Granted Patent B2

US 11,602,527 · App. 17/035,611 · Granted Mar 14, 2023

Inventors: Alfredo C. Castro (Winchester, MA); Michael J. Grogan (Winchester, MA); Karen J. McGovern (Groton, MA); Martin R. Tremblay (Melrose, MA)

Assignee: Infinity Pharmaceuticals, Inc.

A61K31/4355A61K9/0014A61K31/17A61K31/196A61K31/198A61K31/454A61K31/4745A61K31/519A61K31/56A61K31/573A61K31/58A61K31/664A61K31/69A61K31/704A61K31/7068A61K31/7076A61K38/21A61K45/06A61N5/10C07D307/94C07D471/04C07D471/10C07D491/04C07D491/048C07D491/10C07D491/107C07J69/00

Abstract

Claims (20)

1. A method for treating a medulloblastoma, the method comprising administering to a subject an effective amount of a compound having the formula:

or a pharmaceutically acceptable salt thereof;

wherein R 1 is H, alkyl, —OR, amino, sulfonamido, sulfamido, —OC(O)R 5 , —N(R 5 )C(O)R 5 , or a sugar;

R 2 is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, nitrile, or heterocycloalkyl;

or R 1 and R 2 taken together form ═O, ═S, ═N(OR), ═N(R), ═N(NR 2 ), or ═C(R) 2 ;

R 3 is H, alkyl, alkenyl, or alkynyl;

R 4 is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, heteroaralkyl, haloalkyl, —OR 5 , —C(O)R 5 , —CO 2 R 5 , —SO 2 R 5 , —C(O)N(R 5 )(R 5 ), —[C(R) 2 ] q —R 5 , —[(W)—N(R)C(O)] q R 5 , —[(W)—C(O)] q R 5 , —[(W)—C(O)O] q R 5 , —[(W)—OC(O)] q R 5 , —[(W)—SO 2 ] q R 5 , —[(W)—N(R 5 )SO 2 ] q R 5 , —[(W)—C(O)N(R 5 )] q R 5 , —[(W)—O] q R 5 , —[(W)—N(R)] q R 5 , —W—NR 5 3 + X − or —[(W)—S] q R 5 ;

wherein each W is, independently, a diradical;

each q is independently for each occurrence 1, 2, 3, 4, 5, or 6;

X − is a halide;

each R is independently, H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl or aralkyl;

each R 5 is, independently, H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, heteroaralkyl or —[C(R) 2 ] p —R 6 ; wherein p is 0-6; or any two occurrences of R 5 on the same substituent can be taken together to form a 4-8 membered optionally substituted ring which contains 0-3 heteroatoms selected from N, O, S, and P; and

each R 6 is independently hydroxyl, —N(R)COR, —N(R)C(O)OR, —N(R)SO 2 (R), —C(O)N(R) 2 , —OC(O)N(R)(R), —SO 2 N(R)(R), —N(R)(R), —COOR, —C(O)N(OH)(R), —OS(O) 2 OR, —S(O) 2 OR, —OP(O)(OR)(OR), —NP(O)(OR)(OR), or —P(O)(OR)(OR).

2. The method of claim 1 , wherein when R 2 , R 3 , and R 4 are H; R 1 is not hydroxyl or a sugar; and when R 4 is hydroxyl, then R 1 is not a sugar or hydroxyl; and when R 4 is hydroxyl, then R 1 and R 2 together are not C═O.

3. The method of claim 1 , wherein R 1 is sulfonamido.

4. The method of claim 1 , wherein the compound is administered orally.

5. The method of claim 1 , wherein the compound is administered intravenously.

6. The method of claim 1 , wherein the compound is administered topically.

7. The method of claim 1 , wherein the compound is selected from the group consisting of:

or a pharmaceutically acceptable salt thereof.

Assignments (1)

Continuity (11)