AP637A - Heterocyclic ring-fused pyrimidine derivatives. - Google Patents

Info

Publication number

AP637A

AP637A APAP/P/1996/000805A AP9600805A AP637A AP 637 A AP637 A AP 637A AP 9600805 A AP9600805 A AP 9600805A AP 637 A AP637 A AP 637A

Authority

AP

ARIPO

Prior art keywords

pyrimidin

amine

pyrido

phenyl

pyrrolo

Prior art date

1995-06-07

Links

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• 150000003230 pyrimidines Chemical class 0.000 title description 12
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 5
• 125000000623 heterocyclic group Chemical group 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 134
• -1 nitro, hydroxy, amino Chemical group 0.000 claims description 136
• 125000000217 alkyl group Chemical group 0.000 claims description 82
• 238000000034 method Methods 0.000 claims description 63
• 125000003545 alkoxy group Chemical group 0.000 claims description 54
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
• 125000003282 alkyl amino group Chemical group 0.000 claims description 30
• 150000001412 amines Chemical class 0.000 claims description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
• 206010028980 Neoplasm Diseases 0.000 claims description 25
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 230000003463 hyperproliferative effect Effects 0.000 claims description 17
• 238000011282 treatment Methods 0.000 claims description 17
• 125000005518 carboxamido group Chemical group 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 13
• 125000004414 alkyl thio group Chemical group 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 125000004423 acyloxy group Chemical group 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
• 201000011510 cancer Diseases 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• 229910052727 yttrium Inorganic materials 0.000 claims description 10
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 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
• 125000005494 pyridonyl group Chemical group 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 229910014585 C2-Ce Inorganic materials 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 6
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 210000000481 breast Anatomy 0.000 claims description 5
• 125000001589 carboacyl group Chemical group 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• BHPQVEMLECZBDB-UHFFFAOYSA-N n-(1h-indol-5-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C2C(NC=3C=C4C=CNC4=CC=3)=NC=NC2=C1 BHPQVEMLECZBDB-UHFFFAOYSA-N 0.000 claims description 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
• CXAPZNBQPOKHKN-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)pyrido[3,4-d]pyrimidine Chemical compound N1=CC=C2C(N3CCC4=CC=C(C=C43)Cl)=NC=NC2=C1 CXAPZNBQPOKHKN-UHFFFAOYSA-N 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 125000003368 amide group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 230000002496 gastric effect Effects 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 210000004072 lung Anatomy 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• CVPVAPRGSBCQRN-UHFFFAOYSA-N n-(1h-indazol-5-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C2C(NC=3C=C4C=NNC4=CC=3)=NC=NC2=C1 CVPVAPRGSBCQRN-UHFFFAOYSA-N 0.000 claims description 4
• BWXVBEQVOBGQHC-UHFFFAOYSA-N n-(3-bromophenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound BrC1=CC=CC(NC=2C3=CC=NC=C3N=CN=2)=C1 BWXVBEQVOBGQHC-UHFFFAOYSA-N 0.000 claims description 4
• SBAWIIKMDWKPAP-UHFFFAOYSA-N n-(3-chlorophenyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C3=CC=CN=C3N=CN=2)=C1 SBAWIIKMDWKPAP-UHFFFAOYSA-N 0.000 claims description 4
• VMFOIJKDWCGYQN-UHFFFAOYSA-N n-(3-chlorophenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C3=CC=NC=C3N=CN=2)=C1 VMFOIJKDWCGYQN-UHFFFAOYSA-N 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• DXZWKHBMXNTZOI-UHFFFAOYSA-N 4-(3-ethynylanilino)-7h-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid Chemical compound C=12C(C(=O)O)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 DXZWKHBMXNTZOI-UHFFFAOYSA-N 0.000 claims description 3
• VFUAAGBLFHOQAV-UHFFFAOYSA-N 5-bromo-n-(3-ethynylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(Br)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 VFUAAGBLFHOQAV-UHFFFAOYSA-N 0.000 claims description 3
