TW200848417A - Indole derivatives - Google Patents
Indole derivatives Download PDFInfo
- Publication number
- TW200848417A TW200848417A TW097103332A TW97103332A TW200848417A TW 200848417 A TW200848417 A TW 200848417A TW 097103332 A TW097103332 A TW 097103332A TW 97103332 A TW97103332 A TW 97103332A TW 200848417 A TW200848417 A TW 200848417A
- Authority
- TW
- Taiwan
- Prior art keywords
- methyl
- chloro
- tetrahydropyran
- mmol
- alkyl
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title abstract description 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 4
- 208000002193 Pain Diseases 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 208000004296 neuralgia Diseases 0.000 claims abstract description 9
- 208000021722 neuropathic pain Diseases 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
- 206010058019 Cancer Pain Diseases 0.000 claims abstract description 4
- 208000000094 Chronic Pain Diseases 0.000 claims abstract description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000000468 ketone group Chemical group 0.000 claims abstract description 3
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
- 239000000203 mixture Substances 0.000 claims description 78
- -1 tetrahydropyran-4-yl Chemical group 0.000 claims description 72
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 41
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 150000002429 hydrazines Chemical class 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 150000001454 anthracenes Chemical class 0.000 claims description 5
- 150000002923 oximes Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 241001674044 Blattodea Species 0.000 claims description 2
- 208000007101 Muscle Cramp Diseases 0.000 claims description 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 239000000556 agonist Substances 0.000 abstract description 7
- 229930003827 cannabinoid Natural products 0.000 abstract description 7
- 239000003557 cannabinoid Substances 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 abstract description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 abstract description 2
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 239000005977 Ethylene Chemical group 0.000 abstract 1
- 208000008238 Muscle Spasticity Diseases 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 208000018198 spasticity Diseases 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 101
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 100
- 150000001875 compounds Chemical class 0.000 description 92
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 238000000034 method Methods 0.000 description 48
- 235000019439 ethyl acetate Nutrition 0.000 description 46
- 239000000243 solution Substances 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 22
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 108020003175 receptors Proteins 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 102000005962 receptors Human genes 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 235000009518 sodium iodide Nutrition 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 108020004414 DNA Proteins 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- KKFGZKBFBZYLJH-UHFFFAOYSA-N N-ethyl-N-propan-2-ylpropan-2-amine hydrazine Chemical compound C(C)(C)N(CC)C(C)C.NN KKFGZKBFBZYLJH-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 229940005483 opioid analgesics Drugs 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 239000000730 antalgic agent Substances 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- DCBKCZSYJRZBDB-UHFFFAOYSA-N oxan-4-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CCOCC1 DCBKCZSYJRZBDB-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- MTRUTFXFVXYFEH-UHFFFAOYSA-N 1-(oxan-4-ylmethyl)indole Chemical compound C1=CC2=CC=CC=C2N1CC1CCOCC1 MTRUTFXFVXYFEH-UHFFFAOYSA-N 0.000 description 3
