573762-62-6

Basic information

• Product Name: 5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE
• Synonyms: 5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE;5-AMino-3-(trifluroMethyl) picolinonitrile;5-AMino-3-(trifluoroMethyl)pyridine-2-carbonitrile;5-Amino-3-(trifluoromethyl)2-cyanopyridine;5-Amino-2-cyano-3-(trifluoromethyl)pyridine;5-amino-3-((trifluoromethyl))-pyridin-2-carbonitrile;5-Amino-3-(trifluoromethyl)-2-pyridinecarbonitrile
• CAS NO: 573762-62-6
• Molecular Formula: C₇H₄F₃N₃
• Molecular Weight: 187.1219696
• EINECS: -0
• Product Categories: LG
• Mol File: 573762-62-6.mol

Chemical Properties

• Boiling Point: 362.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.45±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -1.52±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE(573762-62-6)
• EPA Substance Registry System: 5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE(573762-62-6)

Safety Data

• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 573762-62-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical properties and reactivity make it a valuable building block in the development of new pharmaceutical compounds.
As a pharmaceutical intermediate, 5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE plays a crucial role in the production of drugs that target a wide range of medical conditions. Its ability to form stable bonds with other molecules allows for the creation of complex drug structures with specific therapeutic properties.

Upstream product

• 573762-57-9 2-cyano-3-(trifluoromethyl)-5-nitropyridine 
• 956104-45-3 5-{[(4-methoxyphenyl)methyl]amino}-3-(trifluoromethyl)pyridine-2-carbonitrile 
• 887707-23-5 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine 
• 887707-25-7 2-chloro-5-iodo-3-(trifluoromethyl)pyridine 
• 956104-44-2 6-chloro-N-[(4-methoxyphenyl)methyl]-5-(trifluoromethyl)pyridin-3-amine 
• 99368-66-8 2-hydroxyl-5-nitro-3-(trifluoromethyl)pyridine 
• 99368-66-8 5-nitro-3-(trifluoromethyl)pyridine-2-(1H)-one 
• 22245-83-6 3-(trifluoromethyl)pyridin-2-ol 
• 3796-23-4 3-(trifluoromethyl)pyridine 
• 22253-72-1 3-(trifluoromethyl)pyridine-N-oxide 
• 406933-21-9 2-cyano-3-(trifluoromethyl)pyridine 
• 22245-83-6 3-(trifluoromethyl)pyridine-2-(1H)-one 
• 65753-47-1 2-chloro-3-trifluoromethyl-pyridine 
• 99368-67-9 2-chloro-5-nitro-3-(trifluoromethyl)pyridine 

Downstream Products

• 956104-40-8 ARN-509 
• 1332392-79-6 5-(5-(4-amino-3-hydroxyphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile 
• 1332388-84-7 5-(5-(4-bromo-3-fluorophenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile 
• 1332388-81-4 5-(5-(3-fluoro-4-hydroxyphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile 
• 1332388-83-6 ethyl 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluorobenzoate 
• 1332390-03-0 5-(5-(3-fluoro-4-(2-(1-methyl-1H-pyrazol-5-yl)ethoxy)phenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile 
• 1332390-04-1 5-[8-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-5-oxo-7-thioxo-6,8-diazaspiro[3.4]octan-6-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile 
• 1332390-05-2 5-(5-(4-(benzyloxy)-3-fluorophenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile 
• 1332390-80-3 5-(5-(3-fluoro-4-methoxyphenyl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile 
• 1332391-11-3 4-[6-[6-cyano-5-(trifluoromethyl)-3-pyridyl]-5-oxo-7-thioxo-6,8-diazaspiro[3.4]octan-8-yl]-2-fluorobenzamide 
• 1332391-14-6 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluoro-N-(2-(pyrrolidin-1-yl)ethyl)benzamide 
• 1332391-15-7 N-benzyl-4-[6-[6-cyano-5-(trifluoromethyl)-3-pyridyl]-5-oxo-7-thioxo-6,8-diazaspiro[3.4]octan-8-yl]-2-fluorobenzamide 
• 1332391-16-8 4-[6-[6-cyano-5-(trifluoromethyl)-3-pyridyl]-5-oxo-7-thioxo-6,8-diazaspiro[3.4] octan-8-yl]-2-fluoro-N-[2-(2-pyridyl)ethyl]benzamide 
• 1332391-17-9 4-[6-[6-cyano-5-(trifluoromethyl)-3-pyridyl]-5-oxo-7-thioxo-6,8-diazaspiro[3.4]octan-8-yl]-2-fluoro-N-(3-pyrrolidin-1-ylpropyl)benzamide 

Relevant articles and documents

DIARYLTHIOHYDANTOIN COMPOUND AS ANDROGEN RECEPTOR ANTAGONIST

The present application belongs to the field of medicine. In particular, the present application relates to a diarylthiohydantoin compound as an androgen receptor antagonist or a pharmaceutically acceptable salt thereof, a preparation method of the same, a pharmaceutical composition comprising the compound, and a use thereof in treating a cell proliferative disease mediated by androgen. The compound of the present application has good antagonistic effect on androgen receptor and exhibits excellent antitumor effect.

