US 12,522,623 B2Granted

Small molecule STAT protein degraders

AssigneeThe Regents of the University of Michigan

InventorsShaomeng Wang, Haibin Zhou, Renqi Xu, Longchuan Bai, Donna McEachern, Jeanne Stuckey, Chao-Yie Yang

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Abstract

The present disclosure provides compounds represented by Formula (I) and the pharmaceutically acceptable salts and solvates thereof, wherein R1a, R1b, R3a, R4, A, E1, E2, M, and Q are as set forth in the specification. Compounds of Formula (I) are STAT protein degraders and thus are useful for the treatment of cancer and other diseases.

Claims20

Dependent claims

A compound of Formula I:

or a pharmaceutically acceptable salt or solvate thereof, wherein
R1a and R1b are independently selected from the group consisting of hydrogen, phenyl, C1-C4 alkyl, aralkyl, —CH2OC(═O)R1c, and —CH(R1d)C(═O)OR1e;
E1 and E2 are independently selected from the group consisting of —O— and —NH—;
R1c is selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, and C1-C6 alkoxy;
R1d is C1-C4 alkyl;
R1e is is C1-C6 alkyl;
M is selected from the group consisting of —O— and —C(R2a)(R2b)—;
R2a and R2b are independently selected from the group consisting of hydrogen and fluoro;
or
R2a and R2b taken together with the carbon atom to which they are attached form a —C(═O)— group;
A is selected from the group consisting of:
wherein the bond designated with a “” is attached to -M-P(═O)(E1R1a)(E2R1b);
each R15 is independently selected from the group consisting of halo, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
R16 is selected from the group consisting of hydrogen, C1-C4 alkyl, and —C(═O)R17;
R17 is C1-C4 alkyl;
p is 0, 1, 2, or 3;
R3a is selected from the group consisting of hydrogen and C1-C4 alkyl;
R4 is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, (heterocyclo)alkyl, —C(═O)R5a, —S(═O)2R5b, (carboxamido)alkyl, (amino)alkyl, and -L-B;
R5a is selected from the group consisting of C1-C6 alkyl, amino, C1-C6 alkoxy, aralkyloxy, optionally substituted C3-C10 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, optionally substituted 5- to 10-membered heteroaryl, aralkyl, and (heteroaryl)alkyl;
R5b is C1-C6 alkyl;
Q is selected from the group consisting of:
R6 is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted aralkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, and optionally substituted 5- to 14-membered heteroaryl;
R7a, R7b, R7c, R7d, R7e, and R7f are each independently selected from the group consisting of —C(═O)NH2, —OC(═O)NH2, —NR12aC(═O)NH2, —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, —OC(═O)NR12cR12d, —N(R12a)C(═O)R12cR12d, —S(═O)2NR12eR12f, —N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
R12a is selected from the group consisting of hydrogen and C1-C3 alkyl;
R12b, R12c, and R12d are each independently C1-C3 alkyl;
R12e and R12f are each independently selected from the group consisting of hydrogen and C1-C3 alkyl;
R13a, and R13b are independently selected from the group consisting of C1-C6 alkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, and optionally substituted 5- to 10-membered heteroaryl;
R8a is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted C2-C6 alkynyl, aralkyl, (heteroaryl)alkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, optionally substituted 5- to 10-membered heteroaryl, (amido)(aryl)alkyl, (amino)(aryl)alkyl, (amino)(heteroaryl)alkyl, and (cycloalkyl)alkyl;
R8b is selected from the group consisting of hydrogen, C1-C4 alkyl, optionally substituted aryl, and aralkyl;
or
R8a and R8b taken together with the nitrogen atom to which they are attached form a 4- to 8-membered optionally substituted heterocyclo;
R8c is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
G1 is selected from the group consisting of —C(R11a)— and —N—;
R11a is selected from the group consisting of hydrogen and C1-C3 alkyl;
R8d is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
R9a is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted C3-C12 cycloalkyl, optionally substituted aryl, aralkyl, (heteroaryl)alkyl, (cycloalkyl)alkyl, and optionally substituted 5- to 9-membered heteroaryl;
R9b is selected from the group consisting of hydrogen and C1-C4 alkyl;
R9c is selected from the group consisting of hydrogen and C1-C4 alkyl;
or
R9a and R9b taken together form a C3-C8 optionally substituted cycloalkyl or C4-C9 optionally substituted heterocyclo;
or
