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282526-98-1

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282526-98-1 Usage

Description

Cetilistat, also known as ATL-962 and marketed under the brand name Oblean, is a novel pancreatic lipase inhibitor approved by the Japanese Ministry of Health, Labor and Welfare in September 2013. It is primarily used for the treatment of obesity in patients with type 2 diabetes mellitus (T2DM) and dyslipidemia, who have a body mass index (BMI) of 25 kg/m2 or higher, despite dietary treatment and/or exercise therapy. Cetilistat works by inhibiting pancreatic lipases in the gut, which in turn reduces fat absorption and caloric uptake from the diet. Cetilistat is characterized by its off-white crystalline appearance.

Uses

Used in Pharmaceutical Industry:
Cetilistat is used as a pancreatic lipase inhibitor for the treatment of obesity in both diabetic and non-diabetic patients. It specifically targets patients with type 2 diabetes mellitus (T2DM) and dyslipidemia, who have a BMI of 25 kg/m2 or higher and have not responded well to dietary treatment and/or exercise therapy. By inhibiting pancreatic lipases, cetilistat reduces fat absorption and caloric uptake from the diet, thus aiding in weight management and potentially improving overall health outcomes for these patients.

Originator

Alizyme PLC (United Kingdom)

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.

Check Digit Verification of cas no

The CAS Registry Mumber 282526-98-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,8,2,5,2 and 6 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 282526-98:
(8*2)+(7*8)+(6*2)+(5*5)+(4*2)+(3*6)+(2*9)+(1*8)=161
161 % 10 = 1
So 282526-98-1 is a valid CAS Registry Number.
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

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  • (Code)Product description
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  • 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%

282526-98-1Downstream Products

282526-98-1Relevant articles and documents

Process for efficiently synthesizing Cetilistat by taking 2-amino-5-methyl benzoic acid as raw material

-

Paragraph 0053; 0058-0059; 0064; 0068-0070, (2020/04/02)

The invention discloses a process for efficiently synthesizing Cetilistat by taking 2-amino-5-methyl benzoic acid as a raw material. The process comprises the steps: taking 2-amino-5-methyl benzoic acid as a raw material, and carrying out transesterification on 2-amino-5-methyl benzoic acid and triphosgene under the action of organic base catalysis to generate an intermediate c, namely 6-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione; carrying out a reaction on sulfonyl chloride (d) with a specific structure with n-hexadecanol under the condition of base catalysis to generate an intermediatef; and finally, carrying out an alkylation reaction on oxygen atoms of the intermediate c and the intermediate f in the presence of organic base to generate the target product Cetilistat. According tothe method, the reaction steps for synthesizing the Cetilistat are few, the process route is short, side reactions are few, the yield of the final product is high, and the purity is more than 99%.

A west for favorable department his preparation method

-

Paragraph 0063; 0064; 0065, (2017/08/25)

The invention discloses a preparation method of cetilistat, which has the advantages of high yield, mild reaction conditions and the like and can easily implement industrial production. The method comprises the following steps: (1) reacting methyl 2-amino-5-halobenzoate with triphosgene to obtain 2-methoxycarbonyl-4-halophenylisocyanate; adding hexadecanol to generate methyl 2-(hexadecaalkoxycarbonylamino)-5-halobenzoate; (2) adding the methyl 2-(hexadecaalkoxycarbonylamino)-5-halobenzoate, methyl boron dihydroxide and alkali into water and an organic solvent, adding a palladium catalyst, and reacting to obtain methyl 2-(hexadecaalkoxycarbonylamino)-5-methylbenzoate; (3) carrying out esterolysis reaction on the methyl 2-(hexadecaalkoxycarbonylamino)-5-methylbenzoate to obtain 2-(hexadecaalkoxycarbonyl)-5-methylbenzoic acid; (4) suspending the 2-(hexadecaalkoxycarbonyl)-5-methylbenzoic acid in pyridine, and cyclizing under the action of a dehydrating agent; and purifying and carrying out crystal transformation to obtain the cetilistat.

A preparing method of a lipase inhibitor

-

, (2016/10/17)

The invention belongs to the technical field of medicines, and particularly relates to a preparing method of 2-(hexadecyloxy)-6-methyl-4H-3,1-benzoxazin-4-one that is a lipase inhibitor. An intermediate that is hexadecyl-2-halogen-5-methyl-benzoyl carbamate shown as a formula (II) is subjected to amide cyclization and rearrangement with N-acyl-2-halogenobenzene under catalysis of a catalyst to prepare 1-(2-halogenbenzyl)-1,3-dione. -NH in imide and halogen are subjected to dehydrohalogenation to form a lactam four-membered ring firstly, and then the benzoxazin-4-one structure is formed by a C-N rearrangement reaction. The method is characterized by high product purity, simple, feasible and safe processes and capability of meeting requirements of industrial production.

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