LU86486A1 - Verfahren zur herstellung von 10 -methoxy-6-methylergolin-derivaten und ihren saeureadditionssalzen - Google Patents
Verfahren zur herstellung von 10 -methoxy-6-methylergolin-derivaten und ihren saeureadditionssalzen Download PDFInfo
- Publication number
- LU86486A1 LU86486A1 LU86486A LU86486A LU86486A1 LU 86486 A1 LU86486 A1 LU 86486A1 LU 86486 A LU86486 A LU 86486A LU 86486 A LU86486 A LU 86486A LU 86486 A1 LU86486 A1 LU 86486A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- methyl
- methoxy
- hydrogen
- general formula
- addition salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 239000002253 acid Substances 0.000 title claims description 20
- 150000003839 salts Chemical class 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 3
- NZOOBXONEYCQDN-ZBFHGGJFSA-N (6aR,10aS)-10a-methoxy-7-methyl-4,6,6a,8,9,10-hexahydroindolo[4,3-fg]quinoline Chemical class CO[C@@]12C=3C=CC=C4NC=C(C[C@H]1N(CCC2)C)C34 NZOOBXONEYCQDN-ZBFHGGJFSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229960003642 nicergoline Drugs 0.000 claims description 9
- 238000006552 photochemical reaction Methods 0.000 claims description 8
- -1 5-bromo-nicotinoyl groups Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000011630 iodine Chemical group 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000000155 melt Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 239000000010 aprotic solvent Substances 0.000 description 7
- 238000007069 methylation reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- 238000001704 evaporation Methods 0.000 description 6
- BIXJFIJYBLJTMK-MEBBXXQBSA-N lysergol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-MEBBXXQBSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
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- 238000004809 thin layer chromatography Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000011987 methylation Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 3
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical group O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- UDIJSKHBACNYIE-YMTOWFKASA-N [(6ar,9r)-5-chloro-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=C(Cl)NC3=C1 UDIJSKHBACNYIE-YMTOWFKASA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- ZOUBAHRISDTOBN-YMTOWFKASA-N [(6ar,9r)-5-bromo-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=C(Br)NC3=C1 ZOUBAHRISDTOBN-YMTOWFKASA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PUBHWOQIXSNMMN-HIFRSBDPSA-N (6ar,10as)-10a-methoxy-6,6a,7,8,9,10-hexahydro-4h-indolo[4,3-fg]quinoline Chemical class C1=CC([C@]2(OC)[C@H](NCCC2)C2)=C3C2=CNC3=C1 PUBHWOQIXSNMMN-HIFRSBDPSA-N 0.000 description 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SVXWLTGAHFBMDF-UHFFFAOYSA-N 1h-imidazole;triphenyl phosphite Chemical compound C1=CNC=N1.C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 SVXWLTGAHFBMDF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- 235000010987 pectin Nutrition 0.000 description 1
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- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 229960002116 peripheral vasodilator Drugs 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- 238000003825 pressing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU852446A HU193781B (en) | 1985-06-21 | 1985-06-21 | Process for producing 10alpha-methoxy-6-methylergoline derivatives and acid additional salts thereof |
| HU244685 | 1985-06-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU86486A1 true LU86486A1 (de) | 1986-12-02 |
Family
ID=10959396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU86486A LU86486A1 (de) | 1985-06-21 | 1986-06-20 | Verfahren zur herstellung von 10 -methoxy-6-methylergolin-derivaten und ihren saeureadditionssalzen |
Country Status (14)
| Country | Link |
|---|---|
| BE (1) | BE904956A (cs) |
| CS (1) | CS255876B2 (cs) |
| DD (1) | DD246110A5 (cs) |
| DE (1) | DE3620487A1 (cs) |
| DK (1) | DK291986A (cs) |
| ES (1) | ES8801263A1 (cs) |
| FR (1) | FR2583755B1 (cs) |
| GB (1) | GB2177090B (cs) |
| GR (1) | GR861619B (cs) |
| HU (1) | HU193781B (cs) |
| IT (1) | IT1190135B (cs) |
| LU (1) | LU86486A1 (cs) |
| NL (1) | NL8601584A (cs) |
| PT (1) | PT82807B (cs) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU196598B (en) * | 1986-04-25 | 1988-12-28 | Richter Gedeon Vegyeszet | Process for producing 1- and/or 8-substituted 2-halogenated ergoline derivatives and pharmaceutics comprising such compounds |
| GB9603226D0 (en) * | 1996-02-15 | 1996-04-17 | Pharmacia Spa | Heterocyclyl-ergoline derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1094965B (it) * | 1978-04-05 | 1985-08-10 | Corvi Mora E | Procedimento di preparazione di derivati del lisergolo |
| HU193782B (en) * | 1985-06-21 | 1987-11-30 | Richter Gedeon Vegyeszet | Process for producing 2-halogeno-nicergoline derivatives and acid additional salts thereof |
-
1985
- 1985-06-21 HU HU852446A patent/HU193781B/hu not_active IP Right Cessation
-
1986
- 1986-06-19 BE BE0/216805A patent/BE904956A/fr not_active IP Right Cessation
- 1986-06-19 NL NL8601584A patent/NL8601584A/nl not_active Application Discontinuation
- 1986-06-19 FR FR868608869A patent/FR2583755B1/fr not_active Expired - Lifetime
- 1986-06-19 IT IT20854/86A patent/IT1190135B/it active
- 1986-06-19 DE DE19863620487 patent/DE3620487A1/de not_active Withdrawn
- 1986-06-20 ES ES556358A patent/ES8801263A1/es not_active Expired
- 1986-06-20 PT PT82807A patent/PT82807B/pt not_active IP Right Cessation
- 1986-06-20 DD DD86291508A patent/DD246110A5/de not_active IP Right Cessation
- 1986-06-20 LU LU86486A patent/LU86486A1/de unknown
- 1986-06-20 CS CS864585A patent/CS255876B2/cs unknown
- 1986-06-20 GR GR861619A patent/GR861619B/el unknown
- 1986-06-20 GB GB8615121A patent/GB2177090B/en not_active Expired
- 1986-06-20 DK DK291986A patent/DK291986A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2177090A (en) | 1987-01-14 |
| HU193781B (en) | 1987-11-30 |
| PT82807B (pt) | 1988-04-21 |
| GR861619B (en) | 1986-10-21 |
| FR2583755A1 (fr) | 1986-12-26 |
| ES8801263A1 (es) | 1988-01-01 |
| HUT41023A (en) | 1987-03-30 |
| PT82807A (en) | 1986-07-01 |
| GB2177090B (en) | 1989-07-12 |
| FR2583755B1 (fr) | 1990-06-22 |
| DD246110A5 (de) | 1987-05-27 |
| DE3620487A1 (de) | 1987-01-02 |
| ES556358A0 (es) | 1988-01-01 |
| IT8620854A1 (it) | 1987-12-19 |
| DK291986D0 (da) | 1986-06-20 |
| DK291986A (da) | 1986-12-22 |
| BE904956A (fr) | 1986-12-19 |
| IT8620854A0 (it) | 1986-06-19 |
| NL8601584A (nl) | 1987-01-16 |
| GB8615121D0 (en) | 1986-07-23 |
| IT1190135B (it) | 1988-02-10 |
| CS255876B2 (en) | 1988-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DT | Application date | ||
| TA | Annual fee |