CA2866302A1 - Carbamate compounds and of making and using same - Google Patents
Carbamate compounds and of making and using same Download PDFInfo
- Publication number
- CA2866302A1 CA2866302A1 CA2866302A CA2866302A CA2866302A1 CA 2866302 A1 CA2866302 A1 CA 2866302A1 CA 2866302 A CA2866302 A CA 2866302A CA 2866302 A CA2866302 A CA 2866302A CA 2866302 A1 CA2866302 A1 CA 2866302A1
- Authority
- CA
- Canada
- Prior art keywords
- carboxylate
- dioxopyrrolidin
- methyl
- 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.)
- Abandoned
Links
- 150000004657 carbamic acid derivatives Chemical class 0.000 title abstract description 15
- 208000002193 Pain Diseases 0.000 claims abstract description 15
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
- 230000036407 pain Effects 0.000 claims abstract description 11
- 208000008589 Obesity Diseases 0.000 claims abstract description 5
- 235000020824 obesity Nutrition 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 284
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 250
- -1 cyano, hydroxyl Chemical group 0.000 claims description 209
- 229910052736 halogen Inorganic materials 0.000 claims description 183
- 150000002367 halogens Chemical class 0.000 claims description 183
- 238000000034 method Methods 0.000 claims description 152
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 145
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 123
- 239000000203 mixture Substances 0.000 claims description 103
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 100
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 96
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 94
- 125000001424 substituent group Chemical group 0.000 claims description 70
- 125000005842 heteroatom Chemical group 0.000 claims description 55
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 125000002950 monocyclic group Chemical group 0.000 claims description 32
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000004043 oxo group Chemical group O=* 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 17
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- FRIRBHKMNMAHAB-UHFFFAOYSA-N 4-(4-methoxyphenyl)piperazine-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1CCN(C(O)=O)CC1 FRIRBHKMNMAHAB-UHFFFAOYSA-N 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
- 201000010374 Down Syndrome Diseases 0.000 claims description 8
- 206010044688 Trisomy 21 Diseases 0.000 claims description 8
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- ZHKCNZFFTQICCD-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(imidazo[1,2-a]pyridin-3-ylmethyl)piperazine-1-carboxylate Chemical compound C1CN(CC=2N3C=CC=CC3=NC=2)CCN1C(=O)ON1C(=O)CCC1=O ZHKCNZFFTQICCD-UHFFFAOYSA-N 0.000 claims description 2
- XKDCVYHPYVBFNC-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(2-chloro-4-pyrrolidin-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound ClC1=CC(N2CCCC2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O XKDCVYHPYVBFNC-UHFFFAOYSA-N 0.000 claims description 2
- CGNKQNOQGZWEIP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(2-fluoro-4-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound FC1=CC(N2CCOCC2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O CGNKQNOQGZWEIP-UHFFFAOYSA-N 0.000 claims description 2
- NGQBQOVBXLOKAX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(3-fluoro-4-pyrazol-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C=1C=C(N2N=CC=C2)C(F)=CC=1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O NGQBQOVBXLOKAX-UHFFFAOYSA-N 0.000 claims description 2
- NHUZHNZDAGGOEV-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(3-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(CC=2C=C(C=CC=2)N2CCOCC2)CCN1C(=O)ON1C(=O)CCC1=O NHUZHNZDAGGOEV-UHFFFAOYSA-N 0.000 claims description 2
- FKEDBBRRMLBJTQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-chlorophenyl)methyl]piperazine-1-carboxylate Chemical compound C1=CC(Cl)=CC=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 FKEDBBRRMLBJTQ-UHFFFAOYSA-N 0.000 claims description 2
- SOHGNKYOVKHJAI-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-(3,4a,5,6,7,7a-hexahydro-2h-cyclopenta[b][1,4]oxazin-4-yl)-4-chlorophenyl]methyl]piperazine-1-carboxylate Chemical compound C1COC2CCCC2N1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O SOHGNKYOVKHJAI-UHFFFAOYSA-N 0.000 claims description 2
- PRSJVEXRBBPDRY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-acetylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)C)CCN1C(=O)ON1C(=O)CCC1=O PRSJVEXRBBPDRY-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- DMANMRRMUSBEOH-UHFFFAOYSA-N 4-methoxyoxadiazole Chemical group COC1=CON=N1 DMANMRRMUSBEOH-UHFFFAOYSA-N 0.000 claims description 2
- HSMPSHPWCOOUJH-UHFFFAOYSA-N anilinyl Chemical group [NH]C1=CC=CC=C1 HSMPSHPWCOOUJH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- XDISMKMQWMVILZ-UHFFFAOYSA-N (1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl) 4-(4-methoxyphenyl)piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)ON2C(C3CCCCC3C2=O)=O)CC1 XDISMKMQWMVILZ-UHFFFAOYSA-N 0.000 claims 1
- RBXYQOCVOBLCLR-UHFFFAOYSA-N (1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-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(C3CCCCC3C2=O)=O)CC1 RBXYQOCVOBLCLR-UHFFFAOYSA-N 0.000 claims 1
- 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
- CYUWVRVMSROECG-UHFFFAOYSA-N (1,3-dioxoisoindol-2-yl) 4-[2-(4-chlorophenyl)ethyl]piperidine-1-carboxylate Chemical compound C1=CC(Cl)=CC=C1CCC1CCN(C(=O)ON2C(C3=CC=CC=C3C2=O)=O)CC1 CYUWVRVMSROECG-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
- BTKSLLXVEQSNRB-UHFFFAOYSA-N (2,5-dioxo-3-phenylpyrrolidin-1-yl) 4-(4-methoxyphenyl)piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)ON2C(C(CC2=O)C=2C=CC=CC=2)=O)CC1 BTKSLLXVEQSNRB-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
- WZGAZCLXYLNBGH-UHFFFAOYSA-N (2,5-dioxo-3-phenylpyrrolidin-1-yl) n,n-dimethylcarbamate Chemical compound O=C1N(OC(=O)N(C)C)C(=O)CC1C1=CC=CC=C1 WZGAZCLXYLNBGH-UHFFFAOYSA-N 0.000 claims 1
- GWNVUXVQIDMSQY-UHFFFAOYSA-N (2,5-dioxo-3-phenylpyrrolidin-1-yl) piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)ON(C1=O)C(=O)CC1C1=CC=CC=C1 GWNVUXVQIDMSQY-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
- SDNNRGMKKYQMAX-UHFFFAOYSA-N (2,5-dioxoimidazolidin-1-yl) 4-[2-(4-chlorophenyl)ethyl]piperidine-1-carboxylate Chemical compound C1=CC(Cl)=CC=C1CCC1CCN(C(=O)ON2C(NCC2=O)=O)CC1 SDNNRGMKKYQMAX-UHFFFAOYSA-N 0.000 claims 1
- CLHILKCNNWLEIP-UHFFFAOYSA-N (2,5-dioxoimidazolidin-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(NCC2=O)=O)CC1 CLHILKCNNWLEIP-UHFFFAOYSA-N 0.000 claims 1
- ZYOLEBDRBWSQHK-UHFFFAOYSA-N (2,5-dioxoimidazolidin-1-yl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)ON1C(=O)CNC1=O ZYOLEBDRBWSQHK-UHFFFAOYSA-N 0.000 claims 1
- SUJAZUIOILZNRA-UHFFFAOYSA-N (2,5-dioxoimidazolidin-1-yl) piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)ON1C(=O)CNC1=O SUJAZUIOILZNRA-UHFFFAOYSA-N 0.000 claims 1
- WDQUAAYVWRCPDJ-OAHLLOKOSA-N (2,5-dioxopyrrolidin-1-yl) (2r)-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-OAHLLOKOSA-N 0.000 claims 1
- GLTFVSXLEKWKAC-OAHLLOKOSA-N (2,5-dioxopyrrolidin-1-yl) (2r)-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-OAHLLOKOSA-N 0.000 claims 1
- DLBPNKZBGRQSNF-OAHLLOKOSA-N (2,5-dioxopyrrolidin-1-yl) (2r)-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-OAHLLOKOSA-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
