AU2007222982A1 - 8-Heteroarylpurine Mnk2 inhibitors for treating metabolic disorders - Google Patents

Info

Publication number

AU2007222982A1

AU2007222982A1 AU2007222982A AU2007222982A AU2007222982A1 AU 2007222982 A1 AU2007222982 A1 AU 2007222982A1 AU 2007222982 A AU2007222982 A AU 2007222982A AU 2007222982 A AU2007222982 A AU 2007222982A AU 2007222982 A1 AU2007222982 A1 AU 2007222982A1

Authority

AU

Australia

Prior art keywords

purin

amine

pyridin

ethyl

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 101710138999 MAP kinase-interacting serine/threonine-protein kinase 2 Proteins 0.000 title claims description 29
• 102100033610 MAP kinase-interacting serine/threonine-protein kinase 2 Human genes 0.000 title claims description 28
• 208000030159 metabolic disease Diseases 0.000 title claims description 16
• 239000003112 inhibitor Substances 0.000 title description 7
• 238000000034 method Methods 0.000 claims description 284
• 150000001875 compounds Chemical class 0.000 claims description 107
• -1 cyano, nitro, amino Chemical group 0.000 claims description 53
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 23
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 208000008589 Obesity Diseases 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• 235000020824 obesity Nutrition 0.000 claims description 19
• 230000002265 prevention Effects 0.000 claims description 19
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 18
• 230000000694 effects Effects 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 206010012601 diabetes mellitus Diseases 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 10
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 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
• 150000001412 amines Chemical class 0.000 claims description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 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 6
• 206010006895 Cachexia Diseases 0.000 claims description 6
• 125000002252 acyl group Chemical group 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 201000001883 cholelithiasis Diseases 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 208000001130 gallstones Diseases 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 201000002859 sleep apnea Diseases 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([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 5
• 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
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 201000008482 osteoarthritis Diseases 0.000 claims description 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#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
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 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 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 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
• ONQZRROTKQAVST-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-n-(3,4-difluorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C(F)=C1 ONQZRROTKQAVST-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
• 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
• 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
• 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
• 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
• 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
• 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
• ZSCUKTFACZMWCO-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(2,5-difluorophenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC(F)=CC=C1F ZSCUKTFACZMWCO-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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• 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
• UJQUJFKXQNLARQ-UHFFFAOYSA-N [4-[2-(4-fluoroanilino)-9-methylpurin-8-yl]pyridin-2-yl]methanol Chemical compound N1=C2N(C)C(C=3C=C(CO)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C=C1 UJQUJFKXQNLARQ-UHFFFAOYSA-N 0.000 claims description 3
• 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
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
• FWHYCPPXCXIERA-UHFFFAOYSA-N ethyl 4-[2-(4-fluoroanilino)-9-methylpurin-8-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OCC)=CC(C=2N(C3=NC(NC=4C=CC(F)=CC=4)=NC=C3N=2)C)=C1 FWHYCPPXCXIERA-UHFFFAOYSA-N 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• DNZFCTAPXIOPCB-UHFFFAOYSA-N n-(3-methoxyphenyl)-9-propan-2-yl-8-pyrimidin-4-ylpurin-2-amine Chemical compound COC1=CC=CC(NC=2N=C3N(C(C)C)C(C=4N=CN=CC=4)=NC3=CN=2)=C1 DNZFCTAPXIOPCB-UHFFFAOYSA-N 0.000 claims description 3
• FVZYADGFRJUBRR-UHFFFAOYSA-N n-(9-cyclopropyl-8-pyridin-4-ylpurin-2-yl)-1,3-benzothiazol-6-amine Chemical compound C1CC1N1C2=NC(NC=3C=C4SC=NC4=CC=3)=NC=C2N=C1C1=CC=NC=C1 FVZYADGFRJUBRR-UHFFFAOYSA-N 0.000 claims description 3
• SXCZYSHPDFNYFF-UHFFFAOYSA-N n-[2-[4-[(9-cyclopropyl-8-pyridin-4-ylpurin-2-yl)amino]phenyl]ethyl]acetamide Chemical compound C1=CC(CCNC(=O)C)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 SXCZYSHPDFNYFF-UHFFFAOYSA-N 0.000 claims description 3
• XZQIWHORMUJUAO-UHFFFAOYSA-N n-[3-(aminomethyl)phenyl]-9-ethyl-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=CC(CN)=C1 XZQIWHORMUJUAO-UHFFFAOYSA-N 0.000 claims description 3
• UBKCUPRGGJDJDT-UHFFFAOYSA-N n-[4-(2-aminoethyl)phenyl]-9-ethyl-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CCN)C=C1 UBKCUPRGGJDJDT-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• BNBWRDTUJSXOCU-UHFFFAOYSA-N n-[4-(2-methoxyethoxy)phenyl]-9-methyl-8-pyridin-4-ylpurin-2-amine Chemical compound C1=CC(OCCOC)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C)C2=N1 BNBWRDTUJSXOCU-UHFFFAOYSA-N 0.000 claims description 3
• RYWLVHKOIQOBEP-UHFFFAOYSA-N n-[4-(aminomethyl)phenyl]-9-ethyl-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CN)C=C1 RYWLVHKOIQOBEP-UHFFFAOYSA-N 0.000 claims description 3
• SBGYWALMFBDTLU-UHFFFAOYSA-N n-[4-(aminomethyl)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(CN)C=C1 SBGYWALMFBDTLU-UHFFFAOYSA-N 0.000 claims description 3
• MXTFGJHPLWKYSA-UHFFFAOYSA-N n-[4-[(cyclopentylamino)methyl]phenyl]-9-ethyl-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=C1)=CC=C1CNC1CCCC1 MXTFGJHPLWKYSA-UHFFFAOYSA-N 0.000 claims description 3
• JMUKEJDKNVEFCR-UHFFFAOYSA-N n-[4-[2-(cyclopentylamino)ethyl]phenyl]-9-ethyl-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=C1)=CC=C1CCNC1CCCC1 JMUKEJDKNVEFCR-UHFFFAOYSA-N 0.000 claims description 3
• WFRIHVMTHVXYFQ-UHFFFAOYSA-N n-[4-[2-(cyclopropylamino)ethyl]phenyl]-9-ethyl-8-pyridin-4-ylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC(C=C1)=CC=C1CCNC1CC1 WFRIHVMTHVXYFQ-UHFFFAOYSA-N 0.000 claims description 3
• COJTYKYQOPTTII-UHFFFAOYSA-N n-[[3-[(9-cyclopropyl-8-pyridin-4-ylpurin-2-yl)amino]phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC(NC=2N=C3N(C4CC4)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 COJTYKYQOPTTII-UHFFFAOYSA-N 0.000 claims description 3
• SXVGDYQGWQGDIK-UHFFFAOYSA-N n-cyclopentyl-9-cyclopropyl-8-pyridin-4-ylpurin-2-amine Chemical compound C1CC1N1C2=NC(NC3CCCC3)=NC=C2N=C1C1=CC=NC=C1 SXVGDYQGWQGDIK-UHFFFAOYSA-N 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• MUAUTBNKPSNTFM-UHFFFAOYSA-N 2-phenylethyl carbamate Chemical compound NC(=O)OCCC1=CC=CC=C1 MUAUTBNKPSNTFM-UHFFFAOYSA-N 0.000 claims description 2
• PXRXHMJQHZQLIM-UHFFFAOYSA-N 4-[8-(2-aminopyrimidin-4-yl)-9-cyclopropylpurin-2-yl]-1-N,1-N-dimethylcyclohexa-1,5-diene-1,4-diamine Chemical compound NC1=NC=CC(=N1)C=1N(C2=NC(=NC=C2N1)C1(CC=C(C=C1)N(C)C)N)C1CC1 PXRXHMJQHZQLIM-UHFFFAOYSA-N 0.000 claims description 2
• NHBSGCNHKNJDPS-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-9-cyclopropyl-n-(3-methoxyphenyl)purin-2-amine Chemical compound COC1=CC=CC(NC=2N=C3N(C4CC4)C(C=4C=C(N)N=CC=4)=NC3=CN=2)=C1 NHBSGCNHKNJDPS-UHFFFAOYSA-N 0.000 claims description 2
• LKOGQCVPWVTMRE-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-9-cyclopropyl-n-phenylpurin-2-amine Chemical compound C1=NC(N)=CC(C=2N(C3=NC(NC=4C=CC=CC=4)=NC=C3N=2)C2CC2)=C1 LKOGQCVPWVTMRE-UHFFFAOYSA-N 0.000 claims description 2
• QUMUQLOQNDKVFM-UHFFFAOYSA-N 8-(2-aminopyridin-4-yl)-9-ethyl-n-(4-fluoro-3-methoxyphenyl)purin-2-amine Chemical compound N1=C2N(CC)C(C=3C=C(N)N=CC=3)=NC2=CN=C1NC1=CC=C(F)C(OC)=C1 QUMUQLOQNDKVFM-UHFFFAOYSA-N 0.000 claims description 2
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