149934-16-7

Usage

Uses

1. Used in Pharmaceutical Applications:
[4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide is used as a pharmaceutical agent for its potential therapeutic effects. The compound's unique structure and functional groups may allow it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
2. Used in Chemical Synthesis:
[4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide can be used as a key intermediate or building block in the synthesis of other complex organic molecules. Its versatile structure and functional groups make it a valuable starting material for the preparation of various chemical compounds, including pharmaceuticals, dyes, and other specialty chemicals.
3. Used in Research and Development:
Due to its unique structure and potential biological activities, [4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide can be employed as a research tool in various scientific fields, such as medicinal chemistry, biochemistry, and pharmacology. It can be used to study the structure-activity relationships of related compounds and to investigate the mechanisms of action of potential drug candidates.
4. Used in Analytical Chemistry:
The compound's unique structure and functional groups may also make it useful as a reagent or analytical standard in various analytical techniques, such as chromatography, spectroscopy, and electrochemistry. It can be employed to develop new methods for the detection and quantification of specific analytes or to improve the sensitivity and selectivity of existing analytical procedures.

Indications

Minoxidil, an antihypertensive agent, produces arteriolar vasodilation by an unknown mechanism. In limited clinical studies, minoxidil increases penile rigidity and has been used in the long-term treatment of organic impotence.

Biological Functions

Minoxidil (Loniten) is an orally effective vasodilator. It is more potent and longer acting than hydralazine and does not accumulate significantly in patients with renal insufficiency. It depends on in vivo metabolism by hepatic enzymes to produce an active metabolite, minoxidil sulfate. Minoxidil sulfate activates potassium channels, resulting in hyperpolarization of vascular smooth muscle and relaxation of the blood vessel.

Pharmacology

The hemodynamic effects of minoxidil are generally similar to those of hydralazine, with the noteworthy exception that a greater decrease in peripheral vascular resistance and consequently a larger reduction in blood pressure can be achieved with minoxidil. Minoxidil produces no important changes in either renal blood flow or glomerular filtration rate. It has little or no effect on venous capacitance and does not inhibit the reflex activation of the sympathetic nervous system. Orthostasis and other side effects of sympathetic blockade are therefore not a problem. As with hydralazine, there is a significant increase in cardiac output that is secondary to reflex increases in sympathetic activity, hyperreninemia, and salt and water retention.These effects can substantially reduce the effectiveness of minoxidil when it is used alone.The addition of a -blocker and a diuretic to the therapeutic regimen will preserve minoxidil’s antihypertensive action while attenuating some of the undesirable side effects.

Clinical Use

The major indications for the use of minoxidil are (1) severe hypertension that may be life threatening and (2) hypertension that is resistant to milder forms of therapy. Compromises in renal function do not prolong either the plasma or the therapeutic half-life of minoxidil, and therefore, it seems to be particularly important for hypertensive patients with chronic renal failure.

Side effects

Signs of toxicity common to vasodilator therapy in general also occur with minoxidil; they are attributable to vasodilation and reflex increases in sympathetic nerve activity. These include headache, nasal congestion, tachycardia, and palpitations. These effects do not have great clinical importance, since minoxidil is almost always administered in combination with a -blocker, which antagonizes the indirect cardiac effects. A more troublesome side effect, particularly in women, is the growth of body hair, possibly due to a direct stimulation of the growth and maturation of cells that form hair shafts. Apparently, minoxidil activates a specific gene that regulates hair shaft protein. In any case, this particular side effect has been capitalized upon, and minoxidil is now marketed as Rogaine for the treatment of male pattern baldness.

Metabolism

Peak concentrations of minoxidil in the blood occur 1 hour after oral administration, although the therapeutic effect may take 2 or more hours to manifest. This is probably related to the time it takes to convert minoxidil to minoxidil sulfate. The antihypertensive action after an oral dose of minoxidil lasts 12 to 24 hours. The long duration of action allows the drug to be administered only once or twice a day, a regimen that may be beneficial for compliance. Interestingly, the therapeutic half-life is considerably longer than the plasma half-life. This may be, as has been suggested for hydralazine, a result either of accumulation of the drug and its active metabolite in arterial walls or a longer plasma half-life of the sulfated metabolite, or both. The ultimate disposition of minoxidil depends primarily on hepatic metabolism and only slightly on renal excretion of unchanged drug. Because of this, pharmacological activity is not cumulative in patients with renal failure.

Upstream product

• 13614-98-7 minocycline Hydrochloride 
• 10118-90-8 MINOCYCLINE 

Downstream Products

• 149934-19-0 [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 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of 9-substituted minocycline derivatives

A number of 9-acylamino and 9-sulfonylamino derivatives of minocycline have been synthesized for structure-activity relationship studies. These compounds showed activity against both tetracycline-susceptible and tetracycline-resistant strains. Many of the

Minocycline-based europium(III) chelate complexes: Synthesis, luminescent properties, and labeling to streptavidin

Two chelate ligands for europium(III) having minocycline (=(4S,4aS,5aR,12aS)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10, 12,12a-tetrahydroxy-1,11-dioxonaphthacene-2-carboxamide; 5) as a VIS-light-absorbing group were synthesized as possible VIS-light-excitable stable Eu3+ complexes for protein labeling. The 9-amino derivative 7 of minocycline was treated with H6TTHA (= triethylenetetraminehexaacetic acid=3,6,9,12-tetrakis(carboxymethyl)-3,6,9,12- tetraazatetradecanedioic acid) or H5DTPA (= diethylenetriaminepentaacetic acid=N,N-bis{2-[bis(carboxymethyl)amino]ethyl} glycine) to link the polycarboxylic acids to minocycline. One of the Eu 3+ chelates, [Eu3+(minocycline-TTHA)] (13), is moderately luminescent in H2O by excitation at 395 nm, whereas [Eu 3+(minocycline-DTPA)] (9) was not luminescent by excitation at the same wavelength. The luminescence and the excitation spectra of [Eu 3+(minocycline-TTHA)] (13) showed that, different from other luminescent EuIII chelate complexes, the emission at 615 nm is caused via direct excitation of the Eu3+ ion, and the chelate ligand is not involved in the excitation of Eu3+. However, the ligand seems to act for the prevention of quenching of the Eu3+ emission by H2O. The fact that the excitation spectrum of [Eu3+(minocycline-TTHA)] is almost identical with the absorption spectrum of Eu3+ aqua ion supports such an excitation mechanism. The high stability of the complexes of [Eu3+(minocycline-DTPA)] (9) and [Eu3+(minocycline-TTHA)] (13) was confirmed by UV-absorption semi-quantitative titrations of H 4(minocycline-DTPA) (8) and H5(minocycline-TTHA) (12) with Eu 3+. The titrations suggested also that an 1:1 ligand Eu3+ complex is formed from 12, whereas an 1:2 complex was formed from 8 minocycline-DTPA. The H5(minocycline-TTHA) (12) was successfully conjugated to streptavidin (SA) (Scheme 5), and thus the applicability of the corresponding Eu3+ complex to label a protein was established.

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).

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).

Isolation of tetracycline derivatives

Provided is a process for the isolation of tetracycline derivatives.