IL119565A - (-2 Aminomethyl) - 2, 3, 8, 9 - Tetrahydro - 7H - 1, 4 - Dioxino- [e-3,2] - Indole- -8 Ones, homologues and their history and pharmaceutical preparations containing them - Google Patents

(-2 Aminomethyl) - 2, 3, 8, 9 - Tetrahydro - 7H - 1, 4 - Dioxino- [e-3,2] - Indole- -8 Ones, homologues and their history and pharmaceutical preparations containing them

Info

Publication number: IL119565A
Authority: IL; Israel
Prior art keywords: carbon atoms; indol; dioxino; compound; tetrahydro
Prior art date: 1995-11-06

Application number

IL11956596A

Other languages

English (en)

Hebrew (he)

Other versions

IL119565A0 (en

Original Assignee

American Home Prod

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.)

1995-11-06

Filing date

1996-11-05

Publication date

2002-11-10

1996-11-05 Application filed by American Home Prod filed Critical American Home Prod

1997-03-18 Publication of IL119565A0 publication Critical patent/IL119565A0/xx

2002-11-10 Publication of IL119565A publication Critical patent/IL119565A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 159
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 74
150000003839 salts Chemical class 0.000 claims abstract description 45
239000001257 hydrogen Substances 0.000 claims abstract description 32
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 26
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 18
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 12
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 12
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 12
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 12
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims abstract description 12
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 10
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims abstract description 7
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims abstract description 7
125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims abstract description 6
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims abstract description 6
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims abstract description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 6
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 6
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 6
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims abstract description 6
125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims abstract description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
229930192474 thiophene Natural products 0.000 claims abstract description 6
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 5
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 5
125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000001118 alkylidene group Chemical group 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 4
125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 13
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 7
-1 3-hydroxy-propylamino Chemical group 0.000 claims description 23
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
229960003638 dopamine Drugs 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 5
BYYPZLZUDUJJTA-UHFFFAOYSA-N [1,4]dioxino[2,3-e]indol-8-one Chemical compound O1C=COC2=C1C=CC1=NC(=O)C=C21 BYYPZLZUDUJJTA-UHFFFAOYSA-N 0.000 claims description 2
XHEHTXUBYLCXSK-UHFFFAOYSA-N 2-[(1-adamantylmethylamino)methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound C1C(C2)CC(C3)CC2CC13CNCC1COC(C=CC2=C3CC(N2)=O)=C3O1 XHEHTXUBYLCXSK-UHFFFAOYSA-N 0.000 claims 1
GFOREZIOZJPIAR-UHFFFAOYSA-N 2-[[3-[3-(dimethylamino)phenoxy]propylamino]methyl]-6-fluoro-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound CN(C)C1=CC=CC(OCCCNCC2OC3=C4CC(=O)NC4=C(F)C=C3OC2)=C1 GFOREZIOZJPIAR-UHFFFAOYSA-N 0.000 claims 1
LUBCYXMQHNMZAR-UHFFFAOYSA-N 2-[[[4-(trifluoromethyl)phenyl]methylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound C1=CC(C(F)(F)F)=CC=C1CNCC1OC2=C3CC(=O)NC3=CC=C2OC1 LUBCYXMQHNMZAR-UHFFFAOYSA-N 0.000 claims 1
PSDXGHNGCKKPMX-UHFFFAOYSA-N 6-fluoro-2-[[3-(1h-indol-3-yl)propylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound C1=CC=C2C(CCCNCC3COC=4C=C(C=5NC(=O)CC=5C=4O3)F)=CNC2=C1 PSDXGHNGCKKPMX-UHFFFAOYSA-N 0.000 claims 1
210000004556 brain Anatomy 0.000 claims 1
230000008482 dysregulation Effects 0.000 claims 1
208000024891 symptom Diseases 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 214
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 188
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 136
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 128
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 125
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 105
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 98
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 96
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 94
239000000203 mixture Substances 0.000 description 92
239000007787 solid Substances 0.000 description 87
229910001868 water Inorganic materials 0.000 description 81
235000011087 fumaric acid Nutrition 0.000 description 71
239000003921 oil Substances 0.000 description 64
235000019198 oils Nutrition 0.000 description 64
239000000243 solution Substances 0.000 description 63
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 58
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 57
239000000741 silica gel Substances 0.000 description 56
229910002027 silica gel Inorganic materials 0.000 description 56
238000000921 elemental analysis Methods 0.000 description 51
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 41
239000001530 fumaric acid Substances 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 35
239000012458 free base Substances 0.000 description 32
