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High Quality 99% Cetilistat 282526-98-1 GMP manufacturer
Cas No: 282526-98-1
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282526-98-1 Usage

Chemical Synthesis

Commercially available hexadecanol (21) was treated with phosgene in THF/toluene to give the corresponding chloroformate (22), which was immediately subjected to commercial 2-amino-5- methylbenzoic acid (23) in pyridine. Subsequent slow addition of methyl chloroformate at room temperature resulted in the formation of cetilistat (IV), which was produced in 31% overall yield from hexadecanol.

Brand name

Oblean

Uses

A novel pancreatic lipase inhibitor for the treatment of obesity in both diabetic and non-diabetic patients.

Originator

Alizyme PLC (United Kingdom)

Chemical Properties

Off-white Cryst

Description

Cetilistat (also known as ATL-962) was approved in September 2013 by the Japanese Ministry of Health, Labor and Welfare for the treatment of obesity, limited to patients with both type 2 diabetes mellitus (T2DM) and dyslipidemia, and with a body mass index (BMI)25 kg/m2 in spite of dietary treatment and/or exercise therapy. As with orlistat, cetilistat works via inhibition of pancreatic lipases in the gut to inhibit fat absorption and thereby reduce caloric uptake from diet. The medicinal chemistry program has not been described in the scientific literature, but the patent describing cetilistat also describes the synthesis of analogs with varied aryl substituents and lipophilic tails. The synthesis of cetilistat involves condensation of a hexadecylcarbonochloridate with 2-amino-5-methylbenzoic acid; other analogs were synthesized by varying the carbonochloridate and 2-aminobenzoic acid components. Cetilistat is a potent inhibitor of human and rat pancreatic lipase with IC50s of 15 and 136 nM, respectively, with little inhibition of trypsin or chymotrypsin.
InChI:InChI=1/C25H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-28-25-26-23-18-17-21(2)20-22(23)24(27)29-25/h17-18,20H,3-16,19H2,1-2H3

282526-98-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (C2745)  Cetilistat  >98.0%(HPLC) 282526-98-1 1g 590.00CNY Detail
TCI America (C2745)  Cetilistat  >98.0%(HPLC) 282526-98-1 5g 1,960.00CNY Detail

282526-98-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Cetilistat

1.2 Other means of identification

Product number -
Other names 2-(Hexadecycloxy)-6-methyl-4H-3,1-benzoxazin-4-one

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:282526-98-1 SDS

282526-98-1Synthetic route

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid
890655-08-0

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Solvent; Reagent/catalyst;96.5%
With 1,1'-carbonyldiimidazole In dichloromethane Reagent/catalyst;92%
With pyridine; chloroformic acid ethyl ester at 0 - 10℃; for 1h; Reagent/catalyst; Concentration;85.5%
hexadecanyl p-trifluoromethylsulfonate

hexadecanyl p-trifluoromethylsulfonate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With triethylamine In dichloromethane Cooling with ice; Reflux;90%
hexadecyl-2-iodo-5-methylbenzoyl-carbamate

hexadecyl-2-iodo-5-methylbenzoyl-carbamate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With copper(l) iodide; calcium chloride In 1,4-dioxane for 3h; Inert atmosphere; Reflux;81%
hexadecyl-2-bromo-5-methylbenzoyl-carbamate

hexadecyl-2-bromo-5-methylbenzoyl-carbamate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With magnesium sulfate; copper(I) bromide In toluene for 3h; Inert atmosphere; Reflux;71%
2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid
890655-08-0

2-(((hexadecyloxy)carbonyl)amino)5-methylbenzoic acid

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
With pyridine In ice-water
1-Hexadecanol
36653-82-4

1-Hexadecanol

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 3 h / 20 °C
2: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: acetonitrile / 2.5 h / 25 - 65 °C
2.1: triethylamine / 7 h / 25 - 90 °C
3.1: pyridine / dichloromethane / 0.17 h / 25 - 30 °C
3.2: 4 h / 0 - 35 °C
View Scheme
cetyl chloroformate
26272-90-2

cetyl chloroformate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / tetrahydrofuran / 4 h / 20 °C / Reflux
2: copper(l) iodide; calcium chloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: periodic acid; chromium(VI) oxide; acetic anhydride / acetonitrile / 1.5 h / 0 - 20 °C
3: copper(l) iodide; calcium chloride / 1,4-dioxane / 3 h / Inert atmosphere; Reflux
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
2: periodic acid; chromium(VI) oxide; acetic anhydride / acetonitrile / 1.5 h / 0 - 20 °C
3: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
Kohlensaeure-di-n-hexadecylester
13784-52-6

Kohlensaeure-di-n-hexadecylester

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap / dichloromethane / 18 h / 20 °C
2: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
hexadecyl-2-bromo-5-methylbenzyl-carbamate

hexadecyl-2-bromo-5-methylbenzyl-carbamate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: periodic acid; chromium(VI) oxide; acetic anhydride / acetonitrile / 1.5 h / 0 - 20 °C
2: copper(I) bromide; magnesium sulfate / toluene / 3 h / Inert atmosphere; Reflux
View Scheme
2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium carbonate / tetrahydrofuran; water
2: 1,1'-carbonyldiimidazole / dichloromethane
View Scheme
2-Amino-5-methylbenzoic acid
2941-78-8

2-Amino-5-methylbenzoic acid

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / 20 °C
2: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling with ice
3: lithium carbonate / tetrahydrofuran; water
4: 1,1'-carbonyldiimidazole / dichloromethane
View Scheme
2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate

2-amino-5-methylbenzoic acid methyl ester hydrogen sulfate

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere; Cooling with ice
2: lithium carbonate / tetrahydrofuran; water
3: 1,1'-carbonyldiimidazole / dichloromethane
View Scheme
2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one
282526-98-1

2-hexadecyloxy-6-methyl-4-chloro-1-benzoxazin-4-one

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

2-(hexadecyloxycarbonyl)amino-5-methylbenzoic acid methyl ester

Conditions
ConditionsYield
In methanol; dichloromethane at 40℃; for 5h; Solvent; Temperature; Reflux;98.1%

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