- PROCESS FOR PREPARING 4- { (S) -2- (4-(4-CHLOROPHENOXY) PHENOXYMETHYL) PYRROLIDIN-1-YL) } BUTYRIC ACID AND SALTS THEREOF
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The present invention relates to a process for preparing 4-{(S)-2-[4-(4-chlorophenoxy)phenoxymethyl]pyrrolidin-1-yl}butyric acid and its salts.
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Page/Page column 16
(2011/02/24)
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- Development of a scalable synthetic process for DG-051B, a first-in-class inhibitior of LTA4H
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DG-051B is a first-in-class small molecule inhibitor of leukotriene A4 hydrolase (LTA4H), currently in Phase II clinical development for the prevention of heart attack. Process optimization led from a linear seven-step synthetic procedure to a convergent
- Enache, Livia A.,Kennedy, Isaac,Sullins, David W.,Chen, Wei,Ristic, Dragan,Stahl, Glenn L.,Dzekhtser, Sergey,Erickson, Robert A.,Yan, Changren,Muellner, Frank W.,Krohn, Michael D.,Winger, Jennifer,Sandanayaka, Vincent,Singh, Jasbir,Zembower, David E.,Kiselyov, Alex S.
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experimental part
p. 1177 - 1184
(2010/04/22)
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- BIARYL SUBSTITUTED HETEROCYCLE INHIBITORS OF LTA4H FOR TREATING INFLAMMATION
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The present invention relates to a chemical genus of biaryl substituted heterocycle inhibitors of LTA4H (leukotriene A4 hydrolase) useful for the treatment and prevention and prophylaxis of inflammatory diseases and disorders. The compounds have general formula Ψ: An example is
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Page/Page column 25; 27; 29
(2008/06/13)
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- ANTIDIABETIC OXAZOLIDINEDIONES AND THIAZOLIDINEDIONES
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Phenoxyphenyl and phenoxybenzyl oxazolidine-2,4-diones and thiazolidine-2,4-diones are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well as dyslipidemia
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Page/Page column 33; 34
(2010/11/25)
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- PROCESS FOR THE PRODUCTION OF ANTIDIABETIC OXAZOLIDINEDIONES
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The present invention provides a convergent process for the preparation of a family of antidiabetic phenoxy-substituted phenoxybenzyl oxazolidinediones shown as structure I. The compounds are selective PPAR gamma partial agonists (SPPARM's), which are use
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Page/Page column 8-10
(2008/06/13)
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- FUSED AROMATIC COMPOUNDS HAVING ANTI-DIABETIC ACTIVITY
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Fused aromatic compounds of Formula (I) are PPAR gamma agonists or partial agonists and are useful in the treatment or control of type II diabetes, including hyperglycemia, dyslipidemia, hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, and obes
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Page/Page column 38-39
(2010/11/23)
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- Selective displacement of aryl fluorides with hydroquinone: Synthesis of 4-phenoxyphenols
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The selective displacement of a variety of aryl fluorides with hydroquinone has been achieved to give substituted 4-phenoxyphenols 3. In some cases the addition of 18-crown-6 resulted in a significant rate enhancement, and the reactions could be carried out at lower temperature. One of these derivatives, 3a (X = Cl) was converted to 2-propyl-4-(4-chlorophenoxy)phenol 2a, a precursor to the PPARγ receptor agonist 1.
- Marcune, Benjamin F.,Hillier, Michael C.,Marcoux, Jean-Fran?ois,Humphrey, Guy R.
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p. 7823 - 7826
(2007/10/03)
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- ANTIDIABETIC OXAZOLIDINEDIONES AND THIAZOLIDINEDIONES
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Phenoxyphenyl and phenoxybenzyl oxazolidine-2,4-diones and thiazolidine-2,4-diones of formula (I) are agonists or partial agonists of PPAR gamma and are useful in the treatment and control of hyperglycemia that is symptomatic of type II diabetes, as well
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Page/Page column 30
(2010/02/13)
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- 5-Aryl thiazolidine-2,4-diones as selective PPARγ agonists
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A series of 5-aryl thiazolidine-2,4-diones containing 4-phenoxyphenyl side chains was designed, synthesized, and evaluated for PPAR agonist activities. One such compound 28 exhibited comparable levels of glucose correction to rosiglitazone in the db/db mouse type 2 diabetes animal model.
- Koyama, Hiroo,Boueres, Julia K.,Han, Wei,Metzger, Edward J.,Bergman, Jeffrey P.,Gratale, Dominick F.,Miller, Daniel J.,Tolman, Richard L.,MacNaul, Karen L.,Berger, Joel P.,Doebber, Thomas W.,Leung, Kwan,Moller, David E.,Heck, James V.,Sahoo, Soumya P.
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p. 1801 - 1804
(2007/10/03)
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- 5-Aryl thiazolidine-2,4-diones: Discovery of PPAR dual α/γ agonists as antidiabetic agents
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A novel series of 5-aryl thiazolidine-2,4-diones based dual PPARα/γ agonists was identified. A number of highly potent and orally bioavailable analogues were synthesized. Efficacy study results of some of these analogues in the db/db mice model of type 2 diabetes showed them superior to rosiglitazone in correcting hyperglycemia and hypertriglyceridemia.
- Desai, Ranjit C.,Han, Wei,Metzger, Edward J.,Bergman, Jeffrey P.,Gratale, Dominick F.,MacNaul, Karen L.,Berger, Joel P.,Doebber, Thomas W.,Leung, Kwan,Moller, David E.,Heck, James V.,Sahoo, Soumya P.
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p. 2795 - 2798
(2007/10/03)
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- Lubricity additive for high-temperature gas turbine engine oils
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A tris[4-(chlorophenoxy)phenyl] phosphate of the formula: STR1 wherein n has a value of 1 to 5. This compound is effective as a lubricity additive for high temperatures lubricants.
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- A convenient method for the preparation of 4-aryloxyphenols
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A convenient method for the preparation of 4-aryloxyphenols via the homologation of preformed phenols is described. Condensation of various 4-substituted phenols with either 4-fluorobenzaldehyde (8) or 4-fluoroacetophenone (9) yielded the corresponding 4-aryl-oxybenzaldehydes, 10, and acetophenones, 11, in 70-93% yield. Baeyer-Villiger oxidation of these materials with 3-chloroperoxybenzoic acid (MCPBA) yielded the corresponding 4-formyloxy and 4-acetoxyphenyl ethers which were hydrolyzed without purification to the desired 4-aryloxyphenols 12 in 72-94% yield. Both 4-fluorobenzaldehyde (8) and 4-fluoroacetophenone (9) are synthetically equivalent to the a4 umpoled synthon 6. Extension of this methodology of the preparation of 4,4'-[arylbis(oxy)]bisphenols from aromatic diols is also described. Condensation of various aromatic diols with 8 or 9 yielded the corresponding 4,4'-[arylbis(oxy)]bisbenzaldehydes 15 and acetophenones 16 in 71-89% yield. Baeyer-Villiger oxidation of these compounds with MCPBA yielded the desired 4,4'-[arylbis(oxy)]bisphenyl bisformates 17 and bisacetates 18 in 67-84% yield. Hydrolysis of these compounds afforded the desired 4,4'-[arylbis(oxy)bisphenols 19 in 70-91% yield.
- Yeager,Schissel
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- Process for the preparation of 4-phenoxyphenols
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Process for the preparation of 4-phenoxyphenols of the formula STR1 in which R1 through R5 are hydrogen, halogen or alkyl, by diazotization of amines of the formula STR2 in a hydrochloric acid medium, and boiling in aqueous sulfuric
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