CN104203943B - 取代的嘧啶化合物及其作为syk抑制剂的用途 - Google Patents

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Publication number

CN104203943B

CN104203943B CN201380015041.1A CN201380015041A CN104203943B CN 104203943 B CN104203943 B CN 104203943B CN 201380015041 A CN201380015041 A CN 201380015041A CN 104203943 B CN104203943 B CN 104203943B

Authority

CN

China

Prior art keywords

bases

methyl

amino

pyrazoles

pyrimidine

Prior art date

2012-01-20

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 pyrimidine compound Chemical class 0.000 title claims description 258
• 239000003112 inhibitor Substances 0.000 title description 16
• 150000001875 compounds Chemical class 0.000 claims abstract description 303
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 75
• 201000010099 disease Diseases 0.000 claims abstract description 61
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 374
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 290
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 96
• HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 94
• 150000002576 ketones Chemical class 0.000 claims description 68
• 229910052736 halogen Inorganic materials 0.000 claims description 58
• 150000002367 halogens Chemical class 0.000 claims description 56
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 55
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 54
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 52
• 150000003235 pyrrolidines Chemical class 0.000 claims description 51
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 49
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 48
• 238000006467 substitution reaction Methods 0.000 claims description 44
• NQZLDYNWFMODIM-UHFFFAOYSA-N 1h-azepin-3-ol Chemical compound OC1=CNC=CC=C1 NQZLDYNWFMODIM-UHFFFAOYSA-N 0.000 claims description 41
• 150000003839 salts Chemical class 0.000 claims description 40
• 125000002950 monocyclic group Chemical group 0.000 claims description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 36
• 239000000203 mixture Substances 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 210000004027 cell Anatomy 0.000 claims description 28
• 229910021529 ammonia Inorganic materials 0.000 claims description 26
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
• 208000006673 asthma Diseases 0.000 claims description 20
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 18
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
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• 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 8
• 230000001684 chronic effect Effects 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 4
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• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• QONGECDDDTYBGS-UHFFFAOYSA-N dimorpholin-4-ylmethanone Chemical compound C1COCCN1C(=O)N1CCOCC1 QONGECDDDTYBGS-UHFFFAOYSA-N 0.000 claims description 3
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• SUHYUUVUQGJUJC-UHFFFAOYSA-N 2-cyclopropylpyridine Chemical compound C1CC1C1=CC=CC=N1 SUHYUUVUQGJUJC-UHFFFAOYSA-N 0.000 claims 2
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 2
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• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
• HPTQKSXAQBHFKL-UHFFFAOYSA-N dipyrrolidin-1-ylmethanone Chemical compound C1CCCN1C(=O)N1CCCC1 HPTQKSXAQBHFKL-UHFFFAOYSA-N 0.000 claims 1
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
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• 125000003118 aryl group Chemical group 0.000 description 54
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 51
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
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• 125000002521 alkyl halide group Chemical group 0.000 description 27
• 239000007787 solid Substances 0.000 description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
• 229910052760 oxygen Inorganic materials 0.000 description 23
• 239000002904 solvent Substances 0.000 description 22
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 19
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• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
• 239000003513 alkali Substances 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
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• QLATXALTCNYKEO-UHFFFAOYSA-N 2-chloro-1-methylindole Chemical class C1=CC=C2N(C)C(Cl)=CC2=C1 QLATXALTCNYKEO-UHFFFAOYSA-N 0.000 description 12
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