EP0019788A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Novel process for the manufacture of thiophene derivatives suited for the manufacture of biotin, process for the manufacture of biotin and novel intermediates in this process
Assignee: F Hoffmann La Roche AG
•
Filing: 1980-05-12
•
Granted: —
•
Expires: 2000-05-12
Abstract
Abstract The invention is concerned with a novel process for the manufacture of novel thiophene derivatives and of biotin, respectively. <??>The process starts from L or DL-cystine esters and proceeds via various novel intermediates, particularly the optically active compounds of the general formulae <CHEM> wherein R<2> is aryl-lower alkyl, R<5> is hydrogen or -COOR<4> and R<4> is lower alkyl, aryl or aryl-lower alkyl, or the corresponding racemates.
Inventors
- 👤 Enrico Giuseppe Baggioline
- 👤 Hsi Lin Lee
- 👤 Milan Radoje Uskokovic
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 18:36
CPC Classifications
C; C07; C07D; C07D495/00; C07D495/02; C07D495/04; C07D281/00; C07D495/08
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
302 words
Process for the manufacture of novel thiophene derivatives and of biotin, respectively, characterized in that a compound of the general formula wherein R 2 is aryl-lower alkyl, is heated at a temperature of from about 50°C to about 200°C in an inert organic solvent, or in that the compound of the formula is heated with an aryl-lower alkyl hydroxylamine at a temperature of from about 80° to about 150°C, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning, is catalytically hydrogenated or treated with zinc powder in a lower alkanoic acid, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning, is acylated, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning and R 4 is lower alkyl, aryl or aryl-lower alkyl, is treated with a base, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning, is esterified, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning and R 6 is lower alkyl or aryl-lower alkyl, is halogenated, that, if desired, a so obtained compound of the general formula wherein R 2 and R 6 have the above meanings and X is halogen, is treated with a non- nucleophilic organic base, that, if desired, a so obtained compound of the general formula wherein R 2 and R 6 have the above meanings, is catalytically hydrogenated, with or without previous saponification, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning and R '6 is hydrogen, lower alkyl or aryl-lower alkyl, is converted into biotin according to methods known per se.
Claim 2
Dependent Claim
302 words
Process for the manufacture of novel thiophene derivatives and of biotin, respectively, characterized in that a compound of the general formula wherein R 2 is aryl-lower alkyl, is heated at a temperature of from about 50°C to about 200°C in an inert organic solvent, or in that the compound of the formula is heated with an aryl-lower alkyl hydroxylamine at a temperature of from about 80° to about 150°C, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning, is catalytically hydrogenated or treated with zinc powder in a lower alkanoic acid, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning, is acylated, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning and R 4 is lower alkyl, aryl or aryl-lower alkyl, is treated with a base, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning, is esterified, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning and R 6 is lower alkyl or aryl-lower alkyl, is halogenated, that, if desired, a so obtained compound of the general formula wherein R 2 and R 6 have the above meanings and X is halogen, is treated with a non- nucleophilic organic base, that, if desired, a so obtained compound of the general formula wherein R 2 and R 6 have the above meanings, is catalytically hydrogenated, with or without previous saponification, that, if desired, a so obtained compound of the general formula wherein R 2 has the above meaning and R '6 is hydrogen, lower alkyl or aryl-lower alkyl, is converted into biotin according to methods known per se.
Claim 3
Dependent Claim
17 words
Optically active compounds of the general formula wherein R 2 is aryl-lower alkyl, and the racemates thereof.
Claim 4
Dependent Claim
17 words
Optically active compounds of the general formula wherein R 2 is aryl-lower alkyl, and the racemates thereof.
Claim 5
Dependent Claim
11 words
A compound according to claim 2, wherein R 2 is benzyl.
Claim 6
Dependent Claim
35 words
Optically active compounds of the general formula wherein R 2 is aryl-lower alkyl, R 5 is hydrogen or - COOR 4 and R 4 is lower alkyl, aryl or aryl-lower alkyl, and the racemates thereof.
Claim 7
Dependent Claim
35 words
Optically active compounds of the general formula wherein R 2 is aryl-lower alkyl, R 5 is hydrogen or - COOR 4 and R 4 is lower alkyl, aryl or aryl-lower alkyl, and the racemates thereof.
Claim 8
Dependent Claim
11 words
A compound according to claim 4, wherein R 5 is hydrogen.
Claim 9
Dependent Claim
13 words
A compound according to claim 4 or 5, wherein R 2 is benzyl.
Claim 10
Dependent Claim
21 words
Compounds according to claim 4, wherein R 5 is -COOR 4 and R 4 is lower alkyl, aryl or aryl-lower alkyl.
Claim 11
Dependent Claim
18 words
A compound according to claim 4 or 7, wherein R 2 is benzyl and R 4 is methyl.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
Maintenance schedule is calculated for granted US utility patents.