Prodrugs of xanomelin, prodrugs of throspium, and methods of use thereof

JP2026516309APending Publication Date: 2026-05-21TERRAN BIOSCIENCES INC
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Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
TERRAN BIOSCIENCES INC
Filing Date
2024-04-24
Publication Date
2026-05-21

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【0022】 本明細書に組み込まれ、本明細書の一部を形成する添付の図面は、本開示のいくつかの実施形態を示し、説明と共に本開示の原理を説明するのに役立つ。図面は、本開示の一実施形態を例示するためのものにすぎず、本発明を限定するものとして解釈されるべきではない。本発明のさらなる目的、特徴及び利点は、本開示の例示的な実施形態を示す添付の図面と併せて以下の詳細な説明から明らかになるであろう。

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Abstract

This specification discloses xanomeline and trospium prodrugs and analogues, as well as methods for preparing and using prodrugs and analogues for, for example, the treatment of neuropsychiatric disorders.
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Claims

1. Formula (1) 【Chemistry 1】 (In the formula, X － It either does not exist or is an anion. R １ teeth, 【Chemistry 2】 And, Each R ５ and R ６ are, independently, hydrogen, deuterium, C １～２４ alkyl, -C １～２４ haloalkyl, C ２～３０ alkenyl, -O-C(O)-C １ ~C ２４ alkyl, -O-C(O)-C ２ ~C ３０ alkenyl, -C(O)-C １ ~C ２４ alkyl, -C(O)-C １～２４ haloalkyl, -C(O)-C ２ ~C ３０ alkenyl, -C(O)-C ２～２４ alkynyl, -(C １～２４ alkylene)-Si(R ｉｉｊ ) ２ -C １～２４ alkyl, -Si(R ｉｉｊ ) ２ -C １～２４ alkyl, -(C ２～３０ alkenylene)-Si(R ｉｉｊ ) ２ -C １～２４ alkyl, -(C ２～２４ alkenylene)-Si(R ｉｉｊ ) ２ -C ２～２４ alkenyl, -Si(R ｉｉｊ ) ２ -C ２～２４ alkenyl, -(C １ ~C ２４ alkylene)-Si(R ｉｉｊ ) ２ -C ２～２４ alkenyl, -(C １～２４ alkylene)-S(O)-C １～２４ alkyl, -(C １～２４ alkylene)-S(O) ２ -C １～２４ alkyl, -(C １～２４ alkylene)-S(O)-C １～２４ alkylene, -(C １～２４ alkylene)-S(O) ２ -C １～２４ alkylene, -(C １～２４ alkylene)-(O-CH ２ CH ２ ) １～５０ -O-R ｉｖ , -C(O)-(C １～２４ Alkylene)-(O-CH ２ CH ２ ) １～５０ -O-R ｉｖ , C ６～１０ Aryl, 5-10 member heteroaryl, 4-10 member heterocyclyl, C ３～８ Cycloalkyl, -C １～６ Alkylene-(C) ６～１０ Aryl), C １～６ Alkylene-(5-10 membered heteroaryl), -C １～６ Alkylene-(C) ３～８ Cycloalkyl), -C １～６ Alkylene-(4-10 membered heterocyclyl),-C(O)-(C) ６～１０ aryl), -C(O)-(5-10 member heteroaryl), -C(O)-(C ３～８ The alkyl, alkenyl, alkylene, alkenylene, cycloalkyl, heterocyclyl, heteroaryl, or aryl are either unsubstituted or optionally substituted, or R ５ and R ６ These combine to form oxo, C ３～８ They form cycloalkyl or 3- to 10-membered heterocyclines, and the cycloalkyl or heterocyclines are either unsubstituted or optionally substituted. Each R ｉｉｊ Independently, C １～６ Alkyl or two R ｉｉｊ These combine with the atoms to which they are bonded to form a 3- to 8-membered ring. Each R ｉｖ These are independently H, deuterium, and C １～２２ Alkyl or C ２～２４ It is alkenyl, R ４ teeth, (ii-a)-C(O)-C １～２４ alkyl, -C(O)-C １～２４ haloalkyl, -C(O)-C ２～３０ alkenyl, -C(O)-C ２～２４ alkynyl, -C(O)-(C １～２４ alkylene)-C ６～１４ aryl, -C(O)-(C ２～２４ alkenylene)-C ６～１４ aryl, -C(O)-(C ２～２４ alkynylene)-C ６～１０ aryl, -C(O)-(C １～２４ alkylene)-C(O)-O-C １～２４ alkyl, -C(O)-(C １～２４ alkylene)-C(O)-O-C ２～２４ alkenylene, -C(O)-(C ２～２４ alkenylene)-C(O)-O-C １～２４ alkyl, -C(O)-C(O)-O-C １～２４ alkyl, -C(O)-C(O)-OH, -C(O)-C(O)-(cholesterol or dihydrocholesterol), -C(O)-C(O)-(bile acid), -C(O)-(C ２～２４ alkynylene)-C(O)-O-C １～２４ alkyl, -C(O)-(C ２～２４ alkynylene)-C(O)-OH, -C(O)-(C １～２４ alkylene)-C(O)-(cholesterol or dihydrocholesterol), -C(O)-(C １～２４ alkylene)-C(O)-(bile acid), -C(O)-(C ２～２４ alkenylene)-C(O)-(cholesterol or dihydrocholesterol), -C(O)-(C ２～２４ alkenylene)-C(O)-(bile acid), -C(O)-(C １～２４ alkylene)-O-C(O)-(cholesterol or dihydrocholesterol), -C(O)-(C １～２４ alkylene)-O-C(O)-(bile acid), -C(O)-(C ２～２４ alkynylene)-C(O)-(cholesterol or dihydrocholesterol), -C(O)-(C ２～２４ Alkynylene)-C(O)-(bile acid),-C(O)-(C １～２４ Alkylene)-C(O)OH, -C(O)-(C ２～２４ Alkenylene)-C(O)OH,-C(O)-C ６～１４ Aryl, -C(O)-C ３～１５ Cycloalkyl, -C(O)-(3-10 member heterocycle), -C(O)-(5-10 member heteroaryl), -C(O)-(C １～２４ Alkylene)-(3-10 membered cycloalkyl),-C(O)-(C １～２４ Alkylene) - (C ６～１４ Aryl), -C(O)-(C １～２２ Alkylene)-(3-10 membered heteroring),-C(O)-(C １～２４ Alkylene)-(5-10 membered heteroaryl),-C(O)-(C) ２～２４ Alkenylene)-(3-10 membered cycloalkyl),-C(O)-(C ２～２４ Alkenylene) - (C ６～１４ Aryl), -C(O)-(C ２～２４ Alkenylene)-(3-10 membered heteroring),-C(O)-(C ２～２４ Alkenylene)-(5-10 membered heteroaryl),-C(O)-(C １～２４ Alkylene)-(cholesterol or dihydrocholesterol),-C(O)-(C １～２４ Alkylene)-(bile acid),-C(O)-(C １～２４ Alkylene)-O-(C) ６～１４ Aryl), -C(O)-(C １～２４ Alkylene)-O-(3-10 membered heteroring),-C(O)-(C １～２４ Alkylene)-O-(5-10 membered heteroaryl),-C(O)-(C １～２４ Alkylene)-O-(bile acid), -C(O)-(cholesterol or dihydrocholesterol), -C(O)-(bile acid), -(bile acid) or -C(O)-(C １～２４ Alkylene)-(O-CH ２ CH ２ ) １～５０ -O-R ｉｉａ’ (Here, the alkyl, alkenyl, alkynyl, alkylene, alkenylene, alkynylene, cycloalkyl, heterocyclyl, heteroaryl, or aryl is either unsubstituted or optionally substituted.) R ｉｉａ’ H, deuterium, C １～２４ Alkyl or C ２～２４ (The alkyl or alkenyl is either unsubstituted or optionally substituted.) (ii-b)-C(O)-OC １～２４ Alkyl, -C(O)-O-C １～２４ Haloalkyl, -C(O)-O-C ２～３０ Alkenyl, -C(O)-O-C ２～２４ Alkinyl, -C(O)-O-(C １～２４ Alkylene)-C ６～１４ Ariel, -C(O)-O-(C ２～２４ Alkenylene)-C ６～１４ Ariel, -C(O)-O-(C １～２４ Alkylene)-C(O)-O-C １～２４ Alkyl, -C(O)-O-(C ２～２４ Alkenylene)-C(O)-O-C １～２４ Alkyl, -C(O)-O-(C １～２４ Alkylene)-C(O)OH,-C(O)-O-(C ２～２４ Alkenylene)-C(O)OH,-C(O)-O-C ６～１４ Ariel, -C(O)-O-C ３～１５ Cycloalkyl, -C(O)-O- (3-10 membered heterocycle), -C(O)-O- (5-10 membered heteroaryl), -C(O)-O-(C １～２４ Alkylene)-(3-10 membered cycloalkyl),-C(O)-O-(C １～２４ Alkylene) - (C ６～１４ Aryl), -C(O)-O-(C １～２４ Alkylene)-(3-10 membered heteroring),-C(O)-O-(C １～２４ Alkylene)-(5-10 membered heteroaryl),-C(O)-O-(C ２～２４ Alkenylene)-(3-10 membered cycloalkyl),-C(O)-O-(C ２～２４ Alkenylene) - (C ６～１４ Aryl), -C(O)-O-(C ２～２４ Alkenylene)-(3-10 membered heteroring),-C(O)-O-(C ２～２４ Alkenylene)-(5-10 membered heteroaryl),-C(O)-O-(C １～２４ Alkylene)-(cholesterol or dihydrocholesterol),-C(O)-O-(C ２～２４ Alkylene)-(bile acid),-C(O)-(C １～２４ Alkylene)-O-(C) ６～１４ Aryl), -C(O)-(C １～２４ Alkylene)-O-(3-10 membered heteroring),-C(O)-(C １～２４ Alkylene)-O-(5-10 membered heteroaryl),-C(O)-(C １～２４ Alkylene)-(cholesterol or dihydrocholesterol),-C(O)-(C １～２４ Alkylene)-O-(bile acid), C(O)-(C １～２４ Alkylene)-C(O)-(cholesterol or dihydrocholesterol),-C(O)-(C １～２４ Alkylene)-C(O)-(bile acid),-C(O)-(cholesterol or dihydrocholesterol),-C(O)-(bile acid),-(bile acid) or-C(O)-O-(C １～２４ Alkylene)-(O-CH ２ CH ２ ) １～５０ -O-R ｉｉｂ’ (Here, the alkyl, alkenyl, alkynyl, alkylene, alkenylene, alkynylene, cycloalkyl, heterocyclyl, heteroaryl, or aryl are either unsubstituted or optionally substituted, and R ｉｉｂ’ H, deuterium, C １～２２ Alkyl or C ２～２４ (The alkyl or alkenyl is either unsubstituted or optionally substituted.) (ii---Si(R Ｓｉ ) ３ (Here, each R Ｓｉ Independently, C １～２４ Alkyl, C ２～３０ Alkenil, C ６～１０ Ariel, -O-C １～２４ Alkyl, -O-C ２～３０ (The alkyl, alkenyl, or -OH group is either unsubstituted or optionally substituted.) And, R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ and R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ (It is alkyl.) A compound of [unclear].

