IL129647A - -4 (-6 Fluoro (-1H) indole - 3 il) - 6,3,2,1 tetrahydro pyridines are converted, their preparation and pharmaceutical preparations containing them for the treatment of disorders of the central nervous system - Google Patents

-4 (-6 Fluoro (-1H) indole - 3 il) - 6,3,2,1 tetrahydro pyridines are converted, their preparation and pharmaceutical preparations containing them for the treatment of disorders of the central nervous system

Info

Publication number: IL129647A
Authority: IL; Israel
Prior art keywords: fluoro; hydrogen; indol; compound; compound according
Prior art date: 1997-01-17

Application number

IL12964798A

Other languages

English (en)

Hebrew (he)

Other versions

IL129647A0 (en

Original Assignee

Lilly Co Eli

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.)

1997-01-17

Filing date

1998-01-14

Publication date

2002-02-10

1998-01-14 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2000-02-29 Publication of IL129647A0 publication Critical patent/IL129647A0/xx

2002-02-10 Publication of IL129647A publication Critical patent/IL129647A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 56
150000003839 salts Chemical class 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
-1 6-Fluoro-lH-indol-3-yl Chemical group 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
JVSYWJKDDRYLMM-UHFFFAOYSA-N 2lambda6-thia-1,3-diazatricyclo[6.3.1.04,12]dodeca-4,6,8(12),9-tetraene 2,2-dioxide Chemical compound C1=CCN2S(=O)(=O)NC3=CC=CC1=C32 JVSYWJKDDRYLMM-UHFFFAOYSA-N 0.000 claims description 3
210000003169 central nervous system Anatomy 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 23
239000007787 solid Substances 0.000 description 19
239000000243 solution Substances 0.000 description 18
239000004480 active ingredient Substances 0.000 description 16
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
235000019359 magnesium stearate Nutrition 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
238000012360 testing method Methods 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
230000027455 binding Effects 0.000 description 6
239000002775 capsule Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
239000008107 starch Substances 0.000 description 6
229940032147 starch Drugs 0.000 description 6
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 5
239000000284 extract Substances 0.000 description 5
239000008101 lactose Substances 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
239000000047 product Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000008109 sodium starch glycolate Substances 0.000 description 4
229940079832 sodium starch glycolate Drugs 0.000 description 4
229920003109 sodium starch glycolate Polymers 0.000 description 4
239000000725 suspension Substances 0.000 description 4
102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 3
108010072564 5-HT2A Serotonin Receptor Proteins 0.000 description 3
YYFFEPUCAKVRJX-UHFFFAOYSA-N 6-fluoro-1h-indole Chemical compound FC1=CC=C2C=CNC2=C1 YYFFEPUCAKVRJX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
101150049660 DRD2 gene Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
235000010980 cellulose Nutrition 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
208000015114 central nervous system disease Diseases 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000005457 ice water Substances 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 3
IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 3
VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 2
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
GBPJZEAYVTZRKQ-UHFFFAOYSA-N 6-fluoro-1,2,3,4-tetrahydroquinolin-8-amine Chemical compound C1CCNC2=C1C=C(F)C=C2N GBPJZEAYVTZRKQ-UHFFFAOYSA-N 0.000 description 2
FBWKDFSEFVFKFY-UHFFFAOYSA-N 6-fluoro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound C=1NC2=CC(F)=CC=C2C=1C1=CCNCC1 FBWKDFSEFVFKFY-UHFFFAOYSA-N 0.000 description 2
LDSAYITYLRHGQV-UHFFFAOYSA-N 6-fluoro-8-nitroquinoline Chemical compound C1=CN=C2C([N+](=O)[O-])=CC(F)=CC2=C1 LDSAYITYLRHGQV-UHFFFAOYSA-N 0.000 description 2
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 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
239000004141 Sodium laurylsulphate Substances 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
COHDHYZHOPQOFD-UHFFFAOYSA-N arsenic pentoxide Chemical compound O=[As](=O)O[As](=O)=O COHDHYZHOPQOFD-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
229940076279 serotonin Drugs 0.000 description 2
230000000697 serotonin reuptake Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
239000012265 solid product Substances 0.000 description 2
208000011117 substance-related disease Diseases 0.000 description 2
239000012485 toluene extract Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
