UA124542C2 - Інгібітори magl - Google Patents
Інгібітори magl Download PDFInfo
- Publication number
- UA124542C2 UA124542C2 UAA201905620A UAA201905620A UA124542C2 UA 124542 C2 UA124542 C2 UA 124542C2 UA A201905620 A UAA201905620 A UA A201905620A UA A201905620 A UAA201905620 A UA A201905620A UA 124542 C2 UA124542 C2 UA 124542C2
- Authority
- UA
- Ukraine
- Prior art keywords
- pharmaceutically acceptable
- acceptable salt
- compound
- solvate
- formula
- Prior art date
Links
- 102100029814 Monoglyceride lipase Human genes 0.000 title abstract 2
- 101710116393 Monoglyceride lipase Proteins 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 783
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims description 737
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 241000750004 Nestor meridionalis Species 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
- 210000004243 sweat Anatomy 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 89
- 208000002193 Pain Diseases 0.000 abstract description 24
- 238000011282 treatment Methods 0.000 abstract description 15
- CWPIBZMCMRNFHK-UHFFFAOYSA-N piperazin-1-ium;carbamate Chemical class NC(O)=O.C1CNCCN1 CWPIBZMCMRNFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 235000002639 sodium chloride Nutrition 0.000 description 726
- 239000012453 solvate Substances 0.000 description 685
- -1 1-propyl (n-propyl) Chemical group 0.000 description 186
- 239000000243 solution Substances 0.000 description 143
- 229910052736 halogen Inorganic materials 0.000 description 112
- 150000002367 halogens Chemical class 0.000 description 110
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 102
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 100
- 238000000034 method Methods 0.000 description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 83
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- 238000003786 synthesis reaction Methods 0.000 description 69
- 230000015572 biosynthetic process Effects 0.000 description 66
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 description 62
- 239000012267 brine Substances 0.000 description 60
- 239000012044 organic layer Substances 0.000 description 60
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 60
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
- 238000002360 preparation method Methods 0.000 description 54
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
- 239000000741 silica gel Substances 0.000 description 52
- 229910002027 silica gel Inorganic materials 0.000 description 52
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 42
- 230000002829 reductive effect Effects 0.000 description 40
- 239000011541 reaction mixture Substances 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000003921 oil Substances 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 35
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 34
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 33
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
- 239000002253 acid Substances 0.000 description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 32
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 125000004432 carbon atom Chemical group C* 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 201000010099 disease Diseases 0.000 description 29
- 239000003814 drug Substances 0.000 description 29
- 125000001072 heteroaryl group Chemical group 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 28
- 125000003118 aryl group Chemical group 0.000 description 28
- 125000000753 cycloalkyl group Chemical group 0.000 description 28
- 239000000126 substance Substances 0.000 description 28
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
- 150000003254 radicals Chemical class 0.000 description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 23
- 241000722363 Piper Species 0.000 description 22
- 239000012043 crude product Substances 0.000 description 22
- 208000008795 neuromyelitis optica Diseases 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 229940124597 therapeutic agent Drugs 0.000 description 21
- 238000002953 preparative HPLC Methods 0.000 description 20
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 20
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 18
- 125000002947 alkylene group Chemical group 0.000 description 18
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 125000003710 aryl alkyl group Chemical group 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 208000035475 disorder Diseases 0.000 description 13
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- 125000003709 fluoroalkyl group Chemical group 0.000 description 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 13
- 239000003208 petroleum Substances 0.000 description 13
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000004450 alkenylene group Chemical group 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 11
- 229910000024 caesium carbonate Inorganic materials 0.000 description 11
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 10
- 239000003937 drug carrier Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 206010015037 epilepsy Diseases 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- 239000000443 aerosol Substances 0.000 description 8
- 150000007942 carboxylates Chemical class 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 201000006417 multiple sclerosis Diseases 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000011591 potassium Chemical class 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 7
- LZZVRRMMBYPJSZ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl piperazine-1-carboxylate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)N1CCNCC1 LZZVRRMMBYPJSZ-UHFFFAOYSA-N 0.000 description 6
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 6
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QHEMKYYZDDGHQP-UHFFFAOYSA-N tert-butyl 2-(6-bromo-2-fluoro-3-methylphenoxy)acetate Chemical compound BrC1=CC=C(C(=C1OCC(=O)OC(C)(C)C)F)C QHEMKYYZDDGHQP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- JQSJVDFGBIVAQI-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl piperazine-1-carboxylate 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(OC(=O)N1CCNCC1)C(F)(F)F JQSJVDFGBIVAQI-UHFFFAOYSA-N 0.000 description 5
- KFEHNXLFIGPWNB-UHFFFAOYSA-N 2-fluoro-4-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC(C(F)(F)F)=CC=C1C=O KFEHNXLFIGPWNB-UHFFFAOYSA-N 0.000 description 5
- 208000004998 Abdominal Pain Diseases 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 5
- 206010065390 Inflammatory pain Diseases 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 208000000323 Tourette Syndrome Diseases 0.000 description 5
- 208000016620 Tourette disease Diseases 0.000 description 5
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- 208000002551 irritable bowel syndrome Diseases 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
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- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 5
- XCKVXVZIVZYKFC-UHFFFAOYSA-N tert-butyl 4-[[3-fluoro-4-methyl-2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]methyl]piperazine-1-carboxylate Chemical compound C(C)(C)(C)OC(COC1=C(CN2CCN(CC2)C(=O)OC(C)(C)C)C=CC(=C1F)C)=O XCKVXVZIVZYKFC-UHFFFAOYSA-N 0.000 description 5
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- YHYNJGHMBMXAFB-UHFFFAOYSA-N 2-hydroxy-4-(trifluoromethyl)benzaldehyde Chemical compound OC1=CC(C(F)(F)F)=CC=C1C=O YHYNJGHMBMXAFB-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- 239000004471 Glycine Substances 0.000 description 4
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- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 4
- 239000000014 opioid analgesic Substances 0.000 description 4
- 239000001301 oxygen Chemical group 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
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- SDONMAYOYNUXFO-UHFFFAOYSA-N tert-butyl 4-[[3-fluoro-4-methyl-2-(trifluoromethylsulfonyloxy)phenyl]methyl]piperazine-1-carboxylate Chemical compound FC=1C(=C(CN2CCN(CC2)C(=O)OC(C)(C)C)C=CC=1C)OS(=O)(=O)C(F)(F)F SDONMAYOYNUXFO-UHFFFAOYSA-N 0.000 description 4
- LTPLDADXDHQQNG-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 4-[[3-fluoro-2-[2-(methanesulfonamido)-2-oxoethoxy]-4-methylphenyl]methyl]piperazine-1-carboxylate Chemical compound FC=1C(=C(CN2CCN(CC2)C(=O)OC(C(F)(F)F)C(F)(F)F)C=CC=1C)OCC(=O)NS(=O)(=O)C LTPLDADXDHQQNG-UHFFFAOYSA-N 0.000 description 3
- BLOZIOWIJIRSSE-UHFFFAOYSA-N 2-[2-fluoro-3-methyl-6-(piperazin-1-ylmethyl)phenoxy]acetic acid Chemical compound FC1=C(OCC(=O)O)C(=CC=C1C)CN1CCNCC1 BLOZIOWIJIRSSE-UHFFFAOYSA-N 0.000 description 3
- WZEZUJBZOJMIPX-UHFFFAOYSA-N 5-[2-(piperazin-1-ylmethyl)-5-(trifluoromethyl)phenyl]pentanoic acid hydrochloride Chemical compound Cl.OC(=O)CCCCc1cc(ccc1CN1CCNCC1)C(F)(F)F WZEZUJBZOJMIPX-UHFFFAOYSA-N 0.000 description 3
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- FCEUHENXNKJCCA-UHFFFAOYSA-N tert-butyl 4-[[3-chloro-2-[(1-ethoxycarbonylcyclopropyl)methoxy]-4-methylphenyl]methyl]piperazine-1-carboxylate Chemical compound ClC=1C(=C(CN2CCN(CC2)C(=O)OC(C)(C)C)C=CC=1C)OCC1(CC1)C(=O)OCC FCEUHENXNKJCCA-UHFFFAOYSA-N 0.000 description 1
- MWRBWPQBGGARAY-UHFFFAOYSA-M tert-butyl acetate;chlorozinc(1+) Chemical compound [Zn+]Cl.CC(C)(C)OC([CH2-])=O MWRBWPQBGGARAY-UHFFFAOYSA-M 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229960004380 tramadol Drugs 0.000 description 1
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000005455 trithianyl group Chemical group 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940093612 zein Drugs 0.000 description 1
- 239000005019 zein Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000016804 zinc Nutrition 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/195—Radicals derived from nitrogen analogues of carboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US201662423099P | 2016-11-16 | 2016-11-16 | |
| PCT/US2017/061868 WO2018093947A1 (en) | 2016-11-16 | 2017-11-15 | Magl inhibitors |
Publications (1)
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| UA124542C2 true UA124542C2 (uk) | 2021-10-05 |
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| UAA201905620A UA124542C2 (uk) | 2016-11-16 | 2017-11-15 | Інгібітори magl |
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| MX (1) | MX391117B (enExample) |
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| PE (1) | PE20191144A1 (enExample) |
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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. |
| US10450302B2 (en) | 2015-05-11 | 2019-10-22 | Lundbeck La Jolla Research Center, Inc. | Methods of treating inflammation or neuropathic pain |
| WO2018053447A1 (en) | 2016-09-19 | 2018-03-22 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
| WO2018093950A1 (en) | 2016-11-16 | 2018-05-24 | Abide Therapeutics, Inc. | Pharmaceutical formulations |
| JOP20190107A1 (ar) | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
| AU2017361257B2 (en) | 2016-11-16 | 2022-02-10 | H. Lundbeck A/S. | Crystalline forms of a MAGL inhibitor |
| LT3630744T (lt) | 2017-05-23 | 2023-03-10 | H. Lundbeck A/S | Pirazolo magl inhibitoriai |
| MX2020002251A (es) | 2017-08-29 | 2020-07-20 | Lundbeck La Jolla Research Center Inc | Compuestos espirociclicos y sus metodos de preparacion y uso. |
| 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 |
| EP3914589A4 (en) * | 2019-01-25 | 2022-11-30 | H. Lundbeck A/S | Methods of treating disease with magl inhibitors |
| CA3159391A1 (en) * | 2019-11-15 | 2021-05-20 | H. Lundbeck A/S | Crystalline forms of a magl inhibitor |
| IT202000007150A1 (it) * | 2020-04-03 | 2021-10-03 | Univ Pisa | Inibitori di monoacilglicerolo lipasi (magl) |
| IL297470A (en) | 2020-04-21 | 2022-12-01 | H Lundbeck As | Synthesis of a monoacylglycerol lipase inhibitor |
| US20250084065A1 (en) | 2021-12-29 | 2025-03-13 | Psy Therapeutics, Inc. | Inhibiting monoacylglycerol lipase (magl) |
| US12378219B2 (en) | 2022-05-04 | 2025-08-05 | H. Lundbeck A/S | Crystalline forms of a MAGL inhibitor |
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| FR1593586A (enExample) | 1967-10-17 | 1970-06-01 | ||
| JPS6183073A (ja) | 1984-10-01 | 1986-04-26 | Oki Electric Ind Co Ltd | 印字装置の用紙送り方法 |
| WO1989011794A1 (fr) | 1988-06-07 | 1989-12-14 | Rikagaku Kenkyusho | Inhibiteur de la croissance de plantes |
| ATE138365T1 (de) | 1991-11-27 | 1996-06-15 | Du Pont | Herbizide acylierte amino-(phenyl-oder-pyridinyl- oder thienyl-)phenyl derivate |
| AU1384795A (en) | 1993-12-22 | 1995-07-10 | Shell Internationale Research Maatschappij B.V. | Process for preparing carbamates |
| EP0863879A1 (en) | 1995-11-15 | 1998-09-16 | Zeneca Limited | Herbicidal substituted pyrazole compounds |
| WO1998000408A1 (en) | 1996-07-02 | 1998-01-08 | Novartis Ag | N-phenylimino heterocyclic derivatives and their use as herbicides |
| RU2167150C2 (ru) | 1998-03-25 | 2001-05-20 | Фокин Александр Васильевич | Полифторалкил-n-арилкарбаматы, обладающие антимикробной активностью |
| EP1226115A4 (en) | 1999-10-04 | 2006-03-15 | Univ New Jersey Med | NEW CARBAMATES AND UREES |
| EP1201298A1 (en) | 2000-10-24 | 2002-05-02 | Urea Casale S.A. | Carbamate condensation unit |
| DE10348022A1 (de) | 2003-10-15 | 2005-05-25 | Imtm Gmbh | Neue Dipeptidylpeptidase IV-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
| FR2864080B1 (fr) | 2003-12-23 | 2006-02-03 | Sanofi Synthelabo | Derives de 1-piperazine-et-1-homopiperazine-carboxylates, leur preparation et leur application en therapeutique |
| AU2003300702A1 (en) | 2003-12-31 | 2005-07-21 | Council Of Scientific And Industrial Research | Process for preparing carbamates |