2. Formula (1-F) 【Transformation 3】 (In the formula, X － It either does not exist or is an anion. Each R １ and R ２ These are defined independently for equation (1), and Each R １Ｆａ , R １Ｆｂ , R １Ｆｃ , R ２Ｆａ , R ２Ｆｂ , R ３Ｆａ , R ３Ｆｂ , R ４Ｆａ , R ４Ｆｂ , R ５Ｆａ , R ５Ｆｂ , R ６Ｆａ , R ６Ｆｂ , R ７Ｆ , R ８Ｆａ , R ８Ｆｂ , R ９Ｆａ and R ９Ｆｂ (These are independently H, D, or F.) A compound of [unclear].

3. Equation (1 - ii - a - i) 【Chemistry 4】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, Each R ５ and R ６ This is defined independently for equation (1), Each R ４’ These are either absent, or H, deuterium, fluorine, or CH, independently. ３ and are optionally substituted by one or more deuterium atoms, and L is -C １～２４ Alkylene, -C １～２４ Haloalkylene, -C ２～３０ Alkenylene or -C ２～２４ (The alkylene, alkenylene, or alkynylene is either unsubstituted or optionally substituted.) The compound according to claim 1, wherein the compound is as described above.

4. One R ４’ The compound according to any one of claims 1 to 3 does not exist.

5. Two R's ４’ The compound according to any one of claims 1 to 4 does not exist.

6. at least one R ４’ The compound according to any one of claims 1 to 5, wherein is H.

7. at least one R ４’ The compound according to any one of claims 1 to 6, wherein is deuterium or fluorine.

8. at least one R ４’ CH ３ The compound according to any one of claims 1 to 7.

9. Each R ４’ The compound according to any one of claims 1 to 8, wherein is H.

10. Each R ４’ The compound according to any one of claims 1 to 9, wherein is deuterium or fluorine.

11. Each R ４’ CH ３ The compound according to any one of claims 1 to 10.

12. L is either unsubstituted or optionally substituted -C １～２４ The compound according to any one of claims 1 to 11, which is an alkylene.

13. L is either unsubstituted or optionally substituted -C １～２４ The compound according to any one of claims 1 to 12, which is a haloalkylene.

14. L is either unsubstituted or optionally substituted -C ２～３０ The compound according to any one of claims 1 to 13, which is an alkenylene.

15. L is either unsubstituted or optionally substituted -C ２～２４ The compound according to any one of claims 1 to 14, wherein it is an alkynylene.

16. L is -C １～２４ The compound according to any one of claims 1 to 15, which is an alkylene.

17. L is -C １～２４ The compound according to any one of claims 1 to 16, which is a haloalkylene.

18. L is -C ２～３０ The compound according to any one of claims 1 to 17, which is an alkenylene.

19. L is -C ２～２４ The compound according to any one of claims 1 to 18, wherein the compound is an alkynylene.

20. L is either unsubstituted or optionally substituted -C １～１８ The compound according to any one of claims 1 to 19, wherein the compound is alkylene.

21. L is either unsubstituted or optionally substituted -C １～１８ The compound according to any one of claims 1 to 20, which is a haloalkylene.

22. L is either unsubstituted or optionally substituted -C ２～１８ The compound according to any one of claims 1 to 21, which is an alkenylene.

23. L is either unsubstituted or optionally substituted -C ２～１８ The compound according to any one of claims 1 to 22, wherein it is an alkynylene.

