JP4147184B2 - ４−アミノ−６−フェニル−ピロロ［２，３−ｄ］ピリミジン誘導体 - Google Patents

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Publication number

JP4147184B2

JP4147184B2 JP2003518550A JP2003518550A JP4147184B2 JP 4147184 B2 JP4147184 B2 JP 4147184B2 JP 2003518550 A JP2003518550 A JP 2003518550A JP 2003518550 A JP2003518550 A JP 2003518550A JP 4147184 B2 JP4147184 B2 JP 4147184B2

Authority

JP

Japan

Prior art keywords

phenyl

pyrrolo

pyrimidin

ylmethyl

amine

Prior art date

2001-08-07

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.)

Expired - Fee Related

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• JSLCFLYSDVRTNX-UHFFFAOYSA-N 6-phenyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C=1C2=C(N)N=CNC2=NC=1C1=CC=CC=C1 JSLCFLYSDVRTNX-UHFFFAOYSA-N 0.000 title 1
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 238000002360 preparation method Methods 0.000 claims abstract description 8
• 150000001875 compounds Chemical class 0.000 claims description 248
• -1 4-ethyl-piperazin-1-ylmethyl Chemical group 0.000 claims description 130
• 150000003839 salts Chemical class 0.000 claims description 55
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 24
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 23
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 15
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• FZPJHQLFSGJVLV-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[4-[4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanone Chemical compound C1CN(CC)CCN1C(=O)C1=CC=C(C=2NC3=NC=NC(OC=4C(=C5C=C(C)NC5=CC=4)F)=C3C=2)C=C1 FZPJHQLFSGJVLV-UHFFFAOYSA-N 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
• LWLFPYBXHSCBJQ-HXUWFJFHSA-N 2-(4-methylpiperazin-1-yl)-n-[[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=1)=CC=CC=1CNC(=O)CN1CCN(C)CC1 LWLFPYBXHSCBJQ-HXUWFJFHSA-N 0.000 claims description 2
• YGVOKLMLPAPRSE-QGZVFWFLSA-N 2-(dimethylamino)-n-[[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(CNC(=O)CN(C)C)=C1 YGVOKLMLPAPRSE-QGZVFWFLSA-N 0.000 claims description 2
• JZKJSOVRPVKVJU-UHFFFAOYSA-N 2-(dimethylamino)-n-[[4-[4-(4-phenylmethoxyanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 JZKJSOVRPVKVJU-UHFFFAOYSA-N 0.000 claims description 2
• RQUNVDLGCLUTSV-UHFFFAOYSA-N 5-[[6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN3CCOCC3)=CC=2)=C1 RQUNVDLGCLUTSV-UHFFFAOYSA-N 0.000 claims description 2
• WVUZPSXFRZJDAH-MRXNPFEDSA-N 6-[3-[(dimethylamino)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(CN(C)C)=C1 WVUZPSXFRZJDAH-MRXNPFEDSA-N 0.000 claims description 2
• UONQWQBISKARJI-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(OC=4C(=C5C=C(C)NC5=CC=4)F)=C3C=2)C=C1 UONQWQBISKARJI-UHFFFAOYSA-N 0.000 claims description 2
• KENDEWHISLNOER-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-[(6-methoxypyridin-3-yl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC=4C=NC(OC)=CC=4)=C3C=2)C=C1 KENDEWHISLNOER-UHFFFAOYSA-N 0.000 claims description 2
• JYYKKUZCOCGFKD-LJQANCHMSA-N 6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCN(C)CC1 JYYKKUZCOCGFKD-LJQANCHMSA-N 0.000 claims description 2
• LMXINPZKDPTNLH-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-(4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 LMXINPZKDPTNLH-UHFFFAOYSA-N 0.000 claims description 2
• SAHIPVAKCHTXJD-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C5OCOC5=CC=4)=C3C=2)C=C1 SAHIPVAKCHTXJD-UHFFFAOYSA-N 0.000 claims description 2
• UQQVZPJUYVXDMY-UHFFFAOYSA-N n-(2-methoxypyridin-4-yl)-6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN3CCOCC3)=CC=2)=C1 UQQVZPJUYVXDMY-UHFFFAOYSA-N 0.000 claims description 2
