HU193496B - Process for production of basic tioether and it salts i - Google Patents
Process for production of basic tioether and it salts i Download PDFInfo
- Publication number
- HU193496B HU193496B HU251483A HU251483A HU193496B HU 193496 B HU193496 B HU 193496B HU 251483 A HU251483 A HU 251483A HU 251483 A HU251483 A HU 251483A HU 193496 B HU193496 B HU 193496B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- hydrochloride
- base
- optionally
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 38
- 150000003839 salts Chemical class 0.000 title claims abstract description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 230000003197 catalytic effect Effects 0.000 claims abstract description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 11
- 239000011707 mineral Substances 0.000 claims abstract description 11
- 150000007524 organic acids Chemical class 0.000 claims abstract description 8
- 239000003085 diluting agent Substances 0.000 claims abstract description 7
- 150000003840 hydrochlorides Chemical class 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 21
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 14
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims description 12
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims description 12
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 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
- 239000000203 mixture Substances 0.000 abstract description 20
- -1 5-dimethylaminomethylfurfuryl alcohol hydride Chemical class 0.000 abstract description 6
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 abstract description 4
- 229960003151 mercaptamine Drugs 0.000 abstract description 4
- 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 abstract description 2
- 238000009472 formulation Methods 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 239000002585 base Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- ZNGPPGHYHNRAEZ-UHFFFAOYSA-N furan;dihydrochloride Chemical compound Cl.Cl.C=1C=COC=1 ZNGPPGHYHNRAEZ-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 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 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- UDLQUVLALYCAMJ-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol;hydron;chloride Chemical compound Cl.CN(C)CC1=CC=C(CO)O1 UDLQUVLALYCAMJ-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 4
- 229960000620 ranitidine Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- DNTYXOAEBUZAJC-UHFFFAOYSA-N chlorosulfinyloxyethane Chemical compound CCOS(Cl)=O DNTYXOAEBUZAJC-UHFFFAOYSA-N 0.000 description 2
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- VXAOKODLROCQJS-UHFFFAOYSA-N furan;hydrochloride Chemical compound Cl.C=1C=COC=1 VXAOKODLROCQJS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CHZXTOCAICMPQR-UHFFFAOYSA-N 2-(2-bromoethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCBr)C(=O)C2=C1 CHZXTOCAICMPQR-UHFFFAOYSA-N 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- ZZDILASZIABWOY-UHFFFAOYSA-N 2-[2-(furan-2-ylmethylsulfanyl)ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCSCC1=CC=CO1 ZZDILASZIABWOY-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
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IGCYDAUZQRJRKB-UHFFFAOYSA-N n,n,5-trimethylfuran-2-amine Chemical compound CN(C)C1=CC=C(C)O1 IGCYDAUZQRJRKB-UHFFFAOYSA-N 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003015 phosphoric acid halides Chemical class 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (17)
| 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 |
| AR84297205A AR242029A1 (es) | 1983-07-15 | 1984-07-13 | Procedimiento para la preparacion del clorhidrato de 1-(2-(5- dimetilaminometil-2-(furilmetiltio)-etil))-amino-1-metilamino-2-nitroetileno |
| GR75307A GR79942B (enrdf_load_stackoverflow) | 1983-07-15 | 1984-07-13 | |
| DK345284A DK162525C (da) | 1983-07-15 | 1984-07-13 | Fremgangsmaade til fremstilling af ranitidin-hydroklorid |
| AT0227284A AT389873B (de) | 1983-07-15 | 1984-07-13 | Verfahren zur herstellung des 1-(2-(5-/ |
| 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 |
| YU122484A YU45634B (sh) | 1983-07-15 | 1984-07-13 | Postupak za dobijanje hidrohlorida 1-/2-/5-dimetilaminometil-2-(furilmetiltio)-etil /-amino-1-metilamino-2-nitroetilena |
| CA000458870A CA1279328C (en) | 1983-07-15 | 1984-07-13 | Process for preparing basic thioethers and the salts thereof |
| FI842822A FI88157C (fi) | 1983-07-15 | 1984-07-13 | Foerfarande foer framstaellning av vaetekloriden av 1- 2-/5-dimetylaminometyl-2-(furylmetyltio)-etyl/ -amino-1-metylamino-2-nitroetylen |
| SU843798790A SU1384197A3 (ru) | 1983-07-15 | 1984-07-13 | Способ получени 1- @ 2-(5-(ди-метиламинометил)-2-(фурилметилтио)-этил) @ амино-1-(метиламино)-2-нитроэтилена или его гидрохлорида и способ получени дигидрохлорида 2-(2-аминоэтил)-тиометил-5-(диметиламинометил)-фурана или его моногидрохлорида |
| KR1019840004164A KR910007966B1 (ko) | 1983-07-15 | 1984-07-14 | 염기성 티오에테르 및 그의 염의 제조방법 |
| ES534363A ES8602732A1 (es) | 1983-07-15 | 1984-07-16 | Procedimiento de preparacion del hidrocloruro de 1-(2-(5-dimetilaminometil-2-(furilmetiltio)-etil)-amino-1-metilamino-2-nitroetileno |
| MX202037A MX159694A (es) | 1983-07-15 | 1984-07-16 | Procedimiento para preparar tioteres basicos y sus sales |
| NO842904A NO842904L (no) | 1983-07-15 | 1984-07-16 | Fremgangsmaate ved fremstilling av basiske thioethere og salter derav |
| BG066276A BG42356A3 (en) | 1983-07-15 | 1984-07-16 | Method for preparing hydrochloride of 1- [2- (5- dimethylaminomethyl- 2- (furylmethylthio)- ethyl]- amino- 1- methylamino- 2= nitroethylene |
| CS845492A CS248717B2 (en) | 1983-07-15 | 1984-07-16 | Production method of the hydrochloride of the 1-(2-(5 dimethylamino-methyl-2-furylmethylthio)ethyl)p)amino-1-methylamino-2-nitroethylene |
| 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 (1)
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT34966A HUT34966A (en) | 1985-05-28 |
| HU193496B true HU193496B (en) | 1987-10-28 |
Family
ID=10959779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU251483A HU193496B (en) | 1983-07-15 | 1983-07-15 | Process for production of basic tioether and it salts i |
Country Status (3)
| Country | Link |
|---|---|
| BG (1) | BG42356A3 (enrdf_load_stackoverflow) |
| GR (1) | GR79942B (enrdf_load_stackoverflow) |
| HU (1) | HU193496B (enrdf_load_stackoverflow) |
-
1983
- 1983-07-15 HU HU251483A patent/HU193496B/hu not_active IP Right Cessation
-
1984
- 1984-07-13 GR GR75307A patent/GR79942B/el unknown
- 1984-07-16 BG BG066276A patent/BG42356A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT34966A (en) | 1985-05-28 |
| BG42356A3 (en) | 1987-11-14 |
| GR79942B (enrdf_load_stackoverflow) | 1984-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: RICHTER GEDEON VEGYESZETI GYAR RT., HU |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee |