CA2368843C - Neurotrophic substituted pyrimidines - Google Patents

Info

Publication number

CA2368843C

CA2368843C CA002368843A CA2368843A CA2368843C CA 2368843 C CA2368843 C CA 2368843C CA 002368843 A CA002368843 A CA 002368843A CA 2368843 A CA2368843 A CA 2368843A CA 2368843 C CA2368843 C CA 2368843C

Authority

CA

Canada

Prior art keywords

pyrimidine

amino

chlorophenoxy

trans

6alkyl

Prior art date

1999-04-08

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

Links

• Espacenet
• Global Dossier
• CIPO
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• 150000003230 pyrimidines Chemical class 0.000 title abstract description 6
• 230000000508 neurotrophic effect Effects 0.000 title description 7
• 230000000626 neurodegenerative effect Effects 0.000 claims abstract description 8
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 150000001875 compounds Chemical class 0.000 claims description 77
• -1 3-oxopiperidino Chemical group 0.000 claims description 56
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 49
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 27
• 150000001408 amides Chemical class 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 22
• 239000012453 solvate Substances 0.000 claims description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• 125000001831 (C6-C10) heteroaryl group Chemical group 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
• 208000024827 Alzheimer disease Diseases 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 210000003169 central nervous system Anatomy 0.000 claims description 8
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 206010039966 Senile dementia Diseases 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 210000001428 peripheral nervous system Anatomy 0.000 claims description 5
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 4
• OOHHUMXTKNJKFW-UHFFFAOYSA-N 2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-one Chemical compound C1CCCC(=O)C1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 OOHHUMXTKNJKFW-UHFFFAOYSA-N 0.000 claims description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 claims description 3
• UZMRXFMJIOWDAR-CABZTGNLSA-N (1s,2s)-2-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclobutan-1-ol Chemical compound C([C@H]1[C@H](CC1)O)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 UZMRXFMJIOWDAR-CABZTGNLSA-N 0.000 claims description 2
• FYLGFXDXZKSTJI-UHFFFAOYSA-N 1-[2-amino-5-[(2-chloro-4-ethylphenyl)methyl]pyrimidin-4-yl]piperidin-4-one Chemical compound ClC1=CC(CC)=CC=C1CC1=CN=C(N)N=C1N1CCC(=O)CC1 FYLGFXDXZKSTJI-UHFFFAOYSA-N 0.000 claims description 2
• QNTSGIHJDBCGDZ-UHFFFAOYSA-N 1-[2-amino-5-[(4-bromo-2-chlorophenyl)methyl]pyrimidin-4-yl]piperidin-4-one Chemical compound C1CC(=O)CCN1C1=NC(N)=NC=C1CC1=CC=C(Br)C=C1Cl QNTSGIHJDBCGDZ-UHFFFAOYSA-N 0.000 claims description 2
• JYSHIPCDPOXBKD-UHFFFAOYSA-N 1-[2-amino-5-[[2-chloro-4-(trifluoromethyl)phenyl]methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound C1CCC(=O)CN1C1=NC(N)=NC=C1CC1=CC=C(C(F)(F)F)C=C1Cl JYSHIPCDPOXBKD-UHFFFAOYSA-N 0.000 claims description 2
• HQHHLBFGVUWFOG-UHFFFAOYSA-N 2-[[2-amino-5-(4-chloro-2-fluorophenoxy)pyrimidin-4-yl]amino]ethanol Chemical compound OCCNC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1F HQHHLBFGVUWFOG-UHFFFAOYSA-N 0.000 claims description 2
• KBNPUQQORGGSDW-UHFFFAOYSA-N 2-[[2-amino-5-(4-chloro-2-methylphenoxy)pyrimidin-4-yl]amino]ethanol Chemical compound CC1=CC(Cl)=CC=C1OC1=CN=C(N)N=C1NCCO KBNPUQQORGGSDW-UHFFFAOYSA-N 0.000 claims description 2
• IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 2
