CA2653777A1 - 2-anilino-4-(heterocyclic)amino-pyrimidines - Google Patents

Info

Publication number

CA2653777A1

CA2653777A1 CA002653777A CA2653777A CA2653777A1 CA 2653777 A1 CA2653777 A1 CA 2653777A1 CA 002653777 A CA002653777 A CA 002653777A CA 2653777 A CA2653777 A CA 2653777A CA 2653777 A1 CA2653777 A1 CA 2653777A1

Authority

CA

Canada

Prior art keywords

pyrimidine

propyl

diamine

phenyl

biphenyl

Prior art date

2006-06-15

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000005005 aminopyrimidines Chemical class 0.000 title abstract description 6
• 239000000203 mixture Substances 0.000 claims abstract description 60
• 206010019280 Heart failures Diseases 0.000 claims abstract description 38
• 239000003112 inhibitor Substances 0.000 claims abstract description 34
• 238000000034 method Methods 0.000 claims abstract description 32
• 230000002107 myocardial effect Effects 0.000 claims abstract description 12
• -1 pyrrolin-1-y1 Chemical group 0.000 claims description 588
• 150000001875 compounds Chemical class 0.000 claims description 110
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 125000000623 heterocyclic group Chemical group 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
• 125000004429 atom Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 125000005647 linker group Chemical group 0.000 claims description 10
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• 206010007556 Cardiac failure acute Diseases 0.000 claims description 9
• 241000282414 Homo sapiens Species 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
• 201000010099 disease Diseases 0.000 claims description 7
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• 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 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 206010003119 arrhythmia Diseases 0.000 claims description 6
• 230000006793 arrhythmia Effects 0.000 claims description 6
• 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 6
• 229940079593 drug Drugs 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 208000017169 kidney disease Diseases 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• 206010020772 Hypertension Diseases 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 150000002632 lipids Chemical class 0.000 claims description 5
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
• 206010007558 Cardiac failure chronic Diseases 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• IPRJXAGUEGOFGG-UHFFFAOYSA-N N-butylbenzenesulfonamide Chemical compound CCCCNS(=O)(=O)C1=CC=CC=C1 IPRJXAGUEGOFGG-UHFFFAOYSA-N 0.000 claims description 4
• 208000029078 coronary artery disease Diseases 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 230000000638 stimulation Effects 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• PKVDVCMRWCLXKR-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-(piperidin-2-ylmethyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(NC=2N=C(NCC3NCCCC3)C=CN=2)=C1 PKVDVCMRWCLXKR-UHFFFAOYSA-N 0.000 claims description 3
• WKPKDVNXMWQVKU-UHFFFAOYSA-N 2-n-(3-methoxyphenyl)-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(NC=2N=C(NCCCN3CCCC3)C=CN=2)=C1 WKPKDVNXMWQVKU-UHFFFAOYSA-N 0.000 claims description 3
