JP2015510938A5 - - Google Patents
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- Publication number
- JP2015510938A5 JP2015510938A5 JP2015501799A JP2015501799A JP2015510938A5 JP 2015510938 A5 JP2015510938 A5 JP 2015510938A5 JP 2015501799 A JP2015501799 A JP 2015501799A JP 2015501799 A JP2015501799 A JP 2015501799A JP 2015510938 A5 JP2015510938 A5 JP 2015510938A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylate
- methyl
- dioxopyrrolidin
- piperazine
- phenyl
- 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 cyano, hydroxyl Chemical group 0.000 claims 192
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 45
- 229910052736 halogen Inorganic materials 0.000 claims 36
- 150000002367 halogens Chemical class 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 25
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000003003 spiro group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- QFRZKYNZMVJOIQ-UHFFFAOYSA-N (1,3-dioxoisoindol-2-yl) 4-(4-methoxyphenyl)piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)ON2C(C3=CC=CC=C3C2=O)=O)CC1 QFRZKYNZMVJOIQ-UHFFFAOYSA-N 0.000 claims 1
- BVMOAQHANHHTHW-UHFFFAOYSA-N (1,3-dioxoisoindol-2-yl) 4-[bis(4-chlorophenyl)methyl]piperazine-1-carboxylate Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CCN(C(=O)ON2C(C3=CC=CC=C3C2=O)=O)CC1 BVMOAQHANHHTHW-UHFFFAOYSA-N 0.000 claims 1
- QMQCCTICGYNZAQ-UHFFFAOYSA-N (2,5-dioxo-3-phenylpyrrolidin-1-yl) 4-[bis(4-chlorophenyl)methyl]piperazine-1-carboxylate Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CCN(C(=O)ON2C(C(CC2=O)C=2C=CC=CC=2)=O)CC1 QMQCCTICGYNZAQ-UHFFFAOYSA-N 0.000 claims 1
- OBHXDNUVOYXSQC-UHFFFAOYSA-N (2,5-dioxo-3-propylpyrrolidin-1-yl) 4-[bis(4-chlorophenyl)methyl]piperazine-1-carboxylate Chemical compound O=C1C(CCC)CC(=O)N1OC(=O)N1CCN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)CC1 OBHXDNUVOYXSQC-UHFFFAOYSA-N 0.000 claims 1
- CHSDEWAINSCEDF-UHFFFAOYSA-N (2,5-dioxo-4-propan-2-ylimidazolidin-1-yl) 4-(4-methoxyphenyl)piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)ON2C(C(C(C)C)NC2=O)=O)CC1 CHSDEWAINSCEDF-UHFFFAOYSA-N 0.000 claims 1
- MRERJVASPRNXRI-UHFFFAOYSA-N (2,5-dioxo-4-propan-2-ylimidazolidin-1-yl) 4-[bis(4-chlorophenyl)methyl]piperazine-1-carboxylate Chemical compound O=C1C(C(C)C)NC(=O)N1OC(=O)N1CCN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)CC1 MRERJVASPRNXRI-UHFFFAOYSA-N 0.000 claims 1
- NFBRLPMNRANKQE-OAHLLOKOSA-N (2,5-dioxopyrrolidin-1-yl) (2r)-4-[(2-fluoro-4-morpholin-4-ylphenyl)methyl]-2-methylpiperazine-1-carboxylate Chemical compound C([C@H](N(CC1)C(=O)ON2C(CCC2=O)=O)C)N1CC(C(=C1)F)=CC=C1N1CCOCC1 NFBRLPMNRANKQE-OAHLLOKOSA-N 0.000 claims 1
- WDQUAAYVWRCPDJ-HNNXBMFYSA-N (2,5-dioxopyrrolidin-1-yl) (2s)-2-methyl-4-[[4-morpholin-4-yl-2-(trifluoromethoxy)phenyl]methyl]piperazine-1-carboxylate Chemical compound C([C@@H](N(CC1)C(=O)ON2C(CCC2=O)=O)C)N1CC(C(=C1)OC(F)(F)F)=CC=C1N1CCOCC1 WDQUAAYVWRCPDJ-HNNXBMFYSA-N 0.000 claims 1
- GLTFVSXLEKWKAC-HNNXBMFYSA-N (2,5-dioxopyrrolidin-1-yl) (2s)-2-methyl-4-[[4-morpholin-4-yl-2-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C([C@@H](N(CC1)C(=O)ON2C(CCC2=O)=O)C)N1CC(C(=C1)C(F)(F)F)=CC=C1N1CCOCC1 GLTFVSXLEKWKAC-HNNXBMFYSA-N 0.000 claims 1
- DLBPNKZBGRQSNF-HNNXBMFYSA-N (2,5-dioxopyrrolidin-1-yl) (2s)-4-[(2-chloro-4-morpholin-4-ylphenyl)methyl]-2-methylpiperazine-1-carboxylate Chemical compound C([C@@H](N(CC1)C(=O)ON2C(CCC2=O)=O)C)N1CC(C(=C1)Cl)=CC=C1N1CCOCC1 DLBPNKZBGRQSNF-HNNXBMFYSA-N 0.000 claims 1
- NFBRLPMNRANKQE-HNNXBMFYSA-N (2,5-dioxopyrrolidin-1-yl) (2s)-4-[(2-fluoro-4-morpholin-4-ylphenyl)methyl]-2-methylpiperazine-1-carboxylate Chemical compound C([C@@H](N(CC1)C(=O)ON2C(CCC2=O)=O)C)N1CC(C(=C1)F)=CC=C1N1CCOCC1 NFBRLPMNRANKQE-HNNXBMFYSA-N 0.000 claims 1
- ZLWUECOTTUWBLP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,2-dimethyl-4-[[4-morpholin-4-yl-2-(trifluoromethoxy)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)C(C)(C)CN1CC(C(=C1)OC(F)(F)F)=CC=C1N1CCOCC1 ZLWUECOTTUWBLP-UHFFFAOYSA-N 0.000 claims 1
- KJHBRWWXPMZIRC-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,2-dimethyl-4-[[4-morpholin-4-yl-2-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)C(C)(C)CN1CC(C(=C1)C(F)(F)F)=CC=C1N1CCOCC1 KJHBRWWXPMZIRC-UHFFFAOYSA-N 0.000 claims 1
- QPVZCYNJSZSASF-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-benzylpiperidine-1-carboxylate Chemical compound C1CCCC(CC=2C=CC=CC=2)N1C(=O)ON1C(=O)CCC1=O QPVZCYNJSZSASF-UHFFFAOYSA-N 0.000 claims 1
- MAGCZBJARIKKBX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-methylpiperidine-1-carboxylate Chemical compound CC1CCCCN1C(=O)ON1C(=O)CCC1=O MAGCZBJARIKKBX-UHFFFAOYSA-N 0.000 claims 1
- WHGHQZYARDIEDU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-phenylpiperidine-1-carboxylate Chemical compound C1CCCC(C=2C=CC=CC=2)N1C(=O)ON1C(=O)CCC1=O WHGHQZYARDIEDU-UHFFFAOYSA-N 0.000 claims 1
- TWZVPDRVNREALZ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-methyl-4-[(4-phenylphenyl)methyl]piperazine-1-carboxylate Chemical compound CC1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC(C=C1)=CC=C1C1=CC=CC=C1 TWZVPDRVNREALZ-UHFFFAOYSA-N 0.000 claims 1
- KYPHYKJNFMMRHE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(3-chlorobenzoyl)piperazine-1-carboxylate Chemical compound ClC1=CC=CC(C(=O)N2CCN(CC2)C(=O)ON2C(CCC2=O)=O)=C1 KYPHYKJNFMMRHE-UHFFFAOYSA-N 0.000 claims 1
- DUFCPBWNKUWAHQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(2-chloro-6-pyrrolidin-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC=1C(Cl)=CC=CC=1N1CCCC1 DUFCPBWNKUWAHQ-UHFFFAOYSA-N 0.000 claims 1
- IHLXUKSIGKCASQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(2-morpholin-4-yl-4-phenylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(CC=2C(=CC(=CC=2)C=2C=CC=CC=2)N2CCOCC2)CCN1C(=O)ON1C(=O)CCC1=O IHLXUKSIGKCASQ-UHFFFAOYSA-N 0.000 claims 1
- PZPWPTRYWCTOGN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(3-fluoro-2-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1COCCN1C=1C(F)=CC=CC=1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O PZPWPTRYWCTOGN-UHFFFAOYSA-N 0.000 claims 1
- HFXWWBNRCRKNLR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-bromo-2-phenoxyphenyl)methyl]piperazine-1-carboxylate Chemical compound C=1C=CC=CC=1OC1=CC(Br)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O HFXWWBNRCRKNLR-UHFFFAOYSA-N 0.000 claims 1
