CA2501575A1 - Inhibitors of fatty acid amide hydrolase - Google Patents
Inhibitors of fatty acid amide hydrolase Download PDFInfo
- Publication number
- CA2501575A1 CA2501575A1 CA002501575A CA2501575A CA2501575A1 CA 2501575 A1 CA2501575 A1 CA 2501575A1 CA 002501575 A CA002501575 A CA 002501575A CA 2501575 A CA2501575 A CA 2501575A CA 2501575 A1 CA2501575 A1 CA 2501575A1
- Authority
- CA
- Canada
- Prior art keywords
- subunit
- group
- fatty acid
- mmol
- acid amide
- 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
- 239000003112 inhibitor Substances 0.000 title claims abstract description 48
- 108010046094 fatty-acid amide hydrolase Proteins 0.000 title claims description 61
- 102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 title claims description 57
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims description 42
- 230000005764 inhibitory process Effects 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- -1 chloro, hydroxyl Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 230000000694 effects Effects 0.000 abstract description 15
- 230000002860 competitive effect Effects 0.000 abstract description 11
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 9
- 150000002916 oxazoles Chemical class 0.000 abstract description 5
- 230000006872 improvement Effects 0.000 abstract description 3
- 150000004866 oxadiazoles Chemical class 0.000 abstract description 3
- 150000004867 thiadiazoles Chemical class 0.000 abstract description 3
- 150000003557 thiazoles Chemical class 0.000 abstract description 3
- 102100027297 Fatty acid 2-hydroxylase Human genes 0.000 abstract 3
- 101000937693 Homo sapiens Fatty acid 2-hydroxylase Proteins 0.000 abstract 3
- 101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 79
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 44
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 229910052681 coesite Inorganic materials 0.000 description 38
- 229910052906 cristobalite Inorganic materials 0.000 description 38
- 229910052682 stishovite Inorganic materials 0.000 description 38
- 229910052905 tridymite Inorganic materials 0.000 description 38
- 230000002829 reductive effect Effects 0.000 description 30
- 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 25
- 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
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 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
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 17
- 239000011592 zinc chloride Substances 0.000 description 16
- 235000005074 zinc chloride Nutrition 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 15
- 229910017974 NH40H Inorganic materials 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 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 8
- 101150041968 CDC13 gene Proteins 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 244000309464 bull Species 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 239000000377 silicon dioxide Substances 0.000 description 6
- 235000012239 silicon dioxide Nutrition 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
- 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-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
- 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 4
- 125000005313 fatty acid group Chemical group 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 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
- DOZFAFYEXMLJRD-UHFFFAOYSA-N 1-(4-pyridin-2-yl-1,3-oxazol-2-yl)octadec-9-en-1-one Chemical compound O1C(C(=O)CCCCCCCC=CCCCCCCCC)=NC(C=2N=CC=CC=2)=C1 DOZFAFYEXMLJRD-UHFFFAOYSA-N 0.000 description 3
- JIVKXULXTMWQMJ-UHFFFAOYSA-N 1-(4-pyridin-3-yl-1,3-oxazol-2-yl)octadec-9-en-1-one Chemical compound O1C(C(=O)CCCCCCCC=CCCCCCCCC)=NC(C=2C=NC=CC=2)=C1 JIVKXULXTMWQMJ-UHFFFAOYSA-N 0.000 description 3
