OA10460A - Heterocyclic ring-fused pyrimidine derivatives - Google Patents
Heterocyclic ring-fused pyrimidine derivatives Download PDFInfo
- Publication number
- OA10460A OA10460A OA60838A OA60838A OA10460A OA 10460 A OA10460 A OA 10460A OA 60838 A OA60838 A OA 60838A OA 60838 A OA60838 A OA 60838A OA 10460 A OA10460 A OA 10460A
- Authority
- OA
- OAPI
- Prior art keywords
- pyrimidin
- amine
- pyrido
- phenyl
- alkyl
- Prior art date
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- 125000000623 heterocyclic group Chemical group 0.000 title description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- 150000003230 pyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000000651 prodrug Substances 0.000 claims abstract description 3
- 229940002612 prodrug Drugs 0.000 claims abstract description 3
- -1 nitro, hydroxy, amino Chemical group 0.000 claims description 128
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 125000003282 alkyl amino group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000005518 carboxamido group Chemical group 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 201000011510 cancer Diseases 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000005605 benzo group Chemical group 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000005494 pyridonyl group Chemical group 0.000 claims description 8
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 210000000481 breast Anatomy 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 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 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 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
- 229910014585 C2-Ce Inorganic materials 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
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 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
- 230000002496 gastric effect Effects 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
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 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
- 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 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
- 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
- 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 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000003118 aryl 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
- 210000004556 brain Anatomy 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 230000002440 hepatic effect Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 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
- 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
- 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 3
- 239000001301 oxygen Chemical group 0.000 claims description 3
- 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 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 125000004760 (C1-C4) alkylsulfonylamino 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
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 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
- 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 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- BSEIRHPCQJAJNT-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-ol Chemical compound C1CC2=CC=C(Cl)C=C2N1C1=C(NC(O)=C2)C2=NC=N1 BSEIRHPCQJAJNT-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- OZMLAELAHCCJQD-UHFFFAOYSA-N 7-(benzenesulfonyl)-n-(3-ethynylphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC2=C(NC=3C=C(C=CC=3)C#C)N=CN=C2N1S(=O)(=O)C1=CC=CC=C1 OZMLAELAHCCJQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004399 C1-C4 alkenyl group Chemical group 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
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005596 alkyl carboxamido group Chemical group 0.000 claims description 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 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
- 125000003843 furanosyl group Chemical group 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
- 150000004702 methyl esters Chemical class 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
- 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 2
- 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 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
- 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 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
- 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 2
- 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 2
- 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 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
- 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 2
- 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 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 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