- OFBYYWAQHBVUSW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(5-chloro-2-pyrrolidin-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(Cl)=CC=C1N1CCCC1 OFBYYWAQHBVUSW-UHFFFAOYSA-N 0.000 claims 1
- QKTQCVZKJHRWRT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-(azetidin-1-yl)-4-chlorophenyl]methyl]piperazine-1-carboxylate Chemical compound C1CCN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O QKTQCVZKJHRWRT-UHFFFAOYSA-N 0.000 claims 1
- QPWWEHIHPNWJQM-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-(dimethylcarbamoyl)-4-phenylphenyl]methyl]piperazine-1-carboxylate Chemical compound CN(C)C(=O)C1=CC(C=2C=CC=CC=2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O QPWWEHIHPNWJQM-UHFFFAOYSA-N 0.000 claims 1
- IMOSOOAXQKHMHX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-chloro-4-(morpholine-4-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound ClC1=CC(C(=O)N2CCOCC2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O IMOSOOAXQKHMHX-UHFFFAOYSA-N 0.000 claims 1
- LAWDPEOLMARFBW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-morpholin-4-yl-4-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1COCCN1C1=CC(C(F)(F)F)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O LAWDPEOLMARFBW-UHFFFAOYSA-N 0.000 claims 1
- MFJMCAKPCKPKNC-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-morpholin-4-yl-5-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(C(F)(F)F)=CC=C1N1CCOCC1 MFJMCAKPCKPKNC-UHFFFAOYSA-N 0.000 claims 1
- FXVGBAGKOKOXOS-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-pyrrolidin-1-yl-5-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(C(F)(F)F)=CC=C1N1CCCC1 FXVGBAGKOKOXOS-UHFFFAOYSA-N 0.000 claims 1
- STUQQBFZIHJLAZ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[3-(2-chlorophenyl)-1-methylpyrazol-4-yl]methyl]piperazine-1-carboxylate Chemical compound C=1C=CC=C(Cl)C=1C1=NN(C)C=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O STUQQBFZIHJLAZ-UHFFFAOYSA-N 0.000 claims 1
- XDVOSHRKZWOOQL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[3-chloro-2-(pyrrolidine-1-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CCCN1C(=O)C=1C(Cl)=CC=CC=1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O XDVOSHRKZWOOQL-UHFFFAOYSA-N 0.000 claims 1
- ZLCHLJDKTDAFSQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(6,8-dihydro-5h-[1,2,4]triazolo[1,5-a]pyrazin-7-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN2N=CN=C2CN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O ZLCHLJDKTDAFSQ-UHFFFAOYSA-N 0.000 claims 1
- UYSGJFPSUXAYRU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(morpholine-4-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1COCCN1C(=O)C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O UYSGJFPSUXAYRU-UHFFFAOYSA-N 0.000 claims 1
- VVBDKDACOMXWHB-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-morpholin-4-yl-2-(trifluoromethoxy)phenyl]methyl]piperazine-1-carboxylate Chemical compound FC(F)(F)OC1=CC(N2CCOCC2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O VVBDKDACOMXWHB-UHFFFAOYSA-N 0.000 claims 1
