- Facile preparation of 5-alkyl-1-aryltetrazoles with arenes, acyl chlorides, hydroxylamine, and diphenylphosphoryl azide
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Successive treatment of arenes with acyl chlorides and AlCl3, the addition of water and removal of solvent, the reaction with NH2OH?HCl and K2CO3, and the reaction with diphenylphosphoryl azide and DBU under warming conditions gave the corresponding 5-alkyl-1-aryltetrazoles efficiently in good to moderate yields. The present method is one-pot transformation of arenes into 5-alkyl-1-aryltetrazoles using the Friedel-Crafts acylation and the Beckmann rearrangement under transition-metal-free conditions.
- Shibasaki, Kaho,Togo, Hideo
-
p. 1816 - 1830
(2020/11/19)
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- ANTIBACTERIAL COMPOUNDS
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The present invention relates to compounds of general formula (II),to compositions comprising these compounds and to methods of treating Enterobacteriaceae bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Enterobacteriaceae.
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Page/Page column 82-83
(2019/05/22)
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- Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
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We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
- Liu, Guangchang,Xu, Bo
-
supporting information
p. 869 - 872
(2018/02/09)
-
- Synthesis, and antitubercular and antimicrobial activity of 1′-(4-chlorophenyl)pyrazole containing 3,5-disubstituted pyrazoline derivatives
-
A new series of 1′-(4-chlorophenyl)-5-(substituted aryl)-3′-(substituted aryl)-3,4-dihydro-2H,1′H-[3,4′]bipyrazolyl derivatives (6a-e, 8a-e, 10a-e) have been synthesized, characterized and screened for antimicrobial and antitubercular activity. Among the synthesized compounds, the minimum inhibition concentration of 10e was found to be as low as 1.56 μg ml-1 and that of 10c was 6.25 μg ml-1 as compared to the standard anti-tb drugs pyrazinamide and streptomycin.
- Harikrishna,Isloor, Arun M.,Ananda,Obaid, Abdulrahman,Fun, Hoong-Kun
-
supporting information
p. 73 - 76
(2016/01/12)
-
- A new solvent system (Cyclopentyl methyl ether-water) in process development of darifenacin HBr
-
Darifenacin is a potent and competitive M3 selective receptor antagonist (M3SRA), and its hydrobromide salt (1) is the active ingredient of pharmaceutical formulations for oral treatment of urinary incontinence. The present work demonstrates an efficient, commercial manufacturing process for darifenacin hydrobromide (1).
- Pramanik, Chinmoy,Bapat, Kiran,Chaudhari, Ashok,Tripathy, Narendra K.,Gurjar, Mukund K.
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p. 1591 - 1597
(2013/02/23)
-
- SUBSTITUTED ALKYNYL PHENOXY COMPOUNDS AS NEW SYNERGISTS IN PESTICIDAL COMPOSITIONS
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A composition comprising an alkynyl phenoxy compound of Formula (I) as a synergist and a pesticidal active ingredient is described, wherein R1 and R2, similar or different, are (C1-C4)alkyl or R1O- an
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Page/Page column 29-30
(2011/04/13)
-
- Substituted alkynyl phenoxy compounds and their uses
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An alkynyl phenoxy compound of Formula (I) is described, wherein R1 and R2, similar or different, are (C1-C4)alkyl or R1O- and R2O- together represent a group -O-CH2-O-, -O-CH(CH
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Page/Page column 14-15
(2011/04/14)
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- CARBINOL DERIVATIVES HAVING CYCLIC LINKER
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[Object] To provide a novel LXRβ agonist that is useful as a preventative and/or therapeutic agent for atherosclerosis; arteriosclerosis such as those resulting from diabetes; dyslipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases that are caused by inflammatory cytokines; skin diseases such as allergic skin diseases; diabetes; or Alzheimer's disease. [Solving Means] A carbinol compound represented by the following general formula (I) or salt thereof, or their solvate.
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Page/Page column 19
(2010/03/31)
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- CARBINOL DERIVATIVES HAVING HETEROCYCLIC LINKER
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[Object] It is to provide a novel LXRβ agonist useful as a preventative and/or therapeutic agent for atherosclerosis; arteriosclerosis such as those resulting from diabetes; dyslipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases that are caused by inflammatory cytokines; skin diseases such as allergic skin diseases; diabetes; or Alzheimer's disease. [Solving Means] A carbinol compound represented by the following general formula (I) or salt thereof, or their solvate: (wherein, each V and W independently show N or C—R7; each X and Y independently show CH2, C═O, SO2, etc; Z shows CH or N; each R1, R2 and R7 independently show a hydrogen atom, C1-8 alkyl group, etc.; R3 shows C1-8 alkyl group; R4 shows an optionally substituted C6-10 aryl group or an optionally substituted 5- to 11-membered heterocyclic group; R5 and R6 show a hydrogen atom, etc.; L shows a C1-8 alkyl chain optionally substituted with an oxo group, etc.; and n shows any integer of 0 to 2.)
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Page/Page column 16
(2010/12/29)
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- SUBSTITUTED PYRROLIDINES
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Disclosed herein are substituted pyrrolidine-based muscarinic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 30; 31
(2009/01/24)
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- 4' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, R5, R6, B, D, E, G, Q, x and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 33
(2009/01/24)
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- 6' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY
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The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1—R4 A, B, D, E, and G are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.
