RU2500677C2 - Производные замещенного индола - Google Patents
Производные замещенного индола Download PDFInfo
- Publication number
- RU2500677C2 RU2500677C2 RU2010138838/04A RU2010138838A RU2500677C2 RU 2500677 C2 RU2500677 C2 RU 2500677C2 RU 2010138838/04 A RU2010138838/04 A RU 2010138838/04A RU 2010138838 A RU2010138838 A RU 2010138838A RU 2500677 C2 RU2500677 C2 RU 2500677C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- dimethylamino
- indol
- piperidin
- phenylpiperidin
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title claims abstract 15
- 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract 2
- 125000001041 indolyl group Chemical group 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims abstract 2
- 108010020615 nociceptin receptor Proteins 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims abstract 2
- -1 cyclic aromatic radical Chemical class 0.000 claims 35
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 10
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 150000003254 radicals Chemical class 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- DAVFFANIZHZZJR-UHFFFAOYSA-N 1-[2-[(5-methoxy-1h-indol-3-yl)methyl-methylamino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C12=CC(OC)=CC=C2NC=C1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 DAVFFANIZHZZJR-UHFFFAOYSA-N 0.000 claims 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 3
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 2
- SDYYCZGLHXWYAP-UHFFFAOYSA-N 1-[2-[(1,2-dimethylindol-3-yl)methyl-methylamino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound CC=1N(C)C2=CC=CC=C2C=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 SDYYCZGLHXWYAP-UHFFFAOYSA-N 0.000 claims 2
- LYGPZEATHDSVTP-UHFFFAOYSA-N 1-[2-[(1-benzyl-5-methoxy-2-methylindol-3-yl)methyl-methylamino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound CC1=C(CN(C)CCN2CCC(CC2)(N(C)C)C=2C=CC=CC=2)C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 LYGPZEATHDSVTP-UHFFFAOYSA-N 0.000 claims 2
- KDAPWPPEWBALMZ-UHFFFAOYSA-N 1-[2-[(5-chloro-1h-indol-3-yl)methyl-methylamino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C=1NC2=CC=C(Cl)C=C2C=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 KDAPWPPEWBALMZ-UHFFFAOYSA-N 0.000 claims 2
- ZOUCEMVEMBRLAS-UHFFFAOYSA-N 1-[2-[(5-chloro-1h-indol-3-yl)methylamino]ethyl]-n,n-dimethyl-4-thiophen-2-ylpiperidin-4-amine Chemical compound C1CN(CCNCC=2C3=CC(Cl)=CC=C3NC=2)CCC1(N(C)C)C1=CC=CS1 ZOUCEMVEMBRLAS-UHFFFAOYSA-N 0.000 claims 2
- RYTISKJHIGCPNM-UHFFFAOYSA-N 1-[2-[(5-methoxy-1h-indol-3-yl)methylamino]ethyl]-n,n-dimethyl-4-thiophen-2-ylpiperidin-4-amine Chemical compound C12=CC(OC)=CC=C2NC=C1CNCCN(CC1)CCC1(N(C)C)C1=CC=CS1 RYTISKJHIGCPNM-UHFFFAOYSA-N 0.000 claims 2
- XKPOKDKPDLQOGR-UHFFFAOYSA-N 1-[2-[1h-indol-3-ylmethyl(methyl)amino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C=1NC2=CC=CC=C2C=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 XKPOKDKPDLQOGR-UHFFFAOYSA-N 0.000 claims 2
- VEFZTKZLWLNPEU-UHFFFAOYSA-N 1-[2-[1h-indol-4-ylmethyl(methyl)amino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C=1C=CC=2NC=CC=2C=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 VEFZTKZLWLNPEU-UHFFFAOYSA-N 0.000 claims 2
- ZECNAZWWPHRNLQ-UHFFFAOYSA-N 1-[2-[1h-indol-6-ylmethyl(methyl)amino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C=1C=C2C=CNC2=CC=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 ZECNAZWWPHRNLQ-UHFFFAOYSA-N 0.000 claims 2
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 claims 2
- GLTZHSDOJGAPGU-UHFFFAOYSA-N 6-chloro-n-[2-[4-(dimethylamino)-4-phenylpiperidin-1-yl]ethyl]-n-methyl-2,3,4,9-tetrahydro-1h-carbazole-1-carboxamide Chemical compound C1CN(CCN(C)C(=O)C2C3=C(C4=CC(Cl)=CC=C4N3)CCC2)CCC1(N(C)C)C1=CC=CC=C1 GLTZHSDOJGAPGU-UHFFFAOYSA-N 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 150000005840 aryl radicals Chemical class 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- GUMAMWSSCLCZAB-UHFFFAOYSA-N n,n-dimethyl-1-[2-[methyl-[(6-propan-2-yl-1h-indol-3-yl)methyl]amino]ethyl]-4-phenylpiperidin-4-amine Chemical compound C=1NC2=CC(C(C)C)=CC=C2C=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 GUMAMWSSCLCZAB-UHFFFAOYSA-N 0.000 claims 2
- DSFBRRNSTBKUNM-UHFFFAOYSA-N n-[2-[4-(dimethylamino)-4-phenylpiperidin-1-yl]ethyl]-2-(6-fluoro-1h-indol-3-yl)-n-methylacetamide Chemical compound C1CN(CCN(C)C(=O)CC=2C3=CC=C(F)C=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 DSFBRRNSTBKUNM-UHFFFAOYSA-N 0.000 claims 2
- SXZWTCAYIXJEOS-UHFFFAOYSA-N n-[2-[4-(dimethylamino)-4-phenylpiperidin-1-yl]ethyl]-3-(1h-indol-3-yl)-n,4-dimethylpentanamide Chemical compound C=1NC2=CC=CC=C2C=1C(C(C)C)CC(=O)N(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 SXZWTCAYIXJEOS-UHFFFAOYSA-N 0.000 claims 2
- OCXWOKQQQRIQKQ-UHFFFAOYSA-N n-[2-[4-(dimethylamino)-4-phenylpiperidin-1-yl]ethyl]-5-fluoro-n-methyl-1h-indole-2-carboxamide Chemical compound C1CN(CCN(C)C(=O)C=2NC3=CC=C(F)C=C3C=2)CCC1(N(C)C)C1=CC=CC=C1 OCXWOKQQQRIQKQ-UHFFFAOYSA-N 0.000 claims 2
- AUKNFZRIIILDET-UHFFFAOYSA-N n-[2-[4-(dimethylamino)-4-phenylpiperidin-1-yl]ethyl]-n-methyl-1h-indole-6-carboxamide Chemical compound C1CN(CCN(C)C(=O)C=2C=C3NC=CC3=CC=2)CCC1(N(C)C)C1=CC=CC=C1 AUKNFZRIIILDET-UHFFFAOYSA-N 0.000 claims 2
- WIZSXFXXNUWCOE-UHFFFAOYSA-N n-[2-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]ethyl]-3-(1h-indol-3-yl)-4-methylpentanamide Chemical compound C=1NC2=CC=CC=C2C=1C(C(C)C)CC(=O)NCCN(CC1)CCC1(N(C)C)C1=CC=CS1 WIZSXFXXNUWCOE-UHFFFAOYSA-N 0.000 claims 2
- YEJTVAXRWBWLGQ-UHFFFAOYSA-N n-[2-[4-butyl-4-(dimethylamino)piperidin-1-yl]ethyl]-2-(6-fluoro-1h-indol-3-yl)-n-methylacetamide Chemical compound C1CC(CCCC)(N(C)C)CCN1CCN(C)C(=O)CC1=CNC2=CC(F)=CC=C12 YEJTVAXRWBWLGQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229940005483 opioid analgesics Drugs 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 2
- 239000000955 prescription drug Substances 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- BPRZKJJPHKRYFH-UHFFFAOYSA-N 1-[2-(1h-indol-3-ylmethylamino)ethyl]-n,n-dimethyl-4-thiophen-2-ylpiperidin-4-amine Chemical compound C1CN(CCNCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CS1 BPRZKJJPHKRYFH-UHFFFAOYSA-N 0.000 claims 1
- CLTCEERPDHANHV-UHFFFAOYSA-N 1-[2-(1h-indol-5-ylmethylamino)ethyl]-n,n-dimethyl-4-thiophen-2-ylpiperidin-4-amine Chemical compound C1CN(CCNCC=2C=C3C=CNC3=CC=2)CCC1(N(C)C)C1=CC=CS1 CLTCEERPDHANHV-UHFFFAOYSA-N 0.000 claims 1
- KDDGRKMLSAKHDH-UHFFFAOYSA-N 1-[2-[(1,2-dimethylindol-3-yl)methylamino]ethyl]-n,n-dimethyl-4-thiophen-2-ylpiperidin-4-amine Chemical compound C1CN(CCNCC=2C3=CC=CC=C3N(C)C=2C)CCC1(N(C)C)C1=CC=CS1 KDDGRKMLSAKHDH-UHFFFAOYSA-N 0.000 claims 1
- VHSKKUSQBLXPFP-UHFFFAOYSA-N 1-[2-[(1-benzyl-5-methoxy-2-methylindol-3-yl)methylamino]ethyl]-n,n-dimethyl-4-thiophen-2-ylpiperidin-4-amine Chemical compound CC1=C(CNCCN2CCC(CC2)(N(C)C)C=2SC=CC=2)C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 VHSKKUSQBLXPFP-UHFFFAOYSA-N 0.000 claims 1
- YSGWYMIEOCTQNJ-UHFFFAOYSA-N 1-[2-[(5-bromo-1h-indol-3-yl)methyl-methylamino]ethyl]-4-butyl-n,n-dimethylpiperidin-4-amine Chemical compound C1CC(CCCC)(N(C)C)CCN1CCN(C)CC1=CNC2=CC=C(Br)C=C12 YSGWYMIEOCTQNJ-UHFFFAOYSA-N 0.000 claims 1
- NLMGZWMPAJIATG-UHFFFAOYSA-N 1-[2-[(5-bromo-1h-indol-3-yl)methyl-methylamino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C=1NC2=CC=C(Br)C=C2C=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 NLMGZWMPAJIATG-UHFFFAOYSA-N 0.000 claims 1
- NSGZTYVDEIVMNX-UHFFFAOYSA-N 1-[2-[1h-indol-5-ylmethyl(methyl)amino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C=1C=C2NC=CC2=CC=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 NSGZTYVDEIVMNX-UHFFFAOYSA-N 0.000 claims 1
- ZFMRHHQMBQAHTE-UHFFFAOYSA-N 1-[2-[[2-(4-fluorophenyl)-1h-indol-3-yl]methyl-methylamino]ethyl]-n,n-dimethyl-4-phenylpiperidin-4-amine Chemical compound C=1C=C(F)C=CC=1C=1NC2=CC=CC=C2C=1CN(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 ZFMRHHQMBQAHTE-UHFFFAOYSA-N 0.000 claims 1
- ZKIJPVQJIMGDAN-UHFFFAOYSA-N 1-[3-[(1,2-dimethylindol-3-yl)methyl-methylamino]propyl]-n,n-dimethyl-4-thiophen-2-ylpiperidin-4-amine Chemical compound CC=1N(C)C2=CC=CC=C2C=1CN(C)CCCN(CC1)CCC1(N(C)C)C1=CC=CS1 ZKIJPVQJIMGDAN-UHFFFAOYSA-N 0.000 claims 1
- NFDSQBOAENBSFZ-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)-4-phenylpiperidine-1-carbonyl]-2,3-dihydroindol-1-yl]-2-(6-fluoro-1h-indol-3-yl)ethanone Chemical compound C1CN(C(=O)C2C3=CC=CC=C3N(C(=O)CC=3C4=CC=C(F)C=C4NC=3)C2)CCC1(N(C)C)C1=CC=CC=C1 NFDSQBOAENBSFZ-UHFFFAOYSA-N 0.000 claims 1
- YKONAAJIUWYMAA-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)-4-phenylpiperidine-1-carbonyl]-2,3-dihydroindol-1-yl]-3-(1h-indol-3-yl)-4-methylpentan-1-one Chemical compound C=1NC2=CC=CC=C2C=1C(C(C)C)CC(=O)N(C1=CC=CC=C11)CC1C(=O)N(CC1)CCC1(N(C)C)C1=CC=CC=C1 YKONAAJIUWYMAA-UHFFFAOYSA-N 0.000 claims 1
- KKQBXQPXCKGZNZ-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)-4-phenylpiperidine-1-carbonyl]piperidin-1-yl]-2-(6-fluoro-1h-indol-3-yl)ethanone Chemical compound C1CN(C(=O)C2CN(CCC2)C(=O)CC=2C3=CC=C(F)C=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 KKQBXQPXCKGZNZ-UHFFFAOYSA-N 0.000 claims 1
- ZWUSTCHZAHKNKU-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)-4-phenylpiperidine-1-carbonyl]piperidin-1-yl]-3-(1-methylindol-3-yl)propan-1-one Chemical compound C1CN(C(=O)C2CN(CCC2)C(=O)CCC=2C3=CC=CC=C3N(C)C=2)CCC1(N(C)C)C1=CC=CC=C1 ZWUSTCHZAHKNKU-UHFFFAOYSA-N 0.000 claims 1
- HJSBDIRAQGXBDE-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)-4-phenylpiperidine-1-carbonyl]piperidin-1-yl]-3-(1h-indol-3-yl)-4-methylpentan-1-one Chemical compound C=1NC2=CC=CC=C2C=1C(C(C)C)CC(=O)N(C1)CCCC1C(=O)N(CC1)CCC1(N(C)C)C1=CC=CC=C1 HJSBDIRAQGXBDE-UHFFFAOYSA-N 0.000 claims 1
- ZZUDSUMWCDCZGQ-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)-4-phenylpiperidine-1-carbonyl]piperidin-1-yl]-3-(1h-indol-3-yl)butan-1-one Chemical compound C=1NC2=CC=CC=C2C=1C(C)CC(=O)N(C1)CCCC1C(=O)N(CC1)CCC1(N(C)C)C1=CC=CC=C1 ZZUDSUMWCDCZGQ-UHFFFAOYSA-N 0.000 claims 1
- SPGUYVPEXLSAJM-UHFFFAOYSA-N 1-[3-[4-(dimethylamino)-4-phenylpiperidine-1-carbonyl]piperidin-1-yl]-3-(1h-indol-3-yl)propan-1-one Chemical compound C1CN(C(=O)C2CN(CCC2)C(=O)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 SPGUYVPEXLSAJM-UHFFFAOYSA-N 0.000 claims 1
- FQXOBOSLXVTBSY-UHFFFAOYSA-N 1-[4-(dimethylamino)-4-phenylpiperidin-1-yl]-2-[1h-indol-5-ylmethyl(methyl)amino]-3-methylbutan-1-one Chemical compound C=1C=C2NC=CC2=CC=1CN(C)C(C(C)C)C(=O)N(CC1)CCC1(N(C)C)C1=CC=CC=C1 FQXOBOSLXVTBSY-UHFFFAOYSA-N 0.000 claims 1
- CMLQUCODDTWZDU-UHFFFAOYSA-N 1-[4-(dimethylamino)-4-phenylpiperidin-1-yl]-3-(1h-indol-3-ylmethylamino)propan-1-one Chemical compound C1CN(C(=O)CCNCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CC=C1 CMLQUCODDTWZDU-UHFFFAOYSA-N 0.000 claims 1
- LWFZHTTWEMCKBU-UHFFFAOYSA-N 1-[4-(dimethylamino)-4-phenylpiperidin-1-yl]-3-(1h-indol-5-ylmethylamino)propan-1-one Chemical compound C1CN(C(=O)CCNCC=2C=C3C=CNC3=CC=2)CCC1(N(C)C)C1=CC=CC=C1 LWFZHTTWEMCKBU-UHFFFAOYSA-N 0.000 claims 1
- JNUGYWAMGKYHBT-UHFFFAOYSA-N 1-[4-(dimethylamino)-4-phenylpiperidin-1-yl]-3-(1h-indol-6-ylmethylamino)propan-1-one Chemical compound C1CN(C(=O)CCNCC=2C=C3NC=CC3=CC=2)CCC1(N(C)C)C1=CC=CC=C1 JNUGYWAMGKYHBT-UHFFFAOYSA-N 0.000 claims 1
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- AUZDCMPSSRJRCO-UHFFFAOYSA-N 1-[4-(dimethylamino)-4-phenylpiperidin-1-yl]-3-[(2-methyl-1h-indol-3-yl)methylamino]propan-1-one Chemical compound C1CN(C(=O)CCNCC=2C3=CC=CC=C3NC=2C)CCC1(N(C)C)C1=CC=CC=C1 AUZDCMPSSRJRCO-UHFFFAOYSA-N 0.000 claims 1
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- KYFSKWCCMKARSR-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]-3-oxo-1-phenylpropyl]-3-(1h-indol-3-yl)-4-methylpentanamide Chemical compound C=1NC2=CC=CC=C2C=1C(C(C)C)CC(=O)NC(C=1C=CC=CC=1)CC(=O)N(CC1)CCC1(N(C)C)C1=CC=CS1 KYFSKWCCMKARSR-UHFFFAOYSA-N 0.000 claims 1
- CVNHJLLTKIUHQC-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-2-(6-fluoro-1h-indol-3-yl)-n-methylacetamide Chemical compound C1CN(CCCN(C)C(=O)CC=2C3=CC=C(F)C=C3NC=2)CCC1(N(C)C)C1=CC=CS1 CVNHJLLTKIUHQC-UHFFFAOYSA-N 0.000 claims 1
- FZMBEKXWDVRUJH-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-3-(1h-indol-3-yl)-n,4-dimethylpentanamide Chemical compound C=1NC2=CC=CC=C2C=1C(C(C)C)CC(=O)N(C)CCCN(CC1)CCC1(N(C)C)C1=CC=CS1 FZMBEKXWDVRUJH-UHFFFAOYSA-N 0.000 claims 1
- CSBJIVRXMQZCCJ-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-3-(1h-indol-3-yl)-n-methylbutanamide Chemical compound C=1NC2=CC=CC=C2C=1C(C)CC(=O)N(C)CCCN(CC1)CCC1(N(C)C)C1=CC=CS1 CSBJIVRXMQZCCJ-UHFFFAOYSA-N 0.000 claims 1
- DMYHYIJJGIAJNA-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-3-(1h-indol-3-yl)-n-methylpropanamide Chemical compound C1CN(CCCN(C)C(=O)CCC=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CS1 DMYHYIJJGIAJNA-UHFFFAOYSA-N 0.000 claims 1
- CZFOXBDTXZWTTA-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-5-methoxy-n-methyl-1h-indole-2-carboxamide Chemical compound C=1C2=CC(OC)=CC=C2NC=1C(=O)N(C)CCCN(CC1)CCC1(N(C)C)C1=CC=CS1 CZFOXBDTXZWTTA-UHFFFAOYSA-N 0.000 claims 1
- AAXNKGAAWBMLOD-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-n,1-dimethylindole-4-carboxamide Chemical compound C=1C=CC=2N(C)C=CC=2C=1C(=O)N(C)CCCN(CC1)CCC1(N(C)C)C1=CC=CS1 AAXNKGAAWBMLOD-UHFFFAOYSA-N 0.000 claims 1
- HBEYVGSNZMPYTN-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-n,1-dimethylindole-6-carboxamide Chemical compound C=1C=C2C=CN(C)C2=CC=1C(=O)N(C)CCCN(CC1)CCC1(N(C)C)C1=CC=CS1 HBEYVGSNZMPYTN-UHFFFAOYSA-N 0.000 claims 1
- TUJIEIMFVPLVBB-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-n-methyl-1h-indole-3-carboxamide Chemical compound C1CN(CCCN(C)C(=O)C=2C3=CC=CC=C3NC=2)CCC1(N(C)C)C1=CC=CS1 TUJIEIMFVPLVBB-UHFFFAOYSA-N 0.000 claims 1
