On November 11, 2010, Kanzawa, Keizo; Kawaguchi, Kenichi; Matsumoto, Shunichiro; Nomura, Takaho; Susumu, Takashi; Seo, Tatsushi published a patent.Category: ethers-buliding-blocks The title of the patent was Preparation of azolecarboxamide compounds or their salts as antagonists of neurotrophic factor receptors (TrkA). And the patent contained the following:
N-Ph, N-pyridyl, or N-pyrazolylthiazole-4-carboxamides and oxazole-4-carboxamides the title compounds [I; X = S, O; R1 = Q, Q1, 3-methoxymethylmorpholin-4-yl, NR1cR1d; R1a = H, HO, lower alkoxy, cycloalkyloxy; R1b = H, lower alkoxy; R1c = H, lower alkyl; R1d = lower alkyl optionally substituted by lower alkoxy; R2 = H, lower alkyl optionally substituted by F or lower alkoxy, 3-tetrahydrofuryl, 4-tetrahydropyranyl; A = R2, Q3, Q4; R3 = CO2Me, Q5, CH2R3B; R00 = lower alkyl; R3B = OH, lower alkoxy, Q6, Q7, Q8, Q10, hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl; R0 = H, lower alkyl; m = 1,2; Ra = H, F, Ph, lower alkoxy-lower alkyl; R4 = lower alkyl optionally substituted by lower alkoxy] or salts thereof are prepared These compounds possess potent inhibitory activity against neurotrophic factor receptors (TrkA) and provide therapeutic and/or preventive agents for various lower urinary tract diseases accompanied by lower urinary tract pains such as interstitial cystitis and chronic prostatitis, urinary frequency accompanied by various lower urinary tract diseases including overactive bladder, feeling of micturition urgency, urinary incontinence, and various diseases accompanied by pain based on the TrkA-inhibitory activity. Thus, 67 mg (8aR)-octahydropyrrolo[1,2-a]pyrazine and 216 mg Cs2CO3 were added to a mixture of 200 mg N-[4-(chloromethyl)-2-[(2-methoxyethyl)carbamoyl]phenyl]-2-((3S)-3-methoxypyrrolidin-1-yl)-1,3-thiazole-4-carboxamide and 2 mL DMF and the resulting mixture was stirred at room temperature for 18 h to give, after workup and silica gel chromatog. and salt formation with fumaric acid, N-[4-[((8aR)-hexahydro-1H-pyrrolo[1,2-a]pyrazin-2-yl)methyl]-2-[(2-methoxyethyl)carbamoyl]phenyl]-2-((3S)-3-methoxypyrrolidin-1-yl)-1,3-thiazole-4-carboxamide (II) difumarate. II difumarate and N-phenylthiazole-4-carboxamide derivative (III) in vitro inhibited the NGF-induced increase in cellular calcium ion in HEK293 cells stably expressing human trkA receptor with IC50 of 19 and 16 nM, resp. The experimental process involved the reaction of (S)-1-Methoxypropan-2-amine hydrochloride(cas: 1162054-86-5).Category: ethers-buliding-blocks
The Article related to azolecarboxamide preparation antagonist neurotrophic factor receptor trka, thiazolecarboxamide oxazolecarboxamide preparation antagonist neurotrophic factor receptor trka, pain urinary tract disease treatment prevention thiazolecarboxamide oxazolecarboxamide preparation and other aspects.Category: ethers-buliding-blocks
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