JP2019523266A5 - - Google Patents
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- Publication number
- JP2019523266A5 JP2019523266A5 JP2019503928A JP2019503928A JP2019523266A5 JP 2019523266 A5 JP2019523266 A5 JP 2019523266A5 JP 2019503928 A JP2019503928 A JP 2019503928A JP 2019503928 A JP2019503928 A JP 2019503928A JP 2019523266 A5 JP2019523266 A5 JP 2019523266A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxy
- phenyl
- oxo
- dihydropyridine
- 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 cycloheteroalkyl Chemical group 0.000 claims 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 51
- 150000001875 compounds Chemical class 0.000 claims 25
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 13
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 238000006467 substitution reaction Methods 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 150000001408 amides Chemical class 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 3
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- KDWQLICBSFIDRM-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 claims 2
- NUHHZFHUJFHYLY-GZGVDWRWSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N-methyl-6-oxo-4-phenyl-N-propan-2-ylpyridine-3-carboxamide Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@@](CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C(C)C)(C)C)C NUHHZFHUJFHYLY-GZGVDWRWSA-N 0.000 claims 2
- NUHHZFHUJFHYLY-QCBOHVIISA-N 1-[[(4S)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N-methyl-6-oxo-4-phenyl-N-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)N(C)C(=O)c1cn(C[C@]2(O)CCN(CC2(C)C)C(=O)[C@H](C)CC2CCCCC2)c(=O)cc1-c1ccccc1 NUHHZFHUJFHYLY-QCBOHVIISA-N 0.000 claims 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 101000644843 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 19 Proteins 0.000 claims 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- NJQRAAHKQQPUIT-UHFFFAOYSA-N 1,2-dihydropyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CNC1 NJQRAAHKQQPUIT-UHFFFAOYSA-N 0.000 claims 1
- OARLHPKZDPIJGN-PMERELPUSA-N 1-[[(10R)-10-hydroxy-7-[4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butanoyl]-7-azaspiro[4.5]decan-10-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound O[C@@]1(CCN(CC11CCCC1)C(C(CC(F)(F)F)CC(F)(F)F)=O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=CC=CC=C1)=O OARLHPKZDPIJGN-PMERELPUSA-N 0.000 claims 1
- VYXDVPIIPAZIGS-ZWVRTZEQSA-N 1-[[(10R)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-(2-fluorophenyl)-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=C(C=CC=C1)F)=O)C VYXDVPIIPAZIGS-ZWVRTZEQSA-N 0.000 claims 1
- AXYOZQRIFBEKEN-KCEHZKJRSA-N 1-[[(10R)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-(2-fluorophenyl)-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C=C(C(=CC1=O)C1=C(C=CC=C1)F)C(=O)N(C)C)C AXYOZQRIFBEKEN-KCEHZKJRSA-N 0.000 claims 1
- XWMYUJFHXPWJCQ-UVDDSOTQSA-N 1-[[(10R)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1CC1)=O)C XWMYUJFHXPWJCQ-UVDDSOTQSA-N 0.000 claims 1
- VGFSGXNOFOIMRV-OLILMLBXSA-N 1-[[(10R)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C=C(C(=CC1=O)C1CC1)C(=O)N(C)C)C VGFSGXNOFOIMRV-OLILMLBXSA-N 0.000 claims 1
- FDHVYVAPVLZMMU-GZGVDWRWSA-N 1-[[(10R)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=CC=CC=C1)=O)C FDHVYVAPVLZMMU-GZGVDWRWSA-N 0.000 claims 1
- IDKDBLILJKLZII-HEIROHQZSA-N 1-[[(10R)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C)C IDKDBLILJKLZII-HEIROHQZSA-N 0.000 claims 1
- VOGZFRIPDJHGII-MJVKXCJRSA-N 1-[[(10R)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-(2-fluorophenyl)-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=C(C=CC=C1)F)=O)C VOGZFRIPDJHGII-MJVKXCJRSA-N 0.000 claims 1
- KRHMMADNMJKZFE-ZWVRTZEQSA-N 1-[[(10R)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-(2-fluorophenyl)-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C=C(C(=CC1=O)C1=C(C=CC=C1)F)C(=O)N(C)C)C KRHMMADNMJKZFE-ZWVRTZEQSA-N 0.000 claims 1
- OVAGKSJENCXFAE-IANOAQMISA-N 1-[[(10R)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1CC1)=O)C OVAGKSJENCXFAE-IANOAQMISA-N 0.000 claims 1
- NKJAZSDAKURUEC-UVDDSOTQSA-N 1-[[(10R)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C=C(C(=CC1=O)C1CC1)C(=O)N(C)C)C NKJAZSDAKURUEC-UVDDSOTQSA-N 0.000 claims 1
- XWIQOVNJMQOLQO-YHZWMNSLSA-N 1-[[(10R)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=CC=CC=C1)=O)C XWIQOVNJMQOLQO-YHZWMNSLSA-N 0.000 claims 1
