JP2019535664A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019535664A5 JP2019535664A5 JP2019520996A JP2019520996A JP2019535664A5 JP 2019535664 A5 JP2019535664 A5 JP 2019535664A5 JP 2019520996 A JP2019520996 A JP 2019520996A JP 2019520996 A JP2019520996 A JP 2019520996A JP 2019535664 A5 JP2019535664 A5 JP 2019535664A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxy
- piperidine
- pyrimidine
- phenylbutanoyl
- Prior art date
- 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.)
- Granted
Links
- -1 ethylamine-substituted pyrazoles Chemical class 0.000 claims 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 52
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 150000003973 alkyl amines Chemical class 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 2
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical group CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical group C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 206010029260 Neuroblastoma Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000000236 Prostatic Neoplasms Diseases 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 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
- 230000008482 dysregulation Effects 0.000 claims 2
- 208000005017 glioblastoma Diseases 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
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-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
- QJOMTVAWFZTEAR-JOCHJYFZSA-N 1-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-8-methyl-9-phenylpurin-6-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)CN1C=NC=2N(C(=NC=2C1=O)C)C1=CC=CC=C1 QJOMTVAWFZTEAR-JOCHJYFZSA-N 0.000 claims 1
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical group CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 claims 1
- UADBFQKKDBJSFR-GOSISDBHSA-N 2-[[1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxopyrimidin-4-yl]amino]-N,N-dimethylacetamide Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCC(=O)N(C)C)cc2=O)CC1)c1ccccc1 UADBFQKKDBJSFR-GOSISDBHSA-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
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- KYTFGQQQPBDGAT-UHFFFAOYSA-N 3-[[1-(3,3-dicyclopropylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-one Chemical compound OC1(Cn2cnc(NCCN3CCCC3)cc2=O)CCN(CC1)C(=O)CC(C1CC1)C1CC1 KYTFGQQQPBDGAT-UHFFFAOYSA-N 0.000 claims 1
- RESVFDNTOQNSRC-UHFFFAOYSA-N 3-[[1-(3-cyclobutylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-one Chemical compound C1(CCC1)CCC(=O)N1CCC(CC1)(O)CN1C=NC(=CC1=O)NCCN1CCCC1 RESVFDNTOQNSRC-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
- 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
- LFXGCWRVSIXDMF-OAQYLSRUSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-oxa-7-azaspiro[3.5]nonan-7-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCC3(COC3)CC2)CC1)c1ccccc1 LFXGCWRVSIXDMF-OAQYLSRUSA-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
- CMUDSNLIFZRAOP-JOCHJYFZSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-piperidin-1-ylethylamino)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCCN3CCCCC3)cc2=O)CC1)c1ccccc1 CMUDSNLIFZRAOP-JOCHJYFZSA-N 0.000 claims 1
- VJDZJAUBPMXVAF-OAQYLSRUSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCCN3CCCC3)cc2=O)CC1)c1ccccc1 VJDZJAUBPMXVAF-OAQYLSRUSA-N 0.000 claims 1
- VQFUJPSPIPFURI-LETIRJCYSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(3-morpholin-4-ylpyrrolidin-1-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCC(C2)N2CCOCC2)CC1)c1ccccc1 VQFUJPSPIPFURI-LETIRJCYSA-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
