Syntex (u.s.a.) Inc.

Albert R Van Horn

Gary F Cooper

Colin C Beard

Douglas L Wren

Tsung-tee Li

John A Edwards

Francisco S Alvarez

Tsung-Tee Li

Pasquale G Gallegra

Gabriel Garay

This invention relates to a process for making a compound of formula I ##STR1## in the form of a stereoisomer or mixture thereof, wherein R is hydrogen, lower alkyl; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta., or a pharmaceutically acceptable, non-toxic salt of the compound wherein R is hydrogen; novel intermediates useful for preparing these compounds; processes for making the intermediates; and a stereoisomer of the compound of formula I wherein R is methyl and X is hydrogen and a process for making same.

Processes and intermediates for making 16-phenoxy- and 16-substituted

This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.

Processes and intermediates for making 16-phenoxy and 16-substituted

This invention covers a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; and X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy; and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..

9-oxo-15.alpha.-hydroxy-16-phenoxy and 16-substituted phenoxy

This invention relates to a process for making an enantiomer or racemic mixture of a compound of the formula ##STR1## wherein R is hydrogen, lower alkyl or a pharmaceutically acceptable, non-toxic salt of a compound wherein R is hydrogen; X is hydrogen, halo, trifluoromethyl, lower alkyl or lower alkoxy, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is a .alpha. the other is .beta.; novel intermediates useful for preparing these compounds; and processes for making the intermediates.

The tricyclic intermediate ##STR1## is prepared in a three step sequence from the bicyclic intermediate ##STR2## The key step of this process involves the addition of a Grignard reagent to a mixed anhydride. Tricyclic compound of formula (I) may be readily converted by known methods to valuable steroids.

Steroid synthesis process using mixed anhydride

Novel 16-phenoxy and 16-(o, m or p)-substituted phenoxy derivatives of (dl)-9-keto-11.alpha.,15.alpha.-dihydroxy-17,18,19,20-tetranorprosta-4,5,1 3-trans-trienoic acid, the pharmaceutically acceptable, non-toxic lower alkyl esters and salts thereof and processes for the production of such compounds. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretion; and as agents for the control of asthmatic attack, because of their bronchodilating activity.

(dl)-16-Phenoxy- and 16-substituted phenoxy-9-keto prostatrienoic acid

5-Substituted-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids of the formula ##STR1## wherein Y is a moiety selected from the group consisting of ##STR2## in which R is hydrogen, methyl, chloro or bromo, the R substitution being at the 3, 4 or 5 positions of the thiophene ring,

1,2-Dihydro-3H-pyrrolo[1,2-a]pyrrole-1-nitriles

Novel prostaglandin intermediates and process for the production thereof. Compounds, and process for the production thereof, useful in the production of (dl)-[1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4 .alpha.-tetrahydropyranyloxy-cyclopent-1.alpha.-yl] acetaldehyde hemiacetal and [1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4.alph a.-tetrahydropyranyloxycyclopent-1.alpha.-yl] acetaldehyde hemiacetal.

Novel prostaglandin intermediates and process for the production thereof

Novel prostaglandin intermediates and process for the production thereof. Compounds, and process for the production thereof, useful in the production of (dl)-[1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4 .alpha.-tetrahydropyranyloxycyclopent-1.alpha.-yl] acetaldehyde hemiacetal and [1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4.alph a.-tetrahydropyranyloxycyclopent-1.alpha.-yl] acetaldehyde hemiacetal.

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San Jose, CA, United States of America

Albert R Van Horn