ES2325686T3 - Inhibidores de amido-hidrolasa de acido graso. - Google Patents
Inhibidores de amido-hidrolasa de acido graso. Download PDFInfo
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- ES2325686T3 ES2325686T3 ES03759771T ES03759771T ES2325686T3 ES 2325686 T3 ES2325686 T3 ES 2325686T3 ES 03759771 T ES03759771 T ES 03759771T ES 03759771 T ES03759771 T ES 03759771T ES 2325686 T3 ES2325686 T3 ES 2325686T3
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- mmol
- fatty acid
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 33
- 239000000194 fatty acid Substances 0.000 title claims abstract description 33
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 33
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 32
- 239000003112 inhibitor Substances 0.000 title claims description 41
- 108090000531 Amidohydrolases Proteins 0.000 claims abstract description 26
- 102000004092 Amidohydrolases Human genes 0.000 claims abstract description 26
- 230000005764 inhibitory process Effects 0.000 claims abstract description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 23
- -1 chloro, hydroxyl Chemical group 0.000 claims abstract description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 15
- 229910052757 nitrogen Chemical group 0.000 claims abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004429 atom Chemical group 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000011593 sulfur Substances 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 230000000694 effects Effects 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000004042 amidohydrolase inhibitor Substances 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 88
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 82
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 43
- 229910052681 coesite Inorganic materials 0.000 description 41
- 229910052906 cristobalite Inorganic materials 0.000 description 41
- 239000000377 silicon dioxide Substances 0.000 description 41
- 235000012239 silicon dioxide Nutrition 0.000 description 41
- 229910052682 stishovite Inorganic materials 0.000 description 41
- 229910052905 tridymite Inorganic materials 0.000 description 41
- 238000000034 method Methods 0.000 description 38
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 36
- 238000004440 column chromatography Methods 0.000 description 28
- 239000000843 powder Substances 0.000 description 28
- 239000000463 material Substances 0.000 description 26
- 229920006395 saturated elastomer Polymers 0.000 description 26
- LUMKXMDGONYZHO-UHFFFAOYSA-N 5-pyridin-2-yl-1,3-oxazole Chemical compound O1C=NC=C1C1=CC=CC=N1 LUMKXMDGONYZHO-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 239000007832 Na2SO4 Substances 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- 235000019439 ethyl acetate Nutrition 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 18
- ILOIOIGZFHGSMS-UHFFFAOYSA-N 7-phenyl-1-(5-pyridin-2-yl-1,3-oxazol-2-yl)heptan-1-one Chemical compound N=1C=C(C=2N=CC=CC=2)OC=1C(=O)CCCCCCC1=CC=CC=C1 ILOIOIGZFHGSMS-UHFFFAOYSA-N 0.000 description 17
- 238000003818 flash chromatography Methods 0.000 description 17
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000000460 chlorine Chemical group 0.000 description 11
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- REOYOKXLUFHOBV-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-piperidin-1-ylpyrazole-3-carboxamide;hydron;chloride Chemical compound Cl.CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 REOYOKXLUFHOBV-UHFFFAOYSA-N 0.000 description 9
