CN107445899A - 一种苯并咪唑类化合物及其制备方法 - Google Patents
一种苯并咪唑类化合物及其制备方法 Download PDFInfo
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- CN107445899A CN107445899A CN201710589775.0A CN201710589775A CN107445899A CN 107445899 A CN107445899 A CN 107445899A CN 201710589775 A CN201710589775 A CN 201710589775A CN 107445899 A CN107445899 A CN 107445899A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- -1 benzimidazoles compound Chemical class 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000001556 benzimidazoles Chemical class 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 23
- 150000003141 primary amines Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 claims 1
- 150000003142 primary aromatic amines Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007363 ring formation reaction Methods 0.000 abstract description 6
- 150000001412 amines Chemical group 0.000 abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 238000005580 one pot reaction Methods 0.000 abstract description 4
- 238000006467 substitution reaction Methods 0.000 abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 2
- 231100000331 toxic Toxicity 0.000 abstract description 2
- 230000002588 toxic effect Effects 0.000 abstract description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003863 metallic catalyst Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 16
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000002390 rotary evaporation Methods 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XNRLBAWFYWNNGE-WUXMJOGZSA-N FC1=C(C=C(C(=C1)C)[N+](=O)[O-])/N=C/N(C)C Chemical compound FC1=C(C=C(C(=C1)C)[N+](=O)[O-])/N=C/N(C)C XNRLBAWFYWNNGE-WUXMJOGZSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IHVAYGOCCIOWQK-UHFFFAOYSA-N 1-cyclobutyl-5-nitrobenzimidazole Chemical compound [O-][N+](=O)C1=CC2=C(C=C1)N(C=N2)C1CCC1 IHVAYGOCCIOWQK-UHFFFAOYSA-N 0.000 description 1
- BJDBLDMPXGUKJW-UHFFFAOYSA-N 1-cyclopropyl-5-nitrobenzimidazole Chemical compound C1(CC1)N1C=NC2=C1C=CC(=C2)[N+](=O)[O-] BJDBLDMPXGUKJW-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- TZLPUNMNOJQZAC-UHFFFAOYSA-N 4-[3-(5-nitrobenzimidazol-1-yl)propyl]morpholine Chemical compound [N+](=O)([O-])C1=CC2=C(N(C=N2)CCCN2CCOCC2)C=C1 TZLPUNMNOJQZAC-UHFFFAOYSA-N 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
- RHJQQKGYLROZRK-UHFFFAOYSA-N 6-methyl-5-nitro-1-(2-pyrrolidin-1-ylethyl)benzimidazole Chemical compound CC=1C(=CC2=C(N(C=N2)CCN2CCCC2)C=1)[N+](=O)[O-] RHJQQKGYLROZRK-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 238000007126 N-alkylation reaction Methods 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002788 crimping Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 238000001511 high performance liquid chromatography nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710589775.0A CN107445899A (zh) | 2017-07-19 | 2017-07-19 | 一种苯并咪唑类化合物及其制备方法 |
| JP2020509138A JP6944682B2 (ja) | 2017-07-19 | 2017-09-28 | ベンゾイミダゾール系化合物の製造方法 |
| PCT/CN2017/103942 WO2019015112A1 (zh) | 2017-07-19 | 2017-09-28 | 一种苯并咪唑类化合物及其制备方法 |
| US16/485,457 US10787420B2 (en) | 2017-07-19 | 2017-09-28 | Benzimidazole compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710589775.0A CN107445899A (zh) | 2017-07-19 | 2017-07-19 | 一种苯并咪唑类化合物及其制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107445899A true CN107445899A (zh) | 2017-12-08 |
Family
ID=60487826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710589775.0A Pending CN107445899A (zh) | 2017-07-19 | 2017-07-19 | 一种苯并咪唑类化合物及其制备方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US10787420B2 (enExample) |
| JP (1) | JP6944682B2 (enExample) |
| CN (1) | CN107445899A (enExample) |
| WO (1) | WO2019015112A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108640876A (zh) * | 2018-08-02 | 2018-10-12 | 华侨大学 | 一种多取代苯并咪唑衍生物及其制备方法 |
| CN108863820A (zh) * | 2018-07-30 | 2018-11-23 | 枣庄学院 | 一种取代邻苯二胺的合成方法 |
| CN109020895A (zh) * | 2018-08-07 | 2018-12-18 | 枣庄学院 | 一种金属催化的1-苄胺基取代苯并咪唑的合成方法 |
| CN110256359A (zh) * | 2019-06-20 | 2019-09-20 | 武汉工程大学 | 2-氨基苯并咪唑衍生物及其合成和应用 |
| CN110759903A (zh) * | 2018-07-26 | 2020-02-07 | 南开大学 | 一种噻苯唑的合成新方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866545A (zh) * | 2017-03-31 | 2017-06-20 | 刘雪静 | 1‑环烷烃‑5‑硝基‑1h‑苯并[d]咪唑类化合物及其制备方法 |
| CN106946862A (zh) * | 2017-03-31 | 2017-07-14 | 刘雪静 | 1‑烷烃‑6‑甲基‑5‑硝基‑1h‑苯并[d]咪唑类化合物及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1576077A (en) * | 1977-04-13 | 1980-10-01 | Roussel Lab Ltd | 4,5-dihydro-4-oxophyrrolo(1,2-)-quinoxaline-2-carboxylic acids and derivatives |
| PT100905A (pt) * | 1991-09-30 | 1994-02-28 | Eisai Co Ltd | Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem |
| JP2006522812A (ja) * | 2003-04-11 | 2006-10-05 | スミスクライン ビーチャム コーポレーション | 複素環ｍｃｈｒ１アンタゴニスト |
| WO2008134354A1 (en) * | 2007-04-27 | 2008-11-06 | Array Biopharma, Inc. | TNF-α PRODUCTION INHIBITOR |
| CN102985405B (zh) * | 2010-07-02 | 2016-07-06 | Aska制药株式会社 | 杂环化合物及p27Kip1分解抑制剂 |
| WO2015171951A1 (en) * | 2014-05-07 | 2015-11-12 | The Regents Of The University Of Colorado, A Body Corporate | 2-(4-aryl-1h-imidazol-1-yl)aniline compounds |
| MA40957A (fr) * | 2014-10-09 | 2017-09-19 | Biomarin Pharm Inc | Inhibiteurs de biosynthèse d'héparane sulfate pour traiter des maladies |
-
2017
- 2017-07-19 CN CN201710589775.0A patent/CN107445899A/zh active Pending
- 2017-09-28 WO PCT/CN2017/103942 patent/WO2019015112A1/zh not_active Ceased
- 2017-09-28 US US16/485,457 patent/US10787420B2/en not_active Expired - Fee Related
- 2017-09-28 JP JP2020509138A patent/JP6944682B2/ja not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866545A (zh) * | 2017-03-31 | 2017-06-20 | 刘雪静 | 1‑环烷烃‑5‑硝基‑1h‑苯并[d]咪唑类化合物及其制备方法 |
| CN106946862A (zh) * | 2017-03-31 | 2017-07-14 | 刘雪静 | 1‑烷烃‑6‑甲基‑5‑硝基‑1h‑苯并[d]咪唑类化合物及其制备方法 |
Non-Patent Citations (2)
| Title |
|---|
| KARL J. OKOLOTOWICZ ET AL.: "1,5-Disubstituted benzimidazoles that direct cardiomyocyte differentiation from mouse embryonic stem cells", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
| 王晶.: "基于原位生成的C=N双键的串联反应研究", 《中国博士学位论文全文数据库·工程科技I辑》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110759903A (zh) * | 2018-07-26 | 2020-02-07 | 南开大学 | 一种噻苯唑的合成新方法 |
| CN110759903B (zh) * | 2018-07-26 | 2022-10-28 | 南开大学 | 一种噻苯唑的合成新方法 |
| CN108863820A (zh) * | 2018-07-30 | 2018-11-23 | 枣庄学院 | 一种取代邻苯二胺的合成方法 |
| CN108640876A (zh) * | 2018-08-02 | 2018-10-12 | 华侨大学 | 一种多取代苯并咪唑衍生物及其制备方法 |
| CN109020895A (zh) * | 2018-08-07 | 2018-12-18 | 枣庄学院 | 一种金属催化的1-苄胺基取代苯并咪唑的合成方法 |
| CN110256359A (zh) * | 2019-06-20 | 2019-09-20 | 武汉工程大学 | 2-氨基苯并咪唑衍生物及其合成和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2020518661A (ja) | 2020-06-25 |
| JP6944682B2 (ja) | 2021-10-06 |
| US10787420B2 (en) | 2020-09-29 |
| US20200002291A1 (en) | 2020-01-02 |
| WO2019015112A1 (zh) | 2019-01-24 |
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