138402-05-8

Basic information

• Product Name: 2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE HYDROCHLORIDE
• Synonyms: 2-BUTYL-1,3-DIAZASPIRO[4.4]NON-1-EN-4-ONE HCL;2-BUTYL-1,3-DIAZASPIRO[4,4]NON-1-ENE-4-ONE HYDROCHLORIDE;2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE HCL;2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE HYDROCHLORIDE;2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE MONOHYDROCHLORIDE;2-Butyl-1,3-diazaspiro4.4non-1-en-4-one;2-Butyl-1,3-Diazaspiro[4,4]Non-1-En-4-One Hydrochloride;2-BUTYL-1,3-DIAZASPSPIRO[4,4]NON-1-EN-4-ONE
• CAS NO: 138402-05-8
• Molecular Formula: C₁₁H₁₈N₂O
• Molecular Weight: 194.28
• Product Categories: Heterocyclic Compounds;Heterocycles
• Mol File: 138402-05-8.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 294.7±23.0 °C(Predicted)
• Appearance: oil
• Density: 1.186 g/cm³
• Refractive Index: 1.592
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.42±0.20(Predicted)
• CAS DataBase Reference: 2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE HYDROCHLORIDE(138402-05-8)
• EPA Substance Registry System: 2-N-BUTYL-1,3-DIAZA-SPIRO[4,4]NON-1-EN-4-ONE HYDROCHLORIDE(138402-05-8)

Safety Data

• Hazardous Substances Data: 138402-05-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-N-Butyl-1,3-Diazaspiro[4,4]Non-1-En-4-One Hydrochloride is used as a chemical intermediate for the production of Irbesartan (Avapro) (I751000), which is a medication used to treat high blood pressure and type 2 diabetes. Its role in the synthesis process is crucial for the development of this medication, as it contributes to the overall structure and function of the final product.

InChI:InChI=1/C11H18N2O/c1-2-3-6-9-12-10(14)11(13-9)7-4-5-8-11/h2-8H2,1H3,(H,12,13,14)

Upstream product

• 1664-35-3 ethyl 1-aminocyclopentanecarboxylate 
• 999-09-7 ethyl valerimidate 
• 638-29-9 n-valeryl chloride 
• 16195-83-8 1-aminocyclopentanecarbonitrile hydrochloride 
• 17193-28-1 1-aminocyclopentane-1-carboxamide 
• 4524-93-0 Cyclopentanecarboxylic acid chloride 
• 931-17-9 1,2-Cyclohexanediol 
• 18257-46-0 pentanamidine hydrochloride 
• 177219-40-8 1-(pentanoylamino)cyclopentanecarboxamide 
• 151257-03-3 2-n-butyl-1,3-diazaspiro<4.4>nonan-4-one 
• 253269-07-7 (N-valeryl)-1-aminocyclopentanecarboxamide 

Downstream Products

• 254744-55-3 2-(1,3-Dioxolan-2-yl)-4-[(2-n-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]bromobenzene 
• 1029083-94-0 irbesartan trifluoroacetate 
• 151257-05-5 tert-butyl-4'-<(2-n-butyl-4-oxo-1,3-diazaspiro<4.4>non-2-en-1-yl)methyl>biphenyl-2-carboxylate 
• 138402-11-6 2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one 
• 151257-04-4 tert-butyl-4'-<(2-n-butyl-4-oxo-1,3-diazaspiro<4.4>nonan-1-yl)methyl>biphenyl-2-carboxylate 
• 151257-08-8 tert-butyl-4'-<(2-n-butyl-4-oxo-1,3-diazaspiro<4.4>nonan-3-yl)methyl>biphenyl-2-carboxylate 
• 138401-34-0 tert-butyl-4'-<(2-n-butyl-4-thioxo-1,3-diazaspiro<4.4>non-1-en-3-yl)methyl>biphenyl-2-carboxylate 
• 467423-51-4 4-{[4-(2-butyl-4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-ylmethyl)-2'-(3,4-dimethyl-isoxazol-5-ylsulfamoyl)-biphenyl-2-ylmethyl]-amino}-2,2-dimethyl-butyric acid 

Relevant articles and documents

Discovery of Irbesartan Derivatives as BLT2 Agonists by Virtual Screening

Leuktriene B4 receptor 2 (BLT2) is a G-protein coupled receptor modulation of which is discussed to be a therapeutic option for healing of intestinal lesions. In this work, new BLT2 agonists were identified by a virtual screening of a repurposing library and in vitro assay of the most promising compounds. Irbesartan, an approved type-1 angiotensin II receptor (AT1) antagonist, was identified as a moderate BLT2 agonist. An initial SAR study on the irbesartan scaffold was performed resulting in the discovery of a new potent BLT2 agonist (8f, EC50 = 67.6 nM). Irbesartan and 8f were shown to promote proliferation of epithelial colon cells, an effect which was reversible by a BLT2 antagonist.

OMS-2 nanorod-supported cobalt catalyst for aerobic dehydrocyclization of vicinal diols and amidines: Access to functionalized imidazolones

The development of reusable base metal catalysts for innovative catalytic transformations is a key technology toward sustainable production of fine chemicals, pharmaceuticals, and other function products. Herein, we report the preparation of a new highly dipersed manganese oxides of octahedral molecular sieve (OMS-2) nanorod-supported cobalt catalyst, which is successfully applied for aerobic dehydrocyclization of vicinal diols and amidines to access structurally diverse imidazolones, a class of valuable compounds found in numerous natural and biomedical products. The developed catalytic transformation proceeds with broad substrate scope, good functional group compability, the use of green molecular oxygen and reusable cobalt catalyst, which offers an important platform for the conversion of abundant and sustainable alcohol resources into functional N-heterocycles. The strategy combining nanocatalyst design with aerobic dehydrocoupling is anticipated to achieve other challenging catalytic transformations.

