IE57250B1 - Process for preparing secondary amines - Google Patents
Process for preparing secondary aminesInfo
- Publication number
- IE57250B1 IE57250B1 IE1022/84A IE102284A IE57250B1 IE 57250 B1 IE57250 B1 IE 57250B1 IE 1022/84 A IE1022/84 A IE 1022/84A IE 102284 A IE102284 A IE 102284A IE 57250 B1 IE57250 B1 IE 57250B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- preparing
- methanol
- chloro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 6
- 150000003335 secondary amines Chemical class 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- RCKHJBKVFQNBOW-UHFFFAOYSA-N 2-[2-(2-chloro-3,4-dimethoxyphenyl)ethylamino]-1-(4-methoxyphenyl)-2-methylsulfanylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(SC)NCCC1=CC=C(OC)C(OC)=C1Cl RCKHJBKVFQNBOW-UHFFFAOYSA-N 0.000 claims 1
- HTKYEDIGHCMFSD-UHFFFAOYSA-N 2-[2-(2-fluoro-3,4-dimethoxyphenyl)ethylamino]-1-(4-methoxyphenyl)-2-methylsulfanylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(SC)NCCC1=CC=C(OC)C(OC)=C1F HTKYEDIGHCMFSD-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 6
- YTKGUKHQYUHYTQ-UHFFFAOYSA-N 2-(2-chloro-3,4-dimethoxyphenyl)ethanamine Chemical compound COC1=CC=C(CCN)C(Cl)=C1OC YTKGUKHQYUHYTQ-UHFFFAOYSA-N 0.000 abstract description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- LNZBSIXPXJKKDF-UHFFFAOYSA-N 2-(4-methoxyphenyl)-2-oxoacetaldehyde Chemical compound COC1=CC=C(C(=O)C=O)C=C1 LNZBSIXPXJKKDF-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- -1 p-hydroxyphenyl Chemical group 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001311 chemical methods and process Methods 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940117803 phenethylamine Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000007039 two-step reaction Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical group N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 1
- LXTNZWGUMORTKT-UHFFFAOYSA-N 1-phenyl-2-(2-phenylethylamino)ethanol Chemical class C=1C=CC=CC=1C(O)CNCCC1=CC=CC=C1 LXTNZWGUMORTKT-UHFFFAOYSA-N 0.000 description 1
- PMTBLRKLMNAJQI-UHFFFAOYSA-N 2-(2-chloro-3,4-dimethoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.COC1=CC=C(CCN)C(Cl)=C1OC PMTBLRKLMNAJQI-UHFFFAOYSA-N 0.000 description 1
- WRGMAUWWSLMQIR-UHFFFAOYSA-N 2-(2-fluoro-3,4-dimethoxyphenyl)ethanamine Chemical compound COC1=CC=C(CCN)C(F)=C1OC WRGMAUWWSLMQIR-UHFFFAOYSA-N 0.000 description 1
- ARHIWOBUUAPVTB-UHFFFAOYSA-N 2-(4-methoxyphenyl)oxirane Chemical compound C1=CC(OC)=CC=C1C1OC1 ARHIWOBUUAPVTB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CGKRFDXHYBJWPO-UHFFFAOYSA-N C(C)[AlH]CC.[Na] Chemical compound C(C)[AlH]CC.[Na] CGKRFDXHYBJWPO-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010062237 Renal impairment Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- JUGGGTWXNOOGNX-UHFFFAOYSA-N dichloromethane;methanesulfonic acid Chemical compound ClCCl.CS(O)(=O)=O JUGGGTWXNOOGNX-UHFFFAOYSA-N 0.000 description 1
- USLKCMBGQFYUFI-UHFFFAOYSA-N dichloromethane;tribromoborane Chemical compound ClCCl.BrB(Br)Br USLKCMBGQFYUFI-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 229940005501 dopaminergic agent Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000003947 ethylamines Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000005977 kidney dysfunction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- QLUZJFBPDLVUQW-UHFFFAOYSA-K sodium zinc trihydroxide Chemical compound [OH-].[OH-].[OH-].[Na+].[Zn++] QLUZJFBPDLVUQW-UHFFFAOYSA-K 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- QGXFDKHOSNJQKE-UHFFFAOYSA-N sulfuric acid;2,2,2-trifluoroacetic acid Chemical compound OS(O)(=O)=O.OC(=O)C(F)(F)F QGXFDKHOSNJQKE-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- G—PHYSICS
- G05—CONTROLLING; REGULATING
