CY1532A - Benzodioxinopyrroles - Google Patents

Benzodioxinopyrroles Download PDF

Info

Publication number: CY1532A
Authority: CY; Cyprus
Prior art keywords: compound; general formula; group; tetrahydro; alkyl
Prior art date: 1984-04-24

Application number

CY1532A

Other languages

English (en)

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

1984-04-24

Filing date

1990-11-16

Publication date

1990-11-16

1984-04-24 Priority claimed from GB848410456A external-priority patent/GB8410456D0/en

1985-02-15 Priority claimed from GB858503975A external-priority patent/GB8503975D0/en

1990-11-16 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1990-11-16 Publication of CY1532A publication Critical patent/CY1532A/en

Links

CEOQGBDEHVSEQC-UHFFFAOYSA-N 1h-[1,4]benzodioxino[2,3-b]pyrrole Chemical class O1C2=CC=CC=C2OC2=C1NC=C2 CEOQGBDEHVSEQC-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 103
150000003839 salts Chemical class 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
230000001430 anti-depressive effect Effects 0.000 claims description 6
239000000935 antidepressant agent Substances 0.000 claims description 6
229940005513 antidepressants Drugs 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
206010010774 Constipation Diseases 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 4
206010021333 Ileus paralytic Diseases 0.000 claims description 4
201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 claims description 4
208000019695 Migraine disease Diseases 0.000 claims description 4
208000008589 Obesity Diseases 0.000 claims description 4
206010039966 Senile dementia Diseases 0.000 claims description 4
208000007536 Thrombosis Diseases 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
206010012601 diabetes mellitus Diseases 0.000 claims description 4
206010027599 migraine Diseases 0.000 claims description 4
235000020824 obesity Nutrition 0.000 claims description 4
201000007620 paralytic ileus Diseases 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
XSOUHEXVEOQRKJ-IUCAKERBSA-N fluparoxan Chemical compound O1[C@H]2CNC[C@@H]2OC2=C1C=CC=C2F XSOUHEXVEOQRKJ-IUCAKERBSA-N 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
229940082496 Adrenoreceptor antagonist Drugs 0.000 abstract description 5
230000009471 action Effects 0.000 abstract description 5
238000005576 amination reaction Methods 0.000 abstract description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000543 intermediate Substances 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
239000000243 solution Substances 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
239000000203 mixture Substances 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
239000002904 solvent Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 19
239000010410 layer Substances 0.000 description 16
-1 Cv^alkoxy Chemical group 0.000 description 14
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000003118 aryl group Chemical group 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000004480 active ingredient Substances 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000002585 base Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 7
150000002009 diols Chemical class 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
125000005002 aryl methyl group Chemical group 0.000 description 6
239000013078 crystal Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000003826 tablet Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
238000011282 treatment Methods 0.000 description 5
LFDGRWDETVOGDT-UHFFFAOYSA-N 1h-pyrrole;hydrochloride Chemical compound Cl.C=1C=CNC=1 LFDGRWDETVOGDT-UHFFFAOYSA-N 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
150000003840 hydrochlorides Chemical class 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
230000004044 response Effects 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
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 description 3
229940124225 Adrenoreceptor agonist Drugs 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
239000012267 brine Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 3
229910000024 caesium carbonate Inorganic materials 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229960002896 clonidine Drugs 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
239000012458 free base Substances 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000008101 lactose Substances 0.000 description 3
229960001375 lactose Drugs 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
229960002748 norepinephrine Drugs 0.000 description 3
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000006722 reduction reaction Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 3
NTGWCGLYKIHPRF-IRXDYDNUSA-N (3as,9as)-2-benzyl-1,3,3a,9a-tetrahydro-[1,4]benzodioxino[2,3-c]pyrrole-5-carbonitrile Chemical compound C([C@@H]1OC=2C=CC=C(C=2O[C@H]1C1)C#N)N1CC1=CC=CC=C1 NTGWCGLYKIHPRF-IRXDYDNUSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
208000020401 Depressive disease Diseases 0.000 description 2
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
229930006000 Sucrose Natural products 0.000 description 2
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 2
OIQPTROHQCGFEF-QIKYXUGXSA-L Sunset Yellow FCF Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-QIKYXUGXSA-L 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
UXWZOFNTXBDTSE-IUCAKERBSA-N [(2s,3s)-5-fluoro-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methanol Chemical compound C1=CC(F)=C2O[C@@H](CO)[C@H](CO)OC2=C1 UXWZOFNTXBDTSE-IUCAKERBSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
229960000836 amitriptyline Drugs 0.000 description 2
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000001908 autoinhibitory effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
238000006900 dealkylation reaction Methods 0.000 description 2
229960003914 desipramine Drugs 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000008713 feedback mechanism Effects 0.000 description 2
235000019256 formaldehyde Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
229960004801 imipramine Drugs 0.000 description 2
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
210000002569 neuron Anatomy 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Hematology (AREA)
Obesity (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Light Receiving Elements (AREA)
Compositions Of Macromolecular Compounds (AREA)
Pyrrole Compounds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Polyesters Or Polycarbonates (AREA)
Luminescent Compositions (AREA)

