TW200815405A - Novel compounds - Google Patents
Novel compounds Download PDFInfo
- 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
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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
- 239000000047 product Substances 0.000 description 7
- 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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Classifications
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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Landscapes
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| KR20120102172A (ko) | 2007-08-31 | 2012-09-17 | 시오노기세이야쿠가부시키가이샤 | 치환-퀴녹살린-형 피페리딘 화합물 및 그의 용도 |
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| BRPI0911031B8 (pt) | 2008-07-21 | 2021-05-25 | Purdue Pharma Lp | compostos de piperidina ligada do tipo quinoxalina substituídos e os usos destes |
| GB0817982D0 (en) * | 2008-10-01 | 2008-11-05 | Glaxo Group Ltd | Compounds |
| TW201211028A (en) * | 2010-08-10 | 2012-03-16 | Dainippon Sumitomo Pharma Co | Fused ring pyrrolidine derivatives |
| AU2012253757B2 (en) | 2011-05-06 | 2017-04-13 | Zafgen Inc. | Partially saturated tricyclic compounds and methods of making and using same |
| JP2015083543A (ja) * | 2012-02-14 | 2015-04-30 | 大日本住友製薬株式会社 | 新規縮環ピロリジン誘導体 |
| US20140171466A1 (en) * | 2012-08-14 | 2014-06-19 | Regents Of The University Of Minnesota | Pain management in sickle cell anemia |
| BR112015006029B1 (pt) * | 2012-09-18 | 2022-01-25 | Heptares Therapeutics Limited | Compostos aza bicíclicos como agonistas de receptor m1 muscarínicos, composição farmacêutica compreendendo ditos compostos e uso dos mesmos para tratar um distúrbio cognitivo ou distúrbio psicótico ou para tratar ou reduzir a gravidade de dores agudas, crônicas, neuropáticas ou inflamatórias |
| BR112015010196A2 (pt) | 2012-11-05 | 2017-07-11 | Zafgen Inc | métodos de tratar doença do fígado |
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| PT1753748E (pt) * | 2004-05-12 | 2009-08-28 | Pfizer Prod Inc | Derivados de prolina e a sua utilização como inibidores de dipeptidil peptidase iv |
| JP2008501031A (ja) * | 2004-05-28 | 2008-01-17 | バーテックス ファーマシューティカルズ インコーポレイテッド | ムスカリン受容体のモジュレーター |
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| US20100173935A1 (en) | 2010-07-08 |
| CA2654147A1 (en) | 2007-12-13 |
| JP2009539833A (ja) | 2009-11-19 |
| ZA200809976B (en) | 2011-04-28 |
| EP2035412A4 (en) | 2011-02-16 |
| IL195427A0 (en) | 2009-08-03 |
| EP2035412A1 (en) | 2009-03-18 |
| CN101501024A (zh) | 2009-08-05 |
| BRPI0712415A2 (pt) | 2012-09-04 |
| WO2007142585A1 (en) | 2007-12-13 |
| KR20090016636A (ko) | 2009-02-16 |
| ECSP088967A (es) | 2009-01-30 |
| AU2007256014A1 (en) | 2007-12-13 |
| NO20085271L (no) | 2009-01-06 |
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