308831-94-9

Basic information

• Product Name: 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester
• Synonyms: 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester
• CAS NO: 308831-94-9
• Molecular Weight: 504.511
• Mol File: 308831-94-9.mol

Chemical Properties

• Boiling Point: 623.4±55.0 °C(Predicted)
• Density: 1.362±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester(308831-94-9)
• EPA Substance Registry System: 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester(308831-94-9)

Safety Data

• Hazardous Substances Data: 308831-94-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester is utilized as a precursor or building block in the synthesis of pharmaceuticals for its potential to exhibit biological activities beneficial in treating various diseases.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, this compound serves as a subject of study for its possible antimicrobial, anti-inflammatory, or antineoplastic activities, which could lead to the development of new drugs targeting these therapeutic areas.
Used in Drug Design and Optimization:
The unique structural elements of 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester make it a candidate for drug design and optimization processes, where its properties can be fine-tuned for specific therapeutic applications.
Used in Antimicrobial Agents Development:
Given its potential antimicrobial properties, 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester is used as a starting point for developing new antimicrobial agents to combat resistant bacterial strains.
Used in Anti-inflammatory Therapies:
2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester may be employed in the creation of anti-inflammatory drugs, leveraging its potential to modulate inflammatory responses for the treatment of conditions characterized by inflammation.
Used in Antineoplastic Drug Development:
2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester is used in the development of antineoplastic drugs, aiming to treat cancer by leveraging its potential to inhibit tumor growth and progression.

Upstream product

• 1313714-59-8 (E/Z)-2-cyano-3-methyl-4-(4-nitrophenyl)but-2-enoic acid ethyl ester 
• 105-56-6 ethyl 2-cyanoacetate 
• 5332-96-7 1-(4-nitrophenyl)propan-2-one 
• 174072-89-0 2-Amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester 
• 308831-93-8 2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester 
• 697-73-4 2,6-difluorobenzyl chloride 

Downstream Products

• 308831-95-0 4-(bromomethyl)-2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester 
• 1589503-95-6 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-((dimethylamino)methyl)-5-(4-nitrophenyl)thiophene-3-carboxylic acid 
• 737789-87-6 TAK-385 
• 737790-70-4 1-{4-[1-(2,6-difluorobenzyl)-5-{[(2-methoxyethyl)(methyl)amino]methyl}-3-(6-methoxypyridin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea 
• 737789-97-8 C₃₃H₃₆F₂N₆O₆S 

Relevant articles and documents

Nitrogen-containing heterocyclic group substituted pyrimidinedione compound and application thereof

The invention belongs to the technical field of medicines, and relates to a nitrogen-containing heterocyclic group substituted pyrimidinedione compound and application thereof, and a pharmaceutical composition containing the compound, which can be used as a gonadotropin releasing hormone receptor antagonist. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and application of the compound and the pharmaceutical composition in prevention or treatment of sex hormone dependent diseases including but not limited to prostate cancer, endometriosis,hysteromyoma, precocious puberty and the like.

Nitrogen-containing heteroaryl substituted pyrimidinedione compound and application thereof

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Bicyclic nitrogen-containing heteroaryl substituted pyrimidinedione compounds and application thereof

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Five-membered nitrogen-containing heteroaryl substituted pyrimidinedione compound and application thereof

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Substituted pyrimidinedione compound and application thereof

The invention belongs to the technical field of medicines, and relates to a substituted pyrimidinedione compound and application thereof, and a pharmaceutical composition containing the compound, which can be used as a gonadotropin releasing hormone receptor antagonist. The invention also relates to a method for preparing the compound and the pharmaceutical composition, and application of the compound and the pharmaceutical composition in prevention or treatment of sex hormone dependent diseases including but not limited to prostate cancer, endometriosis, hysteromyoma, precocious puberty and the like.

Discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6- methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3- d ]pyrimidin-6-yl]phenyl}-3-methoxyurea (TAK-385) as a potent, orally active, non-peptide antagonist of the human gonadotropin-releasing hormone receptor

We previously discovered an orally active human gonadotropin-releasing hormone (GnRH) receptor antagonist, thieno[2,3-d]pyrimidine-2,4-dione derivative 1 (sufugolix). To reduce the cytochrome P450 (CYP) inhibitory activity and improve in vivo GnRH antagonistic activity, further optimization of this scaffold was carried out. We focused our synthetic efforts on chemical modification at the 5 and 3 positions of the thieno[2,3-d]pyrimidine-2,4-dione ring based on computational modeling, which resulted in the discovery of 1-{4-[1-(2,6-difluorobenzyl)-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3- yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl} -3-methoxyurea (16b) as a highly potent and orally active GnRH antagonist. Compound 16b showed potent in vitro GnRH antagonistic activity in the presence of fetal bovine serum (FBS) without CYP inhibition. Oral administration of 16b maintained the suppressive effect of the plasma luteinizing hormone levels in castrated cynomolgus monkeys at a 3 mg/kg dose for more than 24 h. Compound 16b is currently under clinical development with the code name of TAK-385.

Thienopyrimidine compounds, their production and use

A compound of the formula: wherein R1and R2each is hydrogen, hydroxy, C1-4alkoxy, C1-4alkoxy-carbonyl or C1-4alkyl which may be substituted; R3is hydrogen, halogen, hydroxy or C1-4alkoxy which may be substituted; or adjacent two R3may form C1-4alkylenedioxy; R4is hydrogen or C1-4alkyl; R6is C1-4alkyl which may be substituted or a group of the formula: wherein R5is hydrogen or R4and R5may form heterocycle; and n is 0-5, or a salt thereof, has an excellent GnRH-antagonizing activity, and is useful for preventing or treating sex hormone-dependent diseases.

Thienopyrimidine compounds, their production and use

A compound of formula (I) wherein R1and R2each is hydrogen, hydroxy, C1-4alkoxy, C1-4alkoxy-carbonyl or C1-4alkyl which may be substituted; R3is hydrogen, halogen, hydroxy or C1-4alkoxy which may be substituted; or adjacent two R3may form C1-4alkylenedioxy; R4is hydrogen or C1-4alkyl; R6is C1-4alkyl which may be substituted or a group of the formula (A) wherein R5is hydrogen of R4and R5may form heterocycle; and n is 0-5, or a salt thereof, has an excellent GnRH-antagonizing activity, and is useful for preventing or treating sex hormone-dependent diseases.