CN111484493A - 1H-吡咯并[2,3-b]吡啶衍生物及它们作为激酶抑制剂的用途 - Google Patents

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Publication number

CN111484493A

CN111484493A CN202010405942.3A CN202010405942A CN111484493A CN 111484493 A CN111484493 A CN 111484493A CN 202010405942 A CN202010405942 A CN 202010405942A CN 111484493 A CN111484493 A CN 111484493A

Authority

CN

China

Prior art keywords

pyrrolo

pyrazole

mmol

pyridin

benzyl

Prior art date

2012-01-30

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

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• 150000005258 1H-pyrrolo(2,3-b)pyridines Chemical class 0.000 title abstract description 7
• 229940043355 kinase inhibitor Drugs 0.000 title abstract description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 356
• -1 O-methyl Chemical group 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000003107 substituted aryl group Chemical group 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000004450 alkenylene group Chemical group 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000000732 arylene group Chemical group 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000005549 heteroarylene group Chemical group 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 abstract description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 317
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 282
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 200
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 150
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 140
• 239000007787 solid Substances 0.000 description 121
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 115
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 108
• 238000002360 preparation method Methods 0.000 description 103
• 235000019439 ethyl acetate Nutrition 0.000 description 100
• 238000005481 NMR spectroscopy Methods 0.000 description 99
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 97
• 229920006395 saturated elastomer Polymers 0.000 description 96
• KGDOHXYALMXHLF-UHFFFAOYSA-N 1-benzylpyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=CC=C1 KGDOHXYALMXHLF-UHFFFAOYSA-N 0.000 description 93
• 239000000243 solution Substances 0.000 description 89
• 238000006243 chemical reaction Methods 0.000 description 82
• 239000000203 mixture Substances 0.000 description 78
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 76
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 75
• 235000019341 magnesium sulphate Nutrition 0.000 description 75
• 239000011541 reaction mixture Substances 0.000 description 71
• 239000011780 sodium chloride Substances 0.000 description 70
• 238000000034 method Methods 0.000 description 64
• 239000002904 solvent Substances 0.000 description 64
• 239000000047 product Substances 0.000 description 63
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• 238000004440 column chromatography Methods 0.000 description 52
• 239000013058 crude material Substances 0.000 description 48
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• 239000000843 powder Substances 0.000 description 37
• 238000007792 addition Methods 0.000 description 36
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
• 239000000463 material Substances 0.000 description 24
• 238000003756 stirring Methods 0.000 description 23
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
• 239000006071 cream Substances 0.000 description 21
• 238000001914 filtration Methods 0.000 description 21
• AKKPGUPOFLAXRN-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=C(F)C=C1 AKKPGUPOFLAXRN-UHFFFAOYSA-N 0.000 description 20
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
• 239000000284 extract Substances 0.000 description 20
• 238000003818 flash chromatography Methods 0.000 description 20
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 20
• 206010028980 Neoplasm Diseases 0.000 description 19
• 239000008346 aqueous phase Substances 0.000 description 19
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
• 229910000027 potassium carbonate Inorganic materials 0.000 description 18
• 238000002953 preparative HPLC Methods 0.000 description 18
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 17
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 description 13
• 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 description 13
• 239000000706 filtrate Substances 0.000 description 13
• 239000003112 inhibitor Substances 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• WUOQXNWMYLFAHT-MRVPVSSYSA-N tert-butyl n-[(3r)-piperidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H]1CCCNC1 WUOQXNWMYLFAHT-MRVPVSSYSA-N 0.000 description 12
• 201000011510 cancer Diseases 0.000 description 11
• 239000012230 colorless oil Substances 0.000 description 11
• 239000003814 drug Substances 0.000 description 11
• 238000005516 engineering process Methods 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 235000019198 oils Nutrition 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• RJAFVJZCUMEOBR-UHFFFAOYSA-N 1-(pyridin-4-ylmethyl)pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=NC=C1 RJAFVJZCUMEOBR-UHFFFAOYSA-N 0.000 description 10
• 241000400611 Eucalyptus deanei Species 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• 238000010438 heat treatment Methods 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 239000000725 suspension Substances 0.000 description 10
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 9
• 239000007821 HATU Substances 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 238000001035 drying Methods 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 239000011521 glass Substances 0.000 description 9
• 238000005342 ion exchange Methods 0.000 description 9
• 235000015320 potassium carbonate Nutrition 0.000 description 9
• 235000011181 potassium carbonates Nutrition 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
• 235000019270 ammonium chloride Nutrition 0.000 description 8
• 235000011114 ammonium hydroxide Nutrition 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 101150113535 chek1 gene Proteins 0.000 description 8
• 229960005277 gemcitabine Drugs 0.000 description 8
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
• 235000017557 sodium bicarbonate Nutrition 0.000 description 8
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 7
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 7
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
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• HJBGZJMKTOMQRR-UHFFFAOYSA-N (3-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1 HJBGZJMKTOMQRR-UHFFFAOYSA-N 0.000 description 6
• WCMWZVWZYCRAIW-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)pyrazole-4-carboxylic acid Chemical compound C1=C(C(=O)O)C=NN1CC1=CC=CN=C1 WCMWZVWZYCRAIW-UHFFFAOYSA-N 0.000 description 6
• UORKPBOZTFYKBG-UHFFFAOYSA-N 1-benzyl-n-(5-bromo-1h-pyrrolo[2,3-b]pyridin-3-yl)pyrazole-4-carboxamide Chemical compound C12=CC(Br)=CN=C2NC=C1NC(=O)C(=C1)C=NN1CC1=CC=CC=C1 UORKPBOZTFYKBG-UHFFFAOYSA-N 0.000 description 6
• MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 6
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• 101150050673 CHK1 gene Proteins 0.000 description 6
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• 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 6
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• 238000010626 work up procedure Methods 0.000 description 6
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
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