RU2019115115A - Производные пиперидина в качестве ингибиторов убиквитин-специфической протеазы 7 - Google Patents
Производные пиперидина в качестве ингибиторов убиквитин-специфической протеазы 7 Download PDFInfo
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- RU2019115115A RU2019115115A RU2019115115A RU2019115115A RU2019115115A RU 2019115115 A RU2019115115 A RU 2019115115A RU 2019115115 A RU2019115115 A RU 2019115115A RU 2019115115 A RU2019115115 A RU 2019115115A RU 2019115115 A RU2019115115 A RU 2019115115A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- hydroxy
- piperidin
- phenylbutanoyl
- pyrimidin
- Prior art date
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title 1
- 101710180012 Protease 7 Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- -1 ethylamine-substituted pyrazole Chemical class 0.000 claims 76
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 13
- 206010028980 Neoplasm Diseases 0.000 claims 11
- 201000011510 cancer Diseases 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 7
- 150000003973 alkyl amines Chemical class 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims 3
- 206010029260 Neuroblastoma Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000008482 dysregulation Effects 0.000 claims 3
- 208000005017 glioblastoma Diseases 0.000 claims 3
- 230000002489 hematologic effect Effects 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 230000003211 malignant effect Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical group N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims 2
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 claims 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000011737 fluorine Chemical group 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XAWZDWAAJHUPFS-HXUWFJFHSA-N (3R)-1-[4-hydroxy-4-[(5-phenylpyrazin-2-yl)methyl]piperidin-1-yl]-3-phenylbutan-1-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CC1=NC=C(N=C1)C1=CC=CC=C1 XAWZDWAAJHUPFS-HXUWFJFHSA-N 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- GLENYAXDPPRWHZ-UHFFFAOYSA-N 1-[[1-(2-cyclopropyl-1,3-oxazole-5-carbonyl)-4-hydroxypiperidin-4-yl]methyl]-8-methyl-9-phenylpurin-6-one Chemical compound Cc1nc2c(ncn(CC3(O)CCN(CC3)C(=O)c3cnc(o3)C3CC3)c2=O)n1-c1ccccc1 GLENYAXDPPRWHZ-UHFFFAOYSA-N 0.000 claims 1
- KIZPZMXSLXGGHH-UHFFFAOYSA-N 1-[[1-(3,3-dicyclopropylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-8-methyl-9-phenylpurin-6-one Chemical compound C1(CC1)C(CC(=O)N1CCC(CC1)(O)CN1C=NC=2N(C(=NC=2C1=O)C)C1=CC=CC=C1)C1CC1 KIZPZMXSLXGGHH-UHFFFAOYSA-N 0.000 claims 1
- GWBALYGNNQXQPP-OAQYLSRUSA-N 1-[[1-[(3R)-4,4-difluoro-3-phenylbutanoyl]-4-hydroxypiperidin-4-yl]methyl]-9-phenylpurin-6-one Chemical compound FC([C@H](CC(=O)N1CCC(CC1)(O)CN1C=NC=2N(C=NC=2C1=O)C1=CC=CC=C1)C1=CC=CC=C1)F GWBALYGNNQXQPP-OAQYLSRUSA-N 0.000 claims 1
- XNODJWFHCPTPFB-GOSISDBHSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-3H-indol-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(CN2C(=O)Cc3ccccc23)CC1)c1ccccc1 XNODJWFHCPTPFB-GOSISDBHSA-N 0.000 claims 1
- OJFFALBYHADJRI-HXUWFJFHSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-8-methyl-9-phenylpurin-6-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2N(C(=NC=2C1=O)C)C1=CC=CC=C1 OJFFALBYHADJRI-HXUWFJFHSA-N 0.000 claims 1
- JGDQEKPRGWLRAJ-OAHLLOKOSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-9-methyl-8-(trifluoromethyl)purin-6-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2N(C(=NC=2C1=O)C(F)(F)F)C JGDQEKPRGWLRAJ-OAHLLOKOSA-N 0.000 claims 1
- VLBPWNUBKLADBH-HXUWFJFHSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-9-methyl-8-phenylpurin-6-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2N(C(=NC=2C1=O)C1=CC=CC=C1)C VLBPWNUBKLADBH-HXUWFJFHSA-N 0.000 claims 1
- DDILCTCUZBWAMV-MRXNPFEDSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-9-methylpurin-6-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2N(C=NC=2C1=O)C DDILCTCUZBWAMV-MRXNPFEDSA-N 0.000 claims 1
- IGHGWYBXSSYKEF-HXUWFJFHSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-9-phenylpurin-6-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2N(C=NC=2C1=O)C1=CC=CC=C1 IGHGWYBXSSYKEF-HXUWFJFHSA-N 0.000 claims 1
- FYYBIDAVIPMBNE-OAQYLSRUSA-N 1-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-9-phenylpurin-6-one Chemical compound C1=CC=CC=C1N1C2=C(N=C1)C(=O)N(CC1(CCN(C(=O)C[C@H](C3=CC=CC=C3)C(F)(F)F)CC1)O)C=N2 FYYBIDAVIPMBNE-OAQYLSRUSA-N 0.000 claims 1
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical group CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 claims 1
- VPJHNXFJXXHQMI-QSVWIEALSA-N 2-[[1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-1,3-diazinan-4-yl]amino]-N,N-dimethylacetamide Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)NCC(=O)N(C)C)O)C3=CC=CC=C3 VPJHNXFJXXHQMI-QSVWIEALSA-N 0.000 claims 1
- SCLSGOPGWDPMIW-LJQANCHMSA-N 3-(2-aminophenyl)-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4ccccc4N)n(C)nc3c2=O)CC1)c1ccccc1 SCLSGOPGWDPMIW-LJQANCHMSA-N 0.000 claims 1
- PTSGXBFQKPCRMW-LJQANCHMSA-N 3-(2-fluorophenyl)-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4ccccc4F)n(C)nc3c2=O)CC1)c1ccccc1 PTSGXBFQKPCRMW-LJQANCHMSA-N 0.000 claims 1
- MVTJIINPWJPMTH-LJQANCHMSA-N 3-(3-aminophenyl)-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4cccc(N)c4)n(C)nc3c2=O)CC1)c1ccccc1 MVTJIINPWJPMTH-LJQANCHMSA-N 0.000 claims 1
- FXXNIVHGXTWLNC-LJQANCHMSA-N 3-(3-hydroxy-3-methylbut-1-ynyl)-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(C#CC(C)(C)O)n(C)nc3c2=O)CC1)c1ccccc1 FXXNIVHGXTWLNC-LJQANCHMSA-N 0.000 claims 1
- LGEIGCWCSAYZMY-LJQANCHMSA-N 3-(3-hydroxyphenyl)-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4cccc(O)c4)n(C)nc3c2=O)CC1)c1ccccc1 LGEIGCWCSAYZMY-LJQANCHMSA-N 0.000 claims 1
- LPIUXCXUBPJYKP-OAQYLSRUSA-N 3-(cyclohexen-1-yl)-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1(=CCCCC1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O)C LPIUXCXUBPJYKP-OAQYLSRUSA-N 0.000 claims 1
- AHNQOUPXANJVNP-UHFFFAOYSA-N 3-[(1-acetyl-4-hydroxypiperidin-4-yl)methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-one Chemical compound C(C)(=O)N1CCC(CC1)(O)CN1C=NC(=CC1=O)NCCN1CCCC1 AHNQOUPXANJVNP-UHFFFAOYSA-N 0.000 claims 1
- WJBNOQHVRACGGP-HXUWFJFHSA-N 3-[3-(dimethylamino)prop-1-ynyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound N1(C(=C2C(=N1)C(=O)N(CC1(CCN(C(=O)C[C@H](C3=CC=CC=C3)C(F)(F)F)CC1)O)C=N2)C#CCN(C)C)C WJBNOQHVRACGGP-HXUWFJFHSA-N 0.000 claims 1
- RFJZVNGMTRZNKU-JOCHJYFZSA-N 3-[4-(1-aminocyclobutyl)phenyl]-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NC1(CCC1)C1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)O)C RFJZVNGMTRZNKU-JOCHJYFZSA-N 0.000 claims 1
- CBVGSIWRFQUPHT-HSZRJFAPSA-N 3-[4-(1-aminocyclopropyl)phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NC1(CC1)C1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O)C CBVGSIWRFQUPHT-HSZRJFAPSA-N 0.000 claims 1
- WQVUVIBUQLBECF-HSZRJFAPSA-N 3-[4-(2-aminoethyl)phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O)C WQVUVIBUQLBECF-HSZRJFAPSA-N 0.000 claims 1
- STIBUVNAOGWETA-JOCHJYFZSA-N 3-[4-(aminomethyl)-3-(trifluoromethyl)phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C1=C(C(=CC(C=2N(N=C3C=2N=CN(C3=O)CC2(CCN(C(=O)C[C@H](C3=CC=CC=C3)C(F)(F)F)CC2)O)C)=C1)C(F)(F)F)CN STIBUVNAOGWETA-JOCHJYFZSA-N 0.000 claims 1
- YXNMXSSZTNGFEO-OAQYLSRUSA-N 3-[4-(aminomethyl)-3-fluorophenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound FC1=CC(C=2N(N=C3C=2N=CN(C3=O)CC2(CCN(C(=O)C[C@H](C3=CC=CC=C3)C(F)(F)F)CC2)O)C)=CC=C1CN YXNMXSSZTNGFEO-OAQYLSRUSA-N 0.000 claims 1
- RGELMQCRGBFASX-OAQYLSRUSA-N 3-[4-(aminomethyl)phenyl]-2-ethyl-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)O)CC RGELMQCRGBFASX-OAQYLSRUSA-N 0.000 claims 1
- RZXYPQYTEZXQOA-UHFFFAOYSA-N 3-[4-(aminomethyl)phenyl]-6-[[1-(2-cyclopropyl-1,3-oxazole-5-carbonyl)-4-hydroxypiperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1=CN=C(O1)C1CC1)O)C RZXYPQYTEZXQOA-UHFFFAOYSA-N 0.000 claims 1
