NZ566804A - New pyrimidine derivatives and their use in therapy as well as the use of pyrimidine derivatives in the manufacture of a medicament for prevention and/or treatment of alzheimer's disease - Google Patents

Info

Publication number

NZ566804A

NZ566804A NZ566804A NZ56680406A NZ566804A NZ 566804 A NZ566804 A NZ 566804A NZ 566804 A NZ566804 A NZ 566804A NZ 56680406 A NZ56680406 A NZ 56680406A NZ 566804 A NZ566804 A NZ 566804A

Authority

NZ

New Zealand

Prior art keywords

imidazol

pyrimidin

methyl

fluoro

phenyl

Prior art date

2005-10-03

Links

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• Global Dossier
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• 208000024827 Alzheimer disease Diseases 0.000 title claims abstract description 27
• 230000002265 prevention Effects 0.000 title claims abstract description 26
• 238000004519 manufacturing process Methods 0.000 title claims description 18
• 239000003814 drug Substances 0.000 title claims description 17
• 238000002560 therapeutic procedure Methods 0.000 title claims description 6
• 150000003230 pyrimidines Chemical class 0.000 title description 5
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 462
• 150000003839 salts Chemical class 0.000 claims abstract description 89
• 238000000034 method Methods 0.000 claims abstract description 63
• 206010012289 Dementia Diseases 0.000 claims abstract description 24
• 230000008569 process Effects 0.000 claims abstract description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
• 201000011240 Frontotemporal dementia Diseases 0.000 claims abstract description 14
• 201000010099 disease Diseases 0.000 claims abstract description 14
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 10
• 208000017004 dementia pugilistica Diseases 0.000 claims abstract description 10
• 230000007170 pathology Effects 0.000 claims abstract description 10
• 208000037658 Parkinson-dementia complex of Guam Diseases 0.000 claims abstract description 9
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 193
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 187
• 125000000623 heterocyclic group Chemical group 0.000 claims description 172
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 161
• 229910052739 hydrogen Inorganic materials 0.000 claims description 158
• 239000001257 hydrogen Substances 0.000 claims description 157
• -1 Ci_3alkyl Chemical group 0.000 claims description 144
• 125000005843 halogen group Chemical group 0.000 claims description 120
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 95
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 90
• 125000001072 heteroaryl group Chemical group 0.000 claims description 71
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 239000012453 solvate Substances 0.000 claims description 61
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 57
• 125000004429 atom Chemical group 0.000 claims description 56
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 54
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
• 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 38
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 35
• 239000012458 free base Substances 0.000 claims description 35
• 238000006243 chemical reaction Methods 0.000 claims description 33
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 30
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 30
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 28
• 125000005842 heteroatom Chemical group 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 27
• 229910052717 sulfur Inorganic materials 0.000 claims description 27
• MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 18
• YDVHAJGGRNBAER-UHFFFAOYSA-N pyrimidin-2-amine;hydrochloride Chemical compound Cl.NC1=NC=CC=N1 YDVHAJGGRNBAER-UHFFFAOYSA-N 0.000 claims description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 12
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical group COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 11
• 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 10
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 10
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 208000010877 cognitive disease Diseases 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 150000003527 tetrahydropyrans Chemical group 0.000 claims description 8
