JP2016525092A5 - - Google Patents
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- Publication number
- JP2016525092A5 JP2016525092A5 JP2016524330A JP2016524330A JP2016525092A5 JP 2016525092 A5 JP2016525092 A5 JP 2016525092A5 JP 2016524330 A JP2016524330 A JP 2016524330A JP 2016524330 A JP2016524330 A JP 2016524330A JP 2016525092 A5 JP2016525092 A5 JP 2016525092A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrole
- methyl
- carboxylate
- octahydropyrrolo
- hexafluoropropan
- 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, phenyl Chemical group 0.000 claims 112
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 36
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 claims 36
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 150000002367 halogens Chemical class 0.000 claims 30
- 125000001424 substituent group Chemical group 0.000 claims 24
- 150000001875 compounds Chemical class 0.000 claims 19
- BQTIZWACTUVAGT-UHFFFAOYSA-N 2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole-5-carboxylic acid Chemical compound C1NCC2CN(C(=O)O)CC21 BQTIZWACTUVAGT-UHFFFAOYSA-N 0.000 claims 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000001188 haloalkyl group Chemical group 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- QNNXBZWHBVZZTI-UHFFFAOYSA-N Cc1c(CN2CC3CN(CC3C2)C(O)=O)cccc1N1CCC(CC1)NS(C)(=O)=O Chemical compound Cc1c(CN2CC3CN(CC3C2)C(O)=O)cccc1N1CCC(CC1)NS(C)(=O)=O QNNXBZWHBVZZTI-UHFFFAOYSA-N 0.000 claims 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000003386 piperidinyl 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
- SKKMNDJFMBCHFI-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(2-fluoro-4-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound FC1=CC(N2CCOCC2)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O SKKMNDJFMBCHFI-UHFFFAOYSA-N 0.000 claims 1
- GUDNOEUDNIYXST-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(2-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(CC=3C(=CC=CC=3)C=3C=CC=CC=3)CC2CN1C(=O)ON1C(=O)CCC1=O GUDNOEUDNIYXST-UHFFFAOYSA-N 0.000 claims 1
- JVWFRPDSSLUJAL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-chloro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1COCCN1C1=CC(Cl)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O JVWFRPDSSLUJAL-UHFFFAOYSA-N 0.000 claims 1
- RBLUADGCZMXOAX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-chloro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CCCN1C1=CC(Cl)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O RBLUADGCZMXOAX-UHFFFAOYSA-N 0.000 claims 1
- WGCTUGFXQLBHFW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-fluoro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1COCCN1C1=CC(F)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O WGCTUGFXQLBHFW-UHFFFAOYSA-N 0.000 claims 1
- XTJHVWYAYOMXNW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-fluoro-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CCCN1C1=CC(F)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O XTJHVWYAYOMXNW-UHFFFAOYSA-N 0.000 claims 1
- FLEDTRIQUOHVGQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[(4-propan-2-yl-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CCCN1C1=CC(C(C)C)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O FLEDTRIQUOHVGQ-UHFFFAOYSA-N 0.000 claims 1
- OVTWKLNUMXQFBT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[2-(4-acetylpiperazin-1-yl)-4-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 OVTWKLNUMXQFBT-UHFFFAOYSA-N 0.000 claims 1
- KQCMGWLWNGILNW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[2-(4-acetylpiperazin-1-yl)-4-propan-2-ylphenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(C)=O)CCN1C1=CC(C(C)C)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O KQCMGWLWNGILNW-UHFFFAOYSA-N 0.000 claims 1
