ES351168A1 - Un metodo para producir derivados de tiamina. - Google Patents
Un metodo para producir derivados de tiamina.Info
- Publication number
- ES351168A1 ES351168A1 ES351168A ES351168A ES351168A1 ES 351168 A1 ES351168 A1 ES 351168A1 ES 351168 A ES351168 A ES 351168A ES 351168 A ES351168 A ES 351168A ES 351168 A1 ES351168 A1 ES 351168A1
- Authority
- ES
- Spain
- Prior art keywords
- disulphide
- thiamine
- sodium
- obtain thiamine
- ethylthiosulphate
- 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
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 title abstract 22
- 229960003495 thiamine Drugs 0.000 title abstract 22
- 235000019157 thiamine Nutrition 0.000 title abstract 22
- 239000011721 thiamine Substances 0.000 title abstract 22
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 title abstract 20
- 150000002019 disulfides Chemical class 0.000 title 1
- CDRVOBHPRUVIJW-UHFFFAOYSA-N 1,3-dichloro-2-[[(2,6-dichlorophenyl)methyldisulfanyl]methyl]benzene Chemical compound ClC1=CC=CC(Cl)=C1CSSCC1=C(Cl)C=CC=C1Cl CDRVOBHPRUVIJW-UHFFFAOYSA-N 0.000 abstract 4
- NSMBMAITDCNBLF-UHFFFAOYSA-N 1-chloro-2-[[(2-chlorophenyl)methyldisulfanyl]methyl]benzene Chemical compound ClC1=CC=CC=C1CSSCC1=CC=CC=C1Cl NSMBMAITDCNBLF-UHFFFAOYSA-N 0.000 abstract 2
- BECBAQIAXDDXIE-UHFFFAOYSA-M 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride Chemical compound [Cl-].CC1=C(CCO)SC(CCO)=[N+]1CC1=CN=C(C)N=C1N BECBAQIAXDDXIE-UHFFFAOYSA-M 0.000 abstract 2
- SANDDEZKGWNINE-UHFFFAOYSA-M 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl benzoate;chloride Chemical compound [Cl-].S1C=[N+](CC=2C(=NC(C)=NC=2)N)C(C)=C1CCOC(=O)C1=CC=CC=C1 SANDDEZKGWNINE-UHFFFAOYSA-M 0.000 abstract 2
- 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 abstract 2
- OUGQDYANUKKUJN-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CC(C(Cl)=CC=C1)=C1Cl.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CC(C(Cl)=CC=C1)=C1Cl.[Na+].[Na+] OUGQDYANUKKUJN-UHFFFAOYSA-M 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- CETBSQOFQKLHHZ-UHFFFAOYSA-N diethyl disulphide Natural products CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 150000003544 thiamines Chemical class 0.000 abstract 2
- NHTBBVIEMCKTMH-UHFFFAOYSA-N (2-chlorophenyl)methylsulfanyl carbamimidothioate Chemical compound ClC1=C(CSSC(N)=N)C=CC=C1 NHTBBVIEMCKTMH-UHFFFAOYSA-N 0.000 abstract 1
- YWNYPMRWEGWCFK-UHFFFAOYSA-N (3-chlorophenyl)methylsulfanyl carbamimidothioate hydrochloride Chemical compound Cl.ClC=1C=C(CSSC(N)=N)C=CC1 YWNYPMRWEGWCFK-UHFFFAOYSA-N 0.000 abstract 1
- IGIQUNCJQJQRCM-UHFFFAOYSA-N (4-chlorophenyl)methylsulfanyl carbamimidothioate hydrochloride Chemical compound Cl.ClC1=CC=C(CSSC(N)=N)C=C1 IGIQUNCJQJQRCM-UHFFFAOYSA-N 0.000 abstract 1
- DBZBMWDNYRUVMS-UHFFFAOYSA-N (4-chlorophenyl)methylsulfanyl morpholine-4-carbodithioate Chemical compound ClC1=CC=C(CSSC(=S)N2CCOCC2)C=C1 DBZBMWDNYRUVMS-UHFFFAOYSA-N 0.000 abstract 1
- LBDRWFRAVJIWIM-UHFFFAOYSA-N 1,3-dichloro-2-[2-[2-(2,6-dichlorophenyl)ethyldisulfanyl]ethyl]benzene Chemical compound ClC1=C(C(=CC=C1)Cl)CCSSCCC1=C(C=CC=C1Cl)Cl LBDRWFRAVJIWIM-UHFFFAOYSA-N 0.000 abstract 1
- LVOQZTOHAAYJCR-UHFFFAOYSA-N 1-bromo-2-[[(2-bromo-6-chlorophenyl)methyldisulfanyl]methyl]-3-chlorobenzene Chemical compound BrC1=C(CSSCC2=C(C=CC=C2Cl)Br)C(=CC=C1)Cl LVOQZTOHAAYJCR-UHFFFAOYSA-N 0.000 abstract 1
- LHSZDNRBUCVQAB-UHFFFAOYSA-N 1-chloro-2-[(2-chlorophenyl)methylsulfanylmethyl]benzene Chemical compound ClC1=CC=CC=C1CSCC1=CC=CC=C1Cl LHSZDNRBUCVQAB-UHFFFAOYSA-N 0.000 abstract 1
