US 12,077,488 B2
Compounds useful for treating a Mannheimia haemolytica or Histophilus somni infection
Michael Berger, Wiesbaden (DE); Thorsten Meyer, Wiesbaden (DE); Joachim Ullrich, Stadecken-Elsheim (DE); and Ralf Warrass, Alzey (DE)
Assigned to Intervet Inc., Rahway, NJ (US)
Filed by Intervet Inc., Madison, NJ (US)
Filed on May 10, 2021, as Appl. No. 17/316,034.
Application 17/316,034 is a continuation of application No. 16/472,001, granted, now 11,034,650, previously published as PCT/EP2017/084346, filed on Dec. 22, 2017.
Claims priority of application No. 16206790 (EP), filed on Dec. 23, 2016.
Prior Publication US 2022/0041547 A1, Feb. 10, 2022
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/165 (2006.01); A61P 11/00 (2006.01); A61P 31/04 (2006.01); C07C 259/06 (2006.01); C07C 317/50 (2006.01); C07C 323/60 (2006.01); C07D 205/04 (2006.01); C07D 207/14 (2006.01); C07D 213/56 (2006.01); C07D 217/18 (2006.01); C07D 233/64 (2006.01); C07D 235/14 (2006.01); C07D 259/00 (2006.01); C07D 267/10 (2006.01); C07D 277/28 (2006.01); C07D 295/00 (2006.01); C07D 295/155 (2006.01); C07D 307/52 (2006.01); C07D 307/56 (2006.01); C07D 317/50 (2006.01); C07D 333/20 (2006.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 413/12 (2006.01); C07D 417/12 (2006.01)
CPC C07C 259/06 (2013.01) [A61P 11/00 (2018.01); A61P 31/04 (2018.01); C07C 317/50 (2013.01); C07C 323/60 (2013.01); C07D 213/56 (2013.01); C07D 217/18 (2013.01); C07D 235/14 (2013.01); C07D 267/10 (2013.01); C07D 277/28 (2013.01); C07D 295/155 (2013.01); C07D 307/52 (2013.01); C07D 333/20 (2013.01); C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 413/12 (2013.01); C07D 417/12 (2013.01); C07C 2601/02 (2017.05); C07C 2601/04 (2017.05); C07C 2601/08 (2017.05); C07C 2601/14 (2017.05); C07C 2601/16 (2017.05)] 7 Claims
 
1. Compound according to the formula (I):

OG Complex Work Unit Chemistry
or a stereoisomer, or pharmaceutically acceptable salt, thereof, wherein
R1 is selected from the group consisting of —C(R11R12R13), C(═O)R11, —C(═NR14)R11,
R11 is selected from the group consisting of H, and C1-6-alkyl;
R12 is selected from the group consisting of
H, C1-6-alkyl, and C1-6-alkyl substituted with a substituent from the group consisting of —SR8, —OR9, —C(═O)OR9, —NR9R10, —SO2NR9R10, —SO2R8;
R13 is selected from the group consisting of
H, C1-6-alkyl, aryl, —SR8, —OR9, —NR9R10, —SO2R8, nitro, —C(═O)NR9R10, and C1-6-alkyl substituted with a substituent selected from the group consisting of —SR8, —C(═O)NR9R10, —SO2NR9R10, —SO2R8, nitro, cyano, —OR9, —C(═O)OR9, —NR9C(═NR14)NR9R10;
wherein when R13 is OH or NH2 and R12 is methyl then R11 cannot be H and when R13 is NH2 and R12 is methyl then R11 cannot be methyl; and
wherein when R13 is OH and R12 is methyl then R11 cannot be methyl and wherein when R13 is NH2 and R12 is H then R11 cannot be H;
R14 is selected from the group consisting of H, C1-6-alkyl, or —OR9;
R2, R3 is H;
R4 is —OR9;
R5 is H;
R6, R7 are independently selected from the group consisting of
H, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-10-cycloalkyl, aryl, heterocyclyl, heteroaryl, C1-6-alkyloxy-C1-6-alkyl, C1-C6-alkyl substituted with aryl, C1-C6-alkyl substituted with heteroaryl, C1-C6-alkyl substituted with heterocyclyl, or NR6R7 is NO2 or
R6, R7 together with the N atom to which they are attached can form a saturated or unsaturated heterocyclic ring having 3 to 12 ring atoms, wherein 1 ring atom is N and 0, 1, 2, or 3 further ring atoms are selected from N, S, and O, the rest of the ring atoms being C;
wherein the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, alkyloxy or the heterocyclic ring formed by R6, R7 together with the N atom to which they are attached is optionally substituted with a substituent selected from the group consisting of
C1-6-alkyl, C3-8-cycloalkyl, C1-6-alkyloxy, —NR9R10, carbonyl, —C(═O)OR9, halogen atom, C1-6-alkyl substituted with halo, C1-6-alkyloxy-C1-6-alkyl, aryl, heteroaryl, C1-C6-alkyl substituted with aryl, cyano, hydroxyl, —SR8, —SO2R8, SO2NR9R10, —C(═O)NR9R10, C1-6-alkyl substituted with hydroxyl;
R8 is selected from the group consisting of H, C1-6-alkyl;
R9, R10 are independently selected from the group consisting of H, and C1-6-alkyl;
L is C1-6-alkyl;
M is selected from the group consisting of aryl, heteroaryl, C2-4alkenyl;
G is —C≡C—;
Y is aryl; and
X is —C(═O)—.