- XWRIDDGXCXSSNJ-UHFFFAOYSA-N 1-(4-pyridin-4-yl-1,3-oxazol-2-yl)octadec-9-en-1-one Chemical compound O1C(C(=O)CCCCCCCC=CCCCCCCCC)=NC(C=2C=CN=CC=2)=C1 XWRIDDGXCXSSNJ-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
- 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
- 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 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
- 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 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
- 150000002430 hydrocarbons Chemical group 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
- 230000003389 potentiating effect Effects 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 2
- 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
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- 102000004157 Hydrolases Human genes 0.000 description 2
- 108090000604 Hydrolases Proteins 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- KHOZXYSECXUORA-UHFFFAOYSA-N dec-9-ynoic acid Chemical compound OC(=O)CCCCCCCC#C KHOZXYSECXUORA-UHFFFAOYSA-N 0.000 description 2
- 239000003940 fatty acid amidase inhibitor Substances 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 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
- 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
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 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
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 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
- NOUXLRBJQCWNDM-QXMHVHEDSA-N (Z)-N-methoxynonadec-9-enamide Chemical compound CCCCCCCCC/C=C\CCCCCCCC(=O)NOC NOUXLRBJQCWNDM-QXMHVHEDSA-N 0.000 description 1
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- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
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- 210000000170 cell membrane Anatomy 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
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 238000010651 palladium-catalyzed cross coupling reaction Methods 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
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- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 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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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- 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
-
- 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
- A61K31/425—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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (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)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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| US41724702P | 2002-10-08 | 2002-10-08 | |
| US60/417,247 | 2002-10-08 | ||
| PCT/US2003/031975 WO2004033652A2 (en) | 2002-10-08 | 2003-10-08 | Inhibitors of fatty acid amide hydrolase |
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| CA2501575A1 true CA2501575A1 (en) | 2004-04-22 |
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Family Applications (1)
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| CA002501575A Abandoned CA2501575A1 (en) | 2002-10-08 | 2003-10-08 | Inhibitors of fatty acid amide hydrolase |
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| JP (1) | JP4628789B2 (enExample) |
| KR (1) | KR20050070041A (enExample) |
| CN (1) | CN1703407A (enExample) |
| AT (1) | ATE431342T1 (enExample) |
| AU (1) | AU2003275493A1 (enExample) |
| BR (1) | BR0314980A (enExample) |
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| MX (1) | MXPA05003762A (enExample) |
| WO (1) | WO2004033652A2 (enExample) |
| ZA (1) | ZA200501837B (enExample) |
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| US6462054B1 (en) * | 2000-03-27 | 2002-10-08 | The Scripps Research Institute | Inhibitors of fatty acid amide hydrolase |
| DE60327640D1 (enExample) | 2002-10-08 | 2009-06-25 | Scripps Research Inst | |
| 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 |
| US7351724B2 (en) | 2004-10-15 | 2008-04-01 | The Scripps Research Institute | Oxadiazole ketone inhibitors of fatty acid amide hydrolase |
| PL2937341T3 (pl) | 2004-12-30 | 2017-11-30 | Janssen Pharmaceutica N.V. | Pochodne fenyloamidowe kwasu 4-(benzylo)-piperazyno-1-karboksylowego oraz związki powiązane, jako modulatory hydrolazy amidu kwasu tłuszczowego (FAAH) do leczenia lęku, bólu i innych schorzeń |
| PE20070099A1 (es) | 2005-06-30 | 2007-02-06 | Janssen Pharmaceutica Nv | N-heteroarilpiperazinil ureas como moduladores de la amida hidrolasa del acido graso |
| US20090111778A1 (en) | 2005-11-18 | 2009-04-30 | Richard Apodaca | 2-Keto-Oxazoles as Modulators of Fatty Acid Amide Hydrolase |
| WO2007098142A2 (en) | 2006-02-17 | 2007-08-30 | The Scripps Research Institute | Oxazole ketones as modulators of fatty acid amide hydrolase |
| WO2008013963A2 (en) | 2006-07-28 | 2008-01-31 | University Of Connecticut | Fatty acid amide hydrolase inhibitors |
| WO2008030532A2 (en) * | 2006-09-08 | 2008-03-13 | The Scripps Research Institute | Substituted oxazole ketone modulators of fatty acid amide hydrolase |
| AU2008257154B2 (en) * | 2007-05-25 | 2014-03-06 | The Scripps Research Institute | Tetracyclic inhibitors of fatty acid amide hydrolase |
| EP2161997A4 (en) * | 2007-05-31 | 2011-04-06 | Scripps Research Inst | TRICYCLIC INHIBITORS OF FATTY ACID AMIDHYDROLASE |
| EP2254415B1 (en) | 2008-02-19 | 2013-01-23 | Janssen Pharmaceutica, N.V. | Aryl-hydroxyethylamino-pyrimidines and triazines as modulators of fatty acid amide hydrolase |
| US20110184026A1 (en) * | 2008-06-19 | 2011-07-28 | Boger Dale L | C4-substituted alpha-keto oxazoles |
| US8987312B2 (en) | 2008-07-09 | 2015-03-24 | The Scripps Research Institute | Alpha-keto heterocycles as FAAH inhibitors |
| US8673941B2 (en) | 2008-08-04 | 2014-03-18 | Merck Sharp & Dohme Corp. | Oxazole derivatives useful as inhibitors of FAAH |
| WO2010068453A1 (en) | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | 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 |
| AU2009330821B2 (en) * | 2008-12-24 | 2015-06-11 | Bial - Portela & Ca, S.A. | Pharmaceutical compounds |
| 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 |
| WO2010141809A1 (en) | 2009-06-05 | 2010-12-09 | Janssen Pharmaceutica Nv | Aryl-substituted heterocyclic urea modulators of fatty acid amide hydrolase |
| WO2010141817A1 (en) | 2009-06-05 | 2010-12-09 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| WO2011022348A1 (en) | 2009-08-18 | 2011-02-24 | Janssen Pharmaceutica Nv | Ethylene diamine modulators of fatty acid amide hydrolase |
| AU2010293429B2 (en) | 2009-09-09 | 2015-12-17 | Sumitomo Dainippon Pharma Co., Ltd. | 8-oxodihydropurine derivative |
| CN102647984B (zh) | 2009-10-02 | 2015-03-25 | 埃维克辛公司 | 抗炎症的2-羰基噻唑和2-羰基恶唑 |
| US20120225097A1 (en) | 2009-11-12 | 2012-09-06 | Hawryluk Natalie A | Piperazinecarboxamide derivative useful as a modulator of fatty acid amide hydrolase (faah) |
| US20130150346A1 (en) | 2010-01-08 | 2013-06-13 | Quest Ventures Ltd. | Use of FAAH Inhibitors for Treating Parkinson's Disease and Restless Legs Syndrome |
| KR20120123691A (ko) * | 2010-01-28 | 2012-11-09 | 머크 샤프 앤드 돔 코포레이션 | 통증 및 기타의 적응증의 치료를 위한 제약 조성물 |
| WO2011112828A1 (en) | 2010-03-12 | 2011-09-15 | Omeros Corporation | Pde10 inhibitors and related compositions and methods |
| WO2011123719A2 (en) | 2010-03-31 | 2011-10-06 | Ironwood Pharmaceuticals, Inc. | Use of faah inhibitors for treating abdominal, visceral and pelvic pain |
