IP Library › Patent Application 17598569

Patent Application

App. No. 17/598,569

PANTETHENOYLCYSTEINE DERIVATIVES AND USES THEREOF

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App. No.: 17/598,569

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Abstract

The present disclosure relates to compounds of Formula (I) or (II): (Formulae (I), (II)), and pharmaceutically acceptable salts or solvates thereof. The present disclosure also relates to pharmaceutical compositions comprising the compounds and therapeutic and diagnostic uses of the compounds and pharmaceutical compositions.

Claims (150)

1 . A compound of Formula (I) or (II):

or a pharmaceutically acceptable salt or solvate thereof, wherein:

R 1 is H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —C(═O)R 1b , —C(═O)R 1c , —C(═O)R 1z , —C(═O)—(CH═CH) n R 1a , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —R 1a , —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] p —[CH 2 ] q —R 1a , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH(OR 1c )—CH 2 ] r —[CH 2 ] q —R 1a , —C(═O)CH 2 —[C(═O)R 1b ]—[C(═O)CH 2 ] p —[CH(OR 1c )—CH 2 ] r —[CH 2 ] q —R 1a , —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] r [C(═O)CH 2 ] p —[CH 2 ] q —R 1a , —C(═O)OR 1c , —C(═O)N(R 1c ) 2 , —C(═O)—CH═CH—C(═O)OR 1c , —C(═O)—[CH 2 ] q —C(═O)OR 1c , —C(═O)—CH 2 CH 2 —C(═O)OR 1c , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —C(═O)OR 1c , —C(═O)—[CH 2 ] q —C(═O)R 1a , —C(═O)—[CH 2 ] q —C(═O)R 1z , —[C(═O)CH 2 ] q —C(═O)R 1z , —C(═O)—CH 2 CH 2 —C(═O)R 1z , —C(═O)—CH═CH—[C(═O)] p R 1z , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ?]—C(═O)R 1z , —C(═O)CHR 1c —[C(═O)CHR 1c ] p —[CH 2 ] q —R 1a , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —C(═O)R 1a , —SR 1d ,

wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1a , and wherein one or more methylene moieties in the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, or C 2 -C 20 alkynyl are optionally replaced by one or more carbonyl moieties;

each R 1a is independently H, halogen, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, —OR 1c , —C(═O)OR 1c , —C(═O)N(R 1c ) 2 , —N(R 1b ) 2 , —N(R 1c ) 2 , —N(R 1c )C(═O))R 1b , —N(R 1c )C(═O)R 1z , —N(R 1c )C(═O)OR 1c , —OC(═O)R 1b , —OC(═O)R 1z , —OC(═O)OR 1c , —SC(═O)R 1b , —SC(═O)R 1z , —SC(═O)OR 1c , —SC(═O)N(R 1c ) 2 , —C(═O)R 1b , —C(═O)R 1z , —SR 1d , or R 1z , wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, or C 2 -C 20 alkynyl is optionally substituted with one or more R 1e ;

each R 1b is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, —(CH 2 ) q —C(═O)OR 1c , —(CH 2 ) q —C(═O)R 1c , —CH 2 —C(═O)—(CH 2 ) q —C(═O)OR 1c , —CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —C(═O)OR 1c , —CH═CH—C(═O)OR 1c , —C(R 1e )═C(R 1e )—C(═O)OR 1c , —C(═O)OR 1c , —C(═O)N(R 1c ) 2 , or R 1z , wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, or C 2 -C 20 alkynyl is optionally substituted with one or more R 1e ;

each R 1c is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl), wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl) is optionally substituted with one or more R 1e ; or two R 1c together with the one or more intervening atoms to which they are connected, form C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl, wherein the C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl is optionally substituted with one or more R 1e ;

each R 1d is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 10 cycloalkyl, C 1 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 120 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl), wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl) is optionally substituted with one or more R 1e ;

each R 1e is independently H, halogen, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, —OR 1g , —C(═O)OR 1g , —C(═O)N(R 1g ) 2 , —N(R 1g ) 2 , —N(R 1g )C(═O)R 1f , —N(R 1g )C(═NH)R 1f , —N(R 1g )C(═O)R 1z , —N(R 1g )C(═O)OR 1g , —OC(═O)R 1f , —OC(═O)R 1z , —OC(═O)OR 1g , —SR 1g , —N + (R 1g ) 3 , —SC(═O)R 1f , —SC(═O)R 1z , —SC(═O)OR 1g , —SC(═O)N(R 1g ) 2 , —C(═O)R 1f , —C(═O)R 1z , C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, or R 1z , wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1f or R 1z ;

