NO850311L - Fremgangsmaate for fremstilling av terapeutisk aktive naftalen-derivater - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive naftalen-derivaterInfo
- Publication number
- NO850311L NO850311L NO850311A NO850311A NO850311L NO 850311 L NO850311 L NO 850311L NO 850311 A NO850311 A NO 850311A NO 850311 A NO850311 A NO 850311A NO 850311 L NO850311 L NO 850311L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- optionally substituted
- naphthoquinone
- formula
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 31
- 238000002360 preparation method Methods 0.000 title claims description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title description 6
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 95
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 93
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 57
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 19
- 229910052717 sulfur Chemical group 0.000 claims abstract description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
- 239000001301 oxygen Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000011593 sulfur Chemical group 0.000 claims abstract description 18
- 125000006413 ring segment Chemical group 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 11
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 112
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 150000002367 halogens Chemical class 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 230000001590 oxidative effect Effects 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract description 8
- 201000004681 Psoriasis Diseases 0.000 abstract description 7
- 150000002790 naphthalenes Chemical class 0.000 abstract description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- -1 cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy Chemical group 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 11
- 229960005419 nitrogen Drugs 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 6
- OBGBGHKYJAOXRR-UHFFFAOYSA-N 2-methoxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 OBGBGHKYJAOXRR-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- WYIOQBYLZGEHCV-UHFFFAOYSA-N 2-chloro-3-methylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C)=C(Cl)C(=O)C2=C1 WYIOQBYLZGEHCV-UHFFFAOYSA-N 0.000 description 5
- 229940114079 arachidonic acid Drugs 0.000 description 5
- 235000021342 arachidonic acid Nutrition 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 230000000699 topical effect Effects 0.000 description 5
- BGVCGTNXEKDVCB-UHFFFAOYSA-N 4-hydroxy-3-methylnaphthalene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)C(C)=C(O)C2=C1 BGVCGTNXEKDVCB-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LULCPJWUGUVEFU-UHFFFAOYSA-N Phthiocol Natural products C1=CC=C2C(=O)C(C)=C(O)C(=O)C2=C1 LULCPJWUGUVEFU-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 230000002682 anti-psoriatic effect Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000011200 topical administration Methods 0.000 description 4
- MFOPSUMUUNRNTG-UHFFFAOYSA-N (4-acetyloxy-3-butoxynaphthalen-1-yl) acetate Chemical compound C1=CC=CC2=C(OC(C)=O)C(OCCCC)=CC(OC(C)=O)=C21 MFOPSUMUUNRNTG-UHFFFAOYSA-N 0.000 description 3
- SWVQFTWQNQGISY-UHFFFAOYSA-N (4-butanoyloxy-3-propoxynaphthalen-1-yl) butanoate Chemical compound C1=CC=CC2=C(OC(=O)CCC)C(OCCC)=CC(OC(=O)CCC)=C21 SWVQFTWQNQGISY-UHFFFAOYSA-N 0.000 description 3
