Chalcogen Bonded Directly To Ring Carbon Of The Tricyclo Ring System Patents (Class 546/86)
  • Patent number: 4478750
    Abstract: A 1,2,3,4,5,6-hexahydro-6-phenyl-azepino[4,5-b]indole, or a pharmaceutically acceptable acid addition salt thereof is a useful neuroleptic, anti-depressant and anti-allergic agent.
    Type: Grant
    Filed: June 7, 1982
    Date of Patent: October 23, 1984
    Assignee: Sandoz Ltd.
    Inventor: Fulvio Gadient
  • Patent number: 4477669
    Abstract: 1,1-Di(p-fluorophenyl)urea, 2-carbobenzoxy-8-fluoro-5-(p-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4, 3-b]indole, an efficient process for converting the former to the latter, further comprising conversion of the latter to 8-fluoro-5-(p-fluorophenyl)-2-[4-(p-fluorophenyl)-4-hydroxybutyl)]-2,3,4,5 -tetrahydro-1H-pyrido[4,3-b]indole (flutroline) or to 8-fluoro-5-(p-fluorophenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (an alternative flutroline intermediate).
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: October 16, 1984
    Assignee: Pfizer Inc.
    Inventor: Stephen S. Massett
  • Patent number: 4467090
    Abstract: 8-Fluoro-5-(p-fluorophenyl)-2-[4-(p-fluorophenyl)-4-hydroxybutyryl]-2,3,4,5 -tetrahydro-1H-pyrido[4,3-b]-indole; processes therefor; and process for the conversion to flutroline.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: August 21, 1984
    Assignee: Pfizer Inc.
    Inventors: Stephen S. Massett, Harry A. Watson, Jr.
  • Patent number: 4435403
    Abstract: 3-substituted beta-carbolines of the formula ##STR1## wherein R.sup.C is hydrogen, lower alkyl, alkoxyalkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms, aralkyl of up to 8 C-atoms, or (CH.sub.2).sub.n OR.sup.20wherein R.sup.20 is alkyl of up to 6 C-atoms, cycloalkyl of 3-6 C-atoms or aralkyl of up to 8 C-atoms and n is an integer of 1 to 3;Y is oxygen, two hydrogen atoms or NOR.sup.1,wherein R.sup.1 is hydrogen, lower alkyl, aryl or aralkyl of up to 6 C-atoms, COR.sup.2, wherein R.sup.2 is lower alkyl of up to 6 C-atoms,or Y is CHCOOR.sup.3, wherein R.sup.3 is hydrogen or lower alkylor Y is NNR.sup.4 R.sup.5,wherein R.sup.4 and R.sup.5 can be the same or different and each is hydrogen, lower alkyl, C.sub.6-10 -aryl, C.sub.7-10 -aralkyl or CONR.sup.6 R.sup.7,wherein R.sup.6 and R.sup.7 can be the same or different and each is hydrogen or lower alkyl or R.sup.4 and R.sup.
    Type: Grant
    Filed: December 17, 1981
    Date of Patent: March 6, 1984
    Assignee: Schering Aktiengesellschaft
    Inventors: Claus T. Braestrup, Jogen A. Christensen, Mogens Engelstoft, Gunter Neef, Ulrich Eder, Ralph Schmiechen, Andreas Huth, Dieter Rahtz, Dieter Seidelmann, Wolfgang Kehr, Dieter Palenschat
  • Patent number: 4432978
    Abstract: Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole and of (+)enantiomeric, mixtures of (+) and (-)enantiomeric or (.+-.)racemic 2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-position with a carbonylaminoalkyl group or an aminoalkyl group, are neuroleptic agents useful in the treatment of certain psychoses and neuroses.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: February 21, 1984
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Charles A. Harbert
  • Patent number: 4431649
    Abstract: Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole and of (+)enantiomeric, mixtures of (+) and (-)enantiomeric or (.+-.)racemic 2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-position with a carbonylaminoalkyl group or an aminoalkyl group, are neuroleptic agents useful in the treatment of certain psychoses and neuroses.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: February 14, 1984
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Charles A. Harbert
  • Patent number: 4431646
    Abstract: Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole and of (+)enantiomeric, mixtures of (+) and (-)enantiomeric or (.+-.)racemic 2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-position with a carbonylaminoalkyl group or an aminoalkyl group, are neuroleptic agents useful in the treatment of certain psychoses and neuroses.
    Type: Grant
    Filed: May 20, 1982
    Date of Patent: February 14, 1984
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Charles A. Harbert
  • Patent number: 4387098
    Abstract: Novel imidazo[1,2-a]quinolines of the formula ##STR1## wherein R is selected from the group consisting of alkyl of 1 to 8 carbon atoms, thienyl, pyridyl and phenyl optionally substituted with at least one member of the group consisting of halogen, alkyl of 1 to 5 carbon atoms and alkoxy of 1 to 5 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen, halogen, alkyl and alkoxy of 1 to 8 carbon atoms,s cyclohexyl, --NO.sub.2 and phenoxy, R.sub.3 is selected from the group consisting of alkoxy and alkylthio of 1 to 8 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable anxiolytic activity and a hypnotic activity and their preparation.
    Type: Grant
    Filed: March 25, 1982
    Date of Patent: June 7, 1983
    Assignee: Roussel Uclaf
    Inventors: Alan C. Barnes, Peter A. Robson
  • Patent number: 4371536
    Abstract: A .beta.-carbolin-3-carboxylic acid derivative of the formula ##STR1## has valuable pharmacological properties when administered to patients, e.g. humans as a drug, have been shown to possess interesting tranquilizing activity.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: February 1, 1983
    Assignees: A/S Ferrosan, Scherling AG
    Inventors: Claus T. Braestrup, Mogens C. Nielsen, Joergen A. Christensen, Mogens Engelstoft, Henning Schou, Ulrich Eder, Gunter Neef, Andreas Huth, Dieter Rahtz, Ralph Schmiechen
  • Patent number: 4361566
    Abstract: Disclosed are novel tetrahydro .beta.-carbolines of the formula: ##STR1## wherein R is H, OCH.sub.3 or F; R.sub.1 is H or CH.sub.3 and R.sub.2 is H or COOR.sub.3 where R.sub.3 is H or CH.sub.3. These compounds are useful as antihypertensive agents.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: November 30, 1982
    Assignee: Miles Laboratories, Inc.
    Inventors: John W. Van Dyke, Jr., Elva Kurchacova
  • Patent number: 4358451
    Abstract: Pyrimido- and imidazo-pyridoindole derivatives, in the form of racemates or optically active isomers, of formula: ##STR1## in which n=0 or 1, R.sub.1 =H, Hal, alkyl or alkoxy or CF.sub.3, R.sub.2 =H, alkyl, cycloalkyl-alkyl, cycloalkyl, N,N-dialkylaminoalkyl or phenyl, R.sub.3 =H or alkyl and R.sub.4 =H, alkyl or benzyl are useful as anti-anoxia or psychotropic agents in therapy. They are prepared by cyclizing a compound of formula: ##STR2## wherein R.sub.5 is alkyl, by heating it in an acidic medium, such as ethanolic hydrogen chloride.
    Type: Grant
    Filed: January 15, 1980
    Date of Patent: November 9, 1982
    Assignee: Synthelabo
    Inventors: Gabor I. Koletar, Jonathan R. Frost, Regis DuPont, Patrick Lardenois, Claude Morel, Henry Najer
  • Patent number: 4352807
    Abstract: Medicinal agents classed as 2-(aminoalkyl or amidoalkyl)-5-aryl-hexahydro-trans-4a,9b-1(H)-pyrido-[4,3-b]indole derivatives have been synthesized and found to have neuroleptic activity.
    Type: Grant
    Filed: August 28, 1980
    Date of Patent: October 5, 1982
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Charles A. Harbert
  • Patent number: 4336256
    Abstract: Pyridoindole derivatives of formula ##STR1## n=0 or 1; R.sub.1 =H, Hal, alk, alk--O--, CF.sub.3 ; R.sub.2 =--COOalk; --CONHR.sub.5 (R.sub.5 =H or various substituents); R.sub.3 =H, alk, --COOalk; R.sub.4 =H, Ac, alk, --CONHR.sub.6 (R.sub.6 =H or various substituents), and acid addition salts, except certain known compounds, are useful in treating anoxia and depression and in psychotropic therapy. They are prepared from tryptamine or a derivative thereof by reaction thereof with a pyruvic ester or 3-ethoxycarbonyl-1,2-dioxo-1-ethoxypropane to form compounds in which R.sub.4 is H and R.sub.2 is --COOalk. These compounds are reacted with amines, isocyanates or usual N-acylating or N-alkylating reagents to prepare the other compounds.
    Type: Grant
    Filed: September 4, 1980
    Date of Patent: June 22, 1982
    Assignee: Synthelabo
    Inventors: Gabor I. Koletar, Jonathan B. Frost, Regis DuPont, Patrick Lardenois, Claude Morel, Henry Najer
  • Patent number: 4334004
    Abstract: This invention relates to 2-hydroxy-3-naphthoic acid amides of the general formula: ##STR1## wherein R.sub.1 is hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, and R.sub.2 and R.sub.3 are identical or different and are hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, or, together with the nitrogen atom to which they are attached, a substituted or unsubstituted heterocyclic group.
    Type: Grant
    Filed: March 16, 1979
    Date of Patent: June 8, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Siegfried Scheler
  • Patent number: 4291039
    Abstract: Disclosed are novel tetrahydro .beta.-carbolines of the formula: ##STR1## wherein R is H, OCH.sub.3 or F; R.sub.1 is H or CH.sub.3 and R.sub.2 is H or COOR.sub.3 where R.sub.3 is H or CH.sub.3. These compounds are useful as antihypertensive agents.
    Type: Grant
    Filed: August 8, 1980
    Date of Patent: September 22, 1981
    Assignee: Miles Laboratories, Inc.
    Inventors: John W. Van Dyke, Jr., Elva Kurchacova
  • Patent number: 4272539
    Abstract: Pyridoindole derivatives of formula ##STR1## n=0 or 1; R.sub.1 =H, Hal, alk, alk-O-, CF.sub.3 ; R.sub.2 =--COOalk; --CONHR.sub.5 (R.sub.5 =H or various substituents); R.sub.3 =H, alk, --COOalk; R.sub.4 =H, Ac, alk, --CONHR.sub.6 (R.sub.6 =H or various substituents), and acid addition salts, except certain known compounds, are useful in treating anoxia and depression and in psychotropic therapy. They are prepared from tryptamine or a derivative thereof by reaction thereof with a pyruvic ester or 3-ethoxycarbonyl-1,2-dioxo-1-ethoxypropane to form compounds in which R.sub.4 is H and R.sub.2 is --COOalk. These compounds are reacted with amines, isocyanates or usual N-acylating or N-alkylating reagents to prepare the other compounds.
    Type: Grant
    Filed: January 15, 1980
    Date of Patent: June 9, 1981
    Assignee: Synthelabo
    Inventors: Gabor I. Koletar, Jonathan R. Frost, Regis Dupont, Patrick Lardenois, Claude Morel, Henry Najer
  • Patent number: 4252811
    Abstract: Medicinal agents classed as 2-(aminoalkyl or amidoalkyl)-5-aryl-hexahydro-trans-4a,9b-1(H)-pyrido[4,3-b]indole derivatives have been synthesized and found to have neuroleptic activity.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: February 24, 1981
    Assignee: Pfizer Inc.
    Inventors: Willard M. Welch, Charles A. Harbert
  • Patent number: 4220774
    Abstract: The preparation of vincadifformine and some derivatives thereof for use as a starting material for synthesis of the corresponding vincamine derivatives or for synthesis of bisindole alkaloids having clinically important antitumor properties.
    Type: Grant
    Filed: October 26, 1978
    Date of Patent: September 2, 1980
    Assignee: Omnium Chimique
    Inventor: Martin E. Kuehne
  • Patent number: 4218453
    Abstract: The invention relates to new products, in the form of bases or salts, derivatives of hexahydro-6-canthinone which may be substituted and are represented by the general formula: ##STR1## in which R.sub.1 represents a hydrogen atom or hydroxy, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.5 acyloxy, methoxy or halo radical and R.sub.2 represents a hydrogen atom or straight or branched C.sub.1 -C.sub.5 alkyl radical with the proviso that R.sub.1 is not hydrogen or hydroxy in the 8-position when R.sub.2 is methyl or R.sub.1 is not methoxy in the 10-position when R.sub.2 is hydrogen. The new products are especially useful for treating cardio-circulatory, cerebro-vascular and respiratory insufficiencies.The invention also relates to a process in which the hexahydro-6-canthinone compounds are obtained by treating a N.sub.b -alkyltryptamine with .beta.-formylpropionic acid in an aromatic hydrocarbon at the reflux temperature of the reaction medium.
    Type: Grant
    Filed: August 22, 1977
    Date of Patent: August 19, 1980
    Inventor: Jean A. A. J. Hannart
  • Patent number: 4217454
    Abstract: Process for the stereoselective reduction of certain amino-substituted indoles and amino-substituted indole-containing structures to trans-dihydroindoles comprising the sequential steps of (1) reacting a strong acid addition salt of such an indole with a borohydride in an appropriate solvent in the absence of acid, and (2) acidifying the step (1) reaction product by which it is reduced and hydrolyzed to form the corresponding trans-dihydroindole. Many dihydroindoles so produced, for example, the trans-2-(adamantylemethyl)-=2,3,4,4a,5,9b-hexahydro-5-phenyl-1H-pyrido[4,3 -b]indole, are useful as pharmaceutical materials, such as tranquilizers.
    Type: Grant
    Filed: July 26, 1978
    Date of Patent: August 12, 1980
    Assignee: Endo Laboratories, Inc.
    Inventor: Joel G. Berger
  • Patent number: 4174453
    Abstract: Certain trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido-[4,3-b]indoles are useful as analgesics and sedatives. Some are also useful as major (antipsychotics) and/or minor (anxiolytics) tranquilizers, muscle relaxants, or hypotensives. The compounds of this invention are made by (1) reaction of .DELTA..sup.4a,9b -tetrahydro precursors with borane/THF and (2) acidifying the reaction product by which it is reduced and hydrolyzed to form the corresponding trans-hexahydro compound.
    Type: Grant
    Filed: May 22, 1978
    Date of Patent: November 13, 1979
    Assignee: Endo Laboratories, Inc.
    Inventor: Joel G. Berger