AZABENZIMIDAZOLE COMPOUNDS AND A PHARMACEUTICAL COMPOSITION Russian patent published in 2023 - IPC C07D471/04 C07D519/00 A61K31/437 A61K31/444 A61K31/4545 A61K31/46 A61K31/496 A61K31/497 A61K31/551 A61P3/10 A61P13/02 A61P13/10 A61P27/06 A61P43/00 

FIELD: pharmaceuticals.

SUBSTANCE: invention relates to an azabenzimidazole compound of formula [1] or a pharmaceutically acceptable salt or hydrate thereof, where R¹ is C1-C6alkyl, or two R¹ are taken together with an adjacent carbon atom to form a 3–7-membered cycloalkyl; R² is C1-C6alkyl, C1-C6alkoxyC1-C6alkyl; R³ represents a hydrogen atom or C1-C6alkyl; R⁴ is pyridyl optionally substituted with one or two groups selected from the group consisting of C1-C6alkyl, trihaloC1-C6alkyl, C1-C6alkoxy and C3-C6cycloalkyl, or phenyl optionally substituted with 1–3 groups selected from the group consisting of from trihaloC1-C6alkyl, halogen, C1-C6alkoxy and C3-C6cycloalkyl; A is a group of formula A-1, A-2, A-3, A-4, or A-5 where the bond on the left side of each group is attached to the 2-position of azabenzimidazole in formula [1] and the bond on the right side is attached to W in formula [1], and R¹¹ is a group selected from hydrogen, halogen, C1-C6alkyl, C1-C6alkoxy, or nitro; W is a bond or a group of formula W-1, W-2 or W-3, where R²¹ is hydrogen or C1-C6alkyl; B is a group of formula B-1, B-2, B-3, or B-4, where the bond on the left side of each group is attached to W in formula [1], the bond on the right side is attached to Y in formula [1], U¹ is a nitrogen atom or CR⁴¹ and U² is either a nitrogen atom or CR⁴², and R⁴¹ and R⁴² are independently hydrogen, C1-C6alkyl, halogen or hydroxyl, m and n are independently 1, 2 or 3, and R³¹ and R³² are independently hydrogen, C1-C6alkyl, halogen, or C1-C6alkoxyC1-C6alkyl, or R³¹ and R³² are taken together with adjacent carbon atoms to form an alkylene bridge, provided that R³¹ and R³² are substituted in any substitutable position other than U¹ and U²; Y represents a hydrogen atom or a group of any of the formulas Y-1–Y-4 and Y-11–Y-16, where R⁵¹ represents C1-C6alkyl; p is either 1, 2, or 3; q is either 0, 1, or 2; r is either 1, 2, or 3; T represents either O, S, SO₂ or NR⁶¹ where R⁶¹ represents either a hydrogen atom or C1-C6alkyl; s is either 0, 1, 2, or 3; and t is either 0 or 1, provided that (a) when W is a bond, if B is either B-1 or B-2 and U² is a nitrogen atom, then Y is either Y-1, Y- 2, Y-3 or Y-4, if B is B-1 or B-2 and U² is CR⁴² where R⁴² is as defined above, then U¹ is a nitrogen atom and Y is either Y -11, Y-12, Y-13, Y-14, Y-15 or Y-16 and if B is either B-3 or B-4 then Y is a hydrogen atom; (b) when W is W-1, if B is B-1, U¹ is a nitrogen atom and U² is a nitrogen atom, then Y is either Y-1, Y-2, Y-3 or Y -4 and if B is B-1, U¹ is a nitrogen atom and U² is CR⁴² where R⁴² is as defined above, then Y is either Y-11, Y-12, Y-13 , Y-14, Y-15 or Y-16; (c) when W is W-2, if B is either B-1 or B-2, U¹ is a nitrogen atom and U² is a nitrogen atom, then Y is either Y-1, Y-2, Y -3 or Y-4 if B is either B-1 or B-2, U¹ is a nitrogen atom and U² is CR⁴² where R⁴² is as defined above, then Y is either Y-11, Y-12, Y-13, Y-14, Y-15 or Y-16 and if B is either B-3 or B-4 then Y is a hydrogen atom; and (d) when W is W-3, if B is B-1, U¹ is CR⁴¹ where R⁴¹ is as defined above and U² is a nitrogen atom, then Y is either Y-1, Y-2, Y-3 or Y-4. The invention also relates to a pharmaceutical composition with M3 PAM activity based on the said compound [1].

EFFECT: new compounds and a pharmaceutical composition based on them have been obtained, which can be used in medicine as an agent for the prevention or treatment of disorders in the function of excretion and/or accumulation of urine in case of bladder/urethra disease, glaucoma or diabetes.

10 cl, 116 tbl, 213 ex