- 229910004298 SiO 2 Inorganic materials 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000002860 competitive effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 244000309464 bull Species 0.000 description 7
- 239000003940 fatty acid amidase inhibitor Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000011592 zinc chloride Substances 0.000 description 7
- 235000005074 zinc chloride Nutrition 0.000 description 7
- ROAHUIFQLRHKEY-UHFFFAOYSA-N 5-(1,3-thiazol-2-yl)-1,3-oxazole Chemical compound C1=CSC(C=2OC=NC=2)=N1 ROAHUIFQLRHKEY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 125000002971 oxazolyl group Chemical group 0.000 description 5
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical compound C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000005313 fatty acid group Chemical group 0.000 description 4
- 108010046094 fatty-acid amide hydrolase Proteins 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JPZIIIRVMJASPM-UHFFFAOYSA-N 1-(1,3,4-oxadiazol-2-yl)octadec-9-en-1-one Chemical compound CCCCCCCCC=CCCCCCCCC(=O)C1=NN=CO1 JPZIIIRVMJASPM-UHFFFAOYSA-N 0.000 description 3
- OGPJTMSGDUTXCW-UHFFFAOYSA-N 1-(1,3,4-thiadiazol-2-yl)octadec-9-en-1-one Chemical compound CCCCCCCCC=CCCCCCCCC(=O)C1=NN=CS1 OGPJTMSGDUTXCW-UHFFFAOYSA-N 0.000 description 3
- GGPJDZCXDVTNQT-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)butan-1-one Chemical compound O1C(C(=O)CCC)=NC=C1C1=CC=CC=N1 GGPJDZCXDVTNQT-UHFFFAOYSA-N 0.000 description 3
- FPPLZHMASKIGTJ-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)decan-1-one Chemical compound O1C(C(=O)CCCCCCCCC)=NC=C1C1=CC=CC=N1 FPPLZHMASKIGTJ-UHFFFAOYSA-N 0.000 description 3
- VESZWTBYTDWAEO-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)dodecan-1-one Chemical compound O1C(C(=O)CCCCCCCCCCC)=NC=C1C1=CC=CC=N1 VESZWTBYTDWAEO-UHFFFAOYSA-N 0.000 description 3
- UZVWXZPPYMTLQE-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)heptan-1-one Chemical compound O1C(C(=O)CCCCCC)=NC=C1C1=CC=CC=N1 UZVWXZPPYMTLQE-UHFFFAOYSA-N 0.000 description 3
- PCWWRGIJFHIOHI-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)hexadecan-1-one Chemical compound O1C(C(=O)CCCCCCCCCCCCCCC)=NC=C1C1=CC=CC=N1 PCWWRGIJFHIOHI-UHFFFAOYSA-N 0.000 description 3
- IADPDKBSCXXBSP-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)hexan-1-one Chemical compound O1C(C(=O)CCCCC)=NC=C1C1=CC=CC=N1 IADPDKBSCXXBSP-UHFFFAOYSA-N 0.000 description 3
- RYEVVZKCCJNESX-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)nonan-1-one Chemical compound O1C(C(=O)CCCCCCCC)=NC=C1C1=CC=CC=N1 RYEVVZKCCJNESX-UHFFFAOYSA-N 0.000 description 3
- FSLIASFBWRGZPB-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)octadecan-1-one Chemical compound O1C(C(=O)CCCCCCCCCCCCCCCCC)=NC=C1C1=CC=CC=N1 FSLIASFBWRGZPB-UHFFFAOYSA-N 0.000 description 3
- VLJKBQYNIDBQEJ-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)octan-1-one Chemical compound O1C(C(=O)CCCCCCC)=NC=C1C1=CC=CC=N1 VLJKBQYNIDBQEJ-UHFFFAOYSA-N 0.000 description 3
- ZGJFSRIJAXSNIH-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)pentan-1-one Chemical compound O1C(C(=O)CCCC)=NC=C1C1=CC=CC=N1 ZGJFSRIJAXSNIH-UHFFFAOYSA-N 0.000 description 3
- NITIZFVXASLZNL-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)propan-1-one Chemical compound O1C(C(=O)CC)=NC=C1C1=CC=CC=N1 NITIZFVXASLZNL-UHFFFAOYSA-N 0.000 description 3
- CZDQFSCARAYQAZ-UHFFFAOYSA-N 1-(5-pyridin-2-yl-1,3-oxazol-2-yl)tetradecan-1-one Chemical compound O1C(C(=O)CCCCCCCCCCCCC)=NC=C1C1=CC=CC=N1 CZDQFSCARAYQAZ-UHFFFAOYSA-N 0.000 description 3