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 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 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- GLDRNGJKSCNHOB-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C2SC=CC2=CC=1NC1=NC=NC2=C1C=CN2 GLDRNGJKSCNHOB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- BHOIHXVTLUPUES-UHFFFAOYSA-N n-(1h-indazol-5-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C2NN=CC2=CC=1NC1=NC=NC2=C1C=CN2 BHOIHXVTLUPUES-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Nitrogen Condensed Heterocyclic Rings (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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PCT/US1995/007881 WO1996040142A1 (fr) | 1995-06-07 | 1995-06-07 | Derives de pyrimidine heterocycliques a noyaux condenses |
HU9601559A HUP9601559A3 (en) | 1995-06-07 | 1996-06-06 | Heterocyclic ring-fused pyrimidine derivatives, pharmaceutical compositions containing the same and intermediates |
Publications (1)
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OA10460A true OA10460A (en) | 2002-03-28 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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OA60838A OA10460A (en) | 1995-06-07 | 1996-06-07 | Heterocyclic ring-fused pyrimidine derivatives |
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JP (1) | JP3290666B2 (fr) |
CN (1) | CN1141298A (fr) |
AP (1) | AP637A (fr) |
AR (1) | AR002746A1 (fr) |
AT (1) | ATE247469T1 (fr) |
AU (1) | AU5479196A (fr) |
BR (1) | BR9602695A (fr) |
CA (1) | CA2223081C (fr) |
CO (1) | CO4440628A1 (fr) |
CZ (1) | CZ164196A3 (fr) |
DE (1) | DE69531558T2 (fr) |
DK (1) | DK0831829T3 (fr) |
ES (1) | ES2203642T3 (fr) |
FI (1) | FI974443A0 (fr) |
HR (1) | HRP960269A2 (fr) |
HU (1) | HUP9601559A3 (fr) |
IL (1) | IL118487A0 (fr) |
MA (1) | MA26409A1 (fr) |
MX (1) | MX9709867A (fr) |
NO (1) | NO962386L (fr) |
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OA (1) | OA10460A (fr) |
PL (1) | PL314641A1 (fr) |
PT (1) | PT831829E (fr) |
RU (1) | RU2136683C1 (fr) |
SG (1) | SG45483A1 (fr) |
SI (1) | SI9600184A (fr) |
SK (1) | SK72996A3 (fr) |
TR (1) | TR199600474A2 (fr) |
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JPS58157790A (ja) * | 1982-03-16 | 1983-09-19 | Takeda Chem Ind Ltd | 7−デアザプリン誘導体およびその製造法 |
JPS60233080A (ja) * | 1984-05-02 | 1985-11-19 | Takeda Chem Ind Ltd | 7−デアザプリン誘導体 |
IE60433B1 (en) * | 1986-08-26 | 1994-07-13 | Warner Lambert Co | Novel 9-deazaguanines |
NO169490C (no) * | 1988-03-24 | 1992-07-01 | Takeda Chemical Industries Ltd | Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolopyrimidinderivater |
ATE139232T1 (de) * | 1989-10-11 | 1996-06-15 | Teijin Ltd | Bizyklische pyrimidinderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzung |
US5320663A (en) * | 1992-07-02 | 1994-06-14 | E. I. Du Pont De Nemours And Company | Method of obtaining lead and organolead from contaminated media using metal accumulating plants |
ATE177101T1 (de) * | 1992-12-17 | 1999-03-15 | Pfizer | Pyrrolopyrimidine als crf antagonisten |
AU6855594A (en) * | 1993-06-30 | 1995-01-24 | Biocryst Pharmaceuticals, Inc. | 9-deazahypoxanthines as pnp inhibitors |
-
1995
- 1995-06-07 MX MX9709867A patent/MX9709867A/es not_active IP Right Cessation
- 1995-06-07 PT PT95924027T patent/PT831829E/pt unknown
- 1995-06-07 DE DE69531558T patent/DE69531558T2/de not_active Expired - Fee Related
- 1995-06-07 DK DK95924027T patent/DK0831829T3/da active
- 1995-06-07 CA CA002223081A patent/CA2223081C/fr not_active Expired - Fee Related
- 1995-06-07 EP EP95924027A patent/EP0831829B1/fr not_active Expired - Lifetime
- 1995-06-07 AT AT95924027T patent/ATE247469T1/de not_active IP Right Cessation
- 1995-06-07 SK SK729-96A patent/SK72996A3/sk unknown
- 1995-06-07 ES ES95924027T patent/ES2203642T3/es not_active Expired - Lifetime
- 1995-06-07 JP JP50039097A patent/JP3290666B2/ja not_active Expired - Fee Related
- 1995-06-07 WO PCT/US1995/007881 patent/WO1996040142A1/fr active IP Right Grant
-
1996
- 1996-05-09 AP APAP/P/1996/000805A patent/AP637A/en active
- 1996-05-22 AR ARP960102673A patent/AR002746A1/es unknown
- 1996-05-30 IL IL11848796A patent/IL118487A0/xx unknown
- 1996-06-03 MA MA24256A patent/MA26409A1/fr unknown
- 1996-06-05 CN CN96108101A patent/CN1141298A/zh active Pending
- 1996-06-05 SG SG1996009982A patent/SG45483A1/en unknown
- 1996-06-05 PL PL96314641A patent/PL314641A1/xx unknown
- 1996-06-06 HU HU9601559A patent/HUP9601559A3/hu unknown
- 1996-06-06 NZ NZ286755A patent/NZ286755A/en unknown
- 1996-06-06 NO NO962386A patent/NO962386L/no unknown
- 1996-06-06 HR HR95/007,881A patent/HRP960269A2/hr not_active Application Discontinuation
- 1996-06-06 AU AU54791/96A patent/AU5479196A/en not_active Abandoned
- 1996-06-06 TR TR96/00474A patent/TR199600474A2/xx unknown
- 1996-06-06 ZA ZA9604725A patent/ZA964725B/xx unknown
- 1996-06-06 CZ CZ961641A patent/CZ164196A3/cs unknown
- 1996-06-06 SI SI9600184A patent/SI9600184A/sl unknown
- 1996-06-07 BR BR9602695A patent/BR9602695A/pt active Search and Examination
- 1996-06-07 RU RU96111016A patent/RU2136683C1/ru active
- 1996-06-07 OA OA60838A patent/OA10460A/en unknown
- 1996-06-07 CO CO96029731A patent/CO4440628A1/es unknown
-
1997
- 1997-12-05 FI FI974443A patent/FI974443A0/fi unknown
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