WO2011139107A2 - Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and phamaceutical composition comprising the same - Google Patents
Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and phamaceutical composition comprising the same Download PDFInfo
- Publication number
- WO2011139107A2 WO2011139107A2 PCT/KR2011/003362 KR2011003362W WO2011139107A2 WO 2011139107 A2 WO2011139107 A2 WO 2011139107A2 KR 2011003362 W KR2011003362 W KR 2011003362W WO 2011139107 A2 WO2011139107 A2 WO 2011139107A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydroxyadamantan
- picolinamide
- methylpiperazin
- piperazin
- pyrimidine
- Prior art date
Links
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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Abstract
Description
Examples | Structures | MS (ESI) |
17 | 340[M+H]+ | |
18 | 354[M+H]+ | |
19 | 451[M+H]+ | |
20 | 435[M+H]+ | |
21 | 355[M+H]+ | |
22 | 383[M+H]+ |
Examples | Structures | MS (ESI) | Methods |
37 | 440[M+H]+ | B | |
38 | 440[M+H]+ | B | |
39 | 793[2M+Na]+ | B | |
40 | 412[M+H]+ | B | |
41 | 448[M+H]+ | B | |
42 | 386[M+H]+ | B | |
43 | 428[M+H]+ | B | |
44 | 442[M+H]+ | B | |
45 | 439[M+H]+ | A | |
46 | 441[M+H]+ | A | |
47 | 432[M+H]+ | A | |
48 | 457[M+H]+ | B | |
49 | 434[M+H]+ | A | |
50 | 433[M+H]+ | A | |
51 | 458[M+H]+ | A | |
52 | 449[M+H]+ | B | |
53 | 467[M+H]+ | A | |
54 | 501[M+H]+ | A | |
55 | 451[M+H]+ | A | |
56 | 447[M+H]+ | A | |
57 | 463[M+H]+ | A | |
58 | 478[M+H]+ | A | |
59 | 829[2M+Na]+ | A | |
60 | 829[2M+Na]+ | A | |
61 | 370[M+H]+ | A | |
62 | 447[M+H]+ | A |
Examples | Structures | MS (ESI) |
92 | 500[M+H]+ | |
93 | 446[M+H]+ | |
94 | 462[M+H]+ | |
95 | 433[M+H]+ | |
96 | 501[M+H]+ | |
97 | 451[M+H]+ | |
98 | 447[M+H]+ | |
99 | 458[M+H]+ | |
100 | 458[M+H]+ | |
101 | 433[M+H]+ | |
102 | 447[M+H]+ | |
103 | 448[M+H]+ |
Examples | Structures | MS (ESI) |
107 | 472[M+H]+ | |
108 | 525[M+H]+ | |
109 | 525[M+H]+ | |
110 | 525[M+H]+ | |
111 | 477[M+H]+ | |
112 | 495[M+H]+ | |
113 | 495[M+H]+ | |
114 | 507[M+H]+ | |
115 | 490[M+H]+ | |
116 | 531[M+H]+ | |
117 | 492[M+H]+ | |
118 | 478[M+H]+ | |
119 | 478[M+H]+ | |
120 | 462[M+H]+ | |
121 | 493[M+H]+ | |
122 | 448[M+H]+ | |
123 | 525[M+H]+ | |
124 | 495[M+H]+ |
Examples | Structures | MS (ESI) |
136 | 523[M+H]+ | |
137 | 509[M+H]+ | |
138 | 508[M+H]+ | |
139 | 522[M+H]+ | |
140 | 539[M+H]+ | |
141 | 525[M+H]+ | |
142 | 524[M+H]+ | |
143 | 538[M+H]+ | |
144 | 535[M+H]+ | |
145 | 521[M+H]+ | |
146 | 520[M+H]+ | |
147 | 534[M+H]+ | |
148 | 535[M+H]+ | |
149 | 521[M+H]+ | |
150 | 520[M+H]+ | |
151 | 534[M+H]+ | |
152 | 523[M+H]+ | |
153 | 509[M+H]+ | |
154 | 522[M+H]+ | |
155 | 506[M+H]+ | |
156 | 492[M+H]+ | |
157 | 491[M+H]+ | |
158 | 505[M+H]+ |
Examples | Structures | MS (ESI) |
175 | 489[M+H]+ | |
176 | 543[M+H]+ | |
177 | 514[M+H]+ | |
178 | 503[M+H]+ | |
179 | 505[M-OH]+ | |
180 | 505[M-OH]+ | |
181 | 503[M+H]+ | |
182 | 504[M+H]+ | |
183 | 535[M+H]+ |
Examples | Structures | MS (ESI) |
202 | 413[M+H]+ | |
203 | 439[M+H]+ | |
