CS259878B2 - Method of additive salt preparation with acid derived from 2(/2-aminoethyl/thiomethyl)-5-dimethylaminomethyl furane - Google Patents
Method of additive salt preparation with acid derived from 2(/2-aminoethyl/thiomethyl)-5-dimethylaminomethyl furane Download PDFInfo
- Publication number
- CS259878B2 CS259878B2 CS853160A CS316085A CS259878B2 CS 259878 B2 CS259878 B2 CS 259878B2 CS 853160 A CS853160 A CS 853160A CS 316085 A CS316085 A CS 316085A CS 259878 B2 CS259878 B2 CS 259878B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- base
- acid addition
- dimethylaminomethyl
- addition salt
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 45
- 239000002253 acid Substances 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims description 18
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 title abstract description 3
- 239000000654 additive Substances 0.000 title 1
- 230000000996 additive effect Effects 0.000 title 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229960003151 mercaptamine Drugs 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000002585 base Substances 0.000 claims description 41
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims description 8
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims description 8
- 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 6
- 239000012458 free base Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 27
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract description 18
- 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 description 5
- 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
- 230000001131 transforming effect Effects 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 4
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 4
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 239000003610 charcoal Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 2
- -1 (5-dimethylaminomethyl) -2-furylmethyl Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NESLOYMMIUOLMU-UHFFFAOYSA-N 1-n'-methyl-2-nitroethene-1,1-diamine Chemical group CNC(N)=C[N+]([O-])=O NESLOYMMIUOLMU-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
- 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
- VCCTWUFHIQYYHA-UHFFFAOYSA-N 2-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]isoindole-1,3-dione Chemical compound O1C(CN(C)C)=CC=C1CSCCN1C(=O)C2=CC=CC=C2C1=O VCCTWUFHIQYYHA-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
- UYDUNGKPTORWBE-UHFFFAOYSA-N 4-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]-1-n'-methyl-2-nitrobut-1-ene-1,1-diamine Chemical group CNC(N)=C([N+]([O-])=O)CCSCC1=CC=C(CN(C)C)O1 UYDUNGKPTORWBE-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011109 contamination 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
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
- 229940099500 cystamine Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000002542 deteriorative effect Effects 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
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- AFDQGRURHDVABZ-UHFFFAOYSA-N n,n-dimethylformamide;sulfur trioxide Chemical compound O=S(=O)=O.CN(C)C=O AFDQGRURHDVABZ-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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)
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 |
|---|---|
| CS316085A2 CS316085A2 (en) | 1988-03-15 |
| CS259878B2 true CS259878B2 (en) | 1988-11-15 |
Family
ID=10955710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Country Status (16)
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 |
| ES8300732A1 (es) * | 1981-06-10 | 1982-11-01 | Lafarquim | Procedimiento para la obtencion de derivados de furil metil mercaptano y sus sales de interes farmacologico |
| ES8206505A1 (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 MX MX205130A patent/MX161373A/es unknown
- 1985-04-29 SU SU853885802A patent/SU1375133A3/ru active
- 1985-04-30 CS CS853160A patent/CS259878B2/cs unknown
- 1985-04-30 NO NO851727A patent/NO168942C/no unknown
- 1985-04-30 ES ES542782A patent/ES8609292A1/es not_active Expired
- 1985-04-30 YU YU73385A patent/YU45714B/sh unknown
- 1985-05-01 KR KR1019850002962A patent/KR920005828B1/ko not_active Expired
- 1985-05-02 DK DK196785A patent/DK196785A/da not_active Application Discontinuation
- 1985-05-02 FI FI851742A patent/FI88501C/fi not_active IP Right Cessation
- 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 GR GR851062A patent/GR851062B/el unknown
- 1985-05-02 CA CA000480665A patent/CA1268474A/en not_active Expired
- 1985-05-02 PT PT80382A patent/PT80382B/pt not_active IP Right Cessation
- 1985-05-02 AR AR300258A patent/AR240455A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| FI88501B (fi) | 1993-02-15 |
| FI88501C (fi) | 1993-05-25 |
| HU198196B (en) | 1989-08-28 |
| AR240455A1 (es) | 1990-04-30 |
| PT80382B (pt) | 1987-08-19 |
| KR920005828B1 (ko) | 1992-07-20 |
| YU73385A (en) | 1987-12-31 |
| DK196785A (da) | 1985-11-03 |
| FI851742L (fi) | 1985-11-03 |
| ES542782A0 (es) | 1986-08-16 |
| DK196785D0 (da) | 1985-05-02 |
| SU1375133A3 (ru) | 1988-02-15 |
| NO168942B (no) | 1992-01-13 |
| HUT37774A (en) | 1986-02-28 |
| ES8609292A1 (es) | 1986-08-16 |
| NO168942C (no) | 1992-04-22 |
| KR850008671A (ko) | 1985-12-21 |
| CA1268474A (en) | 1990-05-01 |
| CS316085A2 (en) | 1988-03-15 |
| GR851062B (enrdf_load_html_response) | 1985-11-25 |
| IT8520558A0 (it) | 1985-05-02 |
| MX161373A (es) | 1990-09-18 |
| IT1200464B (it) | 1989-01-18 |
| NO851727L (no) | 1985-11-04 |
| ATA129585A (de) | 1988-07-15 |
| PT80382A (en) | 1985-06-01 |
| YU45714B (sh) | 1992-07-20 |
| AT387573B (de) | 1989-02-10 |
| FI851742A0 (fi) | 1985-05-02 |
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