Synthesis of 2-Aminoimidazolones and Imidazolones by (3 + 2) Annulation of Azaoxyallyl Cations

The first examples of (3 + 2) annulations between azaoxyallyl cations and cyanamides and nitriles to give the corresponding 2-aminoimidazolones and imidazolones are reported. On the basis of the isolation of unexpected imidate products with certain substr

Design, synthesis and evaluation of novel potent angiotensin II receptor 1 antagonists

A series of new angiotensin II (Ang II) receptor 1 antagonists were designed, synthesized and evaluated. All compounds showed nanomolar affinities for the angiotensin II type 1 receptor in radioligand binding assays and could reduce blood pressure signifi

Oxidation of substituted imidazolidin-4-ones: New alternative method preparation of 4,5-dihydro-1H-imidazol-5-ones

The reaction of aldehydes (pentanal, benzaldehyde, 4-methoxybenzaldehyde, 4-nitrobenzaldehyde, salicylaldehyde, pyridin-2-carbaldehyde) with 1-aminocyclopentancarboxamide or (S)-2-amino-2,3-dimethylbutanamide has been used to prepare substituted imidazolidin-4-ones 1a-g (a: R1 = CH 3(CH2)3; b: R1 = C6H 5; c: R1 = 4-CH3OC6H4; d: R1 = 4-NO2C6H4; e: R1 = 2-HOC6H4; f: R1 = 2-pyridyl; for R2 = R3 = (CH2)4), and g: R1 = 2-pyridyl; for R2 = CH3; R3 = CH(CH 3)2) in the yields of 53-83%. Subsequent oxidations with various reagents gave the corresponding 4,5-dihydro-1H-imidazol-5-ones 2a-g: Pd/C (72-93%), DDQ (25-80%), and MnO2 (30-77%). Structure of the prepared compounds 1a-g and 2a-g was verified by 1H NMR and 13C NMR spectroscopy, EI-MS and elemental analysis. X-ray diffraction was performed in the case of compounds 1e and 2e.

SUBSTITUTED IMIDAZOLONE DERIVATIVES, PREPARATIONS AND USES

The present invention relates to polysubstituted imidazolone derivatives, to the pharmaceutical compositions comprising them and to the therapeutic uses thereof in the human and animal health fields. The present invention also relates to a process for preparing these derivatives.

PROCESS FOR PURE IRBESARTAN

The present invention provides an improved and commercially viable process for preparation of irbesartan intermediate, 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-n-butyl-4-spirocyclopentane-2-imidazolin-5-one, substantially free of 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-n-propyl-4-spirocyclopentane-2-imidazolin-5-one impurity, thereby producing irbesartan substantially free of the undesired propyl analog impurity, namely 2-propyl-3-[[2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-1,3 -diazaspiro[4.4]non-1-en-4-one. The present invention also provides a process for preparation of irbesartan substantially free of tin content. The present invention further provides a commercially viable process for preparation of irbesartan in high purity and in high yield.

Process for the preparation of 2-alkyl-1-((2'-substituted-biphenyl-4-yl) Methyl)-imidazole, dihydroimidazole or benzimidazloe derivatives

The invention relates to a new process for the preparation of sartans 2-butyl-3-[[2′-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1′-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one is disclosed, which proceeds via novel intermediate, 4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]phenylboronic acid (Formula (II)) or its analogs. Compound (II) reacts with 5-(2-bromophenyl)-1-(triphenylmethyl)-1H-tetrazole (III) in the presence of catalyst, using conditions of Suzuki reaction, to give trityl irbesartan (I), whereas analogs to compound (II) may give candesartan, valsartan, telmisartan, losartan and olmesartan.

Original loading and Suzuki conditions for the solid-phase synthesis of biphenyltetrazoles. Application to the first solid-phase synthesis of irbesartan

Biphenyltetrazoles are recognized privileged structures. Among them, the therapeutically important class of sartans displays antagonistic activity on AT1 receptors. We have developed a method for anchoring tetrazole derivatives via the heterocycle on a hydroxylated resin using zinc triflate. New Suzuki-Miyaura cross-coupling conditions are developed for the quantitative formation of the phenyl-phenyl bond. Our straightforward synthesis scheme, starting from the conserved phenyltetrazole moiety and ending with the appending of the structurally variable moiety, is well suited to the preparation of sartans and their analogues at a laboratory scale. We thus describe here the first solid phase synthesis of irbesartan, a marketed AT1 antagonist.

NOVEL DUAL ACTION RECEPTORS ANTAGONISTS (DARA) AT THE AT1 AND ETA RECEPTORS

The present invention relates to new compounds of the formula [Chemical formula should be inserted here. Please see paper copy] wherein R1, R2, R3, and R31 are as specified herein. The invention also relates to a method for preparation thereof, as well as combinations of the new compounds with previously known agents. The invention also relates to the use of the above-mentioned compounds and combinations for the preparation of a medicament for treating hypertension of different kinds, alleviating organ damage of different kinds, treating or preventing diabetic nephropathy, treating endothelin and angiotensin mediated disorders, and treating prostate cancer.