Method for preparing cyclic ethers and thioethers including oxygen isomers and sulfur analogs of prostacyclin
US4258199A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Mar 13, 1978 |
| Grant date | Mar 24, 1981 |
| Priority date | — |
| Expiry date | Mar 13, 1998 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F7/1804
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Unsaturated alcohols, thiols and thioesters are cyclized by a phenyl selenenyl halide; wherein the conformation flexibility of the unsaturated alcohol, thiol or thioester is selected such that the hydroxy group, thiol group or thioester group is capable of internal addition to at least one unsaturated bond in said alcohol, thiol or thioester; and wherein the ratio of the phenyl selenenyl halide to said unsaturated alcohol, thiol or thioester is 0.9-1.5 to 1. In a preferred embodiment, oxygen isomers and sulfur analogs of prostacyclin of the formula ##STR1## wherein X= ##STR2## Y=(E)- and (Z)- >C.dbd.CH--CH.sub.2 CH.sub.2 CH.sub.2 COOR; (E)- >CH--CH.dbd.CH--CH.sub.2 CH.sub.2 COOR; and PA1 R=any pharmaceutically acceptable cation or lower alkyl group comprising 1 to 4 carbon atoms are formed by: PA2 (1) cyclizing a PGF.sub.2.alpha. prostaglandin derivative or a 9.alpha. thio or 9.alpha. -thioester analog of prostaglandin PGF.sub.2.alpha. by reacting said prostaglandin derivative or analog with a phenyl selenenyl halide, wherein the molar ratio of said phenyl selenenyl halide to said prostaglandin derivative or analog is 0.9-1.5:1; and PA2 (2) oxidizing the product obtained therefrom.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.