- CWIORHAAEFGDBO-YHZWMNSLSA-N 1-[[(10R)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-5-(morpholine-4-carbonyl)-4-phenylpyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCOCC1)C1=CC=CC=C1)=O)C CWIORHAAEFGDBO-YHZWMNSLSA-N 0.000 claims 1
- CGAGIMXDBGNWPN-HEIROHQZSA-N 1-[[(10R)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-6-oxo-4-phenylpyridine-3-carboxylic acid Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@@](CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)O)C CGAGIMXDBGNWPN-HEIROHQZSA-N 0.000 claims 1
- OARLHPKZDPIJGN-SSEXGKCCSA-N 1-[[(10S)-10-hydroxy-7-[4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butanoyl]-7-azaspiro[4.5]decan-10-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound O[C@]1(CCN(CC11CCCC1)C(C(CC(F)(F)F)CC(F)(F)F)=O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=CC=CC=C1)=O OARLHPKZDPIJGN-SSEXGKCCSA-N 0.000 claims 1
- SNCGXAOBCQGOIF-MUUNZHRXSA-N 1-[[(10S)-10-hydroxy-7-[4,4,4-trifluoro-2-(2,2,2-trifluoroethyl)butanoyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound O[C@]1(CCN(CC11CCCC1)C(C(CC(F)(F)F)CC(F)(F)F)=O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C SNCGXAOBCQGOIF-MUUNZHRXSA-N 0.000 claims 1
- VYXDVPIIPAZIGS-PBUKZNKTSA-N 1-[[(10S)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-(2-fluorophenyl)-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=C(C=CC=C1)F)=O)C VYXDVPIIPAZIGS-PBUKZNKTSA-N 0.000 claims 1
- AXYOZQRIFBEKEN-APYJYERMSA-N 1-[[(10S)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-(2-fluorophenyl)-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C=C(C(=CC1=O)C1=C(C=CC=C1)F)C(=O)N(C)C)C AXYOZQRIFBEKEN-APYJYERMSA-N 0.000 claims 1
- XWMYUJFHXPWJCQ-JPZYQRIQSA-N 1-[[(10S)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1CC1)=O)C XWMYUJFHXPWJCQ-JPZYQRIQSA-N 0.000 claims 1
- VGFSGXNOFOIMRV-ACSYHNTCSA-N 1-[[(10S)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C=C(C(=CC1=O)C1CC1)C(=O)N(C)C)C VGFSGXNOFOIMRV-ACSYHNTCSA-N 0.000 claims 1
- FDHVYVAPVLZMMU-QCBOHVIISA-N 1-[[(10S)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=CC=CC=C1)=O)C FDHVYVAPVLZMMU-QCBOHVIISA-N 0.000 claims 1
- IDKDBLILJKLZII-JIYROHSKSA-N 1-[[(10S)-7-[(2R)-3-cyclobutyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C)C IDKDBLILJKLZII-JIYROHSKSA-N 0.000 claims 1
- VOGZFRIPDJHGII-SXZDHJFLSA-N 1-[[(10S)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-(2-fluorophenyl)-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=C(C=CC=C1)F)=O)C VOGZFRIPDJHGII-SXZDHJFLSA-N 0.000 claims 1
- OVAGKSJENCXFAE-GJBXTBEHSA-N 1-[[(10S)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1CC1)=O)C OVAGKSJENCXFAE-GJBXTBEHSA-N 0.000 claims 1
- NKJAZSDAKURUEC-JPZYQRIQSA-N 1-[[(10S)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-cyclopropyl-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C=C(C(=CC1=O)C1CC1)C(=O)N(C)C)C NKJAZSDAKURUEC-JPZYQRIQSA-N 0.000 claims 1
- XWIQOVNJMQOLQO-CXNHSUMOSA-N 1-[[(10S)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=CC=CC=C1)=O)C XWIQOVNJMQOLQO-CXNHSUMOSA-N 0.000 claims 1
- CWIORHAAEFGDBO-CXNHSUMOSA-N 1-[[(10S)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-5-(morpholine-4-carbonyl)-4-phenylpyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@@](O)(Cn2cc(C(=O)N3CCOCC3)c(cc2=O)-c2ccccc2)C2(CCCC2)C1 CWIORHAAEFGDBO-CXNHSUMOSA-N 0.000 claims 1
- CGAGIMXDBGNWPN-JIYROHSKSA-N 1-[[(10S)-7-[(2R)-3-cyclohexyl-2-methylpropanoyl]-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-6-oxo-4-phenylpyridine-3-carboxylic acid Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(CCCC2)[C@](CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)O)C CGAGIMXDBGNWPN-JIYROHSKSA-N 0.000 claims 1
- XKVQWAWAWOOQTN-UVDDSOTQSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-cyclopropyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1CC1)=O)(C)C)C XKVQWAWAWOOQTN-UVDDSOTQSA-N 0.000 claims 1
- LIFOXZNWDAGECW-OLILMLBXSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-cyclopropyl-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@@](CC1)(O)CN1C=C(C(=CC1=O)C1CC1)C(=O)N(C)C)(C)C)C LIFOXZNWDAGECW-OLILMLBXSA-N 0.000 claims 1
- RCKRBLQTXSFTRS-GZGVDWRWSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@](O)(Cn2cc(C(=O)N3CCNCC3)c(cc2=O)-c2ccccc2)C(C)(C)C1 RCKRBLQTXSFTRS-GZGVDWRWSA-N 0.000 claims 1
- JUXXIIWAXSWUHW-GZGVDWRWSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-phenyl-5-(pyrrolidine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCCC1)C1=CC=CC=C1)=O)(C)C)C JUXXIIWAXSWUHW-GZGVDWRWSA-N 0.000 claims 1
- MRYFQWUGZYREMF-XAFBECJHSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-5-[(2S)-2-(hydroxymethyl)piperazine-1-carbonyl]-4-phenylpyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1[C@@H](CNCC1)CO)C1=CC=CC=C1)=O)(C)C)C MRYFQWUGZYREMF-XAFBECJHSA-N 0.000 claims 1
- XKPGXTAAYRECMH-DGHZZKTQSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-5-[(3R)-3-methylpiperazine-1-carbonyl]-4-phenylpyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1C[C@H](NCC1)C)C1=CC=CC=C1)=O)(C)C)C XKPGXTAAYRECMH-DGHZZKTQSA-N 0.000 claims 1
- HFENDYQCVYETLP-HEIROHQZSA-N 1-[[(4R)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@](O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C(C)(C)C1 HFENDYQCVYETLP-HEIROHQZSA-N 0.000 claims 1
- SURQKOABNLFGKI-JHOBJCJYSA-N 1-[[(4R)-1-[(2S)-2-(cyclobutylmethyl)-3-hydroxypropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(C[C@@]2(O)CCN(CC2(C)C)C(=O)[C@H](CO)CC2CCC2)c(=O)cc1-c1ccccc1 SURQKOABNLFGKI-JHOBJCJYSA-N 0.000 claims 1
- KFOBBIDJTVSUCV-UKJJDJLKSA-N 1-[[(4R)-1-[(2S)-2-(cyclohexylmethyl)-3-hydroxypropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(C[C@@]2(O)CCN(CC2(C)C)C(=O)[C@H](CO)CC2CCCCC2)c(=O)cc1-c1ccccc1 KFOBBIDJTVSUCV-UKJJDJLKSA-N 0.000 claims 1
- VVDXKRJCURTCMH-UBOZLPQGSA-N 1-[[(4R)-1-[(2S)-2-(cyclohexylmethyl)-3-methoxypropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@@](CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C)(C)C)COC VVDXKRJCURTCMH-UBOZLPQGSA-N 0.000 claims 1
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- KZKNIPMPHSLYPW-DWXRJYCRSA-N 1-[[(4R)-4-hydroxy-3,3-dimethyl-1-[(2R)-4,4,4-trifluoro-2-methylbutanoyl]piperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound O[C@]1(C(CN(CC1)C([C@@H](CC(F)(F)F)C)=O)(C)C)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C KZKNIPMPHSLYPW-DWXRJYCRSA-N 0.000 claims 1
- XKVQWAWAWOOQTN-JPZYQRIQSA-N 1-[[(4S)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-cyclopropyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@@](O)(Cn2cc(C(=O)N3CCNCC3)c(cc2=O)C2CC2)C(C)(C)C1 XKVQWAWAWOOQTN-JPZYQRIQSA-N 0.000 claims 1
- LIFOXZNWDAGECW-ACSYHNTCSA-N 1-[[(4S)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-cyclopropyl-N,N-dimethyl-6-oxopyridine-3-carboxamide Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@@](O)(Cn2cc(C(=O)N(C)C)c(cc2=O)C2CC2)C(C)(C)C1 LIFOXZNWDAGECW-ACSYHNTCSA-N 0.000 claims 1
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- JUXXIIWAXSWUHW-QCBOHVIISA-N 1-[[(4S)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-phenyl-5-(pyrrolidine-1-carbonyl)pyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@@](O)(Cn2cc(C(=O)N3CCCC3)c(cc2=O)-c2ccccc2)C(C)(C)C1 JUXXIIWAXSWUHW-QCBOHVIISA-N 0.000 claims 1
- MRYFQWUGZYREMF-RSKOIFRYSA-N 1-[[(4S)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-5-[(2S)-2-(hydroxymethyl)piperazine-1-carbonyl]-4-phenylpyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@@](O)(Cn2cc(C(=O)N3CCNC[C@H]3CO)c(cc2=O)-c2ccccc2)C(C)(C)C1 MRYFQWUGZYREMF-RSKOIFRYSA-N 0.000 claims 1
- XKPGXTAAYRECMH-AZAGJHQNSA-N 1-[[(4S)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-5-[(3R)-3-methylpiperazine-1-carbonyl]-4-phenylpyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC([C@](CC1)(O)CN1C(C=C(C(=C1)C(=O)N1C[C@H](NCC1)C)C1=CC=CC=C1)=O)(C)C)C XKPGXTAAYRECMH-AZAGJHQNSA-N 0.000 claims 1
- HFENDYQCVYETLP-JIYROHSKSA-N 1-[[(4S)-1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CC[C@@](O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C(C)(C)C1 HFENDYQCVYETLP-JIYROHSKSA-N 0.000 claims 1
- SURQKOABNLFGKI-YUDQIZAISA-N 1-[[(4S)-1-[(2S)-2-(cyclobutylmethyl)-3-hydroxypropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(C[C@]2(O)CCN(CC2(C)C)C(=O)[C@H](CO)CC2CCC2)c(=O)cc1-c1ccccc1 SURQKOABNLFGKI-YUDQIZAISA-N 0.000 claims 1
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- KNFHVKLLEQLHDP-UTONBFNKSA-N 1-[[(4S)-1-[(2S)-2-(cyclohexylmethyl)-4-hydroxybutanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(C[C@]2(O)CCN(CC2(C)C)C(=O)[C@H](CCO)CC2CCCCC2)c(=O)cc1-c1ccccc1 KNFHVKLLEQLHDP-UTONBFNKSA-N 0.000 claims 1
