US 2026/0199382 A1Published application

Phosphoramidate monosaccarides, pharmaceutical compositions, and diagnostic and therapeutic applications

AssigneeSurio Therapeutics Co., LTD.

InventorsKaimin Cai, Jianjun Cheng

Life of this patent

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Abstract

Provided herein are monosaccharides, e.g., a compound of Formula (I), and pharmaceutical compositions thereof. Also provided herein are methods of their use for cell labeling for diagnostic and/or therapeutic applications.

Claims112

Dependent claims

A compound of Formula (I):

or an enantiomer, a mixture of enantiomers, a diastereomer, a mixture of two or more diastereomers, a tautomer, a mixture of two or more tautomers, or an isotopic variant thereof;
or
a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof;
wherein:
R1 is (i) —C(O)R5a, —C(O)OR5a, or —C(O)NR5bR5c;
or (ii) hydrogen;
and R5 is -L2-P(X)(OR5a)(NR5bR5c);
or R1 is -L2-P(X)(OR5a)(NR5bR5c);
and R5 is (i) hydrogen;
or (ii) —C(O)R5a, —C(O)OR5a, or —C(O)NR5bR5c;
R2 is (i) hydrogen;
(ii) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
or (iii) —C(O)R1a, —C(O)OR1a, —C(O)NR1bR1c, —C(O)SR1a, —C(NR1a)NR1bR1c, —C(S)R1a, —C(S)OR1a, —C(S)NR1bR1c, —S(O)R1a, —S(O)2R1a, —S(O)NR1bR1c, —S(O)2NR1bR1c, or —Si(R1a)3;
R3 and R4 are each independently (i) —OR5a, —OC(O)R5a, —OC(O)OR5a, or —OC(O)NR5bR5c;
or (ii) halo;
or R3 and R4 or R4 and R5 are linked together to form a lactone ring;
each R5a, R5b, and R5c is independently hydrogen, C1-30 alkyl, C1-30 heteroalkyl, C2-30 alkenyl, C2-30 alkynyl, C3-30 cycloalkyl, C6-30 aryl, C7-30 aralkyl, heteroaryl, or heterocyclyl;
A is a bond, O, or N(R1b);
L1 is C1-6 alkylene, C1-6 heteroalkylene, C2-6 alkenylene, C2-6 alkynylene, C3-10 cycloalkylene, C6-14 arylene, C7-15 aralkylene, heteroarylene, or heterocyclylene;
each L2 is independently (i) a bond;
or (ii) —O—C1-6 alkylene, —O—C1-6 heteroalkylene, —O—C2-6 alkenylene, —O—C2-6 alkynylene, —O—C3-10 cycloalkylene, —O—C6-14 arylene, —O—C7-15 aralkylene, —O-heteroarylene, or —O-heterocyclylene;
each X is independently O or S;
Z is azido, hydrogen, halo, isocyano, —C═C(R1a)R1a, —C≡CR1a,
—C(O)R1a, or —SH;
and
each R1a, R1b, and R1c is independently hydrogen, deuterium, C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
wherein each alkyl, alkylene, heteroalkyl, heteroalkylene, alkenyl, alkenylene, alkynyl, alkynylene, cycloalkyl, cycloalkylene, aryl, arylene, aralkyl, aralkylene, heteroaryl, heteroarylene, heterocyclyl, and heterocyclylene is optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q, wherein each Q is independently selected from:
(a) deuterium, cyano, halo, nitro, and oxo;
(b) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, and heterocyclyl, each of which is further optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Qa;
and (c) —C(O)Ra, —C(O)ORa, —C(O)NRbRc, —C(O)SRa, —C(NRa)NRbRc, —C(S)Ra, —C(S)ORa, —C(S)NRbRc, —ORa, —OC(O)Ra, —OC(O)ORa, —OC(O)NRbRc, —OC(O)SRa, —OC(NRa)NRbRc, —OC(S)Ra, —OC(S)ORa, —OC(S)NRbRc, —OP(O)(ORb)ORc, —OS(O)Ra, —OS(O)2Ra, —OS(O)NRbRc, —OS(O)2NRbRc, —NRbRc, —NRaC(O)Rd, —NRaC(O)ORd, —NRaC(O)NRbRc, —NRaC(O)SRd, —NRaC(NRd)NRbRc, —NRaC(S)Rd, —NRaC(S)ORd, —NRaC(S)NRbRc, —NRaS(O)Rd, —N═S(O)RaRd, —NRaS(O)2Rd, —NRaS(O)NRbRc, —NRaS(O)2NRbRc, —SRa, —S(O)Ra, —S(O)2Ra, —S(O)NRbRc, and —S(O)2NRbRc, wherein each Ra, Rb, Rc, and Rd is independently (i) hydrogen or deuterium;
(ii) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl, each of which is optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Qa;
or (iii) Rb and Rc together with the N atom to which they are attached form heterocyclyl, optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Qa;
wherein each Qa is independently selected from:
(a) deuterium, cyano, halo, nitro, and oxo;
(b) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, and heterocyclyl;
and (c) —C(O)Re, —C(O)ORe, —C(O)NRfRg, —C(O)SRe, —C(NRe)NRfRg, —C(S)Re, —C(S)ORe, —C(S)NRfRg, —ORe, —OC(O)Re, —OC(O)ORe, —OC(O)NRfRg, —OC(O)SRc, —OC(NRc)NRfRg, —OC(S)Rc, —OC(S)ORc, —OC(S)NRfRg, —OP(O)(ORf)ORg, —OS(O)Re, —OS(O)2Re, —OS(O)NRfRg, —OS(O)2NRfRg, —NRfRg, —NRcC(O)Rh, —NRcC(O)ORf, —NRcC(O)NRfRg, —NRcC(O)SRf, —NRcC(NRh)NRfRg, —NReC(S)Rh, —NReC(S)ORf, —NReC(S)NRfRg, —NReS(O)Rh, —N═S(O)ReRh, —NReS(O)2Rh, —NReS(O)NRfRg, —NReS(O)2NRfRg, —SRe, —S(O)Re, —S(O)2Re, —S(O)NRfRg, and —S(O)2NRfRg;
wherein each Re, Rf, Rg, and Rh is independently (i) hydrogen or deuterium;
(ii) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
or (iii) Rf and Rg together with the N atom to which they are attached form heterocyclyl.

