- Synthesis method of tedizolid phosphate intermediate 3-fluoro-4-bromoaniline
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The invention provides a synthesis method of a tedizolid phosphate intermediate 3-fluoro-4-bromoaniline. The synthesis method comprises the following steps: (1) performing reacting of a compound 1 with ammonia gas to obtain a compound 2; (2) performing reacting of the compound 2 with hydrobromic acid to obtain a compound 3; and (3) reducing a cyano group in the compound 3 into an amino group to obtain a compound 4. The raw material adopted by the method is cheap and easy to obtain, and the method is mild in reaction condition, simple in equipment requirement, high in safety index and suitablefor large-scale commercial production. The yield of the tedizolid phosphate intermediate 3-fluoro-4-bromoaniline prepared by the process provided by the invention is up to 56.61% or above, the purityis up to 99.70% or above, and the content of isomer impurities in the product is as low as 0.17% or below. The invention provides the cheap and easily available high-quality intermediate for commercial production of tedizolid phosphate bulk drugs, and a wide application prospect is achieved.
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Paragraph 0051-0053; 0062-0065; 0076-0079; 0086-0089
(2020/12/09)
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- Preparation method of 4-amino-3-fluorobenzoic acid
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The invention relates to a preparation method of 4-amino-3-fluorobenzoic acid, which is characterized in that 4-amino-3-fluorobenzoic acid is prepared by taking 3,4-difluorobenzonitrile as a raw material, and perferably, the preparation method comprises the following steps: (1) allowing 3,4-difluorobenzonitrile to react with ammonia to form an intermediate, 3-fluorine-4-aminobenzonitrile, and (2)allowing the intermediate, 3-fluorine-4-aminobenzonitrile, to give a hydrolysis reaction under an alkaline condition to form 4-amino-3-fluorobenzoic acid. The preparation method takes cheap 3,4-difluorobenzonitrile as a main raw material, synthesizes 4-amino-3-fluorobenzoic acid with high yield and high purity through steps of ammoniation and hydrolysis, has the advantages of convenience in operation, low price and low environmental pollution, and can achieve large-scale industrial production.
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Page/Page column 7-12
(2019/05/08)
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- NOVEL GPR119 AGONIST COMPOUNDS
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The present invention relates to novel compounds of formula (I), process for preparation of the same and composition comprising these compounds.
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Paragraph 0533-0535
(2017/10/26)
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- ALKYNE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS
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Provided are compounds of formula (Ia) and pharmaceutically acceptable salts thereof, wherein A, B, R 1, R 2, m and n are as defined herein, which are active as inhibitors of S-Nitrosoglutathione reductase (GSNOR). These compounds prevent, inhibit, or suppress the action of GSNOR and are therefore useful in the treatment of GSNOR mediated diseases, disorders, syndromes or conditions such as, e.g., pulmonary hypertension, acute respiratory distress syndrome (ARDS), asthma, bronchospasm, cough, pneumonia, pulmonary fibrosis, interstitial lung diseases, cystic fibrosis and chronic obstructive pulmonary disease (COPD).
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Page/Page column 56; 57
(2016/05/02)
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- Ethyl cyanoacetate: A new cyanating agent for the palladium-catalyzed cyanation of aryl halides
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A new Pd-catalyzed cyanation reaction has been discovered using ethyl cyanoacetate as the cyanating reagent. A variety of electron-rich and electron-deficient aryl halides were efficiently converted into their corresponding nitriles in good to excellent yields.
- Zheng, Shuyan,Yu, Chunhui,Shen, Zhengwu
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supporting information; experimental part
p. 3644 - 3647
(2012/08/28)
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- Design, synthesis, and biological evaluation of novel diarylalkyl amides as TRPV1 antagonists
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We have developed a new class of diarylalkyl amides as novel TRPV1 antagonists. They exhibited potent 45Ca2+ uptake inhibitions in rat DRG neuron. In particular, the amide 59 was identified as a potent antagonist with IC50 of 57 nM. The synthesis and structure-activity relationship of the diarylalkyl amides are also described.
- Li, Fu-Nan,Kim, Nam-Jung,Paek, Seung-Mann,Kwon, Do-Yeon,Min, Kyung Hoon,Jeong, Yeon-Su,Kim, Sun-Young,Park, Young-Ho,Kim, Hee-Doo,Park, Hyeung-Geun,Suh, Young-Ger
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experimental part
p. 3557 - 3567
(2009/09/27)
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- Synthesis and structural optimization of multiple H-bonding region of diarylalkyl (thio)amides as novel TRPV1 antagonists
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Structural optimization of multiple H-bonding region and structure-activity relationship of diarylalkyl amides/thioamides as novel TRPV1 antagonists are described. In particular, we identified amide 34o and thioamides 35o and 35r, of which antagonistic activities were highly enhanced by an incorporation of cyano or vinyl-substituent to the multiple H-bonding region. They exhibited potent 45Ca2+ uptake inhibitions in rat DRG neuron with IC50s of 25, 32 and 28 nM, respectively.
- Li, Fu-Nan,Kim, Nam-Jung,Chang, Dong-Jo,Jang, Jaebong,Jang, Hannah,Jung, Jong-Wha,Min, Kyung-Hoon,Jeong, Yeon-Su,Kim, Sun-Young,Park, Young-Ho,Kim, Hee-Doo,Park, Hyeung-Geun,Suh, Young-Ger
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experimental part
p. 8149 - 8160
(2010/03/25)
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- NOVEL COMPOUNDS, ISOMER THEREOF, OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF AS VANILLOID RECEPTOR ANTAGONIST; AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
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This present invention relates to novel compounds, isomer thereof or pharmaceutically acceptable salts thereof as vanilloid receptor (Vanilloid Receptor 1; VR1; TRPV1) antagonist; and a pharmaceutical composition containing the same. The present invention provides a pharmaceutical composition for preventing or treating a disease such as pain, inflammatory disease of the joints, neuropathies, HIV-related neuropathy, nerve injury, neurodegeneration, stroke, urinary bladder hypersensitivity including urinary incontinence, cystitis, stomach duodenal ulcer, irritable bowel syndrome (IBS) and inflammatory bowel disease (IBD), fecal urgency, gastro-esophageal reflux disease (GERD), Crohn's disease, asthma, chronic obstructive pulmonary disease, cough, neurotic/allergic/inflammatory skin disease, psoriasis, pruritus, prurigo, irritation of skin, eye or mucous membrane, hyperacusis, tinnitus, vestibular hypersensitivity, episodic vertigo, cardiac diseases such as myocardial ischemia, hair growth-related disorders such as effluvium, alopecia, rhinitis, and pancreatitis.
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Page/Page column 82-83; 129
(2010/11/28)
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- UREAS AS FACTOR XA INHIBITORS
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The present invention is directed to compounds represented by Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, and prodrugs thereof which are inhibitors of Factor Xa. The present invention is also directed to and intermediates used in making such compounds, pharmaceutical compositions containing such compounds, methods to prevent or treat a number of conditions characterized by undesired thrombosis and methods of inhibiting the coagulation of a blood sample.
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Page/Page column 68-69
(2010/11/08)
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- Novel potent antagonists of transient receptor potential channel, vanilloid subfamily member 1: Structure-activity relationship of 1,3-diarylalkyl thioureas possessing new vanilloid equivalents
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Recently, 1,3-diarylalkyl thioureas have merged as one of the promising nonvanilloid TRPV1 antagonists possessing excellent therapeutic potential in pain regulation. In this paper, the full structure-activity relationship for TRPV1 antagonism of a novel series of 1,3-diarylalky thioureas is reported. Exploration of the structure-activity relationship, by systemically modulating three essential pharmacophoric regions, led to six examples of 1,3-dibenzyl thioureas, which exhibit Ca2+ uptake inhibition in rat DRG neuron with IC50 between 10 and 100 nM.
- Suh, Young-Ger,Lee, Yong-Sil,Min, Kyung-Hoon,Park, Ok-Hui,Kim, Jin-Kwan,Seung, Ho-Sun,Seo, Seung-Yong,Lee, Bo-Young,Nam, Yeon-Hee,Lee, Kwang-Ok,Kim, Hee-Doo,Park, Hyeung-Geun,Lee, Jeewoo,Oh, Uhtaek,Lim, Ju-Ok,Kang, Sang-Uk,Kil, Min-Jung,Koo, Jae-Yeon,Shin, Song Seok,Joo, Yung-Hyup,Kim, Jin Kwan,Jeong, Yeon-Su,Kim, Sun-Young,Park, Young-Ho
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p. 5823 - 5836
(2007/10/03)
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- Amide-type triazole compounds
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A compound of formula (I) or a pharmacologically acceptable prodrug or salt thereof which exhibits excellent antifungal activity: wherein Ar1 represents a phenyl group or the like; Ar2 represents a phenylene group or the like. X represents a sulfur atom or a methylene group. R1 represents a hydrogen atom or a C1-3 alkyl group; R2 represents a hydrogen atom or a C1-3 alkyl group; and R3 represents an optionally substituted C6-10 aryl group or the like. Fungal infections may be prevented and/or treated by administering said compound (I) or said prodrug or salt thereof.
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- INHIBITORS OF FACTOR XA WITH A NEUTRAL P1 SPECIFICITY GROUP
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The present application describes inhibitors of factor Xa with a neutral P1 specificity group of formula I: STR1 or pharmaceutically acceptable salt forms thereof, wherein R and E may be groups such as methoxy and halo.
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- Pyrimidine derivatives and liquid crystal compositions including same
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2-phenyl-5-(4'-trans-cyclohexyl) phenyl pyrimidine derivatives represented by the general formula: STR1 wherein R is a straight chain alkyl group having 1 to 10 carbon atoms; X is CN or F; Y is F or H; Z is F or H; and when X is F, at least one of Y and Z is H; and the cyclohexane ring is a trans isomer, exhibiting a nematic phase and having a high nematic phase-isotropic liquid phase transition temperature (N-I Point) and large positive dielectric constant anisotropy (Δε). The pyrimidine derivatives may be included in liquid crystal compositions for improved display devices having a wide temperature range, including a high N-I point, a low threshold voltage and a low driving voltage.
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- 1,3-dioxane derivatives, methods of preparation and liquid crystal compositions including same
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Trans-2-phenyl-5-trans-4'-alkylcyclohexyl-1,3-dioxane derivatives represented by the general formula: STR1 wherein R is a linear alkyl group of 1 to 10 carbon atoms, A is a single covalent bond or a --CH2 CH2 -- group, X is F or CN,
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- Cycloalkanapyrazole-3-carbonitrile herbicides
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Herbicidal cycloalkanapyrazoles of the formula: STR1 where N IS 3, 4 OR 5; R1 is hydrogen or methyl; X is fluorine, chlorine, bromine, iodine, cyano, or methoxy; Y is hydrogen, fluorine, or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine, chlorine or methoxy; provided that (a) when n is 3, R1 must be hydrogen; (b) when n is 5, R1 must be hydrogen, Y must be hydrogen or fluorine, Z and V must both be hydrogen, and X must be fluorine, chlorine or bromine; (c) when V is methoxy, X and Y must be chlorine, and Z must be hydrogen; and (d) when V is fluorine or chlorine, X must be fluorine, chlorine or bromine, and Z must be hydrogen.
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- Substituted isoindoles
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This invention relates to novel compounds of the formulae and their use as herbicides: STR1 wherein X is H, F, Cl, Br, CN, NO2 or OCH3 ; Y is H, F, or CH3 ; and Z is H, F, Cl, Br or OCH3 provided that (1) when Y
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