KR20080107466A - 대사 장애 치료용 8-헤테로아릴퓨린 ｍｎｋ2 억제제 - Google Patents

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Publication number

KR20080107466A

KR20080107466A KR1020087024592A KR20087024592A KR20080107466A KR 20080107466 A KR20080107466 A KR 20080107466A KR 1020087024592 A KR1020087024592 A KR 1020087024592A KR 20087024592 A KR20087024592 A KR 20087024592A KR 20080107466 A KR20080107466 A KR 20080107466A

Authority

KR

South Korea

Prior art keywords

amine

purin

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.)

Withdrawn

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• 238000011282 treatment Methods 0.000 title claims abstract description 25
• 208000030159 metabolic disease Diseases 0.000 title claims abstract description 16
• 239000003112 inhibitor Substances 0.000 title abstract description 6
• 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
• 208000008589 Obesity Diseases 0.000 claims abstract description 21
• 235000020824 obesity Nutrition 0.000 claims abstract description 21
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 20
• 230000002265 prevention Effects 0.000 claims abstract description 18
• 150000001875 compounds Chemical class 0.000 claims description 108
• -1 hydroxy, hydroxy Chemical group 0.000 claims description 100
• 238000000034 method Methods 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 101710139011 MAP kinase-interacting serine/threonine-protein kinase 1 Proteins 0.000 claims description 27
• 102100026299 MAP kinase-interacting serine/threonine-protein kinase 1 Human genes 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 230000000694 effects Effects 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 206010028980 Neoplasm Diseases 0.000 claims description 11
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 206010006895 Cachexia Diseases 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 7
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 201000001883 cholelithiasis Diseases 0.000 claims description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
• 208000001130 gallstones Diseases 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
• 201000008482 osteoarthritis Diseases 0.000 claims description 7
• 201000002859 sleep apnea Diseases 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 208000032839 leukemia 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
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 5
• 235000014632 disordered eating Nutrition 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• QZTXFEFHGSSLLO-UHFFFAOYSA-N n-(4-fluorophenyl)-8-pyridin-4-yl-7h-purin-2-amine Chemical compound C1=CC(F)=CC=C1NC1=NC=C(N=C(N2)C=3C=CN=CC=3)C2=N1 QZTXFEFHGSSLLO-UHFFFAOYSA-N 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
• 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 4
• 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims description 4
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 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
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• WZJMKKBGBBEOHS-UHFFFAOYSA-N 2,2,2-trifluoro-n-[[4-[(9-methyl-8-pyridin-4-ylpurin-2-yl)amino]phenyl]methyl]acetamide Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CNC(=O)C(F)(F)F)C=C1 WZJMKKBGBBEOHS-UHFFFAOYSA-N 0.000 claims description 3
• HYGPEUXRWYLOIN-UHFFFAOYSA-N 3-[2-(3-methoxyanilino)-8-pyrimidin-4-ylpurin-9-yl]propanenitrile Chemical compound COC1=CC=CC(NC=2N=C3N(CCC#N)C(C=4N=CN=CC=4)=NC3=CN=2)=C1 HYGPEUXRWYLOIN-UHFFFAOYSA-N 0.000 claims description 3
• GSSIKTIGYYEYMO-UHFFFAOYSA-N 3-[8-(2-aminopyrimidin-4-yl)-2-(3-methoxyanilino)purin-9-yl]propanenitrile Chemical compound COC1=CC=CC(NC=2N=C3N(CCC#N)C(C=4N=C(N)N=CC=4)=NC3=CN=2)=C1 GSSIKTIGYYEYMO-UHFFFAOYSA-N 0.000 claims description 3
• 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
• NAZLPTWWZCLEGV-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-n-(3-methoxyphenyl)-9-propan-2-ylpurin-2-amine Chemical compound COC1=CC=CC(NC=2N=C3N(C(C)C)C(C=4C=C(N)N=CC=4)=NC3=CN=2)=C1 NAZLPTWWZCLEGV-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
• LBUYYVMDIUYIQM-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-cyclopropyl-n-(3-methylphenyl)purin-2-amine Chemical compound CC1=CC=CC(NC=2N=C3N(C4CC4)C(C=4N=C(N)N=CC=4)=NC3=CN=2)=C1 LBUYYVMDIUYIQM-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
• XBMKEEBOFTZPDJ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(3-fluoro-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(F)=C1 XBMKEEBOFTZPDJ-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
• ZXHUFUJXDSAJCQ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(4-fluoro-2-methylphenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1C ZXHUFUJXDSAJCQ-UHFFFAOYSA-N 0.000 claims description 3
• KDYPIICQVSPKMD-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(4-fluoro-3-methylphenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C(C)=C1 KDYPIICQVSPKMD-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
• DVPGOFKHIYJKOF-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(5,6,7,8-tetrahydronaphthalen-1-yl)purin-2-amine Chemical compound N=1C2=CN=C(NC=3C=4CCCCC=4C=CC=3)N=C2N(CC)C=1C1=CC=NC(N)=N1 DVPGOFKHIYJKOF-UHFFFAOYSA-N 0.000 claims description 3
• ZIKBLUKPDFVYJQ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(5-fluoro-2-methylphenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC(F)=CC=C1C ZIKBLUKPDFVYJQ-UHFFFAOYSA-N 0.000 claims description 3
• CJINNKPHGFAJBZ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,3-difluorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=CC(F)=C1F CJINNKPHGFAJBZ-UHFFFAOYSA-N 0.000 claims description 3
• JROADSMIBPKINP-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,3-dihydro-1h-inden-4-yl)-9-ethylpurin-2-amine Chemical compound N=1C2=CN=C(NC=3C=4CCCC=4C=CC=3)N=C2N(CC)C=1C1=CC=NC(N)=N1 JROADSMIBPKINP-UHFFFAOYSA-N 0.000 claims description 3
• UAOBQSOZRAWNRN-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,3-dihydro-1h-inden-5-yl)-9-ethylpurin-2-amine Chemical compound N=1C2=CN=C(NC=3C=C4CCCC4=CC=3)N=C2N(CC)C=1C1=CC=NC(N)=N1 UAOBQSOZRAWNRN-UHFFFAOYSA-N 0.000 claims description 3
• GZHQOWSFWOKEST-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,3-dimethylphenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=CC(C)=C1C GZHQOWSFWOKEST-UHFFFAOYSA-N 0.000 claims description 3
• LRPGHDNBVLBTRM-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,4-difluorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1F LRPGHDNBVLBTRM-UHFFFAOYSA-N 0.000 claims description 3
• ZXCKOEZXNLZFED-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,4-dimethylphenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(C)C=C1C ZXCKOEZXNLZFED-UHFFFAOYSA-N 0.000 claims description 3
• YMROIJUEVYGXLM-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,5-dimethylphenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC(C)=CC=C1C YMROIJUEVYGXLM-UHFFFAOYSA-N 0.000 claims description 3
• QSUJBCZKUIYDAI-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,6-difluorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=C(F)C=CC=C1F QSUJBCZKUIYDAI-UHFFFAOYSA-N 0.000 claims description 3
• UNYFPFJIOAAHDI-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2-chlorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=CC=C1Cl UNYFPFJIOAAHDI-UHFFFAOYSA-N 0.000 claims description 3
• LKLPSMRQPSLPDC-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3,4-difluorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C(F)=C1 LKLPSMRQPSLPDC-UHFFFAOYSA-N 0.000 claims description 3
• DDXSNLQGUWIDOP-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3,4-dimethylphenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(C)C(C)=C1 DDXSNLQGUWIDOP-UHFFFAOYSA-N 0.000 claims description 3
• PJQSHEDWLPFTEM-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3,5-difluorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC(F)=CC(F)=C1 PJQSHEDWLPFTEM-UHFFFAOYSA-N 0.000 claims description 3
• BYAYUIDASASDNM-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3-chlorophenyl)-9-cyclopropylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C=C(Cl)C=CC=4)=NC=C3N=2)C2CC2)=N1 BYAYUIDASASDNM-UHFFFAOYSA-N 0.000 claims description 3
• OPGGSXVCGUHKTG-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3-chlorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=CC(Cl)=C1 OPGGSXVCGUHKTG-UHFFFAOYSA-N 0.000 claims description 3
• LLKWJSVYFODKGI-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3-methoxyphenyl)-9-propan-2-ylpurin-2-amine Chemical compound COC1=CC=CC(NC=2N=C3N(C(C)C)C(C=4N=C(N)N=CC=4)=NC3=CN=2)=C1 LLKWJSVYFODKGI-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
