Granted Patent B2

US 12,528,783 · App. 17/790,569 · Granted Jan 20, 2026

Inventors: Christian Schütz (Braunschweig, DE); Martin Empting (Braunschweig, DE); Ahmed S. Ahmed (Braunschweig, DE); Mostafa Hamed (Braunschweig, DE); Rolf W. Hartmann (Braunschweig, DE); Teresa Röhrig (Braunschweig, DE); Andreas M. Kany (Braunschweig, DE); Anna K. Hirsch (Braunschweig, DE)

Assignee: HELMHOLTZ-ZENTRUM FUR INFEKTIONSFORSCHUNG GMBH

C07D401/12A61K45/06C07D401/14C07D403/12C07D413/12C07D417/12

Abstract

Claims (29)

1 . A compound of the formula (I):

or a pharmacologically acceptable salt thereof,

wherein

R A represents a hydrogen atom, a halogen atom, NH 2 or NH(C 1-3 alkyl);

X 1 represents CH or N;

L is a group represented by formula (L-1), (L-2) or (L-3):

wherein

R L1 , R L2 and R L3 each, independently of one another, represents a hydrogen atom, F, Cl; or a (C 1 -C 3 )alkyl group, which may be substituted by one or more, identical or different, group(s) selected from a halogen atom, OH, —O, and NH 2 ;

Y 1 and Y 2 each, independently of one another, is NH, O, or S;

each independently of one another, represents a single bond or a double bond, wherein at least one in the ring of formula (L-3) is a double bond;

T 1 is a hydrogen atom; and T 2 represents a hydrogen atom; or an aryl, heteroaryl, aralkyl or hetero-aralkyl group, all of which groups may be substituted by one, two or more, identical or different, group(s) selected from: a halogen atom, OH, ═O, NH 2 , (C 1 -C 3 )alkyl which may be substituted by one or more, identical or different, group(s) selected from a halogen atom, OH, ═O, and NH 2 ; (C 1 -C 3 )alkoxy which may be substituted by one or more, identical or different, group(s) selected from a halogen atom, OH, ═O, and NH 2 ; and C(O)NR T1 R T2 ;

R T1 and R T2 each, independently of one another, represents a hydrogen atom or a (C 1 -C 3 )alkyl group, which may be substituted by one or more, identical or different, group(s) selected from a halogen atom, OH, —O, and NH 2 ;

or

T 1 and T 2 both represent O.

2 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof, wherein L is a group of formula (L-1).

3 . The compound according to claim 2 , or a pharmacologically acceptable salt thereof, wherein R L1 represents a hydrogen atom.

4 . The compound according to claim 2 , or a pharmacologically acceptable salt thereof, wherein X 1 is CH; and R A represents a hydrogen atom or Cl.

5 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof, wherein L is a group of formula (L-2).

6 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof, wherein L is a group of formula (L-3).

7 . The compound according to claim 6 , or a pharmacologically acceptable salt thereof, wherein R A represents a hydrogen atom or NH 2 .

8 . The compound according to claim 6 , or a pharmacologically acceptable salt thereof, wherein the group represented by formula (L-3) contains one of the following groups as a partial structure:

9 . The compound according to claim 2 , or a pharmacologically acceptable salt thereof, wherein T 1 is a hydrogen atom; and T 2 represents a 6-membered aryl or heteroaryl group, which group may be substituted by one, two or more, identical or different, group(s) selected from: a halogen atom, OH, ═O, NH 2 , (C 1 -C 3 )alkyl which may be substituted by one or more, identical or different, group(s) selected from a halogen atom, OH, ═O, and NH 2 ; (C 1 -C 3 )alkoxy which may be substituted by one or more, identical or different, group(s) selected from a halogen atom, OH, ═O, and NH 2 ; and C(O)NR T1 R T2 ;

R T1 and R T2 each, independently of one another, represents a hydrogen atom or a (C 1 -C 3 )alkyl group, which may be substituted by one or more, identical or different, group(s) selected from a halogen atom, OH, ═O, and NH 2 .

10 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof, wherein the group NT 1 T 2 is selected from the groups:

11 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof, wherein the compound is selected from the group consisting of:

12 . A pharmaceutical composition that comprises one or more compound(s) according to claim 1 and, optionally, at least one carrier substance, excipient and/or adjuvant.

13 . A combination preparation comprising at least one compound according to claim 1 , and at least one antibiotic as a further active ingredient.

14 . The compound according to claim 1 , the pharmaceutical composition according to claim 12 , or the combination preparation of claim 13 for use as a medicament.

15 . A coating for medicinal devices containing at least one compound according to claim 1 .

Assignments (2)

Priority Claims (1)

Continuity (1)

References Cited (48)