204 | 449[M+H]+ | |
205 | 475[M+H]+ | |
206 | 541[M+H]+ | |
207 | 579[M+H]+ | |
208 | 553[M+H]+ |
Examples | Structures | MS (ESI) |
236 | 507[M+H]+ | |
237 | 544[M+H]+ | |
238 | 524[M+H]+ | |
239 | 473[M+H]+ | |
240 | 466[M+H]+ | |
241 | 482[M+H]+ | |
242 | 516[M+H]+ | |
243 | 504[M+H]+ | |
244 | 540[M+H]+ | |
245 | 558[M+H]+ | |
246 | 560[M+H]+ | |
247 | 562[M+H]+ | |
248 | 467[M+H]+ | |
249 | 485[M+H]+ | |
250 | 523[M+H]+ | |
251 | 541[M+H]+ | |
252 | 482[M+H]+ | |
253 | 481[M+H]+ | |
254 | 499[M+H]+ | |
255 | 540[M+H]+ | |
256 | 544[M+H]+ | |
257 | 576[M+H]+ | |
258 | 526[M+H]+ | |
259 | 604[M+H]+ | |
260 | 524[M+H]+ | |
261 | 491[M+H]+ | |
262 | 491[M+H]+ | |
263 | 508[M+H]+ |
Examples | Structures | MS (ESI) |
264 | 476[M+H]+ | |
265 | 428[M+H]+ | |
266 | 456[M+H]+ | |
267 | 492[M+H]+ | |
268 | 472[M+H]+ | |
269 | 444[M+H]+ | |
270 | 512[M+H]+ | |
271 | 492[M+H]+ | |
272 | 464[M+H]+ | |
273 | 488[M+H]+ | |
274 | 468[M+H]+ | |
275 | 440[M+H]+ | |
276 | 494[M+H]+ | |
277 | 466[M+H]+ | |
278 | 461[M+H]+ | |
279 | 475[M+H]+ | |
280 | 528[M+H]+ | |
281 | 508[M+H]+ | |
282 | 480[M+H]+ | |
283 | 491[M+H]+ | |
284 | 544[M+H]+ | |
285 | 524[M+H]+ | |
286 | 496[M+H]+ | |
287 | 516[M+H]+ | |
288 | 542[M+H]+ | |
289 | 510[M+H]+ | |
290 | 532[M+H]+ | |
291 | 512[M+H]+ | |
292 | 484[M+H]+ | |
293 | 546[M+H]+ | |
294 | 526[M+H]+ | |
295 | 498[M+H]+ |
Examples | Structures | MS (ESI) |
300 | 511[M+H]+ | |
301 | 562[M+H]+ | |
302 | 615[M+H]+ | |
303 | 517[M+H]+ | |
304 | 535[M+H]+ | |
305 | 438[M+H]+ | |
306 | 452[M+H]+ | |
307 | 456[M+H]+ | |
308 | 506[M+H]+ |
Examples | hHSD1 inhibiting activity | |
%inhibition at 100 μM | %inhibition at 10 μM | |
36 | 99 | 62 |
37 | 97 | 51 |
40 | 98 | 40 |
41 | 96 | 26 |
42 | 97 | 35 |
47 | 96 | 36 |
49 | 96 | 24 |
50 | 97 | 23 |
51 | 99 | 67 |
57 | 82 | 53 |
58 | 85 | 72 |
60 | 82 | 68 |
61 | 83 | 68 |
72 | 83 | 12 |
74 | 80 | 34 |
77 | 87 | 73 |
78 | 84 | 32 |
79 | 87 | 42 |
87 | 79 | 40 |
88 | 84 | 40 |
91 | 76 | 34 |
97 | 77 | 58 |
98 | 78 | 38 |
104 | 87 | 49 |
105 | 91 | 38 |
106 | 90 | 86 |
118 | 84 | 64 |
119 | 81 | 65 |
124 | 85 | 54 |
125 | 79 | 48 |
132 | 87 | 71 |
133 | 85 | 70 |
150 | 87 | 76 |
151 | 85 | 75 |
167 | 85 | 42 |
168 | 88 | 77 |
173 | 87 | 81 |
174 | 82 | 79 |
190 | 89 | 76 |
192 | 85 | 41 |
196 | 86 | 64 |
201 | 78 | 40 |
204 | 76 | 41 |
230 | 82 | 69 |
231 | 78 | 42 |
235 | 85 | 62 |
239 | 76 | 52 |
242 | 77 | 39 |
284 | 86 | 56 |
290 | 83 | 67 |
Claims (7)
- An amide compound represented by the formula 1 below, or a pharmaceutically acceptable salt, solvate, hydrate, prodrug, racemate, or stereoisomer thereof.[Formula 1][In the formula 1,X represents N or CR, and Y represents N or CH, provided that X and Y are not carbon at the same time;Z represents N or CH;R1 and R2 independently represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, norbornyl, adamantyl, noradamantyl, (C6-C20)aryl, (C6-C20)ar(C1-C10)alkyl, or (C3-C20)heteroaryl, or R1 and R2 may be linked to each other, together with nitrogen atoms to which they are bound, to form (C1-C10) saturated or unsaturated heterocycle, biheterocycle or fused heterocycle, provided that both R1 and R2 are not hydrogen at the same time;L represents a single bond, -O-, -NR11-, -CO-, -SO2-, -(CR21R22)-(CH2)c- (c represents an integer of 0 to 5), -CO(CR21R22)d- (d represents an integer of 1 to 6), (C3-C10)cycloalkylene, (C6-C20)arylene or (C3-C20)heteroarylene;R21 and R22 independently represent hydrogen or (C1-C10)alkyl, or R21 and R22 may be linked via alkylene or alkenylene to form a cycloaliphatic ring or an aromatic ring;R and R3 independently represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C1-C10)alkoxy, halogen, hydroxy, cyano, -NR31R32, nitro, -CONH2, -CO2R33, -SO3H, -SO2NR34R35, -SO2R36, -O(CH2)aCO2H (a represents an integer of 1 to 3), -O(CH2)bCONH2 (b represents an integer of 1 to 3), -NH(CO)R37, -NH(SO2)R38, 5- to 7-membered heterocycle, (C6-C20)aryl or (C3-C20)heteroaryl;R4 and R5 independently represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C1-C10)alkoxy, halogen, hydroxy, cyano, amino, nitro, -CONH2 or -CO2R12, and include all of isomers and racemic compounds thereof all, or R4 and R5 may be substituted with adjacent carbon atoms to form (C1-C10) saturated or unsaturated carbocycle, heterocycle, bicarbocycle, biheterocycle, fused carbocycle, or fused heterocycle, or may be linked to R3 to form saturated or unsaturated carbocycle;R6 and R7 independently represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C1-C10)alkoxy, halogen, hydroxy, cyano, amino, nitro, -CONH2 or -CO2R12;the cycloalkylene, arylene or heteroarylene of L; the alkyl, cycloalkyl, norbornyl, adamantyl, noradamantyl, aryl, aralkyl or heteroaryl of R1 and R2; the saturated or unsaturated heterocycle, biheterocycle or fused heterocycle formed by the linkage of R1 and R2; the alkyl, cycloalkyl, alkoxy, heterocycle, aryl or heteroaryl of R and R3; the alkyl, cycloalkyl or alkoxy of R4 and R5; the saturated or unsaturated carbocycle, heterocycle, bicarbocycle, biheterocycle, fused carbocycle or fused heterocycle formed by the substitution of R4 and R5 with adjacent carbon atoms; and the alkyl, cycloalkyl or alkoxy of R6 and R7 may be further substituted with one or more substituent(s)selected from the group consisting of (C1-C10)alkyl, (C3-C10)cycloalkyl, (C1-C10)alkoxy, halo(C1-C10)alkyl, halo(C1-C10)alkoxy, halogen, hydroxy, cyano, -NR41R42, nitro, -CO2R43, -CONH2, -SO3H, -SO2NR44R45, -SO2(CH2)cNR44R45 (c represents an integer of 1 to 3), -SO2R46, -O(CH2)cCO2H (c represents an integer of 1 to 3), -O(CH2)dCONH2 (d represents an integer of 1 to 3), -NH(CO)R47, -NH(SO2)R48, (C6-C20)aryl and (C3-C20)heteroaryl;R11, R12, R31, R32, R33, R34, R35, R36, R37, R38, R41, R42, R43, R44, R45, R46, R47 and R48 independently represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl or (C6-C20)aryl; andm and n independently represent an integer of 0 to 3, provided that m+n represents an integer of 2 or more.]
- The amide compound, or the pharmaceutically acceptable salt, solvate, hydrate, prodrug, racemate, or stereoisomer thereof, of claim 1,wherein R1 and R2 independently represent hydrogen, (C3-C10)cycloalkyl, norbornyl, adamantyl, noradamantyl or (C6-C20)ar(C1-C10)alkyl, or R1 and R2 may be linked to each other to form heterocycle selected from the following:L represents a single bond, -CO-, -SO2-, -(CR21R22)-(CH2)c- (c represents an integer of 0 to 5), , -CO(CR21R22)d- (d represents an integer of 1 to 6), (C3-C10)cycloalkylene, (C6-C20)arylene or (C3-C20)heteroarylene;R21 and R22 independently represent hydrogen or (C1-C10)alkyl;R3 represents hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl, (C1-C10)alkoxy, halogen, hydroxy, cyano, -NR31R32, nitro, -CONH2, -CO2R33, -SO2NR34R35, -SO2R36, -O(CH2)aCO2H (a represents an integer of 1 to 3), -O(CH2)bCONH2 (b represents an integer of 1 to 3), -NH(CO)R37, -NH(SO2)R38, 5- to 7-membered heterocycle, (C6-C20)aryl or (C3-C20)heteroaryl;R6 and R7 independently represent hydrogen, (C1-C10)alkyl or halogen;the cycloalkylene, arylene or heteroarylene of the L; the cycloalkyl, norbornyl, adamantyl, noradamantyl or aralkyl of R1 and R2; the alkyl, cycloalkyl, alkoxy, heterocycle, aryl or heteroaryl of R3; and the alkyl of R6 and R7 may be further substituted with one or more substituent(s)selected from the group consisting of (C1-C10)alkyl, (C3-C10)cycloalkyl, (C1-C10)alkoxy, halo(C1-C10)alkyl, halo(C1-C10)alkoxy, halogen, hydroxy, cyano, -NR41R42, nitro, -CO2R43, -CONH2, -SO3H, -SO2NR44R45, -SO2(CH2)cNR44R45 (c represents an integer of 1 to 3), -SO2R46, -O(CH2)cCO2H (c represents an integer of 1 to 3), -O(CH2)dCONH2 (d represents an integer of 1 to 3), -NH(CO)R47, -NH(SO2)R48, (C6-C20)aryl and (C3-C20) heteroaryl; andR11, R12, R31, R32, R33, R34, R35, R36, R37, R38, R41, R42, R43, R44, R45, R46, R47 and R48 independently represent hydrogen, (C1-C10)alkyl, (C3-C10)cycloalkyl or (C6-C20)aryl.
- The amide compound, or the pharmaceutically acceptable salt, solvate, hydrate, prodrug, racemate, or stereoisomer thereof, of claim 1, selected from the group consisting of:N-cyclohexyl-6-(piperidin-1-yl)picolinamide;N-cyclohexyl-6-(4-methylpiperidin-1-yl)picolinamide;N-cyclohexyl-6-(4-(4-methoxyphenyl)piperidin-1-yl)picolinamide;N-cyclohexyl-6-(4-(4-chlorophenyl)piperidin-1-yl)picolinamide;N-cyclohexyl-6-(4-(4-fluorophenyl)piperidin-1-yl)picolinamide;(4-methylpiperidin-1-yl)(6-(piperidin-1-yl)pyridin-2-yl)methanone;(4-methylpiperidin-1-yl)(6-(4-methylpiperidin-1-yl)pyridin-2-yl)methanone;(6-(4-(4-methoxyphenyl)piperidin-1-yl)pyridin-2-yl)(4-methylpiperidin-1-yl)methanone;(6-(4-(4-chlorophenyl)piperidin-1-yl)pyridin-2-yl)(4-methylpiperidin-1-yl)methanone;(6-(4-(4-fluorophenyl)piperidin-1-yl)pyridin-2-yl)(4-methylpiperidin-1-yl)methanone;(3,3-dimethylpiperidin-1-yl)(6-(4-(4-methoxyphenyl)piperazin-1-yl)pyridin-2-yl)methanone;(3,3-dimethylpiperidin-1-yl)(6-(piperidin-1-yl)pyridin-2-yl)methanone;(3,3-dimethylpiperidin-1-yl)(6-(4-methylpiperidin-1-yl)pyridin-2-yl)methanone;(6-(4-(4-chlorophenyl)piperazin-1-yl)pyridin-2-yl)(3,3-dimethylpiperidin-1-yl)methanone;(6-(4-(4-fluorophenyl)piperazin-1-yl)pyridin-2-yl)(3,3-dimethylpiperidin-1-yl)methanone;(N-(Adamantan-2-yl)-6-(4-(4-methoxyphenyl)piperazin-1-yl)picolinamide)(N-(adamantan-2-yl)-6-(piperidin-1-yl)picolinamide;N-(adamantan-2-yl)-6-(4-methylpiperidin-1-yl)picolinamide;(N-(adamantan-2-yl)-6-(4-(4-chlorophenyl)piperazin-1-yl)picolinamide;N-(adamantan-2-yl)-6-(4-(4-fluorophenyl)piperazin-1-yl)picolinamide;N-(adamantan-2-yl)-6-(4-methylpiperazin-1-yl)picolinamide;N-(adamantan-2-yl)-6-(4-acetylpiperidin-1-yl)picolinamide;(N-(adamantan-2-yl)-6-(piperazin-1-yl)picolinamide;(N-(adamantan-2-yl)-6-(4-(2-hydroxyethyl)piperazin-1-yl)picolinamide;methyl 3-(4-(6-(adamantan-2-ylcarbamoyl)pyridin-2-yl)piperazin-1-yl)propanoate;3-(4-(6-(adamantan-2-ylcarbamoyl)pyridin-2-yl)piperazin-1-yl)propanoic acid;N-(adamantan-2-yl)-6-(4-(3-amino3-oxopropyl)piperazin-1-yl)picolinamide;(S)-(6-(piperidin-1-yl)pyridin-2-yl)(3-(2-(trifluoromethyl)phenyl)pyrrolidine-1-yl)methanone;(6-(piperidin-1-yl)pyridin-2-yl)(2-(pyridin-3-yl)piperidin-1-yl)methanone;(4-hydroxy-4-(trifluoromethyl)piperidin-1-yl)(6-(piperidin-1-yl)pyridin-2-yl)methanone;(3-hydroxy-3-(trifluoromethyl)piperidin-1-yl)(6-(piperidin-1-yl)pyridin-2-yl)methanone;(6-(4-(4-chlorophenyl)piperazin-1-yl)pyridin-2-yl)((S)-3-(2-(trifluoromethyl)phenyl)pyrrolidine-1-yl)methanone;(6-(4-(4-chlorophenyl)piperazin-1-yl)pyridin-2-yl)(2-(pyridin-3-yl)piperidin-1-yl)methanone;(6-(4-(4-chlorophenyl)piperazin-1-yl)pyridin-2-yl)(4-(trifluoromethyl)-4-hydroxypiperidin-1-yl)methanone;(6-(4-(4-chlorophenyl)piperazin-1-yl)pyridin-2-yl)(3-(trifluoromethyl)-3-hydroxypiperidin-1-yl)methanone;N-((E)-5-hydroxyadamantan-2-yl)-6-(piperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(trifluoromethyl)-4-hydroxypiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(3-(trifluoromethyl)-3-hydroxypiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-hydroxy-4-methylpiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-cyclopropyl-4-hydroxypiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-hydroxy-4-phenylpiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(hydroxymethyl)piperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(methoxycarbonylmethyl)piperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(methoxycarbonylethyl)piperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(piperidin-1-yl)piperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-morpholinopiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-phenylpiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-cyanophenyl)piperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(pyridin-2-yl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-phenylpiperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-cyanophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-hydroxyphenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-chlorophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-trifluoromethyl)phenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-fluorophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-p-tolylpiperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-methoxyphenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-nitrophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(3,4-dihydroquinoline-1(2H)-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(3,4-dihydroisoquinoline-2(1H)-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(2-methylpiperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-benzylpiperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(pyridin-3-ylmethyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(pyridin-2-ylmethyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(2-hydroxyethyl)piperazin-1-yl)picolinamide;methyl 