HU198196B - Process for production of basic tioether and its salts - Google Patents
Process for production of basic tioether and its salts Download PDFInfo
- Publication number
- HU198196B HU198196B HU841690A HU169084A HU198196B HU 198196 B HU198196 B HU 198196B HU 841690 A HU841690 A HU 841690A HU 169084 A HU169084 A HU 169084A HU 198196 B HU198196 B HU 198196B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- base
- acid addition
- dimethylaminomethyl
- addition salt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- 150000003839 salts Chemical class 0.000 title claims abstract description 36
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 239000002253 acid Substances 0.000 claims abstract description 29
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960003151 mercaptamine Drugs 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 13
- -1 2 - ((2-aminoethyl) thio-thioethyl) -5- (dimethylaminomethyl) furan Chemical class 0.000 claims description 10
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical group Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims description 5
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 26
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract description 12
- 208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
- 208000000718 duodenal ulcer Diseases 0.000 abstract description 2
- 230000002496 gastric effect Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- MOMRWKLLGUQTFY-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methyl hydrogen sulfate Chemical compound S(=O)(=O)(OCC=1OC(=CC1)CN(C)C)O MOMRWKLLGUQTFY-UHFFFAOYSA-N 0.000 abstract 2
- 230000001131 transforming effect Effects 0.000 abstract 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 6
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 5
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Substances OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JFGCGQJHMUYGLU-UHFFFAOYSA-N 2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethanamine Chemical class CN(C)CC1=CC=C(CSCCN)O1 JFGCGQJHMUYGLU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 238000006683 Mannich reaction Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 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 3
- 229960000620 ranitidine Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KAZRCBVXUOCTIO-UHFFFAOYSA-N 5-(chloromethyl)furan-2-carbaldehyde Chemical compound ClCC1=CC=C(C=O)O1 KAZRCBVXUOCTIO-UHFFFAOYSA-N 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- VJEZYZLITKUTFH-UHFFFAOYSA-N 2-(hydrazinecarbonyl)benzoic acid Chemical class NNC(=O)C1=CC=CC=C1C(O)=O VJEZYZLITKUTFH-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
- AWNXYVUAXXHXQD-UHFFFAOYSA-N 3-(furan-2-yl)propanethioamide Chemical compound NC(=S)CCC1=CC=CO1 AWNXYVUAXXHXQD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229940124447 delivery agent Drugs 0.000 description 1
- 239000002274 desiccant Substances 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
- 230000000694 effects Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 201000005917 gastric ulcer Diseases 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
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- 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)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU841690A HU198196B (en) | 1984-05-02 | 1984-05-02 | Process for production of basic tioether and its salts |
| CN 85103102 CN1011785B (zh) | 1984-05-02 | 1985-04-24 | 2-[2-(氨乙基)硫甲基]-5-二甲基氨甲基呋喃的新型酸加成盐的制备方法 |
| SU853885802A SU1375133A3 (ru) | 1984-05-02 | 1985-04-29 | Способ получени 2- @ (2-аминоэтил)-тиометил @ -5-(диметиламинометил)-фурана или его аддитивных солей с кислотами (его варианты) |
