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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| ES2305844T3 (es) | 2003-09-16 | 2008-11-01 | Astrazeneca Ab | Derivados de quinazolina como inhibidores de tirosina cinasa. |
| GB0322409D0 (en) * | 2003-09-25 | 2003-10-29 | Astrazeneca Ab | Quinazoline derivatives |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| JP5032851B2 (ja) | 2004-02-03 | 2012-09-26 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
| 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 |
| MD20150037A2 (ro) | 2012-11-08 | 2015-11-30 | Pfizer Inc. | Compuşi heteroaromatici şi utilizarea lor ca liganzi de dopamină D1 |
| CN105829296A (zh) | 2013-12-18 | 2016-08-03 | 巴斯夫欧洲公司 | 带有亚胺衍生的取代基的唑类化合物 |
| 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 |
| US20190119284A1 (en) * | 2016-04-19 | 2019-04-25 | The Regents Of The University Of California | ErbB Inhibitors and Uses Thereof |
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-
2005
- 2005-12-12 EP EP05818622A patent/EP1838712B8/en not_active Expired - Lifetime
- 2005-12-12 DE DE602005026865T patent/DE602005026865D1/de not_active Expired - Lifetime
- 2005-12-12 AT AT05818622T patent/ATE501148T1/de not_active IP Right Cessation
- 2005-12-12 CN CN2005800483311A patent/CN101124228B/zh not_active Expired - Fee Related
- 2005-12-12 WO PCT/GB2005/004770 patent/WO2006064196A1/en not_active Ceased
- 2005-12-12 JP JP2007546165A patent/JP4881875B2/ja not_active Expired - Fee Related
- 2005-12-12 US US11/792,921 patent/US7947676B2/en not_active Expired - Fee Related
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