3-(4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)piperazin-1-yl)propanoate;3-(4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)piperazin-1-yl)propanic acid;6-(4-(3-amino-3-oxopropyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(2-amino-2-oxoethyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;2-(1-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)piperidin-4-yl)acetic acid;6-(4-(3-amino-3-oxopropyl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;3-(1-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)piperidin-4-yl)propanic acid;6-(4-(4-carbamoylphenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(4-carbamoylphenyl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(4-aminopheny)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-cyano-3-fluorophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(2-chloro-4-cyanophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(3,4-dimethoxyphenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-(4-(4-ethoxycarbonylmethoxyphenyl)piperazin-1-yl)picolinamide;6-(4-(4-carbamoyl-3-fluorophenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(4-carbamoyl-2-chlorophenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;2-(4-(4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)piperazin-1-yl)phenoxy)acetic acid;6-(4-(5-chloropyridin-2-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-fluoropyridin-2-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-methylpyridin-2-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-cyanopyridin-2-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-carbamoylpyridin-2-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(4-fluorophenyl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(4-(trifluoromethyl)phenyl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-p-tolylpiperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(4-methoxyphenyl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(pyridin-2-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-(trifluoromethyl)pyridin-2-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-fluoropyridin-2-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-methylpyridin-2-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(5-cyanopyridin-2-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(3-cyanopyridin-2-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(pyridin-3-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(6-methylpyridin-3-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(6-aminopyridin-3-yl)piperidin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(1-(4-cyanophenyl)piperidin-4-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(1-(5-cyanopyridin-2-yl)piperidin-4-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-cyanophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((S)-4-(4-cyanophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((S)-2-methyl-4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(3-(methylsulfonyl)phenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide6-((R)-4-(4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(3-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(3,4-dimethoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(dimethylamino)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(4-(trifluoromethoxy)phenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(4-nitrophenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(5-methoxypyridin-2-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(6-methoxypyridin-3-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(6-methylpyridin-3-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(6-nitropyridin-3-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(pyridin-4-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(4-(methylsulfonyl)phenyl)-1,4-diazepan-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-(4-(2-fluoro-4-methoxyphenyl)-1,4-diazepan-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(6-aminopyridin-3-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-aminophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-acetamidophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-(methylsulfoneamido)phenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methylpiperazin-1-yl)picolinamide;methyl 4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)benzoate;4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)benzoic acid;6-((R)-4-(4-carbamoylphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-(methylcarbamoyl)phenyl)piperazin-1-yl)picolinamide;6-((R)-4-(4-(cyclopropylcarbamoyl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-4-(4-((2-hydroxyethyl)carbamoyl)phenyl)-2-methylpiperazin-1-yl)picolinamide;methyl 4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-fluorobenzoate;4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-fluorobenzoic acid;6-((R)-4-(4-carbamoyl-3-fluorophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-(methylcarbamoyl)-3-fluorophenyl)piperazin-1-yl)picolinamide;methyl 4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)3-chlorobenzoate;4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)3-chlorobenzoic acid;6-((R)-4-(4-carbamoyl-2-chlorophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(methylcarbamoyl)-2-chlorophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;methyl 4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-methoxybenzoate;4-((S)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-methoxybenzoic