SU501669A3 - Способ получени -пеницилламина - Google Patents
Способ получени -пеницилламинаInfo
- Publication number
- SU501669A3 SU501669A3 SU1806149A SU1806149A SU501669A3 SU 501669 A3 SU501669 A3 SU 501669A3 SU 1806149 A SU1806149 A SU 1806149A SU 1806149 A SU1806149 A SU 1806149A SU 501669 A3 SU501669 A3 SU 501669A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- penicillamine
- mol
- derivative
- cleavage
- salt
- Prior art date
Links
- 229960001639 penicillamine Drugs 0.000 title description 4
- 238000000034 method Methods 0.000 title description 3
- 150000003839 salts Chemical class 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000003776 cleavage reaction Methods 0.000 description 7
- 230000007017 scission Effects 0.000 description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229960000395 phenylpropanolamine Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002244 precipitate 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 class 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VVNCNSJFMMFHPL-GSVOUGTGSA-N L-penicillamine Chemical class CC(C)(S)[C@H](N)C(O)=O VVNCNSJFMMFHPL-GSVOUGTGSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000000468 ketone group Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Peptides Or Proteins (AREA)
- Tires In General (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2138122A DE2138122C3 (de) | 1971-07-30 | 1971-07-30 | Verfahren zur Gewinnung von D-Penicillamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU501669A3 true SU501669A3 (ru) | 1976-01-30 |
Family
ID=5815277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1806149A SU501669A3 (ru) | 1971-07-30 | 1972-06-30 | Способ получени -пеницилламина |
Country Status (27)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2182892B1 (enrdf_load_stackoverflow) * | 1972-03-25 | 1976-11-05 | Degussa | |
| DE2304055C3 (de) * | 1973-01-27 | 1982-04-29 | Degussa Ag, 6000 Frankfurt | Verfahren zur Gewinnung von D- Penicillamin |
| DE2362687C3 (de) * | 1973-12-17 | 1982-01-14 | Degussa Ag, 6000 Frankfurt | Verfahren zur Gewinnung der optischen Isomeren des Penicillamins |
| US4075219A (en) * | 1977-03-31 | 1978-02-21 | Eli Lilly And Company | Epimerization process |
| DE3134106A1 (de) * | 1981-08-28 | 1983-03-17 | Degussa Ag, 6000 Frankfurt | Verfahren zur trennung des racemats s-(carboxymethyl)-(r,s)-cystein (b) |
| DE3134042A1 (de) * | 1981-08-28 | 1983-03-10 | Degussa Ag, 6000 Frankfurt | Verfahren zur trennung des racemats s-(carboxymethyl)-(r,s)-cystein (a) |
-
0
- BE BE786964D patent/BE786964A/xx not_active IP Right Cessation
-
1971
- 1971-07-30 DE DE2138122A patent/DE2138122C3/de not_active Expired
-
1972
- 1972-05-10 ES ES402609A patent/ES402609A1/es not_active Expired
- 1972-05-16 RO RO7270911A patent/RO70841A/ro unknown
- 1972-05-17 FI FI1403/72A patent/FI56527C/fi active
- 1972-05-22 ZA ZA723486A patent/ZA723486B/xx unknown
- 1972-05-25 DD DD163190A patent/DD98093A5/xx unknown
- 1972-06-06 DK DK280972A patent/DK145780C/da active
- 1972-06-16 NO NO2163/72A patent/NO135903C/no unknown
- 1972-06-20 EG EG269/72A patent/EG10792A/xx active
- 1972-06-22 CS CS7200004425A patent/CS183662B2/cs unknown
- 1972-06-30 NL NL7209189.A patent/NL165153C/xx not_active IP Right Cessation
- 1972-06-30 SU SU1806149A patent/SU501669A3/ru active
- 1972-07-07 YU YU1514/72A patent/YU36016B/xx unknown
- 1972-07-13 GB GB3272672A patent/GB1394855A/en not_active Expired
- 1972-07-17 CH CH1064972A patent/CH580044A5/xx not_active IP Right Cessation
- 1972-07-20 IE IE1016/72A patent/IE36577B1/xx unknown
- 1972-07-21 IL IL39963A patent/IL39963A/xx unknown
- 1972-07-27 FR FR7227091A patent/FR2148050B1/fr not_active Expired
- 1972-07-27 AR AR243308A patent/AR196077A1/es active
- 1972-07-27 AT AT647072A patent/AT320607B/de not_active IP Right Cessation
- 1972-07-28 SE SE7209900A patent/SE383739B/xx unknown
- 1972-07-28 BR BR5067/72A patent/BR7205067D0/pt unknown
- 1972-07-28 CA CA148,203A patent/CA979924A/en not_active Expired
- 1972-07-28 IT IT51845/72A patent/IT1059660B/it active
- 1972-07-28 AU AU45107/72A patent/AU465833B2/en not_active Expired
- 1972-07-31 JP JP7684772A patent/JPS544937B1/ja active Pending
-
1973
- 1973-10-03 YU YU2593/73A patent/YU36017B/xx unknown
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