FI69455C - Foerfarande foer framstaellning av cis-2,6-dimetylmorfolinderivat med fungicid verkan - Google Patents
Foerfarande foer framstaellning av cis-2,6-dimetylmorfolinderivat med fungicid verkan Download PDFInfo
- Publication number
- FI69455C FI69455C FI802418A FI802418A FI69455C FI 69455 C FI69455 C FI 69455C FI 802418 A FI802418 A FI 802418A FI 802418 A FI802418 A FI 802418A FI 69455 C FI69455 C FI 69455C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- cis
- dimethylmorpholine
- compound
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 36
- HNVIQLPOGUDBSU-OLQVQODUSA-N (2s,6r)-2,6-dimethylmorpholine Chemical class C[C@H]1CNC[C@@H](C)O1 HNVIQLPOGUDBSU-OLQVQODUSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- -1 carbonium ion Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 5
- 150000004965 peroxy acids Chemical class 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000001805 chlorine compounds Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000005626 carbonium group Chemical group 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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- 239000003054 catalyst Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-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
- 238000002156 mixing Methods 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YSZJJPVYPTWPHJ-UHFFFAOYSA-N 1-(3-bromo-2-methylpropyl)-4-(2-methylbutan-2-yl)benzene Chemical compound CCC(C)(C)C1=CC=C(CC(C)CBr)C=C1 YSZJJPVYPTWPHJ-UHFFFAOYSA-N 0.000 description 1
- MQHLMHIZUIDKOO-UHFFFAOYSA-N 2,6-dimethyl-4-[2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl]morpholine Chemical compound C1=CC(C(C)(C)CC)=CC=C1CC(C)CN1CC(C)OC(C)C1 MQHLMHIZUIDKOO-UHFFFAOYSA-N 0.000 description 1
- RJOWHRLIQNKYKW-UHFFFAOYSA-N 2-methyl-2-phenylpropanal Chemical class O=CC(C)(C)C1=CC=CC=C1 RJOWHRLIQNKYKW-UHFFFAOYSA-N 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH756079A CH644113A5 (en) | 1979-08-17 | 1979-08-17 | N-substituted 2,6-dimethylmorpholine compounds |
| CH756079 | 1979-08-17 | ||
| CH418780 | 1980-05-29 | ||
| CH418780 | 1980-05-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI802418A7 FI802418A7 (fi) | 1981-02-18 |
| FI69455B FI69455B (fi) | 1985-10-31 |
| FI69455C true FI69455C (fi) | 1986-02-10 |
Family
ID=25694874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI802418A FI69455C (fi) | 1979-08-17 | 1980-08-01 | Foerfarande foer framstaellning av cis-2,6-dimetylmorfolinderivat med fungicid verkan |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0024334B1 (cs) |
| AR (1) | AR225318A1 (cs) |
| AT (1) | ATE4206T1 (cs) |
| AU (1) | AU530398B2 (cs) |
| BG (1) | BG60798B2 (cs) |
| CA (1) | CA1128943A (cs) |
| CS (1) | CS402091A3 (cs) |
| CU (1) | CU35298A (cs) |
| DE (3) | DE3064267D1 (cs) |
| DK (1) | DK150509C (cs) |
| ES (2) | ES494314A0 (cs) |
| FI (1) | FI69455C (cs) |
| FR (1) | FR2463767B1 (cs) |
| GB (1) | GB2056454B (cs) |
| HR (1) | HRP930340B1 (cs) |
| HU (1) | HU182189B (cs) |
| IE (1) | IE52642B1 (cs) |
| IL (1) | IL60813A (cs) |
| IT (1) | IT1220970B (cs) |
| LU (1) | LU82713A1 (cs) |
| MC (1) | MC1345A1 (cs) |
| MY (1) | MY8500272A (cs) |
| NL (1) | NL8004537A (cs) |
| NO (1) | NO153176C (cs) |
| NZ (1) | NZ194628A (cs) |
| PH (1) | PH15480A (cs) |
| PT (1) | PT71708B (cs) |
| SE (1) | SE447730B (cs) |
| SI (1) | SI8011754A8 (cs) |
| YU (1) | YU43475B (cs) |
| ZW (1) | ZW15780A1 (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3421810A1 (de) * | 1984-06-12 | 1985-12-12 | Basf Ag, 6700 Ludwigshafen | Phenylalkylamine - bioregulatoren |
| CA2008775C (en) * | 1989-02-24 | 1998-12-22 | Alberto Ferro | Nail lacquer |
| EP0446585A1 (en) * | 1990-03-12 | 1991-09-18 | F. Hoffmann-La Roche Ag | Control of fungal infections in aquaculture |
| EP1749826A1 (en) | 2005-07-28 | 2007-02-07 | Galderma S.A. | Process of producing bepromoline |
