- LIPID PRODRUGS OF NEUROSTEROIDS
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00584;-00585
(2021/08/13)
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- Unusual transformation of 4-hydroxy/methoxybenzylic alcohols via C[sbnd]C ipso-substitution reaction using proton-exchanged montmorillonite as media
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We present here proton-exchanged montmorillonite-mediated an unusual transformation of 4-hydroxy and 4-methoxybenzylic alcohols to form symmetrical benzylic ethers and diarylmethanes under mild conditions. Nuclear magnetic resonance spectroscopy and density functional theory calculations support a plausible mechanism, which includes a distinctive aromatic C[sbnd]C ipso-substitution reaction with a hydroxymethyl group as the C-based leaving group.
- Chen, Dongyin,Chen, Xuan,Dong, Zezhong,Jiang, Nan,Li, Fei,Yun, Yangfang,Zhou, Yu
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supporting information
(2020/11/12)
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- LIPID PRODRUGS OF PREGNANE NEUROSTEROIDS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, as well as methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00471; 00472
(2020/02/23)
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- LIPID PRODRUGS OF JAK INHIBITORS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00645-00646
(2020/09/12)
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- LIPID PRODRUGS OF BTK INHIBITORS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00405; 00654; 00655
(2020/09/12)
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- LIPID PRODRUGS OF GLUCOCORTICOIDS AND USES THEREOF
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The present invention provides lymphatic system-directing lipid prodrugs, pharmaceutical compositions thereof, methods of producing such prodrugs and compositions, and methods of improving the bioavailability or other properties of a therapeutic agent that comprises part of the lipid prodrug. The present invention also provides methods of treating a disease, disorder, or condition such as those disclosed herein, comprising administering to a patient in need thereof a disclosed lipid prodrug or a pharmaceutical composition thereof.
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Paragraph 00638; 00639
(2020/09/12)
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- Phenolic Oxidation Using H2O2 via in Situ Generated para-Quinone Methides for the Preparation of para-Spiroepoxydienones
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Phenols are attractive starting materials for the preparation of highly substituted cyclohexane rings via dearomative processes. Herein we report an efficient preparation of dearomatized 1-oxaspiro[2.5]octa-4,7-dien-6-ones (para-spiroepoxydienones) via the nucleophilic epoxidation of in situ generated para-quinone methides from 4-(hydroxymethyl)phenols using aqueous H2O2. The developed protocol bypasses the need for stoichiometric bismuth reagents or diazomethane, which are frequently deployed for p-spiroepoxydienone preparation. The p-spiroepoxydienones are further elaborated in numerous downstream complexity-building transformations.
- McLaughlin, Michael F.,Massolo, Elisabetta,Cope, Thomas A.,Johnson, Jeffrey S.
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supporting information
p. 6504 - 6507
(2019/09/04)
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- Optimization of sulfonamide derivatives as highly selective EP1 receptor antagonists
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A series of 4-[(2-{isobutyl[(5-methyl-2-furyl)sulfonyl]amino}phenoxy)methyl]benzoic acids and 4-({2-[isobutyl(1,3-thiazol-2-ylsulfonyl)amino]phenoxy}methyl)benzoic acids were synthesized and evaluated for their EP receptor affinities and EP1 receptor anta
- Naganawa, Atsushi,Matsui, Toshiaki,Ima, Masaki,Yoshida, Koji,Tsuruta, Hiroshi,Yamamoto, Shingo,Yamamoto, Hiroshi,Okada, Hiroki,Maruyama, Takayuki,Nakai, Hisao,Kondo, Kigen,Toda, Masaaki
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p. 7774 - 7789
(2007/10/03)
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- Unexpected 2,4,6-trimethylphenol oxidation in the presence of Fe(III) aquacomplexes
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2,4,6-Trimethylphenol (TMP) was efficiently oxidised by Fe(III) aquacomplexes. HPLC analysis was used to follow the kinetics of the redox process. Two degradation products were detected and identified: 2,6-dimethyl-4-(hydroxymethyl)phenol (P1) and 3,5-dimethyl-4-hydroxybenzaldehyde (P2) accounting for 100% of TMP degradation in the early stages of the reaction. The formation of the products was concomitant with the reduction of Fe(III) into Fe(II). The direct relation between TMP oxidation and the concentration of the monomeric species {Fe(H2O)5(OH)} 2+ gives evidence for the initial reaction to take place between TMP and this particular species. Moreover, the correlation between P2 formation and P1 disappearance during the reaction implies the sequence of reactions: TMP → P1 → P2. A mechanism leading to the two degradation products is proposed. the Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2006.