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Page/Page column 55-56
(2008/12/08)
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- Tricyclic [1,2,4]triazine 1,4-dioxides as hypoxia selective cytotoxins
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A series of novel tricyclic triazine-di-N-oxides (TTOs) related to tirapazamine have been designed and prepared. A wide range of structural arrangements with cycloalkyl, oxygen-, and nitrogen-containing saturated rings fused to the triazine core, coupled with various side chains linked to either hemisphere, resulted in TTO analogues that displayed hypoxia-selective cytotoxicity in vitro. Optimal rates of hypoxic metabolism and tissue diffusion coefficients were achieved with fused cycloalkyl rings in combination with both the 3-aminoalkyl or 3-alkyl substituents linked to weakly basic soluble amines. The selection was further refined using pharmacokinetic/pharmacodynamic model predictions of the in vivo hypoxic potency (AUCreq) and selectivity (HCD) with 12 TTO analogues predicted to be active in vivo, subject to the achievement of adequate plasma pharmacokinetics.
- Hay, Michael P.,Hicks, Kevin O.,Pchalek, Karin,Lee, Ho H.,Blaser, Adrian,Pruijn, Frederik B.,Anderson, Robert F.,Shinde, Sujata S.,Wilson, William R.,Denny, William A.
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supporting information; experimental part
p. 6853 - 6865
(2009/12/03)
-
- TRICYCLIC 1,2,4-TRIAZINE OXIDES AND COMPOSITIONS THEREFROM FOR THERAPEUTIC USE IN CANCER TREATMENTS
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The invention relates to novel tricyclic 1,2,4-triazine-1-oxides and novel tricyclic 1,2,4-triazine-1,4-dioxides of formula: (I); and to related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.
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Page/Page column 135
(2008/06/13)
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- COMPOUNDS HAVING BOTH α7 NICOTINIC AGONIST ACTIVITY AND 5HT3 ANTAGONIST ACTIVITY FOR TREATMENT OF CNS DISEASES
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The invention discloses compounds that are selective α7 nAChR agonists and 5-HT3 antagonists. The compounds are useful for treating many CNS diseases.
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-
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- 2-Hydroxymethyl-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl] -1-benzenesulfonamide (DRF-4367): An orally active COX-2 inhibitor identified through pharmacophoric modulation
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Analogs of 1,5-diarylpyrazoles with a novel pharmacophore at N1 were designed, synthesized and evaluated for the in-vitro cyclooxygenase (COX-1/COX-2) inhibitory activity. The variations at/around position-4 of the C-5 phenyl ring in conjunction with a CF3 and CHF2 groups at C-3 exhibited a high degree of potency and selectivity index (SI) for COX-2 inhibition. The in-vivo evaluation of these potent compounds with a few earlier ones indicated the 4-OMe-phenyl analog 6 and the 4-NHMe-phenyl analog 9 with a CF3, and the 4-OEt-phenyl analog 19 with a CHF2 group at C-3 to possess superior potency than celecoxib. In addition to its impressive anti-inflammatory, antipyretic, analgesic and anti-arthritic properties, compound 6 (DRF-4367) was found to possess an excellent pharmacokinetic profile, gastrointestinal (GI) safety in the long-term arthritis study and COX-2 potency in human whole blood assay. Thus, compound 6 was selected as an orally active anti-inflammatory candidate for pre-clinical evaluation.
- Singh, Sunil Kumar,Vobbalareddy, Saibaba,Kalleda, Srinivasa Rao,Rajjak, Shaikh Abdul,Casturi, Seshagiri Rao,Datla, Srinivasa Raju,Mamidi, Rao N.V.S.,Mullangi, Ramesh,Bhamidipati, Ravikanth,Ramanujam, Rajagopalan,Akella, Venkateswarlu,Yeleswarapu, Koteswar Rao
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p. 2442 - 2450
(2007/10/03)
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- Acetylation of aromatic ethers using acetic anhydride over solid acid catalysts in a solvent-free system. Scope of the reaction for substituted ethers
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The acetylation of aryl ethers using acetic anhydride in the presence of zeolites under modest conditions in a solvent-free system gave the corresponding para-acetylated products in high yields. The zeolite can be recovered, regenerated and reused to give almost the same yields as that given when fresh zeolite is used.
- Smith, Keith,El-Hiti, Gamal A.,Jayne, Anthony J.,Butters, Michael
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p. 1560 - 1564
(2007/10/03)
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- Azabicyclic compounds for the treatment of disease
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The invention provides compounds of Formula I: 1wherein Azabicyclo is 2These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals in which α7 is known to be involved.
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-
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- Endothelin antagonists
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A compound of the formula (I): or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.
- -
-
-
- ENDOTHELIN ANTAGONISTS
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A compound of the formula (I): STR1 or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.
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-
-
- ENDOTHELIN ANTAGONISTS
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A compound of the formula (I): STR1 or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.
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-
-
- The Synthesis of 5-Substituted 2,3-Dihydrobenzofurans
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The preparation of 2,3-dihydrobenzofurans 6 from 2-(2-bromophenoxy)ethyl chlorides 3 by reaction with magnesium in a development of the Parham cyclialkylation reaction is described.A high yielding procedure using phase-transfer catalysis has also been developed for the preparation of the intermediate chloroethyl ethers 3 from bromophenols 2.The 5-hydroxy derivative 15 may be obtained from 2,3-dihydrobenzofuran (6a) by reaction with electrophilic reagents followed by oxidation.
- Alabaster, Ramon J.,Cottrell, Ian F.,Marley, Hugh,Wright, Stanley H. B.
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p. 950 - 952
(2007/10/02)
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