AU2009216920B2 - Substituted indole derivatives - Google Patents

Info

Publication number

AU2009216920B2

AU2009216920B2 AU2009216920A AU2009216920A AU2009216920B2 AU 2009216920 B2 AU2009216920 B2 AU 2009216920B2 AU 2009216920 A AU2009216920 A AU 2009216920A AU 2009216920 A AU2009216920 A AU 2009216920A AU 2009216920 B2 AU2009216920 B2 AU 2009216920B2

Authority

AU

Australia

Prior art keywords

methyl

dimethylamino

indol

piperidin

phenylpiperidin

Prior art date

2008-02-22

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.)

Ceased

Links

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• 150000002475 indoles Chemical class 0.000 title claims abstract description 52
• 229940054051 antipsychotic indole derivative Drugs 0.000 title claims abstract description 36
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 220
• 238000000034 method Methods 0.000 claims description 126
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
• -1 heteroaryl radical Chemical class 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 77
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 75
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 74
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 69
• 239000002253 acid Substances 0.000 claims description 65
• 239000002904 solvent Substances 0.000 claims description 57
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 56
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 55
• 150000001875 compounds Chemical class 0.000 claims description 51
• 239000000203 mixture Substances 0.000 claims description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
• 125000003118 aryl group Chemical group 0.000 claims description 37
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 33
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 30
• 239000011734 sodium Substances 0.000 claims description 29
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 20
• 229910052740 iodine Inorganic materials 0.000 claims description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
• 208000002193 Pain Diseases 0.000 claims description 18
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
• 150000007513 acids Chemical class 0.000 claims description 18
• 229910052794 bromium Inorganic materials 0.000 claims description 18
• 229940126601 medicinal product Drugs 0.000 claims description 18
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 17
• 150000001299 aldehydes Chemical class 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 17
• ILQHKJUYKHRALP-UHFFFAOYSA-N 1,2-dimethyl-4-phenylpiperidin-4-amine Chemical compound C1CN(C)C(C)CC1(N)C1=CC=CC=C1 ILQHKJUYKHRALP-UHFFFAOYSA-N 0.000 claims description 16
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 150000003254 radicals Chemical class 0.000 claims description 16
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 235000019253 formic acid Nutrition 0.000 claims description 15
• 125000001041 indolyl group Chemical group 0.000 claims description 15
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 13
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 12
• 150000001768 cations Chemical class 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 11
• OAOPDYUHWPBJCW-UHFFFAOYSA-N cyanoboron;sodium Chemical compound [Na].[B]C#N OAOPDYUHWPBJCW-UHFFFAOYSA-N 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 10
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 239000004480 active ingredient Substances 0.000 claims description 9
• 150000003857 carboxamides Chemical class 0.000 claims description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 230000036407 pain Effects 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 8
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 7
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• 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 description 6
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 6
• 208000024827 Alzheimer disease Diseases 0.000 claims description 6
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 6
• 229910000024 caesium carbonate Inorganic materials 0.000 claims description 6
• 238000005859 coupling reaction Methods 0.000 claims description 6
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 208000011117 substance-related disease Diseases 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 6
• 208000000094 Chronic Pain Diseases 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 208000004296 neuralgia Diseases 0.000 claims description 5
• 208000021722 neuropathic pain Diseases 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 229940005483 opioid analgesics Drugs 0.000 claims description 5
• 239000003960 organic solvent Substances 0.000 claims description 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 4
• 208000019901 Anxiety disease Diseases 0.000 claims description 4
• 206010012735 Diarrhoea Diseases 0.000 claims description 4