- QWFFFPNIXGPPKL-UHFFFAOYSA-N 3-[4-(aminomethyl)phenyl]-6-[[1-(3,3-dicyclopropylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(CC(C1CC1)C1CC1)=O)O)C QWFFFPNIXGPPKL-UHFFFAOYSA-N 0.000 claims 1
- CUHVPPDLGMPRSC-UHFFFAOYSA-N 3-[4-(aminomethyl)phenyl]-6-[[1-(3-cyclobutylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(CCC1CCC1)=O)O)C CUHVPPDLGMPRSC-UHFFFAOYSA-N 0.000 claims 1
- FLWNDXYQUHZIQJ-JOCHJYFZSA-N 3-[4-(aminomethyl)phenyl]-6-[[1-[(3R)-3-(3,5-difluorophenyl)-4,4,4-trifluorobutanoyl]-4-hydroxypiperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC(=CC(=C1)F)F)=O)O)C FLWNDXYQUHZIQJ-JOCHJYFZSA-N 0.000 claims 1
- YBDNJHPVTVYIFV-JOCHJYFZSA-N 3-[4-(aminomethyl)phenyl]-6-[[1-[(3R)-4,4-difluoro-3-phenylbutanoyl]-4-hydroxypiperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)F)C1=CC=CC=C1)=O)O)C YBDNJHPVTVYIFV-JOCHJYFZSA-N 0.000 claims 1
- NMLXENYXNZMFOB-UHFFFAOYSA-N 3-[4-(aminomethyl)phenyl]-6-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound Cn1nc2c(ncn(CC3(O)CCN(CC3)C(=O)C3(C)CC3)c2=O)c1-c1ccc(CN)cc1 NMLXENYXNZMFOB-UHFFFAOYSA-N 0.000 claims 1
- DGHAUZFDWIZFRM-HXUWFJFHSA-N 3-[4-(aminomethyl)phenyl]-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)O)C DGHAUZFDWIZFRM-HXUWFJFHSA-N 0.000 claims 1
- WXOXRMSONJCXSX-JOCHJYFZSA-N 3-[4-(aminomethyl)phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-(4-fluorophenyl)butanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound NCC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=C(C=C1)F)=O)O)C WXOXRMSONJCXSX-JOCHJYFZSA-N 0.000 claims 1
- RLPQYKGBXQQARM-JOCHJYFZSA-N 3-[4-(aminomethyl)phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound Cn1nc2c(ncn(CC3(O)CCN(CC3)C(=O)C[C@H](c3ccccc3)C(F)(F)F)c2=O)c1-c1ccc(CN)cc1 RLPQYKGBXQQARM-JOCHJYFZSA-N 0.000 claims 1
- IJRSPJXVEIGTHX-HXUWFJFHSA-N 3-[4-(aminomethyl)phenyl]-6-[[4-hydroxy-1-[(3S)-4,4,4-trifluoro-3-(5-methylthiophen-2-yl)butanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound Cc1ccc(s1)[C@@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4ccc(CN)cc4)n(C)nc3c2=O)CC1)C(F)(F)F IJRSPJXVEIGTHX-HXUWFJFHSA-N 0.000 claims 1
- HRHFNXITLYXAQR-HXUWFJFHSA-N 3-[4-(hydroxymethyl)phenyl]-6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4ccc(CO)cc4)n(C)nc3c2=O)CC1)c1ccccc1 HRHFNXITLYXAQR-HXUWFJFHSA-N 0.000 claims 1
- WHRDTLMQXVEBPC-QFQXNSOFSA-N 3-[4-[(1R)-1-amino-2,2,2-trifluoroethyl]phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound N[C@@H](C(F)(F)F)C1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O)C WHRDTLMQXVEBPC-QFQXNSOFSA-N 0.000 claims 1
- APLLAKBPNYCKMS-AUSIDOKSSA-N 3-[4-[(1R)-1-aminoethyl]phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@@H](N)c1ccc(cc1)-c1n(C)nc2c1ncn(CC1(O)CCN(CC1)C(=O)C[C@H](c1ccccc1)C(F)(F)F)c2=O APLLAKBPNYCKMS-AUSIDOKSSA-N 0.000 claims 1
- WHRDTLMQXVEBPC-RLWLMLJZSA-N 3-[4-[(1S)-1-amino-2,2,2-trifluoroethyl]phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound N[C@H](C(F)(F)F)C1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O)C WHRDTLMQXVEBPC-RLWLMLJZSA-N 0.000 claims 1
- DCRWJOARMKWSNR-GGAORHGYSA-N 3-[4-[(1S)-1-amino-2,2-difluoroethyl]phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound N[C@H](C(F)F)C1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O)C DCRWJOARMKWSNR-GGAORHGYSA-N 0.000 claims 1
- APLLAKBPNYCKMS-WMZHIEFXSA-N 3-[4-[(1S)-1-aminoethyl]phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](N)c1ccc(cc1)-c1n(C)nc2c1ncn(CC1(O)CCN(CC1)C(=O)C[C@H](c1ccccc1)C(F)(F)F)c2=O APLLAKBPNYCKMS-WMZHIEFXSA-N 0.000 claims 1
- BUGSRXNPDCXKHB-XMMPIXPASA-N 3-[4-[(dimethylamino)methyl]phenyl]-6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound CN(C)CC1=CC=C(C=C1)C=1N(N=C2C=1N=CN(C2=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O)C BUGSRXNPDCXKHB-XMMPIXPASA-N 0.000 claims 1
- JDLLYACWFFLZNR-LJQANCHMSA-N 3-[6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-7-oxopyrazolo[4,3-d]pyrimidin-3-yl]benzamide Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4cccc(c4)C(N)=O)n(C)nc3c2=O)CC1)c1ccccc1 JDLLYACWFFLZNR-LJQANCHMSA-N 0.000 claims 1
- CGRDUIJOGPNDJQ-LJQANCHMSA-N 3-[6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-7-oxopyrazolo[4,3-d]pyrimidin-3-yl]benzoic acid Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2C(C1=O)=NN(C=2C=1C=C(C(=O)O)C=CC=1)C CGRDUIJOGPNDJQ-LJQANCHMSA-N 0.000 claims 1
- SZWJFTRWJXUMIB-HXUWFJFHSA-N 3-[6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-7-oxopyrazolo[4,3-d]pyrimidin-3-yl]benzonitrile Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4cccc(c4)C#N)n(C)nc3c2=O)CC1)c1ccccc1 SZWJFTRWJXUMIB-HXUWFJFHSA-N 0.000 claims 1
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- GYBVZUILLBUUEW-OAQYLSRUSA-N 3-[[1-[(3R)-4,4-difluoro-3-phenylbutanoyl]-4-hydroxypiperidin-4-yl]methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-one Chemical compound FC([C@H](CC(=O)N1CCC(CC1)(O)CN1C=NC(=CC1=O)NCCN1CCCC1)C1=CC=CC=C1)F GYBVZUILLBUUEW-OAQYLSRUSA-N 0.000 claims 1
- JZUCGLCVLJAKNG-UHFFFAOYSA-N 3-[[1-[2,2-di(cyclobutyl)acetyl]-4-hydroxypiperidin-4-yl]methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-one Chemical compound OC1(Cn2cnc(NCCN3CCCC3)cc2=O)CCN(CC1)C(=O)C(C1CCC1)C1CCC1 JZUCGLCVLJAKNG-UHFFFAOYSA-N 0.000 claims 1
- SACXMRDWUOQUAA-UHFFFAOYSA-N 3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]-4-oxo-7-phenylpyrrolo[2,3-d]pyrimidine-6-carbonitrile Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(cc3c2=O)C#N)-c2ccccc2)CC1 SACXMRDWUOQUAA-UHFFFAOYSA-N 0.000 claims 1
- JMRDJXMTKLVLQV-UHFFFAOYSA-N 3-[[4-hydroxy-1-(3-phenylpropanoyl)piperidin-4-yl]methyl]furo[2,3-d]pyrimidin-4-one Chemical compound OC1(Cn2cnc3occc3c2=O)CCN(CC1)C(=O)CCc1ccccc1 JMRDJXMTKLVLQV-UHFFFAOYSA-N 0.000 claims 1
- YYICLMSQJLANAQ-UHFFFAOYSA-N 3-[[4-hydroxy-1-(3-phenylpropanoyl)piperidin-4-yl]methyl]furo[3,2-d]pyrimidin-4-one Chemical compound OC1(Cn2cnc3ccoc3c2=O)CCN(CC1)C(=O)CCc1ccccc1 YYICLMSQJLANAQ-UHFFFAOYSA-N 0.000 claims 1
- PUMARQOGXIAXIE-QGZVFWFLSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(1H-pyrazol-5-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)-c2ccn[nH]2)CC1)c1ccccc1 PUMARQOGXIAXIE-QGZVFWFLSA-N 0.000 claims 1
- QVPMLWJGHXDRIZ-GOSISDBHSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-methoxyethylamino)pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NCCOC QVPMLWJGHXDRIZ-GOSISDBHSA-N 0.000 claims 1
- PXLGBAZZVIXIFD-PSDZMVHGSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-oxa-7-azaspiro[3.4]octan-7-yl)-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CCC4(C3)COC4)O)C5=CC=CC=C5 PXLGBAZZVIXIFD-PSDZMVHGSA-N 0.000 claims 1
- UZRAYGPNCRCHSB-OSMGYRLQSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-oxa-7-azaspiro[4.4]nonan-7-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCC3(CCOC3)C2)CC1)c1ccccc1 UZRAYGPNCRCHSB-OSMGYRLQSA-N 0.000 claims 1
- PIPBCHIHVSLXPX-JOCHJYFZSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-phenylethynyl)pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)C#CC1=CC=CC=C1 PIPBCHIHVSLXPX-JOCHJYFZSA-N 0.000 claims 1
- MSQCSWCXCJOWLD-PBGLPUTKSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(3-morpholin-4-ylpyrrolidin-1-yl)-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CCC(C3)N4CCOCC4)O)C5=CC=CC=C5 MSQCSWCXCJOWLD-PBGLPUTKSA-N 0.000 claims 1
- JQRXJHOAYLRZOI-LCQOSCCDSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(4-hydroxypiperidin-1-yl)-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CCC(CC3)O)O)C4=CC=CC=C4 JQRXJHOAYLRZOI-LCQOSCCDSA-N 0.000 claims 1
- UEBLWMDAWZAKMN-HXUWFJFHSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(4-methylpiperazin-1-yl)pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)N1CCN(CC1)C UEBLWMDAWZAKMN-HXUWFJFHSA-N 0.000 claims 1
- ANIRAYBZHBFHRM-OAQYLSRUSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(5-methyl-2,5-diazaspiro[3.4]octan-2-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CC3(C2)CCCN3C)CC1)c1ccccc1 ANIRAYBZHBFHRM-OAQYLSRUSA-N 0.000 claims 1
- WLHJTEFNGCLFDP-PSDZMVHGSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(5-oxa-2-azaspiro[3.4]octan-2-yl)-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CC4(C3)CCCO4)O)C5=CC=CC=C5 WLHJTEFNGCLFDP-PSDZMVHGSA-N 0.000 claims 1
