EA025466B1 - Определенные триазолопиридины и триазолопиразины, их композиции и способы их применения - Google Patents

Info

Publication number

EA025466B1

EA025466B1 EA201200951A EA201200951A EA025466B1 EA 025466 B1 EA025466 B1 EA 025466B1 EA 201200951 A EA201200951 A EA 201200951A EA 201200951 A EA201200951 A EA 201200951A EA 025466 B1 EA025466 B1 EA 025466B1

Authority

EA

Eurasian Patent Office

Prior art keywords

mmol

compound

pyridin

cancer

alkyl

Prior art date

2009-12-31

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 87
• 150000008523 triazolopyridines Chemical class 0.000 title abstract description 3
• 239000000203 mixture Substances 0.000 title description 154
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
• 150000001875 compounds Chemical class 0.000 claims description 300
• 125000000217 alkyl group Chemical group 0.000 claims description 127
• 229910052736 halogen Inorganic materials 0.000 claims description 83
• 150000002367 halogens Chemical class 0.000 claims description 83
• 125000003545 alkoxy group Chemical group 0.000 claims description 82
• -1 substituted Chemical class 0.000 claims description 74
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 66
• 150000003839 salts Chemical class 0.000 claims description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 42
• 125000003118 aryl group Chemical group 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 37
• 206010028980 Neoplasm Diseases 0.000 claims description 33
• 201000011510 cancer Diseases 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 239000002246 antineoplastic agent Substances 0.000 claims description 11
• 230000005764 inhibitory process Effects 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 4
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 4
• 230000002401 inhibitory effect Effects 0.000 claims description 4
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 4
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 4
• 201000005202 lung cancer Diseases 0.000 claims description 4
• 208000020816 lung neoplasm Diseases 0.000 claims description 4
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 206010033128 Ovarian cancer Diseases 0.000 claims description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
• 206010038389 Renal cancer Diseases 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 208000014018 liver neoplasm Diseases 0.000 claims description 3
• 201000011549 stomach cancer Diseases 0.000 claims description 3
• 239000005411 L01XE02 - Gefitinib Substances 0.000 claims description 2
• 206010050513 Metastatic renal cell carcinoma Diseases 0.000 claims description 2
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 2
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 2
• 229960003668 docetaxel Drugs 0.000 claims description 2
• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 claims description 2
• 229960002584 gefitinib Drugs 0.000 claims description 2
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
• 201000004101 esophageal cancer Diseases 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
• 201000000498 stomach carcinoma Diseases 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 5
• 230000002062 proliferating effect Effects 0.000 abstract description 3
• 238000004519 manufacturing process Methods 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 description 132
• 239000000243 solution Substances 0.000 description 124
• 239000011541 reaction mixture Substances 0.000 description 104
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 103
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
• 239000012044 organic layer Substances 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
• 238000004587 chromatography analysis Methods 0.000 description 33
• 238000010898 silica gel chromatography Methods 0.000 description 33
• 238000001816 cooling Methods 0.000 description 31
• 230000015572 biosynthetic process Effects 0.000 description 30
• 238000002360 preparation method Methods 0.000 description 30
• 238000003786 synthesis reaction Methods 0.000 description 29
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
• 239000000706 filtrate Substances 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• 239000012267 brine Substances 0.000 description 20
• 239000002244 precipitate Substances 0.000 description 20