• ZNFARSGNRFIBEY-UHFFFAOYSA-N 2-n-[3-(3-methylphenyl)phenyl]-4-n-(3-pyrazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4NCCC4)C=CN=3)C=CC=2)=C1 ZNFARSGNRFIBEY-UHFFFAOYSA-N 0.000 claims description 3
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
• 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 3
• 208000006029 Cardiomegaly Diseases 0.000 claims description 3
• 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 3
• 201000010046 Dilated cardiomyopathy Diseases 0.000 claims description 3
• 206010048554 Endothelial dysfunction Diseases 0.000 claims description 3
• 206010061216 Infarction Diseases 0.000 claims description 3
• 206010028980 Neoplasm Diseases 0.000 claims description 3
• 206010063837 Reperfusion injury Diseases 0.000 claims description 3
• 208000017442 Retinal disease Diseases 0.000 claims description 3
• 206010038923 Retinopathy Diseases 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 206010042434 Sudden death Diseases 0.000 claims description 3
• 208000015294 blood coagulation disease Diseases 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 claims description 3
• 239000002934 diuretic Substances 0.000 claims description 3
• 230000008694 endothelial dysfunction Effects 0.000 claims description 3
• 230000010247 heart contraction Effects 0.000 claims description 3
• 230000007574 infarction Effects 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 208000037906 ischaemic injury Diseases 0.000 claims description 3
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 3
• 230000000302 ischemic effect Effects 0.000 claims description 3
• 239000003226 mitogen Substances 0.000 claims description 3
• 201000001119 neuropathy Diseases 0.000 claims description 3
• 230000007823 neuropathy Effects 0.000 claims description 3
• 208000030613 peripheral artery disease Diseases 0.000 claims description 3
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 3
• 230000036454 renin-angiotensin system Effects 0.000 claims description 3
• 208000037803 restenosis Diseases 0.000 claims description 3
• 208000032598 susceptibility microvascular complications of diabetes Diseases 0.000 claims description 3
• 208000019553 vascular disease Diseases 0.000 claims description 3
• 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
• 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims description 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• PYRBBLDGJYYBKR-UHFFFAOYSA-N 2-N-[3-(1,3-benzothiazol-2-yl)phenyl]-4-N-[3-(1,3-dihydropyrazol-2-yl)propyl]pyrimidine-2,4-diamine Chemical compound S1C(=NC2=C1C=CC=C2)C=2C=C(C=CC2)NC2=NC=CC(=N2)NCCCN2NC=CC2 PYRBBLDGJYYBKR-UHFFFAOYSA-N 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
• LBRCSHJFEHRFMU-UHFFFAOYSA-N 2-n-(3-aminophenyl)-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound NC1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 LBRCSHJFEHRFMU-UHFFFAOYSA-N 0.000 claims description 2
• OFDGVGLYJNTNLR-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NC1=CC=NC(NC=2C=C(Cl)C=CC=2)=N1 OFDGVGLYJNTNLR-UHFFFAOYSA-N 0.000 claims description 2
• RLASDHCNFODFHH-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-(3-pyrazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(NC=2N=C(NCCCN3NCCC3)C=CN=2)=C1 RLASDHCNFODFHH-UHFFFAOYSA-N 0.000 claims description 2
