NO842904L - Fremgangsmaate ved fremstilling av basiske thioethere og salter derav - Google Patents
Fremgangsmaate ved fremstilling av basiske thioethere og salter deravInfo
- Publication number
- NO842904L NO842904L NO842904A NO842904A NO842904L NO 842904 L NO842904 L NO 842904L NO 842904 A NO842904 A NO 842904A NO 842904 A NO842904 A NO 842904A NO 842904 L NO842904 L NO 842904L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- base
- hydrochloride
- monohydrochloride
- dihydrochloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 48
- 238000004519 manufacturing process Methods 0.000 title description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 102
- 150000001875 compounds Chemical class 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 27
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims description 17
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 230000003197 catalytic effect Effects 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- YQFHPXZGXNYYLD-ARJAWSKDSA-N (z)-n-methyl-1-methylsulfanyl-2-nitroethenamine Chemical group CN\C(SC)=C\[N+]([O-])=O YQFHPXZGXNYYLD-ARJAWSKDSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- JFGCGQJHMUYGLU-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine Chemical compound CN(C)CC1=CC=C(CSCCN)O1 JFGCGQJHMUYGLU-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002585 base Substances 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 38
- 239000000047 product Substances 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- -1 alkali metal hydrogen carbonate Chemical class 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- JNTOYGBZXJSVNI-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine;dihydrochloride Chemical compound Cl.Cl.CN(C)CC1=CC=C(CSCCN)O1 JNTOYGBZXJSVNI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- MHYPZOIXCWYNTQ-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine;hydrochloride Chemical compound Cl.CN(C)CC1=CC=C(CSCCN)O1 MHYPZOIXCWYNTQ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 101150052863 THY1 gene Proteins 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- DNTYXOAEBUZAJC-UHFFFAOYSA-N chlorosulfinyloxyethane Chemical compound CCOS(Cl)=O DNTYXOAEBUZAJC-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/341—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO913263A NO170543C (no) | 1983-07-15 | 1991-08-20 | Fremgangsmaate for fremstilling av hydrokloridet av 1-(2-(5-dimethylaminomethyl-2-(furylmethylthio)-ethyl))-amino-1-methylamino-2-nitroethylen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU251583A HU193497B (en) | 1983-07-15 | 1983-07-15 | Process for preparing sanitidine hydrogen halogenides |
| HU251483A HU193496B (en) | 1983-07-15 | 1983-07-15 | Process for production of basic tioether and it salts i |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO842904L true NO842904L (no) | 1985-01-16 |
Family
ID=26317525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO842904A NO842904L (no) | 1983-07-15 | 1984-07-16 | Fremgangsmaate ved fremstilling av basiske thioethere og salter derav |
Country Status (13)
| Country | Link |
|---|---|
| KR (1) | KR910007966B1 (sv) |
| AR (1) | AR242029A1 (sv) |
| AT (1) | AT389873B (sv) |
| CA (1) | CA1279328C (sv) |
| CS (1) | CS248717B2 (sv) |
| DK (1) | DK162525C (sv) |
| ES (1) | ES8602732A1 (sv) |
| FI (1) | FI88157C (sv) |
| MX (1) | MX159694A (sv) |
| NO (1) | NO842904L (sv) |
| SE (1) | SE457082B (sv) |
| SU (1) | SU1384197A3 (sv) |
| YU (1) | YU45634B (sv) |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| JPS56103171A (en) * | 1980-01-08 | 1981-08-18 | Glaxo Group Ltd | Manufacture of furan derivative |
| FI811376L (fi) * | 1980-05-13 | 1981-11-14 | Crc Ricerca Chim | Foerfarande foer framstaellning av n-/2-///5-(dialkylamino)-metyl-2-furanyl/-metyl/-tio/etyl/-n'-alkyl-2-nitro-1,1-etendiaminer och deras mellanprodukter |