acid;6-((R)-4-(4-carbamoyl-3-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(methylcarbamoyl)-3-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;methyl 5-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-methoxybenzoate;5-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-methoxybenzoic acid;6-((R)-4-(3-carbamoyl-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(3-(methylcarbamoyl)-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;methyl 5-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-fluorobenzoate;5-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-2-fluorobenzoic acid;6-((R)-4-(3-(methylcarbamoyl)-4-fluorophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(6-methoxycarbonylpyridin-3-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-2-methyl-4-(6-hydroxycarbonylpyridin-3-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(6-carbamoylpyridin-3-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(6-(methylcarbamoyl)pyridin-3-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;methyl 6-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)nicotinate;6-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)nicotinic acid;6-((R)-4-(5-carbamoylpyridin-2-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(5-(methylcarbamoyl)pyridin-2-yl)piperazin-1-yl)picolinamide;ethyl 6-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-5-chloronicotinate;6-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-5-chloronicotinic acid;6-((R)-4-(5-carbamoyl-3-chloropyridin-2-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(5-(methylcarbamoyl)-3-chloropyridin-2-yl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-sulfamoylphenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-(N-methylsulfamoyl)phenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-sulfamoyl-2-fluorophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-(N-methylsulfamoyl)-2-fluorophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-sulfamoyl-3-fluorophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(4-(N-methylsulfamoyl)-3-fluorophenyl)piperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-4-(4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-4-(6-(2-hydroxypropan-2-yl)pyridin-3-yl)-2-methylpiperazin-1-yl)picolinamide;6-((R)-4-(4-acetylphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-trifluoroacetylphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(2-cyanopropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(ethylcarbonyl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(3-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(1-hydroxycyclopropyl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(dimethylaminomethyl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-(2-methyl-2-hydroxypropoxy)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((2R)-4-(4-(1-hydroxyethyl)phenyl)-2-methylpiperazin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((2R)-2-methyl-4-(4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)piperazin-1-yl)picolinamide;6-((R)-4-(4-(1-amino-2-methyl-1-oxopropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(3-chloro-4-hydroxyphenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;ethyl 2-(2-chloro-4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)phenoxy)acetate;2-(2-chloro-4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)phenoxy)acetic acid;6-((R)-4-(4-(2-amino-2-oxoethoxy)-3-chlorophenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-4-(2-hydroxyethyl)-2-methylpiperazin-1-yl)picolinamide;6-((R)-4-(2-hydroxy-2-methylpropyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(2-(methylsulfonyl)ethyl)piperazin-1-yl)picolinamide;6-((R)-4-((1-cyanocyclopropyl)methyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-((1-carbamoylcyclopropyl)methyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-cyclopropyl-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(tetrahydro-2H-pyran-4-yl)piperazin-1-yl)picolinamide;6-((R)-4-(4-hydroxy-4-methylcyclohexyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(piperidin-4-yl)piperazin-1-yl)picolinamide;6-((R)-4-(1-acetylpiperidin-4-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methyl-4-(1-(methylsulfonyl)piperidin-4-yl)piperazin-1-yl)picolinamide;6-((R)-4-acetyl-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-cyclopropylcarbonyl-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-methylsulfonyl-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-cyclopropylsulfonyl-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-methoxyphenylsulfonyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-trifluoromethylphenylsulfonyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-bromophenylcarbonyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(2-hydroxyacetyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(2-hydroxy-2,2-dimethylacetyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(2-hydroxymethyl-2,2-dimethylacetyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(2-dimethylaminoacetyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(2-methoxycarbonylmethylacetyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;6-((R)-4-(4-amino-4-oxobutanoyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;4-((R)-4-(6-(((E)-5-hydroxyadamantan-2-yl)carbamoyl)pyridin-2-yl)-3-methylpiperazin-1-yl)-4-oxobutanoic acid;5-fluoro-N-((E)-5-hydroxyadamantan-2-yl)-6-((R)-2-methylpiperazin-1-yl)picolinamide;5-fluoro-6-((R)-4-(4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;5-fluoro-6-((R)-4-(2-(2-hydroxypropan-2-yl)pyridin-5-yl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;5-fluoro-6-((R)-4-(4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-5-methyl-6-(piperidin-1-yl)picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-5-methyl-6-(piperazin-1-yl)picolinamide;5-methyl-6-(4-(4-(2-hydroxypropan-2-yl)phenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;5-methyl-6-(4-(2-(2-hydroxypropan-2-yl)pyridin-5-yl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;5-methyl-6-(4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)picolinamide;N-((E)-4-hydroxycyclohexyl)-6-(piperidin-1-yl)picolinamide;N-cyclopropyl-N-((Z)-4-hydroxycyclohexyl)-6-(piperidin-1-yl)picolinamide;N-cyclopropyl-N-((E)-4-hydroxycyclohexyl)-6-(piperidin-1-yl)picolinamide;N-cyclopropyl-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)-6-(piperidin-1-yl)picolinamide;N-cyclopropyl-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)-6-(piperidin-1-yl)picolinamide;N-cyclopropyl-N-((1s,4s)-4-hydroxy-4-(trifluoromethyl)cyclohexyl)-6-(piperidin-1-yl)picolinamide;N-cyclopropyl-N-((1r,4r)-4-hydroxy-4-(trifluoromethyl)cyclohexyl)-6-(piperidin-1-yl)picolinamide;N-((1s,4s)-4-hydroxy-4-(trifluoromethyl)cyclohexyl)-6-(piperidin-1-yl)picolinamide;N-((1r,4r)-4-hydroxy-4-(trifluoromethyl)cyclohexyl)-6-(piperidin-1-yl picolinamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-(4-(4-(methylsulfonyl)phenyl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-(4-(4-methoxyphenyl)piperazin-1-yl)pyrimidine-4-carboxamide;2-((R)-4-benzyl-2-methylpiperazin-1-yl)-N-((E)-5-hydroxyadamantan-2-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-(2-hydroxypropan-2-yl)pyridin-5-yl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-cyanophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-chlorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-trifluoromethylphenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-t-butylphenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-methyl-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-fluoro-4-(ethylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-chloro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2,5-difluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(3-fluoro-pyridin-4-yl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(3,5-difluoro-pyridin-4-yl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-fluoro-4-(dimethylaminomethyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2,6-difluoro-4-(dimethylaminomethyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-amino-4-fluoro-pyridin-5-yl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-amino-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-amino-2,6-difluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(3-methyl-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(3-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-(methylsulfonyl)naphthyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(2-(methylsulfonyl)-5-bromophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-(2-hydroxypropan-2-yl)-3-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-cyano-3-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-cyano-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-4-(4-cyano-2-chlorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-cyclohexyl-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-cyclohexyl-2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-cyclohexyl-2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-(4,4-difluorocyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-(4,4-difluorocyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-(4,4-difluorocyclohexyl)pyrimidine-4-carboxamide;N-(bicyclo[2.2.1]heptan-2-yl)-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2- methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-(bicyclo[2.2.1]heptan-2-yl)-2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-(bicyclo[2.2.1]heptan-2-yl)-2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((2R,3as,5S,6aS)-octahydro-2,5-methanopentalen-3a-yl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((2R,3as,5S,6aS)-octahydro-2,5-methanopentalen-3a-yl)pyrimidine-4-carboxamide;2-((R)-4-(4-cyano-2-fluorophenyl)-2-methylpiperazin-1-yl)-N-((2R,3as,5S,6aS)-octahydro-2,5-methanopentalen-3a-yl)pyrimidine-4-carboxamide;N-(adamantan-2-yl)-2-((R)-4-(4-cyano-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-(adamantan-2-yl)-2-((R)-4-(4-methylsulfonyl-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-(adamantan-2-yl)-2-((R)-4-(4-(2-hydroxypropan-2-yl)-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-(adamantan-2-yl)-2-((R)-4-(4-methoxy-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((S)-4-(4-cyano-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((S)-4-(4-methylsulfonyl-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((S)-4-(4-(2-hydroxypropan-2-yl)-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((S)-4-(4-methoxy-2-fluorophenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;N-(2-fluorobenzyl)-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-methylpyrimidine-4-carboxamide;N-(2-fluorobenzyl)-N-cyclopropyl-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidine-4-carboxamide;(2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)pyrimidin-4-yl)(3,4-dihydroisoquinolin-2(1H)-yl)methanone;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxycyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;N-cyclopropyl-2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1s,4S)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(methylsulfonyl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4R)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-methoxyphenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(4-cyano-2-fluorophenyl)-2-methylpiperazin-1-yl)-N-((1s,4s)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;2-((R)-4-(4-cyano-2-fluorophenyl)-2-methylpiperazin-1-yl)-N-((1r,4r)-4-hydroxy-4-methylcyclohexyl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(4-nitro-2-fluorophenyl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(2,6-difluoro-4-(methylsulfonyl)phenyl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(2-fluoro-4-(3-dimethylaminopropylsulfonyl)phenyl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(3-trifluoromethylpyridin-4-yl) piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(3-trifluoromethyl-5-fluoropyridin-4-yl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(1H-pyrazol-4-yl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(3-methyl-1H-pyrazol-4-yl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(3-fluoro-1H-pyrazol-4-yl)piperazin-1-yl)pyrimidine-4-carboxamide;N-((E)-5-hydroxyadamantan-2-yl)-2-((R)-2-methyl-4-(3-trifluoromethyl-1H-pyrazol-4-yl)piperazin-1-yl)pyrimidine-4-carboxamide.