229910052943 magnesium sulfate Inorganic materials 0.000 description 32
238000001816 cooling Methods 0.000 description 30
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
239000012267 brine Substances 0.000 description 28
239000000047 product Substances 0.000 description 26
229910052938 sodium sulfate Inorganic materials 0.000 description 26
235000011152 sodium sulphate Nutrition 0.000 description 26
239000012299 nitrogen atmosphere Substances 0.000 description 24
229920006395 saturated elastomer Polymers 0.000 description 24
229910052757 nitrogen Inorganic materials 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
235000017557 sodium bicarbonate Nutrition 0.000 description 20
229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
239000002904 solvent Substances 0.000 description 19
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000012300 argon atmosphere Substances 0.000 description 12
238000001914 filtration Methods 0.000 description 12
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
239000007788 liquid Substances 0.000 description 11
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
238000004440 column chromatography Methods 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
238000003756 stirring Methods 0.000 description 9
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
239000012535 impurity Substances 0.000 description 8
238000000034 method Methods 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
235000019502 Orange oil Nutrition 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000010502 orange oil Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000000725 suspension Substances 0.000 description 6
IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
150000001412 amines Chemical group 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
150000003951 lactams Chemical class 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
239000012286 potassium permanganate Substances 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
208000028017 Psychotic disease Diseases 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000003291 dopaminomimetic effect Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
238000012360 testing method Methods 0.000 description 4
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
241000700159 Rattus Species 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
NOQXXYIGRPAZJC-SECBINFHSA-N [(2r)-oxiran-2-yl]methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@@H]1OC1 NOQXXYIGRPAZJC-SECBINFHSA-N 0.000 description 3
239000000556 agonist Substances 0.000 description 3
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
235000010980 cellulose Nutrition 0.000 description 3
125000004311 dioxin-2-yl group Chemical group [H]C1=C([H])OC(*)=C([H])O1 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
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238000009833 condensation Methods 0.000 description 1
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239000012059 conventional drug carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
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125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
238000000605 extraction Methods 0.000 description 1
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239000000945 filler Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
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150000002334 glycols Chemical class 0.000 description 1
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238000006197 hydroboration reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
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238000007912 intraperitoneal administration Methods 0.000 description 1
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LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
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150000004682 monohydrates Chemical class 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
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238000007254 oxidation reaction Methods 0.000 description 1
238000007248 oxidative elimination reaction Methods 0.000 description 1
150000005623 oxindoles Chemical class 0.000 description 1
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QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
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239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
229950001037 quinpirole Drugs 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
229960001534 risperidone Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
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230000000638 stimulation Effects 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
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239000000126 substance Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
TZGODTCAKVHMFG-UHFFFAOYSA-N sulfanylmethoxymethanethiol Chemical compound SCOCS TZGODTCAKVHMFG-UHFFFAOYSA-N 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000015883 synaptic transmission, dopaminergic Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000001993 wax Substances 0.000 description 1

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
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychology (AREA)
Psychiatry (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

IL11956596A 1995-11-06 1996-11-05 (-2 Aminomethyl) - 2, 3, 8, 9 - Tetrahydro - 7H - 1, 4 - Dioxino- [e-3,2] - Indole- -8 Ones, homologues and their history and pharmaceutical preparations containing them IL119565A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US728395P	1995-11-06	1995-11-06
US08/730,267 US5756532A (en)	1995-11-06	1996-10-15	Aminomethyl-2 3 8 9-tetrahydro-7H-1 4-dioxino 2 3-E!-indol-8-ones and derivatives