| MX205130A MX161373A (es) | 1984-05-02 | 1985-04-29 | Procedimiento para la preparacion de las sales de adicion con acidos del 2-((2-amino etil)-tiometil)-5-dimetilaminometilfurano |
| YU73385A YU45714B (sh) | 1984-05-02 | 1985-04-30 | Postupak za dobijanje novih adicionih soli sa kiselinama -2-/2-aminoetil/-tiometil/-5-dimetil aminomftilfurana |
| ES542782A ES8609292A1 (es) | 1984-05-02 | 1985-04-30 | Procedimiento de preparacion de nuevas sales deadicion aci- da de 2-((2-aminoetil)-tiometil)-5-dimetilaminometil-furano |
| NO851727A NO168942C (no) | 1984-05-02 | 1985-04-30 | Fremgangsmaate for fremstilling av 2-((2-aminoethyl)-thiomethyl)-5-dimethylaminomethylfuran og syreaddisjonssalter derav |
| CS853160A CS259878B2 (en) | 1984-05-02 | 1985-04-30 | Method of additive salt preparation with acid derived from 2(/2-aminoethyl/thiomethyl)-5-dimethylaminomethyl furane |
| KR1019850002962A KR920005828B1 (ko) | 1984-05-02 | 1985-05-01 | 2-[(2-아미노에틸)-티오메틸]-5-디메틸아미노메틸 푸란의 산부가염의 제조방법 |
| PT80382A PT80382B (pt) | 1984-05-02 | 1985-05-02 | Processo para a preparacao de novos sais de adicao de acidos de 2-{(2-amiono-etil)-tiometil}-5-dimetilamino-metil-furano |
| FI851742A FI88501C (fi) | 1984-05-02 | 1985-05-02 | Foerfarande foer framstaellning av syraadditionssalter av 2-/(2-aminoetyl)tiometyl/-5-dimetylaminometylfuran |
| IT20558/85A IT1200464B (it) | 1984-05-02 | 1985-05-02 | Sali di addizione con acidi del 2-((2-amminoetil)-tiometil)-5-dimetilamminometilfurano e procedimento per la loro preparazione |
| AR300258A AR240455A1 (es) | 1984-05-02 | 1985-05-02 | Un procedimiento para la preparacion de las sales de adicion de acido de 2-((2-aminoetil)-tiometil)-5-dimetilaminometil furano, obtencion del compuesto utilizado como materia prima en el mismo y el compuesto asi obtenido. |
| DK196785A DK196785A (da) | 1984-05-02 | 1985-05-02 | Syreadditionssalte af en basisk tioaeter og fremgangsmaade til fremstilling deraf |
| AT0129585A AT387573B (de) | 1984-05-02 | 1985-05-02 | Verfahren zur herstellung des basischen thioaethers 2-((2-amino-aethyl)-thiomethyl)-5(dimethyl-aminomethyl)-furan sowie der saeureadditionssalze desselben |
| GR851062A GR851062B (en, 2012) | 1984-05-02 | 1985-05-02 | |
| CA000480665A CA1268474A (en) | 1984-05-02 | 1985-05-02 | Process for preparing a basic thioether and the salts thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU841690A HU198196B (en) | 1984-05-02 | 1984-05-02 | Process for production of basic tioether and its salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT37774A HUT37774A (en) | 1986-02-28 |
| HU198196B true HU198196B (en) | 1989-08-28 |
Family
ID=10955710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU841690A HU198196B (en) | 1984-05-02 | 1984-05-02 | Process for production of basic tioether and its salts |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR920005828B1 (en, 2012) |
| AR (1) | AR240455A1 (en, 2012) |
| AT (1) | AT387573B (en, 2012) |
| CA (1) | CA1268474A (en, 2012) |
| CS (1) | CS259878B2 (en, 2012) |
| DK (1) | DK196785A (en, 2012) |
| ES (1) | ES8609292A1 (en, 2012) |
| FI (1) | FI88501C (en, 2012) |
| GR (1) | GR851062B (en, 2012) |
| HU (1) | HU198196B (en, 2012) |
| IT (1) | IT1200464B (en, 2012) |
| MX (1) | MX161373A (en, 2012) |
| NO (1) | NO168942C (en, 2012) |
| PT (1) | PT80382B (en, 2012) |
| SU (1) | SU1375133A3 (en, 2012) |
| YU (1) | YU45714B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9009437D0 (en) * | 1990-04-26 | 1990-06-20 | Glaxo Group Ltd | Chemical compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1565966A (en) * | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
| CH640846A5 (en) * | 1977-07-29 | 1984-01-31 | Allen & Hanburys Ltd | Aminoalkylfuran derivative |
| ES8205211A1 (es) * | 1980-12-05 | 1981-10-16 | Liade Sa Lab | Procedimiento de obtencion de un derivado de amina primaria heterociclica |