- BYILKVNTBJWPED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-(4-acetylpiperazin-1-yl)-2-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C(C=C1Cl)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 BYILKVNTBJWPED-UHFFFAOYSA-N 0.000 claims 1
- PGNNFIWBKRZBSS-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-(4-acetylpiperazin-1-yl)-2-fluorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C(C=C1F)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 PGNNFIWBKRZBSS-UHFFFAOYSA-N 0.000 claims 1
- RMFWBQDASIAUGU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-chloro-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CC2(C(NCC2)=O)CCN1C1=CC(Cl)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O RMFWBQDASIAUGU-UHFFFAOYSA-N 0.000 claims 1
- YQJQFUVBLIJOOX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-fluoro-2-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C1=CC(F)=CC=C1CN1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 YQJQFUVBLIJOOX-UHFFFAOYSA-N 0.000 claims 1
- GNEAFYKODSFJMK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[[4-morpholin-4-yl-2-(trifluoromethoxy)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound FC(F)(F)OC1=CC(N2CCOCC2)=CC=C1CN(CC1C2)CC1CN2C(=O)ON1C(=O)CCC1=O GNEAFYKODSFJMK-UHFFFAOYSA-N 0.000 claims 1
- MSKRXEICVNFEMQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-[bis(4-chlorophenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC(Cl)=CC=1)N1CC2CN(C(=O)ON3C(CCC3=O)=O)CC2C1 MSKRXEICVNFEMQ-UHFFFAOYSA-N 0.000 claims 1
- CIGBIGGDUAQRLU-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(1-ethyl-3-pyridin-3-ylpyrazol-4-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CN=C1 CIGBIGGDUAQRLU-UHFFFAOYSA-N 0.000 claims 1
- ZQIRVRDHXCQWEF-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-cyclohexyl-5-methylpyrazol-3-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N1=C(C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C1CCCCC1 ZQIRVRDHXCQWEF-UHFFFAOYSA-N 0.000 claims 1
- OOYPIHJULVUGEB-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-cyclohexyl-5-propan-2-ylpyrazol-3-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N1=C(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C1CCCCC1 OOYPIHJULVUGEB-UHFFFAOYSA-N 0.000 claims 1
- VSPCXZZEUGFDAL-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-methyl-3-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=C1N1CCOCC1 VSPCXZZEUGFDAL-UHFFFAOYSA-N 0.000 claims 1
- MEVQYEWUCLPVNX-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-methyl-3-piperidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=C1N1CCCCC1 MEVQYEWUCLPVNX-UHFFFAOYSA-N 0.000 claims 1
- HPKSIINLLINMFO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(2-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC1=CC=CC=C1C1=CC=CC=C1 HPKSIINLLINMFO-UHFFFAOYSA-N 0.000 claims 1
- FRRIOGDSAYLQBH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(3-methyl-2-piperidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1=CC=CC(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)=C1N1CCCCC1 FRRIOGDSAYLQBH-UHFFFAOYSA-N 0.000 claims 1
- HHSUBEJPQGJXKP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(3-phenyl-1-propan-2-ylpyrazol-4-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1=CC=CC=C1 HHSUBEJPQGJXKP-UHFFFAOYSA-N 0.000 claims 1
- BYLBIZIQXNAYTJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-fluoro-2-morpholin-4-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C(F)=CC=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1N1CCOCC1 BYLBIZIQXNAYTJ-UHFFFAOYSA-N 0.000 claims 1
- YPFURSFOBNHDRO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-phenylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC(C=C1)=CC=C1C1=CC=CC=C1 YPFURSFOBNHDRO-UHFFFAOYSA-N 0.000 claims 1
