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199739-10-1

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199739-10-1 Usage

Description

Paliperidone palmitate is an atypical long acting antipsychotics,which can fast onset in acute phase and continuously improve the symptoms in maintenance phase. It has the solid efficacy and convenient ad[1]ministration,which offer a new option for schizophrenia treatment and will help patients to adhere the treatment and prevent relapse. As the sole long acting antipsychotics with monthly injection,it was approved by CFDA in 2011 and indicated for the acute and maintenance treatment of schizophrenia.

Uses

Paliperidone Palmitate is a long-acting injectable atypical antipsychotic used in the treatment of schizophrenia.

Side effects

The review of the literature also underlined that paliperidone palmitate is well tolerated, compared with placebo. Frequency and severity of side-effects such as extrapyramidal symptoms, hyperprolactinemia and weight gain, was similar or less than those found in treatment with other atypical antipsychotics, including long-acting ones.

Check Digit Verification of cas no

The CAS Registry Mumber 199739-10-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,9,7,3 and 9 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 199739-10:
(8*1)+(7*9)+(6*9)+(5*7)+(4*3)+(3*9)+(2*1)+(1*0)=201
201 % 10 = 1
So 199739-10-1 is a valid CAS Registry Number.

199739-10-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Paliperidone Palmitate

1.2 Other means of identification

Product number -
Other names 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido-[1,2-a]pyrimidin-4-one palmitate ester

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:199739-10-1 SDS

199739-10-1Synthetic route

palmitic anhydride
623-65-4

palmitic anhydride

paliperidone
144598-75-4

paliperidone

paliperidone palmitate
199739-10-1

paliperidone palmitate

Conditions
ConditionsYield
Stage #1: palmitic anhydride; paliperidone With dmap In toluene at 20 - 70℃; for 3h;
Stage #2: With tert-butyl methyl ether In toluene at 10℃; for 1h; Product distribution / selectivity;
88.5%
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

paliperidone
144598-75-4

paliperidone

paliperidone palmitate
199739-10-1

paliperidone palmitate

Conditions
ConditionsYield
With dmap; pivaloyl chloride; triethylamine In tetrahydrofuran at 20℃; for 24h; Product distribution / selectivity;80%
3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester
1415488-05-9

3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester

6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride
84163-13-3

6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride

paliperidone palmitate
199739-10-1

paliperidone palmitate

Conditions
ConditionsYield
Stage #1: 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride With potassium carbonate In acetonitrile at 25 - 60℃; for 1.16667h;
Stage #2: 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester With tetrabutylammomium bromide; potassium iodide at 20 - 75℃; for 14h;
80%
Stage #1: 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride With potassium carbonate In acetonitrile at 25 - 60℃; for 1.16667h;
Stage #2: 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-one palmitate ester With tetra-(n-butyl)ammonium iodide; potassium iodide In acetonitrile at 25 - 75℃; for 16h;
80%
paliperidone
144598-75-4

paliperidone

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

paliperidone palmitate
199739-10-1

paliperidone palmitate

Conditions
ConditionsYield
Stage #1: paliperidone With sodium hydride In N,N-dimethyl-formamide at 0℃;
Stage #2: n-hexadecanoyl chloride In N,N-dimethyl-formamide at 0℃; for 5h; Product distribution / selectivity;
53.1%
With dmap; triethylamine In dichloromethane at 15℃; for 8h; Temperature;
3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one sodium
1172995-09-3

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one sodium

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

paliperidone palmitate
199739-10-1

paliperidone palmitate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 2h;10 %Chromat.
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

paliperidone palmitate
199739-10-1

paliperidone palmitate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: dmap; triethylamine / dichloromethane / 0.25 h / 25 - 30 °C
1.2: 2 h / 25 - 40 °C
2.1: potassium carbonate / acetonitrile / 1.17 h / 25 - 60 °C
2.2: 14 h / 20 - 75 °C
View Scheme
paliperidone palmitate
199739-10-1

paliperidone palmitate

paliperidone
144598-75-4

paliperidone

Conditions
ConditionsYield
Stage #1: paliperidone palmitate With hydrogenchloride In water at 75 - 80℃; for 2h;
Stage #2: With sodium hydroxide In methanol; dichloromethane; water; isopropyl alcohol at 10 - 30℃; for 1h; pH=10 - 12; Reflux;
90%
With hydrogenchloride In water at 75 - 80℃; for 2h;90%
paliperidone palmitate
199739-10-1

paliperidone palmitate

A

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7-dihydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
913728-82-2

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7-dihydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

B

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-9-pentadecyl-4H-pyrido[1,2-a]pyrimidin-4-one
913728-83-3

3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-9-pentadecyl-4H-pyrido[1,2-a]pyrimidin-4-one

C

paliperidone
144598-75-4

paliperidone

Conditions
ConditionsYield
Product distribution / selectivity; X-irradiation;

199739-10-1Relevant articles and documents

Synthesis process of paliperidone palmitate

-

Paragraph 0036; 0046-0051; 0061-0066; 0076-0080, (2019/10/04)

Belonging to the technical field of pharmaceutical compositions, the invention relates to a synthesis process of paliperidone palmitate. Through synthesis of P (paliperidone), refinement of P synthesis of PP (paliperidone palmitate) and refinement of PP, the paliperidone palmitate can be prepared. According to the invention, the process is controllable, the cost is low, the impurities are controllable, the refining process is simple and convenient, the product purity is high, and the yield is high.

PREPARATION OF 3-[2-[4-((6-FLUORO-1, 2-BENZISOXAZOL-3-YL)-L-PIPERIDINYL)-6, 7, 8, 9-TETRAHYDRO-9-HYDROXY-2-METHYL-4H-PYRIDO[ 1, 2-A]-PYRIMIDIN-4-ONE (PALIPERIDONE) AND PALIPERIDONE PALMITATE.

-

Page/Page column 11-12, (2013/02/28)

Provided is a process for the synthesis of 3-[2-[4-((6-fluoro-1,2-benzisoxazol-3-y l)-1-piperidinyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]-pyrimidin -4-one (Paliperidone) and Paliperidone Palmitate through a novel intermediate 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido[1,2-a]pyrimidin -4-one palmitate ester. A process for preparing a compound of formula VIII through a compound of formula VII is also provide.

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