- G05B—CONTROL OR REGULATING SYSTEMS IN GENERAL; FUNCTIONAL ELEMENTS OF SUCH SYSTEMS; MONITORING OR TESTING ARRANGEMENTS FOR SUCH SYSTEMS OR ELEMENTS
- G05B2219/00—Program-control systems
- G05B2219/30—Nc systems
- G05B2219/50—Machine tool, machine tool null till machine tool work handling
- G05B2219/50103—Restart, reverse, return along machined path, stop
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/489,654 US4540819A (en) | 1983-04-28 | 1983-04-28 | Process for preparing secondary amines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE841022L IE841022L (en) | 1984-10-28 |
| IE57250B1 true IE57250B1 (en) | 1992-06-17 |
Family
ID=23944726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1022/84A IE57250B1 (en) | 1983-04-28 | 1984-04-26 | Process for preparing secondary amines |
Country Status (13)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4579972A (en) * | 1983-04-28 | 1986-04-01 | Smithkline Beckman Corporation | Intermediates for preparing secondary amines |
| US4781173A (en) * | 1985-06-28 | 1988-11-01 | Juha Ven | Evaporating device and electric supply station provided with such an evaporating device |
| JP2007529569A (ja) * | 2005-01-24 | 2007-10-25 | シコール インコーポレイティド | メシル酸フェノルドパムの調製方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3345416A (en) * | 1963-09-04 | 1967-10-03 | Dept Of Chemistry | Preparation and rearrangement of beta-ketosulfoxides |
| AT338242B (de) * | 1975-09-25 | 1977-08-10 | Tanabe Seiyaku Co | Verfahren zur herstellung neuer racemischer und optisch aktiver 1-hydroxyphenyl-2-(3',4'-dimethoxyphenathyl)aminoathanole-(1) |
| US4197297A (en) * | 1976-11-17 | 1980-04-08 | Smithkline Corporation | 6-Halo-7,8-dihydroxy-1-(hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepines |
| CH637383A5 (en) * | 1978-01-01 | 1983-07-29 | Smithkline Beckman Corp | Trisubstituted 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines, and their salts |
| IT1148741B (it) * | 1980-11-28 | 1986-12-03 | Zambeletti Spa L | Procedimento per la preparazione dell'1-(3,5-dimetossi-4-idrossifenil)-2-(n-metilammino)etanolo cloridrato |
-
1983
- 1983-04-28 US US06/489,654 patent/US4540819A/en not_active Expired - Fee Related
-
1984
- 1984-04-03 ZA ZA842474A patent/ZA842474B/xx unknown
- 1984-04-10 AU AU26680/84A patent/AU573209B2/en not_active Ceased
- 1984-04-11 DK DK188384A patent/DK162980C/da active
- 1984-04-11 CA CA000451717A patent/CA1210780A/en not_active Expired
- 1984-04-13 DE DE8484302552T patent/DE3460757D1/de not_active Expired
- 1984-04-13 AT AT84302552T patent/ATE22285T1/de active
- 1984-04-13 EP EP84302552A patent/EP0125053B1/en not_active Expired
- 1984-04-23 PT PT78470A patent/PT78470B/pt not_active IP Right Cessation
- 1984-04-25 JP JP59085080A patent/JPS59206339A/ja active Granted
- 1984-04-26 IE IE1022/84A patent/IE57250B1/en not_active IP Right Cessation
- 1984-04-26 GR GR74516A patent/GR81490B/el unknown
- 1984-04-27 ES ES531975A patent/ES8506584A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA842474B (en) | 1985-04-24 |
| ATE22285T1 (de) | 1986-10-15 |
| DK162980B (da) | 1992-01-06 |
| JPS59206339A (ja) | 1984-11-22 |
| DE3460757D1 (en) | 1986-10-23 |
| AU573209B2 (en) | 1988-06-02 |
| PT78470A (en) | 1984-05-01 |
| GR81490B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-11 |
| ES531975A0 (es) | 1985-08-01 |
| EP0125053B1 (en) | 1986-09-17 |
| US4540819A (en) | 1985-09-10 |
| CA1210780A (en) | 1986-09-02 |
| PT78470B (en) | 1986-08-28 |
| EP0125053A1 (en) | 1984-11-14 |
| IE841022L (en) | 1984-10-28 |
| DK162980C (da) | 1992-06-01 |
| JPH0472818B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-11-19 |
| DK188384A (da) | 1984-10-29 |
| AU2668084A (en) | 1984-11-01 |
| DK188384D0 (da) | 1984-04-11 |
| ES8506584A1 (es) | 1985-08-01 |
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