JP2019535664A5 - - Google Patents
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- 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
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- -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
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2016
- 2016-10-20 GB GBGB1617758.6A patent/GB201617758D0/en not_active Ceased
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2017
- 2017-10-20 CN CN201780077139.8A patent/CN110088096A/zh not_active Withdrawn
- 2017-10-20 EP EP22157226.6A patent/EP4026832A1/en not_active Withdrawn
- 2017-10-20 BR BR112019007977A patent/BR112019007977A2/pt not_active Application Discontinuation
- 2017-10-20 EP EP17790829.0A patent/EP3529241B1/en not_active Revoked
- 2017-10-20 WO PCT/GB2017/053175 patent/WO2018073602A1/en not_active Ceased
- 2017-10-20 JP JP2019520996A patent/JP7073359B2/ja active Active
- 2017-10-20 DK DK17790829.0T patent/DK3529241T3/da active
- 2017-10-20 MX MX2019004450A patent/MX2019004450A/es unknown
- 2017-10-20 ES ES17790829T patent/ES2914284T3/es active Active
- 2017-10-20 US US16/343,917 patent/US10766903B2/en not_active Expired - Fee Related
- 2017-10-20 SG SG11201903456WA patent/SG11201903456WA/en unknown
- 2017-10-20 RU RU2019115115A patent/RU2019115115A/ru unknown
- 2017-10-20 AU AU2017346516A patent/AU2017346516B2/en not_active Revoked
- 2017-10-20 CA CA3040805A patent/CA3040805A1/en not_active Withdrawn
- 2017-10-20 KR KR1020197014463A patent/KR20190069529A/ko not_active Withdrawn
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2019
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2022
- 2022-05-11 JP JP2022077871A patent/JP2022106953A/ja not_active Withdrawn
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