IL129322A - History of ethylamine and pharmaceutical preparations containing them - Google Patents
History of ethylamine and pharmaceutical preparations containing themInfo
- Publication number
- IL129322A IL129322A IL12932298A IL12932298A IL129322A IL 129322 A IL129322 A IL 129322A IL 12932298 A IL12932298 A IL 12932298A IL 12932298 A IL12932298 A IL 12932298A IL 129322 A IL129322 A IL 129322A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- compound
- compounds
- pharmaceutical compositions
- ring
- Prior art date
Links
- 150000003947 ethylamines Chemical class 0.000 title claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 26
- -1 bicyclic compound Chemical class 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 14
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 13
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 9
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 181
- 239000000203 mixture Substances 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 239000000935 antidepressant agent Substances 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 8
- 229940005513 antidepressants Drugs 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
- 230000000506 psychotropic effect Effects 0.000 claims 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- LJHIBIVAYHQPBT-UHFFFAOYSA-N 1-(1-benzofuran-2-yl)-n-propylpentan-2-amine Chemical compound C1=CC=C2OC(CC(CCC)NCCC)=CC2=C1 LJHIBIVAYHQPBT-UHFFFAOYSA-N 0.000 claims 1
- XSXBOIUXADABRE-UHFFFAOYSA-N 1-(1h-indol-6-yl)-n-propylpentan-2-amine Chemical compound CCCNC(CCC)CC1=CC=C2C=CNC2=C1 XSXBOIUXADABRE-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000001430 anti-depressive effect Effects 0.000 claims 1
- OXTYFLOKCZIREK-UHFFFAOYSA-N n-propylpentan-2-amine Chemical compound CCCNC(C)CCC OXTYFLOKCZIREK-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 230000000694 effects Effects 0.000 description 40
- 238000000034 method Methods 0.000 description 39
- 238000004458 analytical method Methods 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 33
- 239000011734 sodium Substances 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 23
- 239000003814 drug Substances 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 229940079593 drug Drugs 0.000 description 22
- 241000700159 Rattus Species 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 150000003943 catecholamines Chemical class 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000001386 capillary affinity electrophoresis Methods 0.000 description 17
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- 102000010909 Monoamine Oxidase Human genes 0.000 description 12
- 108010062431 Monoamine oxidase Proteins 0.000 description 12
- 229960002748 norepinephrine Drugs 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 210000003568 synaptosome Anatomy 0.000 description 11
- 238000009739 binding Methods 0.000 description 10
- 230000001143 conditioned effect Effects 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 9
- 229940001470 psychoactive drug Drugs 0.000 description 9
- 239000004089 psychotropic agent Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 230000003578 releasing effect Effects 0.000 description 9
- 229960005333 tetrabenazine Drugs 0.000 description 9
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 7
- 210000000133 brain stem Anatomy 0.000 description 7
- 239000012528 membrane Substances 0.000 description 7
- 229940076279 serotonin Drugs 0.000 description 7
- 206010000117 Abnormal behaviour Diseases 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 210000001772 blood platelet Anatomy 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 6
- 102000003855 L-lactate dehydrogenase Human genes 0.000 description 5
- 108700023483 L-lactate dehydrogenases Proteins 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 230000002708 enhancing effect Effects 0.000 description 5
- 230000028023 exocytosis Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 230000011514 reflex Effects 0.000 description 5
- 239000000021 stimulant Substances 0.000 description 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 206010029350 Neurotoxicity Diseases 0.000 description 4
- 101100327316 Schizosaccharomyces pombe (strain 972 / ATCC 24843) cdc18 gene Proteins 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 206010044221 Toxic encephalopathy Diseases 0.000 description 4
- 230000000035 biogenic effect Effects 0.000 description 4
- 210000003169 central nervous system Anatomy 0.000 description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 210000000627 locus coeruleus Anatomy 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 210000001577 neostriatum Anatomy 0.000 description 4
- 230000007135 neurotoxicity Effects 0.000 description 4
- 231100000228 neurotoxicity Toxicity 0.000 description 4
- 239000008055 phosphate buffer solution Substances 0.000 description 4
- 210000004623 platelet-rich plasma Anatomy 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000000284 resting effect Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- 230000000768 catecholaminergic effect Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 210000003494 hepatocyte Anatomy 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 150000002689 maleic acids Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 3
- 229960003946 selegiline Drugs 0.000 description 3
- 210000003523 substantia nigra Anatomy 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229960003732 tyramine Drugs 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 101150032427 Arf1 gene Proteins 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 2
- 101100435275 Dictyostelium discoideum arfA gene Proteins 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 230000036982 action potential Effects 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 210000005013 brain tissue Anatomy 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229960003920 cocaine Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- BWUFCVGRQFOTOA-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)pentan-2-amine Chemical compound CCCC(N)CC1=CC=C2OCOC2=C1 BWUFCVGRQFOTOA-UHFFFAOYSA-N 0.000 description 1
- YXRBVSPNIQKGLW-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-n-propylpentan-2-amine;hydrochloride Chemical compound Cl.O1CCOC2=CC(CC(CCC)NCCC)=CC=C21 YXRBVSPNIQKGLW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- BDRAJGDAPYLXOK-UHFFFAOYSA-N 5-(2-nitropent-1-enyl)-1,3-benzodioxole Chemical compound CCCC([N+]([O-])=O)=CC1=CC=C2OCOC2=C1 BDRAJGDAPYLXOK-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 241000269350 Anura Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- RTLOFEAWXDJWEC-XNSHIZIVSA-N C(CCC(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.C(C(O)C(O)C(=O)O)(=O)O Chemical compound C(CCC(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.C(\C=C/C(=O)O)(=O)O.C(C(O)C(O)C(=O)O)(=O)O RTLOFEAWXDJWEC-XNSHIZIVSA-N 0.000 description 1
- MYBARAXPCQGUIX-UHFFFAOYSA-N CS(=O)(=O)O.[N+](=O)(O)[O-].Br.S(O)(O)(=O)=O.Cl Chemical compound CS(=O)(=O)O.[N+](=O)(O)[O-].Br.S(O)(O)(=O)=O.Cl MYBARAXPCQGUIX-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010060891 General symptom Diseases 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- RNXYXIKLWRRZNU-UHFFFAOYSA-N Kynuramine Natural products NCCCC(=O)C1=CC=CC=N1 RNXYXIKLWRRZNU-UHFFFAOYSA-N 0.000 description 1