Discovery of pyridine tetrahydroisoquinoline thiohydantoin derivatives with low blood-brain barrier penetration as the androgen receptor antagonists

Prostate cancer (PC) is the most diagnosed type of malignancy in men and the major frequently cause of cancer-related death worldwide. The androgen receptor (AR) has become a promising drug target for the treatment of PC. Here, we reported the design, optimization and evaluation of pyridine tetrahydroisoquinoline thiohydantoin derivatives with improved activity and safety as potent AR antagonists. The most promising compound 42f exhibited potent inhibitory activity on AR and strongly blocked AR nuclear translocation. Moreover, 42f displayed promising in vitro antitumor activity toward AR-dependent prostate cancer cell lines (LNCaP) and also demonstrated therapeutic effects in LNCaP xenograft tumor model in mice (TGI: 79%) with no apparent toxicity observed in vivo. More importantly, 42f showed negligible penetration of the brain-blood barrier (BBB) compared with enzalutamide. These results provide a foundation for the development of a new class of androgen receptor antagonists for potential therapeutics against PC with lower seizurogenic risk for patients.

Prostatic cancer treatment medicine

The invention relates to a compound with a prostatic cancer treatment function and nontoxic pharmaceutically acceptable salt of the compound. The structure of the compound is as shown in a formula I,wherein X is C or N, R1 is alkyl of C1-C3 or halogen substituted alkyl, R2 is alkyl of C1-C3 and halogen substituted alkyl or halogen, R3 and R4 are independently selected from H, alkyl and substituted alkyl, and R3 and R4 are connected to form cycloalkyl. The compound has high inhibiting effects on in-situ prostate cancer and transfer of the prostate cancer, and eclamptogenic side effects are lower.

Preparation method of 5 - (S)-3 -(trifluoromethyl) pyrimidin -2 -one (trifluoromethyl) pyridylketone (I) (by machine translation)

The method comprises the following three 5 - steps:3 - halogenating, reacting with a cyanidation -2 - reaction, a reduction reaction and an 2 - isothiocyanate -5 - esterification -3 - reaction in a three-step high yield, wherein the compound is synthesized by three steps in a cyanidation reaction, a 5 - reduction reaction -3 - and a thiocyanation reaction -2 . The preparation method provided by 5 -3 - the invention is high in yield, low -2 - in cost, environment-friendly, easy to operate and suitable for industrial preparation. (by machine translation)

Design, synthesis, and biological evaluation of deuterated apalutamide with improved pharmacokinetic profiles

A series of deuterated apalutamide were designed and prepared. Compared to its prototype compound 18, deuterated analogues 19 and 21 showed obviously higher plasma concentrations and better PK parameters after oral administration in mice. In rats, N-trideuteromethyl compound 19 displayed 1.8-fold peak concentration (Cmax), and nearly doubled its drug exposure in plasma (AUC0–∞) compared to compound 18. Unsurprisingly, compounds 18 and 19 had similar affinity for AR in vitro. In summary, the deuteration strategy could obviously improve PK parameters of apalutamide.

ANDROGEN RECEPTOR MODULATOR FOR TREATMENT OF PROSTATE CANCER AND ANDROGEN RECEPTOR-ASSOCIATED DISEASES

PROBLEM TO BE SOLVED: To provide a series of compounds that modulate the function of the nuclear hormone receptors, especially the androgen receptor. SOLUTION: The present invention relates to hydantoin compounds, methods of using such compounds in the treatment of androgen receptor-associated conditions, such as age-related diseases, for example, prostate cancer, and to pharmaceutical compositions containing such compounds. In an embodiment, a pharmaceutical composition includes a therapeutically effective amount of a compound according to the formula II, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, diluent, or adjuvant. The present invention provides a series of compounds that modulate the function of the nuclear hormone receptors, especially the androgen receptor. These compounds can cause disappearance of prostate cancer cells and tumors. COPYRIGHT: (C)2016,JPOandINPIT

Substituted diazaspiroalkanes as androgen receptor modulators

This invention provides for compounds of the Formula II: wherein A, B, Het, R1, R2 and R3 are as described herein. These compounds are androgen receptor modulators useful for the treatment of androgen receptor-associated conditions.

IMIDAZOLE DIKETONE COMPOUND AND USE THEREOF

Provided are imidazolidinedione compounds of formula (I), processes for preparation, uses and pharmaceutically compositions thereof. Said imidazolidinedione compounds possess androgen receptor antagonist activity and can be used for preventing and treating diseases and disorders related to androgen receptor, such as prostate cancer, alopecia, hair regeneration, acne and adolescent acne.

PROCESSES FOR THE PREPARATION OF A DIARYLTHIOHYDANTOIN COMPOUND

Disclosed are processes and intermediates for the preparation of compound (X), which is currently being investigated for the treatment of prostate cancer.

SYNTHESIS OF THIOHYDANTOINS

A novel synthesis of the anti-androgen, A52, which has been found to be useful in the treatment of prostate cancer, is provided. A52 as well as structurally related analogs may be prepared via the inventive route. This new synthetic scheme may be used to prepare kilogram scale quantities of pure A52.