| ES8200358A1 (es) * | 1980-09-30 | 1981-11-01 | Inke Sa | Procedimiento para la obtencion de la n-2-5-(dimetilamino)metil-2-furanil metil tio-n-metil-2-nitro-1,1-etenodiamina . |
| IL63968A (en) * | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| ES8200101A1 (es) * | 1980-12-03 | 1981-10-16 | Inke Sa | Procedimiento para la obtencion de la n-(2-( ( (5-( (dimeti-lamino)metil)-2-furanil)metil)tio)etil)-n'-metil-2-nitro-1,1-etenodiamina |
| ES8200674A1 (es) * | 1980-12-13 | 1981-11-16 | Parellada Llauger Miguel | Procedimiento para la obtencion de la n-(2-((5-((dimetilami-no)metil)furfuril)tio)etil)-n'- metil -2- nitro-1,1- eteno- diamina |
| DK153481C (da) * | 1980-12-30 | 1989-06-05 | Glaxo Group Ltd | Fremgangsmaade til fremstilling af ranitidin |
| DE3170346D1 (en) * | 1980-12-30 | 1985-06-05 | Glaxo Group Ltd | Process for the preparation of a furan derivative |
| US4399293A (en) * | 1981-02-20 | 1983-08-16 | Glaxo Group Limited | Process for the preparation of a furan derivative |
| ES501844A0 (es) * | 1981-05-02 | 1982-11-01 | Especialidades Farmaco Terape | Procedimiento para la obtencion de un compuesto derivado delalcohol furfurilico |
| AR229878A1 (es) * | 1981-05-07 | 1983-12-30 | Glaxo Group Ltd | Procedimiento para preparar ranitidina |
| ES502940A0 (es) * | 1981-06-10 | 1982-11-01 | Lafarquim | Procedimiento para la obtencion de derivados de furil metil mercaptano y sus sales de interes farmacologico |
| ES507360A0 (es) * | 1981-11-20 | 1982-11-16 | Especialidades Latinas Medic U | Procedimiento de obtencion de n-(2-5-dimetilamino,metil-2-furanil-metil-tio-etil-n'-metil-s-nitro-etano-diamina. |
| ES508693A0 (es) * | 1982-01-13 | 1982-11-01 | Barisintex Sa | "procedimiento para la obtencion de derivados de aminoalkilfuranos". |
| ES511830A0 (es) * | 1982-04-30 | 1983-02-01 | Inke Sa | Procedimiento para la obtencion de la n-2-(5-(dimetilanmino)metil-2-furanil)metil)tio)etil)-n'-metil-2-nitro-1,1-eteno- diamina. |
| ES512315A0 (es) * | 1982-05-19 | 1983-02-01 | Tabah Papo Marcelo | Procedimiento para la obtencion de un nuevo derivado furanico de interes terapeutico. |
-
1984
- 1984-07-13 DK DK345284A patent/DK162525C/da not_active IP Right Cessation
- 1984-07-13 AR AR84297205A patent/AR242029A1/es active
- 1984-07-13 CA CA000458870A patent/CA1279328C/en not_active Expired - Fee Related
- 1984-07-13 SE SE8403717A patent/SE457082B/sv not_active IP Right Cessation
- 1984-07-13 YU YU122484A patent/YU45634B/sh unknown
- 1984-07-13 FI FI842822A patent/FI88157C/sv not_active IP Right Cessation
- 1984-07-13 SU SU843798790A patent/SU1384197A3/ru active
- 1984-07-13 AT AT0227284A patent/AT389873B/de active
- 1984-07-14 KR KR1019840004164A patent/KR910007966B1/ko not_active IP Right Cessation
- 1984-07-16 CS CS845492A patent/CS248717B2/cs unknown
- 1984-07-16 MX MX202037A patent/MX159694A/es unknown
- 1984-07-16 NO NO842904A patent/NO842904L/no unknown
- 1984-07-16 ES ES534363A patent/ES8602732A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE8403717L (sv) | 1985-01-16 |
| KR850001187A (ko) | 1985-03-16 |
| MX159694A (es) | 1989-08-07 |
| YU122484A (sv) | 1986-10-31 |
| SE457082B (sv) | 1988-11-28 |
| AR242029A1 (es) | 1993-02-26 |
| ES534363A0 (es) | 1985-12-01 |
| FI88157B (fi) | 1992-12-31 |
| CS248717B2 (en) | 1987-02-12 |
| AT389873B (de) | 1990-02-12 |
| ES8602732A1 (es) | 1985-12-01 |
| DK162525C (da) | 1992-03-30 |
| ATA227284A (de) | 1989-07-15 |
| SE8403717D0 (sv) | 1984-07-13 |
| DK345284A (da) | 1985-01-16 |
| KR910007966B1 (ko) | 1991-10-04 |
| CA1279328C (en) | 1991-01-22 |
| SU1384197A3 (ru) | 1988-03-23 |
| DK162525B (da) | 1991-11-11 |
| FI842822A (fi) | 1985-01-16 |
| DK345284D0 (da) | 1984-07-13 |
| FI88157C (sv) | 1993-04-13 |
| YU45634B (sh) | 1992-07-20 |
| FI842822A0 (fi) | 1984-07-13 |
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