• IUQRNEUCHKJYDQ-UHFFFAOYSA-N 4-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-one Chemical compound C1CC(=O)CCC1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 IUQRNEUCHKJYDQ-UHFFFAOYSA-N 0.000 claims description 2
• GRFUIFFKLNHNIC-UHFFFAOYSA-N 4-[[5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-one Chemical compound C1=CC(Cl)=CC=C1OC1=CN=CN=C1NC1CCC(=O)CC1 GRFUIFFKLNHNIC-UHFFFAOYSA-N 0.000 claims description 2
• UZCYYVJRMMNKRT-UHFFFAOYSA-N 5-(4-chlorophenoxy)-4-n-cyclohexylpyrimidine-2,4-diamine Chemical compound C1CCCCC1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 UZCYYVJRMMNKRT-UHFFFAOYSA-N 0.000 claims description 2
• XNSDDHKPRDOTSP-SHTZXODSSA-N C1=CC(CC)=CC=C1OC1=CN=CN=C1N[C@@H]1CC[C@@H](O)CC1 Chemical compound C1=CC(CC)=CC=C1OC1=CN=CN=C1N[C@@H]1CC[C@@H](O)CC1 XNSDDHKPRDOTSP-SHTZXODSSA-N 0.000 claims description 2
• KDWGACNVLZXZNR-MQMHXKEQSA-N C1C[C@@H](CO)CC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1 Chemical compound C1C[C@@H](CO)CC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1 KDWGACNVLZXZNR-MQMHXKEQSA-N 0.000 claims description 2
• AXRMMTFWYVQFPL-JOCQHMNTSA-N C1C[C@@H](O)CC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1 Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1 AXRMMTFWYVQFPL-JOCQHMNTSA-N 0.000 claims description 2
• KGPFXCLEMKEENC-HAQNSBGRSA-N C1C[C@@H](O)CC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1F Chemical compound C1C[C@@H](O)CC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1F KGPFXCLEMKEENC-HAQNSBGRSA-N 0.000 claims description 2
• PUVKKJGFDNSRFV-AULYBMBSSA-N N([C@@H]1CC[C@@H](CO)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 Chemical compound N([C@@H]1CC[C@@H](CO)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 PUVKKJGFDNSRFV-AULYBMBSSA-N 0.000 claims description 2
• AWYGONCSOZSLRM-XYPYZODXSA-N N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1Cl Chemical compound N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1Cl AWYGONCSOZSLRM-XYPYZODXSA-N 0.000 claims description 2
• DQTSGKSDZKDJCS-XYPYZODXSA-N N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1F Chemical compound N([C@@H]1CC[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1F DQTSGKSDZKDJCS-XYPYZODXSA-N 0.000 claims description 2
• ZNVWVEWNCWSELJ-UHFFFAOYSA-N [1-[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]pyrrolidin-2-yl]methanol Chemical compound C1CCC(CO)N1C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 ZNVWVEWNCWSELJ-UHFFFAOYSA-N 0.000 claims description 2
• PTRZEOYINPNTSI-UHFFFAOYSA-N [4-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 PTRZEOYINPNTSI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 125000000623 heterocyclic group Chemical group 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• RMNGMDPYIVUTFS-UHFFFAOYSA-N n-[2-amino-5-(4-bromophenoxy)pyrimidin-4-yl]-n-phenylhydroxylamine Chemical compound C=1C=CC=CC=1N(O)C1=NC(N)=NC=C1OC1=CC=C(Br)C=C1 RMNGMDPYIVUTFS-UHFFFAOYSA-N 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• 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 2
• 102200001405 rs377584435 Human genes 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• WDRVZKJGSJDXON-CHWSQXEVSA-N (1r,2r)-2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-ol Chemical compound N([C@H]1[C@@H](CCCC1)O)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 WDRVZKJGSJDXON-CHWSQXEVSA-N 0.000 claims 1
• XPMQRFWGMBVRDV-VXGBXAGGSA-N (1r,2r)-2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclopentan-1-ol Chemical compound N([C@H]1[C@@H](CCC1)O)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 XPMQRFWGMBVRDV-VXGBXAGGSA-N 0.000 claims 1
• IIQRPFMJYHBHFT-CHWSQXEVSA-N (1r,2r)-2-[[5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclopentan-1-ol Chemical compound O[C@@H]1CCC[C@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1 IIQRPFMJYHBHFT-CHWSQXEVSA-N 0.000 claims 1
• UZMRXFMJIOWDAR-JOYOIKCWSA-N (1r,2s)-2-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclobutan-1-ol Chemical compound C([C@H]1[C@@H](CC1)O)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 UZMRXFMJIOWDAR-JOYOIKCWSA-N 0.000 claims 1
• RVKBVGVAFLHOPI-SMDDNHRTSA-N (1r,2s)-2-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclohexan-1-ol Chemical compound C([C@H]1[C@@H](CCCC1)O)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 RVKBVGVAFLHOPI-SMDDNHRTSA-N 0.000 claims 1
• YMLAIIULOFNEBL-GXFFZTMASA-N (1r,2s)-2-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclopentan-1-ol Chemical compound C([C@H]1[C@@H](CCC1)O)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 YMLAIIULOFNEBL-GXFFZTMASA-N 0.000 claims 1
• DQWTZTCKHNOTQM-NWDGAFQWSA-N (1r,3s)-3-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-ol Chemical compound N([C@@H]1C[C@H](O)CCC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 DQWTZTCKHNOTQM-NWDGAFQWSA-N 0.000 claims 1
• VMHKCSIZCDEGEJ-WDEREUQCSA-N (1r,3s)-3-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclopentan-1-ol Chemical compound N([C@@H]1C[C@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 VMHKCSIZCDEGEJ-WDEREUQCSA-N 0.000 claims 1
• NHDLPPJQUWJAEU-QWHCGFSZSA-N (1r,3s)-3-[[5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-ol Chemical compound C1[C@H](O)CCC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1 NHDLPPJQUWJAEU-QWHCGFSZSA-N 0.000 claims 1
• SPNNAWYJVKRRAK-WCQYABFASA-N (1r,3s)-3-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclohexan-1-ol Chemical compound C([C@@H]1C[C@H](O)CCC1)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 SPNNAWYJVKRRAK-WCQYABFASA-N 0.000 claims 1
• OWJCJDQFSBGPRX-CMPLNLGQSA-N (1r,3s)-3-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclopentan-1-ol Chemical compound C([C@@H]1C[C@H](O)CC1)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 OWJCJDQFSBGPRX-CMPLNLGQSA-N 0.000 claims 1
• WDRVZKJGSJDXON-OLZOCXBDSA-N (1s,2r)-2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-ol Chemical compound N([C@H]1[C@H](CCCC1)O)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 WDRVZKJGSJDXON-OLZOCXBDSA-N 0.000 claims 1
• XPMQRFWGMBVRDV-NEPJUHHUSA-N (1s,2r)-2-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclopentan-1-ol Chemical compound N([C@H]1[C@H](CCC1)O)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 XPMQRFWGMBVRDV-NEPJUHHUSA-N 0.000 claims 1
• RVKBVGVAFLHOPI-FZMZJTMJSA-N (1s,2s)-2-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclohexan-1-ol Chemical compound C([C@H]1[C@H](CCCC1)O)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 RVKBVGVAFLHOPI-FZMZJTMJSA-N 0.000 claims 1
• YMLAIIULOFNEBL-GWCFXTLKSA-N (1s,2s)-2-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclopentan-1-ol Chemical compound C([C@H]1[C@H](CCC1)O)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 YMLAIIULOFNEBL-GWCFXTLKSA-N 0.000 claims 1
• DQWTZTCKHNOTQM-RYUDHWBXSA-N (1s,3s)-3-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclohexan-1-ol Chemical compound N([C@@H]1C[C@@H](O)CCC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 DQWTZTCKHNOTQM-RYUDHWBXSA-N 0.000 claims 1
• VMHKCSIZCDEGEJ-QWRGUYRKSA-N (1s,3s)-3-[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclopentan-1-ol Chemical compound N([C@@H]1C[C@@H](O)CC1)C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 VMHKCSIZCDEGEJ-QWRGUYRKSA-N 0.000 claims 1
