HRP970371A2 - Heterocyclic compounds - Google Patents
Heterocyclic compoundsInfo
- Publication number
- HRP970371A2 HRP970371A2 HR9625492.5A HRP970371A HRP970371A2 HR P970371 A2 HRP970371 A2 HR P970371A2 HR P970371 A HRP970371 A HR P970371A HR P970371 A2 HRP970371 A2 HR P970371A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- group
- methyl
- compound
- pyrido
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- -1 nitro, carboxy , formyl Chemical group 0.000 claims description 276
- 150000001875 compounds Chemical class 0.000 claims description 206
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 238000000034 method Methods 0.000 claims description 81
- 125000003282 alkyl amino group Chemical group 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 77
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 239000012453 solvate Substances 0.000 claims description 35
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
- 239000003153 chemical reaction reagent Substances 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 26
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 26
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 25
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 230000000694 effects Effects 0.000 claims description 22
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- QNDFCSITSCMNGP-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)-6-chloropyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 QNDFCSITSCMNGP-UHFFFAOYSA-N 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000001041 indolyl group Chemical group 0.000 claims description 13
- 239000004615 ingredient Substances 0.000 claims description 13
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 13
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 12
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000004175 fluorobenzyl group Chemical group 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 150000003852 triazoles Chemical class 0.000 claims description 11
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 150000004702 methyl esters Chemical class 0.000 claims description 8
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 8
- 150000003536 tetrazoles Chemical class 0.000 claims description 8
- DYYZXRCFCVDSKD-UHFFFAOYSA-N N6,N6-dimethyl-N4-[1-(phenylmethyl)-5-indazolyl]pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 DYYZXRCFCVDSKD-UHFFFAOYSA-N 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 5
- RLCKHNKPUUYNQD-UHFFFAOYSA-N 5-[4-[(1-benzylindazol-5-yl)amino]pyrido[3,4-d]pyrimidin-6-yl]furan-2-carbaldehyde Chemical compound O1C(C=O)=CC=C1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(N(CC=2C=CC=CC=2)N=C2)C2=C1 RLCKHNKPUUYNQD-UHFFFAOYSA-N 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- LTGRUCLMFSREMZ-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(N(CC=2C=CC=CC=2)N=C2)C2=C1 LTGRUCLMFSREMZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- JFXFEXXASOCJBR-UHFFFAOYSA-N 4-n-(1-benzylindazol-5-yl)-6-n-ethyl-6-n-methylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)CC)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 JFXFEXXASOCJBR-UHFFFAOYSA-N 0.000 claims description 4
- BMIOWXJYLRLVHA-UHFFFAOYSA-N 4-n-(1-benzylindazol-5-yl)-6-n-methylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(NC)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 BMIOWXJYLRLVHA-UHFFFAOYSA-N 0.000 claims description 4
- YZZIGXZRNAEFCP-UHFFFAOYSA-N 4-n-(1-benzylindol-5-yl)-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1 YZZIGXZRNAEFCP-UHFFFAOYSA-N 0.000 claims description 4
