FI112947B - Pyrimido[5,4-d]pyrimidiinejä, näitä yhdisteitä sisältävät lääkeaineet, niiden käyttö ja menetelmä niiden valmistamiseksi - Google Patents

Info

Publication number

FI112947B

FI112947B FI970968A FI970968A FI112947B FI 112947 B FI112947 B FI 112947B FI 970968 A FI970968 A FI 970968A FI 970968 A FI970968 A FI 970968A FI 112947 B FI112947 B FI 112947B

Authority

FI

Finland

Prior art keywords

amino

pyrimido

pyrimidine

phenyl

chloro

Prior art date

1994-09-07

Links

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• Global Dossier
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• JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical class N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 title claims abstract description 101
• 150000001875 compounds Chemical class 0.000 title claims description 119
• 238000002360 preparation method Methods 0.000 title claims description 18
• 238000000034 method Methods 0.000 title claims description 9
• 239000003814 drug Substances 0.000 title claims description 6
• 229940079593 drug Drugs 0.000 title description 3
• 150000003839 salts Chemical class 0.000 claims abstract description 18
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 7
• 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
• 150000007524 organic acids Chemical class 0.000 claims abstract description 4
• 235000005985 organic acids Nutrition 0.000 claims abstract description 4
• -1 5-indanyl Chemical group 0.000 claims description 464
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 272
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 172
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 94
• 238000006243 chemical reaction Methods 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 13
• 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 13
• 239000000460 chlorine Substances 0.000 claims description 11
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 150000002431 hydrogen Chemical class 0.000 claims description 9
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
• 230000003647 oxidation Effects 0.000 claims description 7
• 238000007254 oxidation reaction Methods 0.000 claims description 7
• 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 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 230000035755 proliferation Effects 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 230000032050 esterification Effects 0.000 claims description 4
• 238000005886 esterification reaction Methods 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000006239 protecting group Chemical group 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
• WZPKSCHHBFABAA-UHFFFAOYSA-N 4-n-(3-chlorophenyl)-6-n-cyclopropylpyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound ClC1=CC=CC(NC=2C3=NC(NC4CC4)=NC=C3N=CN=2)=C1 WZPKSCHHBFABAA-UHFFFAOYSA-N 0.000 claims description 3
• JKONXQHCEMQILF-UHFFFAOYSA-N 6-(4-aminopiperidin-1-yl)-n-(3-methylphenyl)pyrimido[5,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(NC=2C3=NC(=NC=C3N=CN=2)N2CCC(N)CC2)=C1 JKONXQHCEMQILF-UHFFFAOYSA-N 0.000 claims description 3
• 230000010933 acylation Effects 0.000 claims description 3
• 238000005917 acylation reaction Methods 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 125000004185 ester group Chemical group 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 230000006103 sulfonylation Effects 0.000 claims description 3
• 238000005694 sulfonylation reaction Methods 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• DPNIIKJXOBBCPP-UHFFFAOYSA-N 2-[[4-(3-chloro-4-fluoroanilino)pyrimido[5,4-d]pyrimidin-6-yl]amino]propane-1,3-diol Chemical compound C12=NC(NC(CO)CO)=NC=C2N=CN=C1NC1=CC=C(F)C(Cl)=C1 DPNIIKJXOBBCPP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
• WTTJWXDNHFXWJB-UHFFFAOYSA-N 6-n-(1-azabicyclo[2.2.2]octan-3-yl)-4-n-(3-methylphenyl)pyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound CC1=CC=CC(NC=2C3=NC(NC4C5CCN(CC5)C4)=NC=C3N=CN=2)=C1 WTTJWXDNHFXWJB-UHFFFAOYSA-N 0.000 claims description 2
• BXGFVDDXXYSAGD-UHFFFAOYSA-N 6-n-(4-aminocyclohexyl)-4-n-(3-chloro-4-fluorophenyl)pyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound C1CC(N)CCC1NC1=NC=C(N=CN=C2NC=3C=C(Cl)C(F)=CC=3)C2=N1 BXGFVDDXXYSAGD-UHFFFAOYSA-N 0.000 claims description 2
• PKKNPIGESRYEGT-UHFFFAOYSA-N 6-n-cyclopropyl-4-n-(3,4-dichlorophenyl)pyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(C1=N2)=NC=NC1=CN=C2NC1CC1 PKKNPIGESRYEGT-UHFFFAOYSA-N 0.000 claims description 2
• IHFJJJPICABJOG-UHFFFAOYSA-N 6-n-cyclopropyl-4-n-(4-fluorophenyl)pyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound C1=CC(F)=CC=C1NC(C1=N2)=NC=NC1=CN=C2NC1CC1 IHFJJJPICABJOG-UHFFFAOYSA-N 0.000 claims description 2
