SK12902000A3 - 6,9-disubstituované 2-[trans-(4-aminocyklohexyl)amino]-puríny, farmaceutické prostriedky obsahujúce tieto zlúčeniny a použitie - Google Patents

Info

Publication number

SK12902000A3

SK12902000A3 SK1290-2000A SK12902000A SK12902000A3 SK 12902000 A3 SK12902000 A3 SK 12902000A3 SK 12902000 A SK12902000 A SK 12902000A SK 12902000 A3 SK12902000 A3 SK 12902000A3

Authority

SK

Slovakia

Prior art keywords

group

integer

amino

alkyl

trans

Prior art date

1998-02-26

Links

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• -1 6,9-disubstituted 2-[trans-(4-aminocyclohexyl)amino]purines Chemical class 0.000 title claims abstract description 790
• 150000001875 compounds Chemical class 0.000 claims abstract description 765
• 238000000034 method Methods 0.000 claims abstract description 576
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 99
• 150000003839 salts Chemical class 0.000 claims abstract description 39
• 230000003287 optical effect Effects 0.000 claims abstract description 37
• 150000004677 hydrates Chemical class 0.000 claims abstract description 36
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 34
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 33
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims abstract description 29
• 230000006907 apoptotic process Effects 0.000 claims abstract description 20
• 210000002569 neuron Anatomy 0.000 claims abstract description 16
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
• 239000000203 mixture Substances 0.000 claims abstract description 13
• 101100439046 Caenorhabditis elegans cdk-2 gene Proteins 0.000 claims abstract description 3
• 239000003937 drug carrier Substances 0.000 claims abstract description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 406
• 239000001257 hydrogen Substances 0.000 claims description 168
• 229910052739 hydrogen Inorganic materials 0.000 claims description 168
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 140
• 125000000217 alkyl group Chemical group 0.000 claims description 135
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 121
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 115
• 229910052757 nitrogen Inorganic materials 0.000 claims description 109
• 125000004432 carbon atom Chemical group C* 0.000 claims description 105
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 94
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
• 125000000623 heterocyclic group Chemical group 0.000 claims description 82
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 64
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 62
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 60
• 210000004027 cell Anatomy 0.000 claims description 57
• 125000001424 substituent group Chemical group 0.000 claims description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 31
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 30
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• 208000032839 leukemia Diseases 0.000 claims description 15
• 201000001441 melanoma Diseases 0.000 claims description 14
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 14
• 239000002246 antineoplastic agent Substances 0.000 claims description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 10
• 208000009956 adenocarcinoma Diseases 0.000 claims description 10
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• XDKPTYKTFBDFFM-UHFFFAOYSA-N 9-cyclopentylpurine Chemical compound C1CCCC1N1C2=NC=NC=C2N=C1 XDKPTYKTFBDFFM-UHFFFAOYSA-N 0.000 claims description 9
• 201000009030 Carcinoma Diseases 0.000 claims description 9
• 210000001072 colon Anatomy 0.000 claims description 9
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 8
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 8
• 230000001613 neoplastic effect Effects 0.000 claims description 8
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 7
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 7
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
• 210000000481 breast Anatomy 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 210000004072 lung Anatomy 0.000 claims description 7
• 125000006308 propyl amino group Chemical group 0.000 claims description 7
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 6
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
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• 208000017604 Hodgkin disease Diseases 0.000 claims description 5
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 5
• 206010039491 Sarcoma Diseases 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 229940034982 antineoplastic agent Drugs 0.000 claims description 5
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 5
• 230000003463 hyperproliferative effect Effects 0.000 claims description 5
• 210000002307 prostate Anatomy 0.000 claims description 5
• 210000002784 stomach Anatomy 0.000 claims description 5
• RLIXBNBZBIUHMU-OARLLREQSA-N C1CC(C(CC)OCCC)CCN1NC1=NC(N[C@@H]2CC[C@@H](N)CC2)=NC2=C1N=CN2C1CCCC1 Chemical compound C1CC(C(CC)OCCC)CCN1NC1=NC(N[C@@H]2CC[C@@H](N)CC2)=NC2=C1N=CN2C1CCCC1 RLIXBNBZBIUHMU-OARLLREQSA-N 0.000 claims description 4
• IGBAWHJZIJMWHW-GMQQGASLSA-N Cl.Cl.CCCC(C)N(c1ccccc1)c1nc(N[C@H]2CC[C@H](N)CC2)nc2n(cnc12)C1CCCC1 Chemical compound Cl.Cl.CCCC(C)N(c1ccccc1)c1nc(N[C@H]2CC[C@H](N)CC2)nc2n(cnc12)C1CCCC1 IGBAWHJZIJMWHW-GMQQGASLSA-N 0.000 claims description 4
• FHABNANYALULNA-MXPSUWBQSA-N Cl.Cl.COCCNc1nc(N[C@H]2CC[C@H](N)CC2)nc2n(cnc12)C1CCCC1 Chemical compound Cl.Cl.COCCNc1nc(N[C@H]2CC[C@H](N)CC2)nc2n(cnc12)C1CCCC1 FHABNANYALULNA-MXPSUWBQSA-N 0.000 claims description 4
• OVLQSJGOVKVTGF-VAJGKAQFSA-N Cl.Cl.COc1ccc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C(C)C)cc1OC Chemical compound Cl.Cl.COc1ccc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C(C)C)cc1OC OVLQSJGOVKVTGF-VAJGKAQFSA-N 0.000 claims description 4
• XOVDXKXELSLHIP-PMXFUEHMSA-N Cl.Cl.COc1ccc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 Chemical compound Cl.Cl.COc1ccc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 XOVDXKXELSLHIP-PMXFUEHMSA-N 0.000 claims description 4
• FQMVFSQLVJDBEG-PMXFUEHMSA-N Cl.Cl.COc1cccc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)c1OC Chemical compound Cl.Cl.COc1cccc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)c1OC FQMVFSQLVJDBEG-PMXFUEHMSA-N 0.000 claims description 4
• XNSZKJBCUMSYCW-OPPVHOIFSA-N Cl.Cl.N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)C1CCCC1)NCC1=CC=CC2=CC=CC=C12 Chemical compound Cl.Cl.N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)C1CCCC1)NCC1=CC=CC2=CC=CC=C12 XNSZKJBCUMSYCW-OPPVHOIFSA-N 0.000 claims description 4
• KOCSXSGKVSUPDL-HLDGVKIBSA-N Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2cccc(F)c2)c2ncn(C3CCCC3)c2n1 Chemical compound Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2cccc(F)c2)c2ncn(C3CCCC3)c2n1 KOCSXSGKVSUPDL-HLDGVKIBSA-N 0.000 claims description 4
• DPFVYCFVGBIRHL-HEOZJBRKSA-N Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccccc2)c2ncn(C3CCCC3)c2n1 Chemical compound Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(Nc2ccccc2)c2ncn(C3CCCC3)c2n1 DPFVYCFVGBIRHL-HEOZJBRKSA-N 0.000 claims description 4
• 206010024612 Lipoma Diseases 0.000 claims description 4
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• IYKOUQTWZGUNAB-PPEAWTIOSA-N C1CC(C(CC)OC(C)CC)CCN1NC1=NC(N[C@@H]2CC[C@@H](N)CC2)=NC2=C1N=CN2C1CCCC1 Chemical compound C1CC(C(CC)OC(C)CC)CCN1NC1=NC(N[C@@H]2CC[C@@H](N)CC2)=NC2=C1N=CN2C1CCCC1 IYKOUQTWZGUNAB-PPEAWTIOSA-N 0.000 claims description 3
• DWCUFHSZFVHEQY-MCXZQIONSA-N Cl.Cl.CCCCCCCCCCCCNc1nc(N[C@H]2CC[C@H](N)CC2)nc2n(cnc12)C1CCCC1 Chemical compound Cl.Cl.CCCCCCCCCCCCNc1nc(N[C@H]2CC[C@H](N)CC2)nc2n(cnc12)C1CCCC1 DWCUFHSZFVHEQY-MCXZQIONSA-N 0.000 claims description 3
• FMOANJRWZHUWRK-PMXFUEHMSA-N Cl.Cl.COc1cc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc(OC)c1OC Chemical compound Cl.Cl.COc1cc(CNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc(OC)c1OC FMOANJRWZHUWRK-PMXFUEHMSA-N 0.000 claims description 3
• VFSRIZOMQATVCI-HEWGHVJBSA-N Cl.Cl.COc1ccc(CCNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 Chemical compound Cl.Cl.COc1ccc(CCNc2nc(N[C@H]3CC[C@H](N)CC3)nc3n(cnc23)C2CCCC2)cc1 VFSRIZOMQATVCI-HEWGHVJBSA-N 0.000 claims description 3
• RJFDSLWYTXDUBQ-HJNPFAAISA-N Cl.Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(NCCNc2ccccc2)c2ncn(C3CCCC3)c2n1 Chemical compound Cl.Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(NCCNc2ccccc2)c2ncn(C3CCCC3)c2n1 RJFDSLWYTXDUBQ-HJNPFAAISA-N 0.000 claims description 3
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• AVADVHHRYCGIMB-BCHJJPDRSA-N Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(NNc2ccccc2F)c2ncn(C3CCCC3)c2n1 Chemical compound Cl.Cl.N[C@H]1CC[C@@H](CC1)Nc1nc(NNc2ccccc2F)c2ncn(C3CCCC3)c2n1 AVADVHHRYCGIMB-BCHJJPDRSA-N 0.000 claims description 3
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• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 2
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
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• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
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• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 140
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 15
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• 125000004429 atom Chemical group 0.000 claims 7
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• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 3
• 125000003545 alkoxy group Chemical group 0.000 claims 3
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