메뉴 건너뛰기




Volumn 7, Issue 5, 2002, Pages 303-314

Stereoselective synthesis from a process research perspective

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM DERIVATIVE; DRUG; ENDOTHELIN RECEPTOR; INDAN DERIVATIVE; INDANONE; MUSCARINIC RECEPTOR BLOCKING AGENT; PIPERIDINE DERIVATIVE; SUBSTANCE P; ANTIBIOTIC AGENT; CARBAPENEM; ENDOTHELIN RECEPTOR ANTAGONIST; ERTAPENEM; INDACRINONE; INDINAVIR; PIPERIDINE; SUBSTANCE P ANTAGONIST;

EID: 0036489215     PISSN: 13596446     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-6446(01)02162-6     Document Type: Review
Times cited : (22)

References (68)
  • 3
    • 0025759183 scopus 로고
    • Synthesis of optically active compounds: A large scale perspective
    • (1991) Tetrahedron , vol.47 , pp. 4789-4846
    • Crosby, J.1
  • 7
    • 0024312032 scopus 로고
    • The FDA perspective on the development of stereoisomers
    • (1989) Chirality , vol.1 , pp. 2-6
    • DeCamp, W.H.1
  • 9
    • 0032749158 scopus 로고    scopus 로고
    • FDA policy and regulation of stereoisomers: Paradigm shift and the future of safer, more effective drugs
    • (1999) Food Drug Law J. , vol.54 , pp. 463-487
    • Strong, M.S.1
  • 12
    • 0017879921 scopus 로고
    • (Acylaryloxy)acetic acid diuretics. 2. (2-Alkyl-2-aryl-1-oxo-5-indanyloxy)acetic acids
    • (1978) J. Med. Chem. , vol.21 , pp. 437-443
    • DeSolms, S.J.1
  • 13
    • 0020067247 scopus 로고
    • Stereoselectivity in the disposition and metabolism of the uricosuric-diuretic agent, indacrinone, in rhesus monkeys
    • (1982) Drug Metab. Dispos. , vol.10 , pp. 20-27
    • Zacchei, A.G.1
  • 15
    • 33845470711 scopus 로고
    • Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 446-447
    • Dolling, U.-H.1
  • 16
    • 0000637655 scopus 로고
    • Efficient catalytic asymmetric alkylations. 3. A kinetic and mechanistic study of the enantioselective phase-transfer methylation of 6,7-dichloro-5-methoxy-2-phenyl-1-indanone
    • (1987) J. Org. Chem. , vol.52 , pp. 4745-4752
    • Hughes, D.L.1
  • 17
    • 0000867232 scopus 로고
    • Chiral Michael addition: Methyl vinyl ketone addition catalyzed by cinchona alkaloid derivatives
    • (1986) J. Org. Chem. , vol.51 , pp. 4710-4711
    • Conn, R.S.E.1
  • 20
    • 0028206333 scopus 로고
    • Preliminary findings on the role of neuropeptide suppression by topical agents in the management of rheumatoid arthritis
    • (1994) Semin. Arthritis Rheum. , vol.23 , pp. 18-24
    • Weisman, M.H.1
  • 22
    • 0028226031 scopus 로고
    • Sensory neuropeptides and the human lower airways: Present state and future directions
    • (1994) Eur. Respir. J. , vol.7 , pp. 1161-1171
    • Joos, G.F.1
  • 23
    • 0028339649 scopus 로고
    • Involvement of neurokinin 1 and 2 receptors in viscerosensitive response to rectal distension in rats
    • (1994) Gastroenterology , vol.107 , pp. 94-102
    • Julia, V.1
  • 24
    • 0032508514 scopus 로고    scopus 로고
    • Distinct mechanism for antidepressant activity by blockade of central substance P receptors
    • (1998) Science , vol.281 , pp. 1640-1645
    • Kramer, M.S.1
  • 25
    • 0029878786 scopus 로고    scopus 로고
    • 2(S)-((3,5-Bis(trifluoromethyl)benzyl)-oxy)-3(S)-phenyl-4-((3-oxo-1,2, 4-triazol-5-yl)methyl)morpholine (1): A potent, orally active, morpholine-based human neurokinin-1 receptor antagonist
    • (1996) J. Med. Chem. , vol.39 , pp. 1760-1762
    • Hale, J.J.1
  • 26
    • 15144354434 scopus 로고    scopus 로고
    • Structural optimization affording 2-(R)-(1-(R)-3,5-bis(trifluoromethyl)phenylethoxy)-3-(S)-(4-fluoro)phenyl-4- (3-oxo-1,2,4-triazol-5-yl)methylmorpholine, a potent, orally active, long-acting morpholine acetal human nk-1 receptor antagonist
    • (1998) J. Med. Chem. , vol.41 , pp. 4607-4614
    • Hale, J.J.1
  • 27
    • 84995719995 scopus 로고
    • Eur. Pat. Appl. E. P. 577394 A1
    • (1994)
    • Dorn, C.P.1
  • 29
    • 0031058003 scopus 로고    scopus 로고
    • Synthesis of N-benzyl-3-(S)-(+)-(4-fluorophenyl)-1,4-oxazin-2-one via crystallisation induced asymmetric transformation
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 447-450
    • Alabaster, R.J.1
  • 30
    • 0000400036 scopus 로고
    • Thermodynamically controlled 1,3-asymmetric induction in an acyclic system - Equilibration of α-amino nitriles derived from α-alkylbenzylamines and aldehydes
    • (1991) J. Org. Chem. , vol.56 , pp. 1274-1279
    • Inaba, T.I.1
  • 31
    • 0024801485 scopus 로고
    • Efficient conversion of nitriles to amides with basic hydrogen peroxide
    • (1989) Synthesis , pp. 949-950
    • Katritzky, A.R.1
  • 35
    • 0027997928 scopus 로고
    • Piperidine-ether based hnk1 antagonist 1: Determination of the relative and absolute stereochemical requirements
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 2545-2550
    • Harrison, T.1
  • 38
    • 0035801823 scopus 로고    scopus 로고
    • Asymmetric synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine via ring expansion
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6223-6225
    • Lee, J.1
  • 39
    • 0032542168 scopus 로고    scopus 로고
    • Enantioselective synthesis of 2,3-disubstituted piperidines from (S)-methylpyroglutamate
    • (1998) Tetrahedron Lett. , vol.39 , pp. 9447-9450
    • Calvez, O.1
  • 41
    • 0034681742 scopus 로고    scopus 로고
    • Stereoselective double ring closing metathesis reactions in the synthesis of spirocyclic compounds
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2027-2029
    • Wallace, D.J.1
  • 42
    • 0035826346 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of epimeric 3-aryl-6-phenyl-1-oxa-7-azaspiro[4.5]decane nk-1 receptor antagonist precursor
    • (2001) Org. Lett. , vol.3 , pp. 667-670
    • Kulagowski, J.J.1
  • 43
    • 0035826378 scopus 로고    scopus 로고
    • A double ring closing metathesis reaction in the rapid, enantioselective synthesis of nk-1 receptor antagonists
    • (2001) Org. Lett. , vol.3 , pp. 671-674
    • Wallace, D.J.1
  • 44
    • 0001855961 scopus 로고    scopus 로고
    • Synthesis and applications of RuCl2(=CHR′)(PR3)2: The influence of the alkylidene moiety on metathesis activity
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 100-110
    • Schwab, P.1
  • 46
    • 84995716412 scopus 로고    scopus 로고
    • Carbapenem antibiotic isolation without chromatography or nanofiltration, by extracting crude compound solution with alcohol and crystallizing from aqueous phase. WO patent WO9945010
    • (1998)
    • Williams, J.M.1
  • 47
    • 0034689877 scopus 로고    scopus 로고
    • Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling
    • (2000) Org. Lett. , vol.2 , pp. 1081-1084
    • Jensen, M.S.1
  • 48
    • 0033556115 scopus 로고    scopus 로고
    • Preparation of crystalline p-nitrobenzyl 2-hydroxymethyl carbapenem as a key intermediate for the anti-MRSA carbapenem L-786,392
    • (1999) Tetrahedron Lett. , vol.40 , pp. 427-430
    • Yasuda, N.1
  • 49
    • 0033535386 scopus 로고    scopus 로고
    • Synthesis and properties of 2-(naphthosultamyl)methyl-carbapenems with potent anti-MRSA activity: Discovery of L-786,392
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 679-684
    • Ratcliffe, R.W.1
  • 50
    • 0040886246 scopus 로고    scopus 로고
    • Efficient and practical synthesis of a potent anti-MRSA β-methyl-carbapenem containing a releasable side chain
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11261-11266
    • Humphrey, G.R.1
  • 51
    • 0030782489 scopus 로고    scopus 로고
    • TiCl4/Bu3N/(catalytic TMSOTf): Efficient agent for direct aldol addition and Claisen condensation
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8727-8730
    • Yoshida, Y.1
  • 53
    • 0028147531 scopus 로고
    • Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524
    • (1994) Tetrahedron Lett. , vol.35 , pp. 673-676
    • Askin, D.1
  • 56
    • 0001013911 scopus 로고    scopus 로고
    • A catalytic enantioselective synthesis of the endothelin receptor antagonists SB-209670 and SB-217242. A base-catalyzed stereospecific formal 1,3-hydrogen transfer of a chiral 3-arylindenol
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 4550-4551
    • Clark, W.M.1
  • 57
    • 0032080817 scopus 로고    scopus 로고
    • Stereoselective conjugate addition reactions of α,β-unsaturated tert-butyl esters with aryl lithium reagents
    • (1998) J. Org. Chem. , vol.63 , pp. 3120-3124
    • Frey, L.F.1
  • 58
    • 0033601193 scopus 로고    scopus 로고
    • Practical asymmetric synthesis of an endothelin receptor antagonist
    • (1999) J. Org. Chem. , vol.64 , pp. 9658-9667
    • Song, Z.J.1
  • 59
    • 0001373744 scopus 로고
    • Diastereoselective conjugate addition with acetals, oxazolidines, and imidazolidines as chiral auxiliaries
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4411-4414
    • Alexakis, A.1
  • 60
    • 18044403182 scopus 로고    scopus 로고
    • Practical asymmetric synthesis of a selective endothelin a receptor (ETA) antagonist
    • (2001) Org. Lett. , vol.3 , pp. 3357-3360
    • Song, Z.J.1
  • 62
    • 0035812684 scopus 로고    scopus 로고
    • Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction
    • (2001) J. Org. Chem. , vol.66 , pp. 6775-6786
    • Mase, T.1
  • 63
    • 0034727854 scopus 로고    scopus 로고
    • A potent, long-acting, orally active (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: A novel muscarinic M3 receptor antagonist with high selectivity for M3 over M2 receptors
    • (2000) J. Med. Chem. , vol.43 , pp. 5017-5029
    • Mitsuya, M.1
  • 64
    • 0028899016 scopus 로고
    • Pre-clinical and clinical pharmacology of selective muscarinic M3 receptor antagonists
    • (1995) Life Sci. , vol.56 , pp. 861-868
    • Wallis, R.M.1
  • 65
    • 0001907280 scopus 로고    scopus 로고
    • Characterization of muscarinic receptor subtypes in SO2-induced mucus hypersecretion in rat bronchitis model
    • (1999) J. Pharmacol. , vol.79 , pp. 37P
    • Aoki, I.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.