Abstract: Certain novel 1-(substituted-alkyl)-3-(3-hydroxyphenyl)piperidine compounds, and the pharmaceutically-acceptable acid-addition salts thereof, possess pharmaceutical activity as neuroleptic agents, and they are useful for treating psychotic disorders, e.g. schizophrenia, in human subjects. In particular, they are useful for alleviating such symptoms as anxiety, agitation, excessive agression, tension and social or emotional withdrawal in psychotic patients.Certain 3-(3-methoxyphenyl)piperidine compounds are useful as chemical intermediates to the aforementioned neuroleptic agents.
Abstract: One mole of 2,2,3,3,4,4-hexafluoropentane-1,5-diol is reacted with one mole f formaldehyde in the presence of an excess of trifluoromethanesulfonic acid to produce 1,3-dioxa-5,5,6,6,7,7-hexafluorocyclooctane.
Type:
Grant
Filed:
July 8, 1985
Date of Patent:
June 3, 1986
Assignee:
The United States of America as represented by the Secretary of the Navy
Inventors:
Judah M. Goldwasser, Horst G. Adolph, Cynthia L. Ebner
Abstract: New hexanor-brassinolid-22-ethers are disclosed, of the formula ##STR1## wherein Z is the group ##STR2## OR.sub.2 and OR.sub.3 are oriented cis 2.alpha., 3.alpha. or 2.beta., 3.beta., R.sub.2 and R.sub.3 are the same or different and are each hydrogen formyl, C.sub.2 -C.sub.7 -alkyl-CO--, C.sub.2 -C.sub.7 -alkoxy-C.sub.1 -C.sub.3 -alkyl-CO-- or aryl-CO--, and R.sub.23 is straight-chain or branched C.sub.1 -C.sub.7 -alkyl or C.sub.1 -C.sub.7 -alkoxy-C.sub.1 -C.sub.3 -alkyl. Also disclosed are processes for the production of these compounds as well as compositions containing the same having growth-regulatory activity for plants.
Abstract: Antimicrobial activity is exhibited by compounds having the formula ##STR1## wherein R.sub.1 is hydrogen or aryl;R.sub.2 is hydroxymethyl, carboxyaldehyde, propenalyl, 3-hydroxy-1-propenyl, or 3-hydroxy-1,2-epoxypropyl; andn is 2 and m is 1 or n is 3 and m is 0; with the proviso that if R.sub.1 is hydrogen, n is 2 and m is 1.
Abstract: The compound (-)-trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine and pharmaceutically-acceptable acid addition salts thereof, pharmaceutical compositions thereof, and their use in potentiating the 5-hydroxytryptamine(5-HT) of a subject in need thereof, for the alleviation of any of various physiological abnormalities, are disclosed.
Type:
Grant
Filed:
February 7, 1984
Date of Patent:
April 29, 1986
Assignee:
A/S Ferrosan
Inventors:
Jorgen B. Lassen, Jorgen A. Christensen, Erling N. Petersen, John B. Hansen
Abstract: 6,11-Dihydrodibenz[b,e]oxepin-acetic acids and derivatives having the general formula ##STR1## are prepared by multi-step sequences. X is C.dbd.O, CHCl, CHBr, CH.sub.2 or CHOR.sup.4 ; Y is alkyl or alkoxy of 1 to 4 carbon atoms, halogen or trifluoromethyl; n is 0, 1, 2 or 3; Z is COOR.sup.5, CH.sub.2 OR.sup.5, CONR.sub.2.sup.5 or CONHOR.sup.5 ; and R.sup.1 -R.sup.5 are hydrogen or alkyl of 1 to 4 carbon atoms.These compounds and the physiologically tolerable salts thereof are useful as antiinflammatory and analgesic agents.
Type:
Grant
Filed:
April 10, 1974
Date of Patent:
April 29, 1986
Assignee:
American Hoechst Corporation
Inventors:
Grover C. Helsley, Arthur R. McFadden, David Hoffman
Abstract: The compound 6(R)-[2-8(S)(2,2-dimethylbutyryloxy)-2(S),6(S)-dimethyl-1,2,3,4,4a(S),5,6, 7,8,8a(S)-decahydronaphthyl-1(S)ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-p yran-2-one is prepared in two steps from mevinolin and comprise reduction of the two double bonds and C-methylation of the 8(S)-(2-methylbutyryloxy) group to form the 2,2-dimethylbutyryloxy group. The two steps can be performed in either order.
Type:
Grant
Filed:
May 23, 1985
Date of Patent:
April 22, 1986
Assignee:
Merck & Co., Inc.
Inventors:
Meyer Sletzinger, Thomas R. Verhoeven, Ralph P. Volante
Abstract: In a multistage process for the continuous epoxidation of double bonds of terminal and non-terminal olefins containing more than 12 carbon atoms, unsaturated higher fatty acids and their lower alkanol and lower alkanediol esters and also unsaturated fatty alcohols containing from 8 to 18, preferably 18, carbon atoms and triglycerides of higher fatty acids including unsaturated fatty acids, preferably soyabean oil, using performic acid formed in situ from hydrogen peroxide and formic acid, the reactants, olefin and hydrogen peroxide/formic acid, are passed at ambient pressure in cross-counter flow through an at least three-stage reaction cascade. The olefinic phase is introduced into the first reaction stage, the hydrogen peroxide and the formic acid are introduced in separate streams into the penultimate reaction stage and the olefin phase and the hydrogen peroxide/formic acid phase (acid water phase) are separated from one another in a phase separator after each reaction stage.
Abstract: This invention relates to a novel process for the preparation of 3-hydroxy-3-methylglutarylcoenzyme A (HMG-CoA) reductase inhibitors which contain a 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety, such as compactin and mevinolin, by utilizing an alkyl 4-halo-3(S)-hydroxybutanoate as a chiral synthon for the stereospecific introduction of the 4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one moiety.
Type:
Grant
Filed:
January 31, 1985
Date of Patent:
April 15, 1986
Assignee:
Merck & Co., Inc.
Inventors:
Ralph P. Volante, Thomas R. Verhoeven, Meyer Sletzinger, James M. McNamara, Thomas M. H. Liu, Edward G. Corley
Abstract: Disclosed are novel 5-halo-4H-1,3-dioxin-4-ones and their preparation by treating a compound having the formula ##STR1## with X.sub.2 or SO.sub.2 X.sub.2 wherein X is Cl or Br.
Abstract: A novel sequence of highly selective chemical reactions for conversion of 3-Aryl-2-propyn-1-ols into cis-1-Aryl-3-fluoro-1-propene and into D,L-(threo)-1-Aryl-2-acylamido-3-fluoro-1-propanols is disclosed. Preparation of D-(threo)-1-Aryl-2-acylamido-3-fluoro-1-propanol antibacterial agents including the D-(threo)-3-fluoro-3-deoxy derivatives of chloramphenicol and thiamphenicol is also disclosed.
Type:
Grant
Filed:
September 19, 1984
Date of Patent:
April 15, 1986
Assignee:
Schering Corporation
Inventors:
Tattanahali L. Nagabhushan, Stuart W. McCombie
Abstract: Mevinolin, compactin and dihydro- and tetrahydro derivatives thereof are converted to more active HMG-CoA reductase inhibitors by C-methylation of the natural 2(S)-methylbutyryloxy side chain to form a 2,2-dimethylbutyryloxy side chain.
Type:
Grant
Filed:
May 23, 1985
Date of Patent:
April 15, 1986
Assignee:
Merck & Co., Inc.
Inventors:
Meyer Sleteinger, Thomas R. Verhoeven, Ralph P. Volante
Abstract: Spiro[2H-1,4-benzodioxepin-3(5H)4'-piperidine and -3-pyrrolidine] compounds of the formula ##STR1## where the substituents are as defined herein, are useful in the treatment of hypertension in mammals. Such compounds, their use as antihypertensive agents, pharmaceutical compositions containing the compounds, intermediates and processes for preparing the compounds are provided.
Type:
Grant
Filed:
July 12, 1984
Date of Patent:
April 1, 1986
Assignee:
Hoechst-Roussel Pharmaceuticals Inc.
