Abstract: Novel acetylenic derivatives of amines of the following general structure ##STR1## wherein R is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or ##STR2## wherein R.sub.3 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; each of R.sub.1 and R.sub.2 is hydrogen, halogen selected from fluorine, chlorine, bromine and iodine or a straight or branched lower alkyl group of from 1 to 4 carbon atoms and may be the same or different with the proviso that when both R.sub.1 and R.sub.2 are halogen R.sub.1 and R.sub.2 are the same; and pharmaceutically acceptable salts and individual optical isomers thereof.
Abstract: Compounds of the following general formula are useful as antidepressant and antiparkinson agents: ##STR1## WHEREIN R represents hydrogen, hydroxy, halogen, trifluoromethyl, straight or branched lower alkyl of from 1 to 6 carbon atoms, straight or branched lower alkoxy of from 1 to 6 carbon atoms, acyloxy, alkoxycarbonyloxy, carbamoyloxy, benzoyloxy, or benzoyloxy substituted with straight or branched lower alkyl of from 1 to 6 carbon atoms, straight or branched lower alkoxy of from 1 to 6 carbon atoms or halogen; R.sub.1 represents hydrogen, straight or branched lower alkyl of from 1 to 6 carbon atoms, phenyl or benzyl; R.sub.2 represents hydrogen, straight or branched lower alkyl of from 1 to 6 carbon atoms, ethynyl, ethynyl substituted with straight or branched lower alkyl of from 1 to 6 carbon atoms; aryl, or aralkyl wherein each aryl moiety may be substituted with straight or branched lower alkyl of from 1 to 6 carbon atoms, straight or branched lower alkoxy of from 1 to 6 carbon atoms or halogen; R.sub.
Abstract: Compounds of the following general formula are useful in treating the symptoms of menopause and osteoporosis: ##STR1## wherein R is --CHO or --CH.sub.2 OR.sub.1 ; each of R.sub.1 and R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 20 carbon atoms and is straight or branched, benzoyl, phenylalkylcarbonyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched or cycloalkylcarbonyl wherein the cycloalkyl moiety has from 5 to 10 carbon atoms; R.sub.3 is hydrogen; or R.sub.2 and R.sub.3 together form a double bond between the 17-position carbon atom and the oxygen atom.
Type:
Grant
Filed:
February 22, 1977
Date of Patent:
June 20, 1978
Assignee:
Richardson-Merrell Inc.
Inventors:
Harvey D. Benson, Joyce Francis Grunwell, John O'Neal Johnston, Vladimir Petrow
Abstract: Novel compounds of the formula ##STR1## wherein each of R and R.sub.1 is a lower alkyl group of from 1 to 4 carbon atoms, R.sub.3 is an alkyl group and a process employing said compounds.
Type:
Grant
Filed:
July 1, 1977
Date of Patent:
May 9, 1978
Assignee:
Merrell Toraude et Compagnie
Inventors:
Patrick J. Casara, Michel Jung, Brian Walter Metcalf
Abstract: Compounds of the following general formula are testosterone 5.alpha.-reductase inhibitors rendering said compounds useful in the treatment of acne and oily skin: ##STR1## wherein n is an integer of from 0 to 4; R.sub.1 is --COOR.sub.2, --CONR.sub.3 R.sub.4, --CHO or --CH.sub.2 OR.sub.5 ; R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, or benzyl; each of R.sub.3 and R.sub.4 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms; and R.sub.5 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 20 carbon atoms and is straight or branched, benzoyl, phenylalkylcarbonyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched, or cycloalkylcarbonyl wherein the cycloalkyl moiety has from 5 to 10 carbon atoms.
Abstract: Novel compounds of the following general formula are useful pharmacologic agents and are useful as intermediates for the preparation of pharmacologically useful compounds. ##STR1## wherein R.sub.1 is a straight or branched lower alkyl group having from 1 to 4 carbon atoms, R.sub.2 is trialkylmethyl, phenyl, 1-adamantanyl or 2-furyl; R.sub.3 is methoxy or ethoxy; and acid addition salts thereof.
Abstract: Compounds of the following general formula are useful in treating acne: ##STR1## wherein R is --CHO or --CH.sub.2 OR.sub.1 ; each of R.sub.1 and R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 20 carbon atoms and is straight or branched, benzoyl, phenylalkylcarbonyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched or cycloalkylcarbonyl wherein the cycloalkyl moiety has from 5 to 10 carbon atoms; R.sub.3 is hydrogen; or R.sub.2 and R.sub.3 together form a double bond between the 17- position carbon atom and the oxygen atom.
Type:
Grant
Filed:
May 10, 1976
Date of Patent:
March 7, 1978
Assignee:
Richardson-Merrell Inc.
Inventors:
Harvey D. Benson, Joyce Francis Grunwell, John O'Neal Johnston, Vladimir Petrow
Abstract: Compounds of the following general formula are useful in inducing an estrogenic response in a patient in need thereof: ##STR1## wherein R is --CHO or --CH.sub.2 OR.sub.1 ; each of R.sub.1 and R.sub.2 is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 20 carbon atoms and is straight or branched, benzoyl, phenylalkylcarbonyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched or cycloalkylcarbonyl wherein the cycloalkyl moiety has from 5 to 10 carbon atoms; R.sub.3 is hydrogen; or R.sub.2 and R.sub.3 together form a double bond between the 17-position carbon atom and the oxygen atom.