| 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 |
| ES506422A0 (es) * | 1981-10-21 | 1982-08-16 | Liade Sa Lab | Procedimiento de obtencion de un derivado heterociclico de dimetilamina y sus sales fisiologicamente aceptables. |
| ES8301226A1 (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. |
-
1984
- 1984-05-02 HU HU841690A patent/HU198196B/hu not_active IP Right Cessation
-
1985
- 1985-04-29 SU SU853885802A patent/SU1375133A3/ru active
- 1985-04-29 MX MX205130A patent/MX161373A/es unknown
- 1985-04-30 NO NO851727A patent/NO168942C/no unknown
- 1985-04-30 YU YU73385A patent/YU45714B/sh unknown
- 1985-04-30 ES ES542782A patent/ES8609292A1/es not_active Expired
- 1985-04-30 CS CS853160A patent/CS259878B2/cs unknown
- 1985-05-01 KR KR1019850002962A patent/KR920005828B1/ko not_active Expired
- 1985-05-02 CA CA000480665A patent/CA1268474A/en not_active Expired
- 1985-05-02 DK DK196785A patent/DK196785A/da not_active Application Discontinuation
- 1985-05-02 GR GR851062A patent/GR851062B/el unknown
- 1985-05-02 IT IT20558/85A patent/IT1200464B/it active
- 1985-05-02 AT AT0129585A patent/AT387573B/de not_active IP Right Cessation
- 1985-05-02 AR AR300258A patent/AR240455A1/es active
- 1985-05-02 PT PT80382A patent/PT80382B/pt not_active IP Right Cessation
- 1985-05-02 FI FI851742A patent/FI88501C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO851727L (no) | 1985-11-04 |
| DK196785A (da) | 1985-11-03 |
| FI851742A0 (fi) | 1985-05-02 |
| IT1200464B (it) | 1989-01-18 |
| SU1375133A3 (ru) | 1988-02-15 |
| FI851742L (fi) | 1985-11-03 |
| DK196785D0 (da) | 1985-05-02 |
| AT387573B (de) | 1989-02-10 |
| NO168942C (no) | 1992-04-22 |
| CA1268474A (en) | 1990-05-01 |
| ATA129585A (de) | 1988-07-15 |
| CS259878B2 (en) | 1988-11-15 |
| GR851062B (en, 2012) | 1985-11-25 |
| PT80382B (pt) | 1987-08-19 |
| AR240455A1 (es) | 1990-04-30 |
| CS316085A2 (en) | 1988-03-15 |
| IT8520558A0 (it) | 1985-05-02 |
| KR920005828B1 (ko) | 1992-07-20 |
| KR850008671A (ko) | 1985-12-21 |
| FI88501C (fi) | 1993-05-25 |
| ES8609292A1 (es) | 1986-08-16 |
| YU73385A (en) | 1987-12-31 |
| NO168942B (no) | 1992-01-13 |
| MX161373A (es) | 1990-09-18 |
| HUT37774A (en) | 1986-02-28 |
| FI88501B (fi) | 1993-02-15 |
| ES542782A0 (es) | 1986-08-16 |
| PT80382A (en) | 1985-06-01 |
| YU45714B (sh) | 1992-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS58150568A (ja) | イミダゾ−ル誘導体の製法 | |
| US2703325A (en) | Preparation of 5-benzyloxytryptamines | |
| HU198196B (en) | Process for production of basic tioether and its salts | |
| JP3003946B2 (ja) | 置換エテンの調製 | |
| JPS58134091A (ja) | ２−アシル−１，３，４，６，７，１１ｂ−ヘキサヒドロ−２Ｈ−ピラジノ−〔２，１−ａ〕−４−イソキノリノン及び中間体の製造方法 | |
| JPH0641463B2 (ja) | チオテトロン酸の製造方法 | |
| JPS62155268A (ja) | ナイザチジンの合成法 | |
| EP0119091B1 (en) | 2,2-diethoxypropionic acid derivatives | |
| EP0104403B1 (en) | New method for the synthesis of 5-thio-1,2,3-thiadiazole | |
| US3433802A (en) | 3-(n-lower-alkylanilino)pyrrolidines | |
| FI63758C (fi) | Foerfarande foer framstaellning av 1-(2-tetrahydrofuryl)-5-fluoruracil | |
| JPS6160673A (ja) | グアニジノチアゾ−ル誘導体の製造法 | |
| JP4004082B2 (ja) | 環状ニトログアニジン誘導体の製造法 | |
| EP0066442B1 (en) | Chemical process | |
| HU182272B (en) | Process for preparing rhanitidine | |
| PL189248B1 (pl) | Sposób wytwarzania 1-(p-metoksybenzoilo)-2-pirolidonu | |
| JPS6272680A (ja) | ラニチジン又はその酸付加塩の製造方法 | |
| JPS62103088A (ja) | ４，５，６，７−テトラヒドロチエノ〔３，２−ｃ〕ピリジン又はその塩の製造方法 | |
| JPS622588B2 (en, 2012) | ||
| KR850000427B1 (ko) | 피롤 유도체의 제조방법 | |
| JPS6225664B2 (en, 2012) | ||
| US4701541A (en) | Medroxalol intermediates | |
| KR820000786B1 (ko) | 우라실 유도체의 제조법 | |
| HU193496B (en) | Process for production of basic tioether and it salts i | |
| JPH0639466B2 (ja) | ウレア誘導体 |
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 |