| EP1749825A1 (en) * | 2005-07-28 | 2007-02-07 | Galderma S.A. | Process of producing amorolfine |
| EP1842848A1 (en) * | 2006-04-03 | 2007-10-10 | Galderma S.A. | Process for producing 3-[4-(1,1-dimethyl-propyl)-phenyl]2-methyl-propionaldehyde and cis-4{3-[4-(1,1-dimethyl-propyl)-phenyl]2-methyl-propyl}-2,6-dimethyl-morpholine (amorolfine) |
| EP1935889A1 (en) * | 2006-12-21 | 2008-06-25 | Galderma S.A. | Process of producing amorolfine |
| ITFI20090032A1 (it) | 2009-02-20 | 2010-08-21 | Synteco S P A Prodotti Di Sintesi Per L Ind | Processo di produzione industriale dell'amorolfina cloridrato |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT354187B (de) * | 1976-11-22 | 1979-12-27 | Hoffmann La Roche | Fungizides mittel |
| DE2656747C2 (de) * | 1976-12-15 | 1984-07-05 | Basf Ag, 6700 Ludwigshafen | Morpholinderivate |
| AU4690979A (en) * | 1978-05-16 | 1979-11-29 | F. Hoffmann-La Roche Ag | Heterocyclic compounds |
| DE2830127A1 (de) * | 1978-07-08 | 1980-01-17 | Basf Ag | N-arylpropyl-substituierte cyclische amine |
| DE2830999A1 (de) * | 1978-07-14 | 1980-01-31 | Basf Ag | Verfahren zur herstellung von stereoisomeren n-aralkyl-2,6-dimethylmorpholinen |
| EP0008686B1 (de) * | 1978-08-08 | 1983-04-20 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung von Phenyl-propyl-morpholin- und -piperidin-Derivaten |
| DE2907614A1 (de) * | 1979-02-27 | 1980-09-04 | Basf Ag | Optische aktive formen des 1- eckige klammer auf 3-(p-tert.-buthylphenyl)-2- methylpropyl eckige klammer zu -cis-3,5- dimethylmorpholins |
-
1980
- 1980-07-07 ZW ZW157/80A patent/ZW15780A1/xx unknown
- 1980-07-07 IT IT23283/80A patent/IT1220970B/it active
- 1980-07-08 YU YU1754/80A patent/YU43475B/xx unknown
- 1980-07-08 SI SI8011754A patent/SI8011754A8/sl unknown
- 1980-07-11 CA CA356,038A patent/CA1128943A/en not_active Expired
- 1980-07-25 AR AR281915A patent/AR225318A1/es active
- 1980-07-30 CU CU8035298A patent/CU35298A/es unknown
- 1980-08-01 FI FI802418A patent/FI69455C/fi not_active IP Right Cessation
- 1980-08-05 PH PH24406A patent/PH15480A/en unknown
- 1980-08-07 DE DE8080104656T patent/DE3064267D1/de not_active Expired
- 1980-08-07 DE DE19803029966 patent/DE3029966A1/de not_active Withdrawn
- 1980-08-07 DE DE1993175077 patent/DE19375077I2/de active Active
- 1980-08-07 AT AT80104656T patent/ATE4206T1/de active
- 1980-08-07 EP EP80104656A patent/EP0024334B1/de not_active Expired
- 1980-08-08 NL NL8004537A patent/NL8004537A/nl not_active Application Discontinuation
- 1980-08-11 AU AU61321/80A patent/AU530398B2/en not_active Expired
- 1980-08-11 IL IL60813A patent/IL60813A/xx unknown
- 1980-08-11 NZ NZ194628A patent/NZ194628A/en unknown
- 1980-08-14 FR FR8017977A patent/FR2463767B1/fr not_active Expired
- 1980-08-14 PT PT71708A patent/PT71708B/pt unknown
- 1980-08-14 MC MC801466A patent/MC1345A1/fr unknown
- 1980-08-14 LU LU82713A patent/LU82713A1/de unknown
- 1980-08-15 NO NO802453A patent/NO153176C/no unknown
- 1980-08-15 HU HU802034A patent/HU182189B/hu unknown
- 1980-08-15 GB GB8026709A patent/GB2056454B/en not_active Expired
- 1980-08-15 DK DK355180A patent/DK150509C/da not_active IP Right Cessation
- 1980-08-15 SE SE8005784A patent/SE447730B/sv not_active IP Right Cessation
- 1980-08-15 IE IE1729/80A patent/IE52642B1/en not_active IP Right Cessation
- 1980-08-16 ES ES494314A patent/ES494314A0/es active Granted
-
1981
- 1981-03-02 ES ES499957A patent/ES8201563A1/es not_active Expired
-
1985
- 1985-12-30 MY MY272/85A patent/MY8500272A/xx unknown
-
1991
- 1991-12-23 CS CS914020A patent/CS402091A3/cs unknown
-
1993
- 1993-03-12 HR HRP-1754/80A patent/HRP930340B1/xx not_active IP Right Cessation
-
1994
- 1994-02-25 BG BG098580A patent/BG60798B2/bg unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ND | Supplementary protection certificate (spc) granted | ||
| SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L17 Extension date: 20050801 |
|
| MA | Patent expired |
Owner name: GALDERMA S.A. |