JPS61151172A - インドール、その製造方法及びそれを含有する製薬組成物 - Google Patents

インドール、その製造方法及びそれを含有する製薬組成物

Info

Publication number: JPS61151172A
Authority: JP; Japan
Prior art keywords: group; indole; general formula; formula; hydrogen atom
Prior art date: 1984-12-13
Legal status (The legal status 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 status listed.): Pending

Application number

JP60278124A

Other languages

English (en)

Japanese (ja)

Inventor

デイビツド・エドマンド・ベイズ

コリン・フレデリツク・ウエブ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1984-12-13

Filing date

1985-12-12

Publication date

1986-07-09

1985-12-12 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1986-07-09 Publication of JPS61151172A publication Critical patent/JPS61151172A/ja

Status Pending legal-status Critical Current

Links

SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 43
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title claims description 22
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title claims description 22
238000004519 manufacturing process Methods 0.000 title claims description 9
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 124
150000003839 salts Chemical class 0.000 claims description 40
238000000034 method Methods 0.000 claims description 36
238000006243 chemical reaction Methods 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
230000002829 reductive effect Effects 0.000 claims description 25
239000000126 substance Substances 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 21
-1 3-(2-aminoethyl)-N-([4-(1-pyrrolidinyl)phenyl] methyl)-1H-indole-5-propanamide 3-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]-1H-indole-5-propanamide Chemical compound 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
239000004480 active ingredient Substances 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
239000012453 solvate Substances 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 7
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
150000002475 indoles Chemical class 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
OMGOIMQACYUWJO-UHFFFAOYSA-N 3-[3-(2-aminoethyl)-1H-indol-5-yl]-N-benzylpropanamide Chemical compound NCCC1=CNC2=CC=C(C=C12)CCC(=O)NCC1=CC=CC=C1 OMGOIMQACYUWJO-UHFFFAOYSA-N 0.000 claims 1
ZWVKLUGVAWMZKH-UHFFFAOYSA-N 3-[3-(2-aminoethyl)-1H-indol-5-yl]-N-prop-2-enylpropanamide Chemical compound NCCC1=CNC2=CC=C(C=C12)CCC(=O)NCC=C ZWVKLUGVAWMZKH-UHFFFAOYSA-N 0.000 claims 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 71
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 53
239000000203 mixture Substances 0.000 description 48
238000002844 melting Methods 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
230000008018 melting Effects 0.000 description 44
239000000543 intermediate Substances 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 36
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
239000002253 acid Substances 0.000 description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
239000007787 solid Substances 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
229910021529 ammonia Inorganic materials 0.000 description 18
229910052739 hydrogen Inorganic materials 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
239000000843 powder Substances 0.000 description 17
239000000725 suspension Substances 0.000 description 17
238000004458 analytical method Methods 0.000 description 16
239000000284 extract Substances 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 14
239000003054 catalyst Substances 0.000 description 13
239000001257 hydrogen Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
150000001408 amides Chemical class 0.000 description 11
125000003118 aryl group Chemical group 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
238000007429 general method Methods 0.000 description 10
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
230000009467 reduction Effects 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
238000001914 filtration Methods 0.000 description 9
229910052737 gold Inorganic materials 0.000 description 9
239000010931 gold Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
238000011282 treatment Methods 0.000 description 8
208000019695 Migraine disease Diseases 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
239000003814 drug Substances 0.000 description 7
229940079593 drug Drugs 0.000 description 7
125000005843 halogen group Chemical group 0.000 description 7
238000005259 measurement Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
239000012429 reaction media Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
238000007363 ring formation reaction Methods 0.000 description 7