24. L is -C １～１８ The compound according to any one of claims 1 to 23, which is an alkylene.

25. L is -C １～１８ The compound according to any one of claims 1 to 24, which is a haloalkylene.

26. L is -C ２～１８ The compound according to any one of claims 1 to 25, which is an alkenylene.

27. L is -C ２～１８ The compound according to any one of claims 1 to 26, wherein it is an alkynylene.

28. The compound according to any one of claims 1 to 27, wherein L is methylene.

29. L is methylene, and each R ４’ The compound according to any one of claims 1 to 28, wherein is H.

30. L is C １～６ The compound according to any one of claims 1 to 29, which is an alkylene.

31. L is an unsubstituted C １～６ The compound according to any one of claims 1 to 30, which is an alkylene.

32. L is a linear C １～６ The compound according to any one of claims 1 to 31, wherein it is an alkylene.

33. L is an unsubstituted linear C １～６ The compound according to any one of claims 1 to 32, which is an alkylene.

34. L is C １～１０ The compound according to any one of claims 1 to 33, which is an alkylene.

35. L is an unsubstituted C １～１０ The compound according to any one of claims 1 to 34, which is an alkylene.

36. L is a linear C １～１０ The compound according to any one of claims 1 to 35, which is an alkylene.

37. L is an unsubstituted linear C １～１０ The compound according to any one of claims 1 to 36, which is an alkylene.

38. L is C １～６ The compound according to any one of claims 1 to 37, which is an alkenylene.

39. L is an unsubstituted C １～６ The compound according to any one of claims 1 to 38, which is an alkenylene.

40. L is a linear C １～６ The compound according to any one of claims 1 to 39, which is an alkenylene.

41. L is an unsubstituted linear C １～６ The compound according to any one of claims 1 to 40, which is an alkenylene.

42. L is C １～１０ The compound according to any one of claims 1 to 41, which is an alkenylene.

43. L is an unsubstituted C １～１０ The compound according to any one of claims 1 to 42, which is an alkenylene.

44. L is a linear C １～１０ The compound according to any one of claims 1 to 43, which is an alkenylene.

45. L is an unsubstituted linear C １～１０ The compound according to any one of claims 1 to 44, which is an alkenylene.

46. Formula (1-ii-a-ii) 【Transformation 5】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, Each R ５ and R ６ These are defined independently for equation (1), and n is between 0 and 20. The compound according to claim 1, wherein the compound is as described above.

47. The compound according to any one of claims 1 to 46, wherein n is 0 to 15.

48. The compound according to any one of claims 1 to 47, wherein n is 0 to 10.

49. The compound according to any one of claims 1 to 48, wherein n is 1 to 15.

50. The compound according to any one of claims 1 to 49, wherein n is 1 to 10.

51. Formula (1-ii-a-iii) 【Transformation 6】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, Each R ５ and R ６ This is defined independently for equation (1), L is bond, C １～２４ Alkylene or -C １～２４ It is alkylene-O-*, where * indicates a bond to ring A, and Ring A is, (i) C ６～１４ Ariel, (ii) 3-10 member heteroring, (iii) C ３～１５ Cycloalkyl, (iv) 5-10 member heteroaryl, or (v) Cholesterol, dihydrocholesterol, or bile acid And, The aforementioned aryl, heterocyclic, cycloalkyl, heteroaryl, cholesterol, dihydrocholesterol, or bile acid is either unsubstituted or optionally substituted. The compound according to claim 1, wherein the compound is as described above.

52. L is bond, C １～２４ Alkylene or -C １～２４ It is alkylene-O-*, where -* indicates a bond to ring A, and Ring A is, (i) One or more mono- or G-C １～６ Alkylamino, 4-10 membered heterocycle or C １～６ C is optionally substituted with alkyl groups. ６～１４ Ariel, (ii) One or more mono or G-C １～６ Alkylamino, 4-10 membered heterocycle or C １～６ A 4- to 10-membered heterocycle optionally substituted with an alkyl group. (iii) One or more C １～８ C is optionally substituted with alkyl groups. ３～１５ Cycloalkyl, or (iv) One or more oxo or C １～６ Five- or six-membered heteroaryl compounds optionally substituted with alkyl groups. The compound according to any one of claims 1 to 51.

53. Ring A is, 【Transformation 7】 And, m is 0 to 6, and R Ａ’ is -C(O)-(C which is optionally substituted). ６～１０ aryl), -C(O)- (optionally substituted 5- to 10-membered heteroaryl), -C(O)- (optionally substituted 3- to 10-membered heterocyclyl), -C(O)- (optionally substituted C ３ ~C １５ Cycloalkyl), - (C optionally substituted C ６～１０ aryl), -(optionally substituted 5- to 10-membered heteroaryl), -(optionally substituted 3- to 10-membered heterocyclyl), -C(optionally substituted C ３ ~C １５ Cycloalkyl, halogen, cyano, hydroxyl, C １～６ Alkoxy, monoalkylamino, dialkylamino or C １～６ A compound according to any one of claims 1 to 52, wherein it is alkyl.

54. Ring A is a 4- to 10-membered heteroring, and the heteroring is composed of one or more mono- or di-C １～６ Alkylamino, 4-10 membered heterocycle or C １～６ The compound according to any one of claims 1 to 53, which is optionally substituted with an alkyl group.

