Following is a CAS database record representing a highly cited patent family.
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CAS indexed 173 chemical substances from this document.
CAS subject entries for this document include: Prostaglandins; Prostanoid receptors; Nerve, disease; and 11 additional concepts. | |
CAPLUS COPYRIGHT 2005 ACS on STN
| TITLE:
| Preparation of .omega.-cycloalkyl-prostaglandin E2 derivatives |
| INVENTOR(S):
| Tani, Kousuke; Ohuchida, Shuichi |
| PATENT ASSIGNEE(S):
| Ono Pharmaceutical Co., Ltd., Japan |
| SOURCE:
| Eur. Pat. Appl., 121 pp. CODEN: EPXXDW |
| LANGUAGE:
| English |
PATENT INFORMATION: PATENT NO. KIND DATE APPLICATION NO. DATE
--------------- ---- -------- -------------------- --------
EP 860430 A2 19980826 EP 1998-300769 19980203
EP 860430 A3 19990623
EP 860430 B1 20020612
R: AT, BE, CH, DE, DK, ES, FR, GB, GR, IT, LI, LU, NL, SE, MC, PT,
IE, SI, LT, LV, FI, RO
NO 9800442 A 19980805 NO 1998-442 19980202
JP 11193268 A2 19990721 JP 1998-33526 19980202
JP 3162668 B2 20010508
JP 2000128858 A2 20000509 JP 1999-320457 19980202
ZA 9800879 A 19980803 ZA 1998-879 19980203
AT 219054 E 20020615 AT 1998-300769 19980203
PT 860430 T 20021129 PT 1998-300769 19980203
ES 2178808 T3 20030101 ES 1998-300769 19980203
TW 581756 B 20040401 TW 1998-87101279 19980203
CA 2228828 AA 19980804 CA 1998-2228828 19980204
AU 9852892 A1 19980806 AU 1998-52892 19980204
AU 736271 B2 20010726
US 6110969 A 20000829 US 1998-18565 19980204
US 6576785 B1 20030610 US 2000-570728 20000512
US 2003186939 A1 20031002 US 2002-238623 20020911
ABSTRACT:
.omega.-Cycloalkyl-prostaglandin E2 derivs. I [R = COOH, COOCH2OH; R1 = oxo, CH2, halo; R2 = H, OH, C1-4 alkoxy; R3 = H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C2-8 alkyl, C2-8 alkenyl, C2-8 alkynyl substituted by 1-3 substituents selected from halogen atom, C2-4 alkoxy, C3-7 cycloalkyl, Ph, and Ph substituted by 1-3 substituents selected from halogen atom, C1-4 alkyl, C1-4 alkoxy, nitro and trifluoromethyl; n = 0-4] and their non-toxic salts, their prodrugs their and cyclodextrin clathrates, having strong binding activity on the EP2 subtype receptor, are prepd. Therefore, they are useful for prevention and/or treatment of immunol. diseases (autoimmune diseases, organ transplantation, etc.), asthma, abnormal bone formation, neuronal cell death, liver damage, abortion, premature birth or retina neuropathy of glaucoma etc. Thus, (1E,4RS)-1-iodo-4-tert-butyldimethylsilyloxy-5,5-propanooct-1-ene (also prepd.) was reacted with (5Z)-7-((3R)-3-tert-butyldimethylsilyloxy-5-oxocyclopent-1-en-1-yl)hept-5-en oic acid Me ester in THF contg. lithium 2-thienylcyanocuprate and BuLi to give (5Z,11.alpha.,13E, 16RS)-11,16-bis(tert-butyldimethylsilyloxy)-9-oxo-17,17-propanoprosta-5,13-d ienoic acid Me ester, which in MeCN contg. pyridine was treated with 47% aq. HF to give the title compd. II [R4 = Me]. The more polar epimer of II [R4 = H] (also prepd.). In an exptl. measuring the competition of I for the binding of EP2 receptor in the presence of 0.5 nM 3H-PGE2, the more polar stereoisomer of II [R4 = H] (also prepd.) had a Ki of 0.092 .mu.M. Pharmaceutical compns. contg. I are described.
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Updated 5/3/2007 12:03:52 PM
