US 4,059,614 AGranted

2,2-Difluoro-16-phenoxy-PGE.sub.1 analogs

AssigneeThe Upjohn Company

InventorUdo F. Axen

Life of this patent

Estimating the term…

Loading patent…

Abstract

2,2-Difluoro prostaglandin E, F.sub..alpha., F.sub..beta., A, and B analogs are disclosed with intermediates and with processes for making them. These compounds differ from the prostaglandins in that they have two fluoro atoms at the C-2 position in place of the two hydrogen atoms at C-2 in the prostaglandins. These compounds are useful for a variety of pharmacological purposes, including antiulcer, inhibition of platelet aggregation, increase in nasal patency, labor induction at term, and wound healing.

Drawings

Drawings are temporarily unavailable. Open the PDF at USPTO

Drawings

Claims58

Dependent claims

A compound of the formula ##STR1## OR A MIXTURE COMPRISING THAT COMPOUND AND THE ENANTIOMER THEREOF, WHEREIN G IS 2 TO 4, INCLUSIVE;

Wherein M.sub.1 is ##STR2## wherein R.sub.7 and R.sub.8 are hydrogen or methyl, with the proviso that one of R.sub.7 or R.sub.8 is methyl only when the other is hydrogen;
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;
Wherein R.sub.1 is hydrogen, 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, phenyl substituted with one, 2, or 3 chloro, alkyl of one to 4 carbon atoms, inclusive, or a pharmacologically acceptable cation, ##STR3## WHEREIN R.sub.5 is hydrogen or methyl, with the proviso that R.sub.5 is methyl only when R.sub.7 and R.sub.8 are both hydrogen.

Dependencies are inferred from the claim text.

Description30 words

Detailed description30 words

#The present invention relates to prostaglandin analogs for which the essential material constituting a disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,001,300, issued Jan. 4, 1977.

Facts

Application: 05/724,240Filed 17 Sep 1976 · division
Priority: 25 Feb 1975
Granted: 22 Nov 1977
Term ended: 22 Nov 1994
Estimated · howhide
Pre-1995 term; greater of 17 years from grant or 20 years from filing when eligible. Maintenance-fee lapses, terminal disclaimers and statutory extensions have not been checked. The continuity chain may be incomplete; this is not an enforceability determination.

Classification8 codes

C07D 307/935
Condensed with a ring other than six-membered: not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
C07C 405/00
Compounds containing a five-membered ring having two side-chains in ortho position to
C07D 309/12
Oxygen atoms: only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
C07F 9/4006
The acid moiety containing a substituent or a structure which is considered as characteristic: esters of acyclic acids which can have further…

Family

Serial552,708Parent of this division · filed 25 Feb 1975
US 4,001,300 AParent of this division
US 4,059,614 AThis patent

From the US filing history. Foreign family members aren’t listed.

Timeline

25 Feb 1975Priority claimedParent application 552,708
17 Sep 1976Application filedUS 05/724,240
22 Nov 1977GrantedUS 4,059,614 A
22 Nov 1994Term endedEstimated

USPTO file history isn’t available for this patent, so only indexed dates are shown.

Citations

US 3,775,4621973Axen