- KIYXWQPEKDAVJF-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(4-propan-2-yl-2-pyrrolidin-1-ylphenyl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C=1C(C(C)C)=CC=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1N1CCCC1 KIYXWQPEKDAVJF-UHFFFAOYSA-N 0.000 claims 1
- GROSUVLLDKTZMY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[(5-methyl-2-propan-2-ylpyrazol-3-yl)methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC(C)N1N=C(C)C=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 GROSUVLLDKTZMY-UHFFFAOYSA-N 0.000 claims 1
- OZTNLWMHWOXZQO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(3-morpholin-4-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=1)=CC=CC=1N1CCOCC1 OZTNLWMHWOXZQO-UHFFFAOYSA-N 0.000 claims 1
- ZRWRFCSMVPWYKY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(3-pyrrolidin-1-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=1)=CC=CC=1N1CCCC1 ZRWRFCSMVPWYKY-UHFFFAOYSA-N 0.000 claims 1
- PFSDNZSZQQDAHC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-ethyl-3-(4-morpholin-4-ylphenyl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(CC)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C(C=C1)=CC=C1N1CCOCC1 PFSDNZSZQQDAHC-UHFFFAOYSA-N 0.000 claims 1
- ZYSXWYSHUIAXLB-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[1-methyl-3-(1-methylsulfonylpiperidin-4-yl)pyrazol-4-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N=1N(C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=1C1CCN(S(C)(=O)=O)CC1 ZYSXWYSHUIAXLB-UHFFFAOYSA-N 0.000 claims 1
- GETJHMNSCNZETI-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(1-acetylpiperidin-4-yl)-5-methylpyrazol-3-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCC1N1C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)=CC(C)=N1 GETJHMNSCNZETI-UHFFFAOYSA-N 0.000 claims 1
- RVRCFUYVXYANTH-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(4-acetylpiperazin-1-yl)-4-chlorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 RVRCFUYVXYANTH-UHFFFAOYSA-N 0.000 claims 1
- CERGHDKYTLVEHR-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(4-acetylpiperazin-1-yl)-4-fluorophenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(F)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 CERGHDKYTLVEHR-UHFFFAOYSA-N 0.000 claims 1
- CZPMRGQOYYDTSW-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-(oxan-4-yl)-5-propan-2-ylpyrazol-3-yl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound N1=C(C(C)C)C=C(CN2CC3CN(CC3C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1C1CCOCC1 CZPMRGQOYYDTSW-UHFFFAOYSA-N 0.000 claims 1
- UOAWPMBZAUBMSP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-chloro-3-(2-oxa-7-azaspiro[4.4]nonan-7-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound C1C2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2CN1CC(C=1Cl)=CC=CC=1N(C1)CCC21CCOC2 UOAWPMBZAUBMSP-UHFFFAOYSA-N 0.000 claims 1
- SFZXBXWVBSGAOM-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-[[2-chloro-4-(3-methylmorpholin-4-yl)phenyl]methyl]-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrole-5-carboxylate Chemical compound CC1COCCN1C(C=C1Cl)=CC=C1CN1CC2CN(C(=O)OC(C(F)(F)F)C(F)(F)F)CC2C1 SFZXBXWVBSGAOM-UHFFFAOYSA-N 0.000 claims 1
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- VWQGUYVIBBRZHN-UHFFFAOYSA-N ClC1=C(CN2CC3C(C2)CN(C3)C(=O)ON2C(CCC2=O)=O)C=CC(=C1)C(=O)N1CCCC1 Chemical compound ClC1=C(CN2CC3C(C2)CN(C3)C(=O)ON2C(CCC2=O)=O)C=CC(=C1)C(=O)N1CCCC1 VWQGUYVIBBRZHN-UHFFFAOYSA-N 0.000 claims 1
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- RWPDKIOERSRLRE-UHFFFAOYSA-N ClC1=C(CN2CC3C(C2)CN(C3)C(=O)ON2C(CCC2=O)=O)C=CC(=C1)C(=O)N1CCOCC1 Chemical compound ClC1=C(CN2CC3C(C2)CN(C3)C(=O)ON2C(CCC2=O)=O)C=CC(=C1)C(=O)N1CCOCC1 RWPDKIOERSRLRE-UHFFFAOYSA-N 0.000 claims 1
