308831-93-8

Usage

Uses

Used in Organic Chemistry Research:
2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester is used as a research compound for exploring its chemical properties and potential reactions due to its complex structure and multiple functional groups.
Used in Medicinal Chemistry:
2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester is used as a starting material or intermediate in the synthesis of pharmaceutically relevant molecules, leveraging its structural complexity and reactivity to create new drug candidates.
Used in Pharmaceutical Sciences:
2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester is used as a component in the development of new therapeutic agents, potentially contributing to the discovery of novel treatments for various diseases.
Used in Synthesis of Complex Molecules:
2-((ethoxycarbonyl)amino)-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester is employed as a building block in the synthesis of other complex organic molecules, taking advantage of its multiple reactive sites to facilitate the creation of new chemical entities.

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 174072-89-0 2-Amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester 
• 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 

Downstream Products

• 1589503-97-8 ethyl 2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-4-((dimethylamino)methyl)-5-(4-nitrophenyl)thiophene-3-carboxylate 
• 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 academic research and scientific papers

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

The invention belongs to the technical field of medicines, and relates to a five-membered nitrogen-containing heteroaryl substituted pyrimidinedione compound and application thereof, and a pharmaceutical composition containing the five-membered nitrogen-containing heteroaryl substituted pyrimidinedione compound, and the five-membered nitrogen-containing heteroaryl substituted pyrimidinedione compound and the pharmaceutical composition can be used as gonadotropin releasing hormone receptor antagonists. 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 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

The invention belongs to the technical field of medicines, and relates to a nitrogen-containing heteroaryl substituted pyrimidinedione compound and application thereof, and a pharmaceutical composition containing the compound, and the nitrogen-containing heteroaryl substituted pyrimidinedione compound and the pharmaceutical composition can be used as gonadotropin releasing hormone receptor antagonists. 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.

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.

Bicyclic nitrogen-containing heteroaryl substituted pyrimidinedione compounds and application thereof

The invention belongs to the technical field of medicines, and relates to bicyclic nitrogen-containing heteroaryl substituted pyrimidinedione compounds, application thereof, and a pharmaceutical composition containing the compounds. The compounds can be used as a gonadotropin releasing hormone receptor antagonist. The invention also relates to a method for preparing the compounds and the pharmaceutical composition, and application of the compounds 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.