• VADZPEBTDDGYRI-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN(C)CC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)=C1 VADZPEBTDDGYRI-UHFFFAOYSA-N 0.000 claims description 2
• SNDKGMVRQGGECV-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 SNDKGMVRQGGECV-UHFFFAOYSA-N 0.000 claims description 2
• ZCYUIVDZIUALMV-UHFFFAOYSA-N n-[(3-chlorophenyl)methyl]-6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC=4C=C(Cl)C=CC=4)=C3C=2)C=C1 ZCYUIVDZIUALMV-UHFFFAOYSA-N 0.000 claims description 2
• IHJXHGYVACNQII-UHFFFAOYSA-N n-[[3-[4-(3-chloro-4-fluoroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]-2-(dimethylamino)acetamide Chemical compound CN(C)CC(=O)NCC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)=C1 IHJXHGYVACNQII-UHFFFAOYSA-N 0.000 claims description 2
• YHXKSCKFPZINRT-UHFFFAOYSA-N n-[[4-[4-(3-chloro-4-fluoroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]-2-(dimethylamino)acetamide Chemical compound C1=CC(CNC(=O)CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 YHXKSCKFPZINRT-UHFFFAOYSA-N 0.000 claims description 2
• ULBYRMZHKATTDZ-UHFFFAOYSA-N n-[[4-[4-(3-chloro-4-fluoroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]-3-(diethylamino)propanamide Chemical compound C1=CC(CNC(=O)CCN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 ULBYRMZHKATTDZ-UHFFFAOYSA-N 0.000 claims description 2
• 150000001721 carbon Chemical group 0.000 claims 5
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 3
• CXUGCCOBKBXXQC-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-[(2-methoxypyridin-4-yl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC=4C=C(OC)N=CC=4)=C3C=2)C=C1 CXUGCCOBKBXXQC-UHFFFAOYSA-N 0.000 claims 2
• 125000003118 aryl group Chemical group 0.000 claims 2
• PKDXBDHITIDKIK-OAQYLSRUSA-N 2-(4-ethylpiperazin-1-yl)-n-[[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound C1CN(CC)CCN1CC(=O)NCC1=CC=C(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)C=C1 PKDXBDHITIDKIK-OAQYLSRUSA-N 0.000 claims 1
• FTFBSDWSCZFPGA-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)-n-[[4-[4-(4-phenylmethoxyanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound C1CN(C)CCN1CC(=O)NCC1=CC=C(C=2NC3=NC=NC(NC=4C=CC(OCC=5C=CC=CC=5)=CC=4)=C3C=2)C=C1 FTFBSDWSCZFPGA-UHFFFAOYSA-N 0.000 claims 1
• SYRAZXQPVGXSOZ-QGZVFWFLSA-N 2-(dimethylamino)-n-[[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(CNC(=O)CN(C)C)C=C1 SYRAZXQPVGXSOZ-QGZVFWFLSA-N 0.000 claims 1
• SQWRUZOVFYJZSP-GOSISDBHSA-N 2-[2-hydroxyethyl-[[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]amino]ethanol Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(CN(CCO)CCO)C=C1 SQWRUZOVFYJZSP-GOSISDBHSA-N 0.000 claims 1
• JIBWXMKJDYZULM-UHFFFAOYSA-N 2-methoxy-5-[[6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=C(CN3CCN(C)CC3)C=CC=1)N2 JIBWXMKJDYZULM-UHFFFAOYSA-N 0.000 claims 1
• ZUVPUVVVXOXGKP-UHFFFAOYSA-N 2-methoxy-5-[[6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCOCC3)=CC=1)N2 ZUVPUVVVXOXGKP-UHFFFAOYSA-N 0.000 claims 1
• JCOQTKKATRMBGY-UHFFFAOYSA-N 2-methoxy-5-[[6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]phenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCN(C)CC3)=CC=1)N2 JCOQTKKATRMBGY-UHFFFAOYSA-N 0.000 claims 1
• ZBHOIRLDQFYQNX-UHFFFAOYSA-N 2-methyl-5-[[6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]phenol Chemical compound C1CN(C)CCN1CC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(O)C(C)=CC=4)=C3C=2)=C1 ZBHOIRLDQFYQNX-UHFFFAOYSA-N 0.000 claims 1
• AXKYFALRRYJIEM-UHFFFAOYSA-N 2-methyl-5-[[6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]phenol Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C(O)C(C)=CC=4)=C3C=2)C=C1 AXKYFALRRYJIEM-UHFFFAOYSA-N 0.000 claims 1
• TWSQVFRVEOIOCR-LJQANCHMSA-N 2-morpholin-4-yl-n-[[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]acetamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CNC(=O)CN1CCOCC1 TWSQVFRVEOIOCR-LJQANCHMSA-N 0.000 claims 1
• IVVQDEMOKGQRMX-HXUWFJFHSA-N 3-(diethylamino)-n-[[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]propanamide Chemical compound C1=CC(CNC(=O)CCN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 IVVQDEMOKGQRMX-HXUWFJFHSA-N 0.000 claims 1
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
• MBCKXBTZNDRJQI-LJQANCHMSA-N 4-(dimethylamino)-n-[[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]butanamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(CNC(=O)CCCN(C)C)C=C1 MBCKXBTZNDRJQI-LJQANCHMSA-N 0.000 claims 1
• YFYSEAQFIGPGCR-UHFFFAOYSA-N 4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidine Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(OC=4C(=C5C=C(C)NC5=CC=4)F)=C3C=2)C=C1 YFYSEAQFIGPGCR-UHFFFAOYSA-N 0.000 claims 1
• OUSVRYSWPGRUEW-UHFFFAOYSA-N 4-[[4-[4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]morpholine Chemical compound C=1C=C2NC(C)=CC2=C(F)C=1OC(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCOCC1 OUSVRYSWPGRUEW-UHFFFAOYSA-N 0.000 claims 1
• HZASJPLZTDZQCT-UHFFFAOYSA-N 4-[[6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCOCC3)=CC=1)N2 HZASJPLZTDZQCT-UHFFFAOYSA-N 0.000 claims 1
• JAILEVCUESUCFU-UHFFFAOYSA-N 4-[[6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC4=CC(=O)NC=C4)=C3C=2)C=C1 JAILEVCUESUCFU-UHFFFAOYSA-N 0.000 claims 1
• MEKPURFANDMLRY-UHFFFAOYSA-N 4-[[6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC4=CC(=O)NC=C4)=C3C=2)C=C1 MEKPURFANDMLRY-UHFFFAOYSA-N 0.000 claims 1
• MZCPMOIZOBQRSM-UHFFFAOYSA-N 4-[[6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC(=O)NC=C1 MZCPMOIZOBQRSM-UHFFFAOYSA-N 0.000 claims 1
• KCPZJYXDONJLQD-UHFFFAOYSA-N 4-[[[6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]methyl]-1h-pyridin-2-one Chemical compound C1=CNC(=O)C=C1CNC1=NC=NC2=C1C=C(C=1C=CC(CN3CCOCC3)=CC=1)N2 KCPZJYXDONJLQD-UHFFFAOYSA-N 0.000 claims 1
• GRVDQVPNRYKAAC-UHFFFAOYSA-N 4-[[[6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]methyl]-1h-pyridin-2-one Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC4=CC(=O)NC=C4)=C3C=2)C=C1 GRVDQVPNRYKAAC-UHFFFAOYSA-N 0.000 claims 1
• RBAAISSKLOLFHM-UHFFFAOYSA-N 4-[[[6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]methyl]-1h-pyridin-2-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC4=CC(=O)NC=C4)=C3C=2)C=C1 RBAAISSKLOLFHM-UHFFFAOYSA-N 0.000 claims 1
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
• FWGFRWILELKXQZ-UHFFFAOYSA-N 5-[[6-[3-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=C(CN(C)C)C=CC=1)N2 FWGFRWILELKXQZ-UHFFFAOYSA-N 0.000 claims 1
• RZZHUWWZHXYOEA-UHFFFAOYSA-N 5-[[6-[3-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-2-methylphenol Chemical compound CN(C)CC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(O)C(C)=CC=4)=C3C=2)=C1 RZZHUWWZHXYOEA-UHFFFAOYSA-N 0.000 claims 1
• HNEVNFNSXZMAIY-UHFFFAOYSA-N 5-[[6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC4=CNC(=O)C=C4)=C3C=2)C=C1 HNEVNFNSXZMAIY-UHFFFAOYSA-N 0.000 claims 1
• WCGWWVHEMGKLRA-UHFFFAOYSA-N 5-[[6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC4=CNC(=O)C=C4)=C3C=2)C=C1 WCGWWVHEMGKLRA-UHFFFAOYSA-N 0.000 claims 1