55. The compound according to any one of claims 1 to 54, wherein ring A is a 4- to 10-membered heteroring.

56. The compound according to any one of claims 1 to 55, wherein ring A is a 4- to 10-membered heteroring containing at least one oxygen atom.

57. The compound according to any one of claims 1 to 56, wherein ring A is a four-membered heteroring containing at least one oxygen atom.

58. The compound according to any one of claims 1 to 57, wherein ring A is 2-oxetanyl.

59. The compound according to any one of claims 1 to 58, wherein ring A is 3-oxetanyl.

60. The compound according to any one of claims 1 to 59, wherein ring A is a five-membered heterocycle containing at least one oxygen atom.

61. The compound according to any one of claims 1 to 60, wherein ring A is 2-tetrahydrofuranyl.

62. The compound according to any one of claims 1 to 61, wherein ring A is 3-tetrahydrofuranyl.

63. The compound according to any one of claims 1 to 62, wherein ring A is a six-membered heterocycle containing at least one oxygen atom.

64. The compound according to any one of claims 1 to 63, wherein ring A is 2-tetrahydropyranyl.

65. The compound according to any one of claims 1 to 64, wherein ring A is 3-tetrahydropyranyl.

66. The compound according to any one of claims 1 to 65, wherein ring A is 4-tetrahydropyranyl.

67. The compound according to any one of claims 1 to 66, wherein ring A is a bile acid.

68. The compound according to any one of claims 1 to 67, wherein ring A is cholic acid.

69. The compound according to any one of claims 1 to 68, wherein ring A is glycocholic acid.

70. The compound according to any one of claims 1 to 69, wherein ring A is taurocholic acid.

71. The compound according to any one of claims 1 to 70, wherein ring A is deoxycholic acid.

72. The compound according to any one of claims 1 to 71, wherein ring A is chenodeoxycholic acid.

73. The compound according to any one of claims 1 to 72, wherein ring A is glycochenodeoxycholic acid.

74. The compound according to any one of claims 1 to 73, wherein ring A is taurochenodeoxycholic acid.

75. The compound according to any one of claims 1 to 74, wherein ring A is lithocholic acid.

76. The compound according to any one of claims 1 to 75, wherein L is a bond.

77. Formula (1-ii-a-iv) 【Transformation 8】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, Each R ５ and R ６ This is defined independently for equation (1), L is bond, C １～２４ Alkylene, C ２～２４ Alkenylene or C ２～２４ It is an alkynylene, and R ４’’ is H or C １～２４ Cholesterol, dihydrocholesterol, and bile acids are alkyl or have a bonded oxygen atom. The aforementioned alkylene, alkenylene, alkynylene, cholesterol, dihydrocholesterol, bile acid and C １～２４ Alkyl groups are either unsubstituted or optionally substituted. The compound according to claim 1, wherein the compound is as described above.

78. R ４’’ The compound according to any one of claims 1 to 77, wherein is H.

79. (R ４’’ The compound according to any one of claims 1 to 78, wherein -O-) is a sterol.

80. (R ４’’ The compound according to any one of claims 1 to 79, wherein -O-) is cholesterol, dihydrocholesterol, or bile acid.

81. (R ４’’ The compound according to any one of claims 1 to 80, wherein -O-) is cholesterol.

82. (R ４’’ The compound according to any one of claims 1 to 81, wherein -O-) is a bile acid.

83. (R ４’’ The compound according to any one of claims 1 to 82, wherein -O-) is dihydrocholesterol.

84. R ４’’ C １～２４ The compound according to any one of claims 1 to 83, wherein the alkyl is optionally substituted.

85. Equation (1 - ii - bi - i) 【Chemistry 9】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, Each R ５ and R ６ This is defined independently for equation (1), L is bond, C １～２４ Haloalkylene, C １～２４ Alkylene or C ２～３０ Alkenylene, C ２～２４ It is an alkylene, and the alkylene, alkenylene, or alkylene is either unsubstituted or optionally substituted, and Each R ４’ It is either independent, nonexistent, or H or CH ３ (and is optionally substituted with one or more deuterium atoms.) The compound according to claim 1, wherein the compound is as described above.

86. L is bond, C １～２０ Alkylene or C ２～２０ The alkylene and alkenylene are either unsubstituted or optionally substituted, and Each R ４’ These are independently H or CH ３ The compound according to any one of claims 1 to 85.

87. L is bond, C １～２０ Alkylene or C ２～２０ The compound according to any one of claims 1 to 86, wherein the alkylene and the alkenylene are unsubstituted or optionally substituted.

88. L is C which is optionally substituted. １～２０ The compound according to any one of claims 1 to 87, which is an alkylene.

89. L is C which is optionally substituted. ２～２０ The compound according to any one of claims 1 to 88, which is an alkenylene.

90. L is C which is optionally substituted. １～２０ The compound according to any one of claims 1 to 89, wherein the alkylene is a branched chain.

91. L is C which is optionally substituted. ２～２０ The compound according to any one of claims 1 to 90, wherein the alkenylene is a branched chain.

92. L is C which is optionally substituted. １～２０ The compound according to any one of claims 1 to 91, wherein the alkylene is linear.