- Aguer, Jean-Pierre,Mailhot, Gilles,Bolte, Michele
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p. 191 - 196
(2007/10/03)
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- NOVEL ACYLATING REAGENTS
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Novel acylating agents useful for preparing activated nucleophiles such as terminally activated polymers are disclosed. In preferred aspects, the acylating agents are formula (I) and formula (II) and they used to prepare activated polymers such as PEG's f
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- Quinone methide phosphodiester alkylations under aqueous conditions
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A detailed analysis of the alkylation of phosphodiesters with a p-quinone methide under aqueous conditions has been accomplished. The relative rates of phosphodiester alkylation and hydrolysis have been examined by 1H NMR analysis of the reacti
- Zhou,Turnbull
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p. 7072 - 7077
(2007/10/03)
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- Synthesis of thiophenyl substituted cyclohexa-2,4-dien-1-one and its photocleavage coupling reaction with amines
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Thiophenyl substituted cyclohexa-2,4-dien-1-ones were synthesized and photolyzed in the presence of various amines to afford the amides containing diene moeties via the ketene intermediate under visible light irradiation at 38°C. (C) 2000 Elsevier Science
- Kwon, Tae Woo,Kim, Young Mee,Song, Suk Jin,Kwon, Yong Uk,Chung, Sung Kee
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p. 1551 - 1553
(2007/10/03)
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- Indirect oxidations using electrogenerated hydrogen peroxide
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Hydrogen peroxide is a unique redox reagent in that it may be produced from air and after use in synthesis, manufacturing technology or effluent treatment, it leaves no residual chemicals. New concepts in cell technology for in situ generation of hydrogen peroxide, as well as recent developments in its chemistry, have made more attractive the use of hydrogen peroxide as a mediator in indirect electrolysis. This review discusses some of the factors contributing to these developments.
- Pletcher, Derek
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p. 745 - 750
(2007/10/03)
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- Redox Interactions of Cr(VI) and Substituted Phenols: Products and Mechanism
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The mechanisms of aqueous oxidation-reduction interactions between Cr(VI) and substituted phenols (RArOH) were characterized by kinetic analysis and determinations of reaction products and intermediates. A rapid, peroxidative equilibrium between HCrO4(-) and RArOH forms chromate ester intermediates, as verified by spectroscopy. The subsequent rate-limiting ester decomposition proceeds via innersphere electron transfer. The overall rate dependence on [H(+)] is well accounted for by three parallel redox pathways involving zero, one, and two protons. The two-proton pathway dominates at pH = 5. The parallel reaction rate expression was fitted to data for 4-methyl-, 4-methoxy-, 2,6-dimethoxy-, and 3,4-dimethoxyphenol for pH 1-6. Beside accurately predicting rates for the calibrated conditions, the model predicts a sharp decline in rates at pH >= 6. Rates subsequently measured at pH 7 agreed well with those calculated a priori. Such predictions suggest that the proposed mechanism is robust and accurate. Rate constants were correlated with Hammett-type substituent parameters. Reaction products indicated both one- and two-electron pathways.
- Elovitz, Michael S.,Fish, William
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p. 1933 - 1943
(2007/10/03)
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- 4-oxy-substituted phenoxyalkyl carboxylic acid, ester, and alcohol derivatives as antihyper-cholesterolemic and antiatherosclerotic agents
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Novel 4-oxy substituted phenoxyalkyl carboxylic acid, ester and alcohol derivatives are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful in preventing the intestinal absorption of cholesterol and thus are useful in the treatment of hypercholesterolemia and atherosclerosis.
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- Carboxyalkylthiomethylation of Phenols
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The syntheses of carboxyalkylthiomethyl-substituted phenols, 2,4-, 2,6- and 3,5-xylenols and 2,3,5,6-tetramethylphenol are described.In all cases except 2,6-xylenol, a one-step process based on refluxing the phenol with formalin and the sodium salt of a mercaptoalkanoic acid gave products substituted in all of the vacant ortho and para positions.With 2,6-xylenol a two-step process was necessary.The products are of interest as potential inhibitors of ferrous corrosion.
- Massy, D. J. R.,McKillop, A.
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p. 253 - 255
(2015/06/03)
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- A SIMPLE SINTHESIS OF TROPONES AND RELATED COMPOUNDS
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Cyclohexa-2,4- and 2,5-dienones bearing position 2 or 4 a dihalomethyl group (halogen = chlorine or bromine) are smoothly reduced by tri-butyltin hydride to furnish appropriately substituted tropones.Modification of the substituents permits access to a tropolone and to less substituted tropones.The mechanism of this ring expansion process has been discussed.
- Barbier, Michael,Barton, Derek H. R.,Devys, Michel,Topgi, Ravindra Satish
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p. 5031 - 5038
(2007/10/02)
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