RU2498985C2 - 8-анилиноимидазопиридины и способы их использования - Google Patents

Info

Publication number

RU2498985C2

RU2498985C2 RU2010129910/04A RU2010129910A RU2498985C2 RU 2498985 C2 RU2498985 C2 RU 2498985C2 RU 2010129910/04 A RU2010129910/04 A RU 2010129910/04A RU 2010129910 A RU2010129910 A RU 2010129910A RU 2498985 C2 RU2498985 C2 RU 2498985C2

Authority

RU

Russia

Prior art keywords

alkyl

formula

pyridine

mmol

imidazo

Prior art date

2007-12-19

Links

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• 238000000034 method Methods 0.000 title claims abstract description 70
• 150000001875 compounds Chemical class 0.000 claims abstract description 177
• -1 substituted Chemical class 0.000 claims abstract description 107
• 150000003839 salts Chemical class 0.000 claims abstract description 38
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 30
• 125000004452 carbocyclyl group Chemical group 0.000 claims abstract description 17
• 230000010261 cell growth Effects 0.000 claims abstract description 13
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 178
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
• 241000124008 Mammalia Species 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 31
• 229910052799 carbon Inorganic materials 0.000 claims description 29
• 201000010099 disease Diseases 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 25
• 230000002159 abnormal effect Effects 0.000 claims description 13
• PRGBKVNTMCSGDD-UHFFFAOYSA-N 8-(4-cyclopropyl-2-fluoroanilino)imidazo[1,5-a]pyridine-7-carboxylic acid Chemical compound OC(=O)C=1C=CN2C=NC=C2C=1NC(C(=C1)F)=CC=C1C1CC1 PRGBKVNTMCSGDD-UHFFFAOYSA-N 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• HKUKICKULNJTHG-JTQLQIEISA-N 8-(4-bromo-2-fluoroanilino)-n-[(2s)-2-hydroxypropoxy]imidazo[1,5-a]pyridine-7-carboxamide Chemical compound C[C@H](O)CONC(=O)C=1C=CN2C=NC=C2C=1NC1=CC=C(Br)C=C1F HKUKICKULNJTHG-JTQLQIEISA-N 0.000 claims description 3
• JKDBQRTZRZJBKK-UHFFFAOYSA-N 8-(2-fluoro-4-methylsulfanylanilino)-n-(2-hydroxyethoxy)imidazo[1,5-a]pyridine-7-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)C=CN2C1=CN=C2 JKDBQRTZRZJBKK-UHFFFAOYSA-N 0.000 claims description 2
• KJMWUTLZQJVVQC-UHFFFAOYSA-N 8-(4-cyclobutyl-2-fluoroanilino)-n-(2-hydroxyethoxy)imidazo[1,5-a]pyridine-7-carboxamide Chemical compound OCCONC(=O)C=1C=CN2C=NC=C2C=1NC(C(=C1)F)=CC=C1C1CCC1 KJMWUTLZQJVVQC-UHFFFAOYSA-N 0.000 claims description 2
• SXXAGUWDTVENNX-UHFFFAOYSA-N 8-(4-cyclopropyl-2-fluoroanilino)-n-(2-hydroxyethoxy)imidazo[1,5-a]pyridine-7-carboxamide Chemical compound OCCONC(=O)C=1C=CN2C=NC=C2C=1NC(C(=C1)F)=CC=C1C1CC1 SXXAGUWDTVENNX-UHFFFAOYSA-N 0.000 claims description 2
• GERXWWPNRKXYSR-UHFFFAOYSA-N 8-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)imidazo[1,5-a]pyridine-7-carboxamide Chemical compound OCCONC(=O)C=1C=CN2C=NC=C2C=1NC1=CC=C(I)C=C1F GERXWWPNRKXYSR-UHFFFAOYSA-N 0.000 claims 1
• BTCSRBXVTIUKLJ-UHFFFAOYSA-N 8-(4-bromo-2-chloroanilino)-n-(2-hydroxyethoxy)imidazo[1,5-a]pyridine-7-carboxamide Chemical compound OCCONC(=O)C=1C=CN2C=NC=C2C=1NC1=CC=C(Br)C=C1Cl BTCSRBXVTIUKLJ-UHFFFAOYSA-N 0.000 claims 1
• GSNDENNNEIFRCS-UHFFFAOYSA-N 8-(4-bromo-2-fluoroanilino)-n-(2-hydroxyethoxy)imidazo[1,5-a]pyridine-7-carboxamide Chemical compound OCCONC(=O)C=1C=CN2C=NC=C2C=1NC1=CC=C(Br)C=C1F GSNDENNNEIFRCS-UHFFFAOYSA-N 0.000 claims 1
• WFNLHIXTARCTSK-UHFFFAOYSA-N 8-(4-cyclopropyl-2-fluoroanilino)-n-(1-hydroxy-2-methylpropan-2-yl)oxyimidazo[1,5-a]pyridine-7-carboxamide Chemical compound OCC(C)(C)ONC(=O)C=1C=CN2C=NC=C2C=1NC(C(=C1)F)=CC=C1C1CC1 WFNLHIXTARCTSK-UHFFFAOYSA-N 0.000 claims 1
• 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 abstract description 11
• 230000000694 effects Effects 0.000 abstract description 9
• 239000000126 substance Substances 0.000 abstract description 7
• 125000005843 halogen group Chemical group 0.000 abstract description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
• 230000002547 anomalous effect Effects 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 150
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
• 239000002904 solvent Substances 0.000 description 59
• 239000000203 mixture Substances 0.000 description 47
• 210000004027 cell Anatomy 0.000 description 41
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 35
• 125000000623 heterocyclic group Chemical group 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
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• 239000000243 solution Substances 0.000 description 28
• 206010028980 Neoplasm Diseases 0.000 description 26
• 125000003118 aryl group Chemical group 0.000 description 25
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
• 238000006243 chemical reaction Methods 0.000 description 22
• 239000007787 solid Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 239000002253 acid Substances 0.000 description 21
• 125000001072 heteroaryl group Chemical group 0.000 description 21
• 238000011282 treatment Methods 0.000 description 21
• 125000000217 alkyl group Chemical group 0.000 description 20
• 239000002585 base Substances 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 19
• 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 18
• 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 18
• 229920006395 saturated elastomer Polymers 0.000 description 18
• 239000012453 solvate Substances 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
• 239000012267 brine Substances 0.000 description 17
• 229910052757 nitrogen Inorganic materials 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• 235000019441 ethanol Nutrition 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• 229940002612 prodrug Drugs 0.000 description 16
• 239000000651 prodrug Substances 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
• 208000035475 disorder Diseases 0.000 description 15
• 239000003814 drug Substances 0.000 description 14
• 238000010992 reflux Methods 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 201000011510 cancer Diseases 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 12
• 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 12
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• 235000019253 formic acid Nutrition 0.000 description 12
• 229910052740 iodine Inorganic materials 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• 239000000758 substrate Substances 0.000 description 11
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 10
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
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• 102000043136 MAP kinase family Human genes 0.000 description 8
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• 125000004432 carbon atom Chemical group C* 0.000 description 8
• 208000027866 inflammatory disease Diseases 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
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