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US 12,065,465 B2Granted
Methods for assembly of tetracyclic compounds by stereoselective C9-C10 bond formation
AssigneeTrustees of Dartmouth College
InventorGlenn C. Micalizio
Life of this patent
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Abstract
The present disclosure relates to stereodefined polycyclic (e.g., tetracyclic) compounds that contain quaternary centers at one or multiple ring fusions, synthetic methods for preparing such compounds, and methods of using such compounds to treat a disease, such as a brain tumor and, particularly, a glioma.
Claims14
A compound or salt thereof, wherein the compound has a structure corresponding to Formula (X-A1):
- m is an integer selected from the group consisting of 1, 2, or 3;
- n is an integer selected from the group consisting of 0, 1, 2, 3, and 4;
- each RA is independently selected from the group consisting of hydrogen, C1-10-alkyl, C2-10-alkenyl, C2-10-alkynyl, C1-10-haloalkyl, halogen, —ORAX, —SRAY, —S(O)2NRZ1RZ2, —S(O)2RZ1, —S(O)RZ1, —NRZ1RZ2, —N(RZ1)C(O)RZ2, —N(RZ1)S(O)2RZ2, C6-10-aryl, and 5- to 10-membered heteroaryl,
- wherein RAX is hydrogen, C1-6-alkyl, C2-10-alkenyl, C2-10-alkynyl, C1-10-haloalkyl, —C(O)—C1-10-alkyl, —C(O)—C6-10-aryl, —C(O)-heteroaryl, —C(O)—O—C1-10-alkyl, —C(O)—O—C6-10-aryl, —C(O)—O-heteroaryl, —C(O)—NRZ1RZ2, —S(O)2NRZ1RZ2, —S(O)2RZ1, C6-10-aryl, or 5- to 10-membered heteroaryl,
- wherein RAY is hydrogen, C16-alkyl, C2-10-alkenyl, C2-10-alkynyl, C1-10-haloalkyl, —C(O)—C1-10-alkyl, —C(O)—C6-10-aryl, —C(O)-heteroaryl, C6-10-aryl, or 5- to 10-membered heteroaryl,
- wherein each of RZ1 and RZ2 are independently hydrogen, C1-6-alkyl, C2-10-alkenyl, C2-10-alkynyl, C1-10-haloalkyl, C6-10-aryl, 5- to 10-membered heteroaryl, hydroxy, or C1-6-alkoxy;
- R9 is selected from the group consisting of C1-10-alkyl, C2-10-alkenyl, C2-10-alkynyl, C1-10-haloalkyl, halogen, —(CH2)m—C6-10-aryl, and —(CH2)m-5- to 10-membered heteroaryl;
- R13 is selected from the group consisting of C1-10-alkyl, C2-10-alkenyl, C2-10-alkynyl, C1-10-haloalkyl, —(CH2)m—C6-10-aryl, and —(CH2)m-5- to 10-membered heteroaryl;
- and
- RD is selected from the group consisting of hydrogen, C1-6-alkyl, C2-10-alkenyl, C2-10-alkynyl, C1-10-haloalkyl, —C(O)—C1-10-alkyl, —C(O)—C6-10-aryl, —C(O)-heteroaryl, —C(O)—O—C1-10-alkyl, —C(O)—O—C6-10-aryl, —C(O)—O-heteroaryl, —C(O)—NRZ1RZ2, C6-10-aryl, and 5- to 10-membered heteroaryl;
- wherein any C6-10-aryl or 5- to 10-membered heteroaryl is optionally substituted with one or more halogen, hydroxy, C1-6-alkyl, C1-6-haloalkyl, or C1-6-alkoxy.
8 more elements
Dependencies are inferred from the claim text.