QMSVNDSDEZTYAS-UHFFFAOYSA-N 1-bromo-1-chloroethane Chemical compound CC(Cl)Br QMSVNDSDEZTYAS-UHFFFAOYSA-N 0.000 description 1
BGMZUEKZENQUJY-UHFFFAOYSA-N 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine Chemical compound COC1=CC(CC(C)N)=C(OC)C=C1I BGMZUEKZENQUJY-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
DWHMTTROZUHZMC-UHFFFAOYSA-N 3-methyl-8-nitroquinoline Chemical compound [O-][N+](=O)C1=CC=CC2=CC(C)=CN=C21 DWHMTTROZUHZMC-UHFFFAOYSA-N 0.000 description 1
VAHBEBMTFYQSNV-UHFFFAOYSA-N 3-methyl-8-nitroquinoline sulfuric acid Chemical compound OS(O)(=O)=O.Cc1cnc2c(cccc2c1)[N+]([O-])=O VAHBEBMTFYQSNV-UHFFFAOYSA-N 0.000 description 1
SKWTUNAAJNDEIK-UHFFFAOYSA-N 4-fluoro-1-methyl-2-nitrobenzene Chemical compound CC1=CC=C(F)C=C1[N+]([O-])=O SKWTUNAAJNDEIK-UHFFFAOYSA-N 0.000 description 1
PUGDHSSOXPHLPT-UHFFFAOYSA-N 4-fluoro-2-nitroaniline Chemical compound NC1=CC=C(F)C=C1[N+]([O-])=O PUGDHSSOXPHLPT-UHFFFAOYSA-N 0.000 description 1
LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 1
101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
XOIKVJDBODECPS-UHFFFAOYSA-N 6-fluoro-8-nitroquinoline sulfuric acid Chemical compound S(=O)(=O)(O)O.FC=1C=C2C=CC=NC2=C(C1)[N+](=O)[O-] XOIKVJDBODECPS-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 0.000 description 1
108060003345 Adrenergic Receptor Proteins 0.000 description 1
102000017910 Adrenergic receptor Human genes 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
208000000044 Amnesia Diseases 0.000 description 1
206010002869 Anxiety symptoms Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
208000020925 Bipolar disease Diseases 0.000 description 1
208000032841 Bulimia Diseases 0.000 description 1
206010006550 Bulimia nervosa Diseases 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
206010054089 Depressive symptom Diseases 0.000 description 1
102000004980 Dopamine D2 Receptors Human genes 0.000 description 1
108090001111 Dopamine D2 Receptors Proteins 0.000 description 1
206010013654 Drug abuse Diseases 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
208000019454 Feeding and Eating disease Diseases 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
229920000084 Gum arabic Polymers 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
206010020843 Hyperthermia Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
208000026139 Memory disease Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
208000008589 Obesity Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 1
108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 1
201000001880 Sexual dysfunction Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
DLMLEDJNPUODNO-UHFFFAOYSA-N [N+](=O)([O-])C=1C=CC=C2C=CC=NC12.NC=1C=CC=C2CCCNC12 Chemical compound [N+](=O)([O-])C=1C=CC=C2C=CC=NC12.NC=1C=CC=C2CCCNC12 DLMLEDJNPUODNO-UHFFFAOYSA-N 0.000 description 1
FXYCTPUZPDUEEM-UHFFFAOYSA-N [Pt]=O.NC=1C=CC=C2CC(CNC12)C Chemical compound [Pt]=O.NC=1C=CC=C2CC(CNC12)C FXYCTPUZPDUEEM-UHFFFAOYSA-N 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
201000007930 alcohol dependence Diseases 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
208000022531 anorexia Diseases 0.000 description 1
239000003420 antiserotonin agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
206010061428 decreased appetite Diseases 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000003001 depressive effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
206010013663 drug dependence Diseases 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000011554 guinea pig model Methods 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
230000036031 hyperthermia Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 1
229960005417 ketanserin Drugs 0.000 description 1
229960001375 lactose Drugs 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000006984 memory degeneration Effects 0.000 description 1
208000023060 memory loss Diseases 0.000 description 1
QFXJBPCTHSTOPE-UHFFFAOYSA-N methacrolein diacetate Chemical compound CC(=O)OC(C(C)=C)OC(C)=O QFXJBPCTHSTOPE-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical group COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229960001779 pargyline Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
239000003772 serotonin uptake inhibitor Substances 0.000 description 1
231100000872 sexual dysfunction Toxicity 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
230000005586 smoking cessation Effects 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 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
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-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
- A61P25/04—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
- A61P25/18—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
- 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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

