121840-95-7

Basic information

• Product Name: Rogletimide
• Synonyms: Rogletimide;rac-(R*)-3β*-(4-Pyridyl)-3-ethylpiperidine-2,6-dione;Rogletimida;Rogletimida [inn-spanish];Rogletimidum;Rogletimidum [inn-latin]
• CAS NO: 121840-95-7
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Mol File: 121840-95-7.mol

Chemical Properties

• Boiling Point: 420.5°C at 760 mmHg
• Flash Point: 208.1°C
• Appearance: /
• Density: 1.155g/cm³
• Vapor Pressure: 2.81E-07mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: Rogletimide(CAS DataBase Reference)
• NIST Chemistry Reference: Rogletimide(121840-95-7)
• EPA Substance Registry System: Rogletimide(121840-95-7)

Safety Data

• Hazardous Substances Data: 121840-95-7(Hazardous Substances Data)

Usage

Uses

Antineoplastic.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 28, p. 200, 1985 DOI: 10.1021/jm00380a009

InChI:InChI=1/C12H14N2O2/c1-2-12(9-4-7-13-8-5-9)6-3-10(15)14-11(12)16/h4-5,7-8H,2-3,6H2,1H3,(H,14,15,16)

Upstream product

• 54401-85-3 pyridin-4-yl-acetic acid ethyl ester 
• 75-03-6 ethyl iodide 
• 79-06-1 2-propenamide 
• 13121-99-8 pyridin-4-ylacetonitrile 
• 72434-23-2 2-(4-pyridyl)butyronitrile 
• 121742-49-2 (S)-4-Cyano-2-ethyl-2-pyridin-4-yl-butyric acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 29800-89-3 methyl 4-pyridineacetate 
• 121767-99-5 Pyridin-4-yl-acetic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 121742-48-1 (R)-4-Cyano-2-ethyl-2-pyridin-4-yl-butyric acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 126651-40-9 ethyl,4-cyano-2-ethyl-2-(4-pyridyl)butanoate 
• 92788-12-0 4-cyano-4-(4-pyridyl)-hexanenitrile 
• 126651-39-6 ethyl,4-cyano-2-(4-pyridyl)butanoate 

Downstream Products

• 103284-30-6 3-ethyl-1-octyl-3-(4-pyridyl)piperidine-2,6-dione 

Relevant articles and documents

Analogues of Aminoglutethimide: Selective Inhibition of Aromatase

In exploring further the structural features that influence the relative efficacy of analogues of aminoglutethimide as inhibitors of the cholesterol side-chain cleavage enzyme system desmolase and the estrogen forming system aromatase, analogues have been synthesized in which the aminophenyl substituent is replaced by pyridyl or substituted pyridyl.The 4-pyridyl analogue 5 is a strong competitive inhibitor of aromatase (Ki-1.1 μM; value for 1, 0.60 μM), which exhibits a type II difference spectrum (Ks = 0.28 μM; value for 1, 0.13 μM) but is noninhibitory toward desmolase.The 2- and 3-pyridyl analogues (3 and 4) inhibit neither enzyme system. 1-Amino-3-ethyl-3-phenylpiperidine-2,6-dione (2) is a strong and selective inhibitor of desmolase but the 4-pyridyl analogue 10 is a weak inhibitor of desmolase and aromatase.Analogues of 5 having a less basic aromatic substituent, namely, the N-oxide 11 and the 2,3,5,6-tetrafluoro derivative 13, were also prepared.The latter is a weak inhibitor of aromatase and the former inhibits neither enzyme system

Preparation of 2,6-dioxopiperidine derivatives

3-Alkyl- or fluoroalkyl-3-(4-pyridyl)piperidine-2,6-diones, useful in the treatment of breast cancer, of formula STR1 wherein R represents an alkyl group having 2 to 10 carbon atoms or a fluoroalkyl group having 2 to 5 carbon atoms and A is hydrogen or an alkyl group having 1 to 4 carbon atoms, are prepared by reacting a 4-pyridylacetate with an alkyl or fluoroalkyl iodide, chloride or bromide, in the presence of a sterically bulky base and reacting the product with acrylamide in the presence of a sodium or potassium branched chain alkoxide. Preferably potassium t-butoxide is used in both stages and they are carried out sequentially at room temperature in an alcoholic or polar, aprotic solvent in a single reaction vessel.

2,6-dioxopiperidine derivatives, their preparation and pharmaceutical compositions containing them

PCT No. PCT/GB84/00425 Sec. 371 Date Jul. 16, 1985 Sec. 102(e) Date Jul. 16, 1985 PCT Filed Dec. 10, 1984 PCT Pub. No. WO85/02618 PCT Pub. Date Jun. 20, 1985.In the treatment of estrogen-dependent tumors, it is desirable to improve the therapy obtainable from the compound aminoglutethimide. It has now been found that 3-ethyl-3-(4-pyridyl)glutarimide and derivatives thereof of formula wherein R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms offers advantages over aminoglutethimide. 3-Ethyl-3-(4-pyridyl)glutarimide can be prepared by various ring-closing reactions, especially by heating 4-(4-pyridyl)-hexano-1,4-dinitrile with a strong mineral acid.

A CONCISE SYNTHESIS OF RACEMIC PYRIDOGLUTETHIMIDE AND ITS RESOLUTION USING CHIRAL STATIONARY PHASE HPLC

We describe a 'one-pot' synthesis of the aromatase inhibitor pyridoglutethimide and its 3-octyl-analogue, together with details of the resolution of the former using chiral stationary phase hplc.

Synthesis of the Aromatase Inhibitor 3-Ethyl-3-(4-pyridyl)piperidine-2,6-dione and Its Enantiomers

Convenient syntheses of (R/S)-3-ethyl-3-(4-pyridyl)piperidine-2,6-dione (pyridoglutethimide) and its enantiomers are described; aromatase inhibitory activity was almost entirely confined to the 3R-enantiomer

Glutarimide derivatives for treating oestrogen-dependent tumors

In the treatment of oestrogen-dependent tumors, it is desirable to improve the therapy obtainable from the compound aminoglutethimide. It has now been found that 3-ethyl-3-(4-pyridyl)glutarimide derivatives of formula STR1 wherein: (a) R1 represents an ethyl group and R2 represents a methyl group, an alkyl or cycloalkyl group having 3 to 10 carbon atoms, or a fluoroalkyl group having 2 to 10 carbon atoms; (b) R1 represents an alkyl group having 3 to 10 carbon atoms or a fluoroalkyl group having 2 to 5 carbon atoms and R2 represents a hydrogen atom; or, (c) R1 represents an alkyl group having 3 to 8 carbon atoms or a fluoroalkyl group having 2 to 5 carbon atoms and R2 represents an alkyl or fluoroalkyl group having 2 to 8 carbon atoms, provided that the total number of carbon atoms in R1 and R2 is not more than 10; and therapeutically acceptable acid addition salts of the above compounds.