each R 1f is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, —OR 1g , —CH 2 C(═O)OR 1g , —CH═CH—C(═O)OR 1g , —C(═O)OR 1g , —C(═O)N(R 1g ) 2 , —N(R 1g ) 2 , or R 1z , wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, or C 2 -C 20 alkynyl is optionally substituted with one or more —OR 1g or R 1z ;

each R 1g is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl), wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl) is optionally substituted with one or more R 1z ;

each R 1z is independently

each n is independently an integer ranging from 0 to 20;

each p is independently an integer ranging from 0 to 20;

each q is independently an integer ranging from 0 to 20;

each r is independently an integer ranging from 0 to 20;

R 2 and R 3 are independently H, R 1c , —C(═O)R 1b , —C(═O)OR 1e , —C(═O)N(R 1c ) 2 , —C(═O)R 1z , —C(═O)—CH═CH—C(═O)OR 1c , —C(═O)—CH 2 —CH 2 —C(═O)OR 1c ,

—C(═O)—CH═CH—C(═O)—R 1z , —C(═O)—CH 2 —CH 2 —C(═O)—R 1z ,

each X is independently —OR 1c , —SR 1c , —N(R 1c ) 2 ,

or R 1z ;

or two X, together with the one or more intervening atoms to which they are connected, form C 5 -C 12 heterocycloalkyl or C 5 -C 12 heteroaryl, wherein the C 5 -C 12 heterocycloalkyl or C 5 -C 12 heteroaryl is optionally substituted with one or more R 1a ;

each R 4 is independently H, —C(═O)OR 4a , or —C(═O)N(R 4a ) 2 ;

each R 4a is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 4b ;

each R 4b is independently H, halogen, —OR 4c , —C(═O)OR 4c , —C(═O)N(R 4c ) 2 , or —N(R 4c ) 2 ;

each R 4c is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl;

each R 5 is independently H, —C(═O)OR 5a , or —C(═O)N(R 5a ) 2 ;

each R 5a is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl;

each R 6 is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 6a ;

each R 6a is independently halogen, —OR 6b , —C(═O)OR 6b , —C(═O)N(R 6b ) 2 , —N(R 6b ) 2 , N(R 6b )C(═O)R 1z , —N(R 6b )C(═O)OR 6b , —OC(═O)R 1z , —OC(═O)OR 6b , —SR 6b , —N + (R 6b ) 3 , —SC(═O)R 1z , —SC(═O)OR 6b , —SC(═O)N(R 6b ) 2 , —C(═O)R 1z , or R 1z ;

each R 6b is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1z ;

each R 7 is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 7a ;

each R 7a is independently halogen, —OR 7b , —C(═O)OR 7b , —C(═O)N(R 7b ) 2 , —N(R 7b ) 2 , —N(R 7b )C(═O)R 1z , —N(R 7b )C(═O)OR 7b , —OC(═O)R 1z , —OC(═O)OR 7b , —SR 7b , —N + (R 7b ) 3 , —SC(═O)R 1z , —SC(═O)OR 7b , —SC(═O)N(R 7b ) 2 , —C(═O)R 1z , or R 1z ;

each R 7b is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1z ;

each R 8 is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 8a ;

each R 8a is independently halogen, —OR 8b , —C(═O)OR 8b , —C(═O)N(R 8b ) 2 , —N(R 8b ) 2 , —N(R 8b )C(═O)R 1z , —N(R 8b )C(═O)OR 8b , —OC(═O)R 1z , —OC(═O)OR 8b , —SR 8b , —N + (R 8b ) 3 , —SC(═O)R 1z , —SC(═O)OR 8b , —SC(═O)N(R 8b ) 2 , —C(═O)R 1z , or R 1z ;

each R 8b is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1z ;

each R 9 is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 2 heteroaryl is optionally substituted with one or more R 9a ;

or two R 9 , together with the carbon atom to which they are connected, form C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl, wherein the C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl is optionally substituted with one or more R 9a ;

each R 9a is independently halogen, —OR 9b , —C(═O)OR 9b , —C(═O)N(R 9b ) 2 , —N(R 9b ) 2 , —N(R 9b )C(═O)R 1z , —N(R 9b )C(═O)OR 9b , —OC(═O)R 1z , —OC(═O)OR 9b , —SR 9b , —N + (R 9b ) 3 , —SC(═O)R 1z , —SC(═O)OR 9b , —SC(═O)N(R 9b ) 2 , —C(═O)R 1z , or R 1z ;

