NL8503337A - Indoolderivaten. - Google Patents

Indoolderivaten. Download PDF

Info

Publication number: NL8503337A
Authority: NL; Netherlands
Prior art keywords: group; general formula; formula; ethyl; alkyl
Prior art date: 1984-12-04

Application number

NL8503337A

Other languages

English (en)

Dutch (nl)

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.)

1984-12-04

Filing date

1985-12-03

Publication date

1986-07-01

1984-12-04 Priority claimed from GB848430625A external-priority patent/GB8430625D0/en

1984-12-04 Priority claimed from GB848430624A external-priority patent/GB8430624D0/en

1984-12-04 Priority claimed from GB848430626A external-priority patent/GB8430626D0/en

1984-12-05 Priority claimed from GB848430773A external-priority patent/GB8430773D0/en

1985-12-03 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1986-07-01 Publication of NL8503337A publication Critical patent/NL8503337A/nl

Links

SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title claims description 16
229940054051 antipsychotic indole derivative Drugs 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 124
238000006243 chemical reaction Methods 0.000 claims description 38
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 35
150000003839 salts Chemical class 0.000 claims description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
238000000034 method Methods 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 26
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 20
239000004480 active ingredient Substances 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000004429 atom Chemical group 0.000 claims description 15
239000012453 solvate Substances 0.000 claims description 15
150000002475 indoles Chemical class 0.000 claims description 14
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
229940124530 sulfonamide Drugs 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
DPQJJNLDRIYZBO-UHFFFAOYSA-N 2-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]-n-ethylethanesulfonamide Chemical compound CCNS(=O)(=O)CCC1=CC=C2NC=C(CCN(C)C)C2=C1 DPQJJNLDRIYZBO-UHFFFAOYSA-N 0.000 claims description 2
JDIVGCXFNGUKMR-UHFFFAOYSA-N 3-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]-n-methylpropane-1-sulfonamide Chemical compound CNS(=O)(=O)CCCC1=CC=C2NC=C(CCN(C)C)C2=C1 JDIVGCXFNGUKMR-UHFFFAOYSA-N 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
FTRJOLXTAORPLI-UHFFFAOYSA-N n-cyclopentyl-2-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]ethanesulfonamide Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CCS(=O)(=O)NC1CCCC1 FTRJOLXTAORPLI-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
239000005977 Ethylene Substances 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
-1 for example Chemical class 0.000 description 42
239000000203 mixture Substances 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
235000019441 ethanol Nutrition 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
238000004458 analytical method Methods 0.000 description 21
125000003118 aryl group Chemical group 0.000 description 20
239000002585 base Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000002904 solvent Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000007429 general method Methods 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000001408 amides Chemical class 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000003826 tablet Substances 0.000 description 11
150000002148 esters Chemical class 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
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 9
239000003054 catalyst Substances 0.000 description 9
239000011734 sodium Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-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
239000000543 intermediate Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
238000007363 ring formation reaction Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
238000011282 treatment Methods 0.000 description 8
229940086542 triethylamine Drugs 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
208000019695 Migraine disease Diseases 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
125000004423 acyloxy group Chemical group 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
206010027599 migraine Diseases 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000005526 vasoconstrictor agent Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VHCSBTPOPKFYIU-UHFFFAOYSA-N 2-chloroethanesulfonyl chloride Chemical compound ClCCS(Cl)(=O)=O VHCSBTPOPKFYIU-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
229910000288 alkali metal carbonate Inorganic materials 0.000 description 4
150000008041 alkali metal carbonates Chemical class 0.000 description 4
239000012431 aqueous reaction media Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
229910000073 phosphorus hydride Inorganic materials 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
229940032147 starch Drugs 0.000 description 4
239000008107 starch Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
UAICWIRMGRPHJL-UHFFFAOYSA-N 2-(5-iodo-1h-indol-3-yl)-n,n-dimethylethanamine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(I)C=C2C(CCN(C)C)=CNC2=C1 UAICWIRMGRPHJL-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000000872 buffer Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
235000003599 food sweetener Nutrition 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
229910003445 palladium oxide Inorganic materials 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
239000004576 sand Substances 0.000 description 3
238000006748 scratching Methods 0.000 description 3
230000002393 scratching effect Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003456 sulfonamides Chemical class 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000003765 sweetening agent Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
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 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
229920002785 Croscarmellose sodium Polymers 0.000 description 2
239000004338 Dichlorodifluoromethane Substances 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
229910004809 Na2 SO4 Inorganic materials 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229920000388 Polyphosphate Polymers 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
125000002252 acyl group Chemical group 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
239000008365 aqueous carrier Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
229960001681 croscarmellose sodium Drugs 0.000 description 2
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
WJYHCYBNUJVCEH-UHFFFAOYSA-N cyclohexane;ethoxyethane Chemical compound CCOCC.C1CCCCC1 WJYHCYBNUJVCEH-UHFFFAOYSA-N 0.000 description 2
235000019700 dicalcium phosphate Nutrition 0.000 description 2
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229940016286 microcrystalline cellulose Drugs 0.000 description 1
HEKVEUDNSNLEEF-UHFFFAOYSA-N n-[4-(dimethylamino)butan-2-ylideneamino]-4-iodoaniline Chemical compound CN(C)CCC(C)=NNC1=CC=C(I)C=C1 HEKVEUDNSNLEEF-UHFFFAOYSA-N 0.000 description 1
VMTQGMPPTPYMTA-UHFFFAOYSA-N n-cyclopentylethenesulfonamide Chemical compound C=CS(=O)(=O)NC1CCCC1 VMTQGMPPTPYMTA-UHFFFAOYSA-N 0.000 description 1
MJHNRAISAMBLTM-UHFFFAOYSA-N n-methylprop-2-ene-1-sulfonamide Chemical compound CNS(=O)(=O)CC=C MJHNRAISAMBLTM-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
150000003891 oxalate salts Chemical class 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
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 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
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 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
AAHFRWRQQDVWPX-UHFFFAOYSA-N prop-2-ene-1-sulfonyl chloride Chemical compound ClS(=O)(=O)CC=C AAHFRWRQQDVWPX-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
LZFIOSVZIQOVFW-UHFFFAOYSA-N propyl 2-hydroxybenzoate Chemical class CCCOC(=O)C1=CC=CC=C1O LZFIOSVZIQOVFW-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
230000005588 protonation Effects 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].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.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 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
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000002511 suppository base Substances 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
150000003892 tartrate salts Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
230000002792 vascular Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000010792 warming Methods 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NL8503337A 1984-12-04 1985-12-03 Indoolderivaten. NL8503337A (nl)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
GB848430625A GB8430625D0 (en)	1984-12-04	1984-12-04	Production of chemical compounds
GB8430624		1984-12-04
GB8430626		1984-12-04
GB848430624A GB8430624D0 (en)	1984-12-04	1984-12-04	Chemical compounds
GB848430626A GB8430626D0 (en)	1984-12-04	1984-12-04	Chemical compounds
GB8430625		1984-12-04
GB8430773		1984-12-05
GB848430773A GB8430773D0 (en)	1984-12-05	1984-12-05	Chemical compounds

