C07D209/24

NOVEL MOLECULES THAT SELECTIVELY INHIBIT HISTONE DEACETYLASE 6 RELATIVE TO HISTONE DEACETYLASE

This invention provides a compound having the structure:

##STR00001## wherein R.sub.1 is H, halogen, NR.sub.5R.sub.6, NR.sub.5C(0)-R.sub.6, NHC(O)OR.sub.7, OR.sub.7, NO.sub.2, CN, SR.sub.7, SO.sub.2R.sub.7, CO.sub.2R.sub.7, CF.sub.3, SOR.sub.7, POR.sub.7, C(S)R.sub.7, C(O)NR.sub.5R.sub.6, CH.sub.2C(O)NR.sub.5R.sub.6, C(NR.sub.5)R.sub.6, P(O)(OR.sub.5)(OR.sub.6), P(OR.sub.5)(OR.sub.6), C(S)R.sub.7, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, aryl, heteroaryl, or heterocyclyl, wherein R.sub.5, R.sub.6, and R.sub.7 and are each, independently, H, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; m is an integer from 0 to 2; R.sub.2 and R.sub.3 are each, independently, H, halogen, NH.sub.2, CX.sub.3, C(O)OR.sub.8, C(O)R.sub.8, C(O)NR.sub.9R.sub.10, C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, heteroalkyl, aryl, heteroaryl, or heterocyclyl; wherein X is Cl, Br, or F; R.sub.8, R.sub.9 and R.sub.10 are each, independently, H, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; Q is Ar.sub.1Z or ZAr.sub.1Z, wherein Ar.sub.1 is aryl or heteroaryl; and each occurrence of Z is independently present or absent, and when present is O, S, CH.sub.2, C(O), NH, NHNH, NHC(O), C(O)NH, NHC(O)CH.sub.2NH, NHC(O)CH.sub.2C(O), N(OH), CH.sub.2CH.sub.2 or NHC(O)CHCH; and R.sub.4 is alkyl, OR.sub.11 or NHOR.sub.11, wherein R.sub.11 is H, C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, aryl, heteroaryl, or heterocyclyl, and when Q is Ar.sub.1Z, Z is absent, Ar.sub.1 is phenyl, R.sub.2 and R.sub.3 are H, n=1, and R.sub.4 is NHOH, then R.sub.1 is other than carbazole, tetrahydro--carboline, tetrahydro--carboline, C(O)NR.sub.5R.sub.6 and NR.sub.5C(0)-R.sub.6, wherein one of R.sub.5 or R.sub.6 is quinline and the other of R.sub.5 or R.sub.6 is H;
or a pharmaceutically acceptable salt thereof.

NOVEL MOLECULES THAT SELECTIVELY INHIBIT HISTONE DEACETYLASE 6 RELATIVE TO HISTONE DEACETYLASE

This invention provides a compound having the structure:

##STR00001## wherein R.sub.1 is H, halogen, NR.sub.5R.sub.6, NR.sub.5C(0)-R.sub.6, NHC(O)OR.sub.7, OR.sub.7, NO.sub.2, CN, SR.sub.7, SO.sub.2R.sub.7, CO.sub.2R.sub.7, CF.sub.3, SOR.sub.7, POR.sub.7, C(S)R.sub.7, C(O)NR.sub.5R.sub.6, CH.sub.2C(O)NR.sub.5R.sub.6, C(NR.sub.5)R.sub.6, P(O)(OR.sub.5)(OR.sub.6), P(OR.sub.5)(OR.sub.6), C(S)R.sub.7, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, aryl, heteroaryl, or heterocyclyl, wherein R.sub.5, R.sub.6, and R.sub.7 and are each, independently, H, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; m is an integer from 0 to 2; R.sub.2 and R.sub.3 are each, independently, H, halogen, NH.sub.2, CX.sub.3, C(O)OR.sub.8, C(O)R.sub.8, C(O)NR.sub.9R.sub.10, C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, heteroalkyl, aryl, heteroaryl, or heterocyclyl; wherein X is Cl, Br, or F; R.sub.8, R.sub.9 and R.sub.10 are each, independently, H, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.2-5 alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; Q is Ar.sub.1Z or ZAr.sub.1Z, wherein Ar.sub.1 is aryl or heteroaryl; and each occurrence of Z is independently present or absent, and when present is O, S, CH.sub.2, C(O), NH, NHNH, NHC(O), C(O)NH, NHC(O)CH.sub.2NH, NHC(O)CH.sub.2C(O), N(OH), CH.sub.2CH.sub.2 or NHC(O)CHCH; and R.sub.4 is alkyl, OR.sub.11 or NHOR.sub.11, wherein R.sub.11 is H, C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, aryl, heteroaryl, or heterocyclyl, and when Q is Ar.sub.1Z, Z is absent, Ar.sub.1 is phenyl, R.sub.2 and R.sub.3 are H, n=1, and R.sub.4 is NHOH, then R.sub.1 is other than carbazole, tetrahydro--carboline, tetrahydro--carboline, C(O)NR.sub.5R.sub.6 and NR.sub.5C(0)-R.sub.6, wherein one of R.sub.5 or R.sub.6 is quinline and the other of R.sub.5 or R.sub.6 is H;
or a pharmaceutically acceptable salt thereof.

