174069-44-4

Upstream product

• 697-73-4 2,6-difluorobenzyl chloride 
• 174072-80-1 ethyl 4-hydroxy-3-methyl-2-phenylthieno[2,3-b]pyridine-5-carboxylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 4815-38-7 ethyl 2-amino-4-methyl-5-phenylthiophene-3-carboxylate 
• 174072-77-6 ethyl N-[3-carboxy-4-methyl-5-phenyl-2-thienyl]aminomethylenemalonate 
• 174072-73-2 2-[(3-ethoxycarbonyl-4-methyl-5-phenyl-thiophen-2-ylamino)-methylene]-malonic acid diethyl ester 

Downstream Products

• 174070-98-5 ethyl 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-2-(4-nitrophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylate 
• 174071-01-3 2-(4-aminophenyl)-3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 174069-67-1 3-bromomethyl-7-(2,6-difluorobenzyl)-4,7-dihydro-2-(4-nitrophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 903520-56-9 ({4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-methyl)-carbamic acid tert-butyl ester 
• 903520-57-0 acetic acid 1-{4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-cyclopropyl ester 
• 192886-68-3 3-(N-benzyl-N-methylaminomethyl)-4,7-dihydro-7-(2,6-difluorobenzyl)-2-(4-trifluoroacetylaminophenyl)-4-oxothieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 192886-69-4 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-N-methoxy-N-methyl-4-oxo-2-(4-trifluoroacetamidophenyl)thieno[2,3-b]pyridine-5-carboxamide 
• 253434-02-5 acetic acid 1-{4-[3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-5-isobutyryl-4-oxo-4,7-dihydro-thieno[2,3-b]pyridin-2-yl]-phenylcarbamoyl}-1-methyl-ethyl ester 
• 903520-54-7 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-2-(4-trifluoroacetamidophenyl)-4-oxothieno[2,3-b]pyridine 
• 174071-92-2 3-[(benzyl-methyl-amino)-methyl]-7-(2,6-difluoro-benzyl)-4-oxo-2-(4-propionylamino-phenyl)-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 192886-70-7 3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-2-(4-isobutyrylaminophenyl)-N-methoxy-N-methyl-4-oxothieno[2,3-b]pyridine-5-carboxamide 
• 174072-38-9 7-(2,6-difluorobenzyl)-4,7-dihydro-3-(N-methyl-N-benzylaminomethyl)-2-(4-isobutyrylaminophenyl)-5-isobutyryl-4-oxo-thieno[2,3-b]pyridine 
• 174072-26-5 2-(4-aminophenyl)-3-(N-benzyl-N-methylaminomethyl)-7-(2,6-difluorobenzyl)-4,7-dihydro-5-isobutyryl-4-oxothieno[2,3-b]pyridine 

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.

Combined use of GnRH agonist and antagonist

PCT No. PCT/JP97/01459 Sec. 371 Date Aug. 14, 1997 Sec. 102(e) Date Aug. 14, 1997 PCT Filed Apr. 25, 1997 PCT Pub. No. WO97/40846 PCT Pub. Date Nov. 6, 1997The present invention relates to a pharmaceutical luteinizing hormone releasing hormone agonist in combination with a luteinizing hormone releasing hormone antagonist. By using a luteinizing hormone releasing hormone agonist and a luteinizing hormone releasing hormone antagonist in combination, the transient exacerbation with elevation of serum testosterone and estrogen owing to the pituitary-gonadotropic action (acute action) manifested immediately following an initial dose of the luteinizing hormone releasing hormone agonist can be successfully obviated.

THIENOPYRIDINE COMPOUNDS WHICH HAVE USEFUL PHARMACEUTICAL ACTIVITY

The present thienopyrimidine derivatives and compositions having gonadotropin-releasing hormone antagonistic activity are useful as propylactics or therapeutic agents for the prevention or treatment of several hormone dependent diseases, for example, a se