Publications (1)

Publication Number	Publication Date
NL8503337A true NL8503337A (nl)	1986-07-01

Family

ID=27449610

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8503337A NL8503337A (nl)	1984-12-04	1985-12-03	Indoolderivaten.

Country Status (10)

Country	Link
US (1)	US4785016A (fr)
AU (1)	AU584142B2 (fr)
BE (1)	BE903778A (fr)
CH (1)	CH667647A5 (fr)
DE (1)	DE3542698A1 (fr)
FR (1)	FR2574077A1 (fr)
GB (1)	GB2168973B (fr)
IT (1)	IT1181741B (fr)
NL (1)	NL8503337A (fr)
SE (1)	SE8505715L (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8332437D0 (en) *	1983-12-06	1984-01-11	Glaxo Group Ltd	Chemical compounds
HU196752B (en) *	1983-12-06	1989-01-30	Glaxo Group Ltd	Process for production of medical compositions containing indole-derivatives and these compounds
GB8431426D0 (en) *	1984-12-13	1985-01-23	Glaxo Group Ltd	Chemical compounds
EP0303507B1 (fr) *	1987-08-13	1993-07-28	Glaxo Group Limited	Dérivés d'indole
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
GB8903036D0 (en) *	1989-02-10	1989-03-30	Glaxo Group Ltd	Chemical compounds
PT97888B (pt) *	1990-06-07	1998-12-31	Zeneca Ltd	Processo para a preparacao de compostos heterociclicos derivados de indol e de composicoes farmaceuticas que os contem
AT394895B (de) *	1990-07-05	1992-07-10	Steyr Daimler Puch Ag	Fluessigkeitsreibungskupplung
DE4101686A1 (de) *	1991-01-22	1992-07-23	Merck Patent Gmbh	Indolderivate
GB9207396D0 (en) *	1992-04-03	1992-05-13	Merck Sharp & Dohme	Therapeutic agents
GB9208463D0 (en) *	1992-04-16	1992-06-03	Merck Sharp & Dohme	Therapeutic agents
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
ES2059236B1 (es) *	1992-06-18	1995-06-16	Imidex S A	Procedimiento para la sintesis de la 3-(2-dimetilamino) etil)-n-metil-1h-indol-5-metanosulfonamida.
ES2079323B1 (es) *	1994-06-21	1996-10-16	Vita Invest Sa	Derivados de indol utiles para el tratamiento de la migraña, composicion y uso correspondientes.
US7189753B1 (en)	1997-11-06	2007-03-13	Cady Roger K	Preemptive prophylaxis of migraine
DE19963178A1 (de) *	1999-12-27	2001-07-05	Gruenenthal Gmbh	Substituierte Indol-Mannichbasen
US10736878B2 (en)	2012-01-06	2020-08-11	Tina Pfadenhauer	Treatment of organophosphate exposure with triptans