- HEYAYRTUUKXNTA-PSDZMVHGSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(6-oxa-2-azaspiro[3.4]octan-2-yl)-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CC4(C3)CCOC4)O)C5=CC=CC=C5 HEYAYRTUUKXNTA-PSDZMVHGSA-N 0.000 claims 1
- YWPQOLBATPSNLZ-FKHAVUOCSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(7-oxa-2-azaspiro[3.5]nonan-2-yl)-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CC4(C3)CCOCC4)O)C5=CC=CC=C5 YWPQOLBATPSNLZ-FKHAVUOCSA-N 0.000 claims 1
- QEDGANHLOJDBKL-OAQYLSRUSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(8-methyl-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CC3(C2)CN(C)CCO3)CC1)c1ccccc1 QEDGANHLOJDBKL-OAQYLSRUSA-N 0.000 claims 1
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- TXGLTPBNSHRRQU-KMFTYDHNSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(oxolan-3-ylamino)-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)NC3CCOC3)O)C4=CC=CC=C4 TXGLTPBNSHRRQU-KMFTYDHNSA-N 0.000 claims 1
- ARCMLXVLWVMKQC-XPNTWCBSSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[(1R,5S)-3-methyl-3,6-diazabicyclo[3.2.1]octan-6-yl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2C[C@@H]3C[C@H]2CN(C)C3)CC1)c1ccccc1 ARCMLXVLWVMKQC-XPNTWCBSSA-N 0.000 claims 1
- ARCMLXVLWVMKQC-FUPPJEDESA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[(1S,5R)-3-methyl-3,6-diazabicyclo[3.2.1]octan-6-yl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2C[C@H]3C[C@@H]2CN(C)C3)CC1)c1ccccc1 ARCMLXVLWVMKQC-FUPPJEDESA-N 0.000 claims 1
- APIQKRAHGGWDEV-LJQANCHMSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[(2-methylpyrazol-3-yl)methylamino]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCc3ccnn3C)cc2=O)CC1)c1ccccc1 APIQKRAHGGWDEV-LJQANCHMSA-N 0.000 claims 1
- PMBYMIGYHSAKLU-QSVWIEALSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[(3-methyloxetan-3-yl)amino]-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)NC3(COC3)C)O)C4=CC=CC=C4 PMBYMIGYHSAKLU-QSVWIEALSA-N 0.000 claims 1
- KDRKESWKZXNKES-HWWNHIDJSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[(E)-3-pyrrolidin-1-ylprop-1-enyl]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)\C=C\CN1CCCC1 KDRKESWKZXNKES-HWWNHIDJSA-N 0.000 claims 1
- LKUBKGBLQHOULQ-PSDZMVHGSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[2-(propan-2-ylamino)ethylamino]-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)NCCNC(C)C)O)C3=CC=CC=C3 LKUBKGBLQHOULQ-PSDZMVHGSA-N 0.000 claims 1
- XNSXEQJMVHYWRR-ISKFKSNPSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[2-[(2R)-2-(methoxymethyl)pyrrolidin-1-yl]ethylamino]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NCCN1[C@H](CCC1)COC XNSXEQJMVHYWRR-ISKFKSNPSA-N 0.000 claims 1
- YYZQEEQWZOVQSA-FGZHOGPDSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[2-[(2R)-2-methylpyrrolidin-1-yl]ethylamino]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCCN3CCC[C@H]3C)cc2=O)CC1)c1ccccc1 YYZQEEQWZOVQSA-FGZHOGPDSA-N 0.000 claims 1
- YYZQEEQWZOVQSA-YADHBBJMSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[2-[(2S)-2-methylpyrrolidin-1-yl]ethylamino]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NCCN1[C@H](CCC1)C YYZQEEQWZOVQSA-YADHBBJMSA-N 0.000 claims 1
- GGRRIHVXLZSQRZ-FCHUYYIVSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[2-[(3S)-3-methylpyrrolidin-1-yl]ethylamino]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NCCN1C[C@H](CC1)C GGRRIHVXLZSQRZ-FCHUYYIVSA-N 0.000 claims 1
- ZKCOSMNKHHKYNX-LCQOSCCDSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[2-[[4-(trifluoromethyl)pyrimidin-2-yl]amino]ethylamino]-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)NCCNC3=NC=CC(=N3)C(F)(F)F)O)C4=CC=CC=C4 ZKCOSMNKHHKYNX-LCQOSCCDSA-N 0.000 claims 1
- VEKAAPHOQVTGEN-LCQOSCCDSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[3-(methoxymethyl)azetidin-1-yl]-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CC(C3)COC)O)C4=CC=CC=C4 VEKAAPHOQVTGEN-LCQOSCCDSA-N 0.000 claims 1
- QQHUBLVZRJBSIP-OAQYLSRUSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[4-(1H-pyrazol-5-yl)piperidin-1-yl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCC(CC2)c2ccn[nH]2)CC1)c1ccccc1 QQHUBLVZRJBSIP-OAQYLSRUSA-N 0.000 claims 1
- KDKKOGWGXHDXDO-DXDQHDRFSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[4-(pyridin-2-ylmethyl)piperazin-1-yl]-1,3-diazinan-4-one Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CCN(CC3)CC4=CC=CC=N4)O)C5=CC=CC=C5 KDKKOGWGXHDXDO-DXDQHDRFSA-N 0.000 claims 1
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- RLZJEGKGIHARPJ-LJQANCHMSA-N 6-[2-(dimethylamino)ethylamino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCCN(C)C)cc2=O)CC1)c1ccccc1 RLZJEGKGIHARPJ-LJQANCHMSA-N 0.000 claims 1
- UDCUOYWIYORHSS-IFMALSPDSA-N 6-[2-[(3R)-3-fluoropyrrolidin-1-yl]ethylamino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCCN3CC[C@@H](F)C3)cc2=O)CC1)c1ccccc1 UDCUOYWIYORHSS-IFMALSPDSA-N 0.000 claims 1
- UDCUOYWIYORHSS-IRLDBZIGSA-N 6-[2-[(3S)-3-fluoropyrrolidin-1-yl]ethylamino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCCN3CC[C@H](F)C3)cc2=O)CC1)c1ccccc1 UDCUOYWIYORHSS-IRLDBZIGSA-N 0.000 claims 1
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- DVWSLKHCMCAQJS-HXUWFJFHSA-N 9-[4-(aminomethyl)phenyl]-1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]purin-6-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3n(cnc3c2=O)-c2ccc(CN)cc2)CC1)c1ccccc1 DVWSLKHCMCAQJS-HXUWFJFHSA-N 0.000 claims 1
- FRSKFYIUQPOUFY-HSZRJFAPSA-N 9-[4-(aminomethyl)phenyl]-1-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-8-methylpurin-6-one Chemical compound NCC1=CC=C(C=C1)N1C=2N=CN(C(C=2N=C1C)=O)CC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)O FRSKFYIUQPOUFY-HSZRJFAPSA-N 0.000 claims 1
- LHYLIAZDZACMAZ-JOCHJYFZSA-N 9-[4-(aminomethyl)phenyl]-1-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]purin-6-one Chemical compound NCc1ccc(cc1)-n1cnc2c1ncn(CC1(O)CCN(CC1)C(=O)C[C@H](c1ccccc1)C(F)(F)F)c2=O LHYLIAZDZACMAZ-JOCHJYFZSA-N 0.000 claims 1
- 125000006549 C4-C10 aryl group Chemical group 0.000 claims 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- VMWSLYBMBKVVNH-CGHJUBPDSA-N N-(cyclopropylmethyl)-1-[1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-1,3-diazinan-4-yl]azetidine-3-carboxamide Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)N3CC(C3)C(=O)NCC4CC4)O)C5=CC=CC=C5 VMWSLYBMBKVVNH-CGHJUBPDSA-N 0.000 claims 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 1
- LUBPURPJQVQIOT-ITUIMRKVSA-N N-[2-[[1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-1,3-diazinan-4-yl]amino]ethyl]acetamide Chemical compound C[C@H](CC(=O)N1CCC(CC1)(CN2CNC(CC2=O)NCCNC(=O)C)O)C3=CC=CC=C3 LUBPURPJQVQIOT-ITUIMRKVSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- MTKFBLYNGGWEQD-UHFFFAOYSA-N benzyl 4-[[3-[4-(aminomethyl)phenyl]-2-methyl-7-oxopyrazolo[4,3-d]pyrimidin-6-yl]methyl]-4-hydroxypiperidine-1-carboxylate Chemical compound Cn1nc2c(ncn(CC3(O)CCN(CC3)C(=O)OCc3ccccc3)c2=O)c1-c1ccc(CN)cc1 MTKFBLYNGGWEQD-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims 1
- 150000001934 cyclohexanes Chemical class 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 230000002519 immonomodulatory effect Effects 0.000 claims 1
- 239000003018 immunosuppressive agent Substances 0.000 claims 1
- 229940125721 immunosuppressive agent Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000005981 pentynyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
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- C07D487/08—Bridged systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Landscapes
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
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| GBGB1617758.6A GB201617758D0 (en) | 2016-10-20 | 2016-10-20 | Pharmaceutical compounds |
| GB1617758.6 | 2016-10-20 | ||
| PCT/GB2017/053175 WO2018073602A1 (en) | 2016-10-20 | 2017-10-20 | Piperidine derivatives as inhibitors of ubiquitin specific protease 7 |
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| RU2019115115A true RU2019115115A (ru) | 2020-11-24 |
| RU2019115115A3 RU2019115115A3 (enExample) | 2020-11-24 |
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| WO2019067503A1 (en) * | 2017-09-26 | 2019-04-04 | Dana-Farber Cancer Institute, Inc. | NEW USP7 INHIBITORS FOR THE TREATMENT OF MULTIPLE MYELOMA |
| GB201801562D0 (en) * | 2018-01-31 | 2018-03-14 | Almac Diagnostics Ltd | Pharmaceutical compounds |
| UY38291A (es) * | 2018-07-05 | 2020-06-30 | Servier Lab | Nuevos derivados de amino-pirimidonilo un proceso para su preparación y composiciones farmacéuticas |
| UY38423A (es) * | 2018-10-19 | 2021-02-26 | Servier Lab | Nuevos derivados amino-pirimidonil-piperidinilo, un proceso para su preparación y composiciones farmacéuticas que los contienen |
| EP3870179A4 (en) * | 2018-10-22 | 2022-11-23 | Dana Farber Cancer Institute, Inc. | Usp7 inhibition |
| CN109912598B (zh) * | 2019-03-27 | 2022-09-13 | 四川大学华西医院 | 防治炎症反应的核苷类衍生物及其应用 |
| CN113423709B (zh) * | 2019-04-11 | 2024-02-09 | 四川科伦博泰生物医药股份有限公司 | 三嗪酮并咪唑类化合物及其医药用途 |
| CN111808105B (zh) * | 2019-04-11 | 2023-09-08 | 四川科伦博泰生物医药股份有限公司 | 含有并环基团的嘧啶酮并吡唑类化合物、其制备方法及用途 |
| US20220213059A1 (en) * | 2019-05-06 | 2022-07-07 | Valo Health, Inc. | Inhibiting usp19 |
| CN118108744A (zh) * | 2020-01-08 | 2024-05-31 | 四川科伦博泰生物医药股份有限公司 | 异噻唑并嘧啶酮类化合物,包含其的药物组合物及其用途 |
| CN112608320B (zh) * | 2020-01-16 | 2023-03-17 | 中国药科大学 | 哌啶类化合物及其制备方法和医药用途 |
| GB202001980D0 (en) * | 2020-02-13 | 2020-04-01 | Almac Discovery Ltd | Therapeutic mentods |
| US20230087388A1 (en) | 2020-02-28 | 2023-03-23 | Immunologik Gmbh | Inhibitors of human deubiquitinases for the treatment of coronaviral infections |
| CN113801135B (zh) * | 2020-06-15 | 2025-06-24 | 四川科伦博泰生物医药股份有限公司 | 噻吩并吡唑类化合物,包含其的药物组合物及其用途 |
| CN112047933B (zh) * | 2020-10-15 | 2022-06-14 | 郑州大学 | 喹唑啉酮类usp7抑制剂及其制备方法和应用 |
| CN114478437A (zh) * | 2020-11-11 | 2022-05-13 | 山东特珐曼药业有限公司 | 一种制备n-甲基-2-吡咯烷乙胺或其盐的方法 |
| CN113336714A (zh) * | 2021-06-25 | 2021-09-03 | 山东大学 | 一种化合物及其制备方法和应用 |
| WO2022272133A2 (en) * | 2021-06-25 | 2022-12-29 | Stablix, Inc. | Protein stabilizing compounds containing usp7 ligands |
| AU2022315201A1 (en) * | 2021-07-20 | 2024-01-18 | Dana-Farber Cancer Institute, Inc. | Inhibitors targeting ubiquitin specific protease 7 (usp7) |
| GB202200753D0 (en) | 2022-01-21 | 2022-03-09 | Almac Discovery Ltd | Pharmaceutical compounds |
| CN114507278B (zh) * | 2022-01-27 | 2023-04-25 | 苏州大学 | 一种犹素探针UFM1-Lys-TAMRA及其合成方法 |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPO111096A0 (en) | 1996-07-18 | 1996-08-08 | Fujisawa Pharmaceutical Co., Ltd. | New compound |
| ZA986594B (en) | 1997-07-25 | 1999-01-27 | Abbott Lab | Urokinase inhibitors |
| WO2004058763A1 (en) | 2002-12-23 | 2004-07-15 | Merck & Co., Inc. | 4(spiropiperidinyl)methyl substituted pyrrolidines as modulators of chemokine receptor activity |
| US20050090529A1 (en) | 2003-07-31 | 2005-04-28 | Pfizer Inc | 3,5 Disubstituted indazole compounds with nitrogen-bearing 5-membered heterocycles, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation |
| JP4787529B2 (ja) | 2004-04-09 | 2011-10-05 | 大塚製薬株式会社 | 医薬組成物 |
| EP1765348B1 (en) | 2004-06-18 | 2016-08-03 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| AU2006232375A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
| JP2009502801A (ja) | 2005-07-22 | 2009-01-29 | サネシス ファーマシューティカルズ, インコーポレイテッド | Auroraキナーゼインヒビターとして有用なピラゾロピリミジン |
| DE602005010421D1 (de) | 2005-08-05 | 2008-11-27 | Hybrigenics Sa | Neue Cysteine Protease Hemmers und ihre therapeutische Anwendungen |
| JP2009526747A (ja) | 2006-02-16 | 2009-07-23 | 武田薬品工業株式会社 | 環状アミン化合物および高血圧の予防・治療のための用途 |
| JP5406722B2 (ja) | 2006-10-16 | 2014-02-05 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ブラジキニン1受容体モジュレータとしての置換されたスルホンアミド誘導体 |
| US7875613B2 (en) | 2006-10-30 | 2011-01-25 | Hybrigenics Sa | Tetracyclic inhibitors of cysteine proteases, the pharmaceutical compositions thereof and their therapeutic applications |
| FR2911138B1 (fr) | 2007-01-05 | 2009-02-20 | Sanofi Aventis Sa | Nouveaux derives de n, n'-2,4-dianilinopyrimidines, leur preparation a titre de medicaments, compositions pharmaceutiques et notamment comme inhibiteurs de ikk |