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
• 125000005596 alkyl carboxamido group Chemical group 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 210000004556 brain Anatomy 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims description 3
• 230000002440 hepatic effect Effects 0.000 claims description 3
• UGJFDWWKZWPKSZ-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC=C2C(NC=3C=C4C=CSC4=CC=3)=NC=NC2=C1 UGJFDWWKZWPKSZ-UHFFFAOYSA-N 0.000 claims description 3
• NPMPBDSPHFHHMC-UHFFFAOYSA-N n-(3-ethynylphenyl)-5-methylsulfanyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(SC)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 NPMPBDSPHFHHMC-UHFFFAOYSA-N 0.000 claims description 3
• LNPZJAMDBWPNSF-UHFFFAOYSA-N n-(3-methylphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(NC=2C3=CC=NC=C3N=CN=2)=C1 LNPZJAMDBWPNSF-UHFFFAOYSA-N 0.000 claims description 3
• KHEYWDNIEMRBQT-UHFFFAOYSA-N n-(4-fluoro-3-methylphenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(F)C(C)=C1 KHEYWDNIEMRBQT-UHFFFAOYSA-N 0.000 claims description 3
• 239000001301 oxygen Chemical group 0.000 claims description 3
• 239000000651 prodrug Substances 0.000 claims description 3
• 229940002612 prodrug Drugs 0.000 claims description 3
• 210000002307 prostate Anatomy 0.000 claims description 3
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 3
• YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims description 2
• 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• MDEUNLWIRLXZJC-UHFFFAOYSA-N 2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine;hydrochloride Chemical compound Cl.C1NCCC2=NC(Cl)=NC(Cl)=C21 MDEUNLWIRLXZJC-UHFFFAOYSA-N 0.000 claims description 2
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 2
• ONADPSCFVJZVCN-UHFFFAOYSA-N 2-methyl-4-[(6-methyl-5h-pyrido[4,3-d]pyrimidin-4-yl)amino]phenol Chemical compound N1=CN=C2C=CN(C)CC2=C1NC1=CC=C(O)C(C)=C1 ONADPSCFVJZVCN-UHFFFAOYSA-N 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• QPEFVPDESAJGGO-UHFFFAOYSA-N 4-(6-bromo-5-fluoro-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC2=CC(F)=C(Br)C=C2N1C1=C2C=C(C)N=CC2=NC=N1 QPEFVPDESAJGGO-UHFFFAOYSA-N 0.000 claims description 2
• MZJBVKCTGOKCHG-UHFFFAOYSA-N 4-(6-bromo-7-methyl-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC2=CC=C(Br)C(C)=C2N1C1=C2C=C(C)N=CC2=NC=N1 MZJBVKCTGOKCHG-UHFFFAOYSA-N 0.000 claims description 2
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 239000005864 Sulphur Chemical group 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000000033 alkoxyamino group Chemical group 0.000 claims description 2
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• CRKWNMCCIJMCBS-UHFFFAOYSA-N methyl 4-(3-ethynylanilino)-7h-pyrrolo[2,3-d]pyrimidine-5-carboxylate Chemical compound C=12C(C(=O)OC)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 CRKWNMCCIJMCBS-UHFFFAOYSA-N 0.000 claims description 2
• IRYJVFMQJADQNR-UHFFFAOYSA-N methyl 4-(3-ethynylanilino)-7h-pyrrolo[2,3-d]pyrimidine-5-carboxylate;hydrochloride Chemical compound Cl.C=12C(C(=O)OC)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 IRYJVFMQJADQNR-UHFFFAOYSA-N 0.000 claims description 2
• DODFKGVASNRWJI-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)-6-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=C2SC=CC2=CC(NC2=C3C=C(N=CC3=NC=N2)C)=C1 DODFKGVASNRWJI-UHFFFAOYSA-N 0.000 claims description 2
• FSIWLHREFRIZCX-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)pyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2C(NC=3C=C4C=CSC4=CC=3)=NC=NC2=C1 FSIWLHREFRIZCX-UHFFFAOYSA-N 0.000 claims description 2
• BIPLYRLRZNBNNY-UHFFFAOYSA-N n-(1h-indazol-5-yl)-6-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=C2NN=CC2=CC(NC2=C3C=C(N=CC3=NC=N2)C)=C1 BIPLYRLRZNBNNY-UHFFFAOYSA-N 0.000 claims description 2
• QWBHMRAAZIJOEI-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=C2NC=CC2=CC(NC2=C3C=C(N=CC3=NC=N2)C)=C1 QWBHMRAAZIJOEI-UHFFFAOYSA-N 0.000 claims description 2
• FJMBUNFCISVZGU-UHFFFAOYSA-N n-(1h-indol-5-yl)pyrido[4,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=NC=C2C(NC=3C=C4C=CNC4=CC=3)=NC=NC2=C1 FJMBUNFCISVZGU-UHFFFAOYSA-N 0.000 claims description 2
• CLWFLUMQGXDSSO-UHFFFAOYSA-N n-(3-chlorophenyl)-2h-triazolo[4,5-d]pyrimidin-7-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(NC=2C=3NN=NC=3N=CN=2)=C1 CLWFLUMQGXDSSO-UHFFFAOYSA-N 0.000 claims description 2
• HAWXKROVNIIVEX-UHFFFAOYSA-N n-(3-chlorophenyl)-7-methylpyrido[4,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C=NC(C)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1 HAWXKROVNIIVEX-UHFFFAOYSA-N 0.000 claims description 2
• BCLXVHJHHBULCV-UHFFFAOYSA-N n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 BCLXVHJHHBULCV-UHFFFAOYSA-N 0.000 claims description 2
• HYAREKYBZAMFCX-UHFFFAOYSA-N n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 HYAREKYBZAMFCX-UHFFFAOYSA-N 0.000 claims description 2
• RRCDEIQCICOTKZ-UHFFFAOYSA-N n-(3-chlorophenyl)pyrido[4,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(NC=2C3=CN=CC=C3N=CN=2)=C1 RRCDEIQCICOTKZ-UHFFFAOYSA-N 0.000 claims description 2
• BQQSPQFABLOBEQ-UHFFFAOYSA-N n-(3-ethynylphenyl)-5-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 BQQSPQFABLOBEQ-UHFFFAOYSA-N 0.000 claims description 2
• DQPZEBGUKFCFCP-UHFFFAOYSA-N n-(3-ethynylphenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(C)=CC2=C1NC1=CC=CC(C#C)=C1 DQPZEBGUKFCFCP-UHFFFAOYSA-N 0.000 claims description 2
• YFRSGDRAYOBDPX-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-(2-methoxyethyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N1=CN=C2N(CCOC)C=CC2=C1NC1=CC=CC(C#C)=C1 YFRSGDRAYOBDPX-UHFFFAOYSA-N 0.000 claims description 2
• HDNMPTXODRTFCR-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-[2-(2-methoxyethoxy)ethyl]pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N1=CN=C2N(CCOCCOC)C=CC2=C1NC1=CC=CC(C#C)=C1 HDNMPTXODRTFCR-UHFFFAOYSA-N 0.000 claims description 2
• LVTUVRVZECNLGU-UHFFFAOYSA-N n-(3-ethynylphenyl)-7h-purin-6-amine Chemical compound C#CC1=CC=CC(NC=2C=3N=CNC=3N=CN=2)=C1 LVTUVRVZECNLGU-UHFFFAOYSA-N 0.000 claims description 2
• YMRTUTKEYGTAGC-UHFFFAOYSA-N n-(3-ethynylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C#CC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 YMRTUTKEYGTAGC-UHFFFAOYSA-N 0.000 claims description 2
• CQUCKWCAXJCZRR-UHFFFAOYSA-N n-(3-ethynylphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C#CC1=CC=CC(NC=2C3=CC=NC=C3N=CN=2)=C1 CQUCKWCAXJCZRR-UHFFFAOYSA-N 0.000 claims description 2
• XBMUTDGAFSUQOT-UHFFFAOYSA-N n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.CC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 XBMUTDGAFSUQOT-UHFFFAOYSA-N 0.000 claims description 2
• CWHBDBIIXWUAJA-UHFFFAOYSA-N n-(4-bromo-3-fluorophenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(Br)C(F)=C1 CWHBDBIIXWUAJA-UHFFFAOYSA-N 0.000 claims description 2
• UIWSPJBKFSXXEY-UHFFFAOYSA-N n-(5-iodo-7h-pyrrolo[2,3-d]pyrimidin-4-yl)-n-(3-methylphenyl)acetamide Chemical compound N=1C=NC=2NC=C(I)C=2C=1N(C(=O)C)C1=CC=CC(C)=C1 UIWSPJBKFSXXEY-UHFFFAOYSA-N 0.000 claims description 2
• ZPCDCFLMNLYSGD-UHFFFAOYSA-N n-(6-chloro-5-fluoro-2,3-dihydroindol-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C=C(Cl)C(F)=CC=2CCN1NC1=NC=NC2=C1C=CN2 ZPCDCFLMNLYSGD-UHFFFAOYSA-N 0.000 claims description 2
• YNPDKOLXWRNDHX-UHFFFAOYSA-N n-(6-chloro-5-fluoro-2,3-dihydroindol-1-yl)pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC=C2C(NN3CCC=4C=C(C(=CC=43)Cl)F)=NC=NC2=C1 YNPDKOLXWRNDHX-UHFFFAOYSA-N 0.000 claims description 2
• YMPAUSSHJRQSED-UHFFFAOYSA-N n-(6-iodo-2,3-dihydroindol-1-yl)pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC=C2C(NN3CCC4=CC=C(C=C43)I)=NC=NC2=C1 YMPAUSSHJRQSED-UHFFFAOYSA-N 0.000 claims description 2
• YSXXPSCMGXWKAH-UHFFFAOYSA-N n-(6-methyl-2,3-dihydroindol-1-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C12=CC(C)=CC=C2CCN1NC1=NC=NC2=C1C=CN2 YSXXPSCMGXWKAH-UHFFFAOYSA-N 0.000 claims description 2
• HDARLEDIXFDUNN-UHFFFAOYSA-N n-phenylpyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC2=NC=CC=C2C=1NC1=CC=CC=C1 HDARLEDIXFDUNN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 125000003132 pyranosyl group Chemical group 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 201000002510 thyroid cancer Diseases 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 229910052721 tungsten Inorganic materials 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
• 125000002619 bicyclic group Chemical group 0.000 claims 3
• YQACOZRQAQJJNS-UHFFFAOYSA-N 6-methyl-n-[3-(trifluoromethyl)phenyl]pyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=CC(C(F)(F)F)=C1 YQACOZRQAQJJNS-UHFFFAOYSA-N 0.000 claims 2
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