- CNZJAOOYWYLTEC-UHFFFAOYSA-N 2-methoxy-3-methylnaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(OC)=C(C)C(=O)C2=C1 CNZJAOOYWYLTEC-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- YKLIRAOMPMWZDJ-UHFFFAOYSA-N 6-chloro-2-ethoxynaphthalene-1,4-dione Chemical compound ClC1=CC=C2C(=O)C(OCC)=CC(=O)C2=C1 YKLIRAOMPMWZDJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000003883 ointment base Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- QJECYGRWVGWSQT-UHFFFAOYSA-N (3,4-diacetyloxynaphthalen-1-yl) acetate Chemical compound C1=CC=CC2=C(OC(C)=O)C(OC(=O)C)=CC(OC(C)=O)=C21 QJECYGRWVGWSQT-UHFFFAOYSA-N 0.000 description 2
- AOHPCVCCRJRNID-UHFFFAOYSA-N (4-acetyloxy-2-ethyl-3-phenoxynaphthalen-1-yl) acetate Chemical compound CC(=O)OC1=C2C=CC=CC2=C(OC(C)=O)C(CC)=C1OC1=CC=CC=C1 AOHPCVCCRJRNID-UHFFFAOYSA-N 0.000 description 2
- ABUWWKFXLGAHEP-UHFFFAOYSA-N (4-acetyloxy-3-methoxynaphthalen-1-yl) acetate Chemical compound C1=CC=CC2=C(OC(C)=O)C(OC)=CC(OC(C)=O)=C21 ABUWWKFXLGAHEP-UHFFFAOYSA-N 0.000 description 2
- NWQKAPGACIBKQY-UHFFFAOYSA-N (4-acetyloxy-6,7-dimethyl-3-propoxynaphthalen-1-yl) acetate Chemical compound C1=C(C)C(C)=CC2=C(OC(C)=O)C(OCCC)=CC(OC(C)=O)=C21 NWQKAPGACIBKQY-UHFFFAOYSA-N 0.000 description 2
- ORTFXJGQZJIBAF-UHFFFAOYSA-N (4-benzoyloxy-3-butoxynaphthalen-1-yl) benzoate Chemical compound C=12C=CC=CC2=C(OC(=O)C=2C=CC=CC=2)C(OCCCC)=CC=1OC(=O)C1=CC=CC=C1 ORTFXJGQZJIBAF-UHFFFAOYSA-N 0.000 description 2
- VCULBHGJVVHFMY-UHFFFAOYSA-N (4-benzoyloxy-3-propoxynaphthalen-1-yl) benzoate Chemical compound C=12C=CC=CC2=C(OC(=O)C=2C=CC=CC=2)C(OCCC)=CC=1OC(=O)C1=CC=CC=C1 VCULBHGJVVHFMY-UHFFFAOYSA-N 0.000 description 2
- KCJMZYFXMJNLHQ-UHFFFAOYSA-N (4-benzoyloxy-6-chloro-2-ethoxy-3-ethylnaphthalen-1-yl) benzoate Chemical compound C=12C=C(Cl)C=CC2=C(OC(=O)C=2C=CC=CC=2)C(OCC)=C(CC)C=1OC(=O)C1=CC=CC=C1 KCJMZYFXMJNLHQ-UHFFFAOYSA-N 0.000 description 2
- XDPZXLQKGRKKOA-UHFFFAOYSA-N (4-butanoyloxy-3-butoxynaphthalen-1-yl) butanoate Chemical compound C1=CC=CC2=C(OC(=O)CCC)C(OCCCC)=CC(OC(=O)CCC)=C21 XDPZXLQKGRKKOA-UHFFFAOYSA-N 0.000 description 2
- RHPRUIXNTSKMKD-UHFFFAOYSA-N (4-butanoyloxy-3-ethoxy-2-methylnaphthalen-1-yl) butanoate Chemical compound C1=CC=C2C(OC(=O)CCC)=C(C)C(OCC)=C(OC(=O)CCC)C2=C1 RHPRUIXNTSKMKD-UHFFFAOYSA-N 0.000 description 2
- NSTMSRBWMPUBBU-UHFFFAOYSA-N (4-butanoyloxy-3-methoxy-2-methylnaphthalen-1-yl) butanoate Chemical compound C1=CC=C2C(OC(=O)CCC)=C(C)C(OC)=C(OC(=O)CCC)C2=C1 NSTMSRBWMPUBBU-UHFFFAOYSA-N 0.000 description 2
- QXCRROHGXXEBJV-UHFFFAOYSA-N (4-butanoyloxy-3-methoxynaphthalen-1-yl) butanoate Chemical compound C1=CC=C2C(OC(=O)CCC)=CC(OC)=C(OC(=O)CCC)C2=C1 QXCRROHGXXEBJV-UHFFFAOYSA-N 0.000 description 2
- MYPHKHXZQVKLIM-UHFFFAOYSA-N (4-butanoyloxy-3-phenoxynaphthalen-1-yl) butanoate Chemical compound CCCC(=O)OC=1C2=CC=CC=C2C(OC(=O)CCC)=CC=1OC1=CC=CC=C1 MYPHKHXZQVKLIM-UHFFFAOYSA-N 0.000 description 2
- FSEVMDBNAXAZBF-UHFFFAOYSA-N (4-propanoyloxy-3-propoxynaphthalen-1-yl) propanoate Chemical compound C1=CC=CC2=C(OC(=O)CC)C(OCCC)=CC(OC(=O)CC)=C21 FSEVMDBNAXAZBF-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- BATAHUJPPGPXIN-UHFFFAOYSA-N 2-butoxynaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(OCCCC)=CC(=O)C2=C1 BATAHUJPPGPXIN-UHFFFAOYSA-N 0.000 description 2
- SUWHTOFNNOUEAD-UHFFFAOYSA-N 2-methyl-3-phenylsulfanylnaphthalene-1,4-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C(C)=C1SC1=CC=CC=C1 SUWHTOFNNOUEAD-UHFFFAOYSA-N 0.000 description 2
- HTWMKEKLUZRKTN-UHFFFAOYSA-N 5-chloro-2-hexoxynaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(OCCCCCC)=CC(=O)C2=C1Cl HTWMKEKLUZRKTN-UHFFFAOYSA-N 0.000 description 2
- XCAVTJOLCGEHPM-UHFFFAOYSA-N 5-chloro-2-propoxynaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(OCCC)=CC(=O)C2=C1Cl XCAVTJOLCGEHPM-UHFFFAOYSA-N 0.000 description 2
- SDAQJTSKZNVBPI-UHFFFAOYSA-N 6,7-dimethyl-2-propoxynaphthalene-1,4-dione Chemical compound CC1=C(C)C=C2C(=O)C(OCCC)=CC(=O)C2=C1 SDAQJTSKZNVBPI-UHFFFAOYSA-N 0.000 description 2
- QZFOQZZTNQOJGI-UHFFFAOYSA-N 6-chloro-2-hexoxynaphthalene-1,4-dione Chemical compound ClC1=CC=C2C(=O)C(OCCCCCC)=CC(=O)C2=C1 QZFOQZZTNQOJGI-UHFFFAOYSA-N 0.000 description 2
- KROCUCKORODWTP-UHFFFAOYSA-N 6-chloro-2-methoxynaphthalene-1,4-dione Chemical compound ClC1=CC=C2C(=O)C(OC)=CC(=O)C2=C1 KROCUCKORODWTP-UHFFFAOYSA-N 0.000 description 2
- PYSKAZACTMJRQJ-UHFFFAOYSA-N 6-chloro-2-propoxynaphthalene-1,4-dione Chemical compound ClC1=CC=C2C(=O)C(OCCC)=CC(=O)C2=C1 PYSKAZACTMJRQJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- JTHIPGNWJNDJDQ-UHFFFAOYSA-N C1=C(Cl)C=C2C(=O)C(C)=C(O)C(=O)C2=C1 Chemical compound C1=C(Cl)C=C2C(=O)C(C)=C(O)C(=O)C2=C1 JTHIPGNWJNDJDQ-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 2
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- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 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
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring 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
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- SCXZATZIVUFOFT-UHFFFAOYSA-N undec-5-ene Chemical compound [CH2]CCCC=CCCCCC SCXZATZIVUFOFT-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/10—Quinones the quinoid structure being part of a condensed ring system containing two rings
- C07C50/14—Quinones the quinoid structure being part of a condensed ring system containing two rings with unsaturation outside the ring system, e.g. vitamin K1
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/24—Quinones containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/32—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 to carbon atoms of the hetero ring
- C07D333/64—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
- Organic Insulating Materials (AREA)
- Luminescent Compositions (AREA)
- Medicines Containing Plant Substances (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Paper (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Mechanical Treatment Of Semiconductor (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US57442684A | 1984-01-27 | 1984-01-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO850311L true NO850311L (no) | 1985-07-29 |
Family
ID=24296077
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO850311A NO850311L (no) | 1984-01-27 | 1985-01-25 | Fremgangsmaate for fremstilling av terapeutisk aktive naftalen-derivater |
Country Status (15)
Country | Link |
---|---|
EP (1) | EP0150831B1 (xx) |
JP (1) | JPS60185745A (xx) |
KR (1) | KR900007272B1 (xx) |
AT (1) | ATE36316T1 (xx) |
AU (1) | AU3809885A (xx) |
DE (1) | DE3564259D1 (xx) |
DK (1) | DK35885A (xx) |
ES (1) | ES539866A0 (xx) |
FI (1) | FI850325L (xx) |
HU (1) | HU194533B (xx) |
IE (1) | IE850174L (xx) |
IL (1) | IL74162A0 (xx) |
NO (1) | NO850311L (xx) |
