ES407956A2 - Process for the preparation of penicillamine - Google Patents
Process for the preparation of penicillamineInfo
- Publication number
- ES407956A2 ES407956A2 ES407956A ES407956A ES407956A2 ES 407956 A2 ES407956 A2 ES 407956A2 ES 407956 A ES407956 A ES 407956A ES 407956 A ES407956 A ES 407956A ES 407956 A2 ES407956 A2 ES 407956A2
- Authority
- ES
- Spain
- Prior art keywords
- thiazolidin
- salts
- acids
- carbonitriles
- hydrolysis
- 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
- 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 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 229960001639 penicillamine Drugs 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000003863 ammonium salts Chemical class 0.000 abstract 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 230000009466 transformation Effects 0.000 abstract 2
- AIOMGEMZFLRFJE-UHFFFAOYSA-N 1,3-thiazolidine-4-carboxamide Chemical class NC(=O)C1CSCN1 AIOMGEMZFLRFJE-UHFFFAOYSA-N 0.000 abstract 1
- LTAGPYXZFADOJD-UHFFFAOYSA-N S1CNC(C1)CC(=O)N Chemical class S1CNC(C1)CC(=O)N LTAGPYXZFADOJD-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- -1 aliphatic aldehydes Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical class OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 abstract 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)
Abstract
Improvements introduced in the object of the main patent No. 391,971, applied for on June 5, 1971, by: "Procedure for the preparation of penicillamine and its homologs", by reaction of branched aliphatic aldehydes in the carbon atom in position α with sulfur and ammonia to form thiazolines- Δ, transformation of thiazolines- Δ 3 by anhydrous hydrogen cyanide into thiazolidin-4-carbonitriles, hydrolysis of nitriles under the action of mineral acids, nitriles being transformed first at reduced temperature into salts of thiazolidin-4-carboxamides and subsequently at elevated temperature in thiazolidin-4-carboxylic acid salts and in ammonium salts, treatment of the mixture and separation of ammonium salts, and cleavage by hydrolysis of thiazolidin-4- acids carboxylic acids, characterized in that thiazolidin-4-carbonitriles, for transformation into thiazolidin-4-carboxyamide salts, are u They are used in aqueous hydrochloric acid with at least about 30% by weight of hydrogen chloride content, and temperatures of about 40 to 70ºC are used. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2156601A DE2156601C3 (en) | 1971-11-15 | 1971-11-15 | Process for the production of DX-PeniciUamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES407956A2 true ES407956A2 (en) | 1975-11-01 |
Family
ID=5825136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES407956A Expired ES407956A2 (en) | 1971-11-15 | 1972-10-25 | Process for the preparation of penicillamine |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS566992B2 (en) |
| AU (1) | AU472713B2 (en) |
| BE (1) | BE791411R (en) |
| CH (1) | CH587240A5 (en) |
| CS (1) | CS191252B4 (en) |
| DD (1) | DD101391A6 (en) |
| DE (1) | DE2156601C3 (en) |
| DK (1) | DK145624C (en) |
| EG (1) | EG10782A (en) |
| ES (1) | ES407956A2 (en) |
| FI (1) | FI59398C (en) |
| FR (1) | FR2160483B2 (en) |
| GB (1) | GB1394845A (en) |
| IE (1) | IE36829B1 (en) |
| IL (1) | IL40829A (en) |
| IT (1) | IT1045669B (en) |
| NL (1) | NL175913C (en) |
| NO (1) | NO136193C (en) |
| SE (1) | SE405354B (en) |
| YU (1) | YU39600B (en) |
| ZA (1) | ZA727545B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU715018A3 (en) * | 1976-10-09 | 1980-02-05 | Дегусса (Фирма) | Method of preparing dl-cysteine |
| DE2716476C2 (en) * | 1977-04-14 | 1985-07-11 | Robert Bosch Gmbh, 7000 Stuttgart | Level control device for motor vehicles |
| JPS57195391U (en) * | 1981-06-05 | 1982-12-10 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540234A (en) * | 1968-09-06 | 1973-08-15 | Degussa | Process for the manufacture of penicillamine |
| JPS584587B2 (en) * | 1977-06-14 | 1983-01-27 | 松下電器産業株式会社 | Rotary viscous agent application method and device |
-
0
- BE BE791411D patent/BE791411R/en active
-
1971
- 1971-11-15 DE DE2156601A patent/DE2156601C3/en not_active Expired
- 1971-12-30 SE SE7116964A patent/SE405354B/en unknown
-
1972
- 1972-10-10 NL NLAANVRAGE7213689,A patent/NL175913C/en active Search and Examination
- 1972-10-17 FI FI2867/72A patent/FI59398C/en active
- 1972-10-18 YU YU2599/72A patent/YU39600B/en unknown
- 1972-10-24 ZA ZA727545A patent/ZA727545B/en unknown
- 1972-10-25 ES ES407956A patent/ES407956A2/en not_active Expired
- 1972-10-25 NO NO3846/72A patent/NO136193C/en unknown
- 1972-11-01 GB GB5037572A patent/GB1394845A/en not_active Expired
- 1972-11-10 DK DK559972A patent/DK145624C/en not_active IP Right Cessation
- 1972-11-10 IE IE1537/72A patent/IE36829B1/en unknown
- 1972-11-11 EG EG458/72A patent/EG10782A/en active
- 1972-11-13 CH CH1648372A patent/CH587240A5/xx not_active IP Right Cessation
- 1972-11-13 DD DD166822A patent/DD101391A6/xx unknown
- 1972-11-13 AU AU48812/72A patent/AU472713B2/en not_active Expired
- 1972-11-13 IT IT53994/72A patent/IT1045669B/en active
- 1972-11-14 JP JP11419972A patent/JPS566992B2/ja not_active Expired
- 1972-11-14 CS CS727709A patent/CS191252B4/en unknown
- 1972-11-14 IL IL40829A patent/IL40829A/en unknown
- 1972-11-15 FR FR7240521A patent/FR2160483B2/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EG10782A (en) | 1976-12-31 |
| IL40829A (en) | 1975-06-25 |
| DE2156601A1 (en) | 1973-05-24 |
| JPS566992B2 (en) | 1981-02-14 |
| ZA727545B (en) | 1973-07-25 |
| FR2160483A2 (en) | 1973-06-29 |
| DK145624B (en) | 1983-01-03 |
| DK145624C (en) | 1983-07-11 |
| FI59398B (en) | 1981-04-30 |
| SE405354B (en) | 1978-12-04 |
| DE2156601C3 (en) | 1979-06-07 |
| IT1045669B (en) | 1980-06-10 |
| IE36829L (en) | 1973-05-15 |
| JPS4861421A (en) | 1973-08-28 |
| FR2160483B2 (en) | 1974-08-19 |
| AU4881272A (en) | 1974-05-16 |
| NL7213689A (en) | 1973-05-17 |
| DD101391A6 (en) | 1973-11-12 |
| DE2156601B2 (en) | 1978-10-19 |
| IE36829B1 (en) | 1977-03-02 |
| NO136193B (en) | 1977-04-25 |
| AU472713B2 (en) | 1976-06-03 |
| YU259972A (en) | 1982-06-30 |
| NO136193C (en) | 1977-08-03 |
| CH587240A5 (en) | 1977-04-29 |
| YU39600B (en) | 1985-03-20 |
| GB1394845A (en) | 1975-05-21 |
| NL175913C (en) | 1985-01-16 |
| CS191252B4 (en) | 1979-06-29 |
| BE791411R (en) | 1973-03-01 |
| IL40829A0 (en) | 1973-01-30 |
| FI59398C (en) | 1981-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD2A | Announcement of lapse in spain |
Effective date: 20170704 |