TW200813018A - Novel compounds - Google Patents

Info

Publication number

TW200813018A

TW200813018A TW096119135A TW96119135A TW200813018A TW 200813018 A TW200813018 A TW 200813018A TW 096119135 A TW096119135 A TW 096119135A TW 96119135 A TW96119135 A TW 96119135A TW 200813018 A TW200813018 A TW 200813018A

Authority

TW

Taiwan

Prior art keywords

group

alkyl

alkoxy

cycloalkyl

hexahydro

Prior art date

2006-06-09

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 224
• 150000003839 salts Chemical class 0.000 claims abstract description 39
• 208000002193 Pain Diseases 0.000 claims abstract description 26
• 230000036407 pain Effects 0.000 claims abstract description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 329
• -1 alkoxy fluorene Chemical compound 0.000 claims description 175
• 125000003545 alkoxy group Chemical group 0.000 claims description 161
• 239000000203 mixture Substances 0.000 claims description 134
• 239000001257 hydrogen Substances 0.000 claims description 118
• 229910052739 hydrogen Inorganic materials 0.000 claims description 118
• 150000002431 hydrogen Chemical class 0.000 claims description 85
• 125000003282 alkyl amino group Chemical group 0.000 claims description 79
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 63
• 125000001072 heteroaryl group Chemical group 0.000 claims description 63
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 57
• 229910052736 halogen Inorganic materials 0.000 claims description 51
• 150000002367 halogens Chemical class 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 46
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 37
• 238000000034 method Methods 0.000 claims description 35
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 30
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 28
• 239000000460 chlorine Substances 0.000 claims description 28
• 238000011282 treatment Methods 0.000 claims description 28
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 125000002757 morpholinyl group Chemical group 0.000 claims description 21
• 125000003277 amino group Chemical group 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 19
• 125000002541 furyl group Chemical group 0.000 claims description 19
• 239000007789 gas Substances 0.000 claims description 19
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 18
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 18
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 18
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
• 125000002393 azetidinyl group Chemical group 0.000 claims description 15
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
• 150000002576 ketones Chemical class 0.000 claims description 15
• 125000005493 quinolyl group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 241001465754 Metazoa Species 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
• 241000700159 Rattus Species 0.000 claims description 13
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 10
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
• 150000003973 alkyl amines Chemical class 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 9
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 150000002923 oximes Chemical class 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• 206010036790 Productive cough Diseases 0.000 claims description 7
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 7
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
• UZGLIIJVICEWHF-UHFFFAOYSA-N octogen Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)CN([N+]([O-])=O)C1 UZGLIIJVICEWHF-UHFFFAOYSA-N 0.000 claims description 7
• 210000003802 sputum Anatomy 0.000 claims description 7
• 208000024794 sputum Diseases 0.000 claims description 7
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
• 125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 claims description 6
• 239000000796 flavoring agent Substances 0.000 claims description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 229910052707 ruthenium Inorganic materials 0.000 claims description 6
• 201000000980 schizophrenia Diseases 0.000 claims description 6
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
• 239000000052 vinegar Substances 0.000 claims description 6
• 235000021419 vinegar Nutrition 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 230000001225 therapeutic effect Effects 0.000 claims description 5
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 150000004032 porphyrins Chemical group 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 230000002441 reversible effect Effects 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 208000019901 Anxiety disease Diseases 0.000 claims description 3
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 239000000126 substance Substances 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 2
• WRWMEYIPKHDVRW-UHFFFAOYSA-N 1,2-dihydrobenzo[e]pyrene Chemical compound C1=CC=C2C=CC3=CCCC4=C(C=CC=C5)C5=C1C2=C43 WRWMEYIPKHDVRW-UHFFFAOYSA-N 0.000 claims description 2
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 2
• LMJDWRWZTXQWTI-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indole Chemical compound C1CCC=C2NCCC21 LMJDWRWZTXQWTI-UHFFFAOYSA-N 0.000 claims description 2
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
• 241000238413 Octopus Species 0.000 claims description 2
• 150000001450 anions Chemical group 0.000 claims description 2
• 230000036506 anxiety Effects 0.000 claims description 2
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
• 125000004122 cyclic group Chemical group 0.000 claims description 2
• 150000001924 cycloalkanes Chemical class 0.000 claims description 2
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
• 125000004494 ethyl ester group Chemical group 0.000 claims description 2
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
• 101150055297 SET1 gene Proteins 0.000 claims 2
• 125000006612 decyloxy group Chemical group 0.000 claims 2
• 239000010977 jade Substances 0.000 claims 2
• 229910052747 lanthanoid Inorganic materials 0.000 claims 2
• 150000002602 lanthanoids Chemical class 0.000 claims 2
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 2
• 239000002689 soil Substances 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 1
• CRIZPXKICGBNKG-UHFFFAOYSA-N 3,7-dihydropurin-2-one Chemical compound OC1=NC=C2NC=NC2=N1 CRIZPXKICGBNKG-UHFFFAOYSA-N 0.000 claims 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
• 244000241257 Cucumis melo Species 0.000 claims 1
• 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims 1
• 244000304337 Cuminum cyminum Species 0.000 claims 1
• 235000007129 Cuminum cyminum Nutrition 0.000 claims 1
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 1
• 235000010254 Jasminum officinale Nutrition 0.000 claims 1
• 240000005385 Jasminum sambac Species 0.000 claims 1
• 101100447665 Mus musculus Gas2 gene Proteins 0.000 claims 1
• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims 1
• 150000001336 alkenes Chemical class 0.000 claims 1
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 1
• FXRDPPFLWGSMQT-UHFFFAOYSA-N benzo[f]chromen-3-one Chemical compound C1=CC=C2C(C=CC(O3)=O)=C3C=CC2=C1 FXRDPPFLWGSMQT-UHFFFAOYSA-N 0.000 claims 1
• KXBTULMIMYFPGV-UHFFFAOYSA-N benzo[g]indol-2-one Chemical compound C1=CC=C2C3=NC(=O)C=C3C=CC2=C1 KXBTULMIMYFPGV-UHFFFAOYSA-N 0.000 claims 1
• XKLVLDXNZDIDKQ-UHFFFAOYSA-N butylhydrazine Chemical compound CCCCNN XKLVLDXNZDIDKQ-UHFFFAOYSA-N 0.000 claims 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• 125000004404 heteroalkyl group Chemical group 0.000 claims 1
• 150000002460 imidazoles Chemical class 0.000 claims 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
• 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
• OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 claims 1
• KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 claims 1
• 125000001725 pyrenyl group Chemical group 0.000 claims 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
• 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 claims 1
• 230000009747 swallowing Effects 0.000 claims 1
• 238000002560 therapeutic procedure Methods 0.000 abstract description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 172
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
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• 235000019439 ethyl acetate Nutrition 0.000 description 87
• 239000000243 solution Substances 0.000 description 71
• 238000002360 preparation method Methods 0.000 description 66
• 239000002585 base Substances 0.000 description 50
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 46
• 238000005160 1H NMR spectroscopy Methods 0.000 description 42
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• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
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• 230000002829 reductive effect Effects 0.000 description 25
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• 238000005481 NMR spectroscopy Methods 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
• 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 20
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• 238000006243 chemical reaction Methods 0.000 description 17
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• 230000000694 effects Effects 0.000 description 14
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• 239000011541 reaction mixture Substances 0.000 description 13
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• 238000004128 high performance liquid chromatography Methods 0.000 description 11
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• 239000012044 organic layer Substances 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• 230000014759 maintenance of location Effects 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 208000004296 neuralgia Diseases 0.000 description 8
• 208000021722 neuropathic pain Diseases 0.000 description 8
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