36 more elements

A compound of:

acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A1;
2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A2;
2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-(((1S)-1-(1-phenylethoxy-carbonyl)ethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A3;
2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-((1-methyl-1-(1-phenyl-ethoxycarbonyl)ethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A4;
2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-(((1S)-1-(1-phenylethoxy-carbonyl)-2-methylpropylamino)(phenoxy)phosphoryl)-D-mannopyranoside A5;
2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-((1-methyl-1-(1-methyl-1-phenylethoxycarbonyl)ethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A6;
2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-(((1S)-1-(1-methyl-1-phenylethoxycarbonyl)-2-methylpropylamino)(phenoxy)phosphoryl)-D-mannopyranoside A7;
pyridin-3-ylacetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A8;
3-morpholinopropanoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A9;
4-methylpiperazin-1-ylpropanoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A10;
4-acetylpiperazin-1-ylpropanoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A11;
tetrahydropyran-4-ylcarbonyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A12;
1-methylpiperidin-4-ylcarbonyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A13;
pyrrolidin-1-ylacetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A14;
4-dimethylaminobenzoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A15;
pyridin-3-ylcarbonyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A16;
pyrrol-2-ylcarbonyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A17;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-butoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A18;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-(((1S)-1-sec-butoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A19;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-tert-butoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A20;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-pentoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A21;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-hexoxy-carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A22;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-(2-ethyl-butoxy)carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A23;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-pyridin-3-ylmethoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A24;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-pyridin-4-ylmethoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A25;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-quinolin-4-ylmethoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A26;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-quinolin-5-ylmethoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A27;
pentanoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-quinolin-5-ylmethoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A28;
2-methylbutanoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-quinolin-5-ylmethoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A29;
hexanoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-quinolin-5-ylmethoxycrbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A30;
nonanoyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-quinolin-5-ylmethoxycarbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A31;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-(4-methyl-tetrahydropyran-4-yloxy)carbonylethylamino)(phenoxy)phosphoryl)-D-mannopyranoside A32;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-(((1S)-1-(1-(4-(tert-butoxycarbonylamino)phenyl)ethoxycarbonyl)-2-methylpropylamino)(phenoxy)-phosphoryl)-D-mannopyranoside A33;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O—(((S)-1-isopropoxy-carbonylethylamino)(quinolin-5-yloxy)phosphoryl)-D-mannopyranoside A34;
acetyl 2-(2-azidoacetylamino)-2-deoxy-3,4-di-O-acetyl-6-O-(3-(((S)-1-isoprop-oxycarbonylethylamino)(phenoxy)phosphoryloxy)propanoyl)-D-mannopyranoside A35;
