Richard L. Apodaca

I'm a chemist and software developer living in La Jolla, California. In 2007 I founded Metamolecular, LLC, a company dedicated to helping chemistry-focused organizations worldwide use the Web for better business and research.

Education and Work

Contact

Email: rich...@yahoo.com

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Peer-Reviewed Publications

  1. Karbarz, M.J.; Luo, L.; Chang, L.; Tham, C-S; Palmer, J.A.; Wilson, S.J.; Wennerholm, M.L.; Brown, S.M.; Scott, B.P.; Apodaca, R.L.; Keith, J.M.; Wu, J.; Breitenbucher, J.G.; Chaplan, S.R.; Webb, M. Biochemical and Biological Properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a Mechanism-Based Inhibitor of Fatty Acid Amide Hydrolase Anesth. Analg. 2009, 108, 316-329.

  2. Keith, J.M.; Apodaca, R.; Xiao, W.; Seierstad, M.; Pattabiraman, K.; Wu, J.; Webb, M.; Karbarz, M.J.; Brown, S.; Wilson, S.; Scott, B.; Tham, Cc; Luo, L.; Palmer, J.; Wennerholm, M.; Chaplan, S.; Breitenbucher, J.G. Thiadiazolopiperazinyl ureas as inhibitors of fatty acid amide hydrolase Bioorg. Med. Chem. Lett. 2008, 18, 4838-4843.

  3. Bembenek, S.D.; Keith, J.M.; Letavic, M.A.; Apodaca, R.; Barbier, A.J.; Dvorak, L.; Aluisio, L.; Miller, K.L.; Lovenberg, T.W.; Carruthers, N.I. Lead identification of acetylcholinesterase inhibitors–histamine H3 receptor antagonists from molecular modeling Bioorg. Med. Chem. 2008, 16, 2968-2937.

  4. Timmons, A.; Seierstad, M.; Apodaca, R.; Epperson, M.; Pippel, D.; Brown, S.; Chang, L.; Scott, B.; Webb, M.; Chaplan, S.R.; Breitenbucher, J.G. Novel ketooxazole based inhibitors of fatty acid amide hydrolase (FAAH) Bioorg. Med. Chem. Lett. 2008, 18, 2109-2113.

  5. Romero, F.A.; Du, W.; Hwang, I.; Rayl, T.J.; Kimball, F. S.; Leung, D.; Hoover, H.S.; Apodaca, R.L.; Breitenbucher, J.G.; Cravatt, B.F.; Boger, D. L. Potent and Selective α-Ketoheterocycle-Based Inhibitors of the Anandamide and Oleamide Catabolizing Enzyme, Fatty Acid Amide Hydrolase J. Med. Chem. 2007, 50, 1058-1068.

  6. Swanson, D.M.; Wilson, S.J.; Boggs, J.D.; Xiao, W.; Apodaca, R.; Barbier, A.J.; Lovenberg, T.W.; Carruthers, N.I. Aplysamine-1 and Related Analogs as Histamine H3 Receptor Antagonists. Bioorg. Med. Chem. Lett. 2006, 16, 897-900.

  7. Dvorak, C. A.; Apodaca, R.; Barbier, A.J.; Berridge, C.W.; Wilson, S.J.; Boggs, J.D.; Xiao, W.; Lovenberg, T.W; Carruthers, N.I. 4-Phenoxypiperidines: Potent, Conformationally Restricted, Non-Imidazole Histamine H3 Antagonists. J. Med. Chem. 2005, 48, 2229-2238.

  8. Barbier, A.J.; Berridge, C.; Dugovic, C.; Laposky, A.D.; Wilson, S.J.; Boggs, J.; Aluisio, L.; Lord, B.; Mazur, C.; Pudiak, C.M.; Langlois, X.; Xiao, W.; Apodaca, R.; Carruthers, N.I.; Lovenberg, T.W. Acute wake-promoting actions of JNJ-5207852, a novel, diamine-based H3 antagonist. Br. J. Pharmacol. 2004, 143, 649-661.

  9. Apodaca, Richard; Dvorak, Curt A.; Xiao, Wei; Barbier, Ann J.; Boggs, Jamin D.; Wilson, Sandy J.; Lovenberg, Timothy W.; Carruthers, Nicholas I. A New Class of Diamine-Based Human Histamine H3 Receptor Antagonists: 4-(Aminoalkoxy)benzylamines. J. Med. Chem. 2003, 46, 3938-3944.

  10. Apodaca, R.; Xiao, W. Direct Reductive Amination of Aldehydes and Ketones: Catalysis by Dibutyltin Dichloride. Org. Lett. 2001, 3, 1745-1748.

  11. Lynch, Vincent M.; Apodaca, Richard; Whitesell, James K.; Chou, Ming I. Trans-(R,R)-2,2'-(cyclopenta-1,2-diyl)diphenyl bis[(R)-O-methylmandelate]. Acta Crystallographica, Section C: Crystal Structure Communications 1998, 10, C54.

  12. Apodaca R. Comprehensive Organic Functional Group Transformations. (Book Review) J. Am. Chem Soc. 1997, 119, 2343.

  13. Whitesell, J.K.; Apodaca, R. Synthesis and Resolution of a New Chiral C2‑Symmetrical Bisphenol: trans-1,2-Bis(2-hydroxyphenyl)cyclopentane. Tetrahedron Lett. 1997, 38, 2589-2592.

