IP Library › Patent Application 17298652

Patent Application

App. No. 17/298,652

PANTETHEINE DERIVATIVES AND USES THEREOF

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Patent No.: US None
App. No.: 17/298,652

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Abstract

The present disclosure relates to compounds of Formula (I), (II), or (II′): (I), (II), (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 (57)

1 .- 388 . (canceled)

389 . A compound of Formula (Iaa), (Iab), (Iac), (Iad), (Iae), (Iaf), (Iag), (Iah), (Iai), (Iaj), (Iba), (Ibj):

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(═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(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(H)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 , —SR 1d ,

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 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 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 , —OSi(R 1g ) 3 , —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 1e , or R 1 , 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 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, oxo, 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 1f ) 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 , —OSi(R 1g ) 3 , —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, oxo, C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl, —OSi(R 1g ) 3 , —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 each independently H, —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 , —Si(R 1g ) 3 ,

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 .

390 . The compound of claim 1 , wherein the compound is of Formula (Iaa), (Iab), (Iac), or (Iad), wherein:

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 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 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 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, —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 ;

391 . The compound of claim 389 , wherein the compound is of Formula (Iaa-1), (Iaa-2), (Iab-1), (Iab-2), (Iac-1), (Iac-2), (Iad-1), or (Iad-2):

or a pharmaceutically acceptable salt or solvate thereof;

392 . The compound of claim 389 , wherein the compound is of Formula (Iae-1), (Iae-2), (Iaf-1), (Iaf-2), (Iag-1), (Iag-2), (Iah-1), or (Iah-2):

or a pharmaceutically acceptable salt or solvate thereof;

393 . The compound of claim 389 , wherein the compound is of Formula (Iai-1), (Iai-2), (Iaj-1), (Iaj-2), (Iak-1), (Iak-2), (Ial-1), (Ial-2), (Iam-1), (Iam-2), (Ian-1), or (Ian-2):

or a pharmaceutically acceptable salt or solvate thereof;

394 . The compound of claim 389 , wherein the compound is of Formula (Iba-1) or (Iba-2):

or a pharmaceutically acceptable salt or solvate thereof:

395 . The compound of claim 389 , wherein the compound is of Formula (Ibj-1) or (Ibj-2)

or a pharmaceutically acceptable salt or solvate thereof.

396 . A pharmaceutical composition comprising the compound of claim 389 or a pharmaceutically acceptable salt thereof.

397 . A method of treating or preventing a disease in a subject comprising administering to the subject a therapeutically effective amount of a compound of claim 389 .

398 . A compound having the structure

or a pharmaceutically acceptable salt thereof.

399 . A pharmaceutical composition comprising the compound of claim 398 or a pharmaceutically acceptable salt thereof.

400 . A method of treating or preventing a disease in a subject comprising administering to the subject a therapeutically effective amount of a compound of claim 398 .

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 PREVIOUSLY RECORDED AT REEL: 061138 FRAME: 0210. ASSIGNOR(S) HEREBY CONFIRMS THE CHANGE OF NAME. Recorded Oct 7, 2022

From: COMET THERAPEUTICS, INC.

To: VECTIVBIO COMET AG

Reel/Frame 061625/0348 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2022

From: TAVERAS, ARTHUR GEORGE; SEKIRNIK, ANGELINA ROBERTA; VALLS SERON, MERCEDES; KUSCER, ENEJ; SHAH, DHARINI

To: COMET THERAPEUTICS, INC.

Reel/Frame 061138/0113 →

CHANGE OF NAME Recorded Sep 19, 2022

From: COMET THERAPEUTICS, INC.

To: VECTIVBIO COMET AG

Reel/Frame 061138/0210 →

SECURITY INTEREST Recorded Mar 29, 2022

From: COMET THERAPEUTICS, INC.

To: KREOS CAPITAL VI (UK) LIMITED

Reel/Frame 059420/0866 →