R9b and R9c taken together form a 4- to 9-membered optionally substituted heterocyclo;
R10a is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted C3-C12 cycloalkyl, optionally substituted aryl, aralkyl, (heteroaryl)alkyl, (cycloalkyl)alkyl, and optionally substituted 5- to 9-membered heteroaryl;
R10b is selected from the group consisting of hydrogen and C1-C4 alkyl;
R10c is selected from the group consisting of hydrogen and C1-C4 alkyl;
or
R10a and R10b taken together form a C3-C8 optionally substituted cycloalkyl or C4-C9 optionally substituted heterocyclo;
or
R10b and R10c taken together form a 4- to 9-membered optionally substituted heterocyclo;
G2 is selected from the group consisting of —C(R11b)— and —N—;
R11b is selected from the group consisting of hydrogen and C1-C3 alkyl;
a, b, c, and d are each independently 1, 2, or 3;
e, f, g, h, i, and j are each independently 0, 1, or 2;
L is -J1-Y1-J2-Y2-J3-Z—;
J1 is selected from the group consisting of alkylenyl, heteroalkylenyl, cycloalkylenyl, heterocyclenyl, phenylenyl, and heteroarylenyl;
or J1 is absent;
Y1 is selected from the group consisting of —(CH2)m—, —C≡C—, —CH═CH—, —N(R16a), —C(═O)—, —S(═O)2—, —C(═O)O—, —OC(═O)—, —C(═O)N(R16b)—, and —N(R16b)C(═O)—;
m is 0, 1, 2, or 3;
R16a is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
R16b is selected from the group consisting of hydrogen and C1-C4 alkyl;
J2 is selected from the group consisting of alkylenyl, heteroalkylenyl, cycloalkylenyl, heterocyclenyl, phenylenyl, and heteroarylenyl;
or J2 is absent;
Y2 is selected from the group consisting of —(CH2)n—, —C≡C—, —CH═CH—, —N(R12g), —C(═O)—, —S(═O)2—, —C(═O)O—, —OC(═O)—, —C(═O)N(R12h), and —(R12h)C(═O)N—;
n is 0, 1, 2, 3, 4, 5, or 6;
R12g is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
R12h is selected from the group consisting of hydrogen and C1-C4 alkyl;
J1 is selected from the group consisting of alkylenyl, heteroalkylenyl, cycloalkylenyl, heterocyclenyl, phenylenyl, and heteroarylenyl;
or J3 is absent;
Z and Z2 are independently selected from the group consisting of —(CH2)o—, —C≡C—, —CH═CH—, —C(═O)—, —O—, —S—, and —N(R12i)—;
o is 0, 1, 2, or 3;
R12i is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
wherein Z is attached to B;
L1 is spiroheterocyclenyl;
B is selected from the group consisting of:
E5 is selected from the group consisting of —C(R14a)═ and —N═;
E2 is selected from the group consisting of —C(R14b)═ and —N═;
E3 is selected from the group consisting of —C(R14c)═ and —N═;
E4 is selected from the group consisting of —C(R14d)═ and —N═;
Z1 is selected from the group consisting of —CH2 and —C(═O)—;
R13a is selected from the group consisting of hydrogen, methyl, and fluoro;
R13b is selected from the group consisting of hydrogen and methyl;
and
R14a, R14b, R14c, and R14d are each independently selected from the group consisting of hydrogen, halo, and C1-4 alkyl;
with the provisos:
(1) when R4 is -L-B, then Q is selected from the group consisting of Q1 and Q2;
and
(a) when Q is Q1, and R7a is selected from the group consisting of —C(═O)NH2—OC(═O)NH2, and —NR12aC(═O)NH2, then R6 is optionally substituted 5- to 14-membered heteroaryl;
or
(b) when Q is Q1, and R6 is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted aralkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, and optionally substituted aryl, then R7a is selected from the group consisting of —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, OC(═O)NR12cR12d, —N(R12a)C(═O)NR12cR12d, —S(═O)2NR12eR12f, N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
or
(c) when Q is Q-2, then R7b is selected from the group consisting of —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, OC(═O)NR12cR12d, —N(R12a)C(═O)NR12cR12d, —S(═O)2NR12eR12f, N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
or
(d) B is selected from the group consisting of B-5, B-6, B-7, and B-8;
or
(2) when R4 is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, (heterocyclo)alkyl, C(═O)R5a, and —S(═O)2R5b, then Q is Q-3, Q-4, Q-5, or Q-6;
and
(e) R7c, R7d, R7e, and R7f are each independently selected from the group consisting of —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, —OC(═O)NR12cR12d, —N(R12a)C(═O)NR12cR12d, —S(═O)2NR12eR12f, —N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
or
(f) B is selected from the group consisting of B-5, B-6, B-7, and B-8;
or
(3) when R4 is selected from the group consisting of (carboxamido)alkyl and (amino)alkyl, then Q is Q-3, Q-4, Q-5, or Q-6.

