FI83957C - Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara diarylfoereningar. - Google Patents
Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara diarylfoereningar. Download PDFInfo
- Publication number
- FI83957C FI83957C FI853415A FI853415A FI83957C FI 83957 C FI83957 C FI 83957C FI 853415 A FI853415 A FI 853415A FI 853415 A FI853415 A FI 853415A FI 83957 C FI83957 C FI 83957C
- Authority
- FI
- Finland
- Prior art keywords
- ester
- methyl
- diphenylpiperidyl
- dihydro
- propyl
- Prior art date
Links
- -1 cyano, difluoromethoxy, 1,1,2,2-tetrafluoroethoxy Chemical group 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 52
- 150000002148 esters Chemical class 0.000 claims description 50
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- TZDPJNSHSWMCPN-UHFFFAOYSA-N 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC([N+]([O-])=O)=C1 TZDPJNSHSWMCPN-UHFFFAOYSA-N 0.000 claims description 11
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 8
- 150000002081 enamines Chemical class 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- KWUQQEXPGBUDEN-UHFFFAOYSA-N 2,6-dimethyl-4-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(OC(F)(F)C(F)F)=C1 KWUQQEXPGBUDEN-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
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- 239000005977 Ethylene Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- ZGDIGQLFOVNBBC-UHFFFAOYSA-N 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1C(F)(F)F ZGDIGQLFOVNBBC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- GCUMHOAQJSSYSV-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC(Cl)=C1Cl GCUMHOAQJSSYSV-UHFFFAOYSA-N 0.000 claims description 2
- UFBVEBSZOZXYBE-UHFFFAOYSA-N 4-(2-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C)NC(C)=C(C(O)=O)C1C1=CC=CC=C1Cl UFBVEBSZOZXYBE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004816 2,2-dimethylethylene group Chemical group [H]C([H])([H])C([*:2])(C([H])([H])[H])C([H])([H])[*:1] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- SRWXAEWJDHEZJI-UHFFFAOYSA-N 4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1C1=CC=CC([N+]([O-])=O)=C1 SRWXAEWJDHEZJI-UHFFFAOYSA-N 0.000 claims 1
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- JYEMGSHJTLLSFC-UHFFFAOYSA-N CC1=CC(C(=C(N1)C)C(=O)O)(C2=CC=CC(=C2)C#N)C(=O)O Chemical compound CC1=CC(C(=C(N1)C)C(=O)O)(C2=CC=CC(=C2)C#N)C(=O)O JYEMGSHJTLLSFC-UHFFFAOYSA-N 0.000 claims 1
- 239000004914 cyclooctane Substances 0.000 claims 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 18
- 230000035484 reaction time Effects 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- UKVYVZLTGQVOPX-IHWYPQMZSA-N (z)-3-aminobut-2-enoic acid Chemical compound C\C(N)=C\C(O)=O UKVYVZLTGQVOPX-IHWYPQMZSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
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- 239000007858 starting material Substances 0.000 description 10
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- XKORCTIIRYKLLG-ARJAWSKDSA-N methyl (z)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(\C)N XKORCTIIRYKLLG-ARJAWSKDSA-N 0.000 description 7
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
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- 241000700159 Rattus Species 0.000 description 4
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- 239000004480 active ingredient Substances 0.000 description 4
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- 238000005259 measurement Methods 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
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- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 2
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- 244000144993 groups of animals Species 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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- VCDOXKMVZZSCQK-ARJAWSKDSA-N methyl (z)-2-aminobut-2-enoate Chemical compound COC(=O)C(\N)=C\C VCDOXKMVZZSCQK-ARJAWSKDSA-N 0.000 description 1
- QQXPSPWWWCQBFM-UHFFFAOYSA-N methyl 2-[(2,3-dichlorophenyl)methylidene]-3-oxobutanoate Chemical compound COC(=O)C(C(C)=O)=CC1=CC=CC(Cl)=C1Cl QQXPSPWWWCQBFM-UHFFFAOYSA-N 0.000 description 1
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- LYUBYLJQOZIBQB-UHFFFAOYSA-N methyl 2-[(3-nitrophenyl)methylidene]-3-oxobutanoate Chemical compound COC(=O)C(C(C)=O)=CC1=CC=CC([N+]([O-])=O)=C1 LYUBYLJQOZIBQB-UHFFFAOYSA-N 0.000 description 1