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
• 238000000746 purification Methods 0.000 description 18
• 239000002904 solvent Substances 0.000 description 17
• 125000005842 heteroatom Chemical group 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• 125000003342 alkenyl group Chemical group 0.000 description 15
• 125000000304 alkynyl group Chemical group 0.000 description 15
• 239000000460 chlorine Substances 0.000 description 15
• 238000010992 reflux Methods 0.000 description 15
• 229920006395 saturated elastomer Polymers 0.000 description 15
• 230000000694 effects Effects 0.000 description 14
• 229960000583 acetic acid Drugs 0.000 description 13
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000007864 aqueous solution Substances 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• 239000003153 chemical reaction reagent Substances 0.000 description 12
• 239000011734 sodium Substances 0.000 description 12
• 102100023038 WD and tetratricopeptide repeats protein 1 Human genes 0.000 description 11
• 125000004429 atom Chemical group 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 11
• 125000004122 cyclic group Chemical group 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• 125000004432 carbon atom Chemical group C* 0.000 description 9
• 210000004027 cell Anatomy 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
• 229910021529 ammonia Inorganic materials 0.000 description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 235000019198 oils Nutrition 0.000 description 8
• 150000003254 radicals Chemical class 0.000 description 8
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 239000013256 coordination polymer Substances 0.000 description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• VZMXFSCEGDLKRG-UHFFFAOYSA-N 1h-thieno[3,2-c]pyrazole-5-carboxylic acid Chemical compound N1N=CC2=C1C=C(C(=O)O)S2 VZMXFSCEGDLKRG-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
• 239000003085 diluting agent Substances 0.000 description 6
• XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 6
• 229910052760 oxygen Inorganic materials 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 6
• BFOYAKWJZDQQSO-UHFFFAOYSA-N 2-(bromomethyl)-[1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC(CBr)=NC2=C1 BFOYAKWJZDQQSO-UHFFFAOYSA-N 0.000 description 5
• NVXPSQIYZCKHMN-UHFFFAOYSA-N 2-methyl-[1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC(C)=NC2=C1 NVXPSQIYZCKHMN-UHFFFAOYSA-N 0.000 description 5
• SBNILQRRTOQGGB-UHFFFAOYSA-N 6-bromo-5-fluoroquinoline Chemical compound C1=CC=C2C(F)=C(Br)C=CC2=N1 SBNILQRRTOQGGB-UHFFFAOYSA-N 0.000 description 5
• 239000004215 Carbon black (E152) Substances 0.000 description 5
• 229940126639 Compound 33 Drugs 0.000 description 5
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 5
• 125000005605 benzo group Chemical group 0.000 description 5
• 239000002552 dosage form Substances 0.000 description 5
• 150000002148 esters Chemical class 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• ZMVDETXPQSIIHI-UHFFFAOYSA-N methyl 2-ethylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound S1C(C(=O)OC)=CC2=NN(CC)C=C21 ZMVDETXPQSIIHI-UHFFFAOYSA-N 0.000 description 5
• KSBXLXBYELWDNC-UHFFFAOYSA-N methyl 5-(hydroxymethyl)pyrazolo[1,5-a]pyridine-3-carboxylate Chemical compound C1=CC(CO)=CC2=C(C(=O)OC)C=NN21 KSBXLXBYELWDNC-UHFFFAOYSA-N 0.000 description 5
• 229910052757 nitrogen Inorganic materials 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 5
• 238000001556 precipitation Methods 0.000 description 5
• FUDXQYZITFGAQK-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-5-carbonitrile Chemical compound N1=C(C#N)C=CN2N=CC=C21 FUDXQYZITFGAQK-UHFFFAOYSA-N 0.000 description 5
• 235000017557 sodium bicarbonate Nutrition 0.000 description 5
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
• 239000012453 solvate Substances 0.000 description 5
• 239000011550 stock solution Substances 0.000 description 5
• ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
• UCNGGGYMLHAMJG-UHFFFAOYSA-N 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole Chemical compound C1=NN(C)C=C1B1OC(C)(C)C(C)(C)O1 UCNGGGYMLHAMJG-UHFFFAOYSA-N 0.000 description 4
• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 4
• QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 4
