SI9600184A - Heterocyclic ring-fused pyrimidine derivatives - Google Patents

Info

Publication number

SI9600184A

SI9600184A SI9600184A SI9600184A SI9600184A SI 9600184 A SI9600184 A SI 9600184A SI 9600184 A SI9600184 A SI 9600184A SI 9600184 A SI9600184 A SI 9600184A SI 9600184 A SI9600184 A SI 9600184A

Authority

SI

Slovenia

Prior art keywords

pyrimidin

amine

alkyl

pyrido

phenyl

Prior art date

1995-06-07

Links

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• Global Dossier
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• 150000003230 pyrimidines Chemical class 0.000 title description 5
• 125000000623 heterocyclic group Chemical group 0.000 title description 2
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 147
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 12
• 150000003839 salts Chemical class 0.000 claims abstract description 12
• 241000124008 Mammalia Species 0.000 claims abstract description 7
• 239000000651 prodrug Substances 0.000 claims abstract 2
• 229940002612 prodrug Drugs 0.000 claims abstract 2
• -1 nitro, hydroxy, amino Chemical group 0.000 claims description 219
• 229910052757 nitrogen Inorganic materials 0.000 claims description 99
• 125000000217 alkyl group Chemical group 0.000 claims description 75
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• 125000003282 alkyl amino group Chemical group 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• 150000001412 amines Chemical class 0.000 claims description 33
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
• 125000005518 carboxamido group Chemical group 0.000 claims description 14
• 125000004414 alkyl thio group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 10
• 125000004423 acyloxy group Chemical group 0.000 claims description 9
• 125000005605 benzo group Chemical group 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
• 125000005596 alkyl carboxamido group Chemical group 0.000 claims description 8
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000005494 pyridonyl group Chemical group 0.000 claims description 8
• 229910052727 yttrium Inorganic materials 0.000 claims description 8
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000001589 carboacyl group Chemical group 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 6
• 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 6
• GXHHNATXYAMTDG-UHFFFAOYSA-N n-phenylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C=NC2=CN=CC=C2C=1NC1=CC=CC=C1 GXHHNATXYAMTDG-UHFFFAOYSA-N 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• KAIRQZLXOKATIQ-UHFFFAOYSA-N 4-(3-ethynylanilino)-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile Chemical compound C#CC1=CC=CC(NC=2C=3C(C#N)=CNC=3N=CN=2)=C1 KAIRQZLXOKATIQ-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• OGJKPEXQIVCSBG-UHFFFAOYSA-N CC1=CC(NC2=NC=NC3=C2C=NC=C3)=CC=C1 Chemical compound CC1=CC(NC2=NC=NC3=C2C=NC=C3)=CC=C1 OGJKPEXQIVCSBG-UHFFFAOYSA-N 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
• 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 5
• 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 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 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 5
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 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 4
• OHKQCQFYJDTPBJ-UHFFFAOYSA-N ClC1=CC=C(CCN2C3=NC=NC4=C3C=NC=C4)C2=C1 Chemical compound ClC1=CC=C(CCN2C3=NC=NC4=C3C=NC=C4)C2=C1 OHKQCQFYJDTPBJ-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
• 125000003368 amide group Chemical group 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
• 125000001475 halogen functional group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• JXFAHPCDBDADEP-UHFFFAOYSA-N n-(3-ethynyl-4-fluorophenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(F)C(C#C)=C1 JXFAHPCDBDADEP-UHFFFAOYSA-N 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• UZZQOANSYKQBJS-UHFFFAOYSA-N 2-iodo-4-[(6-methylpyrido[3,4-d]pyrimidin-4-yl)amino]phenol hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(O)C(I)=C1 UZZQOANSYKQBJS-UHFFFAOYSA-N 0.000 claims description 3
• LDZCYEOEHIAAHI-UHFFFAOYSA-N 4-(4-bromo-7-methyl-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine Chemical compound C1CC(C(=CC=C2C)Br)=C2N1C1=C2C=C(C)N=CC2=NC=N1 LDZCYEOEHIAAHI-UHFFFAOYSA-N 0.000 claims description 3
• BGZUKOJRLCOJQL-UHFFFAOYSA-N 4-(6-bromo-5-fluoro-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine Chemical compound C1CC2=CC(F)=C(Br)C=C2N1C1=C2C=C(C)N=CC2=NC=N1 BGZUKOJRLCOJQL-UHFFFAOYSA-N 0.000 claims description 3
• PQTYWQWATNSLSN-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine Chemical compound C1CC2=CC=C(Cl)C=C2N1C1=C2C=C(C)N=CC2=NC=N1 PQTYWQWATNSLSN-UHFFFAOYSA-N 0.000 claims description 3
• RKBKLXOJDZURGJ-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)-7h-pyrrolo[2,3-d]pyrimidine;hydrochloride Chemical compound Cl.C12=CC(Cl)=CC=C2CCN1C1=NC=NC2=C1C=CN2 RKBKLXOJDZURGJ-UHFFFAOYSA-N 0.000 claims description 3
