CA2453881C - 4-amino-6-phenyl-pyrrolo[2,3-d]pyrimidine derivatives - Google Patents

Info

Publication number

CA2453881C

CA2453881C CA2453881A CA2453881A CA2453881C CA 2453881 C CA2453881 C CA 2453881C CA 2453881 A CA2453881 A CA 2453881A CA 2453881 A CA2453881 A CA 2453881A CA 2453881 C CA2453881 C CA 2453881C

Authority

CA

Canada

Prior art keywords

phenyl

formula

compound

pyrrolo

pyrimidin

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
• 238000000034 method Methods 0.000 claims abstract description 68
• 230000008569 process Effects 0.000 claims abstract description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 201000010099 disease Diseases 0.000 claims abstract description 25
• 238000011282 treatment Methods 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
• 238000002360 preparation method Methods 0.000 claims abstract description 20
• 150000001875 compounds Chemical class 0.000 claims description 443
• 150000003839 salts Chemical class 0.000 claims description 222
• -1 2-morpholin-4-yl-ethylamino Chemical group 0.000 claims description 112
• 239000000203 mixture Substances 0.000 claims description 70
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 65
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 229910052799 carbon Inorganic materials 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 32
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 32
• 230000005764 inhibitory process Effects 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 238000006243 chemical reaction Methods 0.000 claims description 22
• 125000004076 pyridyl group Chemical group 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
• 150000002367 halogens Chemical group 0.000 claims description 18
• 125000002757 morpholinyl group Chemical group 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 239000001301 oxygen Substances 0.000 claims description 18
• 125000005936 piperidyl group Chemical group 0.000 claims description 18
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 239000007858 starting material Substances 0.000 claims description 17
• 125000003282 alkyl amino group Chemical group 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 7
• 125000001041 indolyl group Chemical group 0.000 claims description 7
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000000524 functional group Chemical group 0.000 claims description 4
• 239000003638 chemical reducing agent Substances 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 2
• 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 description 2
• COAHCRGSDSNIPV-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCOCC3)=CC=1)N2 COAHCRGSDSNIPV-UHFFFAOYSA-N 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• 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 compound 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
• 125000002947 alkylene group Chemical group 0.000 claims 2
• 150000001721 carbon 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
• 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 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
• NUCCTFFSBFEJKO-HXUWFJFHSA-N 2-(4-methylpiperazin-1-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)CN1CCN(C)CC1 NUCCTFFSBFEJKO-HXUWFJFHSA-N 0.000 claims 1
• 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 1
• 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 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
• 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
• 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
• 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
• JMURKSSONHBBJJ-UHFFFAOYSA-N 4-[[[6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]methyl]-1h-pyridin-2-one Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NCC1=CC(=O)NC=C1 JMURKSSONHBBJJ-UHFFFAOYSA-N 0.000 claims 1
• MUHSAPQIVDUIJZ-UHFFFAOYSA-N 5-[[5-[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=2C3=C(NC4=CNC(=O)C=C4)N=CN=C3NC=2)C=C1 MUHSAPQIVDUIJZ-UHFFFAOYSA-N 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
• 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 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
• 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
• 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
• XETZSJYBDWAHFI-UHFFFAOYSA-N 5-[[[6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]methyl]-1h-pyridin-2-one Chemical compound C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NCC1=CNC(=O)C=C1 XETZSJYBDWAHFI-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
• JHOIDIHVDJYBCZ-GOSISDBHSA-N 6-[3-(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=1)=CC=CC=1CN1CCOCC1 JHOIDIHVDJYBCZ-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 compound 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 compound 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
• 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 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
• AALYMESKEMSIQZ-UHFFFAOYSA-N 6-[4-(diethylaminomethyl)phenyl]-n-[(3-methoxyphenyl)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(OC)=C1 AALYMESKEMSIQZ-UHFFFAOYSA-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
• 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
• WSKVOROEDJJFRR-UHFFFAOYSA-N 6-[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]-n-(2-methoxypyridin-4-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(CC)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C(OC)N=CC=4)=C3C=2)C=C1 WSKVOROEDJJFRR-UHFFFAOYSA-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
• 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
• 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
• JYYKKUZCOCGFKD-LJQANCHMSA-N 6-[4-[(4-methylpiperazin-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=C1CN1CCN(C)CC1 JYYKKUZCOCGFKD-LJQANCHMSA-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
• 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 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
• PJDONVWDQDCMPS-MRXNPFEDSA-N 6-[4-[(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=C(CN(C)C)C=C1 PJDONVWDQDCMPS-MRXNPFEDSA-N 0.000 claims 1
• CHADASGQTPDJDR-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-[(2-methoxypyridin-4-yl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC(CNC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN(C)C)=CC=2)=C1 CHADASGQTPDJDR-UHFFFAOYSA-N 0.000 claims 1
• LCOYUZKCVHQJFW-UHFFFAOYSA-N 6-[4-[(dimethylamino)methyl]phenyl]-n-[(3-methoxyphenyl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC=CC(CNC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN(C)C)=CC=2)=C1 LCOYUZKCVHQJFW-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
• 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 compound 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
• 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 compound C1CN(C)CCN1CC1=CC=C(C=2NC3=NC=NC(NC=4C=C5OCOC5=CC=4)=C3C=2)C=C1 SAHIPVAKCHTXJD-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
• 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 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 compound 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
• 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
• 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 compound 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 compound 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 compound 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 compound 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
• 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 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
• 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
• QEGSXEQNCZZZDA-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C1=CC(CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 QEGSXEQNCZZZDA-UHFFFAOYSA-N 0.000 claims 1
• VYVOFUYUAUGEAZ-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)-6-[4-(piperidin-1-ylmethyl)phenyl]-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=C1CN1CCCCC1 VYVOFUYUAUGEAZ-UHFFFAOYSA-N 0.000 claims 1
• UPRIQUXRYGPJPL-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)-6-[4-(pyrrolidin-1-ylmethyl)phenyl]-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=C1CN1CCCC1 UPRIQUXRYGPJPL-UHFFFAOYSA-N 0.000 claims 1
• IWRFBOAMTCQELH-UHFFFAOYSA-N n-(6-methoxypyridin-3-yl)-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=NC(OC)=CC=C1NC1=NC=NC2=C1C=C(C=1C=CC(CN3CCN(C)CC3)=CC=1)N2 IWRFBOAMTCQELH-UHFFFAOYSA-N 0.000 claims 1
• YXFDPDFSIRHFGA-QGZVFWFLSA-N n-[(1r)-1-(4-chlorophenyl)ethyl]-6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC(Cl)=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCOCC1 YXFDPDFSIRHFGA-QGZVFWFLSA-N 0.000 claims 1
• WCQSZBHPFNOBNU-GOSISDBHSA-N n-[(1r)-1-(4-chlorophenyl)ethyl]-6-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC(Cl)=CC=1)C(C=1C=2)=NC=NC=1NC=2C(C=C1)=CC=C1CN1CCN(C)CC1 WCQSZBHPFNOBNU-GOSISDBHSA-N 0.000 claims 1
• HCOIAHOKGFDSGZ-OAHLLOKOSA-N n-[(1r)-1-(4-chlorophenyl)ethyl]-6-[4-[(dimethylamino)methyl]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC(Cl)=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(CN(C)C)C=C1 HCOIAHOKGFDSGZ-OAHLLOKOSA-N 0.000 claims 1
• QZJHSSLRRSRMPU-QGZVFWFLSA-N n-[(1r)-1-phenylethyl]-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=C2N[C@H](C)C1=CC=CC=C1 QZJHSSLRRSRMPU-QGZVFWFLSA-N 0.000 claims 1
• MFHRHZPIEYORHH-UHFFFAOYSA-N n-[(2,5-dichlorophenyl)methyl]-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=C2NCC1=CC(Cl)=CC=C1Cl MFHRHZPIEYORHH-UHFFFAOYSA-N 0.000 claims 1
• YQCLEPYVIHWRIN-UHFFFAOYSA-N n-[(2,5-dichlorophenyl)methyl]-6-[4-(morpholin-4-ylmethyl)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=C(Cl)C(CNC=2C=3C=C(NC=3N=CN=2)C=2C=CC(CN3CCOCC3)=CC=2)=C1 YQCLEPYVIHWRIN-UHFFFAOYSA-N 0.000 claims 1
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