GB1272866A - Production of penicillamine - Google Patents
Production of penicillamineInfo
- Publication number
- GB1272866A GB1272866A GB42798/69A GB4279869A GB1272866A GB 1272866 A GB1272866 A GB 1272866A GB 42798/69 A GB42798/69 A GB 42798/69A GB 4279869 A GB4279869 A GB 4279869A GB 1272866 A GB1272866 A GB 1272866A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction mixture
- residue
- steam distillation
- optionally
- penicillamine
- 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 3
- 229960001639 penicillamine Drugs 0.000 title abstract 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 6
- 239000011541 reaction mixture Substances 0.000 abstract 6
- 238000001256 steam distillation Methods 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 5
- 238000001704 evaporation Methods 0.000 abstract 5
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 4
- 230000008020 evaporation Effects 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Substances 0.000 abstract 3
- 235000019270 ammonium chloride Nutrition 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000007788 liquid Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 239000007787 solid Substances 0.000 abstract 3
- 239000000126 substance Substances 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- CZDHUFYOXKHLME-UHFFFAOYSA-N 2-amino-3-methyl-3-sulfanylbutanoic acid;hydron;chloride Chemical compound Cl.CC(C)(S)C(N)C(O)=O CZDHUFYOXKHLME-UHFFFAOYSA-N 0.000 abstract 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 abstract 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052737 gold Inorganic materials 0.000 abstract 1
- 239000010931 gold Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- VVNCNSJFMMFHPL-UHFFFAOYSA-N penicillamine Chemical compound CC(C)(S)C(N)C(O)=O VVNCNSJFMMFHPL-UHFFFAOYSA-N 0.000 abstract 1
- 229920001021 polysulfide Polymers 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681795297 DE1795297C3 (de) | 1968-09-06 | Verfahren zur Herstellung von D,L-Penicillamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1272866A true GB1272866A (en) | 1972-05-03 |
Family
ID=5708134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB42798/69A Expired GB1272866A (en) | 1968-09-06 | 1969-08-28 | Production of penicillamine |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE738520A (enrdf_load_stackoverflow) |
| CH (1) | CH540234A (enrdf_load_stackoverflow) |
| FR (1) | FR2017476A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1272866A (enrdf_load_stackoverflow) |
| IL (1) | IL32954A (enrdf_load_stackoverflow) |
| IT (1) | IT1035020B (enrdf_load_stackoverflow) |
| NL (1) | NL169999C (enrdf_load_stackoverflow) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948984A (en) | 1969-09-04 | 1976-04-06 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Process of making penicillamine |
| US4028406A (en) * | 1970-07-03 | 1977-06-07 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Process of preparing penicillamine |
| ES391971A1 (es) * | 1970-07-03 | 1974-05-01 | Degussa | Procedimiento para la preparacion de penicilamina y sus ho-mologos. |
| US4045479A (en) * | 1970-07-03 | 1977-08-30 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Process of preparing penicillamine |
| DE2142336C3 (de) * | 1971-08-24 | 1981-04-09 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Penicillamin und dessen Derivaten durch Ringspaltung von 2-Isopropyl-5,5-dimethylthiazolidinen |
| BE791411R (fr) * | 1971-11-15 | 1973-03-01 | Degussa | Procede de preparation de |
| DE2214814A1 (de) * | 1972-03-25 | 1973-09-27 | Degussa | Zubereitungen, die vollsynthetisch hergestelltes d-penicillamin enthalten |
| HU200177B (en) * | 1985-06-18 | 1990-04-28 | Biogal Gyogyszergyar | Process for producing thiazolidinecarboxylic acids and pharmaceutical compositions comprising such compounds |
-
1969
- 1969-07-31 CH CH1166569A patent/CH540234A/de not_active IP Right Cessation
- 1969-08-20 FR FR6928567A patent/FR2017476A1/fr active Pending
- 1969-08-28 GB GB42798/69A patent/GB1272866A/en not_active Expired
- 1969-08-29 NL NLAANVRAGE6913235,A patent/NL169999C/xx not_active IP Right Cessation
- 1969-09-05 IL IL32954A patent/IL32954A/en unknown
- 1969-09-05 IT IT39855/69A patent/IT1035020B/it active
- 1969-09-05 BE BE738520D patent/BE738520A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH540234A (de) | 1973-08-15 |
| DE1795297A1 (de) | 1972-02-24 |
| FR2017476A1 (enrdf_load_stackoverflow) | 1970-05-22 |
| NL169999C (nl) | 1982-09-16 |
| IL32954A (en) | 1973-02-28 |
| IL32954A0 (en) | 1969-11-30 |
| IT1035020B (it) | 1979-10-20 |
| BE738520A (enrdf_load_stackoverflow) | 1970-02-16 |
| DE1795297B2 (de) | 1976-07-22 |
| NL6913235A (enrdf_load_stackoverflow) | 1970-03-10 |
| NL169999B (nl) | 1982-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |