CA1279328C - Process for preparing basic thioethers and the salts thereof - Google Patents
Process for preparing basic thioethers and the salts thereofInfo
- Publication number
- CA1279328C CA1279328C CA000458870A CA458870A CA1279328C CA 1279328 C CA1279328 C CA 1279328C CA 000458870 A CA000458870 A CA 000458870A CA 458870 A CA458870 A CA 458870A CA 1279328 C CA1279328 C CA 1279328C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- process according
- hydrochloride
- monohydrochloride
- dihydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 150000003839 salts Chemical class 0.000 title description 5
- 150000003568 thioethers Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 97
- 238000000034 method Methods 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 19
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 14
- 239000011707 mineral Substances 0.000 claims abstract description 14
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims abstract description 11
- 230000003197 catalytic effect Effects 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims abstract description 7
- 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 abstract 4
- 239000002585 base Substances 0.000 claims description 61
- 238000002360 preparation method Methods 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 17
- -1 2-[(2-aminoethyl)-thiomethyl]-5-dimethylamino-methylfuran dihydrochloride Chemical compound 0.000 claims description 15
- 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
- 238000011065 in-situ storage Methods 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 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 3
- 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 2
- 239000003054 catalyst Substances 0.000 claims 2
- HDRWLVCQWZUDSF-UHFFFAOYSA-N 5-(2-aminoethylsulfanylmethyl)-n,n,4-trimethylfuran-2-amine Chemical compound CN(C)C1=CC(C)=C(CSCCN)O1 HDRWLVCQWZUDSF-UHFFFAOYSA-N 0.000 claims 1
- IYUSPCPMBILFQR-UHFFFAOYSA-N 5-(2-aminoethylsulfanylmethyl)-n,n,4-trimethylfuran-2-amine;hydrochloride Chemical compound Cl.CN(C)C1=CC(C)=C(CSCCN)O1 IYUSPCPMBILFQR-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 14
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract description 7
- 230000001131 transforming effect Effects 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract 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 abstract 1
- 235000013350 formula milk Nutrition 0.000 description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229940022682 acetone Drugs 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 4
- 229960003151 mercaptamine Drugs 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-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
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum 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
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000001953 recrystallisation 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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- 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 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
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-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
- 230000004075 alteration Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 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
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000004927 fusion Effects 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
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 150000002500 ions Chemical class 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- YQFHPXZGXNYYLD-UHFFFAOYSA-N n-methyl-1-methylsulfanyl-2-nitroethenamine Chemical group CNC(SC)=C[N+]([O-])=O YQFHPXZGXNYYLD-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical compound [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU2515/83 | 1983-07-15 | ||
| HU251483A HU193496B (en) | 1983-07-15 | 1983-07-15 | Process for production of basic tioether and it salts i |
| HU2514/83 | 1983-07-15 | ||
| HU251583A HU193497B (en) | 1983-07-15 | 1983-07-15 | Process for preparing sanitidine hydrogen halogenides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1279328C true CA1279328C (en) | 1991-01-22 |
Family
ID=26317525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000458870A Expired - Lifetime CA1279328C (en) | 1983-07-15 | 1984-07-13 | Process for preparing basic thioethers and the salts thereof |
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 |
| 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 |
| SE457082B (sv) | 1988-11-28 |
| 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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