- HKNPEKHQRROZPD-UHFFFAOYSA-N 4-n-[1-[(3-fluorophenyl)methyl]indazol-5-yl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC(F)=C1 HKNPEKHQRROZPD-UHFFFAOYSA-N 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004989 dicarbonyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- YCPVGYFQXXTANI-UHFFFAOYSA-N n-(2-benzyl-3h-benzimidazol-5-yl)-6-chloropyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1N=2)=CC=C1NC=2CC1=CC=CC=C1 YCPVGYFQXXTANI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical group C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 3
- 125000005955 1H-indazolyl group Chemical group 0.000 claims description 3
- RCDUEGIHNAMABT-UHFFFAOYSA-N 4-n-(2-benzyl-3h-benzimidazol-5-yl)-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1N2)=CC=C1N=C2CC1=CC=CC=C1 RCDUEGIHNAMABT-UHFFFAOYSA-N 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 3
- 229910052770 Uranium Inorganic materials 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- UZXVIZOKQMXWKF-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)-6-(3-methylimidazol-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CN1C=NC=C1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(N(CC=2C=CC=CC=2)N=C2)C2=C1 UZXVIZOKQMXWKF-UHFFFAOYSA-N 0.000 claims description 3
- WWAHWFCQESJGIU-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)-6-(4-methylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(N(CC=2C=CC=CC=2)N=C2)C2=C1 WWAHWFCQESJGIU-UHFFFAOYSA-N 0.000 claims description 3
- GIZAHSJRRRUFEE-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)-6-[5-(1,3-dioxolan-2-yl)furan-2-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC2=CC(NC=3C4=CC(=NC=C4N=CN=3)C=3OC(=CC=3)C3OCCO3)=CC=C2N1CC1=CC=CC=C1 GIZAHSJRRRUFEE-UHFFFAOYSA-N 0.000 claims description 3
- NEHINJYPPQYUQH-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)-6-imidazol-1-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC2=CC(NC=3C4=CC(=NC=C4N=CN=3)N3C=NC=C3)=CC=C2N1CC1=CC=CC=C1 NEHINJYPPQYUQH-UHFFFAOYSA-N 0.000 claims description 3
- WVIYDZAMWSNDDO-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)-6-pyrrolidin-1-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC2=CC(NC=3C4=CC(=NC=C4N=CN=3)N3CCCC3)=CC=C2N1CC1=CC=CC=C1 WVIYDZAMWSNDDO-UHFFFAOYSA-N 0.000 claims description 3
- DUNKZQKFWZSBHG-UHFFFAOYSA-N n-(1-benzylindol-5-yl)-6-chloropyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(Cl)=CC2=C1NC(C=C1C=C2)=CC=C1N2CC1=CC=CC=C1 DUNKZQKFWZSBHG-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- UMFFMOFETJMRSZ-UHFFFAOYSA-N 2-[4-[4-[(1-benzylindazol-5-yl)amino]pyrido[3,4-d]pyrimidin-6-yl]piperazin-1-yl]-1-morpholin-4-ylethanone Chemical compound C1COCCN1C(=O)CN(CC1)CCN1C(N=CC1=NC=N2)=CC1=C2NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1 UMFFMOFETJMRSZ-UHFFFAOYSA-N 0.000 claims description 2
- XKGUJMPYDBMSDA-UHFFFAOYSA-N 4-n-(1-benzyl-3-methylindazol-5-yl)-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C(C)=N2)=CC=C1N2CC1=CC=CC=C1 XKGUJMPYDBMSDA-UHFFFAOYSA-N 0.000 claims description 2
- HBOLGDVBJIQIQE-UHFFFAOYSA-N 4-n-[1-[(2-fluorophenyl)methyl]indazol-5-yl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CC=C1F HBOLGDVBJIQIQE-UHFFFAOYSA-N 0.000 claims description 2
- MQNRGKYCHYKEMO-UHFFFAOYSA-N 4-n-[1-[(4-fluorophenyl)methyl]indazol-5-yl]-6-n,6-n-dimethylpyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=C(F)C=C1 MQNRGKYCHYKEMO-UHFFFAOYSA-N 0.000 claims description 2
- USTNKMJFNDVPLS-UHFFFAOYSA-N 6-n,6-n-dimethyl-4-n-[1-(pyridin-3-ylmethyl)indazol-5-yl]pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N(C)C)=CC2=C1NC(C=C1C=N2)=CC=C1N2CC1=CC=CN=C1 USTNKMJFNDVPLS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- KHBQMWCZKVMBLN-IDEBNGHGSA-N benzenesulfonamide Chemical group NS(=O)(=O)[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 KHBQMWCZKVMBLN-IDEBNGHGSA-N 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- COGNCPVOUZUOSK-UHFFFAOYSA-N n-(1-benzylindazol-5-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC2=CC(NC=3C4=CC=NC=C4N=CN=3)=CC=C2N1CC1=CC=CC=C1 COGNCPVOUZUOSK-UHFFFAOYSA-N 0.000 claims description 2