- NACIBRFWDJOUSZ-UHFFFAOYSA-N methyl 3-oxo-2-[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methylidene]butanoate Chemical compound COC(=O)C(C(C)=O)=CC1=CC=CC(OC(F)(F)C(F)F)=C1 NACIBRFWDJOUSZ-UHFFFAOYSA-N 0.000 description 1
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- 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
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 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
- 230000000704 physical effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
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- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 230000000054 salidiuretic effect Effects 0.000 description 1
- 230000000580 secretagogue effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- 239000003451 thiazide diuretic agent Substances 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
- 238000012549 training Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH465284 | 1984-09-28 | ||
| CH465284 | 1984-09-28 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI853415A0 FI853415A0 (fi) | 1985-09-06 |
| FI853415L FI853415L (fi) | 1986-03-29 |
| FI83957B FI83957B (fi) | 1991-06-14 |
| FI83957C true FI83957C (fi) | 1991-09-25 |
Family
ID=4280111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI853415A FI83957C (fi) | 1984-09-28 | 1985-09-06 | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara diarylfoereningar. |
Country Status (14)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK704488D0 (da) * | 1988-12-19 | 1988-12-19 | Novo Industri As | Nye n-substituerede azaheterocykliske carboxylsyrer |
| DK142287A (da) * | 1986-03-27 | 1987-09-28 | Byk Gulden Lomberg Chem Fab | Optisk aktive 1,4-dihydropyridinderivater |
| WO1989007443A1 (en) * | 1988-02-19 | 1989-08-24 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Optically pure r-(-)-niguldipine and its derivatives for treating tumorous diseases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI793848A7 (fi) * | 1978-12-18 | 1981-01-01 | Sandoz Ag | Bensoksadiatsoleja ja bensotiadiatsoleja, niiden valmistus ja farmaseuttisia yhdisteitä, jotka sisältävät näitä |
-
1985
- 1985-09-06 FI FI853415A patent/FI83957C/fi not_active IP Right Cessation
- 1985-09-25 HU HU853602A patent/HU194210B/hu unknown
- 1985-09-26 KR KR1019850007105A patent/KR930001404B1/ko not_active Expired - Fee Related
- 1985-09-27 ES ES547385A patent/ES8703148A1/es not_active Expired
- 1985-09-27 GR GR852364A patent/GR852364B/el unknown
- 1985-09-27 IE IE238485A patent/IE66677B1/en not_active IP Right Cessation
- 1985-09-27 PT PT81209A patent/PT81209B/pt not_active IP Right Cessation
- 1985-09-27 AU AU47948/85A patent/AU574842B2/en not_active Ceased
- 1985-09-27 IL IL76511A patent/IL76511A/xx not_active IP Right Cessation
- 1985-09-27 ZA ZA857477A patent/ZA857477B/xx unknown
- 1985-09-27 DK DK440885A patent/DK440885A/da not_active Application Discontinuation
- 1985-09-27 CA CA000491694A patent/CA1291137C/en not_active Expired
- 1985-09-27 NO NO853833A patent/NO169586C/no unknown
- 1985-09-27 NZ NZ213629A patent/NZ213629A/xx unknown
-
1986
- 1986-04-16 ES ES554068A patent/ES8708135A1/es not_active Expired
- 1986-04-16 ES ES554067A patent/ES8800201A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK440885A (da) | 1986-03-29 |
| ES554067A0 (es) | 1987-11-01 |
| NO169586B (no) | 1992-04-06 |
| HU194210B (en) | 1988-01-28 |
| GR852364B (enrdf_load_html_response) | 1985-12-13 |
| KR930001404B1 (ko) | 1993-02-27 |
| IE66677B1 (en) | 1996-01-24 |
| FI83957B (fi) | 1991-06-14 |
| AU574842B2 (en) | 1988-07-14 |
| CA1291137C (en) | 1991-10-22 |
| ES8703148A1 (es) | 1987-02-16 |
| IL76511A (en) | 1990-06-10 |
| NO853833L (no) | 1986-04-01 |
| DK440885D0 (da) | 1985-09-27 |
| NZ213629A (en) | 1989-07-27 |
| PT81209B (pt) | 1988-01-22 |
| KR860002497A (ko) | 1986-04-26 |
| ES554068A0 (es) | 1987-10-16 |
| FI853415A0 (fi) | 1985-09-06 |
| FI853415L (fi) | 1986-03-29 |
| NO169586C (no) | 1992-07-15 |
| ZA857477B (en) | 1986-05-28 |
| HUT38627A (en) | 1986-06-30 |
| ES8800201A1 (es) | 1987-11-01 |
| PT81209A (de) | 1985-10-01 |
| ES547385A0 (es) | 1987-02-16 |
| IE852384L (en) | 1986-03-28 |
| AU4794885A (en) | 1986-04-10 |
| ES8708135A1 (es) | 1987-10-16 |
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| Date | Code | Title | Description |
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| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: BYK GULDEN LOMBERG CHEMISCHE FABRIK GMBH |