- NBOSBLXXIPUHJR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-morpholin-4-yl-2-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound FC(F)(F)C1=CC(N2CCOCC2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O NBOSBLXXIPUHJR-UHFFFAOYSA-N 0.000 claims 1
- JFQRNYVGSBDQOQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-benzoylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCN1C(=O)ON1C(=O)CCC1=O JFQRNYVGSBDQOQ-UHFFFAOYSA-N 0.000 claims 1
- CYPQLCVPHKXSLC-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-benzylpiperidine-1-carboxylate Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(=O)ON1C(=O)CCC1=O CYPQLCVPHKXSLC-UHFFFAOYSA-N 0.000 claims 1
- JLIJKTQTFHTURP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) n-benzyl-n-ethylcarbamate Chemical compound O=C1CCC(=O)N1OC(=O)N(CC)CC1=CC=CC=C1 JLIJKTQTFHTURP-UHFFFAOYSA-N 0.000 claims 1
- WTNROUCLQVIOHP-UHFFFAOYSA-N (3,3-dimethyl-2,5-dioxopyrrolidin-1-yl) 4-[bis(4-chlorophenyl)methyl]piperazine-1-carboxylate Chemical compound O=C1C(C)(C)CC(=O)N1OC(=O)N1CCN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)CC1 WTNROUCLQVIOHP-UHFFFAOYSA-N 0.000 claims 1
- NQAUBLXFBAJVCA-UHFFFAOYSA-N (3-methyl-2,5-dioxopyrrolidin-1-yl) 4-[bis(4-chlorophenyl)methyl]piperazine-1-carboxylate Chemical compound O=C1C(C)CC(=O)N1OC(=O)N1CCN(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)CC1 NQAUBLXFBAJVCA-UHFFFAOYSA-N 0.000 claims 1
- ASFXBGZMFVXZGE-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)piperidine-1-carboxylic acid Chemical compound C1CCN(C(C1)N2C(=O)CCC2=O)C(=O)O ASFXBGZMFVXZGE-UHFFFAOYSA-N 0.000 claims 1
- CSLFQWTYCANDCU-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)pyrrolidine-1-carboxylic acid Chemical compound C1CC(N(C1)C(=O)O)N2C(=O)CCC2=O CSLFQWTYCANDCU-UHFFFAOYSA-N 0.000 claims 1
- URLFMRIVRXGQOI-UHFFFAOYSA-N 2-methyl-4-(3-methylphenyl)phenol Chemical compound CC1=CC=CC(C=2C=C(C)C(O)=CC=2)=C1 URLFMRIVRXGQOI-UHFFFAOYSA-N 0.000 claims 1
- MNWZWHOJSQZVGO-UHFFFAOYSA-N 4-acetylpiperidine-1-carboxylic acid Chemical compound CC(=O)C1CCN(C(O)=O)CC1 MNWZWHOJSQZVGO-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- VUUKJHNZJCCEAS-UHFFFAOYSA-N C1CC(=O)N(C1=O)C2COCCN2C(=O)O Chemical compound C1CC(=O)N(C1=O)C2COCCN2C(=O)O VUUKJHNZJCCEAS-UHFFFAOYSA-N 0.000 claims 1
- ZDFVLNWKJUMZGF-UHFFFAOYSA-N C1CN(C1N2C(=O)CCC2=O)C(=O)O Chemical compound C1CN(C1N2C(=O)CCC2=O)C(=O)O ZDFVLNWKJUMZGF-UHFFFAOYSA-N 0.000 claims 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- HILMOVZYRIQYKY-UHFFFAOYSA-N CN(CN1C(=O)CNC1=O)C(=O)O Chemical compound CN(CN1C(=O)CNC1=O)C(=O)O HILMOVZYRIQYKY-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- FHXFODCPGDSJGC-UHFFFAOYSA-N O=C1N(C(CC1C1=CC=CC=C1)=O)C1N(CCCC1)C(=O)O.O=C1N(C(CC1C1=CC=CC=C1)=O)CN(C(O)=O)C Chemical compound O=C1N(C(CC1C1=CC=CC=C1)=O)C1N(CCCC1)C(=O)O.O=C1N(C(CC1C1=CC=CC=C1)=O)CN(C(O)=O)C FHXFODCPGDSJGC-UHFFFAOYSA-N 0.000 claims 1
- XVTTYCLIIHLGIH-UHFFFAOYSA-N OC(N(CCCC1)C1N(C(CN1)=O)C1=O)=O Chemical compound OC(N(CCCC1)C1N(C(CN1)=O)C1=O)=O XVTTYCLIIHLGIH-UHFFFAOYSA-N 0.000 claims 1
