CN101454325A - 用于治疗代谢性疾病的8-杂芳基嘌呤mnk2抑制剂 - Google Patents

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Publication number

CN101454325A

CN101454325A CNA2007800157773A CN200780015777A CN101454325A CN 101454325 A CN101454325 A CN 101454325A CN A2007800157773 A CNA2007800157773 A CN A2007800157773A CN 200780015777 A CN200780015777 A CN 200780015777A CN 101454325 A CN101454325 A CN 101454325A

Authority

CN

China

Prior art keywords

purine

amine

ethyl

pyridin

phenyl

Prior art date

2006-03-09

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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• 208000030159 metabolic disease Diseases 0.000 title claims abstract description 17
• 239000003112 inhibitor Substances 0.000 title abstract description 7
• 101710138999 MAP kinase-interacting serine/threonine-protein kinase 2 Proteins 0.000 claims abstract description 29
• 102100033610 MAP kinase-interacting serine/threonine-protein kinase 2 Human genes 0.000 claims abstract description 28
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 28
• 208000008589 Obesity Diseases 0.000 claims abstract description 21
• 235000020824 obesity Nutrition 0.000 claims abstract description 21
• 230000002265 prevention Effects 0.000 claims abstract description 20
• 150000001875 compounds Chemical class 0.000 claims description 82
• -1 nitro, amino Chemical group 0.000 claims description 75
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 238000000034 method Methods 0.000 claims description 45
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
• 125000003368 amide group Chemical group 0.000 claims description 26
• 101710139011 MAP kinase-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims description 25
• 102100026299 MAP kinase-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims description 25
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 208000016097 disease of metabolism Diseases 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 13
• 238000002360 preparation method Methods 0.000 claims description 12
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 201000011510 cancer Diseases 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 206010006895 Cachexia Diseases 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 208000026500 emaciation Diseases 0.000 claims description 6
• 210000005036 nerve Anatomy 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 6
• 201000002859 sleep apnea Diseases 0.000 claims description 6
• 208000030814 Eating disease Diseases 0.000 claims description 5
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 235000014632 disordered eating Nutrition 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
• PVUIOAOUQPLJTC-UHFFFAOYSA-N 9-cyclopropyl-8-pyridin-4-yl-n-(2-thiophen-2-ylethyl)purin-2-amine Chemical compound N=1C=C2N=C(C=3C=CN=CC=3)N(C3CC3)C2=NC=1NCCC1=CC=CS1 PVUIOAOUQPLJTC-UHFFFAOYSA-N 0.000 claims description 4
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 4
• 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims description 4
• ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• VCVCXSPOZXMIFE-UHFFFAOYSA-N n-[4-(2-aminoethyl)phenyl]-9-methyl-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CCN)C=C1 VCVCXSPOZXMIFE-UHFFFAOYSA-N 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• ZEBHVVDCUCLCHN-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-9-ethyl-n-(3-ethylphenyl)purin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(CC)C(C=4C=C(N)N=CC=4)=NC3=CN=2)=C1 ZEBHVVDCUCLCHN-UHFFFAOYSA-N 0.000 claims description 3