NZ (1) | NZ210938A (xx) |
ZA (1) | ZA85623B (xx) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE943625C (de) * | 1943-06-28 | 1956-05-24 | Ferguson Harry Inc | Seitensteuerungseinrichtung fuer ein landwirtschaftliches Schlepperanbaugeraet |
US4593120A (en) * | 1982-10-27 | 1986-06-03 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
US4792556A (en) * | 1985-09-09 | 1988-12-20 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
JPS6284046A (ja) * | 1985-09-09 | 1987-04-17 | シンテツクス(ユ−・エス・エイ)インコ−ポレイテツド | ナフタレン系抗乾癬剤 |
FI881065A (fi) * | 1987-03-09 | 1988-09-10 | Syntex Inc | Foerfarande foer framstaellning av naftalenfoereningar anvaendbara vid behandling av psoriasis. |
US4786652A (en) * | 1987-03-09 | 1988-11-22 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
US5089657A (en) * | 1987-03-11 | 1992-02-18 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
WO2000008495A2 (en) * | 1998-08-06 | 2000-02-17 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Antiproliferative naphthoquinones, derivatives, compositions, and uses thereof |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4229478A (en) * | 1978-06-05 | 1980-10-21 | Syntex (U.S.A.) Inc. | Naphthaquinone anti-psoriatic agents |
US4255405A (en) * | 1978-06-05 | 1981-03-10 | Syntex (U.S.A.) Inc. | Naphthoquinone anti-psoriatic agents |
US4466981A (en) * | 1982-10-27 | 1984-08-21 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
US4593120A (en) * | 1982-10-27 | 1986-06-03 | Syntex (U.S.A.) Inc. | Naphthalene anti-psoriatic agents |
JPH0520420A (ja) * | 1991-07-12 | 1993-01-29 | Brother Ind Ltd | 図形処理装置 |
-
1985
- 1985-01-25 DK DK35885A patent/DK35885A/da not_active Application Discontinuation
- 1985-01-25 DE DE8585100783T patent/DE3564259D1/de not_active Expired
- 1985-01-25 ZA ZA85623A patent/ZA85623B/xx unknown
- 1985-01-25 AT AT85100783T patent/ATE36316T1/de not_active IP Right Cessation
- 1985-01-25 AU AU38098/85A patent/AU3809885A/en not_active Abandoned
- 1985-01-25 KR KR1019850000475A patent/KR900007272B1/ko active IP Right Grant
- 1985-01-25 NO NO850311A patent/NO850311L/no unknown
- 1985-01-25 FI FI850325A patent/FI850325L/fi not_active Application Discontinuation
- 1985-01-25 JP JP60013390A patent/JPS60185745A/ja active Pending
- 1985-01-25 IL IL74162A patent/IL74162A0/xx unknown
- 1985-01-25 NZ NZ210938A patent/NZ210938A/en unknown
- 1985-01-25 HU HU85292A patent/HU194533B/hu not_active IP Right Cessation
- 1985-01-25 EP EP85100783A patent/EP0150831B1/en not_active Expired
- 1985-01-25 ES ES539866A patent/ES539866A0/es active Granted
- 1985-01-25 IE IE850174A patent/IE850174L/xx unknown
Also Published As
Publication number | Publication date |
---|---|
AU3809885A (en) | 1985-08-01 |
EP0150831A2 (en) | 1985-08-07 |
ATE36316T1 (de) | 1988-08-15 |
ZA85623B (en) | 1986-08-27 |
FI850325L (fi) | 1985-07-28 |
IL74162A0 (en) | 1985-04-30 |
DE3564259D1 (en) | 1988-09-15 |
IE850174L (en) | 1985-07-27 |
KR900007272B1 (ko) | 1990-10-06 |
FI850325A0 (fi) | 1985-01-25 |
EP0150831A3 (en) | 1985-12-18 |
KR850005397A (ko) | 1985-08-24 |
HUT36775A (en) | 1985-10-28 |
NZ210938A (en) | 1988-04-29 |
EP0150831B1 (en) | 1988-08-10 |
ES8601089A1 (es) | 1985-11-16 |
ES539866A0 (es) | 1985-11-16 |
JPS60185745A (ja) | 1985-09-21 |
DK35885A (da) | 1985-07-28 |
HU194533B (en) | 1988-02-29 |
DK35885D0 (da) | 1985-01-25 |
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