- YVORRVFKHZLJGZ-UHFFFAOYSA-N 4,5-Dimethyloxazole Chemical compound CC=1N=COC=1C YVORRVFKHZLJGZ-UHFFFAOYSA-N 0.000 description 3
- RDVIQCGECBBHNA-UHFFFAOYSA-N 5-(1-methylimidazol-2-yl)-1,3-oxazole Chemical compound CN1C=CN=C1C1=CN=CO1 RDVIQCGECBBHNA-UHFFFAOYSA-N 0.000 description 3
- ICIMMICEDXGNOA-UHFFFAOYSA-N 5-thiophen-3-yl-1,3-oxazole Chemical compound S1C=CC(C=2OC=NC=2)=C1 ICIMMICEDXGNOA-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 125000003431 oxalo group Chemical group 0.000 description 3
- RCRCTBLIHCHWDZ-UHFFFAOYSA-N 2-Arachidonoyl Glycerol Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)CO RCRCTBLIHCHWDZ-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- ODKHOKLXMBWVOQ-UHFFFAOYSA-N 4,5-diphenyl-1,3-oxazole Chemical compound O1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ODKHOKLXMBWVOQ-UHFFFAOYSA-N 0.000 description 2
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- ABYBUOHSJCFYNC-UHFFFAOYSA-N 5-(furan-3-yl)-1,3-oxazole Chemical compound O1C=CC(C=2OC=NC=2)=C1 ABYBUOHSJCFYNC-UHFFFAOYSA-N 0.000 description 2
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 108090000353 Histone deacetylase Proteins 0.000 description 2
- 102000003964 Histone deacetylase Human genes 0.000 description 2
- 101000852815 Homo sapiens Insulin receptor Proteins 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 150000002916 oxazoles Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RGTIBVZDHOMOKC-UHFFFAOYSA-N stearolic acid Chemical compound CCCCCCCCC#CCCCCCCCC(O)=O RGTIBVZDHOMOKC-UHFFFAOYSA-N 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- OOXRAGYSSZWMAE-DOFZRALJSA-N (5z,8z,11z,14z)-icosa-5,8,11,14-tetraen-1-amine Chemical class CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCN OOXRAGYSSZWMAE-DOFZRALJSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 1
- ABJVJNOVNSCXRT-UHFFFAOYSA-N 1-(1,3,4-oxadiazol-2-yl)octadec-9-en-1-ol Chemical compound CCCCCCCCC=CCCCCCCCC(O)C1=NN=CO1 ABJVJNOVNSCXRT-UHFFFAOYSA-N 0.000 description 1
- QIBXDPZFAVJEAI-UHFFFAOYSA-N 1-(1,3,4-thiadiazol-2-yl)octadec-9-en-1-ol Chemical compound CCCCCCCCC=CCCCCCCCC(O)C1=NN=CS1 QIBXDPZFAVJEAI-UHFFFAOYSA-N 0.000 description 1
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- 238000003556 assay Methods 0.000 description 1
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- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
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- OFIDNKMQBYGNIW-ZKWNWVNESA-N methyl arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC OFIDNKMQBYGNIW-ZKWNWVNESA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
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- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- NRWMBHYHFFGEEC-UHFFFAOYSA-N selachyl alcohol Natural products CCCCCCCCC=CCCCCCCCCOCC(O)CO NRWMBHYHFFGEEC-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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| US6462054B1 (en) * | 2000-03-27 | 2002-10-08 | The Scripps Research Institute | Inhibitors of fatty acid amide hydrolase |
| AU2003275493A1 (en) | 2002-10-08 | 2004-05-04 | The Scripps Research Institute | Inhibitors of fatty acid amide hydrolase |
| FR2865205B1 (fr) * | 2004-01-16 | 2006-02-24 | Sanofi Synthelabo | Derives de type aryloxyalkylcarbamates, leur preparation et leur application en therapeutique |
| FR2866886B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-akylcarbamates, leur preparation et leur application en therapeutique |
| DE102004039326A1 (de) * | 2004-08-12 | 2006-02-16 | Abbott Gmbh & Co. Kg | Neue medizinische Verwendungen und Verfahren |
| WO2006044617A1 (en) * | 2004-10-15 | 2006-04-27 | The Scripps Research Institute | Oxadiazole ketone inhibitors of fatty acid amide hydrolase |
| 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 |
| US7541359B2 (en) | 2005-06-30 | 2009-06-02 | Janssen Pharmaceutica N.V. | N-heteroarylpiperazinyl ureas as modulators of fatty acid amide hydrolase |
| WO2007061862A2 (en) | 2005-11-18 | 2007-05-31 | Janssen Pharmaceutica N.V. | 2-keto-oxazoles as modulators of fatty acid amide hydrolase |
| US7915270B2 (en) * | 2006-02-17 | 2011-03-29 | The Scripps Research Institute | Oxazole ketones as modulators of fatty acid amide hydrolase |
| EP2051964A4 (en) * | 2006-07-28 | 2012-03-07 | Univ Connecticut | INHIBITORS OF FATTY ACID AMIDHYDROLASE |
| US8268817B2 (en) * | 2006-09-08 | 2012-09-18 | The Scripps Research Institute | Substituted oxazole ketone modulators of fatty acid amide hydrolase |
| JP5406828B2 (ja) * | 2007-05-25 | 2014-02-05 | ザ スクリプス リサーチ インスティテュート | 脂肪酸アミドヒドロラーゼの四環式阻害剤 |
| AU2008260496A1 (en) * | 2007-05-31 | 2008-12-11 | The Scripps Research Institute | Tricyclic inhibitors of fatty acid amide hydrolase |
| CA2714743C (en) * | 2008-02-19 | 2017-01-17 | Janssen Pharmaceutica N.V. | Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase |
| WO2009154785A2 (en) * | 2008-06-19 | 2009-12-23 | The Scripps Research Institute | C4-substituted alpha-keto oxazoles |
| WO2010005572A2 (en) * | 2008-07-09 | 2010-01-14 | The Scripps Research Institute | Alpha-keto heterocycles as faah inhibitors |
| JP5698666B2 (ja) * | 2008-08-04 | 2015-04-08 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | Ｆａａｈの阻害剤として有用なオキサゾール誘導体 |
| US8461159B2 (en) | 2008-11-25 | 2013-06-11 | Jannsen Pharmaceutica BV | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| WO2010068452A1 (en) | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| TWI469979B (zh) * | 2008-12-24 | 2015-01-21 | Bial Portela & Ca Sa | 脂肪酸醯胺水解酶(faah)抑制劑、以及其藥學組成物與用途 |
| AR076687A1 (es) * | 2009-05-18 | 2011-06-29 | Infinity Pharmaceuticals Inc | Isoxazolinas como inhibidores de la amidahidrolasa de acidos grasos y com-posiciones farmaceuticas que los contienen |
| US20120083476A1 (en) | 2009-06-05 | 2012-04-05 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| WO2010141809A1 (en) | 2009-06-05 | 2010-12-09 | Janssen Pharmaceutica Nv | Aryl-substituted heterocyclic urea modulators of fatty acid amide hydrolase |
| US8906914B2 (en) | 2009-08-18 | 2014-12-09 | Janssen Pharmaceutica Nv | Ethylene diamine modulators of fatty acid hydrolase |
| US8735406B2 (en) | 2009-09-09 | 2014-05-27 | Dainippon Sumitomo Pharma Co., Ltd. | 8-oxodihydropurine derivative |
| KR20190082985A (ko) | 2009-10-02 | 2019-07-10 | 아벡신 에이에스 | 소염제 2-옥소티아졸 및 2-옥소옥사졸 |
| US20120225097A1 (en) | 2009-11-12 | 2012-09-06 | Hawryluk Natalie A | Piperazinecarboxamide derivative useful as a modulator of fatty acid amide hydrolase (faah) |
| WO2011085216A2 (en) | 2010-01-08 | 2011-07-14 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating parkinson's disease and restless legs syndrome |
| AU2011209754A1 (en) * | 2010-01-28 | 2012-07-26 | Merck Sharp & Dohme Corp. | Pharmaceutical compositions for the treatment of pain and other indicatons |
| ES2742195T3 (es) | 2010-03-12 | 2020-02-13 | Omeros Corp | Inhibidores de PDE10 y composiciones y métodos relacionados |
