79201-39-1

Usage

Uses

Used in Pharmaceutical Synthesis:
Hydrazinecarboxylic acid, cyclopentylidene-, 1,1-dimethylethyl ester (9CI) is used as a key intermediate in the synthesis of various pharmaceuticals. Its strong electrophilic reactivity enables the formation of new chemical bonds, facilitating the creation of diverse drug molecules.
Used in Organic Chemistry:
In the field of organic chemistry, Hydrazinecarboxylic acid, cyclopentylidene-, 1,1-dimethylethyl ester (9CI) serves as a valuable building block for the production of a wide range of organic compounds. Its versatility in chemical reactivity allows for the synthesis of various organic molecules with different functional groups and properties.
Used in Research and Development:
Hydrazinecarboxylic acid, cyclopentylidene-, 1,1-dimethylethyl ester (9CI) is also utilized in research and development for exploring new chemical reactions and developing innovative synthetic routes. Its unique reactivity and properties make it a valuable tool for chemists in discovering new compounds and optimizing existing synthetic processes.
Safety Precautions:
As with any chemical compound, it is essential to observe proper handling and safety precautions when working with Hydrazinecarboxylic acid, cyclopentylidene-, 1,1-dimethylethyl ester (9CI). This includes minimizing potential health and environmental risks by following established safety guidelines and protocols.

InChI:InChI=1/C10H18N2O2/c1-10(2,3)14-9(13)12-11-8-6-4-5-7-8/h4-7H2,1-3H3,(H,12,13)

Upstream product

• 870-46-2 t-butoxycarbonylhydrazine 
• 120-92-3 cyclopentanone 

Downstream Products

• 646071-31-0 tert-butyl 2-cyclopentylhydrazinecarboxylate 
• 24214-72-0 cyclopentylhydrazine hydrochloride 
• 30923-92-3 cyclopentylhydrazine 
• 693287-72-8 (1-cyclopentyl-5-(4-methylthiophenyl)pyrazol-3-yl)methanol 
• 693287-71-7 methyl 1-cyclopentyl-5-(4-methylthiophenyl)pyrazol-3-carboxylate 
• 693287-73-9 [1-cyclopentyl-5-(4-methanesulfonyl-phenyl)-1H-pyrazol-3-yl]-methanol 
• 1608125-61-6 1-cyclopentyl-3-methyl-5-((3-methyl-1-phenyl-1H-pyrazol-5-yl)methoxy)-1H-pyrazole 

Relevant academic research and scientific papers

Pyrazole Agonist of the Apelin Receptor Improves Symptoms of Metabolic Syndrome in Mice

Apelin receptor agonism improves symptoms of metabolic syndrome. However, endogenous apelin peptides have short half-lives, making their utility as potential drugs limited. Previously, we had identified a novel pyrazole-based agonist scaffold. Systematic modification of this scaffold was performed to produce compounds with improved ADME properties. Compound 13 with favorable agonist potency (cAMPi EC50 = 162 nM), human liver microsome stability (T1/2 = 62 min), and pharmacokinetic profile in rodents was identified. The compound was tested in a mouse model of diet-induced obesity (DIO) and metabolic syndrome for efficacy. Treatment with 13 led to significant weight loss, hypophagia, improved glucose utilization, reduced liver steatosis, and improvement of disease-associated biomarkers. In conclusion, a small-molecule agonist of the apelin receptor has been identified that is suitable for in vivo investigation of the apelinergic system in DIO and perhaps other diseases where this receptor has been implicated to play a role.

Identification of potent pyrazole based APELIN receptor (APJ) agonists

The apelinergic system comprises the apelin receptor and its cognate apelin and elabela peptide ligands of various lengths. This system has become an increasingly attractive target for pulmonary and cardiometabolic diseases. Small molecule regulators of this receptor with good drug-like properties are needed. Recently, we discovered a novel pyrazole based small molecule agonist 8 of the apelin receptor (EC50 = 21.5 μM, Ki = 5.2 μM) through focused screening which was further optimized to initial lead 9 (EC50 = 0.800 μM, Ki = 1.3 μM). In our efforts to synthesize more potent agonists and to explore the structural features important for apelin receptor agonism, we carried out structural modifications at N1 of the pyrazole core as well as the amino acid side-chain of 9. Systematic modifications at these two positions provided potent small molecule agonists exhibiting EC50 values of 100 nM. Recruitment of β-arrestin as a measure of desensitization potential of select compounds was also investigated. Functional selectivity was a feature of several compounds with a bias towards calcium mobilization over β-arrestin recruitment. These compounds may be suitable as tools for in vivo studies of apelin receptor function.

