CH672637A5 - - Google Patents

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Info

Publication number: CH672637A5
Authority: CH; Switzerland
Prior art keywords: compound; ethyl; group; mixture; physiologically acceptable
Prior art date: 1986-01-08

Application number

CH45/87A

Other languages

English (en)

French (fr)

Inventor

Alexander William Oxford

Ian Harold Coates

David Edmund Bays

Colin Frederick Webb

Michael Dennis Dowle

Keith Mills

Colin David Eldred

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.)

1986-01-08

Filing date

1987-01-08

Publication date

1989-12-15

1987-01-08 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1989-12-15 Publication of CH672637A5 publication Critical patent/CH672637A5/fr

Links

150000001875 compounds Chemical class 0.000 claims description 165
-1 alkoxy radical Chemical class 0.000 claims description 46
150000003839 salts Chemical class 0.000 claims description 38
238000000034 method Methods 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
230000008569 process Effects 0.000 claims description 17
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000012453 solvate Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 4
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 2
238000007614 solvation Methods 0.000 claims 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 165
239000000203 mixture Substances 0.000 description 85
239000000243 solution Substances 0.000 description 79
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
239000007787 solid Substances 0.000 description 74
239000000543 intermediate Substances 0.000 description 70
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 56
235000019441 ethanol Nutrition 0.000 description 55
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
239000003921 oil Substances 0.000 description 30
235000019198 oils Nutrition 0.000 description 30
239000000725 suspension Substances 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 27
239000006260 foam Substances 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
239000012458 free base Substances 0.000 description 21
239000010410 layer Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 19
238000004587 chromatography analysis Methods 0.000 description 19
239000000284 extract Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 17
235000006408 oxalic acid Nutrition 0.000 description 17
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 16
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 16
238000010992 reflux Methods 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
230000009467 reduction Effects 0.000 description 15
238000006722 reduction reaction Methods 0.000 description 15
239000002253 acid Substances 0.000 description 14
238000005187 foaming Methods 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
229910000027 potassium carbonate Inorganic materials 0.000 description 13
229910052938 sodium sulfate Inorganic materials 0.000 description 13
235000011152 sodium sulphate Nutrition 0.000 description 13
239000002904 solvent Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
241000400611 Eucalyptus deanei Species 0.000 description 12
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
229910052739 hydrogen Inorganic materials 0.000 description 12
238000003756 stirring Methods 0.000 description 12
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 11
239000004480 active ingredient Substances 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
235000011181 potassium carbonates Nutrition 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
239000000843 powder Substances 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
238000011282 treatment Methods 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
239000012267 brine Substances 0.000 description 8
239000003638 chemical reducing agent Substances 0.000 description 8
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
230000008570 general process Effects 0.000 description 8
229960004592 isopropanol Drugs 0.000 description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
208000019695 Migraine disease Diseases 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
238000007796 conventional method Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000007789 gas Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
238000007363 ring formation reaction Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
239000002585 base Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
206010027599 migraine Diseases 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
MROJXXOCABQVEF-UHFFFAOYSA-N Actarit Chemical compound CC(=O)NC1=CC=C(CC(O)=O)C=C1 MROJXXOCABQVEF-UHFFFAOYSA-N 0.000 description 5
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 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000003377 acid catalyst Substances 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000006228 supernatant Substances 0.000 description 5
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 4
NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
150000001350 alkyl halides Chemical class 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
150000002475 indoles Chemical class 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
239000005526 vasoconstrictor agent Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 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
229920000388 Polyphosphate Polymers 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000011260 aqueous acid Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
125000006360 carbonyl amino methylene group Chemical group [H]N(C([*:1])=O)C([H])([H])[*:2] 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
150000004677 hydrates Chemical class 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910003445 palladium oxide Inorganic materials 0.000 description 3
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 3
239000001205 polyphosphate Substances 0.000 description 3
235000011176 polyphosphates Nutrition 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
229910052703 rhodium Inorganic materials 0.000 description 3
239000010948 rhodium Substances 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
WQKVKXUVNZSAEW-UHFFFAOYSA-N 2-[4-[2-(dimethylamino)-2-oxoethyl]phenyl]acetic acid Chemical compound CN(C)C(=O)CC1=CC=C(CC(O)=O)C=C1 WQKVKXUVNZSAEW-UHFFFAOYSA-N 0.000 description 2
MEVXSUZBFYZPHZ-UHFFFAOYSA-N 2-amino-3-methyl-4h-imidazol-5-one;sulfuric acid Chemical compound OS(O)(=O)=O.CN1CC(=O)N=C1N MEVXSUZBFYZPHZ-UHFFFAOYSA-N 0.000 description 2
REIDAMBAPLIATC-UHFFFAOYSA-N 4-methoxycarbonylbenzoic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229920002785 Croscarmellose sodium Polymers 0.000 description 2
239000004338 Dichlorodifluoromethane Substances 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
206010019233 Headaches Diseases 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
150000001241 acetals Chemical class 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229940054051 antipsychotic indole derivative Drugs 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000012431 aqueous reaction media Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
239000007822 coupling agent Substances 0.000 description 2
229960001681 croscarmellose sodium Drugs 0.000 description 2
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238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000001923 methylcellulose Substances 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
239000012452 mother liquor Substances 0.000 description 1
PQSOLLURQXDZSZ-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate;methanol Chemical compound OC.CCOC(C)=O.CCN(CC)CC PQSOLLURQXDZSZ-UHFFFAOYSA-N 0.000 description 1
XXESGIZABZSFSR-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NCCC1=CC=C(N)C=C1 XXESGIZABZSFSR-UHFFFAOYSA-N 0.000 description 1
FYCFLJQBRXHKQE-UHFFFAOYSA-N n-[2-(4-hydrazinylphenyl)ethyl]-2-(4-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(=O)NCCC1=CC=C(NN)C=C1 FYCFLJQBRXHKQE-UHFFFAOYSA-N 0.000 description 1
XWAGEUUUKVILOE-UHFFFAOYSA-N n-[2-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]ethyl]-2-(4-methoxyphenyl)acetamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1=CC(OC)=CC=C1CC(=O)NCCC1=CC=C(NC=C2CCN(C)C)C2=C1 XWAGEUUUKVILOE-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229940124641 pain reliever Drugs 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
230000005588 protonation Effects 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000002994 raw material Substances 0.000 description 1
235000019515 salmon Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 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
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
230000003639 vasoconstrictive effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH45/87A 1986-01-08 1987-01-08 CH672637A5 (2)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868600397A GB8600397D0 (en)	1986-01-08	1986-01-08	Chemical compounds

Publications (1)

Publication Number	Publication Date
CH672637A5 true CH672637A5 (2)	1989-12-15

Family

ID=10591074

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH45/87A CH672637A5 (2)	1986-01-08	1987-01-08

Country Status (23)

Country	Link
US (1)	US4855314A (2)
EP (1)	EP0240096A1 (2)
JP (1)	JPS62228056A (2)
KR (1)	KR870007116A (2)
CN (1)	CN1030409A (2)
AU (1)	AU597325B2 (2)
BE (1)	BE1000071A4 (2)
CH (1)	CH672637A5 (2)
DE (1)	DE3700408A1 (2)
DK (1)	DK8787A (2)
FI (1)	FI870062A7 (2)
FR (1)	FR2595351B1 (2)
GB (2)	GB8600397D0 (2)
HU (1)	HU198685B (2)
IL (1)	IL81201A (2)
IT (1)	IT1205849B (2)
LU (1)	LU86732A1 (2)
NL (1)	NL8700026A (2)
NO (1)	NO870075L (2)
NZ (1)	NZ218868A (2)
PH (1)	PH24741A (2)
PT (1)	PT84075B (2)
ZA (1)	ZA87105B (2)

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GB8530507D0 (en) *	1985-12-11	1986-01-22	Glaxo Group Plc	Chemical compounds
GB8600398D0 (en) *	1986-01-08	1986-02-12	Glaxo Group Ltd	Chemical compounds
US5225431A (en) *	1987-10-23	1993-07-06	Burroughs Wellcome Co.	Therapeutic substituted indole compounds and compositions thereof
GB8724912D0 (en)	1987-10-23	1987-11-25	Wellcome Found	Indole derivatives
GB8819024D0 (en) *	1988-08-10	1988-09-14	Glaxo Group Ltd	Chemical compounds
GB8823731D0 (en) *	1988-10-10	1988-11-16	Smith Kline French Lab	Biologically active compounds
CZ288351B6 (en) *	1990-06-07	2001-05-16	Astrazeneca Ab	Nitrogenous heterocyclic compound, process of its preparation and use as well as a medicament containing thereof
US5559246A (en) *	1990-10-15	1996-09-24	Pfizer Inc.	Indole derivatives
US5545644A (en) *	1990-10-15	1996-08-13	Pfizer Inc.	Indole derivatives
HU225055B1 (en) *	1990-10-15	2006-05-29	Pfizer	Indole derivatives, their intermediates, process for production them and pharmaceutical compositions containing the compounds
US5559129A (en) *	1990-10-15	1996-09-24	Pfizer Inc	Indole derivatives
US5607951A (en) *	1990-10-15	1997-03-04	Pfizer Inc	Indole derivatives
US5578612A (en) *	1990-10-15	1996-11-26	Pfizer Inc.	Indole derivatives
CA2061520C (en) *	1991-03-27	2003-04-22	Lawrence J. Daher	Delivery system for enhanced onset and increased potency
CA2124206C (en) *	1991-11-25	2001-02-27	John Eugene Macor	Indole derivatives
TW288010B (2) *	1992-03-05	1996-10-11	Pfizer
AU670579B2 (en)	1992-04-07	1996-07-25	Pfizer Inc.	Indole derivatives as 5-HT1 agonists
US6380233B1 (en)	1992-04-07	2002-04-30	Pfizer Inc	Indole derivatives as 5-HT1 agonists
GB9207930D0 (en) *	1992-04-10	1992-05-27	Pfizer Ltd	Indoles
EP0635015B1 (en) *	1992-04-10	1997-01-29	Pfizer Inc.	Acylaminoindole derivatives as 5-ht1 agonists
GB9211277D0 (en)	1992-05-28	1992-07-15	Glaxo Group Inc	Pharmaceutical compositions
TW251284B (2) *	1992-11-02	1995-07-11	Pfizer
FR2707639B1 (fr) *	1993-06-30	1995-10-13	Pf Medicament	Nouveaux composés indoliques dérivés d'arylamines comme ligands sélectifs des récepteurs 5HT1D et 5HT1B.
ES2070772B1 (es) *	1993-08-09	1996-02-16	Pfizer	Derivados de acilaminoindol
AU686654B2 (en) *	1993-08-31	1998-02-12	Pfizer Inc.	5-arylindole derivatives
US5468768A (en) *	1994-01-06	1995-11-21	Bristol-Myers Squibb Company	Antimigraine derivatives of indolylcycloalkanylamines
GB9417310D0 (en)	1994-08-27	1994-10-19	Pfizer Ltd	Therapeutic agents
FR2749846B1 (fr) *	1996-06-17	1998-09-11	Pf Medicament	Sel de methanesulfonate d'une arylpiperazine derivee de tryptamine et ses solvates pour usage pharmaceutique
US7189753B1 (en)	1997-11-06	2007-03-13	Cady Roger K	Preemptive prophylaxis of migraine
US5994352A (en) *	1998-11-13	1999-11-30	Pfizer Inc.	5-arylindole derivatives
EP1311478B1 (en) *	2000-08-21	2006-06-07	Pacific Corporation	Novel (thio)urea compounds and the pharmaceutical compositions containing the same
SI1517909T1 (sl)	2002-06-21	2007-06-30	Suven Life Sciences Ltd	Novi tetraciklični arilkarbonil indoli, ki imajo afiniteto za serotoninski receptor, uporabni kot terapevtska sredstva, postopek za njihovo pripravo in farmacevtski sestavki, ki jih vsebujejo
ES2297216T3 (es) *	2002-06-21	2008-05-01	Suven Life Sciences Limited	Indoles tetraciclicos arilsulfonil que tienen afinidad con el receptor de la serotonina.
BR0312175A (pt) *	2002-06-21	2005-04-05	Suven Life Sciences Ltd	Composto, composição farmacêutica, uso de um composto, método para o tratamento e método para reduzir a morbidez e a mortalidade associadas com o excesso de peso
US7507835B2 (en)	2002-11-28	2009-03-24	Suven Life Sciences Ltd.	N-arylsulfonyl-3-aminoalkoxyindoles
ATE401307T1 (de) *	2002-11-28	2008-08-15	Suven Life Sciences Ltd	N-arylsulfonyl-2-substituierte indole mit affinität zum serotonin rezeptor, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
JP4571507B2 (ja) *	2002-12-18	2010-10-27	スベンライフサイエンシズリミティド	セロトニン受容体親和性を有する四環系３−置換インドール
CA2508290C (en) *	2002-12-20	2017-02-28	Ciba Specialty Chemicals Holding Inc.	Synthesis of amines and intermediates for the synthesis thereof
AU2007257882B2 (en)	2006-06-12	2011-09-08	Secura Bio Inc.	Process for making salts of N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-2E-2-propenamide

