147663-01-2

Basic information

• Product Name: (S)-9-Hydroxy Risperidone
• Synonyms: (S)-9-Hydroxy Risperidone;(9S)-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;(S)-9-Hydroxy Risperidone ((S)-Paliperidone);Paliperidone S-Isomer;(S)-Paliperidone;Pure Paliperidone (-);9-(S)-Paliperidone;3-[2-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-9(S)-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
• CAS NO: 147663-01-2
• Molecular Formula: C23H27FN4O3
• Molecular Weight: 426.4838832
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 147663-01-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-9-Hydroxy Risperidone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-9-Hydroxy Risperidone(147663-01-2)
• EPA Substance Registry System: (S)-9-Hydroxy Risperidone(147663-01-2)

Safety Data

• Hazardous Substances Data: 147663-01-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-9-Hydroxy Risperidone is used as an active pharmaceutical ingredient (API) for the treatment of psychiatric disorders. Its ability to act as a combined serotonin and dopamine receptor antagonist makes it effective in managing symptoms associated with schizophrenia, bipolar disorder, and other related conditions.
Used in Research and Development:
In the field of pharmaceutical research and development, (S)-9-Hydroxy Risperidone serves as a valuable compound for studying the mechanisms of action and potential applications of Risperidone and its metabolites. This knowledge can be applied to develop new drugs with improved efficacy and safety profiles.
Used in Drug Delivery Systems:
Similar to Gallotannin, (S)-9-Hydroxy Risperidone can also benefit from novel drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. By employing various organic and metallic nanoparticles as carriers, the limitations of (S)-9-Hydroxy Risperidone can be overcome, leading to improved treatment options for patients with psychiatric disorders.

Upstream product

• 108-20-3 di-isopropyl ether 
• 84163-13-3 6-fluoro-3-(piperidin-4-yl)benzo[d]isoxazole hydrochloride 
• 108-18-9 diisopropylamine 
• 67-63-0 isopropyl alcohol 
• 130049-82-0 3-(2-chloroethyl)-9-hydroxy-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one 
• 1117803-76-5 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-acetyloxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 
• 1104389-11-8 paliperidone hydrochloride 
• 84163-77-9 6-fluoro-3-(4-piperidinyl)benzo[d]isoxazole 
• 1204248-69-0 C₂₃H₂₆FN₅O₃ 
• 1189516-65-1 R₁₂₅₂₃₉ 
• 766485-15-8 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methyl-4H-pyrido-[1,2-a]pyrimidin-4-one 
• 106266-06-2 Risperidone 
• 1272320-23-6 paliperidone oxalate 
• 1056034-13-9 C₃₀H₂₉FN₄O₃ 

Downstream Products

• 1172995-13-9 paliperidone stearate 
• 1172995-11-7 paliperidone myristate 

Relevant articles and documents

METHODS AND COMPOSITIONS FOR TREATMENT OF CANCER

In an aspect, the disclosure pertains to inhibitors of ANGPTL4; synthesis methods for making disclosed compounds; pharmaceutical compositions comprising disclosed compounds; methods of treating disorders of uncontrolled cellular proliferation, e.g., a cancer; and methods of treating a disease associated with an ANGPTL4 dysfunction using disclosed compounds and pharmaceutical compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

Synthesis process of paliperidone palmitate

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.

Paliperidone intermediate and method for producing paliperidone using the same

Disclosed are novel intermediates of paliperidone which are used as a therapeutic agent for schizophrenia, and to a method for producing paliperidone using the same. The intermediates are a compound represented by chemical formula 3 and a compound represented by chemical formula 5. The method for producing paliperidone comprises a step of conducting a reaction of a compound represented by chemical formula 5 and an acid compound. In the chemical formulas 3 and 5, R is a silyl group, a hydrocarbon group having 1-20 carbon atoms, a protecting group represented by -R_1OR_2 or -R_1SR_2, or a protecting group represented by -C(=O)R_2. In particular, R_1 is a methylene group or a carbonyl group, and R_2 is a substituted or unsubstituted alkyl group, an aryl group, or an alkylaryl group, wherein R_1 and R_2 can bond to each other to form a ring.COPYRIGHT KIPO 2018

New synthesis method of paliperidone

The invention relates to a new synthesis method of paliperidone. 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride and 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one which are used as starting materials are reacted in the presence of a reducing reagent and an acid binding agent to obtain the paliperidone. The reducing agent is added in the reaction, so side reactions are reduced, the content of every impurity in the obtained finished product is significantly reduced, especially the content of the key impurity A is significantly reduced, the product has a high purity, and the method is simple to operate, and is suitable for industrial production.