- VOTLDWSBUFPSHI-CYBMUJFWSA-N (2,5-dioxopyrrolidin-1-yl) (3r)-3-phenylmethoxypyrrolidine-1-carboxylate Chemical compound C([C@@H](CC1)OCC=2C=CC=CC=2)N1C(=O)ON1C(=O)CCC1=O VOTLDWSBUFPSHI-CYBMUJFWSA-N 0.000 claims 1
- VOTLDWSBUFPSHI-ZDUSSCGKSA-N (2,5-dioxopyrrolidin-1-yl) (3s)-3-phenylmethoxypyrrolidine-1-carboxylate Chemical compound C([C@H](CC1)OCC=2C=CC=CC=2)N1C(=O)ON1C(=O)CCC1=O VOTLDWSBUFPSHI-ZDUSSCGKSA-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
- RNLLMPGAIYHZJK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-(2-phenylethyl)piperidine-1-carboxylate Chemical compound C1CCCC(CCC=2C=CC=CC=2)N1C(=O)ON1C(=O)CCC1=O RNLLMPGAIYHZJK-UHFFFAOYSA-N 0.000 claims 1
- PSPGHNGDQFLMFZ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound OCC1CCCCN1C(=O)ON1C(=O)CCC1=O PSPGHNGDQFLMFZ-UHFFFAOYSA-N 0.000 claims 1
- HHRSEWDYYAEMOM-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-(morpholine-4-carbonyl)piperidine-1-carboxylate Chemical compound C1CCCC(C(=O)N2CCOCC2)N1C(=O)ON1C(=O)CCC1=O HHRSEWDYYAEMOM-UHFFFAOYSA-N 0.000 claims 1
- CHGZJFFLOPTVFS-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-(trifluoromethyl)piperidine-1-carboxylate Chemical compound FC(F)(F)C1CCCCN1C(=O)ON1C(=O)CCC1=O CHGZJFFLOPTVFS-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
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- OFHTUYIVPQVOOH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-bromo-2-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1COCCN1C1=CC(Br)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O OFHTUYIVPQVOOH-UHFFFAOYSA-N 0.000 claims 1
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- WCXVBQBYYXVZBA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-bromo-2-pyrrolidin-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CCCN1C1=CC(Br)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O WCXVBQBYYXVZBA-UHFFFAOYSA-N 0.000 claims 1
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- DOGNWZCSZWXJMI-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-chloro-2-piperidin-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CCCCN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O DOGNWZCSZWXJMI-UHFFFAOYSA-N 0.000 claims 1
- IKSYFRMAOGUBQA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-chloro-2-pyrazol-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1=CC=NN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O IKSYFRMAOGUBQA-UHFFFAOYSA-N 0.000 claims 1
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- WXSZKUXEHRVPIN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-fluoro-3-pyrrolidin-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1=C(N2CCCC2)C(F)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O WXSZKUXEHRVPIN-UHFFFAOYSA-N 0.000 claims 1
- MDMCEUXDHWTRPG-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-methoxyphenyl)methyl]piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 MDMCEUXDHWTRPG-UHFFFAOYSA-N 0.000 claims 1
- HGDXBQZJQGTVGU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-methyl-2-piperidin-1-yl-1,3-thiazol-5-yl)methyl]piperazine-1-carboxylate Chemical compound CC=1N=C(N2CCCCC2)SC=1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O HGDXBQZJQGTVGU-UHFFFAOYSA-N 0.000 claims 1
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- UXAHYZWDNURINX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-morpholin-4-yl-2-propan-2-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound CC(C)C1=CC(N2CCOCC2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O UXAHYZWDNURINX-UHFFFAOYSA-N 0.000 claims 1
- BPJQVWRDOSBFHY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(CC=2C=CC(=CC=2)N2CCOCC2)CCN1C(=O)ON1C(=O)CCC1=O BPJQVWRDOSBFHY-UHFFFAOYSA-N 0.000 claims 1
- NCMBXNQJRYTKHE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-phenyl-2-propan-2-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound CC(C)C1=CC(C=2C=CC=CC=2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O NCMBXNQJRYTKHE-UHFFFAOYSA-N 0.000 claims 1
- RBUWFWVNADIIRW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(4-pyrrolidin-1-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(CC=2C=CC(=CC=2)N2CCCC2)CCN1C(=O)ON1C(=O)CCC1=O RBUWFWVNADIIRW-UHFFFAOYSA-N 0.000 claims 1
- KAIVRACPLODHGU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(5-chloro-2-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(Cl)=CC=C1N1CCOCC1 KAIVRACPLODHGU-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
- XZEULGRNZXPAIW-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(5-methyl-2-morpholin-4-ylphenyl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(C)=CC=C1N1CCOCC1 XZEULGRNZXPAIW-UHFFFAOYSA-N 0.000 claims 1
- BIRWPPFHBROJNV-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(5-methyl-2-propan-2-ylpyrazol-3-yl)methyl]piperazine-1-carboxylate Chemical compound CC(C)N1N=C(C)C=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 BIRWPPFHBROJNV-UHFFFAOYSA-N 0.000 claims 1
- WDMAJHKVYFPOAK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[(6-chloro-2-methylimidazo[1,2-a]pyridin-3-yl)methyl]piperazine-1-carboxylate Chemical compound CC=1N=C2C=CC(Cl)=CN2C=1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O WDMAJHKVYFPOAK-UHFFFAOYSA-N 0.000 claims 1
- GRFPCPFXBLGOER-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[2-(4-chlorophenyl)ethyl]piperidine-1-carboxylate Chemical compound C1=CC(Cl)=CC=C1CCC1CCN(C(=O)ON2C(CCC2=O)=O)CC1 GRFPCPFXBLGOER-UHFFFAOYSA-N 0.000 claims 1
- HKAQTSYITLEJEN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[2-(azetidin-1-yl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1C(=O)CN1CCC1 HKAQTSYITLEJEN-UHFFFAOYSA-N 0.000 claims 1
- KQBRSGHEHKKICX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[2-[2-chloro-5-(trifluoromethyl)anilino]-2-oxoethyl]piperazine-1-carboxylate Chemical compound FC(F)(F)C1=CC=C(Cl)C(NC(=O)CN2CCN(CC2)C(=O)ON2C(CCC2=O)=O)=C1 KQBRSGHEHKKICX-UHFFFAOYSA-N 0.000 claims 1
- BNTVWCOJAAZYIQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-(3-acetamidopyrrolidin-1-yl)-4-chlorophenyl]methyl]piperazine-1-carboxylate Chemical compound C1C(NC(=O)C)CCN1C1=CC(Cl)=CC=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 BNTVWCOJAAZYIQ-UHFFFAOYSA-N 0.000 claims 1
- ZIAUHTBYCYBSOV-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-(4-acetylpiperazin-1-yl)-4-chlorophenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)C)CCN1C1=CC(Cl)=CC=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 ZIAUHTBYCYBSOV-UHFFFAOYSA-N 0.000 claims 1
- JBNQXUOLFXOJNK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-(azetidine-1-carbonyl)-4-chlorophenyl]methyl]piperazine-1-carboxylate Chemical compound C1CCN1C(=O)C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O JBNQXUOLFXOJNK-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
- WBAVUFQRHDJXBX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-(morpholine-4-carbonyl)-5-(trifluoromethyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(C(F)(F)F)=CC=C1C(=O)N1CCOCC1 WBAVUFQRHDJXBX-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
- HCYDLVKJGUMXFM-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-chloro-4-(pyrrolidine-1-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound ClC1=CC(C(=O)N2CCCC2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O HCYDLVKJGUMXFM-UHFFFAOYSA-N 0.000 claims 1
- DHNDMTYQSMADRQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-fluoro-4-(2-methylpyridin-4-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1=NC(C)=CC(C=2C=C(F)C(CN3CCN(CC3)C(=O)ON3C(CCC3=O)=O)=CC=2)=C1 DHNDMTYQSMADRQ-UHFFFAOYSA-N 0.000 claims 1
