Pyrrolidine ester derivatives with oxytocin modulating activity

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C548S533000, C548S532000

Reexamination Certificate

active

10471290

ABSTRACT:
The present invention is related to the use of pyrrolidine esters of formula (I) for the treatment and/or prevention of premature labor, premature birth and dysmenorrhea. In particular, the present invention is related to the use of pyrrolidine esters of formula (I) to modulate, notably to antagonize the oxytocin receptor. The present invention is furthermore related to novel pyrrolidine esters. X is selected from the group consisting of CR6R7, NOR6, NNR6R7; R is selected from the group comprising or consisting of C1–C6alkyl, C2–C6alkenyl, C2–C6alkynyl, saturated or unsaturated 3–8-membered cycloalkyl which may contain 1 to 3 heteroatoms selected of N, O, S, aryl, heteroaryl, C1–C6-alkyl aryl, C1–C6-alkyl heteroaryl. R1is selected from the group comprising or consisting of C1–C6-alkyl, C2–C6-alkenyl, C2–C6-alkynyl, aryl, heteroaryl, 3–8-membered cycloalkyl, acyl, C1–C6-alkyl aryl, C1–C6-alkyl heteroaryl, said cycloalkyl or aryl or heteroaryl groups may be fused with 1–2 further cycloalkyl or aryl or heteroaryl group

REFERENCES:
patent: 5481005 (1996-01-01), Wagnon et al.
patent: 5756497 (1998-05-01), Bell et al.
patent: 5780471 (1998-07-01), Venkatesan et al.
patent: 2004/0147511 (2004-07-01), Schwarz et al.
patent: 96/22775 (1996-08-01), None
patent: 99 41757 (1999-10-01), None
patent: 99 52868 (1999-10-01), None
Caprariis et al., Journal of Heterocyclic Chem., 1989, 26:1023-27.
Robert M. Adlington et al.: “A radical route to 2(S)-4-exomethylene proline” TETRAHEDRON, vol. 48, No. 31, pp. 6529-6536.
Elizabeth M. Smith et al.: “Synthesis and Pharmacological activity of angiotensin converting enzyme inhibitors: N-(mercaptoacy)-4-substituted-(S)-prolines” Journal of Medicinal Chemistry, vol. 31, No. 4, pp. 85-885, 1988.
Sharad Kumar Panday et al.: “A short and efficient synthesis of (S)-4-methylene proline benzyl ester from (S)-pyroglutamic acid” Tetrahedron Letters, vol. 35, No. 36, pp. 6673-6676 1994.
RM Adlington et al.: “A radical route to 2(S)-4-exomethylene proline” TETRAHEDRON, vol. 48, No. 31, pp. 6529-6536 1992.
EM Smith et al.: “Synthesis and pharmacological activity of angiotensin converting enzyme inhibitors: N-(mercaptoacyl)-4-substituted-(S)-prolines” Journal of Medicinal Chemistry, vol. 31, No. 4, pp. 85-885, 1998.
SR Panday et al.: “A short oand efficient synthesis of (S)-4-methylene proline benzyl ester from (S)-pyroglutamic acid” Tetrahedron Letters, vol. 35, No. 36, pp. 6673-6676 1994.
Maggi et al. J. Clin. Endocrinol. Metabol., vol. 70, No. 4, pp. 1142-1154 1990.
Evans et al. J. Med. Chem., vol. 35, pp. 3919-3927.
U.S. Appl. No. 11/449,802, filed Jun. 9, 2006, Schwarz et al.
Cook, N., et al., “SPA: A Revolutionary New Technique for Drug Screening,” Phamaceutical Manufacturing International, 1992, pp. 49-53.
Breitmaier, E., et al., “High-Resolution Methods and Applications in Organic Chemistry and Biochemistry,” Carbon-13 NMR Spectroscopy, 3rdEdition, VCH, 1987, pp. 240-241.
Mitchell, B. F., “The Oxytocin and its Receptor in the Process of Parturition,” Journal of the Society for Gynecologic Investigation, 2001, 8, pp. 122-133.
Gimpl, G., et al., “The Oxytocin Receptor System; Structure, Function, and Regulation,” Physiological Reviews, 2001, 81, pp. 629-683.
Jarowicki, K., et al., “Protecting Groups,” J. Chem. Soc., Perkin Trans., 1, 1999, pp. 1589-1615.
Nelson, T. D., et al., “Selective Deprotection of Silyl Ethers,” Synthesis, 1996, pp. 1031-1069.
Kocienski, P. J., “Protecting Groups,” Foundations of Organic Chemistry Series, pp. 1-260, 1994.

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