(3S,4R,5S,6R)-3-(2-azidoacetamido)-6-((((((R)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate A36;
(3S,4R,5S,6R)-3-(2-azidoacetamido)-6-((((((S)-3-methyl-1-oxo-1-(1-phenyl-cyclopropoxy)butan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate A37;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-2-((((((S)-1-oxo-1-(pentyloxy)propan-2-yl)-amino)(phenoxy)phosphoryl)oxy)methyl)-6-((tetrahydro-2H-pyran-4-carbonyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate A38;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-((3-morpholinobenzoyl)oxy)-2-((((((S)-1-oxo-1-(pentyloxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl diacetate A39;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-((3-(4-methylpiperazin-1-yl)benzoyl)-oxy)-2-((((((S)-1-oxo-1-(pentyloxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)-tetrahydro-2H-pyran-3,4-diyl diacetate A40;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-((3-(morpholinomethyl)benzoyl)oxy)-2-((((((S)-1-oxo-1-(pentyloxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl diacetate A41;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-((3-((4-methylpiperazin-1-yl)methyl)-benzoyl)oxy)-2-((((((S)-1-oxo-1-(pentyloxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)-methyl)tetrahydro-2H-pyran-3,4-diyl diacetate A42;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-2-((((((S)-1-oxo-1-(quinolin-4-ylmethoxy)-propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)-6-(pentanoyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate A43;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-((2-methylbutanoyl)oxy)-2-((((((S)-1-oxo-1-(quinolin-4-ylmethoxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl diacetate A44;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-(hexanoyloxy)-2-((((((S)-1-oxo-1-(quinolin-4-ylmethoxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl diacetate A45;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-(nonanoyloxy)-2-((((((S)-1-oxo-1-(quinolin-4-ylmethoxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl diacetate A46;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-2-((((((S)-1-oxo-1-(quinolin-4-ylmethoxy)-propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)-6-((tetrahydro-2H-pyran-4-carbonyl)-oxy)tetrahydro-2H-pyran-3,4-diyl diacetate A47;
(3S,4R,5S,6R)-3-(2-azidoacetamido)-6-((((((S)-1-oxo-1-((tetrahydro-2H-pyran-4-yl)oxy)propan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate A48;
(3S,4R,5S,6R)-3-(2-azidoacetamido)-6-((((((S)-1-((1-methylpiperidin-4-yl)oxy)-1-oxopropan-2-yl)amino)(phenoxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate A49;
(3S,4R,5S,6R)-3-(2-azidoacetamido)-6-((((((S)-1-isopropoxy-1-oxopropan-2-yl)-amino)(quinolin-5-yloxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate A50;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-2-((((((S)-1-isopropoxy-1-oxopropan-2-yl)-amino)(quinolin-5-yloxy)phosphoryl)oxy)methyl)-6-(pentanoyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate A51;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-2-((((((S)-1-isopropoxy-1-oxopropan-2-yl)-amino)(quinolin-5-yloxy)phosphoryl)oxy)methyl)-6-(pivaloyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate A52;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-6-(hexanoyloxy)-2-((((((S)-1-isopropoxy-1-oxopropan-2-yl)amino)(quinolin-5-yloxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-3,4-diyl diacetate A53;
(2R,3S,4R,5S)-5-(2-azidoacetamido)-2-((((((S)-1-isopropoxy-1-oxopropan-2-yl)-amino)(quinolin-5-yloxy)phosphoryl)oxy)methyl)-6-(nonanoyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate A54;
(3S,4R,5S,6R)-3-(2-azidoacetamido)-6-((((((S)-1-oxo-1-(pentyloxy)propan-2-yl)-amino)(quinolin-5-yloxy)phosphoryl)oxy)methyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate A55;
or
(((1S)-1-(1-phenylethoxycarbonyl)-ethylamino)(phenoxy)phosphoryl) 2-(2-azidoacetylamino)-2-deoxy-3,4,6-tri-O-acetyl-D-mannopyranoside B1;
or an enantiomer, a mixture of enantiomers, a diastereomer, a mixture of two or more diastereomers, a tautomer, a mixture of two or more tautomers, or an isotopic variant thereof;
or
a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof.

