78347-96-3Relevant academic research and scientific papers
Novel phenanthrene compounds, a method of making the same and organic electronic devices using the same
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Page/Page column 21; 22; 25; 31; 35; 37, (2019/10/22)
The present invention relates to novel phenanthrene compounds having excellent luminous efficiency and lifespan, a manufacturing method thereof, and an organic electronic device including the novel phenanthrene compounds. The novel phenanthrene compounds according to the present invention can form steric conformation, can improve performance through improvement of electronic density, also can improve performance by regulating the molecular weight and position of a functional group because the molecular weight of the compounds is low, and can minutely regulate luminous wavelength and improve performance according to types of the functional groups. As the result, the organic electronic device including the novel phenanthrene compounds has high brightness, excellent thermal resistance, long lifespan, and high efficiency.
A depression drug impurity of preparing method (by machine translation)
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Paragraph 0021; 0031; 0035; 0036, (2018/09/11)
The invention relates to a depression drug impurity of preparing method, it comprises the following steps: (a) the high sodium iodate, water and mixed DMF; (b) is poured into ice water, adjusting pH with alkali and layered extraction, purification to obtain compound 4; in the 120 - 150 °C reaction after column chromatography separation to obtain compound 5; (c) the compound 3 and said compound 5 by adding ethylene glycol dimethyl ether, in the ice water bath under the conditions of the adding sodium hydride to, heating up to 40 - 60 °C reaction 20 - 40 minutes, further heating up to reflux; (d) the compound 6 with the [...] catalyst, morpholine, methanol and ethanol are mixed, the reaction is carried out in a hydrogen atmosphere, filtered [...] filtrate to obtain compound 7; (e) the compound 7 with formic acid, a sodium mixed, heated to 100 - 120 °C refluxing reaction; (g) the compound 10 in toluene soluble, in an inert gas atmosphere by adding sodium hydride, temperature reaction. This can obtain the high purity of the depression drug impurity isomer, for impurity accurate control. (by machine translation)
Preparation method of impurity isomer key intermediate of anti-depressive drug
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Paragraph 0018; 0033, (2018/09/11)
The invention relates to a preparation method of an impurity isomer key intermediate of an anti-depressive drug. The preparation method comprises the following steps: (a) mixing sodium periodate, water and DMF (Dimethylformamide); (b) pouring in ice water, adjusting pH with an alkaline solution, extracting by layers, purifying to obtain a compound 4, and performing column chromatography isolationafter reacting at 120 to 150 DEG C to obtain a compound 5; (c) adding the compound 3 and the compound 5 into 1,2-dimethoxyethane, adding sodium hydride under the condition of ice water bath, heating to 40 to 60 DEG C for reacting for 20 to 40 minutes, and heating and refluxing; (d) mixing the compound 6 with a rhodium carbon catalyst, morpholine, methanol and ethanol, reacting under a hydrogen atmosphere, and performing suction filtration and spin drying on filtrate to obtain a compound 7; (e) mixing the compound 7 with formic acid and sodium formate, and heating to 100 to 120 DEG C for refluxreaction; (f) adding anhydrous K2CO3,Cu powder and CuBr, performing reaction under the protection of insert gas at the temperature of 150 to 180 DEG C to obtain a compound 9; cooling to 30 to 60 DEGC, adding NaOH solution to perform reaction, filtering, and purfying to obtain a compound 10.. By adopting the preparation method, a high-purity impurity isomer of the anti-depressive drug can be obtained for accurate control of impurities.
Preparation method of chloronitrophenyl intermediate serving as impurity isomer of medicine for treating depression
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Paragraph 0013; 0023-0024; 0028, (2018/11/22)
The invention relates to a preparation method of a chloronitrophenyl intermediate serving as an impurity isomer of medicine for treating depression. The method includes the following steps that a, sodium periodate, water and DMF are mixed, then a DMF solution of a compound 2 is added for a reaction, and after the reaction, a filtrate is taken and purified to obtain a compound 3; b, 2-bromo-4-chlorotoluene, N-bromosuccinimide, dibenzoyl peroxide and carbon tetrachloride are mixed, stirred, heated to 80-100 DEG C for a reaction and then poured into ice water, the pH is adjusted with lye, and layered extraction and purification are conducted to obtain a compound 4; c, the compound 3 and a compound 5 are added into glycol dimethyl ether, sodium hydride is added under the condition of an ice water bath, the temperature is raised to 40-60 DEG C for a reaction for 20-40 minutes, then the temperature is raised for reflux, after the reaction is completed, water and ethyl acetate are added in avolume ratio of 1:1, and solid is precipitated, subjected to suction filtration and dried to obtain a compound 6. In this way, the nitrophenyl intermediate with high purity can be obtained to be usedfor subsequent preparation of the high-purity and high-yield impurity isomer of medicine for treating depression.
EFFLUX-PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
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Page/Page column 69; 86; 87, (2017/03/28)
The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof wherein ASC is -N(R8)ASC-1; ASC-1 is C 2-C 5alkylene-N(R9a)R9b or C(=O)-C 1-C 4alkylene-N(R
PIPERIDINE, PYRROLIDINE AND 2-OXO-1,3-OXAZINANE DERIVATIVES AS INHIBITORS OF BACTERIAL EFFLUX-PUMPS FOR THE TREATMENT OF MICROBIAL INFECTIONS
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Page/Page column 70, (2017/12/28)
The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof wherein ASC is Ring A represents a 4- to 6-membered saturated ring containing carbon atoms as ring members in addition to the nitrogen
EFFLUX-PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
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Page/Page column 187, (2016/12/26)
The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein ASC is -N(R8)(R9)ASC-1 ASC-1 is Ring A represents a 4- to 6-membered saturated ring containing carbon atoms as ring members in addition to the nitrogen atom and wherein one CH2 moiety in ring A is optionally replaced by CH(R21) and wherein one carbon atom in ring A that is not adjacent to the nitrogen atom is optionally replaced by O, and wherein ring A is connected to X via a carbon atom; X represents a bond, -CH2- or -C(=O)-; ARl, AR2 represent independently phenyl or a 5- to 6- membered heteroaryl ring containing one to three heteroatoms selected from O, S and N, wherein AR1 is connected to LI via a carbon atom, and wherein AR2 is connected to L1 and L2 via a carbon atom; R1, R2, R3 represent independently hydrogen, halogen, cyano, hydroxyl, C1-C6alkyl, C1-C6haloalkyl, C3- C8cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, -C1-C6alkylene-N(R12)R13, -N(R12)R13, -C(O)OR11l, - C(O)N(R12)R13, -S(O)OR11 or phenyl; R4 represents hydroxyl, hydrogen, halogen, nitro, cyano, amino, C1-C6alkyl optionally substituted by 1 to 5 R14, C2-C6alkenyl optionally substituted by 1 to 5 R14, C2-C6alkynyl optionally substituted by 1 to 5 R14, C1-C6alkoxy optionally substituted by 1 to 5 R14, C2-C6alkenyloxy optionally substituted by 1 to 5 R14, C2-C6alkynyloxy optionally substituted by 1 to 5 R14, -C(O)OR15, -CHO, -C(O)N(R16)R17, -C1- C6alkylene-N(R9)(R16)R17, -O-Cycle-P or -O-Cycle-Q; R5, R6, R7 represent independently hydrogen, halogen, cyano, Cl-C6alkyl, C1-C6haloalkyl, Cl-C6alkoxy or C1-C6haloalkoxy; R8 represents hydrogen, methyl or ASC-1; R9 is methyl or absent, and wherein when R9 is present the