- CQQXADPTIFZTKE-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1CCC(CC1)F Chemical compound ClC=1C(=C(C=CC=1)CN1CC2C(C1)CN(C2)C(=O)OC(C(F)(F)F)C(F)(F)F)N1CCC(CC1)F CQQXADPTIFZTKE-UHFFFAOYSA-N 0.000 claims 1
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- XGIPKPKBHNEYIE-UHFFFAOYSA-N FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1)C(F)(F)F Chemical compound FC(F)(F)C(OC(=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1)C(F)(F)F XGIPKPKBHNEYIE-UHFFFAOYSA-N 0.000 claims 1
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- QWTJUCPZCOIYSO-UHFFFAOYSA-N FC1CCN(CC1)c1c(Cl)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O Chemical compound FC1CCN(CC1)c1c(Cl)cccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O QWTJUCPZCOIYSO-UHFFFAOYSA-N 0.000 claims 1
- PKFXUWBWCICFQU-UHFFFAOYSA-N Fc1cc(ccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O)C(=O)N1CCC1 Chemical compound Fc1cc(ccc1CN1CC2CN(CC2C1)C(=O)ON1C(=O)CCC1=O)C(=O)N1CCC1 PKFXUWBWCICFQU-UHFFFAOYSA-N 0.000 claims 1
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- 150000001204 N-oxides Chemical class 0.000 claims 1
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- IYBRDNIYDIMXHU-UHFFFAOYSA-N O=C(ON1C(=O)CCC1=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1 Chemical compound O=C(ON1C(=O)CCC1=O)N1CC2CN(Cc3cccc(c3)-c3ccccc3)CC2C1 IYBRDNIYDIMXHU-UHFFFAOYSA-N 0.000 claims 1
- DZVOJFPNKWVRSH-UHFFFAOYSA-N OC(=O)N1CC2CN(Cc3ccc(cc3)-c3ccccc3)CC2C1 Chemical compound OC(=O)N1CC2CN(Cc3ccc(cc3)-c3ccccc3)CC2C1 DZVOJFPNKWVRSH-UHFFFAOYSA-N 0.000 claims 1
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- 235000001484 Trigonella foenum graecum Nutrition 0.000 claims 1
- 244000250129 Trigonella foenum graecum Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
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- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
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- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 125000005551 pyridylene group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
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- 125000003003 spiro group Chemical group 0.000 claims 1
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| PCT/US2014/045145 WO2015003002A1 (en) | 2013-07-03 | 2014-07-01 | Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof |
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| JP2016525092A JP2016525092A (ja) | 2016-08-22 |
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| JP (1) | JP6647592B2 (https=) |
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| CA (1) | CA2917050A1 (https=) |
| MX (1) | MX2015017961A (https=) |
| WO (1) | WO2015003002A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9487495B2 (en) | 2012-01-06 | 2016-11-08 | The Scripts Research Institute | Carbamate compounds and of making and using same |
| CA2917050A1 (en) | 2013-07-03 | 2015-01-08 | Todd K. Jones | Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof |
| UA121775C2 (uk) * | 2015-07-31 | 2020-07-27 | Пфайзер Інк. | 1,1,1-трифтор-3-гідроксипропан-2-ілкарбаматні похідні та 1,1,1-трифтор-4-гідроксибутан-2-ілкарбаматні похідні як інгібітори magl |
| WO2017143283A1 (en) | 2016-02-19 | 2017-08-24 | Abide Therapeutics, Inc. | Radiolabeled monoacylglycerol lipase occupancy probe |
| WO2017197192A1 (en) * | 2016-05-12 | 2017-11-16 | Abide Therapeutics, Inc. | Spirocycle compounds and methods of making and using same |
| JP7042804B2 (ja) * | 2016-09-19 | 2022-03-28 | ルンドベック ラ ホーヤ リサーチ センター，インク． | ピペラジンカルバメート、及びその製造と使用の方法 |
| KR20190085046A (ko) * | 2016-11-16 | 2019-07-17 | 어바이드 테라퓨틱스, 인크. | 약학 제제 |
