SK72996A3 - Heterocyclic ring-fused pyrimidine derivatives and pharmaceutical compositions on their base - Google Patents

Heterocyclic ring-fused pyrimidine derivatives and pharmaceutical compositions on their base Download PDF

Info

Publication number: SK72996A3
Authority: SK; Slovakia
Prior art keywords: pyrimidin; alkyl; carbon atoms; amine; pyrido
Prior art date: 1995-06-07

Application number

SK729-96A

Other languages

English (en)

Slovak (sk)

Inventor

Lee D Arnold

Mikel P Moyer

Susan B Sobolov-Jaynes

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

1995-06-07

Publication date

1997-04-09

1995-06-07 Application filed by Pfizer filed Critical Pfizer

1997-04-09 Publication of SK72996A3 publication Critical patent/SK72996A3/sk

Links

150000003230 pyrimidines Chemical class 0.000 title claims description 18
239000008194 pharmaceutical composition Substances 0.000 title claims description 12
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims description 10
125000000623 heterocyclic group Chemical group 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims abstract description 180
206010028980 Neoplasm Diseases 0.000 claims abstract description 29
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 17
238000011282 treatment Methods 0.000 claims abstract description 14
230000003463 hyperproliferative effect Effects 0.000 claims abstract description 13
201000010099 disease Diseases 0.000 claims abstract description 10
239000000651 prodrug Substances 0.000 claims abstract description 10
229940002612 prodrug Drugs 0.000 claims abstract description 10
241000124008 Mammalia Species 0.000 claims abstract description 5
-1 heterocyclic ring pyrimidine derivative Chemical class 0.000 claims description 213
125000004432 carbon atom Chemical group C* 0.000 claims description 132
125000000217 alkyl group Chemical group 0.000 claims description 119
229910052757 nitrogen Inorganic materials 0.000 claims description 90
125000003545 alkoxy group Chemical group 0.000 claims description 45
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
125000005605 benzo group Chemical group 0.000 claims description 14
125000005236 alkanoylamino group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 13
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
201000011510 cancer Diseases 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
210000004027 cell Anatomy 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
125000005518 carboxamido group Chemical group 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
MFGKTDNWDCJOLN-UHFFFAOYSA-N pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C2C(N)=NC=NC2=C1 MFGKTDNWDCJOLN-UHFFFAOYSA-N 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
125000004423 acyloxy group Chemical group 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 8
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 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 6
125000001475 halogen functional group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
125000004769 (C1-C4) alkylsulfonyl group Chemical group 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 5
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
239000000460 chlorine Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 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
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
GTLNHEXHXYAMKA-UHFFFAOYSA-N pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC=C2C(N)=NC=NC2=C1 GTLNHEXHXYAMKA-UHFFFAOYSA-N 0.000 claims description 5
125000005494 pyridonyl group Chemical group 0.000 claims description 5
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
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 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 4
150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 4
125000004103 aminoalkyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
210000000481 breast Anatomy 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
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 4
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 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
210000003932 urinary bladder Anatomy 0.000 claims description 4
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
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 3
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 3
CUNYDQJCQAWKLK-UHFFFAOYSA-N 3-ethynylaniline;hydrochloride Chemical compound Cl.NC1=CC=CC(C#C)=C1 CUNYDQJCQAWKLK-UHFFFAOYSA-N 0.000 claims description 3
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 3
VYOGNKSYOFTQLH-UHFFFAOYSA-N 4-(4-bromo-7-methyl-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC(C(=CC=C2C)Br)=C2N1C1=C2C=C(C)N=CC2=NC=N1 VYOGNKSYOFTQLH-UHFFFAOYSA-N 0.000 claims description 3
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 3
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 3
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 3
PEHVGBZKEYRQSX-UHFFFAOYSA-N 7-deaza-adenine Chemical compound NC1=NC=NC2=C1C=CN2 PEHVGBZKEYRQSX-UHFFFAOYSA-N 0.000 claims description 3
208000009849 Female Genital Neoplasms Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
210000004556 brain Anatomy 0.000 claims description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
210000003238 esophagus Anatomy 0.000 claims description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
210000003128 head Anatomy 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
210000004185 liver Anatomy 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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 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
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
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
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 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
229910052760 oxygen Inorganic materials 0.000 claims description 3
210000000496 pancreas Anatomy 0.000 claims description 3
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
210000002307 prostate Anatomy 0.000 claims description 3
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 3
210000002784 stomach Anatomy 0.000 claims description 3
125000004964 sulfoalkyl group Chemical group 0.000 claims description 3
208000013076 thyroid tumor Diseases 0.000 claims description 3
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
125000006656 (C2-C4) alkenyl 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
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-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
SGLIJWXMPPZXRW-UHFFFAOYSA-N 4-(6,7-dimethyl-2,3-dihydroindol-1-yl)pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N1=CC=C2C(N3CCC4=CC=C(C(=C43)C)C)=NC=NC2=C1 SGLIJWXMPPZXRW-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
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
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 2
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 2
206010004446 Benign prostatic hyperplasia Diseases 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
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 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
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
FLYXFUHCBXPRBS-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=C2SC=CC2=CC(NC2=C3C=C(N=CC3=NC=N2)C)=C1 FLYXFUHCBXPRBS-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
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 2
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GVUGOAYIVIDWIO-UFWWTJHBSA-N nepidermin Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CS)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C(C)C)C(C)C)C1=CC=C(O)C=C1 GVUGOAYIVIDWIO-UFWWTJHBSA-N 0.000 description 1
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230000002018 overexpression Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
150000005623 oxindoles Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
208000008443 pancreatic carcinoma Diseases 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
230000000865 phosphorylative effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
FJVZDOGVDJCCCR-UHFFFAOYSA-M potassium periodate Chemical compound [K+].[O-]I(=O)(=O)=O FJVZDOGVDJCCCR-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000009696 proliferative response Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 description 1
150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 1
150000004944 pyrrolopyrimidines Chemical class 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
206010038038 rectal cancer Diseases 0.000 description 1
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230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
150000003335 secondary amines Chemical group 0.000 description 1
230000011664 signaling Effects 0.000 description 1
230000007781 signaling event Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
238000011125 single therapy Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229920006301 statistical copolymer Polymers 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
239000012089 stop solution Substances 0.000 description 1
125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
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239000003765 sweetening agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
210000003905 vulva Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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