A is suitable for industrial production of high-purity 9-hydroxy-risperidone

The invention discloses a method suitable for industrial production of high-purity 9-hydroxy-risperidone. According to the method, the 9-hydroxy-risperidone is prepared by carrying out condensation on 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole and 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]-pyrimidin-4-one in a polar solvent system; by optimizing post-treatment operation and improving a refining method, the high-yield and high-purity 9-hydroxy-risperidone can be prepared by utilizing the steps of sedimentation, salifying, alkali regulation, crystallization and the like; the post-treatment and the refining method disclosed by the invention has the advantages of simplicity and convenience in operation, low production cost and high product purity and are suitable for use in the industrial production.

Preparation method for paliperidone palmitate

The invention discloses a preparation method for paliperidone palmitate. The preparation method comprises the following steps: step 1, synthesis of 3-(2-hydroxyethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyltetrahydro-pyridino[1,2-alpha]pyrimidin-4-one; step 2, synthesis of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyltetrahydro-pyridino[1,2-alpha]pyrimidin-4-one; step 3, synthesis of paliperidone; and step 4, synthesis of paliperidone palmitate. Compared with the prior art, the preparation method provided by the invention has the advantages of short reaction time, low cost, controllability of impurities, easiness in purification, high product purity and high yield.

Preparation method of palipefidone

The invention provides a preparation method of palipefidone. The preparation method comprises the following steps: dissolving a palipefidone crude product into a heated alcohol solution; adding active carbon under a heating condition; keeping heat and stirring; filtering when the solution is hot to obtain a filtrate; at a temperature of 45 DEG C to 60 DEG C, adding a reducing agent into the filtrate, and keeping the heat and stirring for 30 to 60 minutes; after stirring, controlling to cool for 8 DEG C to 15 DEG C every hour; slowly cooling and crystallizing; after crystallizing, filtering to obtain a solid and a refined mother solution respectively; performing water washing, alcohol washing and vacuum drying on the obtained solid to obtain palipefidone crystallized powder; decompressing and concentrating the refined mother solution and recycling palipefidone secondary precipitate. The preparation method of the palipefidone is simple in process and convenient to operate, does not need special equipment and is suitable for industrial production; a toxin-free or low-toxin solvent is adopted, so that environmental pollution is lowered; the prepared product has high purity, and the content of 9-keto impurities is reduced to be 0.05 percent, even lower.

PROCESS FOR THE PREPARATION OF PALIPERIDONE

The present invention provides a process for the preparation of paliperidone or a pharmaceutically acceptable salt thereof, wherein the process comprises condensing a compound of formula (II) with a compound of formula (III) or a salt thereof, in a suitable solvent and a base, in the presence of a catalyst and an inhibiting agent, wherein the inhibiting agent is added to the reaction system before the compound of formula (II) and compound of formula (III) have reacted or as the reaction of the compound of formula (II) and compound of formula (III) is initiated, and optionally converting the paliperidone to a salt thereof, wherein X is a suitable leaving group. The present invention also provides substantially pure paliperidone or a salt thereof, paliperidone or a salt thereof as prepared by the process and uses of the paliperidone or salt thereof.

Synthesis and absolute configuration assignment of 9-hydroxyrisperidone enantiomers

The enantiomers of 9-hydroxyrisperidone, the major metabolite of risperidone and the active component of the antipsychotic drug Invega , were synthesized by efficient methods. Their optical rotation and enantiomeric purity were characterized for the first time. The absolute configurations were assigned by comparing 1H NMR chemical shifts of Mosher esters of a key stereoisomeric intermediate. Thus, the stereoisomeric center of (+)-9-hydroxyrisperidone has been assigned as the S configuration, and its enantiomer has the configuration R.

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.

An improved process for the synthesis of 3-[2-[4-((6-fluoro-1,2-benzisoxazol-3-yl)-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 (2-Chloroethyl)-6,7,8,9-tetrahydro-2-methyl-9-hydroxy-4H-pyrido [1,2-a]pyrimidine-4-one Palmitate ester.