DE10217006A1 - Substituierte Indole - Google Patents
Substituierte IndoleInfo
- Publication number
- DE10217006A1 DE10217006A1 DE10217006A DE10217006A DE10217006A1 DE 10217006 A1 DE10217006 A1 DE 10217006A1 DE 10217006 A DE10217006 A DE 10217006A DE 10217006 A DE10217006 A DE 10217006A DE 10217006 A1 DE10217006 A1 DE 10217006A1
- Authority
- DE
- Germany
- Prior art keywords
- het
- chr
- coor
- formula
- hal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000002475 indoles Chemical class 0.000 title abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 206010008118 cerebral infarction Diseases 0.000 claims abstract description 15
- 208000026106 cerebrovascular disease Diseases 0.000 claims abstract description 14
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 10
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 10
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 8
- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 8
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 8
- 206010015037 epilepsy Diseases 0.000 claims abstract description 8
- 230000007574 infarction Effects 0.000 claims abstract description 8
- 208000023105 Huntington disease Diseases 0.000 claims abstract description 6
- 239000003194 amino acid receptor blocking agent Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 127
- 125000004432 carbon atom Chemical group C* 0.000 claims description 83
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 26
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 239000012453 solvate Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229910021645 metal ion Inorganic materials 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 201000006474 Brain Ischemia Diseases 0.000 claims description 7
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 6
- 101150065749 Churc1 gene Proteins 0.000 claims description 6
- 102100038239 Protein Churchill Human genes 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- PXELOZKDYKBIJY-UHFFFAOYSA-N 4-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 PXELOZKDYKBIJY-UHFFFAOYSA-N 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- MOWLYAKTKWMUQE-UHFFFAOYSA-N 4-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 MOWLYAKTKWMUQE-UHFFFAOYSA-N 0.000 claims description 3
- ZIYLVELXOPYOGF-UHFFFAOYSA-N 4-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=3C(C#N)=CNC=3C=CC=2)CC1 ZIYLVELXOPYOGF-UHFFFAOYSA-N 0.000 claims description 3
- VVVQINXECOLIRC-UHFFFAOYSA-N 5-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 VVVQINXECOLIRC-UHFFFAOYSA-N 0.000 claims description 3
- MORGGAAGUJMDJP-UHFFFAOYSA-N 5-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 MORGGAAGUJMDJP-UHFFFAOYSA-N 0.000 claims description 3
- WJQQNOKNWKZKEI-UHFFFAOYSA-N 5-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3C(C#N)=CNC3=CC=2)CC1 WJQQNOKNWKZKEI-UHFFFAOYSA-N 0.000 claims description 3
- MGWLYPWRAOWAGO-UHFFFAOYSA-N 6-[3-[4-(4-fluorophenoxy)piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 MGWLYPWRAOWAGO-UHFFFAOYSA-N 0.000 claims description 3
- GAOVZTNLDBPBEH-UHFFFAOYSA-N 6-[3-[4-[(2,4-difluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 GAOVZTNLDBPBEH-UHFFFAOYSA-N 0.000 claims description 3
- DMWILBQJRHOAJR-UHFFFAOYSA-N 6-[3-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-1h-indole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1CC1CCN(CCCC=2C=C3NC=C(C3=CC=2)C#N)CC1 DMWILBQJRHOAJR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 208000028698 Cognitive impairment Diseases 0.000 claims description 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 2
- 229940088352 Glycine transporter inhibitor Drugs 0.000 claims description 2
- 206010057852 Nicotine dependence Diseases 0.000 claims description 2
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 2
- 208000016620 Tourette disease Diseases 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 230000002461 excitatory amino acid Effects 0.000 claims description 2
- 239000003257 excitatory amino acid Substances 0.000 claims description 2
- 210000004558 lewy body Anatomy 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- -1 neuroleptics Substances 0.000 abstract description 28
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 239000000164 antipsychotic agent Substances 0.000 abstract 1
- 229940005529 antipsychotics Drugs 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- BVSGXWCTWBZFEV-UHFFFAOYSA-N 1h-indol-4-ylmethanol Chemical compound OCC1=CC=CC2=C1C=CN2 BVSGXWCTWBZFEV-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 7
- 102000014649 NMDA glutamate receptor activity proteins Human genes 0.000 description 7
- 150000004678 hydrides Chemical class 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 239000007858 starting material Substances 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- UYNVMODNBIQBMV-UHFFFAOYSA-N 4-[1-hydroxy-2-[4-(phenylmethyl)-1-piperidinyl]propyl]phenol Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(C)C(O)C1=CC=C(O)C=C1 UYNVMODNBIQBMV-UHFFFAOYSA-N 0.000 description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 5
- 229960003998 ifenprodil Drugs 0.000 description 5
- JFDDFGLNZWNJTK-UHFFFAOYSA-N indole-4-carbaldehyde Chemical compound O=CC1=CC=CC2=C1C=CN2 JFDDFGLNZWNJTK-UHFFFAOYSA-N 0.000 description 5
- IDZVEPSCVVUHKV-UHFFFAOYSA-N methyl 3-(1h-indol-4-yl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=CC2=C1C=CN2 IDZVEPSCVVUHKV-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000006196 drop Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GGUSQTSTQSHJAH-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-(4-fluorobenzyl)piperidin-1-yl]ethanol Chemical compound C=1C=C(Cl)C=CC=1C(O)CN(CC1)CCC1CC1=CC=C(F)C=C1 GGUSQTSTQSHJAH-UHFFFAOYSA-N 0.000 description 3
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical compound C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 description 3
- JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 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
- 239000002537 cosmetic Substances 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 229950005455 eliprodil Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 3
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- 239000000454 talc Substances 0.000 description 3
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- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical class C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 102000015404 Amino Acid Receptors Human genes 0.000 description 2
- 108010025177 Amino Acid Receptors Proteins 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/02—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 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Addiction (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Pregnancy & Childbirth (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10217006A DE10217006A1 (de) | 2002-04-16 | 2002-04-16 | Substituierte Indole |
| CA2482655A CA2482655C (en) | 2002-04-16 | 2003-04-11 | Substituted indoles |
| US10/511,155 US7572796B2 (en) | 2002-04-16 | 2003-04-11 | Substituted indoles |
| AU2003224064A AU2003224064A1 (en) | 2002-04-16 | 2003-04-11 | Substituted indoles |
| ES03720455T ES2362871T3 (es) | 2002-04-16 | 2003-04-11 | Indoles sustituidos y su uso como inhibidores de la reabsorción de 5ht y como ligandos 5-ht. |
| DK03720455.9T DK1497279T3 (da) | 2002-04-16 | 2003-04-11 | Substituerede indoler og deres anvendelse som 5HT-reuptake-inhibitorer og som 5HT-ligander |
| AT03720455T ATE501133T1 (de) | 2002-04-16 | 2003-04-11 | Substituierte indole und deren verwendung als 5ht-wiederaufnahme inhibitoren und als 5ht liganden |
| PCT/EP2003/003806 WO2003087086A2 (de) | 2002-04-16 | 2003-04-11 | Substituierte indole und deren verwendung als 5ht-wiederaufnahme inhibitoren und als 5ht liganden |
| DE50313528T DE50313528D1 (de) | 2002-04-16 | 2003-04-11 | Substituierte indole und deren verwendung als 5ht-wiederaufnahme inhibitoren und als 5ht liganden |
| JP2003584042A JP2005523310A (ja) | 2002-04-16 | 2003-04-11 | 置換インドール |
| EP03720455A EP1497279B1 (de) | 2002-04-16 | 2003-04-11 | Substituierte indole und deren verwendung als 5ht-wiederaufnahme inhibitoren und als 5ht liganden |
| US12/245,416 US8058277B2 (en) | 2002-04-16 | 2008-10-03 | Substituted indoles |
| US12/511,320 US20090291963A1 (en) | 2002-04-16 | 2009-07-29 | Substituted indoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10217006A DE10217006A1 (de) | 2002-04-16 | 2002-04-16 | Substituierte Indole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10217006A1 true DE10217006A1 (de) | 2003-11-06 |
Family
ID=28798485
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10217006A Withdrawn DE10217006A1 (de) | 2002-04-16 | 2002-04-16 | Substituierte Indole |
| DE50313528T Expired - Lifetime DE50313528D1 (de) | 2002-04-16 | 2003-04-11 | Substituierte indole und deren verwendung als 5ht-wiederaufnahme inhibitoren und als 5ht liganden |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50313528T Expired - Lifetime DE50313528D1 (de) | 2002-04-16 | 2003-04-11 | Substituierte indole und deren verwendung als 5ht-wiederaufnahme inhibitoren und als 5ht liganden |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US7572796B2 (enExample) |
| EP (1) | EP1497279B1 (enExample) |
| JP (1) | JP2005523310A (enExample) |
| AT (1) | ATE501133T1 (enExample) |
| AU (1) | AU2003224064A1 (enExample) |
| CA (1) | CA2482655C (enExample) |
| DE (2) | DE10217006A1 (enExample) |
| DK (1) | DK1497279T3 (enExample) |
| ES (1) | ES2362871T3 (enExample) |
| WO (1) | WO2003087086A2 (enExample) |
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| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| DE10259244A1 (de) * | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | N-(Indolethyl-)cycloamin-Verbindungen |
| ES2280824T3 (es) * | 2002-12-20 | 2007-09-16 | Merck Patent Gmbh | Benzodioxepinas substituidas. |
| AU2004303461B2 (en) * | 2003-12-23 | 2011-04-28 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-benzyl amine derivatives as SSRI |
| AR052308A1 (es) * | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| EP2400300A1 (en) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Method of screening preventives/remedies for stress urinary incontinence |
| BRPI0515477A (pt) * | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos bicìclicos e o uso dos mesmos como inibidores de estaroil-coa-desaturase (scd) |
| AR051026A1 (es) | 2004-09-20 | 2006-12-13 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| WO2006101521A2 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| US7951805B2 (en) | 2004-09-20 | 2011-05-31 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| AU2005286647A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| AU2005286846A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| EP2316458A1 (en) | 2004-09-20 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| TW200630337A (en) * | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| DE602005022113D1 (de) * | 2005-01-07 | 2010-08-12 | Hoffmann La Roche | Phenyl)methanon-derivate als glycin-transporter 1 (glyt-1) hemmer zur behandlung von neurologischen und neuropsychiatrischen erkrankungen |
| DE102005019670A1 (de) * | 2005-04-26 | 2006-11-02 | Merck Patent Gmbh | Verfahren zur Herstellung von (5-(4-[4-(5-Cyano-3-indolyl)-butyl)-1-piperazinyl)-benzofuran-2-carboxamid |
| JP2009513563A (ja) * | 2005-06-03 | 2009-04-02 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトのステアロイル−CoAデサチュラーゼ阻害剤としてのアミノチアゾール誘導体 |
| TW200800959A (en) * | 2005-06-10 | 2008-01-01 | Wyeth Corp | Piperazine-piperidine antagonists and agonists of the 5-HT1a receptor |
| MX2007015772A (es) | 2005-06-17 | 2008-02-22 | Wyeth Corp | Compuestos utiles como inhibidores de serotonina y agonistas y antagonistas de 5-ht-1a. |
| AR054393A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
| US7629473B2 (en) * | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
| WO2007007910A1 (ja) * | 2005-07-13 | 2007-01-18 | Banyu Pharmaceutical Co., Ltd. | ヘテロ環置換ベンズイミダゾール誘導体 |
| RU2008127501A (ru) * | 2006-01-13 | 2010-02-20 | Вайет (Us) | Сульфонилзамещенные 1н-индолы в качастве лигандов 5-гидрокситриптаминовых рецепторов |
| US8247442B2 (en) * | 2006-03-29 | 2012-08-21 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use |
| US8791264B2 (en) * | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| WO2007118854A1 (en) * | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Benzenesulfonamide compounds and the use thereof |
| WO2007132841A1 (ja) | 2006-05-16 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物およびその用途 |
