Novel heteroatom containing tetracyclic derivatives as selective estrogen receptor modulators
A compound, piperidine technology, applied in the field of tetracyclic derivatives, can solve the problems of high incidence and aggravation of leg cramps, and failure to improve the cognitive function of elderly patients
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[0550] The present invention also relates to the method for preparing the compound of formula (DX) described in detail in Scheme 16.
[0551]
[0552] Process 16
[0553] Accordingly, the appropriately substituted compound of formula (VIII) is a known compound or a compound prepared by a known method, wherein R A , R B , N, R 3 , M, R 4 And Z are the previous definitions, X is O or S, Pg 10 It is a suitable protecting group such as alkyl (e.g. methyl), benzyl, benzoyl, SEM, MOM, BOM, pivaloyl, etc. (see e.g. Protective Groups in Organic Chemistry , Editor-in-Chief J.F.W.McOmie, Plenum Press, 1973; T.W.Greene & P.G.M.Wuts, Protective Groups in Organic Synthesis , JohnWiley & Sons, 1991), react it with a base (such as LiHMDS, LDA, KHMDS, NaHMDS, etc.); preferably the reaction temperature is less than or equal to about room temperature, more preferably about 30°C to about -100°C, more preferably about -10 ℃ to about -30℃; solvent with aprotic organic solvents s...
Embodiment 1
[0582] Acetic acid 3-(2,4-dimethoxyphenyl)-7-hydroxy-4-methyl-2-oxo-2H-chromene-7-yl ester
[0583]
[0584] Combine 2,4-dihydroxyacetophenone (2.233g, 14.67mmol, 1eq), 2,4-dimethoxyphenylacetic acid (2.88g, 14.67mmol, 1eq), acetic anhydride (7.5mL, 78mmol, 5eq) A mixture of) and triethylamine (1.49 mL, 2.05 mmol, 1 eq) was stirred, and heated to reflux for 48 h under a nitrogen atmosphere. After cooling to room temperature, the black slurry reaction mixture was poured into ice water (~450 mL). To the mixture was slowly added solid sodium bicarbonate to neutralize the suspension of viscous semi-solid product. The mixture was then allowed to solidify overnight. The black solid was separated by filtration, washed with water, sucked dry, and recrystallized from acetic acid to obtain the title compound as a milky white crystalline solid. The second batch of product (0.95 g, 18.3%) was isolated from the mother liquor.
[0585] mp: 146-148°C
[0586] MS(CI)m / z355(M+H) +
[0587] 1 H...
Embodiment 2
[0591] Acetic acid 3-(2,4-dimethoxyphenyl)-8-hydroxy-4-methyl-2-oxo-2H-chromene-7-yl ester
[0592]
[0593] The title compound was prepared according to the method described in Example 1, in which 2,3-dihydroxyacetophenone was substituted for 2,4-dihydroxyacetophenone.
[0594] mp140-141℃
[0595] MS(CI)m / z 355, (M+H) + , 377(M+Na) +
[0596] 1 H NMR(300MHz, CDCl 3 ): δ 7.55 (1H, d, d, J = 4.2, 5.32 Hz), 7.29 (1H, d, J = 1.29 Hz), 7.27 (1H, d, J = 4.37 Hz), 7.08 (1H, d, J=8.13 Hz), 6.57-6.55 (2H, m), 3.86 (3H, s), 3.76 (3H, s), 2.43 (3H, s), 2.24 (3H, s).
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