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Stearoyl-CoA desaturase inhibitors: update on patented compounds

, PhD
Pages 1169-1191 | Published online: 19 Aug 2009

Bibliography

  • Miyazaki M, Ntambi JM. Role of stearoyl-Coenzyme A desaturase in lipid metabolism. Prostaglandins Leukot Essent Fatty Acids 2003;68:113-21
  • Enoch HG, Catala A, Strittmatter P. Mechanism of rat liver microsomal stearyl-CoA desaturase. Studies of the substrate specificity, enzyme-substrate interactions, and the function of lipid. J Biol Chem 1976;251:5095-103
  • Dobrzyn A, Ntambi JM. Stearoyl-CoA desaturase as a new drug target for obesity treatment. Obesity Rev 2005;6:169-74
  • Cao H, Gerhold K, Mayers J, et al. Identification of a lipokine, a lipid hormone linking adipose tissue to systemic metabolism. Cell 2008;134:933-44
  • Kaestner KH, Ntambi JM, Kelly TJ Jr, et al. Differentiation-induced gene expression in 3T3-L1 preadipocytes. A second differentially expressed gene encoding stearoyl-coA desaturase. J Biol Chem 1989;264:14755-61
  • Zheng Y, Prouty SM, Harmon A, et al. SCD3--A novel gene of the stearoyl-CoA desaturase family with restricted expression in skin. Genomics 2001;71:182-91
  • Miyazaki M, Jacobson MJ, Man WC, et al. Identification and characterization of murine SCD4, a novel heart-specific stearoyl-CoA desaturase isoform regulated by leptin and dietary factors. J Biol Chem 2003;278:33904-11
  • Zhang L, Ge L, Parimoo S, et al. Human stearoyl-CoA desaturase: Alternative transcripts generated from a single gene by usage of tandem polyadenylation sites. Biochem J 1999;340:255-64
  • Beiraghi S, Zhou M, Talmadge CB, et al. Identification and characterization of a novel gene disrupted by a pericentric inversion Inv(4)(P13.1q21.1) in a family with cleft lip. Gene 2003;309:11-21
  • Zheng Y, Eilertsen KJ, Ge L, et al. SCD1 is expressed in sebaceous glands and is disrupted in the asebia mouse. Nat Genet 1999;23:268-70
  • Ntambi JM, Miyazaki M, Stoehr JP, et al. Loss of stearoyl-CoA desaturase-1 function protects mice against adiposity. Proc Natl Acad Sci USA 2002;99:11482-6
  • Rahman SM, Dobrzyn A, Dobrzyn P, et al. Stearoyl-CoA desaturase 1 deficiency elevates insulin-signaling components and down-regulates protein-tyrosine phosphatase 1B in muscle. Proc Natl Acad Sci USA 2003;100:11110-5
  • Dobrzyn P, Dobrzyn A, Miyazaki M, et al. Stearoyl-CoA desaturase 1 deficiency increases fatty acid oxidation by activating AMP-activated protein kinase in liver. Proc Natl Acad Sci USA 2004;101:6409-14
  • Miyazaki M, Kim YC, Gray-Keller MP, et al. The biosynthesis of hepatic cholesterol esters and triglycerides is impaired in mice with a disruption of the gene for stearoyl-CoA desaturase 1. J Biol Chem 2000;275:30132-8
  • Miyazaki M, Kim HJ, Man WC, et al. Oleoyl-CoA is the major de novo product of stearoyl-CoA desaturase 1 gene isoform and substrate for the biosynthesis of the harderian gland 1-alkyl-2,3-diacylglycerol. J Biol Chem 2001;276:39455-61
  • Flowers JB, Rabaglia ME, Schueler KL, et al. Loss of stearoyl-CoA desaturase-1 improves insulin sensitivity in lean mice but worsens diabetes in leptin-deficient obese mice. Diabetes 2007;56:228-1239
  • Jiang G, Li Z, Liu F, et al. Prevention of obesity in mice by antisense oligonucleotide inhibitors of stearoyl-CoA desaturase-1. J Clin Invest 2005;115:1030-8
  • Gutierrez-Juarez R, Pocai A, Mulas C, et al. Critical role of stearoyl-CoA desaturase-1 (SCD1) in the onset of diet-induced hepatic insulin resistance. J Clin Invest 2006;116:1686-95
  • Miyazaki M, Man WC, Ntambi JM. Targeted disruption of stearoyl-CoA desaturase1 gene in mice causes atrophy of sebaceous and meibomian glands and depletion of wax esters in the eyelid. J Nutr 2001;31:2260-8
  • Binczek E, Jenke B, Holz B, et al. Obesity resistance of the stearoyl-CoA desaturase-deficient (scd1-/-) mouse results from disruption of the epidermal lipid barrier and adaptive thermoregulation. Biol Chem 2007;388:405-18
  • Morgan-Lappe SE, Tucker LA, Huang X, et al. Identification of Ras-related nuclear protein, targeting protein for xenopus kinesin-like protein 2, and stearoyl-CoA desaturase 1 as promising cancer targets from an RNAi-based screen. Cancer Res 2007;67:4390-8
  • Scaglia N, Igal RA. Inhibition of stearoyl-CoA desaturase 1 expression in human lung adenocarcinoma cells impairs tumorigenesis. Int J Oncol 2008;33:839-50
  • Steinar S, Hilde N, Sørensen LN, et al. Thia fatty acids, metabolism and metabolic effects. Biochimica Biophysica Acta 1997;1344:115-31
  • Gomez FE, Bauman DE, Ntambi JM, Fox BG. Effects of sterculic acid on stearoyl-CoA desaturase in differentiating 3T3-l1 adipocytes. Biochem Biophys Res Commun 2003;300:316-26
  • Ntambi JM. Regulation of stearoyl-CoA desaturase by polyunsaturated fatty acids and cholesterol. J Lipid Res 1999;40:1549-58
  • Abreo M, Chafeev M, Chakka N, et al. Pyridazine derivatives and their use as therapeutic agents. WO2005011655; 2005
  • Fu J-M, Kodumuru V, Sun S, et al. Nicotinamide derivatives and their use as therapeutic agents. US20050119251; 2005
  • Fu J-M, Kodumuru V, Sun S, et al. Nicotinamide derivatives and their use as therapeutic agents. US20050119251; 2005
  • Fu J-M, Kodumuru V, Sun S, et al. Nicotinamide derivatives and their use as therapeutic agents. WO2006014168; 2006
  • Kamboj R, Zhang Z, Sviridov S, et al. Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors. WO2006034441; 2006
  • Kamboj R, Fu J-M, Kodumuru V, et al. Bicyclic heterocyclic derivatives and their use as inhibitors of stearoyl-CoA-desaturase (SCD). WO2006034312; 2006
  • Kamboj R, Zhang Z, Fu J-M, et al. Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-CoA desaturase enzymes. WO2006034315; 2006
  • Sun S, Zhang Z, Roth CJ. Piperazine derivatives and their uses as therapeutic agents. WO2006125194; 2006
  • Fu J-M, Liu S. Thiazolidine derivatives and their uses as therapeutic agents. WO2007046868; 2007
  • Fu J-M, Kodumuru V, Sviridov S. Fused piperidine derivatives and their uses as therapeutic agents. WO2007050124; 2007
  • Kamboj R, Zhang Z, Fu J-M, et al. Heterocyclic derivatives and their use as therapeutic agents. WO2006034279; 2006
  • Kamboj R, Zhang Z, Fu J-M, et al. Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase. WO2006034338; 2006;
  • Fu J-M, Kodumuru V, Liu S. Piperidine derivatives and their use as stearoyl-CoA desaturase modulators. WO2006125181; 2006
  • Chowdhury S, Roth CJ. Heteroaryl compounds and their uses as therapeutic agents. WO2007044085; 2007
  • Kodumuru V, Roth CJ. Piperidine derivatives and their uses as therapeutic agents. WO2007046867; 2007
  • Kamboj R, Zhang Z, Fu J-M, et al. Pyridazine derivatives for inhibiting human stearoyl-CoA-desaturase. WO2006034341; 2006
  • Kamboj R, Zhang Z, Fu J-M, et al. Heterocyclic Derivatives and Their Use as Stearoyl-CoA Desaturase Inhibitors. WO2006101521; 2006
  • Fu J-M, Kodumuru V, Sviridov S. Tricyclic compounds and their uses as therapeutic agents. WO2006125179; 2006
  • Kamboj R, Zhang Z, Fu J-M, et al. Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors. WO2006034440; 2006
  • Kamboj R, Kodumuru V, Roth CJ. Pyridine derivatives for inhibiting human stearoyl-CoA-desaturase. WO2006034446; 2006
  • Hou D, Roth CJ. Tricyclic pyridazine compounds and their uses as therapeutic agents. WO2006125178; 2006
  • Fu J-M, Liu S. Piperazine derivatives and their uses as therapeutic agents. WO2006125180; 2006
  • Chowdhury S, Zhang Z. Macrocyclic compounds and their uses as stearoyl-CoA desaturase. WO2007136746; 2007
  • Fu J-M, Hou D, Kamboj R, et al. Aminothiazole derivatives as human stearoyl-CoA desaturase inhibitors. WO2007130075; 2007
  • Dales N, Fonarev J, Fu J-M, et al. Organic Compounds. WO2007143597; 2007
  • Dales N, Zhang Z. 2-(Pyrazin-2-yl)-thiazole and 2-(1H-pyrazol-3-yl)-thiazole derivatives as well as related compounds as stearoyl-CoA desaturase (SCD) inhibitors for the treatment of metabolic, cardiovascular and other disorders. WO2008024390; 2008
  • Dales N, Zhang Z, Kamboj R, et al. Heterocylic organic compounds. WO2008036715; 2008
  • Dales N, Zhang Z, Fonarev J. 2-Substituted 5-membered heterocycles as SCD inhibitors. WO2008074835; 2008
  • Dales N, Fonarev J, Fu J. Organic Compounds. WO2008127349; 2008
  • Li CS, Ramtohul Y, Huang Z, et al. Azacyclohexane derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2006130986; 2006
  • Black C, Deschenes D, Gagnon M, et al. Heteroaromatic compounds as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2007009236; 2007
  • Crane S, Robichaud JS, Leger S, Ramtohul Y. Azacyclohexane derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase. WO2007056846; 2007
  • Ramtohul Y. Azacycloalkane derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2008017161; 2008
  • Leger S, Deschenes D, Fortin R, et al. Preparation of [1,3]thiazolo[4,5-d] pyrimidine derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2008141455; 2008
  • Leblanc Y, Gagnon M. Cyclic amine derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2007134457; 2007
  • Isabel E, Oballa R, Powell D, Robichaud J. Azetidine derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2007143823; 2007
  • Li CS, Ramtohul YK. Azacyclopentane derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2007143824; 2007
  • Oballa RM, Deschenes D, Gagnon M, et al. Azacycloalkane derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2008046226; 2008
  • Lachance N, Li CS, Leclerc J-P, et al. Azacycloalkane derivatives as inhibitors of stearoyl-Coenzyme A delta-9 desaturase. WO2008064474; 2008
  • Lachance N, Li CS, Leclerc J-P, Ramtohul YK. Heteroaromatic compounds as inhibitors of stearoyl-Coenzyme A delta-9 desaturase, their preparation, pharmaceutical compositions, and use in therapy. WO2008128335; 2008
  • Liu G, Lynch JK, Freeman J, et al. Discovery of potent, selective, orally bioavailable stearoyl-coa desaturase 1 inhibitors. J Med Chem 2007;50:3086-100
  • Zhao H, Serby MD, Smith HT, et al. Discovery of 1-(4-phenoxypiperidin-1-yl)-2-arylaminoethanone stearoyl-CoA desaturase 1 inhibitors. Bioorg Med Chem Lett 2007;17:3388-91
  • Xin Z, Zhao H, Serby MD, et al. Discovery of piperidine-aryl urea-based stearoyl-CoA desaturase 1 inhibitors. Bioorg Med Chem Lett 2008;18:4298-302
  • Liu G. Stearoyl-CoA desaturase-1 (SCD1) Inhibitors: Discovery and in vivo evaluation. Emerging Targets for Type 2 Diabetes Symposium, The 233th ACS National Meeting, Chicago, IL, March 2007, MEDI-382
  • Zilbershtein T, Cole A, Zablocki J, et al. Pteridinone derivatives for use as stearoyl CoA desaturase inhibitors. WO2008123891; 2008
  • Zablocki J, Glushkov A, Zilbershtein T, et al. Bicyclic nitrogen-containing heterocyclic compounds for use as stearoyl CoA desaturase inhibitors. WO2008043087; 2008
  • Koltun D, Parkhill E, Boze M, et al. 3-Hydroquinazolin-4-one derivatives for use as stearoyl CoA desaturase inhibitors. WO2008127615; 2008
  • Koltun DO, Parkhill EQ, Vasilevich NI, et al. Potent, selective, and metabolically stable stearoyl-CoA desaturase (SCD) inhibitors for the potential treatment of obesity and diabetes. The 236th ACS National Meeting, Philadelphia, PA, August 2008, MEDI-198
  • Daugan AC-M, Dean AW. Compounds. WO2008074824; 2008
  • Bouillot AMJ, Daugan AC-M, Dean AW, Fillmore MC. Compounds. WO20080074832; 2008
  • Daugan AC-M. Compounds. WO2008074833; 2008
  • Daugan AC-M. Compounds. WO2008074834; 2008
  • Bouillot AMJ, Boyer T, Daugan AC-M, et al. Thiadiazole derivatives, inhibitors of stearoyl-CoA desaturase. WO2008104524; 2008
  • Daugan AC-M. Preparation of pyrazole derivatives and use thereof as inhibitors of stearoyl-CoA desaturase. WO2009010560; 2009
  • Taniguchi T, Miyata K, Kubo O, Matsui J. Preparation of aromatic amine derivatives as stearoyl-CoA desaturase (SCD) inhibitors. WO2008044767; 2008
  • Taniguchi T, Miyata K, Kubo O. Preparation of pyridazine ring-containing spiro compounds as stearoyl-CoA desaturase inhibitors for treatment of obesity, diabetes, etc. WO2008096746; 2008
  • Uto Y, Kiyotsuka Y. Preparation of spiropiperidine derivatives as stearoyl-CoA-desaturase inhibitors. WO2008056687; 2008
  • Utsu Y, Kiyotsuka Y, Kurata H, et al. Preparation of heteroaryl piperidine derivatives as stearoyl CoA desaturase inhibitors. JP2009019013; 2009
  • Uto Y, Kiyotsuka Y, Kurata H, et al. Preparation of azole amide derivatives as inhibitors of stearoyl CoA desaturase. WO2008139845; 2008
  • Iida T, Ubukata M, Mitani I, et al. Five-membered cyclic amide compound and use thereof. WO2008120744; 2008
  • Iida T, Mitani I, Nakagawa Y, Tanaka M. Six-membered amide compound and use thereof. WO2008123469; 2008
  • Iida T, Mitani I, Nakagawa Y, Tanaka M. Preparation of six-membered heterocyclic amide and benzamide derivatives as stearoyl-CoA desaturase 1 (SCD1) inhibitors. WO2008123469; 2008
  • Ubukata M, Maeda K, Iida T, Mitani I. Urea compound and use thereof. WO2008120759; 2008
  • Thomas A, Lingam VSPR, Chaudhari SS, et al. Preparation of oxazolanones as therapeutic stearoyl CoA desaturase inhibitors. WO2008029266; 2008
  • Thomas A, Lincam VSPR, Phatangare SK, et al. Acetylene derivatives as stearoyl CoA desaturase inhibitors and their preparations, pharmaceutical compositions and use in the treatment of diseases. WO2008062276; 2008
  • Lundbaeck T, Climent-Johansson I, Vaagberg J, et al. Preparation of pyrazolo[1,5-a]pyrimidine derivatives for use as inhibitors of stearoyl-CoA desaturase (SCD) activity. WO2008003753; 2008
  • Bremberg U, Linden A, Lundbaeck T, et al. Preparation of pyrazolo[1,5-a]pyrimidines as inhibitors of stearoyl-CoA desaturase. WO2008116898; 2008
  • Bischoff A, Subramanya HS, Sundaresan K, et al. Novel piperazine derivatives as inhibitors of stearoyl-CoA desaturase. WO2008157844; 2008
  • Zoller G, Voss MD, Keil S, et al. Preparation of hexahydropyrrolo[3,4-c]pyrroles as stearoyl CoA desaturase inhibitors. WO2008135141; 2008
  • Attie AD, Krauss RM, Gray-Keller MP, et al. Relationship between stearoyl-CoA desaturase activity and plasma triglycerides in human and mouse hypertriglyceridemia. J Lipid Res 2002;43:1899-907
  • Mar-Heyming R, Miyazaki M, Weissglas-Volkov D, et al. Association of stearoyl-CoA desaturase 1 activity with familial combined hyperlipidemia. Arterioscler Thromb Vasc Biol 2008;28:1193-9
  • Hulver MW, Berggren JR, Carper MJ, et al. Elevated stearoyl-CoA desaturase-1 expression in skeletal muscle contributes to abnormal fatty acid partitioning in obese humans. Cell Metab 2005;2:251-61
  • Stefan N, Peter A, Cegan A, et al. Low hepatic stearoyl-CoA desaturase 1 activity is associated with fatty liver and insulin resistance in obese humans. Diabetologia 2008;51:648-56
  • Kamboj R, Winther M, Fraser R, et al. Combination therapy. WO2006086445; 2006
  • Miyazaki M, Flowers MT, Sampath H, et al. hepatic stearoyl-CoA desaturase-1 deficiency protects mice from carbohydrate-induced adiposity and hepatic steatosis. Cell Metab 2007;6:484-96
  • Brown JM, Chung S, Sawyer JK, et al. Inhibition of stearoyl-Coenzyme A desaturase 1 dissociates insulin resistance and obesity from atherosclerosis. Circulation 2008;118:1467-75
  • Peter A, Weigert C, Staiger H, et al. Induction of stearoyl-CoA desaturase protects human arterial endothelial cells against lipotoxicity. Am J Physiol Endocrinol Metab 2008;295:E339-49
  • Bilich A, Winther MD, Goldberg YP. Preparation of pyridazine derivatives as stearoyl-CoA desaturase inhibitors for treating skin disorders. US20080280916; 2008

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