• DRMUVMMNIQLHAV-UHFFFAOYSA-N 5-[[6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1h-pyridin-2-one Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CNC(=O)C=C1 DRMUVMMNIQLHAV-UHFFFAOYSA-N 0.000 claims 1
• FEZQOBBAEFASGP-UHFFFAOYSA-N 5-[[6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN(C)C)=CC=1)N2 FEZQOBBAEFASGP-UHFFFAOYSA-N 0.000 claims 1
• UFQIDRWSQPCIEQ-UHFFFAOYSA-N 5-[[6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-2-methylphenol Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(C)C(O)=C1 UFQIDRWSQPCIEQ-UHFFFAOYSA-N 0.000 claims 1
• PDXXURIVCLTTQS-UHFFFAOYSA-N 5-[[[6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]methyl]-1h-pyridin-2-one Chemical compound N1C(=O)C=CC(CNC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN3CCOCC3)=CC=2)=C1 PDXXURIVCLTTQS-UHFFFAOYSA-N 0.000 claims 1
• FREBMHFYZIETGX-UHFFFAOYSA-N 5-[[[6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]methyl]-1h-pyridin-2-one Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC4=CNC(=O)C=C4)=C3C=2)C=C1 FREBMHFYZIETGX-UHFFFAOYSA-N 0.000 claims 1
• VZCZFEMBBYYAGU-GOSISDBHSA-N 6-[3-(diethylaminomethyl)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CCN(CC)CC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 VZCZFEMBBYYAGU-GOSISDBHSA-N 0.000 claims 1
• TUOBSOQBBYNZLT-SOAGJPPSSA-N 6-[3-[(3,5-dimethylpiperazin-1-yl)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=1)=CC=CC=1CN1CC(C)NC(C)C1 TUOBSOQBBYNZLT-SOAGJPPSSA-N 0.000 claims 1
• WXTTVWVQKPFYKX-HXUWFJFHSA-N 6-[3-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(CC)CCN1CC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 WXTTVWVQKPFYKX-HXUWFJFHSA-N 0.000 claims 1
• OTAINLPPBNSXTJ-LJQANCHMSA-N 6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=1)=CC=CC=1CN1CCN(C)CC1 OTAINLPPBNSXTJ-LJQANCHMSA-N 0.000 claims 1
• IMZVRJHLNIWPNE-UHFFFAOYSA-N 6-[4-(diethylaminomethyl)phenyl]-n-(4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2NC(C=C1)=CC=C1OCC1=CC=CC=C1 IMZVRJHLNIWPNE-UHFFFAOYSA-N 0.000 claims 1
• KBGWVYSAOZGJDF-GOSISDBHSA-N 6-[4-(diethylaminomethyl)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 KBGWVYSAOZGJDF-GOSISDBHSA-N 0.000 claims 1
• UXERAPXHQFRZBX-UHFFFAOYSA-N 6-[4-(diethylaminomethyl)phenyl]-n-[(3-methylphenyl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2NCC1=CC=CC(C)=C1 UXERAPXHQFRZBX-UHFFFAOYSA-N 0.000 claims 1
• QWBAIXBCXTVTDH-MRXNPFEDSA-N 6-[4-(ethylaminomethyl)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CNCC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 QWBAIXBCXTVTDH-MRXNPFEDSA-N 0.000 claims 1
• NXUOBBWDWKSWQF-OAHLLOKOSA-N 6-[4-(methylaminomethyl)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CNC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 NXUOBBWDWKSWQF-OAHLLOKOSA-N 0.000 claims 1
• URLRWQLHEMZBNO-UHFFFAOYSA-N 6-[4-(morpholin-4-ylmethyl)phenyl]-n-(4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCOCC1 URLRWQLHEMZBNO-UHFFFAOYSA-N 0.000 claims 1
• RLXDINBVLLERRM-GOSISDBHSA-N 6-[4-(morpholin-4-ylmethyl)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCOCC1 RLXDINBVLLERRM-GOSISDBHSA-N 0.000 claims 1
• AROAYADHOHAUQV-HXUWFJFHSA-N 6-[4-[(2-morpholin-4-ylethylamino)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CNCCN1CCOCC1 AROAYADHOHAUQV-HXUWFJFHSA-N 0.000 claims 1
• YEXWJKVIUNKWKU-UHFFFAOYSA-N 6-[4-[(3,5-dimethylpiperazin-1-yl)methyl]phenyl]-n-(4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1C(C)NC(C)CN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=CC(OCC=5C=CC=CC=5)=CC=4)=C3C=2)C=C1 YEXWJKVIUNKWKU-UHFFFAOYSA-N 0.000 claims 1
• YLMXVFUDIPWJEC-SOAGJPPSSA-N 6-[4-[(3,5-dimethylpiperazin-1-yl)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CC(C)NC(C)C1 YLMXVFUDIPWJEC-SOAGJPPSSA-N 0.000 claims 1
• JHVZTRTXZPCMEP-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-(4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=CC(OCC=5C=CC=CC=5)=CC=4)=C3C=2)C=C1 JHVZTRTXZPCMEP-UHFFFAOYSA-N 0.000 claims 1
• BWKMPTUCNHSQLW-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-(6-methoxypyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=NC(OC)=CC=4)=C3C=2)C=C1 BWKMPTUCNHSQLW-UHFFFAOYSA-N 0.000 claims 1
• JKYHVQVPACXKEL-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-[(3-methoxyphenyl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC=4C=C(OC)C=CC=4)=C3C=2)C=C1 JKYHVQVPACXKEL-UHFFFAOYSA-N 0.000 claims 1
• BFQAHALNGLGKPA-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-[(3-methylphenyl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NCC=4C=C(C)C=CC=4)=C3C=2)C=C1 BFQAHALNGLGKPA-UHFFFAOYSA-N 0.000 claims 1
• IVMGPEWRUNJQOE-UHFFFAOYSA-N 6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-n-(4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=CC(OCC=5C=CC=CC=5)=CC=4)=C3C=2)C=C1 IVMGPEWRUNJQOE-UHFFFAOYSA-N 0.000 claims 1
• HMELEGZBVLVVAT-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-(2-methoxypyridin-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN(C)C)=CC=2)=C1 HMELEGZBVLVVAT-UHFFFAOYSA-N 0.000 claims 1
• VPXKYUMKBFXCRO-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-(6-methoxypyridin-3-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN(C)C)=CC=1)N2 VPXKYUMKBFXCRO-UHFFFAOYSA-N 0.000 claims 1
• HTYULQQPSJAQMF-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-[(3-methylphenyl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NCC1=CC=CC(C)=C1 HTYULQQPSJAQMF-UHFFFAOYSA-N 0.000 claims 1
• AORUSTUPGHKJIB-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-[(6-methoxypyridin-3-yl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC=C1CNC1=NC=NC2=C1C=C(C=1C=CC(CN(C)C)=CC=1)N2 AORUSTUPGHKJIB-UHFFFAOYSA-N 0.000 claims 1
• QMRDHSHAFFEVDC-QGZVFWFLSA-N 6-[4-[(tert-butylamino)methyl]phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(CNC(C)(C)C)C=C1 QMRDHSHAFFEVDC-QGZVFWFLSA-N 0.000 claims 1
• OONFNUWBHFSNBT-HXUWFJFHSA-N AEE788 Chemical class C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)C=C1 OONFNUWBHFSNBT-HXUWFJFHSA-N 0.000 claims 1
• RIMPFSUOOATEQH-UHFFFAOYSA-N [4-[4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2NC3=NC=NC(OC=4C(=C5C=C(C)NC5=CC=4)F)=C3C=2)C=C1 RIMPFSUOOATEQH-UHFFFAOYSA-N 0.000 claims 1
• UGMKJZVWTPFHDT-UHFFFAOYSA-N [4-[4-[(4-fluoro-2-methyl-1h-indol-5-yl)oxy]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2NC(C)=CC2=C(F)C=1OC(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1C(=O)N1CCOCC1 UGMKJZVWTPFHDT-UHFFFAOYSA-N 0.000 claims 1
• XDTGUTRFUQTJJE-HXUWFJFHSA-N n',n'-diethyl-n-[[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methyl]ethane-1,2-diamine Chemical compound C1=CC(CNCCN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 XDTGUTRFUQTJJE-HXUWFJFHSA-N 0.000 claims 1
• ZMRQWGOOEGAYKN-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(C=2NC3=NC=NC(NC=4C=C5OCOC5=CC=4)=C3C=2)C=CC=1CN1CCOCC1 ZMRQWGOOEGAYKN-UHFFFAOYSA-N 0.000 claims 1
• JSPLIDXVBSWCRT-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C5OCOC5=CC=4)=C3C=2)C=C1 JSPLIDXVBSWCRT-UHFFFAOYSA-N 0.000 claims 1
• APLXOMABWOKQHT-UHFFFAOYSA-N n-(1,3-benzodioxol-5-yl)-6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(OCO2)C2=C1 APLXOMABWOKQHT-UHFFFAOYSA-N 0.000 claims 1
