165809-38-1

Usage

Uses

Used in Pharmaceutical Applications:
ETHYL 2-AMINO-5-(4-METHOXY-PHENYL)-4-METHYL-THIOPHENE-3-CARBOXYLATE is used as a key intermediate in the synthesis of new drugs, leveraging its unique structure to contribute to the development of pharmaceuticals with novel therapeutic properties.
Used in Research Applications:
In the field of research, ETHYL 2-AMINO-5-(4-METHOXY-PHENYL)-4-METHYL-THIOPHENE-3-CARBOXYLATE serves as a valuable compound for studying various biological processes. Its presence in experiments can help scientists understand the interactions of different functional groups with biological systems.
Used in Organic Chemistry:
ETHYL 2-AMINO-5-(4-METHOXY-PHENYL)-4-METHYL-THIOPHENE-3-CARBOXYLATE is utilized in organic chemistry for its potential to participate in a wide range of chemical reactions, contributing to the synthesis of complex organic molecules and materials.
Used in Materials Science:
In materials science, ETHYL 2-AMINO-5-(4-METHOXY-PHENYL)-4-METHYL-THIOPHENE-3-CARBOXYLATE may find applications due to its capacity to form new materials with unique properties. The diverse functional groups present in its structure can lead to the creation of materials with specific characteristics for various applications.

Upstream product

• 122-84-9 4-methoxybenzyl methyl ketone 
• 105-56-6 ethyl 2-cyanoacetate 
• 20620-37-5 2-Cyan-3-<4-methoxy-benzyl>-crotonsaeure-ethylester 

Downstream Products

• 165807-46-5 ethyl 6-(4-methoxyphenyl)-5-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno<2,3-d>pyrimidine-3-acetate 
• 190062-91-0 {3-Ethoxycarbonyl-5-(4-methoxyphenyl)-4-methylthiophen-2-yl}aminomethylene malonic acid diethyl ester 
• 949528-61-4 [2-({2-[4-(4-chloro-5-methyl-2-thiophen-2-yl-thieno[2,3-d]pyrimidin-6-yl)-phenoxy]-ethyl}-methyl-amino)-ethyl]-carbamic acid t-butyl ester 
• 1057337-60-6 (2-[4-(4-hydrazino-5-methyl-2-thiophen-2-yl-thieno[2,3-d]pyrimidin-6-yl)-phenoxy]-ethyl)-dimethyl-amine 
• 949528-08-9 (2-[4-(4-chloro-5-methyl-2-thiophen-2-yl-thieno[2,3-d]pyrimidin-6-yl)-phenoxy]-ethyl)-dimethyl-amine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel thieno[2,3-d]pyrimidine-based FLT3 inhibitors as anti-leukemic agents

The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML. A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents.

Synthesis and biological evaluation of novel thieno[2,3-d[pyrimidine-based FLT3 inhibitors as anti-leukemic agents

The most common mutations in acute myeloid leukemia (AML) are those that cause the activation of FMS-like tyrosine kinase 3 (FLT3). Therefore, FLT3 is regarded as a potential target for the treatment of AML. A novel series of thieno[2,3-d]pyrimidine-based analogs was designed and synthesized as FLT3 inhibitors. All synthesized compounds were assayed for the tyrosine kinase activity of FLT3 and growth inhibitory activity in four human leukemia cell lines (THP1, MV4-11, K562, and HL-60). Among these compounds, compound 17a, which possesses relatively short and simple substituents at the C6 position of thieno[2,3-d]pyrimidine, emerged as the most promising anti-leukemic agent. Compound 17a exhibited potent inhibition of FLT3-positive leukemic cell growth and of the FLT3 D835Y kinase; such inhibition is required for the successful treatment of AML. The data supports the further investigation of this class of compounds as potential anti-leukemic agents.