• BUWCGYCENTWUQM-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(4-chlorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(Cl)C=C1 BUWCGYCENTWUQM-UHFFFAOYSA-N 0.000 claims description 3
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• 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
• QMYWKEOMADJKGX-UHFFFAOYSA-N 8-(2-chloropyridin-4-yl)-n-(3-methoxyphenyl)-9-propan-2-ylpurin-2-amine Chemical compound COC1=CC=CC(NC=2N=C3N(C(C)C)C(C=4C=C(Cl)N=CC=4)=NC3=CN=2)=C1 QMYWKEOMADJKGX-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
• VKQRYONUADIMLP-UHFFFAOYSA-N 9-cyclopropyl-8-[2-(methylamino)pyrimidin-4-yl]-n-(3-methylphenyl)purin-2-amine Chemical compound CNC1=NC=CC(C=2N(C3=NC(NC=4C=C(C)C=CC=4)=NC=C3N=2)C2CC2)=N1 VKQRYONUADIMLP-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
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• 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
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• 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
• DSRXMYCCMKHUAE-UHFFFAOYSA-N 9-ethyl-n-(4-fluoro-3-methoxyphenyl)-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(F)C(OC)=C1 DSRXMYCCMKHUAE-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
• FQJRBITYKOCDKP-UHFFFAOYSA-N 9-ethyl-n-[3-(2-morpholin-4-ylethoxy)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=1)=CC=CC=1OCCN1CCOCC1 FQJRBITYKOCDKP-UHFFFAOYSA-N 0.000 claims description 3
• SVFRGHJASFOKEE-UHFFFAOYSA-N 9-ethyl-n-[3-(2-piperidin-1-ylethoxy)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=1)=CC=CC=1OCCN1CCCCC1 SVFRGHJASFOKEE-UHFFFAOYSA-N 0.000 claims description 3
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• 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
• UFEPWKZHQMKCAS-UHFFFAOYSA-N 9-ethyl-n-[4-[2-(propan-2-ylamino)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)C)C=C1 UFEPWKZHQMKCAS-UHFFFAOYSA-N 0.000 claims description 3
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• LUCZZVHZJFEMCD-UHFFFAOYSA-N 9-methyl-8-pyridin-4-yl-n-[4-(2-pyrrolidin-1-ylethyl)phenyl]purin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=C1)=CC=C1CCN1CCCC1 LUCZZVHZJFEMCD-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
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• WYCKFLGURNNCKO-UHFFFAOYSA-N 9-methyl-n-[3-[2-(4-methylpiperazin-1-yl)ethyl]phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound C1CN(C)CCN1CCC1=CC=CC(NC=2N=C3N(C)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 WYCKFLGURNNCKO-UHFFFAOYSA-N 0.000 claims description 3
• WICOBPMYLCUPKO-UHFFFAOYSA-N 9-methyl-n-[4-(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=C1)=CC=C1CCN1CCOCC1 WICOBPMYLCUPKO-UHFFFAOYSA-N 0.000 claims description 3
• VDGIEODIGVRUHU-UHFFFAOYSA-N 9-methyl-n-[4-(2-piperidin-1-ylethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=C1)=CC=C1CCN1CCCCC1 VDGIEODIGVRUHU-UHFFFAOYSA-N 0.000 claims description 3
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• QPQLPPDWPUQPRA-UHFFFAOYSA-N 9-methyl-n-[4-(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=C1)=CC=C1CN1CCOCC1 QPQLPPDWPUQPRA-UHFFFAOYSA-N 0.000 claims description 3
• ULGLNVPCXHERLJ-UHFFFAOYSA-N 9-methyl-n-[4-(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=C1)=CC=C1CN1CCNCC1 ULGLNVPCXHERLJ-UHFFFAOYSA-N 0.000 claims description 3
• RAAGZBFPKOIRAF-UHFFFAOYSA-N 9-methyl-n-[4-(piperidin-1-ylmethyl)phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=C1)=CC=C1CN1CCCCC1 RAAGZBFPKOIRAF-UHFFFAOYSA-N 0.000 claims description 3
• OLIBBAODESAITO-UHFFFAOYSA-N 9-methyl-n-[4-[2-(4-methylpiperazin-1-yl)ethyl]phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound C1CN(C)CCN1CCC(C=C1)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C)C2=N1 OLIBBAODESAITO-UHFFFAOYSA-N 0.000 claims description 3
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• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
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• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
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• PZSKMDBKCUQLSQ-UHFFFAOYSA-N n-[2-[4-[(9-ethyl-8-pyridin-4-ylpurin-2-yl)amino]phenyl]ethyl]-n-methylacetamide Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CCN(C)C(C)=O)C=C1 PZSKMDBKCUQLSQ-UHFFFAOYSA-N 0.000 claims description 3
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• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
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