Synthesis of (±)-bimatoprost

Synthetic Communications

Volumn 42, Issue 9, 2012, Pages 1288-1305

  Harikrishna, M ^a   Mohan, H Rama ^a   Dubey, P K ^b   Shankar, M ^a   Subbaraju, Gottumukkala V ^a  

^a Aptuit Laurus Private Limited   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

( ) bimatoprost; ( ) homobimatoprost; Ophthalmic; Prostaglandins

Indexed keywords

BIMATOPROST; HOMOBIMATOPROST; LACTONE; PROSTAGLANDIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84857519116     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.539754     Document Type: Article

References (29)

1. (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
2. (b) Quigley, H. A. Number of people with glaucoma worldwide. Br. J. Ophthalmol. 1991, 80, 389-393 (Pubitemid 26158268)
3. (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
4. (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. (Pubitemid 32441322)
5. (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 (Pubitemid 14012201)
6. 2α isopropyl ester: Potential antiglaucoma agents. J. Med. Chem. 1995, 38, 289-304.
7. Hoyng, P. F.; van Beek, L. M. Pharmacological therapy for glaucoma: A review. Drugs 2000, 59, 411-434. (Pubitemid 30213853)
8. (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 (Pubitemid 20029885)
9. Bito, L. Z. Species differences in the responses of the eye to irritation and trauma. Exp. Eye Res. 1984, 38, 181-194
10. (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.
11. 2 ffagg-isopropyl ester to latanoprost: A review of the development of xalatan, the Proctor lecture, Investig. Ophthalmol. Visual Sci. 2001, 42, 1134-1145 (Pubitemid 32381949)
12. (b) Rajeev, G.; Lata, H.; Narang, S.; Sood, S. Comparison of latanoprost, bimatoprost, and travoprost. Asian J. Ophthalmol. 2003, 5, 13-14.
13. (a) Crawford, K.; Kaufman, P. L. Pilocarpine antagonizes prostaglandin F2a induced ocular hypotension in monkeys. Arch. Ophthumol (Chicago) 1987, 106, 1112-1116
14. (b) Nibeon, S. F. E.; Samueleson, M.; Bill, A.; Stjernechantz, J. Increased PGF2a i-Pr ester in the cynomolgus monkeys. J. Exp. Eye Res. 1989, 48, 707-716.
15. (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 (Pubitemid 23060092)
16. (b) Yankee, E. W.; Axen, U.; Bundy, G. L. Total synthsis of 15-methylprostaglandins. J. Am. Chem. Soc. 1974, 96, 5865-5876
17. (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: Tissueselective uterine stimulants. J. Med. Chem. 1981, 24, 1353-1359 (Pubitemid 12209069)
18. (d) Liljebris, C.; Nilsson, B. M.; Resul, B.; Hacksell, U. Regio-and stereoselective reactions of 17-phenyl-18,19,20-trinorprostaglandin F2a isopropyl ester. J. Org. Chem. 1996, 61, 4028-4036
19. (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;
20. (f) Resul, B. A. Method for synthesis of prostaglandin derivatives. WO Patent 92=02496 A1, 1992.
21. 2A and its derivatives. WO Patent 2002=096868 A2, 2002
22. (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 (Pubitemid 46484332)
23. (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. (Pubitemid 30449709)
24. Gutman, A.; Nisnevich, G.; Zaltzman, I. Process for the preparation of latanoprost. U.S. Patent 2003=0149294 A1, 2003.
25. (a) Montgomery, F. C.; Saunders, W. H. Migration aptitudes in the photolysis of some tertiary alkyl azides. J. Org. Chem. 1976, 41, 2368-2372
26. (b) Hassan, J. G. Jomaa Pharmaka GmbH, Organophosphorus compounds and the use thereof. U.S. Patnet No. 2003=6534489 B1, 2003
27. (c) Ochiai, M.; Nishitani, J.; Nishi, Y. A new route for generation of a-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 (Pubitemid 34700795)
28. (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.
29. 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.