98 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/911,728Filed 26 Mar 2021 · us provisional application
Priority: 26 Mar 2020
Published: US 2023/0159573 A125 May 2023
Granted: 13 Jan 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07F 9/6561
Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom: containing systems of two or more relevant hetero rings condensed among…
A61P 35/00
Antineoplastic agents
C07F 9/655354
The sulfur atom being part of a five-membered ring: condensed with carbocyclic rings or carbocyclic ring systems
C07F
Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen

Family

Application63/000,059Us provisional application · filed 26 Mar 2020
Application63/062,829Us provisional application · filed 7 Aug 2020
US 2023/0159573 A1Pre-grant publication · published 25 May 2023
US 12,522,623 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound of Formula I:

or a pharmaceutically acceptable salt or solvate thereof, wherein
R1a and R1b are independently selected from the group consisting of hydrogen, phenyl, C1-C4 alkyl, aralkyl, —CH2OC(═O)R1c, and —CH(R1d)C(═O)OR1e;
E1 and E2 are independently selected from the group consisting of —O— and —NH—;
R1c is selected from the group consisting of C1-C6 alkyl, C3-C6 cycloalkyl, and C1-C6 alkoxy;
R1d is C1-C4 alkyl;
R1e is is C1-C6 alkyl;
M is selected from the group consisting of —O— and —C(R2a)(R2b)—;
R2a and R2b are independently selected from the group consisting of hydrogen and fluoro;
or
R2a and R2b taken together with the carbon atom to which they are attached form a —C(═O)— group;
A is selected from the group consisting of:
wherein the bond designated with a “” is attached to -M-P(═O)(E1R1a)(E2R1b);
each R15 is independently selected from the group consisting of halo, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy;
R16 is selected from the group consisting of hydrogen, C1-C4 alkyl, and —C(═O)R17;
R17 is C1-C4 alkyl;
p is 0, 1, 2, or 3;
R3a is selected from the group consisting of hydrogen and C1-C4 alkyl;
R4 is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, (heterocyclo)alkyl, —C(═O)R5a, —S(═O)2R5b, (carboxamido)alkyl, (amino)alkyl, and -L-B;
R5a is selected from the group consisting of C1-C6 alkyl, amino, C1-C6 alkoxy, aralkyloxy, optionally substituted C3-C10 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, optionally substituted 5- to 10-membered heteroaryl, aralkyl, and (heteroaryl)alkyl;
R5b is C1-C6 alkyl;
Q is selected from the group consisting of:
R6 is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted aralkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, and optionally substituted 5- to 14-membered heteroaryl;
R7a, R7b, R7c, R7d, R7e, and R7f are each independently selected from the group consisting of —C(═O)NH2, —OC(═O)NH2, —NR12aC(═O)NH2, —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, —OC(═O)NR12cR12d, —N(R12a)C(═O)R12cR12d, —S(═O)2NR12eR12f, —N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
R12a is selected from the group consisting of hydrogen and C1-C3 alkyl;
R12b, R12c, and R12d are each independently C1-C3 alkyl;
R12e and R12f are each independently selected from the group consisting of hydrogen and C1-C3 alkyl;
R13a, and R13b are independently selected from the group consisting of C1-C6 alkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, and optionally substituted 5- to 10-membered heteroaryl;
