JP2008523134A5 - - Google Patents
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- JP2008523134A5 JP2008523134A5 JP2007546165A JP2007546165A JP2008523134A5 JP 2008523134 A5 JP2008523134 A5 JP 2008523134A5 JP 2007546165 A JP2007546165 A JP 2007546165A JP 2007546165 A JP2007546165 A JP 2007546165A JP 2008523134 A5 JP2008523134 A5 JP 2008523134A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyrazolo
- oxy
- amino
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- -1 pyrazolopyrimidine compound Chemical class 0.000 claims description 235
- 125000000217 alkyl group Chemical group 0.000 claims description 202
- 229910052757 nitrogen Inorganic materials 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 55
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000001589 carboacyl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 229910052717 sulfur Chemical group 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 9
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 15
- 125000000524 functional group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 4
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 claims 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 3
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- IZQPBXPMSBFBCG-HXUWFJFHSA-N (2r)-1-[2-[[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]pyrrolidin-2-ol Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC1=NC=NC2=C1C(OCCN1[C@@H](CCC1)O)=NN2 IZQPBXPMSBFBCG-HXUWFJFHSA-N 0.000 claims 1
- IZQPBXPMSBFBCG-FQEVSTJZSA-N (2s)-1-[2-[[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]pyrrolidin-2-ol Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC1=NC=NC2=C1C(OCCN1[C@H](CCC1)O)=NN2 IZQPBXPMSBFBCG-FQEVSTJZSA-N 0.000 claims 1
- UUCPCAZWRGRGCP-QGZVFWFLSA-N (3r)-1-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]pyrrolidin-3-ol Chemical compound C1[C@H](O)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 UUCPCAZWRGRGCP-QGZVFWFLSA-N 0.000 claims 1
- UUCPCAZWRGRGCP-KRWDZBQOSA-N (3s)-1-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 UUCPCAZWRGRGCP-KRWDZBQOSA-N 0.000 claims 1
- UWUFUUGZSOQBCY-UHFFFAOYSA-N 1-[2-[[4-[3-chloro-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C1=NC(C)=CC=C1OC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1C(OCCN1CCC(O)CC1)=NN2 UWUFUUGZSOQBCY-UHFFFAOYSA-N 0.000 claims 1
- OOWWSELYEWEGFH-UHFFFAOYSA-N 1-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 OOWWSELYEWEGFH-UHFFFAOYSA-N 0.000 claims 1
- GBRXUAZIMSFHPJ-UHFFFAOYSA-N 1-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]pyrrolidin-2-one Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(Cl)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCCC1=O GBRXUAZIMSFHPJ-UHFFFAOYSA-N 0.000 claims 1
- ZXQYLBWEILBYIE-UHFFFAOYSA-N 1-[2-[[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)=C12 ZXQYLBWEILBYIE-UHFFFAOYSA-N 0.000 claims 1
- JDUVCKXVGSZRRN-UHFFFAOYSA-N 1-[2-[[4-[3-ethyl-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(CC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCC(O)CC1 JDUVCKXVGSZRRN-UHFFFAOYSA-N 0.000 claims 1
- KOBKLBFNTIJTTR-UHFFFAOYSA-N 1-[2-[[4-[3-fluoro-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C1=NC(C)=CC=C1OC(C(=C1)F)=CC=C1NC1=NC=NC2=C1C(OCCN1CCC(O)CC1)=NN2 KOBKLBFNTIJTTR-UHFFFAOYSA-N 0.000 claims 1
- VMDUWDNQTGHKSN-UHFFFAOYSA-N 1-[2-[[4-[3-methoxy-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(OC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCC(O)CC1 VMDUWDNQTGHKSN-UHFFFAOYSA-N 0.000 claims 1
- LYCPWHYCBIEJPN-UHFFFAOYSA-N 1-[2-[[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC1=NC=NC2=C1C(OCCN1CCC(O)CC1)=NN2 LYCPWHYCBIEJPN-UHFFFAOYSA-N 0.000 claims 1
- GYDNMCFYNSRRTC-UHFFFAOYSA-N 1-[2-[[4-[3-methyl-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(C)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCC(O)CC1 GYDNMCFYNSRRTC-UHFFFAOYSA-N 0.000 claims 1
- PXOQNEQRSUORAM-UHFFFAOYSA-N 1-[2-[[4-[4-[(3-fluorophenyl)methoxy]-3-methoxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCC(O)CC1 PXOQNEQRSUORAM-UHFFFAOYSA-N 0.000 claims 1
- RVSMZHTVMMGSFY-UHFFFAOYSA-N 1-[2-[[4-[4-[(3-fluorophenyl)methoxy]-3-methylanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperidin-4-ol Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(C)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCC(O)CC1 RVSMZHTVMMGSFY-UHFFFAOYSA-N 0.000 claims 1
- YJELZTGEMAQGHU-UHFFFAOYSA-N 1-[3-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]propyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 YJELZTGEMAQGHU-UHFFFAOYSA-N 0.000 claims 1
- QFKHRAMBZLTSDV-UHFFFAOYSA-N 1-[4-[2-[[4-[3-chloro-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OC=4C=NC(C)=CC=4)=CC=3)=C12 QFKHRAMBZLTSDV-UHFFFAOYSA-N 0.000 claims 1
- JNCKWWADGCZZGL-UHFFFAOYSA-N 1-[4-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 JNCKWWADGCZZGL-UHFFFAOYSA-N 0.000 claims 1
- HUFIMPWZKFFPQW-UHFFFAOYSA-N 1-[4-[2-[[4-[3-methyl-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)=C12 HUFIMPWZKFFPQW-UHFFFAOYSA-N 0.000 claims 1
- MCUKWCRQNBUPGQ-UHFFFAOYSA-N 1-[4-[3-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]propyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CCCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 MCUKWCRQNBUPGQ-UHFFFAOYSA-N 0.000 claims 1
- OKMXQCNGZVQOKH-UHFFFAOYSA-N 2-[2-[[4-[3-chloro-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl-methylamino]ethanol Chemical compound C=12C(OCCN(CCO)C)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OC1=CC=C(C)N=C1 OKMXQCNGZVQOKH-UHFFFAOYSA-N 0.000 claims 1
- GTLHFFSIEBUGAS-UHFFFAOYSA-N 2-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl-(2-hydroxyethyl)amino]ethanol Chemical compound C=12C(OCCN(CCO)CCO)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 GTLHFFSIEBUGAS-UHFFFAOYSA-N 0.000 claims 1
- VDCRSOSLUISLAL-UHFFFAOYSA-N 2-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl-methylamino]ethanol Chemical compound C=12C(OCCN(CCO)C)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 VDCRSOSLUISLAL-UHFFFAOYSA-N 0.000 claims 1
- HQKWSNMALVWOBX-UHFFFAOYSA-N 2-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl]isoindole-1,3-dione Chemical compound ClC1=CC(NC=2C=3C(OCCN4C(C5=CC=CC=C5C4=O)=O)=NNC=3N=CN=2)=CC=C1OCC1=CC=CC=N1 HQKWSNMALVWOBX-UHFFFAOYSA-N 0.000 claims 1
- GMOPIFJDXGFMTI-UHFFFAOYSA-N 2-[2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethylamino]ethanol Chemical compound C=12C(OCCNCCO)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 GMOPIFJDXGFMTI-UHFFFAOYSA-N 0.000 claims 1
- VCBCMTRNJOCIDN-UHFFFAOYSA-N 2-[[4-(3-methyl-4-phenylmethoxyanilino)-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethanol Chemical compound CC1=CC(NC=2C=3C(OCCO)=NNC=3N=CN=2)=CC=C1OCC1=CC=CC=C1 VCBCMTRNJOCIDN-UHFFFAOYSA-N 0.000 claims 1
- DWQMEVYRCUVXHE-UHFFFAOYSA-N 2-[[4-(3-methyl-4-phenylmethoxyanilino)-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl methanesulfonate Chemical compound CC1=CC(NC=2C=3C(OCCOS(C)(=O)=O)=NNC=3N=CN=2)=CC=C1OCC1=CC=CC=C1 DWQMEVYRCUVXHE-UHFFFAOYSA-N 0.000 claims 1
- UBCJSZANJDXNGO-UHFFFAOYSA-N 2-[[4-[3-chloro-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethanol Chemical compound C1=NC(C)=CC=C1OC(C(=C1)Cl)=CC=C1NC1=NC=NC2=C1C(OCCO)=NN2 UBCJSZANJDXNGO-UHFFFAOYSA-N 0.000 claims 1
- BVXBBIZFISJCMB-UHFFFAOYSA-N 2-[[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethanol Chemical compound C=12C(OCCO)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 BVXBBIZFISJCMB-UHFFFAOYSA-N 0.000 claims 1
- SKBXFJWEVNAXDN-UHFFFAOYSA-N 2-[[4-[3-chloro-4-[(3-fluorophenyl)methoxy]anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethanol Chemical compound C=12C(OCCO)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 SKBXFJWEVNAXDN-UHFFFAOYSA-N 0.000 claims 1
- QQKPLRVQGDAHMD-UHFFFAOYSA-N 2-[[4-[3-ethyl-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethanol Chemical compound CCC1=CC(NC=2C=3C(OCCO)=NNC=3N=CN=2)=CC=C1OCC1=CC=CC=N1 QQKPLRVQGDAHMD-UHFFFAOYSA-N 0.000 claims 1
- LUUWYBPINNTPHS-UHFFFAOYSA-N 2-[[4-[3-ethyl-4-(pyridin-2-ylmethoxy)anilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethyl methanesulfonate Chemical compound CCC1=CC(NC=2C=3C(OCCOS(C)(=O)=O)=NNC=3N=CN=2)=CC=C1OCC1=CC=CC=N1 LUUWYBPINNTPHS-UHFFFAOYSA-N 0.000 claims 1
- NUVBYFJZLGNHNV-UHFFFAOYSA-N 2-[[4-[3-fluoro-4-(6-methylpyridin-3-yl)oxyanilino]-1h-pyrazolo[3,4-d]pyrimidin-3-yl]oxy]ethanol Chemical compound C1=NC(C)=CC=C1OC(C(=C1)F)=CC=C1NC1=NC=NC2=C1C(OCCO)=NN2 NUVBYFJZLGNHNV-UHFFFAOYSA-N 0.000 claims 1
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- QDOLMCSPGVWMFW-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-ethylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(CC)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 QDOLMCSPGVWMFW-UHFFFAOYSA-N 0.000 claims 1
- KYLCGDSKIUQKFX-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-fluoropiperidin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(F)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 KYLCGDSKIUQKFX-UHFFFAOYSA-N 0.000 claims 1
- BZUIGXZUUGQBLL-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 BZUIGXZUUGQBLL-UHFFFAOYSA-N 0.000 claims 1
- VEWLBJRDDQOQHC-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-propan-2-ylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C(C)C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 VEWLBJRDDQOQHC-UHFFFAOYSA-N 0.000 claims 1
- MPSMEEDGQBLMNI-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(methylamino)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=12C(OCCNC)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 MPSMEEDGQBLMNI-UHFFFAOYSA-N 0.000 claims 1
- BERLNDGSHCXVKP-UHFFFAOYSA-N n-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-3-[3-(4-methylpiperazin-1-yl)propoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4N=CC=CC=4)=CC=3)=C12 BERLNDGSHCXVKP-UHFFFAOYSA-N 0.000 claims 1