57 more elements

Dependencies are inferred from the claim text.

Facts

Application: 19/134,687Filed 7 Dec 2023
Priority: WO PCT/CN2022/1375198 Dec 2022
Published: 16 Jul 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

A61K 31/7048
Compounds having saccharide radicals and heterocyclic rings: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin,…
A61P 35/00
Antineoplastic agents
A61K 31/7024
Carbohydrates; Sugars; Derivatives thereof: esters of saccharides
A61K 31/706
Having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides: containing six-membered rings with nitrogen as a ring hetero atom

Family

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Abstract

A compound of Formula (I):

or an enantiomer, a mixture of enantiomers, a diastereomer, a mixture of two or more diastereomers, a tautomer, a mixture of two or more tautomers, or an isotopic variant thereof;
or
a pharmaceutically acceptable salt, solvate, hydrate, or prodrug thereof;
wherein:
R1 is (i) —C(O)R5a, —C(O)OR5a, or —C(O)NR5bR5c;
or (ii) hydrogen;
and R5 is -L2-P(X)(OR5a)(NR5bR5c);
or R1 is -L2-P(X)(OR5a)(NR5bR5c);
and R5 is (i) hydrogen;
or (ii) —C(O)R5a, —C(O)OR5a, or —C(O)NR5bR5c;
R2 is (i) hydrogen;
(ii) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
or (iii) —C(O)R1a, —C(O)OR1a, —C(O)NR1bR1c, —C(O)SR1a, —C(NR1a)NR1bR1c, —C(S)R1a, —C(S)OR1a, —C(S)NR1bR1c, —S(O)R1a, —S(O)2R1a, —S(O)NR1bR1c, —S(O)2NR1bR1c, or —Si(R1a)3;
R3 and R4 are each independently (i) —OR5a, —OC(O)R5a, —OC(O)OR5a, or —OC(O)NR5bR5c;
or (ii) halo;
or R3 and R4 or R4 and R5 are linked together to form a lactone ring;
each R5a, R5b, and R5c is independently hydrogen, C1-30 alkyl, C1-30 heteroalkyl, C2-30 alkenyl, C2-30 alkynyl, C3-30 cycloalkyl, C6-30 aryl, C7-30 aralkyl, heteroaryl, or heterocyclyl;
A is a bond, O, or N(R1b);
L1 is C1-6 alkylene, C1-6 heteroalkylene, C2-6 alkenylene, C2-6 alkynylene, C3-10 cycloalkylene, C6-14 arylene, C7-15 aralkylene, heteroarylene, or heterocyclylene;
each L2 is independently (i) a bond;
or (ii) —O—C1-6 alkylene, —O—C1-6 heteroalkylene, —O—C2-6 alkenylene, —O—C2-6 alkynylene, —O—C3-10 cycloalkylene, —O—C6-14 arylene, —O—C7-15 aralkylene, —O-heteroarylene, or —O-heterocyclylene;
each X is independently O or S;
Z is azido, hydrogen, halo, isocyano, —C═C(R1a)R1a, —C≡CR1a,
—C(O)R1a, or —SH;
and
each R1a, R1b, and R1c is independently hydrogen, deuterium, C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
wherein each alkyl, alkylene, heteroalkyl, heteroalkylene, alkenyl, alkenylene, alkynyl, alkynylene, cycloalkyl, cycloalkylene, aryl, arylene, aralkyl, aralkylene, heteroaryl, heteroarylene, heterocyclyl, and heterocyclylene is optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Q, wherein each Q is independently selected from:
(a) deuterium, cyano, halo, nitro, and oxo;
(b) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, and heterocyclyl, each of which is further optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Qa;
and (c) —C(O)Ra, —C(O)ORa, —C(O)NRbRc, —C(O)SRa, —C(NRa)NRbRc, —C(S)Ra, —C(S)ORa, —C(S)NRbRc, —ORa, —OC(O)Ra, —OC(O)ORa, —OC(O)NRbRc, —OC(O)SRa, —OC(NRa)NRbRc, —OC(S)Ra, —OC(S)ORa, —OC(S)NRbRc, —OP(O)(ORb)ORc, —OS(O)Ra, —OS(O)2Ra, —OS(O)NRbRc, —OS(O)2NRbRc, —NRbRc, —NRaC(O)Rd, —NRaC(O)ORd, —NRaC(O)NRbRc, —NRaC(O)SRd, —NRaC(NRd)NRbRc, —NRaC(S)Rd, —NRaC(S)ORd, —NRaC(S)NRbRc, —NRaS(O)Rd, —N═S(O)RaRd, —NRaS(O)2Rd, —NRaS(O)NRbRc, —NRaS(O)2NRbRc, —SRa, —S(O)Ra, —S(O)2Ra, —S(O)NRbRc, and —S(O)2NRbRc, wherein each Ra, Rb, Rc, and Rd is independently (i) hydrogen or deuterium;
(ii) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl, each of which is optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Qa;
or (iii) Rb and Rc together with the N atom to which they are attached form heterocyclyl, optionally substituted with one or more, in one embodiment, one, two, three, or four, substituents Qa;
wherein each Qa is independently selected from:
(a) deuterium, cyano, halo, nitro, and oxo;
(b) C1-6 alkyl, C1-6 heteroalkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, and heterocyclyl;
and (c) —C(O)Re, —C(O)ORe, —C(O)NRfRg, —C(O)SRe, —C(NRe)NRfRg, —C(S)Re, —C(S)ORe, —C(S)NRfRg, —ORe, —OC(O)Re, —OC(O)ORe, —OC(O)NRfRg, —OC(O)SRc, —OC(NRc)NRfRg, —OC(S)Rc, —OC(S)ORc, —OC(S)NRfRg, —OP(O)(ORf)ORg, —OS(O)Re, —OS(O)2Re, —OS(O)NRfRg, —OS(O)2NRfRg, —NRfRg, —NRcC(O)Rh, —NRcC(O)ORf, —NRcC(O)NRfRg, —NRcC(O)SRf, —NRcC(NRh)NRfRg, —NReC(S)Rh, —NReC(S)ORf, —NReC(S)NRfRg, —NReS(O)Rh, —N═S(O)ReRh, —NReS(O)2Rh, —NReS(O)NRfRg, —NReS(O)2NRfRg, —SRe, —S(O)Re, —S(O)2Re, —S(O)NRfRg, and —S(O)2NRfRg;
wherein each Re, Rf, Rg, and Rh is independently (i) hydrogen or deuterium;
(ii) C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-10 cycloalkyl, C6-14 aryl, C7-15 aralkyl, heteroaryl, or heterocyclyl;
or (iii) Rf and Rg together with the N atom to which they are attached form heterocyclyl.

36 more elements

Facts

Application

19/134,687Filed 7 Dec 2023

Priority

WO PCT/CN2022/1375198 Dec 2022

Published

16 Jul 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification14 codes

A61K 31/7048
Compounds having saccharide radicals and heterocyclic rings: having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin,…
A61P 35/00
Antineoplastic agents
A61K 31/7024
Carbohydrates; Sugars; Derivatives thereof: esters of saccharides
A61K 31/706
Having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides: containing six-membered rings with nitrogen as a ring hetero atom