- OFILXYRUXDYLLS-UHFFFAOYSA-N 2-piperidin-1-ylacetamide Chemical compound NC(=O)CN1CCCCC1 OFILXYRUXDYLLS-UHFFFAOYSA-N 0.000 description 3
- WMYQAKANKREQLM-UHFFFAOYSA-N 7-chloro-1h-indole Chemical compound ClC1=CC=CC2=C1NC=C2 WMYQAKANKREQLM-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003554 cannabinoid 1 receptor agonist Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- 230000007935 neutral effect Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 2
- AGJMYRPRXJGALC-UHFFFAOYSA-N 4-(chloromethyl)-2-[7-chloro-1-(oxan-4-ylmethyl)indol-3-yl]-1,3-thiazole Chemical compound ClCC1=CSC(C=2C3=CC=CC(Cl)=C3N(CC3CCOCC3)C=2)=N1 AGJMYRPRXJGALC-UHFFFAOYSA-N 0.000 description 2
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
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- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 2
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Nutrition Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07102870 | 2007-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200848417A true TW200848417A (en) | 2008-12-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097103332A TW200848417A (en) | 2007-02-22 | 2008-01-29 | Indole derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7655645B2 (enExample) |
| EP (1) | EP2125795B1 (enExample) |
| JP (1) | JP5324476B2 (enExample) |
| KR (1) | KR20090113383A (enExample) |
| CN (1) | CN101616914B (enExample) |
| AR (1) | AR065393A1 (enExample) |
| AU (1) | AU2008219226B2 (enExample) |
| BR (1) | BRPI0807867A2 (enExample) |
| CA (1) | CA2678147A1 (enExample) |
| CL (1) | CL2008000514A1 (enExample) |
| EC (1) | ECSP099593A (enExample) |
| IL (1) | IL199848A0 (enExample) |
| MX (1) | MX2009008316A (enExample) |
| PE (1) | PE20090112A1 (enExample) |
| RU (1) | RU2009135255A (enExample) |
| TW (1) | TW200848417A (enExample) |
| WO (1) | WO2008101995A1 (enExample) |
| ZA (1) | ZA200905265B (enExample) |
Families Citing this family (8)
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| TWI330635B (en) | 2004-03-05 | 2010-09-21 | Organon Nv | (indol-3-yl)-heterocycle derivatives |
| US7763732B2 (en) * | 2005-08-24 | 2010-07-27 | N.V. Organon | Indole derivatives |
| TW200848417A (en) | 2007-02-22 | 2008-12-16 | Organon Nv | Indole derivatives |
| WO2010036998A2 (en) * | 2008-09-29 | 2010-04-01 | Abbott Laboratories | Indole and indoline derivatives and methods of use thereof |
| US9332757B2 (en) | 2010-10-25 | 2016-05-10 | Vanderbilt University | Composition for inhibition of insect host sensing |
| AU2012254032B2 (en) | 2011-05-06 | 2017-02-23 | Vanderbilt University | Compositions for inhibition of insect sensing |
| CN102757427A (zh) * | 2012-07-09 | 2012-10-31 | 陕西科技大学 | 2-氨基-5-异二氢吲哚-1,3-二酮甲基1,3,4-噻二唑及其制备方法 |
| US10791739B2 (en) | 2015-03-25 | 2020-10-06 | Vanderbilt University | Binary compositions as disruptors of orco-mediated odorant sensing |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4939138A (en) * | 1988-12-29 | 1990-07-03 | Sterling Drug Inc. | 2- and 3-aminomethyl-6-arylcarbonyl-2,3-dihydropyrrolo(1,2,3-DE)-1,4-benzoxazines |
| TWI292316B (en) * | 1999-10-11 | 2008-01-11 | Sod Conseils Rech Applic | Pharmaceutical composition of thiazole derivatives intended to inhibit mao and/or lipidic peroxidation and/or to act as modulators of sodium channels and the use thereof |
