메뉴 건너뛰기




Volumn 51, Issue 21, 2008, Pages 6970-6979

Tetrahydrolipstatin analogues as modulators of endocannabinoid 2-arachidonoylglycerol metabolism

Author keywords

[No Author keywords available]

Indexed keywords

2 ARACHIDONOYLGLYCEROL; ACYLGLYCEROL LIPASE; ANANDAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; ENDOCANNABINOID; FATTY ACID AMIDASE; LIPOPROTEIN LIPASE; N ACETYL ISOLEUCINE 1 [3 HEXYL 4 OXO 2 OXETANYL]METHYL]DODECYL ESTER; N ACETYL VALINE 1 [[3 HEXYL 4 OXO 2 OXETANYL]METHYL]DODECYL ESTER; N FORMYL ALANINE 1 [3 HEXYL 4 OXO 2 OXETANYL]METHYL]DODECYL ESTER; N FORMYL ISOLEUCINE 1 [[3 HEXYL 4 OXO 2 OXETANYL]METHYL]DODECYL ESTER; N FORMYL VALINE 1 [[3 HEXYL 4 OXO 2 OXETANYL]METHYL]DODECYL ESTER; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 56249108088     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800978m     Document Type: Article
Times cited : (75)

References (60)
  • 4
    • 0036019386 scopus 로고    scopus 로고
    • Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological significance
    • Sugiura, T.; Kobayashi, Y.; Oka, S.; Waku, K. Biosynthesis and degradation of anandamide and 2-arachidonoylglycerol and their possible physiological significance. Prostaglandins, Leukotrienes Essent. Fatty Acids 2002, 66, 173-192.
    • (2002) Prostaglandins, Leukotrienes Essent. Fatty Acids , vol.66 , pp. 173-192
    • Sugiura, T.1    Kobayashi, Y.2    Oka, S.3    Waku, K.4
  • 6
    • 33847702499 scopus 로고    scopus 로고
    • Critical enzymes involved in endocannabinoid metabolism
    • (a) Basavarajappa, B. S. Critical enzymes involved in endocannabinoid metabolism. Protein Peptide Lett. 2007, 14, 237-246.
    • (2007) Protein Peptide Lett , vol.14 , pp. 237-246
    • Basavarajappa, B.S.1
  • 8
    • 23444432920 scopus 로고    scopus 로고
    • The endocannabinoid system: Drug targets, lead compounds, and potential therapeutic applications
    • (c) Lambert, D. M.; Fowler, C. J. The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. J. Med. Chem. 2005, 48, 5059-5087.
    • (2005) J. Med. Chem , vol.48 , pp. 5059-5087
    • Lambert, D.M.1    Fowler, C.J.2
  • 9
    • 20444460345 scopus 로고    scopus 로고
    • The endocannabinoid signalling system: Biochemical aspects
    • (d) Bisogno, T.; Ligresti, A.; Di Marzo, V. The endocannabinoid signalling system: biochemical aspects. Pharmacol., Biochem. Behav. 2005, 81, 224-238.
    • (2005) Pharmacol., Biochem. Behav , vol.81 , pp. 224-238
    • Bisogno, T.1    Ligresti, A.2    Di Marzo, V.3
  • 10
    • 1842611887 scopus 로고    scopus 로고
    • The endocannabinoid system: A general view and latest additions
    • (e) De Petrocellis, L.; Cascio, M. G.; Di Marzo, V. The endocannabinoid system: a general view and latest additions. Br. J. Pharmacol. 2004, 141, 765-774.
    • (2004) Br. J. Pharmacol , vol.141 , pp. 765-774
    • De Petrocellis, L.1    Cascio, M.G.2    Di Marzo, V.3
  • 12
    • 43249100162 scopus 로고    scopus 로고
    • Targeting the endocannabinoid system: To enhance or reduce
    • Di Marzo, V. Targeting the endocannabinoid system: to enhance or reduce. Nat. Rev. Drug Discovery 2008, 7, 438-455.
    • (2008) Nat. Rev. Drug Discovery , vol.7 , pp. 438-455
    • Di Marzo, V.1
  • 13
    • 10044228562 scopus 로고    scopus 로고
    • Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol
    • Ghafouri, N.; Tiger, G.; Razdan, R. K.; Mahadevan, A.; Pertwee, R. G.; Martin, B. R.; Fowler, C. J. Inhibition of monoacylglycerol lipase and fatty acid amide hydrolase by analogues of 2-arachidonoylglycerol. Br. J. Pharmacol. 2004, 143, 774-784.
    • (2004) Br. J. Pharmacol , vol.143 , pp. 774-784
    • Ghafouri, N.1    Tiger, G.2    Razdan, R.K.3    Mahadevan, A.4    Pertwee, R.G.5    Martin, B.R.6    Fowler, C.J.7
  • 16
    • 0023626926 scopus 로고    scopus 로고
    • Weibel, E. K.; Hadvary, P.; Hochuli, E.; Kupfer, E.; Lengsfeld, H. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation, and biological activity. J. Antibiot. 1987, 40, 1081-1085.
    • (a) Weibel, E. K.; Hadvary, P.; Hochuli, E.; Kupfer, E.; Lengsfeld, H. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. I. Producing organism, fermentation, isolation, and biological activity. J. Antibiot. 1987, 40, 1081-1085.
  • 17
    • 0023620073 scopus 로고
    • Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. II. Chemistry and structure elucidation
    • (b) Hochuli, E.; Kupfer, E.; Maurer, R.; Meister, W.; Mercadal, Y.; Schmidt, K. Lipstatin, an inhibitor of pancreatic lipase, produced by Streptomyces toxytricini. II. Chemistry and structure elucidation. J. Antibiot. 1987, 40, 1086-1091.
    • (1987) J. Antibiot , vol.40 , pp. 1086-1091
    • Hochuli, E.1    Kupfer, E.2    Maurer, R.3    Meister, W.4    Mercadal, Y.5    Schmidt, K.6
  • 18
    • 0030952712 scopus 로고    scopus 로고
    • Mode of action of Orlistat
    • (a) Guerciolini, R. Mode of action of Orlistat. Int. J. Obes. 1997, 21, S12-S23.
    • (1997) Int. J. Obes , vol.21
    • Guerciolini, R.1
  • 19
    • 0028284103 scopus 로고
    • Interactions of lipoprotein lipase with the active-site inhibitor tetrahydrolipstatin (Orlistat)
    • (b) Lookene, A.; Skottova, N.; Olivecrona, G. Interactions of lipoprotein lipase with the active-site inhibitor tetrahydrolipstatin (Orlistat). Eur. J. Biochem. 1994, 222, 395-103.
    • (1994) Eur. J. Biochem , vol.222 , pp. 395-103
    • Lookene, A.1    Skottova, N.2    Olivecrona, G.3
  • 20
    • 0026757988 scopus 로고
    • Tetrahydrolipstatin: Degradation products produced by human carboxyl-ester lipase
    • (c) Stalder, H.; Oesterhelt, G. Tetrahydrolipstatin: degradation products produced by human carboxyl-ester lipase. Helv. Chim. Acta 1992, 75, 1593-1603.
    • (1992) Helv. Chim. Acta , vol.75 , pp. 1593-1603
    • Stalder, H.1    Oesterhelt, G.2
  • 21
    • 0025911832 scopus 로고
    • The lipase inibitor tetrahydrolipstatin binds covalently to the putative active site serine of pancreatic lipase
    • (d) Hadvary, P.; Sidler, W.; Meister, W.; Vetter, W.; Wolfer, H. The lipase inibitor tetrahydrolipstatin binds covalently to the putative active site serine of pancreatic lipase. J. Biol. Chem. 1991, 266, 2021-2027.
    • (1991) J. Biol. Chem , vol.266 , pp. 2021-2027
    • Hadvary, P.1    Sidler, W.2    Meister, W.3    Vetter, W.4    Wolfer, H.5
  • 22
    • 0023791240 scopus 로고
    • Mode of action of tetrahydroplipstatin: A derivative of the naturally occurring lipase inhibitor lipstatin
    • (e) Borgström, B. Mode of action of tetrahydroplipstatin: a derivative of the naturally occurring lipase inhibitor lipstatin. Biochim. Biophys. Acta 1988, 962, 308-316.
    • (1988) Biochim. Biophys. Acta , vol.962 , pp. 308-316
    • Borgström, B.1
  • 23
    • 37348999202 scopus 로고    scopus 로고
    • Pharmacological evidence for the involvement of diacylglycerol lipase in depolarization-induced endocannabinoid release
    • (a) Hashimotodani, Y.; Ohno-Shosaku, T.; Maejima, T.; Fukami, K.; Kano, M. Pharmacological evidence for the involvement of diacylglycerol lipase in depolarization-induced endocannabinoid release. Neuropharmacology 2008, 54, 58-67.
    • (2008) Neuropharmacology , vol.54 , pp. 58-67
    • Hashimotodani, Y.1    Ohno-Shosaku, T.2    Maejima, T.3    Fukami, K.4    Kano, M.5
  • 24
    • 34147145848 scopus 로고    scopus 로고
    • Subcellular arrangement of molecules for 2-arachidonoylglycerol- mediated retrograde signaling and its physiological contribution to synaptic modulation in the striatum
    • (b) Uchigashima, M.; Narushima, M.; Fukaya, M.; Katona, I.; Kano, M.; Watanabe, M. Subcellular arrangement of molecules for 2-arachidonoylglycerol- mediated retrograde signaling and its physiological contribution to synaptic modulation in the striatum. J. Neurosci. 2007, 27, 3663-3676.
    • (2007) J. Neurosci , vol.27 , pp. 3663-3676
    • Uchigashima, M.1    Narushima, M.2    Fukaya, M.3    Katona, I.4    Kano, M.5    Watanabe, M.6
  • 25
    • 33847341172 scopus 로고    scopus 로고
    • Anandamide regulates postnatal development of long term synaptic plasticity in the rat dorsolateral striatum
    • (c) Ade, K. K.; Lovinger, D. M. Anandamide regulates postnatal development of long term synaptic plasticity in the rat dorsolateral striatum. J. Neurosci. 2007, 27, 2403-2409.
    • (2007) J. Neurosci , vol.27 , pp. 2403-2409
    • Ade, K.K.1    Lovinger, D.M.2
  • 26
    • 33750711997 scopus 로고    scopus 로고
    • Depolarization-induced retrograde synaptic inhibition in the mouse cerebellar cortex is mediated by 2-arachidonoylglycerol
    • (d) Szabo, B.; Urbanski, M. J.; Bisogno, T.; Di Marzo, V.; Mendiguren, A.; Baer, W. U.; Freiman, I. Depolarization-induced retrograde synaptic inhibition in the mouse cerebellar cortex is mediated by 2-arachidonoylglycerol. J. Physiol. 2006, 577, 263-280.
    • (2006) J. Physiol , vol.577 , pp. 263-280
    • Szabo, B.1    Urbanski, M.J.2    Bisogno, T.3    Di Marzo, V.4    Mendiguren, A.5    Baer, W.U.6    Freiman, I.7
  • 27
    • 37149013708 scopus 로고    scopus 로고
    • A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol
    • Blankman, J. L.; Simon, G. M.; Cravatt, B. F. A comprehensive profile of brain enzymes that hydrolyze the endocannabinoid 2-arachidonoylglycerol. Chem. Biol. 2007, 14, 1347-1356.
    • (2007) Chem. Biol , vol.14 , pp. 1347-1356
    • Blankman, J.L.1    Simon, G.M.2    Cravatt, B.F.3
  • 28
    • 34247183643 scopus 로고    scopus 로고
    • 1 receptor-stimulated cannabinoid CB1 receptor activity. J. Biol. Chem. 2007, 282, 7753-7757.
    • 1 receptor-stimulated cannabinoid CB1 receptor activity. J. Biol. Chem. 2007, 282, 7753-7757.
  • 30
    • 36849022663 scopus 로고    scopus 로고
    • Enantioselective total synthesis of (-)-tetrahydrolipstatin using Oppolzer's sultam directed aldol reaction
    • (a) Kumaraswamy, G.; Markondaiah, B. Enantioselective total synthesis of (-)-tetrahydrolipstatin using Oppolzer's sultam directed aldol reaction. Tetrahedron Lett. 2008, 49, 327-330.
    • (2008) Tetrahedron Lett , vol.49 , pp. 327-330
    • Kumaraswamy, G.1    Markondaiah, B.2
  • 31
    • 33750075043 scopus 로고    scopus 로고
    • Total synthesis and comparative analysis of orlistat, valillactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase
    • (b) Ma, G.; Zancanella, M.; Oyola, Y.; Richardson, R. D.; Smith, J. W.; Romo, D. Total synthesis and comparative analysis of orlistat, valillactone, and a transposed orlistat derivative: inhibitors of fatty acid synthase. Org. Lett. 2006, 8, 4497-4500.
    • (2006) Org. Lett , vol.8 , pp. 4497-4500
    • Ma, G.1    Zancanella, M.2    Oyola, Y.3    Richardson, R.D.4    Smith, J.W.5    Romo, D.6
  • 32
    • 33744966868 scopus 로고    scopus 로고
    • Stereselective synthesis of (-)-tetrahydrolipstatin via Prins cyclisations
    • (c) Yadav, J. S.; Sridhar Reddy, M.; Prasad, A. R. Stereselective synthesis of (-)-tetrahydrolipstatin via Prins cyclisations. Tetrahedron Lett. 2006, 47, 4995-1998.
    • (2006) Tetrahedron Lett , vol.47 , pp. 4995-1998
    • Yadav, J.S.1    Sridhar Reddy, M.2    Prasad, A.R.3
  • 33
    • 33845317849 scopus 로고    scopus 로고
    • A chiron approach to (-)-tetrahydrolipstatin
    • (d) Yadav, J. S.; Vishweshwar Rao, K.; Prasad, A. R. A chiron approach to (-)-tetrahydrolipstatin. Synthesis 2006, 3888-3894.
    • (2006) Synthesis , pp. 3888-3894
    • Yadav, J.S.1    Vishweshwar Rao, K.2    Prasad, A.R.3
  • 34
    • 33646791880 scopus 로고    scopus 로고
    • Stereoselective synthesis of (-)-tetrahydrolipstatin via a radical cyclization based strategy
    • (e) Yadav, J. S.; Vishweshwar Rao, K.; Sridhar Reddy, M.; Prasad, A. R. Stereoselective synthesis of (-)-tetrahydrolipstatin via a radical cyclization based strategy. Tetrahedron Lett. 2006, 47, 4393-1395.
    • (2006) Tetrahedron Lett , vol.47 , pp. 4393-1395
    • Yadav, J.S.1    Vishweshwar Rao, K.2    Sridhar Reddy, M.3    Prasad, A.R.4
  • 35
    • 1942472095 scopus 로고    scopus 로고
    • Highly enantioselective hydrogenation of 3,5-diketo esters: A formal synthesis of tetrahydrolipstatin
    • (f) Polkowska, J.; Lukaszewicz, E.; Kiegiel, J.; Jurczak, J. Highly enantioselective hydrogenation of 3,5-diketo esters: a formal synthesis of tetrahydrolipstatin. Tetrahedron Lett. 2004, 45, 3873-3875.
    • (2004) Tetrahedron Lett , vol.45 , pp. 3873-3875
    • Polkowska, J.1    Lukaszewicz, E.2    Kiegiel, J.3    Jurczak, J.4
  • 36
    • 0141571033 scopus 로고    scopus 로고
    • Diastereoselective allylations and crotylations under phase-transfer conditions using trifluoroborate salts: An application to the total synthesis of (-)-tetrahydrolipstatin
    • (g) Thadani, A. N.; Batey, R. A. Diastereoselective allylations and crotylations under phase-transfer conditions using trifluoroborate salts: an application to the total synthesis of (-)-tetrahydrolipstatin. Tetrahedron Lett. 2003, 44, 8051-8055.
    • (2003) Tetrahedron Lett , vol.44 , pp. 8051-8055
    • Thadani, A.N.1    Batey, R.A.2
  • 37
    • 0037474670 scopus 로고    scopus 로고
    • The total synthesis of (-)-tetrahydrolipstatin
    • (h) Bodkin, J. A.; Humphries, E. J.; McLeod, M. D. The total synthesis of (-)-tetrahydrolipstatin. Tetrahedron Lett. 2003, 44, 2869-2872.
    • (2003) Tetrahedron Lett , vol.44 , pp. 2869-2872
    • Bodkin, J.A.1    Humphries, E.J.2    McLeod, M.D.3
  • 38
    • 0041513417 scopus 로고    scopus 로고
    • The total synthesis of (-)-tetrahydrolipstatin
    • (i) Bodkin, J. A.; Humphries, E. J.; McLeod, M. D. The total synthesis of (-)-tetrahydrolipstatin. Aust. J. Chem. 2003, 56, 795-803.
    • (2003) Aust. J. Chem , vol.56 , pp. 795-803
    • Bodkin, J.A.1    Humphries, E.J.2    McLeod, M.D.3
  • 39
    • 0034632366 scopus 로고    scopus 로고
    • Asymmetric synthesis of (-)-tetrahydrolipstatin: An anti-aldol-based strategy
    • (j) Ghosh, A. K.; Fidanze, S. Asymmetric synthesis of (-)-tetrahydrolipstatin: an anti-aldol-based strategy. Org. Lett. 2000, 2, 2405-2407.
    • (2000) Org. Lett , vol.2 , pp. 2405-2407
    • Ghosh, A.K.1    Fidanze, S.2
  • 40
    • 0033972194 scopus 로고    scopus 로고
    • A rapid synthesis of (-)-tetrahydrolipstatin
    • (k) Parsons, P. J.; Cowell, J. K. A rapid synthesis of (-)-tetrahydrolipstatin. Synlett 2000, 107-109.
    • (2000) Synlett , pp. 107-109
    • Parsons, P.J.1    Cowell, J.K.2
  • 41
    • 0033056135 scopus 로고    scopus 로고
    • Wedler, C.; Costisella, B.; Schick, H. Synthesis of enantiomerically pure β-lactones by the tandem aldol-lactonization. A highly efficient access to (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan- 2-one, the key intermediate for the enzyme inhibitors tetrahydrolipstatin and tetrahydroesterastin. J. Org. Chem. 1999, 64, 5301-5303.
    • (l) Wedler, C.; Costisella, B.; Schick, H. Synthesis of enantiomerically pure β-lactones by the tandem aldol-lactonization. A highly efficient access to (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan- 2-one, the key intermediate for the enzyme inhibitors tetrahydrolipstatin and tetrahydroesterastin. J. Org. Chem. 1999, 64, 5301-5303.
  • 42
    • 0033534342 scopus 로고    scopus 로고
    • Anti-aldol reactions of lactate-derived ketones. Application to the synthesis of (-)-tetrahydrolipstatin
    • (m) Paterson, I.; Doughty, V. A. Anti-aldol reactions of lactate-derived ketones. Application to the synthesis of (-)-tetrahydrolipstatin. Tetrahedron Lett. 1999, 40, 393-394.
    • (1999) Tetrahedron Lett , vol.40 , pp. 393-394
    • Paterson, I.1    Doughty, V.A.2
  • 43
    • 0033533447 scopus 로고    scopus 로고
    • A stereoselective synthesis of (-)-tetrahydrolipstatin
    • (n) Ghosh, A. K.; Liu, C. A stereoselective synthesis of (-)-tetrahydrolipstatin. Chem. Commun. 1999, 1743-1744.
    • (1999) Chem. Commun , pp. 1743-1744
    • Ghosh, A.K.1    Liu, C.2
  • 44
    • 0000143188 scopus 로고    scopus 로고
    • Dirat, O.; Kouklovsky, C.; Langlois, Y. Oxazoline N-oxide-mediated [2 + 3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin. Org. Lett. 1999, 1, 753-755.
    • (o) Dirat, O.; Kouklovsky, C.; Langlois, Y. Oxazoline N-oxide-mediated [2 + 3] cycloadditions. Application to a synthesis of (-)-tetrahydrolipstatin. Org. Lett. 1999, 1, 753-755.
  • 45
    • 33748675953 scopus 로고    scopus 로고
    • Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of (-)-tetrahydrolipstatin using the alkylation of a β-silyl ester and the hydroboration of an allylsilane
    • (p) Fleming, I.; Lawrence, N. J. Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of (-)-tetrahydrolipstatin using the alkylation of a β-silyl ester and the hydroboration of an allylsilane. J. Chem. Soc., Perkin Trans. 1 1998, 2679-2686.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 2679-2686
    • Fleming, I.1    Lawrence, N.J.2
  • 47
    • 0023923039 scopus 로고
    • Synthesis of tetrahydrolipstatin and tetrahydroesterastin, compounds with a β-lactone moiety. Stereoselective hydrogenation of a β-keto δ-lactone and conversion of the δ-lactone into a β-lactone
    • (r) Barbier, P.; Schneider, F. Synthesis of tetrahydrolipstatin and tetrahydroesterastin, compounds with a β-lactone moiety. Stereoselective hydrogenation of a β-keto δ-lactone and conversion of the δ-lactone into a β-lactone. J. Org. Chem. 1988, 53, 1218-1221.
    • (1988) J. Org. Chem , vol.53 , pp. 1218-1221
    • Barbier, P.1    Schneider, F.2
  • 48
    • 0023240167 scopus 로고
    • Stereoselective syntheses of tetrahydrolipstatin and of an analogue, potent pancreatic-lipase inhibitors containing a β-lactone moiety
    • (s) Barbier, P.; Schneider, F.; Widmer, U. Stereoselective syntheses of tetrahydrolipstatin and of an analogue, potent pancreatic-lipase inhibitors containing a β-lactone moiety. Helv. Chim. Acta 1987, 70, 1412-1418.
    • (1987) Helv. Chim. Acta , vol.70 , pp. 1412-1418
    • Barbier, P.1    Schneider, F.2    Widmer, U.3
  • 49
    • 0023137327 scopus 로고
    • Syntheses of tetrahydrolipstatin and absolute configuration of tetrahydrolipstatin and lipstatin
    • (t) Barbier, P.; Schneider, F. Syntheses of tetrahydrolipstatin and absolute configuration of tetrahydrolipstatin and lipstatin. Helv. Chim. Acta 1987, 70, 196-202.
    • (1987) Helv. Chim. Acta , vol.70 , pp. 196-202
    • Barbier, P.1    Schneider, F.2
  • 50
    • 56249095723 scopus 로고    scopus 로고
    • 3 for 2 h, followed by flash chromatography on silica gel using hexane/AcOEt = 7/3 as the eluent (the cost of 84 capsules, each containing 120 mg of THL, is ∼100 Euros).
    • 3 for 2 h, followed by flash chromatography on silica gel using hexane/AcOEt = 7/3 as the eluent (the cost of 84 capsules, each containing 120 mg of THL, is ∼100 Euros).
  • 51
    • 56249105713 scopus 로고    scopus 로고
    • Oxetanone derivatives
    • U.S. Patent 2001012852
    • (a) Mullins, J. J. G. Oxetanone derivatives. U.S. Patent 2001012852, 2001.
    • (2001)
    • Mullins, J.J.G.1
  • 52
    • 56249117918 scopus 로고    scopus 로고
    • Use of oxetanone derivatives as lipase inhibitors
    • Int. Patent WO 2001032670
    • (b) Mullins, J. J. G. Use of oxetanone derivatives as lipase inhibitors. Int. Patent WO 2001032670, 2001.
    • (2001)
    • Mullins, J.J.G.1
  • 53
    • 56249119772 scopus 로고    scopus 로고
    • Derungs, R, Maerki, H. P, Stalder, H, Szente, A. Preparation of 4-(acyloxyethyl)oxetan-2-ones. Eur. Patent EP 0444482, 1991
    • Derungs, R.; Maerki, H. P.; Stalder, H.; Szente, A. Preparation of 4-(acyloxyethyl)oxetan-2-ones. Eur. Patent EP 0444482, 1991.
  • 54
    • 56249116463 scopus 로고    scopus 로고
    • Process for the preparation of orlistat via formylation of amino-orlistat with formic acid anhydride
    • Int. Patent WO2007039814
    • (a) Patel, K.; Kanwar, S.; Deo, K.; Prasad, M. Process for the preparation of orlistat via formylation of amino-orlistat with formic acid anhydride. Int. Patent WO2007039814, 2007.
    • (2007)
    • Patel, K.1    Kanwar, S.2    Deo, K.3    Prasad, M.4
  • 55
    • 56249095380 scopus 로고    scopus 로고
    • Process for preparation of oxetan-2-ones
    • WO 2005005403
    • (b) Kumar, Y.; Prasad, M.; Deo, K.; Pandey, A.; Patel, K. Process for preparation of oxetan-2-ones. WO 2005005403, 2005.
    • (2005)
    • Kumar, Y.1    Prasad, M.2    Deo, K.3    Pandey, A.4    Patel, K.5
  • 56
    • 56249101262 scopus 로고    scopus 로고
    • Watanabe, Y, Ikemoto, T. Processes for the production of, -tetrahydrolipstatin and intermediates thereof. WO 2004065346, 2004
    • (c) Watanabe, Y.; Ikemoto, T. Processes for the production of (-)-tetrahydrolipstatin and intermediates thereof. WO 2004065346, 2004.
  • 57
    • 56249149497 scopus 로고
    • Preparation of oxetanones as pancreatic lipase inhibitors
    • Eur. Patent EP 189577
    • (d) Barbier, P.; Schneider, F.; Widmer. U. Preparation of oxetanones as pancreatic lipase inhibitors. Eur. Patent EP 189577, 1986.
    • (1986)
    • Barbier, P.1    Schneider, F.2    Widmer, U.3
  • 58
    • 56249117579 scopus 로고    scopus 로고
    • Preparation of
    • N-formylleucine 1-(oxetanoylmethyl)alkyl esters and analogs as pancreatic lipase inhibitors. U.S. Patent 4931463, 1990
    • (a) Barbier, P.; Schneider, F.; Widmer, U. Preparation of N-formylleucine 1-(oxetanoylmethyl)alkyl esters and analogs as pancreatic lipase inhibitors. U.S. Patent 4931463, 1990.
    • Barbier, P.1    Schneider, F.2    Widmer, U.3
  • 59
  • 60
    • 0028866609 scopus 로고
    • Review of limited systemic absorption of orlistat, a lipase inhibitor, in healthy human volunteers
    • Zhi, J.; Melia, A. T.; Eggers, H.; Joly, R.; Patel, I. H. Review of limited systemic absorption of orlistat, a lipase inhibitor, in healthy human volunteers. J. Clin. Pharmacol. 1995, 35, 1103-1108.
    • (1995) J. Clin. Pharmacol , vol.35 , pp. 1103-1108
    • Zhi, J.1    Melia, A.T.2    Eggers, H.3    Joly, R.4    Patel, I.H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.