- RLYHOSSVOXYCAN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-fluoro-4-(3-fluorophenyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound FC1=CC=CC(C=2C=C(F)C(CN3CCN(CC3)C(=O)ON3C(CCC3=O)=O)=CC=2)=C1 RLYHOSSVOXYCAN-UHFFFAOYSA-N 0.000 claims 1
- USLOOWZYMQDNOE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-fluoro-4-(3-methylpyridin-4-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound CC1=CN=CC=C1C(C=C1F)=CC=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 USLOOWZYMQDNOE-UHFFFAOYSA-N 0.000 claims 1
- KUYJQQVWWWNKDB-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-fluoro-4-(6-methylpyridin-2-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound CC1=CC=CC(C=2C=C(F)C(CN3CCN(CC3)C(=O)ON3C(CCC3=O)=O)=CC=2)=N1 KUYJQQVWWWNKDB-UHFFFAOYSA-N 0.000 claims 1
- KCYTXGFDZSASDL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-methyl-3-(pyrrolidine-1-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1=CC=C(C(=O)N2CCCC2)C(C)=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O KCYTXGFDZSASDL-UHFFFAOYSA-N 0.000 claims 1
- XAWDIYMOHSMECT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-methyl-4-(2-methylpyridin-3-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound CC1=CC(C=2C(=NC=CC=2)C)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O XAWDIYMOHSMECT-UHFFFAOYSA-N 0.000 claims 1
- VMJCPFMKCDWEOQ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-methyl-4-(3-methylpyridin-4-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound CC1=CC(C=2C(=CN=CC=2)C)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O VMJCPFMKCDWEOQ-UHFFFAOYSA-N 0.000 claims 1
- RHMWWVGHHNQRTK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-methyl-4-(6-methylpyridin-2-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound CC1=CC=CC(C=2C=C(C)C(CN3CCN(CC3)C(=O)ON3C(CCC3=O)=O)=CC=2)=N1 RHMWWVGHHNQRTK-UHFFFAOYSA-N 0.000 claims 1
- UTXPSOXRZZUHKY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-methyl-6-(2-methylphenyl)pyridin-3-yl]methyl]piperazine-1-carboxylate Chemical compound CC1=CC=CC=C1C(N=C1C)=CC=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 UTXPSOXRZZUHKY-UHFFFAOYSA-N 0.000 claims 1
- GQEQDBOZQUMISN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[2-methyl-6-(3-methylphenyl)pyridin-3-yl]methyl]piperazine-1-carboxylate Chemical compound CC1=CC=CC(C=2N=C(C)C(CN3CCN(CC3)C(=O)ON3C(CCC3=O)=O)=CC=2)=C1 GQEQDBOZQUMISN-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
- XQDNQTXHFVKMRF-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[3-methyl-5-(morpholine-4-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C=1C(C(=O)N2CCOCC2)=CC(C)=CC=1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O XQDNQTXHFVKMRF-UHFFFAOYSA-N 0.000 claims 1
- YVCDVHOKRAVVOT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-(3-methylphenyl)-2-phenoxyphenyl]methyl]piperazine-1-carboxylate Chemical compound CC1=CC=CC(C=2C=C(OC=3C=CC=CC=3)C(CN3CCN(CC3)C(=O)ON3C(CCC3=O)=O)=CC=2)=C1 YVCDVHOKRAVVOT-UHFFFAOYSA-N 0.000 claims 1
- IGEUHVTXLDXUAE-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CC2(C(NCC2)=O)CCN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O IGEUHVTXLDXUAE-UHFFFAOYSA-N 0.000 claims 1
- ODDFQSKHPXIPBJ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(4-chloropyrazol-1-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1=C(Cl)C=NN1C1=CC(Cl)=CC=C1CN1CCN(C(=O)ON2C(CCC2=O)=O)CC1 ODDFQSKHPXIPBJ-UHFFFAOYSA-N 0.000 claims 1
- ONFUXLSABRNQOH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1C2=CC=CN=C2CN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O ONFUXLSABRNQOH-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
- DALTXBMZHSXRSA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(8-oxa-2-azaspiro[4.5]decan-2-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CC2(CCOCC2)CN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O DALTXBMZHSXRSA-UHFFFAOYSA-N 0.000 claims 1
- BCGSOASBDASVMS-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1C(O2)CCC2CN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O BCGSOASBDASVMS-UHFFFAOYSA-N 0.000 claims 1
- NPQWIZBCTDGAFG-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-(pyrrolidine-1-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CCCN1C(=O)C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O NPQWIZBCTDGAFG-UHFFFAOYSA-N 0.000 claims 1
- ZNJWARGOEQXMCN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-2-[4-(pyrrolidine-1-carbonyl)piperidin-1-yl]phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CC(C(=O)N2CCCC2)CCN1C1=CC(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O ZNJWARGOEQXMCN-UHFFFAOYSA-N 0.000 claims 1
- HGDGZPKAKMKUTP-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-chloro-3-(morpholine-4-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1=C(C(=O)N2CCOCC2)C(Cl)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O HGDGZPKAKMKUTP-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
- GDEDAMYRQFYXNB-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[4-phenyl-2-(pyrrolidine-1-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(CC=2C(=CC(=CC=2)C=2C=CC=CC=2)C(=O)N2CCCC2)CCN1C(=O)ON1C(=O)CCC1=O GDEDAMYRQFYXNB-UHFFFAOYSA-N 0.000 claims 1
- PDZWSHCRNZWZEL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[5-(3-fluorophenyl)-6-methylpyridin-2-yl]methyl]piperazine-1-carboxylate Chemical compound C=1C=C(C=2C=C(F)C=CC=2)C(C)=NC=1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O PDZWSHCRNZWZEL-UHFFFAOYSA-N 0.000 claims 1
- OVJDSDGKYPJNKU-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[5-(4-methoxyphenyl)-1,2-oxazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1C1=CC(CN2CCN(CC2)C(=O)ON2C(CCC2=O)=O)=NO1 OVJDSDGKYPJNKU-UHFFFAOYSA-N 0.000 claims 1
- YQNIYBXNLBUAEI-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[5-chloro-2-(morpholine-4-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(Cl)=CC=C1C(=O)N1CCOCC1 YQNIYBXNLBUAEI-UHFFFAOYSA-N 0.000 claims 1
- CWJSLIGPWHDWML-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[5-methyl-2-(morpholine-4-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(C)=CC=C1C(=O)N1CCOCC1 CWJSLIGPWHDWML-UHFFFAOYSA-N 0.000 claims 1
- ZUHCKPRLCABXAB-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[5-methyl-2-(pyrrolidine-1-carbonyl)phenyl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)ON2C(CCC2=O)=O)CCN1CC1=CC(C)=CC=C1C(=O)N1CCCC1 ZUHCKPRLCABXAB-UHFFFAOYSA-N 0.000 claims 1
- MEYCLXNRTPKCCH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[[6-(3-fluorophenyl)-2-methylpyridin-3-yl]methyl]piperazine-1-carboxylate Chemical compound CC1=NC(C=2C=C(F)C=CC=2)=CC=C1CN(CC1)CCN1C(=O)ON1C(=O)CCC1=O MEYCLXNRTPKCCH-UHFFFAOYSA-N 0.000 claims 1
- MRWYJPLDFYWHKT-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[bis(1,3-benzodioxol-5-yl)-hydroxymethyl]piperidine-1-carboxylate Chemical compound C=1C=C2OCOC2=CC=1C(C=1C=C2OCOC2=CC=1)(O)C(CC1)CCN1C(=O)ON1C(=O)CCC1=O MRWYJPLDFYWHKT-UHFFFAOYSA-N 0.000 claims 1
- DPPOUOYXCUIPJA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[bis(1,3-dihydro-2-benzofuran-5-yl)-hydroxymethyl]piperidine-1-carboxylate Chemical compound C=1C=C2COCC2=CC=1C(C=1C=C2COCC2=CC=1)(O)C(CC1)CCN1C(=O)ON1C(=O)CCC1=O DPPOUOYXCUIPJA-UHFFFAOYSA-N 0.000 claims 1
- SJCBODWIRLGRIR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[bis(1,3-oxazol-4-yl)methyl]piperazine-1-carboxylate Chemical compound C1CN(C(C=2N=COC=2)C=2N=COC=2)CCN1C(=O)ON1C(=O)CCC1=O SJCBODWIRLGRIR-UHFFFAOYSA-N 0.000 claims 1
