Small molecule inhibitors of PFKFB3 and glycolytic flux and their methods of use as anti-cancer therapeutics
US-9403769-B2 · Aug 2, 2016 · US
US11407739B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11407739-B2 |
| Application number | US-201916673385-A |
| Country | US |
| Kind code | B2 |
| Filing date | Nov 4, 2019 |
| Priority date | Apr 18, 2019 |
| Publication date | Aug 9, 2022 |
| Grant date | Aug 9, 2022 |
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Disclosed are a compound represented by Chemical Formula 1, an optical filter, an image sensor, a camera module, and an electronic device.In Chemical Formula 1, R1 to R27 and n are the same as defined in the detailed description.
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What is claimed is: 1. A compound represented by Chemical Formula 1A or 1B: wherein, in Chemical Formulas 1A and 1B, R 1 to R 6 are each independently hydrogen or a C1 to C5 alkyl group, wherein in Chemical Formula 1A, R 7 to R 18 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, a halogen, a cyano group, or a combination thereof, wherein, in Chemical Formula 1A, at least one of R 7 to R 18 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, or a combination thereof, wherein, in Chemical Formula 1A, R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, wherein, in Chemical Formula 1A, n is 1 or 2, wherein, in Chemical Formula 1B, R 7 to R 18 and R 23 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C3 to C20 heterocyclic group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, a halogen, a cyano group, or a combination thereof, wherein, in Chemical Formula 1B, at least one of R 7 to R 18 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, or a combination thereof, and wherein, in Chemical Formula 1B, R a to R j are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. 2. The compound of claim 1 , wherein the compound is represented by Chemical Formula 1A. 3. The compound of claim 1 , wherein in Chemical Formulas 1A and 1B, at least one of R 8 , R 10 , R 14 , and R 16 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, or a combination thereof, and wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. 4. The compound of claim 3 , wherein in Chemical Formulas 1A and 1B, R 8 and R 14 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, or a combination thereof, and wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. 5. The compound of claim 3 , wherein in Chemical Formulas 1A and 1B, R 10 and R 16 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, or a combination thereof, and wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. 6. The compound of claim 1 , wherein R 1 to R 6 are each independently a methyl group, an ethyl group, or a propyl group. 7. The compound of claim 1 , wherein the compound is represented by Chemical Formula 1B. 8. The compound of claim 2 , wherein at least one of R 8 , R 10 , R 14 , and R 16 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, or a combination thereof, and wherein R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. 9. The compound of claim 1 , wherein the compound is represented by one of Chemical Formulae 1A-1, 1A-2, 1B-1, and 1B-2: wherein in Chemical Formulae 1A-1, 1A-2, 1B-1, and 1B-2, R 1 to R 6 are each independently hydrogen or a C1 to C5 alkyl group, R 8 , R 10 , R 14 , and R 16 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C20 alkoxy group, —NR a R b , —NHCOR c , —OCOR d , a hydroxy group, or a combination thereof, R a to R d are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, wherein, in Chemical Formulae 1A-1 and 1A-2, n is 1 or 2, and wherein in Chemical Formulae 1B-1 and 1B-2, R e to R j are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof. 10. An optical filter comprising: the compound of claim 1 or a cured product thereof. 11. An image sensor comprising: a semiconductor substrate, and an optical filter on the semiconductor substrate, the optical filter configured to absorb at least a portion of light in a near-infrared wavelength region, wherein the optical filter includes the compound of claim 1 or a cured product thereof. 12. The image sensor of claim 11 , wherein the semiconductor substrate includes a plurality of photodiodes. 13. The image sensor of claim 11 , further comprising: a color filter on the semiconductor substrate and on or under the optical filter. 14. The image sensor of claim 11 , further comprising: a dual band-pass filter configured to transmit all of a visible wavelength region and a portion of the near-infrared wavelength region. 15. A camera module comprising: the optical filter of claim 10 . 16. A camera module comprising: the image sensor of claim 11 . 17. An electronic device comprising: the optical filter of claim 10 . 18. An electronic device comprising: the image sensor of claim 11 . 19. An electronic device comprising: the camera modul
for generating image signals from different wavelengths · CPC title
from near infrared [NIR] radiation · CPC title
Colour filters · CPC title
Infrared image sensors · CPC title
Colour image sensors · CPC title
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