OA10460A - Heterocyclic ring-fused pyrimidine derivatives - Google Patents

Heterocyclic ring-fused pyrimidine derivatives Download PDF

Info

Publication number: OA10460A
Authority: OA; OAPI
Prior art keywords: pyrimidin; amine; pyrido; phenyl; alkyl
Prior art date: 1995-06-07

Application number

OA60838A

Other languages

English (en)

Inventor

Daniel Arnold Lee

Paul Moyer Mikel

Beth Sobolov-Jaynes Susan

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1995-06-07

Filing date

1996-06-07

Publication date

2002-03-28

1996-06-07 Application filed by Pfizer filed Critical Pfizer

2002-03-28 Publication of OA10460A publication Critical patent/OA10460A/en

Links

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
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 1
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Classifications

- 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
- 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
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Oncology (AREA)
Hematology (AREA)
Dermatology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

OA60838A 1995-06-07 1996-06-07 Heterocyclic ring-fused pyrimidine derivatives OA10460A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/US1995/007881 WO1996040142A1 (en)	1995-06-07	1995-06-07	Heterocyclic ring-fused pyrimidine derivatives
HU9601559A HUP9601559A3 (en)	1995-06-07	1996-06-06	Heterocyclic ring-fused pyrimidine derivatives, pharmaceutical compositions containing the same and intermediates

Publications (1)

Publication Number	Publication Date
OA10460A true OA10460A (en)	2002-03-28

Family

ID=89994036

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60838A OA10460A (en)	1995-06-07	1996-06-07	Heterocyclic ring-fused pyrimidine derivatives

Country Status (32)

Country	Link
EP (1)	EP0831829B1 (cs)
JP (1)	JP3290666B2 (cs)
CN (1)	CN1141298A (cs)
AP (1)	AP637A (cs)
AR (1)	AR002746A1 (cs)
AT (1)	ATE247469T1 (cs)
AU (1)	AU5479196A (cs)
BR (1)	BR9602695A (cs)
CA (1)	CA2223081C (cs)
CO (1)	CO4440628A1 (cs)
CZ (1)	CZ164196A3 (cs)
DE (1)	DE69531558T2 (cs)
DK (1)	DK0831829T3 (cs)
ES (1)	ES2203642T3 (cs)
FI (1)	FI974443A0 (cs)
HR (1)	HRP960269A2 (cs)
HU (1)	HUP9601559A3 (cs)
IL (1)	IL118487A0 (cs)
MA (1)	MA26409A1 (cs)
MX (1)	MX9709867A (cs)
NO (1)	NO962386L (cs)
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1995
- 1995-06-07 DE DE69531558T patent/DE69531558T2/de not_active Expired - Fee Related
- 1995-06-07 CA CA002223081A patent/CA2223081C/en not_active Expired - Fee Related
- 1995-06-07 MX MX9709867A patent/MX9709867A/es not_active IP Right Cessation
- 1995-06-07 FI FI974443A patent/FI974443A0/fi unknown
- 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 PT PT95924027T patent/PT831829E/pt unknown
- 1995-06-07 EP EP95924027A patent/EP0831829B1/en not_active Expired - Lifetime
- 1995-06-07 JP JP50039097A patent/JP3290666B2/ja not_active Expired - Fee Related
- 1995-06-07 ES ES95924027T patent/ES2203642T3/es not_active Expired - Lifetime
- 1995-06-07 WO PCT/US1995/007881 patent/WO1996040142A1/en not_active Ceased
- 1995-06-07 DK DK95924027T patent/DK0831829T3/da active
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 SG SG1996009982A patent/SG45483A1/en unknown
- 1996-06-05 CN CN96108101A patent/CN1141298A/zh active Pending
- 1996-06-05 PL PL96314641A patent/PL314641A1/xx unknown
- 1996-06-06 TR TR96/00474A patent/TR199600474A2/xx unknown
- 1996-06-06 ZA ZA9604725A patent/ZA964725B/xx unknown
- 1996-06-06 HU HU9601559A patent/HUP9601559A3/hu unknown
- 1996-06-06 HR HR95/007,881A patent/HRP960269A2/hr not_active Application Discontinuation
- 1996-06-06 NO NO962386A patent/NO962386L/no unknown
- 1996-06-06 NZ NZ286755A patent/NZ286755A/en unknown
- 1996-06-06 CZ CZ961641A patent/CZ164196A3/cs unknown
- 1996-06-06 SI SI9600184A patent/SI9600184A/sl unknown
- 1996-06-06 AU AU54791/96A patent/AU5479196A/en not_active Abandoned
- 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
- 1996-06-07 BR BR9602695A patent/BR9602695A/pt active Search and Examination

Also Published As

Publication number	Publication date
AR002746A1 (es)	1998-04-29
CA2223081C (en)	2001-03-06
PT831829E (pt)	2003-12-31
ES2203642T3 (es)	2004-04-16
SI9600184A (en)	1997-04-30
FI974443A7 (fi)	1997-12-05
AP9600805A0 (en)	1996-07-31
NO962386L (no)	1996-12-09
EP0831829B1 (en)	2003-08-20
MA26409A1 (fr)	2004-12-20
CA2223081A1 (en)	1996-12-19
SK72996A3 (en)	1997-04-09
JP3290666B2 (ja)	2002-06-10
DE69531558D1 (de)	2003-09-25
CO4440628A1 (es)	1997-05-07
AP637A (en)	1998-04-08
PL314641A1 (en)	1996-12-09
NO962386D0 (no)	1996-06-06
HUP9601559A2 (en)	1997-02-28
BR9602695A (pt)	1998-10-06
ZA964725B (en)	1997-12-08
DE69531558T2 (de)	2004-03-18
TR199600474A2 (tr)	1996-12-21
RU2136683C1 (ru)	1999-09-10
CN1141298A (zh)	1997-01-29
NZ286755A (en)	1998-03-25
FI974443L (fi)	1997-12-05
WO1996040142A1 (en)	1996-12-19
HUP9601559A3 (en)	1997-07-28
IL118487A0 (en)	1996-09-12
SG45483A1 (en)	1998-01-16
DK0831829T3 (da)	2003-12-15
FI974443A0 (fi)	1997-12-05
CZ164196A3 (en)	1996-12-11
MX9709867A (es)	1998-03-31
HRP960269A2 (en)	1997-08-31
HU9601559D0 (en)	1996-08-28
JPH10508875A (ja)	1998-09-02
EP0831829A4 (en)	1998-11-25
EP0831829A1 (en)	1998-04-01
ATE247469T1 (de)	2003-09-15
AU5479196A (en)	1996-12-19

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