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US 2026/0285833 A1Published application
Synthesis of mavorixafor and intermediates thereof
AssigneeX4 Pharmaceuticals, Inc.
InventorsAngelina Roberta Sekirnik, Art Taveras, Roger Hanselmann, Feng Gao, Zhigang Zhao, Tao Xiao
Life of this patent
Estimating the term…
Abstract
The present invention relates to methods for synthesizing the C-X-C receptor type 4 (CXCR4) inhibitor mavorixafor and to intermediates thereto.
Claims67
A method for preparing mavorixafor:
- or a pharmaceutically acceptable salt thereof;
- comprising the steps of:
- (a) coupling a compound of formula A:
- or a salt thereof;
- with a compound of formula C:
- or a salt thereof;
- to prepare a compound of formula D:
- or a salt thereof;
- (b) purifying the compound of formula D to prepare the enantiomerically enriched compound of formula E:
- or a salt thereof;
- (c) coupling the compound of formula E with a compound of formula F:
- or a salt thereof;
- wherein:
- LG1B is a suitable leaving group, ═O, or, taken with the carbon atom to which it is bound, an acetal;
- and
- PG1B is any combination of two amino protecting groups, any single amino protecting group and H, or two H;
- or PG1B is, taken with the nitrogen to which it is bound, a cyclic imide;
- or PG1B is absent and a triple bond is present between the corresponding nitrogen and the carbon to which the nitrogen is bound such that a nitrile is present;
- to prepare a compound of formula G:
- or salt thereof;
- and
- (d) deprotecting the compound of formula G to form mavorixafor or a pharmaceutically acceptable salt thereof.
19 more elements
A method for preparing mavorixafor:
- or a pharmaceutically acceptable salt thereof;
- comprising the steps of:
- (a) coupling a compound of formula A:
- or a salt thereof;
- with a compound of formula F′:
- or a salt thereof;
- wherein:
- PG1B is any combination of two amino protecting groups, any single amino protecting group and H, or two H;
- or PG1B is, taken with the nitrogen to which it is bound, a cyclic imide;
- or PG1B is absent and a triple bond is present between the corresponding nitrogen and the carbon to which the nitrogen is bound such that a nitrile is present;
- to prepare a compound of formula D′:
- or salt thereof;
- (b) purifying the compound of formula D′ to prepare the enantiomerically enriched compound of formula E′:
- or salt thereof;
- (c) coupling the compound of formula E′ with a compound of formula C′:
- or salt thereof;
- wherein:
- R1B is H, or a suitable benzimidazole protecting group;
- and
- LG1B is-O, a suitable leaving group, or, taken with the carbon atom to which it is bound, an acetal;
- to prepare a compound of formula G:
- or salt thereof;
- and
- (d) deprotecting the compound of formula G to form mavorixafor or a pharmaceutically acceptable salt thereof.
21 more elements
A method for preparing mavorixafor:
- or a pharmaceutically acceptable salt thereof;
- comprising the steps of:
- (a) coupling a compound of formula A:
- or a salt thereof;
- with a compound of formula H:
- or a salt thereof;
- to prepare a compound of formula J:
- or a salt thereof;
- (b) coupling the compound of formula J with a compound of formula K:
- or a salt thereof;
- wherein:
- LG1C is a suitable leaving group, ═O, or, taken with the carbon atom to which it is bound, an acetal;
- and
- PG1C is any combination of two amino protecting groups, any single amino protecting group and H, or two H;
- or PG1C is, taken with the nitrogen to which it is bound, a cyclic imide;
- or PG1C is absent and a triple bond is present between the corresponding nitrogen and the carbon to which the nitrogen is bound such that a nitrile is present;
- to prepare a compound of formula L:
- or salt thereof;
- (c) purifying the compound of formula L to prepare the enantiomerically enriched compound of formula M:
- or salt thereof;
- and
- (d) deprotecting the compound of formula M to form mavorixafor or a pharmaceutically acceptable salt thereof.
19 more elements
A method for preparing mavorixafor:
- or a pharmaceutically acceptable salt thereof;
- comprising the steps of:
- (a) coupling a compound of formula A:
- or a salt thereof;
- with a compound of formula K′:
- or salt thereof;
- wherein:
- PG1C is any combination of two amino protecting groups, any single amino protecting group and H, or two H;
- or PG1C is, taken with the nitrogen to which it is bound, a cyclic imide;
- or PG1C is absent and a triple bond is present between the corresponding nitrogen and the carbon to which the nitrogen is bound such that a nitrile is present;
- to prepare a compound of formula J′:
- or salt thereof;
- (b) coupling the compound of formula J′ with a compound of formula H′:
- or salt thereof;
- wherein:
- LG1C is ═O, a suitable leaving group, or, taken with the carbon atom to which it is bound, an acetal;
- to prepare a compound of formula L:
- or salt thereof;
- (c) purifying the compound of formula L to prepare the enantiomerically enriched compound of formula M:
- or salt thereof;
- and
- (d) deprotecting the compound of formula M to form mavorixafor or a pharmaceutically acceptable salt thereof.
19 more elements
A method for the purification of a compound of formula N:
- or a salt thereof;
- to prepare an enantiomerically enriched compound of formula O:
- or a salt thereof.
Dependencies are inferred from the claim text.