| US6653304B2 (en) | 2000-02-11 | 2003-11-25 | Bristol-Myers Squibb Co. | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| AUPR118000A0 (en) | 2000-11-02 | 2000-11-23 | Amrad Operations Pty. Limited | Therapeutic molecules and methods |
| JP2005503998A (ja) | 2001-01-29 | 2005-02-10 | ユニバーシティ オブ コネチカット | 受容体選択性のカンナビミメティックアミノアルキルインドール |
| TWI248438B (en) * | 2001-04-10 | 2006-02-01 | Sod Conseils Rech Applic | Derivatives of heterocycles with 5 members, their preparation and their use as medicaments |
| TW200402417A (en) | 2002-06-21 | 2004-02-16 | Akzo Nobel Nv | 1-[(Indol-3-yl)carbonyl]piperazine derivatives |
| BRPI0417626A (pt) | 2003-12-17 | 2007-03-27 | Akzo Nobel Nv | derivado de 1-[(indol-3-il) carbonil] piperazina tricìclica, composição farmacêutica, uso de um derivado de 1-[(indol-3-il) carbonil] piperazina tricìclica |
| TWI330635B (en) | 2004-03-05 | 2010-09-21 | Organon Nv | (indol-3-yl)-heterocycle derivatives |
| AU2006268680B2 (en) * | 2005-07-11 | 2012-11-22 | Msd Oss B.V. | Synergistic combination for the treatment of pain (cannabioid receptor agonist and opiod receptor agonist) |
| TW200745096A (en) | 2005-08-23 | 2007-12-16 | Organon Nv | Indole derivatives |
| US7763732B2 (en) * | 2005-08-24 | 2010-07-27 | N.V. Organon | Indole derivatives |
| TW200848417A (en) | 2007-02-22 | 2008-12-16 | Organon Nv | Indole derivatives |
-
2008
- 2008-01-29 TW TW097103332A patent/TW200848417A/zh unknown
- 2008-02-15 US US12/031,851 patent/US7655645B2/en not_active Expired - Fee Related
- 2008-02-20 PE PE2008000362A patent/PE20090112A1/es not_active Application Discontinuation
- 2008-02-20 AR ARP080100681A patent/AR065393A1/es unknown
- 2008-02-20 CL CL200800514A patent/CL2008000514A1/es unknown
- 2008-02-21 CA CA002678147A patent/CA2678147A1/en not_active Abandoned
- 2008-02-21 AU AU2008219226A patent/AU2008219226B2/en not_active Ceased
- 2008-02-21 WO PCT/EP2008/052141 patent/WO2008101995A1/en not_active Ceased
- 2008-02-21 MX MX2009008316A patent/MX2009008316A/es active IP Right Grant
- 2008-02-21 BR BRPI0807867-0A2A patent/BRPI0807867A2/pt not_active IP Right Cessation
- 2008-02-21 EP EP08709170A patent/EP2125795B1/en active Active
- 2008-02-21 CN CN2008800057712A patent/CN101616914B/zh not_active Expired - Fee Related
- 2008-02-21 KR KR1020097019668A patent/KR20090113383A/ko not_active Withdrawn
- 2008-02-21 RU RU2009135255/04A patent/RU2009135255A/ru not_active Application Discontinuation
- 2008-02-21 JP JP2009550715A patent/JP5324476B2/ja not_active Expired - Fee Related
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2009
- 2009-07-14 IL IL199848A patent/IL199848A0/en unknown
- 2009-07-28 ZA ZA200905265A patent/ZA200905265B/xx unknown
- 2009-08-21 EC EC2009009593A patent/ECSP099593A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2125795A1 (en) | 2009-12-02 |
| RU2009135255A (ru) | 2011-03-27 |
| PE20090112A1 (es) | 2009-02-26 |
| CL2008000514A1 (es) | 2008-06-20 |
| ECSP099593A (es) | 2009-09-29 |
| KR20090113383A (ko) | 2009-10-30 |
| ZA200905265B (en) | 2010-04-28 |
| US20080207598A1 (en) | 2008-08-28 |
| CN101616914A (zh) | 2009-12-30 |
| AU2008219226A1 (en) | 2008-08-28 |
| BRPI0807867A2 (pt) | 2014-06-03 |
| US7655645B2 (en) | 2010-02-02 |
| JP2010519278A (ja) | 2010-06-03 |
| IL199848A0 (en) | 2010-04-15 |
| AR065393A1 (es) | 2009-06-03 |
| JP5324476B2 (ja) | 2013-10-23 |
| AU2008219226B2 (en) | 2013-02-07 |
| EP2125795B1 (en) | 2013-03-20 |
| CN101616914B (zh) | 2012-10-10 |
| WO2008101995A1 (en) | 2008-08-28 |
| MX2009008316A (es) | 2009-08-12 |
| CA2678147A1 (en) | 2008-08-28 |
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