- WNXBAJLYLKOQPR-UHFFFAOYSA-N n-[3-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]propyl]-n-methyl-1h-indole-6-carboxamide Chemical compound C1CN(CCCN(C)C(=O)C=2C=C3NC=CC3=CC=2)CCC1(N(C)C)C1=CC=CS1 WNXBAJLYLKOQPR-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- NOWKSZRSMXHPHY-UHFFFAOYSA-N n-methyl-n-[2-(4-phenyl-4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]-1h-indole-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C=1C(=O)N(C)CCN(CC1)CCC1(C=1C=CC=CC=1)N1CCCC1 NOWKSZRSMXHPHY-UHFFFAOYSA-N 0.000 claims 1
- YLLVZWAITXFEII-UHFFFAOYSA-N n-methyl-n-[2-(4-phenyl-4-pyrrolidin-1-ylpiperidin-1-yl)ethyl]-1h-indole-6-carboxamide Chemical compound C=1C=C2C=CNC2=CC=1C(=O)N(C)CCN(CC1)CCC1(C=1C=CC=CC=1)N1CCCC1 YLLVZWAITXFEII-UHFFFAOYSA-N 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000002981 neuropathic effect Effects 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 230000003957 neurotransmitter release Effects 0.000 claims 1
- 239000002664 nootropic agent Substances 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 231100000886 tinnitus Toxicity 0.000 claims 1
- 108020001612 μ-opioid receptors Proteins 0.000 claims 1
Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08003238 | 2008-02-22 | ||
| EP08003238.6 | 2008-02-22 | ||
| PCT/EP2009/001232 WO2009103552A1 (en) | 2008-02-22 | 2009-02-20 | Substituted indole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010138838A RU2010138838A (ru) | 2012-03-27 |
| RU2500677C2 true RU2500677C2 (ru) | 2013-12-10 |
Family
ID=39449548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010138838/04A RU2500677C2 (ru) | 2008-02-22 | 2009-02-20 | Производные замещенного индола |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US20090215828A1 (OSRAM) |
| EP (1) | EP2254883B1 (OSRAM) |
| JP (1) | JP5635914B2 (OSRAM) |
| CN (1) | CN102015683B (OSRAM) |
| AR (1) | AR070398A1 (OSRAM) |
| AU (1) | AU2009216920B2 (OSRAM) |
| CA (1) | CA2716270C (OSRAM) |
| CL (1) | CL2009000404A1 (OSRAM) |
| IL (1) | IL207684A (OSRAM) |
| MX (1) | MX2010009045A (OSRAM) |
| PE (1) | PE20091490A1 (OSRAM) |
| RU (1) | RU2500677C2 (OSRAM) |
| WO (1) | WO2009103552A1 (OSRAM) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR070398A1 (es) | 2008-02-22 | 2010-03-31 | Gruenenthal Chemie | Derivados sustituidos de indol |
| HRP20161133T1 (hr) | 2008-07-23 | 2016-12-02 | Arena Pharmaceuticals, Inc. | DERIVATI SUSPSTITUIRANE 1,2,3,4-TETRAHIDROCIKLOPENTA[b]INDOL-3-IL-OCTENE KISELINE KORISNI U LIJEČENJU AUTOIMUNIH I UPALNIH POREMEĆAJA |
| CN105816453B (zh) | 2008-08-27 | 2021-03-05 | 艾尼纳制药公司 | 用于治疗自身免疫性病症和炎性病症的作为s1p1受体激动剂的经取代的三环酸衍生物 |
| TW201020247A (en) * | 2008-11-06 | 2010-06-01 | Gruenenthal Gmbh | Substituierte disulfonamide |
