SE457082B - Foerfarande foer framstaellning av hydrokloriden av 1-/2-/5-dimetylaminometyl-2-(furylmetyltio)-etyl//-amino-1-metylamino-2-nitroetylen - Google Patents
Foerfarande foer framstaellning av hydrokloriden av 1-/2-/5-dimetylaminometyl-2-(furylmetyltio)-etyl//-amino-1-metylamino-2-nitroetylenInfo
- Publication number
- SE457082B SE457082B SE8403717A SE8403717A SE457082B SE 457082 B SE457082 B SE 457082B SE 8403717 A SE8403717 A SE 8403717A SE 8403717 A SE8403717 A SE 8403717A SE 457082 B SE457082 B SE 457082B
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- hydrochloride
- base
- methylamino
- mol
- Prior art date
Links
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 97
- 238000000034 method Methods 0.000 title claims description 47
- 238000002360 preparation method Methods 0.000 title claims description 27
- -1 5-DIMETHYLAMINOMETHYL-2- (FURYLMETHYLTHIO) -ETHYL Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 13
- 239000011707 mineral Substances 0.000 claims abstract description 13
- 230000003197 catalytic effect Effects 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 150000007524 organic acids Chemical class 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 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 11
- 239000003085 diluting agent Substances 0.000 claims description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- 239000000126 substance Substances 0.000 claims description 5
- 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 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract 1
- YQFHPXZGXNYYLD-UHFFFAOYSA-N n-methyl-1-methylsulfanyl-2-nitroethenamine Chemical group CNC(SC)=C[N+]([O-])=O YQFHPXZGXNYYLD-UHFFFAOYSA-N 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 239000002585 base Substances 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 37
- 239000000047 product Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 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
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 235000010755 mineral Nutrition 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 238000011065 in-situ storage Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 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
- 239000013078 crystal Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 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
- 150000003839 salts Chemical class 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- UHMZHYUCMREDRI-UHFFFAOYSA-N ethyl thiohypochlorite Chemical compound CCSCl UHMZHYUCMREDRI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 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
- 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
- FVELDMCOCLJSQN-UHFFFAOYSA-N benzene;1,1-dichloroethane Chemical compound CC(Cl)Cl.C1=CC=CC=C1 FVELDMCOCLJSQN-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013312 flour Nutrition 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
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000155 melt Substances 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
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU251483A HU193496B (en) | 1983-07-15 | 1983-07-15 | Process for production of basic tioether and it salts i |
| HU251583A HU193497B (en) | 1983-07-15 | 1983-07-15 | Process for preparing sanitidine hydrogen halogenides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8403717D0 SE8403717D0 (sv) | 1984-07-13 |
| SE8403717L SE8403717L (sv) | 1985-01-16 |
| SE457082B true SE457082B (sv) | 1988-11-28 |
Family
ID=26317525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8403717A SE457082B (sv) | 1983-07-15 | 1984-07-13 | Foerfarande foer framstaellning av hydrokloriden av 1-/2-/5-dimetylaminometyl-2-(furylmetyltio)-etyl//-amino-1-metylamino-2-nitroetylen |
Country Status (13)
| Country | Link |
|---|---|
| KR (1) | KR910007966B1 (cs) |
| AR (1) | AR242029A1 (cs) |
| AT (1) | AT389873B (cs) |
| CA (1) | CA1279328C (cs) |
| CS (1) | CS248717B2 (cs) |
| DK (1) | DK162525C (cs) |
| ES (1) | ES534363A0 (cs) |
| FI (1) | FI88157C (cs) |
| MX (1) | MX159694A (cs) |
| NO (1) | NO842904L (cs) |
| SE (1) | SE457082B (cs) |
| SU (1) | SU1384197A3 (cs) |
| YU (1) | YU45634B (cs) |
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 |
| FI811376A7 (fi) * | 1980-05-13 | 1981-11-14 | C R C Compagnia Di Ricerca Chimica | Menetelmä N-/2-///5-(dialkyyliamino)- metyyli-2-furanyyli/-me- tyyli/tio/-etyyli/N'-alkyyli-2-nitro-1,1-eteeeteenidiamiinien ja niiden välituotteiden valmistamiseksi. |
| ES495493A0 (es) * | 1980-09-30 | 1981-11-01 | Inke Sa | Ÿprocedimiento para la obtencion de la n-2-5-(dimetilamino)metil-2-furanil metil tio-n-metil-2-nitro-1,1-etenodiaminaÿ. |
| 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 |
| ES497737A0 (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 |
| DE3170348D1 (en) * | 1980-12-30 | 1985-06-05 | Glaxo Group Ltd | Process for the preparation of a furan derivative |
| DK153841C (da) * | 1980-12-30 | 1989-02-20 | Glaxo Group Ltd | Fremgangsmaade til fremstilling af ranitidin |
| ATE11536T1 (de) * | 1981-02-20 | 1985-02-15 | Glaxo Group Limited | Verfahren zur herstellung eines furanderivats. |
| ES8300325A1 (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". |
| ES8303391A1 (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 AR AR84297205A patent/AR242029A1/es active
- 1984-07-13 YU YU122484A patent/YU45634B/sh unknown
- 1984-07-13 SE SE8403717A patent/SE457082B/sv not_active IP Right Cessation
- 1984-07-13 AT AT0227284A patent/AT389873B/de active
- 1984-07-13 SU SU843798790A patent/SU1384197A3/ru active
- 1984-07-13 CA CA000458870A patent/CA1279328C/en not_active Expired - Lifetime
- 1984-07-13 FI FI842822A patent/FI88157C/fi not_active IP Right Cessation
- 1984-07-13 DK DK345284A patent/DK162525C/da not_active IP Right Cessation
- 1984-07-14 KR KR1019840004164A patent/KR910007966B1/ko not_active Expired
- 1984-07-16 MX MX202037A patent/MX159694A/es unknown
- 1984-07-16 ES ES534363A patent/ES534363A0/es active Granted
- 1984-07-16 CS CS845492A patent/CS248717B2/cs unknown
- 1984-07-16 NO NO842904A patent/NO842904L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI88157B (fi) | 1992-12-31 |
| ATA227284A (de) | 1989-07-15 |
| CA1279328C (en) | 1991-01-22 |
| MX159694A (es) | 1989-08-07 |
| KR910007966B1 (ko) | 1991-10-04 |
| KR850001187A (ko) | 1985-03-16 |
| YU45634B (sh) | 1992-07-20 |
| ES8602732A1 (es) | 1985-12-01 |
| AR242029A1 (es) | 1993-02-26 |
| ES534363A0 (es) | 1985-12-01 |
| NO842904L (no) | 1985-01-16 |
| AT389873B (de) | 1990-02-12 |
| DK162525B (da) | 1991-11-11 |
| FI842822L (fi) | 1985-01-16 |
| FI88157C (fi) | 1993-04-13 |
| SE8403717L (sv) | 1985-01-16 |
| YU122484A (cs) | 1986-10-31 |
| SU1384197A3 (ru) | 1988-03-23 |
| DK162525C (da) | 1992-03-30 |
| FI842822A0 (fi) | 1984-07-13 |
| CS248717B2 (en) | 1987-02-12 |
| SE8403717D0 (sv) | 1984-07-13 |
| DK345284D0 (da) | 1984-07-13 |
| DK345284A (da) | 1985-01-16 |
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