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241479-67-4

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241479-67-4 Usage

Description

BAL-8557 (isavuconazonium) is the water-soluble pro-drug of BAL-4815 (isavuconazole). The conversion to isavuconazole is rapid and complete with very little cleavage product detectable – thus this chapter will focus entirely on isavuconazole. Isavuconazole is produced and developed by Basilea Pharmaceutica and, in common with the other azoles, works by inhibition of ergosterol synthesis. Isavuconazole is a water-soluble compound (the only broad-spectrum water soluble triazole) with oral and intravenous formulations and excellent bioavailability. Its long elimination half-life allows up to once-weekly dosing.

Uses

Different sources of media describe the Uses of 241479-67-4 differently. You can refer to the following data:
1. Isavuconazole is a new triazole currently undergoing phase III clinical trials. This compound has shown in vitro activity against a large number of clinical important yeasts and molds including Asperg illus spp., Fusarium spp., Scedosporium spp., Candida spp., the Zygomycetes and Cryptococcus spp.
2. Isavuconazole is a new triazole currently undergoing phase III clinical trials. This compound has shown in vitro activity against a large number of clinical important yeasts and molds including Aspergillus spp., Fusarium spp., Scedosporium spp., Candida spp., the Zygomycetes and Cryptococcus spp.

Definition

ChEBI: A 1,3-thiazole that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,5-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively. It is an antifungal drug used for the treatment of invasive aspergillosis and invasive mucormycosis.

Antimicrobial activity

Isavuconazole is a new broad-spectrum triazole with activity against Candida, Cryptococcus, Aspergillus, Zygomycetes, Rhizopus, and Rhizomucor spp. and dimorphic fungi including Histoplasma capsulatum and Blastomyces dermatitidis and a range of dermatophytes. In animal models, isavuconazole is highly effective against systemic candidiasis and disseminated Aspergillus fumigatus and flavus infections.

Biochem/physiol Actions

Maximum plasma concentrations of BAL 4815 are observed 1.5–3 hours after oral doses or at the end of the 1-hour intravenous infusion. Mean elimination half-lives are remarkably long more than 50 and 70 hours after oral and intravenous doses, respectively, allowing for once-daily (or less frequent) dosing. The volume of distribution is large and systemic clearance low. The protein binding is 98%. Escalation in multiple dosing regimens results in a proportional increase in maximum plasma drug concentration.

Clinical Use

Three regimens of isavuconazonium (BAL 8557) – single 200 mg dose followed by 50 mg daily, single 400 mg followed by 100 mg daily and single 400 mg followed by 400 mg weekly –were demonstrated to be as efficacious as fluconazole in a phase II study conducted on patients with uncomplicated esophageal candidiasis. The results of a phase II open-label dose-escalating trial of intravenous isavuconazonium as prophylaxis in AML (NCT00413439) are pending (NIH, 2008). Two phase III randomized double-blind studies to evaluate the safety and efficacy of isavuconazole are currently under way, versus caspofungin followed by voriconazole in the treatment of candidaemia and invasive candidiasis and versus voriconazole in primary treatment of invasive filamentous fungal infection . A phase III open-label study using isavuconazole in patients with aspergillosis and renal impairment and those with rare fungi is being planned NCT00634049.

Toxicology

In animals, isavuconazole has revealed no mutagenic, allergenic, phototoxic, or irritant potential. In 15 healthy volunteers, single doses of isavuconazole (up to 200 mg) were well tolerated, and no severe or serious adverse events occurred. In a multiple-dose pharmacokinetic study, 24 healthy males received isavuconazole for 21 days of oral or 14 days of intravenous dosing. The most frequent adverse events were headache, nasopharyngitis, and rhinitis, and all were mild or moderate; however one subject on oral high-dose BAL 8557 had mild transient abnormal liver function on day 14 of therapy, which resolved despite continuing the drug. No clinically relevant changes in vital signs or electrocardiogram were observed. In a double-blind randomized phase II trial for the treatment of esophageal candidiasis, BAL 8557 was safe and well tolerated, with an adverse event profile similar to that of fluconazole, the comparator drug.

Drug interactions

Rifampicin, a potent CYP3A4 inducer, decreases the Cmax and AUC of isavuconazole . Ketoconazole increases exposure to isavuconazole. Neither ciclosporin nor warfarin is affected by isavuconazole co-administration. Isavuconazole increases tacrolimus levels.