respective nitrogen atom carries a positive charge; R10 represents hydrogen or methyl; Rl11 represents independently at each occurrence hydrogen or C1-C6alkyl; R12, R13 represent independently at each occurrence hydrogen or C1-C6alkyl; R14 represents independently at each occurrence halogen, cyano, hydroxyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C8cycloalkyl, -C(O)OR11, -CHO, -C(O)N(R12)R13, -C1-C6alkylene-N(R12)R13, Cycle-P, O-Cycle-P, Cycle-Q or O-Cycle-Q; Cycle-P represents independently at each occurrence a saturated or partially unsaturated C3-C8 carbocyclic ring optionally substituted by 1 to 3 R18, or a saturated or partially unsaturated C3-C8 heterocyclic ring optionally substituted by 1 to 3 Rl 8 containing carbon atoms as ring members and one or two ring members independently selected from N(R9)(R12), N(R9) and O; Cycle-Q represents independently at each occurrence phenyl optionally substituted by 1 to 3 R19 or a 5- to 6-membered heteroaryl ring containing one to four heteroatoms selected from O, S and N, optionally substituted by 1 to 3 R19; R15 represents independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R16 and R17 represent independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R18 and R19 represent independently at each occurrence halogen, cyano, hydroxyl, oxo, amino, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, Cl-C4haloalkoxy or -CO(O)R11; R20 represents independently at each occurrence hydrogen or methyl; R21 represents N(R20)2 or CH2-N(R20)2; LI represents -CH=CH-, -CH2-O-, -O-CH2-, -CH2-O-CH2-,-CH2-S-, -S-CH2-, -CH2-S(O)-, -CH2-S(O2)-, -S(O)-CH2-; -S(O2)-CH2-, -C(CH3)(CH3)-, -C(=O)-NH-, -NH-C(=O)-, -CH2-CH2-, -CH=CH-CH2-, - CH2-NH-C(=O)-, -C(=O)-NH-CH2, -C≡C-, -S(O2)-NH-CH2-, -S(02)-NH, -O-CH2-CH2-O-, -O-, -NH- CH2-, -CH2-NH-, -CH2-CH2-O-, or -NH-C(=O)-CH2-O-, or a bond; L2 represents Cl-C7alkylene, wherein one or more CH2 moieties in the alkylene are optionally replaced independently by -N(R9)(R20)-, -CH(N(R9)(R20)(R20))-, or -C(=0)-, wherein within L2 there are no adjacent C(=O) moieties or adjacent -N(R9)(R20)- moieties, and wherein the terminal moiety of L2 is not - N(R9)(R20)-, or L2 represents -O-C1-C6alkylene-, or L2 represents a bond, providing that X represents - CH2- when L2 is a bond; as well as methods of using the compounds of formula I for treating or preventing bacterial infections.
Synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines; key synthons in syntheses of pharmaceutically active compounds
Jorgensen, Tine Krogh,Andersen, Knud Erik,Lau, Jesper,Madsen, Peter,Huusfeldt, Per Olaf
, p. 57 - 64 (2007/10/03)
Substituted 10,11-dihydro-5H-dibenz[b,f]azepines are key synthons in the syntheses of a number of pharmaceutically active compounds such as imipramine, chlorimipramine, and desimipramine analogues. A facile synthesis of substituted 10,11-dihydro-5H-dibenz[b,f]azepines is described, starting out from commercially available 2-bromotoluenes or 2-nitrotoluenes. Initial α-bromination with N-bromosuccinimide and subsequent reaction with triethylphosphite afforded the corresponding benzyl phosphonic ester derivatives. After reaction with benzaldehyde derivatives, the expected Horner-Emmons reaction products were obtained. Hydrogenation gave the amino derivatives which were transformed into the corresponding formamides. Under Goldberg conditions [1], the final ring closing step was performed to give the substituted 10,11-dihydro-5H-dibenz[b,f]azepines in 46-75% yield.
LITHIATION OF SOME 3THIOPHENES AND INTRAMOLECULAR TRANSMETALATION
Gronowitz, Salo,Stenhammar, Karin,Svensson, Leif
, p. 947 - 959 (2007/10/02)
The reaction of some halo-1-(thienyl)-2-phenylethanes such as 3-(2-phenylethyl)thiophene (1), 3-thiophene (2), 4--2-methylthiophene (3) and 4--2-chlorothiophene (4) with butyllithium and lithium diisopropylamide (LDA) under various conditions has been investigated.Competition between halogen-metal exchange in the benzene ring and metalation of thiophene ring was observed and an intramolecular transmetalation reaction was found.