- QLNPJNIYZWVSMB-UHFFFAOYSA-N n-[1-[(3-fluorophenyl)methyl]indazol-5-yl]-6-(5-methyl-1,3,4-oxadiazol-2-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound O1C(C)=NN=C1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(N(CC=2C=C(F)C=CC=2)N=C2)C2=C1 QLNPJNIYZWVSMB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 11
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- MAAXBKQABSWUKL-UHFFFAOYSA-N 2-[4-[4-[(1-benzylindazol-5-yl)amino]pyrido[3,4-d]pyrimidin-6-yl]piperazin-1-yl]-n-propan-2-ylacetamide Chemical compound C1CN(CC(=O)NC(C)C)CCN1C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(N(CC=2C=CC=CC=2)N=C2)C2=C1 MAAXBKQABSWUKL-UHFFFAOYSA-N 0.000 claims 1
- SDNXQWUJWNTDCC-UHFFFAOYSA-N 2-methylsulfonylethanamine Chemical compound CS(=O)(=O)CCN SDNXQWUJWNTDCC-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- 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
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GBGB9614763.2A GB9614763D0 (en) | 1996-07-13 | 1996-07-13 | Heterocyclic compounds |
GBGB9625492.5A GB9625492D0 (en) | 1996-12-07 | 1996-12-07 | Heterocyclic compounds |
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HRP970371A2 true HRP970371A2 (en) | 1998-08-31 |
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HR9625492.5A HRP970371A2 (en) | 1996-07-13 | 1997-07-08 | Heterocyclic compounds |
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US (2) | US6174889B1 (es) |
EP (2) | EP0912570B1 (es) |
JP (1) | JP2000514445A (es) |
KR (1) | KR20000023812A (es) |
CN (1) | CN1230187A (es) |
AP (1) | AP9901434A0 (es) |
AR (1) | AR007856A1 (es) |
AT (1) | ATE249458T1 (es) |
AU (1) | AU3443997A (es) |
BR (1) | BR9710359A (es) |
CA (1) | CA2260061A1 (es) |
CZ (1) | CZ8999A3 (es) |
DE (1) | DE69724789T2 (es) |
EA (1) | EA199900022A1 (es) |
ES (1) | ES2206729T3 (es) |
HR (1) | HRP970371A2 (es) |
ID (1) | ID19403A (es) |
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NO (1) | NO990124L (es) |
PE (1) | PE91198A1 (es) |
PL (1) | PL331221A1 (es) |
TR (1) | TR199900049T2 (es) |
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FR5600M (es) * | 1966-07-19 | 1968-01-08 | ||
CA2083688A1 (en) * | 1990-05-25 | 1991-11-26 | Marc Lippman | Growth factor which inhibits the growth of cells overexpressing the human oncogene erbb-2 |
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IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
US5679683A (en) * | 1994-01-25 | 1997-10-21 | Warner-Lambert Company | Tricyclic compounds capable of inhibiting tyrosine kinases of the epidermal growth factor receptor family |
AU2096895A (en) | 1994-03-07 | 1995-09-25 | Sugen, Incorporated | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
TW414798B (en) | 1994-09-07 | 2000-12-11 | Thomae Gmbh Dr K | Pyrimido (5,4-d) pyrimidines, medicaments comprising these compounds, their use and processes for their preparation |
GB9510757D0 (en) | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
TW321649B (es) | 1994-11-12 | 1997-12-01 | Zeneca Ltd | |
DE69515898T2 (de) | 1994-11-14 | 2000-08-17 | Warner Lambert Co | 6-ARYL-PYRIDO[2,3-d]PYRIMIDINE UND -NAPHTHYRIDINE ZUR HEMMUNG DER DURCH PROTEIN-TYROSIN-KINASE HERVORGERUFENEN ZELLVERMEHRUNG |
GB9424233D0 (en) | 1994-11-30 | 1995-01-18 | Zeneca Ltd | Quinazoline derivatives |
AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
