FI59398C - Foerfarande foer framstaellning av penicillamin och dess homologer - Google Patents
Foerfarande foer framstaellning av penicillamin och dess homologer Download PDFInfo
- Publication number
- FI59398C FI59398C FI2867/72A FI286772A FI59398C FI 59398 C FI59398 C FI 59398C FI 2867/72 A FI2867/72 A FI 2867/72A FI 286772 A FI286772 A FI 286772A FI 59398 C FI59398 C FI 59398C
- Authority
- FI
- Finland
- Prior art keywords
- isopropyl
- thiazolidine
- temperature
- reaction mixture
- dimethylthiazolidine
- Prior art date
Links
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 18
- 150000002825 nitriles Chemical class 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- -1 brine amine Chemical class 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000005521 carbonamide group Chemical group 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 2
- QMUBCEKNQQFXAP-UHFFFAOYSA-N 1,3-thiazolidin-3-ium-3-carboxylate Chemical class OC(=O)N1CCSC1 QMUBCEKNQQFXAP-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229960001639 penicillamine Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UEHKBJZDQOQOLX-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-1,3-thiazolidine Chemical compound CC(C)C1NCC(C)(C)S1 UEHKBJZDQOQOLX-UHFFFAOYSA-N 0.000 description 1
- HHQSUSGDCHSDTO-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-4h-1,3-thiazole Chemical compound CC(C)C1=NCC(C)(C)S1 HHQSUSGDCHSDTO-UHFFFAOYSA-N 0.000 description 1
- VEKORHIUCKLURX-UHFFFAOYSA-N C(C)(C)C1(SC(CN1)(C)C)C#N Chemical compound C(C)(C)C1(SC(CN1)(C)C)C#N VEKORHIUCKLURX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2156601A DE2156601C3 (de) | 1971-11-15 | 1971-11-15 | Verfahren zur Herstellung von DX-PeniciUamin |
| DE2156601 | 1971-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59398B FI59398B (fi) | 1981-04-30 |
| FI59398C true FI59398C (fi) | 1981-08-10 |
Family
ID=5825136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2867/72A FI59398C (fi) | 1971-11-15 | 1972-10-17 | Foerfarande foer framstaellning av penicillamin och dess homologer |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS566992B2 (cs) |
| AU (1) | AU472713B2 (cs) |
| BE (1) | BE791411R (cs) |
| CH (1) | CH587240A5 (cs) |
| CS (1) | CS191252B4 (cs) |
| DD (1) | DD101391A6 (cs) |
| DE (1) | DE2156601C3 (cs) |
| DK (1) | DK145624C (cs) |
| EG (1) | EG10782A (cs) |
| ES (1) | ES407956A2 (cs) |
| FI (1) | FI59398C (cs) |
| FR (1) | FR2160483B2 (cs) |
| GB (1) | GB1394845A (cs) |
| IE (1) | IE36829B1 (cs) |
| IL (1) | IL40829A (cs) |
| IT (1) | IT1045669B (cs) |
| NL (1) | NL175913C (cs) |
| NO (1) | NO136193C (cs) |
| SE (1) | SE405354B (cs) |
| YU (1) | YU39600B (cs) |
| ZA (1) | ZA727545B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1143608B (it) * | 1976-10-09 | 1986-10-22 | Degussa | Procedimento per la produzione di tiazolidin-4-carbonitrili e loro conversione in d,l-cisteina |
| DE2716476C2 (de) * | 1977-04-14 | 1985-07-11 | Robert Bosch Gmbh, 7000 Stuttgart | Niveauregeleinrichtung für Kraftfahrzeuge |
| JPS57195391U (cs) * | 1981-06-05 | 1982-12-10 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540234A (de) * | 1968-09-06 | 1973-08-15 | Degussa | Verfahren zur Herstellung von Penicillamin |
| JPS584587B2 (ja) * | 1977-06-14 | 1983-01-27 | 松下電器産業株式会社 | 回転式粘性剤塗布方法およびその装置 |
-
0
- BE BE791411D patent/BE791411R/xx active
-
1971
- 1971-11-15 DE DE2156601A patent/DE2156601C3/de not_active Expired
- 1971-12-30 SE SE7116964A patent/SE405354B/xx unknown
-
1972
- 1972-10-10 NL NLAANVRAGE7213689,A patent/NL175913C/xx active Search and Examination
- 1972-10-17 FI FI2867/72A patent/FI59398C/fi active
- 1972-10-18 YU YU2599/72A patent/YU39600B/xx unknown
- 1972-10-24 ZA ZA727545A patent/ZA727545B/xx unknown
- 1972-10-25 NO NO3846/72A patent/NO136193C/no unknown
- 1972-10-25 ES ES407956A patent/ES407956A2/es not_active Expired
- 1972-11-01 GB GB5037572A patent/GB1394845A/en not_active Expired
- 1972-11-10 DK DK559972A patent/DK145624C/da not_active IP Right Cessation
- 1972-11-10 IE IE1537/72A patent/IE36829B1/xx unknown
- 1972-11-11 EG EG458/72A patent/EG10782A/xx active
- 1972-11-13 CH CH1648372A patent/CH587240A5/xx not_active IP Right Cessation
- 1972-11-13 AU AU48812/72A patent/AU472713B2/en not_active Expired
- 1972-11-13 DD DD166822A patent/DD101391A6/xx unknown
- 1972-11-13 IT IT53994/72A patent/IT1045669B/it active
- 1972-11-14 JP JP11419972A patent/JPS566992B2/ja not_active Expired
- 1972-11-14 CS CS727709A patent/CS191252B4/cs unknown
- 1972-11-14 IL IL40829A patent/IL40829A/xx unknown
- 1972-11-15 FR FR7240521A patent/FR2160483B2/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO136193B (cs) | 1977-04-25 |
| ES407956A2 (es) | 1975-11-01 |
| IE36829B1 (en) | 1977-03-02 |
| CH587240A5 (cs) | 1977-04-29 |
| NL175913C (nl) | 1985-01-16 |
| JPS4861421A (cs) | 1973-08-28 |
| FR2160483B2 (cs) | 1974-08-19 |
| NL7213689A (cs) | 1973-05-17 |
| DK145624C (da) | 1983-07-11 |
| IL40829A0 (en) | 1973-01-30 |
| IE36829L (en) | 1973-05-15 |
| IT1045669B (it) | 1980-06-10 |
| JPS566992B2 (cs) | 1981-02-14 |
| FR2160483A2 (cs) | 1973-06-29 |
| EG10782A (en) | 1976-12-31 |
| AU4881272A (en) | 1974-05-16 |
| ZA727545B (en) | 1973-07-25 |
| FI59398B (fi) | 1981-04-30 |
| AU472713B2 (en) | 1976-06-03 |
| NO136193C (no) | 1977-08-03 |
| DE2156601A1 (de) | 1973-05-24 |
| CS191252B4 (en) | 1979-06-29 |
| SE405354B (sv) | 1978-12-04 |
| BE791411R (fr) | 1973-03-01 |
| DE2156601B2 (de) | 1978-10-19 |
| DE2156601C3 (de) | 1979-06-07 |
| IL40829A (en) | 1975-06-25 |
| GB1394845A (en) | 1975-05-21 |
| YU39600B (en) | 1985-03-20 |
| DD101391A6 (cs) | 1973-11-12 |
| DK145624B (da) | 1983-01-03 |
| YU259972A (en) | 1982-06-30 |
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