FI59399C - Foerfarande foer framstaellning av penicillamin och dess homologer - Google Patents
Foerfarande foer framstaellning av penicillamin och dess homologer Download PDFInfo
- Publication number
- FI59399C FI59399C FI3007/72A FI300772A FI59399C FI 59399 C FI59399 C FI 59399C FI 3007/72 A FI3007/72 A FI 3007/72A FI 300772 A FI300772 A FI 300772A FI 59399 C FI59399 C FI 59399C
- Authority
- FI
- Finland
- Prior art keywords
- acid
- penicillamine
- weight
- hydrochloric acid
- homologer
- 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 claims description 36
- 239000002253 acid Substances 0.000 claims description 20
- 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 claims description 16
- 229960001639 penicillamine Drugs 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000003548 thiazolidines Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CZDHUFYOXKHLME-DFWYDOINSA-N (2s)-2-amino-3-methyl-3-sulfanylbutanoic acid;hydrochloride Chemical compound Cl.CC(C)(S)[C@@H](N)C(O)=O CZDHUFYOXKHLME-DFWYDOINSA-N 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- -1 diethyl ether Chemical compound 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- VVNCNSJFMMFHPL-UHFFFAOYSA-N penicillamine Chemical compound CC(C)(S)C(N)C(O)=O VVNCNSJFMMFHPL-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003549 thiazolines Chemical class 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
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2163810A DE2163810C3 (de) | 1971-12-22 | 1971-12-22 | Verfahren zur Herstellung von Penicillamin und dessen Homologen |
| DE2163810 | 1971-12-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59399B FI59399B (fi) | 1981-04-30 |
| FI59399C true FI59399C (fi) | 1981-08-10 |
Family
ID=5828848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3007/72A FI59399C (fi) | 1971-12-22 | 1972-10-30 | Foerfarande foer framstaellning av penicillamin och dess homologer |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3946069A (es) |
| JP (1) | JPS5331132B2 (es) |
| AR (1) | AR205784A1 (es) |
| AT (1) | AT318555B (es) |
| BE (1) | BE793165A (es) |
| BR (1) | BR7208980D0 (es) |
| CA (1) | CA966854A (es) |
| CH (1) | CH575918A5 (es) |
| CS (1) | CS190379B2 (es) |
| DD (1) | DD100465A5 (es) |
| DE (1) | DE2163810C3 (es) |
| DK (1) | DK140936C (es) |
| EG (1) | EG10700A (es) |
| ES (1) | ES408183A1 (es) |
| FI (1) | FI59399C (es) |
| FR (1) | FR2165664A5 (es) |
| GB (1) | GB1380368A (es) |
| IE (1) | IE36982B1 (es) |
| IL (1) | IL41150A (es) |
| NL (1) | NL170628C (es) |
| NO (1) | NO137090C (es) |
| RO (1) | RO62764A (es) |
| SE (1) | SE397522B (es) |
| SU (1) | SU516348A3 (es) |
| YU (1) | YU36302B (es) |
| ZA (1) | ZA727939B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061674A (en) * | 1971-12-22 | 1977-12-06 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Process of making penicillamine |
| IT1143608B (it) * | 1976-10-09 | 1986-10-22 | Degussa | Procedimento per la produzione di tiazolidin-4-carbonitrili e loro conversione in d,l-cisteina |
