GB1346198A - Production of penicillamine and its homologues - Google Patents
Production of penicillamine and its homologuesInfo
- Publication number
- GB1346198A GB1346198A GB2963571A GB2963571A GB1346198A GB 1346198 A GB1346198 A GB 1346198A GB 2963571 A GB2963571 A GB 2963571A GB 2963571 A GB2963571 A GB 2963571A GB 1346198 A GB1346198 A GB 1346198A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillamine
- salt
- thiazolidine
- converting
- iii
- 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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.
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1346198A true GB1346198A (en) | 1974-02-06 |
Family
ID=25759383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2963571A Expired GB1346198A (en) | 1970-07-03 | 1971-06-24 | Production of penicillamine and its homologues |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS544936B1 (en) |
| AT (2) | AT322523B (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 SU SU1677804A patent/SU508207A3/en active
- 1971-07-02 IT IT51366/71A patent/IT1035036B/en active
- 1971-07-02 SE SE7108614A patent/SE395001B/en unknown
- 1971-07-02 AT AT819973*1A patent/AT322523B/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
- 1971-07-03 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 |
|---|---|
| IE35409B1 (en) | 1976-02-04 |
| IL37171A0 (en) | 1971-08-25 |
| AT313864B (en) | 1974-03-11 |
| IL37171A (en) | 1974-10-22 |
| NL171891C (en) | 1983-06-01 |
| IT1035036B (en) | 1979-10-20 |
| ES391971A1 (en) | 1974-05-01 |
| SU508207A3 (en) | 1976-03-25 |
| IE35409L (en) | 1972-01-03 |
| BE769390A (en) | 1972-01-03 |
| RO59924A (en) | 1976-07-15 |
| AT322523B (en) | 1975-05-26 |
| DK145180B (en) | 1982-09-27 |
| SE395001B (en) | 1977-07-25 |
| JPS544936B1 (en) | 1979-03-12 |
| CA949977A (en) | 1974-06-25 |
| FR2100257A5 (en) | 1972-03-17 |
| DK145180C (en) | 1983-02-28 |
| NL7108503A (en) | 1972-01-05 |
| CH575388A5 (en) | 1976-05-14 |
| NL171891B (en) | 1983-01-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |