CA2606254A1 - Derives d'acide .beta.-amino - Google Patents
Derives d'acide .beta.-amino Download PDFInfo
- Publication number
- CA2606254A1 CA2606254A1 CA002606254A CA2606254A CA2606254A1 CA 2606254 A1 CA2606254 A1 CA 2606254A1 CA 002606254 A CA002606254 A CA 002606254A CA 2606254 A CA2606254 A CA 2606254A CA 2606254 A1 CA2606254 A1 CA 2606254A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- formula
- compound
- alkyl
- propanoic acid
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 208000002193 Pain Diseases 0.000 claims abstract description 62
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 239000012453 solvate Substances 0.000 claims abstract description 27
- 238000011282 treatment Methods 0.000 claims abstract description 20
- -1 -NR5R5 Chemical group 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 4
- 235000019260 propionic acid Nutrition 0.000 claims description 4
- XHOJQDSCSICOOX-QMMMGPOBSA-N (2s)-2-(azaniumylmethyl)-3-(3-bromophenyl)propanoate Chemical compound NC[C@@H](C(O)=O)CC1=CC=CC(Br)=C1 XHOJQDSCSICOOX-QMMMGPOBSA-N 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- ADYHVNFACLEIPS-UHFFFAOYSA-N 2-(aminomethyl)-3-(2,4,6-trimethylphenyl)propanoic acid Chemical compound CC1=CC(C)=C(CC(CN)C(O)=O)C(C)=C1 ADYHVNFACLEIPS-UHFFFAOYSA-N 0.000 claims description 3
- KYJQGIYPWGMRFG-UHFFFAOYSA-N 2-(aminomethyl)-3-(3,8-dimethoxynaphthalen-1-yl)propanoic acid Chemical compound COC1=CC=CC2=CC(OC)=CC(CC(CN)C(O)=O)=C21 KYJQGIYPWGMRFG-UHFFFAOYSA-N 0.000 claims description 3
- UBDBJOYVCUYTIQ-UHFFFAOYSA-N 2-(aminomethyl)-3-(4-hydroxyphenyl)propanoic acid Chemical compound NCC(C(O)=O)CC1=CC=C(O)C=C1 UBDBJOYVCUYTIQ-UHFFFAOYSA-N 0.000 claims description 3
- KZAMNECKBXDIKV-UHFFFAOYSA-N 2-(aminomethyl)-3-(4-methoxyphenyl)propanoic acid;2-(aminomethyl)-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoic acid Chemical compound COC1=CC=C(CC(CN)C(O)=O)C=C1.CC(C)(C)OC1=CC=C(CC(CN)C(O)=O)C=C1 KZAMNECKBXDIKV-UHFFFAOYSA-N 0.000 claims description 3
- BTLMAFGMHHKSHH-UHFFFAOYSA-N 2-(azaniumylmethyl)-3-(1,3-benzodioxol-5-yl)propanoate Chemical compound NCC(C(O)=O)CC1=CC=C2OCOC2=C1 BTLMAFGMHHKSHH-UHFFFAOYSA-N 0.000 claims description 3
- KJCNFUSUQWTOIN-UHFFFAOYSA-N 2-(azaniumylmethyl)-3-naphthalen-1-ylpropanoate Chemical compound C1=CC=C2C(CC(CN)C(O)=O)=CC=CC2=C1 KJCNFUSUQWTOIN-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 3
- BNHFUDORBVXBPC-ZETCQYMHSA-N (2s)-2-(aminomethyl)-3-(2,5-dichlorophenyl)propanoic acid Chemical compound NC[C@@H](C(O)=O)CC1=CC(Cl)=CC=C1Cl BNHFUDORBVXBPC-ZETCQYMHSA-N 0.000 claims description 2
- MDTRNDQNDDIKBF-ZETCQYMHSA-N (2s)-2-(aminomethyl)-3-(3,5-dichlorophenyl)propanoic acid Chemical compound NC[C@@H](C(O)=O)CC1=CC(Cl)=CC(Cl)=C1 MDTRNDQNDDIKBF-ZETCQYMHSA-N 0.000 claims description 2
- PLDBEBVPTBISTH-VIFPVBQESA-N (2s)-2-(aminomethyl)-3-(3-methylsulfanylphenyl)propanoic acid Chemical compound CSC1=CC=CC(C[C@@H](CN)C(O)=O)=C1 PLDBEBVPTBISTH-VIFPVBQESA-N 0.000 claims description 2
- RJXGEMXSPNQVCP-ZDUSSCGKSA-N (2s)-2-(aminomethyl)-3-[2-(4-fluorophenyl)phenyl]propanoic acid Chemical compound NC[C@@H](C(O)=O)CC1=CC=CC=C1C1=CC=C(F)C=C1 RJXGEMXSPNQVCP-ZDUSSCGKSA-N 0.000 claims description 2
- RTYMKXXEFPPCSL-ZDUSSCGKSA-N (2s)-2-(aminomethyl)-3-[3-(2-methylpropyl)phenyl]propanoic acid Chemical compound CC(C)CC1=CC=CC(C[C@@H](CN)C(O)=O)=C1 RTYMKXXEFPPCSL-ZDUSSCGKSA-N 0.000 claims description 2
- QRHHAFBBXIODHQ-QMMMGPOBSA-N (2s)-2-(azaniumylmethyl)-3-(3-chlorophenyl)propanoate Chemical compound NC[C@@H](C(O)=O)CC1=CC=CC(Cl)=C1 QRHHAFBBXIODHQ-QMMMGPOBSA-N 0.000 claims description 2
- OWUCQTYNFQLYOY-UHFFFAOYSA-N 2-(aminomethyl)-3-(3,4-dichlorophenyl)propanoic acid Chemical compound NCC(C(O)=O)CC1=CC=C(Cl)C(Cl)=C1 OWUCQTYNFQLYOY-UHFFFAOYSA-N 0.000 claims description 2
- UBHBWFINVWXKBO-UHFFFAOYSA-N 2-(aminomethyl)-3-[4-(dimethylamino)phenyl]propanoic acid Chemical compound CN(C)C1=CC=C(CC(CN)C(O)=O)C=C1 UBHBWFINVWXKBO-UHFFFAOYSA-N 0.000 claims description 2
- DHPVJZGGWAJJBV-UHFFFAOYSA-N 2-(azaniumylmethyl)-3-(4-chlorophenyl)propanoate Chemical compound NCC(C(O)=O)CC1=CC=C(Cl)C=C1 DHPVJZGGWAJJBV-UHFFFAOYSA-N 0.000 claims description 2
- VAVGSOFCGOOZRH-UHFFFAOYSA-N 2-(azaniumylmethyl)-3-(4-methylphenyl)propanoate Chemical compound CC1=CC=C(CC(CN)C(O)=O)C=C1 VAVGSOFCGOOZRH-UHFFFAOYSA-N 0.000 claims description 2
- DJYVEBBGKNAHKE-UHFFFAOYSA-N 2-(azaniumylmethyl)-3-phenylpropanoate Chemical compound NCC(C(O)=O)CC1=CC=CC=C1 DJYVEBBGKNAHKE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- IIBVGXXBKONSOJ-UHFFFAOYSA-N ethyl 2-(aminomethyl)-3-phenylpropanoate Chemical compound CCOC(=O)C(CN)CC1=CC=CC=C1 IIBVGXXBKONSOJ-UHFFFAOYSA-N 0.000 claims 1
- ZXJFTFSXKOCPQM-UHFFFAOYSA-N ethyl 2-benzyl-3-(methylamino)propanoate Chemical compound CCOC(=O)C(CNC)CC1=CC=CC=C1 ZXJFTFSXKOCPQM-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- QOEALULCQUCMOP-UHFFFAOYSA-N methyl 2-(aminomethyl)-3-phenylpropanoate Chemical compound COC(=O)C(CN)CC1=CC=CC=C1 QOEALULCQUCMOP-UHFFFAOYSA-N 0.000 claims 1
- LURXPOJHBKSORO-UHFFFAOYSA-N tert-butyl 2-(aminomethyl)-3-phenylpropanoate Chemical compound CC(C)(C)OC(=O)C(CN)CC1=CC=CC=C1 LURXPOJHBKSORO-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 74
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 39
- 238000009472 formulation Methods 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 229940002612 prodrug Drugs 0.000 description 18
- 239000000651 prodrug Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- 239000003826 tablet Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 238000000065 atmospheric pressure chemical ionisation Methods 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000003446 ligand Substances 0.000 description 14
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-MICDWDOJSA-N deuteriomethanol Chemical compound [2H]CO OKKJLVBELUTLKV-MICDWDOJSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 208000014674 injury Diseases 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 230000006378 damage Effects 0.000 description 10
- 239000002552 dosage form Substances 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 208000027418 Wounds and injury Diseases 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 208000004296 neuralgia Diseases 0.000 description 8
- 208000021722 neuropathic pain Diseases 0.000 description 8
- 210000000929 nociceptor Anatomy 0.000 description 8
- 108091008700 nociceptors Proteins 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 208000008035 Back Pain Diseases 0.000 description 7
- 208000035475 disorder Diseases 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 208000009935 visceral pain Diseases 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000002459 sustained effect Effects 0.000 description 6
- 208000011580 syndromic disease Diseases 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
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- 208000000094 Chronic Pain Diseases 0.000 description 5
- 229920000858 Cyclodextrin Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 206010019233 Headaches Diseases 0.000 description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
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- 238000004809 thin layer chromatography Methods 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 238000000844 transformation Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 208000004454 Hyperalgesia Diseases 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
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- 238000001727 in vivo Methods 0.000 description 4
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- 230000001473 noxious effect Effects 0.000 description 4
- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 description 4
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 4
- BDTIXZRGDAZGHK-QRPNPIFTSA-N (2s)-2-(aminomethyl)-3-(3-chlorophenyl)propanoic acid;hydrochloride Chemical compound Cl.NC[C@@H](C(O)=O)CC1=CC=CC(Cl)=C1 BDTIXZRGDAZGHK-QRPNPIFTSA-N 0.000 description 3
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 206010065390 Inflammatory pain Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 208000001294 Nociceptive Pain Diseases 0.000 description 3
- 208000004550 Postoperative Pain Diseases 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/63—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US67852305P | 2005-05-06 | 2005-05-06 | |
US60/678,523 | 2005-05-06 | ||
PCT/IB2006/001209 WO2006120544A1 (fr) | 2005-05-06 | 2006-04-24 | Derives d'acide ?-amino |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2606254A1 true CA2606254A1 (fr) | 2006-11-16 |
Family
ID=36960801
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002606254A Abandoned CA2606254A1 (fr) | 2005-05-06 | 2006-04-24 | Derives d'acide .beta.-amino |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1883620A1 (fr) |
JP (1) | JP2008542198A (fr) |
CA (1) | CA2606254A1 (fr) |
WO (1) | WO2006120544A1 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2653667A1 (fr) | 2006-05-31 | 2007-12-06 | Asubio Pharma Co., Ltd. | Anneau heterocycliques a 7 elements, son procede de production et ses utilisations pharmaceutiques |
US8076516B2 (en) | 2007-11-01 | 2011-12-13 | Acucela, Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
US9096558B2 (en) | 2010-07-09 | 2015-08-04 | Pfizer Limited | N-sulfonylbenzamide compounds |
IT202100011237A1 (it) * | 2021-05-03 | 2022-11-03 | Univ Degli Studi Di Torino | Composti inibitori dell’inflammasoma nlrp3 e loro uso |
-
2006
- 2006-04-24 JP JP2008509534A patent/JP2008542198A/ja not_active Withdrawn
- 2006-04-24 CA CA002606254A patent/CA2606254A1/fr not_active Abandoned
- 2006-04-24 EP EP06744676A patent/EP1883620A1/fr not_active Withdrawn
- 2006-04-24 WO PCT/IB2006/001209 patent/WO2006120544A1/fr not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
WO2006120544A1 (fr) | 2006-11-16 |
JP2008542198A (ja) | 2008-11-27 |
EP1883620A1 (fr) | 2008-02-06 |
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Legal Events
Date | Code | Title | Description |
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EEER | Examination request | ||
FZDE | Dead |