136592-00-2

Upstream product

• 5326-23-8 6-Chloro-3-pyridinecarboxylic acid 
• 79-37-8 oxalyl dichloride 
• 58757-38-3 6-Chloronicotinoyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 186581-53-3 diazomethane 
• 53939-30-3 5-bromo-2-chloropyridine 
• 67442-07-3 2-chloro-N-methoxy-N-methylacetamide 

Downstream Products

• 1251957-86-4 2-[4-(2-{[(2R)-2-(6-chloropyridin-3-yl)-2-hydroxyethyl]amino}-2-methylpropyl)phenyl]-N-(5-methylisoxazol-3-yl)acetamide 
• 1251957-87-5 2-[4-(2-{[(2R)-2-hydroxy-2-(pyridin-3-yl)ethyl]amino}-2-methylpropyl)phenyl]-N-(5-methylisoxazol-3-yl)acetamide 

Relevant academic research and scientific papers

ANTIVIRAL COMPOUNDS

The present invention provides compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

HETEROCYCLIC AMINE DERIVATIVES

The present invention relates to compounds of formula I wherein A, B, X, Y, Ar, R1, R2, R′, m and n are as defined herein and to pharmaceutical active acid addition salts thereof. Compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds can be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

HETEROCYCLIC AMINE DERIVATIVES

The present invention relates to compounds of formula (I) wherein R1 is hydrogen, lower alkyl, halogen, lower alkyl substituted by halogen, lower alkoxy, lower alkoxy substituted by halogen, cyano, nitro, C3-6-cycloalkyl, -CH2-C3-6-cycloalkyl, -O-CH2-C3-6-cycloalkyl, -O-(CH2)2-O-lower alkyl, S(O)2CH3, SF5, -C(O)NH-lower alkyl, phenyl, -O-pyrimidinyl, optionally substituted by lower alkoxy substituted by halogen, or is benzyl, oxetanyl or furanyl; m Ar is aryl or heteroaryl, selected from the group consisting of phenyl, naphthyl, pyrimidinyl, pyridinyl, benzothiazolyl, quinolinyl, quinazolinyl, benzo[d][1.3]dioxolyl, 5,6,7,8- tetrahydro-quinazolinyl, pyrazolyl, pyrazinyl, pyridazinyl, or 1,3,4-oxadiazolyl; Y is a bond, -CH2-, -CH2CH2-, -CH(CF3)- or -CH(CH3)-; R2 is hydrogen or lower alkyl; A is CR or N; and R is hydrogen, cyano, halogen or lower alkyl; R' is hydrogen or halogen; with the proviso that when R' is halogen, then A is CH; B is CH or N; n is 0, 1 or 2; X is a bond, -CH2- or -O-; pharmaceutical active acid addition salts thereof. It has now been found that the compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

The synthesis of two potent β-3 adrenergic receptor agonists

This contribution describes the initial preparation of two potent β-3 receptor agonists 1 and 2. Subsequent scale up of these two compounds was required for further evaluation and proceeded via a common key amine intermediate 24. Synthesis of this key intermediate by way of a Ritter reaction was a vital step in the sequence. Enantioselective Noyori hydrogenation reactions gave access to the chiral epoxides necessary to make the target compounds. Chemistry was developed for the selective dehalogenation of the 2-chloropyridyl group in the presence of a sensitive isoxazole unit to provide access to 1.

The chemistry of pseudomonic acid part 14. Synthesis and in vivo biological activity of heterocyclyl substituted oxazole derivatives

Semisynthetic analogues of pseudomonic acid A have been prepared containing a heterocyclyl substituted oxazole. Derivatives in which the heterocycle was thiophene, furan, pyridine, or isoxazole showed good antibacterial potency and were further evaluated in vivo. Both pharmacokinetic parameters and oral activity against an experimental intraperitoneal sepsis were superior to results obtained from previously described pseudomonic acid A derivatives.