- UUHZEWZYPYVUKW-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-3-(2-pyrrolidin-1-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC=CC(COC=2C(=CC(NC=3C=4C(OCCN5CCCC5)=NNC=4N=CN=3)=CC=2)Cl)=C1 UUHZEWZYPYVUKW-UHFFFAOYSA-N 0.000 claims 1
- SLYDNKVLPRXSBW-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)=C12 SLYDNKVLPRXSBW-UHFFFAOYSA-N 0.000 claims 1
- IKXMFUGPORBDCU-UHFFFAOYSA-N n-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-3-[2-(methylamino)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=12C(OCCNC)=NNC2=NC=NC=1NC(C=C1Cl)=CC=C1OCC1=CC=CC(F)=C1 IKXMFUGPORBDCU-UHFFFAOYSA-N 0.000 claims 1
- YKRIAQZYXBQQGD-UHFFFAOYSA-N n-[3-ethyl-4-(pyridin-2-ylmethoxy)phenyl]-3-(2-morpholin-4-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(CC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCOCC1 YKRIAQZYXBQQGD-UHFFFAOYSA-N 0.000 claims 1
- BDHLBNXTIUYNJR-UHFFFAOYSA-N n-[3-ethyl-4-(pyridin-2-ylmethoxy)phenyl]-3-(2-pyrrolidin-1-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(CC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCCC1 BDHLBNXTIUYNJR-UHFFFAOYSA-N 0.000 claims 1
- GHACSHWDWWMCKR-UHFFFAOYSA-N n-[3-ethyl-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(CC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCN(C)CC1 GHACSHWDWWMCKR-UHFFFAOYSA-N 0.000 claims 1
- MLFHVUFDNZCQAX-UHFFFAOYSA-N n-[3-fluoro-4-(6-methylpyridin-3-yl)oxyphenyl]-3-(2-morpholin-4-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=NC(C)=CC=C1OC(C(=C1)F)=CC=C1NC1=NC=NC2=C1C(OCCN1CCOCC1)=NN2 MLFHVUFDNZCQAX-UHFFFAOYSA-N 0.000 claims 1
- XJIKCEACQPGKHS-UHFFFAOYSA-N n-[3-fluoro-4-(6-methylpyridin-3-yl)oxyphenyl]-3-(2-pyrrolidin-1-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=NC(C)=CC=C1OC(C(=C1)F)=CC=C1NC1=NC=NC2=C1C(OCCN1CCCC1)=NN2 XJIKCEACQPGKHS-UHFFFAOYSA-N 0.000 claims 1
- FZQPWQLURSOWBV-UHFFFAOYSA-N n-[3-fluoro-4-(6-methylpyridin-3-yl)oxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(F)C(OC=4C=NC(C)=CC=4)=CC=3)=C12 FZQPWQLURSOWBV-UHFFFAOYSA-N 0.000 claims 1
- FNYXVRRNSPMXBR-UHFFFAOYSA-N n-[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]-3-(2-pyrrolidin-1-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(OC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCCC1 FNYXVRRNSPMXBR-UHFFFAOYSA-N 0.000 claims 1
- RZOKDOWVJGLDDT-UHFFFAOYSA-N n-[3-methoxy-4-(pyridin-2-ylmethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(OC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCN(C)CC1 RZOKDOWVJGLDDT-UHFFFAOYSA-N 0.000 claims 1
- HOARRNDFFQFMGW-UHFFFAOYSA-N n-[3-methyl-4-(6-methylpyridin-3-yl)oxyphenyl]-3-(2-morpholin-4-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC1=NC=NC2=C1C(OCCN1CCOCC1)=NN2 HOARRNDFFQFMGW-UHFFFAOYSA-N 0.000 claims 1
- AMLYVVGYTYLWDS-UHFFFAOYSA-N n-[3-methyl-4-(6-methylpyridin-3-yl)oxyphenyl]-3-(2-pyrrolidin-1-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1=NC(C)=CC=C1OC(C(=C1)C)=CC=C1NC1=NC=NC2=C1C(OCCN1CCCC1)=NN2 AMLYVVGYTYLWDS-UHFFFAOYSA-N 0.000 claims 1
- RFZKZFQIQQJPLI-UHFFFAOYSA-N n-[3-methyl-4-(6-methylpyridin-3-yl)oxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(C)C(OC=4C=NC(C)=CC=4)=CC=3)=C12 RFZKZFQIQQJPLI-UHFFFAOYSA-N 0.000 claims 1
- DFFAQXMSNPIZHX-UHFFFAOYSA-N n-[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]-3-(2-morpholin-4-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(C)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCOCC1 DFFAQXMSNPIZHX-UHFFFAOYSA-N 0.000 claims 1
- HBMUCTKSTFUXDH-UHFFFAOYSA-N n-[3-methyl-4-(pyridin-2-ylmethoxy)phenyl]-3-(2-pyrrolidin-1-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2N=CC=CC=2)C(C)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCCC1 HBMUCTKSTFUXDH-UHFFFAOYSA-N 0.000 claims 1
- LPAPTKFHFVZVPK-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]-3-(2-pyrrolidin-1-ylethoxy)-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCCC1 LPAPTKFHFVZVPK-UHFFFAOYSA-N 0.000 claims 1
- ONFMFJIKYCBJOF-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]-3-methoxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(OC)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCN(C)CC1 ONFMFJIKYCBJOF-UHFFFAOYSA-N 0.000 claims 1
- ASRZQFXSNXTQMQ-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]-3-methylphenyl]-3-[2-(1,4-oxazepan-4-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C=1C=C(OCC=2C=C(F)C=CC=2)C(C)=CC=1NC(C1=2)=NC=NC=2NN=C1OCCN1CCCOCC1 ASRZQFXSNXTQMQ-UHFFFAOYSA-N 0.000 claims 1
- ZUGVWGZKENQLAU-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]-3-methylphenyl]-3-[2-(4-methoxypiperidin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CC(OC)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(C)C(OCC=4C=C(F)C=CC=4)=CC=3)=C12 ZUGVWGZKENQLAU-UHFFFAOYSA-N 0.000 claims 1
- ASIZGLWKKPLNHP-UHFFFAOYSA-N n-[4-[(3-fluorophenyl)methoxy]-3-methylphenyl]-3-[2-(4-methylpiperazin-1-yl)ethoxy]-1h-pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCOC1=NNC2=NC=NC(NC=3C=C(C)C(OCC=4C=C(F)C=CC=4)=CC=3)=C12 ASIZGLWKKPLNHP-UHFFFAOYSA-N 0.000 claims 1
- 239000012434 nucleophilic reagent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
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| US7569577B2 (en) | 2003-09-16 | 2009-08-04 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| JP2008231004A (ja) * | 2007-03-19 | 2008-10-02 | Sumitomo Seika Chem Co Ltd | アルコキシ−２−メルカプトベンゾチアゾールの製造方法 |
| CA2889572C (en) | 2012-11-08 | 2019-03-05 | Pfizer Inc. | Heteroaromatic compounds as dopamine d1 ligands |
| US20160318897A1 (en) | 2013-12-18 | 2016-11-03 | Basf Se | Azole compounds carrying an imine-derived substituent |
| US9616063B2 (en) * | 2014-12-01 | 2017-04-11 | Astrazeneca Ab | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
| EP3445768A4 (en) * | 2016-04-19 | 2019-12-18 | The Regents of The University of California | HERITAGE INHIBITORS AND USES THEREOF |
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| GB0126433D0 (en) * | 2001-11-03 | 2002-01-02 | Astrazeneca Ab | Compounds |
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| TWI324597B (en) * | 2002-03-28 | 2010-05-11 | Astrazeneca Ab | Quinazoline derivatives |
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| AU2003226705B2 (en) | 2002-03-30 | 2008-11-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 4-(N-phenylamino)-quinazolines / quinolines as tyrosine kinase inhibitors |
| GB0309009D0 (en) * | 2003-04-22 | 2003-05-28 | Astrazeneca Ab | Quinazoline derivatives |
