IE35409L - Penicillamine - Google Patents
PenicillamineInfo
- Publication number
- IE35409L IE35409L IE710829A IE82971A IE35409L IE 35409 L IE35409 L IE 35409L IE 710829 A IE710829 A IE 710829A IE 82971 A IE82971 A IE 82971A IE 35409 L IE35409 L IE 35409L
- Authority
- IE
- Ireland
- Prior art keywords
- penicillamine
- salt
- thiazolidine
- converting
- iii
- Prior art date
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 4
- 229960001639 penicillamine Drugs 0.000 title abstract 4
- 150000003863 ammonium salts Chemical class 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 abstract 2
- PRSDPVKGJUBIAA-UHFFFAOYSA-N 1,3-thiazolidine-4-carbonitrile Chemical compound N#CC1CSCN1 PRSDPVKGJUBIAA-UHFFFAOYSA-N 0.000 abstract 1
- AIOMGEMZFLRFJE-UHFFFAOYSA-N 1,3-thiazolidine-4-carboxamide Chemical compound NC(=O)C1CSCN1 AIOMGEMZFLRFJE-UHFFFAOYSA-N 0.000 abstract 1
- JLLDUMMFTKVTLS-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC(C)C1NC(C(O)=O)C(C)(C)S1 JLLDUMMFTKVTLS-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- -1 aliphatic aldehyde Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 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
- C07D277/08—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
-
- 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)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1346198 Process for penicillamine and its homologues DEUTSCHE GOLD-UND SILBER-SCHEIDEANSTALT 24 June 1971 [3 July 1970 11 May 1971] 29635/71 Heading C2C The invention comprises a process for making penicillamine or a homologue thereof and also salts thereof, by reacting an aliphatic aldehyde, branched on the α-carbon, with sulphur and ammonia to form a #<SP>3</SP>-thiazoline (I), converting (I) by reaction with hydrogen cyanide into a thiazolidine - 4 - carbonitrile (II), converting (II) by mineral acid hydrolysis at below 80‹ C. into a salt of a 4-carbamoylthiazolidine (the free compounds are also described), and thereafter raising the temperature to above 80‹ C. to form a salt of a 4-carboxy-thiazolidine (III) and an ammonium salt (IV); (IV) is removed and (III) or the free acid is hydrolytically degraded to yield the desired product. The following intermediates are also prepared: 2-isopropyl-5,5- dimethylthiazolidine - 4 - carboxylic acid npropyl ester and penicillamine amide hydrochloride; these compounds arise from modifications of the foregoing process.
[GB1346198A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2032952A DE2032952C3 (en) | 1970-07-03 | 1970-07-03 | Process for the preparation of D, L-penicillamine |
| DE19712123232 DE2123232C3 (en) | 1971-05-11 | 1971-05-11 | Process for the preparation of DJ ^ penicillamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35409L true IE35409L (en) | 1972-01-03 |
| IE35409B1 IE35409B1 (en) | 1976-02-04 |
Family
ID=25759383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE829/71A IE35409B1 (en) | 1970-07-03 | 1971-06-29 | Production of penicillamine and its homologues |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS544936B1 (en) |
| AT (2) | AT313864B (en) |
| BE (1) | BE769390A (en) |
| CA (1) | CA949977A (en) |
| CH (1) | CH575388A5 (en) |
| DK (1) | DK145180C (en) |
| ES (1) | ES391971A1 (en) |
| FR (1) | FR2100257A5 (en) |
| GB (1) | GB1346198A (en) |
| IE (1) | IE35409B1 (en) |
| IL (1) | IL37171A (en) |
| IT (1) | IT1035036B (en) |
| NL (1) | NL171891C (en) |
| RO (1) | RO59924A (en) |
| SE (1) | SE395001B (en) |
| SU (1) | SU508207A3 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH540234A (en) * | 1968-09-06 | 1973-08-15 | Degussa | Process for the manufacture of penicillamine |
-
1971
- 1971-06-05 ES ES71391971A patent/ES391971A1/en not_active Expired
- 1971-06-14 DK DK288571A patent/DK145180C/en active
- 1971-06-21 NL NLAANVRAGE7108503,A patent/NL171891C/en not_active IP Right Cessation
- 1971-06-24 GB GB2963571A patent/GB1346198A/en not_active Expired
- 1971-06-25 RO RO67459A patent/RO59924A/ro unknown
- 1971-06-28 IL IL37171A patent/IL37171A/en unknown
- 1971-06-29 IE IE829/71A patent/IE35409B1/en unknown
- 1971-07-01 BE BE769390A patent/BE769390A/en not_active IP Right Cessation
- 1971-07-02 CH CH979471A patent/CH575388A5/xx not_active IP Right Cessation
- 1971-07-02 AT AT576871A patent/AT313864B/en not_active IP Right Cessation
- 1971-07-02 AT AT819973*1A patent/AT322523B/en not_active IP Right Cessation
- 1971-07-02 SU SU1677804A patent/SU508207A3/en active
- 1971-07-02 SE SE7108614A patent/SE395001B/en unknown
- 1971-07-02 IT IT51366/71A patent/IT1035036B/en active
- 1971-07-03 JP JP4917971A patent/JPS544936B1/ja active Pending
- 1971-07-05 CA CA117,354A patent/CA949977A/en not_active Expired
- 1971-07-05 FR FR7124505A patent/FR2100257A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE769390A (en) | 1972-01-03 |
| SU508207A3 (en) | 1976-03-25 |
| IL37171A0 (en) | 1971-08-25 |
| IT1035036B (en) | 1979-10-20 |
| FR2100257A5 (en) | 1972-03-17 |
| IE35409B1 (en) | 1976-02-04 |
| SE395001B (en) | 1977-07-25 |
| CA949977A (en) | 1974-06-25 |
| NL171891B (en) | 1983-01-03 |
| GB1346198A (en) | 1974-02-06 |
| AT313864B (en) | 1974-03-11 |
| NL171891C (en) | 1983-06-01 |
| JPS544936B1 (en) | 1979-03-12 |
| RO59924A (en) | 1976-07-15 |
| CH575388A5 (en) | 1976-05-14 |
| NL7108503A (en) | 1972-01-05 |
| DK145180B (en) | 1982-09-27 |
| ES391971A1 (en) | 1974-05-01 |
| IL37171A (en) | 1974-10-22 |
| AT322523B (en) | 1975-05-26 |
| DK145180C (en) | 1983-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1465229A (en) | Cyclic amino acids | |
| KR870001229A (en) | Process for preparing 7-oxabisi cloheptane substituted diamide and homologous prostaglandin analogs thereof | |
| Gaudry | THE SYNTHESIS OF D, L-α-AMINO-ϵ-HYDROXYCAPROIC ACID AND A NEW SYNTHESIS OF D, L-LYSINE | |
| JPS5767534A (en) | Preparation of alpha,beta-unsaturated carboxylic ester and alpha,beta-unsaturated carboxylic acid | |
| GB1489241A (en) | Use of organophosphonic acid esters and their hydrolysates as anticorrosive coatings and adhesion promoters | |
| GB1262965A (en) | Butyrophenones | |
| GB1268608A (en) | 5-amino-4-aroyl-1,3-dialkylpyrazoles | |
| NO912801L (en) | PROCEDURE FOR THE PREPARATION OF ESTERS AND AMIDES AND CATALYST SYSTEMS FOR THIS. | |
| IE35409L (en) | Penicillamine | |
| US4157342A (en) | Process for preparation of 3-acylamino-4-homoisotwistane | |
| CA1316937C (en) | Preparation of .beta.-alaninediacetic acid or its alkali metal or ammo nium salts | |
| GB1230219A (en) | ||
| EP0054409A1 (en) | Preparation of thiazolidine derivatives | |
| GB1490289A (en) | Intermediates and production thereof for use in the preparation of 6-(2-phenyl-2-(guanylureidoacetamido)acetamido)penicillanic acid | |
| GB1245549A (en) | (thienylideneamino)oxy-alkanoic acid and derivatives thereof | |
| BG43688A3 (en) | METHOD FOR PREPARING DL-BETA-ARYL AMINO ACIDS | |
| JPS5817741B2 (en) | Method for producing α-amino acid amide | |
| GB1387338A (en) | Production of penicillamine and derivatives thereof | |
| IE36829L (en) | Preparation of penicillamine | |
| ES472821A1 (en) | Process for preparing optically active unsubstituted or substituted 2-amino-2-phenyl-acetic acids. | |
| GB1497992A (en) | Production of carboxy-alkane-phosphonic acids and carboxy-alkyl-phosphinic acids | |
| ES8200092A1 (en) | Esters of N-(4'-hydroxyphenyl)acetamide with 5-benzoyl-1-methylpyrrole-2-acetic acids. | |
| ATE2138T1 (en) | PROCESS FOR THE PREPARATION OF SYMMETRIC 1,3-DISUBSTITUTED UREAS. | |
| EP0926135A3 (en) | Processes for producing alpha-aminonitrile derivatives and alpha-amino acids | |
| GB1445668A (en) | Process for obtaining the optical isomers of penicillamine |