| CA2786994C (en) | 2010-01-27 | 2018-01-16 | Arena Pharmaceuticals, Inc. | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| CN105503882B (zh) | 2010-03-03 | 2019-07-05 | 艾尼纳制药公司 | 制备s1p1受体调节剂及其晶体形式的方法 |
| US8536179B2 (en) | 2010-05-07 | 2013-09-17 | Glaxosmithkline Llc | Indoles |
| CA2854447A1 (en) | 2011-11-04 | 2013-05-10 | Glaxosmithkline Intellectual Property (No.2) Limited | Method of treatment |
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| AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| PL3310760T3 (pl) | 2015-06-22 | 2023-03-06 | Arena Pharmaceuticals, Inc. | Krystaliczna sól L-argininy kwasu (R)-2-(7-(4-cyklopentylo-3-(trifluorometylo)benzyloksy)- 1,2,3,4-tetrahydrocyklo-penta[b]indol-3-ilo)octowego do zastosowania w zaburzeniach związanych z receptorem S1P1 |
| CA3043206A1 (en) | 2016-11-18 | 2018-05-24 | Merck Sharp & Dohme Corp. | Indole derivatives useful as inhibitors of diacylglyceride o-acyltransferase 2 |
| JP2020507610A (ja) | 2017-02-16 | 2020-03-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 腸管外症状を伴う炎症性腸疾患の治療のための化合物および方法 |
| KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
| CN110770224B (zh) * | 2017-03-10 | 2022-11-18 | 罗格斯新泽西州立大学 | 作为外排泵抑制剂的吲哚衍生物 |
| AU2019280822A1 (en) | 2018-06-06 | 2021-01-07 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| EP3847158A1 (en) | 2018-09-06 | 2021-07-14 | Arena Pharmaceuticals, Inc. | Compounds useful in the treatment of autoimmune and inflammatory disorders |
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| SU1110380A3 (ru) * | 1977-12-01 | 1984-08-23 | Джон Вайс Энд Бразер Лимитед (Фирма) | Способ получени производных индола или их аддитивных солей |
| EP1242411B1 (en) * | 1999-12-20 | 2006-03-08 | Eli Lilly And Company | Indole derivatives for the treatment of depression and anxiety |
| RU2007147591A (ru) * | 2005-05-26 | 2009-07-10 | Новартис АГ (CH) | 3, 4-замещенные пиперидины в качестве ингибиторов ренина |
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| JP3314938B2 (ja) * | 1995-06-06 | 2002-08-19 | ファイザー・インコーポレーテッド | グリコーゲンホスホリラーゼ抑制剤としての置換されたｎ−（インドール−２−カルボニル）−グリシンアミド類および誘導体 |
| DE10153346A1 (de) | 2001-10-29 | 2004-04-22 | Grünenthal GmbH | Substituierte Indole |
| DE10252650A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| DE10252666A1 (de) | 2002-11-11 | 2004-08-05 | Grünenthal GmbH | N-Piperidyl-cyclohexan-Derivate |
| KR20050045927A (ko) * | 2003-11-12 | 2005-05-17 | 주식회사 엘지생명과학 | 멜라노코틴 수용체의 항진제 |
| CA2641817A1 (en) * | 2006-02-01 | 2007-08-09 | Solvay Pharmaceuticals Gmbh | Novel dual nk2/nk3-antagonists, pharmaceutical compositions comprising them and processes for their preparation |
| US20070219214A1 (en) * | 2006-02-01 | 2007-09-20 | Solvay Pharmaceuticals Gmbh | Dual NK2/NK3-antagonists, pharmaceutical compositions comprising them, and processes for their preparation |
| PE20081897A1 (es) * | 2007-03-29 | 2009-02-09 | Novartis Ag | 3-imidazolil-indoles para el tratamiento de enfermedades proliferativas |
| AR070398A1 (es) | 2008-02-22 | 2010-03-31 | Gruenenthal Chemie | Derivados sustituidos de indol |
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2009
- 2009-02-16 AR ARP090100544A patent/AR070398A1/es not_active Application Discontinuation
- 2009-02-19 US US12/388,977 patent/US20090215828A1/en not_active Abandoned
- 2009-02-20 WO PCT/EP2009/001232 patent/WO2009103552A1/en not_active Ceased
- 2009-02-20 CN CN200980115064.3A patent/CN102015683B/zh not_active Expired - Fee Related
- 2009-02-20 CL CL2009000404A patent/CL2009000404A1/es unknown
- 2009-02-20 MX MX2010009045A patent/MX2010009045A/es active IP Right Grant
- 2009-02-20 PE PE2009000247A patent/PE20091490A1/es not_active Application Discontinuation
- 2009-02-20 RU RU2010138838/04A patent/RU2500677C2/ru not_active IP Right Cessation
- 2009-02-20 JP JP2010547116A patent/JP5635914B2/ja not_active Expired - Fee Related
- 2009-02-20 AU AU2009216920A patent/AU2009216920B2/en not_active Ceased
- 2009-02-20 EP EP09713555.2A patent/EP2254883B1/en not_active Not-in-force
- 2009-02-20 CA CA2716270A patent/CA2716270C/en not_active Expired - Fee Related
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1110380A3 (ru) * | 1977-12-01 | 1984-08-23 | Джон Вайс Энд Бразер Лимитед (Фирма) | Способ получени производных индола или их аддитивных солей |
| EP1242411B1 (en) * | 1999-12-20 | 2006-03-08 | Eli Lilly And Company | Indole derivatives for the treatment of depression and anxiety |
| RU2007147591A (ru) * | 2005-05-26 | 2009-07-10 | Новартис АГ (CH) | 3, 4-замещенные пиперидины в качестве ингибиторов ренина |
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| US20130116283A1 (en) | 2013-05-09 |
| AU2009216920B2 (en) | 2013-06-13 |
| CN102015683A (zh) | 2011-04-13 |
| MX2010009045A (es) | 2010-09-24 |
| CL2009000404A1 (es) | 2010-04-16 |
| HK1149762A1 (en) | 2011-10-14 |
| WO2009103552A1 (en) | 2009-08-27 |
| IL207684A (en) | 2015-08-31 |
| EP2254883A1 (en) | 2010-12-01 |
| US20090215828A1 (en) | 2009-08-27 |
| CA2716270A1 (en) | 2009-08-27 |
| CA2716270C (en) | 2016-01-19 |
| RU2010138838A (ru) | 2012-03-27 |
| PE20091490A1 (es) | 2009-09-26 |
| JP2011512374A (ja) | 2011-04-21 |
| EP2254883B1 (en) | 2014-11-26 |
| JP5635914B2 (ja) | 2014-12-03 |
| AU2009216920A1 (en) | 2009-08-27 |
| AR070398A1 (es) | 2010-03-31 |
| IL207684A0 (en) | 2010-12-30 |
| US9206156B2 (en) | 2015-12-08 |
| CN102015683B (zh) | 2015-08-05 |
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