| EP1716130A1 (en) | 2004-02-18 | 2006-11-02 | AstraZeneca AB | Acetylinic piperazine compounds and their use as metabotropic glutamate receptor antagonists |
| JP2008521768A (ja) | 2004-12-23 | 2008-06-26 | エフ．ホフマン−ラ ロシュ アーゲー | ヘテロ環式カルバミン酸誘導体、それらの製造及び医薬品としての使用 |
| EP2937341B1 (en) | 2004-12-30 | 2017-07-05 | Janssen Pharmaceutica N.V. | 4-(benzyl)-piperazine-1-carboxylic acid phenylamide derivatives and related compounds as modulators of fatty acid amide hydrolase (faah) for the treatment of anxiety, pain and other conditions |
| JP2009514935A (ja) * | 2005-11-05 | 2009-04-09 | アストラゼネカ・アクチエボラーグ | 新規化合物 |
| JP2009523729A (ja) | 2006-01-13 | 2009-06-25 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎の治療方法 |
| US8895745B2 (en) | 2006-12-22 | 2014-11-25 | Astex Therapeutics Limited | Bicyclic heterocyclic compounds as FGFR inhibitors |
| EP2124927A2 (en) | 2007-02-26 | 2009-12-02 | Kosan Biosciences Incorporated | Carbamate compounds |
| US8188098B2 (en) | 2008-05-19 | 2012-05-29 | Hoffmann-La Roche Inc. | GPR119 receptor agonists |
| AU2009270983A1 (en) | 2008-07-16 | 2010-01-21 | Schering Corporation | Bicyclic heterocycle derivatives and their use as GPCR modulators |
| AU2009314629B2 (en) | 2008-11-14 | 2014-09-25 | The Scripps Research Institute | Methods and compositions related to targeting monoacylglycerol lipase |
| JP2012521425A (ja) | 2009-03-23 | 2012-09-13 | Ｍｓｄ株式会社 | オーロラａ選択的阻害作用を有する新規アミノピリジン誘導体 |
| EP2421848A1 (en) * | 2009-04-22 | 2012-02-29 | Janssen Pharmaceutica N.V. | Azetidinyl diamides as monoacylglycerol lipase inhibitors |
| UA107791C2 (en) | 2009-05-05 | 2015-02-25 | Dow Agrosciences Llc | Pesticidal compositions |
| TWI506011B (zh) | 2009-11-03 | 2015-11-01 | Bayer Materialscience Ag | 在光聚合物調配物中作為添加劑之氟胺基甲酸酯 |
| FR2960875B1 (fr) * | 2010-06-04 | 2012-12-28 | Sanofi Aventis | Derives de carbamates d'hexafluoroisopropyle, leur preparation et leur application en therapeutique |
| MX350788B (es) * | 2012-01-06 | 2017-09-13 | Abide Therapeutics Inc | Compuestos de carbamato y preparación y uso de los mismos. |
| CA2860623A1 (en) | 2012-01-06 | 2013-07-11 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
| 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 |
| JP2014005245A (ja) * | 2012-06-26 | 2014-01-16 | Dainippon Sumitomo Pharma Co Ltd | 二環性ピリミジン誘導体を含有する医薬組成物 |
| US9551036B2 (en) | 2013-02-25 | 2017-01-24 | Whitehead Institute For Biomedical Research | Metabolic gene mesenchymal signatures and uses thereof |
| CA2917050A1 (en) * | 2013-07-03 | 2015-01-08 | Todd K. Jones | Pyrrolo-pyrrole carbamate and related organic compounds, pharmaceutical compositions, and medical uses thereof |
| US10570146B2 (en) * | 2014-07-25 | 2020-02-25 | Northeastern University | Urea/carbamates FAAH MAGL or dual FAAH/MAGL inhibitors and uses thereof |
| US9771341B2 (en) | 2015-03-18 | 2017-09-26 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
| WO2018053447A1 (en) * | 2016-09-19 | 2018-03-22 | Abide Therapeutics, Inc. | Piperazine carbamates and methods of making and using same |
| JOP20190105A1 (ar) * | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
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2017
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- 2017-11-15 EP EP17871753.4A patent/EP3541821A4/en not_active Withdrawn
- 2017-11-15 CA CA3043615A patent/CA3043615A1/en active Pending
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- 2017-11-15 WO PCT/US2017/061868 patent/WO2018093947A1/en not_active Ceased
- 2017-11-15 CR CR20190241A patent/CR20190241A/es unknown
- 2017-11-15 RU RU2019116512A patent/RU2754536C1/ru active
- 2017-11-15 UA UAA201905620A patent/UA124542C2/uk unknown
- 2017-11-15 AU AU2017361251A patent/AU2017361251B2/en not_active Ceased
- 2017-11-15 MA MA046857A patent/MA46857A/fr unknown
- 2017-11-15 AR ARP170103184A patent/AR110089A1/es not_active Application Discontinuation
- 2017-11-15 TN TNP/2019/000153A patent/TN2019000153A1/en unknown
- 2017-11-15 KR KR1020197016924A patent/KR20190077544A/ko not_active Abandoned
- 2017-11-15 CN CN201780083663.6A patent/CN110267963B/zh not_active Expired - Fee Related
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- 2017-11-15 JP JP2019523587A patent/JP7042547B2/ja active Active
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2019
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- 2019-05-17 ZA ZA201903100A patent/ZA201903100B/en unknown
Also Published As
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| UA125523C2 (uk) | Інгібітори magl | |
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