NO840712L - Fremgangsmaate for fremstilling av farmasoeytisk aktive imidazo-forbindelser - Google Patents
Fremgangsmaate for fremstilling av farmasoeytisk aktive imidazo-forbindelserInfo
- Publication number
- NO840712L NO840712L NO840712A NO840712A NO840712L NO 840712 L NO840712 L NO 840712L NO 840712 A NO840712 A NO 840712A NO 840712 A NO840712 A NO 840712A NO 840712 L NO840712 L NO 840712L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- general formula
- lower alkyl
- salt
- dihydro
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 130
- 238000000034 method Methods 0.000 title claims description 54
- -1 piperazin-1-ylmethyl Chemical group 0.000 claims description 144
- 150000003839 salts Chemical class 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000005277 alkyl imino group Chemical group 0.000 claims description 11
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004935 benzoxazolinyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000006683 Mannich reaction Methods 0.000 claims description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 238000006476 reductive cyclization reaction Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 132
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 109
- 239000000203 mixture Substances 0.000 description 86
- 238000006243 chemical reaction Methods 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 77
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 69
- 238000002329 infrared spectrum Methods 0.000 description 68
- 238000002844 melting Methods 0.000 description 63
- 230000008018 melting Effects 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000002904 solvent Substances 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 238000000354 decomposition reaction Methods 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 23
- 239000002253 acid Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 238000001914 filtration Methods 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 238000012360 testing method Methods 0.000 description 16
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 15
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 14
- 238000001819 mass spectrum Methods 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 235000011054 acetic acid Nutrition 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 229950011175 aminopicoline Drugs 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000002411 adverse Effects 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- AAAHJISFVMZVQQ-UHFFFAOYSA-N 6-(2-bromopropanoyl)-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound O1C(C)C(=O)NC2=CC(C(=O)C(Br)C)=CC=C21 AAAHJISFVMZVQQ-UHFFFAOYSA-N 0.000 description 8
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000006722 reduction reaction Methods 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 208000025865 Ulcer Diseases 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 231100000397 ulcer Toxicity 0.000 description 6
- WWTGWNWVYBVROH-UHFFFAOYSA-N 5-(2-bromopropanoyl)-3-methyl-1,3-benzoxazol-2-one Chemical compound CC(Br)C(=O)C1=CC=C2OC(=O)N(C)C2=C1 WWTGWNWVYBVROH-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000003973 alkyl amines Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- NMCBWICNRJLKKM-UHFFFAOYSA-N 3-(benzyloxy)pyridin-2-amine Chemical compound NC1=NC=CC=C1OCC1=CC=CC=C1 NMCBWICNRJLKKM-UHFFFAOYSA-N 0.000 description 4
- BSINTJNZZZCJNY-UHFFFAOYSA-N 5-(2-bromopropanoyl)-3-methyl-1,3-benzothiazol-2-one Chemical compound CC(Br)C(=O)C1=CC=C2SC(=O)N(C)C2=C1 BSINTJNZZZCJNY-UHFFFAOYSA-N 0.000 description 4
- QDZVQCASIRHEEF-UHFFFAOYSA-N 5-(2-bromopropanoyl)-3h-1,3-benzoxazol-2-one Chemical compound CC(Br)C(=O)C1=CC=C2OC(=O)NC2=C1 QDZVQCASIRHEEF-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 230000003177 cardiotonic effect Effects 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 3
- GHCFWKFREBNSPC-UHFFFAOYSA-N 2-Amino-4-methylpyrimidine Chemical compound CC1=CC=NC(N)=N1 GHCFWKFREBNSPC-UHFFFAOYSA-N 0.000 description 3
- 150000003930 2-aminopyridines Chemical class 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- LTNXVUMNBIDPNB-UHFFFAOYSA-N 5-(2-bromoacetyl)-3-methyl-1,3-benzothiazol-2-one Chemical compound BrCC(=O)C1=CC=C2SC(=O)N(C)C2=C1 LTNXVUMNBIDPNB-UHFFFAOYSA-N 0.000 description 3
- WZRVPRHEVXBCSB-UHFFFAOYSA-N 5-(2-bromoacetyl)-3h-1,3-benzothiazol-2-one Chemical compound BrCC(=O)C1=CC=C2SC(=O)NC2=C1 WZRVPRHEVXBCSB-UHFFFAOYSA-N 0.000 description 3
- CDMLPKOOANRTBD-UHFFFAOYSA-N 5-(2-bromobutanoyl)-3-methyl-1,3-benzothiazol-2-one Chemical compound CCC(Br)C(=O)C1=CC=C2SC(=O)N(C)C2=C1 CDMLPKOOANRTBD-UHFFFAOYSA-N 0.000 description 3
- ISKDQUNAJGSVLE-UHFFFAOYSA-N 5-(2-bromopropanoyl)-3h-1,3-benzothiazol-2-one Chemical compound CC(Br)C(=O)C1=CC=C2SC(=O)NC2=C1 ISKDQUNAJGSVLE-UHFFFAOYSA-N 0.000 description 3
- QBZMPBVIIKFMLR-UHFFFAOYSA-N 6-(2-bromopropanoyl)-2-ethyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(C(=O)C(C)Br)C=C2NC(=O)C(CC)OC2=C1 QBZMPBVIIKFMLR-UHFFFAOYSA-N 0.000 description 3
- CFIIJMIQBTYXMH-UHFFFAOYSA-N 6-(2-bromopropanoyl)-4-methyl-1,4-benzothiazin-3-one Chemical compound S1CC(=O)N(C)C2=CC(C(=O)C(Br)C)=CC=C21 CFIIJMIQBTYXMH-UHFFFAOYSA-N 0.000 description 3
- XLDRTZBXAQUHCB-UHFFFAOYSA-N 6-(2-bromopropanoyl)-4h-1,4-benzoxazin-3-one Chemical compound O1CC(=O)NC2=CC(C(=O)C(Br)C)=CC=C21 XLDRTZBXAQUHCB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- 230000001746 atrial effect Effects 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 210000002216 heart Anatomy 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 210000005240 left ventricle Anatomy 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- NSBNSZAXNUGWDJ-UHFFFAOYSA-O monopyridin-1-ium tribromide Chemical compound Br[Br-]Br.C1=CC=[NH+]C=C1 NSBNSZAXNUGWDJ-UHFFFAOYSA-O 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical compound C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002417 xiphoid bone Anatomy 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838305245A GB8305245D0 (en) | 1983-02-25 | 1983-02-25 | Imidazo-heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO840712L true NO840712L (no) | 1984-08-27 |
Family
ID=10538591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO840712A NO840712L (no) | 1983-02-25 | 1984-02-24 | Fremgangsmaate for fremstilling av farmasoeytisk aktive imidazo-forbindelser |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4621084A (fi) |
| EP (1) | EP0120589B1 (fi) |
| JP (1) | JPS59186983A (fi) |
| KR (1) | KR840007879A (fi) |
| AT (1) | ATE34984T1 (fi) |
| AU (1) | AU2482284A (fi) |
| DE (1) | DE3471936D1 (fi) |
| DK (1) | DK72784A (fi) |
| ES (1) | ES8505963A1 (fi) |
| FI (1) | FI840653A (fi) |
| GB (1) | GB8305245D0 (fi) |
| GR (1) | GR79810B (fi) |
| NO (1) | NO840712L (fi) |
| ZA (1) | ZA841156B (fi) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3406329A1 (de) * | 1984-02-22 | 1985-08-22 | Merck Patent Gmbh, 6100 Darmstadt | Pyridone |
| GB8432073D0 (en) * | 1984-12-19 | 1985-01-30 | Roussel Lab Ltd | Chemical compounds |
| DE3446812A1 (de) * | 1984-12-21 | 1986-06-26 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazoderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| WO1986007059A2 (en) * | 1985-05-25 | 1986-12-04 | Yoshitomi Pharmaceutical Industries, Ltd. | Oxodiazine compounds |
| CA1256109A (en) * | 1986-09-10 | 1989-06-20 | Franz Rovenszky | Process for the preparation of derivatives of 4, 5-dihydrooxazoles |
| US4791117A (en) * | 1986-09-22 | 1988-12-13 | Ortho Pharmaceutical Corporation | 2- or 3-aryl substituted imidazo[1,2-a]pyridines and their use as calcium channel blockers |
| NZ221996A (en) * | 1986-10-07 | 1989-08-29 | Yamanouchi Pharma Co Ltd | Imidazo-pyridine derivatives and pharmaceutical compositions |
| US4731446A (en) * | 1987-05-01 | 1988-03-15 | The Dow Chemical Company | Imidazo[1,2-a]pyrimidine sulfonic acids and acid halides |
| GB8820231D0 (en) * | 1988-08-25 | 1988-09-28 | Fujisawa Pharmaceutical Co | New benzazole compounds processes for preparation thereof & pharmaceutical composition comprising same |
| EP0375819A1 (en) * | 1988-12-20 | 1990-07-04 | Merrell Dow Pharmaceuticals Inc. | Novel derivatives of 1,7'-[imidazo-[1,2-a]pyridine]5'-(6'H)ones |
| GB8905130D0 (en) * | 1989-03-07 | 1989-04-19 | Pfizer Ltd | Therapeutic agents |
| FR2645149A1 (fi) * | 1989-03-30 | 1990-10-05 | Adir | |
| US5166353A (en) * | 1989-04-28 | 1992-11-24 | Adir Et Compagnie | Benzothiazolinone compounds |