• 208000020925 Bipolar disease Diseases 0.000 claims description 7
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• 230000005764 inhibitory process Effects 0.000 claims description 7
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 6
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
• 208000035475 disorder Diseases 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 238000001727 in vivo Methods 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 206010027175 memory impairment Diseases 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 5
• KWPKLLKLLVEXEJ-UHFFFAOYSA-N 5-fluoro-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-4-[3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C=NC=2)C2CCOCC2)=N1 KWPKLLKLLVEXEJ-UHFFFAOYSA-N 0.000 claims description 5
• 201000004384 Alopecia Diseases 0.000 claims description 5
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• LTHSGGMHLKBAIG-UHFFFAOYSA-N methyl 3-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C)=C1 LTHSGGMHLKBAIG-UHFFFAOYSA-N 0.000 claims description 5
• 230000004770 neurodegeneration Effects 0.000 claims description 5
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
• 238000002821 scintillation proximity assay Methods 0.000 claims description 5
• JUHQUEWVIIDBNH-UHFFFAOYSA-N (3,3-difluoroazetidin-1-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C(=O)N1CC(F)(F)C1 JUHQUEWVIIDBNH-UHFFFAOYSA-N 0.000 claims description 4
• IWTFTXAHVPOGGS-UHFFFAOYSA-N 3-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]-n-(3-methoxypropyl)benzamide;hydrochloride Chemical compound Cl.COCCCNC(=O)C1=CC=CC(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C)=C1 IWTFTXAHVPOGGS-UHFFFAOYSA-N 0.000 claims description 4
• URAFFHFGIKHGML-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C1=CC=NC(N)=N1 URAFFHFGIKHGML-UHFFFAOYSA-N 0.000 claims description 4
• BLFWGFFZXXRNOQ-UHFFFAOYSA-N 5-[5-fluoro-2-[4-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]-1-(oxan-4-yl)imidazole-2-carbonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C#N)=NC=2)C2CCOCC2)=N1 BLFWGFFZXXRNOQ-UHFFFAOYSA-N 0.000 claims description 4
• XWUFNANHAZTEFC-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[3-methylsulfonyl-4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1S(C)(=O)=O)=CC=C1CN1CCOCC1 XWUFNANHAZTEFC-UHFFFAOYSA-N 0.000 claims description 4
• ZCNYDSWSOIKGPQ-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)C(C(F)(F)F)=C1 ZCNYDSWSOIKGPQ-UHFFFAOYSA-N 0.000 claims description 4
• IOLWECNTCVXLQV-UHFFFAOYSA-N 5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]-n-[4-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.N1=C(C(F)(F)F)N(C)C(C=2C(=CN=C(NC=3C=CC(CN4CCOCC4)=CC=3)N=2)F)=C1 IOLWECNTCVXLQV-UHFFFAOYSA-N 0.000 claims description 4
• FNHROSXUOGTTFM-UHFFFAOYSA-N 5-fluoro-n-[3-methyl-4-(morpholin-4-ylmethyl)phenyl]-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1C)=CC=C1CN1CCOCC1 FNHROSXUOGTTFM-UHFFFAOYSA-N 0.000 claims description 4
• DLHJFTBEXSBEFV-UHFFFAOYSA-N 5-fluoro-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C)=N1 DLHJFTBEXSBEFV-UHFFFAOYSA-N 0.000 claims description 4
• QCSSTYNVUYCZAQ-UHFFFAOYSA-N 5-fluoro-n-[4-(morpholin-4-ylmethyl)phenyl]-4-[3-(oxan-4-yl)-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-amine;hydrochloride Chemical compound Cl.N1=C(C=2N(C(=NC=2)C(F)(F)F)C2CCOCC2)C(F)=CN=C1NC(C=C1)=CC=C1CN1CCOCC1 QCSSTYNVUYCZAQ-UHFFFAOYSA-N 0.000 claims description 4
• OQKLTFPVRPDGRN-UHFFFAOYSA-N 6-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-1,1-dioxo-2,3-dihydrothiochromen-4-one;hydrochloride Chemical compound Cl.CC1=NC=C(C=2C(=CN=C(NC=3C=C4C(S(CCC4=O)(=O)=O)=CC=3)N=2)F)N1C1CCOCC1 OQKLTFPVRPDGRN-UHFFFAOYSA-N 0.000 claims description 4
• LDARYERYIPQHMP-UHFFFAOYSA-N 6-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-1,1-dioxo-3,4-dihydro-2h-thiochromen-4-ol;hydrochloride Chemical compound Cl.CC1=NC=C(C=2C(=CN=C(NC=3C=C4C(S(CCC4O)(=O)=O)=CC=3)N=2)F)N1C1CCOCC1 LDARYERYIPQHMP-UHFFFAOYSA-N 0.000 claims description 4
• 208000027089 Parkinsonian disease Diseases 0.000 claims description 4
• 206010034010 Parkinsonism Diseases 0.000 claims description 4
• DBDXVTYNNKXTKP-UHFFFAOYSA-N [4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]-(4-fluoropiperidin-1-yl)methanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C(=O)N1CCC(F)CC1 DBDXVTYNNKXTKP-UHFFFAOYSA-N 0.000 claims description 4
