26844-12-2

Basic information

• Product Name: Indoramin
• Synonyms: Indoramine;N-[1-[2-(1H-Indol-3-yl)ethyl]piperidin-4-yl]benzamide;Wy-21901
• CAS NO: 26844-12-2
• Molecular Formula: C22H25N3O
• Molecular Weight: 347.45
• EINECS: 248-041-5
• Mol File: 26844-12-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 208-210°
• Boiling Point: 600°Cat760mmHg
• Flash Point: 316.7°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 2.36E-14mmHg at 25°C
• Refractive Index: 1.657
• PKA: 14.32±0.20(Predicted)
• CAS DataBase Reference: Indoramin(CAS DataBase Reference)
• NIST Chemistry Reference: Indoramin(26844-12-2)
• EPA Substance Registry System: Indoramin(26844-12-2)

Safety Data

• Hazardous Substances Data: 26844-12-2(Hazardous Substances Data)

Usage

Originator

Baratol,Wyeth,UK,1981

Uses

Antihypertensive.

Manufacturing Process

4-Benzamido-1-[2-(3-indolyl)ethyl] pyridinium bromide (3.0 g) was dissolved in 91% ethanol (300 ml) containing triethylamine (0.08 g) and freshly prepared W7 Raney nickel catalyst (ca 3 g) was added. The mixture was hydrogenated in an autoclave at 400 psi hydrogen pressure and 50°C for 4 hours. After filtering off the catalyst the filtrate was evaporated in vacuo and the residue was shaken with a mixture of chloroform and 2N sodium hydroxide solution. The resulting insoluble material was filtered off and dried to give 1.61 g of product, MP 203°C to 206°C. Recrystallization from ethanol gave the title compound as colorless needles (1.34 g), MP 208°C to 210°C.

Therapeutic Function

Antihypertensive

InChI:InChI=1/C22H25N3O/c26-22(17-6-2-1-3-7-17)24-19-11-14-25(15-12-19)13-10-18-16-23-21-9-5-4-8-20(18)21/h1-9,16,19,23H,10-15H2,(H,24,26)

Upstream product

• 26844-47-3 2-(4-benzoylamino-piperidin-1-yl)-1-indol-3-yl-ethanone 

Relevant articles and documents

THERAPY FOR COMPLICATIONS OF DIABETES

A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.

Method for treating resistant hypertension

A method is provided for lowering blood pressure in a patient having clinically diagnosed resistant hypertension. The method comprises administering darusentan to the patient adjunctively with a baseline antihypertensive regimen that comprises administration of at least one diuretic and at least two antihypertensive drugs selected from at least two of (a) ACE inhibitors and angiotensin II receptor blockers, (b) beta-adrenergic receptor blockers and (c) calcium channel blockers. The darusentan is orally administered at a dose and frequency effective, in combination with the baseline regimen, to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures.

Process for preparing 3-[(benzamidopiperid-1-yl)alkyl] indoles

The invention provides a new process for preparing indoles in which a 4-acylamido-1-[3-indolyl-alylene] pyridinium compound or a corresponding tetrahydropyridine compound is reduced with alkali metal borohydride in special solvents to give a corresponding piperidine compound.