Patents Assigned to Richardson-Merrell Inc.
  • Patent number: 4483988
    Abstract: Novel analgesic and antipsychotic agents having the formula ##STR1## in which R.sub.1 is hydrogen, hydroxy or halogen and R.sub.4 is hydrogen or, R.sub.1 and R.sub.4 are both hydroxy; Z is hydrogen or straight chain lower alkyl having from 1 to 4 carbon atoms and X is methylene, carbonyl, hydroxymethylene, thio, sulfinyl or sulfonyl, or Z and X, taken together, are methylidenyl, with the proviso that when X is sulfonyl or sulfinyl, Z is other than hydrogen; R.sub.5 is hydrogen or halogen, and R.sub.2 is H, a straight or branched lower alkyl group having from 1 to 4 carbon atoms, the group ##STR2## or the group ##STR3## wherein R.sub.3 is hydroxy, amino, alkylamino or dialkylamino wherein the alkyl moiety is straight or branched and has from 1 to 4 carbon atoms, diastereomers, enantiomers and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: November 20, 1984
    Assignee: Richardson Merrell Inc.
    Inventors: Albert A. Carr, Robert A. Farr, John M. Kane
  • Patent number: 4439443
    Abstract: A method of reducing local hemorrhage and tissue necrosis resulting from the bite or sting of a venomous animal whereby an envenomated mammal is treated with a compound of the formula ##STR1## or a corresponding disulfide wherein n is 1, 2 or 3; Z is O, S or NH; R is H, a straight or branched chain lower alkyl group of from 1 to 4 carbon atoms, hydroxy, a straight or branched chain lower alkoxy group of from 1 to 4 carbon atoms, fluoro, chloro, bromo, iodo or trifluoromethyl; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: July 2, 1982
    Date of Patent: March 27, 1984
    Assignee: Richardson-Merrell Inc.
    Inventor: Eugene L. Giroux
  • Patent number: 4435571
    Abstract: The present invention relates to compounds of the formula ##STR1## wherein R' is hydrogen, straight or branched chain lower alkyl having from 1 to 4 carbon atoms or benzyl, Z is hydrogen or straight chain lower alkyl having from 1 to 4 carbon atoms, Y is hydrogen or a nitrogen blocking group selected from the group consisting of tertiary alkoxycarbonyl, benzyloxycarbonyl, cycloalkoxycarbonyl and vinyloxycarbonyl, R.sub.c is hydrogen, halogen or benzyloxy and R.sub.d is hydrogen, or R.sub.c and R.sub.d are benzyloxy; or an individual diastereomer thereof. Said compounds having use as intermediates in the production of enkephalin derivatives which in turn are used as analgesic and antipsychotic agents.
    Type: Grant
    Filed: July 19, 1982
    Date of Patent: March 6, 1984
    Assignee: Richardson Merrell Inc.
    Inventors: Albert A. Carr, Robert A. Farr, John M. Kane
  • Patent number: 4411905
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is H or NH.sub.2 ; R.sub.2 is C.sub.1-6 straight or branched chain alkyl; --CH.sub.2 OH; --(CH.sub.2).sub.n --O--(CH.sub.2).sub.m --CH.sub.3 ; phenyl; or --(CH.sub.2).sub.p NH.sub.2 ;n is 1-3;m is 0-3; andp is 1-5;and the pharmaceutically acceptable acid addition salts of those compounds of basic character,have antisecretory activity.
    Type: Grant
    Filed: June 15, 1981
    Date of Patent: October 25, 1983
    Assignee: Richardson-Merrell Inc.
    Inventors: William L. Albrecht, Winton D. Jones
  • Patent number: 4347255
    Abstract: A method of reducing local hemorrhage and tissue necrosis resulting from the bite or sting of a venomous animal whereby an envenomated mammal is treated with a compound of the formula: ##STR1## or a corresponding disulfide wherein n is 1, 2 or 3; Z is O, S or NH; R is H, a straight or branched chain lower alkyl group of from 1 to 4 carbon atoms, hydroxy, a straight or branched chain lower alkoxy group of from 1 to 4 carbon atoms, fluoro, chloro, bromo, iodo or trifluoromethyl; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: August 7, 1981
    Date of Patent: August 31, 1982
    Assignee: Richardson-Merrell Inc.