Type:
Grant
Filed:
May 10, 1976
Date of Patent:
March 7, 1978
Assignee:
Richardson-Merrell Inc.
Inventors:
Harvey D. Benson, Joyce Francis Grunwell, John O'Neal Johnston, Vladimir Petrow
Abstract: A spill of liquid elemental mercury is cleaned up by contacting the mercury with zinc coated metal wools which have been activated by immersion in an acid activator solution.
Abstract: Disclosed are novel compounds and pharmaceutical formulations having antiviral activity. The disclosed compounds have the formula ##STR1## wherein one R.sup.2 is a hydrogen atom and the other R.sup.2 is the radical ##STR2## A is a straight chain alkylene group having 2 or 3 carbon atoms and each R.sup.3 and R.sup.4 is a hydrogen atom, and alkyl radical having 1 to 3 carbon atoms or each set of R.sup.3 and R.sup.4 taken together with the nitrogen atom to which they are attached is a saturated monocyclic heterocyclic group. Also included are the acid addition salts of these bases. These compounds may be prepared by various methods which are described.
Type:
Grant
Filed:
January 26, 1976
Date of Patent:
February 14, 1978
Assignee:
Richardson-Merrell, Inc.
Inventors:
Robert W. Fleming, Arthur D. Sill, Francis W. Sweet
Abstract: Derivatives of 19-oxygenated-5.alpha.-androstanes are described which are useful in enhancing the libido and related psychic attitudes in mammals.
Abstract: 2-(2,2-Dicyclohexylethyl)piperidine is prepared via the catalytic hydrogenation of 2-(2,2-diphenylethenyl)pyridine in a single step. High yields are obtained using an anhydrous Raney nickel catalyst.
Type:
Grant
Filed:
April 14, 1976
Date of Patent:
January 17, 1978
Assignee:
Richardson-Merrell Inc.
Inventors:
Stephen W. Horgan, Frank P. Palopoli, Edward J. Schwoegler
Abstract: Substituted benzaldehydes of the following general structure are useful as hypolipidemic agents: ##STR1## wherein Y is selected from oxygen and divalent sulfur; R is selected from a straight or branched saturated hydrocarbon chain having from 10 to 20 carbon atoms and a straight or branched unsaturated hydrocarbon chain having from 10 to 20 carbon atoms and from 1 to 4 double bonds.
Type:
Grant
Filed:
October 3, 1975
Date of Patent:
January 3, 1978
Assignee:
Richardson-Merrell Inc.
Inventors:
Thomas R. Blohm, J. Martin Grisar, Roger Alan Parker
Abstract: The novel bis-basic ketones of fluorene and fluorenone of the present invention have antiviral activity when administered orally and parenterally. These compounds are represented by the following formula: ##STR1## wherein Z is oxygen or H.sub.2 ; each A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y isA. the group ##STR2## wherein R.sup.1 and R.sup.2 are individually hydrogen, (lower)alkyl having from 1 to about 6 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, alkenyl of from 3 to 6 carbon atoms and having the vinyl unsaturation in other than the 1-position of the alkenyl group; orB. the group ##STR3## WHEREIN N IS A WHOLE INTEGER FROM 4 TO 6, AND R.sup.3 is hydrogen, (lower)alkyl of 1 to about 4 carbon atoms, phenyl, or benzyl and can be linked to any one of the carbon atoms of the heterocyclic group; orC. the group ##STR4## wherein X is oxygen or NR.sup.4, and R.sup.4 is hydrogen or (lower)alkyl of from 1 to about 4 carbon atoms; orD.
Type:
Grant
Filed:
February 2, 1973
Date of Patent:
December 20, 1977
Assignee:
Richardson-Merrell Inc.
Inventors:
Robert W. Fleming, Arthur D. Sill, William L. Albrecht, Stephen W. Horgan
Abstract: Compounds of the following general formula are useful in the treatment of sickle cell anemia: ##STR1## WHEREIN EACH OF R and R.sub.1 is hydrogen, chlorine, fluorine, bromine, trifluoromethyl, hydroxy, a lower alkoxy group of from 1 to 4 carbon atoms or a straight or branched lower alkyl group of from 1 to 4 carbon atoms; R.sub.2 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms; R.sub.3 is hydrogen or a straight or branched lower alkyl group of from 1 to 4 carbon atoms, or when R.sub.2 is hydrogen, R.sub.3 is .beta.,.beta.,.beta.-trichloroethoxycarbonyl, benzyloxycarbonyl, p-methoxybenzyloxycarbonyl, p-nitrobenzyloxycarbonyl or tert-butoxycarbonyl; or NR.sub.2 R.sub.3 taken together form a monocyclic heterocyclic group selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-(lower)alkylpiperazino; Z is ##STR2## wherein R.sub.4 is hydrogen or lower alkyl of from 1 to 4 carbon atoms, and R.sub.