- 239000002211 L-ascorbic acid Substances 0.000 description 1
- 235000000069 L-ascorbic acid Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
- 208000020369 Polymerase proofreading-related adenomatous polyposis Diseases 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000269435 Rana <genus> Species 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940125713 antianxiety drug Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 230000001447 compensatory effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UNXNGGMLCSMSLH-UHFFFAOYSA-N dihydrogen phosphate;triethylazanium Chemical compound OP(O)(O)=O.CCN(CC)CC UNXNGGMLCSMSLH-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000000835 electrochemical detection Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- QLPVTIQQFGWSQQ-UHFFFAOYSA-N kynuramine Chemical compound NCCC(=O)C1=CC=CC=C1N QLPVTIQQFGWSQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229960001252 methamphetamine Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940057952 methanol Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000008288 physiological mechanism Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000011076 safety test Methods 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- HRQDCDQDOPSGBR-UHFFFAOYSA-M sodium;octane-1-sulfonate Chemical compound [Na+].CCCCCCCCS([O-])(=O)=O HRQDCDQDOPSGBR-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 210000002504 synaptic vesicle Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24744597 | 1997-08-07 | ||
| PCT/JP1998/003468 WO1999007667A1 (fr) | 1997-08-07 | 1998-08-03 | Nouveaux derives d'ethylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL129322A0 IL129322A0 (en) | 2000-02-17 |
| IL129322A true IL129322A (en) | 2004-02-19 |
Family
ID=17163558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12932298A IL129322A (en) | 1997-08-07 | 1998-08-03 | History of ethylamine and pharmaceutical preparations containing them |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6214859B1 (hu) |
| EP (1) | EP0957080B1 (hu) |
| JP (1) | JP4569980B2 (hu) |
| KR (1) | KR100572900B1 (hu) |
| CN (1) | CN1182103C (hu) |
| AT (1) | ATE330930T1 (hu) |
| AU (1) | AU747737B2 (hu) |
| CA (1) | CA2267315C (hu) |
| DE (1) | DE69835004T2 (hu) |
| DK (1) | DK0957080T3 (hu) |
| ES (1) | ES2267190T3 (hu) |
| HK (1) | HK1022682A1 (hu) |
| HU (1) | HU228759B1 (hu) |
| IL (1) | IL129322A (hu) |
| PT (1) | PT957080E (hu) |
| SI (1) | SI9820009A (hu) |
| WO (1) | WO1999007667A1 (hu) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4499208B2 (ja) | 1998-10-29 | 2010-07-07 | 株式会社フジモト・コーポレーション | 新規な光学活性アミノペンタン誘導体 |
| FR2792313A1 (fr) * | 1999-04-13 | 2000-10-20 | Synthelabo | Derives de 2-aminoethyl-indole, leur preparation et leur application en therapeutique |
| JP2003505369A (ja) * | 1999-07-15 | 2003-02-12 | エヌピーエス アレリックス コーポレーション | 偏頭痛を治療するための複素環式化合物 |
| JP4691230B2 (ja) * | 2000-04-11 | 2011-06-01 | 株式会社フジモト・コーポレーション | 光学活性１−（ベンゾフラン−２−イル）−２−プロピルアミノペンタンの製造方法 |
| SE0001438D0 (sv) * | 2000-04-18 | 2000-04-18 | Axon Chemicals Bv | New chemical compounds and their use in therapy |
| JP4888751B2 (ja) * | 2001-09-14 | 2012-02-29 | 株式会社フジモト・コーポレーション | トリフルオロプロピルアミノペンタン誘導体及びその製造方法 |
| JP4953041B2 (ja) * | 2001-09-19 | 2012-06-13 | 株式会社フジモト・コーポレーション | アポトーシス抑制剤 |
| US6991911B2 (en) * | 2003-12-15 | 2006-01-31 | Dade Behring Inc. | Assay for entactogens |
| US20050130243A1 (en) * | 2003-12-15 | 2005-06-16 | Zheng Yi F. | Assay for entactogens |
| US7022492B2 (en) * | 2003-12-15 | 2006-04-04 | Dade Behring Inc. | Ecstasy haptens and immunogens |
