Synthesis of (±)-Bimatoprost

REFERENCES

• (a) Tielsch , J. M. ; Sommer , A. ; Katz , J. ; Royall , R. M. ; Quigley , H. A. ; Javitt , J. Racial variations in the prevalence of primary open-angle glaucoma . Baltimore Eye Survey 1991 , 266 , 369 – 374 ; (b) Quigley , H. A. Number of people with glaucoma worldwide . Br. J. Ophthalmol. 1991 , 80 , 389 – 393 ; (c) Quigley , H. A. ; Vitale , S. Models of open-angle glaucoma prevalence and incidence in the United States . Invest. Ophthalmol. Vis. Sci. 1991 , 38 , 83 – 91 ; (d) Asrani , S. ; Zeimer , R. ; Wilensky , J. ; Gieser , D. ; Vitale , S. ; Lindenmuth , K. Large diurnal fluctuations in intraocular pressure is an independent risk factor in patients with glaucoma . J. Glaucoma 2000 , 9 , 134 – 142 .
   Google Scholar
• (a) Jay , W. M. ; Aziz , M. Z. ; Green , K. Effect of topical epinephrine and timolol on ocular and optic nerve blood flow in phakic and aphakic rabbit eyes . Curr. Eye Res. 1984 , 3 , 1199 – 1202 ; (b) Liljebris , C. ; Selen , G. ; Resul , B. ; Stjernschantz , J. ; Hacksell , U. Derivatives of 17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester: Potential antiglaucoma agents . J. Med. Chem. 1995 , 38 , 289 – 304 .
   PubMed Web of Science ®Google Scholar
• Hoyng , P. F. ; van Beek , L. M. Pharmacological therapy for glaucoma: A review . Drugs 2000 , 59 , 411 – 434 .
   PubMed Web of Science ®Google Scholar
• (a) Villumsen , J. ; Alm , A. ; Soderstrom , M. Prostaglandin F2 α-isopropyl ester eye drops: Effect on intraocular pressure in open-angle glaucoma . Br. J. Ophthalmol. 1989 , 73 , 975 – 979 ; (b) Bito , L. Z. Species differences in the responses of the eye to irritation and trauma . Exp. Eye Res. 1984 , 38 , 181 – 194 (c) Bib , L. Z. ; Camras , C. ; Gum , G. ; Resul , B. In The Ocular Effects of Prostaglandins and Other Eicosanoids; L. Z. Bilto and J. Stjernschantz (Eds.); New York: Alan, R. Liss, 1989, pp. 349–368.
   PubMed Web of Science ®Google Scholar
• (a) Stjernschantz , J. W. From PGF2 {{α}}-isopropyl ester to latanoprost: A review of the development of xalatan, the Proctor lecture, Investig. Ophthalmol. Visual Sci. 2001, 42, 1134–1145 (b) Rajeev , G. ; Lata , H. ; Narang , S. ; Sood , S. Comparison of latanoprost, bimatoprost, and travoprost. Asian J. Ophthalmol. 2003, 5, 13–14.
   Google Scholar
• (a) Crawford , K. ; Kaufman , P. L. Pilocarpine antagonizes prostaglandin F2α induced ocular hypotension in monkeys . Arch. Ophthumol (Chicago) 1987 , 106 , 1112 – 1116 ; (b) Nibeon , S. F. E. ; Samueleson , M. ; Bill , A. ; Stjernechantz , J. Increased PGF2α i-Pr ester in the cynomolgus monkeys . J. Exp. Eye Res. 1989 , 48 , 707 – 716 .
   Google Scholar
• (a) Resul , B. ; Stjernschantz , J. ; No , K. ; Liljebris , C. ; Selen , G. ; Astin , M. ; Karlsson , M. ; Laszlo , Z. Phenyl-substituted prostaglandins: potent and selective antiglaucoma agents . J. Med. Chem. 1993 , 36 , 243 – 248 ; (b) Yankee , E. W. ; Axen , U. ; Bundy , G. L. Total synthsis of 15-methylprostaglandins . J. Am. Chem. Soc. 1974 , 96 , 5865 – 5876 ; (c) Schaaf , T. K. ; Bindra , J. S. ; Eggler , J. F. ; Plattner , J. J. ; Nelson , J. ; Johnson , M. R. ; Constantine , J. W. ; Hess , H. J. N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-selective uterine stimulants. J. Med. Chem. 1981, 24, 1353–1359 (d) Liljebris , C. ; Nilsson , B. M. ; Resul , B. ; Hacksell , U. Regio-and stereoselective reactions of 17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester . J. Org. Chem. 1996 , 61 , 4028 – 4036 ; (e) Boulton , L. T. ; Brick , D. ; Fox , M. E. ; Jackson , M. ; Lennon , I. C. ; McCague , R. ; Parkin , N. ; Rhodes , D. ; Ruecroft , G. Synthesis of the potent antiglaucoma agent, travoprost . Org. Proc. Res. Devel. 2002 , 6 , 138 – 145 ; (f) Resul , B. A. Method for synthesis of prostaglandin derivatives. WO Patent 92/02496 A1, 1992.
   PubMed Web of Science ®Google Scholar
• (a) Gutman , A. L. ; Nisnevich , G. A new process for the preparation of 17-phenyl-18,19,20-trinor-PGF2A and its derivatives. WO Patent 2002/096868 A2, 2002; (b) Roman , G. ; Riley , G. J. ; Vlahakis , N. J. ; Kinobe , T. R. ; Brien , F. J. ; Nakatsu , K. ; Szarek , A. W. Heme oxygenase inhibition by 2-oxy-substituted 1-(1H-imidazol-1-yl)-4-phenylbutanes: Effect of halogen substitution in the phenyl ring . Bioorg. Med. Chem. 2007 , 15 , 3225 – 3234 ; (c) deLong , M. A. ; Amburgey , J. ; Taylor , C. ; Wos , J. A. ; Soper , D. L. ; Wang , Y. ; Hicks , R. Synthesis and in vitro evaluation of human FP-receptor selective prostaglandin analogues . Bioorg. Med. Chem. Lett. 2000 , 10 , 1519 – 1522 .
   PubMed Web of Science ®Google Scholar
• Gutman , A. ; Nisnevich , G. ; Zaltzman , I. Process for the preparation of latanoprost. U.S. Patent 2003/0149294 A1, 2003.
   Google Scholar
• (a) Montgomery , F. C. ; Saunders , W. H. Migration aptitudes in the photolysis of some tertiary alkyl azides . J. Org. Chem. 1976 , 41 , 2368 – 2372 ; (b) Hassan , J. G. Jomaa Pharmaka GmbH, Organophosphorus compounds and the use thereof. U.S. Patnet No. 2003/6534489 B1, 2003 ; (c) Ochiai , M. ; Nishitani , J. ; Nishi , Y. A new route for generation of α-λ3-iodanyl ketones via ester exchange of (Z)-(β-acetoxyvinyl)-λ3-iodanes: Their nucleophilic substitutions with halides and sulfur and phosphorus nucleophiles. J. Org. Chem. 2002, 67, 4407–4413 (d) Zurawinski , R. ; Nakamura , K. ; Drabowicz , J. ; Kielbasinski , P. ; Mikolajczyk , M. Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates . Tetrahedron: Asymmetry 2001 , 12 , 3139 – 3146 .
   Web of Science ®Google Scholar
• Yao , C. H. ; Yang , C. M. ; Chao , H. H. ; Lee , G. R. Method for preparing prostaglandin F analogue. U.S. Patent No. 2009/0259066 A1, 2009.
   Google Scholar