| JOP20190106A1 (ar) * | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| DK3541807T3 (da) | 2016-11-16 | 2021-12-06 | H Lundbeck As | Krystallinsk form af en magl-inhibitor |
| JOP20190105A1 (ar) * | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| EP3571191A1 (en) * | 2017-01-20 | 2019-11-27 | Pfizer Inc | 1,1,1-trifluoro-3-hydroxypropan-2-yl carbamate derivatives as magl inhibitors |
| EP4335848A3 (en) | 2017-03-13 | 2024-06-19 | Lundbeck La Jolla Research Center, Inc. | Dual magl and faah inhibitors |
| CR20200088A (es) * | 2017-08-29 | 2020-04-08 | Lundbeck La Jolla Research Center Inc | Compuestos espirocíclicos y sus métodos de preparación y uso |
| JP7257387B2 (ja) | 2017-08-29 | 2023-04-13 | ハー・ルンドベック・アクチエゼルスカベット | スピロ環化合物並びにその作製及び使用方法 |
| MX2020007318A (es) * | 2017-09-29 | 2020-08-24 | Takeda Pharmaceuticals Co | Compuesto heterociclico. |
| KR20210010475A (ko) | 2018-05-15 | 2021-01-27 | 룬드벡 라 졸라 리서치 센터 인코포레이티드 | Magl 저해제 |
| AU2019304198A1 (en) * | 2018-07-19 | 2021-02-04 | Pfizer Inc. | Heterocyclic spiro compounds as MAGL inhibitors |
| WO2021062232A1 (en) * | 2019-09-26 | 2021-04-01 | The Board Of Trustees Of The Leland Stanford Junior University | Methods for reducing rewarding effects of morphine without affecting its analgesic effects |
| IL297470A (en) | 2020-04-21 | 2022-12-01 | H Lundbeck As | Synthesis of a monoacylglycerol lipase inhibitor |
| TWI904281B (zh) | 2020-11-13 | 2025-11-11 | 丹麥商Ｈ 朗德貝克公司 | Magl抑制劑 |
| TW202304932A (zh) * | 2021-04-01 | 2023-02-01 | 日商小野藥品工業股份有限公司 | Abhd6拮抗劑 |
| CA3242372A1 (en) | 2021-12-29 | 2023-07-06 | Psy Therapeutics, Inc. | Inhibiting monoacylglycerol lipase (magl) |
| KR20250005229A (ko) | 2022-05-04 | 2025-01-09 | 하. 룬드벡 아크티에셀스카브 | 모노아실글리세롤 리파제 억제제로서 1,1,1,3,3,3-헥사플루오로프로판-2-일 (s)-1-(피리다진-3-일카르바모일)-6 아자스피로[2.5]옥탄-6-카르복실레이트의 결정질 형태 |
| JP7852604B2 (ja) * | 2022-09-30 | 2026-04-28 | 小野薬品工業株式会社 | Ａｂｈｄ６アンタゴニストを含有する医薬組成物 |
| EP4665718A1 (en) * | 2023-02-13 | 2025-12-24 | Apogee Pharmaceuticals, Inc. | Small molecules as monoacylglycerol lipase (magl) inhibitors, compositions and use thereof |
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| SE0100326D0 (sv) * | 2001-02-02 | 2001-02-02 | Astrazeneca Ab | New compounds |
| EP1368354A1 (en) * | 2001-03-07 | 2003-12-10 | Pfizer Products Inc. | Modulators of chemokine receptor activity |
| JP2011513421A (ja) * | 2008-03-05 | 2011-04-28 | ターガセプト，インコーポレイテッド | サブタイプ選択的なジアザビシクロアルカンのアミド |
| ME03452B (me) * | 2009-10-23 | 2020-01-20 | Janssen Pharmaceutica Nv | Disupstituisani oktahi-dropirolo[3,4-c]piroli kao modulatori oreksin receptora |
| CA2791672A1 (en) * | 2010-03-04 | 2011-09-09 | Merck Sharp & Dohme Corp. | Positive allosteric modulators of mglur2 |
| EP2444084A1 (en) * | 2010-10-21 | 2012-04-25 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Use of PI3K inibitors for the treatment of obesity |
| MX368615B (es) | 2012-09-25 | 2019-10-09 | Hoffmann La Roche | Derivados bicíclicos como inhibidores de la autotaxina (atx) que son inhibidores de la producción de ácido lisofosfatídico (lpa) y el uso de los mismos. |
| CA2917050A1 (en) | 2013-07-03 | 2015-01-08 | Todd K. Jones | Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof |
-
2014
- 2014-07-01 CA CA2917050A patent/CA2917050A1/en not_active Abandoned
- 2014-07-01 WO PCT/US2014/045145 patent/WO2015003002A1/en not_active Ceased
- 2014-07-01 US US14/902,324 patent/US9828379B2/en not_active Expired - Fee Related
- 2014-07-01 MX MX2015017961A patent/MX2015017961A/es unknown
- 2014-07-01 JP JP2016524330A patent/JP6647592B2/ja not_active Expired - Fee Related
- 2014-07-01 EP EP14820480.3A patent/EP3016653A4/en not_active Withdrawn
- 2014-07-01 CN CN201480048531.6A patent/CN105517547A/zh active Pending
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