93. L is C which is optionally substituted. ２～２０ The compound according to any one of claims 1 to 92, wherein the alkenylene is linear.

94. The compound according to any one of claims 1 to 93, wherein L is a bond.

95. Equation (1 - ii - b - ii) 【Chemistry 10】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, Each R ５ and R ６ These are defined independently for equation (1), and n is between 0 and 20. The compound according to claim 1, wherein the compound is as described above.

96. The compound according to any one of claims 1 to 95, wherein n is 0 to 15.

97. The compound according to any one of claims 1 to 96, wherein n is 0 to 10.

98. The compound according to any one of claims 1 to 97, wherein n is 1 to 15.

99. The compound according to any one of claims 1 to 98, wherein n is 1 to 10.

100. Formula (1-ii-b-iii) 【Chemistry 11】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, R ５ and R ６ This is defined independently for equation (1), L is bond, C １～２４ Alkylene or -C １～２４ It is alkylene-O-*. -* indicates bonding to ring A, and Ring A is, (i) C ６～１４ Ariel, (ii) 3-10 member heteroring, (iii) C ３～１５ Cycloalkyl, (iv) 5-10 member heteroaryl, (v) Cholesterol, dihydrocholesterol, or bile acid And, The aforementioned aryl, heterocyclic, cycloalkyl, heteroaryl, cholesterol, dihydrocholesterol, or bile acid is either unsubstituted or optionally substituted. The compound according to claim 1, wherein the compound is as described above.

101. Ring A is, (i) One or more mono- or G-C １～６ Alkylamino, 4-10 membered heterocycle or C １～６ C is optionally substituted with alkyl groups. ６～１４ Ariel, (ii) One or more mono or G-C １～６ Alkylamino, 4-10 membered heterocycle or C １～６ A 4- to 10-membered heterocycle optionally substituted with an alkyl group. (iii) One or more C １～８ C is optionally substituted with alkyl groups. ３～１５ Cycloalkyl, or (iv) One or more oxo or C １～６ Five- or six-membered heteroaryl compounds optionally substituted with alkyl groups. The compound according to any one of claims 1 to 100.

102. Ring A is a 4- to 10-membered heteroring, and the heteroring is composed of one or more mono- or di-C １～６ Alkylamino, 4-10 membered heterocycle or C １～６ The compound according to any one of claims 1 to 101, which is optionally substituted with an alkyl group.

103. The compound according to any one of claims 1 to 102, wherein ring A is a 4- to 10-membered heteroring.

104. The compound according to any one of claims 1 to 103, wherein ring A is a 4- to 10-membered heteroring containing at least one oxygen atom.

105. The compound according to any one of claims 1 to 104, wherein ring A is a four-membered heterocycle containing at least one oxygen atom.

106. The compound according to any one of claims 1 to 105, wherein ring A is 2-oxetanyl.

107. The compound according to any one of claims 1 to 106, wherein ring A is 3-oxetanyl.

108. The compound according to any one of claims 1 to 107, wherein ring A is a five-membered heteroring containing at least one oxygen atom.

109. The compound according to any one of claims 1 to 108, wherein ring A is 2-tetrahydrofuranyl.

110. The compound according to any one of claims 1 to 109, wherein ring A is 3-tetrahydrofuranyl.

111. The compound according to any one of claims 1 to 110, wherein ring A is a six-membered heteroring containing at least one oxygen atom.

112. The compound according to any one of claims 1 to 111, wherein ring A is 2-tetrahydropyranyl.

113. The compound according to any one of claims 1 to 112, wherein ring A is 3-tetrahydropyranyl.

114. The compound according to any one of claims 1 to 113, wherein ring A is 4-tetrahydropyranyl.

115. Formula (1-ii-c) 【Chemistry 12】 (In the formula, X － It either does not exist or is an anion. R ２ CH ３ ,CH ２ D, CHD ２ or CD ３ And, R ３ C is a carbon atom optionally substituted with one or more fluorine and / or deuterium atoms. １～６ It is alkyl, Each R ５ and R ６ These are defined independently for equation (1), and Each R Ｓｉ Independently, C １～２０ Alkyl, C ６～１０ Ariel, -O-C １～２０ It is alkyl or -OH, The alkyl, aryl, or -O-alkyl groups are either unsubstituted or optionally substituted. The compound according to claim 1, wherein the compound is as described above.

116. Each R Ｓｉ Independently, C １～２０ Alkyl, C ６～１０ Ariel, -O-C １～２０ Alkyl, -O-C ６～１０ The compound according to any one of claims 1 to 115, wherein it is aryl or -OH.

117. R Ｓｉ C １～２０ Alkyl or C ６～１０ The compound according to any one of claims 1 to 116, wherein it is an aryl compound.

118. at least one R Ｓｉ C １～２０ A compound according to any one of claims 1 to 117, wherein it is alkyl.

119. at least one R Ｓｉ C ６～１０ The compound according to any one of claims 1 to 118, wherein it is an aryl compound.

120. at least one R Ｓｉ is, -O-C １～２０ Alkyl, -O-C ６～１０ The compound according to any one of claims 1 to 119, wherein it is aryl or -OH.