• 208000026139 Memory disease Diseases 0.000 claims description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 208000005298 acute pain Diseases 0.000 claims description 4
• 230000003444 anaesthetic effect Effects 0.000 claims description 4
• 230000036506 anxiety Effects 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 4
• HJZVHUQSQGITAM-UHFFFAOYSA-N butanamide Chemical compound CC[CH]C(N)=O HJZVHUQSQGITAM-UHFFFAOYSA-N 0.000 claims description 4
• 230000008878 coupling Effects 0.000 claims description 4
• 238000010168 coupling process Methods 0.000 claims description 4
• 206010061428 decreased appetite Diseases 0.000 claims description 4
• 206010015037 epilepsy Diseases 0.000 claims description 4
• 230000037406 food intake Effects 0.000 claims description 4
• 235000012631 food intake Nutrition 0.000 claims description 4
• 125000002541 furyl group Chemical group 0.000 claims description 4
• 150000007529 inorganic bases Chemical class 0.000 claims description 4
• 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 description 4
• 230000002981 neuropathic effect Effects 0.000 claims description 4
• 230000001777 nootropic effect Effects 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 3
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 206010006895 Cachexia Diseases 0.000 claims description 3
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 206010012335 Dependence Diseases 0.000 claims description 3
• 206010013654 Drug abuse Diseases 0.000 claims description 3
• 208000017228 Gastrointestinal motility disease Diseases 0.000 claims description 3
• 206010020772 Hypertension Diseases 0.000 claims description 3
• 208000001953 Hypotension Diseases 0.000 claims 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 claims description 3
• 208000020358 Learning disease Diseases 0.000 claims description 3
• 208000019695 Migraine disease Diseases 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 208000004880 Polyuria Diseases 0.000 claims description 3
• 208000003251 Pruritus Diseases 0.000 claims description 3
• 206010039966 Senile dementia Diseases 0.000 claims description 3
• 239000012317 TBTU Substances 0.000 claims description 3
• 208000009205 Tinnitus Diseases 0.000 claims description 3
• 206010046543 Urinary incontinence Diseases 0.000 claims description 3
• CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 3
• 239000000654 additive Substances 0.000 claims description 3
• 208000022531 anorexia Diseases 0.000 claims description 3
• MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 claims description 3
• 239000003153 chemical reaction reagent Substances 0.000 claims description 3
• 239000003638 chemical reducing agent Substances 0.000 claims description 3
• 208000010877 cognitive disease Diseases 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• 230000035619 diuresis Effects 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 208000016354 hearing loss disease Diseases 0.000 claims description 3
• 230000036543 hypotension Effects 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 201000003723 learning disability Diseases 0.000 claims description 3
• 230000003137 locomotive effect Effects 0.000 claims description 3
• 206010027599 migraine Diseases 0.000 claims description 3
• 230000037023 motor activity Effects 0.000 claims description 3
• 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 description 3
• DRSGCOMYBWFHBZ-UHFFFAOYSA-N n-[2-[4-(dimethylamino)-4-phenylpiperidin-1-yl]ethyl]-n,1-dimethylindole-6-carboxamide Chemical compound C=1C=C2C=CN(C)C2=CC=1C(=O)N(C)CCN(CC1)CCC1(N(C)C)C1=CC=CC=C1 DRSGCOMYBWFHBZ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
• 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 description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 230000004770 neurodegeneration Effects 0.000 claims description 3
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
• 230000003957 neurotransmitter release Effects 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 150000007530 organic bases Chemical class 0.000 claims description 3
• 230000009467 reduction Effects 0.000 claims description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 229910052708 sodium Inorganic materials 0.000 claims description 3
• 208000011580 syndromic disease Diseases 0.000 claims description 3
• 231100000886 tinnitus Toxicity 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• VAOHLWNZGWBTOK-UHFFFAOYSA-N 1-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]-3-(1h-indol-3-ylmethylamino)-3-phenylpropan-1-one Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCN1C(=O)CC(NCC=1C2=CC=CC=C2NC=1)C1=CC=CC=C1 VAOHLWNZGWBTOK-UHFFFAOYSA-N 0.000 claims description 2
• NGSDKBRWYABHLJ-UHFFFAOYSA-N 1-[4-(dimethylamino)-4-thiophen-2-ylpiperidin-1-yl]-3-(1h-indol-6-ylmethylamino)-3-phenylpropan-1-one Chemical compound C1CC(N(C)C)(C=2SC=CC=2)CCN1C(=O)CC(NCC=1C=C2NC=CC2=CC=1)C1=CC=CC=C1 NGSDKBRWYABHLJ-UHFFFAOYSA-N 0.000 claims description 2
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