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US 2007/0191333 A1Published application
Antibacterial agents
AssigneeWarner-Lambert Company
InventorsKim Marie Hutchings, Jackie Diane Kendall, Sean Timothy Murphy, Tuan Phong Tran, Edmund Lee Ellsworth, Denton Wade Hoyer, Jeremy Tyson Starr
Life of this patent
Estimating the term…
Abstract
Compounds of formula I and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.
Claims19
A compound of formula I:
- or a pharmaceutically acceptable salt thereof, wherein:
- X is N or C, provided that when X is N, R5 is absent at that position;
- R1 is (C1-C6)alkyl,
- halo(C1-C6)alkyl,
- (C3-C6)Cycloalkyl,
- halo(C3-C6)cycloalkyl
- aryl, and
- heteroaryl;
- CH2(C3-C6)cycloalkyl;
- R2 is H,
- NH2,
- NH(C1-C6)alkyl,
- NH(C3-C6)cycloalkyl,
- NH-aryl,
- NH-heteroaryl,
- NHSO2—(C1-C6)alkyl,
- NHSO2-aryl,
- NHSO2-heteroaryl,
- wherein g is an integer from 1 to 10, Q is O, NH, or is absent, and R2a and R2a′ are each independently H or (C1-C6)alkyl, or taken together with the carbons to which they are attached form a 3, 4, 5, or 6-membered substituted or unsubstituted ring, and R2b is (C1-C6)alkyl, aryl, or heteroaryl,
- wherein R2a and R2a′ are as defined above,
- wherein indicates the point of attachment, p is 0 or 1, and R2c is H,
- (C1-C6)alkyl,
- O(C1-C6)alkyl,
- (C3-C7)cycloalkyl,
- aryl,
- heterocyclo,
- heteroaryl, or
- wherein R2a, R2b, and Q, are as defined above, and h and n are each independently integers from 0 to 10, and Y is OH, OPO(OH)2, OPO(O(C1-C6))2, or NR2dR2e, wherein R2d and R2e are each independently H, (C1-C6)alkyl, or (C3-C7)cycloalkyl,
- wherein q is 0 or 1, R2f and R2f′ are each independently H, (C1-C6)alkyl, aryl, or heteroaryl, or taken together with the carbon to which they are attached form a 3, 4, 5, or 6 membered substituted or unsubstituted ring, and R2g is
- (C1-C6)alkyl,
- (C3-C7)cycloalkyl,
- aryl, or
- heterocyclo, or
- heteroaryl;
- R3, R4, and R5 are each independently H,
- halo,
- NH2,
- (C1-C6)alkyl,
- halo(C1-C6)alkyl,
- (C1-C6)alkoxy, or
- halo(C1-C6)alkoxy
- nitrile;
- or
- R1 and R5 taken together with the carbons to which they are attached form a substituted or unsubstituted 5- or 6-membered substituted or unsubstituted ring containing 0, 1, or 2 heteroatoms selected from O, S, SO, SO2, or NRx, wherein Rx is H or (C1-C6)alkyl;
- and
- A is
- wherein z is 0, 1, or 2 and q is 0, 1, 2, or 3;
- Ra and Rb are each independently H, (C1-C6)alkyl, (C1-C6)alkoxy, halo(C1-C6)alkyl, halo, or Ra and Rb taken together with the carbon to which they are attached form C═O, C═NO(C1-C6)alkyl, or a 3, 4, 5 or 6-membered substituted or unsubstituted ring;
- R′, R″, R′″, and R″″ are each independently H,
- (C1-C6)alkyl,
- —O(C1-C6)alkyl,
- halo(C1-C6)alkyl,
- aryl, or
- heteroaryl;
- and B is
- provided that when B is
- R′ is not —O(C1-C6)alkyl, and wherein “ ” indicates the point of attachment;
- Rc and Rd are each independently H,
- (C6-C6)alkylnitrile;
- (C1-C6)alkyl,
- (C3-C6)cycloalkyl,
- heteroaryl,
- SO2—(C1-C6)alkyl,
- SO2-aryl,
- SO2-heteroaryl,
- wherein g is an integer from 1 to 10, Q is as defined above, and R2a and R2a′ are each independently H or (C1-C6)alkyl, or taken together with the carbons to which they are attached form a 3, 4, 5, or 6-membered substituted or unsubstituted ring, and R2b is (C1-C6)alkyl, aryl, or heteroaryl,
- wherein R2a and R2a′ are as defined above,
- wherein indicates the point of attachment, p is 0 or 1, and R2c is H,
- (C1-C6)alkyl,
- O(C1-C6)alkyl,
- (C3-C7)cycloalkyl,
- aryl,
- heterocyclo,
- heteroaryl, or
- wherein R2a, R2b, and Q are as defined above, and h and j are each independently integers from 0 to 10, and Y is OH, OPO(OH)2, OPO(O(C1-C6))2, or NR2dR2e, wherein R2d and R2e are each independently H, (C1-C6)alkyl, or (C3-C7)cycloalkyl,
- wherein q is 0 or 1, R2f and R2f′ are each independently H, (C1-C6)alkyl, aryl, or heteroaryl, or taken together with the carbon to which they are attached form a 3, 4, 5, or 6 membered substituted or unsubstituted ring, and R2g is
- (C1-C6)alkyl,
- (C3-C7)cycloalkyl,
- aryl, or
- heterocyclo, or
- heteroaryl;
- Re , and Rf are each independently X, C1-C6 alkyl, haloalkyl, halo, or Re and Rf taken together with the carbon to which they are attached form a 3, 4, 5 or 6-membered substituted or unsubstituted ring;
- Rg and Rh are each independently H, C1-C6 alkyl, haloalkyl, or taken together with the carbon to which they are attached to form a 3, 4, 5 or 6-membered substituted or unsubstituted ring;
- and
- Rj and Rk, are each independently H, (C1-C6)alkyl, haloalkyl, (C1-C6)alkyl-NRcRd, (C1-C6)alkyl-ORc, aryl, heteroaryl, heterocycle,
- wherein Z is O or NRc, or Rj and Rk taken together with the carbon to which they are attached to form a 3, 4, 5 or 6-membered substituted or unsubstituted ring.
83 more elements
A pharmaceutical formulation comprising a compound of formula I, II, III, IV, V, or VI admixed with a pharmaceutically acceptable diluent, carrier, or excipient.
A method of treating a bacterial infection in a mammal, comprising administering to a mammal in need thereof an effective amount of a compound of formula I, II, III, IV, V, or VI.
Dependencies are inferred from the claim text.