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
239000007788 liquid Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
206010027599 migraine Diseases 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
239000000052 vinegar Substances 0.000 description 5
235000021419 vinegar Nutrition 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
MEVXSUZBFYZPHZ-UHFFFAOYSA-N 2-amino-3-methyl-4h-imidazol-5-one;sulfuric acid Chemical class OS(O)(=O)=O.CN1CC(=O)N=C1N MEVXSUZBFYZPHZ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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 4
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000003513 alkali Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000012431 aqueous reaction media Substances 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
239000005526 vasoconstrictor agent Substances 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000036772 blood pressure Effects 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
229910052799 carbon Inorganic materials 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000006482 condensation reaction Methods 0.000 description 3
229940109239 creatinine Drugs 0.000 description 3
238000001514 detection method Methods 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
238000007907 direct compression Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
235000006408 oxalic acid Nutrition 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
229910052698 phosphorus Inorganic materials 0.000 description 3
229910052697 platinum Inorganic materials 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000001384 succinic acid Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
229910052721 tungsten Inorganic materials 0.000 description 3
230000002792 vascular Effects 0.000 description 3
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
HXCGECBRHHNMQE-UHFFFAOYSA-N 2-acetyloxy-2-chloroacetic acid Chemical compound CC(=O)OC(Cl)C(O)=O HXCGECBRHHNMQE-UHFFFAOYSA-N 0.000 description 2
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
206010019233 Headaches Diseases 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
229910052776 Thorium 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
150000008065 acid anhydrides Chemical class 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
239000002111 antiemetic agent Substances 0.000 description 2
229940125683 antiemetic agent Drugs 0.000 description 2
229940054051 antipsychotic indole derivative Drugs 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
210000003323 beak Anatomy 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
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229910052740 iodine Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
230000003189 isokinetic effect Effects 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
239000002609 medium Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-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
239000001923 methylcellulose Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical group CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
238000007911 parenteral administration Methods 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
150000004714 phosphonium salts Chemical class 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 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
239000010970 precious metal Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003380 propellant Substances 0.000 description 1
FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 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
230000005588 protonation Effects 0.000 description 1
239000008213 purified water Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
150000002910 rare earth metals Chemical class 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
102220006559 rs137853934 Human genes 0.000 description 1
210000003752 saphenous vein Anatomy 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
CKPKEQOGKBPTSV-UHFFFAOYSA-M sodium;hydrogen peroxide;hydroxide Chemical compound [OH-].[Na+].OO CKPKEQOGKBPTSV-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229940071117 starch glycolate Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 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
YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
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
238000007738 vacuum evaporation Methods 0.000 description 1
230000003639 vasoconstrictive effect Effects 0.000 description 1
239000008215 water for injection Substances 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
- 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

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (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)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

JP60278124A 1984-12-13 1985-12-12 インドール、その製造方法及びそれを含有する製薬組成物 Pending JPS61151172A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8431426		1984-12-13
GB848431426A GB8431426D0 (en)	1984-12-13	1984-12-13	Chemical compounds

Publications (1)

Publication Number	Publication Date
JPS61151172A true JPS61151172A (ja)	1986-07-09

Family

ID=10571103

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60278124A Pending JPS61151172A (ja)	1984-12-13	1985-12-12	インドール、その製造方法及びそれを含有する製薬組成物

Country Status (11)

Country	Link
JP (1)	JPS61151172A (it)
AU (1)	AU579687B2 (it)
BE (1)	BE903846A (it)
CH (1)	CH667454A5 (it)
DE (1)	DE3543982A1 (it)
FR (1)	FR2574793B1 (it)
GB (2)	GB8431426D0 (it)
IT (1)	IT1182089B (it)
NL (1)	NL8503424A (it)
SE (1)	SE8505887L (it)
ZA (1)	ZA859520B (it)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2011168608A (ja) *	2002-12-20	2011-09-01	Ciba Holding Inc	アミン類の合成及びその合成のための中間体

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8530507D0 (en) *	1985-12-11	1986-01-22	Glaxo Group Plc	Chemical compounds
GB8607824D0 (en) *	1986-03-27	1986-04-30	Glaxo Group Ltd	Chemical compounds
GB8614287D0 (en) *	1986-06-12	1986-07-16	Glaxo Group Ltd	Chemical compounds
US4894386A (en) *	1987-04-15	1990-01-16	Ici Americas Inc.	Aliphatic carboxamides
GB8719167D0 (en) *	1987-08-13	1987-09-23	Glaxo Group Ltd	Chemical compounds
US5225431A (en) *	1987-10-23	1993-07-06	Burroughs Wellcome Co.	Therapeutic substituted indole compounds and compositions thereof
KR100215627B1 (ko) *	1990-06-07	1999-08-16	레슬리 제인 에드워즈	치료용 헤테로사이클 화합물
GB9209882D0 (en) *	1992-05-07	1992-06-24	Glaxo Lab Sa	Compositions
GB9211277D0 (en)	1992-05-28	1992-07-15	Glaxo Group Inc	Pharmaceutical compositions
GB9216009D0 (en) *	1992-07-28	1992-09-09	Almirall Lab	New indol derivatives
ES2056025B1 (es) *	1992-10-08	1995-05-01	Almirall Lab	Nuevos derivados de indol.
FR2707639B1 (fr) *	1993-06-30	1995-10-13	Pf Medicament	Nouveaux composés indoliques dérivés d'arylamines comme ligands sélectifs des récepteurs 5HT1D et 5HT1B.
US7189753B1 (en)	1997-11-06	2007-03-13	Cady Roger K	Preemptive prophylaxis of migraine
WO2005118551A2 (en)	2004-05-28	2005-12-15	Ligand Pharmaceuticals Inc.	Thrombopoietin activity modulating compounds and methods
MX2007004765A (es) *	2004-10-25	2007-07-09	Ligand Pharm Inc	Compuestos y metodos que modulan la actividad de la trombopoyetina.
KR20090125799A (ko)	2007-03-29	2009-12-07	아스비오파마 가부시키가이샤	Ｃｐｌａ2 저해 활성을 가지는 인돌 유도체 및 그 용도 및 제조 방법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA795239B (en) *	1978-10-12	1980-11-26	Glaxo Group Ltd	Heterocyclic compounds
GB2082175B (en) *	1980-08-12	1984-05-02	Glaxo Group Ltd	Heterocyclic compounds
IT1181741B (it) *	1984-12-04	1987-09-30	Glaxo Group Ltd	Derivati di indolo,procedimento per prepararli e composizioni farmaceutiche che li contengono
GB8530507D0 (en) *	1985-12-11	1986-01-22	Glaxo Group Plc	Chemical compounds

1984
- 1984-12-13 GB GB848431426A patent/GB8431426D0/en active Pending
1985
- 1985-12-12 AU AU51151/85A patent/AU579687B2/en not_active Ceased
- 1985-12-12 SE SE8505887A patent/SE8505887L/xx not_active Application Discontinuation
- 1985-12-12 ZA ZA859520A patent/ZA859520B/xx unknown
- 1985-12-12 DE DE19853543982 patent/DE3543982A1/de not_active Withdrawn
- 1985-12-12 BE BE0/216004A patent/BE903846A/fr not_active IP Right Cessation
- 1985-12-12 JP JP60278124A patent/JPS61151172A/ja active Pending
- 1985-12-12 IT IT48921/85A patent/IT1182089B/it active
- 1985-12-12 NL NL8503424A patent/NL8503424A/nl not_active Application Discontinuation
- 1985-12-12 FR FR8518416A patent/FR2574793B1/fr not_active Expired
- 1985-12-12 GB GB08530591A patent/GB2168347B/en not_active Expired
- 1985-12-12 CH CH5301/85A patent/CH667454A5/fr not_active IP Right Cessation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2011168608A (ja) *	2002-12-20	2011-09-01	Ciba Holding Inc	アミン類の合成及びその合成のための中間体
JP2012072174A (ja) *	2002-12-20	2012-04-12	Ciba Holding Inc	アミン類の合成及びその合成のための中間体
US8710093B2 (en)	2002-12-20	2014-04-29	BASF SE Ludwigshafen	Synthesis of amines and intermediates for the synthesis thereof