• UOYZAQZJEFUCIP-UHFFFAOYSA-N [4-[[5-fluoro-4-[3-(oxan-4-yl)-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C2CCOCC2)=N1 UOYZAQZJEFUCIP-UHFFFAOYSA-N 0.000 claims description 4
• MOOUYDFWJLJXCM-UHFFFAOYSA-N [4-[[5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]-(4-methylpiperazin-1-yl)methanone;hydrochloride Chemical compound Cl.C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C)=N1 MOOUYDFWJLJXCM-UHFFFAOYSA-N 0.000 claims description 4
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
• XCPHTBBUCKHUBS-UHFFFAOYSA-N azetidin-1-yl-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C(=O)N1CCC1 XCPHTBBUCKHUBS-UHFFFAOYSA-N 0.000 claims description 4
• 210000000988 bone and bone Anatomy 0.000 claims description 4
• 230000001684 chronic effect Effects 0.000 claims description 4
• 239000007788 liquid Substances 0.000 claims description 4
• WGLKCJSZMNTANV-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]-n-methylbenzamide;hydrochloride Chemical compound Cl.CN(C)CCCN(C)C(=O)C1=CC=CC(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C)=C1 WGLKCJSZMNTANV-UHFFFAOYSA-N 0.000 claims description 4
• ZRLJFHYCTGWKJS-UHFFFAOYSA-N n-[4-[(dimethylamino)methyl]phenyl]-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=CC(CN(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 ZRLJFHYCTGWKJS-UHFFFAOYSA-N 0.000 claims description 4
• QVNQBICOSFVRIE-UHFFFAOYSA-N n-[4-[1-(azetidin-1-yl)ethyl]phenyl]-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C=1C=C(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)C=CC=1C(C)N1CCC1 QVNQBICOSFVRIE-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• NRTTUJLILQPENP-UHFFFAOYSA-N pyridine-2-carbaldehyde;hydrochloride Chemical compound Cl.O=CC1=CC=CC=N1 NRTTUJLILQPENP-UHFFFAOYSA-N 0.000 claims description 4
• VGSQFKCYTNOWJM-UHFFFAOYSA-N (2,6-dimethylmorpholin-4-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1C(C)OC(C)CN1C(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 VGSQFKCYTNOWJM-UHFFFAOYSA-N 0.000 claims description 3
• UHDXDZQXNNJWDY-UHFFFAOYSA-N (3,3-difluoropyrrolidin-1-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1)=CC=C1C(=O)N1CCC(F)(F)C1 UHDXDZQXNNJWDY-UHFFFAOYSA-N 0.000 claims description 3
• AUDGHHREDWBFOE-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]methanone;hydrochloride Chemical compound Cl.C1CN(CC)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 AUDGHHREDWBFOE-UHFFFAOYSA-N 0.000 claims description 3
• DCDIEFUKOHCORY-UHFFFAOYSA-N 2-[4-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]phenyl]sulfonylethanol Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(=O)(=O)CCO)C=C1 DCDIEFUKOHCORY-UHFFFAOYSA-N 0.000 claims description 3
• LVBDLAPMBZGOMR-UHFFFAOYSA-N 2-aminobenzamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=CC=C1N LVBDLAPMBZGOMR-UHFFFAOYSA-N 0.000 claims description 3
• VTEAOOUKGTUNBL-UHFFFAOYSA-N 4-(2,3-dimethylimidazol-4-yl)-5-fluoro-n-(4-methylsulfonylphenyl)pyrimidin-2-amine Chemical compound CN1C(C)=NC=C1C1=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=NC=C1F VTEAOOUKGTUNBL-UHFFFAOYSA-N 0.000 claims description 3
• XTWRYVIQIXIGHG-UHFFFAOYSA-N 4-(2,3-dimethylimidazol-4-yl)-5-fluoro-n-[3-methyl-4-(4-methylpiperazin-1-yl)sulfonylphenyl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C(C(=C1)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C)=N1 XTWRYVIQIXIGHG-UHFFFAOYSA-N 0.000 claims description 3
• QLNHZJLXRCTCMN-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-methylsulfonylphenyl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(N=1)=CC=NC=1NC1=CC=C(S(C)(=O)=O)C=C1 QLNHZJLXRCTCMN-UHFFFAOYSA-N 0.000 claims description 3
• HYESJXMPFNNNAW-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(4-morpholin-4-ylsulfonylphenyl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(N=1)=CC=NC=1NC(C=C1)=CC=C1S(=O)(=O)N1CCOCC1 HYESJXMPFNNNAW-UHFFFAOYSA-N 0.000 claims description 3
• KJJXNFGGNQIJRQ-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(NC=2N=C(C=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)=C1 KJJXNFGGNQIJRQ-UHFFFAOYSA-N 0.000 claims description 3
• WDBIOFPEYDNNET-UHFFFAOYSA-N 4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=CC(C=2N(C(C)=NC=2)C2CCOCC2)=N1 WDBIOFPEYDNNET-UHFFFAOYSA-N 0.000 claims description 3
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