- XEOOXPKQXKTTLA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[bis(1-methylindazol-5-yl)methyl]piperazine-1-carboxylate Chemical compound C=1C=C2N(C)N=CC2=CC=1C(C=1C=C2C=NN(C)C2=CC=1)N(CC1)CCN1C(=O)ON1C(=O)CCC1=O XEOOXPKQXKTTLA-UHFFFAOYSA-N 0.000 claims 1
- QQNMXIMQYOKCHR-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[bis(4-bromophenyl)methyl]piperazine-1-carboxylate Chemical compound C1=CC(Br)=CC=C1C(C=1C=CC(Br)=CC=1)N1CCN(C(=O)ON2C(CCC2=O)=O)CC1 QQNMXIMQYOKCHR-UHFFFAOYSA-N 0.000 claims 1
- VYZJDJWFINQCKC-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[bis(4-chloro-2-methylphenyl)methyl]piperazine-1-carboxylate Chemical compound CC1=CC(Cl)=CC=C1C(C=1C(=CC(Cl)=CC=1)C)N1CCN(C(=O)ON2C(CCC2=O)=O)CC1 VYZJDJWFINQCKC-UHFFFAOYSA-N 0.000 claims 1
- BILWZNKXAWMVOX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-[bis(4-chlorophenyl)methyl]-3-methylpiperazine-1-carboxylate Chemical compound CC1CN(C(=O)ON2C(CCC2=O)=O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 BILWZNKXAWMVOX-UHFFFAOYSA-N 0.000 claims 1
- BEADRWVIFHOSGN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-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(CCC2=O)=O)CC1 BEADRWVIFHOSGN-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
- XFVLJXSEXKPHPL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-methylsulfonylpiperazine-1-carboxylate Chemical compound C1CN(S(=O)(=O)C)CCN1C(=O)ON1C(=O)CCC1=O XFVLJXSEXKPHPL-UHFFFAOYSA-N 0.000 claims 1
- MWOYFYXQIVRFQK-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-pent-4-ynoylpiperazine-1-carboxylate Chemical compound C1CN(C(CCC#C)=O)CCN1C(=O)ON1C(=O)CCC1=O MWOYFYXQIVRFQK-UHFFFAOYSA-N 0.000 claims 1
- QBSMMGWNXSFHRN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-piperidin-1-ylpiperidine-1-carboxylate Chemical compound C1CC(N2CCCCC2)CCN1C(=O)ON1C(=O)CCC1=O QBSMMGWNXSFHRN-UHFFFAOYSA-N 0.000 claims 1
- BDJKFNBWUNMHIF-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-pyrrolidin-1-ylpiperidine-1-carboxylate Chemical compound C1CC(N2CCCC2)CCN1C(=O)ON1C(=O)CCC1=O BDJKFNBWUNMHIF-UHFFFAOYSA-N 0.000 claims 1
- NZOYQRNIJRBWDZ-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) azetidine-1-carboxylate Chemical compound C1CCN1C(=O)ON1C(=O)CCC1=O NZOYQRNIJRBWDZ-UHFFFAOYSA-N 0.000 claims 1
- NIFUECPCDJUDHA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) morpholine-4-carboxylate Chemical compound C1COCCN1C(=O)ON1C(=O)CCC1=O NIFUECPCDJUDHA-UHFFFAOYSA-N 0.000 claims 1
- LXOBBUSVBIVCBX-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) n,n-dimethylcarbamate Chemical compound CN(C)C(=O)ON1C(=O)CCC1=O LXOBBUSVBIVCBX-UHFFFAOYSA-N 0.000 claims 1
- BGRURZQKIIDYSA-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) n-(1,2,3,4-tetrahydronaphthalen-1-yl)carbamate Chemical compound C1CCC2=CC=CC=C2C1NC(=O)ON1C(=O)CCC1=O BGRURZQKIIDYSA-UHFFFAOYSA-N 0.000 claims 1
- OVKVDSFNYFTCDL-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) n-(2-naphthalen-2-ylethyl)carbamate Chemical compound C=1C=C2C=CC=CC2=CC=1CCNC(=O)ON1C(=O)CCC1=O OVKVDSFNYFTCDL-UHFFFAOYSA-N 0.000 claims 1
- SOOYXTCIQMLHRY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) n-[(4-piperidin-1-ylphenyl)methyl]-n-propylcarbamate Chemical compound O=C1CCC(=O)N1OC(=O)N(CCC)CC(C=C1)=CC=C1N1CCCCC1 SOOYXTCIQMLHRY-UHFFFAOYSA-N 0.000 claims 1
- KHBRZKMTHVBCGP-KTKRTIGZSA-N (2,5-dioxopyrrolidin-1-yl) n-[(z)-octadec-9-enyl]carbamate Chemical compound CCCCCCCC\C=C/CCCCCCCCNC(=O)ON1C(=O)CCC1=O KHBRZKMTHVBCGP-KTKRTIGZSA-N 0.000 claims 1
- LIQPVZAHMOWVPF-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) n-[2-(4-phenoxyphenyl)ethyl]carbamate Chemical compound O=C1CCC(=O)N1OC(=O)NCCC(C=C1)=CC=C1OC1=CC=CC=C1 LIQPVZAHMOWVPF-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
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- C—CHEMISTRY; METALLURGY
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C07D498/08—Bridged systems
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| KR101653473B1 (ko) | 2012-01-06 | 2016-09-01 | 어바이드 테라퓨틱스, 인크. | 카르바메이트 화합물 및 그의 제조 및 이용 방법 |
| US9567302B2 (en) | 2012-03-19 | 2017-02-14 | Abide Therapeutics, Inc. | Carbamate compounds and of making and using same |
| 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 |
| JP6454349B2 (ja) * | 2013-12-26 | 2019-01-16 | 武田薬品工業株式会社 | モノアシルグリセロールリパーゼ(magl)阻害剤としての4−(ピペラジン−1−イル)−ピロリジン−2−オン化合物 |
| 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 |
| DK3122727T3 (en) | 2014-03-24 | 2018-04-09 | Bayer Cropscience Ag | METHOD FOR PREPARING 3,5-BIS (HALOGENAL COOL) PYRAZOLD DERIVATIVES OF ALFA, ALFA-DIHALOGENAMINES AND KETIMINES |
| WO2015179563A2 (en) * | 2014-05-22 | 2015-11-26 | 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 |
| CA2979537C (en) * | 2015-03-18 | 2023-08-29 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
| WO2016183097A1 (en) | 2015-05-11 | 2016-11-17 | Abide Therapeutics, 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 |
| CN109996790B (zh) | 2016-09-19 | 2023-05-16 | H.隆德贝克有限公司 | 哌嗪氨基甲酸酯及其制备和使用方法 |
| JOP20190106A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| KR102508739B1 (ko) | 2016-11-16 | 2023-03-09 | 하. 룬드벡 아크티에셀스카브 | Magl 억제제의 결정형 |
| MX393241B (es) | 2016-11-16 | 2025-03-24 | H Lundbeck As | Formulaciones farmaceuticas. |
| JOP20190105A1 (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 |
| US11274101B2 (en) | 2017-09-29 | 2022-03-15 | Takeda Pharmaceutical Company Limited | Heterocyclic compound |
| AR113926A1 (es) | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| CN111465410B (zh) | 2017-12-14 | 2022-10-25 | H.隆德贝克有限公司 | 包括施用1h-吡唑并[4,3-b]吡啶的组合治疗 |
| US10766893B2 (en) | 2017-12-20 | 2020-09-08 | H. Lundbeck A/S | 1H-pyrazolo[4,3-b]pyridines 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 |
| EP3728250A1 (en) | 2017-12-20 | 2020-10-28 | H. Lundbeck A/S | PYRAZOLO[3,4-beta]PYRIDINES AND IMIDAZO[1,5-beta]PYRIDAZINES AS PDE1 INHIBITORS |
| US11332453B2 (en) | 2018-05-15 | 2022-05-17 | H. Lundbeck A/S | MAGL inhibitors |
| 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 |
| CA3175210A1 (en) | 2020-04-21 | 2021-10-28 | Cheryl A. Grice | 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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| 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 |
| MX2010005711A (es) * | 2007-12-04 | 2010-06-02 | Basilea Pharmaceutica Ag | Proceso de preparacion de derivados del acido 2-(amino primario/secundario)hidrocarbil)-carbamoil-7-oxo-2,6-diaza-bicicl o[3.2.0]heptan-6-sulfonico. |
| EP2252584B1 (en) * | 2008-02-04 | 2016-12-07 | Prozyme, Inc. | Compounds and methods for rapid labeling of n-glycans |
| US9271962B2 (en) * | 2008-03-17 | 2016-03-01 | Northeastern University | Inhibitors of fatty acid amide hydrolase and monoacylglycerol lipase for modulation of cannabinoid receptors |
| JP2012505907A (ja) | 2008-10-17 | 2012-03-08 | アボット・ラボラトリーズ | Trpv1拮抗薬 |
| AU2009314629B2 (en) * | 2008-11-14 | 2014-09-25 | The Scripps Research Institute | Methods and compositions related to targeting monoacylglycerol lipase |
| US9567302B2 (en) | 2012-03-19 | 2017-02-14 | Abide Therapeutics, Inc. | Carbamate compounds and of making and using same |
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Also Published As
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| US9567302B2 (en) | 2017-02-14 |
| MX2014011134A (es) | 2014-12-10 |
| US20150080364A1 (en) | 2015-03-19 |
| WO2013142307A1 (en) | 2013-09-26 |
| JP6100883B2 (ja) | 2017-03-22 |
| CN104379578A (zh) | 2015-02-25 |
| CN104379578B (zh) | 2017-06-09 |
| EP2828253A1 (en) | 2015-01-28 |
| JP2015510938A (ja) | 2015-04-13 |
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