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US3472870A (en) *	1966-08-29	1969-10-14	Mead Johnson & Co	Sulfonamidotryptamines
FR2334358A1 (fr) *	1975-12-12	1977-07-08	Sogeras	Nouveaux medicaments derives de l'indole
ZA795239B (en) *	1978-10-12	1980-11-26	Glaxo Group Ltd	Heterocyclic compounds
ZW19381A1 (en) *	1980-08-12	1983-03-09	Glaxo Group Ltd	Heterocyclic compounds
DK157995C (da) *	1980-08-12	1990-08-06	Glaxo Group Ltd	Analogifremgangsmaade til fremstilling af indolderivater
GB8332437D0 (en) *	1983-12-06	1984-01-11	Glaxo Group Ltd	Chemical compounds
GB8332435D0 (en) *	1983-12-06	1984-01-11	Glaxo Group Ltd	Chemical compounds
GB8332434D0 (en) *	1983-12-06	1984-01-11	Glaxo Group Ltd	Production of chemical compounds
GB8600398D0 (en) *	1986-01-08	1986-02-12	Glaxo Group Ltd	Chemical compounds

1986
- 1986-01-08 GB GB868600397A patent/GB8600397D0/en active Pending
1987
- 1987-01-08 CH CH45/87A patent/CH672637A5/fr not_active IP Right Cessation
- 1987-01-08 GB GB8700382A patent/GB2185020B/en not_active Expired - Fee Related
- 1987-01-08 PT PT84075A patent/PT84075B/pt not_active IP Right Cessation
- 1987-01-08 DE DE19873700408 patent/DE3700408A1/de not_active Withdrawn
- 1987-01-08 PH PH34698A patent/PH24741A/en unknown
- 1987-01-08 NL NL8700026A patent/NL8700026A/nl not_active Application Discontinuation
- 1987-01-08 DK DK008787A patent/DK8787A/da unknown
- 1987-01-08 FI FI870062A patent/FI870062A7/fi not_active Application Discontinuation
- 1987-01-08 AU AU67420/87A patent/AU597325B2/en not_active Ceased
- 1987-01-08 LU LU86732A patent/LU86732A1/fr unknown
- 1987-01-08 ZA ZA87105A patent/ZA87105B/xx unknown
- 1987-01-08 IL IL81201A patent/IL81201A/xx unknown
- 1987-01-08 JP JP62002589A patent/JPS62228056A/ja active Pending
- 1987-01-08 NO NO870075A patent/NO870075L/no unknown
- 1987-01-08 EP EP87300166A patent/EP0240096A1/en not_active Withdrawn
- 1987-01-08 US US07/001,469 patent/US4855314A/en not_active Expired - Lifetime
- 1987-01-08 BE BE8700003A patent/BE1000071A4/fr not_active IP Right Cessation
- 1987-01-08 NZ NZ218868A patent/NZ218868A/xx unknown
- 1987-01-08 KR KR870000068A patent/KR870007116A/ko not_active Withdrawn
- 1987-01-08 FR FR878700107A patent/FR2595351B1/fr not_active Expired - Fee Related
- 1987-01-08 IT IT47507/87A patent/IT1205849B/it active
- 1987-07-03 HU HU873020A patent/HU198685B/hu not_active IP Right Cessation
- 1987-07-06 CN CN87105335A patent/CN1030409A/zh active Pending