each R 9b is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1z ;

each R 10 is independently H, R 10a , —OR 10a , or —N(R 10a ) 2 ;

or two R 10 , together with the carbon atom to which they are connected, form C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl, wherein the C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl is optionally substituted with one or more R 10b ;

each R 10a is independently C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 10b ;

each R 10b is independently halogen, —OR 10c , —C(═O)OR 10c , —C(═CO)N(R 10c ) 2 , —N(R 10c ) 2 , —N(R 10c )C(═O)R 1z , —N(R 10c )C(═O)OR 10c , —OC(O)R 1z , —OC(═O)OR 10c , —SR 10c , —N + (R 10c ) 3 , —SC(═O)R 1z , —SC(═O)OR 10c , —SC(═O)N(R 10c ) 2 , —C(═O)R 1z , or R 1z ;

each R 10c is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1z ;

each R 11 is independently H, R 11a , —OR 11a , or —N(R 11a ) 2 ;

or two R 11 , together with the carbon atom to which they are connected, form C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl, wherein the C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl is optionally substituted with one or more R 11b ;

each R 11a is independently C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 11b ;

each R 11b is independently halogen, —OR 11c , —C(═O)OR 11c , —C(═O)N(R 11c ) 2 , —N(R 11c ) 2 , —N(R 11c )C(═O)R 1z , —N(R 11c )C(═O)OR 11c , —OC(═O)R 1z , —OC(═O)OR 11c , —SR 11c , —N + (R 11c ) 3 , —SC(═O)R 1z , —SC(═O)OR 11c , —SC(═O)N(R 11c ) 2 , —C(═O)R 1z , or R 1z ;

each R 11c is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1z ;

T is a bond,

C(═O)—(CH═CH) n —C(═O)—, —C(═O)—(CHR 1b ) n —C(═O)—, —C(═O)CH 2 —[C(═O)CH 2 ] p —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] p —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH(OR 1c )—CH 2 ] r —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] r —[C(═O)CH 2 ] p —(CH 2 ] q —C(═O)—, —C(═O)—(CHR 1b ) n —[C(═O)CH 2 ] p —(CH 2 ) q —C(O)—, —C(═O)CH 2 —[C(═O)—(CHR 1b ) n ] p —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[C(═O)CH 2 ] p (CHR 1b ) q —C(═O)—, —C(═O)—(CHR 1b ) n —[C(═O)CH 2 ] p —(CHR 1b ) q —C(═O)—, or C 1 -C 20 alkyl optionally substituted with one or more R 1e ;

each R t is independently R 1 , R 1a , or R 1b ; or

two R t , together with the one or more intervening atoms they are attached to, form a C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl, wherein C 3 -C 12 cycloalkyl or C 3 -C 12 heterocycloalkyl is optionally substituted with one or more R 1a ; and

t is an integer ranging from 0 to 5.

2 . A compound of Formula (I′) or (II′):

or a pharmaceutically acceptable salt or solvate thereof, wherein:

R 1 is H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —C(═O)R 1b , —C(═O)R 1c , —C(═O)R 1z , —C(═O)—(CH═CH) n —R 1a , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —R 1a , —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] p —[CH 2 ] q —R 1a , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH(OR 1c )—CH 2 ] r —[CH 2 ] q —R 1a , —C(═O)CH 2 —[C(═O)R 1b ]—[C(═O)CH 2 ] p —[CH(OR 1c )—CH 2 ] r —[CH 2 ] q —R 1a , —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] r [C(═O)CH 2 ] p —[CH 2 ] q —R 1a , —C(═O)OR 1c , —C(═O)N(R 1c ) 2 , —C(═O)—CH═CH—C(═O)OR 1c , —C(═O)—[CH 2 ] q —C(═O)OR 1c , —C(═O)—CH 2 CH 2 —C(═O)OR 1c , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —C(═O)OR 1c , —C(═O)— [CH 2 ] q —C(═O:)R 1a , —C(═O)—[CH 2 ] q —C(═O)R 1z , —[C(═O)CH 2 ] q —C(═O)R 1z , —C(═O)—CH 2 CH 2 —C(═O)R 1z , —C(═O)—CH═CH—[C(═O)] p R 1z , —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —C(═O)R 1z , —C(═O)CHR 1c —[C(═O)CHR 1c ] p —[CH 2 ] q —R 1a , —C(═O)CH 12 —[C(═O)CH 2 )] p —[CH 2 ] q —C(═O)R 1a , —SR 1d ,