• AVGYVMZYRPRURN-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-[(1-methylpiperidin-2-yl)methyl]pyrimidine-2,4-diamine Chemical compound CN1CCCCC1CNC1=CC=NC(NC=2C=C(Cl)C=CC=2)=N1 AVGYVMZYRPRURN-UHFFFAOYSA-N 0.000 claims description 2
• LTGFJAODGMTKNB-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-[(1-propan-2-ylpiperidin-3-yl)methyl]pyrimidine-2,4-diamine Chemical compound C1N(C(C)C)CCCC1CNC1=CC=NC(NC=2C=C(Cl)C=CC=2)=N1 LTGFJAODGMTKNB-UHFFFAOYSA-N 0.000 claims description 2
• JKXMUQDZRLBIKI-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-[3-(2,5-dihydropyrrol-1-yl)propyl]pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(NC=2N=C(NCCCN3CC=CC3)C=CN=2)=C1 JKXMUQDZRLBIKI-UHFFFAOYSA-N 0.000 claims description 2
• DTJLZSSPGOXHKN-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-4-n-[3-(4-methylpiperazin-1-yl)propyl]pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1CCCNC1=CC=NC(NC=2C=C(Cl)C=CC=2)=N1 DTJLZSSPGOXHKN-UHFFFAOYSA-N 0.000 claims description 2
• DMGFVZYGJUBCHC-UHFFFAOYSA-N 2-n-(3-fluorophenyl)-4-n-(3-pyrazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(NC=2N=C(NCCCN3NCCC3)C=CN=2)=C1 DMGFVZYGJUBCHC-UHFFFAOYSA-N 0.000 claims description 2
• VSXSYBPOCRUEPR-UHFFFAOYSA-N 2-n-(3-fluorophenyl)-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(NC=2N=C(NCCCN3CCCC3)C=CN=2)=C1 VSXSYBPOCRUEPR-UHFFFAOYSA-N 0.000 claims description 2
• FNHJXAGCTBEYAS-UHFFFAOYSA-N 2-n-(3-methoxyphenyl)-4-n-(3-piperidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(NC=2N=C(NCCCN3CCCCC3)C=CN=2)=C1 FNHJXAGCTBEYAS-UHFFFAOYSA-N 0.000 claims description 2
• BZVRLRJICNHAST-UHFFFAOYSA-N 2-n-(3-methylphenyl)-4-n-(3-piperazin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(NC=2N=C(NCCCN3CCNCC3)C=CN=2)=C1 BZVRLRJICNHAST-UHFFFAOYSA-N 0.000 claims description 2
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• IYYKCJDTDYYACK-UHFFFAOYSA-N 2-n-[3-(1,3-benzothiazol-2-yl)phenyl]-4-n-(3-imidazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound C=1C=NC(NC=2C=C(C=CC=2)C=2SC3=CC=CC=C3N=2)=NC=1NCCCN1CCNC1 IYYKCJDTDYYACK-UHFFFAOYSA-N 0.000 claims description 2
• UNGPDXMAWQFHTL-UHFFFAOYSA-N 2-n-[3-(1,3-benzothiazol-2-yl)phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound C=1C=NC(NC=2C=C(C=CC=2)C=2SC3=CC=CC=C3N=2)=NC=1NCCCN1CCOCC1 UNGPDXMAWQFHTL-UHFFFAOYSA-N 0.000 claims description 2
• PMJITVPUALMFNF-UHFFFAOYSA-N 2-n-[3-(3-chlorophenyl)phenyl]-4-n-[3-(2,4-dihydroimidazol-3-yl)propyl]pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CN=CC4)C=CN=3)C=CC=2)=C1 PMJITVPUALMFNF-UHFFFAOYSA-N 0.000 claims description 2
• KIZFSNZKWNKQOF-UHFFFAOYSA-N 2-n-[3-(3-fluorophenyl)phenyl]-4-n-(3-piperidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCCC4)C=CN=3)C=CC=2)=C1 KIZFSNZKWNKQOF-UHFFFAOYSA-N 0.000 claims description 2
• HELVSIKGTDLMHN-UHFFFAOYSA-N 2-n-[3-(3-fluorophenyl)phenyl]-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCC4)C=CN=3)C=CC=2)=C1 HELVSIKGTDLMHN-UHFFFAOYSA-N 0.000 claims description 2
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• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
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• FGFMJNBXUYBHFU-UHFFFAOYSA-N 4-(dimethylamino)-n-[3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]phenyl]benzamide Chemical compound C1=CC(N(C)C)=CC=C1C(=O)NC1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 FGFMJNBXUYBHFU-UHFFFAOYSA-N 0.000 claims description 2
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
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• JGSSICROHXOQNF-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-[3-(1h-indol-2-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C=NC(NC=2C=C(C=CC=2)C=2NC3=CC=CC=C3C=2)=NC=1NCCCN1CCNC1 JGSSICROHXOQNF-UHFFFAOYSA-N 0.000 claims description 2
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• LETHIGCPPHQENA-UHFFFAOYSA-N 2-n-[3-(1h-indol-4-yl)phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound C=1C=NC(NC=2C=C(C=CC=2)C=2C=3C=CNC=3C=CC=2)=NC=1NCCCN1CCOCC1 LETHIGCPPHQENA-UHFFFAOYSA-N 0.000 claims 1
• DLDVBNTXUHTKGC-UHFFFAOYSA-N 2-n-[3-(1h-indol-6-yl)phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound C=1C=NC(NC=2C=C(C=CC=2)C=2C=C3NC=CC3=CC=2)=NC=1NCCCN1CCOCC1 DLDVBNTXUHTKGC-UHFFFAOYSA-N 0.000 claims 1
• NHURYRNPCZWBGE-UHFFFAOYSA-N 2-n-[3-(3-chlorophenyl)phenyl]-4-n-(3-imidazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CNCC4)C=CN=3)C=CC=2)=C1 NHURYRNPCZWBGE-UHFFFAOYSA-N 0.000 claims 1
• NGEKDJPAZURXRB-UHFFFAOYSA-N 2-n-[3-(3-chlorophenyl)phenyl]-4-n-(3-piperazin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCNCC4)C=CN=3)C=CC=2)=C1 NGEKDJPAZURXRB-UHFFFAOYSA-N 0.000 claims 1
• VDVRLABOTJYFBB-UHFFFAOYSA-N 2-n-[3-(3-chlorophenyl)phenyl]-4-n-(3-piperidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCCC4)C=CN=3)C=CC=2)=C1 VDVRLABOTJYFBB-UHFFFAOYSA-N 0.000 claims 1
• TZNYKXMGFKVINJ-UHFFFAOYSA-N 2-n-[3-(3-chlorophenyl)phenyl]-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCC4)C=CN=3)C=CC=2)=C1 TZNYKXMGFKVINJ-UHFFFAOYSA-N 0.000 claims 1
• ZCVBTGGIBUXRQM-UHFFFAOYSA-N 2-n-[3-(3-chlorophenyl)phenyl]-4-n-[3-(2,5-dihydropyrrol-1-yl)propyl]pyrimidine-2,4-diamine Chemical compound ClC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CC=CC4)C=CN=3)C=CC=2)=C1 ZCVBTGGIBUXRQM-UHFFFAOYSA-N 0.000 claims 1
• QIXDNCRXICMHPZ-UHFFFAOYSA-N 2-n-[3-(3-fluorophenyl)phenyl]-4-n-(3-imidazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CNCC4)C=CN=3)C=CC=2)=C1 QIXDNCRXICMHPZ-UHFFFAOYSA-N 0.000 claims 1
• VPGACPUGPURFRA-UHFFFAOYSA-N 2-n-[3-(3-fluorophenyl)phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCOCC4)C=CN=3)C=CC=2)=C1 VPGACPUGPURFRA-UHFFFAOYSA-N 0.000 claims 1
• ZJCAUUIBBZFDER-UHFFFAOYSA-N 2-n-[3-(3-fluorophenyl)phenyl]-4-n-(3-piperazin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCNCC4)C=CN=3)C=CC=2)=C1 ZJCAUUIBBZFDER-UHFFFAOYSA-N 0.000 claims 1
• DHPUPZWHXSXKME-UHFFFAOYSA-N 2-n-[3-(3-fluorophenyl)phenyl]-4-n-(3-pyrazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound FC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4NCCC4)C=CN=3)C=CC=2)=C1 DHPUPZWHXSXKME-UHFFFAOYSA-N 0.000 claims 1
• LVEDYWIXQKNSQE-UHFFFAOYSA-N 2-n-[3-(3-methoxyphenyl)phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCOCC4)C=CN=3)C=CC=2)=C1 LVEDYWIXQKNSQE-UHFFFAOYSA-N 0.000 claims 1
• HHGNLLDQLPHBQU-UHFFFAOYSA-N 2-n-[3-(3-methoxyphenyl)phenyl]-4-n-(3-piperazin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCNCC4)C=CN=3)C=CC=2)=C1 HHGNLLDQLPHBQU-UHFFFAOYSA-N 0.000 claims 1
• UDOOTIPQENXNFE-UHFFFAOYSA-N 2-n-[3-(3-methoxyphenyl)phenyl]-4-n-(3-piperidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCCC4)C=CN=3)C=CC=2)=C1 UDOOTIPQENXNFE-UHFFFAOYSA-N 0.000 claims 1
• DIIYLUJVKUMIJR-UHFFFAOYSA-N 2-n-[3-(3-methoxyphenyl)phenyl]-4-n-(3-pyrazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4NCCC4)C=CN=3)C=CC=2)=C1 DIIYLUJVKUMIJR-UHFFFAOYSA-N 0.000 claims 1
• WAVVMXYIANZRQD-UHFFFAOYSA-N 2-n-[3-(3-methoxyphenyl)phenyl]-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCC4)C=CN=3)C=CC=2)=C1 WAVVMXYIANZRQD-UHFFFAOYSA-N 0.000 claims 1
• MBRFFGMQFZTKLE-UHFFFAOYSA-N 2-n-[3-(3-methylphenyl)phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCOCC4)C=CN=3)C=CC=2)=C1 MBRFFGMQFZTKLE-UHFFFAOYSA-N 0.000 claims 1
• HEUUGZXKJFAHRF-UHFFFAOYSA-N 2-n-[3-(3-methylphenyl)phenyl]-4-n-(3-piperazin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCNCC4)C=CN=3)C=CC=2)=C1 HEUUGZXKJFAHRF-UHFFFAOYSA-N 0.000 claims 1
• FVJVMLJJBKOXMT-UHFFFAOYSA-N 2-n-[3-(3-methylphenyl)phenyl]-4-n-(3-piperidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCCC4)C=CN=3)C=CC=2)=C1 FVJVMLJJBKOXMT-UHFFFAOYSA-N 0.000 claims 1
• GWIDTTZIFGSPRZ-UHFFFAOYSA-N 2-n-[3-(3-methylphenyl)phenyl]-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCC4)C=CN=3)C=CC=2)=C1 GWIDTTZIFGSPRZ-UHFFFAOYSA-N 0.000 claims 1
• WXCZJQFGGCUHEA-UHFFFAOYSA-N 2-n-[3-(3-nitrophenyl)phenyl]-4-n-(3-piperazin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCNCC4)C=CN=3)C=CC=2)=C1 WXCZJQFGGCUHEA-UHFFFAOYSA-N 0.000 claims 1
• VPOKKEJCVJZNEB-UHFFFAOYSA-N 2-n-[3-(3-nitrophenyl)phenyl]-4-n-(3-piperidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCCC4)C=CN=3)C=CC=2)=C1 VPOKKEJCVJZNEB-UHFFFAOYSA-N 0.000 claims 1
• CIZDMRAWHBQFPF-UHFFFAOYSA-N 2-n-[3-(3-nitrophenyl)phenyl]-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCC4)C=CN=3)C=CC=2)=C1 CIZDMRAWHBQFPF-UHFFFAOYSA-N 0.000 claims 1
• PYEIXRVQPDFIGT-UHFFFAOYSA-N 2-n-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 PYEIXRVQPDFIGT-UHFFFAOYSA-N 0.000 claims 1
• ULMDLASXYZRPFQ-UHFFFAOYSA-N 2-n-[3-(imidazol-1-ylmethyl)phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound C1COCCN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1CN1C=CN=C1 ULMDLASXYZRPFQ-UHFFFAOYSA-N 0.000 claims 1
• SNWICGLQSPUODB-UHFFFAOYSA-N 2-n-[3-[3-(dimethylamino)phenyl]phenyl]-4-n-(3-imidazolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CNCC4)C=CN=3)C=CC=2)=C1 SNWICGLQSPUODB-UHFFFAOYSA-N 0.000 claims 1
• GAGQDAZTGZZHSS-UHFFFAOYSA-N 2-n-[3-[3-(dimethylamino)phenyl]phenyl]-4-n-(3-morpholin-4-ylpropyl)pyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCOCC4)C=CN=3)C=CC=2)=C1 GAGQDAZTGZZHSS-UHFFFAOYSA-N 0.000 claims 1
• WJOLMDOMRMQIOW-UHFFFAOYSA-N 2-n-[3-[3-(dimethylamino)phenyl]phenyl]-4-n-(3-piperidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCCC4)C=CN=3)C=CC=2)=C1 WJOLMDOMRMQIOW-UHFFFAOYSA-N 0.000 claims 1
• JHGDAGAWAIZOQM-UHFFFAOYSA-N 2-n-[3-[3-(dimethylamino)phenyl]phenyl]-4-n-(3-pyrrolidin-1-ylpropyl)pyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCCC4)C=CN=3)C=CC=2)=C1 JHGDAGAWAIZOQM-UHFFFAOYSA-N 0.000 claims 1
• SWOGFIPFTSZKFV-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]-n-(2-pyridin-3-ylethyl)benzenesulfonamide Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=CC=1S(=O)(=O)NCCC1=CC=CN=C1 SWOGFIPFTSZKFV-UHFFFAOYSA-N 0.000 claims 1
• HSRLMIUTLYTNCA-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]-n-(pyridin-3-ylmethyl)benzenesulfonamide Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=CC=1S(=O)(=O)NCC1=CC=CN=C1 HSRLMIUTLYTNCA-UHFFFAOYSA-N 0.000 claims 1
