173206-13-8

Basic information

• Product Name: 4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one
• Synonyms: 4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one;3(2H)-Pyridazinone, 4,5-Dichloro-2-(Tetrahydro-2H-Pyran-2-Yl)-;5-dichloro-2-(tetrahydropyran -2-yl)-2H-pyridazin-3-one;3(2H)-Pyridazinone, 4,5-Dichloro-2-(Tetrahydro-2H-Pyran-2-Yl)-(WX636096)
• CAS NO: 173206-13-8
• Molecular Formula: C₉H₁₀Cl₂N₂O₂
• Molecular Weight: 249.0939
• Mol File: 173206-13-8.mol

Chemical Properties

• Melting Point: 75-77 °C(Solv: ethyl acetate (141-78-6); cyclohexane (110-82-7))
• Boiling Point: 318.7±52.0 °C(Predicted)
• Appearance: /
• Density: 1.57±0.1 g/cm3(Predicted)
• PKA: -3.81±0.20(Predicted)
• CAS DataBase Reference: 4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one(173206-13-8)
• EPA Substance Registry System: 4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one(173206-13-8)

Safety Data

• Hazardous Substances Data: 173206-13-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one is used as a building block for the synthesis of various drugs and biologically active molecules. Its unique structure allows for the development of new pharmaceutical compounds with potential therapeutic applications.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one serves as a valuable intermediate for the synthesis of novel compounds with potential biological activities. Its structural features can be further modified to explore new chemical entities with improved pharmacological properties.
Used in Drug Discovery and Development:
4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one is utilized in drug discovery and development processes to identify and optimize new lead compounds with therapeutic potential. Its unique chemical properties can contribute to the design of innovative drugs targeting various diseases and conditions.
Used in Chemical Synthesis:
In the realm of chemical synthesis, 4,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one is employed as a versatile reagent for the preparation of a wide range of chemical products. Its ability to participate in various chemical reactions makes it a valuable component in the synthesis of complex organic molecules.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 932-22-9 4,5-dichloro-2H-pyridazin-3-one 
• 932-22-9 4,5-Dichloro-3-hydroxypyridazine 

Downstream Products

• 645405-25-0 4-(3,4-dimethoxyphenethyl)-7-(tetrahydro-2H-pyran-2-yl)-2H-pyridazino[4,5-b][1,4]oxazine-3,8(4H,7H)-dione 
• 645405-29-4 2-[5-chloro-6-oxo-1-(tetrahydro-pyran-2-yl)-1,6-dihydro-pyridazin-4-yloxy]-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide 
• 1164166-19-1 4,5-bis[3-(4-bromophenyl)-5-methyl-1H-pyrazol-1-yl]-2-(tetrahydro-2H-pyran-2-yl)-3(2H)-pyridazinone 
• 1191455-61-4 4-chloro-5-(methyl-phenyl-amino)-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one 
• 1353565-31-7 2-(tetrahydro-2H-pyran-2-yl)-5-(p-tolyl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-1,6(2H,5H)-dione 
• 1353565-43-1 3-(tetrahydro-2H-pyran-2-yl)-5-(p-tolyl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-4,6(3H,5H)-dione 
• 1353565-29-3 5-(4-chlorophenyl)-2-(tetrahydro-2H-pyran-2-yl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-1,6(2H,5H)-dione 
• 1353565-41-9 5-(4-chlorophenyl)-3-(tetrahydro-2H-pyran-2-yl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-4,6(3H,5H)-dione 
• 1353565-30-6 5-(4-bromophenyl)-2-(tetrahydro-2H-pyran-2-yl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-1,6(2H,5H)-dione 
• 1353565-42-0 5-(4-bromophenyl)-3-(tetrahydro-2H-pyran-2-yl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-4,6(3H,5H)-dione 
• 1353565-32-8 5-(4-methoxyphenyl)-2-(tetrahydro-2H-pyran-2-yl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-1,6(2H,5H)-dione 
• 1353565-44-2 5-(4-methoxyphenyl)-3-(tetrahydro-2H-pyran-2-yl)pyrrolo[1',2':1,6]pyrazino[2,3-d]pyridazine-4,6(3H,5H)-dione 
• 1353565-46-4 9-methoxy-2-(tetrahydro-2H-pyran-2-yl)-5-(p-tolyl)pyridazino[4',5':5,6]pyrazino[1,2-a]indole-1,6(2H,5H)-dione 
• 1353565-51-1 9-methoxy-3-(tetrahydro-2H-pyran-2-yl)-5-(p-tolyl)pyridazino[4',5':5,6]pyrazino[1,2-a]indole-4,6(3H,5H)-dione 

Relevant articles and documents

COMPOUNDS AND METHODS FOR CD73 MODULATION AND INDICATIONS THEREFOR

Disclosed are compounds of Formula I: or a pharmaceutically acceptable salt, a solvate, a tautomer, a stereoisomer or a deuterated analog thereof, wherein R1, R2, R3, A, L, and G are as described in any of the embodiments described in this disclosure; compositions thereof; and uses thereof.

COMPOUNDS AND METHODS FOR CD73 MODULATION AND INDICATIONS THEREFOR

Disclosed are compounds of Formula (I): or a pharmaceutically acceptable salt, a solvate, a tautomer, a stereoisomer or a deuterated analog thereof, wherein R1, R2, R3, A, E, L, and G are as described in any of the embodiments described in this disclosure; compositions thereof; and uses thereof.