| GB0309850D0 (en) * | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0413066A (pt) * | 2003-07-29 | 2006-10-17 | Astrazeneca Ab | derivado de quinazolina, ou um sal farmaceuticamente aceitável, ou um éster farmaceuticamente aceitável do mesmo, da fórmula i, uso e processo para a preparação do mesmo, composto, composição farmacêutica, e, métodos para a produção de um efeito antiproliferativo em um animal de sangue quente, para a prevenção ou tratamento de um tumor, para prover um efeito inibitório de tirosina quinase de egfr seletivo, e para tratar um cáncer em um animal de sangue quente |
| GB0317665D0 (en) * | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| EP1664030A1 (en) * | 2003-09-16 | 2006-06-07 | AstraZeneca AB | Quinazoline derivatives |
| GB0321648D0 (en) * | 2003-09-16 | 2003-10-15 | Astrazeneca Ab | Quinazoline derivatives |
| BRPI0414488A (pt) * | 2003-09-16 | 2006-11-14 | Astrazeneca Ab | derivado de quinazolina, composição farmacêutica, uso de um derivado de quinazolina, métodos para produzir um efeito anti - proliferativo em um animal de sangue quente, para prevenção ou tratamento de tumores em um aminal de sangue quente, para fornecer um efeito inibidor da tirosina quinase de egfr seletivo em um animal de sangue quente e para tratar um cáncer em um animal de sangue quente e, processo para a preparação de um derivado de quinazolina |
| AU2004272350A1 (en) * | 2003-09-16 | 2005-03-24 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| US7569577B2 (en) * | 2003-09-16 | 2009-08-04 | Astrazeneca Ab | Quinazoline derivatives as tyrosine kinase inhibitors |
| JP4036885B2 (ja) * | 2003-09-19 | 2008-01-23 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
| DE602004004811T2 (de) * | 2003-09-19 | 2007-11-22 | Astrazeneca Ab | Chinazolinderivate |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
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| GB0326459D0 (en) * | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| ATE413389T1 (de) * | 2004-02-03 | 2008-11-15 | Astrazeneca Ab | Chinazolinderivate |
| CA2567832A1 (en) * | 2004-06-04 | 2005-12-15 | Astrazeneca Ab | Quinazoline derivatives as erbb receptor tyrosine kinases |
| GB0504474D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0504475D0 (en) * | 2005-03-04 | 2005-04-13 | Astrazeneca Ab | Chemical compounds |
| GB0508717D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| GB0508715D0 (en) * | 2005-04-29 | 2005-06-08 | Astrazeneca Ab | Chemical compounds |
| US7820683B2 (en) * | 2005-09-20 | 2010-10-26 | Astrazeneca Ab | 4-(1H-indazol-5-yl-amino)-quinazoline compounds as erbB receptor tyrosine kinase inhibitors for the treatment of cancer |
| US20090239861A1 (en) * | 2005-09-20 | 2009-09-24 | Robert Hugh Bradbury | Quinazoline derivatives as anticancer agents |
| ATE443053T1 (de) * | 2005-12-02 | 2009-10-15 | Astrazeneca Ab | Als inhibitoren von erbb-tyrosinkinase verwendete chinazoleinderivate |
-
2005
- 2005-12-12 CN CN2005800483311A patent/CN101124228B/zh not_active Expired - Fee Related
- 2005-12-12 US US11/792,921 patent/US7947676B2/en not_active Expired - Fee Related
- 2005-12-12 AT AT05818622T patent/ATE501148T1/de not_active IP Right Cessation
- 2005-12-12 JP JP2007546165A patent/JP4881875B2/ja not_active Expired - Fee Related
- 2005-12-12 WO PCT/GB2005/004770 patent/WO2006064196A1/en not_active Ceased
- 2005-12-12 EP EP05818622A patent/EP1838712B8/en not_active Expired - Lifetime
- 2005-12-12 DE DE602005026865T patent/DE602005026865D1/de not_active Expired - Lifetime
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