ES2552841T3 - Imidazo[1,2-a]pirimidinas y -piridinas sustituidas - Google Patents

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Publication number

ES2552841T3

ES2552841T3 ES11730003.8T ES11730003T ES2552841T3 ES 2552841 T3 ES2552841 T3 ES 2552841T3 ES 11730003 T ES11730003 T ES 11730003T ES 2552841 T3 ES2552841 T3 ES 2552841T3

Authority

ES

Spain

Prior art keywords

phenyl

imidazo

pyridin

cyclobutyl

int

Prior art date

2010-07-12

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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• -1 substituted -pyridines Chemical class 0.000 title claims abstract description 167
• 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 137
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
• 239000001257 hydrogen Substances 0.000 claims abstract description 63
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 63
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 39
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
• 238000000034 method Methods 0.000 claims description 203
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• ZFZVEUDOVBTELB-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenyl-1h-imidazo[1,2-a]pyridin-7-one Chemical compound C=1C=C(C2=C(N3C=CC(=O)C=C3N2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 ZFZVEUDOVBTELB-UHFFFAOYSA-N 0.000 claims description 2
• SYCVULGNXZQCGX-UHFFFAOYSA-N 1-[4-(7-ethynyl-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C#C)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 SYCVULGNXZQCGX-UHFFFAOYSA-N 0.000 claims 1
• MNKWQDBCRJYVMM-UHFFFAOYSA-N 1-[4-[6-(5-methyl-1h-pyrazol-3-yl)-3-phenylimidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1N=C(C)C=C1C1=CN2C(C=3C=CC=CC=3)=C(C=3C=CC(=CC=3)C3(N)CCC3)N=C2C=C1 MNKWQDBCRJYVMM-UHFFFAOYSA-N 0.000 claims 1
• WTRPETLHOOKVDX-UHFFFAOYSA-N 1-[4-[8-methoxy-3-phenyl-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound N1=C2C(OC)=CC(C3=CNN=C3)=CN2C(C=2C=CC=CC=2)=C1C(C=C1)=CC=C1C1(N)CCC1 WTRPETLHOOKVDX-UHFFFAOYSA-N 0.000 claims 1
• VHGGDRGBYFHHAS-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-8-chloro-3-phenylimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C=1C=C(C2=C(N3C=C(C=C(Cl)C3=N2)C#N)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 VHGGDRGBYFHHAS-UHFFFAOYSA-N 0.000 claims 1
• AFBOMFWMMSRZBK-UHFFFAOYSA-N 3-[2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridin-6-yl]-1h-pyridin-2-one Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C=2C(=NC=CC=2)O)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 AFBOMFWMMSRZBK-UHFFFAOYSA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• 229940080818 propionamide Drugs 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 40
• 150000002367 halogens Chemical group 0.000 abstract description 38
• 125000004093 cyano group Chemical group *C#N 0.000 abstract description 27
• 125000003118 aryl group Chemical group 0.000 abstract description 26
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 25
• 125000000623 heterocyclic group Chemical group 0.000 abstract description 24
• 150000003839 salts Chemical class 0.000 abstract description 23
• 125000001424 substituent group Chemical group 0.000 abstract description 21
• 229920006395 saturated elastomer Polymers 0.000 abstract description 19
• 150000001204 N-oxides Chemical class 0.000 abstract description 17
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 17
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract description 15
• 125000001072 heteroaryl group Chemical group 0.000 abstract description 13
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 10
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract description 10
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract description 10
• 229910052799 carbon Inorganic materials 0.000 abstract description 10
• 125000000217 alkyl group Chemical group 0.000 abstract description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 1
• 125000003342 alkenyl group Chemical group 0.000 abstract 1
• 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 106
• 239000000543 intermediate Substances 0.000 description 100
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 91
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 90
• 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 90
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 73
• 238000000132 electrospray ionisation Methods 0.000 description 73
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 63
• 239000000203 mixture Substances 0.000 description 60
• 235000019439 ethyl acetate Nutrition 0.000 description 48
• 239000000243 solution Substances 0.000 description 40
• 206010028980 Neoplasm Diseases 0.000 description 36
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 34
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
• 239000002253 acid Substances 0.000 description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 26
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• 238000000746 purification Methods 0.000 description 24
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 23
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
• 239000012074 organic phase Substances 0.000 description 21
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 20
• 239000002904 solvent Substances 0.000 description 20
• 201000010099 disease Diseases 0.000 description 19
• 230000035755 proliferation Effects 0.000 description 19
• 238000011282 treatment Methods 0.000 description 19
• 238000005160 1H NMR spectroscopy Methods 0.000 description 18
• 239000012267 brine Substances 0.000 description 18
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• 239000008194 pharmaceutical composition Substances 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
• 239000011541 reaction mixture Substances 0.000 description 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 13
• 239000003480 eluent Substances 0.000 description 13
• 239000007858 starting material Substances 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 230000009826 neoplastic cell growth Effects 0.000 description 12
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 201000011510 cancer Diseases 0.000 description 11
• 238000006243 chemical reaction Methods 0.000 description 11
• 238000001816 cooling Methods 0.000 description 11
• 150000002148 esters Chemical class 0.000 description 11
• 235000019253 formic acid Nutrition 0.000 description 11
• 230000003211 malignant effect Effects 0.000 description 11
