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US 2019/0367736 A1Published application
Deuterated fluorophores
AssigneeHoward Hughes Medical Institute
InventorsLuke Lavis, Jonathan B. Grimm
Life of this patent
Estimating the term…
Abstract
The present invention is generally directed to the synthesis and use of fluorophores. It is more specifically directed to the synthesis and use of deuterated fluorophores. In one case, the present invention provides a compound of the structure shown in FIG. 44.
Claims10
A compound of the following structure:
- wherein
- R1 is independently selected from halogen, H, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), N3, NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl, aryl and substituted aryl, alkenyl and substituted alkenyl, or where the R1 substituents, taken together with the carbon atoms to which they are bonded, form a substituted or unsubstituted cycloalkyl or cycloalkenyl ring containing 3, 4, 5, 6, 7, 8, or 9 carbon atoms;
- R1′ is independently selected from halogen, H, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), N3, NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl, aryl and substituted aryl, alkenyl and substituted alkenyl, and only one of R1 and R1′ can be D when X is CF3, and only one of R1 and R1′ can be CD3 when Q is O;
- R2, R3 and R4 are independently selected from H, halogen, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), N3, NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl, aryl and substituted aryl, alkenyl and substituted alkenyl;
- Q is selected from C(alkyl), C(alkyl)2, N(alkyl), O, S, Si(alkyl)2, SO2, P(O)(alkyl), P(O)(aryl), PO2H, and Se;
- W is selected from C and N;
- X is selected from H, D, alkyl, substituted alkyl, aryl, substituted aryl, alkenyl, substituted alkenyl, halogen, CN, O, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), N3, NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H;
- Y is selected from H, D, C(alkyl), C(aryl), C(alkenyl), C(alkyl)2, N(alkyl), N(alkyl)2, N(aryl), N(aryl)2, O and S;
- Z is selected from H, D, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), N3, NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl, aryl and substituted aryl, alkenyl and substituted alkenyl, or Z and Y, taken together with the carbon atoms to which they are bonded, form a substituted or unsubstituted cycloalkyl or cycloalkenyl ring containing 4, 5, 6, 7 or 8 ring carbon atoms, or Z and Y, taken together with the carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring.
6 more elements
A compound of the following structure:
- wherein
- R1 is independently selected from halogen, H, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl or where the R1 substituents, taken together with the carbon atoms to which they are bonded, form a substituted or unsubstituted cycloalkyl ring containing 3, 4, 5, 6, 7, 8, or 9 carbon atoms;
- R1′ is independently selected from halogen, H, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl, and only one of R1 and R1′ can be D when X is CF3, and only one of R1 and R1′ can be CD3;
- R2, R3 and R4 are independently selected from H, halogen, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, NH(alkyl), N(alkyl)2, NH(aryl), NH(aryl)2, NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), C(O)NH(alkyl), C(O)NH(aryl), PO3H2, SO3H, alkyl and substituted alkyl;
- Q is selected from C(alkyl)2, N(alkyl), O, S, Si(alkyl)2, SO2, P(O)(aryl) and Se;
- W is selected from C and N;
- X is selected from H, alkyl, substituted alkyl, aryl, substituted aryl, halogen, CN, OH, O(alkyl), SH, S(alkyl), S(aryl), NH2, N(alkyl), N(aryl), NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H;
- Y is selected from H, C(alkyl)2, N(alkyl), N(alkyl)2, O and S;
- Z is selected from H, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), NH2, N(alkyl), N(aryl), NO2, CHO, C(O)(alkyl), C(O)(aryl), COOH, COO(alkyl), COO(aryl), PO3H2, SO3H, alkyl, and substituted alkyl or Z and Y, taken together with the carbon atoms to which they are bonded, form a substituted or unsubstituted cycloalkyl ring containing 4, 5, 6, 7 or 8 ring carbon atoms, or Z and Y, taken together with the carbon atoms to which they are bonded, form a substituted of unsubstituted aryl ring.
6 more elements
A compound of the following structure:
- wherein
- R1 is independently selected from halogen, H, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H, alkyl and substituted alkyl or where the R1 substituents, taken together with the carbon atoms to which they are bonded, form a substituted or unsubstituted cycloalkyl ring containing 3, 4, 5, 6, 7, 8, or 9 carbon atoms;
- R1′, is independently selected from halogen, H, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H, alkyl and substituted alkyl, and only one of R1 and R1′, can be D when X is CF3, and only one of R1 and R1′ can be CD3;
- R2, R3 and R4 are independently selected from H, halogen, D, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H, alkyl and substituted alkyl;
- Q is selected from C(alkyl)2, N(alkyl), O, S, Si(alkyl)2, SO2, P(O)(alkyl) and Se;
- W is selected from C and N;
- X is selected from H, alkyl, substituted alkyl, aryl, substituted aryl, halogen, CN, OH, O(alkyl), SH, S(alkyl), S(aryl), amine, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2 and SO3H;
- Y is selected from H, C(alkyl)2, N(alkyl), N(alkyl)2, O and S;
- Z is selected from H, halogen, CN, OH, O(alkyl), O(aryl), SH, S(alkyl), S(aryl), amine, NO2, CHO, COOH, COO(alkyl), COO(aryl), PO3H2, SO3H, alkyl, and substituted alkyl or Z and Y, taken together with the carbon atoms to which they are bonded, form a substituted or unsubstituted cycloalkyl ring containing 4, 5, 6, 7 or 8 ring carbon atoms, or Z and Y, taken together with the carbon atoms to which they are bonded, form a substituted of unsubstituted aryl ring.
6 more elements
Dependencies are inferred from the claim text.