• MXUDTTFTVAZJRN-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]-n-phenylbenzenesulfonamide Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=CC=1S(=O)(=O)NC1=CC=CC=C1 MXUDTTFTVAZJRN-UHFFFAOYSA-N 0.000 claims 1
• DSYWRSXCWXRZEB-UHFFFAOYSA-N 3-[[4-(3-morpholin-4-ylpropylamino)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 DSYWRSXCWXRZEB-UHFFFAOYSA-N 0.000 claims 1
• LHKCQPJAMFNZGW-UHFFFAOYSA-N 4-N-[3-(1,3-dihydropyrazol-2-yl)propyl]-2-N-(3-pyridin-2-ylphenyl)pyrimidine-2,4-diamine Chemical compound N1=C(C=CC=C1)C=1C=C(C=CC1)NC1=NC=CC(=N1)NCCCN1NC=CC1 LHKCQPJAMFNZGW-UHFFFAOYSA-N 0.000 claims 1
• POLFANULUAIITR-UHFFFAOYSA-N 4-N-[3-(1,3-dihydropyrazol-2-yl)propyl]-2-N-(3-pyridin-4-ylphenyl)pyrimidine-2,4-diamine Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC1)NC1=NC=CC(=N1)NCCCN1NC=CC1 POLFANULUAIITR-UHFFFAOYSA-N 0.000 claims 1
• YFUHGYYFIWFNGS-UHFFFAOYSA-N 4-N-[3-(1,3-dihydropyrazol-2-yl)propyl]-2-N-[3-(1H-indol-2-yl)phenyl]pyrimidine-2,4-diamine Chemical compound N1C(=CC2=CC=CC=C12)C=1C=C(C=CC1)NC1=NC=CC(=N1)NCCCN1NC=CC1 YFUHGYYFIWFNGS-UHFFFAOYSA-N 0.000 claims 1
• OYQJBNAWZJIZGM-UHFFFAOYSA-N 4-N-[3-(1,3-dihydropyrazol-2-yl)propyl]-2-N-[3-(1H-indol-3-yl)phenyl]pyrimidine-2,4-diamine Chemical compound N1C=C(C2=CC=CC=C12)C=1C=C(C=CC1)NC1=NC=CC(=N1)NCCCN1NC=CC1 OYQJBNAWZJIZGM-UHFFFAOYSA-N 0.000 claims 1
• XKRXCKOBPDMRDU-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-(3-methoxyphenyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(NC=2N=C(NCCCN3CNCC3)C=CN=2)=C1 XKRXCKOBPDMRDU-UHFFFAOYSA-N 0.000 claims 1
• ODURSVMQJVPUIU-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-(3-methylphenyl)pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(NC=2N=C(NCCCN3CNCC3)C=CN=2)=C1 ODURSVMQJVPUIU-UHFFFAOYSA-N 0.000 claims 1
• QVONEGDJVIEGKZ-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-(3-pyridin-2-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1CNCN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CC=CC=N1 QVONEGDJVIEGKZ-UHFFFAOYSA-N 0.000 claims 1
• TYSUBSHOTHJKTE-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-[3-(1h-indol-3-yl)phenyl]pyrimidine-2,4-diamine Chemical compound C=1C=NC(NC=2C=C(C=CC=2)C=2C3=CC=CC=C3NC=2)=NC=1NCCCN1CCNC1 TYSUBSHOTHJKTE-UHFFFAOYSA-N 0.000 claims 1
• HESKQVBHXRUQJJ-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-[3-(3-methoxyphenyl)phenyl]pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CNCC4)C=CN=3)C=CC=2)=C1 HESKQVBHXRUQJJ-UHFFFAOYSA-N 0.000 claims 1
• LCYBSNIRVWIUNV-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-[3-(3-methylphenyl)phenyl]pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CNCC4)C=CN=3)C=CC=2)=C1 LCYBSNIRVWIUNV-UHFFFAOYSA-N 0.000 claims 1
• PUZDXVXSPPXJGA-UHFFFAOYSA-N 4-n-(3-imidazolidin-1-ylpropyl)-2-n-[3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C(NCCCN3CNCC3)C=CN=2)=C1 PUZDXVXSPPXJGA-UHFFFAOYSA-N 0.000 claims 1
• CPFYARNRBHUZCY-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-(3-morpholin-4-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound C=1C=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=CC=1S(=O)(=O)N1CCOCC1 CPFYARNRBHUZCY-UHFFFAOYSA-N 0.000 claims 1
• UAWAXTZVIVXSKG-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-(3-nitrophenyl)pyrimidine-2,4-diamine Chemical compound [O-][N+](=O)C1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 UAWAXTZVIVXSKG-UHFFFAOYSA-N 0.000 claims 1