| WO2008015516A1 (en) * | 2006-07-28 | 2008-02-07 | Pfizer Products Inc. | Fused tricyclic heterocycles for the treatment of schizophrenia |
| US8399486B2 (en) | 2007-04-09 | 2013-03-19 | Purdue Pharma L.P. | Benzenesulfonyl compounds and the use thereof |
| JP2010527915A (ja) * | 2007-04-26 | 2010-08-19 | アバロン ファーマシューティカルズ,インコーポレイテッド | 多重環化合物及びその用途 |
| EP2178842A2 (en) | 2007-08-22 | 2010-04-28 | Abbott GmbH & Co. KG | 4-benzylaminoquinolines, pharmaceutical compositions containing them and their use |
| WO2009040659A2 (en) * | 2007-09-28 | 2009-04-02 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| AU2009212259A1 (en) | 2008-02-07 | 2009-08-13 | Abbott Laboratories | Amide derivatives as positive allosteric modulators and methods of use thereof |
| EP2527328A1 (en) * | 2008-04-01 | 2012-11-28 | Abbott GmbH & Co. KG | Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| GB0813142D0 (en) | 2008-07-17 | 2008-08-27 | Glaxo Group Ltd | Novel compounds |
| GB0813144D0 (en) | 2008-07-17 | 2008-08-27 | Glaxo Group Ltd | Novel compounds |
| CN102498095A (zh) | 2009-02-05 | 2012-06-13 | 国立大学法人京都大学 | 二氢吲哚衍生物 |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| EP2413696A4 (en) * | 2009-04-03 | 2012-10-24 | Sinai School Medicine | COMPOSITIONS FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| US8912220B2 (en) * | 2009-08-10 | 2014-12-16 | Galenea Pharmaceuticals | Compounds and methods of use thereof |
| TWI535440B (zh) * | 2009-10-26 | 2016-06-01 | Lg生命科學有限公司 | 包括吲哚化合物之醫藥組成物 |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| WO2011106039A1 (en) * | 2010-02-24 | 2011-09-01 | Research Triangle Institute | Arylpiperazone opioid receptor antagonists |
| WO2012014127A1 (en) | 2010-07-30 | 2012-02-02 | Ranbaxy Laboratories Limited | 5-lipoxygenase inhibitors |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| PL395470A1 (pl) | 2011-06-29 | 2013-01-07 | Adamed Spólka Z Ograniczona Odpowiedzialnoscia | Sulfonamidowe pochodne amin alicyklicznych do leczenia chorób osrodkowego ukladu nerwowego |
| CN103889968A (zh) | 2011-08-05 | 2014-06-25 | 艾伯维德国有限责任两合公司 | 氨基苯并二氢吡喃、氨基苯并二氢噻喃及氨基-1,2,3,4-四氢喹啉衍生物,包含这些化合物的药用组合物,及其在治疗中的用途 |
| MX2014006004A (es) | 2011-11-18 | 2015-04-16 | Abbvie Deutschland | Derivados de aminobenzociclohepteno, aminotetralina, aminoindano y fenalcilamina n-sustituidas, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| JO3425B1 (ar) | 2013-07-15 | 2019-10-20 | Novartis Ag | مشتقات البابيريدينيل-اندول واستخدامها كعامل متمم لمثبطات b |
| AU2014336154A1 (en) | 2013-10-17 | 2016-04-28 | AbbVie Deutschland GmbH & Co. KG | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| JP2016537323A (ja) | 2013-10-17 | 2016-12-01 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | アミノクロマン誘導体、アミノチオクロマン誘導体およびアミノ−1,2,3,4−テトラヒドロキノリン誘導体、これらを含有する医薬組成物、および治療におけるこれらの使用 |
| US9550754B2 (en) | 2014-09-11 | 2017-01-24 | AbbVie Deutschland GmbH & Co. KG | 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US10633336B2 (en) | 2014-12-19 | 2020-04-28 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
| US10752588B2 (en) | 2014-12-19 | 2020-08-25 | The Broad Institute, Inc. | Dopamine D2 receptor ligands |
| EP3597186B1 (en) | 2015-01-05 | 2021-12-08 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Myc g-quadruplex stabilizing small molecules and their use |
| CA3077383A1 (en) | 2017-09-29 | 2019-04-04 | Sunshine Lake Pharma Co., Ltd. | Substituted pyrimidine piperazine compound and use thereof |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| CN112851641B (zh) * | 2019-11-28 | 2023-08-15 | 广东东阳光药业股份有限公司 | 嘧啶苯甲酰胺化合物的盐酸盐及其用途 |
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| GB132130A (enExample) | 1917-11-10 | |||
| FR1344579A (fr) | 1961-11-23 | 1963-11-29 | Sandoz Sa | Nouveaux dérivés de l'indole et leur préparation |
| CH421107A (de) | 1963-06-04 | 1966-09-30 | Sandoz Ag | Verfahren zur Herstellung neuer heterocyclischer Verbindungen |
| JPS63301862A (ja) * | 1987-01-23 | 1988-12-08 | Yoshitomi Pharmaceut Ind Ltd | 5−ヒドロキシインドール−3−カルボン酸アミド化合物 |
| EP0299076A4 (en) * | 1987-01-23 | 1991-01-09 | Yoshitomi Pharmaceutical Industries, Ltd. | 5-hydroxyindole-3-carboxamide compound and medicinal use thereof |
| DE4101686A1 (de) | 1991-01-22 | 1992-07-23 | Merck Patent Gmbh | Indolderivate |
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| DE4333254A1 (de) * | 1993-09-30 | 1995-04-06 | Merck Patent Gmbh | Piperidine und Piperazine |
| FR2712591B1 (fr) * | 1993-11-19 | 1996-02-09 | Pf Medicament | Nouvelles arylpipérazines dérivées d'indole, leur préparation et leur utilisation thérapeutique. |
| DE4414113A1 (de) * | 1994-04-22 | 1995-10-26 | Merck Patent Gmbh | 3-Indolylpiperidine |
| CA2194984C (en) | 1994-07-26 | 2002-07-02 | John Eugene Macor | 4-indole derivatives as serotonin agonists and antagonists |
| DE59504622D1 (de) * | 1994-10-31 | 1999-02-04 | Merck Patent Gmbh | Benzylpiperidinderivate mit hoher Affinität zu Bindungsstellen von Aminosäure-Rezeptoren |
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| US5962473A (en) | 1996-08-16 | 1999-10-05 | Eli Lilly And Company | Methods of treating or ameliorating the symptoms of common cold or allergic rhinitis with serotonin 5-HT1F |
| DE19730989A1 (de) * | 1997-07-18 | 1999-01-21 | Merck Patent Gmbh | Piperazin-Derivate |
| DE69919436T2 (de) * | 1998-04-16 | 2005-09-15 | Pfizer Products Inc., Groton | N-Acyl und N-Aroyl Aralkylamide |
| US6399619B1 (en) * | 1999-04-06 | 2002-06-04 | Merck & Co., Inc. | Pyrrolidine modulators of chemokine receptor activity |
| TW518218B (en) * | 1999-05-27 | 2003-01-21 | Merck Patent Gmbh | Pharmaceutical compositions comprising 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine or its physiologically acceptable salts for use in the treatment of sub-type anxiety disorders |
| DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
| DE19934432A1 (de) * | 1999-07-22 | 2001-02-01 | Merck Patent Gmbh | Indolderivate |
| FR2797874B1 (fr) * | 1999-08-27 | 2002-03-29 | Adir | Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE10041574A1 (de) * | 2000-08-24 | 2002-03-07 | Merck Patent Gmbh | Chromenonderivate |
| GB0203778D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| AU2003268464A1 (en) * | 2002-09-03 | 2004-03-29 | Scios Inc. | INDOLE-TYPE DERIVATIVES AS INHIBITORS OF p38 KINASE |
| US6844362B2 (en) | 2002-10-11 | 2005-01-18 | Pfizer Inc | Indole derivatives useful for the treatment of diseases |
| EP1440966A1 (en) | 2003-01-10 | 2004-07-28 | Pfizer Limited | Indole derivatives useful for the treatment of diseases |
| EP1460064A1 (en) | 2003-03-14 | 2004-09-22 | Pfizer Limited | Indole-2-carboxamide derivatives useful as beta-2 agonists |
-
2002
- 2002-04-16 DE DE10217006A patent/DE10217006A1/de not_active Withdrawn
-
2003
- 2003-04-11 JP JP2003584042A patent/JP2005523310A/ja active Pending
- 2003-04-11 DK DK03720455.9T patent/DK1497279T3/da active
- 2003-04-11 DE DE50313528T patent/DE50313528D1/de not_active Expired - Lifetime
- 2003-04-11 AT AT03720455T patent/ATE501133T1/de active
- 2003-04-11 US US10/511,155 patent/US7572796B2/en not_active Expired - Fee Related
- 2003-04-11 WO PCT/EP2003/003806 patent/WO2003087086A2/de not_active Ceased
- 2003-04-11 EP EP03720455A patent/EP1497279B1/de not_active Expired - Lifetime
- 2003-04-11 CA CA2482655A patent/CA2482655C/en not_active Expired - Fee Related
- 2003-04-11 ES ES03720455T patent/ES2362871T3/es not_active Expired - Lifetime
- 2003-04-11 AU AU2003224064A patent/AU2003224064A1/en not_active Abandoned
-
2008
- 2008-10-03 US US12/245,416 patent/US8058277B2/en not_active Expired - Fee Related
-
2009
- 2009-07-29 US US12/511,320 patent/US20090291963A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20050153980A1 (en) | 2005-07-14 |
| US20090054459A1 (en) | 2009-02-26 |
| EP1497279A2 (de) | 2005-01-19 |
| AU2003224064A8 (en) | 2003-10-27 |
| CA2482655A1 (en) | 2003-10-23 |
| JP2005523310A (ja) | 2005-08-04 |
| CA2482655C (en) | 2011-08-16 |
| US8058277B2 (en) | 2011-11-15 |
| ATE501133T1 (de) | 2011-03-15 |
| DK1497279T3 (da) | 2011-06-14 |
| US7572796B2 (en) | 2009-08-11 |
| US20090291963A1 (en) | 2009-11-26 |
| ES2362871T3 (es) | 2011-07-14 |
| WO2003087086A2 (de) | 2003-10-23 |
| AU2003224064A1 (en) | 2003-10-27 |
| DE50313528D1 (de) | 2011-04-21 |
| WO2003087086A3 (de) | 2004-07-22 |
| EP1497279B1 (de) | 2011-03-09 |
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