TWI238824B - 4-amino-5-phenyl-7-cyclobutyl-pyrrolo[2,3-d]pyrimidine derivatives - Google Patents

Info

Publication number

TWI238824B

TWI238824B TW091109801A TW91109801A TWI238824B TW I238824 B TWI238824 B TW I238824B TW 091109801 A TW091109801 A TW 091109801A TW 91109801 A TW91109801 A TW 91109801A TW I238824 B TWI238824 B TW I238824B

Authority

TW

Taiwan

Prior art keywords

lower alkyl

amino

group

pyrimidin

pyrrolo

Prior art date

2001-05-14

Links

• Espacenet
• Global Dossier
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• OVPLBDSXFCRGJY-UHFFFAOYSA-N 7-cyclobutyl-5-phenylpyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1=2C(N)=NC=NC=2N(C2CCC2)C=C1C1=CC=CC=C1 OVPLBDSXFCRGJY-UHFFFAOYSA-N 0.000 title abstract 2
• 238000002360 preparation method Methods 0.000 claims abstract description 69
• 238000000034 method Methods 0.000 claims abstract description 55
• 230000008569 process Effects 0.000 claims abstract description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
• 201000010099 disease Diseases 0.000 claims abstract description 26
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 239000003814 drug Substances 0.000 claims abstract description 6
• 230000002062 proliferating effect Effects 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 454
• -1 lactyl group Chemical group 0.000 claims description 349
• 150000001875 compounds Chemical class 0.000 claims description 301
• 229910052757 nitrogen Inorganic materials 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 63
• 238000006243 chemical reaction Methods 0.000 claims description 62
• 125000003277 amino group Chemical group 0.000 claims description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 47
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 42
• 229910052760 oxygen Inorganic materials 0.000 claims description 42
• 239000001301 oxygen Substances 0.000 claims description 42
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 41
• 125000003545 alkoxy group Chemical group 0.000 claims description 40
• 125000003282 alkyl amino group Chemical group 0.000 claims description 37
• 150000001412 amines Chemical class 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 239000000203 mixture Substances 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 239000007858 starting material Substances 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 239000011593 sulfur Substances 0.000 claims description 14
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 12
• 102000003425 Tyrosinase Human genes 0.000 claims description 11
• 108060008724 Tyrosinase Proteins 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
• 125000006239 protecting group Chemical group 0.000 claims description 10
• 102000004190 Enzymes Human genes 0.000 claims description 8
• 108090000790 Enzymes Proteins 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 230000004663 cell proliferation Effects 0.000 claims description 8
• PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical compound NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 239000003795 chemical substances by application Substances 0.000 claims description 6
• 125000000524 functional group Chemical group 0.000 claims description 6
• 230000005764 inhibitory process Effects 0.000 claims description 6
• 239000012280 lithium aluminium hydride Substances 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 5
• 150000003973 alkyl amines Chemical class 0.000 claims description 5
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 239000007789 gas Substances 0.000 claims description 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 4
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
• CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 125000004494 ethyl ester group Chemical group 0.000 claims description 3
• 108020003175 receptors Proteins 0.000 claims description 3
• 102000005962 receptors Human genes 0.000 claims description 3
• ZEBFPAXSQXIPNF-UHFFFAOYSA-N 2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1 ZEBFPAXSQXIPNF-UHFFFAOYSA-N 0.000 claims description 2
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 239000007818 Grignard reagent Substances 0.000 claims description 2
• 229910000831 Steel Inorganic materials 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• VMWZRHGIAVCFNS-UHFFFAOYSA-J aluminum;lithium;tetrahydroxide Chemical compound [Li+].[OH-].[OH-].[OH-].[OH-].[Al+3] VMWZRHGIAVCFNS-UHFFFAOYSA-J 0.000 claims description 2
• 150000004795 grignard reagents Chemical class 0.000 claims description 2
• 150000004820 halides Chemical class 0.000 claims description 2
• BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 239000010959 steel Substances 0.000 claims description 2
• 239000000052 vinegar Substances 0.000 claims description 2
• 235000021419 vinegar Nutrition 0.000 claims description 2
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 2
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
• PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
• IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 claims 1
• TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 claims 1
• YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 claims 1
• ZOGISVNCCRKCKA-UHFFFAOYSA-N 2-morpholin-4-ylethanimidamide Chemical compound NC(=N)CN1CCOCC1 ZOGISVNCCRKCKA-UHFFFAOYSA-N 0.000 claims 1
• UMLZJALTCYNZCE-UHFFFAOYSA-N 3-morpholin-4-ylpropylurea Chemical compound NC(=O)NCCCN1CCOCC1 UMLZJALTCYNZCE-UHFFFAOYSA-N 0.000 claims 1
• GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims 1
• BPQZYUXXADLZJG-UHFFFAOYSA-N 4-methyloctan-4-amine Chemical compound CCCCC(C)(N)CCC BPQZYUXXADLZJG-UHFFFAOYSA-N 0.000 claims 1
• MGADSANUGJPJTF-MXVIHJGJSA-N C1[C@@H](C(=O)OC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1C Chemical compound C1[C@@H](C(=O)OC)C[C@@H]1N1C2=NC=NC(N)=C2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1C MGADSANUGJPJTF-MXVIHJGJSA-N 0.000 claims 1
• 241000283074 Equus asinus Species 0.000 claims 1
• JZKXXXDKRQWDET-QMMMGPOBSA-N L-m-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-QMMMGPOBSA-N 0.000 claims 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
• 229920000877 Melamine resin Polymers 0.000 claims 1
• 229910002651 NO3 Inorganic materials 0.000 claims 1
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
• 150000005224 alkoxybenzenes Chemical class 0.000 claims 1
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
• 125000002393 azetidinyl group Chemical group 0.000 claims 1
• 125000005605 benzo group Chemical group 0.000 claims 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
• RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 1
• 229910000071 diazene Inorganic materials 0.000 claims 1
• MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical class CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims 1
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 1
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
• 239000010931 gold Substances 0.000 claims 1
• 229910052737 gold Inorganic materials 0.000 claims 1
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
• 125000002883 imidazolyl group Chemical group 0.000 claims 1
• 125000000879 imine group Chemical group 0.000 claims 1
• 230000001404 mediated effect Effects 0.000 claims 1
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
• 229960005181 morphine Drugs 0.000 claims 1
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
• 125000001189 phytyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@](C([H])([H])[H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims 1
• XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 claims 1
• HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 claims 1
• 239000011677 pyridoxine Substances 0.000 claims 1
• 239000002689 soil Substances 0.000 claims 1
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
• 229940011671 vitamin b6 Drugs 0.000 claims 1
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• 241001465754 Metazoa Species 0.000 abstract description 8
• 241000282412 Homo Species 0.000 abstract description 4
• 241000124008 Mammalia Species 0.000 abstract description 2
• 238000004128 high performance liquid chromatography Methods 0.000 description 136
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 127
• 238000004458 analytical method Methods 0.000 description 109
• 241000208199 Buxus sempervirens Species 0.000 description 76
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 239000000243 solution Substances 0.000 description 33
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 238000005481 NMR spectroscopy Methods 0.000 description 23
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 239000002904 solvent Substances 0.000 description 22
• 210000004027 cell Anatomy 0.000 description 20
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 18
• 230000000694 effects Effects 0.000 description 18
• 239000012442 inert solvent Substances 0.000 description 18
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 16
• 229910052786 argon Inorganic materials 0.000 description 15
• 239000011541 reaction mixture Substances 0.000 description 15
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
• 239000004480 active ingredient Substances 0.000 description 14
• 239000002585 base Substances 0.000 description 13
• 238000003756 stirring Methods 0.000 description 13
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
• 229910052801 chlorine Inorganic materials 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 9
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
• 230000001028 anti-proliverative effect Effects 0.000 description 8
• 239000011261 inert gas Substances 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• 238000000746 purification Methods 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
• 101100335081 Mus musculus Flt3 gene Proteins 0.000 description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
• 238000004519 manufacturing process Methods 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
• 102000004127 Cytokines Human genes 0.000 description 6
• 108090000695 Cytokines Proteins 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000004202 carbamide Substances 0.000 description 6
• 238000003818 flash chromatography Methods 0.000 description 6
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
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