  14. Whitesell, J.K.; Apodaca, R. A Convenient Synthesis of Protected and Free Homallylic Alcohols: Catalytic Use of Dibutyltin Dichloride in the Allylation of Aldehydes with Allyltributyltin. Tetrahedron Lett. 1996, 37, 3955-3958.

  15. Whitesell, J.K.; Apodaca, R. Trimethylsilylcyanation of Aldehydes and Ketones Catalyzed by Diorganotin Dichlorides. Tetrahedron Lett. 1996, 37, 2525-2528.

Issued Patents

  1. Apodaca; Richard, Deng; Xiaohu, Jablonowski; Jill A., Mani; Neelakandha, Pandit; Chennagiri R., Xiao; Wei Phenylalkynes US 7,482,364

  2. Apodaca; Richard, Deng; Xiaohu, Jablonowski; Jill A., Mani; Neelakandha, Pandit; Chennagiri R., Xiao; Wei Phenylalkynes US 7,446,104

  3. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Rudolph; Dale A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxyalkylamines US 7,429,586

  4. Apodaca; Richard L., Jablonowski; Jill A., Ly; Kiev S., Shah; Chandravadan R., Swanson; Devin M., Xiao; Wei Piperazinyl and diazapanyl benzamides and benzthioamides US 7,414,047

  5. Apodaca; Richard, Deng; Xiaohu, Jablonowski; Jill A., Mani; Neelakandha, Pandit; Chennagiri R., Xiao; Wei Phenylalkynes US 7,288,540

  6. Apodaca; Richard L., Dvorak; Curt A., Shah; Chandravadan R., Xiao; Wei Phenylpiperidines and phenylpyrrolidines US 7,279,491

  7. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxypiperidines US 7,241,778

  8. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Rudolph; Dale A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxyalkylamines US 7,186,732

  9. Apodaca; Richard, Carruthers; Nicholas I., Dvorak; Curt A., Shah; Chandravadan R., Xiao; Wei Non-imidazole aryloxypiperidines US 7,071,191

  10. Apodaca; Richard, Xiao; Wei, Jablonowski; Jill A. Phenylalkynes US 6,884,803

Patent Applications

  1. Apodaca, Richard; Breitenbucher, J. Guy; Pattabiraman, Kanaka; Seierstad, Mark; Xiao, Wei. Preparation of thiadiazolylpiperazinecarboxamides as modulators of fatty acid amide hydrolase (FAAH). US 2007004741

  2. Apodaca, Richard; Barbier, Ann J.; Carruthers, Nicholas I.; Gomez, Leslie A.; Keith, John M.; Lovenberg, Timothy W.; Wolin, Ronald L. Hexahydropyrroloisoquinoline compounds as histamine H3 receptor and serotonin transporter modulators and their preparation, pharmaceutical compositions and use in the treatment of CNS disorders. WO 2006138604

  3. Apodaca, Richard; Breitenbucher, J. Guy; Pattabiraman, Kanaka; Seierstad, Mark; Xiao, Wei. Piperazinyl and piperidinyl ureas as modulators of fatty acid amide hydrolase. WO 2006074025

  4. Apodaca, Richard L.; Dvorak, Curt A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of phenylpiperidines and phenylpyrrolidines as histamine H3 receptor inhibitors. US 2004087573

  5. Apodaca, Richard L.; Jablonowski, Jill A.; Ly, Kiev S.; Shah, Chandravadan R.; Swanson, Devin M.; Xiao, Wei. Preparation of piperazinyl and diazepanyl benzamides and benzothioamides as inhibitors of histamine H3 receptor. WO 2004037801

  6. Apodaca, Richard L.; Dvorak, Curt A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of phenylpiperidines and phenylpyrrolidines as histamine H3 receptor modulators. WO 2004037257

  7. Apodaca, Richard; Deng, Xiaohu; Jablonowski, Jill A.; Mani, Neelakandha; Pandit, Chennagiri R.; Xiao, Wei. Preparation of substituted phenylalkynes as H3 receptor ligands. US 2004002604

  8. Apodaca, Richard; Xiao, Wei; Jablonoski, Jill A. Preparation of substituted phenylalkynes for use in histamine-mediated disorders. 2003050099

  9. Apodaca, Richard; Carruthers, Nicholas I.; Carson, John R.; Chai, Wenying; Kwok, Annette K.; Li, Xiaobing; Lovenberg, Timothy W.; Rudolph, Dale A.; Shah, Chandravadan R. Octahydroindolizine and quinolizine and hexahydropyrrolizine derivatives as histaminic H1 and H3 antagonists. WO 2002024695

  10. Apodaca, Richard; Carruthers, Nicholas I.; Dvorak, Curt A.; Rudolph, Dale A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of non-imidazole aryloxyalkylamines as histamine H3 receptor antagonists. WO 2002012214

  11. Apodaca, Richard; Carruthers, Nicholas I.; Dvorak, Curt A.; Shah, Chandravadan R.; Xiao, Wei. Preparation of aryloxypiperidines as histamine H3 receptor antagonists. WO 2002012190