US 2025/0206753 A1Published application

Fused bicyclic compounds for the treatment of disease

AssigneeAkarna Therapeutics, Ltd.

InventorsRaju MOHAN, Benjamin Anthony PRATT

Life of this patent

Estimating the term…

Abstract

Described herein are fused bicyclic compounds, compositions, and methods for their use for the treatment of disease.

Claims73

Dependent claims

A compound having the Formula (I), or a pharmaceutically acceptable salt, solvate, or prodrug thereof:

wherein:
R1 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R2 is selected from the group consisting of —CN, —C(O)OR25, —C(O)N(R25)R26,
or R1 and R2 together with the carbon atoms to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring or an optionally substituted heteroaryl ring;
R3 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted heteroaryl, optionally substituted C2-C9heterocycloalkyl, optionally substituted —(C1-C2alkylene)-(heteroaryl), —C(O)R20, —C(O)OR20, —S(O)2R20, —C(O)N(R21)R22, —C(O)N(R21)S(O)2R24, —C(O)N(R23)N(R21)R22, —C(O)N(R23)N(R21)S(O)2R24, —N(R23)C(O)R20, —N(R23)C(O)N(R21)R22, —N(R23)C(O)N(R21)S(O)2R24, —N(R20)C(O)N(R23)N(R21)R22, —N(R20)C(O)N(R23)N(R21)S(O)2R24, —N(R23)C(O)OR20, —P(O)OR20, and —P(O)(OR19)OR20;
R4 and R5 are each independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
or R4 and R5 together with the carbon atom to which they are attached, form an optionally substituted C3-C6cycloalkyl ring or an optionally substituted C2-C7heterocycloalkyl ring;
R6 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, and —C(O)N(R27)R28;
R7 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
R8 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted heteroaryl, optionally substituted C2-C9heterocycloalkyl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R9 and R10 together with the carbon atoms to which they are attached, form an optionally substituted nitrogen containing 6-membered heteroaryl ring;
R19, R20, and R23 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R21 and R22 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
or R21 and R22 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
R24 is selected from the group consisting of optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted, aryl optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
and
R25 and R26 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R27 and R28 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
or R27 and R28 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring.

16 more elements

A compound having the structure of Formula (II), or a pharmaceutically acceptable salt, solvate, or prodrug thereof:

wherein:
R1 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R2 is selected from the group consisting of —CN, —C(O)OR25, —C(O)N(R25)R26,
or R1 and R2 together with the carbon atoms to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring or an optionally substituted heteroaryl ring;
R4 and R5 are each independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
or R4 and R5 together with the carbon atom to which they are attached, form an optionally substituted C3-C6cycloalkyl ring or an optionally substituted C2-C7heterocycloalkyl ring;
R6 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, and —C(O)N(R27)R28;
R7 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
R8 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted heteroaryl, optionally substituted C2-C9heterocycloalkyl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R9 and R10 together with the carbon atoms to which they are attached, form an optionally substituted nitrogen containing 6-membered heteroaryl ring;
R25 and R26 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R27 and R28 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
or R27 and R28 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
R30 is halogen,
each R31 is independently halogen, —OH, —CN, —NO2, —NH2, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkylamine, optionally substituted C3-C8cycloalkyl, optionally substituted C2-C9heterocycloalkyl, aryl, or heteroaryl;
each R32 and R33 are each independently selected from the group consisting of hydrogen, halogen, and C1-C6alkyl;
R34 and R35 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, and optionally substituted C2-C9heterocycloalkyl;
or R34 and R35 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
p is 0, 1, 2, 3, or 4;
r is 0, 1, 2, 3, or 4;
and
t is 2, 3, or 4.

19 more elements

A compound having the structure of Formula (III), or a pharmaceutically acceptable salt, solvate, or prodrug thereof:

wherein:
R1 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R2 is selected from the group consisting of —CN, —C(O)OR25, —C(O)N(R25)R26,
or R1 and R2 together with the carbon atoms to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring or an optionally substituted heteroaryl ring;
R4 and R5 are each independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
or R4 and R5 together with the carbon atom to which they are attached, form an optionally substituted C3-C6cycloalkyl ring or an optionally substituted C2-C7heterocycloalkyl ring;
R6 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, and —C(O)N(R27)R28;
R7 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
R8 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted heteroaryl, optionally substituted C2-C9heterocycloalkyl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
each R12 is independently selected from the group consisting of hydrogen and C1-C6alkyl;
each R13 and R14 are each independently selected from the group consisting of hydrogen and C1-C6alkyl;
or R13 and R14 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
each R15 is independently selected from the group consisting of halogen, —OH, —CN, —NO2, —NH2, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkylamine, optionally substituted C3-C8cycloalkyl, optionally substituted C2-C9heterocycloalkyl, aryl, heteroaryl, —C(O)OR12, —C(O)N(R13)R14, —OC(O)OR12, —OC(O)N(R13)R14, —N(R13)C(O)OR12, and —N(R13)C(O)N(R13)R14;
R25 and R26 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R27 and R28 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
or R27 and R28 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
R30 is halogen, —OH, —CN, —NO2, —NH2, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkylamine, optionally substituted C3-C8cycloalkyl, optionally substituted C2-C9heterocycloalkyl, aryl, heteroaryl,
each R31 is independently halogen, —OH, —CN, —NO2, —NH2, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkylamine, optionally substituted C3-C8cycloalkyl, optionally substituted C2-C9heterocycloalkyl, aryl, or heteroaryl;
each R32 and R33 are each independently selected from the group consisting of hydrogen, halogen, and C1-C6alkyl;
R34 and R35 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, and optionally substituted C2-C9heterocycloalkyl;
or R34 and R35 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
n is 0, 1, 2, or 3
p is 0, 1, 2, 3, or 4;
r is 0, 1, 2, 3, or 4;
and
t is 2, 3, or 4.

23 more elements

A compound having the structure of Formula (IV), or a pharmaceutically acceptable salt, solvate, or prodrug thereof:

wherein:
R1 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R2 is selected from the group consisting of —CN, —C(O)OR25, —C(O)N(R25)R26,
or R1 and R2 together with the carbon atoms to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring or an optionally substituted heteroaryl ring;
R4 and R5 are each independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
or R4 and R5 together with the carbon atom to which they are attached, form an optionally substituted C3-C6cycloalkyl ring or an optionally substituted C2-C7heterocycloalkyl ring;
R6 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, and —C(O)N(R27)R28;
R7 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
R8 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted heteroaryl, optionally substituted C2-C9heterocycloalkyl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
each R12 is independently selected from the group consisting of hydrogen and C1-C6alkyl;
each R13 and R14 are each independently selected from the group consisting of hydrogen and C1-C6alkyl;
or R13 and R14 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
each R15 is independently selected from the group consisting of halogen, —OH, —CN, —NO2, —NH2, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkylamine, optionally substituted C3-C8cycloalkyl, optionally substituted C2-C9heterocycloalkyl, aryl, heteroaryl, —C(O)OR12, —C(O)N(R13)R14, —OC(O)OR12, —OC(O)N(R13)R14, —N(R13)C(O)OR12, and —N(R13)C(O)N(R13)R14;
R25 and R26 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R27 and R28 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
or R27 and R28 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
R30 is halogen, —OH, —CN, —NO2, —NH2, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkylamine, optionally substituted C3-C8cycloalkyl, optionally substituted C2-C9heterocycloalkyl, aryl, heteroaryl,
each R31 is independently halogen, —OH, —CN, —NO2, —NH2, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C1-C6alkylamine, optionally substituted C3-C8cycloalkyl, optionally substituted C2-C9heterocycloalkyl, aryl, or heteroaryl;
each R32 and R33 are each independently selected from the group consisting of hydrogen, halogen, and C1-C6alkyl;
R34 and R35 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, and optionally substituted C2-C9heterocycloalkyl;
or R34 and R35 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
n is 0, 1, 2, or 3
p is 0, 1, 2, 3, or 4;
r is 0, 1, 2, 3, or 4;
and
t is 2, 3, or 4.

23 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/925,911Filed 24 Oct 2024
Priority: 22 Dec 2014
Published: 26 Jun 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 487/14
In which the condensed system contains three hetero rings: ortho-condensed systems
A61K 31/407
Having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil: condensed with other…
A61P 3/00
Drugs for disorders of the metabolism
C07D
Heterocyclic compounds

Family

Application62/095,646Us provisional application · filed 22 Dec 2014
Application15/630,189Continuation · filed 22 Jun 2017
Application16/237,017Continuation · filed 31 Dec 2018
Application17/024,095Continuation · filed 17 Sep 2020
Application18/311,171Continuation · filed 2 May 2023
Application18/925,911Continuation
US 10,167,294 B2Related patent
US 10,793,577 B2Related patent
US 2017/0355704 A1Published application
US 2019/0211026 A1Published application
US 2021/0139490 A1Published application
US 2024/0025914 A1Published application
US 2025/0206753 A1This patent

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

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A compound having the Formula (I), or a pharmaceutically acceptable salt, solvate, or prodrug thereof:

wherein:
R1 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R2 is selected from the group consisting of —CN, —C(O)OR25, —C(O)N(R25)R26,
or R1 and R2 together with the carbon atoms to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring or an optionally substituted heteroaryl ring;
R3 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted heteroaryl, optionally substituted C2-C9heterocycloalkyl, optionally substituted —(C1-C2alkylene)-(heteroaryl), —C(O)R20, —C(O)OR20, —S(O)2R20, —C(O)N(R21)R22, —C(O)N(R21)S(O)2R24, —C(O)N(R23)N(R21)R22, —C(O)N(R23)N(R21)S(O)2R24, —N(R23)C(O)R20, —N(R23)C(O)N(R21)R22, —N(R23)C(O)N(R21)S(O)2R24, —N(R20)C(O)N(R23)N(R21)R22, —N(R20)C(O)N(R23)N(R21)S(O)2R24, —N(R23)C(O)OR20, —P(O)OR20, and —P(O)(OR19)OR20;
R4 and R5 are each independently selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
or R4 and R5 together with the carbon atom to which they are attached, form an optionally substituted C3-C6cycloalkyl ring or an optionally substituted C2-C7heterocycloalkyl ring;
R6 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, and —C(O)N(R27)R28;
R7 is selected from the group consisting of hydrogen, halogen, optionally substituted C1-C6alkyl, optionally substituted C1-C6alkoxy, optionally substituted C2-C6alkenyl, and optionally substituted C2-C6alkynyl;
R8 is selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted heteroaryl, optionally substituted C2-C9heterocycloalkyl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R9 and R10 together with the carbon atoms to which they are attached, form an optionally substituted nitrogen containing 6-membered heteroaryl ring;
R19, R20, and R23 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R21 and R22 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
or R21 and R22 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring;
R24 is selected from the group consisting of optionally substituted C1-C6alkyl, optionally substituted C2-C6alkenyl, optionally substituted C2-C6alkynyl, optionally substituted C3-C8 cycloalkyl, optionally substituted, aryl optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
and
R25 and R26 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
R27 and R28 are each independently selected from the group consisting of hydrogen, optionally substituted C1-C6alkyl, optionally substituted C3-C8cycloalkyl, optionally substituted aryl, optionally substituted —(C1-C2alkylene)-(aryl), optionally substituted C2-C9heterocycloalkyl, optionally substituted heteroaryl, and optionally substituted —(C1-C2alkylene)-(heteroaryl);
or R27 and R28 together with the nitrogen atom to which they are attached, form an optionally substituted C2-C9heterocycloalkyl ring.

16 more elements

Facts

Application

18/925,911Filed 24 Oct 2024

Priority

22 Dec 2014

Published

26 Jun 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 487/14
In which the condensed system contains three hetero rings: ortho-condensed systems
A61K 31/407
Having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil: condensed with other…
A61P 3/00
Drugs for disorders of the metabolism
C07D
Heterocyclic compounds

Family

Application62/095,646Us provisional application · filed 22 Dec 2014

Application15/630,189Continuation · filed 22 Jun 2017

Application16/237,017Continuation · filed 31 Dec 2018

Application17/024,095Continuation · filed 17 Sep 2020

Application18/311,171Continuation · filed 2 May 2023

Application18/925,911Continuation

US 10,167,294 B2Related patent

US 10,793,577 B2Related patent

US 2017/0355704 A1Published application

US 2019/0211026 A1Published application

US 2021/0139490 A1Published application

US 2024/0025914 A1Published application

US 2025/0206753 A1This patent

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