- MOLECULES HAVING CERTAIN PESTICIDAL UTILITIES, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES RELATED THERETO
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This disclosure relates to compounds having pesticidal utility against pests in phyla Nematoda, Arthropoda, and/or Mollusca, processes to produce such compounds and intermediates used in such processes, compositions containing such compounds, and processes of using such compounds against such pests. These compounds/molecules may be used, for example, as nematicides, acaricides, insecticides, miticides, and/or molluscicides. This document discloses compounds having the following formula (Formula One and/or Formula One-A).
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Page/Page column 215
(2021/02/12)
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- Synthesis of 5,9-Diaza[5]helicenes
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A new method for the synthesis of 5,9-diaza[5]helicenes is presented using 2,3-bis(acylamino)-substituted ortho-terphenyls as precursors. Activation of the amide groups and electrophilic substitution at the ortho positions of the adjacent phenyl groups leads to the 5,9-diaza[5]helicenes. A stepwise reaction including protection of the first amino group, amide formation at the second amino group with subsequent cyclization, followed by deprotection, amide formation and cyclization at the first amino group ensures that both electrophilic substitutions take place at sufficiently activated arenes and allows for the different substituents at the diaza[5]helicenes brought in with the amide groups. The terphenyl precursors are synthesized by two Suzuki couplings of suitably substituted building blocks. Three different 5,9-diaza[5]helicenes with aliphatic, alkenyl and methoxycarbonylalkyl substituents were prepared; the latter would allow to attach further functionalities by ester or amide linkage.
- Wei?, Aaron,Podlech, Joachim
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supporting information
p. 6697 - 6701
(2019/11/02)
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- Induction of Axial Chirality in 8-Arylquinolines through Halogenation Reactions Using Bifunctional Organocatalysts
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The enantioselective syntheses of axially chiral heterobiaryls were accomplished through the aromatic electrophilic halogenation of 3-(quinolin-8-yl)phenols with bifunctional organocatalysts that control the molecular conformations during successive halogenations. Axially chiral quinoline derivatives, which have rarely been synthesized in an enantioselective catalytic manner, were afforded in moderate-to-good enantioselectivities through bromination, and an analogous protocol also enabled enantioselective iodination. In addition, this catalytic reaction, which allows enantioselective control through the use of mono-ortho-substituted substrates, allowed the asymmetric synthesis of 8-arylquinoline derivatives bearing two different halogen groups in high enantioselectivities.
- Miyaji, Ryota,Asano, Keisuke,Matsubara, Seijiro
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supporting information
p. 9996 - 10000
(2017/08/01)
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- Ammonium formate-based one-pot reductive Heck reactions for the construction of cyclic sulfonamides
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A modified method is reported for the conversion of unsaturated sulfonamides into their cyclic saturated counterparts. This method utilises a single palladium catalyst for an intramolecular Heck reaction and subsequent transfer hydrogenation, which is ach
- Khalifa, Aisha,Conway, Lorna,Geoghegan, Kimberly,Evans, Paul
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supporting information
p. 4559 - 4562
(2017/11/03)
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- Homogenous suspension of immunopotentiating compounds and uses thereof
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The present invention generally relates to homogeneous suspensions of small molecule immune potentiators (SMIPs) that are capable of stimulating or modulating an immune response in a subject in need thereof. The homogeneous suspensions may be used in combinations with various antigens or adjuvants for vaccine therapies.
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Page/Page column 61
(2016/09/12)
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- Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation
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An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.
- Shen, Tao,Zhang, Yiqun,Liang, Yu-Feng,Jiao, Ning
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supporting information
p. 13147 - 13150
(2016/10/24)
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- Rh2(II)-catalyzed ester migration to afford 3 H-indoles from trisubstituted styryl azides
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Rh2(II)-Complexes trigger the formation of 3H-indoles from ortho-alkenyl substituted aryl azides. This reaction occurs through a 4π-electron-5-atom electrocyclization of the rhodium N-aryl nitrene followed by a [1,2]-migration to afford only 3H-indoles. The selectivity of the migration is dependent on the identity of the β-styryl substituent.
- Kong, Chen,Driver, Tom G.
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supporting information
p. 802 - 805
(2015/04/27)
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- Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
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The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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Paragraph 0355
(2015/09/22)
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- Indole synthesis based on a modified koser reagent
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A new metal-free method for the rapid and productive preparation of indoles has been developed. This process is based on sterically congested hypervalent iodine compounds of the family of Koser reagents, and iodosobenzene in combination with 2,4,5-tris-isopropylbenzene sulfonic acid provides the highest yields and fastest reaction times. This reagent alone promotes the chemoselective oxidative cyclization of 2-amino styrenes to indoles in high yields under mild conditions. Convenient route to indole: A fast, productive, and operationally simple indole synthesis was developed.
- Fra, Laura,Millán, Alba,Souto, José A.,Mu?iz, Kilian
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supporting information
p. 7349 - 7353
(2014/07/21)
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- MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS
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The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating ABC transporter mediated diseases using such modulators.
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- INHIBITORS OF HEPATITIS C VIRUS
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A class of compounds that inhibit Hepatitis C Virus (HCV) is disclosed, along with compositions containing the compound, and methods of using the composition for treating individuals infected with HCV.
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Page/Page column 124
(2012/05/19)
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- COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
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The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.
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- NOVEL INHIBITORS OF HEPATITIS C VIRUS REPLICATION
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The embodiments provide compounds of the general Formulae I, II, III, IV, or V as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.
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Page/Page column 156-158
(2011/07/06)
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- Ex situ generation of stoichiometric and substoichiometric 12CO and 13CO and its efficient incorporation in palladium catalyzed aminocarbonylations
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A new technique for the ex situ generation of carbon monoxide (CO) and its efficient incorporation in palladium catalyzed carbonylation reactions was achieved using a simple sealed two-chamber system. The ex situ generation of CO was derived by a palladium catalyzed decarbonylation of tertiary acid chlorides using a catalyst originating from Pd(dba)2 and P(tBu)3. Preliminary studies using pivaloyl chloride as the CO-precursor provided an alternative approach for the aminocarbonylation of 2-pyridyl tosylate derivatives using only 1.5 equiv of CO. Further design of the acid chloride CO-precursor led to the development of a new solid, stable, and easy to handle source of CO for chemical transformations. The synthesis of this CO-precursor also provided an entry point for the late installment of an isotopically carbon-labeled acid chloride for the subsequent release of gaseous [ 13C]CO. In combination with studies aimed toward application of CO as the limiting reagent, this method provided highly efficient palladium catalyzed aminocarbonylations with CO-incorporations up to 96%. The ex situ generated CO and the two-chamber system were tested in the synthesis of several compounds of pharmaceutical interest and all of them were labeled as their [ 13C]carbonyl counterparts in good to excellent yields based on limiting CO. Finally, palladium catalyzed decarbonylation at room temperature also allowed for a successful double carbonylation. This new protocol provides a facile and clean source of gaseous CO, which is safely handled and stored. Furthermore, since the CO is generated ex situ, excellent functional group tolerance is secured in the carbonylation chamber. Finally, CO is only generated and released in minute amounts, hence, eliminating the need for specialized equipment such as CO-detectors and equipment for running high pressure reactions.
- Hermange, Philippe,Lindhardt, Anders T.,Taaning, Rolf H.,Bjerglund, Klaus,Lupp, Daniel,Skrydstrup, Troels
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supporting information; experimental part
p. 6061 - 6071
(2011/06/19)
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- Selective activation of enantiotopic C(sp3)-hydrogen by means of chiral phosphoric acid: Asymmetric synthesis of tetrahydroquinoline derivatives
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Chiral phosphoric acid-catalyzed asymmetric C-H functionalization has been achieved. In this process, enantiotopic C(sp3)-hydrogen is selectively activated by chiral phosphoric acid to afford tetrahydroquinoline derivatives with excellent enantioselectivities (up to 97% ee).
- Mori, Keiji,Ehara, Kensuke,Kurihara, Kazuki,Akiyama, Takahiko
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supporting information; scheme or table
p. 6166 - 6169
(2011/06/21)
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- Synthesis and reactivity of dimethoxy-functionalised Troeger's base analogues
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Troeger's base analogues were prepared bearing methoxy groups in the 1,7-, 2,8-, 3,9- or 4,10-positions. These compounds were converted to their dihydroxy analogues in excellent yields upon treatment with boron tribromide and the 4,10-dihydroxy analogue could be prepared by directly from 4-hydroxyaniline. The synthetic utility of the dihydroxy-functionalised compounds as building blocks was demonstrated by the synthesis of a dialkoxy and a diester Troeger's base analogue.
- Malik, Qasim M.,Ijaz, Sadia,Craig, Donald C.,Try, Andrew C.
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experimental part
p. 5798 - 5805
(2011/08/21)
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- Rhodium-catalyzed domino conjugate addition-cyclization reactions for the synthesis of a variety of N- and O-heterocycles: Arylboroxines as effective carbon nucleophiles
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Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.