• WMAOJUAPQNRXMN-UHFFFAOYSA-N 5-iodo-n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(NC=2C=3C(I)=CNC=3N=CN=2)=C1 WMAOJUAPQNRXMN-UHFFFAOYSA-N 0.000 claims description 3
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
• 150000001721 carbon Chemical group 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• QMJOVHBPLRUCLQ-UHFFFAOYSA-N n-(1h-indazol-5-yl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=C2NN=CC2=CC(NC2=C3C=C(N=CC3=NC=N2)C)=C1 QMJOVHBPLRUCLQ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• OUBTWUSFURPWEL-UHFFFAOYSA-N n-(1h-indazol-5-yl)pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC=C2C(NC=3C=C4C=NNC4=CC=3)=NC=NC2=C1 OUBTWUSFURPWEL-UHFFFAOYSA-N 0.000 claims description 3
• RAISXOMJIRTPRU-UHFFFAOYSA-N n-(1h-indol-5-yl)-7h-purin-6-amine;hydrochloride Chemical compound Cl.C=1C=C2NC=CC2=CC=1NC1=NC=NC2=C1N=CN2 RAISXOMJIRTPRU-UHFFFAOYSA-N 0.000 claims description 3
• FGCYZSQHCWZARH-UHFFFAOYSA-N n-(1h-indol-5-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=1C=C2NC=CC2=CC=1NC1=NC=NC2=C1C=CN2 FGCYZSQHCWZARH-UHFFFAOYSA-N 0.000 claims description 3
• OAVGTUPPZGFJPZ-UHFFFAOYSA-N n-(1h-indol-5-yl)pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC=C2C(NC=3C=C4C=CNC4=CC=3)=NC=NC2=C1 OAVGTUPPZGFJPZ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• KXQSONXECJTULQ-UHFFFAOYSA-N n-(3-bromophenyl)pyrido[4,3-d]pyrimidin-4-amine Chemical compound BrC1=CC=CC(NC=2C3=CN=CC=C3N=CN=2)=C1 KXQSONXECJTULQ-UHFFFAOYSA-N 0.000 claims description 3
• WMSTVSZIKRBBNP-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 WMSTVSZIKRBBNP-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• ZKISXEYMMCKORH-UHFFFAOYSA-N n-(3-chlorophenyl)-7h-purin-6-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(NC=2C=3N=CNC=3N=CN=2)=C1 ZKISXEYMMCKORH-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• UTDASZLSKTXCQQ-UHFFFAOYSA-N n-(3-chlorophenyl)pyrido[4,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C3=CN=CC=C3N=CN=2)=C1 UTDASZLSKTXCQQ-UHFFFAOYSA-N 0.000 claims description 3
• DWNRTKDSVRXCDR-UHFFFAOYSA-N n-(3-ethynylphenyl)-5-iodo-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(I)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 DWNRTKDSVRXCDR-UHFFFAOYSA-N 0.000 claims description 3
• YRRBOKHSOVSHSI-UHFFFAOYSA-N n-(3-ethynylphenyl)-5-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C(C)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 YRRBOKHSOVSHSI-UHFFFAOYSA-N 0.000 claims description 3
• XGPRAWMNWHDJKI-UHFFFAOYSA-N n-(3-ethynylphenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=CC(C#C)=C1 XGPRAWMNWHDJKI-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• LOXLJUYFTDRFPO-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-methylpyrido[4,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C=NC(C)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 LOXLJUYFTDRFPO-UHFFFAOYSA-N 0.000 claims description 3
• NDKPPINOPXHVPF-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-methylpyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2N(C)C=CC2=C1NC1=CC=CC(C#C)=C1 NDKPPINOPXHVPF-UHFFFAOYSA-N 0.000 claims description 3
• QFRDWIHAVDMHPE-UHFFFAOYSA-N n-(3-ethynylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C#CC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 QFRDWIHAVDMHPE-UHFFFAOYSA-N 0.000 claims description 3
• HNGRZKXBWKRSCA-UHFFFAOYSA-N n-(3-ethynylphenyl)pyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C#CC1=CC=CC(NC=2C3=CC=NC=C3N=CN=2)=C1 HNGRZKXBWKRSCA-UHFFFAOYSA-N 0.000 claims description 3
• IWJGFLQPYWJHAV-UHFFFAOYSA-N n-(3-ethynylphenyl)pyrido[4,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C#CC1=CC=CC(NC=2C3=CN=CC=C3N=CN=2)=C1 IWJGFLQPYWJHAV-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 239000001301 oxygen Chemical group 0.000 claims description 3
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• 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
• DKLGVCDKNBPBEQ-UHFFFAOYSA-N 1-[4-(3-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]ethanone;hydrochloride Chemical compound Cl.N1=CN=C2N(C(=O)C)C=CC2=C1NC1=CC=CC(C)=C1 DKLGVCDKNBPBEQ-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
• XWQYVWRXHMSKRB-UHFFFAOYSA-N 2-methyl-4-[(6-methylpyrido[3,4-d]pyrimidin-4-yl)amino]phenol dihydrochloride Chemical compound Cl.Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(O)C(C)=C1 XWQYVWRXHMSKRB-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
• FUYJBBSAMAELRK-UHFFFAOYSA-N 4-(6-bromo-7-methyl-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine Chemical compound C1CC2=CC=C(Br)C(C)=C2N1C1=C2C=C(C)N=CC2=NC=N1 FUYJBBSAMAELRK-UHFFFAOYSA-N 0.000 claims description 2
• LOPBUDCQZDQIQH-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one Chemical compound ClC1=CC=C2CCN(C2=C1)C=1C2=C(N=CN=1)N=C(C2)O LOPBUDCQZDQIQH-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 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
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000003843 furanosyl group Chemical group 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
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