RU2420526C2 - ИМИДАЗО[1,2-a]ПИРИДИНОВЫЕ ПРОИЗВОДНЫЕ, КОТОРЫЕ МОЖНО ИСПОЛЬЗОВАТЬ В КАЧЕСТВЕ ИНГИБИТОРОВ ПЕПТИДДЕФОРМИЛАЗЫ (ПДФ) - Google Patents

Info

Publication number

RU2420526C2

RU2420526C2 RU2007143512/04A RU2007143512A RU2420526C2 RU 2420526 C2 RU2420526 C2 RU 2420526C2 RU 2007143512/04 A RU2007143512/04 A RU 2007143512/04A RU 2007143512 A RU2007143512 A RU 2007143512A RU 2420526 C2 RU2420526 C2 RU 2420526C2

Authority

RU

Russia

Prior art keywords

hydroxy

imidazo

ylamino

acetamide

pyridin

Prior art date

2005-04-25

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• 108010026809 Peptide deformylase Proteins 0.000 title claims abstract description 9
• 239000003112 inhibitor Substances 0.000 title description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
• -1 aralkyl radical Chemical class 0.000 claims abstract description 80
• 150000001875 compounds Chemical class 0.000 claims abstract description 36
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
• 229910052760 oxygen Chemical group 0.000 claims abstract description 21
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
• 125000003118 aryl group Chemical group 0.000 claims abstract description 20
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
• 239000001301 oxygen Chemical group 0.000 claims abstract description 14
• 150000003254 radicals Chemical class 0.000 claims abstract description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
• 150000003839 salts Chemical class 0.000 claims abstract description 10
• 125000003277 amino group Chemical group 0.000 claims abstract description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
• 125000005843 halogen group Chemical group 0.000 claims abstract description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
• 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
• 150000005840 aryl radicals Chemical class 0.000 claims abstract 2
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
• 125000005842 heteroatom Chemical group 0.000 claims abstract 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
• 230000002401 inhibitory effect Effects 0.000 claims abstract 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 2
• 239000003814 drug Substances 0.000 abstract description 6
• 239000003242 anti bacterial agent Substances 0.000 abstract description 3
• 229940088710 antibiotic agent Drugs 0.000 abstract description 3
• 230000000694 effects Effects 0.000 abstract description 2
• 239000000126 substance Substances 0.000 abstract description 2
• 125000006193 alkinyl group Chemical group 0.000 abstract 1
• 125000004432 carbon atom Chemical group C* 0.000 description 25
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 229910052717 sulfur Inorganic materials 0.000 description 18
• 229960001171 acetohydroxamic acid Drugs 0.000 description 10
• 125000004404 heteroalkyl group Chemical group 0.000 description 9
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
• 239000011593 sulfur Substances 0.000 description 8
• 239000000460 chlorine Substances 0.000 description 7
• 229910052731 fluorine Inorganic materials 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
• 239000011737 fluorine Substances 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
• 229910052698 phosphorus Inorganic materials 0.000 description 5
• 239000011574 phosphorus Substances 0.000 description 5
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 239000003937 drug carrier Substances 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• 229910052711 selenium Inorganic materials 0.000 description 4