ES2159760T3 (es) * | 1995-11-14 | 2001-10-16 | Pharmacia & Upjohn Spa | Derivados de aril purina y piridopirimidina y de heteroaril purina y piridopirimidina. |
ID19430A (id) * | 1996-07-13 | 1998-07-09 | Glaxo Group Ltd | Senyawa senyawa heterosiklik |
PT912559E (pt) | 1996-07-13 | 2003-03-31 | Glaxo Group Ltd | Compostos heterociclicos fundidos como inibidores de proteina tirosina quinase |
HRP970371A2 (en) | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
US6413971B1 (en) * | 1996-11-27 | 2002-07-02 | Pfizer Inc | Fused bicyclic pyrimidine derivatives |
-
1997
- 1997-07-08 HR HR9625492.5A patent/HRP970371A2/hr not_active Application Discontinuation
- 1997-07-11 TR TR1999/00049T patent/TR199900049T2/xx unknown
- 1997-07-11 ID IDP972412A patent/ID19403A/id unknown
- 1997-07-11 ES ES97930518T patent/ES2206729T3/es not_active Expired - Lifetime
- 1997-07-11 PL PL97331221A patent/PL331221A1/xx unknown
- 1997-07-11 DE DE69724789T patent/DE69724789T2/de not_active Expired - Fee Related
- 1997-07-11 EP EP97930518A patent/EP0912570B1/en not_active Expired - Lifetime
- 1997-07-11 IL IL12779697A patent/IL127796A0/xx unknown
- 1997-07-11 YU YU1099A patent/YU1099A/sr unknown
- 1997-07-11 BR BR9710359A patent/BR9710359A/pt not_active Application Discontinuation
- 1997-07-11 PE PE1997000611A patent/PE91198A1/es not_active Application Discontinuation
- 1997-07-11 AP APAP/P/1999/001434A patent/AP9901434A0/en unknown
- 1997-07-11 CA CA002260061A patent/CA2260061A1/en not_active Abandoned
- 1997-07-11 AR ARP970103102A patent/AR007856A1/es unknown
- 1997-07-11 EA EA199900022A patent/EA199900022A1/ru unknown
- 1997-07-11 AT AT97930518T patent/ATE249458T1/de not_active IP Right Cessation
- 1997-07-11 US US09/214,270 patent/US6174889B1/en not_active Expired - Fee Related
- 1997-07-11 EP EP02080417A patent/EP1304110A3/en not_active Withdrawn
- 1997-07-11 AU AU34439/97A patent/AU3443997A/en not_active Abandoned
- 1997-07-11 WO PCT/EP1997/003674 patent/WO1998002438A1/en active IP Right Grant
- 1997-07-11 CN CN97197876A patent/CN1230187A/zh active Pending
- 1997-07-11 CZ CZ9989A patent/CZ8999A3/cs unknown
- 1997-07-11 JP JP10505598A patent/JP2000514445A/ja not_active Ceased
-
1998
- 1998-12-31 IS IS4939A patent/IS4939A/is unknown
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1999
- 1999-01-12 NO NO990124A patent/NO990124L/no not_active Application Discontinuation
- 1999-01-13 KR KR1019997000298A patent/KR20000023812A/ko not_active Application Discontinuation
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2000
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Also Published As
Publication number | Publication date |
---|---|
DE69724789D1 (de) | 2003-10-16 |
DE69724789T2 (de) | 2004-07-01 |
JP2000514445A (ja) | 2000-10-31 |
NO990124L (no) | 1999-03-11 |
TR199900049T2 (xx) | 1999-04-21 |
EP0912570B1 (en) | 2003-09-10 |
KR20000023812A (ko) | 2000-04-25 |
EA199900022A1 (ru) | 1999-08-26 |
CN1230187A (zh) | 1999-09-29 |
ES2206729T3 (es) | 2004-05-16 |
NO990124D0 (no) | 1999-01-12 |
US6723726B1 (en) | 2004-04-20 |
AU3443997A (en) | 1998-02-09 |
YU1099A (en) | 1999-11-22 |
ATE249458T1 (de) | 2003-09-15 |
EP1304110A2 (en) | 2003-04-23 |
IL127796A0 (en) | 1999-10-28 |
WO1998002438A1 (en) | 1998-01-22 |
IS4939A (is) | 1998-12-31 |
CZ8999A3 (cs) | 1999-06-16 |
PL331221A1 (en) | 1999-07-05 |
CA2260061A1 (en) | 1998-01-22 |
AP9901434A0 (en) | 1999-03-31 |
BR9710359A (pt) | 1999-08-17 |
EP1304110A3 (en) | 2003-12-17 |
US6174889B1 (en) | 2001-01-16 |
AR007856A1 (es) | 1999-11-24 |
ID19403A (id) | 1998-07-09 |
EP0912570A1 (en) | 1999-05-06 |
PE91198A1 (es) | 1999-01-15 |
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