Also Published As

Publication number	Publication date
AU579687B2 (en)	1988-12-01
SE8505887D0 (sv)	1985-12-12
FR2574793A1 (fr)	1986-06-20
FR2574793B1 (fr)	1988-10-14
IT8548921A0 (it)	1985-12-12
GB8530591D0 (en)	1986-01-22
IT1182089B (it)	1987-09-30
AU5115185A (en)	1986-06-19
CH667454A5 (fr)	1988-10-14
DE3543982A1 (de)	1986-06-19
BE903846A (fr)	1986-06-12
GB2168347B (en)	1988-02-03
ZA859520B (en)	1986-08-27
GB2168347A (en)	1986-06-18
NL8503424A (nl)	1986-07-01
SE8505887L (sv)	1986-06-14
GB8431426D0 (en)	1985-01-23

Publication	Publication Date	Title
TW530048B (en)	2003-05-01	New hydroxyindoles, their use as inhibitors of phosphodiesterase 4 and processes for their preparation
TW472045B (en)	2002-01-11	Protein kinase C inhibitor compounds, method for their preparation, pharmaceutical composition thereof and intermediate used for their preparation
TWI338684B (en)	2011-03-11	Tetrahydroquinoline derivatives and a process for preparing the same
RU2351588C2 (ru)	2009-04-10	Производные n-фенил(пиперидин-2-ил)метил-бензамида и их применение в терапии
TW593278B (en)	2004-06-21	1-aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands
JPH06508816A (ja)	1994-10-06	（ｓ）（＋）−２−エトキシ−４−［ｎ−［１−（２−ピペリジノ−フェニル）−３−メチル−１−ブチル〕アミノカルボニルメチル〕−安息香酸、この化合物を含む医薬組成物及びその調製方法
US5077293A (en)	1991-12-31	1-indolyalkyl-4-(alkoxypyrimidinyl)piperazines
ES2232168T3 (es)	2005-05-16	Pirroloquinolinas para el tratamiento de la obesidad.
JPH07508993A (ja)	1995-10-05	アザサイクリック化合物
JPH11512701A (ja)	1999-11-02	選択的なβ▲下３▼アドレナリン作動性アゴニスト
JPH02231486A (ja)	1990-09-13	新規β―アドレナリン作動剤
JPH08501559A (ja)	1996-02-20	セロトニン受容体剤
JPH11508283A (ja)	1999-07-21	ベンゾフリル誘導体類及びそれらの用途
CZ282652B6 (cs)	1997-08-13	Indolové deriváty, způsob jejich přípravy, meziprodukty tohoto postupu, farmaceutické prostředky obsahující tyto deriváty a použití těchto derivátů
JP5026633B2 (ja)	2012-09-12	細胞増殖の阻害のための置換ビスインドリルマレイミド類
TW438746B (en)	2001-06-07	New phenylamidine derivatives, processes for preparing them and their use as pharmaceutical compositions
CH667454A5 (fr)	1988-10-14	Derives d'indoles.
TW294595B (it)	1997-01-01
JP2001504501A (ja)	2001-04-03	５−ｈｔ▲下１ｄ▼レセプターのリガンドとしての５−シクロインドール化合物
EP1021442B1 (fr)	2002-01-30	Derives de 8-azabicyclo 3.2.1] octane-3-methanamine en tant que ligands des recepteurs de dopamine d2 et d3 et de serotonine 5ht1a et 5ht2
JP3242652B2 (ja)	2001-12-25	ピロロアゼピン誘導体
CA2022236A1 (en)	1991-02-01	Coumarin derivatives, their preparation and their use in the treatment of cerebrovascular disorders
WO2003002532A1 (fr)	2003-01-09	Composes de diamine cyclique possedant des groupes a noyau fusionne
JPS6322068A (ja)	1988-01-29	インド−ル誘導体
ES2336047T3 (es)	2010-04-07	Derivados de 3-azabiciclo-(4,1,0)heptano para el tratamiento de la depresion.