R8a is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted C2-C6 alkynyl, aralkyl, (heteroaryl)alkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, optionally substituted aryl, optionally substituted 5- to 10-membered heteroaryl, (amido)(aryl)alkyl, (amino)(aryl)alkyl, (amino)(heteroaryl)alkyl, and (cycloalkyl)alkyl;
R8b is selected from the group consisting of hydrogen, C1-C4 alkyl, optionally substituted aryl, and aralkyl;
or
R8a and R8b taken together with the nitrogen atom to which they are attached form a 4- to 8-membered optionally substituted heterocyclo;
R8c is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
G1 is selected from the group consisting of —C(R11a)— and —N—;
R11a is selected from the group consisting of hydrogen and C1-C3 alkyl;
R8d is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
R9a is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted C3-C12 cycloalkyl, optionally substituted aryl, aralkyl, (heteroaryl)alkyl, (cycloalkyl)alkyl, and optionally substituted 5- to 9-membered heteroaryl;
R9b is selected from the group consisting of hydrogen and C1-C4 alkyl;
R9c is selected from the group consisting of hydrogen and C1-C4 alkyl;
or
R9a and R9b taken together form a C3-C8 optionally substituted cycloalkyl or C4-C9 optionally substituted heterocyclo;
or
R9b and R9c taken together form a 4- to 9-membered optionally substituted heterocyclo;
R10a is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted C3-C12 cycloalkyl, optionally substituted aryl, aralkyl, (heteroaryl)alkyl, (cycloalkyl)alkyl, and optionally substituted 5- to 9-membered heteroaryl;
R10b is selected from the group consisting of hydrogen and C1-C4 alkyl;
R10c is selected from the group consisting of hydrogen and C1-C4 alkyl;
or
R10a and R10b taken together form a C3-C8 optionally substituted cycloalkyl or C4-C9 optionally substituted heterocyclo;
or
R10b and R10c taken together form a 4- to 9-membered optionally substituted heterocyclo;
G2 is selected from the group consisting of —C(R11b)— and —N—;
R11b is selected from the group consisting of hydrogen and C1-C3 alkyl;
a, b, c, and d are each independently 1, 2, or 3;
e, f, g, h, i, and j are each independently 0, 1, or 2;
L is -J1-Y1-J2-Y2-J3-Z—;
J1 is selected from the group consisting of alkylenyl, heteroalkylenyl, cycloalkylenyl, heterocyclenyl, phenylenyl, and heteroarylenyl;
or J1 is absent;
Y1 is selected from the group consisting of —(CH2)m—, —C≡C—, —CH═CH—, —N(R16a), —C(═O)—, —S(═O)2—, —C(═O)O—, —OC(═O)—, —C(═O)N(R16b)—, and —N(R16b)C(═O)—;
m is 0, 1, 2, or 3;
R16a is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
R16b is selected from the group consisting of hydrogen and C1-C4 alkyl;
J2 is selected from the group consisting of alkylenyl, heteroalkylenyl, cycloalkylenyl, heterocyclenyl, phenylenyl, and heteroarylenyl;
or J2 is absent;
Y2 is selected from the group consisting of —(CH2)n—, —C≡C—, —CH═CH—, —N(R12g), —C(═O)—, —S(═O)2—, —C(═O)O—, —OC(═O)—, —C(═O)N(R12h), and —(R12h)C(═O)N—;
n is 0, 1, 2, 3, 4, 5, or 6;
R12g is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
R12h is selected from the group consisting of hydrogen and C1-C4 alkyl;
J1 is selected from the group consisting of alkylenyl, heteroalkylenyl, cycloalkylenyl, heterocyclenyl, phenylenyl, and heteroarylenyl;
or J3 is absent;