• 238000002360 preparation method Methods 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• 101150045355 akt1 gene Proteins 0.000 description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 239000000463 material Substances 0.000 description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 239000004480 active ingredient Substances 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• ONOJJCTXSDBVSP-UHFFFAOYSA-N imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C1=C(C(=O)O)C=CC2=NC=CN21 ONOJJCTXSDBVSP-UHFFFAOYSA-N 0.000 description 9
• 230000002829 reductive effect Effects 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
• 239000007832 Na2SO4 Substances 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 239000002808 molecular sieve Substances 0.000 description 8
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 7
• KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 7
• 239000003085 diluting agent Substances 0.000 description 7
• 239000000284 extract Substances 0.000 description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 description 7
• 238000002560 therapeutic procedure Methods 0.000 description 7
• 238000004704 ultra performance liquid chromatography Methods 0.000 description 7
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 description 6
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• 125000002947 alkylene group Chemical group 0.000 description 6
• 230000000118 anti-neoplastic effect Effects 0.000 description 6
• 239000002246 antineoplastic agent Substances 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• 208000035475 disorder Diseases 0.000 description 6
• 239000003937 drug carrier Substances 0.000 description 6
• 238000004128 high performance liquid chromatography Methods 0.000 description 6
• 230000006882 induction of apoptosis Effects 0.000 description 6
• 239000000741 silica gel Substances 0.000 description 6
• 229910002027 silica gel Inorganic materials 0.000 description 6
• 239000011780 sodium chloride Substances 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• KVAOMOBHQYDUCN-UHFFFAOYSA-N 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound C=1C=C(C2=C(N3C=C(C=CC3=N2)C(O)=O)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 KVAOMOBHQYDUCN-UHFFFAOYSA-N 0.000 description 5
• 241001465754 Metazoa Species 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
• 235000019270 ammonium chloride Nutrition 0.000 description 5
• 239000011737 fluorine Chemical group 0.000 description 5
• 229910052731 fluorine Inorganic materials 0.000 description 5
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
• 201000001441 melanoma Diseases 0.000 description 5
• 150000004702 methyl esters Chemical class 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
• 125000004430 oxygen atom Chemical group O* 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 5
• 239000003981 vehicle Substances 0.000 description 5
• 239000003643 water by type Substances 0.000 description 5
• 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 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 230000000973 chemotherapeutic effect Effects 0.000 description 4
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 238000000105 evaporative light scattering detection Methods 0.000 description 4
• 239000011152 fibreglass Substances 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 238000009472 formulation Methods 0.000 description 4
• NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 4
• 230000003463 hyperproliferative effect Effects 0.000 description 4
• 239000007924 injection Substances 0.000 description 4
• 238000002347 injection Methods 0.000 description 4
• 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 4
• 239000000843 powder Substances 0.000 description 4
• 238000011321 prophylaxis Methods 0.000 description 4
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
• 238000010898 silica gel chromatography Methods 0.000 description 4
• 235000017557 sodium bicarbonate Nutrition 0.000 description 4
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
• 125000006850 spacer group Chemical group 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• MVZPOTHSWMRTJZ-UHFFFAOYSA-N tert-butyl n-[1-(4-cyanophenyl)cyclobutyl]carbamate Chemical compound C=1C=C(C#N)C=CC=1C1(NC(=O)OC(C)(C)C)CCC1 MVZPOTHSWMRTJZ-UHFFFAOYSA-N 0.000 description 4
• SHPCHVHCGOJFTD-UHFFFAOYSA-N tert-butyl n-[1-[4-(7-bromo-3-phenylimidazo[1,2-a]pyridin-2-yl)phenyl]cyclobutyl]carbamate Chemical compound C=1C=C(C2=C(N3C=CC(Br)=CC3=N2)C=2C=CC=CC=2)C=CC=1C1(NC(=O)OC(C)(C)C)CCC1 SHPCHVHCGOJFTD-UHFFFAOYSA-N 0.000 description 4
• 238000012360 testing method Methods 0.000 description 4
• 210000004881 tumor cell Anatomy 0.000 description 4
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 3
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 3
• HPQFDZVVQQRZHS-UHFFFAOYSA-N 1-[4-[3-phenyl-7-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]phenyl]cyclobutan-1-amine Chemical compound C=1C=C(C2=C(N3C=CC(=CC3=N2)C2=CNN=C2)C=2C=CC=CC=2)C=CC=1C1(N)CCC1 HPQFDZVVQQRZHS-UHFFFAOYSA-N 0.000 description 3
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 3
• 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 3
• PTRQGJGYJJUYFU-UHFFFAOYSA-N 4-[(6-methoxypyridin-3-yl)methoxy]pyrimidin-2-amine Chemical compound C1=NC(OC)=CC=C1COC1=CC=NC(N)=N1 PTRQGJGYJJUYFU-UHFFFAOYSA-N 0.000 description 3
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
• 125000003545 alkoxy group Chemical group 0.000 description 3
• 229940034982 antineoplastic agent Drugs 0.000 description 3
• 239000008346 aqueous phase Substances 0.000 description 3
• 239000012300 argon atmosphere Substances 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000000460 chlorine Chemical group 0.000 description 3
• 229910052801 chlorine Inorganic materials 0.000 description 3
• 239000012043 crude product Substances 0.000 description 3
• 229940127089 cytotoxic agent Drugs 0.000 description 3
• 238000010828 elution Methods 0.000 description 3
• 125000005842 heteroatom Chemical group 0.000 description 3
• 150000002576 ketones Chemical class 0.000 description 3
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
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• NTSJNWHEEKZFQL-UHFFFAOYSA-N methyl 2-[4-[1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclobutyl]phenyl]-3-phenylimidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2C=CC(=CC=2)C2(CCC2)NC(=O)OC(C)(C)C)=C1C1=CC=CC=C1 NTSJNWHEEKZFQL-UHFFFAOYSA-N 0.000 description 3
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