121. at least one R Ｓｉ is, -O-C １～２０ A compound according to any one of claims 1 to 120, wherein it is alkyl.

122. at least one R Ｓｉ is, -O-C ６～１０ The compound according to any one of claims 1 to 121, wherein it is an aryl compound.

123. at least one R Ｓｉ The compound according to any one of claims 1 to 122, wherein is -OH.

124. R ２ CH ３ or CD ３ The compound according to any one of claims 1 to 123.

125. R ２ CH ３ The compound according to any one of claims 1 to 124.

126. R ２ CD ３ The compound according to any one of claims 1 to 125.

127. R ３ C is optionally substituted with one or more deuterium and / or fluorine atoms. ６ A compound according to any one of claims 1 to 126, wherein it is alkyl.

128. R ３ C is a carbon atom that is optionally substituted with one or more deuterium atoms. ６ A compound according to any one of claims 1 to 127, wherein it is alkyl.

129. R ３ C is a C atom that is optionally substituted with one or more fluorine atoms. ６ A compound according to any one of claims 1 to 128, wherein it is alkyl.

130. R ３ C ６ Alkyl, and the C ６ The compound according to any one of claims 1 to 129, wherein the alkyl is a linear alkyl group.

131. R ３ C ６ Alkyl, and the C ６ The compound according to any one of claims 1 to 130, wherein the alkyl is a branched-chain alkyl.

132. R ３ is unsubstituted C ６ A compound according to any one of claims 1 to 131, wherein it is alkyl.

133. R ３ is unsubstituted C ６ Alkyl, and the C ６ The compound according to any one of claims 1 to 132, wherein the alkyl is a linear alkyl group.

134. R ３ is unsubstituted C ６ Alkyl, and the C ６ The compound according to any one of claims 1 to 133, wherein the alkyl is a branched-chain alkyl.

135. Each R ５ and R ６ These are, independently, hydrogen, C １～１８ Alkyl, C ２～３０ Alkenil, C ３～８ Cycloalkyl, 3-10 membered heterocyclyl, 3-10 membered heteroaryl, or C ６～１０ It is aryl, and the C １～１８ Alkyl or C ２～３０ Alkenil is C ６～１０ Ariel, C ３～８ The C is optionally substituted with a cycloalkyl, a 3-10 membered heterocyclyl, or a 3-10 membered heteroaryl, and the C ６～１０ Aryl is either OH or C １～６ It is optionally substituted with an alkoxy, or R ５ and R ６ These combine to form oxo, C ３～８ The compound according to any one of claims 1 to 134, which forms a cycloalkyl or a 3- to 10-membered heterocycline.

136. R ５ or R ６ The compound according to any one of claims 1 to 135, wherein at least one of is hydrogen.

137. R ５ The compound according to any one of claims 1 to 136, wherein is hydrogen.

138. R ５ C １～１８ A compound according to any one of claims 1 to 137, wherein it is alkyl.

139. R ５ C １～１０ A compound according to any one of claims 1 to 138, wherein it is alkyl.

140. R ５ The compound according to any one of claims 1 to 139, wherein is a linear alkyl group.

141. R ５ The compound according to any one of claims 1 to 140, wherein is a branched alkyl group.

142. R ５ The compound according to any one of claims 1 to 141, wherein is an unsubstituted alkyl group.

143. R ５ is unsubstituted C １～１０ Alkyl, and the C １～１０ The compound according to any one of claims 1 to 142, wherein the alkyl is a linear alkyl.

144. R ５ is unsubstituted C １～１０ Alkyl, and the C １～１０ The compound according to any one of claims 1 to 143, wherein the alkyl is a branched-chain alkyl.

145. R ５ C ２～３０ The compound according to any one of claims 1 to 144, wherein the compound is an alkenyl.

146. R ５ C ２～２５ The compound according to any one of claims 1 to 145, wherein it is an alkenyl.

147. R ５ The compound according to any one of claims 1 to 146, wherein is a linear alkenyl.

148. R ５ The compound according to any one of claims 1 to 147, wherein is a branched alkenyl.

149. R ５ The compound according to any one of claims 1 to 148, wherein is an unsubstituted alkenyl.

150. R ５ is unsubstituted C ２～２５ It is an alkenyl, and the C ２～２５ The compound according to any one of claims 1 to 149, wherein the alkenyl is a linear alkenyl.

151. R ５ is unsubstituted C ２～２５ It is an alkenyl, and the C ２～２５ The compound according to any one of claims 1 to 150, wherein the alkenyl is a branched-chain alkenyl.

