38336-06-0Relevant articles and documents
Chemoselective deprotection of teriary benzylamines and reduction of carbon-carbon double bonds in the presence of benzyl and benzyloxymethyl ethers
Bajwa,Slade,Repic
, p. 6025 - 6028 (2000)
Catalytic transfer hydrogenation using 10% Pd-C in the presence of 1,4-cyclohexadiene as the hydrogen donor selectively debenzylates amines and reduces carbon-carbon double bonds while leaving benzyl and benzyloxymethyl ethers intact. (C) 2000 Elsevier Sc
Discovery of Novel Indazole Derivatives as Orally Available β3-Adrenergic Receptor Agonists Lacking Off-Target-Based Cardiovascular Side Effects
Wada, Yasuhiro,Nakano, Seiji,Morimoto, Akifumi,Kasahara, Ken-ichi,Hayashi, Takahiko,Takada, Yoshio,Suzuki, Hiroko,Niwa-Sakai, Michiko,Ohashi, Shigeki,Mori, Mutsuhiro,Hirokawa, Takatsugu,Shuto, Satoshi
, p. 3252 - 3265 (2017/05/05)
We previously discovered that indazole derivative 8 was a highly selective β3-adrenergic receptor (β3-AR) agonist, but it appeared to be metabolically unstable. To improve metabolic stability, further optimization of this scaffold was carried out. We focused on the sulfonamide moiety of this scaffold, which resulted in the discovery of compound 15 as a highly potent β3-AR agonist (EC50 = 18 nM) being inactive to β1-, β2-, and α1A-AR (β1/β3, β2/β3, and α1A/β3 > 556-fold). Compound 15 showed dose-dependent β3-AR-mediated responses in marmoset urinary bladder smooth muscle, had a desirable metabolic stability and pharmacokinetic profile (Cmax and AUC), and did not obviously affect heart rate or mean blood pressure when administered intravenously (3 mg/kg) to anesthetized rats. Thus, compound 15 is a highly potent, selective, and orally available β3-AR agonist, which may serve as a candidate drug for the treatment of overactive bladder without off-target-based cardiovascular side effects.
INDAZOLE ANALOGUE
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Page/Page column 110, (2012/08/14)
[Objective] To provide a drug that selectively stimulates the β3-adrenergic receptors, particularly a drug capable of preferentially stimulating the β3-adrenergic receptors over the α1-adrenergic receptors. This drug can be used in the treatment and prevention of diabetes, obesity, hyperlipidemia, depression, cholelithiasis, diseases caused by biliary hyperkinesia, diseases caused by hyperfunction of the gastrointestinal tract, interstitial cystitis, overactive bladder or urinary incontinence, diseases associated with decreased lacrimation, and the like. [Solution] Indazole analogs represented by the general formula (I) or a salt thereof. Drugs that contains these indazole analogs or a salt thereof as the active ingredient.
INDAZOLE DERIVATIVES
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Page/Page column 59-60, (2010/06/22)
Compounds represented by the Formula (A-1) and the Formula (1) or salt thereof are provided. The compounds represented by the Formula (A-1) and the Formula (1) or salt thereof have a β3 adrenergic receptor agonist activity, and therefore are useful as an agent for the prevention and treatment of diabetes, obesity, hyperlipidemia, depression, biliary stone, a disorder derived from hyperactivity of biliary tract, a disorder derived from hyperactivity of digestive tract, interstitial cystitis, overactive bladder, urinary incontinence or a disorder derived from decreased tear secretion, etc.
INDAZOLE COMPOUNDS
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Page/Page column 80, (2010/07/04)
Provided are compounds represented by the following formula (A-1) and formula (1), or salts thereof. The compounds of formula (A-1) and formula (1) or salts thereof have 133 adrenergic receptor agonist activity, and thus are useful as therapeutic and prophylactic agent for diabetes mellitus, obesity, hyperlipidemia, depression, diseases caused by gallstones or hypermotility of the biliary tract, diseases caused by hyperactivity of the digestive tract, interstitial cystitis, overactive bladder or urinary incontinence, or as therapeutic and prophylactic agents for diseases concomitant with decreased tears.
A novel series of urea-based peptidomimetic calpain inhibitors
Sanders, M. Lee,Donkor, Isaac O.
, p. 1965 - 1968 (2007/10/03)
A series of peptide aldehyde derivatives in which the P2 chiral carbon has been replaced with nitrogen were synthesized as urea-based peptidomimetic inhibitors of μ-calpain. The compounds mirrored the general SAR of peptidyl aldehyde calpain inhibitors but displayed greater selectivity for μ-calpain over cathepsin B.
Chemoselective oxidative debenzylation of tertiary N-benzyl amines
Bull, Steven D.,Davies, Stephen G.,Fenton, Garry,Mulvaney, Andrew W.,Prasad, R. Shyam,Smith, Andrew D.
, p. 337 - 338 (2007/10/03)
Treatment of tertiary amines containing one or more N-benzyl protecting groups with aqueous ceric ammonium nitrate results in clean N-debenzylation to afford the corresponding secondary amine.
Chemoselective debenzylation of N-benzyl tertiary amines with ceric ammonium nitrate
Bull, Steven D.,Davies, Stephen G.,Fenton, Carry,Mulvaney, Andrew W.,Shyam Prasad,Smith, Andrew D.
, p. 3765 - 3774 (2007/10/03)
Treatment of a range of N-benzyl tertiary amines with aqueous eerie ammonium nitrate results in N-debenzylation to afford the corresponding secondary amine. Chemoselective mono-W-debenzylation of N-benzyl tertiary amines is shown to occur in the presence of N-benzyl amides, O-benzyl ethers, O-benzyl esters, O-benzyl phenolates and 5-benzyl ethers. The Royal Society of Chemistry 2000.
Selective O-benzylation of aminoalkanols
Hu,Cassady
, p. 907 - 913 (2007/10/02)
A simple and one-step method has been developed for selective O-benzylation of aminoalkanols. Study of steric effects shows the best selectivity in adjacent 1°-OH vs 2°-CHNH2 and decreased selectivity in 2°-OH vs 1°-CH2NH2 and non adjacent aminoalkanol.
SYNTHESIS OF N-SUBSTITUTED IMIDOETHYL-3-AMINOMETHYL-2,3-DIHYDRO-1,4-DIOXINOPYRIDINES
Benarab, Abdelhakim,Comoy, Corinne,Guillaumet, Gerald
, p. 1641 - 1650 (2007/10/02)
The multistep synthesis of N-substituted imidoethyl-3-aminomethyl-2,3-dihydro-1,4-dioxinopyridines using as a final step the Mitsunobu reaction between aliphatic alcohols and imides is described.