• WCGXTJTYWBFRCH-RYUDHWBXSA-N (1s,3s)-3-[[5-(4-chlorophenoxy)pyrimidin-4-yl]amino]cyclopentan-1-ol Chemical compound C1[C@@H](O)CC[C@@H]1NC1=NC=NC=C1OC1=CC=C(Cl)C=C1 WCGXTJTYWBFRCH-RYUDHWBXSA-N 0.000 claims 1
• SPNNAWYJVKRRAK-AAEUAGOBSA-N (1s,3s)-3-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclohexan-1-ol Chemical compound C([C@@H]1C[C@@H](O)CCC1)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 SPNNAWYJVKRRAK-AAEUAGOBSA-N 0.000 claims 1
• OWJCJDQFSBGPRX-JQWIXIFHSA-N (1s,3s)-3-[[[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]amino]methyl]cyclopentan-1-ol Chemical compound C([C@@H]1C[C@@H](O)CC1)NC1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 OWJCJDQFSBGPRX-JQWIXIFHSA-N 0.000 claims 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• HMVXMQDEQZMYTM-UHFFFAOYSA-N 1-[2-amino-5-(4-chlorophenoxy)pyrimidin-4-yl]pyrrolidin-3-ol Chemical compound C1CC(O)CN1C1=NC(N)=NC=C1OC1=CC=C(Cl)C=C1 HMVXMQDEQZMYTM-UHFFFAOYSA-N 0.000 claims 1
• DLQKRKXAPMSNIU-UHFFFAOYSA-N 1-[2-amino-5-[(2,4-dichlorophenyl)methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound C1CCC(=O)CN1C1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1Cl DLQKRKXAPMSNIU-UHFFFAOYSA-N 0.000 claims 1
• PSDOJMKHHBVUKY-UHFFFAOYSA-N 1-[2-amino-5-[(2,4-dichlorophenyl)methyl]pyrimidin-4-yl]piperidin-4-one Chemical compound C1CC(=O)CCN1C1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1Cl PSDOJMKHHBVUKY-UHFFFAOYSA-N 0.000 claims 1
• MFLSOPKYZJZSBT-UHFFFAOYSA-N 1-[2-amino-5-[(2-chloro-4-ethylphenyl)methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound ClC1=CC(CC)=CC=C1CC1=CN=C(N)N=C1N1CC(=O)CCC1 MFLSOPKYZJZSBT-UHFFFAOYSA-N 0.000 claims 1
• PQCHKBRHYRPMQA-UHFFFAOYSA-N 1-[2-amino-5-[(2-chloro-4-methylphenyl)methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound ClC1=CC(C)=CC=C1CC1=CN=C(N)N=C1N1CC(=O)CCC1 PQCHKBRHYRPMQA-UHFFFAOYSA-N 0.000 claims 1
• MNDXSQASUHYHSJ-UHFFFAOYSA-N 1-[2-amino-5-[(2-chloro-4-methylphenyl)methyl]pyrimidin-4-yl]piperidin-4-one Chemical compound ClC1=CC(C)=CC=C1CC1=CN=C(N)N=C1N1CCC(=O)CC1 MNDXSQASUHYHSJ-UHFFFAOYSA-N 0.000 claims 1
• BBBPAIHLXDVRDM-UHFFFAOYSA-N 1-[2-amino-5-[(4-bromo-2-chlorophenyl)methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound C1CCC(=O)CN1C1=NC(N)=NC=C1CC1=CC=C(Br)C=C1Cl BBBPAIHLXDVRDM-UHFFFAOYSA-N 0.000 claims 1
• DHIZPSVXNNFCRI-UHFFFAOYSA-N 1-[2-amino-5-[(4-bromophenyl)methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound C1CCC(=O)CN1C1=NC(N)=NC=C1CC1=CC=C(Br)C=C1 DHIZPSVXNNFCRI-UHFFFAOYSA-N 0.000 claims 1
• XTGCAFJJANFPJK-UHFFFAOYSA-N 1-[2-amino-5-[(4-bromophenyl)methyl]pyrimidin-4-yl]piperidin-4-one Chemical compound C1CC(=O)CCN1C1=NC(N)=NC=C1CC1=CC=C(Br)C=C1 XTGCAFJJANFPJK-UHFFFAOYSA-N 0.000 claims 1
• ISYITNRSSWFOQN-UHFFFAOYSA-N 1-[2-amino-5-[(4-chlorophenyl)methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound C1CCC(=O)CN1C1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1 ISYITNRSSWFOQN-UHFFFAOYSA-N 0.000 claims 1
• URNSBDYTIUKUCV-UHFFFAOYSA-N 1-[2-amino-5-[(4-chlorophenyl)methyl]pyrimidin-4-yl]piperidin-4-one Chemical compound C1CC(=O)CCN1C1=NC(N)=NC=C1CC1=CC=C(Cl)C=C1 URNSBDYTIUKUCV-UHFFFAOYSA-N 0.000 claims 1
• UUSDFVXOGINRFP-UHFFFAOYSA-N 1-[2-amino-5-[(4-ethylphenyl)methyl]pyrimidin-4-yl]piperidin-3-one Chemical compound C1=CC(CC)=CC=C1CC1=CN=C(N)N=C1N1CC(=O)CCC1 UUSDFVXOGINRFP-UHFFFAOYSA-N 0.000 claims 1
• XWWPKPYRRPVEFR-UHFFFAOYSA-N 1-[2-amino-5-[(4-ethylphenyl)methyl]pyrimidin-4-yl]piperidin-4-one Chemical compound C1=CC(CC)=CC=C1CC1=CN=C(N)N=C1N1CCC(=O)CC1 XWWPKPYRRPVEFR-UHFFFAOYSA-N 0.000 claims 1
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