| FR2646350B1 (fr) * | 1989-04-28 | 1991-06-28 | Adir | Nouveaux derives benzothiazolinoniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| KR910011852A (ko) * | 1989-12-04 | 1991-08-07 | 폴 디. 매튜카이티스 | 신경독 장해 치료용 이미다조[1,2-a]피리디닐알킬 화합물 |
| US5716964A (en) * | 1989-12-04 | 1998-02-10 | G.D. Searle & Co. | Tetrazolyl substituted imidazo 1,2-a!pyridinylalkyl compounds for treatment of neurotoxic injury |
| US5464843A (en) * | 1992-06-23 | 1995-11-07 | G.D. Searle & Co. | Imidazo[1,2-a]pyridinyldiacid compounds for cognitive enhancement and for treatment of cognitive disorders and neutrotoxic injury |
| HRP950330A2 (en) * | 1994-07-05 | 1997-10-31 | Ciba Geigy Ag | New herbicides |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| ME00524B (me) | 2003-03-10 | 2011-10-10 | Astrazeneca Ab | Novi postupak za dobijanje roflumilasta |
| GT200600042A (es) * | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| CA2601250C (en) | 2005-03-16 | 2014-10-28 | Nycomed Gmbh | Taste masked dosage form containing roflumilast |
| TW201018678A (en) | 2006-01-27 | 2010-05-16 | Astrazeneca Ab | Novel heteroaryl substituted benzothiazoles |
| TW200813035A (en) | 2006-06-19 | 2008-03-16 | Astrazeneca Ab | Novel heteroaryl substituted benzoxazoles |
| KR20090101469A (ko) * | 2007-01-22 | 2009-09-28 | 아스트라제네카 아베 | 신규 헤테로아릴 치환된 이미다조〔１，２ａ〕피리딘 유도체 |
| TW200901998A (en) | 2007-03-06 | 2009-01-16 | Astrazeneca Ab | Novel 2-heteroaryl substituted benzothiophenes and benzofuranes |
| JP5774982B2 (ja) * | 2008-05-19 | 2015-09-09 | サノビオン ファーマシューティカルズ インクＳｕｎｏｖｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | イミダゾ［１，２−ａ］ピリジン化合物 |
| JP2012520887A (ja) * | 2009-03-18 | 2012-09-10 | シェーリング コーポレイション | ジアシルグリセロールアシルトランスフェラーゼの阻害剤としての二環式化合物 |
| SG11201509650YA (en) * | 2013-05-24 | 2015-12-30 | Iomet Pharma Ltd | Slc2a transporter inhibitors |
| CN107810188B (zh) * | 2015-04-08 | 2020-09-22 | 拜耳作物科学股份公司 | 作为害虫防治剂和中间体产物的稠合双环杂环衍生物 |
| GB201509893D0 (en) * | 2015-06-08 | 2015-07-22 | Ucb Biopharma Sprl | Therapeutic agents |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU600143A1 (ru) * | 1976-12-06 | 1978-03-30 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср | Способ получени гетероциклических систем, содержащих бормзамещенный имидазол |
| JPS57102888A (en) * | 1980-12-18 | 1982-06-26 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| CA1164459A (en) * | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| JPS5782390A (en) * | 1980-11-11 | 1982-05-22 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| DE3269604D1 (en) * | 1981-06-26 | 1986-04-10 | Schering Corp | Novel imidazo(1,2-a)pyridines and pyrazines, processes for their preparation and pharmaceutical compositions containing them |
-
1983
- 1983-02-25 GB GB838305245A patent/GB8305245D0/en active Pending
-
1984
- 1984-02-15 GR GR73804A patent/GR79810B/el unknown
- 1984-02-16 ZA ZA841156A patent/ZA841156B/xx unknown
- 1984-02-16 DK DK72784A patent/DK72784A/da not_active Application Discontinuation
- 1984-02-17 AT AT84301058T patent/ATE34984T1/de not_active IP Right Cessation
- 1984-02-17 DE DE8484301058T patent/DE3471936D1/de not_active Expired
- 1984-02-17 EP EP84301058A patent/EP0120589B1/en not_active Expired
- 1984-02-17 FI FI840653A patent/FI840653A/fi not_active Application Discontinuation
- 1984-02-22 AU AU24822/84A patent/AU2482284A/en not_active Abandoned
- 1984-02-22 KR KR1019840000871A patent/KR840007879A/ko not_active Application Discontinuation
- 1984-02-24 ES ES530011A patent/ES8505963A1/es not_active Expired
- 1984-02-24 NO NO840712A patent/NO840712L/no unknown
- 1984-02-24 JP JP59035072A patent/JPS59186983A/ja active Granted
- 1984-02-27 US US06/583,609 patent/US4621084A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2482284A (en) | 1984-08-30 |
| US4621084A (en) | 1986-11-04 |
| FI840653A (fi) | 1984-08-26 |
| EP0120589A1 (en) | 1984-10-03 |
| GB8305245D0 (en) | 1983-03-30 |
| GR79810B (fi) | 1984-10-31 |
| EP0120589B1 (en) | 1988-06-08 |
| DE3471936D1 (en) | 1988-07-14 |
| JPS59186983A (ja) | 1984-10-23 |
| ATE34984T1 (de) | 1988-06-15 |
| ES530011A0 (es) | 1985-06-16 |
| ZA841156B (en) | 1984-09-26 |
| ES8505963A1 (es) | 1985-06-16 |
| DK72784D0 (da) | 1984-02-16 |
| FI840653A0 (fi) | 1984-02-17 |
| KR840007879A (ko) | 1984-12-11 |
| DK72784A (da) | 1984-08-26 |
| JPH0557989B2 (fi) | 1993-08-25 |
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