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Details for Patent: 4,322,525

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Details for Patent: 4,322,525

Title: PGI.sub.2 11,15-Ether intermediates
Abstract:The present invention relates to PGI.sub.2 11,15-ether intermediates, having pharmacological activity. Particularly, the compounds described herein are useful as platelet aggregation inhibitors. The present invention describes PGI.sub.2 11,15-ether intermediates. These compounds are intermediates for preparing corresponding prostacylcin-type compounds with pharmacological utility, e.g., platelet aggregation inhibitors.
Inventor(s): Johnson; Roy A. (Kalamazoo, MI), Lincoln; Frank H. (Portage, MI), Pike; John E. (Kalamazoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Oct 27, 1980
Application Number:06/200,699
Claims:1. A compound of the formula ##STR2## or a mixture comprising that compound and the enantiomer thereof, wherein W.sub.3 is .alpha.-OR.sub.33 :.beta.-H, .alpha.-H:.beta.-OR.sub.33, or .alpha.:CH.sub.2 OR.sub.33 :.beta.-H, wherein R.sub.33 is

(a) tetrahydropyranyl,

(b) tetrahydrofuranyl,

(c) a group of the formula --C(OR.sub.14)(R.sub.15)--CH(R.sub.16)(R.sub.17), wherein R.sub.14 is alkyl of one to 18 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 alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.15 and R.sub.16 are the same or different, being hydrogen, alkyl of one to 4 carbon atoms, inclusive, phenyl or phenyl substituted with one, 2, or 3 alkyl or one to 4 carbon atoms, inclusive, or, when R.sub.15 and R.sub.16 are taken together, --(CH.sub.2)a-- or --(CH.sub.2)b--O--(CH.sub.2)c, wherein a is 3, 4, or 5, b is one, 2, or 3, and c is one, 2, or 3 with the proviso that b plus c is 2, 3, or 4, and wherein R.sub.17 is hydrogen or phenyl, or

(d) carboxyacyl including

(a') --CO--(Ph II), wherein (Ph II) is phenyl optionally substituted by one-5 is alkyl of one to 4 carbon atoms, inclusive, bromo, phenylalkyl of 7 to 10 carbon atoms, inclusive, or nitro, provided that not more than two such substituents are other than alkyl, and that the total number of carbon atoms, in the substituents does not exceed 10 carbon atoms,

(') --CO--(Ph III), wherein (Ph III) is phenyl substituted by --COOR.sub.30, wherein R.sub.30 is alkyl of one to 4 carbon atoms, inclusive,

(c') --CO--(Np I), wherein (Np I) is naphthyl optionally substituted as is (Ph II)

(d') --CO--R.sub.31, wherein R.sub.31 is alkyl of one to 7 carbon atoms, inclusive,

wherein L is

(1) --(CH.sub.2).sub.d--C(R.sub.2).sub.2 --,

(2) --CH.sub.2 --O--CH.sub.2 --Y--, or

(3) --CH.sub.2 CH.dbd.CH--,

wherein d is zero to 5, R.sub.2 is hydrogen, methyl, or fluoro, being the same or different with the proviso that one of R.sub.2 is not methyl when the other is fluoro, and Y is a valence bond, --CH.sub.2 --, or --(CH.sub.2).sub.2 --,

wherein Q.sub.2 is oxo, .alpha.-H:.beta.-H, .alpha.-OR.sub.33 :.beta.-R.sub.8, or .alpha.-R.sub.8 :.beta.-OR.sub.33, wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, and R.sub.33 is as defined above.

wherein R.sub.1 is

(1) --COOR.sub.3,

(2) --CH.sub.2 OH,

(3) --CH.sub.2 N(R.sub.9)(R.sub.18),

(4) --CO--N(R.sub.9)(R.sub.18 ) or

(5) tetrazolyl, wherein R.sub.3 is

(a) hydrogen,

(b) alkyl of one to 12 carbon atoms, inclusive,

(c) cycloalkyl of 3 to 10 carbon atoms, inclusive,

(d) aralkyl of 7 to 12 carbon atoms, inclusive

(e) phenyl,

(f) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive,

(g) --(p-Ph)--NH--CO--(p-Ph)--NH--CO--CH.sub.3,

(h) --(p-Ph)--NH--CO--(Ph),

(i) --(p-Ph)--NH--CO--CH.sub.3,

(j) --(p-Ph)--NH--CO--NH.sub.2,

(k) --(p-Ph)--CH.dbd.N--NH--CO--NH.sub.2,

(l) 2-naphthyl,

(m) CH(R.sub.11)--CO--R.sub.10, wherein R.sub.10 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, wherein R.sub.11 is hydrogen or benzoyl, (Ph) is phenyl and (p-Ph) is 1,4-phenylene or

(n) a pharmacologically acceptable cation;

wherein R.sub.9 is hydrogen, methyl, or ethyl, and wherein R.sub.18 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with alkyl of one to 4 carbon atoms, inclusive,

wherein R.sub.4 is

--C(R.sub.5) (R.sub.6)C.sub.g H.sub.2g --CH.sub.3,

--C (R.sub.5) (R.sub.6)--Z--(PH I), or

--CH.sub.2 --CH.dbd.CH--CH.sub.2 CH.sub.3,

wherein C.sub.g H.sub.2g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR.sub.5 R.sub.6 and terminal methyl, wherein R.sub.5 and R.sub.6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R.sub.5 and R.sub.6 is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R.sub.5 nor R.sub.6 is fluoro when Z is oxa (--0--); wherein Z represents an oxa atom (--0--) or C.sub.j H.sub.2j where in C.sub.j H.sub.2j is a valence bond or alkylene or one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR.sub.5 R.sub.6 --and (Ph I); wherein (Ph I) is phenyl optionally substituted by one, 2, or 3 alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.7 -- wherein R.sub.7 is alkyl to one to 4 carbon atoms, inclusive, with the proviso that not more than two such substituents are other than alkyl and such substituents being either the same or different; and

wherein X is

(1) trans--CH.dbd.CH--,

(2) cis--CH.dbd.CH--,

(3) --C.tbd.C--, or

(4) --CH.sub.2 CH.sub.2 --;

including the lower alkanoates thereof.
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