| CA2707105C (en) | 2007-12-11 | 2013-02-12 | F. Hoffmann-La Roche Ag | Inhibitors of stearoyl-coa desaturase |
| EP2254888B1 (en) | 2008-02-22 | 2014-12-24 | Msd K.K. | Novel aminopyridine derivatives having aurora a selective inhibitory action |
| CN102099339A (zh) | 2008-07-18 | 2011-06-15 | 武田药品工业株式会社 | 苯并氮杂衍生物及其作为组胺h3拮抗剂的用途 |
| BRPI0916931A2 (pt) | 2008-08-01 | 2015-11-24 | Biocryst Pharm Inc | agentes terapêuticos |
| EP2331518A1 (en) | 2008-08-22 | 2011-06-15 | Evotec AG | New bradykinin b1 antagonists |
| EP2208725A1 (en) | 2009-01-13 | 2010-07-21 | Hybrigenics S.A. | Novel specific inhibitors of ubiquitin specific protease 7, the pharmaceutical compositions thereof and their therapeutic applications |
| US8680139B2 (en) | 2009-04-01 | 2014-03-25 | Progenra | Anti-neoplastic compounds, compositions and methods |
| EP2515657A4 (en) | 2009-12-21 | 2013-07-03 | Merck Sharp & Dohme | Tyrosine kinase inhibitor |
| US20110177105A1 (en) | 2010-01-15 | 2011-07-21 | Roman Lopez | Novel Selective Inhibitors of Ubiquitin Specific Protease 7, the Pharmaceutical Compositions Thereof and Their Therapeutic Applications |
| TWI503323B (zh) | 2010-03-29 | 2015-10-11 | Oncotherapy Science Inc | 三環化合物以及含此化合物之pbk抑制劑 |
| EP2604601B1 (en) | 2010-08-10 | 2016-02-24 | Astellas Pharma Inc. | Hetero ring compound |
| JP2012072067A (ja) | 2010-09-28 | 2012-04-12 | Astellas Pharma Inc | 含窒素芳香族へテロ環化合物 |
| GB201114448D0 (en) | 2011-08-22 | 2011-10-05 | Takeda Pharmaceutical | Compounds and their use |
| EP2565186A1 (en) * | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| JP6117191B2 (ja) * | 2011-10-07 | 2017-04-19 | 武田薬品工業株式会社 | 神経変性疾患の治療に有用な1−アリールカルボニル−4−オキシ−ピペリジン化合物 |
| EP2785717B1 (en) | 2011-11-29 | 2016-01-13 | Novartis AG | Pyrazolopyrrolidine compounds |
| KR102085121B1 (ko) | 2012-03-09 | 2020-03-05 | 렉시컨 파마슈티컬스 인코퍼레이티드 | 이미다조[1,2-b]피리다진계 화합물, 그를 포함하는 조성물 및 그의 용도 |
| WO2014045101A1 (en) * | 2012-09-21 | 2014-03-27 | Cellzome Gmbh | Tetrazolo quinoxaline derivatives as tankyrase inhibitors |
| WO2014139144A1 (en) | 2013-03-15 | 2014-09-18 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
| MX368059B (es) | 2013-07-18 | 2019-09-18 | Novartis Ag | Inhibidores de autotaxina que comprenden un núcleo de anillo heteroaromático de bencil-amida cíclica. |
| JPWO2015046193A1 (ja) | 2013-09-25 | 2017-03-09 | 塩野義製薬株式会社 | Trpv4阻害活性を有する芳香族複素環式アミン誘導体 |
| KR20170090476A (ko) | 2014-12-05 | 2017-08-07 | 어레이 바이오파마 인크. | 야누스 키나제 저해제로서의 4,6-치환된-피라졸로[1,5-a]피라진 |
| MA41291A (fr) | 2014-12-30 | 2017-11-07 | Forma Therapeutics Inc | Dérivés de la pyrrolotriazinone et de l'imidazotriazinone en tant qu'inhibiteurs de la protéase spécifique de l'ubiquitine n° 7 (usp7) pour le traitement d'un cancer |
| AR103297A1 (es) * | 2014-12-30 | 2017-05-03 | Forma Therapeutics Inc | Pirrolo y pirazolopirimidinas como inhibidores de la proteasa 7 específica de ubiquitina |
| JP2018504430A (ja) * | 2015-02-05 | 2018-02-15 | フォーマ セラピューティクス,インコーポレイテッド | ユビキチン特異的プロテアーゼ7阻害物質としてのキナゾリノン及びアザキナゾリノン |
| HK1248221A1 (zh) * | 2015-02-05 | 2018-10-12 | Forma Therapeutics, Inc. | 异噻唑啉酮类,吡唑并嘧啶酮类和吡咯并嘧啶酮作为泛蛋白特异性蛋白酶7抑制剂 |
| JP2018504431A (ja) * | 2015-02-05 | 2018-02-15 | フォーマ セラピューティクス,インコーポレイテッド | ユビキチン特異的プロテアーゼ7阻害物質としてのチエノピリミジノン |
| JP7109919B2 (ja) | 2015-03-20 | 2022-08-01 | エフ・ホフマン-ラ・ロシュ・アクチェンゲゼルシャフト | Usp7阻害剤化合物及び使用方法 |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201612938D0 (en) | 2016-07-26 | 2016-09-07 | Almac Discovery Ltd | Pharmaceutical compounds |
| AU2017332721B2 (en) * | 2016-09-20 | 2023-11-09 | Sara BUHRLAGE | Compositions and methods for identification, assessment, prevention, and treatment of AML using USP10 biomarkers and modulators |
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| US20190256518A1 (en) | 2019-08-22 |
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| ES2914284T3 (es) | 2022-06-08 |
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