    Inventor: Eugene L. Giroux
  • Patent number: 4341698
    Abstract: Novel analgesic and antipsychotic agents having the formula ##STR1## wherein Q is ##STR2## in which R.sub.1 is hydrogen, hydroxy or halogen and R.sub.4 is hydrogen or, R.sub.1 and R.sub.4 are both hydroxy; Z is hydrogen or straight chain lower alkyl having from 1 to 4 carbon atoms and X is methylene, carbonyl, hydroxymethylene, thio, sulfinyl or sulfonyl, or Z and X, taken together, are methylidenyl, with the proviso that when X is sulfonyl or sulfinyl, Z is other than hydrogen; R.sub.5 is hydrogen or halogen, and R.sub.2 is H, a straight or branched lower alkyl group having from 1 to 4 carbon atoms, the group ##STR3## or the group ##STR4## wherein R.sub.3 is hydroxy, amino, alkylamino or dialkylamino wherein the alkyl moiety is straight or branched and has from 1 to 4 carbon atoms, diastereomers, enantiomers and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: March 14, 1980
    Date of Patent: July 27, 1982
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, Robert A. Farr, John M. Kane
  • Patent number: 4325877
    Abstract: 5-Amino-4-oxo-pentanoic acids of the formula ##STR1## wherein R is CF.sub.3, CHF.sub.2 or CH.sub.2 F; R.sub.1 is H or akyl of 1-4 carbon atoms; and R.sub.2 is H or alkyl or 1-4 carbon atoms or benzyl, which are intermediates to ACE inhibitors or elastase inhibitors, are produced by reacting a 1-(methylthio)-1-methylsulfinyl)-2-R.sub.1 -ethylmetal with an ester of a 3-R-acrylic acid; optionally R.sub.2 -alkylating the thus-produced ester enolate anion of 4-(methylsulfinyl)-4-(methylthio)-5-R.sub.1 R-pentanoic acid followed by splitting off of methylsulfinic acid; reacting the thus-produced 2-R.sub.2 -5-R.sub.1 -4-(methylthio)-3-R-4-pentenoic acid ester with a source of Br.sup.+ to produce a 5-bromo-substituted acid or ester thereof otherwise corresponding to the desired 5-amino-4-oxo-pentanoic acid; and replacing the bromine atom with an amino group, e.g., via the corresponding 5-azido- and 5-N-acylamino- compounds, with hydrolysis of the ester group, if still remaining.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: April 20, 1982
    Assignee: Richardson-Merrell Inc.
    Inventors: Brian W. Metcalf, Jerry L. Adams
  • Patent number: 4321382
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, a straight or branched chain alkyl of 1-5 carbon atoms or a straight or branched chain alkanoyl of 1-5 carbon atoms;R.sub.2 is hydrogen, a straight or branched chain alkyl of 1-5 carbon atoms, phenyl, phenyl substituted with halogen, a straight or branched chain alkoxy of 1-5 carbon atoms, a straight or branched chain alkyl of 1-5 carbon atoms or trifluoromethyl or, when R.sub.1 is hydrogen, R.sub.2 can also be a straight or branched chain alkanoyl of 1-5 carbon atoms; orR.sub.1 and R.sub.2 taken together with the nitrogen atom to which they are attached form a saturated heterocyclic ring of 4-7 total ring atoms and 0 or 1 hetero N or O atom in addition to the connecting N atom; or the corresponding heterocyclic ring substituted by a C.sub.1-5 straight or branched chain alkyl group, aryl or aralkyl;R.sub.
    Type: Grant
    Filed: August 10, 1979
    Date of Patent: March 23, 1982
    Assignee: Richardson-Merrell Inc.
    Inventors: Charles A. Lundberg, Jr., Robert A. Farr
  • Patent number: 4317818
    Abstract: Compounds of the following general formula are useful in treating prostatic carcinoma: ##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 28, 1980
    Date of Patent: March 2, 1982
    Assignee: Richardson-Merrell Inc.
    Inventors: Harvey D. Benson, Joyce F. Grunwell, John O. Johnston, Vladimir Petrow
  • Patent number: 4317817
    Abstract: Compounds of the following general formula are testosterone 5.alpha.-reductase inhibitors rendering the compounds useful in the treatment of acne and oily skin and benign prostatic hypertrophy: ##STR1## wherein R is: .dbd.O, --OH, --OCO--alkyl C.sub.1-5, --COOH, --CH.sub.2 OH, --COO--alkyl C.sub.1-6, --COCH.sub.
    Type: Grant
    Filed: December 15, 1980
    Date of Patent: March 2, 1982
    Assignee: Richardson-Merrell Inc.
    Inventors: Thomas R. Blohm, Brian W. Metcalf
  • Patent number: 4312879
    Abstract: Clonidine and lofexidine and the pharmaceutically acceptable salts thereof, which are, inter alia, known antihypertensives, also possess very potent antidiarrheal activity which is non-narcotic and more potent than that of conventional antidiarrheal drugs, such as diphenoxylate.
    Type: Grant
    Filed: August 14, 1980
    Date of Patent: January 26, 1982
    Assignee: Richardson-Merrell Inc.
    Inventor: Harbans Lal
  • Patent number: 4310524
    Abstract: A method is provided for treating depression in a patient therefrom and requiring rapid symptomatic relief, which comprises administering to said patient concurrently (a) an effective antidepressant amount of a tricyclic antidepressant or a pharmaceutically effective acid addition salt thereof, and (b) an amount of an .alpha.-adrenergic receptor blocking agent effective to achieve rapid onset of the antidepressant action of (a), whereby the onset of said antidepressant action is achieved within from 1 to 7 days.A pharmaceutical composition is also provided which is especially adapted for use with the foregoing method.
