HRP20050252A2 - Novel imidazole compounds as transforming growth factor (tfg) inhibitors - Google Patents

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Publication number

HRP20050252A2

HRP20050252A2 HR20050252A HRP20050252A HRP20050252A2 HR P20050252 A2 HRP20050252 A2 HR P20050252A2 HR 20050252 A HR20050252 A HR 20050252A HR P20050252 A HRP20050252 A HR P20050252A HR P20050252 A2 HRP20050252 A2 HR P20050252A2

Authority

HR

Croatia

Prior art keywords

alkyl

phenyl

cycloalkyl

heteroaryl

heterocycle

Prior art date

2002-09-18

Links

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• 102000009618 Transforming Growth Factors Human genes 0.000 title description 16
• 108010009583 Transforming Growth Factors Proteins 0.000 title description 16
• 239000003112 inhibitor Substances 0.000 title description 8
• 150000002460 imidazoles Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 179
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 138
• -1 hydroxy, oxo, mercapto Chemical class 0.000 claims description 60
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
• 125000004122 cyclic group Chemical group 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 125000003118 aryl group Chemical group 0.000 claims description 25
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 239000000651 prodrug Substances 0.000 claims description 21
• 229940002612 prodrug Drugs 0.000 claims description 21
• 201000010099 disease Diseases 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
• 241001465754 Metazoa Species 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
• 125000000172 C5-C10 aryl group Chemical group 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 150000002148 esters Chemical class 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 125000003368 amide group Chemical group 0.000 claims description 5
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000003367 polycyclic group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000006721 (C5-C10) heteroaryl (C1-C6) alkyl group Chemical group 0.000 claims description 2
• 208000032544 Cicatrix Diseases 0.000 claims description 2
• 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
• 206010039710 Scleroderma Diseases 0.000 claims description 2
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
• 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
• 206010020718 hyperplasia Diseases 0.000 claims description 2
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
• 208000037803 restenosis Diseases 0.000 claims description 2
• 231100000241 scar Toxicity 0.000 claims description 2
• 230000037387 scars Effects 0.000 claims description 2
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
• 125000001475 halogen functional group Chemical group 0.000 claims 1
• 238000002360 preparation method Methods 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 27
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 27
• 230000014759 maintenance of location Effects 0.000 description 27
• 238000004128 high performance liquid chromatography Methods 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 25
• 239000002904 solvent Substances 0.000 description 25
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
• 239000002253 acid Substances 0.000 description 20
• 239000000243 solution Substances 0.000 description 20
• 239000002585 base Substances 0.000 description 18
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
• 239000000203 mixture Substances 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 239000003814 drug Substances 0.000 description 11
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• 239000000443 aerosol Substances 0.000 description 9
• 235000019441 ethanol Nutrition 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 239000003480 eluent Substances 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 239000000741 silica gel Substances 0.000 description 7
• 229910002027 silica gel Inorganic materials 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 239000007788 liquid Substances 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 6
• 230000019491 signal transduction Effects 0.000 description 6
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
• 150000001768 cations Chemical class 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 231100000252 nontoxic Toxicity 0.000 description 5
• 230000003000 nontoxic effect Effects 0.000 description 5
• 239000008194 pharmaceutical composition Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052938 sodium sulfate Inorganic materials 0.000 description 5
• 235000011152 sodium sulphate Nutrition 0.000 description 5
• XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 4
• WLTWCMQCVCPRCY-UHFFFAOYSA-N 1-methyl-6-[5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]benzotriazole Chemical compound CC1=CC=CC(C2=C(N=CN2)C=2C=C3N(C)N=NC3=CC=2)=N1 WLTWCMQCVCPRCY-UHFFFAOYSA-N 0.000 description 4
• KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 4
• ABSLAQUFYQRRFB-UHFFFAOYSA-N 4-(2-methylbenzotriazol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazole-2-carbaldehyde Chemical compound CC1=CC=CC(C2=C(N=C(C=O)N2)C2=CC3=NN(C)N=C3C=C2)=N1 ABSLAQUFYQRRFB-UHFFFAOYSA-N 0.000 description 4
• ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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• 229910019142 PO4 Inorganic materials 0.000 description 4
• 108091000080 Phosphotransferase Proteins 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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• 150000007513 acids Chemical class 0.000 description 4
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 125000005843 halogen group Chemical group 0.000 description 4
• 150000004677 hydrates Chemical class 0.000 description 4
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
• 239000012074 organic phase Substances 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
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• 239000000758 substrate Substances 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
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• YUNXAXZNLFOROV-UHFFFAOYSA-N 5-[2-(dimethoxymethyl)-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]-2-methylbenzotriazole Chemical compound N1C(C(OC)OC)=NC(C2=CC3=NN(C)N=C3C=C2)=C1C1=CC=CC(C)=N1 YUNXAXZNLFOROV-UHFFFAOYSA-N 0.000 description 3
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• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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• 102000047918 Myelin Basic Human genes 0.000 description 3
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• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 3
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• PJIWHRSVFSFEHB-UHFFFAOYSA-N [4-(2-methylbenzotriazol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]methanol Chemical compound CC1=CC=CC(C2=C(N=C(CO)N2)C2=CC3=NN(C)N=C3C=C2)=N1 PJIWHRSVFSFEHB-UHFFFAOYSA-N 0.000 description 3
• 150000001447 alkali salts Chemical class 0.000 description 3
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
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• 125000002883 imidazolyl group Chemical group 0.000 description 3
• XHQASXFGRWCGKI-UHFFFAOYSA-N n-methoxy-n,3-dimethylbenzotriazole-5-carboxamide Chemical compound CON(C)C(=O)C1=CC=C2N=NN(C)C2=C1 XHQASXFGRWCGKI-UHFFFAOYSA-N 0.000 description 3
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• 239000003981 vehicle Substances 0.000 description 3
• QLXIPJYIGDXZHN-UHFFFAOYSA-N 1-(3-methylbenzotriazol-5-yl)-2-(6-methylpyridin-2-yl)ethane-1,2-dione Chemical compound CC1=CC=CC(C(=O)C(=O)C=2C=C3N(C)N=NC3=CC=2)=N1 QLXIPJYIGDXZHN-UHFFFAOYSA-N 0.000 description 2
• NXNZBWZYLNESLH-UHFFFAOYSA-N 1-(3-methylbenzotriazol-5-yl)-2-(6-methylpyridin-2-yl)ethanone Chemical compound CC1=CC=CC(CC(=O)C=2C=C3N(C)N=NC3=CC=2)=N1 NXNZBWZYLNESLH-UHFFFAOYSA-N 0.000 description 2
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
• QDBYZWRPHYFSDF-UHFFFAOYSA-N 2-[2-methyl-4-(6-methylpyridin-2-yl)-1h-imidazol-5-yl]-1,5-naphthyridine Chemical compound N1C(C)=NC(C=2N=C3C=CC=NC3=CC=2)=C1C1=CC=CC(C)=N1 QDBYZWRPHYFSDF-UHFFFAOYSA-N 0.000 description 2
• CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
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