- KZKNIPMPHSLYPW-WXTAPIANSA-N 1-[[(4S)-4-hydroxy-3,3-dimethyl-1-[(2R)-4,4,4-trifluoro-2-methylbutanoyl]piperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC(F)(F)F)C(=O)N1CC[C@@](O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C(C)(C)C1 KZKNIPMPHSLYPW-WXTAPIANSA-N 0.000 claims 1
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- HWLFCAJFCMCLIQ-BPADPFCFSA-N 1-[[1-[(2R)-3-cyclobutyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC1CCC1)C(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C(C)(C)C1 HWLFCAJFCMCLIQ-BPADPFCFSA-N 0.000 claims 1
- KKKREGKIJYHSPR-CPPKSAKYSA-N 1-[[1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-4-(2-fluorophenyl)-5-pyridin-2-ylpyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CCC(O)(Cn2cc(-c3ccccn3)c(cc2=O)-c2ccccc2F)C(C)(C)C1 KKKREGKIJYHSPR-CPPKSAKYSA-N 0.000 claims 1
- IXCLNCSANLEGLM-IYOGPWPASA-N 1-[[1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-5-(1,3-oxazol-2-yl)-4-phenylpyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CCC(O)(Cn2cc(-c3ncco3)c(cc2=O)-c2ccccc2)C(C)(C)C1 IXCLNCSANLEGLM-IYOGPWPASA-N 0.000 claims 1
- WGCKUDGWLLGKES-HSGLFRJESA-N 1-[[1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-5-(morpholine-4-carbonyl)-4-phenylpyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CCC(O)(Cn2cc(C(=O)N3CCOCC3)c(cc2=O)-c2ccccc2)C(C)(C)C1 WGCKUDGWLLGKES-HSGLFRJESA-N 0.000 claims 1
- VELNUIZXDNMOQK-BPADPFCFSA-N 1-[[1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-6-oxo-4-phenylpyridine-3-carboxylic acid Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CCC(O)(Cn2cc(C(O)=O)c(cc2=O)-c2ccccc2)C(C)(C)C1 VELNUIZXDNMOQK-BPADPFCFSA-N 0.000 claims 1
- HYWCUGKNNQOOSO-RUZDIDTESA-N 1-[[1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxypiperidin-4-yl]methyl]-4-phenyl-5-(piperidine-1-carbonyl)pyridin-2-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CCC(O)(Cn2cc(C(=O)N3CCCCC3)c(cc2=O)-c2ccccc2)CC1 HYWCUGKNNQOOSO-RUZDIDTESA-N 0.000 claims 1
- BNISCJPTVMTNFA-XMMPIXPASA-N 1-[[1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxypiperidin-4-yl]methyl]-N-methyl-6-oxo-4-phenyl-N-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)N(C)C(=O)c1cn(CC2(O)CCN(CC2)C(=O)[C@H](C)CC2CCCCC2)c(=O)cc1-c1ccccc1 BNISCJPTVMTNFA-XMMPIXPASA-N 0.000 claims 1
- CVRHKJTZTXWULA-CUXXENAFSA-N 1-[[1-[(2R)-3-cyclopropyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC1CC1)C(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C(C)(C)C1 CVRHKJTZTXWULA-CUXXENAFSA-N 0.000 claims 1
- AKGJERKUDFRVOB-DKHGMYDOSA-N 1-[[1-[(2S)-2-(cyclohexylmethyl)-3-phenylmethoxypropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(CC2(O)CCN(CC2(C)C)C(=O)[C@H](COCc2ccccc2)CC2CCCCC2)c(=O)cc1-c1ccccc1 AKGJERKUDFRVOB-DKHGMYDOSA-N 0.000 claims 1
- BNFIZGAJUSNHOJ-SANMLTNESA-N 1-[[1-[(3S)-4,4-difluoro-3-phenylbutanoyl]-4-hydroxypiperidin-4-yl]methyl]-N-methyl-6-oxo-4-phenyl-N-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)N(C)C(=O)c1cn(CC2(O)CCN(CC2)C(=O)C[C@H](C(F)F)c2ccccc2)c(=O)cc1-c1ccccc1 BNFIZGAJUSNHOJ-SANMLTNESA-N 0.000 claims 1
- KJRZSHWRTPLALA-UHFFFAOYSA-N 1-[[10-hydroxy-7-(1-methylcyclohexanecarbonyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C1(CCCCC1)C)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C KJRZSHWRTPLALA-UHFFFAOYSA-N 0.000 claims 1
- VFTXGOAJIDJKPZ-UHFFFAOYSA-N 1-[[10-hydroxy-7-(1-methylcyclopentanecarbonyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C1(CCCC1)C)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C VFTXGOAJIDJKPZ-UHFFFAOYSA-N 0.000 claims 1
- BNCTZIXWRHFQSM-UHFFFAOYSA-N 1-[[10-hydroxy-7-(1H-indazole-3-carbonyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C1=NNC2=CC=CC=C12)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C BNCTZIXWRHFQSM-UHFFFAOYSA-N 0.000 claims 1
- OSZDOUIEPTZXOM-UHFFFAOYSA-N 1-[[10-hydroxy-7-(1H-indole-3-carbonyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C1=CNC2=CC=CC=C12)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C OSZDOUIEPTZXOM-UHFFFAOYSA-N 0.000 claims 1
- LJCXRLFRKVRYFB-UHFFFAOYSA-N 1-[[10-hydroxy-7-(1H-pyrazole-5-carbonyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C1=NNC=C1)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C LJCXRLFRKVRYFB-UHFFFAOYSA-N 0.000 claims 1
- NNODZHZJKMAGPL-UHFFFAOYSA-N 1-[[10-hydroxy-7-(2-hydroxy-3-phenylpropanoyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(CC2(O)CCN(CC22CCCC2)C(=O)C(O)Cc2ccccc2)c(=O)cc1-c1ccccc1 NNODZHZJKMAGPL-UHFFFAOYSA-N 0.000 claims 1
