Merck + Co., Inc.

Marcia E Christy

Gerald S Ponticello

Paul S Anderson

John J Baldwin

Ben E Evans

David C Remy

Kenneth L Shepard

Edward L Engelhardt

Sandor L Varga

Robert G Strachan

Daniel F Veber

Frederick W Holly, Deceased

Aromatic sulfonamides with a saturated heterocycle fused thereto are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure.

Substituted aromatic sulfonamides as antiglaucoma agents, compositions

Thieno thiopyran sulfonamide derivatives, pharmaceutical compositions

Antiglaucoma thieno-thiopyran and thieno-thiepin sulfonamide

Novel substituted imidazoles and methods for their preparation are disclosed. These imidazoles, and their salts, exhibit cardioselective .beta.-adrenergic blocking activity, and are useful as antihypertensive agents, cardioprotective agents, antiarrythmic agents, antianginal agents with reduced side effects; e.g., they are devoid of intrinsic sympathomimetic activity.

Novel substituted imidazoles, their preparation and use

There are disclosed cyclic octapeptide analogs of the tridecapeptide, neurotensin.

Cyclic octapeptide analogs of neurotensin

There are disclosed metabolically protected linear analogs of the carboxy terminal pentapeptide fragment of the tridecapeptide, neurotensin.

Metabolically protected analogs of neurotensin

Dibenzo[a,d]cycloocten-5,12-(and 6,12)-imines, derivatives and pharmaceutically acceptable salts thereof are useful as anxiolytics, antidepressants, anticonvulsants, muscle relaxants and in the treatment of mixed anxiety-depression, minimal brain dysfunction and extrapyramidal disorders such as Parkinson's disease.

Dibenzo[a,d]cycloocten-5,12-imines

5-Substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines, derivatives and pharmaceutically acceptable salts thereof are useful as anticonvulsants.

5-Alkyl or hydroxyalkyl

Dibenzo[a,d]cycloocten-5,12-(and 6,12)-imines

Dibenzo[a,d]cycloocten-6,12-imines

New fluoro derivatives of aralkylamine compounds, particularly 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine, as well as the N-alkyl and the N,N-dialkyl derivatives thereof are prepared by reaction of 2-bromobenzonitrile with benzylmagnesium chloride to produce 2'-bromo-2-phenylacetophenone; oxidation of said acetophenone with selenous acid to produce 2-bromobenzil; conversion of the benzil compound by treatment with sulfur tetrafluoride to the corresponding 2-bromo-.alpha.,.alpha.-.alpha.',.alpha.'-tetrafluorobibenzyl;followed by reaction of the 2-bromobibenzyl compound with a metal cyanide to produce the corresponding 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzonitrile. This nitrile compound is then reduced with lithium aluminum hydride to produce the corresponding benzylamine, which is then converted, if desired, to the N-alkyl and/or N,N-dialkyl 2-(2-phenyl-1,1,2,2-tetrafluoroethyl)benzylamine. Alternatively, the nitrile or the precursor bromobibenzyl can be converted by Grignard reactions to the corresponding .alpha.-alkyl or .alpha.,.alpha.-dialkylbenzylamine which can then be converted if desired to the corresponding N-alkyl and/or N,N-dialkyl substituted benzylamine compound. The phenyltetrafluoroethylbenzylamine as well as its N-alkyl and N,N-dialkyl derivatives are active as antiarrhythmic agents.

Arylperfluoroalkanes

Tetrafluoro derivatives of 10,11-dihydrodibenzo[a,d]cyclohepten-5-aminomethyl compounds and the corresponding N-substituted derivatives thereof, useful as antiarrhythmic agents, are prepared from tetrafluoro derivatives of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one by reduction to the corresponding 5-ol compound and subsequently converting said 5-ol compound to the corresponding 5-halo and the 5-aminomethyl derivatives by reactions known in the prior art.

10,11-Dihydro-10,10

Substituted 9,10-dihydroanthracen-9,10-imines are disclosed to be minor tranquilizers, anticonvulsnts, muscle relaxants, and to be useful in the treatment of extrapyramidal disorders such as Parkinson's disease; also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions.

Substituted 9,10-dihydroanthracen-9,10-imines

Phenylthioaralkylamines and 2-phenylthiobenzylamines are prepared by reaction of the corresponding phenylthiobenzoyl chloride or homologs thereof with ammonia or an amine to produce the corresponding phenylthiobenzamide or N-substituted or N,N-disubstituted derivative thereof followed by reduction with lithium aluminum hydride to produce the corresponding phenylthiobenzylamine or the N-substituted or N,N-disubstituted derivative thereof. The compounds are also prepared by reaction of the corresponding phenylthiobenzyl halide with ammonia or a selected amine. The compounds are active as antiarrhythmics.

Treating arrythmia with phenylthioaralkylamines

Heterocyclic dihydroanthracen imines are disclosed to be useful as minor tranquilizers, anticonvulsants, muscle relaxants and to be useful in the treatment of extrapyramidal disorders such as Parkinson's disease; also disclosed are processes for the preparation of such compounds; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions.

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Perkasie, PA, United States of America

Marcia E Christy