US 12,649,723 B2Granted

Carbonohydrazonoyl dicyanide compounds comprising 2 or more aryl or heteroaryl connected via linker and use thereof

AssigneeKorea Institute of Science and Technology

InventorsAe Nim Pae, Yun Kyung Kim, Sang Min Lim, Sungsu Lim, Haeun Lee, Woo Seung Son, Hye Yeon Lee

Life of this patent

Estimating the term…

Abstract

Provided are novel carbonohydrazonoyl dicyanide compounds including two or more aryl or heteroaryl groups connected via a linker and uses thereof.

Claims9

Dependent claims

A compound represented by Formula 1 below or a pharmaceutically acceptable salt thereof:

wherein, in Formula 1 above,
L is —NHCO—, —CONH—, —NHSO2—, —SO2NH—, or -(straight-chain or branched C0-3 alkylene)′-O-(straight-chain or branched C0-3 alkylene)″-;
R1 is hydrogen, C1-6 alkyl, or C1-6 alkylcarbonyl;
(Het)Ar1 is C6-10 arylene or 5- to 10-membered heteroarylene;
and
(Het)Ar2 is C6-10 aryl or 5- to 10-membered heteroaryl;
wherein the C6-10 aryl(ene) and 5- to 10-membered heteroaryl(ene) are each independently unsubstituted or substituted with at least one selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, halogen, cyano, C1-6 haloalkyl, and C1-6 haloalkoxy,
wherein the compound is
1. (6-(5-methylpyrazine-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
2. (4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
3. (2-fluoro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
4. (2-methoxy-4-(5-methylpyrazine-2-carboxamido)phenyl) carbonohydrazonoyl dicyanide,
5. (2-chloro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
6. (2-methyl-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
7. (3-fluoro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
8. (3-methyl-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
9. methyl(3-methyl-4-(5-methylpyrazine-2-carboxamido)phenyl) carbonohydrazonoyl dicyanide,
10. (3-methoxy-4-(5-methylpyrazine-2-carboxamido)phenyl) carbonohydrazonoyl dicyanide,
11. (3-chloro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
12. (5-methyl-6-(5-methylpyrazine-2-carboxamido)pyridin-3-yl) carbonohydrazonoyl dicyanide,
13. (4-methyl-6-(5-methylpyrazine-2-carboxamido)pyridin-3-yl) carbonohydrazonoyl dicyanide,
14. (5-(5-methylpyrazine-2-carboxamido)pyridin-2-yl) carbonohydrazonoyl dicyanide,
15. (6-benzamidopyridin-3-yl)carbonohydrazonoyl dicyanide,
16. (6-(4-fluorobenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
17. (6-(2-fluorobenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
18. (6-(3-fluorobenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
19. (6-(3-fluoro-5-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
20. (6-(2-fluoro-3-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
21. (6-(4-fluoro-3-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
22. (6-(3-fluoro-4-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
23. (6-(4-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
24. (6-(3-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
25. (6-(2-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
26. (6-(3-(trifluoromethyl)benzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
27. (6-(4-(trifluoromethyl)benzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
28. (6-(2-(trifluoromethyl)benzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
29. (6-(pyrimidine-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
30. (6-(thiophene-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
31. (6-(benzo[d]thiazole-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
32. (6-(quinoxaline-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
33. (2-(5-methylpyrazine-2-carboxamido)thiazolo[4,5-b]pyridin-6-yl) carbonohydrazonoyl dicyanide,
34. (6-(p-tolylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
35. (6-(4-methoxyphenylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
36. (6-(5-methylpyrazin-2-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
37. (6-(4-chlorophenylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
38. (6-(6-methylpyridin-3-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
39. (6-(5-methylpyridin-3-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
40. (6-(pyridin-3-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
41. (6-(6-methylpyrazin-2-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
42. (6-(pyrimidin-5-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
43. (6-(pyrimidin-2-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
44. (4-(4-methoxyphenylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
45. (4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
46. (4-(6-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
47. (4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
48. (4-(5-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
49. (4-(pyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
50. (4-(pyrimidin-5-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
51. (2-methoxy-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
52. (3-methyl-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
53. (3-methyl-4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
54. (3-methyl-4-(6-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
55. (2-methyl-4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
56. (2-fluoro-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
57. (2-methoxy-4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
58. (6-(phenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
59. (6-(4-methoxyphenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
60. (6-(pyridine-3-sulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
61. (6-(1-methyl-1H-pyrazole-4-sulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
62. (6-(thiophene-2-sulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
63. (6-(4-methylphenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
64. (6-(4-fluorophenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
65. (4-(N-(6-methylpyridin-3-yl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide,
66. (4-(N-(4-methoxyphenyl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide,
67. (4-(N-(5-methylpyrazin-2-yl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide,
68. (6-phenoxypyridin-3-yl)carbonohydrazonoyl dicyanide,
69. (6-(3-fluorophenoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
70. (5-phenoxypyridin-2-yl)carbonohydrazonoyl dicyanide,
71. (3-fluoro-4-phenoxyphenyl)carbonohydrazonoyl dicyanide,
72. (3-fluoro-4-(pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
73. (4-phenoxy-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
74. (3-methyl-4-(pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
75. methyl(5-phenoxypyridin-2-yl)carbonohydrazonoyl dicyanide,
76. (6-(3-fluorophenoxy)pyridin-3-yl)(methyl)carbonohydrazonoyl dicyanide,
77. (3-fluoro-4-phenoxyphenyl)(methyl)carbonohydrazonoyl dicyanide,
78. methyl(4-phenoxy-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
79. (3-methyl-4-(pyridin-4-yloxy)phenyl)carbonohydrazonoyl dicyanide,
80. (3-fluoro-4-(pyridin-4-yloxy)phenyl)carbonohydrazonoyl dicyanide,
81. (3-methyl-4-(pyrimidin-5-yloxy)phenyl)carbonohydrazonoyl dicyanide,
82. (3-fluoro-4-(pyrimidin-5-yloxy)phenyl)carbonohydrazonoyl dicyanide,
83. (4-(pyridin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
84. (4-(pyrazin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
85. (4-(pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
86. (4-(2-cyanophenoxy)phenyl)carbonohydrazonoyl dicyanide,
87. (4-(4-cyanophenoxy)phenyl)carbonohydrazonoyl dicyanide,
88. (4-(3-cyanophenoxy)phenyl)carbonohydrazonoyl dicyanide,
89. (4-(6-(trifluoromethyl)pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
90. (4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
91. (4-(pyrimidin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
92. (4-(pyridazin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
93. (4-(2-fluorophenoxy)phenyl)carbonohydrazonoyl dicyanide,
94. (4-(3-fluorophenoxy)phenyl)carbonohydrazonoyl dicyanide,
95. (6-(benzyloxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
96. (6-(4-(trifluoromethyl)benzyloxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
97. (4-(benzyloxy)-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
98. (3-(trifluoromethyl)-4-(4-(trifluoromethyl)benzyloxy)Phenyl) carbonohydrazonoyl dicyanide,
99. (6-(4-methylbenzyloxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
100. (6-phenethoxypyridin-3-yl)carbonohydrazonoyl dicyanide,
101. (4-phenethoxy-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
102. (6-(4-methoxyphenethoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
103. (6-(4-(trifluoromethyl)phenethoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
104. (3-methoxy-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
105. (3-methoxy-4-(6-methylpyrazin-2-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
106. (3-chloro-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
107. (3-methoxy-4-(5-methylpyridin-3-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
108. (3-methoxy-4-(p-tolylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
109. (3-methoxy-4-(4-methoxyphenylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
110. (6-(furan-3-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
111. (3-methyl-4-(thiazole-4-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
112. (6-(thiazole-4-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
113. (6-(oxazole-4-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
114. (6-(oxazole-5-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
115. (6-(isoxazole-3-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
116. (4-(thiazol-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
118. (4-(4-(trifluoromethyl)benzyloxy)phenyl)carbonohydrazonoyl dicyanide,
119. (4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide,
120. (4-(4-methoxyphenethoxy)phenyl)carbonohydrazonoyl dicyanide,
121. (4-(4-(trifluoromethyl)phenethoxy)phenyl)carbonohydrazonoyl dicyanide,
122. (4-phenethoxyphenyl)carbonohydrazonoyl dicyanide,
123. (4-(4-chlorophenethoxy)phenyl)carbonohydrazonoyl dicyanide,
124. (4-(pyridin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
125. (4-(pyrazin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
126. (4-((1H-benzo[d]imidazol-2-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
127. (4-(pyridazin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
128. (4-(benzo[d]oxazol-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
129. (4-(benzo[d]thiazol-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
130. (4-(benzo[b]thiophen-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
131. (6-(4-chlorophenethoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
132. (4-(4-methylbenzyloxy)-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
133. (4-(4-chlorophenethoxy)-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
134. (4-(4-methoxyphenethoxy)-3-(trifluoromethyl)phenyl) carbonohydrazonoyl dicyanide,
135. (3-(trifluoromethyl)-4-(4-(trifluoromethyl)phenethoxy)phenyl) carbonohydrazonoyl dicyanide,
136. (4-(pyrimidin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
137. (4-((1H-pyrazol-4-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
138. (4-((5-methylpyrazin-2-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
139. (4-(1-(4-(trifluoromethyl)phenyl)ethoxy)phenyl)carbonohydrazonoyl dicyanide,
140. (4-(1-(pyridin-3-yl)ethoxy)phenyl)carbonohydrazonoyl dicyanide,
141. (4-(benzyloxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
142. (3-methyl-4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide,
143. 3-methyl-4-(pyrimidin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
144. (3-methyl-4-(pyrazin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
145. (3-methyl-4-(pyridin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
146. (4-((1H-benzo[d]imidazol-2-yl)methoxy)-3-methylphenyl) carbonohydrazonoyl dicyanide,
147. (3-methyl-4-((5-methylpyrazin-2-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
148. (3-methyl-4-(4-(trifluoromethyl)benzyloxy)phenyl)carbonohydrazonoyl dicyanide,
149. (3-methyl-4-(pyridazin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
150. (4-(benzo[b]thiophen-2-ylmethoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
151. (4-((1H-pyrazol-3-yl)methoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
152. (3-methyl-4-(thiazol-4-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
153. (4-(benzyloxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
154. (3-methoxy-4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide,
155. (3-methoxy-4-(4-(trifluoromethyl)benzyloxy)phenyl)carbonohydrazonoyl dicyanide,
156. (4-(benzo[d]oxazol-2-ylmethoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
157. (4-(benzo[d]thiazol-2-ylmethoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
158. (4-(benzo[b]thiophen-2-ylmethoxy)-3-methoxyphenyl) carbonohydrazonoyl dicyanide,
159. (3-methoxy-4-(pyrazin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
160. (3-methoxy-4-(pyridin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
161. (3-methoxy-4-(pyrimidin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
162. (3-methoxy-4-((5-methylpyrazin-2-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide,
163. (4-((1H-benzo[d]imidazol-2-yl)methoxy)-3-methoxyphenyl) carbonohydrazonoyl dicyanide,
164. (3-methoxy-4-(pyridazin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
165. (4-(benzo[d]thiazol-2-ylmethoxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
166. (4-(benzo[d]oxazol-2-ylmethoxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
167. (3-methoxy-4-(thiazol-4-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
168. (4-((1H-pyrazol-3-yl)methoxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
169. (3-methoxy-4-(pyridin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
170. (3-methoxy-4-((6-methylpyridin-3-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide,
171. (3-methoxy-4-((2-methylthiazol-4-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide,
172. (3-methoxy-4-(thiophen-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
173. (3-methoxy-4-(thiophen-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
174. (3-methoxy-4-((1-methyl-1H-pyrazol-4-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide, or
175. acetyl(3-methyl-4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide.