- ZZHYJGCPERVICG-UHFFFAOYSA-N 1-chloro-3-[2-[2-(3-chlorophenyl)ethyldisulfanyl]ethyl]benzene Chemical compound ClC1=CC=CC(CCSSCCC=2C=C(Cl)C=CC=2)=C1 ZZHYJGCPERVICG-UHFFFAOYSA-N 0.000 abstract 1
- VJTHYIKPMULQHG-UHFFFAOYSA-N 1-chloro-3-[[(3-chlorophenyl)methyldisulfanyl]methyl]benzene Chemical compound ClC1=CC=CC(CSSCC=2C=C(Cl)C=CC=2)=C1 VJTHYIKPMULQHG-UHFFFAOYSA-N 0.000 abstract 1
- MTBQUGQTCLLOKD-UHFFFAOYSA-N 1-chloro-4-[2-[2-(4-chlorophenyl)ethyldisulfanyl]ethyl]benzene Chemical compound C1=CC(Cl)=CC=C1CCSSCCC1=CC=C(Cl)C=C1 MTBQUGQTCLLOKD-UHFFFAOYSA-N 0.000 abstract 1
- ANYQNNLRPAIVBO-UHFFFAOYSA-N 1-chloro-4-[[(4-chlorophenyl)methyldisulfanyl]methyl]benzene Chemical compound C1=CC(Cl)=CC=C1CSSCC1=CC=C(Cl)C=C1 ANYQNNLRPAIVBO-UHFFFAOYSA-N 0.000 abstract 1
- FVNQKCWPIPQZGT-UHFFFAOYSA-N 1-fluoro-2-[2-[2-(2-fluorophenyl)ethyldisulfanyl]ethyl]benzene Chemical compound FC1=CC=CC=C1CCSSCCC1=CC=CC=C1F FVNQKCWPIPQZGT-UHFFFAOYSA-N 0.000 abstract 1
- JKPNWQQVFNNOFR-UHFFFAOYSA-N 1-fluoro-2-[[(2-fluorophenyl)methyldisulfanyl]methyl]benzene Chemical compound FC1=CC=CC=C1CSSCC1=CC=CC=C1F JKPNWQQVFNNOFR-UHFFFAOYSA-N 0.000 abstract 1
- AYPVWLXXXMFKCI-UHFFFAOYSA-N 1-fluoro-3-[[(3-fluorophenyl)methyldisulfanyl]methyl]benzene Chemical compound FC1=CC=CC(CSSCC=2C=C(F)C=CC=2)=C1 AYPVWLXXXMFKCI-UHFFFAOYSA-N 0.000 abstract 1
- TVCLHSCUNDIOEP-UHFFFAOYSA-N 1-fluoro-4-[[(4-fluorophenyl)methyldisulfanyl]methyl]benzene Chemical compound C1=CC(F)=CC=C1CSSCC1=CC=C(F)C=C1 TVCLHSCUNDIOEP-UHFFFAOYSA-N 0.000 abstract 1
- ZONAAIMTFOFSID-UHFFFAOYSA-N 1-iodo-2-[[(2-iodophenyl)methyldisulfanyl]methyl]benzene Chemical compound IC1=CC=CC=C1CSSCC1=CC=CC=C1I ZONAAIMTFOFSID-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 1
- DGITXFGOJVFTIN-UHFFFAOYSA-N [O-]S(O)(=O)=[S+]CC(C(Cl)=CC=C1)=C1Cl Chemical compound [O-]S(O)(=O)=[S+]CC(C(Cl)=CC=C1)=C1Cl DGITXFGOJVFTIN-UHFFFAOYSA-N 0.000 abstract 1
- HYZVROFHZSOXQY-UHFFFAOYSA-N [O-]S(O)(=O)=[S+]CC(C=CC=C1)=C1Cl Chemical compound [O-]S(O)(=O)=[S+]CC(C=CC=C1)=C1Cl HYZVROFHZSOXQY-UHFFFAOYSA-N 0.000 abstract 1
- NHUPTELBUJPPJP-UHFFFAOYSA-N [O-]S(O)(=O)=[S+]CC1=CC(F)=CC=C1 Chemical compound [O-]S(O)(=O)=[S+]CC1=CC(F)=CC=C1 NHUPTELBUJPPJP-UHFFFAOYSA-N 0.000 abstract 1
- UIVXPUGGSMCBKV-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CC(C(Cl)=CC=C1)=C1Br.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CC(C(Cl)=CC=C1)=C1Br.[Na+].[Na+] UIVXPUGGSMCBKV-UHFFFAOYSA-M 0.000 abstract 1
- DIBOKWTXCGBEJG-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CC(C=C1)=CC=C1F.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CC(C=C1)=CC=C1F.[Na+].[Na+] DIBOKWTXCGBEJG-UHFFFAOYSA-M 0.000 abstract 1
- QIJNATCMYXXJSL-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CC(C=CC=C1)=C1F.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CC(C=CC=C1)=C1F.[Na+].[Na+] QIJNATCMYXXJSL-UHFFFAOYSA-M 0.000 abstract 1
- LKLVYXKHZFJKQA-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CC(C=CC=C1)=C1I.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CC(C=CC=C1)=C1I.[Na+].[Na+] LKLVYXKHZFJKQA-UHFFFAOYSA-M 0.000 abstract 1
- QXIBFGRZSXPJJU-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CCC(C(Cl)=CC=C1)=C1Cl.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CCC(C(Cl)=CC=C1)=C1Cl.[Na+].[Na+] QXIBFGRZSXPJJU-UHFFFAOYSA-M 0.000 abstract 1
- ANLGNEIQEWRYPD-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CCC(C=C1)=CC=C1Cl.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CCC(C=C1)=CC=C1Cl.[Na+].[Na+] ANLGNEIQEWRYPD-UHFFFAOYSA-M 0.000 abstract 1