| US20130224151A1 (en) | 2010-03-31 | 2013-08-29 | United States Of America | Use of FAAH Inhibitors for Treating Abdominal, Visceral and Pelvic Pain |
| US9006433B2 (en) | 2010-04-21 | 2015-04-14 | Merck Sharp & Dohme Corp. | Substituted pyrimidines |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| EP3943114B1 (en) * | 2010-09-20 | 2024-08-07 | Sirna Therapeutics, Inc. | Novel low molecular weight cationic lipids for oligonucleotide delivery |
| CN102964311B (zh) * | 2011-09-01 | 2016-03-09 | 大丰海嘉诺药业有限公司 | 一种合成4-甲基-5-烷氧基噁唑的方法 |
| CN104244948B (zh) * | 2012-02-17 | 2016-11-16 | 爱普泰克集团有限公司 | 在炎症性疾病的治疗中使用的用于调节n-酰基乙醇胺的特异性酰胺酶的组合物和方法 |
| AU2014211489A1 (en) | 2013-01-29 | 2015-08-13 | Avexxin As | Antiinflammatory and antitumor 2-oxothiazoles and 2-oxothiophenes compounds |
| AU2014342241B2 (en) | 2013-11-01 | 2017-09-14 | Boehringer Ingelheim Animal Health USA Inc. | Antiparasitic and pesticidal isoxazoline compounds |
| NZ716494A (en) | 2014-04-28 | 2017-07-28 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
| NZ716462A (en) | 2014-04-28 | 2017-11-24 | Omeros Corp | Optically active pde10 inhibitor |
| GB201413695D0 (en) | 2014-08-01 | 2014-09-17 | Avexxin As | Compound |
| US20160244860A1 (en) * | 2015-02-20 | 2016-08-25 | Cytec Industries Inc. | Aliphatic-aromatic heterocyclic compounds and uses thereof in metal extractant compositions |
| AU2016250843A1 (en) | 2015-04-24 | 2017-10-12 | Omeros Corporation | PDE10 inhibitors and related compositions and methods |
| EP3095787A1 (en) * | 2015-05-22 | 2016-11-23 | Universiteit Leiden | Pharmaceutically active compounds as dag-lipase inhibitors |
| WO2017079678A1 (en) | 2015-11-04 | 2017-05-11 | Omeros Corporation | Solid state forms of a pde10 inhibitor |
| GB201604318D0 (en) | 2016-03-14 | 2016-04-27 | Avexxin As | Combination therapy |
| JP7531351B2 (ja) | 2019-11-13 | 2024-08-09 | 東京エレクトロン株式会社 | 基板処理方法、基板処理装置、および基板処理システム |
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| MA19269A1 (fr) * | 1980-09-16 | 1982-04-01 | Lilly Co Eli | Perfectionnement relatif a des derives de n-arylbenzamides . |
| US5929247A (en) * | 1994-10-24 | 1999-07-27 | Eli Lilly And Company | Heterocyclic compounds and their preparation and use |
| TW200404789A (en) * | 1999-03-15 | 2004-04-01 | Axys Pharm Inc | Novel compounds and compositions as protease inhibitors |
| US6462054B1 (en) | 2000-03-27 | 2002-10-08 | The Scripps Research Institute | Inhibitors of fatty acid amide hydrolase |
| US20020103192A1 (en) * | 2000-10-26 | 2002-08-01 | Curtin Michael L. | Inhibitors of histone deacetylase |
| AU2003275493A1 (en) | 2002-10-08 | 2004-05-04 | The Scripps Research Institute | Inhibitors of fatty acid amide hydrolase |
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| MXPA05003762A (es) | 2005-07-22 |
| EP1549624A4 (en) | 2006-09-20 |
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| AU2003275493A1 (en) | 2004-05-04 |
| ZA200501837B (en) | 2006-06-28 |
| EP2093220A3 (en) | 2009-11-11 |
| EP1549624A2 (en) | 2005-07-06 |
| WO2004033652A2 (en) | 2004-04-22 |
| EA200500633A1 (ru) | 2005-10-27 |
| US7662971B2 (en) | 2010-02-16 |
| US20060111359A1 (en) | 2006-05-25 |
| BR0314980A (pt) | 2005-08-09 |
| KR20050070041A (ko) | 2005-07-05 |
| CA2501575A1 (en) | 2004-04-22 |
| EA008767B1 (ru) | 2007-08-31 |
| EP1549624B1 (en) | 2009-05-13 |
| JP2006502229A (ja) | 2006-01-19 |
| WO2004033652A3 (en) | 2004-09-16 |
| CN1703407A (zh) | 2005-11-30 |
| ATE431342T1 (de) | 2009-05-15 |
| EP2093220A2 (en) | 2009-08-26 |
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