On March 10, 2005, Kumagai, Toshihito; Kuwada, Takeshi; Shibata, Tsuyoshi; Hayashi, Masato; Fujisawa, Yuri; Sekiguchi, Yoshinori published a patent.Computed Properties of 141940-37-6 The title of the patent was Preparation of 1-[1-(benzenesulfonyl)-3-phenyl-2-oxo-1,3-dihydro-2H-indol-3-yl]-4-fluoro-L-proline derivatives as antagonists of arginine-vasopressin V1b receptor. And the patent contained the following:
1,3-Dihydro-2H-indol-2-one derivatives represented by the formula (I) (wherein R1 = halogeno, C1-4 alkyl, C1-4 alkoxy, CF3, CF3O; R2 = H, halogeno, C1-4 alkyl, C1-4 alkoxy, CF3; or R2 is present in the 6-position of the indol-2-one and is bonded to R1 to form C3-6 alkylene; R3 = halogeno, hydroxy, C1-4 alkyl, C1-4 alkoxy, CF3O; R4 = H, halogeno, C1-4 alkyl, C1-4 alkoxy; or R4 is present in the 3-position of the Ph and is bonded to R3 to form methylenedioxy; R5 = H, F; R6 = ethylamino, dimethylamino, azetidin-1-yl, C1-4 alkoxy; R7, R8 = C1-4 alkoxy) or pharmaceutically acceptable salts thereof are prepared These compounds have antagonistic activity against an arginine-vasopressin V1b receptor and are useful for the prevention or treatment of depression, anxiety, Alzheimer’s disease, Parkinson’s disease, Huntington chorea, eating disorder, hypertension, digestive tract diseases, drug dependence, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, head trauma, inflammation, immune diseases, and alopecia. Thus, 3.78 g 3,5-dichloro-3-(2-methoxyphenyl)-1,3-dihydro-2H-indol-2-one and 7.27 g (4R)-4-fluoro-N,N-dimethyl-L-prolinamide trifluoroacetate were suspended in 40 mL CHCl3, treated with 7.47 g Et3N, and stirred at room temperature for 13 h to give, after silica gel chromatog., (+)- and (-)-(4R)-1-[5-chloro-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-fluoro-N,N-dimethyl-L-prolinamide (II). (-)-II (2.00 g) was added to a mixture of 0.215 g NaH and 20 mL DMF under ice-cooling, stirred for 40 min, treated with a solution of 1.27 g 2,4-dimethoxybenzenesulfonyl chloride in 5 mL DMF, and stirred for 35 min under ice-cooling and then at room temperature for 1 h to give (-)-(4R)-1-[5-chloro-1-[(2,4-dimethoxyphenyl)sulfonyl]-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-fluoro-N,N-dimethyl-L-prolinamide (III). III inhibited the binding of [3H]Arg-vasopressin to arginine-vasopressin receptor VIb and VIa by 50% at 1-100 x 10-9 M and 10-8-10-6 M, resp. The experimental process involved the reaction of tert-Butyl (4-(trifluoromethyl)phenyl)carbamate(cas: 141940-37-6).Computed Properties of 141940-37-6
The Article related to benzenesulfonylphenyloxodihydroindolylfluoroproline preparation antagonist arginine vasopressin v1b receptor, oxodihydroindolylfluoroprolinamide preparation antagonist arginine vasopressin v1b receptor, oxodihydroindolylfluoroproline preparation antagonist arginine vasopressin v1b receptor and other aspects.Computed Properties of 141940-37-6
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