• XQNSTUNYRQGUTD-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-9-ethyl-n-(4-fluorophenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3C=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1 XQNSTUNYRQGUTD-UHFFFAOYSA-N 0.000 claims description 3
• XYQZJJVYRGHMIH-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-n-(4-fluorophenyl)-9-methylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1 XYQZJJVYRGHMIH-UHFFFAOYSA-N 0.000 claims description 3
• BJXSTXQFDAMJBO-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-cyclopropyl-n-(3-ethylphenyl)purin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(C4CC4)C(C=4N=C(N)N=CC=4)=NC3=CN=2)=C1 BJXSTXQFDAMJBO-UHFFFAOYSA-N 0.000 claims description 3
• NZBVUKPKBZXNEM-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-cyclopropyl-n-(3-fluorophenyl)purin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C=C(F)C=CC=4)=NC=C3N=2)C2CC2)=N1 NZBVUKPKBZXNEM-UHFFFAOYSA-N 0.000 claims description 3
• YIBMLVFQUNJWTN-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-cyclopropyl-n-(4-fluorophenyl)purin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C=CC(F)=CC=4)=NC=C3N=2)C2CC2)=N1 YIBMLVFQUNJWTN-UHFFFAOYSA-N 0.000 claims description 3
• ZWVBYQWMUYSQFE-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-cyclopropyl-n-phenylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C=CC=CC=4)=NC=C3N=2)C2CC2)=N1 ZWVBYQWMUYSQFE-UHFFFAOYSA-N 0.000 claims description 3
• RTJAUHQFEDUFFL-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(2-methylphenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=CC=C1C RTJAUHQFEDUFFL-UHFFFAOYSA-N 0.000 claims description 3
• XQBFABALBUOMFZ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(3-fluorophenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=CC(F)=C1 XQBFABALBUOMFZ-UHFFFAOYSA-N 0.000 claims description 3
• XPWBIWZPFJXZAP-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(4-ethylphenyl)purin-2-amine Chemical compound C1=CC(CC)=CC=C1NC1=NC=C(N=C(C=2N=C(N)N=CC=2)N2CC)C2=N1 XPWBIWZPFJXZAP-UHFFFAOYSA-N 0.000 claims description 3
• YKXGRIRISAGLQD-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(4-fluorophenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1 YKXGRIRISAGLQD-UHFFFAOYSA-N 0.000 claims description 3
• ZKXXIMSVOLKANW-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(4-methylphenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(C)C=C1 ZKXXIMSVOLKANW-UHFFFAOYSA-N 0.000 claims description 3
• WAVDPBGCYDVJMF-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2-chloro-4-fluorophenyl)-9-cyclopropylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C(=CC(F)=CC=4)Cl)=NC=C3N=2)C2CC2)=N1 WAVDPBGCYDVJMF-UHFFFAOYSA-N 0.000 claims description 3
• MJSFVHQRTFALHV-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2-chloro-5-fluorophenyl)-9-cyclopropylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C(=CC=C(F)C=4)Cl)=NC=C3N=2)C2CC2)=N1 MJSFVHQRTFALHV-UHFFFAOYSA-N 0.000 claims description 3
• KCWHWBDLUBKRON-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3-chloro-2-fluorophenyl)-9-cyclopropylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C(=C(Cl)C=CC=4)F)=NC=C3N=2)C2CC2)=N1 KCWHWBDLUBKRON-UHFFFAOYSA-N 0.000 claims description 3
• WXPIEKTXAWQUCR-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3-chloro-4-fluorophenyl)-9-cyclopropylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C=C(Cl)C(F)=CC=4)=NC=C3N=2)C2CC2)=N1 WXPIEKTXAWQUCR-UHFFFAOYSA-N 0.000 claims description 3
• JZRNPHRSVLUEDZ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(4-chloro-2-fluorophenyl)-9-cyclopropylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C(=CC(Cl)=CC=4)F)=NC=C3N=2)C2CC2)=N1 JZRNPHRSVLUEDZ-UHFFFAOYSA-N 0.000 claims description 3
• KNDQGRSIMXKUSP-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(4-fluorophenyl)-9-methylpurin-2-amine Chemical compound N1=C2N(C)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1 KNDQGRSIMXKUSP-UHFFFAOYSA-N 0.000 claims description 3
• GISBRRIKYIRFBV-UHFFFAOYSA-N 8-(2-chloropyridin-4-yl)-9-cyclopropyl-n-(2-thiophen-2-ylethyl)purin-2-amine Chemical compound C1=NC(Cl)=CC(C=2N(C3=NC(NCCC=4SC=CC=4)=NC=C3N=2)C2CC2)=C1 GISBRRIKYIRFBV-UHFFFAOYSA-N 0.000 claims description 3
• PQTLIVNTYOKNQG-UHFFFAOYSA-N 8-(2-chloropyridin-4-yl)-9-cyclopropyl-n-phenylpurin-2-amine Chemical compound C1=NC(Cl)=CC(C=2N(C3=NC(NC=4C=CC=CC=4)=NC=C3N=2)C2CC2)=C1 PQTLIVNTYOKNQG-UHFFFAOYSA-N 0.000 claims description 3
• WVKZPZQQIQZLRA-UHFFFAOYSA-N 8-(2-chloropyridin-4-yl)-9-ethyl-n-(3-ethylphenyl)purin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(CC)C(C=4C=C(Cl)N=CC=4)=NC3=CN=2)=C1 WVKZPZQQIQZLRA-UHFFFAOYSA-N 0.000 claims description 3
• WYQFVKIKCKBYHG-UHFFFAOYSA-N 8-(6-aminopyridin-3-yl)-9-ethyl-n-(3-ethylphenyl)purin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(CC)C(C=4C=NC(N)=CC=4)=NC3=CN=2)=C1 WYQFVKIKCKBYHG-UHFFFAOYSA-N 0.000 claims description 3
• YNDWIOYGPZEHHJ-UHFFFAOYSA-N 8-(6-aminopyridin-3-yl)-9-ethyl-n-(4-fluorophenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3C=NC(N)=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1 YNDWIOYGPZEHHJ-UHFFFAOYSA-N 0.000 claims description 3
• PAPJNYYKUHRNAN-UHFFFAOYSA-N 8-pyridin-4-yl-n-(2-thiophen-2-ylethyl)-7h-purin-2-amine Chemical compound N=1C=C2N=C(C=3C=CN=CC=3)NC2=NC=1NCCC1=CC=CS1 PAPJNYYKUHRNAN-UHFFFAOYSA-N 0.000 claims description 3
• OSBKRHDCCLRWLM-UHFFFAOYSA-N 9-cyclopropyl-8-[2-(methylamino)pyrimidin-4-yl]-n-phenylpurin-2-amine Chemical compound CNC1=NC=CC(C=2N(C3=NC(NC=4C=CC=CC=4)=NC=C3N=2)C2CC2)=N1 OSBKRHDCCLRWLM-UHFFFAOYSA-N 0.000 claims description 3
• XVNMGGMAZPTHIV-UHFFFAOYSA-N 9-cyclopropyl-8-pyridin-4-yl-n-[3-(trifluoromethoxy)phenyl]purin-2-amine Chemical compound FC(F)(F)OC1=CC=CC(NC=2N=C3N(C4CC4)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 XVNMGGMAZPTHIV-UHFFFAOYSA-N 0.000 claims description 3
• NGGDOPRXNBBLKF-UHFFFAOYSA-N 9-cyclopropyl-8-pyrimidin-4-yl-n-(2-thiophen-2-ylethyl)purin-2-amine Chemical compound N=1C=C2N=C(C=3N=CN=CC=3)N(C3CC3)C2=NC=1NCCC1=CC=CS1 NGGDOPRXNBBLKF-UHFFFAOYSA-N 0.000 claims description 3
• PYWHJJIUMDLXKQ-UHFFFAOYSA-N 9-cyclopropyl-n-(2-fluorophenyl)-8-pyridin-4-ylpurin-2-amine Chemical compound FC1=CC=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 PYWHJJIUMDLXKQ-UHFFFAOYSA-N 0.000 claims description 3
• MNZMPTJPAKSVHS-UHFFFAOYSA-N 9-cyclopropyl-n-(3-ethylphenyl)-8-[2-(methylamino)pyrimidin-4-yl]purin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(C4CC4)C(C=4N=C(NC)N=CC=4)=NC3=CN=2)=C1 MNZMPTJPAKSVHS-UHFFFAOYSA-N 0.000 claims description 3
• ZZQRWDRUNISRQQ-UHFFFAOYSA-N 9-cyclopropyl-n-(3-fluorophenyl)-8-[2-(methylamino)pyrimidin-4-yl]purin-2-amine Chemical compound CNC1=NC=CC(C=2N(C3=NC(NC=4C=C(F)C=CC=4)=NC=C3N=2)C2CC2)=N1 ZZQRWDRUNISRQQ-UHFFFAOYSA-N 0.000 claims description 3
• XZGGGDHKYSGMNC-UHFFFAOYSA-N 9-cyclopropyl-n-(4-fluorophenyl)-8-[2-(methylamino)pyrimidin-4-yl]purin-2-amine Chemical compound CNC1=NC=CC(C=2N(C3=NC(NC=4C=CC(F)=CC=4)=NC=C3N=2)C2CC2)=N1 XZGGGDHKYSGMNC-UHFFFAOYSA-N 0.000 claims description 3
• DMHMLTMJTDGBPZ-UHFFFAOYSA-N 9-cyclopropyl-n-[4-(methylaminomethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound C1=CC(CNC)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 DMHMLTMJTDGBPZ-UHFFFAOYSA-N 0.000 claims description 3
• CTAJMNAZMJJEDD-UHFFFAOYSA-N 9-cyclopropyl-n-[4-[2-(methylamino)ethyl]phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound C1=CC(CCNC)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 CTAJMNAZMJJEDD-UHFFFAOYSA-N 0.000 claims description 3
• KSFYQXBAGPACQL-UHFFFAOYSA-N 9-cyclopropyl-n-phenyl-8-pyridin-4-ylpurin-2-amine Chemical compound C1CC1N1C2=NC(NC=3C=CC=CC=3)=NC=C2N=C1C1=CC=NC=C1 KSFYQXBAGPACQL-UHFFFAOYSA-N 0.000 claims description 3
• LIIWSMMSGDTMAE-UHFFFAOYSA-N 9-ethyl-n-(3-ethylphenyl)-8-[2-(methylamino)pyrimidin-4-yl]purin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(CC)C(C=4N=C(NC)N=CC=4)=NC3=CN=2)=C1 LIIWSMMSGDTMAE-UHFFFAOYSA-N 0.000 claims description 3
• RWUGJXUJUMDRNM-UHFFFAOYSA-N 9-ethyl-n-[3-(2-methoxyethoxy)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=CC(OCCOC)=C1 RWUGJXUJUMDRNM-UHFFFAOYSA-N 0.000 claims description 3
• PWQVITAVWFKFIW-UHFFFAOYSA-N 9-ethyl-n-[3-(ethylaminomethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound CCNCC1=CC=CC(NC=2N=C3N(CC)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 PWQVITAVWFKFIW-UHFFFAOYSA-N 0.000 claims description 3
• ZVULPPVKKPIYNY-UHFFFAOYSA-N 9-ethyl-n-[3-[2-(ethylamino)ethyl]phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound CCNCCC1=CC=CC(NC=2N=C3N(CC)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 ZVULPPVKKPIYNY-UHFFFAOYSA-N 0.000 claims description 3
• RMIGYMSGAIENSJ-UHFFFAOYSA-N 9-ethyl-n-[4-(2-methoxyethoxy)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(OCCOC)C=C1 RMIGYMSGAIENSJ-UHFFFAOYSA-N 0.000 claims description 3
• AGQPZCNJZAXRBB-UHFFFAOYSA-N 9-ethyl-n-[4-(ethylaminomethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound C1=CC(CNCC)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2CC)C2=N1 AGQPZCNJZAXRBB-UHFFFAOYSA-N 0.000 claims description 3
• VRVGCRZYHMPPEW-UHFFFAOYSA-N 9-ethyl-n-[4-(methylaminomethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CNC)C=C1 VRVGCRZYHMPPEW-UHFFFAOYSA-N 0.000 claims description 3
• AZFBBBZAAXJYDR-UHFFFAOYSA-N 9-ethyl-n-[4-[2-(ethylamino)ethyl]phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound C1=CC(CCNCC)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2CC)C2=N1 AZFBBBZAAXJYDR-UHFFFAOYSA-N 0.000 claims description 3
• LNBJHYNELVITJQ-UHFFFAOYSA-N 9-ethyl-n-[4-[2-(methylamino)ethyl]phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CCNC)C=C1 LNBJHYNELVITJQ-UHFFFAOYSA-N 0.000 claims description 3
• PRMFGMRJTDHQLR-UHFFFAOYSA-N 9-methyl-n-[3-(2-morpholin-4-ylethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=1)=CC=CC=1CCN1CCOCC1 PRMFGMRJTDHQLR-UHFFFAOYSA-N 0.000 claims description 3
• LAKWSPNLJOWAPV-UHFFFAOYSA-N 9-methyl-n-[3-(2-piperazin-1-ylethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=1)=CC=CC=1CCN1CCNCC1 LAKWSPNLJOWAPV-UHFFFAOYSA-N 0.000 claims description 3
• AJELQPXEYGUQPF-UHFFFAOYSA-N 9-methyl-n-[3-(morpholin-4-ylmethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=1)=CC=CC=1CN1CCOCC1 AJELQPXEYGUQPF-UHFFFAOYSA-N 0.000 claims description 3
• BPEWWPDJYWGJER-UHFFFAOYSA-N 9-methyl-n-[3-(piperazin-1-ylmethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=1)=CC=CC=1CN1CCNCC1 BPEWWPDJYWGJER-UHFFFAOYSA-N 0.000 claims description 3
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