Designing Functionally Selective Noncatechol Dopamine D1 Receptor Agonists with Potent in Vivo Antiparkinsonian Activity

Dopamine receptors are important G protein-coupled receptors (GPCRs) with therapeutic opportunities for treating Parkinson's Disease (PD) motor and cognitive deficits. Biased D1 dopamine ligands that differentially activate G protein over β-arrestin recruitment pathways are valuable chemical tools for dissecting positive versus negative effects in drugs for PD. Here, we reveal an iterative approach toward modification of a D1-selective noncatechol scaffold critical for G protein-biased agonism. This approach provided enhanced understanding of the structural components critical for activity and signaling bias and led to the discovery of several novel compounds with useful pharmacological properties, including three highly GS-biased partial agonists. Administration of a potent, balanced, and brain-penetrant lead compound from this series results in robust antiparkinsonian effects in a rodent model of PD. This study suggests that the noncatechol ligands developed through this approach are valuable tools for probing D1 receptor signaling biology and biased agonism in models of neurologic disease.

PYRIDAZINONES AND METHODS OF USE THEREOF

Disclosed are compounds according to Formula (A), and related tautomers and pharmaceutical compositions. Also disclosed are therapeutic methods, e.g., of treating kidney diseases, using the compounds of Formula (A).

One-Pot Highly Regioselective Synthesis of Indole-Fused Pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones by a Smiles Rearrangement

A simple and convenient synthesis of indole-fused pyridazino[4,5- b ][1,4]benzoxazepin-4(3 H)-ones is described. A range of 2-(1 H -indol-2-yl)phenols and 4,5-dichloropyridazin-3-ones are compatible with this reaction. A Smiles rearrangement is proposed as a key step in the highly regioselective construction of the products. The easy availability of the starting materials makes this an appealing method in organic synthesis.

Melanin-Concentrating Hormone Receptor 1 Antagonists Lacking an Aliphatic Amine: Synthesis and Structure-Activity Relationships of Novel 1-(Imidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one Derivatives

Aiming to discover melanin-concentrating hormone receptor 1 (MCHR1) antagonists with improved safety profiles, we hypothesized that the aliphatic amine employed in most antagonists reported to date could be removed if the bicyclic motif of the compound scaffold interacted with Asp123 and/or Tyr272 of MCHR1. We excluded aliphatic amines from our compound designs, with a cutoff value of pKa 8, and explored aliphatic amine-free MCHR1 antagonists in a CNS-oriented chemical space limited by four descriptors (TPSA, ClogP, MW, and HBD count). Screening of novel bicyclic motifs with high intrinsic binding affinity for MCHR1 identified the imidazo[1,2-a]pyridine ring (represented in compounds 6a and 6b), and subsequent cyclization of the central aliphatic amide linkage led to the discovery of a potent, orally bioavailable MCHR1 antagonist 4-[(4-chlorobenzyl)oxy]-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one 10a. It exhibited low potential for hERG inhibition and phospholipidosis induction as well as sufficient brain concentration to exert antiobesity effects in diet-induced obese rats.

HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS

The present invention provides, in part, compounds of Formula (I): and pharmaceutically acceptable salts thereof; processes for the preparation of; intermediates used in the preparation of; and compositions containing such compounds or salts, and their uses for treating D1-mediated (or D1 -associated) disorders including, e.g., schizophrenia (e.g., its cognitive and negative symptoms), schizotypal personality disorder, cognitive impairment (e.g., cognitive impairment associated with schizophrenia, AD, PD, or pharmacotherapy therapy), ADHD, Parkinson's disease, anxiety, and depression.

HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS

The present invention provides, in part, compounds of Formula (I) and pharmaceutically acceptable salts thereof; processes for the preparation of; intermediates used in the preparation of; and compositions containing such compounds or salts, and their uses for treating D1-mediated (or D1 -associated) disorders including, e.g., schizophrenia (e.g., its cognitive and negative symptoms), schizotypal personality disorder, cognitive impairment (e.g., cognitive impairment associated with schizophrenia, AD, PD, or pharmacotherapy therapy), ADHD, Parkinson's disease, anxiety, and depression.

HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS

The present invention provides, in part, compounds of Formula I: and pharmaceutically acceptable salts thereof; processes for the preparation of; intermediates used in the preparation of; and compositions containing such compounds or salts, and their uses for treating D1-mediated (or D1 -associated) disorders including, e.g., schizophrenia (e.g., its cognitive and negative symptoms), schizotypal personality disorder, cognitive impairment (e.g., cognitive impairment associated with schizophrenia, AD, PD, or pharmacotherapy therapy), ADHD, Parkinson's disease, anxiety, and depression.

HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS

The present invention provides, in part, compounds of Formula I: and pharmaceutically acceptable salts thereof and N-oxides of the foregoing; processes for the preparation of; intermediates used in the preparation of; and compositions containing such compounds, salts or N-oxides, and their uses for treating D1-mediated (or D1-associated) disorders including, e.g., schizophrenia (e.g., its cognitive and negative symptoms), cognitive impairment (e.g., cognitive impairment associated with schizophrenia, AD, PD, or pharmacotherapy therapy), ADHD, impulsivity, compulsive gambling, overeating, autism spectrum disorder, MCI, age-related cognitive decline, dementia, RLS, Parkinson's disease, Huntington's chorea, anxiety, depression, MDD, TRD, and bipolar disorder.