• GVQGUTKYAOUIOL-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-(3-phenoxyphenyl)pyrimidine-2,4-diamine Chemical compound C1COCCN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1OC1=CC=CC=C1 GVQGUTKYAOUIOL-UHFFFAOYSA-N 0.000 claims 1
• FOPOSDAUTHQIJZ-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-(3-phenylphenyl)pyrimidine-2,4-diamine Chemical compound C1COCCN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CC=CC=C1 FOPOSDAUTHQIJZ-UHFFFAOYSA-N 0.000 claims 1
• AGCFCICTIANIFV-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-(3-propan-2-ylphenyl)pyrimidine-2,4-diamine Chemical compound CC(C)C1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 AGCFCICTIANIFV-UHFFFAOYSA-N 0.000 claims 1
• ILNDGPHXALBAEY-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-(3-pyridin-3-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1COCCN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CC=CN=C1 ILNDGPHXALBAEY-UHFFFAOYSA-N 0.000 claims 1
• OOFZVQWYSZCNKT-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound FC(F)C(F)(F)OC1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 OOFZVQWYSZCNKT-UHFFFAOYSA-N 0.000 claims 1
• CNKBGOHGKZIVSY-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-[3-(3-nitrophenyl)phenyl]pyrimidine-2,4-diamine Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C(NC=3N=C(NCCCN4CCOCC4)C=CN=3)C=CC=2)=C1 CNKBGOHGKZIVSY-UHFFFAOYSA-N 0.000 claims 1
• ANVPWSDPMHXJCQ-UHFFFAOYSA-N 4-n-(3-morpholin-4-ylpropyl)-2-n-[3-(trifluoromethoxy)phenyl]pyrimidine-2,4-diamine Chemical compound FC(F)(F)OC1=CC=CC(NC=2N=C(NCCCN3CCOCC3)C=CN=2)=C1 ANVPWSDPMHXJCQ-UHFFFAOYSA-N 0.000 claims 1
• PRLVAZIMLUMRHM-UHFFFAOYSA-N 4-n-(3-piperazin-1-ylpropyl)-2-n-(3-pyridin-4-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1CNCCN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CC=NC=C1 PRLVAZIMLUMRHM-UHFFFAOYSA-N 0.000 claims 1
• GUIMDRFWHCVAFD-UHFFFAOYSA-N 4-n-(3-piperazin-1-ylpropyl)-2-n-[3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C(NCCCN3CCNCC3)C=CN=2)=C1 GUIMDRFWHCVAFD-UHFFFAOYSA-N 0.000 claims 1
• ZVTXUGRLHFKASZ-UHFFFAOYSA-N 4-n-(3-piperidin-1-ylpropyl)-2-n-(3-pyridin-4-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1CCCCN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CC=NC=C1 ZVTXUGRLHFKASZ-UHFFFAOYSA-N 0.000 claims 1
• JEZXVKQJZXQQSU-UHFFFAOYSA-N 4-n-(3-piperidin-1-ylpropyl)-2-n-[3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C(NCCCN3CCCCC3)C=CN=2)=C1 JEZXVKQJZXQQSU-UHFFFAOYSA-N 0.000 claims 1
• JFUBCYAHCZCJOK-UHFFFAOYSA-N 4-n-(3-pyrazolidin-1-ylpropyl)-2-n-(3-pyridin-2-ylphenyl)pyrimidine-2,4-diamine Chemical compound C1CCNN1CCCNC(N=1)=CC=NC=1NC(C=1)=CC=CC=1C1=CC=CC=N1 JFUBCYAHCZCJOK-UHFFFAOYSA-N 0.000 claims 1
• DGUOVCILYNQCQX-UHFFFAOYSA-N 4-n-(3-pyrazolidin-1-ylpropyl)-2-n-[3-(trifluoromethyl)phenyl]pyrimidine-2,4-diamine Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C(NCCCN3NCCC3)C=CN=2)=C1 DGUOVCILYNQCQX-UHFFFAOYSA-N 0.000 claims 1
• UNMOYDQUEBTDBW-UHFFFAOYSA-N 4-n-[3-(2,4-dihydroimidazol-3-yl)propyl]-2-n-(3-methoxyphenyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(NC=2N=C(NCCCN3CN=CC3)C=CN=2)=C1 UNMOYDQUEBTDBW-UHFFFAOYSA-N 0.000 claims 1
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