• DYCSIZGWVXFEIP-UHFFFAOYSA-N n-(2-methoxypyridin-4-yl)-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1=NC(OC)=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN3CCN(C)CC3)=CC=2)=C1 DYCSIZGWVXFEIP-UHFFFAOYSA-N 0.000 claims 1
• SSBQTQHXVUSCTF-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-(diethylaminomethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CCN(CC)CC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)=C1 SSBQTQHXVUSCTF-UHFFFAOYSA-N 0.000 claims 1
• MMIMOVRWILIGKW-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=C(CN3CCOCC3)C=CC=1)N2 MMIMOVRWILIGKW-UHFFFAOYSA-N 0.000 claims 1
• GWMMPZXJPITCGQ-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-(piperidin-1-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=C(CN3CCCCC3)C=CC=1)N2 GWMMPZXJPITCGQ-UHFFFAOYSA-N 0.000 claims 1
• QNTMOGBXCJRMMV-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-(pyrrolidin-1-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=C(CN3CCCC3)C=CC=1)N2 QNTMOGBXCJRMMV-UHFFFAOYSA-N 0.000 claims 1
• VFMSVKPGGFGFEO-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(CC)CCN1CC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)=C1 VFMSVKPGGFGFEO-UHFFFAOYSA-N 0.000 claims 1
• LONCHVVLSOBRRD-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(C)CCN1CC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)=C1 LONCHVVLSOBRRD-UHFFFAOYSA-N 0.000 claims 1
• UZVDJBUBADEWMP-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-(diethylaminomethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CN(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 UZVDJBUBADEWMP-UHFFFAOYSA-N 0.000 claims 1
• SWMJBVNXBMUZIA-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCOCC3)=CC=1)N2 SWMJBVNXBMUZIA-UHFFFAOYSA-N 0.000 claims 1
• DBFICXSZHXAZOH-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-(piperidin-1-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCCCC3)=CC=1)N2 DBFICXSZHXAZOH-UHFFFAOYSA-N 0.000 claims 1
• XYSBMUQFGYDYPD-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-(pyrrolidin-1-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCCC3)=CC=1)N2 XYSBMUQFGYDYPD-UHFFFAOYSA-N 0.000 claims 1
• PPUFDICGNSVHNB-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-[(2-morpholin-4-ylethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CNCCN3CCOCC3)=CC=1)N2 PPUFDICGNSVHNB-UHFFFAOYSA-N 0.000 claims 1
• DAVAGKYYDDUIQJ-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-[(3,5-dimethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1C(C)NC(C)CN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)C=C1 DAVAGKYYDDUIQJ-UHFFFAOYSA-N 0.000 claims 1
• CZRCGPMKRUUDAR-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)C=C1 CZRCGPMKRUUDAR-UHFFFAOYSA-N 0.000 claims 1
• FDDLRCSDXGQPKF-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical class C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C(Cl)C(F)=CC=4)=C3C=2)C=C1 FDDLRCSDXGQPKF-UHFFFAOYSA-N 0.000 claims 1
• GGBOOTGKEIRYNN-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-[(oxan-4-ylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CNC3CCOCC3)=CC=1)N2 GGBOOTGKEIRYNN-UHFFFAOYSA-N 0.000 claims 1
• VLPVEMUWGJCQSJ-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[4-[(propan-2-ylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(CNC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 VLPVEMUWGJCQSJ-UHFFFAOYSA-N 0.000 claims 1
• BBADZLKFCFSARF-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN3CCOCC3)=CC=2)=C1 BBADZLKFCFSARF-UHFFFAOYSA-N 0.000 claims 1
• NTJIYJSKOJXKTB-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)C=C1 NTJIYJSKOJXKTB-UHFFFAOYSA-N 0.000 claims 1
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