Metabolism

Molecular weight (daltons) 814.8 (as isavuconazonium sulphate) % Protein binding >99 % Excreted unchanged in urine <1 Volume of distribution (L/kg) 450 Litres Half-life - normal/ESRF (hrs) 2-4 (as isavuconazole); 80-130 (as isavuconazonium) / Unchanged

Check Digit Verification of cas no

The CAS Registry Mumber 241479-67-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,4,1,4,7 and 9 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 241479-67:
(8*2)+(7*4)+(6*1)+(5*4)+(4*7)+(3*9)+(2*6)+(1*7)=144
144 % 10 = 4
So 241479-67-4 is a valid CAS Registry Number.

241479-67-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name isavuconazole

1.2 Other means of identification

Product number -
Other names 4-[2-[(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:241479-67-4 SDS

241479-67-4Synthetic route

isavuconazole hydrobromide

isavuconazole hydrobromide

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate92.6%
(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide

(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanethioamide

4-Cyanophenacyl bromide
20099-89-2

4-Cyanophenacyl bromide

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol86%
In ethanol at 60 - 65℃; for 15h;81.6%
In ethanol at 78℃; for 3h;77.4%
In ethanol at 70℃;
4-Cyanophenacyl bromide
20099-89-2

4-Cyanophenacyl bromide

C13H19FN4OS

C13H19FN4OS

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
In ethanol at 60℃; for 2h;70%
(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile
241479-74-3

(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butyronitrile

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogen sulfide; sulfuric acid / ethanol / 5 h / Autoclave; Heating
2.1: ethanol / 8 h / 60 - 70 °C
2.2: 5 h / 20 - 70 °C / pH 4 - 5
View Scheme
Multi-step reaction with 2 steps
1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C
2: ethanol / 3 h / 78 °C
View Scheme
Multi-step reaction with 2 steps
1: diammonium sulfide / tetrahydrofuran / 96 h / 27 - 30 °C / Reflux
2: ethanol / 15 h / 60 - 65 °C
View Scheme
(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide hydrogensulphate

(2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide hydrogensulphate

4-(2-chloroacetyl)benzenecarbonitrile
40805-50-3

4-(2-chloroacetyl)benzenecarbonitrile

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Stage #1: (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)thiobutyramide hydrogensulphate; 4-(2-chloroacetyl)benzenecarbonitrile In ethanol at 60 - 70℃; for 8h;
Stage #2: With triethylamine In ethanol; water at 20 - 70℃; for 5h; pH=4 - 5;
3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol

3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid / toluene / 20 - 70 °C
2: sodium hydrogencarbonate / dichloromethane; water
View Scheme
(2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol (1R)-10-camphorsulfonate

(2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol (1R)-10-camphorsulfonate

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water
3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile

3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetone; methanol / 20 °C / Reflux
2.1: sodium hydroxide / dichloromethane; water
3.1: hydrogen sulfide; sulfuric acid / ethanol / 5 h / Autoclave; Heating
4.1: ethanol / 8 h / 60 - 70 °C
4.2: 5 h / 20 - 70 °C / pH 4 - 5
View Scheme
(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile-(1R)-10-camphorsulfonate

(2S,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl)butanenitrile-(1R)-10-camphorsulfonate

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / dichloromethane; water
2.1: hydrogen sulfide; sulfuric acid / ethanol / 5 h / Autoclave; Heating
3.1: ethanol / 8 h / 60 - 70 °C
3.2: 5 h / 20 - 70 °C / pH 4 - 5
View Scheme
(2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol hydrobromide

(2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-1-(1H-1,2,4-triazol-1-yl)-2-(2,5-difluorophenyl)-butan-2-ol hydrobromide

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane; water18.5 g
α-chloro-2',5'-difluoroacetophenone
60468-36-2

α-chloro-2',5'-difluoroacetophenone

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triphenylphosphine; dichloro bis(acetonitrile) palladium(II) / tetrahydrofuran / 0.17 h / -20 °C / Inert atmosphere
1.2: 3 h / -10 °C
2.1: sodium carbonate / dimethyl sulfoxide / 4 h / 70 °C
3.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C
4.1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C
5.1: ethanol / 3 h / 78 °C
View Scheme
C11H10ClF2NO

C11H10ClF2NO

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium carbonate / dimethyl sulfoxide / 4 h / 70 °C
2: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C
3: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C
4: ethanol / 3 h / 78 °C
View Scheme
1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone
1157938-97-0

1-(2,5-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
1.2: 0.33 h
1.3: 2 h / -50 °C
2.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C
3.1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C
4.1: ethanol / 3 h / 78 °C
View Scheme
Multi-step reaction with 4 steps
1.1: indium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
1.2: 10 h / -10 °C
2.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C
3.1: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C
4.1: ethanol / 3 h / 78 °C
View Scheme
3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl) butyronitrile

3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-(1H-1,2,4-triazol-1-yl) butyronitrile

Isavuconazole
241479-67-4

Isavuconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid / toluene; tert-butyl methyl ether; methanol / 1 h / 60 °C
2: O,O-Diethyl hydrogen phosphorodithioate / water / 6 h / 78 °C
3: ethanol / 3 h / 78 °C
View Scheme
N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester
338990-31-1

N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester

Isavuconazole
241479-67-4

Isavuconazole

1-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]-triazo-4-ium iodide

1-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]-triazo-4-ium iodide

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 70℃; for 3h; Inert atmosphere;98%
With sodium iodide In acetonitrile at 45 - 50℃; for 15h;88.4%
With sodium iodide In acetonitrile at 50 - 60℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;83%
2(S)-[acetoxymethyl]-1-[chloromethyloxycarbonyl]pyrrolidine
338990-23-1

2(S)-[acetoxymethyl]-1-[chloromethyloxycarbonyl]pyrrolidine

Isavuconazole
241479-67-4

Isavuconazole

[[2(S)-(acetoxymethyl)pyrrolidin-1-yl]carbonyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

[[2(S)-(acetoxymethyl)pyrrolidin-1-yl]carbonyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 50℃;92%
N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester
338990-31-1

N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester

Isavuconazole
241479-67-4

Isavuconazole

C40H43F2N8O7S(1+)*Br(1-)

C40H43F2N8O7S(1+)*Br(1-)

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium bromide In acetonitrile at 25 - 30℃; for 48h; Reagent/catalyst; Temperature;89.2%
[N-ethyl-N-(tert-butoxycarbonylethylamino)ethyl]carbamic acid 1-chloroethyl ester
338990-56-0

[N-ethyl-N-(tert-butoxycarbonylethylamino)ethyl]carbamic acid 1-chloroethyl ester

Isavuconazole
241479-67-4

Isavuconazole

1-[[N-ethyl-N-2-(t-butoxycarbonylethylamino)ethyl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

1-[[N-ethyl-N-2-(t-butoxycarbonylethylamino)ethyl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions
ConditionsYield
sodium iodide In acetonitrile at 60℃;86%
4-tert-butoxycarbonyl-methyl-aminoacetoxy-3,5-dimethyl-benzyl bromide

4-tert-butoxycarbonyl-methyl-aminoacetoxy-3,5-dimethyl-benzyl bromide

Isavuconazole
241479-67-4

Isavuconazole

4-{4-[(tert-Butoxycarbonyl-methyl-amino)-acetoxy]-3,5-dimethyl-benzyl}-1-[(2R,3R)-3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium bromide

4-{4-[(tert-Butoxycarbonyl-methyl-amino)-acetoxy]-3,5-dimethyl-benzyl}-1-[(2R,3R)-3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium bromide

Conditions
ConditionsYield
In acetonitrile84%
[N-methyl-N-3-(acetoxy)propyl]carbamic acid chloromethyl ester

[N-methyl-N-3-(acetoxy)propyl]carbamic acid chloromethyl ester

Isavuconazole
241479-67-4

Isavuconazole

[[N-methyl-N-3-(acetoxy)propyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

[[N-methyl-N-3-(acetoxy)propyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 50℃;82%
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-4-fluoro-phenyl]carbamic acid 1-chloroethyl ester
338990-35-5

[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-4-fluoro-phenyl]carbamic acid 1-chloroethyl ester

Isavuconazole
241479-67-4

Isavuconazole

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-4-fluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-4-fluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 70℃;72%
N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester
338990-31-1

N-methyl N-(3-[((N-tert-butoxycarbonyl-N-methylamino)acetoxy)methyl]pyridin-2-yl)carbamic acid (1-chloroethyl) ester

Isavuconazole
241479-67-4

Isavuconazole

1-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

1-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino)acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 50℃;65%
[N-methyl-N-2-(acetoxymethyl)phenyl]carbamic acid chloromethyl ester
338990-20-8

[N-methyl-N-2-(acetoxymethyl)phenyl]carbamic acid chloromethyl ester

Isavuconazole
241479-67-4

Isavuconazole

[[N-methyl-N-2-(acetoxymethyl)phenyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

[[N-methyl-N-2-(acetoxymethyl)phenyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions
ConditionsYield
With sodium iodide In acetonitrile Heating;63%
sodium iodide In acetonitrile at 20 - 80℃; for 9h;63%
[N-methyl-N-phenyl]carbamic acid chloromethyl ester
186353-05-9