- 241000610375 Sparisoma viride Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-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
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 0 C*CC(C)(C(C)(*)C(N1OC(N2CC(C)/C=I(\C3CC3)/N(C)CC2)=O)=O)C1=O Chemical compound C*CC(C)(C(C)(*)C(N1OC(N2CC(C)/C=I(\C3CC3)/N(C)CC2)=O)=O)C1=O 0.000 description 1
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| US61/685,511 | 2012-03-19 | ||
| PCT/US2013/031907 WO2013142307A1 (en) | 2012-03-19 | 2013-03-15 | Carbamate compounds and of making and using same |
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| MX350788B (es) | 2012-01-06 | 2017-09-13 | Abide Therapeutics Inc | Compuestos de carbamato y preparación y uso de los mismos. |
| JP6100883B2 (ja) | 2012-03-19 | 2017-03-22 | アビデ セラピューティクス，インク． | カルバマート化合物、及びその製造並びに使用 |
| TW201601632A (zh) * | 2013-11-20 | 2016-01-16 | 杜邦股份有限公司 | １－芳基－３－烷基吡唑殺蟲劑 |
| US9624170B2 (en) * | 2013-12-26 | 2017-04-18 | Takeda Pharmaceutical Company Limited | 4-(piperrazin-1-yl)-pyrrolidin-2-one compounds as monoacylglycerol lipase (MAGL) inhibitors |
| JP6431088B2 (ja) | 2014-03-24 | 2018-11-28 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | α，α−ジハロアミン類およびケチミン類からの３，５−ビス（ハロアルキル）ピラゾール誘導体の製造方法 |
| EP3015458A1 (en) * | 2014-11-03 | 2016-05-04 | Bayer CropScience AG | Process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from a,a-dihaloamines and ketimines |
| US9981972B2 (en) | 2014-05-22 | 2018-05-29 | Abide Therapeutics, Inc. | N-hydroxy bicyclic hydantoin carbamates as tools for identification of serine hydrolase targets |
| KR101555033B1 (ko) * | 2014-07-28 | 2015-09-23 | 충남대학교산학협력단 | 신규한 메타논 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 망막 질환의 예방 또는 치료용 약학적 조성물 |
| US9771341B2 (en) | 2015-03-18 | 2017-09-26 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
| US10450302B2 (en) * | 2015-05-11 | 2019-10-22 | Lundbeck La Jolla Research Center, Inc. | Methods of treating inflammation or neuropathic pain |
| WO2017059135A1 (en) * | 2015-10-02 | 2017-04-06 | Abide Therapeutics, Inc. | Lp-pla2 inhibitors |
| WO2017143283A1 (en) | 2016-02-19 | 2017-08-24 | Abide Therapeutics, Inc. | Radiolabeled monoacylglycerol lipase occupancy probe |
| US10034861B2 (en) | 2016-07-04 | 2018-07-31 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| WO2018053447A1 (en) | 2016-09-19 | 2018-03-22 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
| AU2017361257B2 (en) | 2016-11-16 | 2022-02-10 | H. Lundbeck A/S. | Crystalline forms of a MAGL inhibitor |
| WO2018093950A1 (en) | 2016-11-16 | 2018-05-24 | Abide Therapeutics, Inc. | Pharmaceutical formulations |
| JOP20190105A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| JOP20190106A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| JOP20190126A1 (ar) | 2016-12-22 | 2019-05-28 | H Lundbeck As | بيرازولو [3، 4-b] بيريدينات وإيميدازو [1، 5-b] بيريدازينات على هيئة مثبطات PDE1 |
| WO2019008595A1 (en) * | 2017-07-03 | 2019-01-10 | Jubilant Generics Limited (Formerly A Division Of Jubilant Life Sciences Limited) | PROCESS FOR THE PREPARATION OF 1- (4-FLUOROBENZYL) -3- (4-ISOBUTOXYBENZYL) -1- (1-METHYLPIPERIDIN-4-YL) UREA AND ITS SALTS |