- A pharmaceutical composition comprising the amide compound or the pharmaceutically acceptable salt, solvate, hydrate, prodrug, racemate, or stereoisomer thereof according to any one of claims 1 to 3, and a pharmaceutical acceptable carrier.
- An 11β-HSD1 inhibitor comprising the amide compound or the pharmaceutically acceptable salt, solvate, hydrate, prodrug, racemate, or stereoisomer thereof according to any one of claims 1 to 3.
- A pharmaceutical composition for treating and/or preventing diseases caused, mediated, and/or spread by the high cortisol level, the pharmaceutical composition comprising the amide compound or the pharmaceutically acceptable salt, solvate, hydrate, prodrug, racemate, or stereoisomer thereof according to any one of claims 1 to 3, and a pharmaceutically acceptable carrier.
- A pharmaceutical composition for treating and/or preventing metabolic syndromes, diabetes, especially non-insulin dependent diabetes, prediabetes, insulin tolerance, low glucose tolerance, hyperglycemia, obesity and weight - related disorders, dyslipidemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, lipid disorders such as low HDL levels or high LDL levels, glaucoma, osteoporosis, cognitive disorders, glucocorticoid- mediated effects on neuron functions, such as anxiety or depression, neurodegenerative diseases, immune disorders such as tuberculosis, leprosy or psoriasis, hypertension, atherosclerosis and complications thereof, vessel restenosis, cardiovascular disease, pancreatitis, retinitis, neuropathy, or nephropathy, the pharmaceutical composition comprising the amide compound or the pharmaceutically acceptable salt, solvate, hydrate, prodrug, racemate, or stereoisomer thereof according to any one of claims 1 to 3, and a pharmaceutically acceptable carrier.
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RU2012152639/04A RU2566827C2 (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, method of obtaining thereof and thereof-containing pharmaceutical composition |
EP11777588.2A EP2566859B1 (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and pharmaceutical composition comprising the same |
AU2011249167A AU2011249167B2 (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and pharmaceutical composition comprising the same |
MX2012012972A MX336376B (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and phamaceutical composition comprising the same. |
CN201180023031.3A CN103025721B (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and pharmaceutical composition comprising the same |
JP2013508998A JP5837573B2 (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, process for producing the same and pharmaceutical compositions containing the same |
US13/696,400 US9096571B2 (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and pharmaceutical composition comprising the same |
CA2798360A CA2798360C (en) | 2010-05-07 | 2011-05-04 | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and pharmaceutical composition comprising the same |
BR112012028527A BR112012028527B8 (en) | 2010-05-07 | 2011-05-04 | Amide compound and its derivatives, use thereof and pharmaceutical composition |
ZA2012/08198A ZA201208198B (en) | 2010-05-07 | 2012-10-31 | Picolinamide and pyrimidine-4-carboxamine compounds, process for preparing and pharmaceutical composition comprising the same |
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- 2011-05-04 WO PCT/KR2011/003362 patent/WO2011139107A2/en active Application Filing
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Also Published As
Publication number | Publication date |
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CA2798360A1 (en) | 2011-11-10 |
AU2011249167B2 (en) | 2016-02-25 |
CN103025721A (en) | 2013-04-03 |
WO2011139107A3 (en) | 2012-05-18 |
MX2012012972A (en) | 2013-02-26 |
JP5837573B2 (en) | 2015-12-24 |
BR112012028527B8 (en) | 2021-10-26 |
AU2011249167A1 (en) | 2012-11-29 |
CN103025721B (en) | 2015-06-17 |
MX336376B (en) | 2016-01-15 |
TW201144294A (en) | 2011-12-16 |
EP2566859A2 (en) | 2013-03-13 |
AR081905A1 (en) | 2012-10-31 |
US9096571B2 (en) | 2015-08-04 |
EP2566859A4 (en) | 2014-07-30 |
JP2013525479A (en) | 2013-06-20 |
US20130210811A1 (en) | 2013-08-15 |
TWI491603B (en) | 2015-07-11 |
SA111320433B1 (en) | 2015-06-10 |
RU2566827C2 (en) | 2015-10-27 |
ZA201208198B (en) | 2014-01-29 |
KR20110123657A (en) | 2011-11-15 |
BR112012028527A2 (en) | 2020-08-25 |
CA2798360C (en) | 2018-10-30 |
RU2012152639A (en) | 2014-06-20 |
EP2566859B1 (en) | 2016-12-21 |
BR112012028527B1 (en) | 2021-10-05 |
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