149934-19-0

Basic information

• Product Name: [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
• Synonyms: [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
• CAS NO: 149934-19-0
• Molecular Weight: 472.498
• Mol File: 149934-19-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 830.7±65.0 °C(Predicted)
• Density: 1.58±0.1 g/cm3(Predicted)
• CAS DataBase Reference: [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide(149934-19-0)
• EPA Substance Registry System: [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide(149934-19-0)

Safety Data

• Hazardous Substances Data: 149934-19-0(Hazardous Substances Data)

Usage

General Description

The chemical "[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide" is a complex compound with a long and specific name. It appears to be a derivative of the antibiotic doxorubicin, which is used in cancer treatment. The chemical structure suggests that it may have similar properties to doxorubicin, including the ability to inhibit DNA replication and damage cancer cells. However, further research and testing would be needed to fully understand its potential applications and effects. Additionally, the long and complex nature of the compound's name indicates its highly specific and specialized nature in the field of chemistry and pharmaceuticals.

Upstream product

• 13614-98-7 minocycline Hydrochloride 
• 179471-95-5 demethylchlortetracycline hydrochloride 
• 149934-17-8 9-nitrominocycline sulfate 
• 10118-90-8 MINOCYCLINE 
• 149934-16-7 (4S,4aS,5aR,12S)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxanaphthacene-2-carboxamide 

Downstream Products

• 220620-09-7 tigecycline 
• 10118-90-8 MINOCYCLINE 

Relevant articles and documents

An improved process for the preparation of Tigecycline intermediate and process for the preparation of Tigecycline therefrom

The present invention relates to a process for the preparation of Tigecycline intermediate i.e. 9-amino minocycline of formula-1(C). More particularly, the present invention relates to a process for the preparation of 9-amino minocycline of formula 1(C) and a process for the preparation of Tigecycline of formula 1 from 9-nitro minocycline of formula 1(B).

NITRATION OF TETRACYCLINES

The invention in one embodiment is directed to a method of preparing a compound of formula (1), or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are each independently chosen from hydrogen, (C1-C6)alkyl, and cycloalkyl, R is -NR3R4, where R3 and R4 are each independently chosen from hydrogen, and (C1-C4)alkyl; and n ranges from 1-4, comprising: (a) reacting a C1-C12 alkyl nitrate with a compound of formula (2), or a salt thereof, in the presence of an acid at a concentration greater than 70% weight of acid / weight of solution, the acid being selected from the group consisting of sulfuric acid, and R5-SO3H wherein R5 is C1-C4 alkyl optionally substituted with one or more halogen, or R5 is C6-C10 aryl optionally substituted with one or more C1-C4 alkyl or halogen, to produce a reaction mixture containing a compound of formula (3) or a salt thereof; (b) reducing the compound of formula (3) or a salt thereof to form a compound of formula (4) or a salt thereof; (c) acylating the compound of formula (4) to form a compound of formula (1), and (d) optionally forming a pharmaceutically acceptable salt of the compound of formula (1).

TIGECYCLINE AND METHODS OF PREPARING INTERMEDIATES

Methods of preparing and purifying 9-nitrominocycline and 9-aminominocycline and salts thereof used in the process of making tigecycline, are disclosed. In one embodiment, the invention is directed to a method of preparing the compound of formula 1 or a pharmaceutically acceptable salt thereof, comprising: (a) reacting nitric acid with the compound of formula 2, or a salt thereof, to produce a reaction mixture comprising an intermediate; and (b) further reacting the intermediate to form the compound of formula 1, wherein the intermediate is isolated from the reaction mixture, the method further comprising sparging with an inert gas prior to step (a).