- NURCFGMOWHQNSH-UHFFFAOYSA-N 1-[[10-hydroxy-7-(2-methyl-3-morpholin-4-ylpropanoyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CC(CN1CCOCC1)C(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C2(CCCC2)C1 NURCFGMOWHQNSH-UHFFFAOYSA-N 0.000 claims 1
- UMNZJTGCFAYDSQ-UHFFFAOYSA-N 1-[[10-hydroxy-7-(2-methyl-3-piperidin-1-ylpropanoyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CC(CN1CCCCC1)C(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C2(CCCC2)C1 UMNZJTGCFAYDSQ-UHFFFAOYSA-N 0.000 claims 1
- RYTMHHDMXTZORB-UHFFFAOYSA-N 1-[[10-hydroxy-7-(2-methylpropanoyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CC(C)C(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C2(CCCC2)C1 RYTMHHDMXTZORB-UHFFFAOYSA-N 0.000 claims 1
- ODZLEAHZFMHHTG-UHFFFAOYSA-N 1-[[10-hydroxy-7-(4,4,4-trifluoro-3-methylbutanoyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(CC(C(F)(F)F)C)=O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C ODZLEAHZFMHHTG-UHFFFAOYSA-N 0.000 claims 1
- FNLGKTXSNHCRSZ-UHFFFAOYSA-N 1-[[10-hydroxy-7-(4,4,4-trifluorobutanoyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(CCC(F)(F)F)=O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C FNLGKTXSNHCRSZ-UHFFFAOYSA-N 0.000 claims 1
- JGZZCVDFNAPRQB-UHFFFAOYSA-N 1-[[10-hydroxy-7-(5-phenyl-1,3-oxazole-4-carbonyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C=1N=COC=1C1=CC=CC=C1)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C JGZZCVDFNAPRQB-UHFFFAOYSA-N 0.000 claims 1
- VMHSVSRVGMWIFC-UHFFFAOYSA-N 1-[[10-hydroxy-7-(spiro[2.2]pentane-2-carbonyl)-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C1CC11CC1)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C VMHSVSRVGMWIFC-UHFFFAOYSA-N 0.000 claims 1
- VYFZCYUMYGWCPN-KDZLRESVSA-N 1-[[10-hydroxy-7-[(1R,2S)-2-phenylcyclopropanecarbonyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)[C@H]1[C@H](C1)C1=CC=CC=C1)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C VYFZCYUMYGWCPN-KDZLRESVSA-N 0.000 claims 1
- KCLCRDVIHOZLRB-QYWNIODHSA-N 1-[[10-hydroxy-7-[(2R)-2-methylbutanoyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CC[C@@H](C)C(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C2(CCCC2)C1 KCLCRDVIHOZLRB-QYWNIODHSA-N 0.000 claims 1
- IVVZFDORCHYKRJ-HSGLFRJESA-N 1-[[10-hydroxy-7-[(3R)-3-phenylbutanoyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C IVVZFDORCHYKRJ-HSGLFRJESA-N 0.000 claims 1
- IVVZFDORCHYKRJ-VOTTXDMFSA-N 1-[[10-hydroxy-7-[(3S)-3-phenylbutanoyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(C[C@H](C)C1=CC=CC=C1)=O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C IVVZFDORCHYKRJ-VOTTXDMFSA-N 0.000 claims 1
- YPSORFIXTXMPAY-UHFFFAOYSA-N 1-[[10-hydroxy-7-[3-(oxolan-3-yl)propanoyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(CCC1COCC1)=O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C YPSORFIXTXMPAY-UHFFFAOYSA-N 0.000 claims 1
- WLKOJJVQWRLGIV-UHFFFAOYSA-N 1-[[10-hydroxy-7-[3-(trifluoromethyl)cyclobutanecarbonyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(CC2(O)CCN(CC22CCCC2)C(=O)C2CC(C2)C(F)(F)F)c(=O)cc1-c1ccccc1 WLKOJJVQWRLGIV-UHFFFAOYSA-N 0.000 claims 1
- IKWDJOGTDGPLAW-UHFFFAOYSA-N 1-[[10-hydroxy-7-[3-(trifluoromethyl)cyclopentanecarbonyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound OC1(CCN(CC11CCCC1)C(=O)C1CC(CC1)C(F)(F)F)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C IKWDJOGTDGPLAW-UHFFFAOYSA-N 0.000 claims 1
- MXCQCJWRUCKUPX-UHFFFAOYSA-N 1-[[10-hydroxy-7-[4-(trifluoromethyl)-1,3-thiazole-2-carbonyl]-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(CC2(O)CCN(CC22CCCC2)C(=O)c2nc(cs2)C(F)(F)F)c(=O)cc1-c1ccccc1 MXCQCJWRUCKUPX-UHFFFAOYSA-N 0.000 claims 1
- QNWIAEHNUJSMBE-SMQAERNASA-N 1-[[2-[(2R)-3-cyclohexyl-2-methylpropanoyl]-5-hydroxy-2-azaspiro[5.5]undecan-5-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(C(CC1)(O)CN1C(C=C(C(=C1)C(=O)N1CCNCC1)C1=CC=CC=C1)=O)CCCCC2)C QNWIAEHNUJSMBE-SMQAERNASA-N 0.000 claims 1
- ZMARSXVIDDWELK-NAVQMUAQSA-N 1-[[2-[(2R)-3-cyclohexyl-2-methylpropanoyl]-5-hydroxy-2-azaspiro[5.5]undecan-5-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CCCCC1)C[C@H](C(=O)N1CC2(C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C)CCCCC2)C ZMARSXVIDDWELK-NAVQMUAQSA-N 0.000 claims 1
- SGPKCVIQPWQXJB-UHFFFAOYSA-N 1-[[4-hydroxy-1-(1-thiophen-2-ylcyclopropanecarbonyl)piperidin-4-yl]methyl]-N-methyl-6-oxo-4-phenyl-N-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)N(C)C(=O)c1cn(CC2(O)CCN(CC2)C(=O)C2(CC2)c2cccs2)c(=O)cc1-c1ccccc1 SGPKCVIQPWQXJB-UHFFFAOYSA-N 0.000 claims 1
- CZWNOIWMYUORDB-RUZDIDTESA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4,5-diphenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(-c3ccccc3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 CZWNOIWMYUORDB-RUZDIDTESA-N 0.000 claims 1
- CHTFZUHGTFXRPB-XMMPIXPASA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-(2-methoxyphenyl)-N-methyl-6-oxo-N-propan-2-ylpyridine-3-carboxamide Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=C(C(=CC1=O)C1=C(C=CC=C1)OC)C(=O)N(C)C(C)C CHTFZUHGTFXRPB-XMMPIXPASA-N 0.000 claims 1
- HLOJJTUSLGWBIT-XMMPIXPASA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenyl-5-(piperazine-1-carbonyl)pyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N3CCNCC3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 HLOJJTUSLGWBIT-XMMPIXPASA-N 0.000 claims 1
- DSQCYHNINZHRRP-RUZDIDTESA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenyl-5-(piperidine-1-carbonyl)pyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N3CCCCC3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 DSQCYHNINZHRRP-RUZDIDTESA-N 0.000 claims 1
- HCNMZDJEACWVJP-XMMPIXPASA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenyl-5-(pyrrolidine-1-carbonyl)pyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N3CCCC3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 HCNMZDJEACWVJP-XMMPIXPASA-N 0.000 claims 1
- KNQYGFQMEHODTO-XMMPIXPASA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenyl-5-pyridin-2-ylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(-c3ccccn3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 KNQYGFQMEHODTO-XMMPIXPASA-N 0.000 claims 1
- NZXILBZOXKURII-XMMPIXPASA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenyl-5-pyridin-3-ylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(-c3cccnc3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 NZXILBZOXKURII-XMMPIXPASA-N 0.000 claims 1
- FKZBRPBIASGKPY-HSZRJFAPSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenyl-5-pyrimidin-5-ylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(-c3cncnc3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 FKZBRPBIASGKPY-HSZRJFAPSA-N 0.000 claims 1
- ZOOIZEFXRVLMLU-OAQYLSRUSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2ccc(cc2=O)-c2ccccc2)CC1)c1ccccc1 ZOOIZEFXRVLMLU-OAQYLSRUSA-N 0.000 claims 1
- GXAYCXUMEQVMJL-HSZRJFAPSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-5-(1-methylpyrazol-4-yl)-4-phenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(-c3cnn(C)c3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 GXAYCXUMEQVMJL-HSZRJFAPSA-N 0.000 claims 1
- BAUXYCVLIJZDCC-HSZRJFAPSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-5-(2-methylpyrazol-3-yl)-4-phenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(-c3ccnn3C)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 BAUXYCVLIJZDCC-HSZRJFAPSA-N 0.000 claims 1
- ONOXQSUKPKDNKR-XMMPIXPASA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-5-(morpholine-4-carbonyl)-4-phenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N3CCOCC3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 ONOXQSUKPKDNKR-XMMPIXPASA-N 0.000 claims 1
- ACKONZHQDLRWJA-RPBOFIJWSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-5-[(2S)-2-methylpyrrolidine-1-carbonyl]-4-phenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N3CCC[C@@H]3C)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 ACKONZHQDLRWJA-RPBOFIJWSA-N 0.000 claims 1
- JAPPELWQRDSXSV-OAQYLSRUSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-5-methyl-4-phenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 JAPPELWQRDSXSV-OAQYLSRUSA-N 0.000 claims 1
- LZZMLUJJQZJONP-HSZRJFAPSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-5-phenyl-4-prop-1-en-2-ylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(-c3ccccc3)c(cc2=O)C(C)=C)CC1)c1ccccc1 LZZMLUJJQZJONP-HSZRJFAPSA-N 0.000 claims 1
- UJYHEUDTQPFTEL-OAQYLSRUSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-4-phenylpyridine-3-carbaldehyde Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C=O)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 UJYHEUDTQPFTEL-OAQYLSRUSA-N 0.000 claims 1