152. R ５ C ６～１０ The compound according to any one of claims 1 to 151, wherein it is an aryl compound.

153. R ５ The compound according to any one of claims 1 to 152, wherein is phenyl.

154. R ５ C ３～８ A compound according to any one of claims 1 to 153, wherein it is a cycloalkyl compound.

155. R ５ The compound according to any one of claims 1 to 154, wherein is a 3 to 10-membered heterocycline.

156. R ６ The compound according to any one of claims 1 to 155, wherein is hydrogen.

157. R ６ C １～１８ A compound according to any one of claims 1 to 156, wherein it is alkyl.

158. R ６ C １～１０ A compound according to any one of claims 1 to 157, wherein it is alkyl.

159. R ６ The compound according to any one of claims 1 to 158, wherein is a linear alkyl group.

160. R ６ The compound according to any one of claims 1 to 159, wherein is a branched alkyl group.

161. R ６ The compound according to any one of claims 1 to 160, wherein is an unsubstituted alkyl group.

162. R ６ is unsubstituted C １～１０ Alkyl, and the C １～１０ The compound according to any one of claims 1 to 161, wherein the alkyl is a linear alkyl group.

163. R ６ is unsubstituted C １～１０ Alkyl, and the C １～１０ The compound according to any one of claims 1 to 162, wherein the alkyl is a branched-chain alkyl.

164. R ６ C ２～３０ The compound according to any one of claims 1 to 163, wherein it is an alkenyl.

165. R ６ C ２～２５ The compound according to any one of claims 1 to 164, wherein it is an alkenyl.

166. R ６ The compound according to any one of claims 1 to 165, wherein is a linear alkenyl.

167. R ６ The compound according to any one of claims 1 to 166, wherein is a branched alkenyl.

168. R ６ The compound according to any one of claims 1 to 167, wherein is an unsubstituted alkenyl.

169. R ６ is unsubstituted C ２～２５ It is an alkenyl, and the C ２～２５ The compound according to any one of claims 1 to 168, wherein the alkenyl is a linear alkenyl.

170. R ６ is unsubstituted C ２～２５ It is an alkenyl, and the C ２～２５ The compound according to any one of claims 1 to 169, wherein the alkenyl is a branched-chain alkenyl.

171. R ６ C ６～１０ The compound according to any one of claims 1 to 170, wherein it is an aryl compound.

172. R ６ The compound according to any one of claims 1 to 171, wherein is phenyl.

173. R ６ C ３～８ A compound according to any one of claims 1 to 172, wherein it is a cycloalkyl compound.

174. R ６ The compound according to any one of claims 1 to 173, wherein is a 3- to 10-membered heterocycline.

175. R ５ and R ６ The compound according to any one of claims 1 to 174, wherein the compounds combine to form an oxo.

176. R ５ and R ６ These combine to form C ３～８ A compound according to any one of claims 1 to 175, which forms a cycloalkyl group.

177. X － The compound according to any one of claims 1 to 176, wherein is a pharmaceutically acceptable anion.

178. X － The compound according to any one of claims 1 to 177, wherein the compound is an acetate.

179. The compound according to any one of claims 1 to 178, as shown in Table 1.

180. Compounds listed in Table 1.

181. A method for preparing the compound according to any one of claims 1 to 180.

182. pharmaceutically acceptable salts of the compounds in Table 1.

183. A pharmaceutical composition comprising a compound according to any one of claims 1 to 180 and a pharmaceutically acceptable excipient.

184. A pharmaceutical composition comprising the compound of formula (1) and a pharmaceutically acceptable excipient.

185. A pharmaceutical composition comprising a compound of formula (1-F) and a pharmaceutically acceptable excipient.

186. A pharmaceutical composition comprising a compound shown in this disclosure and a pharmaceutically acceptable excipient.

187. A method for treating a neuropsychiatric disorder according to any one of the claims of this disclosure.

188. A method for treating a neuropsychiatric disorder, comprising administering an effective amount of a compound described in any one of claims 1 to 180.

189. A method for treating a neuropsychiatric disorder, comprising administering an effective amount of the pharmaceutical composition described in any one of claims 183 to 186.

190. A method for treating a neuropsychiatric disorder in a person in need thereof, comprising administering a compound of formula (1) to the person.

191. A method for treating a neuropsychiatric disorder in a person in need thereof, comprising administering a compound of formula (1-F) to the person.

192. A method for treating a neuropsychiatric disorder in a person in need of such treatment, comprising administering the compounds listed in Table 1 to the person.

193. The method according to any one of claims 187 to 192, wherein the neuropsychiatric disorder is migraine, headache (e.g., cluster headache), post-traumatic stress disorder (PTSD), anxiety, depression, neurodegenerative disorder, Alzheimer's disease, Parkinson's disease, psychological disorder, treatment-resistant depression, suicidal ideation, major depressive disorder, bipolar disorder, schizophrenia, stroke, traumatic brain injury, or addiction (e.g., substance use disorder).

194. Use of the compound according to any one of claims 1 to 180 for preparing a pharmaceutical product for treating neuropsychiatric disorders in a person in need thereof.

195. The use of a compound according to any one of claims 1 to 180 in a method for treating a neuropsychiatric disorder in a person in need thereof.

196. A compound according to any one of claims 1 to 180, for use in a method of treating neuropsychiatric disorders in a person in need thereof.

197. The method according to any one of claims 187 to 193, wherein the neuropsychiatric disorder is schizophrenia.

198. The method according to any one of claims 187 to 193 or 197, wherein the neuropsychiatric disorder is a psychosis in Alzheimer's disease.