Antimicrobials and methods of making and using same
AssigneeMelinta Therapeutics, Inc.
InventorsErin M. Duffy, Ashoke Bhattacharjee, Zoltan F. Kanyo, Joseph A. Ippolito
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Abstract
The present disclosure relates generally to the field of antimicrobial compounds and to methods of making and using them. These compounds are useful for treating, preventing, reducing the risk of, and delaying the onset of microbial infections in humans and animals. In some embodiments, the present disclosure provides a compound of Formula (I) or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer.
Claims64
A compound of Formula (I):
- or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer, wherein:
- R1 is selected from H and halo;
- R2 is selected from H, halo, C1-6 alkyl, C1-4 haloalkyl, and ORa1;
- R3 is selected from H, C1-6 alkyl, and C1-4 haloalkyl;
- W is selected from N and CR4;
- R4 is selected from H, halo, ORa2, SRa2, 5-6 membered heterocycloalkyl, S(O)2Rb2, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with a substituent selected from ORa2;
- R5 is selected from H, halo, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with a substituent selected from ORa2;
- R6 is selected from H, C1-6 alkyl, and C2-6 alkenyl, wherein said C1-6 alkyl is optionally substituted with ORa3;
- R7 is selected from H and C1-6 alkyl;
- or
- R6 and R7 together with the carbon atoms to which they are attached and the nitrogen atom connecting said two carbon atoms form a ring of formula:
- R8 is selected from H, C1-6 alkyl, and C1-4 haloalkyl;
- X is selected from O and NRN;
- RN is selected from H and C1-4 alkyl;
- RA is H;
- RB is H;
- or
- RA and RB together with the nitrogen atom to which they are attached form a 5- to 6-membered heterocycloalkyl ring containing 1 or 2 heteroatoms selected from N, O and S, wherein said 5- to 6-membered heterocycloalkyl is optionally substituted with halo;
- R9 is selected from C1-6 alkyl, C2-6 alkenyl, C3-5 cycloalkyl, wherein said C1-6 alkyl is optionally substituted with a substituent selected from ORa3 and SRa3;
- R10 is selected from H, C2-4 alkenyl, C1-4 haloalkyl and C1-4 alkyl optionally substituted with a substituent selected from amino, C1-4 alkoxy, C3-5 cycloalkyl, and 3- to 6-membered heterocycloalkyl;
- R11 is H or C1-3 alkyl, wherein the C1-3 alkyl is optionally substituted with OH;
- each Ra1, Ra2, and Ra3 is independently selected from H, C1-6 alkyl and C1-4 haloalkyl.
A compound of Formula (II):
- or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer, wherein:
- R1 is selected from H and halo;
- R2 is selected from H, halo, C1-6 alkyl, C1-4 haloalkyl, and ORa1;
- R3 is selected from H, C1-6 alkyl, and C1-4 haloalkyl;
- W is selected from N and CR4;
- R4 is selected from H, halo, ORa2, SRa2, 5-6 membered heterocycloalkyl, S(O)2Rb2, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with a substituent selected from ORa2;
- R5 is selected from H, halo, C1-6 alkyl, and C2-6 alkenyl, wherein the C1-6 alkyl is optionally substituted with a substituent selected from ORa2;
- R6 is selected from H, C1-6 alkyl, and C2-6 alkenyl, wherein said C1-6 alkyl is optionally substituted with ORa3;
- R7 is selected from H and C1-6 alkyl;
- or
- R6 and R7 together with the carbon atoms to which they are attached and the nitrogen atom connecting said two carbon atoms form a ring of formula:
- R8 is selected from H, C1-6 alkyl, and C1-4 haloalkyl;
- X is selected from O and NRN;
- RN is selected from H and C1-4 alkyl;
- RA is H;
- RB is H;
- or
- RA and RB together with the nitrogen atom to which they are attached form a 5- to 6-membered heterocycloalkyl ring containing 1 or 2 heteroatoms selected from N, O and S, wherein said 5- to 6-membered heterocycloalkyl is optionally substituted with halo;
- R9 is selected from C1-6 alkyl, C3-5 cycloalkyl, wherein said C1-6 alkyl is optionally substituted with a substituent selected from ORa3 and SRa3;
- R10 is selected from H, C2-4 alkenyl, C1-4 haloalkyl and C1-4 alkyl optionally substituted with a substituent selected from amino, C1-4 alkoxy, C3-5 cycloalkyl, and 3- to 6-membered heterocycloalkyl;
- and
- each Ra1, Ra2, and Ra3 is independently selected from H, C1-6 alkyl and C1-4 haloalkyl.
The compound of claim 50 or 51, wherein R6 and R7 form a ring of formula:
- wherein # indicates the ring carbon attached to the ring containing W.
A compound of Formula (I) or Formula (II) selected from any one of the compounds listed in Table 1, Table 1a, Table 1b, or Table 1c, or a tautomer thereof or a pharmaceutically acceptable salt of the compound or tautomer.
Dependencies are inferred from the claim text.