- Native Amine-Directed ortho -C-H Halogenation and Acetoxylation /Condensation of Benzylamines
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Free or unfunctionalized benzylamines are well known to participate in C-H activation in the presence of palladium salts. Despite the ease with which these complexes can be activated, subsequent functionalization of the dimeric cyclometalates can be chall
- Chand-Thakuri, Pratibha,Alahakoon, Indunil,Liu, Daniel,Kapoor, Mohit,Kennedy, John F.,Jenkins, Kenneth W.,Rabon, Allison M.,Young, Michael C.
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p. 341 - 354
(2021/10/07)
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- Process for a CETP Inhibitor
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An efficient process is disclosed for producing the compound of formula I, which is the CETP inhibitor anacetrapib, which raises HDL-cholesterol and reduces LDL-cholesterol in human patients and may be effective for treating or reducing the risk of developing atherosclerosis:
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Paragraph 0038
(2014/10/16)
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- PROCESS FOR A CETP INHIBITOR
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An efficient process is disclosed for producing the compound of formula I, which is the CETP inhibitor anacetrapib, which raises HDL-cholesterol and reduces LDL-cholesterol in human patients and may be effective for treating or reducing the risk of developing atherosclerosis:.
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Page/Page column 6-7
(2013/05/22)
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- SYNTHESIS OF INTERMEDIATES FOR PREPARING ANACETRAPIB AND DERIVATIVES THEREOF
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The present invention relates to the field of organic chemistry, more specifically to the synthesis of intermediate compounds which can be used in the synthesis of pharmaceutically active agents such as anacetrapib or derivatives thereof.
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Page/Page column 34
(2013/07/05)
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- SYNTHESIS OF INTERMEDIATES FOR PREPARING ANACETRAPIB AND DERIVATIVES THEREOF
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The present invention relates to the field of organic chemistry, more specifically to the synthesis of intermediate compounds which can be used in the synthesis of pharmaceutically active agents such as anacetrapib or derivatives thereof.
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Page/Page column 45-46
(2012/07/13)
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- Synthesis of intermediates for preparing anacetrapib and derivates thereof
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The present invention relates to the field of organic chemistry, more specifically to the synthesis of intermediate compounds which can be used in the synthesis of pharmaceutically active agents such as anacetrapib or derivatives thereof.
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Page/Page column 35
(2012/07/03)
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- Synthesis of intermediates for preparing anacetrapib and derivates thereof
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The present invention relates to the field of organic chemistry, more specifically to the synthesis of intermediate compounds which can be used in the synthesis of pharmaceutically active agents such as anacetrapib or derivatives thereof.
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Page/Page column 29
(2012/07/03)
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- Biphenyl-substituted oxazolidinones as cholesteryl ester transfer protein inhibitors: Modifications of the oxazolidinone ring leading to the discovery of anacetrapib
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The development of the structure-activity studies leading to the discovery of anacetrapib is described. These studies focused on varying the substitution of the oxazolidinone ring of the 5-aryloxazolidinone system. Specifically, it was found that substitution of the 4-position with a methyl group with the cis-stereochemistry relative to the 5-aryl group afforded compounds with increased cholesteryl ester transfer protein (CETP) inhibition potency and a robust in vivo effect on increasing HDL-C levels in transgenic mice expressing cynomolgus monkey CETP.
- Smith, Cameron J.,Ali, Amjad,Hammond, Milton L.,Li, Hong,Lu, Zhijian,Napolitano, Joann,Taylor, Gayle E.,Thompson, Christopher F.,Anderson, Matt S.,Chen, Ying,Eveland, Suzanne S.,Guo, Qiu,Hyland, Sheryl A.,Milot, Denise P.,Sparrow, Carl P.,Wright, Samuel D.,Cumiskey, Anne-Marie,Latham, Melanie,Peterson, Laurence B.,Rosa, Ray,Pivnichny, James V.,Tong, Xinchun,Xu, Suoyu S.,Sinclair, Peter J.
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experimental part
p. 4880 - 4895
(2011/09/20)
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- PROCESS FOR SYNTHESIZING A CETP INHIBITOR
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An efficient process is disclosed for producing a compound that is an inhibitor of CETP. The last step of the process is the coupling of an oxazolidinone derivative with a biphenyl moiety to provide a compound of formula (I). In a specific embodiment of this synthesis, a crystalline product is produced which is characterized as a non-solvated crystalline polymorph.