IL12964798A 1997-01-17 1998-01-14 -4 (-6 Fluoro (-1H) indole - 3 il) - 6,3,2,1 tetrahydro pyridines are converted, their preparation and pharmaceutical preparations containing them for the treatment of disorders of the central nervous system IL129647A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9700895.7A GB9700895D0 (en)	1997-01-17	1997-01-17	Pharmaceutical compounds
PCT/GB1998/000113 WO1998031686A1 (en)	1997-01-17	1998-01-14	Substituted 4-(6-fluoro-(1h)-indol-3-yl)-1,2,3,6-tetrahydropyridine for the treatment of cns-disorders

Publications (2)

Publication Number	Publication Date
IL129647A0 IL129647A0 (en)	2000-02-29
IL129647A true IL129647A (en)	2002-02-10

Family

ID=10806121

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12964798A IL129647A (en)	1997-01-17	1998-01-14	-4 (-6 Fluoro (-1H) indole - 3 il) - 6,3,2,1 tetrahydro pyridines are converted, their preparation and pharmaceutical preparations containing them for the treatment of disorders of the central nervous system

Country Status (29)

Country	Link
US (1)	US20010053783A1 (id)
EP (1)	EP0854146B1 (id)
JP (1)	JPH10204090A (id)
KR (1)	KR20000070221A (id)
AR (1)	AR011422A1 (id)
AT (1)	ATE190617T1 (id)
AU (1)	AU5569298A (id)
CA (1)	CA2227132A1 (id)
CZ (1)	CZ290318B6 (id)
DE (1)	DE69800092T2 (id)
DK (1)	DK0854146T3 (id)
EA (1)	EA001469B1 (id)
ES (1)	ES2144888T3 (id)
GB (1)	GB9700895D0 (id)
GR (1)	GR3033316T3 (id)
HU (1)	HUP0000854A3 (id)
ID (1)	ID21920A (id)
IL (1)	IL129647A (id)
NO (1)	NO993372D0 (id)
NZ (1)	NZ335493A (id)
PE (1)	PE99399A1 (id)
PL (1)	PL334569A1 (id)
PT (1)	PT854146E (id)
SI (1)	SI0854146T1 (id)
SV (1)	SV1998000088A (id)
TR (1)	TR199901583T2 (id)
TW (1)	TW396156B (id)
WO (1)	WO1998031686A1 (id)
ZA (1)	ZA98300B (id)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU8743098A (en) *	1997-08-22	1999-03-16	Eli Lilly And Company Limited	Benzothiadiazinyl-indole derivatives and their use as serotonin receptor ligands
GB9825413D0 (en) *	1998-11-19	1999-01-13	Lilly Co Eli	Pharmaceutical compounds
GB9903784D0 (en) *	1999-02-18	1999-04-14	Lilly Co Eli	Pharmaceutical compounds
AR028945A1 (es) *	2000-06-19	2003-05-28	Lundbeck & Co As H	Derivados de indol
KR101165996B1 (ko)	2010-04-23	2012-07-18	주식회사 녹십자	프탈라지논 유도체, 이의 제조방법 및 이를 함유하는 약학적 조성물
CN105949190B (zh) *	2016-07-04	2018-06-29	烟台凯博医药科技有限公司	一种制备1，8-萘啶及衍生物的方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2662696A2 (fr) *	1989-12-13	1991-12-06	Rhone Poulenc Sante	Antagonistes de la serotonine, leur preparation et medicaments les contenant.
DK158590D0 (da) *	1990-07-02	1990-07-02	Lundbeck & Co As H	Indolderivater
FR2675801A1 (fr) *	1991-04-24	1992-10-30	Rhone Poulenc Rorer Sa	Piperidines, leur preparation et les medicaments les contenant.
DE19500689A1 (de) *	1995-01-12	1996-07-18	Merck Patent Gmbh	Indolpiperidin-Derivate
US5576321A (en) *	1995-01-17	1996-11-19	Eli Lilly And Company	Compounds having effects on serotonin-related systems

