SI9620103A - Pirolopirimidini in postopki za njihovo pripravo - Google Patents

Info

Publication number

SI9620103A

SI9620103A SI9620103A SI9620103A SI9620103A SI 9620103 A SI9620103 A SI 9620103A SI 9620103 A SI9620103 A SI 9620103A SI 9620103 A SI9620103 A SI 9620103A SI 9620103 A SI9620103 A SI 9620103A

Authority

SI

Slovenia

Prior art keywords

phenyl

pyrrolo

pyrimidine

chloro

amino

Prior art date

1995-07-06

Links

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• 238000000034 method Methods 0.000 title claims description 43
• 238000002360 preparation method Methods 0.000 title claims description 38
• 230000008569 process Effects 0.000 title claims description 16
• 150000004944 pyrrolopyrimidines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 294
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
• JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical class N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims abstract description 9
• -1 cyano, amino Chemical group 0.000 claims description 255
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 187
• 125000000217 alkyl group Chemical group 0.000 claims description 165
• 125000003282 alkyl amino group Chemical group 0.000 claims description 155
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 106
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 103
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 102
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 91
• 229910052739 hydrogen Inorganic materials 0.000 claims description 82
• 239000001257 hydrogen Substances 0.000 claims description 80
• 150000003839 salts Chemical class 0.000 claims description 80
• 229910052736 halogen Inorganic materials 0.000 claims description 76
• 150000002367 halogens Chemical group 0.000 claims description 75
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 69
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 59
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 57
• 125000003545 alkoxy group Chemical group 0.000 claims description 57
• 125000006239 protecting group Chemical group 0.000 claims description 56
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 50
• 125000004423 acyloxy group Chemical group 0.000 claims description 49
• 125000001424 substituent group Chemical group 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 125000004432 carbon atom Chemical group C* 0.000 claims description 33
• 150000002431 hydrogen Chemical class 0.000 claims description 30
• 125000001624 naphthyl group Chemical group 0.000 claims description 29
• 125000004076 pyridyl group Chemical group 0.000 claims description 29
• 125000003431 oxalo group Chemical group 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 25
• 125000000524 functional group Chemical group 0.000 claims description 25
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 24
• 125000005843 halogen group Chemical group 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 18
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 16
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• 150000003254 radicals Chemical class 0.000 claims description 15
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• JLYIDLKBGFXUTE-UHFFFAOYSA-N ethyl 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carboxylate Chemical compound N1=CN=C2NC(C(=O)OCC)=CC2=C1NC1=CC=CC(Cl)=C1 JLYIDLKBGFXUTE-UHFFFAOYSA-N 0.000 claims description 9
• 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 claims description 8
• 241001465754 Metazoa Species 0.000 claims description 7
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• YOAQRPAYMXTKQI-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N1=CN=C2NC(C(=O)O)=CC2=C1NC1=CC=CC(Cl)=C1 YOAQRPAYMXTKQI-UHFFFAOYSA-N 0.000 claims description 6
• 239000012024 dehydrating agents‎ Substances 0.000 claims description 6
• 150000003512 tertiary amines Chemical class 0.000 claims description 5
• WTGCGBNMDUJBEX-UHFFFAOYSA-N 4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 WTGCGBNMDUJBEX-UHFFFAOYSA-N 0.000 claims description 4
• UZDFIMXOVIIKQO-UHFFFAOYSA-N 6-(4-aminophenyl)-n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 UZDFIMXOVIIKQO-UHFFFAOYSA-N 0.000 claims description 4
• 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• FLBNYSVQCAAWOC-UHFFFAOYSA-N ethyl 4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 FLBNYSVQCAAWOC-UHFFFAOYSA-N 0.000 claims description 4
• SIVRSPUOZPNICK-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[(dimethylamino)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N1=CN=C2NC(CN(C)C)=CC2=C1NC1=CC=CC(Cl)=C1 SIVRSPUOZPNICK-UHFFFAOYSA-N 0.000 claims description 4
• RFOKKVGXGZFMQU-OAHLLOKOSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 RFOKKVGXGZFMQU-OAHLLOKOSA-N 0.000 claims description 4
• 150000003233 pyrroles Chemical class 0.000 claims description 4
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• DKRKYQJAGJAZRT-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carbonitrile Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C#N)=C1 DKRKYQJAGJAZRT-UHFFFAOYSA-N 0.000 claims description 3
• HRRSTGSFDNCRBK-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=CN=C2NC(C(=O)N)=CC2=C1NC1=CC=CC(Cl)=C1 HRRSTGSFDNCRBK-UHFFFAOYSA-N 0.000 claims description 3
• QYVBDLWIXVYDDY-UHFFFAOYSA-N 4-(3-chloroanilino)-n-(3-methylbutyl)-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=CN=C2NC(C(=O)NCCC(C)C)=CC2=C1NC1=CC=CC(Cl)=C1 QYVBDLWIXVYDDY-UHFFFAOYSA-N 0.000 claims description 3
• KWAKLZADYVJMGC-UHFFFAOYSA-N 4-[4-(3-chloroanilino)-5-[(dimethylamino)methyl]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenol Chemical compound C=12C(CN(C)C)=C(C=3C=CC(O)=CC=3)NC2=NC=NC=1NC1=CC=CC(Cl)=C1 KWAKLZADYVJMGC-UHFFFAOYSA-N 0.000 claims description 3
• YFOPRDNSBLGPMI-UHFFFAOYSA-N 4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenol Chemical compound C1=CC(O)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 YFOPRDNSBLGPMI-UHFFFAOYSA-N 0.000 claims description 3
• OZEGDEJMJWEICF-QGZVFWFLSA-N 6-[4-(diethylamino)phenyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N(CC)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 OZEGDEJMJWEICF-QGZVFWFLSA-N 0.000 claims description 3
• UPDHEPFPHMXRKP-UHFFFAOYSA-N [4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]methanol Chemical compound N1=CN=C2NC(CO)=CC2=C1NC1=CC=CC(Cl)=C1 UPDHEPFPHMXRKP-UHFFFAOYSA-N 0.000 claims description 3
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
• KXVFXQNQBCHBKL-UHFFFAOYSA-N n-(3-chlorophenyl)-5-methyl-6-pyridin-2-yl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(C)=C(C=3N=CC=CC=3)NC2=NC=NC=1NC1=CC=CC(Cl)=C1 KXVFXQNQBCHBKL-UHFFFAOYSA-N 0.000 claims description 3
• DHSPAWKUZSBXHS-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(4-nitrophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 DHSPAWKUZSBXHS-UHFFFAOYSA-N 0.000 claims description 3
• PGTNANTWNTYJNR-UHFFFAOYSA-N n-benzyl-4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C(=O)NCC=2C=CC=CC=2)=C1 PGTNANTWNTYJNR-UHFFFAOYSA-N 0.000 claims description 3
• ZPPJQVOJGAAFFM-MRXNPFEDSA-N 2,2-dimethyl-n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propanamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(NC(=O)C(C)(C)C)=C1 ZPPJQVOJGAAFFM-MRXNPFEDSA-N 0.000 claims description 2
• QWTLRAWOLQZKFX-MRXNPFEDSA-N 2,2-dimethyl-n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propanamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(NC(=O)C(C)(C)C)C=C1 QWTLRAWOLQZKFX-MRXNPFEDSA-N 0.000 claims description 2
• VEBRIZYASKCCKZ-UHFFFAOYSA-N 2-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenoxy]acetamide Chemical compound NC(=O)COC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 VEBRIZYASKCCKZ-UHFFFAOYSA-N 0.000 claims description 2
• AHBMPRJMHUNHRS-UHFFFAOYSA-N 2-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenoxy]acetamide Chemical compound C1=CC(OCC(=O)N)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 AHBMPRJMHUNHRS-UHFFFAOYSA-N 0.000 claims description 2
• GYFHQWOKLLBICP-UHFFFAOYSA-N 2-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 GYFHQWOKLLBICP-UHFFFAOYSA-N 0.000 claims description 2
• SUEXSSUXWXXPNN-MRXNPFEDSA-N 2-methyl-n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propanamide Chemical compound CC(C)C(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 SUEXSSUXWXXPNN-MRXNPFEDSA-N 0.000 claims description 2
• QEMJSPGYFNYBPQ-UHFFFAOYSA-N 2-methylpropyl 4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]benzoate Chemical compound C1=CC(C(=O)OCC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 QEMJSPGYFNYBPQ-UHFFFAOYSA-N 0.000 claims description 2
• IVXPKMHNZJSHQA-UHFFFAOYSA-N 4-(3-chloroanilino)-5-methyl-7h-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde Chemical compound C=12C(C)=C(C=O)NC2=NC=NC=1NC1=CC=CC(Cl)=C1 IVXPKMHNZJSHQA-UHFFFAOYSA-N 0.000 claims description 2
• VIYAUNPLBAEUSN-UHFFFAOYSA-N 4-(3-chloroanilino)-5-methyl-7h-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid Chemical compound C=12C(C)=C(C(O)=O)NC2=NC=NC=1NC1=CC=CC(Cl)=C1 VIYAUNPLBAEUSN-UHFFFAOYSA-N 0.000 claims description 2
• LNWOKFXJMDSXCT-UHFFFAOYSA-N 4-(3-chloroanilino)-6-methyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde Chemical compound C=12C(C=O)=C(C)NC2=NC=NC=1NC1=CC=CC(Cl)=C1 LNWOKFXJMDSXCT-UHFFFAOYSA-N 0.000 claims description 2
• FBMVGKKWZJCOEZ-UHFFFAOYSA-N 4-(3-chloroanilino)-6-methyl-7h-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid Chemical compound C=12C(C(O)=O)=C(C)NC2=NC=NC=1NC1=CC=CC(Cl)=C1 FBMVGKKWZJCOEZ-UHFFFAOYSA-N 0.000 claims description 2
• BYYLPECJKOEHBV-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde Chemical compound ClC1=CC=CC(NC=2C=3C=C(C=O)NC=3N=CN=2)=C1 BYYLPECJKOEHBV-UHFFFAOYSA-N 0.000 claims description 2
• KFIICRGOUMCPQI-UHFFFAOYSA-N 4-(3-chloroanilino)-n,n-dimethyl-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=CN=C2NC(C(=O)N(C)C)=CC2=C1NC1=CC=CC(Cl)=C1 KFIICRGOUMCPQI-UHFFFAOYSA-N 0.000 claims description 2
• HTUAWMQFTGNRIW-UHFFFAOYSA-N 4-(3-chloroanilino)-n-methyl-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound N1=CN=C2NC(C(=O)NC)=CC2=C1NC1=CC=CC(Cl)=C1 HTUAWMQFTGNRIW-UHFFFAOYSA-N 0.000 claims description 2
• KWPPCQGFDDELRR-SNVBAGLBSA-N 4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde Chemical compound C1([C@H](NC=2C=3C=C(C=O)NC=3N=CN=2)C)=CC=CC=C1 KWPPCQGFDDELRR-SNVBAGLBSA-N 0.000 claims description 2
• TVNJDLRYYVDKJX-SNVBAGLBSA-N 4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidine-6-carbonitrile Chemical compound C1([C@H](NC=2C=3C=C(NC=3N=CN=2)C#N)C)=CC=CC=C1 TVNJDLRYYVDKJX-SNVBAGLBSA-N 0.000 claims description 2
• IQNYCLWUBSTSKY-SECBINFHSA-N 4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C1([C@H](NC=2C=3C=C(NC=3N=CN=2)C(N)=O)C)=CC=CC=C1 IQNYCLWUBSTSKY-SECBINFHSA-N 0.000 claims description 2
• YBUPNHZFCNMZET-GFCCVEGCSA-N 5,6-dimethyl-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1([C@H](NC=2C=3C(C)=C(C)NC=3N=CN=2)C)=CC=CC=C1 YBUPNHZFCNMZET-GFCCVEGCSA-N 0.000 claims description 2
• YBUPNHZFCNMZET-LBPRGKRZSA-N 5,6-dimethyl-n-[(1s)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1([C@@H](NC=2C=3C(C)=C(C)NC=3N=CN=2)C)=CC=CC=C1 YBUPNHZFCNMZET-LBPRGKRZSA-N 0.000 claims description 2
• KFNHYCUETQTMIC-UHFFFAOYSA-N 6-(3-aminophenyl)-n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 KFNHYCUETQTMIC-UHFFFAOYSA-N 0.000 claims description 2
• OVWSZWFGFGIFNR-CYBMUJFWSA-N 6-(3-aminophenyl)-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(N)=C1 OVWSZWFGFGIFNR-CYBMUJFWSA-N 0.000 claims description 2
• GCFYJDAFLTYJQQ-UHFFFAOYSA-N 6-(4-aminophenyl)-n-(3-chloro-4-fluorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 GCFYJDAFLTYJQQ-UHFFFAOYSA-N 0.000 claims description 2
• HBEXKMFNANAKRL-UHFFFAOYSA-N 6-(4-aminophenyl)-n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(N)=CC=2)=C1 HBEXKMFNANAKRL-UHFFFAOYSA-N 0.000 claims description 2
• SRSAKUNDUJJZAN-CYBMUJFWSA-N 6-(4-aminophenyl)-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(N)C=C1 SRSAKUNDUJJZAN-CYBMUJFWSA-N 0.000 claims description 2
• SRSAKUNDUJJZAN-ZDUSSCGKSA-N 6-(4-aminophenyl)-n-[(1s)-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(N)C=C1 SRSAKUNDUJJZAN-ZDUSSCGKSA-N 0.000 claims description 2
• YILGPGFTIGZEMT-UHFFFAOYSA-N 6-(4-aminophenyl)-n-[(3-chlorophenyl)methyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N)=CC=C1C(NC1=NC=N2)=CC1=C2NCC1=CC=CC(Cl)=C1 YILGPGFTIGZEMT-UHFFFAOYSA-N 0.000 claims description 2
• NQGFVQYELMDSEE-UHFFFAOYSA-N 6-(4-aminophenyl)-n-benzyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(N)=CC=C1C(NC1=NC=N2)=CC1=C2NCC1=CC=CC=C1 NQGFVQYELMDSEE-UHFFFAOYSA-N 0.000 claims description 2
• RSJMXGTWBRPXFK-UHFFFAOYSA-N 6-(aminomethyl)-n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N1=CN=C2NC(CN)=CC2=C1NC1=CC=CC(Cl)=C1 RSJMXGTWBRPXFK-UHFFFAOYSA-N 0.000 claims description 2
• OSIXZWGGFJMMGB-SNVBAGLBSA-N 6-(aminomethyl)-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1([C@H](NC=2C=3C=C(CN)NC=3N=CN=2)C)=CC=CC=C1 OSIXZWGGFJMMGB-SNVBAGLBSA-N 0.000 claims description 2
• GGDWKXPIGAHORY-GFCCVEGCSA-N 6-[(dimethylamino)methyl]-n-[(1r)-1-phenylethyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1([C@H](NC=2C=3C=C(CN(C)C)NC=3N=CN=2)C)=CC=CC=C1 GGDWKXPIGAHORY-GFCCVEGCSA-N 0.000 claims description 2
• GNVWZEIUTBVYLZ-UHFFFAOYSA-N 6-[4-(dimethylamino)phenyl]-n-(1-phenylethyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1C(C)NC(C=1C=2)=NC=NC=1NC=2C1=CC=C(N(C)C)C=C1 GNVWZEIUTBVYLZ-UHFFFAOYSA-N 0.000 claims description 2
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