Substituted 2-Aminothiopen-derivatives: A potential new class of GluR6-Antagonists

In the course of search for new therapeutic agents against epilepsy new inhibitors for the kainate receptor subtypes GluR5 and GluR6 were synthesized. We were able to synthesize new substituted thieno[2,3-d]pyrimidines 3a,b, 4a,b, 5a,b as well as thiophene-3-carboxamides 2a-d and a multitude of substituted 4-methyl-5-phenylthiophene-3-carboxylic acids. All compounds described herein were tested for their antagonistic effect towards the kainate receptor subtypes GluR5 and GluR6. The highest activity was observed for ethyl 2-amino-4-methyl-5-phenylthiophene-3-carboxylate 1c with an IC50 = 0.75 μM at the GluR6 receptor.

NOVEL THIENOPYRIMIDINE DERIVATIVES OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF, PROCESS FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention relates to a novel thienopyrimidine derivative having an excellent anti? inflammatory and anti-cancer activity, or a pharmaceutically acceptable salt thereof, a process for the preparation thereof and a pharmaceutical composition comprising the same. The compound according to the present invention strongly inhibits IKB kinase-β (IKK-β) involved in the activation of a transcriptional factor, NF-κB, which is associated with inducing various immune and inflammatory diseases, whereby a composition comprising the compound is a useful therapeutic agent against inflammatory diseases, in particular, arthritis and cancer.

Discovery of a thieno[2,3-d]pyrimidine-2,4-dione bearing a p-methoxyureidophenyl moiety at the 6-position: A highly potent and orally bioavailable non-peptide antagonist for the human luteinizing hormone-releasing hormone receptor

We have previously disclosed the first potent and orally effective non-peptide antagonist for the human luteinizing hormone-releasing hormone (LHRH) receptor, a thieno[2,3-b]pyridin-4-one derivative, T-98475 (1). Extensive research on developing non-peptide LHRH antagonists has been carried out by employing a strategy of replacing the thienopyridin-4-one nucleus with other heterocyclic surrogates. We describe herein the design and synthesis of a series of thieno-[2,3-d]pyrimidine-2,4-dione derivatives containing a biaryl moiety, which led to the discovery of a highly potent and orally active non-peptide LHRH antagonist, 5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-[4- (3-methoxyureido)phenyl]-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (9k: TAK-013). Compound 9k showed high binding affinity and potent in vitro antagonistic activity for the human receptor with half-maximal inhibition concentration (IC50) values of 0.1 and 0.06 nM, respectively. Oral administration of 9k caused almost complete suppression of the plasma LH levels in castrated male cynomolgus monkeys at a 30 mg/kg dose with sufficient duration of action (more than 24 h). The results demonstrated that the thienopyrimidine-2,4-dione core is an excellent surrogate for the thienopyridin-4-one and that thienopyrimidine-2,4-diones and thienopyridin-4-ones constitute a new class of potent and orally bioavailable LHRH receptor antagonists. Furthermore, molecular modeling studies indicate that the unique methoxyurea side chain of 9k preferentially forms an intramolecular hydrogen bond between the aniline NH and the methoxy oxygen atom. The hydrogen bond will shield the hydrogen bonding moieties from the solvent and reduce the desolvation energy cost. It is therefore speculated that the intramolecular hydrogen bond resulting from judicious incorporation of an oxygen atom into the terminal alkyl group of the urea may increase the apparent lipophilicity to allow increased membrane permeability and consequently to improve the oral absorption of 9k in monkeys. On the basis of its profile, compound 9k has been selected as a candidate for clinical trials and it is expected that it will provide a new class of potential therapeutic agents for the clinical treatment of a variety of sex-hormone-dependent diseases.

Processes for the production of thienopyrimidine derivatives

The present invention provides a process for producing an intermediate for thienopyrimidine derivatives having the GnRH antagonistic activity at an industrial large scale. The process for production of the present invention relates to a process for produc

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.

Thienopyrimidine derivatives, their production and use

Thienopyrimidine derivatives are disclosed. Also disclosed are methods for the production and use of these compounds.

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