Landscapes

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)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Urology & Nephrology (AREA)
Oncology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Hematology (AREA)
Dermatology (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)

SK729-96A 1995-06-07 1995-06-07 Heterocyclic ring-fused pyrimidine derivatives and pharmaceutical compositions on their base SK72996A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
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)

Publication Number	Publication Date
SK72996A3 true SK72996A3 (en)	1997-04-09

Family

ID=89994036

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK729-96A SK72996A3 (en)	1995-06-07	1995-06-07	Heterocyclic ring-fused pyrimidine derivatives and pharmaceutical compositions on their base

Country Status (32)

Country	Link
EP (1)	EP0831829B1 (fr)
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)	FI974443A7 (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)
NZ (1)	NZ286755A (fr)
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)
WO (1)	WO1996040142A1 (fr)
ZA (1)	ZA964725B (fr)

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ES2109796T3 (es) *	1994-05-03	1998-01-16	Ciba Geigy Ag	Derivados de pirrolopirimidilo con efecto antiproliferante.
TW321649B (fr) *	1994-11-12	1997-12-01	Zeneca Ltd
GB9424233D0 (en) *	1994-11-30	1995-01-18	Zeneca Ltd	Quinazoline derivatives
JP4249804B2 (ja) *	1995-04-03	2009-04-08	ノバルティス・アクチエンゲゼルシャフト	ピラゾール誘導体およびその製造法
EP0824525B1 (fr) *	1995-04-27	2001-06-13	AstraZeneca AB	Derives de quinazoline
GB9508565D0 (en) *	1995-04-27	1995-06-14	Zeneca Ltd	Quiazoline derivative
GB9508537D0 (en) *	1995-04-27	1995-06-14	Zeneca Ltd	Quinazoline derivatives
GB9508538D0 (en) *	1995-04-27	1995-06-14	Zeneca Ltd	Quinazoline derivatives
GB9508535D0 (en) *	1995-04-27	1995-06-14	Zeneca Ltd	Quinazoline derivative
PL188959B1 (pl) *	1995-07-06	2005-05-31	Novartis Ag	Pirolopirymidyny i sposoby ich wytwarzania
GB9624482D0 (en)	1995-12-18	1997-01-15	Zeneca Phaema S A	Chemical compounds
US6140317A (en) *	1996-01-23	2000-10-31	Novartis Ag	Pyrrolopyrimidines and processes for their preparation
CA2242425C (fr)	1996-02-13	2006-07-18	Zeneca Limited	Derives de la quinazoline utilises comme inhibiteurs du vegf
GB9603095D0 (en)	1996-02-14	1996-04-10	Zeneca Ltd	Quinazoline derivatives
GB9603097D0 (en) *	1996-02-14	1996-04-10	Zeneca Ltd	Quinazoline compounds
NZ331191A (en)	1996-03-05	2000-03-27	Zeneca Ltd	4-anilinoquinazoline derivatives and pharmaceutical compositions thereof
CN100503580C (zh)	1996-04-12	2009-06-24	沃尼尔·朗伯公司	酪氨酸激酶的不可逆抑制剂
GB9607729D0 (en) *	1996-04-13	1996-06-19	Zeneca Ltd	Quinazoline derivatives
AU3176297A (en) *	1996-06-25	1998-01-14	Novartis Ag	Substituted 7-amino-pyrrolo{3,2-d}pyrimidines and the use thereof
PT938486E (pt)	1996-08-23	2008-03-27	Novartis Ag	Pirrolopirimidinas substituídas e processos para a sua preparação
CA2266519C (fr)	1996-10-02	2007-01-23	Novartis Ag	Derives de pyrimidine et procedes de preparation de ces derniers
US6225318B1 (en)	1996-10-17	2001-05-01	Pfizer Inc	4-aminoquinazolone derivatives
IL129825A0 (en) *	1996-11-27	2000-02-29	Pfizer	Fused bicyclic pyrimidine derivatives
