174072-82-3

Upstream product

• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 4815-38-7 ethyl 2-amino-4-methyl-5-phenylthiophene-3-carboxylate 
• 174072-73-2 2-[(3-ethoxycarbonyl-4-methyl-5-phenyl-thiophen-2-ylamino)-methylene]-malonic acid diethyl ester 
• 174072-77-6 ethyl N-[3-carboxy-4-methyl-5-phenyl-2-thienyl]aminomethylenemalonate 
• 174072-80-1 ethyl 4-hydroxy-3-methyl-2-phenylthieno[2,3-b]pyridine-5-carboxylate 

Downstream Products

• 174071-46-6 4,7-Dihydro-7-(2-fluorobenzyl)-3-(N-methyl-N-benzylaminomethyl)-2-(4-N'-methylureidophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 174070-97-4 ethyl 3-(N-benzyl-N-methylaminomethyl)-4,7-dihydro-7-(2-fluorobenzyl)-2-(4-nitrophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylate 
• 174071-00-2 2-(4-amino-phenyl)-3-[(benzyl-methyl-amino)-methyl]-7-(2-fluoro-benzyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 174069-65-9 3-bromomethyl-7-(2-fluoro-benzyl)-2-(4-nitro-phenyl)-4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 174069-39-7 ethyl 4,7-dihydro-7-(2-fluorobenzyl)-3-methyl-2-(4-nitrophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylate 

Relevant academic research and scientific papers

Design, synthesis, and structure-activity relationships of thieno[2,3-b]pyridin-4-one derivatives as a novel class of potent, orally active, non-peptide luteinizing hormone-releasing hormone receptor antagonists

Design, synthesis, and structure-activity relationships of thieno[2,3-b]pyridin-4-one-based non-peptide luteinizing hormone-releasing hormone (LHRH) receptor antagonists are described. Starting with the thienopyridin-4-one derivative 26d (T-98475) an optimization study was performed, which resulted in the identification of a highly potent and orally bioavailable LHRH receptor antagonist, 3-(N-benzyl-N-methylaminomethyl)-7-(2,6- difluorobenzyl)-4,7-dihydro-2-[4-(1-hydroxy-1-cyclopropanecarboxamido)phen-yl] -5-isobutyryl-4-oxothieno[2,3-b]pyridine (33c). Compound 33c displayed subnanomolar in vitro activities for the human receptor and its oral administration caused effective suppression of the plasma LH levels in castrated male cynomolgus monkeys. Furthermore, SAR studies revealed that a hydroxyalkylamido moiety on the 2-phenyl ring is virtually equivalent to an alkylureido moiety, at least in this series of compounds.

Thienopyridine compounds, their production and use

The compound of the present invention possesses excellent gonadotropin-releasing hormone antagonizing activity, and is useful for preventing or treating sex hormone-dependent diseases, e.g., sex hormone-dependent cancers (e.g., prostatic cancer, uterine cancer, breast cancer, pituitary tumor), prostatic hypertrophy, hysteromyoma, endometriosis, precocious puberty, amenorrhea syndrome, multilocular ovary syndrome, pimples etc, or as a pregnancy regulator (e.g., contraceptive), infertility remedy or menstruation regulator.