1997
- 1997-01-17 GB GBGB9700895.7A patent/GB9700895D0/en active Pending
1998
- 1998-01-13 TW TW087100373A patent/TW396156B/zh not_active IP Right Cessation
- 1998-01-13 US US09/005,995 patent/US20010053783A1/en not_active Abandoned
- 1998-01-14 HU HU0000854A patent/HUP0000854A3/hu unknown
- 1998-01-14 ES ES98300249T patent/ES2144888T3/es not_active Expired - Lifetime
- 1998-01-14 SI SI9830009T patent/SI0854146T1/xx unknown
- 1998-01-14 AT AT98300249T patent/ATE190617T1/de not_active IP Right Cessation
- 1998-01-14 EP EP98300249A patent/EP0854146B1/en not_active Expired - Lifetime
- 1998-01-14 ID IDW990623A patent/ID21920A/id unknown
- 1998-01-14 NZ NZ335493A patent/NZ335493A/xx unknown
- 1998-01-14 JP JP10005897A patent/JPH10204090A/ja active Pending
- 1998-01-14 DE DE69800092T patent/DE69800092T2/de not_active Expired - Fee Related
- 1998-01-14 AU AU55692/98A patent/AU5569298A/en not_active Abandoned
- 1998-01-14 CZ CZ19991510A patent/CZ290318B6/cs not_active IP Right Cessation
- 1998-01-14 TR TR1999/01583T patent/TR199901583T2/xx unknown
- 1998-01-14 IL IL12964798A patent/IL129647A/en not_active IP Right Cessation
- 1998-01-14 WO PCT/GB1998/000113 patent/WO1998031686A1/en not_active Ceased
- 1998-01-14 PL PL98334569A patent/PL334569A1/xx unknown
- 1998-01-14 KR KR1019997006447A patent/KR20000070221A/ko not_active Withdrawn
- 1998-01-14 PT PT98300249T patent/PT854146E/pt unknown
- 1998-01-14 DK DK98300249T patent/DK0854146T3/da active
- 1998-01-14 ZA ZA98300A patent/ZA98300B/xx unknown
- 1998-01-14 EA EA199900667A patent/EA001469B1/ru not_active IP Right Cessation
- 1998-01-15 CA CA002227132A patent/CA2227132A1/en not_active Abandoned
- 1998-01-16 AR ARP980100185A patent/AR011422A1/es unknown
- 1998-07-09 PE PE1998000607A patent/PE99399A1/es not_active Application Discontinuation
- 1998-07-16 SV SV1998000088A patent/SV1998000088A/es unknown
1999
- 1999-07-08 NO NO993372A patent/NO993372D0/no not_active Application Discontinuation
2000
- 2000-04-26 GR GR20000401000T patent/GR3033316T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
PT854146E (pt)	2000-08-31
EA199900667A1 (ru)	2000-02-28
CA2227132A1 (en)	1998-07-17
ES2144888T3 (es)	2000-06-16
HUP0000854A2 (hu)	2000-11-28
SI0854146T1 (en)	2000-10-31
SV1998000088A (es)	2000-10-10
AU5569298A (en)	1998-08-07
EA001469B1 (ru)	2001-04-23
NZ335493A (en)	2000-09-29
PE99399A1 (es)	1999-11-11
NO993372L (no)	1999-07-08
DK0854146T3 (da)	2000-06-05
DE69800092T2 (de)	2000-09-14
CZ290318B6 (cs)	2002-07-17
AR011422A1 (es)	2000-08-16
WO1998031686A1 (en)	1998-07-23
ID21920A (id)	1999-08-12
NO993372D0 (no)	1999-07-08
DE69800092D1 (de)	2000-04-20
GB9700895D0 (en)	1997-03-05
JPH10204090A (ja)	1998-08-04
US20010053783A1 (en)	2001-12-20
EP0854146B1 (en)	2000-03-15
ZA98300B (en)	1998-09-10
CZ151099A3 (cs)	1999-09-15
HUP0000854A3 (en)	2002-06-28
TW396156B (en)	2000-07-01
ATE190617T1 (de)	2000-04-15
EP0854146A1 (en)	1998-07-22
PL334569A1 (en)	2000-03-13
TR199901583T2 (xx)	1999-11-22
KR20000070221A (ko)	2000-11-25
IL129647A0 (en)	2000-02-29
GR3033316T3 (en)	2000-09-29

Legal Events

Date	Code	Title	Description
2002-06-30	FF	Patent granted
2003-05-29	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0553191B1 (en)	1995-05-17	Pyridine and pyridine n-oxide derivatives of diarylmethyl- piperidines or piperazines, compositions and use thereof
US5834493A (en)	1998-11-10	Indole derivatives as 5-HT1A and/or 5-HT2 ligands
IE58122B1 (en)	1993-07-14	An indole derivative
NO335015B1 (no)	2014-08-25	Fremgangsmåte for fremstilling av 5-HT(serotonin)-ligander
US5563147A (en)	1996-10-08	Serotonerbic tetrahydropyridoindoles
CA1296730C (en)	1992-03-03	6,7,8,9-tetrahydropyrido[1,2-a] indole derivatives
US5929072A (en)	1999-07-27	1H-2,1,3-benzothiadiazine-2,2-dioxide compounds or derivatives thereof
EP0854146B1 (en)	2000-03-15	Substituted 4-(6-fluoro-[1H]-indol-3-yl)-1,2,3,6-tetrahydropyridine for the treatment of CNS-disorders
AU683700B2 (en)	1997-11-20	Phenylindole compounds
US4447434A (en)	1984-05-08	Substituted dibenzodiazepinones
HU201543B (en)	1990-11-28	Process for production of derivatives of 2-(/piperin-4-il/-methil/)-1,2,3,4-tetrahydro-izoquinoline and medical compositions containing them
NZ205786A (en)	1985-12-13	Heterocyclic-substituted phenylindene derivatives and pharmaceutical compositions
TW589312B (en)	2004-06-01	Aryl-8-azabicyclo[3.2.1]octanes for the treatment of depression
WO2000049017A1 (en)	2000-08-24	1-((indoly azacycloalkyl) alkyl)-2,1, 3-benzothiadiazole 2,2-dioxides exhibiting 5-ht2a receptor activity
HK1015364A (en)	1999-10-15	Substituted 4-(6-fluoro-[1h]-indol-3-yl)-1,2,3,6-tetrahydropyridine for the treatment of cns-disorders
MXPA99005277A (en)	2000-01-01	Substituted 4-(6-fluoro-(1h)-indol-3-yl)-1,2,3,6-tetrahydropyridine for the treatment of cns-disorders
EP0743946A1 (en)	1996-11-27	5ht2b receptor antagonists condensed indoles
JPH05230057A (ja)	1993-09-07	光学活性インダゾール―３―カルボキサミド誘導体及びそれを有効成分とする制吐剤
NZ240146A (en)	1994-02-25	Pyridine (n-oxide) derivatives of di-aryl methyl piperidine or piperazines;