TW200815405A - Novel compounds - Google Patents

Info

Publication number

TW200815405A

TW200815405A TW096119136A TW96119136A TW200815405A TW 200815405 A TW200815405 A TW 200815405A TW 096119136 A TW096119136 A TW 096119136A TW 96119136 A TW96119136 A TW 96119136A TW 200815405 A TW200815405 A TW 200815405A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

alkoxy

aryl

heterocycloalkyl

Prior art date

2006-06-09

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 200
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 208000002193 Pain Diseases 0.000 claims abstract description 25
• 230000036407 pain Effects 0.000 claims abstract description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
• 125000000217 alkyl group Chemical group 0.000 claims description 315
• 125000003545 alkoxy group Chemical group 0.000 claims description 211
• 125000003282 alkyl amino group Chemical group 0.000 claims description 104
• -1 hydroxy, decyloxy Chemical group 0.000 claims description 104
• 229910052739 hydrogen Inorganic materials 0.000 claims description 96
• 239000001257 hydrogen Substances 0.000 claims description 95
• 125000001072 heteroaryl group Chemical group 0.000 claims description 89
• 150000002431 hydrogen Chemical group 0.000 claims description 77
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 73
• 125000003118 aryl group Chemical group 0.000 claims description 59
• 238000000034 method Methods 0.000 claims description 50
• 239000000203 mixture Substances 0.000 claims description 50
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 48
• 125000003342 alkenyl group Chemical group 0.000 claims description 47
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
• 150000002367 halogens Chemical group 0.000 claims description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 34
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 32
• 239000000460 chlorine Substances 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 31
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 29
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 29
• 125000004104 aryloxy group Chemical group 0.000 claims description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
• 241000700159 Rattus Species 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 20
• 125000003277 amino group Chemical group 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 15
• 239000000052 vinegar Substances 0.000 claims description 15
• 235000021419 vinegar Nutrition 0.000 claims description 15
• 241001465754 Metazoa Species 0.000 claims description 14
• 150000001412 amines Chemical group 0.000 claims description 14
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 13
• 150000003973 alkyl amines Chemical class 0.000 claims description 13
• 239000007789 gas Substances 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 235000019253 formic acid Nutrition 0.000 claims description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
• 201000010099 disease Diseases 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
• WGTHNNRORWFTFA-UHFFFAOYSA-N ethyl pyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCCC1 WGTHNNRORWFTFA-UHFFFAOYSA-N 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 8
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 8
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 239000003638 chemical reducing agent Substances 0.000 claims description 7
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 239000003153 chemical reaction reagent Substances 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 5
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 201000000980 schizophrenia Diseases 0.000 claims description 5
• LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 claims description 5
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 4
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 239000000126 substance Substances 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
• GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
• 238000006268 reductive amination reaction Methods 0.000 claims description 3
• 229910052707 ruthenium Inorganic materials 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 229910052786 argon Inorganic materials 0.000 claims description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
• MZTZYHFBBOZYFC-UHFFFAOYSA-N benzene;9h-fluorene Chemical compound C1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 MZTZYHFBBOZYFC-UHFFFAOYSA-N 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000006612 decyloxy group Chemical group 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• BFNBQFYHSZVMJZ-UHFFFAOYSA-N ethyl formate pyrrolidine Chemical compound C(=O)OCC.N1CCCC1 BFNBQFYHSZVMJZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 claims description 2
• 239000001814 pectin Substances 0.000 claims description 2
• 235000010987 pectin Nutrition 0.000 claims description 2
• 229920001277 pectin Polymers 0.000 claims description 2
• 229940067157 phenylhydrazine Drugs 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
• VMAVSXGGXUCSCI-UHFFFAOYSA-N 1,2,2,3,3,4-hexamethylpyrazine Chemical compound CN1C(C(N(C=C1)C)(C)C)(C)C VMAVSXGGXUCSCI-UHFFFAOYSA-N 0.000 claims 1
• ZSBPGGQJRPMLCZ-UHFFFAOYSA-N 1,2,3,4,4a,10-hexahydroacridine Chemical compound C1=CC=C2NC(CCCC3)C3=CC2=C1 ZSBPGGQJRPMLCZ-UHFFFAOYSA-N 0.000 claims 1
• UJOTVXGAKNBKFW-UHFFFAOYSA-N 1H-benzimidazole 2,3-dihydro-1H-indole Chemical compound N1=CNC2=C1C=CC=C2.N2CCC1=CC=CC=C21 UJOTVXGAKNBKFW-UHFFFAOYSA-N 0.000 claims 1
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
• 235000016425 Arthrospira platensis Nutrition 0.000 claims 1
• 240000002900 Arthrospira platensis Species 0.000 claims 1
• RYFJOHIKHMVYRF-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(CCCCCCCCCN1CCCC1)=O Chemical compound C(C1=CC=CC=C1)OC(CCCCCCCCCN1CCCC1)=O RYFJOHIKHMVYRF-UHFFFAOYSA-N 0.000 claims 1
• GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims 1
• 239000005640 Methyl decanoate Substances 0.000 claims 1
• 241000699670 Mus sp. Species 0.000 claims 1
• MMFCPVLNTIBLNE-UHFFFAOYSA-N O1C=NC2=C1C=CC=C2.C2=CC=CC=1C3=CC=CC=C3CC21 Chemical compound O1C=NC2=C1C=CC=C2.C2=CC=CC=1C3=CC=CC=C3CC21 MMFCPVLNTIBLNE-UHFFFAOYSA-N 0.000 claims 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
• 238000003324 Six Sigma (6σ) Methods 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• 125000005427 anthranyl group Chemical group 0.000 claims 1
• JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 1
• 150000007942 carboxylates Chemical class 0.000 claims 1
• 125000004404 heteroalkyl group Chemical group 0.000 claims 1
• 210000003127 knee Anatomy 0.000 claims 1
• 239000008267 milk Substances 0.000 claims 1
• 210000004080 milk Anatomy 0.000 claims 1
• 235000013336 milk Nutrition 0.000 claims 1
• 229910052762 osmium Inorganic materials 0.000 claims 1
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims 1
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 1
• 102200067153 rs28897672 Human genes 0.000 claims 1
• 229940082787 spirulina Drugs 0.000 claims 1
• 239000000758 substrate Substances 0.000 claims 1
• 150000003505 terpenes Chemical class 0.000 claims 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 31
• 238000002360 preparation method Methods 0.000 description 29
• 239000002585 base Substances 0.000 description 27
• 239000007787 solid Substances 0.000 description 27
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 25
• 235000019439 ethyl acetate Nutrition 0.000 description 23
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 22
• 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 22
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 20
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• 238000005481 NMR spectroscopy Methods 0.000 description 15
• 238000004128 high performance liquid chromatography Methods 0.000 description 15
• 239000000243 solution Substances 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 239000002207 metabolite Substances 0.000 description 13
• 102000005962 receptors Human genes 0.000 description 13
• 108020003175 receptors Proteins 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 239000000556 agonist Substances 0.000 description 12
• 239000003795 chemical substances by application Substances 0.000 description 12
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 10
• 208000004296 neuralgia Diseases 0.000 description 10
• 208000021722 neuropathic pain Diseases 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000012267 brine Substances 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
• 210000004978 chinese hamster ovary cell Anatomy 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• 239000005557 antagonist Substances 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 230000027455 binding Effects 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 238000002474 experimental method Methods 0.000 description 7
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 6
• ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 239000008346 aqueous phase Substances 0.000 description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 239000012528 membrane Substances 0.000 description 6
• 229960005181 morphine Drugs 0.000 description 6
• 239000012044 organic layer Substances 0.000 description 6
• 108090000623 proteins and genes Proteins 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• 150000003573 thiols Chemical class 0.000 description 6
• MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 6
• 229960000604 valproic acid Drugs 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
• 229960004373 acetylcholine Drugs 0.000 description 5
• 230000006870 function Effects 0.000 description 5
• 230000005764 inhibitory process Effects 0.000 description 5
• 125000002950 monocyclic group Chemical group 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• 229940102566 valproate Drugs 0.000 description 5
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical compound O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
• 102000017926 CHRM2 Human genes 0.000 description 4
• 101150012960 Chrm2 gene Proteins 0.000 description 4
• 208000000094 Chronic Pain Diseases 0.000 description 4
• 208000004454 Hyperalgesia Diseases 0.000 description 4
• 206010020751 Hypersensitivity Diseases 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
• 239000011324 bead Substances 0.000 description 4
• 125000005605 benzo group Chemical group 0.000 description 4
• FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
• 229960000623 carbamazepine Drugs 0.000 description 4
• 229960001231 choline Drugs 0.000 description 4
• 230000001684 chronic effect Effects 0.000 description 4
• 231100000673 dose–response relationship Toxicity 0.000 description 4
• 125000004494 ethyl ester group Chemical group 0.000 description 4
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 4
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