Also Published As

Publication number	Publication date
IT1205849B (it)	1989-03-31
GB8600397D0 (en)	1986-02-12
PH24741A (en)	1990-10-01
EP0240096A1 (en)	1987-10-07
NO870075D0 (no)	1987-01-08
GB2185020A (en)	1987-07-08
US4855314A (en)	1989-08-08
KR870007116A (ko)	1987-08-14
IL81201A0 (en)	1987-08-31
CN1030409A (zh)	1989-01-18
IT8747507A0 (it)	1987-01-08
FR2595351A1 (fr)	1987-09-11
GB8700382D0 (en)	1987-02-11
FR2595351B1 (fr)	1990-07-13
JPS62228056A (ja)	1987-10-06
NZ218868A (en)	1990-04-26
DE3700408A1 (de)	1987-07-09
PT84075A (en)	1987-02-01
ZA87105B (en)	1987-09-30
NL8700026A (nl)	1987-08-03
IL81201A (en)	1991-06-10
FI870062A0 (fi)	1987-01-08
GB2185020B (en)	1990-05-16
PT84075B (pt)	1989-07-31
HU198685B (en)	1989-11-28
HUT46891A (en)	1988-12-28
LU86732A1 (fr)	1988-02-02
FI870062A7 (fi)	1987-07-09
NO870075L (no)	1987-07-09
DK8787A (da)	1987-07-09
DK8787D0 (da)	1987-01-08
AU597325B2 (en)	1990-05-31
AU6742087A (en)	1987-07-09
BE1000071A4 (fr)	1988-02-02

Legal Events

Date	Code	Title	Description
1994-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
BE1000071A4 (fr)	1988-02-02	Derives d'indole, procede pour leur preparation et compositions pharmaceutiques les contenant.
EP0950047B1 (fr)	2003-10-15	Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant
CH657359A5 (fr)	1986-08-29	Derives d'indole, procedes pour leur preparation et composition pharmaceutique les contenant.
EP0591057B1 (fr)	1996-07-10	Arylalkyl(thio)amides ayant une affinité sélective pour les récepteurs de la mélatonine et leur procédé de préparation
JP2755560B2 (ja)	1998-05-20	三環式ピラゾール誘導体
CH666026A5 (fr)	1988-06-30	Derive d'indole.
EP0658546B1 (fr)	2001-05-23	Dérivés de 3-pyrazolecarboxamide avec une affinité pour le récepteur des cannabinoides
CH663411A5 (fr)	1987-12-15	Derives d'indole utiles comme medicaments.
CH651550A5 (fr)	1985-09-30	Derives de l'indole, leur preparation et compositions pharmaceutiques les contenant.
CH651551A5 (fr)	1985-09-30	Derives de l'indole, leur preparation et compositions pharmaceutiques les contenant.
LU87414A1 (fr)	1989-07-07	Derives de l'adenosine
CH667647A5 (fr)	1988-10-31	5-alkenesulfonamides indoles.
CH622254A5 (2)	1981-03-31
EP0984960B1 (fr)	2003-02-05	N-triazolyl-2-indolecarboxamides et leur utilisation comme agonistes de cck-a
CH652394A5 (fr)	1985-11-15	Derives indoliques, leur preparation et medicaments les renfermant.
EP0677042B1 (fr)	1998-07-22	Ligands selectifs des recepteurs 5ht1d-5ht1b derives d'indole-piperazine utiles comme medicaments
BE1000072A4 (fr)	1988-02-02	Derives de l'indole utiles comme medicaments et procede et intermediaires pour leur preparation.
CH667454A5 (fr)	1988-10-14	Derives d'indoles.
EP0611766A1 (fr)	1994-08-24	Dérivés de 2-amido-thiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament
EP0662971B1 (fr)	1998-05-13	DERIVES DE 5H,10H-IMIDAZO[1,2-a]INDENO[1,2-e]PYRAZINE-4-ONE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
EP1507758B1 (fr)	2005-11-02	Derives d'indole et leur utilisation en tant que ligands des recepteurs cb2
EP0620221A1 (fr)	1994-10-19	5-Acylamino 1,2,4-thiadiazoles comme antagonistes ou agonistes de la cholécystokinine
EP1242389A2 (fr)	2002-09-25	Nouveaux derives amino substitues ramifies du 3-amino-1-phenyl-1h[1,2,4]triazole, procedes pour leur preparation et compositions pharmaceutiques les contenant
WO1995001334A1 (fr)	1995-01-12	Composes indoliques derives d'arylamines comme ligands selectifs des recepteurs 5ht1d et 5ht¿1b?
FR2600061A1 (fr)	1987-12-18	Derives d'indole, composition pharmaceutique les contenant et procede pour leur preparation