• KDVBYUUGYXUXNL-UHFFFAOYSA-N 6-aminopyridine-3-carbonitrile Chemical compound NC1=CC=C(C#N)C=N1 KDVBYUUGYXUXNL-UHFFFAOYSA-N 0.000 description 4
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 239000012131 assay buffer Substances 0.000 description 4
• 239000000872 buffer Substances 0.000 description 4
• 238000011088 calibration curve Methods 0.000 description 4
• 125000002837 carbocyclic group Chemical group 0.000 description 4
• 238000004296 chiral HPLC Methods 0.000 description 4
• 229940125904 compound 1 Drugs 0.000 description 4
• 239000006071 cream Substances 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 229940127089 cytotoxic agent Drugs 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• 239000002270 dispersing agent Substances 0.000 description 4
• RNNORVZOWRXGAE-UHFFFAOYSA-N ethyl 2-[(4-chloropyridin-3-yl)amino]-2-oxoacetate Chemical compound CCOC(=O)C(=O)NC1=CN=CC=C1Cl RNNORVZOWRXGAE-UHFFFAOYSA-N 0.000 description 4
• 235000011389 fruit/vegetable juice Nutrition 0.000 description 4
• 150000002430 hydrocarbons Chemical class 0.000 description 4
• MVAGUPORAONUGQ-UHFFFAOYSA-N imidazo[1,2-a]pyrazine-6-carbonitrile Chemical compound C1=NC(C#N)=CN2C=CN=C21 MVAGUPORAONUGQ-UHFFFAOYSA-N 0.000 description 4
• 230000003993 interaction Effects 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• HWOQCGSIDCQVRM-UHFFFAOYSA-N methyl 1h-pyrrolo[2,3-b]pyridine-2-carboxylate Chemical compound C1=CN=C2NC(C(=O)OC)=CC2=C1 HWOQCGSIDCQVRM-UHFFFAOYSA-N 0.000 description 4
• BXBHZLHTTHMUTG-UHFFFAOYSA-N methyl 1h-pyrrolo[3,2-b]pyridine-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=CC2=N1 BXBHZLHTTHMUTG-UHFFFAOYSA-N 0.000 description 4
• XJFHCHXRJZRZKP-UHFFFAOYSA-N methyl 1h-thieno[3,2-c]pyrazole-5-carboxylate Chemical compound N1N=CC2=C1C=C(C(=O)OC)S2 XJFHCHXRJZRZKP-UHFFFAOYSA-N 0.000 description 4
• 239000002480 mineral oil Substances 0.000 description 4
• KWZIDENWDCKKPW-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)acetamide Chemical compound CC(=O)NC1=CC=CN=C1Cl KWZIDENWDCKKPW-UHFFFAOYSA-N 0.000 description 4
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
• 239000002674 ointment Substances 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• 125000004076 pyridyl group Chemical group 0.000 description 4
• 230000010076 replication Effects 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 239000010802 sludge Substances 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 208000024891 symptom Diseases 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• 229940124597 therapeutic agent Drugs 0.000 description 4
• WIWIOUAFBHZLNQ-UHFFFAOYSA-N 1-(2-chloropyridin-3-yl)ethanone Chemical compound CC(=O)C1=CC=CN=C1Cl WIWIOUAFBHZLNQ-UHFFFAOYSA-N 0.000 description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
• CZXPBOPRQAPKGX-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2NC(C(=O)N)=CC2=C1 CZXPBOPRQAPKGX-UHFFFAOYSA-N 0.000 description 3
• KAIWRKYDYWYFIT-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=N1 KAIWRKYDYWYFIT-UHFFFAOYSA-N 0.000 description 3
• HNLYSYKLOTUMJR-UHFFFAOYSA-N 1h-thieno[3,2-c]pyrazol-5-ylmethanol Chemical compound N1N=CC2=C1C=C(CO)S2 HNLYSYKLOTUMJR-UHFFFAOYSA-N 0.000 description 3
• KJVKGYRFRFXCQQ-UHFFFAOYSA-N 2,6-dichloro-3-nitropyridin-4-amine Chemical compound NC1=CC(Cl)=NC(Cl)=C1[N+]([O-])=O KJVKGYRFRFXCQQ-UHFFFAOYSA-N 0.000 description 3
• YVECTFRPHLELMG-UHFFFAOYSA-N 2-(chloromethyl)thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC(CCl)=CC2=N1 YVECTFRPHLELMG-UHFFFAOYSA-N 0.000 description 3
• OZMLUMPWPFZWTP-UHFFFAOYSA-N 2-(tributyl-$l^{5}-phosphanylidene)acetonitrile Chemical compound CCCCP(CCCC)(CCCC)=CC#N OZMLUMPWPFZWTP-UHFFFAOYSA-N 0.000 description 3
• BJRXZMCJFCAZDL-UHFFFAOYSA-N 2-bromopropanal Chemical compound CC(Br)C=O BJRXZMCJFCAZDL-UHFFFAOYSA-N 0.000 description 3
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 3
• AEWIVRMYTGWLOX-UHFFFAOYSA-N 3-(bromomethyl)-2h-pyrazolo[3,4-b]pyridine Chemical compound N1=CC=CC2=C(CBr)NN=C21 AEWIVRMYTGWLOX-UHFFFAOYSA-N 0.000 description 3
• AUCGLTFMKPYVNT-UHFFFAOYSA-N 3-amino-6-chloro-1h-pyridine-2-thione Chemical compound NC1=CC=C(Cl)N=C1S AUCGLTFMKPYVNT-UHFFFAOYSA-N 0.000 description 3
• KAIWLFPPQNJAHO-UHFFFAOYSA-N 3-bromothieno[2,3-b]pyridine Chemical compound C1=CC=C2C(Br)=CSC2=N1 KAIWLFPPQNJAHO-UHFFFAOYSA-N 0.000 description 3
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