Drug Discovery against Psoriasis: Identification of a New Potent FMS-like Tyrosine Kinase 3 (FLT3) Inhibitor, 1-(4-((1H-Pyrazolo[3,4-d]pyrimidin-4-yl)oxy)-3-fluorophenyl)-3-(5-(tert-butyl)isoxazol-3-yl)urea, That Showed Potent Activity in a Psoriatic Animal Model

Psoriasis is a chronic T-cell-mediated autoimmune disease, and FMS-like tyrosine kinase 3 (FLT3) has been considered as a potential molecular target for the treatment of psoriasis. In this investigation, structural optimization was performed on a lead compound, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (1), which showed a moderate inhibitory activity againt FLT3. A series of pyrazolo[3,4-d]pyrimidine derivatives were synthesized, and structure-activity relationship analysis led to the discovery of a number of potent FLT3 inhibitors. One of the most active compounds, 1-(4-(1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)-3-fluorophenyl)-3-(5-tert-butylisoxazol-3-yl)urea (18b), was then chosen for in-depth antipsoriasis studies because this compound displayed the highest potency in a preliminary antipsoriasis test. Compound 18b exhibited significant antipsoriatic effects in the K14-VEGF transgenic mouse model of psoriasis, and no recurrence was found 15 days later after the last administration. Detailed mechanisms of action of compound 18b were also investigated. Collectively, compound 18b could be a potential drug candidate for psoriasis treatment.

PROTEIN KINASE INHIBITORS

The present invention relates to a novel family of inhibitors of protein kinases. In particular, the present invention relates to inhibitors of the members of the Tec and Src protein kinase families.

Structure-activity relationships of pyrazole derivatives as potential therapeutics for immune thrombocytopenias

Idiopathic or immune thrombocytopenia (ITP) is a serious clinical disorder involving the destruction of platelets by macrophages. Small molecule therapeutics are highly sought after to ease the burden on current therapies derived from human sources. Earlier, we discovered that dimers of five-membered heterocycles exhibited potential to inhibit phagocytosis of human RBCs by macrophages. Here, we reveal a structure-activity relationship of the bis-pyrazole class of molecules with -C-C-, -C-N- and -C-O- linkers, and their evaluation as inhibitors of phagocytosis of antibody-opsonized human RBCs as potential therapeutics for ITP. We have uncovered three potential candidates, 37, 47 and 50, all carrying a different linker connecting the two pyrazole moieties. Among these compounds, hydroxypyrazole derivative 50 is the most potent compound with an IC50 of 14 ± 9 μM for inhibiting the phagocytosis of antibody-opsonized human RBCs by macrophages. None of the compounds exhibited significant potential to induce apoptosis in peripheral blood mononuclear cells (PBMCs). Current study has revealed specific functional features, such as up to 2-atom spacer arm and alkyl substitution at one of the N1 positions of the bivalent pyrazole core to be important for the inhibitory activity.

PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE DERIVATIVES AS PDE9 INHIBITORS

A compound of the general formula (I) wherein R1 is selected from the group consisting of phenyl unsubstituted or substituted with 1 to 3 substituents selected from F, Cl, Br, I, CN, -O-C1-C3-alkyl, fluorinated -O-C1-C3-alkyl, -(CH2)mOH and 5-membered heterocyclic group with 1 or 2 heteroatoms selected from N, O and S; and 6- or 10-membered heteroaryl with 1 to 3 heteroatoms selected from O, N and S; R2 and R3 independently of each other represent H atom or straight or branched C1-C3 alkyl; R4 is selected from the group consisting of 4- to 6- membered cycloalkyl, wherein one of carbon atoms can be replaced by O atom, and which is unsubstituted or substituted with one or two halogen atoms,and straight or branched C1-C4 alkyl; Q represents a bond or C1-C3-alkylene, which can be optionally substituted by one to three C1-C3-alkyls; X is selected from the group consisting of O, NR5, and S(O)p; R5 represents H atom or C1-C3alkyl; m is 1, 2 or 3; p is 0, 1 or 2; and salts thereof, for use as a medicament, in particular for treating cognitive function disorders and neurodegenerative diseases.

PYRAZOLE DERIVATIVES AND THEIR USES THEREOF

The present disclosure relates to a compound of formula (I) or a pharmaceutically acceptable salt thereof; wherein U, R1, R2, R3 and Q are as defined herein. The disclosure also provides a method for treating or preventing a method for the prevention, treatment and/or alleviation of one or more autoimmune or alloimmune disease, pharmaceutical compositions and combination comprising a therapeutically effective amount of a compound, as defined herein.

PROTEIN KINASE INHIBITORS

The present invention relates to a novel family of inhibitors of protein kinases. In particular, the present invention relates to inhibitors of the members of the Tec and Src protein kinase families.

PROCESS FOR THE SYNTHESIS OF BETA-AMINOCARBONYLS

The present application provides processes and intermediates useful in the production of β- aminocarbonyl- or β-aminothiocarbonyl-containing compounds. Provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazone. Also provided herein is a process for synthesizing β-aminocarbonyl- or β-aminothiocarbonyl-containing compounds from an alkene and a hydrazine. The present application further provides intermediate aminoisocyanate and iminoisocyanate compounds, and methods for synthesizing the starting hydrazone and hydrazine compounds.

A tunable route for the synthesis of azomethine imines and β-aminocarbonyl compounds from alkenes

Cyclic azomethine imines possessing a β-aminocarbonyl motif are accessed from simple alkene and hydrazone starting materials. A thermal, concerted alkene aminocarbonylation pathway involving an imino-isocyanate intermediate is proposed and supported by DF