| US7037669B2 (en) * | 2004-03-22 | 2006-05-02 | Dade Behring Inc. | Assays for amphetamine and methamphetamine using stereospecific reagents |
| US7115383B2 (en) * | 2004-03-22 | 2006-10-03 | Dade Behring Inc. | Assays for amphetamine and methamphetamine |
| US9155792B2 (en) | 2006-02-13 | 2015-10-13 | Trustees Of Boston University | RecA inhibitors with antibiotic activity, compositions and methods of use |
| DK2158908T3 (da) | 2007-06-21 | 2013-07-29 | Fujimoto Co Ltd | Sammensætning til transdermal administrering |
| EA027748B1 (ru) * | 2012-04-04 | 2017-08-31 | Тева Фармасьютикалз Интернэшнл Гмбх | Применение придопидина в комбинации с тетрабеназином для лечения двигательных нарушений и ожирения |
| CN106163514B (zh) * | 2013-12-25 | 2019-07-19 | 藤本株式会社 | 注意缺陷和多动性障碍的预防及治疗剂 |
| EP3226851B1 (en) | 2014-12-05 | 2020-03-18 | Semmelweis University | Arylalkylamine compounds for use in the prevention or treatment of cancer |
| CN114028616A (zh) * | 2021-09-28 | 2022-02-11 | 遵义医科大学 | 一种用于牙槽骨缺损修复的组织工程化材料制备方法 |
| WO2024064825A1 (en) * | 2022-09-21 | 2024-03-28 | Axsome Therapeutics, Inc. | Compounds and combinations thereof for treating neurological and psychiatric conditions |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB855115A (en) * | 1958-07-11 | 1960-11-30 | Smith Kline French Lab | Improvements in or relating to ª‰-aminoalkylthianaphthene and ª‰-aminoalkylbenzofuran derivatives |
| GB901919A (en) * | 1959-02-12 | 1962-07-25 | Upjohn Co | Therapeutic compositions comprising alpha-alkyl-tryptamines |
| GB893707A (en) * | 1960-03-01 | 1962-04-11 | Roche Products Ltd | Novel tryptamine derivatives and a process for the manufacture thereof |
| FR1344579A (fr) * | 1961-11-23 | 1963-11-29 | Sandoz Sa | Nouveaux dérivés de l'indole et leur préparation |
| US3296072A (en) * | 1962-06-11 | 1967-01-03 | Upjohn Co | Method of treating mental depression |
| US3472870A (en) | 1966-08-29 | 1969-10-14 | Mead Johnson & Co | Sulfonamidotryptamines |
| US3883560A (en) | 1973-07-05 | 1975-05-13 | Colgate Palmolive Co | Salicylamidophenethanolamines |
| FR2536749A1 (fr) * | 1982-11-25 | 1984-06-01 | Cerm Cent Europ Rech Mauvernay | (amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique |
| US5220068A (en) * | 1986-09-25 | 1993-06-15 | Chinoin Gyogyszer - Es Vegyeszeti Termekek Gyara Rt. | Psychostimulant agent |
| HU207280B (en) * | 1986-09-25 | 1993-03-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new phenyl-alkyl-amines and pharmaceutical compositions containing them |
| TW270114B (hu) | 1993-10-22 | 1996-02-11 | Hoffmann La Roche | |
| US5627200A (en) | 1994-09-26 | 1997-05-06 | Pfizer Inc | β3 -Adrenoceptor agonists and antagonists for the treatment of intestinal motility disorders, depression, prostate disease and dyslipidemia |
| FR2729147A1 (fr) * | 1995-01-11 | 1996-07-12 | Adir | Nouveaux composes (hetero) cycliques alkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2734814B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes alkoxy-aryles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2734816B1 (fr) * | 1995-05-31 | 1997-07-04 | Adir | Nouveaux aryl (alkyl) propylamides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB9702310D0 (en) * | 1997-02-05 | 1997-03-26 | Univ Hertfordshire | Invention |
-
1998
- 1998-08-03 PT PT98935352T patent/PT957080E/pt unknown
- 1998-08-03 ES ES98935352T patent/ES2267190T3/es not_active Expired - Lifetime
- 1998-08-03 SI SI9820009A patent/SI9820009A/sl not_active IP Right Cessation
- 1998-08-03 JP JP51196699A patent/JP4569980B2/ja not_active Expired - Fee Related
- 1998-08-03 US US09/269,718 patent/US6214859B1/en not_active Expired - Lifetime
- 1998-08-03 DK DK98935352T patent/DK0957080T3/da active
