TWI297684B - Substituted pyrimidines - Google Patents

Info

Publication number

TWI297684B

TWI297684B TW096112205A TW96112205A TWI297684B TW I297684 B TWI297684 B TW I297684B TW 096112205 A TW096112205 A TW 096112205A TW 96112205 A TW96112205 A TW 96112205A TW I297684 B TWI297684 B TW I297684B

Authority

TW

Taiwan

Prior art keywords

group

ring

compound

doc

formula

Prior art date

2002-06-20

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• 150000003230 pyrimidines Chemical class 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 129
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 83
• 238000000034 method Methods 0.000 claims description 79
• 125000001931 aliphatic group Chemical group 0.000 claims description 78
• 239000000203 mixture Substances 0.000 claims description 61
• 125000001424 substituent group Chemical group 0.000 claims description 56
• 229910052757 nitrogen Inorganic materials 0.000 claims description 51
• -1 p-nitrophenylsulfonyl Chemical group 0.000 claims description 49
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
• 229910052760 oxygen Inorganic materials 0.000 claims description 41
• 239000001301 oxygen Substances 0.000 claims description 41
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 40
• 229910052717 sulfur Inorganic materials 0.000 claims description 40
• 239000011593 sulfur Substances 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 36
• 239000002904 solvent Substances 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
• 229920006395 saturated elastomer Polymers 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 23
• 150000003839 salts Chemical class 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000002619 bicyclic group Chemical group 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 17
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 239000011630 iodine Substances 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
• 238000012360 testing method Methods 0.000 claims description 6
• 239000007789 gas Substances 0.000 claims description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 239000000010 aprotic solvent Substances 0.000 claims description 4
• 150000002430 hydrocarbons Chemical class 0.000 claims description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
• 239000012312 sodium hydride Substances 0.000 claims description 4
• 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• 239000004215 Carbon black (E152) Substances 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 229930195733 hydrocarbon Natural products 0.000 claims description 3
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
• 125000003107 substituted aryl group Chemical group 0.000 claims description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
• 125000005233 alkylalcohol group Chemical group 0.000 claims description 2
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 229910052751 metal Inorganic materials 0.000 claims description 2
• 239000002184 metal Substances 0.000 claims description 2
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 2
• 229910000105 potassium hydride Inorganic materials 0.000 claims description 2
• 239000003586 protic polar solvent Substances 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 150000003304 ruthenium compounds Chemical class 0.000 claims description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
• 125000005270 trialkylamine group Chemical group 0.000 claims description 2
• 239000002689 soil Substances 0.000 claims 3
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
• 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
• 230000037429 base substitution Effects 0.000 claims 1
• 229940049676 bismuth hydroxide Drugs 0.000 claims 1
• TZSXPYWRDWEXHG-UHFFFAOYSA-K bismuth;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Bi+3] TZSXPYWRDWEXHG-UHFFFAOYSA-K 0.000 claims 1
• VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 claims 1
• BTZNPZMHENLISZ-UHFFFAOYSA-M fluoromethanesulfonate Chemical compound [O-]S(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-M 0.000 claims 1
• 229910052987 metal hydride Inorganic materials 0.000 claims 1
• 150000004681 metal hydrides Chemical class 0.000 claims 1
• 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
• 150000004692 metal hydroxides Chemical class 0.000 claims 1
• 150000002923 oximes Chemical class 0.000 claims 1
• 235000011181 potassium carbonates Nutrition 0.000 claims 1
• 235000011182 sodium carbonates Nutrition 0.000 claims 1
• 150000003573 thiols Chemical group 0.000 claims 1
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
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• 108090000461 Aurora Kinase A Proteins 0.000 description 20
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• FSPQCTGGIANIJZ-UHFFFAOYSA-N 2-[[(3,4-dimethoxyphenyl)-oxomethyl]amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)NC1=C(C(N)=O)C(CCCC2)=C2S1 FSPQCTGGIANIJZ-UHFFFAOYSA-N 0.000 description 10
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