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3472870A (en) *	1966-08-29	1969-10-14	Mead Johnson & Co	Sulfonamidotryptamines
GB8332437D0 (en) *	1983-12-06	1984-01-11	Glaxo Group Ltd	Chemical compounds
HU196752B (en) *	1983-12-06	1989-01-30	Glaxo Group Ltd	Process for production of medical compositions containing indole-derivatives and these compounds

1985
- 1985-12-03 IT IT48869/85A patent/IT1181741B/it active
- 1985-12-03 DE DE19853542698 patent/DE3542698A1/de not_active Withdrawn
- 1985-12-03 NL NL8503337A patent/NL8503337A/nl not_active Application Discontinuation
- 1985-12-03 FR FR8517858A patent/FR2574077A1/fr active Pending
- 1985-12-03 BE BE0/215954A patent/BE903778A/fr not_active IP Right Cessation
- 1985-12-03 US US06/804,102 patent/US4785016A/en not_active Expired - Fee Related
- 1985-12-03 AU AU50705/85A patent/AU584142B2/en not_active Ceased
- 1985-12-03 SE SE8505715A patent/SE8505715L/xx not_active Application Discontinuation
- 1985-12-03 GB GB08529799A patent/GB2168973B/en not_active Expired
- 1985-12-04 CH CH5158/85A patent/CH667647A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
US4785016A (en)	1988-11-15
GB2168973A (en)	1986-07-02
GB8529799D0 (en)	1986-01-08
IT1181741B (it)	1987-09-30
AU5070585A (en)	1986-06-12
FR2574077A1 (fr)	1986-06-06
AU584142B2 (en)	1989-05-18
SE8505715D0 (sv)	1985-12-03
GB2168973B (en)	1988-02-03
BE903778A (fr)	1986-06-03
IT8548869A0 (it)	1985-12-03
CH667647A5 (fr)	1988-10-31
SE8505715L (sv)	1986-06-05
DE3542698A1 (de)	1986-06-05

Legal Events

Date	Code	Title	Description
1993-02-01	BV	The patent application has lapsed

Publication	Publication Date	Title
NL8503337A (nl)	1986-07-01	Indoolderivaten.
JPS62228056A (ja)	1987-10-06	化学的化合物
FI92397C (fi)	1994-11-10	Menetelmä valmistaa farmaseuttisesti käyttökelpoisia indolijohdoksia
US4816470A (en)	1989-03-28	Heterocyclic compounds
AU623900B2 (en)	1992-05-28	Novel hydroxamate derivatives of selected nonsteroidal antiinflammatory acyl residues having cyclooxygenase and 5-lipoxygenase inhibition
EP0147107B1 (fr)	1989-08-02	Derivés du noyau indole
JPH062733B2 (ja)	1994-01-12	インド−ル誘導体、その製法及びそれを含む医薬組成物
AU2003211617A1 (en)	2003-09-09	Ester compound and medicinal use thereof
IE51492B1 (en)	1987-01-07	Heterocyclic compounds
SE452460B (sv)	1987-11-30	3-/2-(dimetylamino)etyl/-n-metyl-1h-indol-5-metansulfonamid, en farmaceutisk komposition innehallande denna och ett forfarande for framstellning av foreningen
MXPA03006597A (es)	2004-10-15	Derivados de glutaramida sustituida con n-fenpropilciclopentilo como inhibidores de nep para fsad.
JPH0625104B2 (ja)	1994-04-06	Ｎ−インドリルエチル−スルホン酸アミド類、その製法及び用途
JP6867998B2 (ja)	2021-05-12	ガンを処置するのに使用するための置換疎水性ベンゼンスルホンアミドチアゾール化合物
NL8503424A (nl)	1986-07-01	Indoolverbindingen; werkwijze voor het bereiden daarvan; farmaceutische preparaten.
EP0677042A1 (fr)	1995-10-18	Ligands selectifs des recepteurs 5ht 1d?-5ht 1b? derives d'indole-piperazine utiles comme medicaments
US7432392B2 (en)	2008-10-07	Ester derivatives and medical use thereof
NO170482B (no)	1992-07-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive karboksamid-derivater
NL8700027A (nl)	1987-08-03	Chemische verbindingen.
US4870096A (en)	1989-09-26	5-substituted 3-aninoalkyl indoles
EP0782568B1 (fr)	2002-04-24	Ethers aromatiques derives d'indoles comme "5ht1-like" ligands
NL8701372A (nl)	1988-01-04	Indoolderivaten, werkwijze ter bereiding daarvan alsmede farmaceutische preparaten die deze derivaten als actieve component bevatten.
MX2007014954A (es)	2008-02-15	Derivados de 2-(1h-indolilsulfanil)-aril-amina.
FI98519C (fi)	1997-07-10	Menetelmä substituoitujen indolien valmistamiseksi
HU211519A9 (en)	1995-11-28	A novel substituted-amine compound and a process for the preparation thereof
US5405873A (en)	1995-04-11	Substituted acetamide derivatives