737789-93-4

Usage

Molecular structure

A complex organic compound with a thiophene core and various substituents such as benzyl, ethoxycarbonyl, methoxycarbamoyl, and methoxyethylamino groups.

Potential pharmaceutical activity

The presence of functional groups commonly associated with pharmaceutical drugs suggests that 2-[(2,6-difluorobenzyl)(ethoxycarbonyl)amino]-5-{4-[(methoxycarbamoyl)amino]phenyl}-4-{[(2-methoxyethyl)(methyl)amino]methyl}thiophene-3-carboxylic acid may have potential pharmaceutical or biological activity.

Further research and testing

The specific properties and applications of 2-[(2,6-difluorobenzyl)(ethoxycarbonyl)amino]-5-{4-[(methoxycarbamoyl)amino]phenyl}-4-{[(2-methoxyethyl)(methyl)amino]methyl}thiophene-3-carboxylic acid would need to be determined through additional research and testing to confirm its potential uses and effectiveness.

Structural features

The compound contains a benzyl ring with two fluorine atoms at the 2nd and 6th positions, an ethoxycarbonyl group, a methoxycarbamoyl group, and a methoxyethylamino group attached to the thiophene core.

Functional groups

The compound has various functional groups such as amino, carboxyl, and methoxy groups that contribute to its potential pharmaceutical or biological activity.

Complexity

The compound's long chemical name and complex structure indicate that it may have a wide range of interactions with biological systems, which could be explored for potential therapeutic applications.

Upstream product

• 174072-89-0 2-Amino-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester 
• 577780-07-5 ethyl 5-(4-aminophenyl)-2-[(2,6-difluorobenzyl)(ethoxycarbonyl)amino]-4-{[(2-methoxyethyl)(methyl)amino]methyl}thiophene-3-carboxylate 
• 308832-01-1 ethyl 2-[(2,6-difluorobenzyl)(ethoxycarbonyl)amino]-4-{[(2-methoxyethyl)(methyl)amino]methyl}-5-(4-nitrophenyl)thiophene-3-carboxylate 
• 308831-95-0 4-(bromomethyl)-2-((2,6-difluorobenzyl)(ethoxycarbonyl)amino)-5-(4-nitrophenyl)thiophene-3-carboxylic acid ethyl ester 
• 308831-94-9 2-((2,6-difluorobenzyl)(ethoxycarbonyl)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 
• 737789-92-3 ethyl 2-[(2,6-difluorobenzyl)(ethoxycarbonyl)amino]-5-{4-[(methoxycarbamoyl)amino]phenyl}-4-{[(2-methoxyethyl)(methyl)amino]methyl}thiophene-3-carboxylate 

Downstream Products

• 737789-97-8 C₃₃H₃₆F₂N₆O₆S 
• 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 
• 737789-87-6 TAK-385 

Relevant academic research and scientific papers

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.

PREMATURE OVULATION PREVENTIVE AGENT

The present invention provides a premature ovulation inhibitor for use in in vitro fertilization or embryo transfer process, which contains a nonpeptidic compound having a gonadotropin releasing hormone antagonistic action. The premature ovulation inhibitor for use in in vitro fertilization or embryo transfer process of the present invention is low toxic, permits oral administration, and has a superior inhibitory effect on premature ovulation in in vitro fertilization or embryo transfer process.

THIENOPYRIMIDINE COMPOUNDS AND USE THEREOF

The present invention provides a compound represented by the formula: wherein R1 is a C1-4 alkyl; R2 is (1) a 5- to 7-membered nitrogen-containing heterocyclic group which may have a substituent selected from the group consisting of (1') a halogen, (2') a hydroxy group, (3') a C1-4 alkyl and (4') a C1-4 alkoxy, (2) a phenyl which may have a substituent selected from the group consisting of (1') a halogen, (2') a C1-4 alkoxy-C1-4 alkyl, (3') a mono-C1-4 alkyl-carbamoyl-C1-4 alkyl, (4') a C1-4 alkoxy and (5') a mono-C1-4 alkylcarbamoyl-C1-4 alkoxy, or the like; R3 is a C1-4 alkyl; R4 is a C1-4 alkoxy, or the like; n is an integer of 1 to 4; or a salt thereof, as a thienopyrimidine compound having gonadotropin-releasing hormone antagonistic activity.