179 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/011,469Filed 18 Jun 2021
Priority: KR 10-2020-007504219 Jun 2020
Published: US 2023/0278965 A17 Sep 2023
Granted: 9 Jun 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…
C07D 241/24
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07D 213/30
Radicals substituted by singly-bound oxygen or sulphur atoms: oxygen atoms
C07D 213/75
Nitrogen atoms: amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Family

US 2023/0278965 A1Pre-grant publication · published 7 Sep 2023
US 12,649,723 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

Provided are novel carbonohydrazonoyl dicyanide compounds including two or more aryl or heteroaryl groups connected via a linker and uses thereof.

A compound represented by Formula 1 below or a pharmaceutically acceptable salt thereof:

wherein, in Formula 1 above,
L is —NHCO—, —CONH—, —NHSO2—, —SO2NH—, or -(straight-chain or branched C0-3 alkylene)′-O-(straight-chain or branched C0-3 alkylene)″-;
R1 is hydrogen, C1-6 alkyl, or C1-6 alkylcarbonyl;
(Het)Ar1 is C6-10 arylene or 5- to 10-membered heteroarylene;
and
(Het)Ar2 is C6-10 aryl or 5- to 10-membered heteroaryl;
wherein the C6-10 aryl(ene) and 5- to 10-membered heteroaryl(ene) are each independently unsubstituted or substituted with at least one selected from the group consisting of C1-6 alkyl, C1-6 alkoxy, halogen, cyano, C1-6 haloalkyl, and C1-6 haloalkoxy,
wherein the compound is
1. (6-(5-methylpyrazine-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
2. (4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
3. (2-fluoro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
4. (2-methoxy-4-(5-methylpyrazine-2-carboxamido)phenyl) carbonohydrazonoyl dicyanide,
5. (2-chloro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
6. (2-methyl-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
7. (3-fluoro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
8. (3-methyl-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
9. methyl(3-methyl-4-(5-methylpyrazine-2-carboxamido)phenyl) carbonohydrazonoyl dicyanide,
10. (3-methoxy-4-(5-methylpyrazine-2-carboxamido)phenyl) carbonohydrazonoyl dicyanide,
11. (3-chloro-4-(5-methylpyrazine-2-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
12. (5-methyl-6-(5-methylpyrazine-2-carboxamido)pyridin-3-yl) carbonohydrazonoyl dicyanide,
13. (4-methyl-6-(5-methylpyrazine-2-carboxamido)pyridin-3-yl) carbonohydrazonoyl dicyanide,
14. (5-(5-methylpyrazine-2-carboxamido)pyridin-2-yl) carbonohydrazonoyl dicyanide,
15. (6-benzamidopyridin-3-yl)carbonohydrazonoyl dicyanide,
16. (6-(4-fluorobenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
17. (6-(2-fluorobenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
18. (6-(3-fluorobenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
19. (6-(3-fluoro-5-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
20. (6-(2-fluoro-3-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
21. (6-(4-fluoro-3-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
22. (6-(3-fluoro-4-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
23. (6-(4-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
24. (6-(3-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
25. (6-(2-methylbenzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
26. (6-(3-(trifluoromethyl)benzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
27. (6-(4-(trifluoromethyl)benzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
28. (6-(2-(trifluoromethyl)benzamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
29. (6-(pyrimidine-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
30. (6-(thiophene-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
31. (6-(benzo[d]thiazole-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
32. (6-(quinoxaline-2-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
33. (2-(5-methylpyrazine-2-carboxamido)thiazolo[4,5-b]pyridin-6-yl) carbonohydrazonoyl dicyanide,
34. (6-(p-tolylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
35. (6-(4-methoxyphenylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
36. (6-(5-methylpyrazin-2-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
37. (6-(4-chlorophenylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
38. (6-(6-methylpyridin-3-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
39. (6-(5-methylpyridin-3-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
40. (6-(pyridin-3-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
41. (6-(6-methylpyrazin-2-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
42. (6-(pyrimidin-5-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
43. (6-(pyrimidin-2-ylcarbamoyl)pyridin-3-yl)carbonohydrazonoyl dicyanide,
44. (4-(4-methoxyphenylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
45. (4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
46. (4-(6-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
47. (4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
48. (4-(5-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
49. (4-(pyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
50. (4-(pyrimidin-5-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
51. (2-methoxy-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
52. (3-methyl-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
53. (3-methyl-4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
54. (3-methyl-4-(6-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
55. (2-methyl-4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
56. (2-fluoro-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
57. (2-methoxy-4-(6-methylpyridin-3-ylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
58. (6-(phenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
59. (6-(4-methoxyphenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
60. (6-(pyridine-3-sulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
61. (6-(1-methyl-1H-pyrazole-4-sulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
62. (6-(thiophene-2-sulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
63. (6-(4-methylphenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
64. (6-(4-fluorophenylsulfonamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
65. (4-(N-(6-methylpyridin-3-yl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide,
66. (4-(N-(4-methoxyphenyl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide,
67. (4-(N-(5-methylpyrazin-2-yl)sulfamoyl)phenyl)carbonohydrazonoyl dicyanide,
68. (6-phenoxypyridin-3-yl)carbonohydrazonoyl dicyanide,
69. (6-(3-fluorophenoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
70. (5-phenoxypyridin-2-yl)carbonohydrazonoyl dicyanide,
71. (3-fluoro-4-phenoxyphenyl)carbonohydrazonoyl dicyanide,
72. (3-fluoro-4-(pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
73. (4-phenoxy-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
74. (3-methyl-4-(pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
75. methyl(5-phenoxypyridin-2-yl)carbonohydrazonoyl dicyanide,
76. (6-(3-fluorophenoxy)pyridin-3-yl)(methyl)carbonohydrazonoyl dicyanide,
77. (3-fluoro-4-phenoxyphenyl)(methyl)carbonohydrazonoyl dicyanide,
78. methyl(4-phenoxy-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
79. (3-methyl-4-(pyridin-4-yloxy)phenyl)carbonohydrazonoyl dicyanide,
80. (3-fluoro-4-(pyridin-4-yloxy)phenyl)carbonohydrazonoyl dicyanide,
81. (3-methyl-4-(pyrimidin-5-yloxy)phenyl)carbonohydrazonoyl dicyanide,
82. (3-fluoro-4-(pyrimidin-5-yloxy)phenyl)carbonohydrazonoyl dicyanide,
83. (4-(pyridin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
84. (4-(pyrazin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
85. (4-(pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
86. (4-(2-cyanophenoxy)phenyl)carbonohydrazonoyl dicyanide,
87. (4-(4-cyanophenoxy)phenyl)carbonohydrazonoyl dicyanide,
88. (4-(3-cyanophenoxy)phenyl)carbonohydrazonoyl dicyanide,
89. (4-(6-(trifluoromethyl)pyridin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
90. (4-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
91. (4-(pyrimidin-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
92. (4-(pyridazin-3-yloxy)phenyl)carbonohydrazonoyl dicyanide,
93. (4-(2-fluorophenoxy)phenyl)carbonohydrazonoyl dicyanide,
94. (4-(3-fluorophenoxy)phenyl)carbonohydrazonoyl dicyanide,
95. (6-(benzyloxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
96. (6-(4-(trifluoromethyl)benzyloxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
97. (4-(benzyloxy)-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
98. (3-(trifluoromethyl)-4-(4-(trifluoromethyl)benzyloxy)Phenyl) carbonohydrazonoyl dicyanide,
99. (6-(4-methylbenzyloxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
100. (6-phenethoxypyridin-3-yl)carbonohydrazonoyl dicyanide,
101. (4-phenethoxy-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
102. (6-(4-methoxyphenethoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
103. (6-(4-(trifluoromethyl)phenethoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
104. (3-methoxy-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
105. (3-methoxy-4-(6-methylpyrazin-2-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
106. (3-chloro-4-(5-methylpyrazin-2-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
107. (3-methoxy-4-(5-methylpyridin-3-ylcarbamoyl)phenyl) carbonohydrazonoyl dicyanide,
108. (3-methoxy-4-(p-tolylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
109. (3-methoxy-4-(4-methoxyphenylcarbamoyl)phenyl)carbonohydrazonoyl dicyanide,
110. (6-(furan-3-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
111. (3-methyl-4-(thiazole-4-carboxamido)phenyl)carbonohydrazonoyl dicyanide,
112. (6-(thiazole-4-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
113. (6-(oxazole-4-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
114. (6-(oxazole-5-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
115. (6-(isoxazole-3-carboxamido)pyridin-3-yl)carbonohydrazonoyl dicyanide,
116. (4-(thiazol-2-yloxy)phenyl)carbonohydrazonoyl dicyanide,
118. (4-(4-(trifluoromethyl)benzyloxy)phenyl)carbonohydrazonoyl dicyanide,
