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]
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- 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
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- 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
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- 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)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Nutrition Science (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 |
| CN102227431A (zh) * | 2008-09-29 | 2011-10-26 | 雅培制药有限公司 | 吲哚和二氢吲哚衍生物及其应用方法 |
| EP2632257B1 (en) | 2010-10-25 | 2021-03-31 | Vanderbilt University | Compositions for inhibition of insect host sensing |
| WO2012154403A2 (en) | 2011-05-06 | 2012-11-15 | Vanderbilt University | Composition 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 |
| CN107529746B (zh) | 2015-03-25 | 2021-09-07 | 范德比尔特大学 | 作为orco介导的气味感觉干扰剂的二元组合物 |
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| 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 |
| TWI283577B (en) * | 1999-10-11 | 2007-07-11 | Sod Conseils Rech Applic | Pharmaceutical composition of imidazole derivatives acting as modulators of sodium channels and the use thereof |
| WO2001058869A2 (en) | 2000-02-11 | 2001-08-16 | Bristol-Myers Squibb Company | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases |
| AUPR118000A0 (en) | 2000-11-02 | 2000-11-23 | Amrad Operations Pty. Limited | Therapeutic molecules and methods |
| CA2436133A1 (en) | 2001-01-29 | 2002-08-08 | University Of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
| 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 |
| US7772227B2 (en) | 2003-12-17 | 2010-08-10 | N.V. Organon | Tricyclic 1-[(indol-3-yl)carbonyl]piperazine derivatives as cannabinoid CB1 receptor agonists |
| TWI330635B (en) | 2004-03-05 | 2010-09-21 | Organon Nv | (indol-3-yl)-heterocycle derivatives |
| JP2009500439A (ja) * | 2005-07-11 | 2009-01-08 | ナームローゼ・フエンノートチヤツプ・オルガノン | 疼痛の治療のための相乗的組み合わせ（カンナビノイド受容体アゴニスト及びオピオイド受容体アゴニスト） |
| 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 |
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2008
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- 2008-02-20 AR ARP080100681A patent/AR065393A1/es unknown
- 2008-02-20 CL CL200800514A patent/CL2008000514A1/es unknown
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- 2008-02-21 CN CN2008800057712A patent/CN101616914B/zh not_active Expired - Fee Related
- 2008-02-21 CA CA002678147A patent/CA2678147A1/en not_active Abandoned
- 2008-02-21 RU RU2009135255/04A patent/RU2009135255A/ru not_active Application Discontinuation
- 2008-02-21 BR BRPI0807867-0A2A patent/BRPI0807867A2/pt not_active IP Right Cessation
- 2008-02-21 KR KR1020097019668A patent/KR20090113383A/ko not_active Withdrawn
- 2008-02-21 AU AU2008219226A patent/AU2008219226B2/en not_active Ceased
- 2008-02-21 JP JP2009550715A patent/JP5324476B2/ja not_active Expired - Fee Related
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- 2008-02-21 MX MX2009008316A patent/MX2009008316A/es active IP Right Grant
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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 |
|---|---|
| PE20090112A1 (es) | 2009-02-26 |
| BRPI0807867A2 (pt) | 2014-06-03 |
| JP2010519278A (ja) | 2010-06-03 |
| US20080207598A1 (en) | 2008-08-28 |
| IL199848A0 (en) | 2010-04-15 |
| RU2009135255A (ru) | 2011-03-27 |
| AU2008219226A1 (en) | 2008-08-28 |
| MX2009008316A (es) | 2009-08-12 |
| CA2678147A1 (en) | 2008-08-28 |
| EP2125795B1 (en) | 2013-03-20 |
| JP5324476B2 (ja) | 2013-10-23 |
| CN101616914A (zh) | 2009-12-30 |
| KR20090113383A (ko) | 2009-10-30 |
| AU2008219226B2 (en) | 2013-02-07 |
| CL2008000514A1 (es) | 2008-06-20 |
| WO2008101995A1 (en) | 2008-08-28 |
| AR065393A1 (es) | 2009-06-03 |
| EP2125795A1 (en) | 2009-12-02 |
| ECSP099593A (es) | 2009-09-29 |
| ZA200905265B (en) | 2010-04-28 |
| CN101616914B (zh) | 2012-10-10 |
| US7655645B2 (en) | 2010-02-02 |
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