37686-84-3

Usage

References

1) Akai et al. (1993), Effects of terguride, a partial D2 agonist, on MPTP-lesioned parkinsonian cynomolgus monkeys; Ann. Neurol., 133 507 2) Klewe et al. (2008), Recruitment of beta-arrestin2 to the dopamine D2 receptor: insights into anti-psychotic and anti-parkinsonian drug receptor signaling; Neuropharmacology, 54 1215 3) Dumitrascu et al. (2011), Terguride ameliorates monocrotaline-induced pulmonary hypertension in rats; Eur. Respir. J., 37 1104

InChI:InChI=1/C20H28N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,11,14,16,18,21H,4-5,9-10,12H2,1-3H3,(H,22,25)/t14-,16+,18+/m0/s1

Upstream product

• 96860-91-2 1-<(5R,8S,10R)-6-cyano-8-ergolinyl>-3,3-diethylurea 
• 18016-80-3 lisuride 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 59043-22-0 8alpha-Amino-6-methylergoline 
• 106347-60-8 1-<(5R,8S,10R)-6-methyl-8-ergolinyl>-3,3-diethylurea dihydrogen citrate 

Downstream Products

• 178443-53-3 8α-[[2-(benzoylsulfanyl)acetyl]amino]-6-methylergoline 
• 178476-60-3 8α-[[2-(benzoylsulfanyl)propionyl]amino]-6-methylergoline 
• 122888-36-2 (6aR,9S,10aR)-9-(3,3-Diethyl-ureido)-7-methyl-6,6a,7,8,9,10-hexahydro-4H-indolo[4,3-fg]quinoline-10a-carboxylic acid phenylamide 
• 122888-33-9 (6aR,9S,10aR)-4-(tert-Butyl-dimethyl-silanyl)-9-(3,3-diethyl-ureido)-7-methyl-6,6a,7,8,9,10-hexahydro-4H-indolo[4,3-fg]quinoline-10a-carboxylic acid phenylamide 
• 77650-95-4 1-<(5R,8S,10R)-6-propyl-8-ergolinyl>-3,3-diethylurea 

Relevant academic research and scientific papers

Molecular structure of cis- and trans-tergurides

Four isomers of terguride, a semisynthetic ergot alkaloid derivative, have been prepared by catalytic hydrogenation of (5R.8S)- and (5S,8S)-lisuride [1,1-diethyl-3-(6-methyl-8-ergolenyl)urea]. Relative stereochemistry of the isomers is based on NMR and CD spectra. Absolute configuration of all the series has been confirmed by the X-ray crystal structure determination of (5R,8S,10S)-terguride 2-bromobenzoate [1,1-diethyl-3-(6-methyl-8-isoergolenyl)urea, cis-dihydrolisuride].

ERGOLINE DERIVATIVES FOR USE IN MEDICINE

The present invention provides novel neuromodulatory compounds and compositions thereof. The invention also relates to methods of treating various diseases, disorders, and conditions using the compounds of this invention; processes for preparing the compounds of this invention; as well as intermediates for the preparation compounds.

Process for the production ergoline derivatives

Ergoline derivatives of general Formula I STR1 wherein C8 C9 and C9 C10 are both CC-single bonds or one is a C=C-double bond, R6 is C1-4 alkyl, R8 is methyl, hydroxymethyl, carbonylmethoxy, ureido or N,N-diethylureido, each in the α- or β-position, and R is hydrogen or nitro, are prepared by dehydrogenation of corresponding 2,3-dihydroergoline derivatives using an electrophilic reagent in an apolar solvent and a base.

Use of 1-(8-alpha-ergolinyl)-3,3-diethyl urea derivatives in the treatment of endometritis

A composition for the treatment of endometritis in mammalian females which comprises as the physiologically active component a 1-(8alpha-ergolinyl)-3,3-diethylurea of the general formula I in which R1 represents an alkyl group containing from 1 to 3 carbon atoms, R2 represents a hydrogen atom or an alkyl group containing from 1 to 3 carbon atoms and either X stands for a hydrogen atom or both of them form jointly an additional bond between carbon atoms in positions 9 and 10, or a pharmaceutically acceptable acid addition salt thereof. The subject composition of the invention is suitable for treating acute puerperal inflammations and chronic endometritis in mammalian females, especially farm animal females, e.g. cows.

SOLVOLYSIS OF SOME 1-(8α-ERGOLINYL)-3,3-DIETHYLUREAS AND THEIR SALTS

Nine salts of 1-(8α-ergolinyl)-3,3-diethylurea (II) were prepared and their solubility in water and the stability of the aqueous solutions at 60 and 100 deg C were studied.The main product of hydrolysis is 6-methyl-8α-aminoergoline IV.The urethan VII is formed in the ethanolic solution.Both decomposition products are also formed under long-term storage at +5 deg C.The course of hydrolysis of N-propyl homologue III is similar.The decomposition of 9,10-didehydro derivative I is much slower under the conditions used.

Method for treatment of endometritis in mammalian females

This invention relates to a method for the treatment of endometritis (chronic and/or acute puerperal inflammations) in mammalian females comprising the administration of 1-(8-alpha-ergolinyl)-3,3-diethylurea derivatives of Formula I STR1 in which R1 represents an alkyl group containing 1 to 3 carbon atoms, R2 represents a hydrogen atom or an alkyl group containing 1 to 3 carbon atoms, and X represents a hydrogen atom or a double bond between the carbon atoms at positions 9 and 10. The compound according to Formula I, or a pharmaceutically acceptable acid addition salt thereof, is the physiologically active component of the therapeutic composition and method. The compound may be combined with a pharmaceutically acceptable diluent, vehicle, excipient, auxiliary, or carrier. The invention is particularly advantageous in veterinary medicine, when applied to the treatment of farm animals, such a cows.