    Type: Grant
    Filed: April 11, 1980
    Date of Patent: January 12, 1982
    Assignee: Richardson-Merrell, Inc.
    Inventors: Norbert L. Wiech, Richard C. Ursillo
  • Patent number: 4309426
    Abstract: A method of achieving a muscle-relaxing effect in a patient comprises administering to a patient in which a muscle relaxing effect is desired an amount effective to achieve a muscle-relaxing effect of a compound of the formula ##STR1## wherein R is H, or C.sub.1-7 straight or branched chain alkyl;R.sub.1 is H, C.sub.1-7 straight or branched chain alkyl, allyl or phenyl;R.sub.2 is phenyl, phenyl monosubstituted with F, Cl, C.sub.1-4 straight or branched chain alkyl or phenyl disubstituted in the 2- and 4-positions with Cl or C.sub.1-4 straight or branched chain alkyl; andR.sub.3 is H or C.sub.1-4 straight or branched chain alkyl, with the proviso that when R.sub.3 is straight or branched chain alkyl, R.sub.2 is unsubstituted phenyl;or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: November 20, 1980
    Date of Patent: January 5, 1982
    Assignee: Richardson-Merrell Inc.
    Inventors: Winton D. Jones, Jr., Francis P. Miller
  • Patent number: 4302581
    Abstract: Novel 7-(1,3-dithiolan-2-imino)cephalosporin derivatives are described which are particularly useful for their antibacterial properties.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: November 24, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Boyd L. Harrison, Joseph E. Dolfini
  • Patent number: 4291160
    Abstract: Novel 7-(1,3-dithiolan-2-imino)-.DELTA..sup.2 -cephalosporanic acid derivatives are described which possess useful antibacterial properties.
    Type: Grant
    Filed: November 5, 1979
    Date of Patent: September 22, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Boyd L. Harrison, Joseph E. Dolfini
  • Patent number: 4289767
    Abstract: Compounds of the formula ##STR1## wherein R is H, C.sub.1-5 or 7 -straight or branched chain alkyl or allyl and R.sub.1 is H or Cl andthe pharmacologically acceptable acid addition salts thereof are pharmacologically active as anticonvulsant and anxiolytic agents.
    Type: Grant
    Filed: September 4, 1979
    Date of Patent: September 15, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Winton D. Jones, Francis P. Miller
  • Patent number: 4285957
    Abstract: Novel compounds of the following formula: ##STR1## wherein R.sub.1 is hydrogen or hydroxy; R.sub.2 is hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is an integer of from 1 to 5; R.sub.3 is --CH.sub.3, --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and each of A and B is hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R.sub.3 is --CH.sub.3 ; and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: October 14, 1980
    Date of Patent: August 25, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
  • Patent number: 4285958
    Abstract: Pharmaceutically useful compounds of the following formula: ##STR1## wherein R.sub.1 represents hydrogen or hydroxy; R.sub.2 represents hydrogen; or R.sub.1 and R.sub.2 taken together form a second bond between the carbon atoms bearing R.sub.1 and R.sub.2 ; n is a positive whole integer of from 1 to 5; R.sub.3 is --CH.sub.3, --CH.sub.2 OH, --COOH or --COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; and A and B are individually hydrogen or hydroxy; with the provisos that at least one of A or B is hydrogen and one of A or B is other than hydrogen when R.sub.3 is --CH.sub.3 ; and pharmaceutically acceptable acid addition salts thereof.
    Type: Grant
    Filed: October 14, 1980
    Date of Patent: August 25, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, Joseph E. Dolfini, George J. Wright
  • Patent number: 4284636
    Abstract: Cinnamoylpiperidinobutyrophenone derivatives and pharmaceutically acceptable salts thereof of the following general structure: ##STR1## wherein R is hydrogen, alkyl, alkoxy, halogen or trifluoromethyl; and R' is hydrogen or halogen; are useful as antipsychotic agents. The novel compounds are produced by aldol condensation of a benzaldehyde with a protected 4-(4-acetyl-1-piperidino)-butyrophenone.
    Type: Grant
    Filed: September 4, 1979
    Date of Patent: August 18, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Albert A. Carr, Robert A. Farr
  • Patent number: 4283385
    Abstract: Dentifrice preparations having improved soluble fluoride availability are obtained by incorporation of ethylenediamine tetraacetic acid and sodium salts thereof.
    Type: Grant
    Filed: May 9, 1980
    Date of Patent: August 11, 1981
    Assignee: Richardson-Merrell Inc.
    Inventors: Dadi J. Dhabhar, Nutan B. Shah