- LWDGNPMRZPWKPQ-HXUWFJFHSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(5-oxa-2-azaspiro[3.4]octan-2-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CC3(C2)CCCO3)CC1)c1ccccc1 LWDGNPMRZPWKPQ-HXUWFJFHSA-N 0.000 claims 1
- AKJLLZGMNCCRKW-HXUWFJFHSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(6-oxa-2-azaspiro[3.4]octan-2-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CC3(C2)CCOC3)CC1)c1ccccc1 AKJLLZGMNCCRKW-HXUWFJFHSA-N 0.000 claims 1
- UZLDTOMFKZIRDT-OAQYLSRUSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(7-oxa-2-azaspiro[3.5]nonan-2-yl)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CC3(C2)CCOCC3)CC1)c1ccccc1 UZLDTOMFKZIRDT-OAQYLSRUSA-N 0.000 claims 1
- YPWLKAWCFNNFNE-HXUWFJFHSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[2-(propan-2-ylamino)ethylamino]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NCCNC(C)C YPWLKAWCFNNFNE-HXUWFJFHSA-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
- VEFOCJWDURIQPH-XMMPIXPASA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[4-(pyridin-2-ylmethyl)piperazin-1-yl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCN(Cc3ccccn3)CC2)CC1)c1ccccc1 VEFOCJWDURIQPH-XMMPIXPASA-N 0.000 claims 1
- ROXKJRMFEYMPDF-XMMPIXPASA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[4-(pyridin-3-ylmethyl)piperazin-1-yl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCN(Cc3cccnc3)CC2)CC1)c1ccccc1 ROXKJRMFEYMPDF-XMMPIXPASA-N 0.000 claims 1
- BUAWYQRRLMBFKJ-AREMUKBSSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[N-(2-pyrrolidin-1-ylethyl)anilino]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N(CCN2CCCC2)c2ccccc2)CC1)c1ccccc1 BUAWYQRRLMBFKJ-AREMUKBSSA-N 0.000 claims 1
- CFNWNJAJDWBACV-IRLDBZIGSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[[(2S)-1-methylpyrrolidin-2-yl]methylamino]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NC[C@H]1N(CCC1)C CFNWNJAJDWBACV-IRLDBZIGSA-N 0.000 claims 1
- FWWVSMLHIJRJNB-YADHBBJMSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-[[(2S)-2-pyrrolidin-1-ylpropyl]amino]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NC[C@H](C)N1CCCC1 FWWVSMLHIJRJNB-YADHBBJMSA-N 0.000 claims 1
- ULIMOUOCKZAUCQ-MRXNPFEDSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-methoxypyrimidin-4-one Chemical compound COc1cc(=O)n(CC2(O)CCN(CC2)C(=O)C[C@@H](C)c2ccccc2)cn1 ULIMOUOCKZAUCQ-MRXNPFEDSA-N 0.000 claims 1
- UZVVJKANFHXNAI-LJQANCHMSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-morpholin-4-ylpyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCOCC2)CC1)c1ccccc1 UZVVJKANFHXNAI-LJQANCHMSA-N 0.000 claims 1
- MPDNUHAXCAJRBI-GOSISDBHSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-propan-2-ylpyrimidin-4-one Chemical compound CC(C)c1cc(=O)n(CC2(O)CCN(CC2)C(=O)C[C@@H](C)c2ccccc2)cn1 MPDNUHAXCAJRBI-GOSISDBHSA-N 0.000 claims 1
- YGLCIZVWVSDQPW-LJQANCHMSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-pyridin-4-ylpyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)-c2ccncc2)CC1)c1ccccc1 YGLCIZVWVSDQPW-LJQANCHMSA-N 0.000 claims 1
- ZAHDFPGQNJLNGD-HXUWFJFHSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-8-phenylpyrazolo[1,5-a][1,3,5]triazin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2N(C1=O)N=CC=2C1=CC=CC=C1 ZAHDFPGQNJLNGD-HXUWFJFHSA-N 0.000 claims 1
- QGUCOZPMFVERAW-JOCHJYFZSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-9-phenylpyrido[1,2-a]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cc2cnc3c(cccn3c2=O)-c2ccccc2)CC1)c1ccccc1 QGUCOZPMFVERAW-JOCHJYFZSA-N 0.000 claims 1
- KBQRPWDFHJGDGH-MRXNPFEDSA-N 3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnccc2=O)CC1)c1ccccc1 KBQRPWDFHJGDGH-MRXNPFEDSA-N 0.000 claims 1
- YQQWQDIFFQTIHI-OAHLLOKOSA-N 3-bromo-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(Br)n(C)nc3c2=O)CC1)c1ccccc1 YQQWQDIFFQTIHI-OAHLLOKOSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- RJTQDCHFCDOCGT-OAQYLSRUSA-N 3-cyclohexyl-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 C1C(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)CCCC1 RJTQDCHFCDOCGT-OAQYLSRUSA-N 0.000 claims 1
- ABRGPVVIVBNDCQ-QGZVFWFLSA-N 3-ethynyl-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#C)n(C)nc3c2=O)CC1)c1ccccc1 ABRGPVVIVBNDCQ-QGZVFWFLSA-N 0.000 claims 1
- IYIJPHCKVHORNJ-LJQANCHMSA-N 4-[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=2C1=CC=C(C(=O)O)C=C1)C IYIJPHCKVHORNJ-LJQANCHMSA-N 0.000 claims 1
- ZORUQUCYMCNMIB-CQSZACIVSA-N 5-amino-6-chloro-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(Cl)c(N)c2=O)CC1)c1ccccc1 ZORUQUCYMCNMIB-CQSZACIVSA-N 0.000 claims 1
- AVWDHNLLZONPJR-HXUWFJFHSA-N 5-bromo-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCCN3CCCC3)c(Br)c2=O)CC1)c1ccccc1 AVWDHNLLZONPJR-HXUWFJFHSA-N 0.000 claims 1
- LRDFDWLZMVJNFY-JOCHJYFZSA-N 6-(2,8-diazaspiro[4.5]decan-8-yl)-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)N1CCC2(CCNC2)CC1 LRDFDWLZMVJNFY-JOCHJYFZSA-N 0.000 claims 1
- VVOWOEPVPXDEGB-QGZVFWFLSA-N 6-(2-hydroxyethylamino)-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC(=CC1=O)NCCO VVOWOEPVPXDEGB-QGZVFWFLSA-N 0.000 claims 1
- PTXJRJPGVGXZFW-QGZVFWFLSA-N 6-(3-aminoazetidin-1-yl)-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CC(N)C2)CC1)c1ccccc1 PTXJRJPGVGXZFW-QGZVFWFLSA-N 0.000 claims 1
- YBDKHMNIHFGXCW-LJQANCHMSA-N 6-(4,4-difluoropiperidin-1-yl)-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCC(F)(F)CC2)CC1)c1ccccc1 YBDKHMNIHFGXCW-LJQANCHMSA-N 0.000 claims 1
- QEYOTKDZXAIFQC-LJQANCHMSA-N 6-(4-aminopiperidin-1-yl)-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCC(N)CC2)CC1)c1ccccc1 QEYOTKDZXAIFQC-LJQANCHMSA-N 0.000 claims 1
- ZQGCSHQSCQLVTK-LJQANCHMSA-N 6-(7,7-difluoro-2-azaspiro[3.3]heptan-2-yl)-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound FC1(C2(CN(C2)C2=CC(N(C=N2)CC2(CCN(CC2)C(C[C@@H](C)C2=CC=CC=C2)=O)O)=O)CC1)F ZQGCSHQSCQLVTK-LJQANCHMSA-N 0.000 claims 1
- NJGKUHXXMQHYFM-LJQANCHMSA-N 6-(cyclopentylamino)-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NC3CCCC3)cc2=O)CC1)c1ccccc1 NJGKUHXXMQHYFM-LJQANCHMSA-N 0.000 claims 1
- JLQACNMAEYKPQX-GOSISDBHSA-N 6-[(1,3-dimethylpyrazol-4-yl)amino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(Nc3cn(C)nc3C)cc2=O)CC1)c1ccccc1 JLQACNMAEYKPQX-GOSISDBHSA-N 0.000 claims 1
- KLKAHNQGBFQFAP-TZIWHRDSSA-N 6-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N2CCC[C@@H]2CO)CC1)c1ccccc1 KLKAHNQGBFQFAP-TZIWHRDSSA-N 0.000 claims 1
- CWHGUODVYIDZQY-GGAORHGYSA-N 6-[(3S)-3-(dimethylamino)piperidin-1-yl]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound CN([C@@H]1CN(CCC1)C1=CC(N(C=N1)CC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)O)=O)C CWHGUODVYIDZQY-GGAORHGYSA-N 0.000 claims 1
- ZPMAAYXKYAKTTB-HXUWFJFHSA-N 6-[(4-chlorophenyl)methylamino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(NCc3ccc(Cl)cc3)cc2=O)CC1)c1ccccc1 ZPMAAYXKYAKTTB-HXUWFJFHSA-N 0.000 claims 1
- LLODDDVAUOIGSH-JOCHJYFZSA-N 6-[2-(4-fluoro-1,3-dihydroisoindol-2-yl)ethylamino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound FC1=C2CN(CC2=CC=C1)CCNC1=CC(N(C=N1)CC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)O)=O LLODDDVAUOIGSH-JOCHJYFZSA-N 0.000 claims 1
- RBRREEMWQUOJRG-LJQANCHMSA-N 6-[2-(dimethylamino)ethoxy]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(OCCN(C)C)cc2=O)CC1)c1ccccc1 RBRREEMWQUOJRG-LJQANCHMSA-N 0.000 claims 1
- JKYURQGUWCHEMD-HXUWFJFHSA-N 6-[2-(dimethylamino)ethyl-methylamino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N(C)CCN(C)C)CC1)c1ccccc1 JKYURQGUWCHEMD-HXUWFJFHSA-N 0.000 claims 1
- 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
- UILGUEJAPMIOKR-GOSISDBHSA-N 6-[2-hydroxyethyl(methyl)amino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N(C)CCO)CC1)c1ccccc1 UILGUEJAPMIOKR-GOSISDBHSA-N 0.000 claims 1
- PYEMKSNKGAFLDN-JOCHJYFZSA-N 6-[2-hydroxyethyl(pyridin-3-ylmethyl)amino]-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(cc2=O)N(CCO)Cc2cccnc2)CC1)c1ccccc1 PYEMKSNKGAFLDN-JOCHJYFZSA-N 0.000 claims 1
- LMIOGDRAIURVCW-UHFFFAOYSA-N 6-[[1-(3,3-dicyclopropylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-2-methyl-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound Cn1nc2c(ncn(CC3(O)CCN(CC3)C(=O)CC(C3CC3)C3CC3)c2=O)c1-c1ccccc1 LMIOGDRAIURVCW-UHFFFAOYSA-N 0.000 claims 1
- WSOFOVXFRFJFAT-UHFFFAOYSA-N 6-[[1-(3,3-dicyclopropylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-3-phenyltriazolo[4,5-d]pyrimidin-7-one Chemical compound OC1(Cn2cnc3n(nnc3c2=O)-c2ccccc2)CCN(CC1)C(=O)CC(C1CC1)C1CC1 WSOFOVXFRFJFAT-UHFFFAOYSA-N 0.000 claims 1
- ANEFYICPMBFDOJ-UHFFFAOYSA-N 6-[[1-(3-cyclobutylpropanoyl)-4-hydroxypiperidin-4-yl]methyl]-3-phenyltriazolo[4,5-d]pyrimidin-7-one Chemical compound OC1(Cn2cnc3n(nnc3c2=O)-c2ccccc2)CCN(CC1)C(=O)CCC1CCC1 ANEFYICPMBFDOJ-UHFFFAOYSA-N 0.000 claims 1
- XCFGSGDVHPTWJN-GOSISDBHSA-N 6-[[1-[(3R)-3,4-dimethylpent-4-enoyl]-4-hydroxypiperidin-4-yl]methyl]-2-methyl-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4ccccc4)n(C)nc3c2=O)CC1)C(C)=C XCFGSGDVHPTWJN-GOSISDBHSA-N 0.000 claims 1
- ZAUHIYZMRNKYRW-UHFFFAOYSA-N 6-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]-3-phenyltriazolo[4,5-d]pyrimidin-7-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(nnc3c2=O)-c2ccccc2)CC1 ZAUHIYZMRNKYRW-UHFFFAOYSA-N 0.000 claims 1
- KRTGJWPIMQGLBZ-UHFFFAOYSA-N 6-[[4-hydroxy-1-(3-phenylpropanoyl)piperidin-4-yl]methyl]-2-(methylamino)-[1,3]thiazolo[4,5-d]pyrimidin-7-one Chemical compound CNc1nc2ncn(CC3(O)CCN(CC3)C(=O)CCc3ccccc3)c(=O)c2s1 KRTGJWPIMQGLBZ-UHFFFAOYSA-N 0.000 claims 1
- UECQGLAZBLIFRP-UHFFFAOYSA-N 6-[[4-hydroxy-1-(3-phenylpropanoyl)piperidin-4-yl]methyl]-2-methyl-3-(trifluoromethyl)pyrazolo[4,3-d]pyrimidin-7-one Chemical compound Cn1nc2c(ncn(CC3(O)CCN(CC3)C(=O)CCc3ccccc3)c2=O)c1C(F)(F)F UECQGLAZBLIFRP-UHFFFAOYSA-N 0.000 claims 1
- HYAOKTNLZUXZES-UHFFFAOYSA-N 6-[[4-hydroxy-1-(3-phenylpropanoyl)piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound Cn1cc2ncn(CC3(O)CCN(CC3)C(=O)CCc3ccccc3)c(=O)c2n1 HYAOKTNLZUXZES-UHFFFAOYSA-N 0.000 claims 1
- FVXOVIARIHNBSE-OAHLLOKOSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-(trifluoromethyl)pyrazolo[4,3-d]pyrimidin-7-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2C(C1=O)=NN(C=2C(F)(F)F)C FVXOVIARIHNBSE-OAHLLOKOSA-N 0.000 claims 1
- OADPKEBCNTYBHU-XMMPIXPASA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-[3-(morpholin-4-ylmethyl)phenyl]pyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4cccc(CN5CCOCC5)c4)n(C)nc3c2=O)CC1)c1ccccc1 OADPKEBCNTYBHU-XMMPIXPASA-N 0.000 claims 1
- XARMGQZVMSMTHK-HXUWFJFHSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4ccccc4)n(C)nc3c2=O)CC1)c1ccccc1 XARMGQZVMSMTHK-HXUWFJFHSA-N 0.000 claims 1
- DCUPIMILEVPMGQ-GOSISDBHSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-prop-1-en-2-ylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(C(C)=C)n(C)nc3c2=O)CC1)c1ccccc1 DCUPIMILEVPMGQ-GOSISDBHSA-N 0.000 claims 1
- PLYPTJNVWXGIQI-GOSISDBHSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-propan-2-yl-4,5-dihydropyrazolo[4,3-d]pyrimidin-7-one Chemical compound CC(C)c1c2NCN(CC3(O)CCN(CC3)C(=O)C[C@@H](C)c3ccccc3)C(=O)c2nn1C PLYPTJNVWXGIQI-GOSISDBHSA-N 0.000 claims 1
- CMWVDWXFTJRJAH-GOSISDBHSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-propan-2-ylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound CC(C)c1n(C)nc2c1ncn(CC1(O)CCN(CC1)C(=O)C[C@@H](C)c1ccccc1)c2=O CMWVDWXFTJRJAH-GOSISDBHSA-N 0.000 claims 1
- SOSGUQNAAJYBBO-LJQANCHMSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-pyridin-4-ylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc3c(-c4ccncc4)n(C)nc3c2=O)CC1)c1ccccc1 SOSGUQNAAJYBBO-LJQANCHMSA-N 0.000 claims 1
- BCPHMISHUWIMEJ-MRXNPFEDSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC=2C(C1=O)=NN(C=2)C BCPHMISHUWIMEJ-MRXNPFEDSA-N 0.000 claims 1
- ZNOZBWDZPVWDSL-LJQANCHMSA-N 6-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-3-phenyltriazolo[4,5-d]pyrimidin-7-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=NC2=C(C1=O)N=NN2C1=CC=CC=C1 ZNOZBWDZPVWDSL-LJQANCHMSA-N 0.000 claims 1
- QTHDOEWXCFYHTP-OAQYLSRUSA-N 6-[[4-hydroxy-1-[(3R)-4,4,4-trifluoro-3-phenylbutanoyl]piperidin-4-yl]methyl]-2-methyl-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound OC1(CCN(CC1)C(C[C@@H](C(F)(F)F)C1=CC=CC=C1)=O)CN1C=NC=2C(C1=O)=NN(C=2C1=CC=CC=C1)C QTHDOEWXCFYHTP-OAQYLSRUSA-N 0.000 claims 1
- TVMZBTLHTBHFQI-GOSISDBHSA-N 6-[[4-hydroxy-1-[(3R)-4-methyl-3-(trifluoromethyl)pent-4-enoyl]piperidin-4-yl]methyl]-2-methyl-3-phenylpyrazolo[4,3-d]pyrimidin-7-one Chemical compound OC1(CCN(CC1)C(C[C@H](C(=C)C)C(F)(F)F)=O)CN1C=NC=2C(C1=O)=NN(C=2C1=CC=CC=C1)C TVMZBTLHTBHFQI-GOSISDBHSA-N 0.000 claims 1
- UTGDWIVPYKAJII-OAHLLOKOSA-N 6-amino-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(N)cc2=O)CC1)c1ccccc1 UTGDWIVPYKAJII-OAHLLOKOSA-N 0.000 claims 1
- WFMXEEPSEBBFMS-HXUWFJFHSA-N 6-anilino-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(Nc3ccccc3)cc2=O)CC1)c1ccccc1 WFMXEEPSEBBFMS-HXUWFJFHSA-N 0.000 claims 1
- UKCUCPXBHFHGSE-OAQYLSRUSA-N 6-benzyl-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C(C1=CC=CC=C1)C1=CC(N(C=N1)CC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)O)=O UKCUCPXBHFHGSE-OAQYLSRUSA-N 0.000 claims 1
- AWGRXZOQUOQGQM-UHFFFAOYSA-N 6-chloro-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]-7-(3-morpholin-4-ylphenyl)pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2cccc(c2)N2CCOCC2)CC1 AWGRXZOQUOQGQM-UHFFFAOYSA-N 0.000 claims 1
- NZEKXGTUNFWFSN-UHFFFAOYSA-N 6-chloro-3-[[4-hydroxy-1-(1-methylpyrazole-4-carbonyl)piperidin-4-yl]methyl]-7-phenylpyrrolo[2,3-d]pyrimidin-4-one Chemical compound Cn1cc(cn1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2ccccc2)CC1 NZEKXGTUNFWFSN-UHFFFAOYSA-N 0.000 claims 1
- GKXWECHRCPLJLT-OAHLLOKOSA-N 6-chloro-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-5-methylpyrimidin-4-one Chemical compound ClC1=C(C(N(C=N1)CC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)O)=O)C GKXWECHRCPLJLT-OAHLLOKOSA-N 0.000 claims 1
- GMXANMXNFQWAJY-OAHLLOKOSA-N 6-chloro-3-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cnc(Cl)cc2=O)CC1)c1ccccc1 GMXANMXNFQWAJY-OAHLLOKOSA-N 0.000 claims 1
- ZFTNBWYOYXUJNY-UHFFFAOYSA-N 6-chloro-7-(3,4-dimethoxyphenyl)-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound COc1ccc(cc1OC)-n1c(Cl)cc2c1ncn(CC1(O)CCN(CC1)C(=O)C1(C)CC1)c2=O ZFTNBWYOYXUJNY-UHFFFAOYSA-N 0.000 claims 1
- CJNLCUGUFYDMGB-UHFFFAOYSA-N 6-chloro-7-(3-cyclopropylphenyl)-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2cccc(c2)C2CC2)CC1 CJNLCUGUFYDMGB-UHFFFAOYSA-N 0.000 claims 1
- YMACSKAKXGZLMX-UHFFFAOYSA-N 6-chloro-7-(3-cyclopropylphenyl)-3-[[4-hydroxy-1-(1-methylpyrazole-4-carbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound Cn1cc(cn1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2cccc(c2)C2CC2)CC1 YMACSKAKXGZLMX-UHFFFAOYSA-N 0.000 claims 1
- RXQWPAXTMFVIFX-UHFFFAOYSA-N 6-chloro-7-(4-chlorophenyl)-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2ccc(Cl)cc2)CC1 RXQWPAXTMFVIFX-UHFFFAOYSA-N 0.000 claims 1
- LJEBGGCVTHSGOV-UHFFFAOYSA-N 6-chloro-7-(4-cyclopropylphenyl)-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2ccc(cc2)C2CC2)CC1 LJEBGGCVTHSGOV-UHFFFAOYSA-N 0.000 claims 1
- PPWWRHSUDVFEPC-UHFFFAOYSA-N 6-chloro-7-(4-fluorophenyl)-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2ccc(F)cc2)CC1 PPWWRHSUDVFEPC-UHFFFAOYSA-N 0.000 claims 1
- HQHQDIGQORKBKP-UHFFFAOYSA-N 7-(1,3-benzodioxol-5-yl)-6-chloro-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2ccc3OCOc3c2)CC1 HQHQDIGQORKBKP-UHFFFAOYSA-N 0.000 claims 1
- FSIQZSIMUHDTAL-UHFFFAOYSA-N 7-(3-bromophenyl)-6-chloro-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound CC1(CC1)C(=O)N1CCC(O)(Cn2cnc3n(c(Cl)cc3c2=O)-c2cccc(Br)c2)CC1 FSIQZSIMUHDTAL-UHFFFAOYSA-N 0.000 claims 1
- ZHKUBFGVDIZPMG-UHFFFAOYSA-N 7-[4-(aminomethyl)phenyl]-6-chloro-3-[[4-hydroxy-1-(1-methylcyclopropanecarbonyl)piperidin-4-yl]methyl]pyrrolo[2,3-d]pyrimidin-4-one Chemical compound NCC1=CC=C(C=C1)N1C(=CC2=C1N=CN(C2=O)CC1(CCN(CC1)C(=O)C1(CC1)C)O)Cl ZHKUBFGVDIZPMG-UHFFFAOYSA-N 0.000 claims 1
- FJQXZZBTUUNIBK-UHFFFAOYSA-N 8-methyl-5-oxa-2,8-diazaspiro[3.5]nonane Chemical compound C1N(C)CCOC11CNC1 FJQXZZBTUUNIBK-UHFFFAOYSA-N 0.000 claims 1
- 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
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 125000006549 C4-C10 aryl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical group NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 1
- BCFOGQHIHLDGIV-UHFFFAOYSA-N OC(CC1)CCN1C(CC(C(F)(F)F)C1=CC(F)=CC(F)=C1)=O Chemical compound OC(CC1)CCN1C(CC(C(F)(F)F)C1=CC(F)=CC(F)=C1)=O BCFOGQHIHLDGIV-UHFFFAOYSA-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
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 229940125708 antidiabetic agent Drugs 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 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
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical group 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
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000000524 functional 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
- 210000005036 nerve Anatomy 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
- 125000005981 pentynyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 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
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 C*(**[C@@]12)C1*=C*(C)C2=O Chemical compound C*(**[C@@]12)C1*=C*(C)C2=O 0.000 description 3
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022077871A JP2022106953A (ja) | 2016-10-20 | 2022-05-11 | ユビキチン特異的プロテアーゼ７の阻害剤としてのピペリジン誘導体 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022077871A Division JP2022106953A (ja) | 2016-10-20 | 2022-05-11 | ユビキチン特異的プロテアーゼ７の阻害剤としてのピペリジン誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019535664A JP2019535664A (ja) | 2019-12-12 |
| JP2019535664A5 true JP2019535664A5 (cg-RX-API-DMAC7.html) | 2020-10-15 |
| JP7073359B2 JP7073359B2 (ja) | 2022-05-23 |
Family
ID=57738053
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019520996A Active JP7073359B2 (ja) | 2016-10-20 | 2017-10-20 | ユビキチン特異的プロテアーゼ７の阻害剤としてのピペリジン誘導体 |
| JP2022077871A Withdrawn JP2022106953A (ja) | 2016-10-20 | 2022-05-11 | ユビキチン特異的プロテアーゼ７の阻害剤としてのピペリジン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022077871A Withdrawn JP2022106953A (ja) | 2016-10-20 | 2022-05-11 | ユビキチン特異的プロテアーゼ７の阻害剤としてのピペリジン誘導体 |
Country Status (16)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201612938D0 (en) | 2016-07-26 | 2016-09-07 | Almac Discovery Ltd | Pharmaceutical compounds |
| JP7402792B2 (ja) * | 2017-09-26 | 2023-12-21 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | 多発性骨髄腫を治療するための新規なｕｓｐ７阻害剤 |
| 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 |
| JP7508449B2 (ja) * | 2018-10-22 | 2024-07-01 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | Ｕｓｐ７の阻害 |
