BIARILE MONOBACTAM COMPOUNDS AND METHODS OF THEIR APPLICATION FOR TREATMENT OF BACTERIAL INFECTIONS Russian patent published in 2021 - IPC C07D471/04 C07D417/14 C07F9/6558 C07C53/18 A61K31/397 A61P31/04 

FIELD: pharmaceuticals.

SUBSTANCE: invention relates to biaryl monobactam compounds of Formula I and their pharmaceutically acceptable salts, where W is a bond or O; R^x and R^z independently represent hydrogen, C₁-C₃alkyl; X represents N or CR¹; R¹ represents hydrogen, C_1-C₃alkyl or halogen; in each case R^a independently represents hydrogen, halogen, C₁-C₃alkyl or -OR^e; Z represents C₁-C₃alkylene, optionally substituted with 1-3 R^b; in each case R^b independently represents -C₁-C₈alkyl, -C₃-C₇cycloalkyl, -C(O)OR^e, -C(O)NR^cR^d, tetrazolyl or -P(O)(R^e)_p, wherein the specified -C₁-C₈alkyl and the specified -C₃-C₇cycloalkyl are optionally substituted with 1-3 R^a; AryA is a 5-6 membered monocyclic aromatic ring with 0, 1, 2 or 3 ring atoms independently selected from N, N as a quaternary salt, optionally substituted with 1-4 R⁴; Y represents O; R² represents hydrogen or -C₁-C₃alkyl, wherein the above -C₁-C₃alkyl is optionally substituted with 1-3 R^a; A¹ represents AryA; A² represents the groups of pyrazole, imidazole and pyridine (given in the claims), where * indicates attachment to Q and ** indicates attachment to M; in each case R⁴ represents halogen; HetB it is a 3-6-membered saturated or monounsaturated monocyclic ring with 1, 2, or 3 heteroatoms in the ring, independently selected from N, N as a quaternary salt, and O, optionally substituted with 1-3 R^a; Q represents bond, CH₂, O, S, -(CH₂)_nNR³- or -NR³(CH₂)_n-, wherein each CH₂ is unsubstituted, or substituted by 1-2 substituents selected from halogen, -C₁-C₆alkyl, OR^e and -(CH₂)_nNR^cR^d; R³ represents hydrogen or -C₁-C₃alkyl, wherein the -C₁-C₃alkyl is optionally substituted with 1-3 R^a; M represents -(CH₂)_nR⁵ or R⁵; R⁵ is H, C₂-C₁₀alkyl, C₃-C₇cycloalkyl, HetB or -NH(C₁-C₆alkyl), wherein the specified C₂-C₁₀alkyl and the above C₃-C₇cycloalkyl are optionally substituted with 1-4 R⁶; in each case R⁶ is independently selected from a group consisting of halogen, -OR^e, -NR^cR^d, -(CH₂)_nNR^cR^d and HetB; in each case R^c and R^d independently represent hydrogen, -C₁-C₁₀alkyl or -C₁-C₁₀alkylene-HetB and wherein each R^c and R^d is optionally substituted with 1-3 R^f; in each case R^e independently represents hydrogen, -C₁-C₁₀alkyl, -OH or -OC₁-C₄alkyl, wherein each R^e is optionally substituted with 1-3 R^h; in each case R^f independently represents halogen, -C₁-C₁₀alkyl, -OH, -OC₁-C₄alkyl or NH₂, wherein the specified -C₁-C₁₀alkyl is optionally substituted with 1-3 substituents independently selected from -OH, halogen, cyano and -S(O)₂CH₃; every n is independently equal to 0, 1, 2, 3, or 4; every m is independently equal to 0, 1, or 2, and every p is independently equal to 1 or 2. The invention also relates to the salt of trifluoroacetic acid of the compound of Formula I, as well as to specific biaryl compounds.

EFFECT: technical result is biaryl compounds exhibiting antibacterial activity.

16 cl, 7 tbl, 126 ex