- Sequential SNAr Reaction/Suzuki-Miyaura Coupling/C-H Direct Arylations Approach for the Rapid Synthesis of Tetraaryl-Substituted Pyrazoles
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A rapid synthesis of 1,3,4,5-tetraaryl-substituted pyrazoles has been achieved through a sequence of SNAr reaction/Suzuki-Miyaura coupling/Pd-catalyzed direct arylations that used 3-iodo-1H-pyrazole as a scaffold. Pyrazoles with four different aryl groups were synthesized in a straightforward manner with no extra synthetic steps, such as protection/deprotection or the introduction of activating/directing groups, using readily available substrates and reagents. The developed synthetic approach enabled the structurally diverse synthesis of multiaryl-substituted pyrazoles without using a glovebox technique.
- Morita, Taiki,Kobayashi, Daisuke,Matsumura, Keisuke,Johmoto, Kohei,Uekusa, Hidehiro,Fuse, Shinichiro,Takahashi, Takashi
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supporting information
p. 1626 - 1630
(2015/08/06)
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- THIAZOLOPYRIMIDINONES AS MODULATORS OF NMDA RECEPTOR ACTIVITY
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The present invention relates to certain thiazolopyrimidinone compounds for use in modulating NMDA receptor activity, pharmaceutical compositions comprising such compounds and methods of treating neurological and psychiatric conditions.
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Paragraph 0498
(2015/04/28)
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- Selective palladium-catalyzed direct C-H arylation of unsubstituted N-protected pyrazoles
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A highly selective C-5 arylation of N-dimethylaminosulfamoyl-protected pyrazole with aryl bromides is catalyzed by 2-5 mol% palladium in the presence of triphenylphosphine ligand and carboxylic acid additive. Selectivities up to 45:1 (C-5:C-4) can be achieved by running the reaction in non-polar solvents. A thorough study of scope and limitations shows good general tolerance of aryl bromide substitution. However, limitations on tolerance of ortho-subsitution and protic functional groups were established. Together with a telescoped deprotection step this method presents a viable alternative for the synthesis of C-3 arylated pyrazole building blocks.
- Kumpulainen, Esa T. T.,Pohjakallio, Antti
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supporting information
p. 1555 - 1561
(2014/06/09)
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- HETEROCYCLIC COMPOUND
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The present invention provides an agent for the prophylaxis or treatment of autoimmune diseases (e.g., psoriasis, rheumatoid arthritis, inflammatory bowel disease, Sjogren's syndrome, Behcet's disease, multiple sclerosis, systemic lupus erythematosus etc.) and the like, which has a superior Tyk2 inhibitory action. The present invention relates to a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof.
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Paragraph 0581
(2015/01/18)
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- HETEROCYCLIC COMPOUND
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Provided is a compound useful for the prophylaxis or treatment of cancer. The present invention relates to a compound represented by formula (I): wherein each symbol in the formula is as defined in the specification, or a salt thereof or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer.
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Page/Page column 53
(2013/02/28)
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- THIENOPYRIMIDINE AS CDC7 KINASE INHIBITORS
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The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof, or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer
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Page/Page column 209-210
(2010/09/18)
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- METHYL SULFANYL PYRMIDMES USEFUL AS ANTIINFLAMMATORIES, ANALGESICS, AND ANTIEPILEPTICS
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The present invention relates to pyrimidine derivatives of Formula (Ia) and (Ib) (including tautomers, isomers, prodrugs, and pharmaceutically acceptable salts thereof). Said compounds are useful in the treatment of pain (such as neuropathic pain), inflammation, and epilepsy (by acting as anticonvulsants). Methods of medical treatment making use of said compounds, as well as additional compounds of Formula (IIa) and (IIb), are also disclosed.
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Page/Page column 183-184
(2010/12/18)
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- FUNGICIDAL MIXTURES
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Disclosed is a fungicidal composition comprising (a) at least one compound selected from the compounds of Formula 1 N-oxides, and salts thereof, insert Formula 1 here wherein R1, R2, A, G, Q, W1, W2, X and n are otherwise as defined in the disclosure, and (b) at least one additional fungicidal compound. Also disclosed is a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of the aforesaid composition.
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Page/Page column 87
(2008/12/07)
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- HETEROCYCLIC HYDRAZIDE COMPOUND AND PESTICIDAL USE OF THE SAME
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A hydrazide compound represented by the formula (I), an N-oxide thereof or suitable salt thereof: has excellent pesticidal activity.
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Page/Page column 389-390
(2008/12/08)
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- HYDRAZIDE COMPOUND AND PESTICIDAL USE OF THE SAME
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A hydrazide compound represented by the formula (1): has excellent pesticidal activity.
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Page/Page column 487
(2008/06/13)
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- FUNGICIDAL CARBOXAMIDES
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This invention is directed to compounds of Formula (1) including all geometric and stereoisomers, N oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use as fungicides, ( l ) provided that the compound of Formula 1 is other than 2-[1-[(2-chlorophenyl)acetyl]-4-piperidinyl]-N-methyl-N-[(1R)-1-phenylethyl]-4-thiazolecarboxamide and R1 is other than 4-fluorophenyl; wherein R1, R2, A, G, Q, W1, W2, X and n are otherwise as defined in the disclosure, Also disclosed are compositions containing the a compound having a formula corresponding to Formula 1 where the provisos are both omitted; and methods for controlling plant diseases caused by fungal plant pathogens which involves applying an effective amount of a compound having a formula corresponding to Formula (1) where the provisos are both omitted.
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Page/Page column 70
(2010/11/25)
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- IMIDAZO (1, 2-A) PYRIDINE COMPOUNDS AS VEGF-R2 INHIBITORS
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The present invention provides compounds that are inhibitors of VEGF-R2 of the formula: (I) and methods of using these compounds.
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Page/Page column 25
(2008/06/13)
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- Efficient and β-stereoselective synthesis of pyrazole C-nucleosides
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3(5)-(β-D-Ribofuranosyl)pyrazole 1 and 3(5)-(2-deoxy-β-D- ribofuranosyl)pyrazole (2) were stereoselectively synthesized by cyclization of 1,2-diazafulvene intermediates obtained from 2,3,5-tri-O-benzyl-D-ribose (5) and 3,5-di-O-benzyl-2-deoxy-D-ribose (10
- Harusawa, Shinya,Matsuda, Chiharu,Araki, Lisa,Kurihara, Takushi
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p. 793 - 798
(2007/10/03)
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- ARYL-ALKYLAMINES AND HETEROARYL-ALKYLAMINES AS PROTEIN KINASE INHIBITORS
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The invention provides a compound of the formula (II): or a salt, solvate, tautomer or N-oxide thereof; wherein n is 0 or 1; one of Y1 and Y2 is CH and the other is selected from CH, CR8 and N; q is 0, 1 or 2 provided that q is 0 or 1 when Y1 or Y2 is CR8; R1 is an aryl or heteroaryl group of 5 to 10 ring members; R2a and R3a each are hydrogen, C1-4 hydrocarbyl or C1-4 acyl wherein the hydrocarbyl and acyl moieties are optionally substituted by fluorine, hydroxy, amino, methylamino, dimethylamino or methoxy; or NR2aR3a forms an imidazole group or a saturated monocyclic 4-7 membered heterocyclic group optionally containing a second heteroatom ring member selected from O and N; R18 is hydrogen or methyl; R19 is hydrogen or methyl; R24 is hydrogen or R24, R2a and the intervening nitrogen atom and carbon atoms together form an azetidine, pyrrolidine or piperidine ring; R25 is hydrogen or a C1-4 alkyl group wherein the C1-4 alkyl group is optionally substituted by hydroxy or amino provided that there are at least two carbon atoms between the hydroxy or amino group and the oxygen atom to which R25 is attached; and R4 and R5 each are hydrogen or a substituent as defined in the claims