CY1532A 1984-04-24 1990-11-16 Benzodioxinopyrroles CY1532A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB848410456A GB8410456D0 (en)	1984-04-24	1984-04-24	Chemical compounds
GB858503975A GB8503975D0 (en)	1985-02-15	1985-02-15	Chemical compounds

Publications (1)

Publication Number	Publication Date
CY1532A true CY1532A (en)	1990-11-16

Family

ID=26287645

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CY1532A CY1532A (en)	1984-04-24	1990-11-16	Benzodioxinopyrroles
CY169594A CY1695A (en)	1984-04-24	1994-01-14	Heterocyclic amino compounds

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CY169594A CY1695A (en)	1984-04-24	1994-01-14	Heterocyclic amino compounds

Country Status (21)

Country	Link
US (1)	US4880801A (da)
EP (2)	EP0162593B1 (da)
JP (2)	JPH02270878A (da)
KR (1)	KR920003065B1 (da)
AT (1)	ATE55605T1 (da)
AU (1)	AU577367B2 (da)
CA (1)	CA1256111A (da)
CS (1)	CS402491A3 (da)
CY (2)	CY1532A (da)
DE (2)	DE3579189D1 (da)
DK (2)	DK160556C (da)
ES (2)	ES8607311A1 (da)
FI (1)	FI84069C (da)
GB (3)	GB2201414B (da)
GR (1)	GR850993B (da)
HK (2)	HK42890A (da)
IL (1)	IL75011A (da)
MX (1)	MX9203233A (da)
NZ (1)	NZ211885A (da)
PT (1)	PT80344B (da)
SG (2)	SG23590G (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8526210D0 (en) *	1985-10-23	1985-11-27	Glaxo Group Ltd	Chemical compounds
GB8526209D0 (en) *	1985-10-23	1985-11-27	Glaxo Group Ltd	Chemical process
US5225431A (en) *	1987-10-23	1993-07-06	Burroughs Wellcome Co.	Therapeutic substituted indole compounds and compositions thereof
GB8828032D0 (en) *	1988-12-01	1989-01-05	Glaxo Group Ltd	Medicaments
GB9012469D0 (en) *	1990-06-05	1990-07-25	Glaxo Group Ltd	Medicaments
GB9119466D0 (en) *	1991-09-12	1991-10-23	Glaxo Group Ltd	Chemical compounds
US6451806B2 (en)	1999-09-29	2002-09-17	Adolor Corporation	Methods and compositions involving opioids and antagonists thereof
US6469030B2 (en)	1999-11-29	2002-10-22	Adolor Corporation	Methods for the treatment and prevention of ileus
BRPI0409492A (pt) *	2003-04-18	2006-05-02	Pharmacia & Up John Company Ll	terapias de combinação
GB2503187A (en) *	2011-09-15	2013-12-25	Univ Sussex	Composition for use in the treatment of neurodevelopmental disorders

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2485539A1 (fr) *	1980-06-26	1981-12-31	Sori Soc Rech Ind	Nouveau derive de pyranno-indole, son procede de preparation et son application en therapeutique
IL70034A0 (en) *	1982-10-25	1984-01-31	Glaxo Group Ltd	Heterocyclic amino compounds,their preparation and pharmaceutical compositions containing them

1985
- 1985-04-24 GB GB08802949A patent/GB2201414B/en not_active Expired
- 1985-04-24 AU AU41667/85A patent/AU577367B2/en not_active Ceased
- 1985-04-24 DE DE8585302854T patent/DE3579189D1/de not_active Expired - Fee Related
- 1985-04-24 ES ES542516A patent/ES8607311A1/es not_active Expired
- 1985-04-24 AT AT85302854T patent/ATE55605T1/de not_active IP Right Cessation
- 1985-04-24 PT PT80344A patent/PT80344B/pt not_active IP Right Cessation
- 1985-04-24 DE DE89117732T patent/DE3587511T2/de not_active Expired - Fee Related
- 1985-04-24 NZ NZ211885A patent/NZ211885A/xx unknown
- 1985-04-24 GB GB8510449A patent/GB2157691B/en not_active Expired
- 1985-04-24 IL IL75011A patent/IL75011A/xx not_active IP Right Cessation
- 1985-04-24 KR KR1019850002771A patent/KR920003065B1/ko not_active Expired
- 1985-04-24 GR GR850993A patent/GR850993B/el unknown
- 1985-04-24 EP EP85302854A patent/EP0162593B1/en not_active Expired - Lifetime
- 1985-04-24 EP EP89117732A patent/EP0359290B1/en not_active Expired - Lifetime
- 1985-04-24 FI FI851611A patent/FI84069C/fi not_active IP Right Cessation
- 1985-04-24 DK DK184085A patent/DK160556C/da not_active IP Right Cessation
- 1985-04-24 CA CA000479944A patent/CA1256111A/en not_active Expired
1986
- 1986-01-31 ES ES551509A patent/ES8801545A1/es not_active Expired
1987
- 1987-12-11 GB GB878728949A patent/GB8728949D0/en active Pending
1988
- 1988-05-26 US US07/198,971 patent/US4880801A/en not_active Expired - Fee Related
1990
- 1990-03-22 JP JP2073144A patent/JPH02270878A/ja active Pending
- 1990-03-22 JP JP2073145A patent/JPH02270819A/ja active Pending
- 1990-03-24 SG SG235/90A patent/SG23590G/en unknown
- 1990-05-31 HK HK428/90A patent/HK42890A/xx unknown
- 1990-06-08 DK DK141590A patent/DK160824C/da not_active IP Right Cessation
- 1990-11-16 CY CY1532A patent/CY1532A/en unknown
1991
- 1991-12-23 CS CS914024A patent/CS402491A3/cs unknown
1992
- 1992-06-24 MX MX9203233A patent/MX9203233A/es unknown
1993
- 1993-02-05 SG SG122/93A patent/SG12293G/en unknown
- 1993-10-21 HK HK1120/93A patent/HK112093A/en not_active IP Right Cessation
1994
- 1994-01-14 CY CY169594A patent/CY1695A/xx unknown

Also Published As

Publication number	Publication date
FI851611A0 (fi)	1985-04-24
PT80344B (pt)	1987-09-30
ES8801545A1 (es)	1988-02-01
FI84069B (fi)	1991-06-28
DK160556B (da)	1991-03-25
DK184085D0 (da)	1985-04-24
DK184085A (da)	1985-10-25
DK160556C (da)	1991-09-02
GB2157691A (en)	1985-10-30
DK141590A (da)	1990-06-08
FI851611L (fi)	1985-10-25
IL75011A (en)	1990-02-09
CY1695A (en)	1994-01-14
CS402491A3 (en)	1992-10-14
PT80344A (en)	1985-05-01
NZ211885A (en)	1988-09-29
EP0162593B1 (en)	1990-08-16
GB8728949D0 (en)	1988-01-27
ATE55605T1 (de)	1990-09-15
GB8510449D0 (en)	1985-05-30
DK160824B (da)	1991-04-22
JPH02270819A (ja)	1990-11-05
DE3587511T2 (de)	1993-11-18
EP0359290B1 (en)	1993-08-04
GB2157691B (en)	1989-07-05
AU577367B2 (en)	1988-09-22
SG23590G (en)	1990-07-13
CA1256111A (en)	1989-06-20
EP0162593A1 (en)	1985-11-27
MX9203233A (es)	1992-07-01
DE3579189D1 (de)	1990-09-20
SG12293G (en)	1993-04-16
GR850993B (da)	1985-11-25
ES8607311A1 (es)	1986-06-16
GB8802949D0 (en)	1988-03-09
GB2201414A (en)	1988-09-01
ES542516A0 (es)	1986-06-16
HK112093A (en)	1993-10-29
US4880801A (en)	1989-11-14
AU4166785A (en)	1985-10-31
EP0359290A1 (en)	1990-03-21
DK160824C (da)	1991-10-07
DK141590D0 (da)	1990-06-08
KR920003065B1 (ko)	1992-04-13
FI84069C (fi)	1991-10-10
GB2201414B (en)	1988-12-29
KR850007259A (ko)	1985-12-02
DE3587511D1 (de)	1993-09-09
ES551509A0 (es)	1988-02-01
HK42890A (en)	1990-06-08
JPH02270878A (ja)	1990-11-05

Publication	Publication Date	Title
PL109672B1 (en)	1980-06-30	Method of producing new derivatives of 1-phenylo-2,3,4,5-tetrahydro-1h-3-benzazepine
WO2002085896A1 (en)	2002-10-31	Antidepressant azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-benzodioxan
CA1256111A (en)	1989-06-20	Benzodiioxinopyrrole derivatives
US4496579A (en)	1985-01-29	Benzodioxinopyrrole derivatives and processes for their preparation
Grol et al.	1985	Resolution of 5, 6-dihydroxy-2-(N, N-di-n-propylamino) tetralin in relation to the structural and stereochemical requirements for centrally acting dopamine agonists
US5126366A (en)	1992-06-30	Aminophenoxyalkyl derivatives of benzodioxan
US5166367A (en)	1992-11-24	Antipsychotic benzodioxan derivatives
NO173865B (no)	1993-11-08	Analogifremgangsmaate for fremstilling av terapeutisk aktive 2,3,4,5-tetrahydro-1h-3-benzazepiner
US4769367A (en)	1988-09-06	Heterocyclic amino compounds
EP0162592B1 (en)	1989-03-22	Heterocyclic amino compounds
US5189171A (en)	1993-02-23	Antipsychotic benzodioxan derivatives
US6800641B2 (en)	2004-10-05	Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-6,9-dioxa-2,3-diaza-cyclopenta[a]naphthalene
US6800648B2 (en)	2004-10-05	Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-1,6,9-trioxa-3-AZA-cyclopenta[a]naphthalen-2-one
Diouf et al.	1997	5-HT1A and 5-HT2A ligands with anxiolytic and antipanic-like properties
EP0224332B1 (en)	1990-08-08	Heterocyclic amino compounds
EP0520674B1 (en)	1995-08-16	Antipsychotic benzodioxan derivatives
JPS60132981A (ja)	1985-07-16	新規なインドール誘導体
GB2174087A (en)	1986-10-29	Heterocyclic amino compounds
IE67793B1 (en)	1996-05-01	Antipsychotic benzodioxan derivatives
JPS60233083A (ja)	1985-11-19	複素環式アミノ化合物
PL152909B1 (pl)	1991-02-28	Sposób wytwarzania nowych pochodnych pilokarpiny