- IMYTTWDMSGNBGB-OAQYLSRUSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-4-phenylpyridine-3-carbonitrile Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C#N)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 IMYTTWDMSGNBGB-OAQYLSRUSA-N 0.000 claims 1
- RPWZDLLRYGQFQE-JOCHJYFZSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 RPWZDLLRYGQFQE-JOCHJYFZSA-N 0.000 claims 1
- JZJNRTRPQDVBRD-JOCHJYFZSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-N-methoxy-N-methyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CON(C)C(=O)c1cn(CC2(O)CCN(CC2)C(=O)C[C@@H](C)c2ccccc2)c(=O)cc1-c1ccccc1 JZJNRTRPQDVBRD-JOCHJYFZSA-N 0.000 claims 1
- INBOFXODFCGVCP-RUZDIDTESA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-N-methyl-4-(3-methylphenyl)-6-oxo-N-propan-2-ylpyridine-3-carboxamide Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=C(C(=CC1=O)C=1C=C(C=CC=1)C)C(=O)N(C)C(C)C INBOFXODFCGVCP-RUZDIDTESA-N 0.000 claims 1
- BOAGDSFECJZRPO-RUZDIDTESA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-N-methyl-4-(4-methylphenyl)-6-oxo-N-propan-2-ylpyridine-3-carboxamide Chemical compound CC(C)N(C)C(=O)c1cn(CC2(O)CCN(CC2)C(=O)C[C@@H](C)c2ccccc2)c(=O)cc1-c1ccc(C)cc1 BOAGDSFECJZRPO-RUZDIDTESA-N 0.000 claims 1
- DIXNDMSCYYXFHT-AREMUKBSSA-N 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-N-methyl-6-oxo-N,4-diphenylpyridine-3-carboxamide Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N(C)c3ccccc3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 DIXNDMSCYYXFHT-AREMUKBSSA-N 0.000 claims 1
- YTZVUBCEXUKFFW-UHFFFAOYSA-N 1-[[7-(1-benzylpyrrole-2-carbonyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C(C1=CC=CC=C1)N1C(=CC=C1)C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C YTZVUBCEXUKFFW-UHFFFAOYSA-N 0.000 claims 1
- SYRALSKYHODGRH-UHFFFAOYSA-N 1-[[7-(2,4-dimethylpentanoyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CC(C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C)CC(C)C SYRALSKYHODGRH-UHFFFAOYSA-N 0.000 claims 1
- CDGNGVUMRVPJQG-UHFFFAOYSA-N 1-[[7-(2-cyclobutyloxyacetyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(CC2(O)CCN(CC22CCCC2)C(=O)COC2CCC2)c(=O)cc1-c1ccccc1 CDGNGVUMRVPJQG-UHFFFAOYSA-N 0.000 claims 1
- ZKJRPHCLIQLNJF-UHFFFAOYSA-N 1-[[7-(2-cyclohexyloxyacetyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CCCCC1)OCC(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C ZKJRPHCLIQLNJF-UHFFFAOYSA-N 0.000 claims 1
- SSPOGKKUCUPHNF-UHFFFAOYSA-N 1-[[7-(2-cyclohexyloxypropanoyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CCCCC1)OC(C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C)C SSPOGKKUCUPHNF-UHFFFAOYSA-N 0.000 claims 1
- LJPIFELIPPKJAQ-UHFFFAOYSA-N 1-[[7-(3,3-difluorocyclopentanecarbonyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(CC2(O)CCN(CC22CCCC2)C(=O)C2CCC(F)(F)C2)c(=O)cc1-c1ccccc1 LJPIFELIPPKJAQ-UHFFFAOYSA-N 0.000 claims 1
- HNLWMZKWOHTTEI-UHFFFAOYSA-N 1-[[7-(3-fluorocyclopentanecarbonyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound FC1CC(CC1)C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C HNLWMZKWOHTTEI-UHFFFAOYSA-N 0.000 claims 1
- FSCCLAQWCAFAEQ-UHFFFAOYSA-N 1-[[7-(4,4-difluoro-2,2-dimethylbutanoyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CN(C)C(=O)c1cn(CC2(O)CCN(CC22CCCC2)C(=O)C(C)(C)CC(F)F)c(=O)cc1-c1ccccc1 FSCCLAQWCAFAEQ-UHFFFAOYSA-N 0.000 claims 1
- CDFDTEINBWVJDO-UHFFFAOYSA-N 1-[[7-(4,4-difluoro-2-methylbutanoyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound CC(CC(F)F)C(=O)N1CCC(O)(Cn2cc(C(=O)N(C)C)c(cc2=O)-c2ccccc2)C2(CCCC2)C1 CDFDTEINBWVJDO-UHFFFAOYSA-N 0.000 claims 1
- GKXPSFMJISFYNK-UHFFFAOYSA-N 1-[[7-(5-cyclohexyl-1H-pyrazole-4-carbonyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CCCCC1)C1=NNC=C1C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C GKXPSFMJISFYNK-UHFFFAOYSA-N 0.000 claims 1
- BBQQYGHHOZXDOX-UHFFFAOYSA-N 1-[[7-(5-cyclopropyl-1,3-oxazole-4-carbonyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C1(CC1)C1=C(N=CO1)C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C BBQQYGHHOZXDOX-UHFFFAOYSA-N 0.000 claims 1
- DGLZHTNHILTWDR-UHFFFAOYSA-N 1-[[7-(bicyclo[1.1.1]pentane-1-carbonyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C12(CC(C1)C2)C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C DGLZHTNHILTWDR-UHFFFAOYSA-N 0.000 claims 1
