CA1268474A - Process for preparing a basic thioether and the salts thereof - Google Patents
Process for preparing a basic thioether and the salts thereofInfo
- Publication number
- CA1268474A CA1268474A CA000480665A CA480665A CA1268474A CA 1268474 A CA1268474 A CA 1268474A CA 000480665 A CA000480665 A CA 000480665A CA 480665 A CA480665 A CA 480665A CA 1268474 A CA1268474 A CA 1268474A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- base
- acid addition
- addition salt
- iii
- 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
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 150000003568 thioethers Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 56
- 239000002253 acid Substances 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 28
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229960003151 mercaptamine Drugs 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 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 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 claims description 4
- 229940097265 cysteamine hydrochloride Drugs 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 2
- GAGYFOWVLJNTNY-UHFFFAOYSA-N 1-[5-(dimethylamino)furan-2-yl]ethyl hydrogen sulfate Chemical compound S(=O)(=O)(OC(C=1OC(=CC1)N(C)C)C)O GAGYFOWVLJNTNY-UHFFFAOYSA-N 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 3
- 208000007107 Stomach Ulcer Diseases 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 208000000718 duodenal ulcer Diseases 0.000 abstract description 2
- 230000002496 gastric effect Effects 0.000 abstract description 2
- HDRWLVCQWZUDSF-UHFFFAOYSA-N 5-(2-aminoethylsulfanylmethyl)-n,n,4-trimethylfuran-2-amine Chemical class CN(C)C1=CC(C)=C(CSCCN)O1 HDRWLVCQWZUDSF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 description 51
- 238000007792 addition Methods 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000003756 stirring Methods 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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- -1 5-dimethylaminomethyl-2-furylmethyl Chemical group 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001914 filtration Methods 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
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 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
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VJEZYZLITKUTFH-UHFFFAOYSA-N 2-(hydrazinecarbonyl)benzoic acid Chemical compound NNC(=O)C1=CC=CC=C1C(O)=O VJEZYZLITKUTFH-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 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
- 239000002274 desiccant Substances 0.000 description 1
- 230000006866 deterioration 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
- 230000003292 diminished effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 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
- 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
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- FZUJWWOKDIGOKH-UHFFFAOYSA-N sulfuric acid hydrochloride Chemical compound Cl.OS(O)(=O)=O FZUJWWOKDIGOKH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005303 weighing 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1690/84 | 1984-05-02 | ||
| HU841690A HU198196B (en) | 1984-05-02 | 1984-05-02 | Process for production of basic tioether and its salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1268474A true CA1268474A (en) | 1990-05-01 |
Family
ID=10955710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000480665A Expired CA1268474A (en) | 1984-05-02 | 1985-05-02 | Process for preparing a basic thioether and the salts thereof |
Country Status (16)
| Country | Link |
|---|---|
| KR (1) | KR920005828B1 (fi) |
| AR (1) | AR240455A1 (fi) |
| AT (1) | AT387573B (fi) |
| CA (1) | CA1268474A (fi) |
| CS (1) | CS259878B2 (fi) |
| DK (1) | DK196785A (fi) |
| ES (1) | ES8609292A1 (fi) |
| FI (1) | FI88501C (fi) |
| GR (1) | GR851062B (fi) |
| HU (1) | HU198196B (fi) |
| IT (1) | IT1200464B (fi) |
| MX (1) | MX161373A (fi) |
| NO (1) | NO168942C (fi) |
| PT (1) | PT80382B (fi) |
| SU (1) | SU1375133A3 (fi) |
| YU (1) | YU45714B (fi) |
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 |
| 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 SU SU853885802A patent/SU1375133A3/ru active
- 1985-04-29 MX MX205130A patent/MX161373A/es unknown
- 1985-04-30 ES ES542782A patent/ES8609292A1/es not_active Expired
- 1985-04-30 NO NO851727A patent/NO168942C/no unknown
- 1985-04-30 CS CS853160A patent/CS259878B2/cs unknown
- 1985-04-30 YU YU73385A patent/YU45714B/sh unknown
- 1985-05-01 KR KR1019850002962A patent/KR920005828B1/ko not_active IP Right Cessation
- 1985-05-02 DK DK196785A patent/DK196785A/da not_active Application Discontinuation
- 1985-05-02 AR AR300258A patent/AR240455A1/es active
- 1985-05-02 AT AT0129585A patent/AT387573B/de not_active IP Right Cessation
- 1985-05-02 IT IT20558/85A patent/IT1200464B/it active
- 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 FI FI851742A patent/FI88501C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU45714B (sh) | 1992-07-20 |
| KR850008671A (ko) | 1985-12-21 |
| ES8609292A1 (es) | 1986-08-16 |
| NO168942B (no) | 1992-01-13 |
| IT8520558A0 (it) | 1985-05-02 |
| AR240455A1 (es) | 1990-04-30 |
| HU198196B (en) | 1989-08-28 |
| YU73385A (en) | 1987-12-31 |
| FI851742A0 (fi) | 1985-05-02 |
| PT80382A (en) | 1985-06-01 |
| DK196785D0 (da) | 1985-05-02 |
| NO168942C (no) | 1992-04-22 |
| GR851062B (fi) | 1985-11-25 |
| CS259878B2 (en) | 1988-11-15 |
| ES542782A0 (es) | 1986-08-16 |
| FI88501B (fi) | 1993-02-15 |
| ATA129585A (de) | 1988-07-15 |
| DK196785A (da) | 1985-11-03 |
| IT1200464B (it) | 1989-01-18 |
| PT80382B (pt) | 1987-08-19 |
| FI88501C (fi) | 1993-05-25 |
| MX161373A (es) | 1990-09-18 |
| SU1375133A3 (ru) | 1988-02-15 |
| HUT37774A (en) | 1986-02-28 |
| NO851727L (no) | 1985-11-04 |
| AT387573B (de) | 1989-02-10 |
| FI851742L (fi) | 1985-11-03 |
| KR920005828B1 (ko) | 1992-07-20 |
| CS316085A2 (en) | 1988-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |