphur atom
- a —NRp- group with Rp being a hydrogen atom or a (C1-C4)alkyl group
- one of the following groups
- R5 and R7 being the same or different
- Rb represents
- an halogen atom,
- a —ORc or —SRc group with Rc being a hydrogen atom,
- a —COORc group with Rc being a hydrogen atom,
- a —NRnRz with Rn and Rz being independently from each other a hydrogen atom, a (C1-C4)alkyl group, a (C3-C6)cycloalkyl group, a phenyl group or a pyridyl group,
- an azide group,
- a maleimidyl group,
- a (C1-C4)alkynyl group,
- an imidazolyl group,
- a pyridinyl group,
- a 1,2,4-triazine of formula (a2), when Ra is a 1,2,4,5-tetrazine of formula (b1)
- with R8 being either in position 3 or 6 of said 1,2,4-triazine of formula (a2) is selected from
- a 1,2,4,5-tetrazine of formula (b2), when Ra is a 1,2,4-triazine of formula (a1)
- with R9 selected from:
- an oxygen atom, a sulphur atom and
- a —NH— group
- and with R10 selected from:
- a chlorine atom
- —OCH3 and —SCH3 and
- —N(CH3)2, and
- s1, t1, u1, s2, t2 and u2 same or different being integers between 0 and 10.
35 more elements
Dependencies are inferred from the claim text.