• 239000011669 selenium Substances 0.000 description 4
• 229910052710 silicon Inorganic materials 0.000 description 4
• 239000010703 silicon Substances 0.000 description 4
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
• 241000894006 Bacteria Species 0.000 description 3
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 235000019198 oils Nutrition 0.000 description 3
• 239000000081 peptide deformylase inhibitor Substances 0.000 description 3
• 239000003208 petroleum Substances 0.000 description 3
• 229920005862 polyol Polymers 0.000 description 3
• 150000003077 polyols Chemical class 0.000 description 3
• 125000004434 sulfur atom Chemical group 0.000 description 3
• 235000015112 vegetable and seed oil Nutrition 0.000 description 3
• 239000008158 vegetable oil Substances 0.000 description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• 108090000790 Enzymes Proteins 0.000 description 2
• 102000004190 Enzymes Human genes 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 235000011054 acetic acid Nutrition 0.000 description 2
• 125000002252 acyl group Chemical group 0.000 description 2
• 125000004423 acyloxy group Chemical group 0.000 description 2
• 239000000654 additive Substances 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 229910052796 boron Inorganic materials 0.000 description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
• BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
• 239000008298 dragée Substances 0.000 description 2
• 239000003925 fat Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 125000004475 heteroaralkyl group Chemical group 0.000 description 2
• 150000002430 hydrocarbons Chemical group 0.000 description 2
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 description 2
• 239000012188 paraffin wax Substances 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
• 235000019260 propionic acid Nutrition 0.000 description 2
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 239000007901 soft capsule Substances 0.000 description 2
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• 125000001424 substituent group Chemical group 0.000 description 2
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• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 229910052720 vanadium Inorganic materials 0.000 description 2
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 description 1
• KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
• MMZYCBHLNZVROM-UHFFFAOYSA-N 1-fluoro-2-methylbenzene Chemical compound CC1=CC=CC=C1F MMZYCBHLNZVROM-UHFFFAOYSA-N 0.000 description 1
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
• YGYVIHNNPMYSGI-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-3-[[2-(hydroxyamino)-2-oxoethyl]amino]imidazo[1,2-a]pyridine-8-carboxylic acid Chemical compound CC(CC=1N=C2N(C=CC=C2C(=O)O)C1NCC(NO)=O)(C)C YGYVIHNNPMYSGI-UHFFFAOYSA-N 0.000 description 1
• HBKUJMXTZUZIGJ-UHFFFAOYSA-N 2-[(2,5-diethylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C)C=1N=C2N(C(=CC=C2)CC)C=1NCC(=O)NO HBKUJMXTZUZIGJ-UHFFFAOYSA-N 0.000 description 1
• HVEPZNPWHNCWMW-UHFFFAOYSA-N 2-[(2,5-dipropylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(CC)C=1N=C2N(C(=CC=C2)CCC)C=1NCC(=O)NO HVEPZNPWHNCWMW-UHFFFAOYSA-N 0.000 description 1
• HRKQOYAKINDTJD-UHFFFAOYSA-N 2-[(2-benzyl-5,7-dimethylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C(=CC(=C2)C)C)C=1NCC(=O)NO HRKQOYAKINDTJD-UHFFFAOYSA-N 0.000 description 1
• RCAIABPZWCDHFA-UHFFFAOYSA-N 2-[(2-benzyl-5-methylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C(=CC=C2)C)C=1NCC(=O)NO RCAIABPZWCDHFA-UHFFFAOYSA-N 0.000 description 1
• TXGKEOMGESNVCU-UHFFFAOYSA-N 2-[(2-benzyl-5-propylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C(=CC=C2)CCC)C=1NCC(=O)NO TXGKEOMGESNVCU-UHFFFAOYSA-N 0.000 description 1
• NRUIGVRHIOVKDK-UHFFFAOYSA-N 2-[(2-benzyl-6,8-dibromo-5,7-dimethylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C(=C(C(=C2Br)C)Br)C)C=1NCC(=O)NO NRUIGVRHIOVKDK-UHFFFAOYSA-N 0.000 description 1
• KYBTVGCTTZAHMF-UHFFFAOYSA-N 2-[(2-benzyl-6,8-dibromo-5-methylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C(=C(C=C2Br)Br)C)C=1NCC(=O)NO KYBTVGCTTZAHMF-UHFFFAOYSA-N 0.000 description 1
• OMJAKAKNCCOALM-UHFFFAOYSA-N 2-[(2-benzyl-6,8-dibromoimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C=C(C=C2Br)Br)C=1NCC(=O)NO OMJAKAKNCCOALM-UHFFFAOYSA-N 0.000 description 1
• IHPRIXAHTNNENX-UHFFFAOYSA-N 2-[(2-benzyl-6-bromo-5-methylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C(=C(C=C2)Br)C)C=1NCC(=O)NO IHPRIXAHTNNENX-UHFFFAOYSA-N 0.000 description 1
• VHUIVXMOIZBODM-UHFFFAOYSA-N 2-[(2-benzyl-6-nitroimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C=C(C=C2)[N+](=O)[O-])C=1NCC(=O)NO VHUIVXMOIZBODM-UHFFFAOYSA-N 0.000 description 1
• AMQPHGUCUZEZRD-UHFFFAOYSA-N 2-[(2-benzyl-7-ethylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C=CC(=C2)CC)C=1NCC(=O)NO AMQPHGUCUZEZRD-UHFFFAOYSA-N 0.000 description 1
• DHCUEZOOAIUHEM-UHFFFAOYSA-N 2-[(2-benzyl-8-ethyl-5-methylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C(=CC=C2CC)C)C=1NCC(=O)NO DHCUEZOOAIUHEM-UHFFFAOYSA-N 0.000 description 1
• RTRBGNVAWPSGFR-UHFFFAOYSA-N 2-[(2-benzyl-8-hydroxyimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C=CC=C2O)C=1NCC(=O)NO RTRBGNVAWPSGFR-UHFFFAOYSA-N 0.000 description 1
• HNWNZOTXRVCGIE-UHFFFAOYSA-N 2-[(2-benzyl-8-methylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C=CC=C2C)C=1NCC(=O)NO HNWNZOTXRVCGIE-UHFFFAOYSA-N 0.000 description 1
• GGOFOLKFDFXYQO-UHFFFAOYSA-N 2-[(2-benzylimidazo[1,2-a]quinolin-1-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C3=CC=CC=C3C=C2)C=1NCC(=O)NO GGOFOLKFDFXYQO-UHFFFAOYSA-N 0.000 description 1
• NZLDJCNRINCLAP-UHFFFAOYSA-N 2-[(2-benzylimidazo[2,1-a]isoquinolin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(C1=CC=CC=C1)C=1N=C2N(C=CC3=CC=CC=C23)C=1NCC(=O)NO NZLDJCNRINCLAP-UHFFFAOYSA-N 0.000 description 1
• PWHFUVHALWSNNK-UHFFFAOYSA-N 2-[(2-butyl-5,7-dimethylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(CCC)C=1N=C2N(C(=CC(=C2)C)C)C=1NCC(=O)NO PWHFUVHALWSNNK-UHFFFAOYSA-N 0.000 description 1
• HMWFILJPOZIYGH-UHFFFAOYSA-N 2-[(2-butyl-5-chloroimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(CCC)C=1N=C2N(C(=CC=C2)Cl)C=1NCC(=O)NO HMWFILJPOZIYGH-UHFFFAOYSA-N 0.000 description 1
• AZQPVKMLAVIROZ-UHFFFAOYSA-N 2-[(2-butyl-5-ethylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(CCC)C=1N=C2N(C(=CC=C2)CC)C1NCC(=O)NO AZQPVKMLAVIROZ-UHFFFAOYSA-N 0.000 description 1
• ABHQRNRFUIFGAD-UHFFFAOYSA-N 2-[(2-butyl-5-methylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(CCC)C=1N=C2N(C(=CC=C2)C)C=1NCC(=O)NO ABHQRNRFUIFGAD-UHFFFAOYSA-N 0.000 description 1
• AODSXOGYMJNYCG-UHFFFAOYSA-N 2-[(2-butyl-6,8-difluoroimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(CCC)C=1N=C2N(C=C(C=C2F)F)C=1NCC(=O)NO AODSXOGYMJNYCG-UHFFFAOYSA-N 0.000 description 1
• LVEXKCFWVCVNRS-UHFFFAOYSA-N 2-[(2-butyl-6-methylimidazo[1,2-a]pyridin-3-yl)amino]-N-hydroxyacetamide Chemical compound C(CCC)C=1N=C2N(C=C(C=C2)C)C=1NCC(=O)NO LVEXKCFWVCVNRS-UHFFFAOYSA-N 0.000 description 1
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