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Page/Page column 7
(2010/11/25)
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- POLYMER FORMULATIONS OF CETP INHIBITORS
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A pharmaceutical composition comprises (a) a CETP inhibiting compound, or a pharmaceutically acceptable salt thereof; (b) a concentration-enhancing polymer; and (c) optionally one or more surfactants; wherein the compound has the structure shown as Formula I below. The composition raises HDL-cholesterol and lowers LDL-cholesterol.
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Page/Page column 20
(2010/11/28)
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- CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITORS
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Compounds of Formula (I), including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In the compounds of Formula
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Page/Page column 32
(2008/06/13)
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- CHOLESTERYL ESTER TRANSFER PROTEIN INHIBITORS
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Compounds of Formula (I), including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In the compounds of Formula (I), A1 is a cyclic group, and B is a cyclic group which is attached to the heterocyclic ring directly or through a methylene group.
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Page/Page column 29
(2008/06/13)
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- CETP INHIBITORS
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Compounds having the structure of Formula (I), including pharmaceutically acceptable salts of the compounds, are CETP inhibitors and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis. In the compounds of Formula (I), B is a cyclic group other than phenyl, and B has a cyclic substituent at a position that is ortho to the position at which B is connected to the remainder of the structure of Formula (I). The 5-membered ring of Formula (I) has a second cyclic substituent in addition to B.
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Page/Page column 35
(2008/06/13)
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- CETP INHIBITORS
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Compounds having the structures of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis: In the compounds of Formula I, B or R2 is a phenyl group which has an ortho aryl, heterocyclic, benzoheterocyclic or benzocycloalky substituent, and one other position on the 5-membered ring has an aromatic, heterocyclic, cycloalkyl, benzoheterocyclic or benzocycloalky substituent connected directly to the ring or attached to the ring through a -CH2-.
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Page/Page column 84
(2010/10/19)
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- Ring-substituted 1,1,2,2-tetraalkylated 1,2-bis(hydroxyphenyl)ethanes. 4. Synthesis, estrogen receptor binding affinity, and evaluation of antiestrogenic and mammary tumor inhibiting activity of symmetrically disubstituted 1,1,2,2-tetramethyl-1,2-bis(hydroxyphenyl)ethanes
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The syntheses of symmetrically 2,2'-disubstituted derivatives of 1,1,2,2-tetramethyl-1,2bis(4-hydroxyphenyl)ethane (1) are and of 5,5'-, and 6,6'-disubstituted derivatives of 1,1,2,2-tetramethyl-1,2-bis(3-hydroxyphenyl)ethane (6) are described (1 and 6 are strong antiestrogens with mammary tumor inhibiting activity exhibiting only slight estrogenic properties): (2,2'-substituents) F (2), Cl (3), OCH3 (4), CH3 (5); (5,5'-substituents) Cl (7); (6,6'-substituents) F (8), Cl (9), OCH3 (10), CH3 (11). The synthesis of 1-11 was accomplished by reductive coupling of the corresponding 2-phenyl-2-propanols with TiCl3 and LiAlH4. The binding affinity of the compounds to the calf uterine estrogen receptor was measured relative to that of [3H]estradiol by a competitive binding assay. With the exception of 7 and 10 all other compounds showed relative binding affinity (RBA) values between 0.5 and 6.4% that of estradiol, 2 (RBA value 6.4), and 8 and 9 (4.0 and 3.5), exceeding those of the corresponding unsubstituted 1 and 6 (3.6 and 3.0). Compounds exhibiting RBA values of >2.5% were evaluated in the mouse uterine weight test. The substituted derivatives showed an increase in uterotrophic and a decrease in antiuterotrophic activity compared to 1 and 6. Compound 2 showed a strong, dose-dependent inhibition on the DMBA-induced hormone-dependent mammary tumor of the SD-rat, exceeding that of the parent compound 1. At a dose of 5 mg/kg per day, 2 reduced total tumor area by 47% and caused a complete remission in 74% of the tumors.
- Hartmann,Schwarz,Heindl,Schonenberger
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p. 1295 - 1301
(2007/10/02)
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