The Upjohn Co.

Pharmacia & Upjohn Company

Upjohn

E Jon Jacobsen

John M McCall

Donald E Ayer

John R Palmer

Frederick J VanDoornik

Harold A Karnes

John Nicholas Freskos

David Louis Brown

Yvette M Fobian

Michael B Tollefson

Ronald B Gammill

Andrew Simon Bell

Ruth Elizabeth TenBrink

Robert Owen Hughes

Dafydd Rhys Owen

Brent V Mischke

Michael John Palmer

Todd M Maddux

David Graham Brown

John M Molyneaux

Stephen J Humphrey

John K Walker

Christopher Phillips

James Taylor Curry

Joseph B Moon

Steven E Heasley

Frederick J Van Doornik

D Joseph Rogier, Jr

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I: wherein R, R, Rand Rare as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, synthetic methods, and intermediates are also disclosed.

Pyridine [3,4-b] pyrazinones

A diuretic compound of Formula I ##STR1## or pharmaceutically acceptable salt thereof where R.sup.1 is a C.sub.1-6 alkyl; R.sup.2 is halogen, C.sub.1-4 alkyl; and R.sup.3 is C.sub.1-4 alkoxy are disclosed, preferably, benzamide, 3-chloro-N-(2-ethyl-2-(3-methoxyphenyl)-4-(1-piperidinyl)butyl), monohydrochloride. The compounds are effective diuretics which increase the excretion of water with little increase in electrolyte excretion.

Diuretic compound

The present invention provides novel hydroxamic acid derivatives represented by the compound of formula I ##STR1## or pharmaceutical acceptable salts thereof, wherein the compounds of the present invention inhibit various enzymes from the matrix metalloproteinase family, including collagenase, stromelysin, and gelatinase, and hence are useful for the treatment of matrix metallo endoproteinase diseases such as osteoarthrits, rheumatoid arthritis, septic arthritis, osteopenias such as osteoporosis, tumor metastasis (invasion and growth), periodontitis, gingivitis, corneal ulceration, dermal ulceration, gastric ulceration, and other diseases related to connective tissue degradation.

Hydroxamic acid derivatives useful for the treatment of diseases related

The invention discloses imidazo[1,5-a]quinoxalines (I) ##STR1## which do not contain an endocyclic carbonyl group that are useful as anxiolytic and sedative/hypnotic agents.

5,6-cyclicimidazo [1,5-a] Quinoxalines

An invention relating to Imidazo[1,5-a]quinoxalines (I) ##STR1## which do not contain an endocyclic carbonyl group and which are useful as anxiolytic and sedative/hypnotic agents.

Imidazo[1,5-A]quinoxalines

Disclosed are amino substituted steroids (XI) which contain an imidazolylpiperazinyl group attached to the terminal carbon atom of the C.sub.17 -side chain which are useful as pharmaceutical agents for treating a number of conditions.

Imidazolylpiperazinyl steroids

Disclosed are amino substituted steroids (XI) which contain a phenylpiperazinyl group attached to the terminal carbon atoms of the C.sub.17 -side chain, which are useful as pharmaceutical agents for treating a number of conditions.

Phenylpiperazinyl steroids

Disclosed are amino substituted steroids (XI) which contain a pyridinylpiperazinyl group group attached to the terminal carbon atom of the C.sub.17 -side chain of the steroid which are useful as pharmaceutical agents for treating a number of conditions.

Pyridinylpiperazinyl steroids

Disclosed are amino substituted steroids (XI) which contain 4-[1,3,5-triazin-2-yl]- or 4-[1,2,4-triazin-3-yl]- 1-piperazinyl group attached to the terminal carbon atom of the C.sub.17 -side chain which are useful as pharmaceutical agents for treating a number of conditions.

Triazinylpiperazinyl steroids

The claimed invention is to triazin-2-yl and triazin-3-yl piperazines which are useful intermediates in the preparation of amino substituted steroid (XI) which are useful pharmaceutical agents.

Triazinylpiperazinyl amine intermediates

The aromatic amines (I), alkyl amines (II), bicyclic amines (III). ##STR1## cycloalkyl amines (IV), aromatic bicyclic amines (V), hydroquinone amines (VI), quinone amines (VII), amino-ethers (VIII) and bicyclic amino ethers (IX) are useful as pharmaceutical agents for treating a number of conditions including spinal trauma, mild and/or moderate to severe head injury, etc. Also disclosed is a method of treatment using the 3,4-dihydrobenzopyrans (XI).

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Plainwell, MI, United States of America

E Jon Jacobsen