- 1998-08-03 HU HU0001466A patent/HU228759B1/hu not_active IP Right Cessation
- 1998-08-03 KR KR1019997003005A patent/KR100572900B1/ko not_active IP Right Cessation
- 1998-08-03 AT AT98935352T patent/ATE330930T1/de active
- 1998-08-03 WO PCT/JP1998/003468 patent/WO1999007667A1/ja active IP Right Grant
- 1998-08-03 EP EP98935352A patent/EP0957080B1/en not_active Expired - Lifetime
- 1998-08-03 IL IL12932298A patent/IL129322A/en not_active IP Right Cessation
- 1998-08-03 CA CA002267315A patent/CA2267315C/en not_active Expired - Fee Related
- 1998-08-03 CN CNB988011190A patent/CN1182103C/zh not_active Expired - Fee Related
- 1998-08-03 DE DE69835004T patent/DE69835004T2/de not_active Expired - Lifetime
- 1998-08-03 AU AU84635/98A patent/AU747737B2/en not_active Ceased
-
2000
- 2000-03-09 HK HK00101470A patent/HK1022682A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU747737B2 (en) | 2002-05-23 |
| DE69835004D1 (de) | 2006-08-03 |
| IL129322A0 (en) | 2000-02-17 |
| KR20000068728A (ko) | 2000-11-25 |
| CA2267315C (en) | 2008-01-08 |
| CN1182103C (zh) | 2004-12-29 |
| ES2267190T3 (es) | 2007-03-01 |
| PT957080E (pt) | 2006-10-31 |
| SI9820009A (sl) | 1999-10-31 |
| CA2267315A1 (en) | 1999-02-18 |
| HUP0001466A3 (en) | 2001-09-28 |
| US6214859B1 (en) | 2001-04-10 |
| KR100572900B1 (ko) | 2006-04-24 |
| DK0957080T3 (da) | 2006-10-23 |
| HUP0001466A2 (hu) | 2001-05-28 |
| EP0957080B1 (en) | 2006-06-21 |
| HU228759B1 (en) | 2013-05-28 |
| DE69835004T2 (de) | 2007-03-01 |
| AU8463598A (en) | 1999-03-01 |
| ATE330930T1 (de) | 2006-07-15 |
| WO1999007667A1 (fr) | 1999-02-18 |
| CN1236356A (zh) | 1999-11-24 |
| JP4569980B2 (ja) | 2010-10-27 |
| EP0957080A4 (en) | 2004-10-20 |
| HK1022682A1 (en) | 2000-08-18 |
| EP0957080A1 (en) | 1999-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL129322A (en) | History of ethylamine and pharmaceutical preparations containing them | |
| FI77018B (fi) | Analogifoerfarande foer framstaellning av antidepressivt aktiv (-)-enantiomer av n-metyl-n-/3-(2-metylfenoxi) -3-fenylpropyl/amin och dess farmaceutiskt godtagbara salt. | |
| US7026320B2 (en) | Serotonergic agents | |
| CA2705833A1 (en) | 3,5-substituted indole compounds having nos and norepinephrine reuptake inhibitory activity | |
| US5618947A (en) | Process of preparing enantiomers of carbazole derivatives | |
| AU762995B2 (en) | Novel optically active aminopentane derivative | |
| CA2307114A1 (en) | Arylpiperazines as serotonin reuptake inhibitors and 5-ht1d.alpha. antagonists | |
| CA2327360A1 (en) | Indol-3-yl-cyclohexyl amine derivatives for the treatment of depression (5-ht1 receptor antagonists) | |
| WO1999051575A1 (en) | N-aryloxyethyl-indoly-alkylamines for the treatment of depression (5-ht1a receptor active agents) | |
| NZ231243A (en) | Diphenylalkylamide derivatives and pharmaceutical compositions thereof | |
| JPH11507024A (ja) | 尿失禁の治療のためのアルファ−１ｃ−選択的アドレナリン受容体作動薬の使用 | |
| US20050192344A1 (en) | Treatment or prophylaxis of migraine or headache disorders using citalopram, escitalopram or citalopram metabolites | |
| US6894188B1 (en) | Tamsulosin derivative | |
| EP0940386B1 (fr) | Nouveaux composés du benzocyclobutane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| EP1516871A1 (fr) | Dérivés de benzoindoline avec une activité adrénergique | |
| KR100590827B1 (ko) | 테트라히드로이소퀴놀린알칸올 유도체 및 이를 함유하는약학적 조성물 | |
| JP2006503037A (ja) | 抗うつ作用を有する２，３−ジヒドロ−１，４−ベンゾジオキサンのシクロアルキルアミン誘導体 | |
| JP2931190B2 (ja) | ２，３−ジヒドロベンゾフラン誘導体 | |
| EA012752B1 (ru) | Производные 2-(1н-индолилсульфанил)бензиламина в качестве ssri | |
| JPH02264780A (ja) | α―アドレナリン作動性受容体拮杭剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |