72821-79-5Relevant articles and documents
Synthesis of European pharmacopoeial impurities A, B, C, and D of cabergoline
Wagger, Jernej,Pozes, Aljaz,Pozgan, Franc
, p. 23146 - 23156 (2013/11/19)
For the use of analytics, European pharmacopoeial impurities A, B, C, and D of cabergoline were synthesized. Ergocryptine was chosen as a starting material and synthesis was accomplished via two approaches, different in length and stereochemical outcome. A longer, indirect approach was realized through otherwise problematic oxidations of the 9,10-dihidrolysergol derivative, to the corresponding aldehyde and carboxylic acid. This was achieved by the use of activated DMSO and a Pinnick oxidation sequence. All four synthesized impurities are used as analytical standards in cabergoline manufacturing processes.
Synthesis of novel analogs of cabergoline: Improving cardiovascular safety by removing 5-HT2B receptor agonism
Dosa, Peter I.,Ward, Tim,Walters, Michael A.,Kim, Suck Won
, p. 254 - 258 (2013/04/10)
The dopamine agonist cabergoline has been used to treat prolactinomas, Parkinson's disease, Cushing's disease, and sexual dysfunction. However, its clinical use was severely curtailed when it was found that patients taking cabergoline had an increased risk of developing cardiac-valve regurgitation. This potentially life-threatening condition has been associated with drugs, such as cabergoline, that are 5-HT2B receptor agonists. We prepared analogs of cabergoline and have identified several that have limited or no agonism at the 5-HT2B receptor.
New and efficient process for the preperation of cabergoline and its intermediates
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Page/Page column 13, (2008/12/08)
This invention relates to a new and efficient process for the production of dopamine agonists such as Cabergoline and the intermediates thereof.
EPIMERIZATION OF ESTERS OF STEREOISOMERIC 8-ERGOLINECARBOXYLIC ACIDS ON CARBON C(8)
Benes, Jan,Cerny, Antonin,Miller, Vladimir,Kudrnac, Stanislav
, p. 1333 - 1340 (2007/10/02)
Esters of 8β-ergolinecarboxylic acids, I-XI, exposed to strong bases, such as lithium diisopropylamide, in polar aprotic solvents gave enolates, which were decomposed by suitable proton donors to a mixture of epimers.This contained, apart from the starting 8β-esters, the corresponding 8α-esters, Ia-IVa and VIa-XIa (65-80percent) and Va (about 16percent).Exposure of 8α-ester XIIa to these conditions produced epimerization on C(8) (about 54percent) and, to a small extent, isomerization on C(10), affording ester I(c. 1percent) and Ia (c. 5percent).
Antihypertensive ergolinepropionamides
Bernardi,Bosisio,Mantegani,Sapini,Temperilli,Salvati,di Salle,Arcari,Bianchi
, p. 1094 - 1098 (2007/10/02)
The synthesis and the antihypertensive activity in rats of a series of 6-methylergolin-8β-yl-propionic acid derivatives are reported. The prolactin lowering activity (nidation inhibition test) in rats and the acute toxicity in mice were also studied as a measure of the specificity and safety of the potential antihypertensive compounds. From the structure-activity considerations reported here it is clear how modifications at the C8 side chain can improve the selectivity of the antihypertensive effects, whilst introducing substituents in other positions of the ergoline skeleton afforded unfavourable results in this respect. Compound 5, namely 2(R,S)-cyano-3-(6-methylergolin-8β-yl)-propionamide, emerged as the most interesting antihypertensive derivative.
6-N-Propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds
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, (2008/06/13)
6-n-Propyl (ethyl or allyl)-8β-methoxy-(methylsulfinyl, methylsulfonyl, or methylmercapto) methylergolines, 8-ergolenes or 9-ergolenes, useful as prolactin inhibitors and in the treatment of Parkinsonism.