• DRJOMFDNRDKRCE-SHTZXODSSA-N Fc1ccc(Nc2ncnc3cnc(N[C@H]4CC[C@@H](CC4)C(=O)N4CCOCC4)nc23)cc1Cl Chemical compound Fc1ccc(Nc2ncnc3cnc(N[C@H]4CC[C@@H](CC4)C(=O)N4CCOCC4)nc23)cc1Cl DRJOMFDNRDKRCE-SHTZXODSSA-N 0.000 claims description 2
• FTFRZXFNZVCRSK-UHFFFAOYSA-N N4-(3-chloro-4-fluorophenyl)-N6-(1-methyl-4-piperidinyl)pyrimido[5,4-d]pyrimidine-4,6-diamine Chemical compound C1CN(C)CCC1NC1=NC=C(N=CN=C2NC=3C=C(Cl)C(F)=CC=3)C2=N1 FTFRZXFNZVCRSK-UHFFFAOYSA-N 0.000 claims description 2
• 206010029113 Neovascularisation Diseases 0.000 claims description 2
• 230000009435 amidation Effects 0.000 claims description 2
• 238000007112 amidation reaction Methods 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
• BAEJGQHYQGIINS-UHFFFAOYSA-N methyl n-[1-[4-(3-methylanilino)pyrimido[5,4-d]pyrimidin-6-yl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC)CCN1C1=NC=C(N=CN=C2NC=3C=C(C)C=CC=3)C2=N1 BAEJGQHYQGIINS-UHFFFAOYSA-N 0.000 claims description 2
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
• DHCJFRRMDKHIRW-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-morpholin-4-ylpyrimido[5,4-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=CN=C(N3CCOCC3)N=C12 DHCJFRRMDKHIRW-UHFFFAOYSA-N 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 210000003556 vascular endothelial cell Anatomy 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
• 239000000969 carrier Substances 0.000 claims 2
• 239000003085 diluting agent Substances 0.000 claims 2
• 229910052731 fluorine Inorganic materials 0.000 claims 2
• 239000011737 fluorine Substances 0.000 claims 2
• PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical group CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims 1
• ORWYJGVIENCCJN-UHFFFAOYSA-N 2-[[4-(3-chloro-4-fluoroanilino)pyrimido[5,4-d]pyrimidin-6-yl]amino]-2-methylpropan-1-ol Chemical compound C12=NC(NC(C)(CO)C)=NC=C2N=CN=C1NC1=CC=C(F)C(Cl)=C1 ORWYJGVIENCCJN-UHFFFAOYSA-N 0.000 claims 1
• XJRGSGWOXFKLBX-UHFFFAOYSA-N 2-[[4-(3-chloro-4-fluoroanilino)pyrimido[5,4-d]pyrimidin-6-yl]amino]propan-1-ol Chemical compound C12=NC(NC(CO)C)=NC=C2N=CN=C1NC1=CC=C(F)C(Cl)=C1 XJRGSGWOXFKLBX-UHFFFAOYSA-N 0.000 claims 1
• 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
• XBARGVDOISHQKQ-HOMQSWHASA-N C1=C(Br)C(N)=C(Br)C=C1NC(C1=N2)=NC=NC1=CN=C2N[C@@H]1CC[C@@H](O)CC1 Chemical compound C1=C(Br)C(N)=C(Br)C=C1NC(C1=N2)=NC=NC1=CN=C2N[C@@H]1CC[C@@H](O)CC1 XBARGVDOISHQKQ-HOMQSWHASA-N 0.000 claims 1
• HDBREMCJUIQJGV-HOMQSWHASA-N C1=C(Cl)C(N)=C(Cl)C=C1NC(C1=N2)=NC=NC1=CN=C2N[C@@H]1CC[C@@H](O)CC1 Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1NC(C1=N2)=NC=NC1=CN=C2N[C@@H]1CC[C@@H](O)CC1 HDBREMCJUIQJGV-HOMQSWHASA-N 0.000 claims 1
• YRBCCCMUSVSEJS-SHTZXODSSA-N Fc1ccc(Nc2ncnc3cnc(N[C@H]4CC[C@@H](CC4)C(=O)N4CCCC4)nc23)cc1Cl Chemical compound Fc1ccc(Nc2ncnc3cnc(N[C@H]4CC[C@@H](CC4)C(=O)N4CCCC4)nc23)cc1Cl YRBCCCMUSVSEJS-SHTZXODSSA-N 0.000 claims 1
• 125000005382 boronyl group Chemical group 0.000 claims 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
• GMXHCXURJBRRDO-UHFFFAOYSA-N ethyl 4-[[4-(3-methylanilino)pyrimido[5,4-d]pyrimidin-6-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC=C(N=CN=C2NC=3C=C(C)C=CC=3)C2=N1 GMXHCXURJBRRDO-UHFFFAOYSA-N 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
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• 230000001394 metastastic effect Effects 0.000 claims 1
• 206010061289 metastatic neoplasm Diseases 0.000 claims 1
• DNTPGJBQLKOSOS-UHFFFAOYSA-N n-[1-[4-(3-methylanilino)pyrimido[5,4-d]pyrimidin-6-yl]piperidin-4-yl]formamide Chemical compound CC1=CC=CC(NC=2C3=NC(=NC=C3N=CN=2)N2CCC(CC2)NC=O)=C1 DNTPGJBQLKOSOS-UHFFFAOYSA-N 0.000 claims 1
• 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
• 239000000126 substance Substances 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 abstract description 6
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract description 5
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract description 5
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 573
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• 238000002844 melting Methods 0.000 description 253
• 230000008018 melting Effects 0.000 description 253
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 249
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• 239000000741 silica gel Substances 0.000 description 246
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• 238000001819 mass spectrum Methods 0.000 description 48
• 239000002904 solvent Substances 0.000 description 47
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• 239000000243 solution Substances 0.000 description 34
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• 238000010992 reflux Methods 0.000 description 13
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