| 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 |
| CN117050086A (zh) * | 2019-04-11 | 2023-11-14 | 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 |
| 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 |
| EP3965749A4 (en) * | 2019-05-06 | 2023-06-21 | Valo Health, Inc. | INHIBITION OF 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 |
| CA3167473A1 (en) | 2020-02-28 | 2021-09-02 | 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 |
| CN118401507A (zh) * | 2021-07-20 | 2024-07-26 | 丹娜法伯癌症研究院 | 靶向泛素特异性蛋白酶7（usp7）的抑制剂 |
| 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 |
| AU2003301095A1 (en) | 2002-12-23 | 2004-07-22 | Merck And 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 |
| US7884207B2 (en) * | 2004-06-18 | 2011-02-08 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US7943636B2 (en) * | 2005-04-01 | 2011-05-17 | 3M Innovative Properties Company | 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 |
| EP1749822B1 (en) | 2005-08-05 | 2008-10-15 | Hybrigenics S.A. | Novel cysteine protease inhibitors and their therapeutic applications |
| US20100121048A1 (en) * | 2006-02-16 | 2010-05-13 | Takanobu Kuroita | Cyclic Amine Compound and Use Thereof for the Prophylaxis or Treatment of Hypertension |
| CA2666406A1 (en) * | 2006-10-16 | 2008-04-24 | Gruenenthal Gmbh | Substituted sulfonamide derivatives for use as bradykinin 1 receptor modulators |
| 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 |
| CN101896473B (zh) | 2007-12-11 | 2012-07-25 | 霍夫曼-拉罗奇有限公司 | 硬脂酰基辅酶a去饱和酶抑制剂 |
| ES2531398T3 (es) * | 2008-02-22 | 2015-03-13 | Msd Kk | Nuevos derivados de aminopiridina que tienen una acción inhibidora selectiva de Aurora A |
| 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 |
| CA2732628A1 (en) | 2008-08-01 | 2010-02-04 | Biocryst Pharmaceuticals, Inc. | Therapeutic agents |
| WO2010020556A1 (en) * | 2008-08-22 | 2010-02-25 | Evotec Neurosciences Gmbh | 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 |
| EP2357176A1 (en) | 2010-01-15 | 2011-08-17 | Hybrigenics S.A. | Amidoacridine derivatives useful as selective inhibitors of ubiquitin specific protease 7 |
| 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 |
| JP5765342B2 (ja) * | 2010-08-10 | 2015-08-19 | アステラス製薬株式会社 | へテロ環化合物 |
| 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 |
| UA115133C2 (uk) * | 2011-10-07 | 2017-09-25 | Такеда Фармасьютікал Компані Лімітед | Сполуки 1-арилкарбоніл-4-оксипіперидину, придатні для лікування нейродегенеративних захворювань |
| WO2013080141A1 (en) * | 2011-11-29 | 2013-06-06 | Novartis Ag | Pyrazolopyrrolidine compounds |
| MX347917B (es) | 2012-03-09 | 2017-05-17 | Lexicon Pharmaceuticals Inc | Compuestos a base de imidazo[1,2-b]piridazina, composiciones que los comprenden, y metodos para su uso. |
| 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 |
| AP2016009020A0 (en) * | 2013-07-18 | 2016-02-29 | Novartis Ag | Autotaxin inhibitors comprising a heteroaromatic ring-benzyl-amide-cycle core |
| WO2015046193A1 (ja) * | 2013-09-25 | 2015-04-02 | 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 |
| RU2021102805A (ru) * | 2014-12-05 | 2021-02-12 | Эррэй Биофарма Инк. | 4,6-ЗАМЕЩЕННЫЕ ПИРАЗОЛО[1,5-a]ПИРАЗИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ ЯНУС-КИНАЗЫ |
| TWI698436B (zh) * | 2014-12-30 | 2020-07-11 | 美商佛瑪治療公司 | 作為泛素特異性蛋白酶７抑制劑之吡咯并及吡唑并嘧啶 |
| 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 |
| US9932351B2 (en) * | 2015-02-05 | 2018-04-03 | Forma Therapeutics, Inc. | Thienopyrimidinones as ubiquitin-specific protease 7 inhibitors |
| 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 |