119. (4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide,
120. (4-(4-methoxyphenethoxy)phenyl)carbonohydrazonoyl dicyanide,
121. (4-(4-(trifluoromethyl)phenethoxy)phenyl)carbonohydrazonoyl dicyanide,
122. (4-phenethoxyphenyl)carbonohydrazonoyl dicyanide,
123. (4-(4-chlorophenethoxy)phenyl)carbonohydrazonoyl dicyanide,
124. (4-(pyridin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
125. (4-(pyrazin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
126. (4-((1H-benzo[d]imidazol-2-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
127. (4-(pyridazin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
128. (4-(benzo[d]oxazol-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
129. (4-(benzo[d]thiazol-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
130. (4-(benzo[b]thiophen-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
131. (6-(4-chlorophenethoxy)pyridin-3-yl)carbonohydrazonoyl dicyanide,
132. (4-(4-methylbenzyloxy)-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
133. (4-(4-chlorophenethoxy)-3-(trifluoromethyl)phenyl)carbonohydrazonoyl dicyanide,
134. (4-(4-methoxyphenethoxy)-3-(trifluoromethyl)phenyl) carbonohydrazonoyl dicyanide,
135. (3-(trifluoromethyl)-4-(4-(trifluoromethyl)phenethoxy)phenyl) carbonohydrazonoyl dicyanide,
136. (4-(pyrimidin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
137. (4-((1H-pyrazol-4-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
138. (4-((5-methylpyrazin-2-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
139. (4-(1-(4-(trifluoromethyl)phenyl)ethoxy)phenyl)carbonohydrazonoyl dicyanide,
140. (4-(1-(pyridin-3-yl)ethoxy)phenyl)carbonohydrazonoyl dicyanide,
141. (4-(benzyloxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
142. (3-methyl-4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide,
143. 3-methyl-4-(pyrimidin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
144. (3-methyl-4-(pyrazin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
145. (3-methyl-4-(pyridin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
146. (4-((1H-benzo[d]imidazol-2-yl)methoxy)-3-methylphenyl) carbonohydrazonoyl dicyanide,
147. (3-methyl-4-((5-methylpyrazin-2-yl)methoxy)phenyl)carbonohydrazonoyl dicyanide,
148. (3-methyl-4-(4-(trifluoromethyl)benzyloxy)phenyl)carbonohydrazonoyl dicyanide,
149. (3-methyl-4-(pyridazin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
150. (4-(benzo[b]thiophen-2-ylmethoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
151. (4-((1H-pyrazol-3-yl)methoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
152. (3-methyl-4-(thiazol-4-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
153. (4-(benzyloxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
154. (3-methoxy-4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide,
155. (3-methoxy-4-(4-(trifluoromethyl)benzyloxy)phenyl)carbonohydrazonoyl dicyanide,
156. (4-(benzo[d]oxazol-2-ylmethoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
157. (4-(benzo[d]thiazol-2-ylmethoxy)-3-methylphenyl)carbonohydrazonoyl dicyanide,
158. (4-(benzo[b]thiophen-2-ylmethoxy)-3-methoxyphenyl) carbonohydrazonoyl dicyanide,
159. (3-methoxy-4-(pyrazin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
160. (3-methoxy-4-(pyridin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
161. (3-methoxy-4-(pyrimidin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
162. (3-methoxy-4-((5-methylpyrazin-2-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide,
163. (4-((1H-benzo[d]imidazol-2-yl)methoxy)-3-methoxyphenyl) carbonohydrazonoyl dicyanide,
164. (3-methoxy-4-(pyridazin-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
165. (4-(benzo[d]thiazol-2-ylmethoxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
166. (4-(benzo[d]oxazol-2-ylmethoxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
167. (3-methoxy-4-(thiazol-4-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
168. (4-((1H-pyrazol-3-yl)methoxy)-3-methoxyphenyl)carbonohydrazonoyl dicyanide,
169. (3-methoxy-4-(pyridin-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
170. (3-methoxy-4-((6-methylpyridin-3-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide,
171. (3-methoxy-4-((2-methylthiazol-4-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide,
172. (3-methoxy-4-(thiophen-2-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
173. (3-methoxy-4-(thiophen-3-ylmethoxy)phenyl)carbonohydrazonoyl dicyanide,
174. (3-methoxy-4-((1-methyl-1H-pyrazol-4-yl)methoxy)phenyl) carbonohydrazonoyl dicyanide, or
175. acetyl(3-methyl-4-(4-methylbenzyloxy)phenyl)carbonohydrazonoyl dicyanide.

179 more elements

Facts

Application

18/011,469Filed 18 Jun 2021

Priority

KR 10-2020-007504219 Jun 2020

Published

US 2023/0278965 A17 Sep 2023

Granted

9 Jun 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…
C07D 241/24
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07D 213/30
Radicals substituted by singly-bound oxygen or sulphur atoms: oxygen atoms
C07D 213/75
Nitrogen atoms: amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates