US 12,331,199 B2
Silicon containing detectable compounds
Ronald Graham, Carlsbad, CA (US); and Rodrigo Rodriguez, San Diego, CA (US)
Assigned to Singular Genomics Systems, Inc., San Diego, CA (US)
Filed by Singular Genomics Systems, Inc., San Diego, CA (US)
Filed on Apr. 3, 2023, as Appl. No. 18/130,212.
Application 18/130,212 is a continuation of application No. 16/415,700, filed on May 17, 2019, granted, now 11,697,736.
Claims priority of provisional application 62/673,579, filed on May 18, 2018.
Prior Publication US 2023/0295437 A1, Sep. 21, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C09B 11/24 (2006.01); C07F 7/08 (2006.01); C07H 21/02 (2006.01); C07H 21/04 (2006.01); C07H 23/00 (2006.01); C09B 69/00 (2006.01)
CPC C09B 11/24 (2013.01) [C07F 7/0803 (2013.01); C07F 7/0825 (2013.01); C07F 7/083 (2013.01); C07H 21/02 (2013.01); C07H 21/04 (2013.01); C09B 69/008 (2013.01); C07F 7/0816 (2013.01); C07H 23/00 (2013.01)] 17 Claims
 
1. A compound, or salt thereof, having the formula:

OG Complex Work Unit Chemistry
wherein,
L3 is

OG Complex Work Unit Chemistry
L1-L2-comprises

OG Complex Work Unit Chemistry
R1 is substituted or unsubstituted alkyl, halogen, —CF3, —CBr3, —CCl3, —CI3, —CHF2, —CHBr2, —CHCl2, —CHI2, —CH2F, —CH2Br, —CH2Cl, —CH2I, —OH, —NH2, —COOH, —CONH2, —SH, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R2 and R3 are independently substituted or unsubstituted alkyl, or substituted or unsubstituted heteroalkyl;
R4 is hydrogen, R34-substituted or unsubstituted alkyl, halogen, —CF3, —CBr3, —CCl3, —CI3, —CHF2, —CHBr2, —CHCl2, —CHI2, —CH2F, —CH2Br, —CH2Cl, —CH2I, —OH, —NH2, —COOH, —CONH2, —SH, R34-substituted or unsubstituted heteroalkyl, R34-substituted or unsubstituted cycloalkyl, or R34-substituted or unsubstituted heterocycloalkyl;
R5 is hydrogen, R35-substituted or unsubstituted alkyl, halogen, —CF3, —CBr3, —CCl3, —CI3, —CHF2, —CHBr2, —CHCl2, —CHI2, —CH2F, —CH2Br, —CH2Cl, —CH2I, —OH, —NH2, —COOH, —CONH2, —SH, R35-substituted or unsubstituted heteroalkyl, R35-substituted or unsubstituted cycloalkyl, or R35-substituted or unsubstituted heterocycloalkyl;
R6 is hydrogen, R36-substituted or unsubstituted alkyl, halogen, —CF3, —CBr3, —CCl3, —CI3, —CHF2, —CHBr2, —CHCl2, —CHI2, —CH2F, —CH2Br, —CH2Cl, —CH2I, —OH, —NH2, —COOH, —CONH2, —SH, R36-substituted or unsubstituted heteroalkyl, R36-substituted or unsubstituted cycloalkyl, or R36-substituted or unsubstituted heterocycloalkyl;
R7 is hydrogen, R37-substituted or unsubstituted alkyl, halogen, —CF3, —CBr3, —CCl3, —CI3, —CHF2, —CHBr2, —CHCl2, —CHI2, —CH2F, —CH2Br, —CH2Cl, —CH2I, —OH, —NH2, —COOH, —CONH2, —SH, R37-substituted or unsubstituted heteroalkyl, R37-substituted or unsubstituted cycloalkyl, or R37-substituted or unsubstituted heterocycloalkyl;
R8 is a nucleotide;
R9 is hydrogen, R39-substituted or unsubstituted alkyl, or R39-substituted or unsubstituted heteroalkyl;
R10 is hydrogen, R40-substituted or unsubstituted alkyl, or R40-substituted or unsubstituted heteroalkyl;
R11 is hydrogen, R41-substituted or unsubstituted alkyl, or R41-substituted or unsubstituted heteroalkyl;
R12 is hydrogen, R42-substituted or unsubstituted alkyl, or R42-substituted or unsubstituted heteroalkyl;
R4 and R5 substituents bonded to the same nitrogen atom may optionally be joined to form a R34-substituted or unsubstituted heterocycloalkyl;
R6 and R7 substituents bonded to the same nitrogen atom may optionally be joined to form a R36-substituted or unsubstituted heterocycloalkyl;
R4 and R9 substituents may optionally be joined to form a R34-substituted or unsubstituted heterocycloalkyl, or R39-substituted or unsubstituted heteroaryl;
R7 and R10 substituents may optionally be joined to form a R37-substituted or unsubstituted heterocycloalkyl, or R37-substituted or unsubstituted heteroaryl;
R5 and R11 substituents may optionally be joined to form a R35-substituted or unsubstituted heterocycloalkyl, or R35-substituted or unsubstituted heteroaryl;
R6 and R12 substituents may optionally be joined to form a R36-substituted or unsubstituted heterocycloalkyl, or R36-substituted or unsubstituted heteroaryl;
R34 is independently oxo, halogen, —CF3, —CCl3, —CI3, —CBr3, —CHF2, —CHCl2, —CHI2, —CHBr2, —CH2F, —CH2Cl, —CH2I, —CH2Br, —OCH2F, —OCH2Cl, —OCH2I, —OCH2Br, —OCHF2, —OCHCl2, —OCHI2, —OCHBr2, —OCF3, —OCCl3, —OCI3, —OCBr3, —CN, —OH, —NH2, —COOH, —CONH2, —NO2, —SH, —SO3H, —SO4H, —SO2NH2, —NHNH2, —ONH2, —NHC═(O)NHNH2, —NHC═(O)NH2, —NHSO2H, —NHC═(O)H, —NHC(O)OH, —NHOH, —PO4H, —PO3H, —N3, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, or unsubstituted heterocycloalkyl;
R35 is independently oxo, halogen, —CF3, —CCl3, —CI3, —CBr3, —CHF2, —CHCl2, —CHI2, —CHBr2, —CH2F, —CH2Cl, —CH2I, —CH2Br, —OCH2F, —OCH2Cl, —OCH2I, —OCH2Br, —OCHF2, —OCHCl2, —OCHI2, —OCHBr2, —OCF3, —OCCl3, —OCI3, —OCBr3, —CN, —OH, —NH2, —COOH, —CONH2, —NO2, —SH, —SO3H, —SO4H, —SO2NH2, —NHNH2, —ONH2, —NHC═(O)NHNH2, —NHC═(O)NH2, —NHSO2H, —NHC═(O)H, —NHC(O)OH, —NHOH, —PO4H, —PO3H, —N3, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, or unsubstituted heterocycloalkyl;
R36 is independently oxo, halogen, —CF3, —CCl3, —CI3, —CBr3, —CHF2, —CHCl2, —CHI2, —CHBr2, —CH2F, —CH2Cl, —CH2I, —CH2Br, —OCH2F, —OCH2Cl, —OCH2I, —OCH2Br, —OCHF2, —OCHCl2, —OCHI2, —OCHBr2, —OCF3, —OCCl3, —OCI3, —OCBr3, —CN, —OH, —NH2, —COOH, —CONH2, —NO2, —SH, —SO3H, —SO4H, —SO2NH2, —NHNH2, —ONH2, —NHC═(O)NHNH2, —NHC═(O)NH2, —NHSO2H, —NHC═(O)H, —NHC(O)OH, —NHOH, —PO4H, —PO3H, —N3, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, or unsubstituted heterocycloalkyl;
R37 is independently oxo, halogen, —CF3, —CCl3, —CI3, —CBr3, —CHF2, —CHCl2, —CHI2, —CHBr2, —CH2F, —CH2Cl, —CH2I, —CH2Br, —OCH2F, —OCH2Cl, —OCH2I, —OCH2Br, —OCHF2, —OCHCl2, —OCHI2, —OCHBr2, —OCF3, —OCCl3, —OCI3, —OCBr3, —CN, —OH, —NH2, —COOH, —CONH2, —NO2, —SH, —SO3H, —SO4H, —SO2NH2, —NHNH2, —ONH2, —NHC═(O)NHNH2, —NHC═(O)NH2, —NHSO2H, —NHC═(O)H, —NHC(O)OH, —NHOH, —PO4H, —PO3H, —N3, unsubstituted alkyl, unsubstituted heteroalkyl, unsubstituted cycloalkyl, or unsubstituted heterocycloalkyl;
R39 is independently —PO3H, —PO4H, —SO2NH2, —SO3H, or —SO4H;
R40 is independently —PO3H, —PO4H, —SO2NH2, —SO3H, or —SO4H;
R41 is independently —PO3H, —PO4H, —SO2NH2, —SO3H, or —SO4H; and
R42 is independently —PO3H, —PO4H, —SO2NH2, —SO3H, or —SO4H.