TREA

16-Phenoxy PGE.sub.2 compounds

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Information

  • Patent Grant
  • 4301294
  • Patent Number
    4,301,294
  • Date Filed
    Friday, December 19, 1980
    45 years ago
  • Date Issued
    Tuesday, November 17, 1981
    44 years ago
Information
Abstract
Prostaglandin-type compounds with a phenoxy or substituted-phenoxy substituent at the C-16 position are disclosed, with processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.
Description
Claims
  • 1. An optically active compound of the formula ##STR1## or a racemic compound of that formula and the mirror immage thereof, wherein g is an integer from 2 to 5, inclusive;
  • wherein M is .alpha.-OH:.beta.-H or .beta.-OH:.alpha.-H;
  • wherein R.sub.1 is hydrogen or alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive;
  • wherein R.sub.2 and R.sub.3 are hydrogen, methyl, or ethyl;
  • wherein T is alkyl of one to 3 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.4, wherein R.sub.4 is alkyl of one to 3 carbon atoms, inclusive, and
  • wherein s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl, including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.
  • 2. A compound according to claim 1 wherein g is 3.
  • 3. A compound according to claim 2 wherein M is .alpha.-OH:.beta.-H.
  • 4. A compound according to claim 3 wherein R.sub.2 and R.sub.3 are hydrogen, and is zero.
  • 5. 16-Phenoxy-17,18,19,20-tetranor-PGE.sub.2, methyl ester, an optically active compound according to claim 4 wherein R.sub.1 is methyl.
  • 6. A compound according to claim 3 wherein R.sub.2 and R.sub.3 are methyl, and s is zero.
  • 7. 16-Methyl-16-phenoxy-18,19,20-trinor-PGE.sub.2, an optically active compound according to claim 6 wherein R.sub.1 is hydrogen.
  • 8. 16-Methyl-16-phenoxy-18,19,20-trinor-PGE.sub.2, methyl ester, an optically active compound according to claim 6 wherein R.sub.1 is methyl.
Parent Case Info

The present application is a divisional application of Ser. No. 426,058, filed Dec. 19, 1973, now pending which is a division of Ser. No. 252,030 filed May 10, 1972.

Non-Patent Literature Citations (1)
Entry
Kirton, B. B. et al., Proceedings of the Society for Experimental Biology and Medicine, vol. 33, No. 1, pp. 314-316, Jan. 1970.
Divisions (2)
Number Date Country
Parent 426058 Dec 1973
Parent 252030 May 1972