Inventors:
Raymond W. Kosley, Jr., Robert J. Cherill
Abstract: Novel phosphorus containing antibiotic compounds that are antitumor agents designated CL 1565-A, CL 1565-B, CL 1565-T and their salts, a process for the production and the method of using said compounds, and pharmaceutical compositions containing various salts of the compounds of the invention alone or in combination with other antitumor agents in the treatment of microbial infections and neoplastic diseases, are provided.
Type:
Grant
Filed:
July 2, 1984
Date of Patent:
March 25, 1986
Assignee:
Warner-Lambert Company
Inventors:
Suresh S. Stampwala, James C. French, Josefino B. Tunac, Timothy R. Hurley, Richard H. Bunge
Abstract: Spiro[2H-1,4-benzodioxepin-3(5H)4'-piperidine and -3-pyrrolidine] compounds of the formula ##STR1## where the substituents are as defined herein, are useful in the treatment of hypertension in mammals. Such compounds, their use as antihypertensive agents, pharmaceutical compositions containing the compounds, intermediates and processes for preparing the compounds are provided.
Type:
Grant
Filed:
July 12, 1984
Date of Patent:
March 18, 1986
Assignee:
Hoechst-Roussel Pharmaceuticals Inc.
Inventors:
Raymond W. Kosley, Jr., Robert J. Cherill
Abstract: Perfluoroalkyl-alkyl-thio, sulfinyl or sulfonyl-alkylene glycidyl ethers of the formula ##STR1## wherein R.sub.f is perfluoroalkyl or perfluoralkoxyperfluoroalkyl of 3 to 18 carbon atoms;R.sub.1 is alkylene, carboxamidoalkylene or sulfonamidoalkylene of up to six carbon atoms and wherein the amido nitrogen is unsubstituted or substituted by lower alkyl;m is 0, 1 or 2; andR is alkylene of 2 to 12 carbon atoms, are useful as intermediates in preparing surfactants.
Abstract: A process for the optical resolution of the enantiomers of trans-3-[(4-methoxyphenoxy)-methyl]-1-methyl-4-phenylpiperidine, which involves reaction with an enantiomer of mandelic acid to form a mixture of diastereomeric compounds, precipitating one of the diastereoisomers, and converting it to the desirable free (+)-trans isomer, as well as the key diastereomeric isomer intermediate, is disclosed.
Abstract: Spiro[2H-1,4-benzodioxepin-3(5H)4'-piperidine and -3'-pyrrolidine] compounds of the formula ##STR1## where the substituents are as defined herein, are useful in the treatment of hypertension in mammals. Such compounds, their use as antihypertensive agents, pharmaceutical compositions containing the compounds, intermediates and processes for preparing the compounds are provided.
Type:
Grant
Filed:
July 12, 1984
Date of Patent:
February 11, 1986
Assignee:
Hoechst-Roussel Pharmaceuticals Inc.
Inventors:
Raymond W. Kosley, Jr., Robert J. Cherill
Abstract: This invention is a process for the preparation of an epoxide which comprises contacting a 2-haloalkyl or 2,3-dihaloalkyl carbonate, bis(2-haloalkyl- or 2,3-dihaloalkyl)carbonate, or 2-haloalkyl or 2,3-dihaloalkyl ester dissolved in a water-miscible alcohol with a sufficient amount of an aqueous solution of an alkali metal or alkaline earth metal hydroxide to provide at least one equivalent of alkali metal or alkaline earth metal hydroxide per equivalent of ester or carbonate, at a temperature of between about 0.degree. C. and 70.degree. C. under conditions such that an epoxide is prepared.
Abstract: Thio-bis-(hydrocarbyl substituted diacid materials), such as thio-bis-(polyalkyl lactone acid) and/or their precursors, the adducts of sulfur chloride and unsaturated diacid materials, e.g., 4,8-bis-polyalkyl-4,8-dichloro-5-thiaundecane-1,2,10,11-tetracarboxylic acid bis-anhydride and their dehydrochlorinated analogs, when esterified with an alcohol, preferably a polyol, such as pentaerythritol, polypentaerythritol or a polyalkylene glycol with or without acid catalysts and/or metal template reagents yield thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) which can be characterized in part, as macrocyclic and/or macrocyclic-like structures, are useful as stable additives in lubricating compositions, e.g. as varnish inhibiting dispersants for lubricating oils and fuels.