each R 1a is independently H, halogen, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, —OR 1c , —C(═O)OR 1c , —C(═O)N(R 1c ) 2 , —N(R 1b ) 2 , —N(R 1c ) 2 , —N(R 1c )C(═O)R 1b , —N(R 1c )C(═O)R 1z , —N(R 1c )C(═O)OR 1c , —OC(═O)R 1b , —OC(═O)R 1z , —OC(═O)OR 1c , —SC(═O)R 1b , —SC(═O)R 1z , —SC(═O,)OR 1c , —SC(═O)N(R 1c ) 2 , —C(═O)R 1b , —C(═O)R 1z , —SR 1d , or R 1z , wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, or C 2 -C 20 alkynyl is optionally substituted with one or more R 1e ;

each R 1b is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, —(CH 2 ) q —C(═O)OR 1c , —(CH 2 ) q —C(═O)R 1c , —CH 2 —C(═O)—(CH 2 )—C(═O)OR 1c , —CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —C(═O)OR 1c , —CH═CH—C(═O)OR 1c , —C(R 1e )═C(R 1e )—C(═O)OR 1c , —C(═O)OR 1c , —C(═O)N(R 1c ) 2 , or R 1z , wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, or C 2 -C 20 alkynyl is optionally substituted with one or more R 1e ;

each R 1d is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl), wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, —(C 1 -C 20 alkyl)-(C 3 -C 12 cycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 heterocycloalkyl), —(C 1 -C 20 alkyl)-(C 3 -C 12 aryl), or —(C 1 -C 20 alkyl)-(C 3 -C 12 heteroaryl) is optionally substituted with one or more R 1e ;

each R 1e is independently H, halogen, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, —OR 1g , —C(═O)OR 1g , C(═O)N(R 1g ) 2 , —N(R 1g ) 2 , —N(R 1g )C(═O) 1f , —N(R 1g )C(═NH)R 1f , —N(R 1g )C(═O)R 1z , —N(R 1g )C(═O)OR 1g , —OC(═O)R 1f , —OC(═O)R 1z , —OC(═O)OR 1g , —SR 1g , —N + (R 1g ) 3 , —SC(═O)R 1f , —SC(═O)R 1z , —SC(═O)OR 1g , —SC(═O)N(R 1g ) 2 , —C(═O)R 1f , —C(═O)R 1z , C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, C 3 -C 12 heteroaryl, or R 1z , wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 1f or R 1z ;

each R 1z is independently

each n is independently an integer ranging from 0 to 20;

each p is independently an integer ranging from 0 to 20;

each q is independently an integer ranging from 0 to 20;

each r is independently an integer ranging from 0 to 20;

R 2 and R 3 are independently H, R 1c , —C(═O)R 1b , —C(═O)OR 1c —C(═O)N(R 1c ) 2 , —C(═O)R 1z , —C(═O)—CH═CH—C(═O)OR 1c , C(═O)—CH 2 —CH 2 —C(═O)OR 1c ,

—C(═O)—CH═CH—C(═O)—R 1z , —C(═O)—CH 2 —CH 2 —C(═O)—R 1z ,

each X is independently —OR 1c , —SR 1c , —N(R 1c ) 2 ,

or R 1z ;

each R 4 is independently H, —C(═O)OR 4a , or —C(═O)N(R 4a ) 2 ;

each R 4a is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 11 aryl, or C 3 -C 12 heteroaryl, wherein the C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl is optionally substituted with one or more R 4b ;

each R 4b is independently H, halogen, —OR 4c , —C(═O)OR 4c , —C(═O)N(R 4c ) 2 , or —N(R 4c ) 2 ;

each R 4c is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl;

each R 5 is independently H, —C(═O)OR 5a , or —C(═O)N(R 5a ) 2 ;

each R 5a is independently H, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, C 3 -C 12 cycloalkyl, C 3 -C 12 heterocycloalkyl, C 3 -C 12 aryl, or C 3 -C 12 heteroaryl;

T is a bond,

C(═O)—(CH═CH) n —C(═O)—, —C(═O)—(CHR 1b )—C(═O)—, —C(═O)CH 2 —[C(═O)CH 2 ] p —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] p —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH(OR 1c )—CH 2 ] r —, (CH 2 ) q —C(═O)—, —C(═O)CH 2 —[CH(OR 1c )—CH 2 ] r —[C(═O)CH 2 ] p —(CH 2 ] q —C(═O)—, —C(═O)—(CHR 1b ) n —[C(═O)CH 2 ] p —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[C(═O)—(CHR 1b ) n ] p —(CH 2 ) q —C(═O)—, —C(═O)CH 2 —[C(═O)CH 2 ] p —(CHR 1b ) q —C(═O)—, —C(═O)—(CHR 1b ) n —[C(═O)CH 2 ] p —(CHR 1b ) q —C(═O)—, or C 1 -C 20 alkyl optionally substituted with one or more R 1e ;

each R t is independently R 1 , R 1a , or R 1b ; or

t is an integer ranging from 0 to 5.

3 . The compound of any one of the preceding claims, wherein R 1 is —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —R 1a and R 3 is H.

4 . The compound of any one of the preceding claims, wherein R 3 is H, at least one R 4 ; is H, and at least one R 5 is H.

5 . The compound of any one of the preceding claims, wherein R 1 is —C(═O)CH 2 —[C(═O)CH 2 ] p —[CH 2 ] q —R 1a and at least one of R 2 , R 3 , and R 5 is H.

6 . The compound of any one of the preceding claims, wherein the compound is of Formula (Iaa), (Iab), (Iac), or (Iad):

or a pharmaceutically acceptable salt or solvate thereof.

7 . The compound of any one of the preceding claims, wherein the compound is of Formula (Iaa-1), (Iab-1), (Iac-1), or (Iad-1):

or a pharmaceutically acceptable salt or solvate thereof.

8 . The compound of any one of the preceding claims, being selected from the compounds described in Table 1 and pharmaceutically acceptable salts thereof.

9 . The compound of any one of the preceding claims, wherein the compound is not Compound No. 1 or any pharmaceutically acceptable salt thereof.

10 . The compound of any one of the preceding claims, being selected from Compound No. 2-699 and pharmaceutically acceptable salts thereof.

11 . The compound of any one of the preceding claims, being selected from Compound No. 2-699.

12 . The compound of any one of the preceding claims, being selected from:

Compound No.

Structure

213

214

215

216

219

220

695

696

697

698

699

and pharmaceutically acceptable salts thereof.

13 . The compound of any one of the preceding claims, being selected from:

Compound

No.

Structure

213

214

215

216

219

220

695

696

697

698

699

14 . A pharmaceutical composition comprising the compound of any one of the preceding claims or a pharmaceutically acceptable salt thereof.

15 . A method of treating or preventing a disease in a subject, comprising administering to the subject a therapeutically effective amount of a compound of any one of the preceding claims.

16 . The compound of any one of the preceding claims for use in treating or preventing a disease in a subject, wherein the compound is for administration to the subject in at least one therapeutically effective amount.

17 . A use of the compound of any one of the preceding claims for the manufacture of a medicament for treating or preventing a disease in a subject, wherein the compound is for administration to the subject in at least one therapeutically effective amount.

Assignments (5)

RELEASE OF SECURITY INTEREST Recorded Aug 24, 2023

From: KREOS CAPITAL VI (UK) LIMITED

To: VECTIVBIO COMET AG, F/K/A COMET THERAPEUTICS, INC.

Reel/Frame 064702/0362 →

CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE SHOULD BE MERGER WITH AN EFFECTIVE DATE OF 07/07/2022 PREVIOUSLY RECORDED AT REEL: 061123 FRAME: 0841. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 7, 2022

From: COMET THERAPEUTICS, INC.

To: VECTIVBIO COMET AG

Reel/Frame 061625/0493 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2022

From: TAVERAS, ARTHUR GEORGE; KUSCER, ENEJ; SEKIRNIK, ANGELINA ROBERTA

To: COMET THERAPEUTICS, INC.

Reel/Frame 061123/0768 →

CHANGE OF NAME Recorded Sep 16, 2022

From: COMET THERAPEUTICS, INC.

To: VECTIVBIO COMET AG

Reel/Frame 061123/0841 →

SECURITY INTEREST Recorded Mar 29, 2022

From: COMET THERAPEUTICS, INC.

To: KREOS CAPITAL VI (UK) LIMITED

Reel/Frame 059420/0866 →