| MX2020007318A (es) * | 2017-09-29 | 2020-08-24 | Takeda Pharmaceuticals Co | Compuesto heterociclico. |
| RU2020118913A (ru) | 2017-12-14 | 2022-01-14 | Х. Лундбекк А/С (H. Lundbeck A/S) | Виды комбинированного лечения, предусматривающего введение 1h-пиразолo[4,3-b]пиридинов |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| US11535611B2 (en) | 2017-12-20 | 2022-12-27 | H. Lundbeck A/S | Pyrazolo[3,4-B]pyridines and imidazo[1,5-B]pyridazines as PDE1 inhibitors |
| TW201927784A (zh) | 2017-12-20 | 2019-07-16 | 丹麥商Ｈ 朗德貝克公司 | 作為pde1抑制劑之大環 |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines as PDE1 inhibitors |
| CN112088001A (zh) | 2018-05-15 | 2020-12-15 | 隆德贝克拉荷亚研究中心有限公司 | Magl抑制剂 |
| KR102261931B1 (ko) * | 2018-09-17 | 2021-06-07 | 제이투에이치바이오텍 (주) | 에다라본 전구체 약물 화합물 및 이들의 신경퇴행성 또는 운동신경 질환의 치료 또는 개선을 위한 의약 용도 |
| PL244071B1 (pl) * | 2019-01-07 | 2023-11-27 | Univ Jagiellonski | Pochodne (2,5-dioksopirolidyn-1-ylo)(fenylo)-acetamidu i ich zastosowanie do leczenia chorób o podłożu neurologicznym |
| IL297470A (en) | 2020-04-21 | 2022-12-01 | H Lundbeck As | Synthesis of a monoacylglycerol lipase inhibitor |
| CN119431211B (zh) * | 2023-08-07 | 2025-08-01 | 北京隆熙生物科技有限公司 | 一种中间体及其制备方法和应用 |
| WO2025153718A1 (en) * | 2024-01-19 | 2025-07-24 | Scenic Biotech Bv | Pla2g15 inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003912A (en) | 1973-06-11 | 1977-01-18 | Monsanto Company | Dicarboximido-N-phenylsubstituted carbamates and derivatives |
| JP4090843B2 (ja) * | 2002-09-30 | 2008-05-28 | 富士フイルム株式会社 | 赤外線感光性組成物 |
| CN102216303A (zh) * | 2007-12-04 | 2011-10-12 | 巴斯利尔药物股份公司 | 制备2-(伯/仲氨基)烃基)氨基甲酰基-7-氧代-2,6-二氮杂双环[3.2.0.]庚烷-6-磺酸衍生物的方法 |
| DK2252584T3 (en) | 2008-02-04 | 2017-01-16 | Prozyme Inc | COMPOUNDS AND PROCEDURES FOR QUICK LABELING OF N-GLYCANS |
| WO2009117444A1 (en) * | 2008-03-17 | 2009-09-24 | Northeastern University | Inhibitors of fatty acid amide hydrolase and monoacylglycerol lipase for modulation of cannabinoid receptors |
| AR073631A1 (es) * | 2008-10-17 | 2010-11-17 | Abbott Lab | Antagonistas del receptor transitorio potencial de vanilloides 1 ( trpv1) utiles para tratar inflamacion y dolor |
| AU2009314629B2 (en) * | 2008-11-14 | 2014-09-25 | The Scripps Research Institute | Methods and compositions related to targeting monoacylglycerol lipase |
| JP6100883B2 (ja) | 2012-03-19 | 2017-03-22 | アビデ セラピューティクス，インク． | カルバマート化合物、及びその製造並びに使用 |
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2013
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- 2013-03-15 EP EP13713040.7A patent/EP2828253A1/en not_active Withdrawn
- 2013-03-15 CA CA2866302A patent/CA2866302A1/en not_active Abandoned
- 2013-03-15 US US14/383,076 patent/US9567302B2/en not_active Expired - Fee Related
- 2013-03-15 CN CN201380026119.XA patent/CN104379578B/zh not_active Expired - Fee Related
- 2013-03-15 MX MX2014011134A patent/MX2014011134A/es unknown
- 2013-03-15 WO PCT/US2013/031907 patent/WO2013142307A1/en not_active Ceased
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