Low-molecular-compound for improving production, maintenance and proliferation of pluripotent stem cells, composition comprising the same, and culture method

Provided herein are novel indoleacrylic acid-based compounds, and pharmaceutically acceptable salts thereof, useful for the production, maintenance and proliferation of pluripotent stem cells. Also provided are cell culture compositions comprising these compounds, and methods of using these compounds in the production and maintenance of pluripotent stem cells.

Low-molecular-compound for improving production, maintenance and proliferation of pluripotent stem cells, composition comprising the same, and culture method

Provided herein are novel indoleacrylic acid-based compounds, and pharmaceutically acceptable salts thereof, useful for the production, maintenance and proliferation of pluripotent stem cells. Also provided are cell culture compositions comprising these compounds, and methods of using these compounds in the production and maintenance of pluripotent stem cells.

SQUARAINE FLUOROPHORES
20250109104 · 2025-04-03 ·

The present invention is directed to squaraine fluorophores, methods of making squaraine fluorophores, and methods of using squaraine fluorophores. In some embodiments, squaraine fluorophores can be used as imaging agents, for example for imaging cancer. In some embodiments, the squaraine fluorophores can be used to guide surgical tumor resection.

SQUARAINE FLUOROPHORES
20250109104 · 2025-04-03 ·

The present invention is directed to squaraine fluorophores, methods of making squaraine fluorophores, and methods of using squaraine fluorophores. In some embodiments, squaraine fluorophores can be used as imaging agents, for example for imaging cancer. In some embodiments, the squaraine fluorophores can be used to guide surgical tumor resection.

Platform drug delivery system utilizing crystal engineering and theanine dissolution

A platform drug delivery system and a method of improving the delivery of low solubility pharmaceuticals utilizing crystal engineering and Theanine dissolution resulting in enhanced bioactivity, dissolution rate, and solid state stability.

Platform drug delivery system utilizing crystal engineering and theanine dissolution

A platform drug delivery system and a method of improving the delivery of low solubility pharmaceuticals utilizing crystal engineering and Theanine dissolution resulting in enhanced bioactivity, dissolution rate, and solid state stability.

Halogenated compounds for photodynamic therapy

Halo-organic heterocyclic compounds are described, in which at least two halogen atoms are bound to a nitrogen-containing heterocyclic terminal moiety of the compound, with at least one of such halogen atoms being iodine or bromine. Also described are polymethine dyes based on these heterocyclic compounds, and dendrimeric compounds and conjugates of such polymethine dyes. The polymethine dyes are characterized by enhanced properties, e.g., brightness, photostability, sensitivity and/or selective affinity that make them useful to target cancer cells, pathogenic microorganisms, and/or other biological materials, in applications such as photodynamic therapy, photodynamic antimicrobial chemotherapy (PACT), cancer treatment, selective removal or attachment of biological materials, antimicrobial coating materials, and other diagnostic, theranostic, spectrum shifting, deposition/growth, and analytic applications.

Halogenated compounds for photodynamic therapy

Halo-organic heterocyclic compounds are described, in which at least two halogen atoms are bound to a nitrogen-containing heterocyclic terminal moiety of the compound, with at least one of such halogen atoms being iodine or bromine. Also described are polymethine dyes based on these heterocyclic compounds, and dendrimeric compounds and conjugates of such polymethine dyes. The polymethine dyes are characterized by enhanced properties, e.g., brightness, photostability, sensitivity and/or selective affinity that make them useful to target cancer cells, pathogenic microorganisms, and/or other biological materials, in applications such as photodynamic therapy, photodynamic antimicrobial chemotherapy (PACT), cancer treatment, selective removal or attachment of biological materials, antimicrobial coating materials, and other diagnostic, theranostic, spectrum shifting, deposition/growth, and analytic applications.