BRPI0709007A2 - inibidores de 8-heteroarilpurina mnk2 para tratamento de distúrbios metabólicos - Google Patents

Info

Publication number

BRPI0709007A2

BRPI0709007A2 BRPI0709007-2A BRPI0709007A BRPI0709007A2 BR PI0709007 A2 BRPI0709007 A2 BR PI0709007A2 BR PI0709007 A BRPI0709007 A BR PI0709007A BR PI0709007 A2 BRPI0709007 A2 BR PI0709007A2

Authority

BR

Brazil

Prior art keywords

purin

amine

ethyl

pyridin

phenyl

Prior art date

2006-03-09

Links

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• 238000011282 treatment Methods 0.000 title claims abstract description 23
• 208000030159 metabolic disease Diseases 0.000 title claims abstract description 19
• 239000003112 inhibitor Substances 0.000 title abstract description 9
• 101710138999 MAP kinase-interacting serine/threonine-protein kinase 2 Proteins 0.000 claims abstract description 32
• 102100033610 MAP kinase-interacting serine/threonine-protein kinase 2 Human genes 0.000 claims abstract description 31
• 208000008589 Obesity Diseases 0.000 claims abstract description 20
• 235000020824 obesity Nutrition 0.000 claims abstract description 20
• 230000002265 prevention Effects 0.000 claims abstract description 19
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 18
• -1 alkylmin Chemical group 0.000 claims description 250
• 150000001875 compounds Chemical class 0.000 claims description 100
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 77
• 238000000034 method Methods 0.000 claims description 76
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 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 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 13
• 208000035475 disorder Diseases 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 9
• MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical compound NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 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 8
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 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 6
• 206010006895 Cachexia Diseases 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 208000001130 gallstones Diseases 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 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
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
• 235000014632 disordered eating Nutrition 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
• 208000032839 leukemia Diseases 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
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 101100335081 Mus musculus Flt3 gene Proteins 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 201000001883 cholelithiasis Diseases 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
• GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 3
• 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 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
• 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
• 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
• 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
• 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
• 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
• UIVQKYBCYIRMFQ-UHFFFAOYSA-N 9-methyl-n-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-8-pyridin-4-ylpurin-2-amine Chemical compound C1CN(C)CCN1CC1=CC=CC(NC=2N=C3N(C)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 UIVQKYBCYIRMFQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004453 alkoxycarbonyl 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
• 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• IRPQXSQAPKVCNJ-UHFFFAOYSA-N n-(3-methoxyphenyl)-8-[2-(methylamino)pyrimidin-4-yl]-9-propan-2-ylpurin-2-amine Chemical compound CNC1=NC=CC(C=2N(C3=NC(NC=4C=C(OC)C=CC=4)=NC=C3N=2)C(C)C)=N1 IRPQXSQAPKVCNJ-UHFFFAOYSA-N 0.000 claims description 3
• YSPRFZGDWDJEIV-UHFFFAOYSA-N n-[3-[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=1)=CC=CC=1CCNC1CCCC1 YSPRFZGDWDJEIV-UHFFFAOYSA-N 0.000 claims description 3
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-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
• KQPCWOZUTPDLAJ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-ethyl-n-(3-ethylphenyl)purin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(CC)C(C=4N=C(N)N=CC=4)=NC3=CN=2)=C1 KQPCWOZUTPDLAJ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• FLUDWWGAKZXMQI-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(5-chloro-2-fluorophenyl)-9-cyclopropylpurin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NC=4C(=CC=C(Cl)C=4)F)=NC=C3N=2)C2CC2)=N1 FLUDWWGAKZXMQI-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• APENBSBUJLGQKP-UHFFFAOYSA-N 9-cyclopropyl-8-(1-methylpyrrol-2-yl)-n-(2-thiophen-2-ylethyl)purin-2-amine Chemical compound CN1C=CC=C1C(N(C1=N2)C3CC3)=NC1=CN=C2NCCC1=CC=CS1 APENBSBUJLGQKP-UHFFFAOYSA-N 0.000 claims description 2
• NPAPKEPLPPFZHX-UHFFFAOYSA-N 9-cyclopropyl-n-(2,4-dimethoxyphenyl)-8-pyridin-4-ylpurin-2-amine Chemical compound COC1=CC(OC)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 NPAPKEPLPPFZHX-UHFFFAOYSA-N 0.000 claims description 2
• CDWRRSAITRSBIC-UHFFFAOYSA-N 9-cyclopropyl-n-(3-methoxyphenyl)-8-pyridin-4-ylpurin-2-amine Chemical compound COC1=CC=CC(NC=2N=C3N(C4CC4)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 CDWRRSAITRSBIC-UHFFFAOYSA-N 0.000 claims description 2
• UDPLWYLPGZGTPB-UHFFFAOYSA-N 9-cyclopropyl-n-(4-fluorophenyl)-8-pyridin-4-ylpurin-2-amine Chemical compound C1=CC(F)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 UDPLWYLPGZGTPB-UHFFFAOYSA-N 0.000 claims description 2
• NYAGIYGPFIPWSK-UHFFFAOYSA-N 9-cyclopropyl-n-[2-(2-fluorophenyl)ethyl]-8-pyridin-4-ylpurin-2-amine Chemical compound FC1=CC=CC=C1CCNC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 NYAGIYGPFIPWSK-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• GYFMZCFUFXNHJD-UHFFFAOYSA-N 9-ethyl-n-(3-ethylphenyl)-8-pyridin-4-ylpurin-2-amine Chemical compound CCC1=CC=CC(NC=2N=C3N(CC)C(C=4C=CN=CC=4)=NC3=CN=2)=C1 GYFMZCFUFXNHJD-UHFFFAOYSA-N 0.000 claims description 2
• HATJPVJOVWDDHI-UHFFFAOYSA-N 9-methyl-8-pyridin-4-yl-n-(2-thiophen-2-ylethyl)purin-2-amine Chemical compound N1=C2N(C)C(C=3C=CN=CC=3)=NC2=CN=C1NCCC1=CC=CS1 HATJPVJOVWDDHI-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
• QZFRMJLDOBBTNQ-UHFFFAOYSA-N n-(3-chlorophenyl)-9-cyclopropyl-8-[2-(methylamino)pyrimidin-4-yl]purin-2-amine Chemical compound CNC1=NC=CC(C=2N(C3=NC(NC=4C=C(Cl)C=CC=4)=NC=C3N=2)C2CC2)=N1 QZFRMJLDOBBTNQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• PMYVIYLCXFHEFG-UHFFFAOYSA-N n-[3-[(dimethylamino)methyl]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(C)C)=C1 PMYVIYLCXFHEFG-UHFFFAOYSA-N 0.000 claims description 2
• ARKUPPIJRKHOQJ-UHFFFAOYSA-N n-[4-(2-aminoethyl)phenyl]-9-cyclopropyl-8-pyridin-4-ylpurin-2-amine Chemical compound C1=CC(CCN)=CC=C1NC1=NC=C(N=C(C=2C=CN=CC=2)N2C3CC3)C2=N1 ARKUPPIJRKHOQJ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• WEWBMCRSGXJWDU-UHFFFAOYSA-N n-[[4-[(9-ethyl-8-pyridin-4-ylpurin-2-yl)amino]phenyl]methyl]-n-methylacetamide Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CN(C)C(C)=O)C=C1 WEWBMCRSGXJWDU-UHFFFAOYSA-N 0.000 claims description 2
• RIIQCCYYKOYGOR-UHFFFAOYSA-N n-[[4-[(9-ethyl-8-pyridin-4-ylpurin-2-yl)amino]phenyl]methyl]acetamide Chemical compound N1=C2N(CC)C(C=3C=CN=CC=3)=NC2=CN=C1NC1=CC=C(CNC(C)=O)C=C1 RIIQCCYYKOYGOR-UHFFFAOYSA-N 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
• VBTAVQSPPPMSFA-UHFFFAOYSA-N FC1=CC=C(C=C1)NC1=NC=C2N=CN(C2=N1)C Chemical compound FC1=CC=C(C=C1)NC1=NC=C2N=CN(C2=N1)C VBTAVQSPPPMSFA-UHFFFAOYSA-N 0.000 claims 2
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• XHPZHWMPLBBVBI-UHFFFAOYSA-N 1H-pyrimidine-2,2-diamine Chemical compound NC1(NC=CC=N1)N XHPZHWMPLBBVBI-UHFFFAOYSA-N 0.000 claims 1
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
• BUKDRFCAGJUZMF-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)ethyl]aniline Chemical compound C1CN(C)CCN1CCC1=CC=CC(N)=C1 BUKDRFCAGJUZMF-UHFFFAOYSA-N 0.000 claims 1
• LSNIYGFKFNDXFJ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-9-cyclopropyl-n-(2-thiophen-2-ylethyl)purin-2-amine Chemical compound NC1=NC=CC(C=2N(C3=NC(NCCC=4SC=CC=4)=NC=C3N=2)C2CC2)=N1 LSNIYGFKFNDXFJ-UHFFFAOYSA-N 0.000 claims 1
• NUTDEBPDDVELNJ-UHFFFAOYSA-N 8-(2-aminopyrimidin-4-yl)-n-(3,5-dimethylphenyl)-9-ethylpurin-2-amine Chemical compound N1=C2N(CC)C(C=3N=C(N)N=CC=3)=NC2=CN=C1NC1=CC(C)=CC(C)=C1 NUTDEBPDDVELNJ-UHFFFAOYSA-N 0.000 claims 1
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