| US9938300B2 (en) * | 2015-02-05 | 2018-04-10 | Forma Therapeutics, Inc. | Isothiazolopyrimidinones, pyrazolopyrimidinones, and pyrrolopyrimidinones as ubiquitin-specific protease 7 inhibitors |
| EP3271333B1 (en) | 2015-03-20 | 2022-01-12 | F. Hoffmann-La Roche AG | Usp7 inhibitor compounds and methods of use |
| 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 |
| ES3033182T3 (en) * | 2016-09-20 | 2025-07-31 | Dana Farber Cancer Inst Inc | Compositions and methods for identification, assessment, prevention, and treatment of aml using usp10 biomarkers and modulators |
-
2016
- 2016-10-20 GB GBGB1617758.6A patent/GB201617758D0/en not_active Ceased
-
2017
- 2017-10-20 WO PCT/GB2017/053175 patent/WO2018073602A1/en not_active Ceased
- 2017-10-20 DK DK17790829.0T patent/DK3529241T3/da active
- 2017-10-20 SG SG11201903456WA patent/SG11201903456WA/en unknown
- 2017-10-20 KR KR1020197014463A patent/KR20190069529A/ko not_active Withdrawn
- 2017-10-20 JP JP2019520996A patent/JP7073359B2/ja active Active
- 2017-10-20 CN CN201780077139.8A patent/CN110088096A/zh not_active Withdrawn
- 2017-10-20 AU AU2017346516A patent/AU2017346516B2/en not_active Revoked
- 2017-10-20 MX MX2019004450A patent/MX2019004450A/es unknown
- 2017-10-20 ES ES17790829T patent/ES2914284T3/es active Active
- 2017-10-20 BR BR112019007977A patent/BR112019007977A2/pt not_active Application Discontinuation
- 2017-10-20 CA CA3040805A patent/CA3040805A1/en not_active Withdrawn
- 2017-10-20 RU RU2019115115A patent/RU2019115115A/ru unknown
- 2017-10-20 EP EP17790829.0A patent/EP3529241B1/en not_active Revoked
- 2017-10-20 US US16/343,917 patent/US10766903B2/en not_active Expired - Fee Related
- 2017-10-20 EP EP22157226.6A patent/EP4026832A1/en not_active Withdrawn
-
2019
- 2019-04-16 MX MX2021012589A patent/MX2021012589A/es unknown
- 2019-04-18 IL IL266146A patent/IL266146A/en unknown
-
2022
- 2022-05-11 JP JP2022077871A patent/JP2022106953A/ja not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019535664A5 (cg-RX-API-DMAC7.html) | ||
| RU2019115115A (ru) | Производные пиперидина в качестве ингибиторов убиквитин-специфической протеазы 7 | |
| RU2473549C2 (ru) | Пиримидиновые соединения, композиции и способы применения | |
| JP2024532735A (ja) | 複素環式化合物及び使用方法 | |
| JP2024517693A (ja) | ２－アミノベンゾチアゾール化合物及びその使用方法 | |
| JP7654071B2 (ja) | 複素環スピロ化合物及び使用方法 | |
| JP2025508702A (ja) | キナゾリン化合物、及び変異ｋｒａｓタンパク質の阻害剤としてのその使用 | |
| JP2021506858A5 (cg-RX-API-DMAC7.html) | ||
| SI3083625T1 (en) | Pyrimidopyrimidinones, useful as Wee-1 kinase inhibitors | |
| WO2022093856A1 (en) | Heterocyclic spiro compounds and methods of use | |
| RU2018138471A (ru) | Гетероциклические соединения в качестве ингибиторов киназы RET | |
| AU2011343477A1 (en) | Bicyclic triazole and pyrazole lactams as allosteric modulators of mGluR5 receptors | |
| HRP20171913T1 (hr) | Aminopirimidinilni spojevi kao inhibitori jak | |
| RU2011116447A (ru) | Модуляторы амилоида бета | |
| JP2013515729A5 (cg-RX-API-DMAC7.html) | ||
| JP2011511034A5 (cg-RX-API-DMAC7.html) | ||
| HRP20192151T1 (hr) | Derivati izokromena kao inhibitori fosfoinozitid 3-kinaza | |
| JP2025535046A (ja) | Ｋｒａｓ ｇ１２ｃ変異タンパク質の複素環阻害剤及びその使用 | |
| JP2017518326A5 (cg-RX-API-DMAC7.html) | ||
| RU2014151004A (ru) | Пирролопиримидоновые и пирролопиридоновые ингибиторы танкиразы | |
| JP2016537384A5 (cg-RX-API-DMAC7.html) | ||
| RU2020127848A (ru) | Производные 4-гидроксипиперидина и их применение в качестве ингибиторов убиквитин-специфической протеазы 19 (usp19) | |
| JP2013518823A5 (cg-RX-API-DMAC7.html) | ||
| US9682980B2 (en) | Positive allosteric modulators of mGluR2 | |
| WO1999059584A1 (en) | Combination of phentolamine and cyclic gmp phosphodiesterase inhibitors for the treatment of sexual dysfunction |