Publications (2)

Publication Number	Publication Date
IL119565A0 IL119565A0 (en)	1997-03-18
IL119565A true IL119565A (en)	2002-11-10

Family

ID=26676776

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11956596A IL119565A (en)	1995-11-06	1996-11-05	(-2 Aminomethyl) - 2, 3, 8, 9 - Tetrahydro - 7H - 1, 4 - Dioxino- [e-3,2] - Indole- -8 Ones, homologues and their history and pharmaceutical preparations containing them

Country Status (21)

Country	Link
US (2)	US5756532A (ja)
EP (3)	EP0771800A3 (ja)
JP (1)	JP4311770B2 (ja)
KR (1)	KR100566678B1 (ja)
CN (1)	CN1084748C (ja)
AR (2)	AR004284A1 (ja)
AT (1)	ATE349450T1 (ja)
AU (1)	AU701624B2 (ja)
CA (1)	CA2189524C (ja)
CZ (1)	CZ291731B6 (ja)
DE (1)	DE69636801T2 (ja)
DK (1)	DK1375503T3 (ja)
ES (1)	ES2277014T3 (ja)
HU (1)	HU224841B1 (ja)
IL (1)	IL119565A (ja)
MX (1)	MX9605367A (ja)
NO (1)	NO317054B1 (ja)
NZ (1)	NZ299693A (ja)
PT (1)	PT1375503E (ja)
RU (1)	RU2178416C2 (ja)
SK (1)	SK282168B6 (ja)

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US6350773B1 (en) *	1999-12-10	2002-02-26	American Home Products Corporation	Therapeutic combinations of (S)-2-(benzylamino-methyl)-2,3,8,9,-tetrahydro 7H-1,4-dioxino{2,3-e}indol-8-one and neuroleptics for the treatment or prevention of psychotic disorders
CA2396351C (en) *	1999-12-10	2009-11-10	Wyeth	New therapeutic combinations of (s)-2-(benzylamino-methyl)-2,3,8,9,-tetrahydro-7h-1,4-dioxino[2,3-e]indol-8-one and neuroleptics for the treatment or prevention of psychotic disorders
US20060287335A1 (en) *	2000-11-28	2006-12-21	Wyeth	Serotonergic agents for treating sexual dysfunction
US20060223824A1 (en) *	2000-11-28	2006-10-05	Wyeth	Serotonergic agents
US6458802B1 (en)	2001-03-14	2002-10-01	Wyeth	Antidepressant azaheterocyclymethyl derivatives of 2,3-dihydro-1,4-dioxino [2,3-f]quinoline
US6803368B2 (en)	2001-04-25	2004-10-12	Wyeth	Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalene
US6800641B2 (en)	2001-04-26	2004-10-05	Wyeth	Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-6,9-dioxa-2,3-diaza-cyclopenta[a]naphthalene
US6861434B2 (en)	2001-04-26	2005-03-01	Wyeth	Antipsychotic aminomethyl derivatives of 1,3,7,8-tetrahydro-6,9-dioxa-1,3-diaza-cyclopenta[a]-naphthalen-2-one
US7008944B2 (en) *	2001-04-26	2006-03-07	Wyeth	Antidepressant azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-Dioxino[2,3-f]quinoxaline
US6656947B2 (en)	2001-04-26	2003-12-02	Wyeth	Antidepressant azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]quinazoline
US6800648B2 (en)	2001-04-26	2004-10-05	Wyeth	Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-1,6,9-trioxa-3-AZA-cyclopenta[a]naphthalen-2-one
US6821981B2 (en)	2001-04-26	2004-11-23	Wyeth	Azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]-quinoline as 5-HT1A antagonists
JP2004527563A (ja) *	2001-04-26	2004-09-09	ワイス	抗うつ作用を有する、２，３−ジヒドロ−１，４−ジオキシノ［２，３−ｆ］キノキサリンのアザへテロシクリルメチル誘導体
ES2247327T3 (es)	2001-04-26	2006-03-01	Wyeth	Derivados azaheterociclimetilicos antidepresivos (isrs) de 7,8-dihidro-3h-6,9-dioxa-1,3-diazaciclopenta(a) naftaleno.
US6861427B2 (en) *	2001-04-26	2005-03-01	Wyeth	Azabicyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]quinoline as 5-HT1A antagonists
US6927226B2 (en)	2001-04-26	2005-08-09	Wyeth	Antidepressant azaheterocyclymethyl derivatives of 7,8-dihydro-3H-6,9-dioxa-1,3-diazacyclopenta[a]naphthalene
US6800642B2 (en)	2001-04-26	2004-10-05	Wyeth	Antipsychotic aminomethyl derivatives of 7,8-dihydro-2,6,9-trioxa-3-aza-cyclopenta[a]naphthalene
US6906206B2 (en)	2001-04-30	2005-06-14	Wyeth	Antidepressant azaheterocyclylmethyl derivatives of 1,4,5-trioxa-phenanthrene
US6555560B2 (en) *	2001-04-30	2003-04-29	Wyeth	Antidepressant azaheterocyclylmethyl derivatives of 1,4,5-trioxa-phenanthrene
MXPA03010524A (es) *	2001-05-17	2005-03-07	Wyeth Corp	Proceso para la sintesis de derivados de la 2,3-dihidro-1,4-dioxino-[2,3-f]-quinolina.
US6541502B1 (en)	2001-07-20	2003-04-01	Wyeth	2-(aminomethyl)-tetrahydro-9-oxa-1,3-diaza-cyclopenta[a]-naphthalenyl derivatives with antipsychotic activity
US6541501B2 (en)	2001-07-20	2003-04-01	Wyeth	2-(aminomethyl)-tetrahydro-9-oxa-1,3-diaza-cyclopenta[a]-naphthalenyl derivatives with antipsychotic activity
US6903110B2 (en)	2001-07-25	2005-06-07	Wyeth	Antidepressant azaheterocyclylmethyl derivatives of 7,8-dihydro-6H-5-oxa-1-aza-phenanthrene
US6800637B2 (en) *	2002-09-12	2004-10-05	Wyeth	Antidepressant indolealkyl derivatives of heterocycle-fused benzodioxan methylamines
US7135479B2 (en)	2002-09-12	2006-11-14	Wyeth	Antidepressant azaheterocyclylmethyl derivatives of heterocycle-fused benzodioxans
US7153849B2 (en) *	2002-09-12	2006-12-26	Wyeth	Antidepressant arylpiperazine derivatives of hetrocycle-fused benzodioxans
US6939877B2 (en) *	2002-09-12	2005-09-06	Wyeth	Antidepressant piperidine derivatives of heterocycle-fused benzodioxans
CN100352820C (zh) *	2002-09-12	2007-12-05	惠氏公司	抗抑郁的杂环稠合的苯并二噁烷的氮杂环甲基衍生物
ES2405404T3 (es) *	2003-10-29	2013-05-31	Wyeth Llc	Composiciones farmacéuticas de liberación sostenida que comprenden aplindore y sus derivados
CA2566196A1 (en) *	2004-05-05	2005-11-10	F. Hoffmann-La Roche Ag	Arylsulfonyl benzodioxanes useful for modulating the 5-ht6 receptor, the 5-ht2a receptor or both
JP2008530229A (ja)	2005-02-17	2008-08-07	ワイス	シクロアルキル縮合インドール、ベンゾチオフェン、ベンゾフランおよびインデン誘導体
TW200700413A (en) *	2005-03-01	2007-01-01	Wyeth Corp	Crystalline and amorphous 4-cyano-n-{(2r)-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazin-1-yl]-propyl}-n-pyridin-2-yl-benzamide hydrochloride
CA2604915A1 (en) *	2005-04-22	2006-11-02	Wyeth	New therapeutic combinations for the treatment or prevention of depression
TW200811182A (en) *	2006-05-25	2008-03-01	Wyeth Corp	Oxindoledioxans, synthesis thereof, and intermediates thereto
US8466296B2 (en) *	2007-03-26	2013-06-18	Ligand Pharmaceuticals	Compounds and processes for preparing substituted aminomethyl-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-ones
CN102378574B (zh)	2009-03-30	2013-11-20	转化技术制药公司	取代的偶氮蒽衍生物、药物组合物及其使用方法
RU2554883C1 (ru) *	2014-05-27	2015-06-27	Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Казанский (Приволжский) Федеральный Университет" (ФГАОУ ВПО КФУ)	Применение производных ацеталей пиридоксина в качестве антагонистов пуринорецепторов
RU2554885C1 (ru) *	2014-05-27	2015-06-27	Федеральное государственное автономное образовательное учреждение высшего профессионального образования "Казанский (Приволжский) Федеральный Университет" (ФГАОУ ВПО КФУ)	Антагонисты пуринорецепторов на основе новых производных пиридоксина

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US5126366A (en) *	1991-06-21	1992-06-30	American Home Products Corporation	Aminophenoxyalkyl derivatives of benzodioxan
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1996
- 1996-10-15 US US08/730,267 patent/US5756532A/en not_active Expired - Lifetime
- 1996-10-22 EP EP96307616A patent/EP0771800A3/en not_active Ceased
- 1996-10-22 EP EP06015712A patent/EP1726592A1/en not_active Withdrawn
- 1996-10-22 AT AT03021780T patent/ATE349450T1/de active
- 1996-10-22 ES ES03021780T patent/ES2277014T3/es not_active Expired - Lifetime
- 1996-10-22 PT PT03021780T patent/PT1375503E/pt unknown
- 1996-10-22 DK DK03021780T patent/DK1375503T3/da active
- 1996-10-22 EP EP03021780A patent/EP1375503B1/en not_active Expired - Lifetime
- 1996-10-22 DE DE69636801T patent/DE69636801T2/de not_active Expired - Lifetime
- 1996-10-31 SK SK1414-96A patent/SK282168B6/sk not_active IP Right Cessation
- 1996-11-01 AU AU70553/96A patent/AU701624B2/en not_active Ceased
- 1996-11-04 CA CA002189524A patent/CA2189524C/en not_active Expired - Fee Related
- 1996-11-04 NZ NZ299693A patent/NZ299693A/xx not_active IP Right Cessation
- 1996-11-04 RU RU96121824/04A patent/RU2178416C2/ru not_active IP Right Cessation
- 1996-11-05 MX MX9605367A patent/MX9605367A/es unknown
- 1996-11-05 JP JP29247996A patent/JP4311770B2/ja not_active Expired - Fee Related
- 1996-11-05 HU HU9603057A patent/HU224841B1/hu not_active IP Right Cessation
- 1996-11-05 NO NO19964686A patent/NO317054B1/no not_active IP Right Cessation
- 1996-11-05 AR ARP960105059A patent/AR004284A1/es active IP Right Grant
- 1996-11-05 IL IL11956596A patent/IL119565A/en not_active IP Right Cessation
- 1996-11-05 CN CN96121650A patent/CN1084748C/zh not_active Expired - Fee Related
- 1996-11-05 CZ CZ19963241A patent/CZ291731B6/cs not_active IP Right Cessation
- 1996-11-05 KR KR1019960051969A patent/KR100566678B1/ko not_active Expired - Fee Related
1998
- 1998-01-29 US US09/015,149 patent/US5962465A/en not_active Expired - Lifetime
2000
- 2000-09-15 AR ARP000104875A patent/AR025698A1/es unknown

Also Published As

Publication number	Publication date
EP1375503B1 (en)	2006-12-27
NO964686L (no)	1997-05-07
IL119565A0 (en)	1997-03-18
EP1375503A1 (en)	2004-01-02
NO964686D0 (no)	1996-11-05
CN1155546A (zh)	1997-07-30
CA2189524A1 (en)	1997-05-07
HUP9603057A3 (en)	1998-12-28
KR970027068A (ko)	1997-06-24
ATE349450T1 (de)	2007-01-15
NO317054B1 (no)	2004-08-02
DK1375503T3 (da)	2007-01-22
AU7055396A (en)	1997-05-15
DE69636801T2 (de)	2007-04-26
US5756532A (en)	1998-05-26
CA2189524C (en)	2007-05-01
AU701624B2 (en)	1999-02-04
HU224841B1 (en)	2006-03-28
EP1726592A1 (en)	2006-11-29
DE69636801D1 (de)	2007-02-08
JPH09249671A (ja)	1997-09-22
SK282168B6 (sk)	2001-11-06
HU9603057D0 (en)	1996-12-30
CZ291731B6 (cs)	2003-05-14
PT1375503E (pt)	2007-03-30
SK141496A3 (en)	1997-08-06
EP0771800A3 (en)	1998-01-28
EP0771800A2 (en)	1997-05-07
JP4311770B2 (ja)	2009-08-12
US5962465A (en)	1999-10-05
AR004284A1 (es)	1998-11-04
MX9605367A (es)	1997-10-31
RU2178416C2 (ru)	2002-01-20
CZ324196A3 (en)	1997-12-17
NZ299693A (en)	1997-09-22
ES2277014T3 (es)	2007-07-01
KR100566678B1 (ko)	2006-11-30
CN1084748C (zh)	2002-05-15
HUP9603057A2 (en)	1997-05-28
AR025698A1 (es)	2002-12-11

Legal Events

Date	Code	Title
2003-04-10	FF	Patent granted
2003-05-29	KB	Patent renewed
2006-12-27	KB	Patent renewed
2010-12-30	KB	Patent renewed
2015-06-30	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US5962465A (en)	1999-10-05	Aminomethyl-2,3,8,9-tetrahydro-7H-1,4-dioxino- 2,3-e!-indol-8-ones and derivatives
US5869490A (en)	1999-02-09	Azaheterocyclymethyl derivatives of 2,3,8,9-tetrahydro-7h-1,4-dioxino (2,3-e) indol-8-one
EP0932609B1 (en)	2003-05-14	AZAHETEROCYCLYMETHYL DERIVATIVES OF 2,3,8,9-TETRAHYDRO-7H-1,4-DIOXINO 2,3-e]INDOL-8-ONE
US6800637B2 (en)	2004-10-05	Antidepressant indolealkyl derivatives of heterocycle-fused benzodioxan methylamines
CA2445552A1 (en)	2002-11-07	Antidepressant (sssri) azaheterocyclymethyl derivatives of 7,8-dihydro-3h-t,9-dioxa-1,3-diazacyclopenta[a]naphthalene
US6800641B2 (en)	2004-10-05	Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-6,9-dioxa-2,3-diaza-cyclopenta[a]naphthalene
US20040147523A1 (en)	2004-07-29	Antidepressant piperidine derivatives of heterocycle-fused benzodioxans
HK1010103A (en)	1999-06-11	Dioxino derivatives and their use as dopamine agonists
HK1098154A (en)	2007-07-13	Dioxino derivatives and their use as dopamine agonists
EP0520674B1 (en)	1995-08-16	Antipsychotic benzodioxan derivatives
US6803368B2 (en)	2004-10-12	Antipsychotic aminomethyl derivatives of 7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalene
WO2002088134A2 (en)	2002-11-07	Antipsychotic aminomethyl derivatives of 1,3,7,8-tetrahydro-6,9-dioxa-1,3-diaza-cyclopenta[a]-naphthalen-2-one
HK1060878A1 (en)	2004-08-27	Dioxino derivatives and their use as dopamine agonists
HK1060878B (en)	2007-03-23	Dioxino derivatives and their use as dopamine agonists
IE67793B1 (en)	1996-05-01	Antipsychotic benzodioxan derivatives