JP4242928B2 - 置換ピロロピリミジンおよびその製造方法 - Google Patents

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Publication number

JP4242928B2

JP4242928B2 JP51042598A JP51042598A JP4242928B2 JP 4242928 B2 JP4242928 B2 JP 4242928B2 JP 51042598 A JP51042598 A JP 51042598A JP 51042598 A JP51042598 A JP 51042598A JP 4242928 B2 JP4242928 B2 JP 4242928B2

Authority

JP

Japan

Prior art keywords

pyrrolo

pyrimidine

chloroanilino

phenyl

formula

Prior art date

1996-08-23

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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• 238000000034 method Methods 0.000 title description 42
• 230000008569 process Effects 0.000 title description 5
• 150000004944 pyrrolopyrimidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 146
• JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical class N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 claims abstract description 7
• -1 3 -phenylureido Chemical group 0.000 claims description 185
• 125000000217 alkyl group Chemical group 0.000 claims description 101
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 36
• 125000003282 alkyl amino group Chemical group 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 239000000460 chlorine Substances 0.000 claims description 13
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 12
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 8
• 241001465754 Metazoa Species 0.000 claims description 7
• 125000005281 alkyl ureido group Chemical group 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 5
• BNMRACHWXQYRHO-UHFFFAOYSA-N 4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidine-6-carbothioamide Chemical compound N1=CN=C2NC(C(=S)N)=CC2=C1NC1=CC=CC(Cl)=C1 BNMRACHWXQYRHO-UHFFFAOYSA-N 0.000 claims description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims description 3
• LDUVGYTUBRSPKL-UBKPWBPPSA-N (NE)-N-[[4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]methylidene]hydroxylamine Chemical compound N1=CN=C2NC(/C=N/O)=CC2=C1NC1=CC=CC(Cl)=C1 LDUVGYTUBRSPKL-UBKPWBPPSA-N 0.000 claims description 2
• LDUVGYTUBRSPKL-FMQZQXMHSA-N (NZ)-N-[[4-(3-chloroanilino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]methylidene]hydroxylamine Chemical compound N1=CN=C2NC(\C=N/O)=CC2=C1NC1=CC=CC(Cl)=C1 LDUVGYTUBRSPKL-FMQZQXMHSA-N 0.000 claims description 2
• CYMAZKIEYPVYOH-UHFFFAOYSA-N 2-methoxy-4-[4-(3-methylanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenol Chemical compound C1=C(O)C(OC)=CC(C=2NC3=NC=NC(NC=4C=C(C)C=CC=4)=C3C=2)=C1 CYMAZKIEYPVYOH-UHFFFAOYSA-N 0.000 claims description 2
• VAKYVBRASQJLDI-UHFFFAOYSA-N 2-methylpropyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 VAKYVBRASQJLDI-UHFFFAOYSA-N 0.000 claims description 2
• VGFSMURRDQKEKB-UHFFFAOYSA-N 6-(3-methoxy-4-phenylmethoxyphenyl)-n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC(C=2NC3=NC=NC(NC=4C=C(C)C=CC=4)=C3C=2)=CC=C1OCC1=CC=CC=C1 VGFSMURRDQKEKB-UHFFFAOYSA-N 0.000 claims description 2
• QOLIVYYSALQXGF-LJQANCHMSA-N 6-[3-(benzylamino)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=1NCC1=CC=CC=C1 QOLIVYYSALQXGF-LJQANCHMSA-N 0.000 claims description 2
• NIFHYNGZYDVDBU-UHFFFAOYSA-N 6-[4-(benzylamino)phenyl]-n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(NCC=3C=CC=CC=3)=CC=2)=C1 NIFHYNGZYDVDBU-UHFFFAOYSA-N 0.000 claims description 2
• DZMUFMFMZLAPEB-UHFFFAOYSA-N ClC=1C=C(NC=2C3=C(N=CN2)NC(=C3)C3=CC=C(C=C3)N=CN(CC)CC)C=CC1 Chemical compound ClC=1C=C(NC=2C3=C(N=CN2)NC(=C3)C3=CC=C(C=C3)N=CN(CC)CC)C=CC1 DZMUFMFMZLAPEB-UHFFFAOYSA-N 0.000 claims description 2
• CXAYSCXJHBBHSR-UHFFFAOYSA-N ClC=1C=C(NC=2C3=C(N=CN2)NC(=C3)C3=CC=C(C=C3)N=CN3CCCCC3)C=CC1 Chemical compound ClC=1C=C(NC=2C3=C(N=CN2)NC(=C3)C3=CC=C(C=C3)N=CN3CCCCC3)C=CC1 CXAYSCXJHBBHSR-UHFFFAOYSA-N 0.000 claims description 2
• QOPHSBUZTVLVBJ-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(1-methyltetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN1N=NN=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 QOPHSBUZTVLVBJ-UHFFFAOYSA-N 0.000 claims description 2
• BCZCVGXQOLPACI-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(2-methyltetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CN1N=NC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 BCZCVGXQOLPACI-UHFFFAOYSA-N 0.000 claims description 2
• OGEBYZFAAZVIHT-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(2H-tetrazol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2NN=NN=2)=C1 OGEBYZFAAZVIHT-UHFFFAOYSA-N 0.000 claims description 2
• GAABGZUDSKAVGH-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(4,5-dimethyl-1,3-thiazol-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound S1C(C)=C(C)N=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 GAABGZUDSKAVGH-UHFFFAOYSA-N 0.000 claims description 2
• FSZWTIFZYUHKJN-UHFFFAOYSA-N N-(3-chlorophenyl)-6-(methoxyiminomethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N1=CN=C2NC(C=NOC)=CC2=C1NC1=CC=CC(Cl)=C1 FSZWTIFZYUHKJN-UHFFFAOYSA-N 0.000 claims description 2
• BPEIBTXCKPKWLE-UHFFFAOYSA-N N-(3-chlorophenyl)-6-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1C1=CSC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=N1 BPEIBTXCKPKWLE-UHFFFAOYSA-N 0.000 claims description 2
• LNPXDMGETBINDL-UHFFFAOYSA-N [4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 LNPXDMGETBINDL-UHFFFAOYSA-N 0.000 claims description 2
• KJCWFUJEFVWZSE-UHFFFAOYSA-N [4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]-morpholin-4-ylmethanone Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C(=O)N2CCOCC2)=C1 KJCWFUJEFVWZSE-UHFFFAOYSA-N 0.000 claims description 2
• SWTAWOJNKFZMMT-UHFFFAOYSA-N [4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-morpholin-4-ylmethanone Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(=CC=2)C(=O)N2CCOCC2)=C1 SWTAWOJNKFZMMT-UHFFFAOYSA-N 0.000 claims description 2
• NUXWAOSDMYECDX-UHFFFAOYSA-N ethyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 NUXWAOSDMYECDX-UHFFFAOYSA-N 0.000 claims description 2
• ROZJWSLFOMITNR-UHFFFAOYSA-N methyl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 ROZJWSLFOMITNR-UHFFFAOYSA-N 0.000 claims description 2
• BRBPDQKNOPJHDS-UHFFFAOYSA-N n'-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-n,n-diethylmethanimidamide Chemical compound CCN(CC)C=NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 BRBPDQKNOPJHDS-UHFFFAOYSA-N 0.000 claims description 2
• HYSPQBYMQIZTMH-UHFFFAOYSA-N n'-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 HYSPQBYMQIZTMH-UHFFFAOYSA-N 0.000 claims description 2
• YBZDNHCFYNZPHI-UHFFFAOYSA-N n'-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-n,n-dimethylmethanimidamide Chemical compound C1=CC(N=CN(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 YBZDNHCFYNZPHI-UHFFFAOYSA-N 0.000 claims description 2
• SDSLGPIDULPJQG-MRXNPFEDSA-N n,n-dimethyl-n'-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanimidamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(N=CN(C)C)=C1 SDSLGPIDULPJQG-MRXNPFEDSA-N 0.000 claims description 2
• UNUHIYOQLRIQNQ-MRXNPFEDSA-N n,n-dimethyl-n'-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanimidamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(N=CN(C)C)C=C1 UNUHIYOQLRIQNQ-MRXNPFEDSA-N 0.000 claims description 2
• PRVIBBCNUUBOSX-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(1,3-thiazol-2-yl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2SC=CN=2)=C1 PRVIBBCNUUBOSX-UHFFFAOYSA-N 0.000 claims description 2
• LIPUGMMVKJZMRG-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(3-methoxy-4-phenylmethoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound COC1=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=CC=C1OCC1=CC=CC=C1 LIPUGMMVKJZMRG-UHFFFAOYSA-N 0.000 claims description 2
• MIZGMBWXPIRGEE-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[3-(morpholin-4-ylmethylideneamino)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=C(C=CC=2)N=CN2CCOCC2)=C1 MIZGMBWXPIRGEE-UHFFFAOYSA-N 0.000 claims description 2
• OKQBRJKNDDAIKW-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-(morpholin-4-ylmethylideneamino)phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(=CC=2)N=CN2CCOCC2)=C1 OKQBRJKNDDAIKW-UHFFFAOYSA-N 0.000 claims description 2
• GBCGNNNFIRWGCW-UHFFFAOYSA-N n-(3-chlorophenyl)-6-[4-[(4-methylpiperazin-1-yl)methylideneamino]phenyl]-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C=NC1=CC=C(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)C=C1 GBCGNNNFIRWGCW-UHFFFAOYSA-N 0.000 claims description 2
• ROLDUDKLNYYONL-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 ROLDUDKLNYYONL-UHFFFAOYSA-N 0.000 claims description 2
• RBEFWIDYHAIBSL-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 RBEFWIDYHAIBSL-UHFFFAOYSA-N 0.000 claims description 2
• PKNAMUVGIGLHAY-UHFFFAOYSA-N n-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 PKNAMUVGIGLHAY-UHFFFAOYSA-N 0.000 claims description 2
• WVICNPJYDFMIGL-OAHLLOKOSA-N n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound CCS(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 WVICNPJYDFMIGL-OAHLLOKOSA-N 0.000 claims description 2
• KQWSURRAHQPGAF-CQSZACIVSA-N n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=CC(NS(C)(=O)=O)=C1 KQWSURRAHQPGAF-CQSZACIVSA-N 0.000 claims description 2
• DZRXPIWDNCNPOM-MRXNPFEDSA-N n-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 DZRXPIWDNCNPOM-MRXNPFEDSA-N 0.000 claims description 2
• WLMINMLKCZPIDN-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]benzenesulfonamide Chemical compound ClC1=CC=CC(NC=2C=3C=C(NC=3N=CN=2)C=2C=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=2)=C1 WLMINMLKCZPIDN-UHFFFAOYSA-N 0.000 claims description 2
• RJHPCDDFUQAQPU-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 RJHPCDDFUQAQPU-UHFFFAOYSA-N 0.000 claims description 2
• WBVNHFVJQUXGDJ-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 WBVNHFVJQUXGDJ-UHFFFAOYSA-N 0.000 claims description 2
• NDIAGRBKTSAOQM-UHFFFAOYSA-N n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 NDIAGRBKTSAOQM-UHFFFAOYSA-N 0.000 claims description 2
• ZXEAZQRLYXDOIU-OAHLLOKOSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 ZXEAZQRLYXDOIU-OAHLLOKOSA-N 0.000 claims description 2
• PSKGKFLVQJOKPI-CQSZACIVSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]methanesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C=2)=NC=NC=1NC=2C1=CC=C(NS(C)(=O)=O)C=C1 PSKGKFLVQJOKPI-CQSZACIVSA-N 0.000 claims description 2
• KJPHJVDDQOMOSH-MRXNPFEDSA-N n-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]propane-2-sulfonamide Chemical compound C1=CC(NS(=O)(=O)C(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 KJPHJVDDQOMOSH-MRXNPFEDSA-N 0.000 claims description 2
• MKLSHESXKCZSML-UHFFFAOYSA-N propan-2-yl n-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC(C)C)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 MKLSHESXKCZSML-UHFFFAOYSA-N 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• YYELWCZQXDCXCI-UHFFFAOYSA-N 1-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound CCNC(=O)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 YYELWCZQXDCXCI-UHFFFAOYSA-N 0.000 claims 1
• UTIXVEICQYJJRY-UHFFFAOYSA-N 1-[3-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-methylthiourea Chemical compound CNC(=S)NC1=CC=CC(C=2NC3=NC=NC(NC=4C=C(Cl)C=CC=4)=C3C=2)=C1 UTIXVEICQYJJRY-UHFFFAOYSA-N 0.000 claims 1
• TWNRMTYWTBYQQS-UHFFFAOYSA-N 1-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 TWNRMTYWTBYQQS-UHFFFAOYSA-N 0.000 claims 1
• UCRKSQGCZVGBGX-UHFFFAOYSA-N 1-[4-[4-(3-chloroanilino)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]-3-methylthiourea Chemical compound C1=CC(NC(=S)NC)=CC=C1C(NC1=NC=N2)=CC1=C2NC1=CC=CC(Cl)=C1 UCRKSQGCZVGBGX-UHFFFAOYSA-N 0.000 claims 1
• CGSVJQVCEGIWCF-OAHLLOKOSA-N 1-ethyl-3-[3-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound CCNC(=O)NC1=CC=CC(C=2NC3=NC=NC(N[C@H](C)C=4C=CC=CC=4)=C3C=2)=C1 CGSVJQVCEGIWCF-OAHLLOKOSA-N 0.000 claims 1
• YPCURGZEPMFYLX-OAHLLOKOSA-N 1-ethyl-3-[4-[4-[[(1r)-1-phenylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(NC1=NC=N2)=CC1=C2N[C@H](C)C1=CC=CC=C1 YPCURGZEPMFYLX-OAHLLOKOSA-N 0.000 claims 1
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