| WO2011133444A1 (en) | 2010-04-21 | 2011-10-27 | Merck Sharp & Dohme Corp. | Substituted pyrimidines |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| BR112013004585B1 (pt) * | 2010-09-20 | 2021-09-08 | Merck Sharp & Dohme Corp | Lipídeo catiônico, composição de lnp, e, uso de um lipídeo catiônico |
| 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 |
| ES2648188T3 (es) * | 2012-02-17 | 2017-12-29 | Epitech Group S.P.A. | Composiciones y métodos para la modulación de amidasas específicas para N-aciletanolaminas para ser usadas en la terapia de enfermedades inflamatorias |
| US20150376161A1 (en) | 2013-01-29 | 2015-12-31 | Avexxin As | Antiiflammatory and antitumor 2-oxothiazoles abd 2-oxothiophenes compounds |
| NZ719916A (en) | 2013-11-01 | 2017-09-29 | Merial Inc | Antiparasitic and pesticidal isoxazoline compounds |
| NZ630810A (en) | 2014-04-28 | 2016-03-31 | Omeros Corp | Processes and intermediates for the preparation of a pde10 inhibitor |
| NZ630803A (en) | 2014-04-28 | 2016-03-31 | Omeros Corp | Optically active pde10 inhibitor |
| GB201413695D0 (en) | 2014-08-01 | 2014-09-17 | Avexxin As | Compound |
| WO2016160168A1 (en) * | 2015-02-20 | 2016-10-06 | Cytec Industries Inc. | Aliphatic-aromatic heterocyclic compounds and uses thereof in metal extractant compositions |
| RU2017134509A (ru) | 2015-04-24 | 2019-04-04 | Омерос Корпорейшн | Ингибиторы pde10 и соответствующие композиции и способы |
| 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 . |
| US5821371A (en) * | 1994-10-24 | 1998-10-13 | Eli Lilly And Comany | 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 |
| DE60327640D1 (enExample) | 2002-10-08 | 2009-06-25 | Scripps Research Inst |
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2003
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- 2003-10-08 EA EA200500633A patent/EA008767B1/ru unknown
- 2003-10-08 AT AT03759771T patent/ATE431342T1/de not_active IP Right Cessation
- 2003-10-08 EP EP03759771A patent/EP1549624B1/en not_active Expired - Lifetime
- 2003-10-08 CN CNA2003801009944A patent/CN1703407A/zh active Pending
- 2003-10-08 WO PCT/US2003/031975 patent/WO2004033652A2/en not_active Ceased
- 2003-10-08 CA CA002501575A patent/CA2501575A1/en not_active Abandoned
- 2003-10-08 US US10/528,552 patent/US7662971B2/en not_active Expired - Fee Related
- 2003-10-08 EP EP09006391A patent/EP2093220A3/en not_active Withdrawn
- 2003-10-08 AU AU2003275493A patent/AU2003275493A1/en not_active Abandoned
- 2003-10-08 ES ES03759771T patent/ES2325686T3/es not_active Expired - Lifetime
- 2003-10-08 JP JP2004543576A patent/JP4628789B2/ja not_active Expired - Fee Related
- 2003-10-08 BR BR0314980-3A patent/BR0314980A/pt not_active IP Right Cessation
- 2003-10-08 KR KR1020057006019A patent/KR20050070041A/ko not_active Withdrawn
- 2003-10-08 MX MXPA05003762A patent/MXPA05003762A/es not_active Application Discontinuation
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2005
- 2005-03-03 ZA ZA200501837A patent/ZA200501837B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2093220A3 (en) | 2009-11-11 |
| EA008767B1 (ru) | 2007-08-31 |
| EP1549624B1 (en) | 2009-05-13 |
| KR20050070041A (ko) | 2005-07-05 |
| WO2004033652A2 (en) | 2004-04-22 |
| EA200500633A1 (ru) | 2005-10-27 |
| JP2006502229A (ja) | 2006-01-19 |
| EP2093220A2 (en) | 2009-08-26 |
| EP1549624A2 (en) | 2005-07-06 |
| MXPA05003762A (es) | 2005-07-22 |
| ZA200501837B (en) | 2006-06-28 |
| ES2325686T3 (es) | 2009-09-14 |
| JP4628789B2 (ja) | 2011-02-09 |
| EP1549624A4 (en) | 2006-09-20 |
| BR0314980A (pt) | 2005-08-09 |
| AU2003275493A1 (en) | 2004-05-04 |
| US20060111359A1 (en) | 2006-05-25 |
| DE60327640D1 (enExample) | 2009-06-25 |
| US7662971B2 (en) | 2010-02-16 |
| ATE431342T1 (de) | 2009-05-15 |
| CN1703407A (zh) | 2005-11-30 |
| WO2004033652A3 (en) | 2004-09-16 |
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| FZDE | Discontinued |