[N-methyl-N-phenyl]carbamic acid chloromethyl ester

Isavuconazole
241479-67-4

Isavuconazole

[[N-methyl-N-phenyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

[[N-methyl-N-phenyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions
ConditionsYield
In acetonitrile at 80℃;60%
[N-methyl-N-2-((tert-butoxycarbonylisopropylamino)methyl)phenyl]carbamic acid 1-chloroethyl ester
338990-27-5

[N-methyl-N-2-((tert-butoxycarbonylisopropylamino)methyl)phenyl]carbamic acid 1-chloroethyl ester

Isavuconazole
241479-67-4

Isavuconazole

1-[[N-methyl-N-2-(t-butoxycarbonyl-isopropylaminomethyl)phenyl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride
338990-62-8

1-[[N-methyl-N-2-(t-butoxycarbonyl-isopropylaminomethyl)phenyl]carbamoyloxy]ethyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium chloride

Conditions
ConditionsYield
sodium iodide In acetonitrile at 70℃;51%
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-4,5-difluoro-phenyl]carbamic acid 1-chloroethyl ester
338990-34-4

[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-4,5-difluoro-phenyl]carbamic acid 1-chloroethyl ester

Isavuconazole
241479-67-4

Isavuconazole

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-4,5-difluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-4,5-difluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 80℃;50%
acetic acid 2-(iodomethoxycarbonyl-methyl-amino)-ethyl ester

acetic acid 2-(iodomethoxycarbonyl-methyl-amino)-ethyl ester

Isavuconazole
241479-67-4

Isavuconazole

[[N-methyl-N-2-(acetoxy)ethyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

[[N-methyl-N-2-(acetoxy)ethyl]carbamoyloxy]methyl-1-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-1H-[1,2,4]triazol-4-ium iodide

Conditions
ConditionsYield
In acetonitrile at 50℃;
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-5-chlorophenyl]carbamic acid 1-chloroethyl ester
338990-41-3

[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-5-chlorophenyl]carbamic acid 1-chloroethyl ester

Isavuconazole
241479-67-4

Isavuconazole

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-5-chloro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-5-chloro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions
ConditionsYield
In acetonitrile at 65℃;
[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-3-fluorophenyl]carbamic acid 1-chloroethyl ester
338990-44-6

[N-methyl-N-2-[(tert-butoxycarbonylmethylamino)acetoxymethyl]-3-fluorophenyl]carbamic acid 1-chloroethyl ester

Isavuconazole
241479-67-4

Isavuconazole

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-3-fluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

4-[1-({2-[(tert-butoxycarbonyl-methyl-amino)-acetoxymethyl]-3-fluoro-phenyl}-methyl-carbamoyloxy)-ethyl]-1-[3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium; chloride

Conditions
ConditionsYield
With sodium iodide In acetonitrile Heating;
Isavuconazole
241479-67-4

Isavuconazole

C35H35F2N8O5S(1+)*I(1-)

C35H35F2N8O5S(1+)*I(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium iodide / acetonitrile / 12 h / 50 - 60 °C / Inert atmosphere
2: sulfuric acid / ethyl acetate; ethanol / 1 h / 30 °C / Reflux; Large scale
View Scheme

241479-67-4Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF TRIAZOLE DERIVATIVES

-

, (2021/12/31)

The present invention relates to an improved process for the preparation of triazole derivatives such as ravuconazole and isavuconazole.

Crystal form of isavuconazole and preparation method thereof

-

Paragraph 0106-0117; 0120-0125, (2019/01/24)

The invention relates to a crystal form I of isavuconazole, a preparation method and application thereof. X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, hygroscopicity analysis and other means are employed for comprehensive characterization of the crystal form I of isavuconazole, and the invention finds that the crystal form I has more excellent stability than amorphism. The preparation method of the crystal form I of isavuconazole has the characteristics of simple operation, easy control and good reproducibility.

Method for manufacturing isavuconazole or ravuconazole

-

, (2017/08/27)

The invention provides a method for manufacturing a triazole compound isavuconazole or ravuconazole which is enriched by a diastereoisomer and enantiomer. The method comprises the following steps: a Reformatsky reaction is carried out between ketone and dihalogeno metal propionitrile; an enantiomer mixture is generated, and separation is carried out. The method can obviously reduce steps for synthesis of isavuconazole or ravuconazole, yield of products is improved, and production cost is reduced.

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