- Park, Ja Ock,Youn, So Won
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supporting information; experimental part
p. 2258 - 2261
(2010/07/17)
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- A synthetic approach to carbazoles using electrochemically generated hypervalent iodine oxidant
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Carbazoles were successfully synthesized by oxidative cyclization of the corresponding diaryl derivatives using electrochemically generated hypervalent iodine oxidant. Electron-withdrawing nitro and donating methoxy groups at the para position of the acetamide group interfered with cyclization. Glycozoline (8) was successfully synthesized in five steps with 50% overall yield.
- Kajiyama, Daichi,Inoue, Keisuke,Ishikawa, Yuichi,Nishiyama, Shigeru
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experimental part
p. 9779 - 9784
(2011/03/17)
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- THIENO [2, 3-B] PYRIDINE DERIVATIVES AS VIRAL REPLICATION INHIBITORS
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The present invention relates to a series of compounds of formula (A) having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutical amount of such compounds, optionally combined with one or more other drugs having anti-viral activity.
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Page/Page column 236-237
(2010/12/17)
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- INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
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Compounds of formula (I): wherein R4, R6 and R7 are defined herein, are useful as inhibitors of HIV replication.
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Page/Page column 116
(2009/06/27)
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- Regioselective access to substituted oxindoles via rhodium-catalyzed carbene C-H insertion
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Rhodium-catalyzed decomposition of diazoamides followed by insertion of the resulting carbenes into an aromatic C-H bond gives access to substituted oxindoles. The reaction takes place with aromatic rings substituted by either electron-donating or -withdrawing groups at ortho, meta or para positions and the regioselectivity can be controlled by a substitution α to the diazo functionality. In the presence of an ester, the reaction leads to the formation of 2-silyloxyindole-3-carboxylates in 40-85% yields and regioselectivities up to 80% are observed in the case of meta-substituted substrates. This selectivity mainly relies on steric factors and use of a more bulky N,N-diethylamide then affords 2-silyloxyindole-3-carboxamides in 42-91% yields with complete regioselectivity.
- Gauthier, Delphine,Dodd, Robert H.,Dauban, Philippe
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experimental part
p. 8542 - 8555
(2009/12/24)
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- COMPOUNDS AND COMPOSITIONS AS TLR ACTIVITY MODULATORS
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The invention provides a novel class of compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with Toll-Like Receptors, including TLR7 and TLR8. In one aspect, the compounds are useful as adjuvants for enhancing the effectiveness of a vaccine (formula I) wherein: X3 is N; X4 is N Or CR3; X5 is -CR4=CR5.
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Page/Page column 167
(2009/10/22)
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- Generation and suppression of 3-/4-functionalized benzynes using zinc ate base (TMP-Zn-ate): New approaches to multisubstituted benzenes
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We present full details of our new methods for preparing functionalized benzynes with lithium di-alkyl(2,2,6,6-tetramethylpiperidino)zincate (R 2Zn(TMP)Li) through deprotonative zincation as a key reaction. In this system, by choosing appropriate ligands for the zincate, either regioselective zincation of functionalized haloaromatics or the generation of substituted benzynes can be controlled in good yields with excellent chemoselectivity, using the same substrate. Zincation with tBu 2Zn(TMP)Li followed by electrophilic trapping or zincation with Me2Zn(TMP)Li followed by nucleophilic or diene trapping is shown to be a powerful tool for the chemoselective preparation of 1,2,3-/1,2,4- trisubstituted benzene derivatives. These methods offer far greater generality than previous methods for the synthesis of multifunctionalized benzenes. Computational/theoretical studies of the reaction mechanism of this unique benzyne formation indicated that preferential coordination of the dialkylzinc moiety of zincate to halogen is the reason for the reduced activation energy of the elimination, that is, for the formation of the benzyne. The role of the ligands on Zn in accelerating/decelerating the elimination is also discussed.
- Uchiyama, Masanobu,Kobayashi, Yuri,Furuyama, Taniyuki,Nakamura, Shinji,Kajihara, Yumiko,Miyoshi, Tomoko,Sakamoto, Takao,Kondo, Yoshinori,Morokuma, Keiji
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p. 472 - 480
(2008/10/09)
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- Regioselective photochemical and microwave mediated monobromination of aromatic compounds using 2,4,4,6-tetrabromo-2,5-cyclohexadienone
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Bromination of different aromatic substrates have been described using 2,4,4,6-tetrabromo-2,5-cyclohexadienone in conjunction with microwave and ultraviolet radiations. Important features of the work include high regioselectivity obtained in very short to moderate reaction time, atom economy, and recyclability of the reagent. Copyright Taylor & Francis Group, LLC.
- Gupta, Neeraj,Kad, Goverdhan L.,Singh, Vasundhara,Singh, Jasvinder
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p. 3421 - 3428
(2008/02/12)
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- Investigation of the asymmetric Birch reduction-alkylation of a chiral 5-arylbenzamide containing a carbamate group
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The synthesis and asymmetric Birch reduction-alkylation of chiral benzamide 17 are described. Birch reductive alkylation of benzamide 17 was optimized to give the corresponding cyclohexa-1,4-diene products in 66-78% isolated yield and with high diastereoselectivity (dr: >98:2). The effects of performing the reduction in the presence and in the absence of tert-butyl alcohol are discussed.
- Casimiro-Garcia, Agustin,Schultz, Arthur G.
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p. 2739 - 2742
(2007/10/03)
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- Polymer-supported organotin reagents for regioselective halogenation of aromatic amines
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(Chemical Equation Presented) Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.
- Chretien, Jean-Mathieu,Zammattio, Francoise,Le Grognec, Erwan,Paris, Michael,Cahingt, Blanche,Montavon, Gilles,Quintard, Jean-Paul
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p. 2870 - 2873
(2007/10/03)
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- Substituted 2-aryl-4-arylaminopyrimidines and analogs as activators or caspases and inducers of apoptosis and the use thereof
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The present invention is directed to substituted 2-aryl-4-arylaminopyrimidine and analogs thereof, represented by the general Formula I: wherein A, Ar1, Ar2, R1 and R3 are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. The compounds of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.
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- Phenyl heterocyclyl ethers
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The invention relates to compounds of formula I
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- Quinoline derivatives or salt thereof and remedy for cardiac diseases containing the same
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A quinoline derivative represented by general formula (1), a medicinally acceptable salt thereof, and a remedy for cardiac diseases containing the same: STR1 [wherein ring A represents a furan, dihydrofuran or dioxolane ring, and R1 represents an aminoalkyl group]. The compound (1) has a positively inotropic effect on myocardia and an antiarrhythmic effect, and can dilate blood vessels without extremely increasing the heart rate. Therefore, a remedy for cardiac diseases containing the same as the active ingredient is remarkably useful for treating cardiac insufficiency, arrhythmia, and so forth.
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- Computer-Aided Molecular Modeling, Synthesis, and Biological Evaluation of 8-(Benzyloxy)-2-phenylpyrazoloquinoline as a Novel Benzodiazepine Receptor Agonist Ligand
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Using computer-aided conformational analysis, based on molecular dynamics simulation, cluster analysis, and Monte Carlo techniques, we have designed and synthesized compounds in which a benzyloxy substituent has been incorporated into a series of pyrazoloquinoline benzodiazepine receptor (BZR) ligands.Earlier studies had shown that the benzyloxy group could act as part of the agonist pharmacophoric determinant in the β-carboline ring system.Furthermore, the agonist β-carboline had been correlated with a binding site orientation and volume fit for an agonist 6-phenylimidazobenzodiazepine carboxylate.The present study was undertaken to determine whether the benzyloxy substituent could be used as an agonist pharmacophoric descriptor for the phenylpyrazoloquinolin-3-one BZR ligands.The results of a determination of GABA shift ratios for the synthetic ligands indicate that 8-(benzyloxy)-2-phenylpyrazoloquinolin-3-one can be predicted to be an agonist at the BZR.
- Wang, C.-G.,Langer, T.,Kamath, P. G.,Gu, Z.-Q.,Skolnick, P.,Fryer, R. Ian
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p. 950 - 957
(2007/10/02)
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- Synthesis of polysubstituted indoles and indolines by means of zirconocene-stabilized benzyne complexes
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The development of a new method for the regiospecific synthesis of polysubstituted indoles and indolines is reported. The key steps involve the generation of zirconocene-stabilized benzyne complexes and subsequent intramolecular olefin insertion reactions to provide tricyclic indoline zirconacycles. The zirconacyclic intermediates were cleaved with iodine to yield diiodo indolines, which were converted to a wide variety of indole and indoline products, such as analogs of tryptamine, serotonin, tryptophan, and the pharmacophore of CC-1065.
- Tidwell, Jeffrey H.,Buchwald, Stephen L.
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p. 11797 - 11810
(2007/10/02)
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- A New Approach to the Synthesis of the CC-1065/Duocarmycin Pharmacophore
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The spirocyclic 1,2,7,7a-tetrahydrocyclopropindol-4-one subunit of CC-1065 and duocarmycin A, which comprises the common pharmacophore of the two antibiotics, has been efficiently synthesized in six steps from readily available starting materials.The key step of the synthesis utilizes a zirconocene-stabilized benzyne complex.
- Tidwell, Jeffrey H.,Buchwald, Stephen L.
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p. 6380 - 6382
(2007/10/02)
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