- HSQFWTGIVURUDW-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CCC(C=C1)=CC=C1F.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CCC(C=C1)=CC=C1F.[Na+].[Na+] HSQFWTGIVURUDW-UHFFFAOYSA-M 0.000 abstract 1
- XVDDGTSMDYZCDL-UHFFFAOYSA-M [O-]S([O-])(=O)=[S+]CCC1=CC(Cl)=CC=C1.[Na+].[Na+] Chemical compound [O-]S([O-])(=O)=[S+]CCC1=CC(Cl)=CC=C1.[Na+].[Na+] XVDDGTSMDYZCDL-UHFFFAOYSA-M 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Chemical group 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- WUBUHPZTDFJNDA-UHFFFAOYSA-N ethoxy-hydroxy-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound CCOS(O)(=O)=S WUBUHPZTDFJNDA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 239000011630 iodine Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 abstract 1
- 229960000344 thiamine hydrochloride Drugs 0.000 abstract 1
- 235000019190 thiamine hydrochloride Nutrition 0.000 abstract 1
- 239000011747 thiamine hydrochloride Substances 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D415/00—Heterocyclic compounds containing the thiamine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1347567 | 1967-03-03 | ||
| JP3381867 | 1967-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES351168A1 true ES351168A1 (es) | 1969-05-16 |
Family
ID=26349284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES351168A Expired ES351168A1 (es) | 1967-03-03 | 1968-03-02 | Un metodo para producir derivados de tiamina. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3544574A (en, 2012) |
| BE (1) | BE711509A (en, 2012) |
| CH (1) | CH507291A (en, 2012) |
| DE (1) | DE1695924A1 (en, 2012) |
| DK (1) | DK116059B (en, 2012) |
| ES (1) | ES351168A1 (en, 2012) |
| FR (1) | FR7802M (en, 2012) |
| GB (1) | GB1210104A (en, 2012) |
| NL (1) | NL6802936A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992012138A1 (en) * | 1990-12-28 | 1992-07-23 | Takeda Chemical Industries, Ltd. | Process for producing disulfide derivative of thiamine |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833768A (en) * | 1958-05-06 | Compounds with vitamin brlike activity | ||
| US3090785A (en) * | 1963-05-21 | New process for preparing acylated | ||
| DE1620675A1 (de) * | 1966-01-25 | 1970-07-23 | Warner Lambert Pharmaceutical | Verfahren zur Herstellung von S-Benzoyloxymethylthiaminverbindungen |
| DE3321437A1 (de) * | 1983-06-14 | 1984-12-20 | Hilti Ag, Schaan | Kupferlegierungs-lot und kupferlegierung |
-
1968
- 1968-02-29 BE BE711509D patent/BE711509A/xx unknown
- 1968-03-01 NL NL6802936A patent/NL6802936A/xx unknown
- 1968-03-01 FR FR142123A patent/FR7802M/fr not_active Expired
- 1968-03-01 CH CH308868A patent/CH507291A/de not_active IP Right Cessation
- 1968-03-01 DK DK84068AA patent/DK116059B/da unknown
- 1968-03-02 DE DE19681695924 patent/DE1695924A1/de active Pending
- 1968-03-02 ES ES351168A patent/ES351168A1/es not_active Expired
- 1968-03-04 GB GB00487/68A patent/GB1210104A/en not_active Expired
- 1968-03-04 US US709920A patent/US3544574A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL6802936A (en, 2012) | 1968-09-04 |
| DK116059B (da) | 1969-12-08 |
| GB1210104A (en) | 1970-10-28 |
| FR7802M (en, 2012) | 1970-05-11 |
| DE1695924A1 (de) | 1971-05-06 |
| CH507291A (de) | 1971-05-15 |
| US3544574A (en) | 1970-12-01 |
| BE711509A (en, 2012) | 1968-07-01 |
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