| DE3607167A1 (de) * | 1986-03-05 | 1987-09-10 | Degussa | Verfahren zur ringspaltung von in 4-stellung substituierten 2-isopropyl-5,5-dimethylthiazolidinen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666770A (en) * | 1970-01-27 | 1972-05-30 | Sterling Drug Inc | Process for preparing d-5,5-dimethyl-{66 {11 -thiazoline-4-carboxylic derivatives |
-
0
- BE BE793165D patent/BE793165A/xx not_active IP Right Cessation
-
1971
- 1971-12-22 DE DE2163810A patent/DE2163810C3/de not_active Expired
-
1972
- 1972-01-01 AR AR245652A patent/AR205784A1/es active
- 1972-10-26 SU SU1840863A patent/SU516348A3/ru active
- 1972-10-30 FI FI3007/72A patent/FI59399C/fi active
- 1972-10-30 NL NLAANVRAGE7214677,A patent/NL170628C/xx not_active IP Right Cessation
- 1972-11-01 NO NO3952/72A patent/NO137090C/no unknown
- 1972-11-02 ES ES408183A patent/ES408183A1/es not_active Expired
- 1972-11-09 ZA ZA727939A patent/ZA727939B/xx unknown
- 1972-11-14 DD DD166842A patent/DD100465A5/xx unknown
- 1972-11-23 CH CH1704472A patent/CH575918A5/xx not_active IP Right Cessation
- 1972-11-28 YU YU2972/72A patent/YU36302B/xx unknown
- 1972-11-28 GB GB5496672A patent/GB1380368A/en not_active Expired
- 1972-12-04 IE IE1683/72A patent/IE36982B1/xx unknown
- 1972-12-06 CS CS728342A patent/CS190379B2/cs unknown
- 1972-12-09 EG EG506/72A patent/EG10700A/xx active
- 1972-12-19 RO RO7200073210A patent/RO62764A/ro unknown
- 1972-12-20 US US05/317,403 patent/US3946069A/en not_active Expired - Lifetime
- 1972-12-20 AT AT1088872A patent/AT318555B/de not_active IP Right Cessation
- 1972-12-20 BR BR8980/72A patent/BR7208980D0/pt unknown
- 1972-12-20 DK DK637172A patent/DK140936C/da not_active IP Right Cessation
- 1972-12-20 JP JP12805172A patent/JPS5331132B2/ja not_active Expired
- 1972-12-21 CA CA159,703A patent/CA966854A/en not_active Expired
- 1972-12-21 SE SE7216834A patent/SE397522B/xx unknown
- 1972-12-22 IL IL41150A patent/IL41150A/xx unknown
- 1972-12-22 FR FR7245863A patent/FR2165664A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2165664A5 (es) | 1973-08-03 |
| IL41150A0 (en) | 1973-02-28 |
| DE2163810C3 (de) | 1979-04-26 |
| NL170628B (nl) | 1982-07-01 |
| GB1380368A (en) | 1975-01-15 |
| IL41150A (en) | 1975-04-25 |
| FI59399B (fi) | 1981-04-30 |
| CS190379B2 (en) | 1979-05-31 |
| YU36302B (en) | 1982-06-18 |
| JPS5331132B2 (es) | 1978-08-31 |
| CA966854A (en) | 1975-04-29 |
| AT318555B (de) | 1974-10-25 |
| SE397522B (sv) | 1977-11-07 |
| DD100465A5 (es) | 1973-09-20 |
| YU297272A (en) | 1981-08-31 |
| JPS4868522A (es) | 1973-09-18 |
| ZA727939B (en) | 1973-07-25 |
| RO62764A (fr) | 1977-10-15 |
| AR205784A1 (es) | 1976-06-07 |
| CH575918A5 (es) | 1976-05-31 |
| DK140936C (da) | 1980-05-19 |
| NO137090B (no) | 1977-09-19 |
| US3946069A (en) | 1976-03-23 |
| EG10700A (en) | 1976-05-31 |
| IE36982B1 (en) | 1977-04-13 |
| NO137090C (no) | 1977-12-28 |
| ES408183A1 (es) | 1975-11-01 |
| IE36982L (en) | 1973-06-22 |
| DE2163810B2 (de) | 1978-08-31 |
| SU516348A3 (ru) | 1976-05-30 |
| DE2163810A1 (de) | 1973-07-26 |
| BR7208980D0 (pt) | 1973-09-25 |
| BE793165A (fr) | 1973-04-16 |
| NL170628C (nl) | 1982-12-01 |
| DK140936B (da) | 1979-12-10 |
| NL7214677A (es) | 1973-06-26 |
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