The Upjohn Co.

The Upjoin Company

Norman A Nelson

Gordon L Bundy

Robert C Kelly

The present invention comprises certain aromatic and inter-oxa analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. These prostaglandin F.alpha. analogs exhibit prostaglandin F.alpha. activity and are accordingly useful for the same pharmacological purposes as the corresponding prostaglandins.

Aromatic or inter-oxa 2-decarboxy-2-hydroxymethyl-PGF.alpha. compounds

The present invention provides novel pyridinyl-benzimidazoles and quinoxalines which are useful as thromboxane A.sub.2 (TXA.sub.2) synthetase inhibitors and as such represent potent pharmacological agents.

Pyridinyl substituted benzimidazoles and quinoxalines

The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.

Inter-phenylene CBA compounds

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.

Bicyclo lactone intermediates for prostaglandin analogs

16-Phenoxy prostaglandin F.sub.2.alpha. analogs

16-Phenoxy PGE.sub.2 compounds

The present invention relates to novel amido and sulfonamido derivatives of 2-decarboxy-2-amino-methyl-PG-type compounds. These analogs are useful as nasal decongestants, antifertility agents, and as cytoprotection agents.

Amide and sulfonamide derivatives of 2-decarboxy-2-aminomethyl-PG-type

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

2-Decarboxy-2-hydroxymethyl-16-fluoro-PGE.sub.2 compounds

This invention comprises 11-deoxy-17-phenyl-18,19,20-trinor-prostaglandin-type compounds which exhibit prostaglandin-type pharmacological activity, such as lowering blood pressure, inhibiting gastric secretion, regulating the reproductive cycle, and the like.

11-Deoxy-17-phenyl-PGE.sub.1 analogs

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

2-Decarboxy-2-hydroxymethyl PGF.sub.2 .alpha.analogs

2-Decarboxy-2-hydroxyme

2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro PGF.sub.1 compounds

2-Decarboxy-2-hydroxymethyl-deoxy-9,10-didehydro-PGD.sub.2 analogs

5,6-Dihydro-prostacyclin (PGI.sub.1) analogs substituted with hydroxyphenyl groups, illustrated for example, by a compound of the formula ##STR1## i.e. 9-deoxy-6S,9.alpha.-epoxy-17-(o-hydroxyphenyl)-18,19,20-trinor-PGF.sub.1, said products having pharmacological utility.

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Galesburg, MI, United States of America

Norman A Nelson