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Page/Page column 190-191
(2010/11/25)
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- PHARMACEUTICAL COMPOUNDS
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The invention provides a compound of the formula (I) or a salt, solvate, tautomer or N-oxide thereof; wherein A is a saturated hydrocarbon linker group; E is a monocyclic or bicyclic carbocyclic or heterocyclic group; L1 is a bond or a linker selected from C1-C4 alkenylene, C1-C4 alkynylene, -CONR’, -NR’CO, -S, -C(O)-, -C(NR11)-, -C(S)-, -N(R11)2, C(=CHR11), -SO- and -SO2-; or L1 together with t R16 forms and 8-12 membered fused bicyclic heteroaryl ring system; L3 is a bond or a linker selected from CONH and HNCO; provided that L1 and L3 cannot both be linkers simultaneously; and provided also that L1 and L3 cannot both be a bond simultaneously; R16 is an optionally substituted 5- to 12-membered monocyclic or bicyclic carbocyclic or heterocyclic ring; L2 is absent or is a linker selected from C]-C4 alkylene, Ci-C4 alkenylene, Ci-C4 alkynylene, -CONR’-, -NR’CO-, -O-, -S-, -C(O)-, C(=CHR11), C(S)-, -N(R11)2, C3-4 cycloalkanediyl, -SO- and -SO2-; R17 is absent or is C1-6 alkyl or an optionally substituted 5 to 12 membered carbocyclic or heterocyclic ring; provided that when R17 is absent, then L2 is also absent; and R2, R3, R4, R5, R11 and R’ are as defined in the claims.
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Page/Page column 129
(2010/11/25)
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- Pyrazole derivatives having herbicidal activity and their use
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Compounds of formula (I): STR1 (in which: R1 and R2 are each hydrogen, optionally substituted alkyl, optionally substituted alkenyl, alkynyl, alkoxy, aryl or pyridyl, or R1 and R2 together represent alkylene; A and B are each hydrogen, halogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, alkylthio, alkylsulfonyl, dialkylsulfamoyl, aliphatic carboxylic acyl, carboxy, --CONRa Rb where Ra and Rb are each hydrogen or alkyl, formyl or cyano groups; D represents optionally substituted phenyl, benzyl, pyridyl or pyrimidinyl; and n is 0, 1 or 2; and salts and esters thereof) have valuable herbicidal properties, and, since they are totally innocuous to rice plants, are especially useful for the treatment of paddy fields.
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- Carbodesilylation of (Trimethylsilyl)imidazoles and -pyrazoles
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The preparation of the 1-methyl(trimethylsilyl) (TMS)-substituted imidazoles 3a, 4a, 8, 9, and 11a by silylation of the corresponding metallated imidazoles is described.Carbodesilylation of 3 with aldehydes or carboxylic halogenides occurs selectively in 2-position.In the presence of a strong base (CsF) the reactivity against carbon electrophiles correlates well with the stability of the imidazolyl anions; regioselective carbodesilylation in 2-, 5-, or 4-position of the twofold TMS-substituted imidazoles 3a and 9 therefore is possible, which allows the synthesis of a great variety of hydroxyalkyl-substituted imidazoles and of acylimidazoles.By using the dimethylsulfamoyl substituent as an N-protecting group, the N-unsubstituted 5-benzoylimidazole (26) as well as the comparable 5-benzoyl-pyrazole (30b) and 5-(hydroxyphenylmethyl)pyrazole (30a) are accessible. Key Words : Imidazoles, (trimethylsilyl)-, carbodesilylation of / Pyrazoles, (trimethylsilyl)-, carbodesilylation of / Carbodesilylation
- Effenberger, Franz,Roos, Michael,Ahmad, Roshan,Krebs, Andreas
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p. 1639 - 1650
(2007/10/02)
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