WO1999011643A1 (fr) *	1997-09-02	1999-03-11	Du Pont Pharmaceuticals Company	Pyridines a cycle fusionne et a substitution heterocyclyle, antagonistes du facteur de liberation de la cortitropine (crf), utiles dans le traitement des troubles lies au snc et au stress
SK6652000A3 (en) *	1997-11-11	2002-05-09	Pfizer Prod Inc	Thienopyrimidine and thienopyridine derivatives useful as anticancer agents
JPH11236333A (ja) *	1997-12-30	1999-08-31	Pfizer Prod Inc	抗ガン剤として有用なイミダゾリン−４−オン誘導体
RS49779B (sr)	1998-01-12	2008-06-05	Glaxo Group Limited,	Biciklična heteroaromatična jedinjenja kao inhibitori protein tirozin kinaze
US6187777B1 (en) *	1998-02-06	2001-02-13	Amgen Inc.	Compounds and methods which modulate feeding behavior and related diseases
DE69943144D1 (de)	1998-03-31	2011-03-03	Kyowa Hakko Kirin Co Ltd	Stickstoffenthaltende heterocyclische verbindungen
PA8474101A1 (es) *	1998-06-19	2000-09-29	Pfizer Prod Inc	Compuestos de pirrolo [2,3-d] pirimidina
AU3951899A (en)	1998-06-19	2000-01-05	Pfizer Products Inc.	Pyrrolo(2,3-d)pyrimidine compounds
WO2000023444A1 (fr) *	1998-10-21	2000-04-27	Abbott Laboratories	Composes de 4-aminopyrido[2,3-d]pyrimidine a disubstitution 5,7
US6174903B1 (en)	1998-12-28	2001-01-16	Pfizer Inc.	Imidazolidin-4-one derivatives useful as anticancer agents
JP3270834B2 (ja)	1999-01-27	2002-04-02	ファイザー・プロダクツ・インク	抗がん剤として有用なヘテロ芳香族二環式誘導体
UA71945C2 (en)	1999-01-27	2005-01-17	Pfizer Prod Inc	Substituted bicyclic derivatives being used as anticancer agents
JP2003504363A (ja)	1999-07-09	2003-02-04	グラクソグループリミテッド	プロテインチロシンキナーゼ阻害剤としてのアニリノキナゾリン類
US6933299B1 (en)	1999-07-09	2005-08-23	Smithkline Beecham Corporation	Anilinoquinazolines as protein tyrosine kinase inhibitors
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1995
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- 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 DK DK95924027T patent/DK0831829T3/da active
- 1995-06-07 JP JP50039097A patent/JP3290666B2/ja not_active Expired - Fee Related
- 1995-06-07 PT PT95924027T patent/PT831829E/pt unknown
- 1995-06-07 EP EP95924027A patent/EP0831829B1/fr not_active Expired - Lifetime
- 1995-06-07 MX MX9709867A patent/MX9709867A/es not_active IP Right Cessation
- 1995-06-07 FI FI974443A patent/FI974443A7/fi unknown
- 1995-06-07 WO PCT/US1995/007881 patent/WO1996040142A1/fr not_active Ceased
- 1995-06-07 AT AT95924027T patent/ATE247469T1/de not_active IP Right Cessation
- 1995-06-07 DE DE69531558T patent/DE69531558T2/de not_active Expired - Fee Related
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 SI SI9600184A patent/SI9600184A/sl unknown
- 1996-06-06 TR TR96/00474A patent/TR199600474A2/xx unknown
- 1996-06-06 NZ NZ286755A patent/NZ286755A/en unknown
- 1996-06-06 HU HU9601559A patent/HUP9601559A3/hu unknown
- 1996-06-06 AU AU54791/96A patent/AU5479196A/en not_active Abandoned
- 1996-06-06 ZA ZA9604725A patent/ZA964725B/xx unknown
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- 1996-06-06 HR HR95/007,881A patent/HRP960269A2/hr not_active Application Discontinuation
- 1996-06-06 CZ CZ961641A patent/CZ164196A3/cs unknown
- 1996-06-07 RU RU96111016A patent/RU2136683C1/ru active
- 1996-06-07 OA OA60838A patent/OA10460A/en unknown
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Also Published As

Publication number	Publication date
AR002746A1 (es)	1998-04-29
AP637A (en)	1998-04-08
EP0831829A1 (fr)	1998-04-01
SI9600184A (en)	1997-04-30
NZ286755A (en)	1998-03-25
CO4440628A1 (es)	1997-05-07
CN1141298A (zh)	1997-01-29
CZ164196A3 (en)	1996-12-11
JP3290666B2 (ja)	2002-06-10
AU5479196A (en)	1996-12-19
PL314641A1 (en)	1996-12-09
HRP960269A2 (en)	1997-08-31
TR199600474A2 (tr)	1996-12-21
DE69531558D1 (de)	2003-09-25
ZA964725B (en)	1997-12-08
PT831829E (pt)	2003-12-31
FI974443L (fi)	1997-12-05
DK0831829T3 (da)	2003-12-15
OA10460A (en)	2002-03-28
ATE247469T1 (de)	2003-09-15
DE69531558T2 (de)	2004-03-18
MX9709867A (es)	1998-03-31
HU9601559D0 (en)	1996-08-28
AP9600805A0 (en)	1996-07-31
RU2136683C1 (ru)	1999-09-10
MA26409A1 (fr)	2004-12-20
EP0831829B1 (fr)	2003-08-20
BR9602695A (pt)	1998-10-06
CA2223081A1 (fr)	1996-12-19
FI974443A0 (fi)	1997-12-05
ES2203642T3 (es)	2004-04-16
EP0831829A4 (fr)	1998-11-25
SG45483A1 (en)	1998-01-16
JPH10508875A (ja)	1998-09-02
FI974443A7 (fi)	1997-12-05
NO962386L (no)	1996-12-09
HUP9601559A2 (en)	1997-02-28
WO1996040142A1 (fr)	1996-12-19
CA2223081C (fr)	2001-03-06
HUP9601559A3 (en)	1997-07-28
IL118487A0 (en)	1996-09-12
NO962386D0 (no)	1996-06-06

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