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US 10,590,167 B2Granted
NMDA receptor modulators and prodrugs, salts, and uses thereof
AssigneeNaurex, Inc.
InventorAmin Khan
Life of this patent
Estimating the term…
Abstract
Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.
Claims12
A peptidyl compound of the formula:
- wherein:
- R1, R2, and R3 are independently selected from the group consisting of hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted, aryl;
- substituted or unsubstituted heteroaryl;
- —ORx;
- —NO2;
- —N3;
- —CN;
- —SCN;
- —SRx;
- —C(O)Rx;
- —CO2(Rx);
- —C(O)N(Rx)2;
- —C(NRx)N(Rx)2;
- —OC(O)Rx;
- —OCO2Rx;
- —OC(O)N(Rx)2;
- —N(Rx)2;
- —SORx;
- —S(O)2Rx;
- —NRxC(O)Rx;
- —NRxC(O)N(Rx)2;
- —NRxC(O)ORx;
- —NRxC(NRx)N(Rx)2;
- and —C(Rx)3;
- wherein each occurrence of Rx is independently selected from the group consisting of hydrogen;
- halogen;
- acyl;
- optionally substituted aliphatic;
- optionally substituted heteroaliphatic;
- optionally substituted aryl;
- and optionally substituted heteroaryl;
- R5 and R6 are independently selected from the group consisting of -Q-Ar and hydrogen;
- wherein Q is independently selected from the group consisting of cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- and a bond;
- and wherein Ar is selected from the group consisting substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
- or R5 and R6, together with the atoms to which they are attached, form a substituted or unsubstituted 4-6 membered heterocyclic or cycloalkyl ring;
- R7 and R8 are independently selected from the group consisting of hydrogen;
- halogen;
- hydroxyl;
- substituted or unsubstituted C1-C6 alkyl;
- substituted or unsubstituted C1-C6 alkoxy;
- and substituted or unsubstituted aryl;
- or R7 and R8, together with the atoms to which they are attached, form a substituted or unsubstituted 4-6 membered heterocyclic or cycloalkyl ring;
- R16 is selected from the group consisting of hydrogen;
- C1-C6 alkyl, optionally substituted by one or more substituents each independently selected from the group consisting of halogen, oxo, and hydroxyl;
- C2-6alkenyl, optionally substituted, by one or more substituents each independently selected from the group consisting of halogen, oxo, and hydroxyl;
- C2-6alkynyl, optionally substituted by one or more substituents each independently selected from the group consisting of halogen, oxo, and hydroxyl;
- C3-6cycloalkyl, optionally substituted by one or more substituents each independently selected from the group consisting of C1-6alkyl, halogen, oxo, and hydroxyl;
- and phenyl, optionally substituted by one or more substituents each independently selected from the group consisting of C1-6alkyl, C1-6alkoxy;
- halogen, and hydroxyl;
- —C(O)Rx;
- —CO2(Rx);
- —C(O)N(Rx)2;
- —C(NRx)N(Rx)2;
- and —C(Rx)3;
- wherein each occurrence of Rx is independently selected from the group consisting of hydrogen;
- halogen;
- C1-6alkyl;
- C2-6alkenyl;
- C2-6alkynyl;
- C3-6cycloalkyl;
- and phenyl;
- L is selected from the group consisting of cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted aryl;
- and substituted or unsubstituted heteroaryl;
- and pharmaceutically acceptable salts, and stereoisomers thereof.
69 more elements
A compound represented by:
- wherein:
- A1 is —(C1-C6 alkyl)-aryl-;
- R1, R2, R3 are independently selected from the group consisting of hydrogen;
- halogen;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted aryl;
- substituted or unsubstituted, heteroaryl;
- —ORx;
- —NO2;
- —N3;
- —CN;
- —SCN;
- —SRx;
- —C(O)Rx;
- —CO2(Rx);
- —C(O)N(Rx)2;
- —C(NRx)N(Rx)2;
- —OC(O)Rx;
- —OCO2Rx;
- —OC(O)N(Rx)2;
- —N(Rx)2;
- —SORx;
- —S(O)2Rx;
- —NRxC(O)Rx;
- —NRxC(O)N(Rx)2;
- —NRxC(O)ORx;
- —NRxC(NRx)N(Rx)2;
- and —C(Rx)3;
- wherein each occurrence of Rxis independently selected from the group consisting of hydrogen;
- halogen;
- acyl;
- optionally substituted aliphatic;
- optionally substituted heteroaliphatic;
- optionally substituted aryl;
- and optionally substituted heteroaryl;
- R5 and R6 are independently selected from the group consisting of -Q-Ar and hydrogen;
- wherein Q is independently selected from the group consisting of cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- and a bond;
- and wherein Ar is selected from the group consisting substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
- or R5 and R6, together with the atoms to which they are attached, form a substituted or unsubstituted 4-6 membered heterocyclic or cycloalkyl ring;
- R7 and R8 are independently selected from the group consisting of hydrogen;
- halogen;
- hydroxyl;
- substituted or unsubstituted C1-C6 alkyl;
- substituted or unsubstituted C1-C6 alkoxy;
- and substituted or unsubstituted aryl;
- or R7 and R8, together with the atoms to which they are attached, form a substituted or unsubstituted 4-6 membered heterocyclic or cycloalkyl ring;
- R16 is selected from the group consisting of hydrogen;
- C1-C6 alkyl, optionally substituted by one or more substituents each independently selected from the group consisting of halogen, oxo, and hydroxyl;
- C2-6alkenyl, optionally substituted by one or more substituents each independently selected from the group consisting of halogen, oxo, and hydroxyl;
- C2-6alkynyl, optionally substituted by one or more substituents each independently selected from the group consisting of halogen, oxo, and hydroxyl;
- C3-6cycloalkyl, optionally substituted by one or more substituents each independently selected from the group consisting of C1-6alkyl, halogen, oxo, and hydroxyl;
- and phenyl, optionally substituted by one or more substituents each independently selected from the group consisting of C1-6alkyl,C1-6alkoxy;
- halogen, and hydroxyl;
- —C(O)Rx;
- —CO2(Rx);
- —C(O)N(Rx)2;
- —C(NRx)N(Rx)2;
- and —C(Rx)3;
- wherein each occurrence of Rx is independently selected from the group consisting of hydrogen;
- halogen;
- C1-6alkyl;
- C2-6alkynyl;
- C2-6alkynyl;
- C3-6cycloalkyl;
- and phenyl;
- L is selected from the group consisting of cyclic of acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
- cycle or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
- substituted or unsubstituted aryl;
- and substituted or unsubstituted heteroaryl;
- and pharmaceutically acceptable salts, and stereoisomers thereof.
70 more elements
A compound represented by:
A compound represented by:
Dependencies are inferred from the claim text.