- OUOKJCMGBSGMTJ-UHFFFAOYSA-N 1-[[7-(bicyclo[2.2.1]heptane-1-carbonyl)-10-hydroxy-7-azaspiro[4.5]decan-10-yl]methyl]-N,N-dimethyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C12(CCC(CC1)C2)C(=O)N1CC2(CCCC2)C(CC1)(O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)N(C)C OUOKJCMGBSGMTJ-UHFFFAOYSA-N 0.000 claims 1
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- UFECLNBFAPXMMT-HSZRJFAPSA-N 5-[(dimethylamino)methyl]-1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-4-phenylpyridin-2-one Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(CN(C)C)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 UFECLNBFAPXMMT-HSZRJFAPSA-N 0.000 claims 1
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- QPFVKDKXQRETEI-QYWNIODHSA-N 6-[4-(aminomethyl)phenyl]-3-[[1-[(2R)-3-cyclohexyl-2-methylpropanoyl]-4-hydroxy-3,3-dimethylpiperidin-4-yl]methyl]pyrimidin-4-one Chemical compound C[C@H](CC1CCCCC1)C(=O)N1CCC(O)(Cn2cnc(cc2=O)-c2ccc(CN)cc2)C(C)(C)C1 QPFVKDKXQRETEI-QYWNIODHSA-N 0.000 claims 1
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- BXALFGQEFJIKMM-HSZRJFAPSA-N N-(cyclopropylmethyl)-1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)NCC3CC3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 BXALFGQEFJIKMM-HSZRJFAPSA-N 0.000 claims 1
- GBQYTZTZHCIGIZ-HHHXNRCGSA-N N-benzyl-1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-N-methyl-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)N(C)Cc3ccccc3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 GBQYTZTZHCIGIZ-HHHXNRCGSA-N 0.000 claims 1
- MDPRXNGQKGGOGF-RUZDIDTESA-N N-cyclohexyl-1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-4-phenylpyridine-3-carboxamide Chemical compound C[C@H](CC(=O)N1CCC(O)(Cn2cc(C(=O)NC3CCCCC3)c(cc2=O)-c2ccccc2)CC1)c1ccccc1 MDPRXNGQKGGOGF-RUZDIDTESA-N 0.000 claims 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
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- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
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- 125000004432 carbon atom Chemical group C* 0.000 claims 1
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- 239000003085 diluting agent Substances 0.000 claims 1
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- NFDYWLXUHHNNOT-JOCHJYFZSA-N ethyl 1-[[4-hydroxy-1-[(3R)-3-phenylbutanoyl]piperidin-4-yl]methyl]-6-oxo-4-phenylpyridine-3-carboxylate Chemical compound OC1(CCN(CC1)C(C[C@@H](C)C1=CC=CC=C1)=O)CN1C=C(C(=CC1=O)C1=CC=CC=C1)C(=O)OCC NFDYWLXUHHNNOT-JOCHJYFZSA-N 0.000 claims 1
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- 102000051028 human USP19 Human genes 0.000 claims 1
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
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| GB201617758D0 (en) * | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| 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 |
| KR20210100127A (ko) | 2018-12-06 | 2021-08-13 | 알막 디스커버리 리미티드 | 치료용 usp19 억제제 |
| US20220033397A1 (en) * | 2018-12-06 | 2022-02-03 | Almac Discovery Limited | Pharmaceutical compounds and their use as inhibitors of ubiquitin specific protease 19 (usp19) |
| AU2020267757B2 (en) * | 2019-05-06 | 2025-03-27 | Valo Health, Inc. | Inhibiting USP19 |
| JP2023501576A (ja) * | 2019-11-13 | 2023-01-18 | テンプル・ユニバーシティ－オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | ５－ヒドロキシトリプタミン受容体７の調節因子としての新規官能化ラクトンおよびその使用方法 |
| CN111039860B (zh) * | 2019-12-02 | 2022-09-13 | 河北科技大学 | 2-羟基-n-(4’-氯联苯-2-基)烟酰胺的合成方法及应用 |
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| IL146824A0 (en) | 1999-06-02 | 2002-07-25 | Janssen Pharmaceutica Nv | Pyrrolidinyl, piperidinyl or homopiperidinyl substituted (benzodioxan, benzofuran or benzopyran) derivatives |
| EP2552013A1 (en) * | 2011-07-27 | 2013-01-30 | Siemens Aktiengesellschaft | Reduction of noise and vibrations of an electromechanical transducer by using a modified stator coil drive signal comprising harmonic components |
| 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 |
| JP6535007B2 (ja) | 2013-12-20 | 2019-06-26 | インスティテュート オブ ファーマコロジー アンド トキシコロジー アカデミー オブ ミリタリー メディカル サイエンシズ ピー．エル．エー．チャイナ | 新規ピペリジンカルボキサミド化合物、その調製方法及び使用 |
| 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 |
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| GB201617758D0 (en) | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
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