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US 12,358,929 B2Granted
NMDA receptor modulators and uses thereof
AssigneeNovartis AG
InventorsDavid R. Anderson, Robert A. Volkmann, Frank S. Menniti, Christopher Fanger, Yuelian Xu
Life of this patent
Estimating the term…
Abstract
Disclosed herein, in part, are heteroaromatic compounds and methods of use in treating neuropsychiatric disorders, e.g., schizophrenia and major depressive disorder. Pharmaceutical compositions and methods of making heteroaromatic compounds are provided. The compounds are contemplated to modulate the NMDA receptor.
Claims14
A compound of the Formula Ic:
- or a pharmaceutically acceptable salt thereof, wherein
- R1 is selected from the group consisting of hydrogen, halogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C1-6alkoxy, C3-6cycloalkyl, —C(O)OH, —C(O)OC1-6alkyl, (C3-6) cycloalkyl and phenyl (optionally substituted by one, two or three substituents each selected from halogen, C1-6alkyl, C1-6alkoxy, —C(O)OH, —C(O)OC1-6alkyl and NRaRb);
- R4 is selected from the group consisting of hydrogen, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, —CO2H, —CO2C1-6alkyl, —CO2 NRaRb, NRaRb, C3-6cycloalkyl and phenyl (optionally substituted by one or two substituents each selected from halogen or methyl);
- R5 independently for each occurrence is selected from the group consisting of hydrogen, C1-6alkyl, C1-6alkoxy, halogen, cyano, OH, C2-6alkenyl, C2-6alkynyl, C3-6cycloalkyl, heteroaryl, phenyl, —NRaRb, —C(O)OH, C1-6alkylcarbonyl, C1-6alkoxycarbonyl, (NRaRb) carbonyl-, C1-6alkyl-S(O)w— (where w is 0, 1 or 2), and RaRbN—SOw— (where w is 0, 1 or 2);
- wherein heteroaryl and phenyl may optionally be substituted by one, two or three substituents each selected from the group consisting of halogen, cyano, C1-6alkyl, C1-6alkoxy, and —NRaRb;
- wherein one or more carbon atoms of said C3-6cycloalkyl may be optionally replaced by N or O;
- or two R5, together with two adjacent carbons on ring A to which they are attached, form a 5-7 membered unsaturated, partially unsaturated or saturated carbocyclic or heterocyclic ring;
- R6 for each occurrence is independently selected from the group consisting of hydrogen, C1-6alkyl, C3-6cycloalkyl, —C(O)—C1-6alkyl, and phenyl (optionally substituted by one or two substituents each selected from halogen or methyl);
- Ring A is pyridinyl, pyrimidinyl or pyridazinyl;
- RC is selected from the group consisting of cyano, hydrogen, halogen, S(C1-6) alkyl, S(O)(C1-6) alkyl, SO2(C1-6)alkyl, C(O)NRaRb, —C(O)OH, —C(O)O(C1-6)alkyl, (C1-6)alkyl, (C2-6) alkenyl, (C2-6) alkynyl and heteroaryl (optionally substituted by C1-4alkyl or halogen);
- Ra and Rb are independently selected, for each occurrence, from the group consisting of:
- hydrogen, C1-4alkylcarbonyl, C1-6alkoxycarbonyl, cyclopropyl, and C1-3alkyl;
- wherein C1-3alkyl may optionally be substituted on a carbon not bound to the nitrogen by one or more substituents each selected from the group consisting of fluorine, cyano, oxo and hydroxyl;
- or Ra and Rb, together with the nitrogen to which they are attached, form a 4-6 membered heterocyclic ring which may have an additional heteroatom selected from O, S, or N (optionally substituted by one or two methyl groups);
- and wherein the 4-6 membered heterocyclic ring may optionally be substituted on a carbon not bound to the nitrogen by one or more substituents;
- and
- p is 0, 1, 2 or 3.
14 more elements
A compound, wherein the compound is selected from:
- or a pharmaceutically acceptable salt of any of the foregoing.
Dependencies are inferred from the claim text.