Z and Z2 are independently selected from the group consisting of —(CH2)o—, —C≡C—, —CH═CH—, —C(═O)—, —O—, —S—, and —N(R12i)—;
o is 0, 1, 2, or 3;
R12i is selected from the group consisting of hydrogen, C1-C4 alkyl, and aralkyl;
wherein Z is attached to B;
L1 is spiroheterocyclenyl;
B is selected from the group consisting of:
E5 is selected from the group consisting of —C(R14a)═ and —N═;
E2 is selected from the group consisting of —C(R14b)═ and —N═;
E3 is selected from the group consisting of —C(R14c)═ and —N═;
E4 is selected from the group consisting of —C(R14d)═ and —N═;
Z1 is selected from the group consisting of —CH2 and —C(═O)—;
R13a is selected from the group consisting of hydrogen, methyl, and fluoro;
R13b is selected from the group consisting of hydrogen and methyl;
and
R14a, R14b, R14c, and R14d are each independently selected from the group consisting of hydrogen, halo, and C1-4 alkyl;
with the provisos:
(1) when R4 is -L-B, then Q is selected from the group consisting of Q1 and Q2;
and
(a) when Q is Q1, and R7a is selected from the group consisting of —C(═O)NH2—OC(═O)NH2, and —NR12aC(═O)NH2, then R6 is optionally substituted 5- to 14-membered heteroaryl;
or
(b) when Q is Q1, and R6 is selected from the group consisting of hydrogen, C1-C6 alkyl, optionally substituted aralkyl, optionally substituted C3-C6 cycloalkyl, optionally substituted 4- to 8-membered heterocyclo, and optionally substituted aryl, then R7a is selected from the group consisting of —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, OC(═O)NR12cR12d, —N(R12a)C(═O)NR12cR12d, —S(═O)2NR12eR12f, N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
or
(c) when Q is Q-2, then R7b is selected from the group consisting of —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, OC(═O)NR12cR12d, —N(R12a)C(═O)NR12cR12d, —S(═O)2NR12eR12f, N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
or
(d) B is selected from the group consisting of B-5, B-6, B-7, and B-8;
or
(2) when R4 is selected from the group consisting of C1-C6 alkyl, C1-C6 haloalkyl, (heterocyclo)alkyl, C(═O)R5a, and —S(═O)2R5b, then Q is Q-3, Q-4, Q-5, or Q-6;
and
(e) R7c, R7d, R7e, and R7f are each independently selected from the group consisting of —C(═O)NHR12b, —OC(═O)NHR12b, —NR12aC(═O)NHR12b, —NR12aC(═NH)NHR12b, —C(═O)NR12cR12d, —OC(═O)NR12cR12d, —N(R12a)C(═O)NR12cR12d, —S(═O)2NR12eR12f, —N(R12a)S(═O)2NR12eR12f, —N(R12a)S(═O)2R13a, —S(═O)2R13b, amino, cyano, optionally substituted 5- or 6-membered heterocyclo, and optionally substituted 5- or 6-membered heteroaryl;
or
(f) B is selected from the group consisting of B-5, B-6, B-7, and B-8;
or
(3) when R4 is selected from the group consisting of (carboxamido)alkyl and (amino)alkyl, then Q is Q-3, Q-4, Q-5, or Q-6.

98 more elements

Facts

Application

17/911,728Filed 26 Mar 2021 · us provisional application

Priority

26 Mar 2020

Published

US 2023/0159573 A125 May 2023

Granted

13 Jan 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification5 codes

C07F 9/6561
Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom: containing systems of two or more relevant hetero rings condensed among…
A61P 35/00
Antineoplastic agents
C07F 9/655354
The sulfur atom being part of a five-membered ring: condensed with carbocyclic rings or carbocyclic ring systems
C07F
Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen